Monoclinic-to-ortho­rhom­bic phase transition of the hexa­methyl­ene­tetra­mine–2-methyl­benzoic acid (1/2) cocrystal with temperature-dependent dynamic mol­ecular disorder

Chia, T.S.; Quah, C.K.

doi:10.1107/S2053229616016831

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Monoclinic-to-orthorhombic phase transition of the hexamethylenetetramine–2-methylbenzoic acid (1/2) cocrystal with temperature-dependent dynamic molecular disorder

T. S. Chia and C. K. Quah

As a function of temperature, the hexamethylenetetramine–2-methylbenzoic acid (1/2) cocrystal, C₆H₁₂N₄·2C₈H₈O₂, undergoes a reversible structural phase transition. The orthorhombic high-temperature phase in the space group Pccn has been studied in the temperature range between 165 and 300 K. At 164 K, a t₂ phase transition to the monoclinic subgroup P2₁/c space group occurs; the resulting twinned low-temperature phase was investigated in the temperature range between 164 and 100 K. The domains in the pseudomerohedral twin are related by a twofold rotation corresponding to the matrix (100/0 $\overline{1}$ 0/00 $\overline{1}$ ). Systematic absence violations represent a sensitive criterium for the decision about the correct space-group assignment at each temperature. The fractional volume contributions of the minor twin domain in the low-temperature phase increases in the order 0.259 (2) → 0.318 (2) → 0.336 (2) → 0.341 (3) as the temperature increases in the order 150 → 160 → 163 → 164 K. The transformation occurs between the nonpolar point group mmm and the nonpolar point group 2/m, and corresponds to a ferroelastic transition or to a t₂ structural phase transition. The asymmetric unit of the low-temperature phase consists of two hexamethylenetetramine molecules and four molecules of 2-methylbenzoic acid; it is smaller by a factor of 2 in the high-temperature phase and contains two half molecules of hexamethylenetetramine, which sit across twofold axes, and two molecules of the organic acid. In both phases, the hexamethylenetetramine residue and two benzoic acid molecules form a three-molecule aggregate; the low-temperature phase contains two of these aggregates in general positions, whereas they are situated on a crystallographic twofold axis in the high-temperature phase. In both phases, one of these three-molecule aggregates is disordered. For this disordered unit, the ratio between the major and minor conformer increases upon cooling from 0.567 (7):0.433 (7) at 170 K via 0.674 (6):0.326 (6) and 0.808 (5):0.192 (5) at 160 K to 0.803 (6):0.197 (6) and 0.900 (4):0.100 (4) at 150 K, indicating temperature-dependent dynamic molecular disorder. Even upon further cooling to 100 K, the disorder is retained in principle, albeit with very low site occupancies for the minor conformer.

Keywords: pseudomerohedral twin; second-order phase transition; dynamic disorder; crystal structure; temperature-dependent diffraction; ferroelastic; acid–base; cocrystal.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616016831/eg3207sup1.cif Contains datablocks 100K, 150K, 160K, 163K, 164K, 165K, 166K, 170K, 300K, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207100Ksup20.hkl Contains datablock 100K
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207150Ksup21.hkl Contains datablock 150K
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207160Ksup22.hkl Contains datablock 160K
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207163Ksup23.hkl Contains datablock 163K
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207164Ksup24.hkl Contains datablock 164K
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207165Ksup25.hkl Contains datablock 165K
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207166Ksup26.hkl Contains datablock 166K
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207170Ksup27.hkl Contains datablock 170K
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207300Ksup28.hkl Contains datablock 300K

CCDC references: 1492798; 1492797; 1492796; 1492795; 1492794; 1492793; 1492792; 1492791; 1492790

Computing details top

For all compounds, data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008a) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

(100K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top

Crystal data top

C₆H₁₂N₄·2C₈H₈O₂	F(000) = 1760
M_r = 412.48	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 30.904 (5) Å	Cell parameters from 9953 reflections
b = 9.3351 (16) Å	θ = 2.3–29.1°
c = 14.353 (2) Å	µ = 0.09 mm⁻¹
β = 90.222 (3)°	T = 100 K
V = 4140.7 (11) Å³	Block, colourless
Z = 8	0.39 × 0.33 × 0.26 mm

Data collection top

Bruker APEX DUO CCD area detector diffractometer	8099 independent reflections
Radiation source: fine-focus sealed tube	7204 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
φ and ω scans	θ_max = 26.0°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −38→37
T_min = 0.810, T_max = 0.947	k = −11→11
54203 measured reflections	l = −17→17

Refinement top

Refinement on F²	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.160	w = 1/[σ²(F_o²) + (0.0773P)² + 4.1888P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
8099 reflections	Δρ_max = 0.64 e Å⁻³
562 parameters	Δρ_min = −0.23 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.16429 (8)	0.2381 (3)	0.33462 (19)	0.0406 (6)
H1O1	0.1784 (12)	0.246 (4)	0.2839 (19)	0.049 (12)*
O2	0.12836 (9)	0.4229 (3)	0.27456 (16)	0.0439 (6)
O3	0.36626 (7)	0.1744 (2)	0.28027 (15)	0.0312 (5)
H1O3	0.3453 (11)	0.195 (5)	0.245 (3)	0.062 (14)*
O4	0.33504 (7)	0.3309 (2)	0.37521 (17)	0.0358 (5)
O5	0.13407 (9)	0.8279 (3)	0.52668 (19)	0.0448 (6)
H1O5	0.1575 (15)	0.802 (8)	0.502 (5)	0.15 (3)*
O6	0.15604 (8)	0.6793 (3)	0.6378 (2)	0.0492 (7)
O7	0.36420 (8)	0.6942 (3)	0.51812 (18)	0.0400 (6)
H1O7	0.3382 (9)	0.712 (6)	0.501 (4)	0.077 (17)*
O8	0.33995 (8)	0.7980 (3)	0.6463 (2)	0.0486 (7)
N1	0.21740 (8)	0.2517 (2)	0.19156 (17)	0.0216 (5)
N2	0.29592 (8)	0.2296 (2)	0.17519 (17)	0.0217 (5)
N3	0.24672 (8)	0.1153 (2)	0.06219 (17)	0.0224 (5)
N4	0.25374 (8)	0.3772 (2)	0.06589 (16)	0.0220 (5)
N5	0.20935 (8)	0.7764 (2)	0.43961 (18)	0.0223 (5)
N6	0.28718 (8)	0.7342 (2)	0.43796 (18)	0.0226 (5)
N7	0.24047 (8)	0.6228 (2)	0.32030 (16)	0.0217 (5)
N8	0.25341 (8)	0.8813 (2)	0.31670 (17)	0.0227 (5)
C1	0.10787 (9)	0.3302 (3)	0.4244 (2)	0.0242 (6)
C2	0.07828 (10)	0.4407 (3)	0.4460 (2)	0.0281 (7)
C3	0.05609 (11)	0.4302 (4)	0.5292 (2)	0.0353 (8)
H3A	0.0362	0.5035	0.5455	0.042*
C4	0.06208 (12)	0.3159 (4)	0.5895 (2)	0.0418 (9)
H4A	0.0466	0.3127	0.6465	0.050*
C5	0.09058 (12)	0.2060 (4)	0.5674 (2)	0.0383 (8)
H5A	0.0946	0.1271	0.6083	0.046*
C6	0.11286 (10)	0.2145 (3)	0.4849 (2)	0.0292 (7)
H6A	0.1322	0.1394	0.4687	0.035*
C7	0.13352 (10)	0.3367 (3)	0.3367 (2)	0.0279 (6)
C8	0.06932 (11)	0.5691 (3)	0.3850 (3)	0.0357 (8)
H8A	0.0591	0.5368	0.3238	0.054*
H8B	0.0959	0.6248	0.3775	0.054*
H8C	0.0471	0.6290	0.4142	0.054*
C9	0.39527 (9)	0.2020 (3)	0.4344 (2)	0.0196 (6)
C10	0.41867 (9)	0.0726 (3)	0.4376 (2)	0.0209 (6)
C11	0.44576 (10)	0.0493 (3)	0.5151 (2)	0.0262 (6)
H11A	0.4615	−0.0379	0.5190	0.031*
C12	0.45028 (10)	0.1487 (3)	0.5857 (2)	0.0301 (7)
H12A	0.4691	0.1294	0.6367	0.036*
C13	0.42751 (10)	0.2764 (3)	0.5824 (2)	0.0293 (7)
H13A	0.4305	0.3451	0.6308	0.035*
C14	0.40033 (10)	0.3023 (3)	0.5073 (2)	0.0239 (6)
H14A	0.3847	0.3898	0.5047	0.029*
C15	0.36291 (9)	0.2421 (3)	0.3609 (2)	0.0208 (6)
C16	0.41711 (10)	−0.0412 (3)	0.3634 (2)	0.0278 (6)
H16A	0.3869	−0.0602	0.3463	0.042*
H16B	0.4304	−0.1293	0.3872	0.042*
H16C	0.4330	−0.0082	0.3084	0.042*
C17	0.08182 (9)	0.7499 (3)	0.6339 (2)	0.0251 (6)
C18	0.06742 (11)	0.6690 (3)	0.7095 (2)	0.0320 (7)
C19	0.02328 (10)	0.6728 (4)	0.7311 (3)	0.0366 (8)
H19A	0.0129	0.6192	0.7827	0.044*
C20	−0.00563 (11)	0.7533 (4)	0.6788 (3)	0.0384 (8)
H20A	−0.0354	0.7532	0.6948	0.046*
C21	0.00832 (11)	0.8344 (4)	0.6032 (3)	0.0380 (8)
H21A	−0.0116	0.8897	0.5676	0.046*
C22	0.05122 (11)	0.8323 (3)	0.5817 (3)	0.0338 (7)
H22A	0.0611	0.8873	0.5303	0.041*
C23	0.12698 (10)	0.7495 (3)	0.6005 (2)	0.0314 (7)
C24	0.09609 (12)	0.5781 (4)	0.7694 (3)	0.0416 (8)
H24A	0.0786	0.5288	0.8163	0.062*
H24B	0.1176	0.6388	0.8006	0.062*
H24C	0.1109	0.5071	0.7306	0.062*
C25	0.41586 (9)	0.7485 (3)	0.6351 (2)	0.0227 (6)
C26	0.43051 (10)	0.8278 (3)	0.7111 (2)	0.0267 (6)
C27	0.47509 (10)	0.8216 (3)	0.7337 (2)	0.0310 (7)
H27A	0.4856	0.8749	0.7854	0.037*
C28	0.50350 (10)	0.7411 (3)	0.6829 (2)	0.0319 (7)
H28A	0.5333	0.7392	0.6997	0.038*
C29	0.48885 (11)	0.6614 (3)	0.6064 (2)	0.0317 (7)
H29A	0.5085	0.6047	0.5715	0.038*
C30	0.44569 (10)	0.6658 (3)	0.5820 (2)	0.0272 (7)
H30A	0.4357	0.6134	0.5293	0.033*
C31	0.36989 (10)	0.7496 (3)	0.6010 (2)	0.0253 (6)
C32	0.40246 (11)	0.9198 (4)	0.7693 (2)	0.0357 (7)
H32A	0.4204	0.9752	0.8127	0.054*
H32B	0.3823	0.8598	0.8045	0.054*
H32C	0.3861	0.9855	0.7292	0.054*
C33	0.25954 (9)	0.2388 (3)	0.24103 (19)	0.0216 (6)
H33A	0.2637	0.3230	0.2821	0.026*
H33B	0.2592	0.1521	0.2807	0.026*
C34	0.28807 (10)	0.1046 (3)	0.1134 (2)	0.0236 (6)
H34A	0.3120	0.0970	0.0682	0.028*
H34B	0.2880	0.0162	0.1515	0.028*
C35	0.21168 (10)	0.1256 (3)	0.1296 (2)	0.0225 (6)
H35A	0.2109	0.0373	0.1678	0.027*
H35B	0.1837	0.1337	0.0961	0.027*
C36	0.21844 (10)	0.3830 (3)	0.1331 (2)	0.0235 (6)
H36A	0.1906	0.3931	0.0996	0.028*
H36B	0.2222	0.4680	0.1737	0.028*
C37	0.29503 (10)	0.3608 (3)	0.1167 (2)	0.0235 (6)
H37A	0.2997	0.4457	0.1569	0.028*
H37B	0.3191	0.3568	0.0713	0.028*
C38	0.24733 (11)	0.2484 (3)	0.00687 (18)	0.0241 (6)
H38A	0.2196	0.2575	−0.0275	0.029*
H38B	0.2709	0.2428	−0.0394	0.029*
C39	0.24873 (10)	0.7575 (3)	0.49655 (18)	0.0238 (6)
H39A	0.2449	0.6744	0.5386	0.029*
H39B	0.2533	0.8436	0.5356	0.029*
C40	0.27919 (10)	0.6067 (3)	0.3790 (2)	0.0242 (6)
H40A	0.3046	0.5902	0.3388	0.029*
H40B	0.2757	0.5217	0.4195	0.029*
C41	0.20344 (10)	0.6471 (3)	0.3803 (2)	0.0245 (6)
H41A	0.1992	0.5624	0.4207	0.029*
H41B	0.1772	0.6590	0.3414	0.029*
C42	0.21598 (10)	0.9010 (3)	0.3770 (2)	0.0236 (6)
H42A	0.1898	0.9149	0.3380	0.028*
H42B	0.2201	0.9885	0.4150	0.028*
C43	0.29158 (10)	0.8604 (3)	0.3755 (2)	0.0262 (6)
H43A	0.2963	0.9472	0.4138	0.031*
H43B	0.3173	0.8473	0.3354	0.031*
C44	0.24618 (11)	0.7498 (3)	0.26074 (19)	0.0261 (6)
H44A	0.2201	0.7626	0.2213	0.031*
H44B	0.2712	0.7345	0.2191	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0366 (13)	0.0444 (14)	0.0410 (15)	0.0105 (11)	0.0137 (11)	0.0071 (11)
O2	0.0523 (15)	0.0502 (15)	0.0293 (12)	0.0141 (12)	0.0077 (11)	0.0083 (11)
O3	0.0304 (12)	0.0352 (12)	0.0279 (11)	0.0116 (10)	−0.0038 (10)	−0.0041 (9)
O4	0.0316 (12)	0.0318 (12)	0.0440 (13)	0.0155 (10)	−0.0100 (10)	−0.0129 (10)
O5	0.0409 (15)	0.0492 (15)	0.0443 (15)	0.0019 (12)	0.0110 (12)	0.0066 (12)
O6	0.0229 (12)	0.0493 (15)	0.075 (2)	0.0089 (11)	0.0036 (13)	0.0094 (14)
O7	0.0332 (13)	0.0494 (15)	0.0373 (13)	0.0057 (11)	−0.0069 (11)	−0.0089 (11)
O8	0.0271 (12)	0.0605 (16)	0.0581 (17)	0.0082 (12)	0.0022 (12)	−0.0152 (14)
N1	0.0275 (12)	0.0187 (11)	0.0185 (12)	−0.0008 (10)	0.0019 (10)	−0.0030 (9)
N2	0.0262 (12)	0.0175 (11)	0.0215 (12)	0.0000 (9)	−0.0018 (10)	0.0019 (9)
N3	0.0331 (14)	0.0132 (10)	0.0209 (12)	0.0007 (9)	0.0016 (11)	−0.0007 (9)
N4	0.0351 (14)	0.0131 (10)	0.0177 (12)	−0.0003 (9)	−0.0016 (11)	0.0004 (9)
N5	0.0225 (12)	0.0180 (11)	0.0266 (13)	−0.0014 (9)	0.0073 (11)	−0.0019 (10)
N6	0.0226 (12)	0.0176 (11)	0.0277 (13)	0.0004 (9)	−0.0053 (11)	0.0017 (10)
N7	0.0308 (13)	0.0150 (11)	0.0194 (12)	0.0000 (10)	−0.0008 (10)	−0.0026 (9)
N8	0.0290 (13)	0.0169 (11)	0.0222 (12)	0.0004 (10)	−0.0020 (10)	0.0039 (9)
C1	0.0214 (14)	0.0281 (15)	0.0231 (14)	−0.0035 (11)	−0.0012 (12)	−0.0054 (12)
C2	0.0277 (15)	0.0270 (15)	0.0297 (16)	−0.0076 (12)	−0.0001 (13)	−0.0056 (12)
C3	0.0318 (17)	0.0376 (18)	0.0367 (18)	−0.0066 (14)	0.0115 (15)	−0.0150 (15)
C4	0.046 (2)	0.054 (2)	0.0253 (17)	−0.0248 (17)	0.0137 (15)	−0.0138 (16)
C5	0.048 (2)	0.0378 (17)	0.0292 (17)	−0.0180 (16)	−0.0028 (16)	0.0061 (14)
C6	0.0268 (15)	0.0324 (16)	0.0283 (16)	−0.0022 (13)	−0.0063 (13)	−0.0030 (13)
C7	0.0251 (15)	0.0272 (14)	0.0314 (16)	−0.0019 (12)	−0.0006 (13)	−0.0051 (13)
C8	0.0353 (17)	0.0260 (15)	0.046 (2)	−0.0028 (13)	0.0019 (15)	0.0004 (14)
C9	0.0164 (13)	0.0191 (12)	0.0232 (14)	−0.0021 (10)	0.0026 (11)	0.0025 (11)
C10	0.0181 (13)	0.0197 (13)	0.0250 (14)	−0.0030 (10)	0.0052 (12)	0.0019 (11)
C11	0.0236 (14)	0.0211 (13)	0.0341 (16)	−0.0007 (12)	0.0034 (13)	0.0071 (12)
C12	0.0343 (17)	0.0274 (15)	0.0287 (17)	−0.0081 (13)	−0.0037 (14)	0.0076 (13)
C13	0.0376 (17)	0.0297 (15)	0.0208 (15)	−0.0072 (13)	0.0027 (13)	−0.0037 (12)
C14	0.0253 (15)	0.0201 (13)	0.0263 (15)	0.0003 (11)	0.0054 (12)	−0.0002 (11)
C15	0.0204 (13)	0.0171 (12)	0.0249 (14)	−0.0020 (11)	0.0001 (11)	0.0013 (11)
C16	0.0254 (15)	0.0193 (13)	0.0387 (17)	0.0030 (11)	0.0020 (13)	−0.0026 (12)
C17	0.0217 (14)	0.0238 (13)	0.0298 (16)	−0.0020 (12)	0.0018 (13)	−0.0088 (12)
C18	0.0313 (17)	0.0301 (16)	0.0345 (17)	−0.0029 (13)	−0.0006 (14)	−0.0067 (13)
C19	0.0259 (16)	0.0442 (19)	0.0396 (19)	−0.0100 (14)	0.0073 (14)	−0.0186 (16)
C20	0.0314 (17)	0.0460 (19)	0.0377 (19)	−0.0064 (16)	0.0044 (15)	−0.0141 (16)
C21	0.0286 (17)	0.0420 (19)	0.043 (2)	0.0110 (15)	−0.0093 (15)	−0.0112 (16)
C22	0.0332 (17)	0.0310 (16)	0.0371 (18)	0.0012 (14)	−0.0003 (15)	−0.0062 (14)
C23	0.0280 (16)	0.0278 (15)	0.0386 (19)	−0.0055 (14)	0.0040 (15)	−0.0098 (14)
C24	0.046 (2)	0.0392 (19)	0.040 (2)	−0.0005 (16)	−0.0031 (17)	−0.0007 (15)
C25	0.0246 (14)	0.0187 (12)	0.0248 (15)	−0.0033 (11)	−0.0009 (12)	0.0064 (11)
C26	0.0334 (16)	0.0224 (14)	0.0242 (15)	−0.0046 (12)	0.0025 (13)	0.0067 (12)
C27	0.0288 (16)	0.0287 (16)	0.0355 (18)	−0.0064 (13)	−0.0042 (14)	0.0138 (14)
C28	0.0296 (16)	0.0319 (16)	0.0342 (18)	−0.0069 (14)	−0.0028 (14)	0.0103 (13)
C29	0.0308 (16)	0.0263 (15)	0.0382 (18)	0.0046 (13)	0.0084 (14)	0.0058 (13)
C30	0.0301 (16)	0.0232 (14)	0.0283 (16)	−0.0005 (12)	−0.0014 (13)	0.0025 (12)
C31	0.0252 (15)	0.0174 (12)	0.0331 (17)	−0.0020 (12)	−0.0038 (13)	0.0039 (12)
C32	0.0398 (19)	0.0306 (16)	0.0369 (18)	0.0002 (14)	0.0070 (15)	−0.0012 (14)
C33	0.0298 (15)	0.0202 (13)	0.0146 (13)	−0.0013 (12)	−0.0010 (11)	0.0009 (11)
C34	0.0304 (16)	0.0168 (12)	0.0235 (14)	0.0011 (11)	0.0013 (12)	−0.0013 (11)
C35	0.0305 (15)	0.0151 (12)	0.0219 (14)	−0.0043 (11)	0.0003 (12)	−0.0008 (11)
C36	0.0312 (16)	0.0153 (13)	0.0238 (15)	0.0032 (11)	−0.0032 (13)	−0.0051 (11)
C37	0.0304 (16)	0.0163 (12)	0.0238 (15)	−0.0040 (11)	0.0014 (12)	0.0015 (11)
C38	0.0395 (16)	0.0183 (12)	0.0146 (12)	0.0020 (11)	−0.0014 (13)	0.0002 (12)
C39	0.0370 (15)	0.0157 (12)	0.0185 (13)	−0.0008 (11)	0.0020 (14)	−0.0023 (11)
C40	0.0271 (15)	0.0161 (13)	0.0293 (15)	0.0072 (11)	−0.0012 (12)	−0.0008 (12)
C41	0.0258 (15)	0.0158 (12)	0.0317 (16)	−0.0081 (11)	0.0005 (13)	−0.0029 (12)
C42	0.0274 (15)	0.0138 (12)	0.0297 (16)	0.0050 (11)	−0.0033 (13)	−0.0009 (12)
C43	0.0211 (14)	0.0214 (13)	0.0361 (17)	−0.0055 (11)	0.0023 (13)	0.0009 (13)
C44	0.0404 (17)	0.0212 (13)	0.0168 (13)	0.0012 (12)	−0.0004 (14)	0.0017 (12)

Geometric parameters (Å, º) top

O1—C7	1.324 (4)	C13—C14	1.385 (4)
O1—H1O1	0.853 (19)	C13—H13A	0.9500
O2—C7	1.211 (4)	C14—H14A	0.9500
O3—C15	1.323 (4)	C16—H16A	0.9800
O3—H1O3	0.845 (19)	C16—H16B	0.9800
O4—C15	1.213 (3)	C16—H16C	0.9800
O5—C23	1.307 (4)	C17—C18	1.396 (5)
O5—H1O5	0.85 (2)	C17—C22	1.429 (5)
O6—C23	1.232 (4)	C17—C23	1.478 (4)
O7—C31	1.308 (4)	C18—C19	1.401 (5)
O7—H1O7	0.854 (19)	C18—C24	1.496 (5)
O8—C31	1.220 (4)	C19—C20	1.386 (5)
N1—C35	1.485 (3)	C19—H19A	0.9500
N1—C36	1.485 (4)	C20—C21	1.393 (6)
N1—C33	1.486 (4)	C20—H20A	0.9500
N2—C33	1.474 (4)	C21—C22	1.363 (5)
N2—C34	1.485 (4)	C21—H21A	0.9500
N2—C37	1.485 (3)	C22—H22A	0.9500
N3—C35	1.458 (4)	C24—H24A	0.9800
N3—C38	1.475 (4)	C24—H24B	0.9800
N3—C34	1.475 (4)	C24—H24C	0.9800
N4—C36	1.461 (4)	C25—C26	1.392 (4)
N4—C37	1.475 (4)	C25—C30	1.426 (4)
N4—C38	1.484 (4)	C25—C31	1.501 (4)
N5—C39	1.474 (4)	C26—C27	1.415 (4)
N5—C42	1.485 (4)	C26—C32	1.481 (4)
N5—C41	1.488 (4)	C27—C28	1.368 (5)
N6—C39	1.474 (4)	C27—H27A	0.9500
N6—C40	1.480 (4)	C28—C29	1.401 (5)
N6—C43	1.487 (4)	C28—H28A	0.9500
N7—C41	1.453 (4)	C29—C30	1.378 (5)
N7—C40	1.469 (4)	C29—H29A	0.9500
N7—C44	1.473 (4)	C30—H30A	0.9500
N8—C42	1.459 (4)	C32—H32A	0.9800
N8—C43	1.461 (4)	C32—H32B	0.9800
N8—C44	1.483 (4)	C32—H32C	0.9800
C1—C6	1.395 (4)	C33—H33A	0.9900
C1—C2	1.414 (4)	C33—H33B	0.9900
C1—C7	1.491 (4)	C34—H34A	0.9900
C2—C3	1.383 (5)	C34—H34B	0.9900
C2—C8	1.509 (4)	C35—H35A	0.9900
C3—C4	1.386 (5)	C35—H35B	0.9900
C3—H3A	0.9500	C36—H36A	0.9900
C4—C5	1.389 (5)	C36—H36B	0.9900
C4—H4A	0.9500	C37—H37A	0.9900
C5—C6	1.374 (5)	C37—H37B	0.9900
C5—H5A	0.9500	C38—H38A	0.9900
C6—H6A	0.9500	C38—H38B	0.9900
C8—H8A	0.9800	C39—H39A	0.9900
C8—H8B	0.9800	C39—H39B	0.9900
C8—H8C	0.9800	C40—H40A	0.9900
C9—C10	1.408 (4)	C40—H40B	0.9900
C9—C14	1.412 (4)	C41—H41A	0.9900
C9—C15	1.499 (4)	C41—H41B	0.9900
C10—C11	1.406 (4)	C42—H42A	0.9900
C10—C16	1.506 (4)	C42—H42B	0.9900
C11—C12	1.380 (4)	C43—H43A	0.9900
C11—H11A	0.9500	C43—H43B	0.9900
C12—C13	1.385 (5)	C44—H44A	0.9900
C12—H12A	0.9500	C44—H44B	0.9900

C7—O1—H1O1	109 (3)	C18—C24—H24B	109.5
C15—O3—H1O3	111 (3)	H24A—C24—H24B	109.5
C23—O5—H1O5	109 (6)	C18—C24—H24C	109.5
C31—O7—H1O7	108 (4)	H24A—C24—H24C	109.5
C35—N1—C36	108.6 (2)	H24B—C24—H24C	109.5
C35—N1—C33	108.9 (2)	C26—C25—C30	119.9 (3)
C36—N1—C33	108.4 (2)	C26—C25—C31	123.8 (3)
C33—N2—C34	107.8 (2)	C30—C25—C31	116.2 (3)
C33—N2—C37	107.6 (2)	C25—C26—C27	118.1 (3)
C34—N2—C37	107.9 (2)	C25—C26—C32	124.1 (3)
C35—N3—C38	108.2 (2)	C27—C26—C32	117.8 (3)
C35—N3—C34	108.5 (2)	C28—C27—C26	121.8 (3)
C38—N3—C34	108.2 (2)	C28—C27—H27A	119.1
C36—N4—C37	108.9 (2)	C26—C27—H27A	119.1
C36—N4—C38	108.0 (2)	C27—C28—C29	120.2 (3)
C37—N4—C38	108.2 (2)	C27—C28—H28A	119.9
C39—N5—C42	108.3 (2)	C29—C28—H28A	119.9
C39—N5—C41	108.6 (2)	C30—C29—C28	119.5 (3)
C42—N5—C41	107.8 (2)	C30—C29—H29A	120.2
C39—N6—C40	108.2 (2)	C28—C29—H29A	120.2
C39—N6—C43	107.6 (2)	C29—C30—C25	120.5 (3)
C40—N6—C43	107.9 (2)	C29—C30—H30A	119.8
C41—N7—C40	108.5 (2)	C25—C30—H30A	119.8
C41—N7—C44	108.3 (2)	O8—C31—O7	122.1 (3)
C40—N7—C44	108.5 (2)	O8—C31—C25	123.2 (3)
C42—N8—C43	108.3 (2)	O7—C31—C25	114.7 (3)
C42—N8—C44	107.9 (2)	C26—C32—H32A	109.5
C43—N8—C44	108.8 (2)	C26—C32—H32B	109.5
C6—C1—C2	119.9 (3)	H32A—C32—H32B	109.5
C6—C1—C7	120.0 (3)	C26—C32—H32C	109.5
C2—C1—C7	120.1 (3)	H32A—C32—H32C	109.5
C3—C2—C1	117.5 (3)	H32B—C32—H32C	109.5
C3—C2—C8	117.8 (3)	N2—C33—N1	111.6 (2)
C1—C2—C8	124.8 (3)	N2—C33—H33A	109.3
C2—C3—C4	121.9 (3)	N1—C33—H33A	109.3
C2—C3—H3A	119.1	N2—C33—H33B	109.3
C4—C3—H3A	119.1	N1—C33—H33B	109.3
C3—C4—C5	120.6 (3)	H33A—C33—H33B	108.0
C3—C4—H4A	119.7	N3—C34—N2	112.6 (2)
C5—C4—H4A	119.7	N3—C34—H34A	109.1
C6—C5—C4	118.3 (3)	N2—C34—H34A	109.1
C6—C5—H5A	120.8	N3—C34—H34B	109.1
C4—C5—H5A	120.8	N2—C34—H34B	109.1
C5—C6—C1	121.8 (3)	H34A—C34—H34B	107.8
C5—C6—H6A	119.1	N3—C35—N1	111.3 (2)
C1—C6—H6A	119.1	N3—C35—H35A	109.4
O2—C7—O1	122.5 (3)	N1—C35—H35A	109.4
O2—C7—C1	125.4 (3)	N3—C35—H35B	109.4
O1—C7—C1	112.0 (3)	N1—C35—H35B	109.4
C2—C8—H8A	109.5	H35A—C35—H35B	108.0
C2—C8—H8B	109.5	N4—C36—N1	111.1 (2)
H8A—C8—H8B	109.5	N4—C36—H36A	109.4
C2—C8—H8C	109.5	N1—C36—H36A	109.4
H8A—C8—H8C	109.5	N4—C36—H36B	109.4
H8B—C8—H8C	109.5	N1—C36—H36B	109.4
C10—C9—C14	119.2 (3)	H36A—C36—H36B	108.0
C10—C9—C15	125.4 (3)	N4—C37—N2	112.3 (2)
C14—C9—C15	115.3 (2)	N4—C37—H37A	109.2
C11—C10—C9	117.6 (3)	N2—C37—H37A	109.2
C11—C10—C16	117.9 (2)	N4—C37—H37B	109.2
C9—C10—C16	124.5 (3)	N2—C37—H37B	109.2
C12—C11—C10	122.3 (3)	H37A—C37—H37B	107.9
C12—C11—H11A	118.8	N3—C38—N4	112.2 (2)
C10—C11—H11A	118.8	N3—C38—H38A	109.2
C11—C12—C13	120.2 (3)	N4—C38—H38A	109.2
C11—C12—H12A	119.9	N3—C38—H38B	109.2
C13—C12—H12A	119.9	N4—C38—H38B	109.2
C12—C13—C14	118.9 (3)	H38A—C38—H38B	107.9
C12—C13—H13A	120.5	N5—C39—N6	111.5 (2)
C14—C13—H13A	120.5	N5—C39—H39A	109.3
C13—C14—C9	121.7 (3)	N6—C39—H39A	109.3
C13—C14—H14A	119.1	N5—C39—H39B	109.3
C9—C14—H14A	119.1	N6—C39—H39B	109.3
O4—C15—O3	122.2 (3)	H39A—C39—H39B	108.0
O4—C15—C9	121.5 (3)	N7—C40—N6	112.3 (2)
O3—C15—C9	116.2 (2)	N7—C40—H40A	109.1
C10—C16—H16A	109.5	N6—C40—H40A	109.1
C10—C16—H16B	109.5	N7—C40—H40B	109.1
H16A—C16—H16B	109.5	N6—C40—H40B	109.1
C10—C16—H16C	109.5	H40A—C40—H40B	107.9
H16A—C16—H16C	109.5	N7—C41—N5	111.8 (2)
H16B—C16—H16C	109.5	N7—C41—H41A	109.3
C18—C17—C22	119.1 (3)	N5—C41—H41A	109.3
C18—C17—C23	123.7 (3)	N7—C41—H41B	109.3
C22—C17—C23	117.0 (3)	N5—C41—H41B	109.3
C17—C18—C19	118.2 (3)	H41A—C41—H41B	107.9
C17—C18—C24	124.3 (3)	N8—C42—N5	111.8 (2)
C19—C18—C24	117.5 (3)	N8—C42—H42A	109.3
C20—C19—C18	121.3 (3)	N5—C42—H42A	109.3
C20—C19—H19A	119.3	N8—C42—H42B	109.3
C18—C19—H19A	119.3	N5—C42—H42B	109.3
C19—C20—C21	121.1 (3)	H42A—C42—H42B	107.9
C19—C20—H20A	119.5	N8—C43—N6	112.3 (2)
C21—C20—H20A	119.5	N8—C43—H43A	109.2
C22—C21—C20	118.2 (3)	N6—C43—H43A	109.2
C22—C21—H21A	120.9	N8—C43—H43B	109.2
C20—C21—H21A	120.9	N6—C43—H43B	109.2
C21—C22—C17	122.1 (3)	H43A—C43—H43B	107.9
C21—C22—H22A	119.0	N7—C44—N8	111.7 (2)
C17—C22—H22A	119.0	N7—C44—H44A	109.3
O6—C23—O5	121.7 (3)	N8—C44—H44A	109.3
O6—C23—C17	123.2 (3)	N7—C44—H44B	109.3
O5—C23—C17	115.0 (3)	N8—C44—H44B	109.3
C18—C24—H24A	109.5	H44A—C44—H44B	107.9

C6—C1—C2—C3	1.7 (4)	C26—C25—C30—C29	1.3 (4)
C7—C1—C2—C3	−178.7 (3)	C31—C25—C30—C29	178.3 (3)
C6—C1—C2—C8	−178.5 (3)	C26—C25—C31—O8	−14.1 (5)
C7—C1—C2—C8	1.1 (4)	C30—C25—C31—O8	169.1 (3)
C1—C2—C3—C4	−0.4 (5)	C26—C25—C31—O7	165.9 (3)
C8—C2—C3—C4	179.8 (3)	C30—C25—C31—O7	−10.9 (4)
C2—C3—C4—C5	−0.7 (5)	C34—N2—C33—N1	−57.6 (3)
C3—C4—C5—C6	0.6 (5)	C37—N2—C33—N1	58.6 (3)
C4—C5—C6—C1	0.7 (5)	C35—N1—C33—N2	58.5 (3)
C2—C1—C6—C5	−1.9 (4)	C36—N1—C33—N2	−59.5 (3)
C7—C1—C6—C5	178.5 (3)	C35—N3—C34—N2	−59.1 (3)
C6—C1—C7—O2	171.3 (3)	C38—N3—C34—N2	58.1 (3)
C2—C1—C7—O2	−8.3 (5)	C33—N2—C34—N3	58.2 (3)
C6—C1—C7—O1	−10.5 (4)	C37—N2—C34—N3	−57.7 (3)
C2—C1—C7—O1	169.9 (3)	C38—N3—C35—N1	−58.6 (3)
C14—C9—C10—C11	0.8 (4)	C34—N3—C35—N1	58.6 (3)
C15—C9—C10—C11	−176.1 (3)	C36—N1—C35—N3	59.1 (3)
C14—C9—C10—C16	−178.3 (3)	C33—N1—C35—N3	−58.8 (3)
C15—C9—C10—C16	4.8 (4)	C37—N4—C36—N1	−58.6 (3)
C9—C10—C11—C12	−0.9 (4)	C38—N4—C36—N1	58.7 (3)
C16—C10—C11—C12	178.3 (3)	C35—N1—C36—N4	−59.2 (3)
C10—C11—C12—C13	0.5 (4)	C33—N1—C36—N4	59.0 (3)
C11—C12—C13—C14	−0.1 (4)	C36—N4—C37—N2	58.8 (3)
C12—C13—C14—C9	0.1 (4)	C38—N4—C37—N2	−58.3 (3)
C10—C9—C14—C13	−0.5 (4)	C33—N2—C37—N4	−58.3 (3)
C15—C9—C14—C13	176.8 (3)	C34—N2—C37—N4	57.8 (3)
C10—C9—C15—O4	157.5 (3)	C35—N3—C38—N4	59.0 (3)
C14—C9—C15—O4	−19.6 (4)	C34—N3—C38—N4	−58.4 (3)
C10—C9—C15—O3	−21.9 (4)	C36—N4—C38—N3	−59.1 (3)
C14—C9—C15—O3	161.0 (3)	C37—N4—C38—N3	58.6 (3)
C22—C17—C18—C19	−0.3 (4)	C42—N5—C39—N6	−58.7 (3)
C23—C17—C18—C19	−176.6 (3)	C41—N5—C39—N6	58.1 (3)
C22—C17—C18—C24	179.8 (3)	C40—N6—C39—N5	−57.9 (3)
C23—C17—C18—C24	3.5 (5)	C43—N6—C39—N5	58.5 (3)
C17—C18—C19—C20	0.6 (5)	C41—N7—C40—N6	−58.8 (3)
C24—C18—C19—C20	−179.5 (3)	C44—N7—C40—N6	58.7 (3)
C18—C19—C20—C21	−0.6 (5)	C39—N6—C40—N7	58.3 (3)
C19—C20—C21—C22	0.2 (5)	C43—N6—C40—N7	−57.9 (3)
C20—C21—C22—C17	0.1 (5)	C40—N7—C41—N5	58.4 (3)
C18—C17—C22—C21	0.0 (5)	C44—N7—C41—N5	−59.1 (3)
C23—C17—C22—C21	176.5 (3)	C39—N5—C41—N7	−58.6 (3)
C18—C17—C23—O6	−1.4 (5)	C42—N5—C41—N7	58.6 (3)
C22—C17—C23—O6	−177.7 (3)	C43—N8—C42—N5	−58.7 (3)
C18—C17—C23—O5	177.6 (3)	C44—N8—C42—N5	59.0 (3)
C22—C17—C23—O5	1.2 (4)	C39—N5—C42—N8	58.7 (3)
C30—C25—C26—C27	−0.8 (4)	C41—N5—C42—N8	−58.6 (3)
C31—C25—C26—C27	−177.4 (3)	C42—N8—C43—N6	59.1 (3)
C30—C25—C26—C32	178.4 (3)	C44—N8—C43—N6	−57.9 (3)
C31—C25—C26—C32	1.7 (4)	C39—N6—C43—N8	−58.9 (3)
C25—C26—C27—C28	0.2 (4)	C40—N6—C43—N8	57.6 (3)
C32—C26—C27—C28	−179.0 (3)	C41—N7—C44—N8	59.4 (3)
C26—C27—C28—C29	−0.1 (5)	C40—N7—C44—N8	−58.2 (3)
C27—C28—C29—C30	0.6 (5)	C42—N8—C44—N7	−59.2 (3)
C28—C29—C30—C25	−1.3 (5)	C43—N8—C44—N7	58.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.85 (3)	1.80 (3)	2.637 (4)	168 (4)
O3—H1O3···N2	0.84 (4)	1.85 (4)	2.691 (3)	174 (4)
O5—H1O5···N5	0.84 (5)	1.85 (5)	2.689 (4)	170 (7)
O7—H1O7···N6	0.86 (3)	1.83 (4)	2.666 (4)	166 (6)
C6—H6A···O1	0.95	2.36	2.693 (4)	100
C16—H16A···O3	0.98	2.47	2.816 (4)	100
C22—H22A···O5	0.95	2.32	2.683 (4)	102
C30—H30A···O7	0.95	2.34	2.690 (4)	101
C33—H33A···O4	0.99	2.57	3.140 (4)	116
C33—H33B···N8ⁱ	0.99	2.59	3.515 (3)	156
C36—H36B···N7	0.99	2.61	3.561 (4)	160
C38—H38B···O4ⁱⁱ	0.99	2.43	3.392 (4)	163
C40—H40B···N3ⁱⁱⁱ	0.99	2.58	3.498 (4)	155
C44—H44A···O6^iv	0.99	2.37	3.358 (4)	173
C44—H44B···O8^iv	0.99	2.39	3.366 (4)	169

Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) x, −y+3/2, z−1/2.

(150K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top

Crystal data top

C₆H₁₂N₄·2C₈H₈O₂	F(000) = 1760
M_r = 412.48	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 30.920 (3) Å	Cell parameters from 9985 reflections
b = 9.3363 (9) Å	θ = 2.3–26.6°
c = 14.3462 (14) Å	µ = 0.09 mm⁻¹
β = 90.314 (2)°	T = 150 K
V = 4141.4 (7) Å³	Block, colourless
Z = 8	0.43 × 0.17 × 0.15 mm

Data collection top

Bruker APEX DUO CCD area detector diffractometer	9989 independent reflections
Radiation source: fine-focus sealed tube	7832 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
φ and ω scans	θ_max = 28.0°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −40→40
T_min = 0.769, T_max = 0.963	k = −12→12
65004 measured reflections	l = −18→18

Refinement top

Refinement on F²	1222 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.197	w = 1/[σ²(F_o²) + (0.1018P)² + 2.4093P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
9989 reflections	Δρ_max = 0.43 e Å⁻³
837 parameters	Δρ_min = −0.24 e Å⁻³

Special details top

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.16458 (10)	0.2389 (4)	0.3356 (2)	0.0453 (8)	0.803 (6)
H1O1	0.1813 (13)	0.250 (5)	0.291 (2)	0.054 (14)*	0.803 (6)
O2	0.12827 (12)	0.4205 (5)	0.2743 (2)	0.0547 (9)	0.803 (6)
C7	0.13377 (12)	0.3353 (4)	0.3370 (3)	0.0306 (8)	0.803 (6)
C1	0.10771 (18)	0.3308 (5)	0.4241 (3)	0.0284 (8)	0.803 (6)
C2	0.0784 (3)	0.4407 (6)	0.4467 (4)	0.0324 (9)	0.803 (6)
C3	0.0562 (3)	0.4293 (7)	0.5308 (4)	0.0405 (12)	0.803 (6)
H3A	0.0364	0.5024	0.5477	0.049*	0.803 (6)
C4	0.06230 (18)	0.3153 (6)	0.5898 (3)	0.0435 (11)	0.803 (6)
H4A	0.0470	0.3113	0.6470	0.052*	0.803 (6)
C5	0.09044 (18)	0.2066 (5)	0.5668 (3)	0.0412 (10)	0.803 (6)
H5A	0.0943	0.1273	0.6075	0.049*	0.803 (6)
C6	0.11288 (14)	0.2137 (5)	0.4845 (3)	0.0325 (8)	0.803 (6)
H6A	0.1321	0.1385	0.4683	0.039*	0.803 (6)
C8	0.06987 (17)	0.5688 (5)	0.3856 (4)	0.0400 (11)	0.803 (6)
H8A	0.0968	0.6223	0.3769	0.060*	0.803 (6)
H8B	0.0484	0.6308	0.4152	0.060*	0.803 (6)
H8C	0.0589	0.5367	0.3249	0.060*	0.803 (6)
O1X	0.1334 (5)	0.3388 (18)	0.2842 (10)	0.056 (3)	0.197 (6)
H2O1	0.1520	0.3118	0.2454	0.084*	0.197 (6)
O2X	0.1648 (4)	0.1732 (16)	0.3752 (11)	0.058 (3)	0.197 (6)
C7X	0.1373 (5)	0.2632 (18)	0.3608 (10)	0.036 (2)	0.197 (6)
C1X	0.1061 (9)	0.300 (2)	0.4369 (14)	0.031 (2)	0.197 (6)
C2X	0.0822 (13)	0.427 (3)	0.436 (2)	0.034 (2)	0.197 (6)
C3X	0.0550 (11)	0.447 (3)	0.5112 (18)	0.036 (2)	0.197 (6)
H3XA	0.0385	0.5329	0.5130	0.043*	0.197 (6)
C4X	0.0505 (7)	0.353 (2)	0.5830 (15)	0.039 (2)	0.197 (6)
H4XA	0.0318	0.3746	0.6334	0.047*	0.197 (6)
C5X	0.0733 (7)	0.225 (2)	0.5822 (12)	0.037 (2)	0.197 (6)
H5XA	0.0695	0.1561	0.6300	0.044*	0.197 (6)
C6X	0.1012 (6)	0.2017 (19)	0.5108 (13)	0.034 (2)	0.197 (6)
H6XA	0.1180	0.1164	0.5108	0.041*	0.197 (6)
C8X	0.0817 (8)	0.542 (2)	0.3619 (14)	0.041 (4)	0.197 (6)
H8XA	0.1045	0.6126	0.3756	0.062*	0.197 (6)
H8XB	0.0535	0.5903	0.3617	0.062*	0.197 (6)
H8XC	0.0869	0.4996	0.3006	0.062*	0.197 (6)
O3	0.36593 (9)	0.1747 (3)	0.28202 (17)	0.0422 (6)	0.900 (4)
H1O3	0.3433 (11)	0.188 (6)	0.251 (3)	0.081 (16)*	0.900 (4)
O4	0.33475 (8)	0.3294 (3)	0.3771 (2)	0.0469 (7)	0.900 (4)
C15	0.36249 (10)	0.2416 (3)	0.3621 (2)	0.0293 (6)	0.900 (4)
C9	0.39507 (12)	0.2020 (3)	0.4356 (2)	0.0251 (6)	0.900 (4)
C10	0.4184 (2)	0.0731 (6)	0.4380 (4)	0.0266 (6)	0.900 (4)
C11	0.44569 (16)	0.0493 (4)	0.5148 (3)	0.0326 (7)	0.900 (4)
H11A	0.4613	−0.0381	0.5186	0.039*	0.900 (4)
C12	0.45049 (13)	0.1496 (4)	0.5852 (2)	0.0363 (8)	0.900 (4)
H12A	0.4697	0.1314	0.6358	0.044*	0.900 (4)
C13	0.42739 (13)	0.2761 (4)	0.5820 (2)	0.0356 (7)	0.900 (4)
H13A	0.4303	0.3448	0.6305	0.043*	0.900 (4)
C14	0.40008 (11)	0.3016 (3)	0.5076 (3)	0.0303 (7)	0.900 (4)
H14A	0.3843	0.3889	0.5052	0.036*	0.900 (4)
C16	0.41689 (13)	−0.0414 (3)	0.3644 (3)	0.0352 (8)	0.900 (4)
H16A	0.3868	−0.0578	0.3452	0.053*	0.900 (4)
H16B	0.4291	−0.1303	0.3896	0.053*	0.900 (4)
H16C	0.4338	−0.0108	0.3104	0.053*	0.900 (4)
O3X	0.3342 (6)	0.263 (2)	0.3362 (17)	0.041 (4)	0.100 (4)
H2O3	0.3201	0.2567	0.2861	0.061*	0.100 (4)
O4X	0.3724 (7)	0.087 (3)	0.2731 (13)	0.044 (4)	0.100 (4)
C15X	0.3654 (8)	0.168 (3)	0.3366 (16)	0.031 (3)	0.100 (4)
C9X	0.3938 (12)	0.166 (3)	0.423 (2)	0.029 (2)	0.100 (4)
C10X	0.424 (2)	0.059 (6)	0.446 (4)	0.030 (2)	0.100 (4)
C11X	0.4451 (16)	0.078 (4)	0.531 (2)	0.032 (3)	0.100 (4)
H11B	0.4670	0.0114	0.5486	0.039*	0.100 (4)
C12X	0.4359 (11)	0.189 (4)	0.5921 (19)	0.033 (2)	0.100 (4)
H12B	0.4485	0.1898	0.6526	0.039*	0.100 (4)
C13X	0.4089 (11)	0.298 (3)	0.565 (2)	0.032 (2)	0.100 (4)
H13B	0.4044	0.3790	0.6040	0.038*	0.100 (4)
C14X	0.3887 (10)	0.284 (3)	0.481 (2)	0.031 (2)	0.100 (4)
H14B	0.3702	0.3596	0.4612	0.037*	0.100 (4)
C16X	0.4323 (12)	−0.069 (3)	0.384 (2)	0.036 (5)	0.100 (4)
H16D	0.4550	−0.1288	0.4118	0.054*	0.100 (4)
H16E	0.4419	−0.0358	0.3223	0.054*	0.100 (4)
H16F	0.4058	−0.1255	0.3765	0.054*	0.100 (4)
O5	0.13451 (8)	0.8236 (3)	0.52665 (18)	0.0538 (6)
H1O5	0.1600 (9)	0.799 (6)	0.510 (4)	0.105 (19)*
O6	0.15657 (8)	0.6816 (3)	0.6407 (2)	0.0614 (7)
O7	0.36404 (8)	0.6928 (3)	0.52055 (17)	0.0520 (6)
H1O7	0.3380 (8)	0.705 (5)	0.500 (3)	0.075 (14)*
O8	0.34069 (8)	0.8009 (3)	0.6472 (2)	0.0641 (7)
N5	0.20988 (7)	0.7751 (2)	0.44080 (16)	0.0296 (5)
N6	0.28740 (7)	0.7330 (2)	0.44014 (16)	0.0294 (5)
N7	0.24123 (8)	0.6228 (2)	0.32180 (15)	0.0299 (5)
N8	0.25407 (7)	0.8806 (2)	0.31915 (15)	0.0303 (5)
C17	0.08235 (9)	0.7497 (3)	0.6344 (2)	0.0313 (6)
C18	0.06768 (10)	0.6693 (3)	0.7096 (2)	0.0382 (6)
C19	0.02389 (10)	0.6739 (4)	0.7308 (2)	0.0433 (7)
H19A	0.0135	0.6202	0.7823	0.052*
C20	−0.00495 (10)	0.7543 (4)	0.6791 (2)	0.0458 (8)
H20A	−0.0347	0.7545	0.6951	0.055*
C21	0.00916 (11)	0.8349 (4)	0.6040 (2)	0.0454 (8)
H21A	−0.0106	0.8911	0.5686	0.054*
C22	0.05226 (10)	0.8317 (3)	0.5821 (2)	0.0403 (7)
H22A	0.0622	0.8860	0.5305	0.048*
C23	0.12775 (10)	0.7481 (3)	0.6022 (2)	0.0374 (6)
C24	0.09651 (12)	0.5783 (4)	0.7695 (2)	0.0503 (8)
H24A	0.0791	0.5292	0.8166	0.075*
H24B	0.1181	0.6390	0.8004	0.075*
H24C	0.1112	0.5072	0.7306	0.075*
C25	0.41597 (9)	0.7483 (3)	0.63499 (19)	0.0301 (5)
C26	0.43075 (10)	0.8279 (3)	0.7114 (2)	0.0339 (6)
C27	0.47511 (10)	0.8220 (3)	0.7329 (2)	0.0377 (6)
H27A	0.4857	0.8756	0.7845	0.045*
C28	0.50337 (10)	0.7420 (3)	0.6822 (2)	0.0400 (7)
H28A	0.5332	0.7406	0.6986	0.048*
C29	0.48874 (10)	0.6624 (3)	0.6066 (2)	0.0394 (7)
H29A	0.5083	0.6056	0.5717	0.047*
C30	0.44564 (10)	0.6667 (3)	0.5829 (2)	0.0349 (6)
H30A	0.4357	0.6137	0.5305	0.042*
C31	0.37001 (9)	0.7499 (3)	0.6025 (2)	0.0336 (6)
C32	0.40265 (11)	0.9200 (4)	0.7698 (2)	0.0456 (7)
H32A	0.4206	0.9748	0.8137	0.068*
H32B	0.3824	0.8598	0.8046	0.068*
H32C	0.3864	0.9862	0.7298	0.068*
N1	0.21757 (13)	0.2511 (3)	0.1930 (2)	0.0265 (7)	0.867 (11)
N2	0.29590 (14)	0.2293 (3)	0.1772 (2)	0.0268 (7)	0.867 (11)
N3	0.24768 (13)	0.1163 (5)	0.0639 (3)	0.0275 (7)	0.867 (11)
N4	0.25464 (14)	0.3768 (5)	0.0682 (3)	0.0304 (8)	0.867 (11)
C33	0.25936 (17)	0.2382 (4)	0.2423 (2)	0.0267 (8)	0.867 (11)
H33A	0.2634	0.3222	0.2836	0.032*	0.867 (11)
H33B	0.2590	0.1514	0.2819	0.032*	0.867 (11)
C34	0.28840 (15)	0.1051 (4)	0.1152 (3)	0.0309 (8)	0.867 (11)
H34A	0.3125	0.0978	0.0703	0.037*	0.867 (11)
H34B	0.2882	0.0164	0.1530	0.037*	0.867 (11)
C35	0.21243 (15)	0.1254 (4)	0.1304 (3)	0.0286 (8)	0.867 (11)
H35A	0.2117	0.0368	0.1683	0.034*	0.867 (11)
H35B	0.1846	0.1331	0.0963	0.034*	0.867 (11)
C36	0.21907 (14)	0.3819 (4)	0.1351 (3)	0.0306 (8)	0.867 (11)
H36A	0.1913	0.3926	0.1011	0.037*	0.867 (11)
H36B	0.2227	0.4665	0.1761	0.037*	0.867 (11)
C37	0.29518 (15)	0.3608 (4)	0.1191 (3)	0.0308 (8)	0.867 (11)
H37A	0.2996	0.4454	0.1596	0.037*	0.867 (11)
H37B	0.3194	0.3572	0.0742	0.037*	0.867 (11)
C38	0.2486 (2)	0.2487 (7)	0.0091 (3)	0.0330 (9)	0.867 (11)
H38A	0.2211	0.2579	−0.0262	0.040*	0.867 (11)
H38B	0.2724	0.2433	−0.0366	0.040*	0.867 (11)
N1X	0.2021 (8)	0.278 (2)	0.1822 (14)	0.030 (2)	0.133 (11)
N2X	0.2807 (8)	0.245 (2)	0.1924 (15)	0.0285 (19)	0.133 (11)
N3X	0.2378 (8)	0.122 (3)	0.0709 (19)	0.029 (2)	0.133 (11)
N4X	0.2475 (9)	0.382 (4)	0.065 (2)	0.030 (2)	0.133 (11)
C33X	0.2401 (9)	0.263 (2)	0.2427 (13)	0.027 (2)	0.133 (11)
H33C	0.2424	0.3484	0.2831	0.032*	0.133 (11)
H33D	0.2359	0.1785	0.2836	0.032*	0.133 (11)
C34X	0.2758 (8)	0.116 (2)	0.1317 (18)	0.030 (2)	0.133 (11)
H34C	0.3019	0.1064	0.0927	0.036*	0.133 (11)
H34D	0.2738	0.0302	0.1716	0.036*	0.133 (11)
C35X	0.1990 (8)	0.144 (2)	0.1262 (18)	0.029 (2)	0.133 (11)
H35C	0.1949	0.0617	0.1685	0.034*	0.133 (11)
H35D	0.1735	0.1499	0.0843	0.034*	0.133 (11)
C36X	0.2080 (9)	0.399 (2)	0.1185 (19)	0.030 (2)	0.133 (11)
H36C	0.1828	0.4045	0.0755	0.036*	0.133 (11)
H36D	0.2094	0.4888	0.1546	0.036*	0.133 (11)
C37X	0.2840 (9)	0.370 (3)	0.126 (2)	0.030 (2)	0.133 (11)
H37C	0.2866	0.4596	0.1631	0.036*	0.133 (11)
H37D	0.3106	0.3597	0.0890	0.036*	0.133 (11)
C38X	0.2426 (14)	0.248 (4)	0.0098 (19)	0.031 (2)	0.133 (11)
H38C	0.2168	0.2562	−0.0312	0.037*	0.133 (11)
H38D	0.2682	0.2351	−0.0303	0.037*	0.133 (11)
C39	0.24894 (10)	0.7556 (3)	0.49808 (15)	0.0308 (5)
H39A	0.2450	0.6721	0.5397	0.037*
H39B	0.2533	0.8414	0.5376	0.037*
C40	0.27945 (10)	0.6057 (3)	0.38076 (19)	0.0313 (6)
H40A	0.3050	0.5890	0.3409	0.038*
H40B	0.2757	0.5205	0.4210	0.038*
C41	0.20427 (9)	0.6466 (3)	0.3813 (2)	0.0331 (6)
H41A	0.2000	0.5616	0.4214	0.040*
H41B	0.1781	0.6585	0.3421	0.040*
C42	0.21668 (9)	0.8994 (3)	0.3788 (2)	0.0316 (6)
H42A	0.1906	0.9135	0.3394	0.038*
H42B	0.2207	0.9866	0.4171	0.038*
C43	0.29197 (9)	0.8587 (3)	0.3784 (2)	0.0339 (6)
H43A	0.2967	0.9453	0.4169	0.041*
H43B	0.3177	0.8455	0.3385	0.041*
C44	0.24732 (11)	0.7496 (3)	0.26304 (16)	0.0346 (6)
H44A	0.2216	0.7625	0.2226	0.041*
H44B	0.2727	0.7346	0.2223	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0479 (17)	0.0485 (18)	0.0396 (16)	0.0164 (14)	0.0163 (13)	0.0130 (14)
O2	0.074 (2)	0.055 (2)	0.0352 (14)	0.0250 (17)	0.0121 (14)	0.0127 (14)
C7	0.0388 (17)	0.0292 (19)	0.0238 (16)	0.0001 (14)	−0.0016 (14)	−0.0021 (15)
C1	0.0311 (16)	0.028 (2)	0.0260 (17)	−0.0042 (17)	−0.0004 (13)	−0.0028 (13)
C2	0.038 (2)	0.0293 (19)	0.030 (2)	−0.0057 (15)	0.0020 (16)	−0.0097 (16)
C3	0.044 (2)	0.040 (2)	0.038 (3)	−0.0067 (19)	0.012 (2)	−0.0129 (19)
C4	0.050 (3)	0.048 (3)	0.0326 (18)	−0.012 (2)	0.0105 (19)	−0.0067 (18)
C5	0.048 (3)	0.044 (2)	0.031 (2)	−0.0134 (19)	0.0031 (19)	0.0053 (16)
C6	0.035 (2)	0.0355 (17)	0.0274 (19)	−0.0041 (15)	0.0010 (14)	0.0001 (14)
C8	0.041 (3)	0.030 (2)	0.049 (3)	0.0017 (18)	0.0053 (19)	−0.0028 (18)
O1X	0.083 (7)	0.046 (7)	0.039 (5)	0.020 (6)	0.019 (6)	0.005 (6)
O2X	0.059 (7)	0.052 (7)	0.062 (7)	0.024 (5)	0.011 (6)	0.005 (6)
C7X	0.040 (4)	0.035 (4)	0.031 (4)	0.003 (4)	0.002 (4)	−0.001 (4)
C1X	0.035 (4)	0.030 (4)	0.027 (4)	0.001 (4)	0.001 (3)	−0.006 (3)
C2X	0.039 (4)	0.032 (4)	0.031 (4)	−0.005 (4)	0.003 (4)	−0.003 (4)
C3X	0.042 (4)	0.033 (4)	0.033 (5)	−0.004 (4)	0.002 (4)	−0.003 (4)
C4X	0.046 (5)	0.039 (5)	0.032 (4)	−0.002 (4)	0.004 (4)	−0.004 (4)
C5X	0.043 (5)	0.039 (4)	0.027 (4)	−0.002 (4)	0.004 (4)	0.001 (4)
C6X	0.039 (4)	0.034 (4)	0.029 (4)	−0.001 (4)	0.004 (4)	0.001 (4)
C8X	0.046 (9)	0.034 (7)	0.043 (8)	0.003 (7)	0.003 (7)	0.001 (6)
O3	0.0470 (14)	0.0465 (16)	0.0330 (13)	0.0167 (12)	−0.0043 (11)	−0.0066 (11)
O4	0.0488 (15)	0.0379 (14)	0.0539 (15)	0.0203 (11)	−0.0127 (12)	−0.0149 (12)
C15	0.0288 (14)	0.0232 (14)	0.0359 (14)	−0.0013 (12)	0.0003 (11)	0.0007 (11)
C9	0.0271 (13)	0.0194 (15)	0.0287 (14)	−0.0010 (13)	0.0026 (11)	0.0010 (11)
C10	0.026 (2)	0.0201 (16)	0.0339 (16)	−0.0014 (11)	0.0031 (12)	0.0028 (14)
C11	0.0376 (15)	0.0191 (17)	0.0412 (19)	0.0001 (14)	−0.0004 (15)	0.0055 (12)
C12	0.046 (2)	0.0303 (17)	0.0326 (15)	−0.0032 (14)	−0.0050 (14)	0.0053 (13)
C13	0.0433 (19)	0.0329 (17)	0.0308 (15)	−0.0035 (15)	0.0005 (13)	−0.0034 (13)
C14	0.0345 (17)	0.0247 (13)	0.0319 (17)	0.0016 (12)	0.0019 (12)	−0.0015 (12)
C16	0.0352 (19)	0.0209 (14)	0.049 (2)	0.0044 (13)	0.0006 (15)	−0.0045 (13)
O3X	0.038 (7)	0.035 (8)	0.049 (8)	0.004 (6)	−0.015 (7)	−0.016 (7)
O4X	0.046 (9)	0.052 (9)	0.035 (7)	0.022 (8)	−0.009 (7)	−0.009 (7)
C15X	0.033 (5)	0.029 (5)	0.031 (5)	0.005 (5)	−0.001 (4)	−0.001 (5)
C9X	0.031 (4)	0.025 (4)	0.031 (4)	−0.004 (4)	0.001 (4)	−0.001 (4)
C10X	0.032 (5)	0.022 (4)	0.035 (4)	0.000 (4)	0.001 (4)	0.002 (4)
C11X	0.037 (5)	0.026 (5)	0.035 (4)	0.000 (4)	−0.003 (4)	0.003 (4)
C12X	0.040 (4)	0.027 (4)	0.032 (4)	0.002 (4)	−0.004 (4)	0.000 (4)
C13X	0.038 (5)	0.027 (4)	0.031 (4)	0.000 (4)	−0.004 (5)	−0.001 (4)
C14X	0.035 (4)	0.025 (4)	0.032 (4)	−0.003 (4)	−0.003 (4)	0.001 (4)
C16X	0.039 (11)	0.030 (9)	0.038 (9)	0.005 (8)	−0.012 (9)	0.000 (7)
O5	0.0484 (15)	0.0605 (15)	0.0527 (13)	0.0073 (12)	0.0152 (11)	0.0113 (12)
O6	0.0342 (12)	0.0663 (16)	0.0835 (19)	0.0099 (11)	0.0025 (12)	0.0190 (15)
O7	0.0433 (13)	0.0664 (16)	0.0460 (12)	0.0090 (12)	−0.0117 (10)	−0.0125 (12)
O8	0.0393 (13)	0.0851 (19)	0.0679 (17)	0.0113 (13)	0.0008 (12)	−0.0225 (15)
N5	0.0333 (12)	0.0231 (10)	0.0326 (11)	−0.0018 (9)	0.0057 (9)	−0.0015 (9)
N6	0.0343 (12)	0.0239 (10)	0.0301 (11)	0.0018 (9)	−0.0066 (9)	0.0006 (9)
N7	0.0455 (13)	0.0186 (10)	0.0256 (10)	−0.0001 (9)	−0.0025 (9)	−0.0043 (8)
N8	0.0406 (13)	0.0214 (10)	0.0288 (11)	0.0009 (9)	−0.0001 (9)	0.0068 (8)
C17	0.0301 (13)	0.0266 (12)	0.0373 (14)	−0.0024 (11)	0.0015 (11)	−0.0089 (11)
C18	0.0440 (17)	0.0310 (14)	0.0395 (15)	−0.0049 (12)	0.0003 (13)	−0.0082 (12)
C19	0.0356 (16)	0.0491 (18)	0.0451 (17)	−0.0077 (14)	0.0037 (13)	−0.0163 (15)
C20	0.0368 (16)	0.0563 (19)	0.0442 (17)	−0.0038 (15)	0.0023 (13)	−0.0188 (15)
C21	0.0384 (17)	0.0499 (18)	0.0477 (17)	0.0116 (14)	−0.0061 (14)	−0.0117 (15)
C22	0.0435 (17)	0.0337 (15)	0.0437 (16)	0.0025 (13)	−0.0011 (13)	−0.0059 (12)
C23	0.0368 (15)	0.0312 (14)	0.0442 (16)	−0.0040 (13)	0.0065 (13)	−0.0102 (12)
C24	0.056 (2)	0.0470 (18)	0.0481 (18)	−0.0010 (16)	−0.0028 (16)	0.0044 (15)
C25	0.0329 (13)	0.0236 (12)	0.0337 (13)	−0.0022 (11)	−0.0010 (11)	0.0086 (10)
C26	0.0420 (16)	0.0252 (13)	0.0343 (13)	−0.0042 (11)	0.0012 (12)	0.0054 (11)
C27	0.0393 (16)	0.0344 (15)	0.0394 (15)	−0.0075 (12)	−0.0057 (12)	0.0099 (12)
C28	0.0379 (15)	0.0395 (16)	0.0426 (16)	−0.0038 (13)	−0.0038 (13)	0.0115 (13)
C29	0.0407 (16)	0.0323 (14)	0.0454 (16)	0.0062 (12)	0.0071 (13)	0.0053 (12)
C30	0.0408 (16)	0.0271 (13)	0.0369 (14)	0.0008 (12)	−0.0018 (12)	0.0037 (11)
C31	0.0341 (14)	0.0263 (12)	0.0404 (15)	0.0000 (12)	−0.0034 (12)	0.0035 (11)
C32	0.0512 (19)	0.0407 (17)	0.0450 (17)	−0.0005 (14)	0.0050 (14)	−0.0038 (14)
N1	0.0308 (17)	0.0224 (13)	0.0262 (12)	0.0022 (12)	0.0011 (12)	−0.0031 (10)
N2	0.0334 (17)	0.0229 (12)	0.0242 (12)	0.0027 (12)	0.0007 (12)	0.0016 (10)
N3	0.043 (2)	0.0161 (11)	0.0238 (12)	0.0026 (13)	0.0021 (13)	−0.0033 (10)
N4	0.050 (2)	0.0163 (12)	0.0248 (12)	0.0011 (14)	−0.0029 (14)	0.0029 (10)
C33	0.037 (2)	0.0254 (14)	0.0181 (11)	0.0015 (15)	0.0012 (12)	0.0012 (10)
C34	0.040 (2)	0.0208 (13)	0.0313 (16)	0.0072 (13)	0.0027 (14)	−0.0012 (12)
C35	0.035 (2)	0.0195 (14)	0.0313 (14)	−0.0019 (13)	0.0000 (15)	−0.0040 (12)
C36	0.040 (2)	0.0194 (14)	0.0322 (17)	0.0087 (13)	−0.0072 (14)	−0.0047 (12)
C37	0.039 (2)	0.0207 (14)	0.0324 (16)	−0.0041 (14)	0.0010 (15)	0.0012 (12)
C38	0.056 (3)	0.0240 (13)	0.0190 (12)	0.0017 (15)	−0.0018 (15)	−0.0005 (12)
N1X	0.038 (4)	0.021 (4)	0.030 (4)	0.005 (4)	−0.002 (4)	−0.003 (4)
N2X	0.037 (4)	0.024 (3)	0.025 (3)	0.004 (4)	0.002 (3)	0.001 (3)
N3X	0.043 (4)	0.018 (4)	0.025 (4)	0.003 (4)	0.001 (4)	−0.001 (3)
N4X	0.045 (4)	0.021 (4)	0.026 (4)	0.001 (4)	−0.006 (3)	0.001 (3)
C33X	0.034 (4)	0.025 (4)	0.022 (4)	0.006 (4)	0.001 (4)	0.000 (4)
C34X	0.040 (4)	0.023 (4)	0.027 (4)	0.004 (4)	0.005 (4)	0.001 (4)
C35X	0.039 (4)	0.021 (4)	0.026 (4)	0.003 (4)	0.001 (4)	−0.002 (4)
C36X	0.042 (4)	0.020 (4)	0.029 (4)	0.005 (4)	−0.006 (4)	−0.001 (4)
C37X	0.040 (4)	0.023 (4)	0.028 (4)	−0.001 (4)	0.005 (4)	0.004 (4)
C38X	0.048 (5)	0.020 (4)	0.024 (4)	0.002 (4)	0.001 (4)	0.001 (4)
C39	0.0501 (15)	0.0215 (10)	0.0209 (9)	−0.0010 (10)	0.0008 (12)	−0.0008 (10)
C40	0.0415 (15)	0.0206 (12)	0.0319 (13)	0.0089 (11)	0.0003 (11)	−0.0010 (10)
C41	0.0360 (14)	0.0230 (12)	0.0403 (14)	−0.0082 (11)	−0.0012 (12)	−0.0046 (11)
C42	0.0383 (14)	0.0199 (11)	0.0368 (13)	0.0070 (11)	−0.0023 (11)	0.0005 (10)
C43	0.0346 (14)	0.0242 (12)	0.0429 (15)	−0.0088 (11)	0.0017 (12)	0.0036 (11)
C44	0.0534 (16)	0.0293 (12)	0.0210 (10)	0.0041 (11)	−0.0004 (12)	0.0015 (11)

Geometric parameters (Å, º) top

O1—C7	1.311 (5)	C17—C18	1.393 (4)
O1—H1O1	0.830 (19)	C17—C22	1.416 (4)
O2—C7	1.212 (5)	C17—C23	1.481 (4)
C7—C1	1.491 (5)	C18—C19	1.390 (4)
C1—C6	1.403 (5)	C18—C24	1.499 (5)
C1—C2	1.408 (5)	C19—C20	1.378 (5)
C2—C3	1.394 (5)	C19—H19A	0.9500
C2—C8	1.505 (5)	C20—C21	1.387 (5)
C3—C4	1.372 (7)	C20—H20A	0.9500
C3—H3A	0.9500	C21—C22	1.371 (5)
C4—C5	1.378 (7)	C21—H21A	0.9500
C4—H4A	0.9500	C22—H22A	0.9500
C5—C6	1.375 (5)	C24—H24A	0.9800
C5—H5A	0.9500	C24—H24B	0.9800
C6—H6A	0.9500	C24—H24C	0.9800
C8—H8A	0.9800	C25—C26	1.399 (4)
C8—H8B	0.9800	C25—C30	1.410 (4)
C8—H8C	0.9800	C25—C31	1.493 (4)
O1X—C7X	1.311 (14)	C26—C27	1.405 (4)
O1X—H2O1	0.8400	C26—C32	1.485 (4)
O2X—C7X	1.211 (14)	C27—C28	1.363 (5)
C7X—C1X	1.503 (14)	C27—H27A	0.9500
C1X—C2X	1.393 (15)	C28—C29	1.388 (5)
C1X—C6X	1.411 (15)	C28—H28A	0.9500
C2X—C3X	1.391 (16)	C29—C30	1.374 (4)
C2X—C8X	1.512 (15)	C29—H29A	0.9500
C3X—C4X	1.363 (16)	C30—H30A	0.9500
C3X—H3XA	0.9500	C32—H32A	0.9800
C4X—C5X	1.383 (16)	C32—H32B	0.9800
C4X—H4XA	0.9500	C32—H32C	0.9800
C5X—C6X	1.361 (16)	N1—C33	1.475 (4)
C5X—H5XA	0.9500	N1—C36	1.477 (4)
C6X—H6XA	0.9500	N1—C35	1.485 (4)
C8X—H8XA	0.9800	N2—C33	1.472 (4)
C8X—H8XB	0.9800	N2—C34	1.480 (4)
C8X—H8XC	0.9800	N2—C37	1.484 (4)
O3—C15	1.313 (4)	N3—C35	1.455 (4)
O3—H1O3	0.84 (2)	N3—C34	1.459 (4)
O4—C15	1.207 (4)	N3—C38	1.465 (4)
C15—C9	1.501 (4)	N4—C37	1.455 (4)
C9—C14	1.399 (4)	N4—C36	1.465 (5)
C9—C10	1.402 (4)	N4—C38	1.477 (4)
C10—C11	1.403 (4)	C33—H33A	0.9900
C10—C16	1.503 (4)	C33—H33B	0.9900
C11—C12	1.386 (5)	C34—H34A	0.9900
C11—H11A	0.9500	C34—H34B	0.9900
C12—C13	1.381 (5)	C35—H35A	0.9900
C12—H12A	0.9500	C35—H35B	0.9900
C13—C14	1.378 (5)	C36—H36A	0.9900
C13—H13A	0.9500	C36—H36B	0.9900
C14—H14A	0.9500	C37—H37A	0.9900
C16—H16A	0.9800	C37—H37B	0.9900
C16—H16B	0.9800	C38—H38A	0.9900
C16—H16C	0.9800	C38—H38B	0.9900
O3X—C15X	1.314 (17)	N1X—C36X	1.460 (17)
O3X—H2O3	0.8400	N1X—C33X	1.466 (17)
O4X—C15X	1.204 (17)	N1X—C35X	1.489 (16)
C15X—C9X	1.517 (17)	N2X—C33X	1.460 (17)
C9X—C14X	1.393 (17)	N2X—C34X	1.494 (16)
C9X—C10X	1.397 (17)	N2X—C37X	1.505 (17)
C10X—C11X	1.403 (17)	N3X—C35X	1.457 (17)
C10X—C16X	1.518 (17)	N3X—C34X	1.459 (17)
C11X—C12X	1.383 (18)	N3X—C38X	1.474 (17)
C11X—H11B	0.9500	N4X—C37X	1.437 (17)
C12X—C13X	1.368 (19)	N4X—C36X	1.458 (17)
C12X—H12B	0.9500	N4X—C38X	1.482 (17)
C13X—C14X	1.362 (18)	C33X—H33C	0.9900
C13X—H13B	0.9500	C33X—H33D	0.9900
C14X—H14B	0.9500	C34X—H34C	0.9900
C16X—H16D	0.9800	C34X—H34D	0.9900
C16X—H16E	0.9800	C35X—H35C	0.9900
C16X—H16F	0.9800	C35X—H35D	0.9900
O5—C23	1.310 (4)	C36X—H36C	0.9900
O5—H1O5	0.85 (2)	C36X—H36D	0.9900
O6—C23	1.217 (4)	C37X—H37C	0.9900
O7—C31	1.303 (4)	C37X—H37D	0.9900
O7—H1O7	0.861 (19)	C38X—H38C	0.9900
O8—C31	1.211 (4)	C38X—H38D	0.9900
N5—C39	1.469 (4)	C39—H39A	0.9900
N5—C42	1.479 (3)	C39—H39B	0.9900
N5—C41	1.482 (3)	C40—H40A	0.9900
N6—C39	1.470 (4)	C40—H40B	0.9900
N6—C43	1.478 (3)	C41—H41A	0.9900
N6—C40	1.482 (3)	C41—H41B	0.9900
N7—C41	1.447 (4)	C42—H42A	0.9900
N7—C40	1.458 (4)	C42—H42B	0.9900
N7—C44	1.466 (3)	C43—H43A	0.9900
N8—C42	1.452 (4)	C43—H43B	0.9900
N8—C43	1.458 (4)	C44—H44A	0.9900
N8—C44	1.478 (4)	C44—H44B	0.9900

C7—O1—H1O1	113 (3)	C25—C26—C27	117.8 (3)
O2—C7—O1	122.5 (4)	C25—C26—C32	124.1 (3)
O2—C7—C1	124.5 (3)	C27—C26—C32	118.2 (3)
O1—C7—C1	112.9 (4)	C28—C27—C26	122.1 (3)
C6—C1—C2	119.8 (4)	C28—C27—H27A	118.9
C6—C1—C7	118.6 (4)	C26—C27—H27A	118.9
C2—C1—C7	121.6 (4)	C27—C28—C29	120.2 (3)
C3—C2—C1	117.6 (4)	C27—C28—H28A	119.9
C3—C2—C8	118.7 (4)	C29—C28—H28A	119.9
C1—C2—C8	123.7 (4)	C30—C29—C28	119.3 (3)
C4—C3—C2	121.8 (5)	C30—C29—H29A	120.3
C4—C3—H3A	119.1	C28—C29—H29A	120.3
C2—C3—H3A	119.1	C29—C30—C25	121.1 (3)
C3—C4—C5	120.6 (4)	C29—C30—H30A	119.4
C3—C4—H4A	119.7	C25—C30—H30A	119.4
C5—C4—H4A	119.7	O8—C31—O7	122.4 (3)
C6—C5—C4	119.5 (4)	O8—C31—C25	123.6 (3)
C6—C5—H5A	120.3	O7—C31—C25	114.0 (3)
C4—C5—H5A	120.3	C26—C32—H32A	109.5
C5—C6—C1	120.8 (4)	C26—C32—H32B	109.5
C5—C6—H6A	119.6	H32A—C32—H32B	109.5
C1—C6—H6A	119.6	C26—C32—H32C	109.5
C2—C8—H8A	109.5	H32A—C32—H32C	109.5
C2—C8—H8B	109.5	H32B—C32—H32C	109.5
H8A—C8—H8B	109.5	C33—N1—C36	107.9 (2)
C2—C8—H8C	109.5	C33—N1—C35	108.4 (2)
H8A—C8—H8C	109.5	C36—N1—C35	108.5 (3)
H8B—C8—H8C	109.5	C33—N2—C34	107.9 (2)
C7X—O1X—H2O1	109.5	C33—N2—C37	107.5 (2)
O2X—C7X—O1X	125.3 (15)	C34—N2—C37	108.0 (3)
O2X—C7X—C1X	119.2 (14)	C35—N3—C34	108.7 (3)
O1X—C7X—C1X	115.4 (12)	C35—N3—C38	108.6 (3)
C2X—C1X—C6X	120.3 (13)	C34—N3—C38	108.2 (3)
C2X—C1X—C7X	121.8 (14)	C37—N4—C36	108.8 (3)
C6X—C1X—C7X	117.9 (13)	C37—N4—C38	108.1 (3)
C3X—C2X—C1X	115.4 (15)	C36—N4—C38	108.0 (3)
C3X—C2X—C8X	116.3 (15)	N2—C33—N1	111.9 (2)
C1X—C2X—C8X	128.3 (16)	N2—C33—H33A	109.2
C4X—C3X—C2X	124.5 (18)	N1—C33—H33A	109.2
C4X—C3X—H3XA	117.8	N2—C33—H33B	109.2
C2X—C3X—H3XA	117.8	N1—C33—H33B	109.2
C3X—C4X—C5X	119.7 (17)	H33A—C33—H33B	107.9
C3X—C4X—H4XA	120.1	N3—C34—N2	112.3 (3)
C5X—C4X—H4XA	120.1	N3—C34—H34A	109.1
C6X—C5X—C4X	118.1 (15)	N2—C34—H34A	109.1
C6X—C5X—H5XA	120.9	N3—C34—H34B	109.1
C4X—C5X—H5XA	120.9	N2—C34—H34B	109.1
C5X—C6X—C1X	122.0 (14)	H34A—C34—H34B	107.9
C5X—C6X—H6XA	119.0	N3—C35—N1	111.4 (3)
C1X—C6X—H6XA	119.0	N3—C35—H35A	109.4
C2X—C8X—H8XA	109.5	N1—C35—H35A	109.4
C2X—C8X—H8XB	109.5	N3—C35—H35B	109.4
H8XA—C8X—H8XB	109.5	N1—C35—H35B	109.4
C2X—C8X—H8XC	109.5	H35A—C35—H35B	108.0
H8XA—C8X—H8XC	109.5	N4—C36—N1	111.5 (3)
H8XB—C8X—H8XC	109.5	N4—C36—H36A	109.3
C15—O3—H1O3	109 (4)	N1—C36—H36A	109.3
O4—C15—O3	122.8 (3)	N4—C36—H36B	109.3
O4—C15—C9	121.1 (3)	N1—C36—H36B	109.3
O3—C15—C9	116.1 (3)	H36A—C36—H36B	108.0
C14—C9—C10	119.9 (3)	N4—C37—N2	112.2 (3)
C14—C9—C15	115.2 (3)	N4—C37—H37A	109.2
C10—C9—C15	124.9 (3)	N2—C37—H37A	109.2
C9—C10—C11	117.5 (3)	N4—C37—H37B	109.2
C9—C10—C16	125.4 (3)	N2—C37—H37B	109.2
C11—C10—C16	117.0 (3)	H37A—C37—H37B	107.9
C12—C11—C10	121.8 (3)	N3—C38—N4	112.2 (3)
C12—C11—H11A	119.1	N3—C38—H38A	109.2
C10—C11—H11A	119.1	N4—C38—H38A	109.2
C13—C12—C11	120.1 (3)	N3—C38—H38B	109.2
C13—C12—H12A	120.0	N4—C38—H38B	109.2
C11—C12—H12A	120.0	H38A—C38—H38B	107.9
C14—C13—C12	119.2 (3)	C36X—N1X—C33X	110.1 (15)
C14—C13—H13A	120.4	C36X—N1X—C35X	108.4 (16)
C12—C13—H13A	120.4	C33X—N1X—C35X	106.6 (15)
C13—C14—C9	121.5 (3)	C33X—N2X—C34X	107.0 (15)
C13—C14—H14A	119.3	C33X—N2X—C37X	106.7 (15)
C9—C14—H14A	119.3	C34X—N2X—C37X	105.3 (17)
C10—C16—H16A	109.5	C35X—N3X—C34X	110.0 (18)
C10—C16—H16B	109.5	C35X—N3X—C38X	107.2 (19)
H16A—C16—H16B	109.5	C34X—N3X—C38X	107.6 (19)
C10—C16—H16C	109.5	C37X—N4X—C36X	109.9 (19)
H16A—C16—H16C	109.5	C37X—N4X—C38X	110 (2)
H16B—C16—H16C	109.5	C36X—N4X—C38X	107 (2)
C15X—O3X—H2O3	109.5	N2X—C33X—N1X	114.1 (14)
O4X—C15X—O3X	124 (2)	N2X—C33X—H33C	108.7
O4X—C15X—C9X	120.6 (17)	N1X—C33X—H33C	108.7
O3X—C15X—C9X	115.6 (17)	N2X—C33X—H33D	108.7
C14X—C9X—C10X	120.3 (17)	N1X—C33X—H33D	108.7
C14X—C9X—C15X	114.5 (17)	H33C—C33X—H33D	107.6
C10X—C9X—C15X	125.2 (17)	N3X—C34X—N2X	113.4 (16)
C9X—C10X—C11X	114.9 (18)	N3X—C34X—H34C	108.9
C9X—C10X—C16X	123 (2)	N2X—C34X—H34C	108.9
C11X—C10X—C16X	122.0 (19)	N3X—C34X—H34D	108.9
C12X—C11X—C10X	123 (2)	N2X—C34X—H34D	108.9
C12X—C11X—H11B	118.4	H34C—C34X—H34D	107.7
C10X—C11X—H11B	118.4	N3X—C35X—N1X	111.2 (16)
C13X—C12X—C11X	121 (2)	N3X—C35X—H35C	109.4
C13X—C12X—H12B	119.7	N1X—C35X—H35C	109.4
C11X—C12X—H12B	119.7	N3X—C35X—H35D	109.4
C14X—C13X—C12X	117 (2)	N1X—C35X—H35D	109.4
C14X—C13X—H13B	121.4	H35C—C35X—H35D	108.0
C12X—C13X—H13B	121.4	N4X—C36X—N1X	110.9 (16)
C13X—C14X—C9X	123 (2)	N4X—C36X—H36C	109.5
C13X—C14X—H14B	118.3	N1X—C36X—H36C	109.5
C9X—C14X—H14B	118.3	N4X—C36X—H36D	109.5
C10X—C16X—H16D	109.5	N1X—C36X—H36D	109.5
C10X—C16X—H16E	109.5	H36C—C36X—H36D	108.0
H16D—C16X—H16E	109.5	N4X—C37X—N2X	113.0 (17)
C10X—C16X—H16F	109.5	N4X—C37X—H37C	109.0
H16D—C16X—H16F	109.5	N2X—C37X—H37C	109.0
H16E—C16X—H16F	109.5	N4X—C37X—H37D	109.0
C23—O5—H1O5	104 (4)	N2X—C37X—H37D	109.0
C31—O7—H1O7	112 (3)	H37C—C37X—H37D	107.8
C39—N5—C42	108.3 (2)	N3X—C38X—N4X	111.5 (18)
C39—N5—C41	108.4 (2)	N3X—C38X—H38C	109.3
C42—N5—C41	107.8 (2)	N4X—C38X—H38C	109.3
C39—N6—C43	107.8 (2)	N3X—C38X—H38D	109.3
C39—N6—C40	108.0 (2)	N4X—C38X—H38D	109.3
C43—N6—C40	107.9 (2)	H38C—C38X—H38D	108.0
C41—N7—C40	108.4 (2)	N5—C39—N6	111.52 (18)
C41—N7—C44	108.6 (2)	N5—C39—H39A	109.3
C40—N7—C44	108.4 (2)	N6—C39—H39A	109.3
C42—N8—C43	108.3 (2)	N5—C39—H39B	109.3
C42—N8—C44	108.1 (2)	N6—C39—H39B	109.3
C43—N8—C44	108.2 (2)	H39A—C39—H39B	108.0
C18—C17—C22	119.1 (3)	N7—C40—N6	112.1 (2)
C18—C17—C23	123.4 (3)	N7—C40—H40A	109.2
C22—C17—C23	117.5 (3)	N6—C40—H40A	109.2
C19—C18—C17	118.3 (3)	N7—C40—H40B	109.2
C19—C18—C24	118.0 (3)	N6—C40—H40B	109.2
C17—C18—C24	123.7 (3)	H40A—C40—H40B	107.9
C20—C19—C18	121.8 (3)	N7—C41—N5	112.0 (2)
C20—C19—H19A	119.1	N7—C41—H41A	109.2
C18—C19—H19A	119.1	N5—C41—H41A	109.2
C19—C20—C21	120.5 (3)	N7—C41—H41B	109.2
C19—C20—H20A	119.7	N5—C41—H41B	109.2
C21—C20—H20A	119.7	H41A—C41—H41B	107.9
C22—C21—C20	118.4 (3)	N8—C42—N5	112.1 (2)
C22—C21—H21A	120.8	N8—C42—H42A	109.2
C20—C21—H21A	120.8	N5—C42—H42A	109.2
C21—C22—C17	121.8 (3)	N8—C42—H42B	109.2
C21—C22—H22A	119.1	N5—C42—H42B	109.2
C17—C22—H22A	119.1	H42A—C42—H42B	107.9
O6—C23—O5	122.0 (3)	N8—C43—N6	112.4 (2)
O6—C23—C17	123.9 (3)	N8—C43—H43A	109.1
O5—C23—C17	114.1 (3)	N6—C43—H43A	109.1
C18—C24—H24A	109.5	N8—C43—H43B	109.1
C18—C24—H24B	109.5	N6—C43—H43B	109.1
H24A—C24—H24B	109.5	H43A—C43—H43B	107.8
C18—C24—H24C	109.5	N7—C44—N8	111.92 (18)
H24A—C24—H24C	109.5	N7—C44—H44A	109.2
H24B—C24—H24C	109.5	N8—C44—H44A	109.2
C26—C25—C30	119.5 (3)	N7—C44—H44B	109.2
C26—C25—C31	123.1 (3)	N8—C44—H44B	109.2
C30—C25—C31	117.4 (3)	H44A—C44—H44B	107.9

O2—C7—C1—C6	170.3 (5)	C26—C27—C28—C29	−0.1 (4)
O1—C7—C1—C6	−11.5 (6)	C27—C28—C29—C30	0.8 (4)
O2—C7—C1—C2	−9.8 (9)	C28—C29—C30—C25	−1.1 (4)
O1—C7—C1—C2	168.5 (7)	C26—C25—C30—C29	0.9 (4)
C6—C1—C2—C3	1.6 (12)	C31—C25—C30—C29	178.3 (3)
C7—C1—C2—C3	−178.4 (7)	C26—C25—C31—O8	−12.0 (4)
C6—C1—C2—C8	−178.7 (7)	C30—C25—C31—O8	170.6 (3)
C7—C1—C2—C8	1.4 (12)	C26—C25—C31—O7	167.1 (3)
C1—C2—C3—C4	−0.4 (13)	C30—C25—C31—O7	−10.3 (4)
C8—C2—C3—C4	179.9 (7)	C34—N2—C33—N1	−57.6 (3)
C2—C3—C4—C5	−0.8 (11)	C37—N2—C33—N1	58.7 (3)
C3—C4—C5—C6	0.7 (8)	C36—N1—C33—N2	−59.3 (3)
C4—C5—C6—C1	0.5 (7)	C35—N1—C33—N2	58.0 (3)
C2—C1—C6—C5	−1.7 (9)	C35—N3—C34—N2	−59.4 (4)
C7—C1—C6—C5	178.3 (4)	C38—N3—C34—N2	58.4 (4)
O2X—C7X—C1X—C2X	162 (3)	C33—N2—C34—N3	58.2 (3)
O1X—C7X—C1X—C2X	−15 (4)	C37—N2—C34—N3	−57.7 (4)
O2X—C7X—C1X—C6X	−19 (3)	C34—N3—C35—N1	59.0 (4)
O1X—C7X—C1X—C6X	165 (2)	C38—N3—C35—N1	−58.5 (4)
C6X—C1X—C2X—C3X	1 (6)	C33—N1—C35—N3	−58.4 (3)
C7X—C1X—C2X—C3X	−179 (3)	C36—N1—C35—N3	58.5 (3)
C6X—C1X—C2X—C8X	−178 (3)	C37—N4—C36—N1	−58.9 (4)
C7X—C1X—C2X—C8X	2 (6)	C38—N4—C36—N1	58.3 (4)
C1X—C2X—C3X—C4X	−1 (6)	C33—N1—C36—N4	58.8 (4)
C8X—C2X—C3X—C4X	178 (3)	C35—N1—C36—N4	−58.5 (4)
C2X—C3X—C4X—C5X	−1 (5)	C36—N4—C37—N2	58.8 (4)
C3X—C4X—C5X—C6X	3 (4)	C38—N4—C37—N2	−58.2 (4)
C4X—C5X—C6X—C1X	−3 (3)	C33—N2—C37—N4	−58.4 (4)
C2X—C1X—C6X—C5X	1 (4)	C34—N2—C37—N4	57.8 (4)
C7X—C1X—C6X—C5X	−179 (2)	C35—N3—C38—N4	59.0 (5)
O4—C15—C9—C14	−19.8 (5)	C34—N3—C38—N4	−58.8 (5)
O3—C15—C9—C14	160.7 (3)	C37—N4—C38—N3	58.9 (5)
O4—C15—C9—C10	157.4 (6)	C36—N4—C38—N3	−58.6 (5)
O3—C15—C9—C10	−22.1 (7)	C34X—N2X—C33X—N1X	−58 (2)
C14—C9—C10—C11	0.8 (10)	C37X—N2X—C33X—N1X	54 (2)
C15—C9—C10—C11	−176.2 (5)	C36X—N1X—C33X—N2X	−56 (2)
C14—C9—C10—C16	−178.5 (5)	C35X—N1X—C33X—N2X	61 (2)
C15—C9—C10—C16	4.5 (11)	C35X—N3X—C34X—N2X	−56 (2)
C9—C10—C11—C12	−1.3 (10)	C38X—N3X—C34X—N2X	61 (2)
C16—C10—C11—C12	178.1 (5)	C33X—N2X—C34X—N3X	54 (2)
C10—C11—C12—C13	1.3 (8)	C37X—N2X—C34X—N3X	−59 (2)
C11—C12—C13—C14	−0.8 (6)	C34X—N3X—C35X—N1X	58 (2)
C12—C13—C14—C9	0.3 (5)	C38X—N3X—C35X—N1X	−59 (2)
C10—C9—C14—C13	−0.4 (7)	C36X—N1X—C35X—N3X	59 (2)
C15—C9—C14—C13	177.0 (3)	C33X—N1X—C35X—N3X	−59 (2)
O4X—C15X—C9X—C14X	166 (4)	C37X—N4X—C36X—N1X	−58 (2)
O3X—C15X—C9X—C14X	−13 (5)	C38X—N4X—C36X—N1X	61 (2)
O4X—C15X—C9X—C10X	−13 (8)	C33X—N1X—C36X—N4X	56 (2)
O3X—C15X—C9X—C10X	168 (6)	C35X—N1X—C36X—N4X	−60 (2)
C14X—C9X—C10X—C11X	3 (10)	C36X—N4X—C37X—N2X	59 (3)
C15X—C9X—C10X—C11X	−178 (5)	C38X—N4X—C37X—N2X	−58 (3)
C14X—C9X—C10X—C16X	−177 (6)	C33X—N2X—C37X—N4X	−56 (2)
C15X—C9X—C10X—C16X	2 (11)	C34X—N2X—C37X—N4X	57 (2)
C9X—C10X—C11X—C12X	4 (11)	C35X—N3X—C38X—N4X	61 (3)
C16X—C10X—C11X—C12X	−176 (6)	C34X—N3X—C38X—N4X	−58 (3)
C10X—C11X—C12X—C13X	−9 (9)	C37X—N4X—C38X—N3X	57 (3)
C11X—C12X—C13X—C14X	6 (6)	C36X—N4X—C38X—N3X	−62 (3)
C12X—C13X—C14X—C9X	1 (6)	C42—N5—C39—N6	−58.5 (3)
C10X—C9X—C14X—C13X	−6 (8)	C41—N5—C39—N6	58.2 (3)
C15X—C9X—C14X—C13X	175 (3)	C43—N6—C39—N5	58.4 (3)
C22—C17—C18—C19	−0.5 (4)	C40—N6—C39—N5	−58.0 (3)
C23—C17—C18—C19	−176.9 (3)	C41—N7—C40—N6	−59.1 (3)
C22—C17—C18—C24	179.7 (3)	C44—N7—C40—N6	58.6 (3)
C23—C17—C18—C24	3.3 (4)	C39—N6—C40—N7	58.6 (3)
C17—C18—C19—C20	0.5 (4)	C43—N6—C40—N7	−57.7 (3)
C24—C18—C19—C20	−179.7 (3)	C40—N7—C41—N5	58.9 (3)
C18—C19—C20—C21	−0.5 (5)	C44—N7—C41—N5	−58.7 (3)
C19—C20—C21—C22	0.5 (5)	C39—N5—C41—N7	−58.7 (3)
C20—C21—C22—C17	−0.5 (5)	C42—N5—C41—N7	58.3 (3)
C18—C17—C22—C21	0.5 (4)	C43—N8—C42—N5	−58.3 (3)
C23—C17—C22—C21	177.1 (3)	C44—N8—C42—N5	58.6 (3)
C18—C17—C23—O6	−3.3 (5)	C39—N5—C42—N8	58.6 (3)
C22—C17—C23—O6	−179.7 (3)	C41—N5—C42—N8	−58.5 (3)
C18—C17—C23—O5	175.7 (3)	C42—N8—C43—N6	58.7 (3)
C22—C17—C23—O5	−0.7 (4)	C44—N8—C43—N6	−58.2 (3)
C30—C25—C26—C27	−0.2 (4)	C39—N6—C43—N8	−58.7 (3)
C31—C25—C26—C27	−177.5 (2)	C40—N6—C43—N8	57.7 (3)
C30—C25—C26—C32	178.6 (3)	C41—N7—C44—N8	58.6 (3)
C31—C25—C26—C32	1.3 (4)	C40—N7—C44—N8	−58.9 (3)
C25—C26—C27—C28	−0.2 (4)	C42—N8—C44—N7	−58.4 (3)
C32—C26—C27—C28	−179.0 (3)	C43—N8—C44—N7	58.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.83 (3)	1.80 (3)	2.631 (4)	173 (5)
O3—H1O3···N2	0.84 (4)	1.84 (4)	2.679 (5)	175 (3)
O5—H1O5···N5	0.86 (3)	1.85 (4)	2.680 (3)	162 (5)
O7—H1O7···N6	0.86 (3)	1.80 (3)	2.657 (3)	171 (4)
C6—H6A···O1	0.95	2.35	2.685 (5)	100
C16—H16A···O3	0.98	2.44	2.816 (4)	102
C22—H22A···O5	0.95	2.31	2.670 (4)	102
C30—H30A···O7	0.95	2.34	2.683 (4)	101
C33—H33A···O4	0.99	2.58	3.138 (5)	116
C33—H33B···N8ⁱ	0.99	2.59	3.520 (4)	157
C36—H36B···N7	0.99	2.61	3.561 (5)	161
C38—H38B···O4ⁱⁱ	0.99	2.40	3.357 (6)	164
C40—H40B···N3ⁱⁱⁱ	0.99	2.57	3.492 (5)	155
C44—H44A···O6^iv	0.99	2.38	3.363 (4)	172
C44—H44B···O8^iv	0.99	2.39	3.372 (4)	171

Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) x, −y+3/2, z−1/2.

(160K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top

Crystal data top

C₆H₁₂N₄·2C₈H₈O₂	F(000) = 1760
M_r = 412.48	D_x = 1.318 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 30.975 (2) Å	Cell parameters from 9990 reflections
b = 9.3542 (7) Å	θ = 2.2–27.2°
c = 14.3524 (10) Å	µ = 0.09 mm⁻¹
β = 90.1490 (14)°	T = 160 K
V = 4158.5 (5) Å³	Block, colourless
Z = 8	0.43 × 0.17 × 0.15 mm

Data collection top

Bruker APEX DUO CCD area detector diffractometer	10026 independent reflections
Radiation source: fine-focus sealed tube	7762 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 28.0°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −36→40
T_min = 0.879, T_max = 0.963	k = −12→12
65634 measured reflections	l = −18→18

Refinement top

Refinement on F²	1222 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.151	w = 1/[σ²(F_o²) + (0.0691P)² + 1.5753P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
10026 reflections	Δρ_max = 0.43 e Å⁻³
837 parameters	Δρ_min = −0.19 e Å⁻³

Special details top

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.16460 (10)	0.2389 (4)	0.3352 (2)	0.0479 (9)	0.674 (6)
H1O1	0.1796 (14)	0.248 (5)	0.287 (2)	0.071 (15)*	0.674 (6)
O2	0.12825 (12)	0.4193 (5)	0.2741 (2)	0.0582 (10)	0.674 (6)
C7	0.13364 (12)	0.3346 (5)	0.3365 (3)	0.0315 (8)	0.674 (6)
C1	0.1076 (3)	0.3297 (7)	0.4233 (4)	0.0321 (10)	0.674 (6)
C2	0.0784 (4)	0.4398 (10)	0.4470 (6)	0.0342 (12)	0.674 (6)
C3	0.0566 (3)	0.4287 (9)	0.5317 (5)	0.0414 (14)	0.674 (6)
H3A	0.0373	0.5025	0.5494	0.050*	0.674 (6)
C4	0.06240 (19)	0.3139 (7)	0.5904 (4)	0.0442 (13)	0.674 (6)
H4A	0.0470	0.3092	0.6474	0.053*	0.674 (6)
C5	0.09058 (19)	0.2052 (6)	0.5665 (4)	0.0438 (11)	0.674 (6)
H5A	0.0945	0.1255	0.6067	0.053*	0.674 (6)
C6	0.11282 (16)	0.2143 (6)	0.4838 (4)	0.0359 (10)	0.674 (6)
H6A	0.1323	0.1399	0.4675	0.043*	0.674 (6)
C8	0.0704 (2)	0.5680 (7)	0.3862 (5)	0.0444 (13)	0.674 (6)
H8A	0.0976	0.6185	0.3755	0.067*	0.674 (6)
H8B	0.0500	0.6324	0.4172	0.067*	0.674 (6)
H8C	0.0583	0.5368	0.3264	0.067*	0.674 (6)
O1X	0.1342 (3)	0.3366 (10)	0.2843 (6)	0.062 (2)	0.326 (6)
H2O1	0.1529	0.3083	0.2463	0.092*	0.326 (6)
O2X	0.1652 (2)	0.1740 (9)	0.3765 (7)	0.062 (2)	0.326 (6)
C7X	0.1376 (3)	0.2638 (11)	0.3619 (6)	0.0386 (16)	0.326 (6)
C1X	0.1068 (6)	0.3027 (15)	0.4375 (10)	0.0309 (17)	0.326 (6)
C2X	0.0817 (9)	0.427 (2)	0.4364 (14)	0.034 (2)	0.326 (6)
C3X	0.0542 (6)	0.4473 (18)	0.5117 (10)	0.037 (2)	0.326 (6)
H3XA	0.0372	0.5316	0.5137	0.044*	0.326 (6)
C4X	0.0506 (4)	0.3508 (13)	0.5834 (9)	0.039 (2)	0.326 (6)
H4XA	0.0318	0.3700	0.6340	0.047*	0.326 (6)
C5X	0.0744 (4)	0.2253 (13)	0.5817 (7)	0.0374 (18)	0.326 (6)
H5XA	0.0718	0.1572	0.6305	0.045*	0.326 (6)
C6X	0.1018 (4)	0.2009 (11)	0.5086 (8)	0.0350 (17)	0.326 (6)
H6XA	0.1176	0.1141	0.5059	0.042*	0.326 (6)
C8X	0.0813 (5)	0.5426 (14)	0.3628 (9)	0.044 (3)	0.326 (6)
H8XA	0.1103	0.5837	0.3571	0.067*	0.326 (6)
H8XB	0.0609	0.6177	0.3806	0.067*	0.326 (6)
H8XC	0.0726	0.5013	0.3030	0.067*	0.326 (6)
O3	0.36553 (9)	0.1741 (3)	0.28273 (19)	0.0467 (7)	0.808 (5)
H1O3	0.3429 (11)	0.188 (5)	0.251 (3)	0.096 (16)*	0.808 (5)
O4	0.33478 (8)	0.3290 (3)	0.3775 (2)	0.0526 (7)	0.808 (5)
C15	0.36227 (9)	0.2410 (3)	0.3628 (2)	0.0311 (6)	0.808 (5)
C9	0.39495 (15)	0.2026 (4)	0.4358 (3)	0.0264 (7)	0.808 (5)
C10	0.4180 (3)	0.0731 (7)	0.4382 (5)	0.0288 (8)	0.808 (5)
C11	0.44583 (18)	0.0499 (5)	0.5142 (3)	0.0342 (9)	0.808 (5)
H11A	0.4620	−0.0363	0.5173	0.041*	0.808 (5)
C12	0.45020 (13)	0.1496 (4)	0.5849 (3)	0.0374 (8)	0.808 (5)
H12A	0.4691	0.1311	0.6356	0.045*	0.808 (5)
C13	0.42726 (14)	0.2756 (4)	0.5820 (3)	0.0385 (8)	0.808 (5)
H13A	0.4303	0.3440	0.6306	0.046*	0.808 (5)
C14	0.39981 (13)	0.3017 (4)	0.5080 (3)	0.0341 (8)	0.808 (5)
H14A	0.3839	0.3885	0.5061	0.041*	0.808 (5)
C16	0.41693 (14)	−0.0407 (4)	0.3645 (3)	0.0393 (9)	0.808 (5)
H16A	0.3870	−0.0585	0.3459	0.059*	0.808 (5)
H16B	0.4296	−0.1289	0.3894	0.059*	0.808 (5)
H16C	0.4335	−0.0090	0.3103	0.059*	0.808 (5)
O3X	0.3346 (3)	0.2636 (13)	0.3362 (9)	0.050 (3)	0.192 (5)
H2O3	0.3206	0.2574	0.2862	0.076*	0.192 (5)
O4X	0.3723 (4)	0.0870 (16)	0.2730 (7)	0.057 (3)	0.192 (5)
C15X	0.3659 (4)	0.1692 (15)	0.3361 (9)	0.033 (2)	0.192 (5)
C9X	0.3933 (7)	0.168 (2)	0.4246 (13)	0.032 (2)	0.192 (5)
C10X	0.4230 (13)	0.060 (3)	0.446 (2)	0.032 (2)	0.192 (5)
C11X	0.4427 (9)	0.073 (2)	0.5334 (14)	0.035 (2)	0.192 (5)
H11B	0.4607	−0.0030	0.5541	0.042*	0.192 (5)
C12X	0.4372 (6)	0.188 (2)	0.5910 (11)	0.036 (2)	0.192 (5)
H12B	0.4524	0.1921	0.6485	0.044*	0.192 (5)
C13X	0.4101 (6)	0.2965 (17)	0.5663 (12)	0.037 (2)	0.192 (5)
H13B	0.4060	0.3768	0.6058	0.045*	0.192 (5)
C14X	0.3893 (6)	0.2858 (19)	0.4829 (12)	0.035 (2)	0.192 (5)
H14B	0.3712	0.3625	0.4637	0.042*	0.192 (5)
C16X	0.4292 (7)	−0.0692 (19)	0.3837 (13)	0.042 (4)	0.192 (5)
H16D	0.4560	−0.1180	0.4010	0.063*	0.192 (5)
H16E	0.4307	−0.0387	0.3185	0.063*	0.192 (5)
H16F	0.4048	−0.1347	0.3917	0.063*	0.192 (5)
O5	0.13483 (7)	0.8207 (2)	0.52603 (15)	0.0583 (6)
H1O5	0.1601 (8)	0.795 (4)	0.506 (3)	0.099 (14)*
O6	0.15701 (6)	0.6838 (3)	0.64232 (18)	0.0661 (6)
O7	0.36416 (7)	0.6911 (2)	0.52179 (15)	0.0565 (5)
H1O7	0.3381 (8)	0.706 (5)	0.501 (3)	0.111 (16)*
O8	0.34103 (6)	0.8033 (3)	0.64657 (17)	0.0695 (7)
N5	0.21031 (6)	0.7734 (2)	0.44106 (14)	0.0314 (4)
N6	0.28772 (6)	0.7318 (2)	0.44058 (13)	0.0312 (4)
N7	0.24204 (6)	0.6224 (2)	0.32186 (13)	0.0323 (4)
N8	0.25475 (6)	0.8797 (2)	0.31999 (13)	0.0323 (4)
C17	0.08270 (7)	0.7497 (2)	0.63474 (17)	0.0332 (5)
C18	0.06809 (8)	0.6694 (3)	0.71020 (18)	0.0396 (6)
C19	0.02397 (8)	0.6743 (3)	0.7314 (2)	0.0465 (7)
H19A	0.0135	0.6205	0.7827	0.056*
C20	−0.00436 (8)	0.7547 (3)	0.6801 (2)	0.0478 (6)
H20A	−0.0341	0.7555	0.6963	0.057*
C21	0.00971 (9)	0.8351 (3)	0.6046 (2)	0.0476 (6)
H21A	−0.0100	0.8910	0.5692	0.057*
C22	0.05274 (8)	0.8316 (3)	0.5826 (2)	0.0426 (6)
H22A	0.0627	0.8857	0.5309	0.051*
C23	0.12816 (8)	0.7482 (3)	0.60258 (19)	0.0391 (5)
C24	0.09662 (10)	0.5787 (3)	0.7700 (2)	0.0529 (7)
H24A	0.0791	0.5300	0.8171	0.079*
H24B	0.1182	0.6391	0.8009	0.079*
H24C	0.1112	0.5074	0.7312	0.079*
C25	0.41607 (7)	0.7488 (2)	0.63496 (16)	0.0320 (5)
C26	0.43092 (8)	0.8279 (2)	0.71130 (17)	0.0365 (5)
C27	0.47515 (8)	0.8225 (3)	0.73245 (18)	0.0405 (6)
H27A	0.4858	0.8760	0.7839	0.049*
C28	0.50336 (8)	0.7428 (3)	0.6816 (2)	0.0431 (6)
H28A	0.5331	0.7416	0.6977	0.052*
C29	0.48867 (9)	0.6633 (3)	0.6061 (2)	0.0441 (6)
H29A	0.5082	0.6068	0.5709	0.053*
C30	0.44575 (8)	0.6670 (3)	0.58300 (18)	0.0383 (5)
H30A	0.4358	0.6134	0.5310	0.046*
C31	0.37034 (7)	0.7506 (3)	0.60273 (18)	0.0363 (5)
C32	0.40293 (10)	0.9203 (3)	0.7700 (2)	0.0505 (7)
H32A	0.4209	0.9745	0.8139	0.076*
H32B	0.3826	0.8606	0.8047	0.076*
H32C	0.3869	0.9869	0.7301	0.076*
N1	0.21767 (14)	0.2508 (4)	0.1936 (3)	0.0283 (7)	0.754 (11)
N2	0.29591 (14)	0.2284 (4)	0.1776 (3)	0.0298 (7)	0.754 (11)
N3	0.24781 (18)	0.1184 (8)	0.0638 (4)	0.0330 (9)	0.754 (11)
N4	0.2546 (2)	0.3785 (8)	0.0700 (4)	0.0346 (9)	0.754 (11)
C33	0.25947 (18)	0.2377 (4)	0.2431 (2)	0.0288 (8)	0.754 (11)
H33A	0.2635	0.3216	0.2843	0.035*	0.754 (11)
H33B	0.2590	0.1511	0.2828	0.035*	0.754 (11)
C34	0.28840 (16)	0.1054 (5)	0.1155 (3)	0.0341 (9)	0.754 (11)
H34A	0.3126	0.0978	0.0709	0.041*	0.754 (11)
H34B	0.2878	0.0166	0.1531	0.041*	0.754 (11)
C35	0.21258 (17)	0.1256 (5)	0.1313 (4)	0.0334 (10)	0.754 (11)
H35A	0.2122	0.0370	0.1690	0.040*	0.754 (11)
H35B	0.1847	0.1326	0.0977	0.040*	0.754 (11)
C36	0.21917 (17)	0.3826 (5)	0.1365 (4)	0.0347 (9)	0.754 (11)
H36A	0.1915	0.3935	0.1024	0.042*	0.754 (11)
H36B	0.2227	0.4664	0.1779	0.042*	0.754 (11)
C37	0.29536 (17)	0.3599 (5)	0.1196 (4)	0.0334 (10)	0.754 (11)
H37A	0.3004	0.4440	0.1601	0.040*	0.754 (11)
H37B	0.3192	0.3552	0.0739	0.040*	0.754 (11)
C38	0.2478 (3)	0.2524 (8)	0.0098 (5)	0.0375 (10)	0.754 (11)
H38A	0.2199	0.2622	−0.0233	0.045*	0.754 (11)
H38B	0.2710	0.2483	−0.0376	0.045*	0.754 (11)
N1X	0.2035 (4)	0.2748 (12)	0.1787 (8)	0.0328 (17)	0.246 (11)
N2X	0.2820 (4)	0.2476 (13)	0.1937 (8)	0.0305 (16)	0.246 (11)
N3X	0.2418 (6)	0.118 (2)	0.0718 (13)	0.0334 (19)	0.246 (11)
N4X	0.2512 (6)	0.376 (2)	0.0611 (13)	0.0336 (19)	0.246 (11)
C33X	0.2407 (5)	0.2619 (13)	0.2421 (7)	0.0292 (18)	0.246 (11)
H33C	0.2419	0.3474	0.2827	0.035*	0.246 (11)
H33D	0.2365	0.1774	0.2826	0.035*	0.246 (11)
C34X	0.2788 (5)	0.1158 (16)	0.1357 (11)	0.036 (2)	0.246 (11)
H34C	0.3057	0.1051	0.0991	0.043*	0.246 (11)
H34D	0.2763	0.0317	0.1772	0.043*	0.246 (11)
C35X	0.2021 (5)	0.1424 (17)	0.1228 (13)	0.034 (2)	0.246 (11)
H35C	0.1968	0.0601	0.1646	0.040*	0.246 (11)
H35D	0.1778	0.1481	0.0781	0.040*	0.246 (11)
C36X	0.2115 (5)	0.3937 (16)	0.1142 (11)	0.031 (2)	0.246 (11)
H36C	0.1869	0.4018	0.0704	0.037*	0.246 (11)
H36D	0.2133	0.4839	0.1501	0.037*	0.246 (11)
C37X	0.2862 (6)	0.3738 (18)	0.1293 (13)	0.035 (2)	0.246 (11)
H37C	0.2855	0.4632	0.1662	0.042*	0.246 (11)
H37D	0.3142	0.3690	0.0966	0.042*	0.246 (11)
C38X	0.2502 (10)	0.240 (2)	0.0094 (14)	0.036 (2)	0.246 (11)
H38C	0.2782	0.2258	−0.0224	0.043*	0.246 (11)
H38D	0.2273	0.2444	−0.0388	0.043*	0.246 (11)
C39	0.24924 (9)	0.7536 (3)	0.49864 (11)	0.0328 (4)
H39A	0.2535	0.8389	0.5385	0.039*
H39B	0.2452	0.6699	0.5399	0.039*
C40	0.28017 (8)	0.6056 (2)	0.38094 (17)	0.0331 (5)
H40A	0.3058	0.5897	0.3411	0.040*
H40B	0.2765	0.5201	0.4208	0.040*
C41	0.20489 (8)	0.6454 (2)	0.38152 (18)	0.0351 (5)
H41A	0.2007	0.5604	0.4216	0.042*
H41B	0.1788	0.6570	0.3424	0.042*
C42	0.21719 (8)	0.8982 (2)	0.37966 (17)	0.0338 (5)
H42A	0.1912	0.9126	0.3403	0.041*
H42B	0.2212	0.9848	0.4184	0.041*
C43	0.29240 (8)	0.8579 (2)	0.37922 (18)	0.0360 (5)
H43A	0.2970	0.9440	0.4181	0.043*
H43B	0.3182	0.8452	0.3395	0.043*
C44	0.24807 (10)	0.7497 (3)	0.26333 (12)	0.0367 (4)
H44A	0.2224	0.7628	0.2231	0.044*
H44B	0.2734	0.7352	0.2224	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0478 (17)	0.054 (2)	0.0418 (17)	0.0200 (14)	0.0182 (13)	0.0151 (15)
O2	0.074 (2)	0.060 (2)	0.0407 (15)	0.0275 (18)	0.0134 (15)	0.0145 (16)
C7	0.0358 (17)	0.034 (2)	0.0247 (17)	0.0008 (15)	−0.0010 (15)	−0.0007 (17)
C1	0.0339 (18)	0.036 (2)	0.027 (2)	−0.0049 (19)	−0.0031 (16)	−0.0012 (15)
C2	0.035 (3)	0.033 (2)	0.035 (3)	−0.0060 (17)	0.0009 (19)	−0.009 (2)
C3	0.044 (2)	0.044 (3)	0.036 (3)	−0.005 (2)	0.012 (2)	−0.013 (2)
C4	0.048 (3)	0.050 (3)	0.0341 (19)	−0.009 (2)	0.011 (2)	−0.006 (2)
C5	0.048 (3)	0.048 (2)	0.036 (2)	−0.010 (2)	0.006 (2)	0.0038 (18)
C6	0.035 (2)	0.044 (2)	0.028 (2)	−0.0045 (17)	0.0025 (15)	0.0008 (17)
C8	0.046 (3)	0.037 (3)	0.050 (3)	0.001 (2)	0.006 (2)	−0.003 (2)
O1X	0.091 (5)	0.054 (5)	0.040 (4)	0.025 (4)	0.020 (4)	0.005 (4)
O2X	0.055 (4)	0.059 (4)	0.071 (5)	0.027 (3)	0.015 (3)	0.010 (4)
C7X	0.039 (3)	0.041 (4)	0.035 (3)	0.001 (3)	0.001 (3)	0.002 (3)
C1X	0.030 (3)	0.035 (4)	0.028 (3)	0.003 (3)	0.002 (3)	−0.005 (3)
C2X	0.037 (4)	0.035 (4)	0.031 (4)	−0.005 (3)	0.000 (3)	−0.003 (3)
C3X	0.041 (3)	0.031 (3)	0.038 (4)	0.001 (3)	−0.001 (4)	−0.001 (3)
C4X	0.047 (4)	0.036 (4)	0.034 (3)	0.005 (3)	0.002 (3)	−0.004 (3)
C5X	0.043 (4)	0.039 (3)	0.030 (3)	0.004 (4)	0.003 (3)	0.004 (3)
C6X	0.038 (4)	0.036 (3)	0.031 (4)	0.005 (3)	0.004 (3)	0.002 (3)
C8X	0.049 (7)	0.035 (5)	0.049 (6)	−0.004 (4)	0.002 (5)	0.004 (4)
O3	0.0499 (14)	0.0536 (17)	0.0365 (14)	0.0202 (12)	−0.0062 (12)	−0.0084 (13)
O4	0.0506 (14)	0.0459 (15)	0.0612 (17)	0.0233 (11)	−0.0153 (12)	−0.0167 (13)
C15	0.0282 (13)	0.0267 (14)	0.0384 (15)	0.0001 (12)	0.0020 (12)	0.0004 (12)
C9	0.0269 (13)	0.0212 (17)	0.0313 (15)	0.0000 (14)	0.0038 (11)	0.0028 (13)
C10	0.026 (2)	0.0248 (18)	0.0358 (18)	−0.0013 (12)	0.0036 (13)	0.0028 (15)
C11	0.0368 (16)	0.0247 (17)	0.041 (2)	0.0013 (13)	0.0016 (17)	0.0057 (13)
C12	0.044 (2)	0.0317 (19)	0.0362 (15)	0.0003 (14)	−0.0042 (15)	0.0054 (14)
C13	0.044 (2)	0.0387 (19)	0.0326 (15)	−0.0024 (17)	−0.0009 (14)	−0.0035 (14)
C14	0.0390 (19)	0.0278 (14)	0.036 (2)	0.0008 (13)	0.0036 (14)	−0.0024 (14)
C16	0.037 (2)	0.0268 (17)	0.054 (2)	0.0057 (14)	0.0005 (17)	−0.0043 (16)
O3X	0.043 (5)	0.050 (6)	0.058 (6)	0.011 (4)	−0.016 (5)	−0.015 (5)
O4X	0.068 (6)	0.070 (7)	0.033 (4)	0.034 (5)	−0.012 (4)	−0.012 (5)
C15X	0.037 (4)	0.035 (4)	0.029 (4)	0.009 (4)	−0.001 (4)	0.000 (4)
C9X	0.032 (4)	0.031 (4)	0.032 (3)	−0.006 (4)	0.003 (3)	−0.004 (3)
C10X	0.033 (4)	0.026 (4)	0.037 (4)	0.000 (4)	0.002 (4)	0.005 (4)
C11X	0.037 (4)	0.030 (4)	0.037 (4)	−0.001 (4)	−0.004 (4)	0.007 (4)
C12X	0.044 (4)	0.034 (4)	0.031 (4)	0.002 (4)	−0.005 (4)	−0.002 (4)
C13X	0.042 (5)	0.032 (4)	0.037 (4)	0.001 (4)	−0.005 (4)	−0.003 (4)
C14X	0.037 (4)	0.033 (4)	0.035 (4)	−0.005 (4)	−0.001 (4)	0.000 (3)
C16X	0.047 (9)	0.039 (7)	0.041 (7)	0.007 (6)	−0.009 (6)	0.006 (5)
O5	0.0490 (12)	0.0709 (14)	0.0551 (12)	0.0087 (10)	0.0158 (10)	0.0139 (11)
O6	0.0337 (10)	0.0780 (15)	0.0865 (16)	0.0104 (10)	0.0053 (11)	0.0234 (13)
O7	0.0441 (11)	0.0731 (14)	0.0521 (11)	0.0104 (10)	−0.0122 (9)	−0.0147 (10)
O8	0.0386 (10)	0.0950 (17)	0.0750 (15)	0.0109 (11)	0.0018 (11)	−0.0250 (14)
N5	0.0328 (9)	0.0271 (9)	0.0344 (10)	−0.0003 (8)	0.0070 (8)	−0.0016 (8)
N6	0.0334 (9)	0.0284 (9)	0.0319 (9)	0.0013 (8)	−0.0068 (8)	0.0006 (8)
N7	0.0446 (11)	0.0237 (9)	0.0287 (9)	−0.0003 (8)	−0.0019 (8)	−0.0050 (7)
N8	0.0424 (11)	0.0243 (9)	0.0303 (10)	0.0017 (8)	0.0013 (8)	0.0067 (7)
C17	0.0323 (11)	0.0288 (11)	0.0385 (12)	−0.0026 (10)	0.0014 (10)	−0.0093 (10)
C18	0.0432 (14)	0.0364 (13)	0.0394 (13)	−0.0051 (10)	−0.0003 (11)	−0.0090 (10)
C19	0.0354 (13)	0.0537 (16)	0.0504 (15)	−0.0092 (12)	0.0063 (12)	−0.0177 (13)
C20	0.0375 (13)	0.0569 (16)	0.0490 (15)	−0.0032 (13)	0.0034 (12)	−0.0179 (13)
C21	0.0379 (13)	0.0518 (16)	0.0530 (15)	0.0120 (12)	−0.0050 (12)	−0.0109 (13)
C22	0.0443 (14)	0.0366 (13)	0.0470 (14)	0.0026 (11)	0.0000 (12)	−0.0056 (11)
C23	0.0373 (12)	0.0350 (12)	0.0448 (14)	−0.0031 (11)	0.0058 (11)	−0.0075 (11)
C24	0.0536 (16)	0.0532 (17)	0.0520 (16)	−0.0004 (13)	−0.0024 (14)	0.0031 (14)
C25	0.0326 (11)	0.0270 (10)	0.0363 (11)	−0.0024 (9)	−0.0006 (9)	0.0076 (9)
C26	0.0396 (13)	0.0317 (12)	0.0383 (12)	−0.0030 (10)	0.0030 (10)	0.0080 (10)
C27	0.0390 (13)	0.0393 (13)	0.0431 (14)	−0.0071 (10)	−0.0051 (11)	0.0108 (11)
C28	0.0359 (12)	0.0464 (14)	0.0471 (14)	−0.0051 (12)	−0.0042 (11)	0.0125 (12)
C29	0.0415 (13)	0.0411 (14)	0.0498 (15)	0.0079 (11)	0.0089 (12)	0.0073 (12)
C30	0.0399 (13)	0.0328 (12)	0.0421 (13)	0.0018 (10)	0.0004 (11)	0.0036 (10)
C31	0.0346 (12)	0.0311 (11)	0.0433 (13)	−0.0010 (11)	−0.0027 (10)	0.0038 (10)
C32	0.0553 (16)	0.0477 (15)	0.0485 (15)	−0.0008 (13)	0.0063 (13)	−0.0057 (13)
N1	0.0328 (17)	0.0259 (14)	0.0262 (14)	0.0003 (13)	0.0010 (13)	−0.0011 (11)
N2	0.0365 (18)	0.0275 (14)	0.0253 (14)	0.0047 (12)	0.0028 (12)	0.0000 (11)
N3	0.051 (2)	0.0224 (14)	0.0258 (16)	0.0000 (15)	0.0034 (14)	−0.0026 (13)
N4	0.060 (2)	0.0196 (14)	0.0244 (18)	0.0001 (15)	−0.0013 (16)	0.0011 (13)
C33	0.036 (2)	0.0298 (16)	0.0207 (13)	0.0015 (15)	−0.0009 (14)	0.0019 (11)
C34	0.048 (2)	0.0235 (15)	0.0304 (19)	0.0052 (14)	0.0051 (15)	−0.0011 (14)
C35	0.042 (2)	0.0242 (17)	0.0342 (18)	−0.0040 (16)	−0.0026 (17)	−0.0041 (15)
C36	0.048 (2)	0.0274 (17)	0.029 (2)	0.0081 (15)	−0.0097 (15)	−0.0065 (15)
C37	0.042 (2)	0.0237 (16)	0.0344 (19)	−0.0030 (15)	0.0028 (16)	0.0026 (14)
C38	0.068 (2)	0.026 (2)	0.0188 (14)	0.0044 (18)	−0.0007 (17)	0.0028 (15)
N1X	0.044 (4)	0.026 (3)	0.029 (3)	0.005 (3)	−0.005 (3)	0.000 (3)
N2X	0.039 (3)	0.027 (3)	0.025 (3)	0.004 (3)	0.002 (3)	0.002 (3)
N3X	0.054 (4)	0.021 (3)	0.025 (3)	0.001 (3)	0.000 (3)	0.001 (3)
N4X	0.050 (3)	0.027 (3)	0.024 (3)	0.003 (3)	−0.008 (3)	0.003 (3)
C33X	0.037 (4)	0.030 (4)	0.020 (3)	0.005 (3)	0.002 (3)	0.005 (3)
C34X	0.050 (4)	0.027 (3)	0.031 (4)	0.008 (4)	0.009 (4)	0.004 (3)
C35X	0.044 (4)	0.027 (4)	0.029 (4)	0.001 (4)	−0.003 (4)	0.003 (3)
C36X	0.049 (4)	0.019 (3)	0.026 (4)	0.004 (3)	−0.007 (4)	−0.003 (3)
C37X	0.047 (4)	0.030 (4)	0.028 (4)	−0.003 (4)	0.006 (4)	0.008 (3)
C38X	0.062 (4)	0.025 (4)	0.022 (4)	0.002 (4)	0.000 (4)	−0.006 (3)
C39	0.0500 (11)	0.0261 (8)	0.0223 (7)	−0.0010 (7)	0.0001 (11)	−0.0013 (10)
C40	0.0392 (12)	0.0246 (11)	0.0356 (11)	0.0070 (9)	0.0009 (10)	−0.0006 (9)
C41	0.0366 (12)	0.0267 (11)	0.0419 (13)	−0.0087 (9)	−0.0001 (10)	−0.0032 (10)
C42	0.0406 (12)	0.0224 (10)	0.0385 (12)	0.0082 (9)	0.0007 (10)	0.0012 (9)
C43	0.0341 (12)	0.0297 (11)	0.0443 (13)	−0.0086 (9)	0.0038 (10)	0.0038 (10)
C44	0.0533 (12)	0.0353 (9)	0.0216 (8)	0.0044 (8)	0.0003 (12)	0.0009 (11)

Geometric parameters (Å, º) top

O1—C7	1.313 (5)	C17—C18	1.394 (4)
O1—H1O1	0.83 (2)	C17—C22	1.416 (4)
O2—C7	1.207 (5)	C17—C23	1.483 (3)
C7—C1	1.488 (6)	C18—C19	1.402 (3)
C1—C6	1.395 (6)	C18—C24	1.495 (4)
C1—C2	1.411 (6)	C19—C20	1.369 (4)
C2—C3	1.396 (6)	C19—H19A	0.9500
C2—C8	1.504 (7)	C20—C21	1.390 (4)
C3—C4	1.376 (7)	C20—H20A	0.9500
C3—H3A	0.9500	C21—C22	1.371 (4)
C4—C5	1.383 (7)	C21—H21A	0.9500
C4—H4A	0.9500	C22—H22A	0.9500
C5—C6	1.377 (6)	C24—H24A	0.9800
C5—H5A	0.9500	C24—H24B	0.9800
C6—H6A	0.9500	C24—H24C	0.9800
C8—H8A	0.9800	C25—C26	1.399 (3)
C8—H8B	0.9800	C25—C30	1.411 (3)
C8—H8C	0.9800	C25—C31	1.489 (3)
O1X—C7X	1.310 (9)	C26—C27	1.403 (3)
O1X—H2O1	0.8400	C26—C32	1.487 (4)
O2X—C7X	1.215 (10)	C27—C28	1.362 (4)
C7X—C1X	1.492 (11)	C27—H27A	0.9500
C1X—C2X	1.401 (12)	C28—C29	1.389 (4)
C1X—C6X	1.404 (11)	C28—H28A	0.9500
C2X—C3X	1.390 (13)	C29—C30	1.370 (4)
C2X—C8X	1.509 (12)	C29—H29A	0.9500
C3X—C4X	1.373 (12)	C30—H30A	0.9500
C3X—H3XA	0.9500	C32—H32A	0.9800
C4X—C5X	1.386 (11)	C32—H32B	0.9800
C4X—H4XA	0.9500	C32—H32C	0.9800
C5X—C6X	1.370 (11)	N1—C33	1.481 (4)
C5X—H5XA	0.9500	N1—C36	1.481 (5)
C6X—H6XA	0.9500	N1—C35	1.481 (5)
C8X—H8XA	0.9800	N2—C33	1.473 (4)
C8X—H8XB	0.9800	N2—C34	1.474 (5)
C8X—H8XC	0.9800	N2—C37	1.485 (5)
O3—C15	1.313 (4)	N3—C35	1.462 (5)
O3—H1O3	0.844 (19)	N3—C34	1.463 (5)
O4—C15	1.203 (4)	N3—C38	1.474 (6)
C15—C9	1.498 (4)	N4—C36	1.457 (6)
C9—C14	1.398 (4)	N4—C37	1.458 (6)
C9—C10	1.407 (4)	N4—C38	1.477 (6)
C10—C11	1.405 (5)	C33—H33A	0.9900
C10—C16	1.501 (5)	C33—H33B	0.9900
C11—C12	1.384 (5)	C34—H34A	0.9900
C11—H11A	0.9500	C34—H34B	0.9900
C12—C13	1.377 (5)	C35—H35A	0.9900
C12—H12A	0.9500	C35—H35B	0.9900
C13—C14	1.381 (5)	C36—H36A	0.9900
C13—H13A	0.9500	C36—H36B	0.9900
C14—H14A	0.9500	C37—H37A	0.9900
C16—H16A	0.9800	C37—H37B	0.9900
C16—H16B	0.9800	C38—H38A	0.9900
C16—H16C	0.9800	C38—H38B	0.9900
O3X—C15X	1.311 (13)	N1X—C36X	1.470 (13)
O3X—H2O3	0.8400	N1X—C33X	1.473 (11)
O4X—C15X	1.206 (13)	N1X—C35X	1.476 (13)
C15X—C9X	1.524 (14)	N2X—C33X	1.462 (11)
C9X—C14X	1.388 (14)	N2X—C34X	1.490 (13)
C9X—C10X	1.397 (15)	N2X—C37X	1.505 (13)
C10X—C11X	1.404 (15)	N3X—C35X	1.451 (14)
C10X—C16X	1.515 (15)	N3X—C34X	1.464 (14)
C11X—C12X	1.368 (15)	N3X—C38X	1.474 (15)
C11X—H11B	0.9500	N4X—C36X	1.457 (15)
C12X—C13X	1.364 (15)	N4X—C37X	1.458 (15)
C12X—H12B	0.9500	N4X—C38X	1.470 (15)
C13X—C14X	1.362 (15)	C33X—H33C	0.9900
C13X—H13B	0.9500	C33X—H33D	0.9900
C14X—H14B	0.9500	C34X—H34C	0.9900
C16X—H16D	0.9800	C34X—H34D	0.9900
C16X—H16E	0.9800	C35X—H35C	0.9900
C16X—H16F	0.9800	C35X—H35D	0.9900
O5—C23	1.308 (3)	C36X—H36C	0.9900
O5—H1O5	0.870 (19)	C36X—H36D	0.9900
O6—C23	1.218 (3)	C37X—H37C	0.9900
O7—C31	1.302 (3)	C37X—H37D	0.9900
O7—H1O7	0.869 (19)	C38X—H38C	0.9900
O8—C31	1.211 (3)	C38X—H38D	0.9900
N5—C39	1.472 (3)	C39—H39A	0.9900
N5—C42	1.478 (3)	C39—H39B	0.9900
N5—C41	1.481 (3)	C40—H40A	0.9900
N6—C39	1.470 (3)	C40—H40B	0.9900
N6—C40	1.477 (3)	C41—H41A	0.9900
N6—C43	1.479 (3)	C41—H41B	0.9900
N7—C41	1.452 (3)	C42—H42A	0.9900
N7—C40	1.461 (3)	C42—H42B	0.9900
N7—C44	1.469 (3)	C43—H43A	0.9900
N8—C43	1.456 (3)	C43—H43B	0.9900
N8—C42	1.457 (3)	C44—H44A	0.9900
N8—C44	1.477 (3)	C44—H44B	0.9900

C7—O1—H1O1	111 (3)	C25—C26—C27	118.0 (2)
O2—C7—O1	122.5 (4)	C25—C26—C32	124.1 (2)
O2—C7—C1	124.6 (4)	C27—C26—C32	117.9 (2)
O1—C7—C1	112.9 (4)	C28—C27—C26	122.1 (3)
C6—C1—C2	119.2 (5)	C28—C27—H27A	119.0
C6—C1—C7	118.9 (5)	C26—C27—H27A	119.0
C2—C1—C7	121.9 (5)	C27—C28—C29	120.1 (2)
C3—C2—C1	117.8 (6)	C27—C28—H28A	119.9
C3—C2—C8	119.0 (5)	C29—C28—H28A	119.9
C1—C2—C8	123.2 (5)	C30—C29—C28	119.4 (2)
C4—C3—C2	121.9 (6)	C30—C29—H29A	120.3
C4—C3—H3A	119.0	C28—C29—H29A	120.3
C2—C3—H3A	119.0	C29—C30—C25	121.3 (2)
C3—C4—C5	120.2 (5)	C29—C30—H30A	119.4
C3—C4—H4A	119.9	C25—C30—H30A	119.4
C5—C4—H4A	119.9	O8—C31—O7	121.9 (2)
C6—C5—C4	119.0 (5)	O8—C31—C25	123.9 (2)
C6—C5—H5A	120.5	O7—C31—C25	114.2 (2)
C4—C5—H5A	120.5	C26—C32—H32A	109.5
C5—C6—C1	121.8 (5)	C26—C32—H32B	109.5
C5—C6—H6A	119.1	H32A—C32—H32B	109.5
C1—C6—H6A	119.1	C26—C32—H32C	109.5
C2—C8—H8A	109.5	H32A—C32—H32C	109.5
C2—C8—H8B	109.5	H32B—C32—H32C	109.5
H8A—C8—H8B	109.5	C33—N1—C36	107.8 (3)
C2—C8—H8C	109.5	C33—N1—C35	108.4 (3)
H8A—C8—H8C	109.5	C36—N1—C35	109.1 (3)
H8B—C8—H8C	109.5	C33—N2—C34	108.2 (3)
C7X—O1X—H2O1	109.5	C33—N2—C37	107.5 (3)
O2X—C7X—O1X	124.1 (9)	C34—N2—C37	107.8 (3)
O2X—C7X—C1X	119.6 (9)	C35—N3—C34	108.1 (4)
O1X—C7X—C1X	116.2 (8)	C35—N3—C38	108.1 (5)
C2X—C1X—C6X	120.7 (10)	C34—N3—C38	109.6 (5)
C2X—C1X—C7X	123.5 (10)	C36—N4—C37	109.6 (4)
C6X—C1X—C7X	115.8 (9)	C36—N4—C38	107.3 (5)
C3X—C2X—C1X	116.3 (11)	C37—N4—C38	108.2 (6)
C3X—C2X—C8X	116.4 (10)	N2—C33—N1	111.6 (3)
C1X—C2X—C8X	127.2 (11)	N2—C33—H33A	109.3
C4X—C3X—C2X	123.1 (13)	N1—C33—H33A	109.3
C4X—C3X—H3XA	118.5	N2—C33—H33B	109.3
C2X—C3X—H3XA	118.5	N1—C33—H33B	109.3
C3X—C4X—C5X	119.9 (11)	H33A—C33—H33B	108.0
C3X—C4X—H4XA	120.0	N3—C34—N2	112.1 (4)
C5X—C4X—H4XA	120.0	N3—C34—H34A	109.2
C6X—C5X—C4X	119.0 (10)	N2—C34—H34A	109.2
C6X—C5X—H5XA	120.5	N3—C34—H34B	109.2
C4X—C5X—H5XA	120.5	N2—C34—H34B	109.2
C5X—C6X—C1X	120.9 (9)	H34A—C34—H34B	107.9
C5X—C6X—H6XA	119.6	N3—C35—N1	111.0 (4)
C1X—C6X—H6XA	119.6	N3—C35—H35A	109.4
C2X—C8X—H8XA	109.5	N1—C35—H35A	109.4
C2X—C8X—H8XB	109.5	N3—C35—H35B	109.4
H8XA—C8X—H8XB	109.5	N1—C35—H35B	109.4
C2X—C8X—H8XC	109.5	H35A—C35—H35B	108.0
H8XA—C8X—H8XC	109.5	N4—C36—N1	111.4 (4)
H8XB—C8X—H8XC	109.5	N4—C36—H36A	109.3
C15—O3—H1O3	109 (3)	N1—C36—H36A	109.3
O4—C15—O3	122.4 (3)	N4—C36—H36B	109.3
O4—C15—C9	121.2 (3)	N1—C36—H36B	109.3
O3—C15—C9	116.4 (3)	H36A—C36—H36B	108.0
C14—C9—C10	119.9 (3)	N4—C37—N2	112.4 (4)
C14—C9—C15	115.5 (3)	N4—C37—H37A	109.1
C10—C9—C15	124.5 (3)	N2—C37—H37A	109.1
C11—C10—C9	117.6 (4)	N4—C37—H37B	109.1
C11—C10—C16	116.7 (3)	N2—C37—H37B	109.1
C9—C10—C16	125.6 (3)	H37A—C37—H37B	107.8
C12—C11—C10	121.5 (4)	N3—C38—N4	111.8 (5)
C12—C11—H11A	119.2	N3—C38—H38A	109.3
C10—C11—H11A	119.2	N4—C38—H38A	109.3
C13—C12—C11	120.4 (3)	N3—C38—H38B	109.3
C13—C12—H12A	119.8	N4—C38—H38B	109.3
C11—C12—H12A	119.8	H38A—C38—H38B	107.9
C12—C13—C14	119.4 (3)	C36X—N1X—C33X	108.5 (9)
C12—C13—H13A	120.3	C36X—N1X—C35X	107.3 (11)
C14—C13—H13A	120.3	C33X—N1X—C35X	106.7 (9)
C13—C14—C9	121.2 (3)	C33X—N2X—C34X	106.5 (9)
C13—C14—H14A	119.4	C33X—N2X—C37X	107.3 (9)
C9—C14—H14A	119.4	C34X—N2X—C37X	108.1 (11)
C10—C16—H16A	109.5	C35X—N3X—C34X	110.4 (13)
C10—C16—H16B	109.5	C35X—N3X—C38X	109.6 (16)
H16A—C16—H16B	109.5	C34X—N3X—C38X	104.7 (15)
C10—C16—H16C	109.5	C36X—N4X—C37X	106.0 (14)
H16A—C16—H16C	109.5	C36X—N4X—C38X	110.3 (16)
H16B—C16—H16C	109.5	C37X—N4X—C38X	110.1 (17)
C15X—O3X—H2O3	109.5	N2X—C33X—N1X	113.5 (8)
O4X—C15X—O3X	123.5 (12)	N2X—C33X—H33C	108.9
O4X—C15X—C9X	122.1 (11)	N1X—C33X—H33C	108.9
O3X—C15X—C9X	114.4 (12)	N2X—C33X—H33D	108.9
C14X—C9X—C10X	120.1 (13)	N1X—C33X—H33D	108.9
C14X—C9X—C15X	116.6 (13)	H33C—C33X—H33D	107.7
C10X—C9X—C15X	123.3 (13)	N3X—C34X—N2X	112.9 (11)
C9X—C10X—C11X	114.7 (15)	N3X—C34X—H34C	109.0
C9X—C10X—C16X	122.4 (14)	N2X—C34X—H34C	109.0
C11X—C10X—C16X	122.5 (15)	N3X—C34X—H34D	109.0
C12X—C11X—C10X	123.6 (16)	N2X—C34X—H34D	109.0
C12X—C11X—H11B	118.2	H34C—C34X—H34D	107.8
C10X—C11X—H11B	118.2	N3X—C35X—N1X	112.5 (12)
C13X—C12X—C11X	120.4 (14)	N3X—C35X—H35C	109.1
C13X—C12X—H12B	119.8	N1X—C35X—H35C	109.1
C11X—C12X—H12B	119.8	N3X—C35X—H35D	109.1
C14X—C13X—C12X	117.6 (14)	N1X—C35X—H35D	109.1
C14X—C13X—H13B	121.2	H35C—C35X—H35D	107.8
C12X—C13X—H13B	121.2	N4X—C36X—N1X	112.7 (12)
C13X—C14X—C9X	123.1 (15)	N4X—C36X—H36C	109.0
C13X—C14X—H14B	118.5	N1X—C36X—H36C	109.0
C9X—C14X—H14B	118.5	N4X—C36X—H36D	109.0
C10X—C16X—H16D	109.5	N1X—C36X—H36D	109.0
C10X—C16X—H16E	109.5	H36C—C36X—H36D	107.8
H16D—C16X—H16E	109.5	N4X—C37X—N2X	110.9 (13)
C10X—C16X—H16F	109.5	N4X—C37X—H37C	109.5
H16D—C16X—H16F	109.5	N2X—C37X—H37C	109.5
H16E—C16X—H16F	109.5	N4X—C37X—H37D	109.5
C23—O5—H1O5	106 (3)	N2X—C37X—H37D	109.5
C31—O7—H1O7	112 (3)	H37C—C37X—H37D	108.1
C39—N5—C42	108.35 (18)	N4X—C38X—N3X	111.4 (15)
C39—N5—C41	108.29 (18)	N4X—C38X—H38C	109.3
C42—N5—C41	108.12 (18)	N3X—C38X—H38C	109.3
C39—N6—C40	108.19 (18)	N4X—C38X—H38D	109.3
C39—N6—C43	107.92 (18)	N3X—C38X—H38D	109.3
C40—N6—C43	107.94 (18)	H38C—C38X—H38D	108.0
C41—N7—C40	108.33 (18)	N6—C39—N5	111.30 (13)
C41—N7—C44	108.64 (18)	N6—C39—H39A	109.4
C40—N7—C44	108.39 (19)	N5—C39—H39A	109.4
C43—N8—C42	108.25 (19)	N6—C39—H39B	109.4
C43—N8—C44	108.47 (18)	N5—C39—H39B	109.4
C42—N8—C44	108.10 (18)	H39A—C39—H39B	108.0
C18—C17—C22	119.2 (2)	N7—C40—N6	112.13 (17)
C18—C17—C23	123.2 (2)	N7—C40—H40A	109.2
C22—C17—C23	117.5 (2)	N6—C40—H40A	109.2
C17—C18—C19	118.0 (3)	N7—C40—H40B	109.2
C17—C18—C24	124.0 (2)	N6—C40—H40B	109.2
C19—C18—C24	118.0 (3)	H40A—C40—H40B	107.9
C20—C19—C18	121.7 (3)	N7—C41—N5	111.78 (17)
C20—C19—H19A	119.2	N7—C41—H41A	109.3
C18—C19—H19A	119.2	N5—C41—H41A	109.3
C19—C20—C21	121.0 (2)	N7—C41—H41B	109.3
C19—C20—H20A	119.5	N5—C41—H41B	109.3
C21—C20—H20A	119.5	H41A—C41—H41B	107.9
C22—C21—C20	118.3 (3)	N8—C42—N5	111.92 (17)
C22—C21—H21A	120.9	N8—C42—H42A	109.2
C20—C21—H21A	120.9	N5—C42—H42A	109.2
C21—C22—C17	121.8 (3)	N8—C42—H42B	109.2
C21—C22—H22A	119.1	N5—C42—H42B	109.2
C17—C22—H22A	119.1	H42A—C42—H42B	107.9
O6—C23—O5	122.2 (2)	N8—C43—N6	112.32 (18)
O6—C23—C17	123.7 (2)	N8—C43—H43A	109.1
O5—C23—C17	114.1 (2)	N6—C43—H43A	109.1
C18—C24—H24A	109.5	N8—C43—H43B	109.1
C18—C24—H24B	109.5	N6—C43—H43B	109.1
H24A—C24—H24B	109.5	H43A—C43—H43B	107.9
C18—C24—H24C	109.5	N7—C44—N8	111.72 (13)
H24A—C24—H24C	109.5	N7—C44—H44A	109.3
H24B—C24—H24C	109.5	N8—C44—H44A	109.3
C26—C25—C30	119.2 (2)	N7—C44—H44B	109.3
C26—C25—C31	123.2 (2)	N8—C44—H44B	109.3
C30—C25—C31	117.5 (2)	H44A—C44—H44B	107.9

O2—C7—C1—C6	170.8 (6)	C26—C27—C28—C29	−0.1 (4)
O1—C7—C1—C6	−11.1 (9)	C27—C28—C29—C30	0.6 (4)
O2—C7—C1—C2	−10.7 (13)	C28—C29—C30—C25	−0.7 (4)
O1—C7—C1—C2	167.4 (10)	C26—C25—C30—C29	0.2 (4)
C6—C1—C2—C3	1.0 (17)	C31—C25—C30—C29	177.9 (2)
C7—C1—C2—C3	−177.5 (9)	C26—C25—C31—O8	−10.9 (4)
C6—C1—C2—C8	−179.7 (9)	C30—C25—C31—O8	171.5 (3)
C7—C1—C2—C8	1.8 (18)	C26—C25—C31—O7	168.5 (2)
C1—C2—C3—C4	−1.0 (18)	C30—C25—C31—O7	−9.0 (3)
C8—C2—C3—C4	179.7 (9)	C34—N2—C33—N1	−57.3 (4)
C2—C3—C4—C5	0.3 (13)	C37—N2—C33—N1	58.9 (4)
C3—C4—C5—C6	0.4 (9)	C36—N1—C33—N2	−60.0 (4)
C4—C5—C6—C1	−0.3 (8)	C35—N1—C33—N2	58.0 (4)
C2—C1—C6—C5	−0.4 (12)	C35—N3—C34—N2	−60.3 (5)
C7—C1—C6—C5	178.1 (6)	C38—N3—C34—N2	57.2 (5)
O2X—C7X—C1X—C2X	163 (2)	C33—N2—C34—N3	58.7 (4)
O1X—C7X—C1X—C2X	−13 (3)	C37—N2—C34—N3	−57.3 (4)
O2X—C7X—C1X—C6X	−21 (2)	C34—N3—C35—N1	60.2 (5)
O1X—C7X—C1X—C6X	162.3 (13)	C38—N3—C35—N1	−58.4 (6)
C6X—C1X—C2X—C3X	4 (4)	C33—N1—C35—N3	−59.3 (5)
C7X—C1X—C2X—C3X	179 (2)	C36—N1—C35—N3	57.9 (5)
C6X—C1X—C2X—C8X	−176 (2)	C37—N4—C36—N1	−58.0 (5)
C7X—C1X—C2X—C8X	−1 (4)	C38—N4—C36—N1	59.2 (5)
C1X—C2X—C3X—C4X	−1 (4)	C33—N1—C36—N4	58.8 (4)
C8X—C2X—C3X—C4X	179 (2)	C35—N1—C36—N4	−58.7 (4)
C2X—C3X—C4X—C5X	−1 (3)	C36—N4—C37—N2	57.6 (6)
C3X—C4X—C5X—C6X	1.0 (19)	C38—N4—C37—N2	−59.1 (6)
C4X—C5X—C6X—C1X	1.8 (18)	C33—N2—C37—N4	−57.5 (5)
C2X—C1X—C6X—C5X	−4 (3)	C34—N2—C37—N4	58.9 (5)
C7X—C1X—C6X—C5X	179.9 (12)	C35—N3—C38—N4	60.6 (7)
O4—C15—C9—C14	−18.6 (5)	C34—N3—C38—N4	−57.0 (7)
O3—C15—C9—C14	161.2 (4)	C36—N4—C38—N3	−60.7 (7)
O4—C15—C9—C10	157.5 (7)	C37—N4—C38—N3	57.5 (7)
O3—C15—C9—C10	−22.8 (8)	C34X—N2X—C33X—N1X	−59.9 (12)
C14—C9—C10—C11	−0.6 (12)	C37X—N2X—C33X—N1X	55.7 (13)
C15—C9—C10—C11	−176.5 (6)	C36X—N1X—C33X—N2X	−54.3 (12)
C14—C9—C10—C16	−178.2 (7)	C35X—N1X—C33X—N2X	61.0 (12)
C15—C9—C10—C16	5.9 (13)	C35X—N3X—C34X—N2X	−55.2 (18)
C9—C10—C11—C12	0.5 (12)	C38X—N3X—C34X—N2X	62.6 (16)
C16—C10—C11—C12	178.3 (6)	C33X—N2X—C34X—N3X	55.8 (14)
C10—C11—C12—C13	−0.2 (9)	C37X—N2X—C34X—N3X	−59.3 (14)
C11—C12—C13—C14	0.0 (6)	C34X—N3X—C35X—N1X	56.1 (18)
C12—C13—C14—C9	−0.1 (6)	C38X—N3X—C35X—N1X	−58.7 (18)
C10—C9—C14—C13	0.5 (8)	C36X—N1X—C35X—N3X	58.7 (15)
C15—C9—C14—C13	176.7 (3)	C33X—N1X—C35X—N3X	−57.5 (15)
O4X—C15X—C9X—C14X	166.4 (18)	C37X—N4X—C36X—N1X	−62.3 (17)
O3X—C15X—C9X—C14X	−15 (3)	C38X—N4X—C36X—N1X	56.8 (17)
O4X—C15X—C9X—C10X	−10 (4)	C33X—N1X—C36X—N4X	57.5 (15)
O3X—C15X—C9X—C10X	168 (3)	C35X—N1X—C36X—N4X	−57.4 (15)
C14X—C9X—C10X—C11X	8 (6)	C36X—N4X—C37X—N2X	63.4 (18)
C15X—C9X—C10X—C11X	−175 (3)	C38X—N4X—C37X—N2X	−55.9 (18)
C14X—C9X—C10X—C16X	−179 (3)	C33X—N2X—C37X—N4X	−60.7 (15)
C15X—C9X—C10X—C16X	−3 (6)	C34X—N2X—C37X—N4X	53.8 (16)
C9X—C10X—C11X—C12X	−7 (6)	C36X—N4X—C38X—N3X	−55 (2)
C16X—C10X—C11X—C12X	−179 (3)	C37X—N4X—C38X—N3X	62 (2)
C10X—C11X—C12X—C13X	3 (5)	C35X—N3X—C38X—N4X	56 (2)
C11X—C12X—C13X—C14X	0 (3)	C34X—N3X—C38X—N4X	−63 (2)
C12X—C13X—C14X—C9X	2 (3)	C40—N6—C39—N5	−58.2 (3)
C10X—C9X—C14X—C13X	−7 (4)	C43—N6—C39—N5	58.4 (3)
C15X—C9X—C14X—C13X	176.8 (18)	C42—N5—C39—N6	−58.6 (3)
C22—C17—C18—C19	−0.3 (3)	C41—N5—C39—N6	58.5 (3)
C23—C17—C18—C19	−177.0 (2)	C41—N7—C40—N6	−58.9 (2)
C22—C17—C18—C24	179.8 (2)	C44—N7—C40—N6	58.8 (2)
C23—C17—C18—C24	3.1 (4)	C39—N6—C40—N7	58.6 (2)
C17—C18—C19—C20	0.1 (4)	C43—N6—C40—N7	−58.0 (2)
C24—C18—C19—C20	−179.9 (2)	C40—N7—C41—N5	59.0 (2)
C18—C19—C20—C21	−0.1 (4)	C44—N7—C41—N5	−58.6 (2)
C19—C20—C21—C22	0.2 (4)	C39—N5—C41—N7	−59.1 (2)
C20—C21—C22—C17	−0.4 (4)	C42—N5—C41—N7	58.1 (2)
C18—C17—C22—C21	0.4 (4)	C43—N8—C42—N5	−58.6 (2)
C23—C17—C22—C21	177.3 (2)	C44—N8—C42—N5	58.7 (2)
C18—C17—C23—O6	−4.5 (4)	C39—N5—C42—N8	58.8 (2)
C22—C17—C23—O6	178.8 (3)	C41—N5—C42—N8	−58.4 (2)
C18—C17—C23—O5	174.4 (2)	C42—N8—C43—N6	58.9 (2)
C22—C17—C23—O5	−2.3 (3)	C44—N8—C43—N6	−58.2 (2)
C30—C25—C26—C27	0.3 (3)	C39—N6—C43—N8	−58.9 (2)
C31—C25—C26—C27	−177.2 (2)	C40—N6—C43—N8	57.8 (2)
C30—C25—C26—C32	178.7 (2)	C41—N7—C44—N8	58.9 (3)
C31—C25—C26—C32	1.2 (4)	C40—N7—C44—N8	−58.6 (3)
C25—C26—C27—C28	−0.4 (4)	C43—N8—C44—N7	58.4 (3)
C32—C26—C27—C28	−178.8 (2)	C42—N8—C44—N7	−58.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.84 (3)	1.79 (4)	2.620 (5)	171 (4)
O3—H1O3···N2	0.85 (4)	1.83 (4)	2.677 (5)	176 (3)
O5—H1O5···N5	0.87 (3)	1.83 (3)	2.677 (3)	166 (4)
O7—H1O7···N6	0.87 (3)	1.80 (3)	2.664 (3)	171 (4)
C6—H6A···O1	0.95	2.34	2.682 (6)	101
C16—H16A···O3	0.98	2.45	2.818 (5)	102
C22—H22A···O5	0.95	2.32	2.673 (3)	101
C30—H30A···O7	0.95	2.34	2.683 (3)	101
C33—H33A···O4	0.99	2.58	3.141 (5)	116
C33—H33B···N8ⁱ	0.99	2.60	3.529 (4)	157
C36—H36B···N7	0.99	2.60	3.550 (6)	161
C38—H38B···O4ⁱⁱ	0.99	2.43	3.387 (9)	161
C40—H40B···N3ⁱⁱⁱ	0.99	2.59	3.507 (7)	155
C44—H44A···O6^iv	0.99	2.38	3.367 (4)	172
C44—H44B···O8^iv	0.99	2.39	3.372 (3)	171

Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) x, −y+3/2, z−1/2.

(163K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top

Crystal data top

C₆H₁₂N₄·2C₈H₈O₂	F(000) = 1760
M_r = 412.48	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 30.9991 (17) Å	Cell parameters from 9880 reflections
b = 9.3611 (5) Å	θ = 2.2–27.1°
c = 14.3546 (8) Å	µ = 0.09 mm⁻¹
β = 90.0906 (12)°	T = 163 K
V = 4165.5 (4) Å³	Block, colourless
Z = 8	0.43 × 0.17 × 0.15 mm

Data collection top

Bruker APEX DUO CCD area detector diffractometer	10040 independent reflections
Radiation source: fine-focus sealed tube	7515 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 28.0°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −36→40
T_min = 0.915, T_max = 0.963	k = −12→12
66066 measured reflections	l = −18→18

Refinement top

Refinement on F²	1222 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.150	w = 1/[σ²(F_o²) + (0.0704P)² + 1.4929P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
10040 reflections	Δρ_max = 0.46 e Å⁻³
837 parameters	Δρ_min = −0.19 e Å⁻³

Special details top

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.16463 (12)	0.2382 (5)	0.3350 (3)	0.0500 (10)	0.602 (7)
H1O1	0.1784 (14)	0.250 (5)	0.286 (2)	0.064 (15)*	0.602 (7)
O2	0.12826 (14)	0.4183 (6)	0.2738 (3)	0.0601 (12)	0.602 (7)
C7	0.13364 (15)	0.3336 (6)	0.3363 (4)	0.0333 (10)	0.602 (7)
C1	0.1077 (3)	0.3295 (8)	0.4233 (5)	0.0326 (12)	0.602 (7)
C2	0.0784 (5)	0.4393 (11)	0.4473 (8)	0.0347 (14)	0.602 (7)
C3	0.0564 (4)	0.4281 (10)	0.5315 (6)	0.0425 (15)	0.602 (7)
H3A	0.0369	0.5016	0.5489	0.051*	0.602 (7)
C4	0.0622 (2)	0.3137 (8)	0.5901 (5)	0.0448 (14)	0.602 (7)
H4A	0.0469	0.3092	0.6473	0.054*	0.602 (7)
C5	0.0901 (2)	0.2053 (7)	0.5661 (5)	0.0432 (13)	0.602 (7)
H5A	0.0937	0.1250	0.6058	0.052*	0.602 (7)
C6	0.11278 (19)	0.2145 (7)	0.4839 (4)	0.0371 (11)	0.602 (7)
H6A	0.1324	0.1404	0.4681	0.044*	0.602 (7)
C8	0.0708 (3)	0.5682 (8)	0.3862 (6)	0.0478 (16)	0.602 (7)
H8A	0.0983	0.6157	0.3736	0.072*	0.602 (7)
H8B	0.0514	0.6348	0.4180	0.072*	0.602 (7)
H8C	0.0577	0.5377	0.3273	0.072*	0.602 (7)
O1X	0.1346 (2)	0.3338 (8)	0.2843 (5)	0.0570 (17)	0.398 (7)
H2O1	0.1534	0.3048	0.2469	0.085*	0.398 (7)
O2X	0.16553 (18)	0.1741 (7)	0.3768 (5)	0.0601 (18)	0.398 (7)
C7X	0.1376 (2)	0.2623 (9)	0.3623 (5)	0.0381 (14)	0.398 (7)
C1X	0.1062 (5)	0.3008 (12)	0.4371 (8)	0.0310 (16)	0.398 (7)
C2X	0.0817 (7)	0.4269 (18)	0.4368 (12)	0.0345 (18)	0.398 (7)
C3X	0.0548 (6)	0.4492 (15)	0.5126 (9)	0.0359 (18)	0.398 (7)
H3XA	0.0386	0.5351	0.5154	0.043*	0.398 (7)
C4X	0.0507 (3)	0.3516 (11)	0.5841 (8)	0.0387 (18)	0.398 (7)
H4XA	0.0319	0.3714	0.6347	0.046*	0.398 (7)
C5X	0.0739 (3)	0.2250 (10)	0.5824 (6)	0.0384 (17)	0.398 (7)
H5XA	0.0709	0.1566	0.6308	0.046*	0.398 (7)
C6X	0.1014 (3)	0.2006 (10)	0.5082 (7)	0.0350 (16)	0.398 (7)
H6XA	0.1173	0.1140	0.5056	0.042*	0.398 (7)
C8X	0.0814 (4)	0.5416 (12)	0.3626 (8)	0.044 (2)	0.398 (7)
H8XA	0.1105	0.5811	0.3556	0.065*	0.398 (7)
H8XB	0.0614	0.6179	0.3808	0.065*	0.398 (7)
H8XC	0.0720	0.5003	0.3032	0.065*	0.398 (7)
O3	0.36536 (10)	0.1735 (4)	0.2832 (2)	0.0507 (8)	0.743 (6)
H1O3	0.3429 (12)	0.190 (6)	0.252 (4)	0.106 (19)*	0.743 (6)
O4	0.33481 (9)	0.3290 (3)	0.3777 (3)	0.0550 (9)	0.743 (6)
C15	0.36216 (11)	0.2404 (4)	0.3630 (3)	0.0328 (8)	0.743 (6)
C9	0.39463 (19)	0.2023 (5)	0.4360 (3)	0.0271 (9)	0.743 (6)
C10	0.4180 (3)	0.0734 (8)	0.4381 (5)	0.0291 (9)	0.743 (6)
C11	0.4460 (2)	0.0506 (6)	0.5142 (4)	0.0343 (10)	0.743 (6)
H11A	0.4623	−0.0351	0.5170	0.041*	0.743 (6)
C12	0.45015 (16)	0.1496 (5)	0.5844 (3)	0.0390 (10)	0.743 (6)
H12A	0.4691	0.1311	0.6350	0.047*	0.743 (6)
C13	0.42712 (16)	0.2752 (5)	0.5822 (3)	0.0392 (9)	0.743 (6)
H13A	0.4301	0.3432	0.6309	0.047*	0.743 (6)
C14	0.39956 (15)	0.3015 (5)	0.5082 (3)	0.0344 (9)	0.743 (6)
H14A	0.3837	0.3883	0.5063	0.041*	0.743 (6)
C16	0.41691 (16)	−0.0406 (5)	0.3648 (4)	0.0384 (11)	0.743 (6)
H16A	0.3871	−0.0559	0.3445	0.058*	0.743 (6)
H16B	0.4285	−0.1297	0.3906	0.058*	0.743 (6)
H16C	0.4344	−0.0108	0.3115	0.058*	0.743 (6)
O3X	0.3347 (3)	0.2631 (10)	0.3371 (7)	0.050 (2)	0.257 (6)
H2O3	0.3206	0.2573	0.2873	0.074*	0.257 (6)
O4X	0.3723 (3)	0.0866 (13)	0.2726 (6)	0.061 (3)	0.257 (6)
C15X	0.3659 (3)	0.1679 (12)	0.3366 (8)	0.0339 (19)	0.257 (6)
C9X	0.3936 (6)	0.1691 (17)	0.4239 (11)	0.0324 (19)	0.257 (6)
C10X	0.4223 (11)	0.059 (3)	0.4462 (17)	0.032 (2)	0.257 (6)
C11X	0.4425 (7)	0.0711 (19)	0.5337 (11)	0.037 (2)	0.257 (6)
H11B	0.4605	−0.0047	0.5542	0.044*	0.257 (6)
C12X	0.4373 (5)	0.1866 (17)	0.5904 (10)	0.039 (2)	0.257 (6)
H12B	0.4528	0.1910	0.6475	0.047*	0.257 (6)
C13X	0.4102 (5)	0.2972 (14)	0.5665 (10)	0.041 (2)	0.257 (6)
H13B	0.4064	0.3777	0.6060	0.049*	0.257 (6)
C14X	0.3888 (5)	0.2860 (16)	0.4829 (10)	0.0372 (19)	0.257 (6)
H14B	0.3700	0.3610	0.4646	0.045*	0.257 (6)
C16X	0.4297 (5)	−0.0691 (15)	0.3843 (10)	0.041 (3)	0.257 (6)
H16D	0.4552	−0.1214	0.4060	0.062*	0.257 (6)
H16E	0.4343	−0.0371	0.3200	0.062*	0.257 (6)
H16F	0.4045	−0.1320	0.3867	0.062*	0.257 (6)
O5	0.13505 (7)	0.8190 (3)	0.52576 (16)	0.0593 (6)
H1O5	0.1598 (10)	0.791 (5)	0.505 (4)	0.13 (2)*
O6	0.15736 (6)	0.6856 (3)	0.64314 (19)	0.0681 (7)
O7	0.36434 (7)	0.6897 (2)	0.52239 (15)	0.0574 (6)
H1O7	0.3380 (7)	0.703 (4)	0.501 (3)	0.081 (12)*
O8	0.34134 (7)	0.8053 (3)	0.64595 (18)	0.0719 (7)
N5	0.21061 (6)	0.7725 (2)	0.44110 (14)	0.0321 (4)
N6	0.28804 (6)	0.7312 (2)	0.44080 (14)	0.0316 (4)
N7	0.24257 (7)	0.6222 (2)	0.32184 (14)	0.0328 (4)
N8	0.25518 (6)	0.8794 (2)	0.32030 (14)	0.0334 (5)
C17	0.08288 (7)	0.7498 (3)	0.63494 (18)	0.0336 (5)
C18	0.06827 (9)	0.6695 (3)	0.7105 (2)	0.0406 (6)
C19	0.02412 (8)	0.6747 (3)	0.7313 (2)	0.0463 (7)
H19A	0.0136	0.6209	0.7825	0.056*
C20	−0.00433 (8)	0.7550 (3)	0.6800 (2)	0.0486 (7)
H20A	−0.0340	0.7557	0.6961	0.058*
C21	0.01005 (9)	0.8351 (3)	0.6048 (2)	0.0479 (7)
H21A	−0.0095	0.8913	0.5693	0.057*
C22	0.05288 (9)	0.8314 (3)	0.5830 (2)	0.0432 (6)
H22A	0.0629	0.8853	0.5313	0.052*
C23	0.12847 (8)	0.7480 (3)	0.6029 (2)	0.0394 (6)
C24	0.09667 (10)	0.5784 (3)	0.7700 (2)	0.0538 (7)
H24A	0.0791	0.5294	0.8169	0.081*
H24B	0.1182	0.6385	0.8012	0.081*
H24C	0.1113	0.5075	0.7311	0.081*
C25	0.41632 (7)	0.7494 (3)	0.63504 (17)	0.0325 (5)
C26	0.43104 (8)	0.8284 (3)	0.71115 (18)	0.0370 (6)
C27	0.47513 (8)	0.8230 (3)	0.7323 (2)	0.0419 (6)
H27A	0.4857	0.8767	0.7837	0.050*
C28	0.50328 (8)	0.7432 (3)	0.6815 (2)	0.0444 (6)
H28A	0.5330	0.7420	0.6978	0.053*
C29	0.48886 (9)	0.6636 (3)	0.6060 (2)	0.0459 (6)
H29A	0.5085	0.6074	0.5708	0.055*
C30	0.44577 (8)	0.6672 (3)	0.58292 (19)	0.0393 (6)
H30A	0.4357	0.6135	0.5311	0.047*
C31	0.37056 (8)	0.7507 (3)	0.60274 (19)	0.0375 (5)
C32	0.40299 (10)	0.9204 (3)	0.7700 (2)	0.0505 (7)
H32A	0.4209	0.9737	0.8144	0.076*
H32B	0.3825	0.8605	0.8041	0.076*
H32C	0.3872	0.9876	0.7303	0.076*
N1	0.21773 (17)	0.2511 (5)	0.1932 (3)	0.0301 (8)	0.675 (11)
N2	0.29601 (17)	0.2286 (5)	0.1778 (3)	0.0307 (9)	0.675 (11)
N3	0.2481 (2)	0.1196 (9)	0.0635 (5)	0.0337 (11)	0.675 (11)
N4	0.2553 (3)	0.3795 (9)	0.0699 (5)	0.0347 (11)	0.675 (11)
C33	0.2596 (2)	0.2378 (5)	0.2433 (3)	0.0287 (9)	0.675 (11)
H33A	0.2637	0.3216	0.2844	0.034*	0.675 (11)
H33B	0.2591	0.1511	0.2828	0.034*	0.675 (11)
C34	0.2886 (2)	0.1058 (6)	0.1149 (4)	0.0347 (11)	0.675 (11)
H34A	0.3128	0.0989	0.0702	0.042*	0.675 (11)
H34B	0.2881	0.0167	0.1520	0.042*	0.675 (11)
C35	0.2128 (2)	0.1254 (7)	0.1312 (5)	0.0345 (12)	0.675 (11)
H35A	0.2128	0.0370	0.1691	0.041*	0.675 (11)
H35B	0.1849	0.1313	0.0979	0.041*	0.675 (11)
C36	0.2197 (2)	0.3825 (7)	0.1366 (4)	0.0359 (11)	0.675 (11)
H36A	0.1922	0.3943	0.1024	0.043*	0.675 (11)
H36B	0.2233	0.4659	0.1783	0.043*	0.675 (11)
C37	0.2957 (2)	0.3596 (7)	0.1199 (5)	0.0351 (12)	0.675 (11)
H37A	0.3009	0.4435	0.1605	0.042*	0.675 (11)
H37B	0.3197	0.3546	0.0745	0.042*	0.675 (11)
C38	0.2488 (4)	0.2534 (10)	0.0097 (6)	0.0390 (12)	0.675 (11)
H38A	0.2211	0.2638	−0.0242	0.047*	0.675 (11)
H38B	0.2722	0.2489	−0.0369	0.047*	0.675 (11)
N1X	0.2035 (4)	0.2742 (10)	0.1791 (7)	0.0338 (16)	0.325 (11)
N2X	0.2819 (4)	0.2475 (11)	0.1941 (7)	0.0304 (15)	0.325 (11)
N3X	0.2425 (5)	0.1176 (19)	0.0720 (11)	0.0338 (18)	0.325 (11)
N4X	0.2509 (5)	0.376 (2)	0.0625 (12)	0.0351 (18)	0.325 (11)
C33X	0.2409 (4)	0.2618 (10)	0.2431 (6)	0.0290 (16)	0.325 (11)
H33C	0.2421	0.3476	0.2833	0.035*	0.325 (11)
H33D	0.2368	0.1777	0.2838	0.035*	0.325 (11)
C34X	0.2795 (4)	0.1142 (14)	0.1363 (9)	0.0356 (19)	0.325 (11)
H34C	0.3065	0.1039	0.1001	0.043*	0.325 (11)
H34D	0.2769	0.0302	0.1778	0.043*	0.325 (11)
C35X	0.2027 (4)	0.1419 (15)	0.1231 (11)	0.034 (2)	0.325 (11)
H35C	0.1974	0.0596	0.1648	0.040*	0.325 (11)
H35D	0.1784	0.1471	0.0783	0.040*	0.325 (11)
C36X	0.2114 (4)	0.3940 (14)	0.1163 (9)	0.0343 (19)	0.325 (11)
H36C	0.2134	0.4831	0.1532	0.041*	0.325 (11)
H36D	0.1867	0.4038	0.0730	0.041*	0.325 (11)
C37X	0.2865 (5)	0.3718 (16)	0.1291 (11)	0.036 (2)	0.325 (11)
H37C	0.2870	0.4617	0.1654	0.043*	0.325 (11)
H37D	0.3142	0.3640	0.0951	0.043*	0.325 (11)
C38X	0.2492 (8)	0.241 (2)	0.0104 (13)	0.037 (2)	0.325 (11)
H38C	0.2254	0.2451	−0.0356	0.045*	0.325 (11)
H38D	0.2765	0.2278	−0.0243	0.045*	0.325 (11)
C39	0.24947 (9)	0.7532 (3)	0.49880 (11)	0.0334 (4)
H39A	0.2455	0.6696	0.5402	0.040*
H39B	0.2537	0.8385	0.5385	0.040*
C40	0.28060 (8)	0.6051 (2)	0.38089 (18)	0.0343 (5)
H40A	0.3062	0.5895	0.3411	0.041*
H40B	0.2769	0.5195	0.4206	0.041*
C41	0.20532 (8)	0.6449 (3)	0.38142 (19)	0.0363 (5)
H41A	0.2010	0.5598	0.4213	0.044*
H41B	0.1793	0.6566	0.3422	0.044*
C42	0.21762 (8)	0.8975 (2)	0.37986 (18)	0.0343 (5)
H42A	0.1918	0.9122	0.3405	0.041*
H42B	0.2215	0.9839	0.4187	0.041*
C43	0.29271 (8)	0.8572 (3)	0.37947 (19)	0.0370 (6)
H43A	0.2973	0.9432	0.4183	0.044*
H43B	0.3185	0.8445	0.3398	0.044*
C44	0.24879 (10)	0.7495 (3)	0.26355 (11)	0.0376 (4)
H44A	0.2232	0.7625	0.2229	0.045*
H44B	0.2742	0.7351	0.2230	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.049 (2)	0.059 (2)	0.042 (2)	0.0198 (18)	0.0177 (16)	0.0162 (18)
O2	0.075 (2)	0.066 (3)	0.0398 (18)	0.029 (2)	0.0127 (17)	0.0141 (19)
C7	0.0362 (19)	0.039 (2)	0.025 (2)	0.0024 (18)	−0.0030 (17)	−0.001 (2)
C1	0.033 (2)	0.037 (3)	0.029 (2)	−0.005 (2)	−0.0056 (18)	−0.0007 (18)
C2	0.034 (3)	0.032 (2)	0.038 (3)	−0.006 (2)	0.001 (2)	−0.009 (2)
C3	0.044 (3)	0.044 (3)	0.040 (3)	−0.005 (3)	0.015 (3)	−0.012 (2)
C4	0.050 (3)	0.048 (3)	0.036 (2)	−0.010 (3)	0.011 (2)	−0.006 (2)
C5	0.044 (3)	0.048 (3)	0.037 (3)	−0.007 (2)	0.005 (2)	0.004 (2)
C6	0.036 (2)	0.046 (2)	0.030 (2)	−0.005 (2)	0.0034 (18)	0.0019 (19)
C8	0.049 (4)	0.041 (3)	0.053 (4)	0.002 (3)	0.005 (3)	−0.004 (3)
O1X	0.078 (4)	0.054 (4)	0.039 (3)	0.027 (3)	0.015 (3)	0.007 (3)
O2X	0.051 (3)	0.064 (4)	0.065 (4)	0.027 (3)	0.012 (3)	0.012 (3)
C7X	0.036 (3)	0.042 (3)	0.037 (3)	0.002 (3)	−0.002 (2)	0.003 (3)
C1X	0.029 (3)	0.036 (3)	0.029 (3)	0.002 (3)	0.002 (3)	−0.006 (3)
C2X	0.035 (4)	0.036 (3)	0.033 (3)	−0.005 (3)	−0.002 (3)	−0.003 (3)
C3X	0.041 (3)	0.028 (3)	0.039 (4)	−0.002 (3)	0.000 (3)	−0.001 (3)
C4X	0.046 (4)	0.035 (4)	0.036 (3)	0.006 (3)	0.004 (3)	−0.004 (3)
C5X	0.044 (4)	0.039 (3)	0.033 (3)	0.005 (3)	0.004 (3)	0.001 (3)
C6X	0.036 (4)	0.035 (3)	0.033 (3)	0.002 (3)	0.001 (3)	0.002 (3)
C8X	0.045 (6)	0.038 (5)	0.048 (5)	−0.003 (4)	0.001 (4)	0.002 (4)
O3	0.0529 (17)	0.060 (2)	0.0394 (17)	0.0222 (15)	−0.0065 (14)	−0.0092 (16)
O4	0.0534 (17)	0.0462 (17)	0.065 (2)	0.0264 (13)	−0.0183 (15)	−0.0185 (15)
C15	0.0299 (16)	0.0275 (17)	0.0411 (17)	−0.0005 (14)	0.0016 (14)	0.0021 (14)
C9	0.0274 (15)	0.023 (2)	0.0314 (18)	0.0019 (16)	0.0035 (14)	0.0025 (15)
C10	0.024 (2)	0.028 (2)	0.036 (2)	−0.0008 (15)	0.0024 (15)	0.0031 (18)
C11	0.0347 (19)	0.028 (2)	0.040 (2)	0.0021 (15)	0.0023 (19)	0.0061 (16)
C12	0.045 (2)	0.033 (2)	0.0387 (18)	0.0012 (16)	−0.0047 (17)	0.0069 (16)
C13	0.045 (2)	0.038 (2)	0.0344 (18)	0.0017 (19)	−0.0027 (16)	−0.0032 (16)
C14	0.037 (2)	0.0280 (16)	0.038 (2)	0.0015 (15)	0.0002 (16)	−0.0035 (16)
C16	0.034 (3)	0.0263 (19)	0.055 (3)	0.0054 (16)	−0.0007 (19)	−0.0038 (19)
O3X	0.044 (4)	0.045 (5)	0.060 (5)	0.013 (4)	−0.016 (4)	−0.015 (4)
O4X	0.072 (5)	0.075 (6)	0.035 (4)	0.034 (5)	−0.014 (4)	−0.014 (4)
C15X	0.037 (4)	0.034 (4)	0.031 (4)	0.008 (3)	0.001 (3)	0.002 (4)
C9X	0.033 (3)	0.032 (4)	0.033 (3)	−0.007 (3)	0.002 (3)	−0.003 (3)
C10X	0.031 (4)	0.027 (4)	0.039 (4)	0.000 (3)	0.001 (3)	0.004 (3)
C11X	0.036 (4)	0.034 (4)	0.041 (4)	−0.004 (4)	−0.005 (4)	0.006 (3)
C12X	0.044 (4)	0.039 (4)	0.034 (3)	0.002 (4)	−0.007 (3)	0.000 (3)
C13X	0.045 (4)	0.036 (4)	0.040 (4)	0.000 (4)	−0.008 (4)	−0.001 (4)
C14X	0.041 (4)	0.034 (4)	0.037 (4)	−0.004 (3)	−0.002 (3)	0.000 (3)
C16X	0.040 (7)	0.038 (6)	0.044 (6)	0.003 (5)	−0.010 (5)	0.007 (5)
O5	0.0488 (13)	0.0734 (15)	0.0558 (13)	0.0082 (11)	0.0138 (11)	0.0151 (11)
O6	0.0337 (10)	0.0845 (16)	0.0862 (17)	0.0117 (10)	0.0044 (11)	0.0247 (14)
O7	0.0425 (11)	0.0771 (15)	0.0525 (12)	0.0112 (10)	−0.0141 (10)	−0.0145 (11)
O8	0.0380 (11)	0.0984 (18)	0.0793 (16)	0.0120 (11)	0.0014 (11)	−0.0268 (15)
N5	0.0324 (10)	0.0289 (10)	0.0350 (11)	0.0000 (8)	0.0064 (9)	−0.0004 (9)
N6	0.0331 (10)	0.0296 (10)	0.0319 (10)	0.0005 (8)	−0.0074 (9)	0.0012 (8)
N7	0.0446 (11)	0.0246 (10)	0.0290 (10)	−0.0005 (8)	−0.0035 (9)	−0.0054 (8)
N8	0.0428 (11)	0.0259 (10)	0.0316 (11)	0.0021 (8)	0.0005 (9)	0.0073 (8)
C17	0.0312 (11)	0.0307 (11)	0.0390 (13)	−0.0024 (10)	−0.0001 (10)	−0.0098 (10)
C18	0.0420 (14)	0.0381 (14)	0.0417 (14)	−0.0040 (11)	−0.0007 (12)	−0.0091 (11)
C19	0.0350 (13)	0.0532 (16)	0.0509 (16)	−0.0091 (12)	0.0057 (13)	−0.0177 (14)
C20	0.0350 (13)	0.0589 (17)	0.0519 (16)	−0.0014 (14)	0.0008 (13)	−0.0169 (14)
C21	0.0373 (14)	0.0526 (17)	0.0538 (16)	0.0120 (12)	−0.0069 (13)	−0.0116 (14)
C22	0.0435 (15)	0.0370 (14)	0.0490 (16)	0.0033 (11)	−0.0018 (13)	−0.0056 (12)
C23	0.0373 (13)	0.0352 (13)	0.0458 (15)	−0.0042 (12)	0.0040 (12)	−0.0075 (12)
C24	0.0547 (17)	0.0542 (17)	0.0525 (17)	−0.0008 (14)	−0.0051 (15)	0.0054 (14)
C25	0.0323 (11)	0.0284 (11)	0.0369 (12)	−0.0015 (10)	−0.0016 (10)	0.0064 (10)
C26	0.0403 (14)	0.0316 (13)	0.0390 (13)	−0.0034 (10)	0.0024 (11)	0.0063 (11)
C27	0.0380 (13)	0.0430 (14)	0.0447 (15)	−0.0066 (11)	−0.0074 (12)	0.0109 (12)
C28	0.0366 (13)	0.0486 (15)	0.0481 (15)	−0.0057 (13)	−0.0058 (12)	0.0137 (13)
C29	0.0428 (14)	0.0446 (15)	0.0505 (16)	0.0080 (12)	0.0078 (13)	0.0077 (13)
C30	0.0406 (14)	0.0353 (13)	0.0422 (14)	0.0009 (11)	−0.0017 (12)	0.0033 (11)
C31	0.0345 (12)	0.0348 (13)	0.0431 (14)	−0.0018 (12)	−0.0035 (11)	0.0050 (11)
C32	0.0510 (16)	0.0495 (16)	0.0510 (16)	−0.0005 (13)	0.0036 (14)	−0.0049 (14)
N1	0.0343 (19)	0.0280 (17)	0.0280 (17)	0.0014 (15)	0.0006 (16)	−0.0020 (13)
N2	0.037 (2)	0.0303 (17)	0.0249 (16)	0.0053 (15)	0.0030 (15)	0.0000 (13)
N3	0.051 (2)	0.0240 (17)	0.026 (2)	−0.0013 (17)	0.0031 (16)	−0.0028 (16)
N4	0.060 (3)	0.0195 (16)	0.024 (2)	−0.0007 (18)	−0.0018 (19)	0.0009 (16)
C33	0.035 (2)	0.0304 (18)	0.0205 (15)	0.0034 (17)	−0.0007 (18)	0.0000 (13)
C34	0.050 (3)	0.0246 (17)	0.030 (2)	0.0044 (17)	0.0042 (18)	0.0006 (17)
C35	0.041 (3)	0.026 (2)	0.036 (2)	−0.0027 (19)	−0.003 (2)	−0.0055 (17)
C36	0.047 (3)	0.0273 (19)	0.033 (2)	0.0087 (18)	−0.0108 (19)	−0.0057 (18)
C37	0.043 (3)	0.0258 (19)	0.037 (2)	−0.0049 (18)	0.0036 (19)	0.0025 (17)
C38	0.070 (2)	0.026 (2)	0.0208 (19)	0.004 (2)	−0.002 (2)	0.0049 (19)
N1X	0.044 (3)	0.026 (3)	0.032 (3)	0.004 (3)	−0.005 (3)	0.000 (2)
N2X	0.038 (3)	0.030 (3)	0.023 (3)	0.001 (3)	0.001 (3)	0.003 (2)
N3X	0.055 (4)	0.023 (3)	0.024 (3)	0.001 (3)	0.000 (3)	0.002 (3)
N4X	0.051 (3)	0.027 (3)	0.027 (3)	0.001 (3)	−0.009 (3)	0.004 (3)
C33X	0.033 (3)	0.031 (3)	0.023 (3)	0.004 (3)	0.001 (3)	0.003 (2)
C34X	0.046 (4)	0.031 (3)	0.029 (4)	0.007 (3)	0.009 (3)	0.003 (3)
C35X	0.041 (4)	0.027 (3)	0.032 (3)	0.000 (3)	−0.003 (3)	−0.001 (3)
C36X	0.051 (4)	0.021 (3)	0.031 (4)	0.005 (3)	−0.010 (3)	−0.002 (3)
C37X	0.046 (4)	0.030 (3)	0.031 (3)	−0.004 (3)	0.005 (3)	0.007 (3)
C38X	0.065 (4)	0.025 (4)	0.022 (4)	0.002 (4)	−0.001 (3)	−0.007 (3)
C39	0.0488 (10)	0.0284 (8)	0.0231 (7)	−0.0009 (7)	0.0005 (13)	−0.0013 (11)
C40	0.0393 (13)	0.0270 (12)	0.0368 (13)	0.0089 (10)	0.0005 (11)	−0.0004 (10)
C41	0.0350 (13)	0.0298 (12)	0.0440 (14)	−0.0088 (10)	−0.0007 (11)	−0.0033 (11)
C42	0.0408 (13)	0.0230 (11)	0.0390 (13)	0.0076 (10)	−0.0004 (11)	0.0006 (10)
C43	0.0359 (13)	0.0316 (12)	0.0435 (14)	−0.0092 (10)	0.0032 (11)	0.0032 (11)
C44	0.0540 (11)	0.0373 (9)	0.0217 (7)	0.0045 (8)	−0.0002 (13)	0.0007 (12)

Geometric parameters (Å, º) top

O1—C7	1.312 (6)	C17—C18	1.395 (4)
O1—H1O1	0.83 (2)	C17—C22	1.415 (4)
O2—C7	1.208 (6)	C17—C23	1.487 (3)
C7—C1	1.486 (7)	C18—C19	1.402 (4)
C1—C6	1.393 (7)	C18—C24	1.494 (4)
C1—C2	1.415 (8)	C19—C20	1.372 (4)
C2—C3	1.392 (8)	C19—H19A	0.9500
C2—C8	1.511 (8)	C20—C21	1.389 (5)
C3—C4	1.373 (8)	C20—H20A	0.9500
C3—H3A	0.9500	C21—C22	1.365 (4)
C4—C5	1.379 (7)	C21—H21A	0.9500
C4—H4A	0.9500	C22—H22A	0.9500
C5—C6	1.375 (7)	C24—H24A	0.9800
C5—H5A	0.9500	C24—H24B	0.9800
C6—H6A	0.9500	C24—H24C	0.9800
C8—H8A	0.9800	C25—C26	1.395 (4)
C8—H8B	0.9800	C25—C30	1.410 (4)
C8—H8C	0.9800	C25—C31	1.492 (3)
O1X—C7X	1.308 (8)	C26—C27	1.401 (4)
O1X—H2O1	0.8400	C26—C32	1.488 (4)
O2X—C7X	1.214 (8)	C27—C28	1.361 (4)
C7X—C1X	1.495 (10)	C27—H27A	0.9500
C1X—C6X	1.394 (10)	C28—C29	1.389 (4)
C1X—C2X	1.403 (11)	C28—H28A	0.9500
C2X—C3X	1.388 (12)	C29—C30	1.376 (4)
C2X—C8X	1.512 (11)	C29—H29A	0.9500
C3X—C4X	1.379 (10)	C30—H30A	0.9500
C3X—H3XA	0.9500	C32—H32A	0.9800
C4X—C5X	1.386 (9)	C32—H32B	0.9800
C4X—H4XA	0.9500	C32—H32C	0.9800
C5X—C6X	1.385 (10)	N1—C36	1.476 (6)
C5X—H5XA	0.9500	N1—C35	1.483 (6)
C6X—H6XA	0.9500	N1—C33	1.489 (5)
C8X—H8XA	0.9800	N2—C33	1.472 (5)
C8X—H8XB	0.9800	N2—C34	1.479 (6)
C8X—H8XC	0.9800	N2—C37	1.482 (6)
O3—C15	1.309 (5)	N3—C34	1.462 (7)
O3—H1O3	0.84 (2)	N3—C35	1.466 (7)
O4—C15	1.205 (4)	N3—C38	1.472 (7)
C15—C9	1.495 (5)	N4—C37	1.454 (7)
C9—C14	1.399 (5)	N4—C36	1.462 (7)
C9—C10	1.408 (5)	N4—C38	1.476 (7)
C10—C11	1.408 (6)	C33—H33A	0.9900
C10—C16	1.499 (5)	C33—H33B	0.9900
C11—C12	1.375 (6)	C34—H34A	0.9900
C11—H11A	0.9500	C34—H34B	0.9900
C12—C13	1.376 (5)	C35—H35A	0.9900
C12—H12A	0.9500	C35—H35B	0.9900
C13—C14	1.384 (6)	C36—H36A	0.9900
C13—H13A	0.9500	C36—H36B	0.9900
C14—H14A	0.9500	C37—H37A	0.9900
C16—H16A	0.9800	C37—H37B	0.9900
C16—H16B	0.9800	C38—H38A	0.9900
C16—H16C	0.9800	C38—H38B	0.9900
O3X—C15X	1.316 (11)	N1X—C36X	1.460 (11)
O3X—H2O3	0.8400	N1X—C35X	1.477 (12)
O4X—C15X	1.211 (12)	N1X—C33X	1.483 (10)
C15X—C9X	1.519 (13)	N2X—C33X	1.458 (9)
C9X—C14X	1.391 (13)	N2X—C37X	1.499 (12)
C9X—C10X	1.397 (13)	N2X—C34X	1.501 (11)
C10X—C11X	1.407 (14)	N3X—C35X	1.456 (13)
C10X—C16X	1.511 (14)	N3X—C38X	1.467 (13)
C11X—C12X	1.363 (14)	N3X—C34X	1.470 (13)
C11X—H11B	0.9500	N4X—C37X	1.458 (13)
C12X—C13X	1.378 (13)	N4X—C36X	1.461 (13)
C12X—H12B	0.9500	N4X—C38X	1.470 (13)
C13X—C14X	1.374 (13)	C33X—H33C	0.9900
C13X—H13B	0.9500	C33X—H33D	0.9900
C14X—H14B	0.9500	C34X—H34C	0.9900
C16X—H16D	0.9800	C34X—H34D	0.9900
C16X—H16E	0.9800	C35X—H35C	0.9900
C16X—H16F	0.9800	C35X—H35D	0.9900
O5—C23	1.308 (4)	C36X—H36C	0.9900
O5—H1O5	0.865 (19)	C36X—H36D	0.9900
O6—C23	1.214 (3)	C37X—H37C	0.9900
O7—C31	1.301 (3)	C37X—H37D	0.9900
O7—H1O7	0.882 (18)	C38X—H38C	0.9900
O8—C31	1.212 (3)	C38X—H38D	0.9900
N5—C39	1.472 (3)	C39—H39A	0.9900
N5—C41	1.479 (3)	C39—H39B	0.9900
N5—C42	1.480 (3)	C40—H40A	0.9900
N6—C39	1.472 (3)	C40—H40B	0.9900
N6—C40	1.479 (3)	C41—H41A	0.9900
N6—C43	1.479 (3)	C41—H41B	0.9900
N7—C41	1.454 (3)	C42—H42A	0.9900
N7—C40	1.460 (3)	C42—H42B	0.9900
N7—C44	1.469 (3)	C43—H43A	0.9900
N8—C43	1.454 (3)	C43—H43B	0.9900
N8—C42	1.455 (3)	C44—H44A	0.9900
N8—C44	1.477 (3)	C44—H44B	0.9900

C7—O1—H1O1	107 (4)	C25—C26—C27	117.9 (2)
O2—C7—O1	122.4 (5)	C25—C26—C32	124.1 (2)
O2—C7—C1	124.5 (5)	C27—C26—C32	117.9 (3)
O1—C7—C1	113.1 (5)	C28—C27—C26	122.0 (3)
C6—C1—C2	118.7 (6)	C28—C27—H27A	119.0
C6—C1—C7	119.0 (5)	C26—C27—H27A	119.0
C2—C1—C7	122.3 (6)	C27—C28—C29	120.4 (2)
C3—C2—C1	118.2 (7)	C27—C28—H28A	119.8
C3—C2—C8	119.2 (6)	C29—C28—H28A	119.8
C1—C2—C8	122.6 (6)	C30—C29—C28	119.1 (3)
C4—C3—C2	121.8 (7)	C30—C29—H29A	120.5
C4—C3—H3A	119.1	C28—C29—H29A	120.5
C2—C3—H3A	119.1	C29—C30—C25	121.0 (3)
C3—C4—C5	120.1 (6)	C29—C30—H30A	119.5
C3—C4—H4A	119.9	C25—C30—H30A	119.5
C5—C4—H4A	119.9	O8—C31—O7	121.9 (3)
C6—C5—C4	119.4 (6)	O8—C31—C25	123.8 (3)
C6—C5—H5A	120.3	O7—C31—C25	114.3 (2)
C4—C5—H5A	120.3	C26—C32—H32A	109.5
C5—C6—C1	121.8 (6)	C26—C32—H32B	109.5
C5—C6—H6A	119.1	H32A—C32—H32B	109.5
C1—C6—H6A	119.1	C26—C32—H32C	109.5
C2—C8—H8A	109.5	H32A—C32—H32C	109.5
C2—C8—H8B	109.5	H32B—C32—H32C	109.5
H8A—C8—H8B	109.5	C36—N1—C35	109.6 (4)
C2—C8—H8C	109.5	C36—N1—C33	107.4 (3)
H8A—C8—H8C	109.5	C35—N1—C33	108.1 (3)
H8B—C8—H8C	109.5	C33—N2—C34	108.5 (3)
C7X—O1X—H2O1	109.5	C33—N2—C37	107.8 (3)
O2X—C7X—O1X	123.0 (7)	C34—N2—C37	107.5 (4)
O2X—C7X—C1X	120.4 (8)	C34—N3—C35	108.0 (5)
O1X—C7X—C1X	116.4 (7)	C34—N3—C38	109.1 (6)
C6X—C1X—C2X	120.7 (9)	C35—N3—C38	109.1 (7)
C6X—C1X—C7X	115.6 (8)	C37—N4—C36	109.3 (5)
C2X—C1X—C7X	123.6 (9)	C37—N4—C38	107.8 (7)
C3X—C2X—C1X	116.7 (10)	C36—N4—C38	107.1 (6)
C3X—C2X—C8X	116.2 (9)	N2—C33—N1	111.4 (3)
C1X—C2X—C8X	127.1 (10)	N2—C33—H33A	109.3
C4X—C3X—C2X	122.7 (11)	N1—C33—H33A	109.3
C4X—C3X—H3XA	118.7	N2—C33—H33B	109.3
C2X—C3X—H3XA	118.7	N1—C33—H33B	109.3
C3X—C4X—C5X	120.3 (10)	H33A—C33—H33B	108.0
C3X—C4X—H4XA	119.9	N3—C34—N2	111.8 (5)
C5X—C4X—H4XA	119.9	N3—C34—H34A	109.3
C6X—C5X—C4X	118.3 (8)	N2—C34—H34A	109.3
C6X—C5X—H5XA	120.8	N3—C34—H34B	109.3
C4X—C5X—H5XA	120.8	N2—C34—H34B	109.3
C5X—C6X—C1X	121.2 (8)	H34A—C34—H34B	107.9
C5X—C6X—H6XA	119.4	N3—C35—N1	110.6 (5)
C1X—C6X—H6XA	119.4	N3—C35—H35A	109.5
C2X—C8X—H8XA	109.5	N1—C35—H35A	109.5
C2X—C8X—H8XB	109.5	N3—C35—H35B	109.5
H8XA—C8X—H8XB	109.5	N1—C35—H35B	109.5
C2X—C8X—H8XC	109.5	H35A—C35—H35B	108.1
H8XA—C8X—H8XC	109.5	N4—C36—N1	112.1 (5)
H8XB—C8X—H8XC	109.5	N4—C36—H36A	109.2
C15—O3—H1O3	108 (4)	N1—C36—H36A	109.2
O4—C15—O3	122.5 (4)	N4—C36—H36B	109.2
O4—C15—C9	121.0 (4)	N1—C36—H36B	109.2
O3—C15—C9	116.5 (3)	H36A—C36—H36B	107.9
C14—C9—C10	119.8 (4)	N4—C37—N2	112.7 (5)
C14—C9—C15	115.7 (3)	N4—C37—H37A	109.0
C10—C9—C15	124.5 (4)	N2—C37—H37A	109.0
C9—C10—C11	117.6 (4)	N4—C37—H37B	109.0
C9—C10—C16	125.7 (4)	N2—C37—H37B	109.0
C11—C10—C16	116.7 (4)	H37A—C37—H37B	107.8
C12—C11—C10	121.6 (5)	N3—C38—N4	112.0 (6)
C12—C11—H11A	119.2	N3—C38—H38A	109.2
C10—C11—H11A	119.2	N4—C38—H38A	109.2
C11—C12—C13	120.7 (4)	N3—C38—H38B	109.2
C11—C12—H12A	119.7	N4—C38—H38B	109.2
C13—C12—H12A	119.7	H38A—C38—H38B	107.9
C12—C13—C14	119.3 (4)	C36X—N1X—C35X	108.1 (9)
C12—C13—H13A	120.3	C36X—N1X—C33X	108.1 (7)
C14—C13—H13A	120.3	C35X—N1X—C33X	106.6 (7)
C13—C14—C9	121.1 (4)	C33X—N2X—C37X	108.2 (8)
C13—C14—H14A	119.4	C33X—N2X—C34X	107.5 (7)
C9—C14—H14A	119.4	C37X—N2X—C34X	107.8 (9)
C10—C16—H16A	109.5	C35X—N3X—C38X	107.6 (14)
C10—C16—H16B	109.5	C35X—N3X—C34X	110.4 (11)
H16A—C16—H16B	109.5	C38X—N3X—C34X	106.6 (13)
C10—C16—H16C	109.5	C37X—N4X—C36X	106.9 (12)
H16A—C16—H16C	109.5	C37X—N4X—C38X	109.9 (15)
H16B—C16—H16C	109.5	C36X—N4X—C38X	109.9 (14)
C15X—O3X—H2O3	109.5	N2X—C33X—N1X	113.0 (7)
O4X—C15X—O3X	123.5 (10)	N2X—C33X—H33C	109.0
O4X—C15X—C9X	122.5 (9)	N1X—C33X—H33C	109.0
O3X—C15X—C9X	114.0 (10)	N2X—C33X—H33D	109.0
C14X—C9X—C10X	120.6 (11)	N1X—C33X—H33D	109.0
C14X—C9X—C15X	116.5 (11)	H33C—C33X—H33D	107.8
C10X—C9X—C15X	122.9 (11)	N3X—C34X—N2X	111.5 (10)
C9X—C10X—C11X	115.3 (13)	N3X—C34X—H34C	109.3
C9X—C10X—C16X	123.3 (12)	N2X—C34X—H34C	109.3
C11X—C10X—C16X	121.4 (12)	N3X—C34X—H34D	109.3
C12X—C11X—C10X	122.9 (14)	N2X—C34X—H34D	109.3
C12X—C11X—H11B	118.5	H34C—C34X—H34D	108.0
C10X—C11X—H11B	118.5	N3X—C35X—N1X	113.0 (10)
C11X—C12X—C13X	121.3 (12)	N3X—C35X—H35C	109.0
C11X—C12X—H12B	119.3	N1X—C35X—H35C	109.0
C13X—C12X—H12B	119.3	N3X—C35X—H35D	109.0
C14X—C13X—C12X	117.0 (12)	N1X—C35X—H35D	109.0
C14X—C13X—H13B	121.5	H35C—C35X—H35D	107.8
C12X—C13X—H13B	121.5	N1X—C36X—N4X	112.2 (10)
C13X—C14X—C9X	122.6 (12)	N1X—C36X—H36C	109.2
C13X—C14X—H14B	118.7	N4X—C36X—H36C	109.2
C9X—C14X—H14B	118.7	N1X—C36X—H36D	109.2
C10X—C16X—H16D	109.5	N4X—C36X—H36D	109.2
C10X—C16X—H16E	109.5	H36C—C36X—H36D	107.9
H16D—C16X—H16E	109.5	N4X—C37X—N2X	110.7 (11)
C10X—C16X—H16F	109.5	N4X—C37X—H37C	109.5
H16D—C16X—H16F	109.5	N2X—C37X—H37C	109.5
H16E—C16X—H16F	109.5	N4X—C37X—H37D	109.5
C23—O5—H1O5	106 (4)	N2X—C37X—H37D	109.5
C31—O7—H1O7	113 (3)	H37C—C37X—H37D	108.1
C39—N5—C41	108.4 (2)	N3X—C38X—N4X	111.9 (13)
C39—N5—C42	108.09 (19)	N3X—C38X—H38C	109.2
C41—N5—C42	108.11 (18)	N4X—C38X—H38C	109.2
C39—N6—C40	108.31 (19)	N3X—C38X—H38D	109.2
C39—N6—C43	107.80 (19)	N4X—C38X—H38D	109.2
C40—N6—C43	107.81 (19)	H38C—C38X—H38D	107.9
C41—N7—C40	108.43 (19)	N5—C39—N6	111.33 (12)
C41—N7—C44	108.7 (2)	N5—C39—H39A	109.4
C40—N7—C44	108.3 (2)	N6—C39—H39A	109.4
C43—N8—C42	108.3 (2)	N5—C39—H39B	109.4
C43—N8—C44	108.11 (19)	N6—C39—H39B	109.4
C42—N8—C44	108.3 (2)	H39A—C39—H39B	108.0
C18—C17—C22	119.1 (2)	N7—C40—N6	112.04 (18)
C18—C17—C23	123.0 (2)	N7—C40—H40A	109.2
C22—C17—C23	117.9 (2)	N6—C40—H40A	109.2
C17—C18—C19	117.7 (3)	N7—C40—H40B	109.2
C17—C18—C24	124.1 (2)	N6—C40—H40B	109.2
C19—C18—C24	118.2 (3)	H40A—C40—H40B	107.9
C20—C19—C18	122.1 (3)	N7—C41—N5	111.81 (18)
C20—C19—H19A	118.9	N7—C41—H41A	109.3
C18—C19—H19A	118.9	N5—C41—H41A	109.3
C19—C20—C21	120.4 (3)	N7—C41—H41B	109.3
C19—C20—H20A	119.8	N5—C41—H41B	109.3
C21—C20—H20A	119.8	H41A—C41—H41B	107.9
C22—C21—C20	118.6 (3)	N8—C42—N5	112.04 (17)
C22—C21—H21A	120.7	N8—C42—H42A	109.2
C20—C21—H21A	120.7	N5—C42—H42A	109.2
C21—C22—C17	122.1 (3)	N8—C42—H42B	109.2
C21—C22—H22A	118.9	N5—C42—H42B	109.2
C17—C22—H22A	118.9	H42A—C42—H42B	107.9
O6—C23—O5	122.1 (3)	N8—C43—N6	112.50 (19)
O6—C23—C17	124.0 (3)	N8—C43—H43A	109.1
O5—C23—C17	113.9 (2)	N6—C43—H43A	109.1
C18—C24—H24A	109.5	N8—C43—H43B	109.1
C18—C24—H24B	109.5	N6—C43—H43B	109.1
H24A—C24—H24B	109.5	H43A—C43—H43B	107.8
C18—C24—H24C	109.5	N7—C44—N8	111.80 (12)
H24A—C24—H24C	109.5	N7—C44—H44A	109.3
H24B—C24—H24C	109.5	N8—C44—H44A	109.3
C26—C25—C30	119.6 (2)	N7—C44—H44B	109.3
C26—C25—C31	123.3 (2)	N8—C44—H44B	109.3
C30—C25—C31	117.1 (2)	H44A—C44—H44B	107.9

O2—C7—C1—C6	170.7 (7)	C26—C27—C28—C29	0.0 (4)
O1—C7—C1—C6	−11.7 (10)	C27—C28—C29—C30	0.4 (4)
O2—C7—C1—C2	−10.1 (15)	C28—C29—C30—C25	−0.4 (4)
O1—C7—C1—C2	167.5 (11)	C26—C25—C30—C29	0.0 (4)
C6—C1—C2—C3	1 (2)	C31—C25—C30—C29	177.9 (2)
C7—C1—C2—C3	−178.2 (11)	C26—C25—C31—O8	−9.6 (4)
C6—C1—C2—C8	179.9 (11)	C30—C25—C31—O8	172.6 (3)
C7—C1—C2—C8	1 (2)	C26—C25—C31—O7	169.3 (2)
C1—C2—C3—C4	−1 (2)	C30—C25—C31—O7	−8.5 (3)
C8—C2—C3—C4	−179.7 (11)	C34—N2—C33—N1	−57.1 (4)
C2—C3—C4—C5	−0.4 (16)	C37—N2—C33—N1	59.0 (5)
C3—C4—C5—C6	1.3 (10)	C36—N1—C33—N2	−59.9 (4)
C4—C5—C6—C1	−1.1 (10)	C35—N1—C33—N2	58.3 (5)
C2—C1—C6—C5	−0.1 (14)	C35—N3—C34—N2	−60.6 (7)
C7—C1—C6—C5	179.2 (7)	C38—N3—C34—N2	57.9 (7)
O2X—C7X—C1X—C6X	−20.9 (16)	C33—N2—C34—N3	58.6 (5)
O1X—C7X—C1X—C6X	162.7 (10)	C37—N2—C34—N3	−57.8 (5)
O2X—C7X—C1X—C2X	160.7 (18)	C34—N3—C35—N1	61.2 (7)
O1X—C7X—C1X—C2X	−16 (2)	C38—N3—C35—N1	−57.3 (7)
C6X—C1X—C2X—C3X	3 (3)	C36—N1—C35—N3	56.7 (6)
C7X—C1X—C2X—C3X	−178.2 (17)	C33—N1—C35—N3	−60.1 (6)
C6X—C1X—C2X—C8X	−176.5 (18)	C37—N4—C36—N1	−57.9 (7)
C7X—C1X—C2X—C8X	2 (4)	C38—N4—C36—N1	58.7 (7)
C1X—C2X—C3X—C4X	−2 (3)	C35—N1—C36—N4	−58.4 (5)
C8X—C2X—C3X—C4X	177.8 (17)	C33—N1—C36—N4	58.9 (5)
C2X—C3X—C4X—C5X	0 (3)	C36—N4—C37—N2	57.0 (7)
C3X—C4X—C5X—C6X	0.9 (16)	C38—N4—C37—N2	−59.1 (7)
C4X—C5X—C6X—C1X	0.5 (15)	C33—N2—C37—N4	−57.6 (6)
C2X—C1X—C6X—C5X	−3 (2)	C34—N2—C37—N4	59.2 (6)
C7X—C1X—C6X—C5X	178.8 (10)	C34—N3—C38—N4	−57.8 (9)
O4—C15—C9—C14	−18.4 (7)	C35—N3—C38—N4	60.0 (10)
O3—C15—C9—C14	161.2 (4)	C37—N4—C38—N3	57.9 (9)
O4—C15—C9—C10	158.4 (8)	C36—N4—C38—N3	−59.6 (9)
O3—C15—C9—C10	−22.0 (10)	C37X—N2X—C33X—N1X	55.7 (10)
C14—C9—C10—C11	−0.3 (14)	C34X—N2X—C33X—N1X	−60.4 (10)
C15—C9—C10—C11	−177.0 (7)	C36X—N1X—C33X—N2X	−55.6 (10)
C14—C9—C10—C16	−178.3 (8)	C35X—N1X—C33X—N2X	60.4 (10)
C15—C9—C10—C16	5.0 (15)	C35X—N3X—C34X—N2X	−55.4 (15)
C9—C10—C11—C12	0.5 (15)	C38X—N3X—C34X—N2X	61.2 (14)
C16—C10—C11—C12	178.7 (7)	C33X—N2X—C34X—N3X	56.6 (11)
C10—C11—C12—C13	−0.3 (11)	C37X—N2X—C34X—N3X	−59.9 (12)
C11—C12—C13—C14	−0.1 (7)	C38X—N3X—C35X—N1X	−59.2 (15)
C12—C13—C14—C9	0.3 (7)	C34X—N3X—C35X—N1X	56.8 (15)
C10—C9—C14—C13	−0.1 (10)	C36X—N1X—C35X—N3X	58.6 (13)
C15—C9—C14—C13	176.9 (4)	C33X—N1X—C35X—N3X	−57.3 (13)
O4X—C15X—C9X—C14X	166.7 (15)	C35X—N1X—C36X—N4X	−56.2 (12)
O3X—C15X—C9X—C14X	−13 (2)	C33X—N1X—C36X—N4X	58.8 (12)
O4X—C15X—C9X—C10X	−14 (3)	C37X—N4X—C36X—N1X	−62.7 (15)
O3X—C15X—C9X—C10X	166 (3)	C38X—N4X—C36X—N1X	56.5 (15)
C14X—C9X—C10X—C11X	5 (5)	C36X—N4X—C37X—N2X	61.8 (15)
C15X—C9X—C10X—C11X	−174 (2)	C38X—N4X—C37X—N2X	−57.4 (16)
C14X—C9X—C10X—C16X	−179 (3)	C33X—N2X—C37X—N4X	−59.1 (13)
C15X—C9X—C10X—C16X	2 (5)	C34X—N2X—C37X—N4X	56.8 (13)
C9X—C10X—C11X—C12X	−5 (5)	C35X—N3X—C38X—N4X	57.7 (19)
C16X—C10X—C11X—C12X	178 (2)	C34X—N3X—C38X—N4X	−60.7 (19)
C10X—C11X—C12X—C13X	3 (4)	C37X—N4X—C38X—N3X	60.2 (19)
C11X—C12X—C13X—C14X	0 (2)	C36X—N4X—C38X—N3X	−57.2 (19)
C12X—C13X—C14X—C9X	0 (2)	C41—N5—C39—N6	58.2 (3)
C10X—C9X—C14X—C13X	−3 (3)	C42—N5—C39—N6	−58.8 (3)
C15X—C9X—C14X—C13X	176.5 (14)	C40—N6—C39—N5	−57.9 (3)
C22—C17—C18—C19	−0.2 (4)	C43—N6—C39—N5	58.5 (3)
C23—C17—C18—C19	−176.9 (2)	C41—N7—C40—N6	−58.9 (2)
C22—C17—C18—C24	179.5 (2)	C44—N7—C40—N6	58.9 (3)
C23—C17—C18—C24	2.8 (4)	C39—N6—C40—N7	58.4 (2)
C17—C18—C19—C20	0.1 (4)	C43—N6—C40—N7	−58.0 (3)
C24—C18—C19—C20	−179.7 (3)	C40—N7—C41—N5	59.0 (3)
C18—C19—C20—C21	−0.1 (4)	C44—N7—C41—N5	−58.5 (2)
C19—C20—C21—C22	0.3 (4)	C39—N5—C41—N7	−58.9 (2)
C20—C21—C22—C17	−0.5 (4)	C42—N5—C41—N7	58.1 (3)
C18—C17—C22—C21	0.5 (4)	C43—N8—C42—N5	−58.5 (2)
C23—C17—C22—C21	177.4 (2)	C44—N8—C42—N5	58.4 (2)
C18—C17—C23—O6	−5.6 (4)	C39—N5—C42—N8	58.9 (2)
C22—C17—C23—O6	177.7 (3)	C41—N5—C42—N8	−58.3 (2)
C18—C17—C23—O5	173.7 (2)	C42—N8—C43—N6	58.7 (3)
C22—C17—C23—O5	−3.1 (3)	C44—N8—C43—N6	−58.4 (3)
C30—C25—C26—C27	0.4 (4)	C39—N6—C43—N8	−58.7 (3)
C31—C25—C26—C27	−177.4 (2)	C40—N6—C43—N8	58.0 (3)
C30—C25—C26—C32	179.0 (2)	C41—N7—C44—N8	58.6 (3)
C31—C25—C26—C32	1.3 (4)	C40—N7—C44—N8	−59.0 (3)
C25—C26—C27—C28	−0.4 (4)	C43—N8—C44—N7	58.7 (3)
C32—C26—C27—C28	−179.2 (2)	C42—N8—C44—N7	−58.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.83 (3)	1.81 (4)	2.623 (6)	167 (4)
O3—H1O3···N2	0.84 (4)	1.84 (5)	2.677 (6)	177 (6)
O5—H1O5···N5	0.86 (4)	1.83 (4)	2.676 (3)	165 (5)
O7—H1O7···N6	0.88 (3)	1.79 (3)	2.666 (3)	172 (4)
C6—H6A···O1	0.95	2.34	2.686 (7)	101
C16—H16A···O3	0.98	2.42	2.817 (6)	104
C22—H22A···O5	0.95	2.32	2.680 (4)	102
C30—H30A···O7	0.95	2.33	2.677 (3)	101
C33—H33A···O4	0.99	2.58	3.142 (6)	116
C33—H33B···N8ⁱ	0.99	2.60	3.535 (5)	157
C36—H36B···N7	0.99	2.60	3.550 (6)	162
C38—H38B···O4ⁱⁱ	0.99	2.41	3.366 (12)	162
C40—H40B···N3ⁱⁱⁱ	0.99	2.59	3.510 (8)	155
C44—H44A···O6^iv	0.99	2.39	3.373 (4)	172
C44—H44B···O8^iv	0.99	2.39	3.371 (4)	172

Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) x, −y+3/2, z−1/2.

(164K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top

Crystal data top

C₆H₁₂N₄·2C₈H₈O₂	F(000) = 1760
M_r = 412.48	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 31.0071 (16) Å	Cell parameters from 9956 reflections
b = 9.3634 (5) Å	θ = 2.2–27.2°
c = 14.3544 (7) Å	µ = 0.09 mm⁻¹
β = 90.0656 (10)°	T = 164 K
V = 4167.5 (4) Å³	Block, colourless
Z = 8	0.43 × 0.17 × 0.15 mm

Data collection top

Bruker APEX DUO CCD area detector diffractometer	10052 independent reflections
Radiation source: fine-focus sealed tube	7429 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 28.0°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −40→40
T_min = 0.918, T_max = 0.963	k = −12→12
66182 measured reflections	l = −18→18

Refinement top

Refinement on F²	1216 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0609P)² + 1.6705P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.003
10052 reflections	Δρ_max = 0.43 e Å⁻³
837 parameters	Δρ_min = −0.23 e Å⁻³

Special details top

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.16467 (14)	0.2381 (6)	0.3349 (3)	0.0497 (12)	0.553 (7)
H1O1	0.1798 (16)	0.247 (6)	0.288 (3)	0.067 (18)*	0.553 (7)
O2	0.12823 (16)	0.4183 (7)	0.2737 (3)	0.0610 (14)	0.553 (7)
C7	0.13364 (17)	0.3336 (7)	0.3360 (4)	0.0331 (11)	0.553 (7)
C1	0.1074 (4)	0.3295 (9)	0.4231 (6)	0.0331 (13)	0.553 (7)
C2	0.0787 (5)	0.4399 (13)	0.4470 (9)	0.0346 (15)	0.553 (7)
C3	0.0569 (4)	0.4286 (12)	0.5318 (7)	0.0429 (17)	0.553 (7)
H3A	0.0376	0.5023	0.5497	0.052*	0.553 (7)
C4	0.0627 (3)	0.3140 (9)	0.5899 (6)	0.0460 (16)	0.553 (7)
H4A	0.0474	0.3098	0.6471	0.055*	0.553 (7)
C5	0.0904 (2)	0.2055 (8)	0.5665 (5)	0.0440 (14)	0.553 (7)
H5A	0.0941	0.1255	0.6065	0.053*	0.553 (7)
C6	0.1128 (2)	0.2149 (8)	0.4838 (5)	0.0372 (13)	0.553 (7)
H6A	0.1324	0.1410	0.4678	0.045*	0.553 (7)
C8	0.0706 (3)	0.5676 (10)	0.3848 (7)	0.048 (2)	0.553 (7)
H8A	0.0971	0.6242	0.3796	0.071*	0.553 (7)
H8B	0.0477	0.6266	0.4117	0.071*	0.553 (7)
H8C	0.0618	0.5347	0.3228	0.071*	0.553 (7)
O1X	0.1344 (2)	0.3327 (8)	0.2840 (5)	0.0587 (17)	0.447 (7)
H2O1	0.1533	0.3034	0.2467	0.088*	0.447 (7)
O2X	0.16546 (17)	0.1734 (7)	0.3771 (5)	0.0613 (18)	0.447 (7)
C7X	0.1376 (2)	0.2626 (8)	0.3624 (5)	0.0394 (14)	0.447 (7)
C1X	0.1063 (5)	0.3015 (12)	0.4369 (8)	0.0319 (16)	0.447 (7)
C2X	0.0812 (7)	0.4251 (17)	0.4374 (11)	0.0351 (18)	0.447 (7)
C3X	0.0541 (5)	0.4480 (14)	0.5134 (8)	0.0384 (18)	0.447 (7)
H3XA	0.0378	0.5338	0.5162	0.046*	0.447 (7)
C4X	0.0502 (3)	0.3499 (10)	0.5848 (7)	0.0386 (17)	0.447 (7)
H4XA	0.0316	0.3687	0.6358	0.046*	0.447 (7)
C5X	0.0736 (3)	0.2243 (10)	0.5816 (6)	0.0386 (16)	0.447 (7)
H5XA	0.0706	0.1550	0.6295	0.046*	0.447 (7)
C6X	0.1013 (3)	0.2004 (9)	0.5079 (7)	0.0355 (16)	0.447 (7)
H6XA	0.1172	0.1139	0.5055	0.043*	0.447 (7)
C8X	0.0824 (4)	0.5415 (12)	0.3644 (8)	0.047 (2)	0.447 (7)
H8XA	0.1121	0.5759	0.3573	0.070*	0.447 (7)
H8XB	0.0638	0.6207	0.3839	0.070*	0.447 (7)
H8XC	0.0721	0.5034	0.3048	0.070*	0.447 (7)
O3	0.36527 (12)	0.1727 (5)	0.2834 (3)	0.0500 (10)	0.701 (6)
H1O3	0.3422 (13)	0.188 (7)	0.255 (5)	0.14 (3)*	0.701 (6)
O4	0.33484 (11)	0.3284 (4)	0.3778 (3)	0.0562 (10)	0.701 (6)
C15	0.36205 (13)	0.2401 (5)	0.3631 (3)	0.0327 (9)	0.701 (6)
C9	0.3946 (2)	0.2022 (5)	0.4361 (4)	0.0274 (10)	0.701 (6)
C10	0.4180 (4)	0.0736 (9)	0.4378 (6)	0.0298 (11)	0.701 (6)
C11	0.4457 (3)	0.0504 (7)	0.5138 (4)	0.0343 (11)	0.701 (6)
H11A	0.4619	−0.0356	0.5165	0.041*	0.701 (6)
C12	0.45004 (18)	0.1491 (5)	0.5845 (4)	0.0376 (11)	0.701 (6)
H12A	0.4690	0.1304	0.6350	0.045*	0.701 (6)
C13	0.42687 (18)	0.2753 (6)	0.5821 (4)	0.0399 (11)	0.701 (6)
H13A	0.4298	0.3434	0.6308	0.048*	0.701 (6)
C14	0.39952 (17)	0.3011 (5)	0.5084 (4)	0.0341 (10)	0.701 (6)
H14A	0.3836	0.3879	0.5067	0.041*	0.701 (6)
C16	0.41716 (19)	−0.0404 (6)	0.3644 (4)	0.0385 (12)	0.701 (6)
H16A	0.3875	−0.0541	0.3426	0.058*	0.701 (6)
H16B	0.4280	−0.1301	0.3907	0.058*	0.701 (6)
H16C	0.4354	−0.0116	0.3120	0.058*	0.701 (6)
O3X	0.3348 (2)	0.2633 (10)	0.3362 (7)	0.051 (2)	0.299 (6)
H2O3	0.3208	0.2570	0.2863	0.076*	0.299 (6)
O4X	0.3721 (3)	0.0864 (11)	0.2729 (5)	0.062 (2)	0.299 (6)
C15X	0.3656 (3)	0.1681 (11)	0.3365 (7)	0.0334 (18)	0.299 (6)
C9X	0.3935 (6)	0.1699 (15)	0.4238 (10)	0.0324 (18)	0.299 (6)
C10X	0.4215 (10)	0.059 (2)	0.4473 (16)	0.032 (2)	0.299 (6)
C11X	0.4429 (7)	0.0728 (18)	0.5332 (11)	0.038 (2)	0.299 (6)
H11B	0.4618	−0.0014	0.5526	0.045*	0.299 (6)
C12X	0.4378 (4)	0.1888 (15)	0.5901 (9)	0.039 (2)	0.299 (6)
H12B	0.4536	0.1944	0.6468	0.047*	0.299 (6)
C13X	0.4102 (4)	0.2966 (13)	0.5664 (10)	0.042 (2)	0.299 (6)
H13B	0.4062	0.3763	0.6064	0.050*	0.299 (6)
C14X	0.3884 (4)	0.2868 (14)	0.4827 (9)	0.0373 (19)	0.299 (6)
H14B	0.3695	0.3618	0.4649	0.045*	0.299 (6)
C16X	0.4293 (5)	−0.0695 (13)	0.3850 (10)	0.044 (3)	0.299 (6)
H16D	0.4489	−0.1362	0.4163	0.065*	0.299 (6)
H16E	0.4423	−0.0377	0.3263	0.065*	0.299 (6)
H16F	0.4018	−0.1173	0.3720	0.065*	0.299 (6)
O5	0.13515 (8)	0.8180 (3)	0.52528 (17)	0.0600 (6)
H1O5	0.1590 (16)	0.783 (9)	0.510 (7)	0.30 (5)*
O6	0.15757 (7)	0.6868 (3)	0.6437 (2)	0.0694 (7)
O7	0.36445 (7)	0.6891 (3)	0.52275 (16)	0.0580 (6)
H1O7	0.3376 (6)	0.701 (3)	0.502 (2)	0.051 (8)*
O8	0.34157 (7)	0.8063 (3)	0.6456 (2)	0.0721 (8)
N5	0.21074 (6)	0.7721 (2)	0.44119 (15)	0.0322 (5)
N6	0.28816 (6)	0.7308 (2)	0.44074 (15)	0.0318 (5)
N7	0.24280 (7)	0.6218 (2)	0.32166 (15)	0.0328 (5)
N8	0.25541 (7)	0.8792 (2)	0.32050 (15)	0.0335 (5)
C17	0.08298 (7)	0.7497 (3)	0.63491 (19)	0.0335 (6)
C18	0.06833 (9)	0.6696 (3)	0.7104 (2)	0.0405 (6)
C19	0.02424 (9)	0.6746 (3)	0.7315 (2)	0.0466 (7)
H19A	0.0137	0.6208	0.7827	0.056*
C20	−0.00413 (9)	0.7551 (4)	0.6801 (2)	0.0484 (7)
H20A	−0.0338	0.7560	0.6962	0.058*
C21	0.01014 (10)	0.8352 (3)	0.6048 (2)	0.0484 (7)
H21A	−0.0094	0.8914	0.5693	0.058*
C22	0.05305 (9)	0.8312 (3)	0.5831 (2)	0.0439 (7)
H22A	0.0631	0.8851	0.5313	0.053*
C23	0.12862 (9)	0.7482 (3)	0.6029 (2)	0.0399 (6)
C24	0.09664 (11)	0.5788 (3)	0.7701 (2)	0.0539 (8)
H24A	0.0791	0.5301	0.8171	0.081*
H24B	0.1182	0.6390	0.8011	0.081*
H24C	0.1113	0.5077	0.7313	0.081*
C25	0.41644 (7)	0.7495 (3)	0.63496 (19)	0.0330 (5)
C26	0.43100 (9)	0.8284 (3)	0.7112 (2)	0.0378 (6)
C27	0.47530 (9)	0.8233 (3)	0.7322 (2)	0.0420 (7)
H27A	0.4859	0.8774	0.7833	0.050*
C28	0.50335 (9)	0.7435 (3)	0.6815 (2)	0.0451 (7)
H28A	0.5330	0.7421	0.6978	0.054*
C29	0.48888 (10)	0.6636 (3)	0.6058 (2)	0.0469 (7)
H29A	0.5085	0.6074	0.5706	0.056*
C30	0.44592 (9)	0.6673 (3)	0.5830 (2)	0.0394 (6)
H30A	0.4359	0.6135	0.5312	0.047*
C31	0.37072 (8)	0.7510 (3)	0.6027 (2)	0.0376 (6)
C32	0.40309 (10)	0.9208 (3)	0.7701 (2)	0.0511 (8)
H32A	0.4211	0.9746	0.8140	0.077*
H32B	0.3827	0.8612	0.8047	0.077*
H32C	0.3872	0.9876	0.7303	0.077*
N1	0.2177 (2)	0.2512 (6)	0.1937 (4)	0.0300 (10)	0.633 (13)
N2	0.2960 (2)	0.2281 (6)	0.1778 (4)	0.0311 (10)	0.633 (13)
N3	0.2483 (3)	0.1200 (11)	0.0633 (6)	0.0347 (12)	0.633 (13)
N4	0.2556 (3)	0.3799 (10)	0.0705 (6)	0.0351 (12)	0.633 (13)
C33	0.2596 (3)	0.2375 (5)	0.2431 (4)	0.0300 (10)	0.633 (13)
H33A	0.2637	0.3211	0.2843	0.036*	0.633 (13)
H33B	0.2591	0.1509	0.2826	0.036*	0.633 (13)
C34	0.2887 (2)	0.1052 (7)	0.1150 (5)	0.0347 (12)	0.633 (13)
H34A	0.3130	0.0981	0.0705	0.042*	0.633 (13)
H34B	0.2880	0.0161	0.1521	0.042*	0.633 (13)
C35	0.2128 (3)	0.1257 (8)	0.1311 (6)	0.0360 (14)	0.633 (13)
H35A	0.2127	0.0370	0.1687	0.043*	0.633 (13)
H35B	0.1850	0.1320	0.0977	0.043*	0.633 (13)
C36	0.2200 (2)	0.3822 (8)	0.1366 (5)	0.0364 (13)	0.633 (13)
H36A	0.1926	0.3937	0.1021	0.044*	0.633 (13)
H36B	0.2234	0.4658	0.1783	0.044*	0.633 (13)
C37	0.2958 (2)	0.3590 (8)	0.1200 (6)	0.0353 (14)	0.633 (13)
H37A	0.3011	0.4427	0.1605	0.042*	0.633 (13)
H37B	0.3196	0.3536	0.0744	0.042*	0.633 (13)
C38	0.2493 (5)	0.2546 (11)	0.0099 (7)	0.0402 (13)	0.633 (13)
H38A	0.2731	0.2503	−0.0361	0.048*	0.633 (13)
H38B	0.2219	0.2654	−0.0248	0.048*	0.633 (13)
N1X	0.2038 (4)	0.2737 (10)	0.1784 (7)	0.0342 (15)	0.367 (13)
N2X	0.2823 (4)	0.2485 (11)	0.1938 (7)	0.0321 (15)	0.367 (13)
N3X	0.2428 (5)	0.1170 (18)	0.0716 (11)	0.0345 (17)	0.367 (13)
N4X	0.2509 (5)	0.3760 (19)	0.0625 (11)	0.0356 (17)	0.367 (13)
C33X	0.2410 (4)	0.2628 (10)	0.2435 (6)	0.0290 (15)	0.367 (13)
H33C	0.2420	0.3491	0.2833	0.035*	0.367 (13)
H33D	0.2370	0.1789	0.2846	0.035*	0.367 (13)
C34X	0.2795 (4)	0.1157 (13)	0.1361 (9)	0.0375 (19)	0.367 (13)
H34C	0.3064	0.1048	0.1000	0.045*	0.367 (13)
H34D	0.2768	0.0321	0.1779	0.045*	0.367 (13)
C35X	0.2027 (4)	0.1408 (14)	0.1231 (10)	0.0348 (19)	0.367 (13)
H35C	0.1976	0.0588	0.1652	0.042*	0.367 (13)
H35D	0.1784	0.1454	0.0785	0.042*	0.367 (13)
C36X	0.2114 (4)	0.3948 (13)	0.1167 (9)	0.0344 (18)	0.367 (13)
H36C	0.2137	0.4832	0.1542	0.041*	0.367 (13)
H36D	0.1867	0.4056	0.0737	0.041*	0.367 (13)
C37X	0.2864 (5)	0.3726 (15)	0.1291 (10)	0.0355 (19)	0.367 (13)
H37C	0.2865	0.4623	0.1655	0.043*	0.367 (13)
H37D	0.3140	0.3660	0.0951	0.043*	0.367 (13)
C38X	0.2487 (8)	0.2411 (18)	0.0102 (12)	0.0383 (19)	0.367 (13)
H38C	0.2245	0.2457	−0.0345	0.046*	0.367 (13)
H38D	0.2757	0.2288	−0.0258	0.046*	0.367 (13)
C39	0.24965 (10)	0.7525 (4)	0.49886 (11)	0.0335 (4)
H39A	0.2539	0.8376	0.5387	0.040*
H39B	0.2457	0.6687	0.5401	0.040*
C40	0.28079 (9)	0.6048 (3)	0.3808 (2)	0.0345 (6)
H40A	0.3064	0.5892	0.3411	0.041*
H40B	0.2771	0.5192	0.4206	0.041*
C41	0.20552 (9)	0.6445 (3)	0.3811 (2)	0.0361 (6)
H41A	0.2012	0.5593	0.4208	0.043*
H41B	0.1795	0.6564	0.3418	0.043*
C42	0.21791 (9)	0.8971 (3)	0.3801 (2)	0.0348 (6)
H42A	0.1921	0.9120	0.3407	0.042*
H42B	0.2219	0.9833	0.4191	0.042*
C43	0.29284 (9)	0.8573 (3)	0.3799 (2)	0.0380 (6)
H43A	0.2972	0.9431	0.4191	0.046*
H43B	0.3187	0.8454	0.3404	0.046*
C44	0.24907 (12)	0.7491 (4)	0.26356 (11)	0.0382 (4)
H44A	0.2236	0.7622	0.2228	0.046*
H44B	0.2746	0.7348	0.2231	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.050 (2)	0.057 (3)	0.043 (2)	0.019 (2)	0.0175 (19)	0.016 (2)
O2	0.076 (3)	0.066 (3)	0.041 (2)	0.029 (2)	0.010 (2)	0.014 (2)
C7	0.036 (2)	0.038 (3)	0.025 (2)	0.003 (2)	−0.005 (2)	−0.002 (2)
C1	0.033 (2)	0.037 (3)	0.029 (3)	−0.003 (2)	−0.005 (2)	−0.002 (2)
C2	0.034 (3)	0.032 (3)	0.037 (3)	−0.005 (2)	−0.002 (2)	−0.010 (2)
C3	0.044 (3)	0.045 (3)	0.040 (3)	−0.004 (3)	0.012 (3)	−0.015 (3)
C4	0.049 (3)	0.050 (4)	0.039 (2)	−0.007 (3)	0.011 (3)	−0.009 (3)
C5	0.044 (3)	0.049 (3)	0.039 (3)	−0.009 (3)	0.004 (3)	0.003 (2)
C6	0.035 (3)	0.047 (3)	0.030 (3)	−0.004 (2)	0.004 (2)	0.000 (2)
C8	0.043 (5)	0.045 (4)	0.056 (4)	0.002 (3)	0.003 (3)	−0.001 (3)
O1X	0.076 (4)	0.059 (4)	0.041 (3)	0.026 (3)	0.014 (3)	0.006 (3)
O2X	0.052 (3)	0.061 (4)	0.071 (4)	0.027 (3)	0.015 (3)	0.010 (3)
C7X	0.037 (3)	0.041 (3)	0.040 (3)	0.002 (3)	−0.003 (2)	0.003 (3)
C1X	0.029 (3)	0.037 (3)	0.030 (3)	0.002 (3)	−0.002 (2)	−0.004 (3)
C2X	0.034 (3)	0.036 (4)	0.035 (3)	−0.005 (3)	−0.002 (3)	0.000 (3)
C3X	0.039 (3)	0.035 (3)	0.042 (4)	0.000 (3)	−0.002 (3)	−0.004 (3)
C4X	0.040 (4)	0.040 (4)	0.036 (3)	0.004 (3)	0.006 (3)	−0.004 (3)
C5X	0.042 (4)	0.040 (3)	0.034 (3)	0.003 (3)	0.004 (3)	0.002 (3)
C6X	0.036 (3)	0.037 (3)	0.034 (3)	0.001 (3)	0.000 (3)	0.001 (3)
C8X	0.045 (6)	0.038 (5)	0.058 (5)	−0.003 (4)	−0.003 (4)	0.005 (4)
O3	0.0538 (19)	0.057 (2)	0.0388 (19)	0.0237 (17)	−0.0081 (17)	−0.0105 (18)
O4	0.0538 (19)	0.048 (2)	0.067 (2)	0.0258 (15)	−0.0208 (17)	−0.0218 (18)
C15	0.0307 (18)	0.0265 (18)	0.0408 (19)	−0.0003 (16)	0.0002 (16)	0.0022 (16)
C9	0.0285 (17)	0.022 (2)	0.032 (2)	0.0017 (18)	0.0020 (16)	0.0029 (16)
C10	0.025 (2)	0.028 (2)	0.037 (2)	−0.0028 (18)	0.0026 (17)	0.005 (2)
C11	0.036 (2)	0.023 (2)	0.044 (3)	0.0018 (17)	0.002 (2)	0.0038 (17)
C12	0.047 (3)	0.028 (2)	0.038 (2)	0.0015 (17)	−0.0064 (19)	0.0070 (18)
C13	0.044 (3)	0.040 (2)	0.036 (2)	0.002 (2)	−0.0029 (19)	−0.0053 (19)
C14	0.036 (2)	0.0279 (18)	0.038 (2)	0.0032 (17)	−0.0013 (18)	−0.0037 (18)
C16	0.036 (3)	0.025 (2)	0.054 (3)	0.0064 (18)	−0.001 (2)	−0.004 (2)
O3X	0.039 (4)	0.057 (5)	0.056 (5)	0.013 (3)	−0.017 (3)	−0.011 (4)
O4X	0.078 (5)	0.073 (6)	0.034 (4)	0.038 (4)	−0.016 (4)	−0.018 (4)
C15X	0.035 (3)	0.035 (4)	0.030 (4)	0.006 (3)	0.001 (3)	0.000 (4)
C9X	0.032 (3)	0.033 (4)	0.032 (3)	−0.007 (3)	0.002 (3)	−0.002 (3)
C10X	0.030 (4)	0.026 (4)	0.040 (4)	−0.001 (3)	0.002 (3)	0.007 (3)
C11X	0.037 (4)	0.034 (4)	0.042 (4)	−0.004 (4)	−0.008 (4)	0.007 (3)
C12X	0.045 (4)	0.038 (4)	0.034 (3)	0.000 (4)	−0.009 (3)	0.000 (3)
C13X	0.046 (4)	0.040 (4)	0.039 (4)	0.002 (4)	−0.006 (4)	−0.002 (3)
C14X	0.039 (4)	0.037 (3)	0.036 (4)	−0.006 (3)	−0.003 (3)	0.000 (3)
C16X	0.047 (8)	0.034 (5)	0.049 (6)	−0.002 (5)	−0.010 (5)	0.010 (4)
O5	0.0514 (13)	0.0737 (16)	0.0548 (14)	0.0074 (12)	0.0131 (12)	0.0148 (12)
O6	0.0328 (11)	0.0881 (18)	0.0874 (19)	0.0106 (11)	0.0036 (12)	0.0254 (16)
O7	0.0398 (12)	0.0792 (17)	0.0550 (13)	0.0122 (11)	−0.0149 (11)	−0.0159 (12)
O8	0.0381 (12)	0.099 (2)	0.0788 (18)	0.0127 (12)	0.0000 (13)	−0.0271 (16)
N5	0.0333 (11)	0.0292 (11)	0.0342 (11)	−0.0004 (9)	0.0051 (10)	−0.0011 (9)
N6	0.0322 (10)	0.0302 (11)	0.0330 (11)	0.0005 (9)	−0.0086 (9)	0.0005 (9)
N7	0.0436 (12)	0.0249 (11)	0.0299 (11)	−0.0007 (9)	−0.0050 (10)	−0.0050 (9)
N8	0.0435 (13)	0.0259 (11)	0.0311 (12)	0.0020 (9)	0.0000 (10)	0.0066 (9)
C17	0.0306 (12)	0.0300 (12)	0.0398 (14)	−0.0020 (11)	−0.0011 (11)	−0.0089 (11)
C18	0.0422 (16)	0.0372 (15)	0.0423 (15)	−0.0036 (12)	−0.0012 (13)	−0.0095 (12)
C19	0.0352 (15)	0.0537 (18)	0.0509 (18)	−0.0096 (13)	0.0054 (14)	−0.0183 (15)
C20	0.0369 (14)	0.0578 (18)	0.0505 (17)	−0.0020 (15)	0.0008 (14)	−0.0165 (15)
C21	0.0376 (15)	0.0534 (18)	0.0544 (18)	0.0117 (14)	−0.0066 (14)	−0.0106 (15)
C22	0.0438 (16)	0.0395 (15)	0.0484 (17)	0.0034 (13)	−0.0008 (14)	−0.0057 (13)
C23	0.0376 (14)	0.0357 (14)	0.0463 (16)	−0.0034 (13)	0.0037 (13)	−0.0081 (13)
C24	0.0550 (19)	0.0525 (18)	0.0542 (19)	0.0002 (15)	−0.0066 (17)	0.0055 (16)
C25	0.0327 (12)	0.0285 (12)	0.0377 (14)	−0.0030 (11)	−0.0026 (11)	0.0078 (11)
C26	0.0405 (15)	0.0337 (14)	0.0391 (15)	−0.0040 (12)	0.0021 (12)	0.0071 (12)
C27	0.0371 (15)	0.0428 (16)	0.0461 (16)	−0.0058 (12)	−0.0061 (13)	0.0105 (14)
C28	0.0339 (14)	0.0509 (17)	0.0506 (17)	−0.0063 (14)	−0.0055 (14)	0.0137 (14)
C29	0.0421 (16)	0.0443 (16)	0.0542 (18)	0.0084 (13)	0.0081 (14)	0.0086 (14)
C30	0.0394 (15)	0.0334 (14)	0.0454 (16)	0.0017 (12)	−0.0014 (13)	0.0038 (12)
C31	0.0351 (13)	0.0339 (13)	0.0438 (15)	−0.0016 (13)	−0.0036 (12)	0.0045 (12)
C32	0.0509 (18)	0.0508 (17)	0.0516 (18)	−0.0014 (14)	0.0035 (16)	−0.0047 (15)
N1	0.036 (2)	0.0266 (18)	0.028 (2)	0.0016 (17)	−0.0014 (18)	−0.0012 (15)
N2	0.040 (2)	0.0288 (19)	0.0241 (19)	0.0062 (17)	0.0011 (17)	−0.0008 (15)
N3	0.053 (3)	0.0243 (19)	0.027 (2)	−0.0018 (19)	0.0033 (19)	−0.0021 (18)
N4	0.060 (3)	0.0201 (18)	0.025 (2)	0.000 (2)	−0.001 (2)	0.0010 (17)
C33	0.039 (3)	0.029 (2)	0.0216 (18)	0.0040 (19)	−0.003 (2)	0.0001 (15)
C34	0.050 (3)	0.0232 (19)	0.031 (3)	0.0061 (19)	0.004 (2)	−0.0006 (18)
C35	0.045 (3)	0.027 (2)	0.036 (2)	−0.005 (2)	−0.004 (2)	−0.0042 (19)
C36	0.047 (3)	0.028 (2)	0.034 (3)	0.011 (2)	−0.011 (2)	−0.006 (2)
C37	0.044 (3)	0.025 (2)	0.037 (2)	−0.003 (2)	0.001 (2)	0.0024 (19)
C38	0.071 (3)	0.028 (3)	0.021 (2)	0.004 (2)	−0.003 (2)	0.005 (2)
N1X	0.044 (3)	0.029 (3)	0.029 (3)	0.003 (3)	−0.003 (3)	0.000 (2)
N2X	0.041 (3)	0.031 (3)	0.024 (3)	0.001 (3)	0.002 (3)	0.003 (2)
N3X	0.057 (4)	0.023 (3)	0.023 (3)	0.001 (3)	0.001 (3)	0.001 (3)
N4X	0.052 (3)	0.026 (3)	0.029 (3)	0.000 (3)	−0.008 (3)	0.004 (3)
C33X	0.036 (3)	0.031 (3)	0.020 (3)	0.004 (3)	0.002 (3)	0.003 (2)
C34X	0.050 (4)	0.032 (3)	0.031 (4)	0.010 (3)	0.012 (3)	0.003 (3)
C35X	0.044 (4)	0.029 (3)	0.032 (3)	−0.002 (3)	−0.001 (3)	0.001 (3)
C36X	0.052 (4)	0.022 (3)	0.029 (4)	0.005 (3)	−0.007 (3)	−0.001 (3)
C37X	0.045 (4)	0.030 (3)	0.032 (3)	−0.004 (3)	0.009 (3)	0.009 (3)
C38X	0.068 (4)	0.025 (4)	0.022 (3)	0.000 (3)	0.001 (3)	−0.008 (3)
C39	0.0495 (10)	0.0280 (8)	0.0231 (7)	−0.0016 (7)	0.0005 (14)	−0.0008 (13)
C40	0.0412 (15)	0.0251 (12)	0.0371 (14)	0.0082 (11)	0.0000 (12)	−0.0003 (11)
C41	0.0351 (14)	0.0292 (13)	0.0441 (15)	−0.0088 (11)	−0.0011 (12)	−0.0027 (12)
C42	0.0412 (15)	0.0248 (12)	0.0384 (14)	0.0075 (11)	−0.0003 (12)	0.0016 (11)
C43	0.0371 (14)	0.0329 (13)	0.0441 (15)	−0.0099 (11)	0.0035 (12)	0.0041 (12)
C44	0.0542 (11)	0.0375 (9)	0.0228 (7)	0.0051 (8)	−0.0017 (15)	0.0017 (14)

Geometric parameters (Å, º) top

O1—C7	1.313 (6)	C17—C18	1.394 (4)
O1—H1O1	0.83 (2)	C17—C22	1.413 (4)
O2—C7	1.208 (7)	C17—C23	1.489 (4)
C7—C1	1.492 (8)	C18—C19	1.401 (4)
C1—C6	1.392 (8)	C18—C24	1.492 (4)
C1—C2	1.408 (8)	C19—C20	1.373 (4)
C2—C3	1.397 (9)	C19—H19A	0.9500
C2—C8	1.513 (9)	C20—C21	1.389 (5)
C3—C4	1.370 (9)	C20—H20A	0.9500
C3—H3A	0.9500	C21—C22	1.367 (4)
C4—C5	1.372 (8)	C21—H21A	0.9500
C4—H4A	0.9500	C22—H22A	0.9500
C5—C6	1.379 (8)	C24—H24A	0.9800
C5—H5A	0.9500	C24—H24B	0.9800
C6—H6A	0.9500	C24—H24C	0.9800
C8—H8A	0.9800	C25—C26	1.395 (4)
C8—H8B	0.9800	C25—C30	1.410 (4)
C8—H8C	0.9800	C25—C31	1.491 (3)
O1X—C7X	1.306 (8)	C26—C27	1.407 (4)
O1X—H2O1	0.8400	C26—C32	1.488 (4)
O2X—C7X	1.220 (8)	C27—C28	1.359 (4)
C7X—C1X	1.489 (10)	C27—H27A	0.9500
C1X—C2X	1.395 (10)	C28—C29	1.393 (5)
C1X—C6X	1.400 (10)	C28—H28A	0.9500
C2X—C3X	1.395 (11)	C29—C30	1.372 (4)
C2X—C8X	1.513 (10)	C29—H29A	0.9500
C3X—C4X	1.381 (10)	C30—H30A	0.9500
C3X—H3XA	0.9500	C32—H32A	0.9800
C4X—C5X	1.383 (9)	C32—H32B	0.9800
C4X—H4XA	0.9500	C32—H32C	0.9800
C5X—C6X	1.381 (9)	N1—C36	1.477 (6)
C5X—H5XA	0.9500	N1—C33	1.483 (5)
C6X—H6XA	0.9500	N1—C35	1.487 (7)
C8X—H8XA	0.9800	N2—C33	1.469 (6)
C8X—H8XB	0.9800	N2—C34	1.478 (6)
C8X—H8XC	0.9800	N2—C37	1.481 (7)
O3—C15	1.311 (5)	N3—C34	1.463 (7)
O3—H1O3	0.84 (2)	N3—C35	1.470 (7)
O4—C15	1.201 (5)	N3—C38	1.476 (8)
C15—C9	1.497 (6)	N4—C37	1.446 (7)
C9—C14	1.400 (6)	N4—C36	1.457 (8)
C9—C10	1.406 (6)	N4—C38	1.473 (8)
C10—C11	1.404 (7)	C33—H33A	0.9900
C10—C16	1.500 (6)	C33—H33B	0.9900
C11—C12	1.379 (6)	C34—H34A	0.9900
C11—H11A	0.9500	C34—H34B	0.9900
C12—C13	1.383 (6)	C35—H35A	0.9900
C12—H12A	0.9500	C35—H35B	0.9900
C13—C14	1.376 (6)	C36—H36A	0.9900
C13—H13A	0.9500	C36—H36B	0.9900
C14—H14A	0.9500	C37—H37A	0.9900
C16—H16A	0.9800	C37—H37B	0.9900
C16—H16B	0.9800	C38—H38A	0.9900
C16—H16C	0.9800	C38—H38B	0.9900
O3X—C15X	1.307 (10)	N1X—C36X	1.459 (10)
O3X—H2O3	0.8400	N1X—C35X	1.477 (11)
O4X—C15X	1.208 (11)	N1X—C33X	1.488 (9)
C15X—C9X	1.520 (12)	N2X—C33X	1.471 (9)
C9X—C14X	1.392 (12)	N2X—C37X	1.493 (11)
C9X—C10X	1.397 (13)	N2X—C34X	1.496 (11)
C10X—C11X	1.406 (13)	N3X—C35X	1.464 (12)
C10X—C16X	1.516 (13)	N3X—C34X	1.465 (12)
C11X—C12X	1.369 (13)	N3X—C38X	1.470 (13)
C11X—H11B	0.9500	N4X—C37X	1.456 (12)
C12X—C13X	1.365 (12)	N4X—C36X	1.462 (12)
C12X—H12B	0.9500	N4X—C38X	1.470 (13)
C13X—C14X	1.381 (12)	C33X—H33C	0.9900
C13X—H13B	0.9500	C33X—H33D	0.9900
C14X—H14B	0.9500	C34X—H34C	0.9900
C16X—H16D	0.9800	C34X—H34D	0.9900
C16X—H16E	0.9800	C35X—H35C	0.9900
C16X—H16F	0.9800	C35X—H35D	0.9900
O5—C23	1.308 (4)	C36X—H36C	0.9900
O5—H1O5	0.84 (2)	C36X—H36D	0.9900
O6—C23	1.216 (4)	C37X—H37C	0.9900
O7—C31	1.301 (4)	C37X—H37D	0.9900
O7—H1O7	0.889 (17)	C38X—H38C	0.9900
O8—C31	1.210 (3)	C38X—H38D	0.9900
N5—C39	1.474 (3)	C39—H39A	0.9900
N5—C42	1.479 (3)	C39—H39B	0.9900
N5—C41	1.482 (3)	C40—H40A	0.9900
N6—C39	1.471 (3)	C40—H40B	0.9900
N6—C40	1.478 (3)	C41—H41A	0.9900
N6—C43	1.479 (3)	C41—H41B	0.9900
N7—C41	1.453 (3)	C42—H42A	0.9900
N7—C40	1.460 (3)	C42—H42B	0.9900
N7—C44	1.468 (4)	C43—H43A	0.9900
N8—C43	1.454 (3)	C43—H43B	0.9900
N8—C42	1.454 (3)	C44—H44A	0.9900
N8—C44	1.480 (4)	C44—H44B	0.9900

C7—O1—H1O1	111 (4)	C25—C26—C27	117.7 (3)
O2—C7—O1	122.6 (5)	C25—C26—C32	124.5 (3)
O2—C7—C1	124.2 (5)	C27—C26—C32	117.8 (3)
O1—C7—C1	113.1 (6)	C28—C27—C26	122.0 (3)
C6—C1—C2	119.2 (7)	C28—C27—H27A	119.0
C6—C1—C7	118.7 (6)	C26—C27—H27A	119.0
C2—C1—C7	122.1 (6)	C27—C28—C29	120.5 (3)
C3—C2—C1	117.6 (8)	C27—C28—H28A	119.8
C3—C2—C8	119.6 (7)	C29—C28—H28A	119.8
C1—C2—C8	122.8 (7)	C30—C29—C28	119.0 (3)
C4—C3—C2	121.7 (8)	C30—C29—H29A	120.5
C4—C3—H3A	119.1	C28—C29—H29A	120.5
C2—C3—H3A	119.1	C29—C30—C25	121.1 (3)
C3—C4—C5	120.9 (7)	C29—C30—H30A	119.4
C3—C4—H4A	119.6	C25—C30—H30A	119.4
C5—C4—H4A	119.6	O8—C31—O7	121.9 (3)
C4—C5—C6	118.6 (7)	O8—C31—C25	123.8 (3)
C4—C5—H5A	120.7	O7—C31—C25	114.3 (3)
C6—C5—H5A	120.7	C26—C32—H32A	109.5
C5—C6—C1	122.0 (7)	C26—C32—H32B	109.5
C5—C6—H6A	119.0	H32A—C32—H32B	109.5
C1—C6—H6A	119.0	C26—C32—H32C	109.5
C2—C8—H8A	109.5	H32A—C32—H32C	109.5
C2—C8—H8B	109.5	H32B—C32—H32C	109.5
H8A—C8—H8B	109.5	C36—N1—C33	107.1 (4)
C2—C8—H8C	109.5	C36—N1—C35	109.1 (5)
H8A—C8—H8C	109.5	C33—N1—C35	108.0 (4)
H8B—C8—H8C	109.5	C33—N2—C34	108.6 (4)
C7X—O1X—H2O1	109.5	C33—N2—C37	107.8 (4)
O2X—C7X—O1X	123.1 (7)	C34—N2—C37	107.6 (5)
O2X—C7X—C1X	120.3 (7)	C34—N3—C35	108.0 (6)
O1X—C7X—C1X	116.6 (7)	C34—N3—C38	109.0 (7)
C2X—C1X—C6X	119.6 (8)	C35—N3—C38	109.3 (8)
C2X—C1X—C7X	124.8 (8)	C37—N4—C36	109.5 (6)
C6X—C1X—C7X	115.5 (7)	C37—N4—C38	107.2 (8)
C3X—C2X—C1X	118.0 (9)	C36—N4—C38	107.3 (7)
C3X—C2X—C8X	116.5 (9)	N2—C33—N1	111.8 (4)
C1X—C2X—C8X	125.5 (9)	N2—C33—H33A	109.2
C4X—C3X—C2X	122.0 (10)	N1—C33—H33A	109.2
C4X—C3X—H3XA	119.0	N2—C33—H33B	109.2
C2X—C3X—H3XA	119.0	N1—C33—H33B	109.2
C3X—C4X—C5X	119.7 (9)	H33A—C33—H33B	107.9
C3X—C4X—H4XA	120.2	N3—C34—N2	111.4 (5)
C5X—C4X—H4XA	120.2	N3—C34—H34A	109.3
C6X—C5X—C4X	119.3 (8)	N2—C34—H34A	109.3
C6X—C5X—H5XA	120.4	N3—C34—H34B	109.3
C4X—C5X—H5XA	120.4	N2—C34—H34B	109.3
C5X—C6X—C1X	121.2 (7)	H34A—C34—H34B	108.0
C5X—C6X—H6XA	119.4	N3—C35—N1	110.6 (6)
C1X—C6X—H6XA	119.4	N3—C35—H35A	109.5
C2X—C8X—H8XA	109.5	N1—C35—H35A	109.5
C2X—C8X—H8XB	109.5	N3—C35—H35B	109.5
H8XA—C8X—H8XB	109.5	N1—C35—H35B	109.5
C2X—C8X—H8XC	109.5	H35A—C35—H35B	108.1
H8XA—C8X—H8XC	109.5	N4—C36—N1	112.7 (5)
H8XB—C8X—H8XC	109.5	N4—C36—H36A	109.1
C15—O3—H1O3	106 (5)	N1—C36—H36A	109.1
O4—C15—O3	122.6 (4)	N4—C36—H36B	109.1
O4—C15—C9	120.9 (4)	N1—C36—H36B	109.1
O3—C15—C9	116.4 (4)	H36A—C36—H36B	107.8
C14—C9—C10	119.8 (5)	N4—C37—N2	112.9 (6)
C14—C9—C15	115.8 (4)	N4—C37—H37A	109.0
C10—C9—C15	124.3 (4)	N2—C37—H37A	109.0
C11—C10—C9	117.5 (5)	N4—C37—H37B	109.0
C11—C10—C16	116.5 (5)	N2—C37—H37B	109.0
C9—C10—C16	126.0 (5)	H37A—C37—H37B	107.8
C12—C11—C10	121.8 (5)	N4—C38—N3	112.1 (7)
C12—C11—H11A	119.1	N4—C38—H38A	109.2
C10—C11—H11A	119.1	N3—C38—H38A	109.2
C11—C12—C13	120.3 (5)	N4—C38—H38B	109.2
C11—C12—H12A	119.9	N3—C38—H38B	109.2
C13—C12—H12A	119.9	H38A—C38—H38B	107.9
C14—C13—C12	119.3 (4)	C36X—N1X—C35X	109.4 (9)
C14—C13—H13A	120.4	C36X—N1X—C33X	107.9 (7)
C12—C13—H13A	120.4	C35X—N1X—C33X	107.3 (7)
C13—C14—C9	121.3 (4)	C33X—N2X—C37X	107.7 (7)
C13—C14—H14A	119.3	C33X—N2X—C34X	107.0 (7)
C9—C14—H14A	119.3	C37X—N2X—C34X	107.9 (9)
C10—C16—H16A	109.5	C35X—N3X—C34X	110.0 (10)
C10—C16—H16B	109.5	C35X—N3X—C38X	106.8 (13)
H16A—C16—H16B	109.5	C34X—N3X—C38X	106.7 (12)
C10—C16—H16C	109.5	C37X—N4X—C36X	106.5 (11)
H16A—C16—H16C	109.5	C37X—N4X—C38X	110.5 (14)
H16B—C16—H16C	109.5	C36X—N4X—C38X	109.7 (13)
C15X—O3X—H2O3	109.5	N2X—C33X—N1X	112.1 (7)
O4X—C15X—O3X	123.5 (10)	N2X—C33X—H33C	109.2
O4X—C15X—C9X	122.3 (9)	N1X—C33X—H33C	109.2
O3X—C15X—C9X	114.2 (10)	N2X—C33X—H33D	109.2
C14X—C9X—C10X	120.7 (11)	N1X—C33X—H33D	109.2
C14X—C9X—C15X	116.4 (10)	H33C—C33X—H33D	107.9
C10X—C9X—C15X	122.8 (11)	N3X—C34X—N2X	112.8 (9)
C9X—C10X—C11X	115.7 (12)	N3X—C34X—H34C	109.0
C9X—C10X—C16X	123.2 (12)	N2X—C34X—H34C	109.0
C11X—C10X—C16X	121.1 (11)	N3X—C34X—H34D	109.0
C12X—C11X—C10X	123.0 (13)	N2X—C34X—H34D	109.0
C12X—C11X—H11B	118.5	H34C—C34X—H34D	107.8
C10X—C11X—H11B	118.5	N3X—C35X—N1X	112.4 (10)
C13X—C12X—C11X	120.7 (11)	N3X—C35X—H35C	109.1
C13X—C12X—H12B	119.7	N1X—C35X—H35C	109.1
C11X—C12X—H12B	119.7	N3X—C35X—H35D	109.1
C12X—C13X—C14X	118.3 (11)	N1X—C35X—H35D	109.1
C12X—C13X—H13B	120.9	H35C—C35X—H35D	107.9
C14X—C13X—H13B	120.9	N1X—C36X—N4X	111.5 (10)
C13X—C14X—C9X	121.7 (12)	N1X—C36X—H36C	109.3
C13X—C14X—H14B	119.2	N4X—C36X—H36C	109.3
C9X—C14X—H14B	119.2	N1X—C36X—H36D	109.3
C10X—C16X—H16D	109.5	N4X—C36X—H36D	109.3
C10X—C16X—H16E	109.5	H36C—C36X—H36D	108.0
H16D—C16X—H16E	109.5	N4X—C37X—N2X	111.2 (10)
C10X—C16X—H16F	109.5	N4X—C37X—H37C	109.4
H16D—C16X—H16F	109.5	N2X—C37X—H37C	109.4
H16E—C16X—H16F	109.5	N4X—C37X—H37D	109.4
C23—O5—H1O5	100 (7)	N2X—C37X—H37D	109.4
C31—O7—H1O7	112.2 (19)	H37C—C37X—H37D	108.0
C39—N5—C42	108.0 (2)	N3X—C38X—N4X	112.3 (12)
C39—N5—C41	108.4 (2)	N3X—C38X—H38C	109.1
C42—N5—C41	108.0 (2)	N4X—C38X—H38C	109.1
C39—N6—C40	108.4 (2)	N3X—C38X—H38D	109.1
C39—N6—C43	107.7 (2)	N4X—C38X—H38D	109.1
C40—N6—C43	108.1 (2)	H38C—C38X—H38D	107.9
C41—N7—C40	108.4 (2)	N6—C39—N5	111.29 (12)
C41—N7—C44	108.7 (2)	N6—C39—H39A	109.4
C40—N7—C44	108.2 (2)	N5—C39—H39A	109.4
C43—N8—C42	108.0 (2)	N6—C39—H39B	109.4
C43—N8—C44	108.3 (2)	N5—C39—H39B	109.4
C42—N8—C44	108.3 (2)	H39A—C39—H39B	108.0
C18—C17—C22	119.1 (2)	N7—C40—N6	112.03 (19)
C18—C17—C23	123.0 (3)	N7—C40—H40A	109.2
C22—C17—C23	117.8 (3)	N6—C40—H40A	109.2
C17—C18—C19	117.9 (3)	N7—C40—H40B	109.2
C17—C18—C24	124.1 (3)	N6—C40—H40B	109.2
C19—C18—C24	117.9 (3)	H40A—C40—H40B	107.9
C20—C19—C18	121.8 (3)	N7—C41—N5	111.9 (2)
C20—C19—H19A	119.1	N7—C41—H41A	109.2
C18—C19—H19A	119.1	N5—C41—H41A	109.2
C19—C20—C21	120.7 (3)	N7—C41—H41B	109.2
C19—C20—H20A	119.7	N5—C41—H41B	109.2
C21—C20—H20A	119.7	H41A—C41—H41B	107.9
C22—C21—C20	118.3 (3)	N8—C42—N5	112.25 (19)
C22—C21—H21A	120.9	N8—C42—H42A	109.2
C20—C21—H21A	120.9	N5—C42—H42A	109.2
C21—C22—C17	122.2 (3)	N8—C42—H42B	109.2
C21—C22—H22A	118.9	N5—C42—H42B	109.2
C17—C22—H22A	118.9	H42A—C42—H42B	107.9
O6—C23—O5	122.1 (3)	N8—C43—N6	112.3 (2)
O6—C23—C17	123.9 (3)	N8—C43—H43A	109.1
O5—C23—C17	114.0 (3)	N6—C43—H43A	109.1
C18—C24—H24A	109.5	N8—C43—H43B	109.1
C18—C24—H24B	109.5	N6—C43—H43B	109.1
H24A—C24—H24B	109.5	H43A—C43—H43B	107.9
C18—C24—H24C	109.5	N7—C44—N8	111.84 (12)
H24A—C24—H24C	109.5	N7—C44—H44A	109.2
H24B—C24—H24C	109.5	N8—C44—H44A	109.2
C26—C25—C30	119.7 (2)	N7—C44—H44B	109.2
C26—C25—C31	123.0 (3)	N8—C44—H44B	109.2
C30—C25—C31	117.2 (2)	H44A—C44—H44B	107.9

O2—C7—C1—C6	171.2 (8)	C26—C27—C28—C29	0.3 (4)
O1—C7—C1—C6	−11.2 (12)	C27—C28—C29—C30	0.3 (4)
O2—C7—C1—C2	−11.0 (17)	C28—C29—C30—C25	−0.4 (4)
O1—C7—C1—C2	166.7 (13)	C26—C25—C30—C29	−0.2 (4)
C6—C1—C2—C3	0 (2)	C31—C25—C30—C29	177.8 (3)
C7—C1—C2—C3	−177.6 (13)	C26—C25—C31—O8	−9.1 (4)
C6—C1—C2—C8	−179.4 (13)	C30—C25—C31—O8	173.0 (3)
C7—C1—C2—C8	3 (2)	C26—C25—C31—O7	170.0 (2)
C1—C2—C3—C4	−1 (2)	C30—C25—C31—O7	−8.0 (4)
C8—C2—C3—C4	179.1 (13)	C34—N2—C33—N1	−57.3 (5)
C2—C3—C4—C5	0.0 (19)	C37—N2—C33—N1	58.9 (5)
C3—C4—C5—C6	0.9 (12)	C36—N1—C33—N2	−59.4 (5)
C4—C5—C6—C1	−1.2 (11)	C35—N1—C33—N2	57.9 (5)
C2—C1—C6—C5	0.6 (17)	C35—N3—C34—N2	−60.8 (8)
C7—C1—C6—C5	178.5 (8)	C38—N3—C34—N2	57.8 (8)
O2X—C7X—C1X—C2X	162.0 (17)	C33—N2—C34—N3	58.8 (6)
O1X—C7X—C1X—C2X	−15 (2)	C37—N2—C34—N3	−57.6 (6)
O2X—C7X—C1X—C6X	−21.1 (16)	C34—N3—C35—N1	61.3 (8)
O1X—C7X—C1X—C6X	161.7 (10)	C38—N3—C35—N1	−57.1 (8)
C6X—C1X—C2X—C3X	5 (3)	C36—N1—C35—N3	56.5 (7)
C7X—C1X—C2X—C3X	−178.5 (17)	C33—N1—C35—N3	−59.6 (7)
C6X—C1X—C2X—C8X	−178.6 (17)	C37—N4—C36—N1	−57.1 (8)
C7X—C1X—C2X—C8X	−2 (3)	C38—N4—C36—N1	58.9 (8)
C1X—C2X—C3X—C4X	−3 (3)	C33—N1—C36—N4	58.0 (6)
C8X—C2X—C3X—C4X	−179.9 (15)	C35—N1—C36—N4	−58.6 (6)
C2X—C3X—C4X—C5X	0 (2)	C36—N4—C37—N2	56.4 (8)
C3X—C4X—C5X—C6X	1.5 (14)	C38—N4—C37—N2	−59.7 (8)
C4X—C5X—C6X—C1X	0.4 (14)	C33—N2—C37—N4	−57.2 (7)
C2X—C1X—C6X—C5X	−4 (2)	C34—N2—C37—N4	59.8 (7)
C7X—C1X—C6X—C5X	179.4 (9)	C37—N4—C38—N3	58.5 (10)
O4—C15—C9—C14	−18.0 (8)	C36—N4—C38—N3	−59.1 (10)
O3—C15—C9—C14	161.5 (5)	C34—N3—C38—N4	−58.4 (10)
O4—C15—C9—C10	158.7 (9)	C35—N3—C38—N4	59.4 (11)
O3—C15—C9—C10	−21.8 (11)	C37X—N2X—C33X—N1X	56.0 (10)
C14—C9—C10—C11	0.1 (16)	C34X—N2X—C33X—N1X	−59.8 (9)
C15—C9—C10—C11	−176.5 (9)	C36X—N1X—C33X—N2X	−56.9 (9)
C14—C9—C10—C16	−178.2 (9)	C35X—N1X—C33X—N2X	60.9 (10)
C15—C9—C10—C16	5.2 (18)	C35X—N3X—C34X—N2X	−55.7 (14)
C9—C10—C11—C12	0.0 (17)	C38X—N3X—C34X—N2X	59.8 (13)
C16—C10—C11—C12	178.5 (8)	C33X—N2X—C34X—N3X	56.8 (11)
C10—C11—C12—C13	−0.1 (12)	C37X—N2X—C34X—N3X	−58.9 (11)
C11—C12—C13—C14	0.0 (8)	C34X—N3X—C35X—N1X	56.5 (14)
C12—C13—C14—C9	0.1 (8)	C38X—N3X—C35X—N1X	−59.0 (14)
C10—C9—C14—C13	−0.2 (11)	C36X—N1X—C35X—N3X	58.7 (12)
C15—C9—C14—C13	176.7 (5)	C33X—N1X—C35X—N3X	−58.2 (12)
O4X—C15X—C9X—C14X	167.2 (14)	C35X—N1X—C36X—N4X	−56.0 (11)
O3X—C15X—C9X—C14X	−12 (2)	C33X—N1X—C36X—N4X	60.4 (11)
O4X—C15X—C9X—C10X	−16 (3)	C37X—N4X—C36X—N1X	−63.5 (14)
O3X—C15X—C9X—C10X	165 (2)	C38X—N4X—C36X—N1X	56.1 (14)
C14X—C9X—C10X—C11X	1 (4)	C36X—N4X—C37X—N2X	62.5 (14)
C15X—C9X—C10X—C11X	−176 (2)	C38X—N4X—C37X—N2X	−56.5 (15)
C14X—C9X—C10X—C16X	−178 (2)	C33X—N2X—C37X—N4X	−59.6 (13)
C15X—C9X—C10X—C16X	5 (4)	C34X—N2X—C37X—N4X	55.7 (12)
C9X—C10X—C11X—C12X	−1 (4)	C35X—N3X—C38X—N4X	58.8 (17)
C16X—C10X—C11X—C12X	178 (2)	C34X—N3X—C38X—N4X	−58.8 (17)
C10X—C11X—C12X—C13X	2 (3)	C37X—N4X—C38X—N3X	58.8 (18)
C11X—C12X—C13X—C14X	−1 (2)	C36X—N4X—C38X—N3X	−58.3 (18)
C12X—C13X—C14X—C9X	1 (2)	C40—N6—C39—N5	−58.1 (3)
C10X—C9X—C14X—C13X	−1 (3)	C43—N6—C39—N5	58.7 (3)
C15X—C9X—C14X—C13X	176.5 (13)	C42—N5—C39—N6	−58.6 (3)
C22—C17—C18—C19	−0.3 (4)	C41—N5—C39—N6	58.1 (3)
C23—C17—C18—C19	−177.1 (3)	C41—N7—C40—N6	−58.9 (3)
C22—C17—C18—C24	179.7 (3)	C44—N7—C40—N6	58.9 (3)
C23—C17—C18—C24	2.9 (4)	C39—N6—C40—N7	58.6 (3)
C17—C18—C19—C20	0.1 (4)	C43—N6—C40—N7	−57.9 (3)
C24—C18—C19—C20	−179.9 (3)	C40—N7—C41—N5	58.8 (3)
C18—C19—C20—C21	−0.1 (5)	C44—N7—C41—N5	−58.6 (3)
C19—C20—C21—C22	0.3 (5)	C39—N5—C41—N7	−58.7 (3)
C20—C21—C22—C17	−0.5 (4)	C42—N5—C41—N7	58.0 (3)
C18—C17—C22—C21	0.6 (4)	C43—N8—C42—N5	−58.8 (3)
C23—C17—C22—C21	177.5 (3)	C44—N8—C42—N5	58.3 (3)
C18—C17—C23—O6	−6.1 (5)	C39—N5—C42—N8	58.8 (3)
C22—C17—C23—O6	177.0 (3)	C41—N5—C42—N8	−58.1 (3)
C18—C17—C23—O5	173.0 (3)	C42—N8—C43—N6	59.1 (3)
C22—C17—C23—O5	−3.8 (4)	C44—N8—C43—N6	−58.0 (3)
C30—C25—C26—C27	0.8 (4)	C39—N6—C43—N8	−59.2 (3)
C31—C25—C26—C27	−177.1 (2)	C40—N6—C43—N8	57.7 (3)
C30—C25—C26—C32	178.9 (3)	C41—N7—C44—N8	58.5 (3)
C31—C25—C26—C32	1.0 (4)	C40—N7—C44—N8	−59.0 (3)
C25—C26—C27—C28	−0.9 (4)	C43—N8—C44—N7	58.7 (3)
C32—C26—C27—C28	−179.1 (3)	C42—N8—C44—N7	−58.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.83 (5)	1.79 (5)	2.614 (7)	172 (5)
O3—H1O3···N2	0.84 (5)	1.85 (6)	2.678 (7)	172 (6)
O5—H1O5···N5	0.84 (6)	1.89 (7)	2.672 (3)	155 (9)
O7—H1O7···N6	0.89 (2)	1.79 (2)	2.670 (3)	170 (3)
C6—H6A···O1	0.95	2.34	2.685 (8)	101
C8—H8C···O2	0.98	2.44	2.774 (11)	100
C16—H16A···O3	0.98	2.39	2.814 (7)	106
C22—H22A···O5	0.95	2.32	2.681 (4)	102
C30—H30A···O7	0.95	2.33	2.677 (4)	101
C33—H33A···O4	0.99	2.58	3.146 (9)	116
C33—H33B···N8ⁱ	0.99	2.60	3.537 (5)	157
C36—H36B···N7	0.99	2.59	3.548 (8)	162
C38—H38A···O4ⁱⁱ	0.99	2.40	3.354 (14)	162
C40—H40B···N3ⁱⁱⁱ	0.99	2.59	3.509 (10)	155
C44—H44A···O6^iv	0.99	2.39	3.370 (4)	171
C44—H44B···O8^iv	0.99	2.39	3.373 (4)	172

Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) x, −y+3/2, z−1/2.

(165K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top

Crystal data top

C₆H₁₂N₄·2C₈H₈O₂	D_x = 1.314 Mg m⁻³
M_r = 412.48	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pccn	Cell parameters from 5919 reflections
a = 31.0109 (19) Å	θ = 2.3–26.6°
b = 9.3651 (6) Å	µ = 0.09 mm⁻¹
c = 14.3551 (9) Å	T = 165 K
V = 4169.0 (5) Å³	Block, colourless
Z = 8	0.43 × 0.17 × 0.15 mm
F(000) = 1760

Data collection top

Bruker APEX DUO CCD area detector diffractometer	5032 independent reflections
Radiation source: fine-focus sealed tube	3743 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 28.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −40→34
T_min = 0.919, T_max = 0.963	k = −12→12
30982 measured reflections	l = −18→18

Refinement top

Refinement on F²	387 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.167	w = 1/[σ²(F_o²) + (0.0679P)² + 2.5402P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
5032 reflections	Δρ_max = 0.43 e Å⁻³
379 parameters	Δρ_min = −0.37 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1A	0.63532 (5)	0.8145 (2)	0.52416 (12)	0.0600 (5)
H1O1	0.6610 (7)	0.798 (4)	0.504 (2)	0.110 (12)*
O2A	0.65799 (5)	0.6901 (2)	0.64468 (13)	0.0711 (5)
N1A	0.71130 (5)	0.77065 (15)	0.44111 (10)	0.0326 (3)
N2A	0.74366 (5)	0.62130 (15)	0.32109 (10)	0.0342 (3)
C1A	0.58337 (6)	0.75012 (19)	0.63499 (13)	0.0339 (4)
C2A	0.56865 (6)	0.6705 (2)	0.71097 (13)	0.0394 (4)
C3A	0.52458 (6)	0.6755 (2)	0.73178 (15)	0.0453 (5)
H3AA	0.5140	0.6215	0.7829	0.054*
C4A	0.49627 (7)	0.7558 (2)	0.68068 (15)	0.0473 (5)
H4AA	0.4666	0.7569	0.6968	0.057*
C5A	0.51067 (7)	0.8359 (2)	0.60536 (16)	0.0479 (5)
H5AA	0.4911	0.8921	0.5701	0.057*
C6A	0.55357 (6)	0.8323 (2)	0.58287 (15)	0.0421 (4)
H6AA	0.5636	0.8861	0.5311	0.051*
C7A	0.62893 (6)	0.7486 (2)	0.60296 (14)	0.0395 (4)
C8A	0.59679 (7)	0.5792 (2)	0.76997 (16)	0.0528 (5)
H8AA	0.5790	0.5268	0.8150	0.079*
H8AB	0.6175	0.6393	0.8034	0.079*
H8AC	0.6124	0.5112	0.7305	0.079*
C9A	0.70630 (6)	0.6439 (2)	0.38057 (14)	0.0382 (4)
H9AA	0.7019	0.5584	0.4199	0.046*
H9AB	0.6804	0.6561	0.3411	0.046*
C10A	0.78144 (6)	0.60384 (18)	0.38056 (13)	0.0353 (4)
H10A	0.8072	0.5886	0.3410	0.042*
H10B	0.7776	0.5180	0.4199	0.042*
C11A	0.7500	0.7500	0.49884 (16)	0.0342 (5)
H11A	0.7462	0.6693	0.5380	0.041*
C12A	0.7500	0.7500	0.26379 (17)	0.0394 (6)
H12A	0.7255	0.7624	0.2246	0.047*
O1B	0.86517 (12)	0.1709 (5)	0.2839 (3)	0.0540 (10)	0.567 (7)
H2O1	0.8453 (16)	0.197 (7)	0.250 (4)	0.11 (2)*	0.567 (7)
O2B	0.83472 (9)	0.3280 (4)	0.3777 (3)	0.0582 (11)	0.567 (7)
C1B	0.8940 (4)	0.2010 (10)	0.4375 (6)	0.0277 (14)	0.567 (7)
C2B	0.9181 (7)	0.0740 (16)	0.4388 (12)	0.0308 (18)	0.567 (7)
C3B	0.9453 (6)	0.0517 (15)	0.5144 (9)	0.0370 (17)	0.567 (7)
H3BA	0.9611	−0.0351	0.5180	0.044*	0.567 (7)
C4B	0.9502 (2)	0.1512 (10)	0.5842 (6)	0.0405 (15)	0.567 (7)
H4BA	0.9697	0.1334	0.6340	0.049*	0.567 (7)
C5B	0.9268 (2)	0.2773 (8)	0.5822 (4)	0.0396 (12)	0.567 (7)
H5BA	0.9296	0.3457	0.6306	0.048*	0.567 (7)
C6B	0.8991 (2)	0.3014 (6)	0.5078 (5)	0.0334 (12)	0.567 (7)
H6BA	0.8834	0.3884	0.5049	0.040*	0.567 (7)
C7B	0.86225 (12)	0.2392 (5)	0.3629 (3)	0.0352 (9)	0.567 (7)
C8B	0.9175 (2)	−0.0409 (6)	0.3643 (5)	0.0404 (12)	0.567 (7)
H8BA	0.8876	−0.0630	0.3476	0.061*	0.567 (7)
H8BB	0.9316	−0.1272	0.3881	0.061*	0.567 (7)
H8BC	0.9329	−0.0068	0.3090	0.061*	0.567 (7)
O1Y	0.83517 (13)	0.2629 (6)	0.3356 (3)	0.0514 (13)	0.433 (7)
H3O1	0.820 (3)	0.252 (12)	0.289 (5)	0.16 (4)*	0.433 (7)
O2Y	0.87182 (15)	0.0848 (7)	0.2732 (3)	0.0648 (15)	0.433 (7)
C1Y	0.8934 (5)	0.1700 (14)	0.4221 (8)	0.034 (2)	0.433 (7)
C2Y	0.9216 (9)	0.059 (2)	0.4455 (16)	0.037 (3)	0.433 (7)
C3Y	0.9435 (8)	0.072 (2)	0.5312 (12)	0.047 (3)	0.433 (7)
H3YA	0.9632	−0.0011	0.5487	0.056*	0.433 (7)
C4Y	0.9373 (3)	0.1844 (13)	0.5899 (7)	0.048 (2)	0.433 (7)
H4YA	0.9521	0.1875	0.6478	0.057*	0.433 (7)
C5Y	0.9098 (3)	0.2935 (10)	0.5661 (7)	0.0469 (19)	0.433 (7)
H5YA	0.9061	0.3735	0.6059	0.056*	0.433 (7)
C6Y	0.8877 (3)	0.2841 (11)	0.4832 (7)	0.0415 (18)	0.433 (7)
H6YA	0.8679	0.3576	0.4672	0.050*	0.433 (7)
C7Y	0.86596 (15)	0.1669 (7)	0.3360 (4)	0.0343 (12)	0.433 (7)
C8Y	0.9294 (3)	−0.0685 (10)	0.3851 (7)	0.0497 (18)	0.433 (7)
H8YA	0.9516	−0.1289	0.4135	0.075*	0.433 (7)
H8YB	0.9392	−0.0371	0.3235	0.075*	0.433 (7)
H8YC	0.9026	−0.1229	0.3787	0.075*	0.433 (7)
N1B	0.78896 (8)	0.2381 (2)	0.18589 (12)	0.0621 (6)
N2B	0.74629 (6)	0.12017 (15)	0.06696 (10)	0.0387 (4)
C9B	0.78427 (8)	0.1110 (2)	0.12596 (17)	0.0545 (6)
H9BA	0.8102	0.1012	0.0863	0.065*
H9BB	0.7822	0.0248	0.1656	0.065*
C10B	0.70825 (8)	0.1340 (2)	0.12585 (14)	0.0481 (5)
H10C	0.7054	0.0478	0.1653	0.058*
H10D	0.6822	0.1407	0.0862	0.058*
C11B	0.7500	0.2500	0.24366 (19)	0.0788 (14)
H11C	0.7526	0.3313	0.2828	0.095*
C12B	0.7500	0.2500	0.00997 (17)	0.0425 (6)
H12C	0.7254	0.2590	−0.0292	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0455 (9)	0.0794 (12)	0.0551 (9)	0.0093 (8)	0.0144 (7)	0.0161 (9)
O2A	0.0355 (8)	0.0950 (14)	0.0828 (12)	0.0119 (8)	0.0006 (8)	0.0248 (11)
N1A	0.0329 (8)	0.0312 (8)	0.0337 (7)	0.0007 (6)	0.0070 (6)	−0.0004 (6)
N2A	0.0446 (9)	0.0268 (7)	0.0311 (7)	0.0002 (6)	−0.0027 (6)	−0.0067 (6)
C1A	0.0334 (9)	0.0308 (8)	0.0375 (9)	−0.0021 (7)	0.0008 (7)	−0.0086 (7)
C2A	0.0409 (10)	0.0375 (10)	0.0398 (9)	−0.0047 (8)	−0.0022 (8)	−0.0070 (8)
C3A	0.0356 (10)	0.0504 (12)	0.0498 (11)	−0.0083 (9)	0.0051 (9)	−0.0153 (10)
C4A	0.0360 (10)	0.0553 (12)	0.0506 (12)	−0.0028 (9)	0.0030 (9)	−0.0151 (10)
C5A	0.0400 (11)	0.0501 (12)	0.0535 (12)	0.0106 (9)	−0.0080 (9)	−0.0099 (10)
C6A	0.0412 (10)	0.0380 (10)	0.0472 (11)	0.0026 (8)	−0.0005 (8)	−0.0052 (8)
C7A	0.0365 (10)	0.0362 (9)	0.0458 (10)	−0.0021 (8)	0.0032 (8)	−0.0068 (8)
C8A	0.0513 (12)	0.0538 (13)	0.0533 (12)	−0.0004 (10)	−0.0044 (10)	0.0065 (10)
C9A	0.0362 (9)	0.0335 (9)	0.0448 (10)	−0.0090 (7)	−0.0022 (8)	−0.0035 (8)
C10A	0.0411 (10)	0.0266 (8)	0.0381 (9)	0.0083 (7)	−0.0006 (8)	−0.0010 (7)
C11A	0.0492 (15)	0.0295 (12)	0.0237 (10)	−0.0026 (11)	0.000	0.000
C12A	0.0552 (16)	0.0397 (14)	0.0232 (11)	0.0038 (12)	0.000	0.000
O1B	0.063 (2)	0.060 (3)	0.0385 (18)	0.0279 (17)	−0.0100 (16)	−0.0097 (18)
O2B	0.0516 (17)	0.055 (2)	0.068 (2)	0.0275 (14)	−0.0198 (14)	−0.0187 (18)
C1B	0.029 (2)	0.028 (3)	0.026 (3)	0.007 (2)	0.001 (2)	0.000 (2)
C2B	0.029 (4)	0.027 (3)	0.037 (3)	−0.002 (2)	0.001 (2)	0.000 (3)
C3B	0.037 (3)	0.029 (3)	0.044 (4)	0.003 (2)	0.001 (3)	0.005 (2)
C4B	0.043 (4)	0.040 (3)	0.039 (2)	0.001 (2)	−0.005 (2)	0.007 (2)
C5B	0.045 (3)	0.040 (3)	0.034 (3)	−0.003 (3)	−0.002 (2)	−0.006 (2)
C6B	0.034 (3)	0.0280 (19)	0.038 (3)	0.0013 (19)	0.002 (2)	−0.007 (2)
C7B	0.0317 (19)	0.031 (2)	0.043 (2)	0.0016 (15)	0.0004 (15)	0.0001 (17)
C8B	0.038 (3)	0.029 (2)	0.054 (3)	0.0026 (19)	0.000 (2)	−0.005 (2)
O1Y	0.048 (2)	0.056 (3)	0.051 (2)	0.0176 (18)	−0.0148 (19)	−0.013 (2)
O2Y	0.079 (3)	0.078 (4)	0.0378 (19)	0.038 (3)	−0.0137 (18)	−0.015 (2)
C1Y	0.037 (3)	0.040 (5)	0.025 (3)	−0.006 (4)	0.009 (3)	−0.002 (3)
C2Y	0.029 (5)	0.038 (5)	0.045 (5)	−0.002 (3)	0.005 (4)	0.011 (3)
C3Y	0.044 (7)	0.047 (7)	0.049 (6)	−0.011 (4)	−0.018 (6)	0.019 (4)
C4Y	0.048 (6)	0.060 (7)	0.034 (3)	−0.016 (4)	−0.010 (4)	0.006 (4)
C5Y	0.049 (5)	0.054 (4)	0.037 (4)	−0.012 (4)	−0.005 (4)	−0.005 (3)
C6Y	0.039 (4)	0.050 (4)	0.035 (4)	−0.011 (3)	−0.004 (3)	−0.002 (3)
C7Y	0.039 (2)	0.036 (3)	0.028 (2)	0.002 (2)	0.003 (2)	0.003 (2)
C8Y	0.052 (5)	0.041 (4)	0.057 (4)	0.001 (3)	−0.008 (3)	0.007 (3)
N1B	0.1025 (17)	0.0425 (10)	0.0412 (9)	−0.0271 (10)	−0.0320 (10)	0.0172 (8)
N2B	0.0634 (10)	0.0239 (7)	0.0289 (7)	0.0003 (7)	−0.0015 (7)	−0.0014 (6)
C9B	0.0735 (15)	0.0317 (10)	0.0583 (13)	−0.0015 (10)	−0.0178 (11)	0.0133 (9)
C10B	0.0707 (14)	0.0330 (10)	0.0405 (10)	−0.0159 (9)	0.0073 (10)	−0.0093 (8)
C11B	0.167 (4)	0.0519 (19)	0.0172 (12)	−0.052 (2)	0.000	0.000
C12B	0.0737 (19)	0.0334 (13)	0.0202 (11)	0.0029 (13)	0.000	0.000

Geometric parameters (Å, º) top

O1A—C7A	1.304 (3)	C3B—H3BA	0.9500
O1A—H1O1	0.862 (18)	C4B—C5B	1.388 (7)
O2A—C7A	1.213 (2)	C4B—H4BA	0.9500
N1A—C11A	1.4713 (19)	C5B—C6B	1.388 (7)
N1A—C9A	1.479 (2)	C5B—H5BA	0.9500
N1A—C10Aⁱ	1.479 (2)	C6B—H6BA	0.9500
N2A—C9A	1.455 (2)	C8B—H8BA	0.9800
N2A—C10A	1.459 (2)	C8B—H8BB	0.9800
N2A—C12A	1.4724 (19)	C8B—H8BC	0.9800
C1A—C2A	1.398 (3)	O1Y—C7Y	1.311 (6)
C1A—C6A	1.416 (3)	O1Y—H3O1	0.83 (2)
C1A—C7A	1.486 (3)	O2Y—C7Y	1.198 (7)
C2A—C3A	1.400 (3)	C1Y—C6Y	1.394 (10)
C2A—C8A	1.487 (3)	C1Y—C2Y	1.399 (14)
C3A—C4A	1.369 (3)	C1Y—C7Y	1.501 (9)
C3A—H3AA	0.9500	C2Y—C3Y	1.408 (15)
C4A—C5A	1.389 (3)	C2Y—C8Y	1.497 (18)
C4A—H4AA	0.9500	C3Y—C4Y	1.365 (13)
C5A—C6A	1.369 (3)	C3Y—H3YA	0.9500
C5A—H5AA	0.9500	C4Y—C5Y	1.374 (10)
C6A—H6AA	0.9500	C4Y—H4YA	0.9500
C8A—H8AA	0.9800	C5Y—C6Y	1.375 (8)
C8A—H8AB	0.9800	C5Y—H5YA	0.9500
C8A—H8AC	0.9800	C6Y—H6YA	0.9500
C9A—H9AA	0.9900	C8Y—H8YA	0.9800
C9A—H9AB	0.9900	C8Y—H8YB	0.9800
C10A—N1Aⁱ	1.479 (2)	C8Y—H8YC	0.9800
C10A—H10A	0.9900	N1B—C11B	1.470 (3)
C10A—H10B	0.9900	N1B—C9B	1.475 (3)
C11A—N1Aⁱ	1.4713 (19)	N1B—C10Bⁱⁱ	1.479 (2)
C11A—H11A	0.9493	N2B—C9B	1.453 (3)
C12A—N2Aⁱ	1.4723 (19)	N2B—C10B	1.457 (3)
C12A—H12A	0.9520	N2B—C12B	1.4700 (19)
O1B—C7B	1.305 (5)	C9B—H9BA	0.9900
O1B—H2O1	0.82 (2)	C9B—H9BB	0.9900
O2B—C7B	1.211 (5)	C10B—N1Bⁱⁱ	1.479 (2)
C1B—C6B	1.389 (7)	C10B—H10C	0.9900
C1B—C2B	1.405 (10)	C10B—H10D	0.9900
C1B—C7B	1.498 (7)	C11B—N1Bⁱⁱ	1.470 (3)
C2B—C3B	1.391 (11)	C11B—H11C	0.9492
C2B—C8B	1.518 (12)	C12B—N2Bⁱⁱ	1.4700 (19)
C3B—C4B	1.377 (9)	C12B—H12C	0.9519

C7A—O1A—H1O1	111 (2)	C4B—C5B—H5BA	120.7
C11A—N1A—C9A	108.12 (12)	C6B—C5B—H5BA	120.7
C11A—N1A—C10Aⁱ	108.12 (12)	C5B—C6B—C1B	121.3 (5)
C9A—N1A—C10Aⁱ	107.95 (13)	C5B—C6B—H6BA	119.3
C9A—N2A—C10A	108.20 (14)	C1B—C6B—H6BA	119.3
C9A—N2A—C12A	108.37 (13)	O2B—C7B—O1B	122.5 (4)
C10A—N2A—C12A	108.14 (13)	O2B—C7B—C1B	120.2 (5)
C2A—C1A—C6A	119.26 (17)	O1B—C7B—C1B	117.3 (4)
C2A—C1A—C7A	123.15 (17)	C2B—C8B—H8BA	109.5
C6A—C1A—C7A	117.54 (17)	C2B—C8B—H8BB	109.5
C1A—C2A—C3A	117.87 (19)	H8BA—C8B—H8BB	109.5
C1A—C2A—C8A	124.03 (18)	C2B—C8B—H8BC	109.5
C3A—C2A—C8A	118.09 (19)	H8BA—C8B—H8BC	109.5
C4A—C3A—C2A	122.0 (2)	H8BB—C8B—H8BC	109.5
C4A—C3A—H3AA	119.0	C7Y—O1Y—H3O1	110 (8)
C2A—C3A—H3AA	119.0	C6Y—C1Y—C2Y	119.8 (9)
C3A—C4A—C5A	120.47 (19)	C6Y—C1Y—C7Y	117.5 (9)
C3A—C4A—H4AA	119.8	C2Y—C1Y—C7Y	122.6 (10)
C5A—C4A—H4AA	119.8	C1Y—C2Y—C3Y	116.7 (13)
C6A—C5A—C4A	118.8 (2)	C1Y—C2Y—C8Y	123.6 (12)
C6A—C5A—H5AA	120.6	C3Y—C2Y—C8Y	119.6 (11)
C4A—C5A—H5AA	120.6	C4Y—C3Y—C2Y	122.4 (12)
C5A—C6A—C1A	121.5 (2)	C4Y—C3Y—H3YA	118.8
C5A—C6A—H6AA	119.2	C2Y—C3Y—H3YA	118.8
C1A—C6A—H6AA	119.2	C3Y—C4Y—C5Y	120.6 (9)
O2A—C7A—O1A	121.97 (19)	C3Y—C4Y—H4YA	119.7
O2A—C7A—C1A	123.93 (19)	C5Y—C4Y—H4YA	119.7
O1A—C7A—C1A	114.10 (18)	C4Y—C5Y—C6Y	118.5 (9)
C2A—C8A—H8AA	109.5	C4Y—C5Y—H5YA	120.8
C2A—C8A—H8AB	109.5	C6Y—C5Y—H5YA	120.8
H8AA—C8A—H8AB	109.5	C5Y—C6Y—C1Y	122.0 (9)
C2A—C8A—H8AC	109.5	C5Y—C6Y—H6YA	119.0
H8AA—C8A—H8AC	109.5	C1Y—C6Y—H6YA	119.0
H8AB—C8A—H8AC	109.5	O2Y—C7Y—O1Y	123.2 (5)
N2A—C9A—N1A	112.23 (14)	O2Y—C7Y—C1Y	123.1 (6)
N2A—C9A—H9AA	109.2	O1Y—C7Y—C1Y	113.8 (7)
N1A—C9A—H9AA	109.2	C2Y—C8Y—H8YA	109.5
N2A—C9A—H9AB	109.2	C2Y—C8Y—H8YB	109.5
N1A—C9A—H9AB	109.2	H8YA—C8Y—H8YB	109.5
H9AA—C9A—H9AB	107.9	C2Y—C8Y—H8YC	109.5
N2A—C10A—N1Aⁱ	112.16 (13)	H8YA—C8Y—H8YC	109.5
N2A—C10A—H10A	109.2	H8YB—C8Y—H8YC	109.5
N1Aⁱ—C10A—H10A	109.2	C11B—N1B—C9B	108.01 (17)
N2A—C10A—H10B	109.2	C11B—N1B—C10Bⁱⁱ	108.38 (18)
N1Aⁱ—C10A—H10B	109.2	C9B—N1B—C10Bⁱⁱ	108.63 (16)
H10A—C10A—H10B	107.9	C9B—N2B—C10B	108.86 (16)
N1A—C11A—N1Aⁱ	111.44 (18)	C9B—N2B—C12B	108.04 (14)
N1A—C11A—H11A	109.7	C10B—N2B—C12B	108.23 (14)
N1Aⁱ—C11A—H11A	109.3	N2B—C9B—N1B	111.86 (18)
N2Aⁱ—C12A—N2A	112.08 (18)	N2B—C9B—H9BA	109.2
N2Aⁱ—C12A—H12A	109.7	N1B—C9B—H9BA	109.2
N2A—C12A—H12A	108.9	N2B—C9B—H9BB	109.2
C7B—O1B—H2O1	108 (5)	N1B—C9B—H9BB	109.2
C6B—C1B—C2B	120.2 (6)	H9BA—C9B—H9BB	107.9
C6B—C1B—C7B	115.6 (5)	N2B—C10B—N1Bⁱⁱ	111.27 (16)
C2B—C1B—C7B	124.2 (6)	N2B—C10B—H10C	109.4
C3B—C2B—C1B	117.5 (9)	N1Bⁱⁱ—C10B—H10C	109.4
C3B—C2B—C8B	116.8 (8)	N2B—C10B—H10D	109.4
C1B—C2B—C8B	125.7 (8)	N1Bⁱⁱ—C10B—H10D	109.4
C4B—C3B—C2B	122.2 (9)	H10C—C10B—H10D	108.0
C4B—C3B—H3BA	118.9	N1Bⁱⁱ—C11B—N1B	111.3 (2)
C2B—C3B—H3BA	118.9	N1Bⁱⁱ—C11B—H11C	110.1
C3B—C4B—C5B	120.2 (7)	N1B—C11B—H11C	108.9
C3B—C4B—H4BA	119.9	N2Bⁱⁱ—C12B—N2B	112.37 (19)
C5B—C4B—H4BA	119.9	N2Bⁱⁱ—C12B—H12C	108.6
C4B—C5B—C6B	118.6 (6)	N2B—C12B—H12C	109.8

C6A—C1A—C2A—C3A	0.3 (3)	C4B—C5B—C6B—C1B	1.5 (12)
C7A—C1A—C2A—C3A	−177.04 (17)	C2B—C1B—C6B—C5B	−2 (2)
C6A—C1A—C2A—C8A	179.25 (18)	C7B—C1B—C6B—C5B	178.4 (7)
C7A—C1A—C2A—C8A	1.9 (3)	C6B—C1B—C7B—O2B	−20.6 (13)
C1A—C2A—C3A—C4A	−0.4 (3)	C2B—C1B—C7B—O2B	160.1 (16)
C8A—C2A—C3A—C4A	−179.47 (19)	C6B—C1B—C7B—O1B	160.8 (8)
C2A—C3A—C4A—C5A	0.1 (3)	C2B—C1B—C7B—O1B	−18 (2)
C3A—C4A—C5A—C6A	0.4 (3)	C6Y—C1Y—C2Y—C3Y	−1 (4)
C4A—C5A—C6A—C1A	−0.5 (3)	C7Y—C1Y—C2Y—C3Y	−176 (2)
C2A—C1A—C6A—C5A	0.2 (3)	C6Y—C1Y—C2Y—C8Y	179 (2)
C7A—C1A—C6A—C5A	177.67 (18)	C7Y—C1Y—C2Y—C8Y	4 (4)
C2A—C1A—C7A—O2A	−7.5 (3)	C1Y—C2Y—C3Y—C4Y	1 (5)
C6A—C1A—C7A—O2A	175.1 (2)	C8Y—C2Y—C3Y—C4Y	−179 (2)
C2A—C1A—C7A—O1A	171.50 (18)	C2Y—C3Y—C4Y—C5Y	−2 (4)
C6A—C1A—C7A—O1A	−5.9 (2)	C3Y—C4Y—C5Y—C6Y	2 (2)
C10A—N2A—C9A—N1A	58.75 (19)	C4Y—C5Y—C6Y—C1Y	−2.0 (16)
C12A—N2A—C9A—N1A	−58.29 (18)	C2Y—C1Y—C6Y—C5Y	1 (3)
C11A—N1A—C9A—N2A	−58.79 (18)	C7Y—C1Y—C6Y—C5Y	176.9 (10)
C10Aⁱ—N1A—C9A—N2A	57.95 (19)	C6Y—C1Y—C7Y—O2Y	170.2 (10)
C9A—N2A—C10A—N1Aⁱ	−58.69 (18)	C2Y—C1Y—C7Y—O2Y	−14 (3)
C12A—N2A—C10A—N1Aⁱ	58.49 (18)	C6Y—C1Y—C7Y—O1Y	−9.4 (17)
C9A—N1A—C11A—N1Aⁱ	58.32 (10)	C2Y—C1Y—C7Y—O1Y	166 (2)
C10Aⁱ—N1A—C11A—N1Aⁱ	−58.32 (10)	C10B—N2B—C9B—N1B	−59.2 (2)
C9A—N2A—C12A—N2Aⁱ	58.53 (10)	C12B—N2B—C9B—N1B	58.2 (2)
C10A—N2A—C12A—N2Aⁱ	−58.54 (10)	C11B—N1B—C9B—N2B	58.8 (2)
C6B—C1B—C2B—C3B	3 (3)	C10Bⁱⁱ—N1B—C9B—N2B	−58.5 (3)
C7B—C1B—C2B—C3B	−178.0 (17)	C9B—N2B—C10B—N1Bⁱⁱ	58.8 (2)
C6B—C1B—C2B—C8B	−176.6 (16)	C12B—N2B—C10B—N1Bⁱⁱ	−58.4 (2)
C7B—C1B—C2B—C8B	3 (3)	C9B—N1B—C11B—N1Bⁱⁱ	−58.64 (11)
C1B—C2B—C3B—C4B	−2 (3)	C10Bⁱⁱ—N1B—C11B—N1Bⁱⁱ	58.88 (11)
C8B—C2B—C3B—C4B	176.9 (17)	C9B—N2B—C12B—N2Bⁱⁱ	−58.69 (13)
C2B—C3B—C4B—C5B	2 (3)	C10B—N2B—C12B—N2Bⁱⁱ	59.04 (11)
C3B—C4B—C5B—C6B	−1.1 (15)

Symmetry codes: (i) −x+3/2, −y+3/2, z; (ii) −x+3/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O1···N1A	0.86 (2)	1.82 (2)	2.672 (2)	170 (3)
O1B—H2O1···N1B	0.82 (5)	2.01 (5)	2.822 (5)	168 (6)
C6A—H6AA···O1A	0.95	2.33	2.677 (2)	101
C10A—H10B···O2B	0.99	2.58	3.067 (4)	110
C12A—H12A···O2Aⁱⁱⁱ	0.95	2.43	3.373 (2)	172
C12B—H12C···O2B^iv	0.95	2.38	3.323 (4)	169
C8B—H8BA···O1B	0.98	2.47	2.811 (7)	100

Symmetry codes: (iii) x, −y+3/2, z−1/2; (iv) −x+3/2, y, z−1/2.

(166K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top

Crystal data top

C₆H₁₂N₄·2C₈H₈O₂	D_x = 1.314 Mg m⁻³
M_r = 412.48	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pccn	Cell parameters from 9951 reflections
a = 31.0133 (15) Å	θ = 2.2–26.6°
b = 9.3657 (5) Å	µ = 0.09 mm⁻¹
c = 14.3540 (7) Å	T = 166 K
V = 4169.3 (4) Å³	Block, colourless
Z = 8	0.43 × 0.17 × 0.15 mm
F(000) = 1760

Data collection top

Bruker APEX DUO CCD area detector diffractometer	5038 independent reflections
Radiation source: fine-focus sealed tube	3971 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
φ and ω scans	θ_max = 28.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −40→40
T_min = 0.921, T_max = 0.963	k = −12→12
61779 measured reflections	l = −18→18

Refinement top

Refinement on F²	387 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.159	w = 1/[σ²(F_o²) + (0.0582P)² + 3.0812P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
5038 reflections	Δρ_max = 0.48 e Å⁻³
379 parameters	Δρ_min = −0.41 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1A	0.63536 (5)	0.8145 (2)	0.52402 (11)	0.0596 (4)
H1O1	0.6614 (7)	0.799 (4)	0.505 (2)	0.111 (12)*
O2A	0.65797 (5)	0.6902 (2)	0.64472 (13)	0.0709 (5)
N1A	0.71130 (4)	0.77067 (15)	0.44104 (10)	0.0323 (3)
N2A	0.74367 (5)	0.62131 (15)	0.32111 (10)	0.0339 (3)
C1A	0.58330 (5)	0.75008 (19)	0.63496 (12)	0.0333 (4)
C2A	0.56865 (6)	0.6706 (2)	0.71089 (13)	0.0389 (4)
C3A	0.52448 (6)	0.6757 (2)	0.73172 (15)	0.0446 (5)
H3AA	0.5139	0.6216	0.7828	0.054*
C4A	0.49630 (6)	0.7560 (2)	0.68069 (15)	0.0471 (5)
H4AA	0.4666	0.7572	0.6968	0.057*
C5A	0.51073 (7)	0.8359 (2)	0.60537 (15)	0.0483 (5)
H5AA	0.4912	0.8922	0.5701	0.058*
C6A	0.55360 (6)	0.8321 (2)	0.58284 (14)	0.0415 (4)
H6AA	0.5636	0.8858	0.5310	0.050*
C7A	0.62901 (6)	0.7486 (2)	0.60292 (13)	0.0390 (4)
C8A	0.59677 (7)	0.5790 (2)	0.77028 (16)	0.0526 (5)
H8AA	0.5789	0.5264	0.8149	0.079*
H8AB	0.6174	0.6392	0.8041	0.079*
H8AC	0.6125	0.5113	0.7309	0.079*
C9A	0.70628 (6)	0.64386 (19)	0.38051 (13)	0.0373 (4)
H9AA	0.7018	0.5584	0.4199	0.045*
H9AB	0.6804	0.6561	0.3410	0.045*
C10A	0.78146 (6)	0.60390 (18)	0.38054 (13)	0.0351 (4)
H10A	0.8072	0.5887	0.3410	0.042*
H10B	0.7776	0.5180	0.4199	0.042*
C11A	0.7500	0.7500	0.49893 (16)	0.0343 (5)
H11A	0.7462	0.6693	0.5381	0.041*
C12A	0.7500	0.7500	0.26392 (16)	0.0396 (6)
H12A	0.7255	0.7624	0.2247	0.047*
O1B	0.86512 (11)	0.1713 (5)	0.2838 (3)	0.0529 (10)	0.562 (6)
H2O1	0.8456 (16)	0.194 (7)	0.248 (4)	0.11 (2)*	0.562 (6)
O2B	0.83470 (9)	0.3282 (4)	0.3781 (3)	0.0576 (10)	0.562 (6)
C1B	0.8941 (4)	0.2011 (10)	0.4372 (6)	0.0269 (14)	0.562 (6)
C2B	0.9188 (7)	0.0748 (19)	0.4377 (12)	0.031 (2)	0.562 (6)
C3B	0.9451 (6)	0.0518 (16)	0.5142 (10)	0.0382 (17)	0.562 (6)
H3BA	0.9604	−0.0358	0.5182	0.046*	0.562 (6)
C4B	0.9500 (3)	0.1500 (9)	0.5848 (6)	0.0410 (15)	0.562 (6)
H4BA	0.9692	0.1313	0.6349	0.049*	0.562 (6)
C5B	0.9267 (2)	0.2771 (7)	0.5820 (4)	0.0379 (12)	0.562 (6)
H5BA	0.9296	0.3462	0.6301	0.046*	0.562 (6)
C6B	0.8992 (2)	0.3005 (6)	0.5078 (5)	0.0339 (12)	0.562 (6)
H6BA	0.8833	0.3872	0.5052	0.041*	0.562 (6)
C7B	0.86200 (12)	0.2395 (5)	0.3630 (3)	0.0341 (9)	0.562 (6)
C8B	0.9173 (2)	−0.0406 (7)	0.3642 (5)	0.0407 (12)	0.562 (6)
H8BA	0.8872	−0.0618	0.3484	0.061*	0.562 (6)
H8BB	0.9313	−0.1271	0.3881	0.061*	0.562 (6)
H8BC	0.9326	−0.0079	0.3083	0.061*	0.562 (6)
O1Y	0.83519 (13)	0.2633 (6)	0.3357 (3)	0.0534 (13)	0.438 (6)
H3O1	0.818 (2)	0.250 (10)	0.292 (4)	0.12 (3)*	0.438 (6)
O2Y	0.87177 (15)	0.0850 (7)	0.2733 (3)	0.0653 (15)	0.438 (6)
C1Y	0.8931 (6)	0.1705 (15)	0.4228 (9)	0.035 (2)	0.438 (6)
C2Y	0.9206 (10)	0.059 (3)	0.4468 (17)	0.035 (3)	0.438 (6)
C3Y	0.9439 (8)	0.070 (2)	0.5307 (13)	0.045 (3)	0.438 (6)
H3YA	0.9641	−0.0019	0.5470	0.054*	0.438 (6)
C4Y	0.9377 (4)	0.1853 (13)	0.5894 (7)	0.049 (2)	0.438 (6)
H4YA	0.9530	0.1897	0.6467	0.058*	0.438 (6)
C5Y	0.9098 (3)	0.2939 (10)	0.5660 (6)	0.0475 (18)	0.438 (6)
H5YA	0.9059	0.3730	0.6065	0.057*	0.438 (6)
C6Y	0.8876 (3)	0.2862 (11)	0.4835 (7)	0.0412 (17)	0.438 (6)
H6YA	0.8682	0.3606	0.4672	0.049*	0.438 (6)
C7Y	0.86598 (15)	0.1673 (7)	0.3360 (4)	0.0343 (12)	0.438 (6)
C8Y	0.9292 (3)	−0.0681 (9)	0.3845 (7)	0.0487 (17)	0.438 (6)
H8YA	0.9516	−0.1282	0.4126	0.073*	0.438 (6)
H8YB	0.9390	−0.0347	0.3233	0.073*	0.438 (6)
H8YC	0.9026	−0.1237	0.3772	0.073*	0.438 (6)
N1B	0.78896 (8)	0.2380 (2)	0.18602 (12)	0.0620 (6)
N2B	0.74625 (6)	0.12017 (15)	0.06701 (10)	0.0384 (4)
C9B	0.78417 (8)	0.1109 (2)	0.12608 (16)	0.0542 (6)
H9BA	0.8101	0.1008	0.0865	0.065*
H9BB	0.7820	0.0247	0.1657	0.065*
C10B	0.70831 (8)	0.1340 (2)	0.12595 (14)	0.0477 (5)
H10C	0.7055	0.0479	0.1655	0.057*
H10D	0.6823	0.1406	0.0863	0.057*
C11B	0.7500	0.2500	0.24375 (19)	0.0792 (14)
H11C	0.7526	0.3313	0.2829	0.095*
C12B	0.7500	0.2500	0.01012 (16)	0.0420 (6)
H12C	0.7254	0.2590	−0.0291	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0452 (9)	0.0787 (11)	0.0548 (9)	0.0094 (8)	0.0141 (7)	0.0158 (8)
O2A	0.0355 (8)	0.0938 (13)	0.0834 (12)	0.0125 (8)	0.0016 (8)	0.0264 (11)
N1A	0.0331 (7)	0.0298 (7)	0.0341 (7)	0.0001 (6)	0.0070 (6)	−0.0005 (6)
N2A	0.0443 (8)	0.0256 (7)	0.0319 (7)	0.0006 (6)	−0.0022 (6)	−0.0068 (6)
C1A	0.0322 (8)	0.0289 (8)	0.0387 (9)	−0.0024 (7)	0.0010 (7)	−0.0084 (7)
C2A	0.0402 (10)	0.0349 (9)	0.0414 (9)	−0.0036 (8)	−0.0023 (8)	−0.0069 (8)
C3A	0.0355 (10)	0.0495 (11)	0.0490 (11)	−0.0083 (8)	0.0051 (8)	−0.0142 (9)
C4A	0.0355 (9)	0.0543 (12)	0.0516 (11)	−0.0035 (9)	0.0026 (8)	−0.0152 (10)
C5A	0.0404 (10)	0.0497 (12)	0.0547 (12)	0.0102 (9)	−0.0070 (9)	−0.0098 (10)
C6A	0.0416 (10)	0.0366 (10)	0.0465 (10)	0.0025 (8)	−0.0005 (8)	−0.0048 (8)
C7A	0.0362 (9)	0.0348 (9)	0.0459 (10)	−0.0017 (8)	0.0044 (8)	−0.0062 (8)
C8A	0.0524 (12)	0.0521 (12)	0.0534 (12)	−0.0003 (10)	−0.0035 (10)	0.0064 (10)
C9A	0.0359 (9)	0.0308 (9)	0.0451 (10)	−0.0090 (7)	−0.0021 (8)	−0.0030 (7)
C10A	0.0412 (9)	0.0251 (8)	0.0389 (9)	0.0081 (7)	−0.0008 (7)	−0.0007 (7)
C11A	0.0488 (14)	0.0300 (11)	0.0241 (10)	−0.0020 (11)	0.000	0.000
C12A	0.0578 (16)	0.0389 (13)	0.0220 (10)	0.0042 (12)	0.000	0.000
O1B	0.063 (2)	0.058 (2)	0.0373 (17)	0.0275 (16)	−0.0110 (15)	−0.0076 (17)
O2B	0.0524 (17)	0.0523 (19)	0.068 (2)	0.0275 (13)	−0.0192 (14)	−0.0201 (17)
C1B	0.025 (2)	0.026 (3)	0.030 (3)	0.004 (2)	0.001 (2)	0.003 (2)
C2B	0.029 (3)	0.029 (4)	0.035 (3)	−0.002 (3)	0.003 (3)	0.002 (4)
C3B	0.040 (4)	0.029 (3)	0.046 (4)	0.000 (3)	0.000 (3)	0.006 (2)
C4B	0.047 (4)	0.035 (3)	0.041 (2)	0.000 (2)	−0.008 (2)	0.009 (2)
C5B	0.042 (3)	0.038 (2)	0.033 (2)	−0.002 (3)	−0.003 (2)	−0.0041 (18)
C6B	0.034 (3)	0.030 (2)	0.037 (3)	0.003 (2)	0.000 (2)	−0.003 (2)
C7B	0.0315 (18)	0.0294 (19)	0.0415 (19)	0.0013 (15)	−0.0006 (15)	0.0006 (16)
C8B	0.037 (3)	0.030 (2)	0.056 (3)	0.0034 (19)	0.000 (2)	−0.004 (2)
O1Y	0.047 (2)	0.059 (3)	0.054 (2)	0.0187 (18)	−0.0166 (19)	−0.012 (2)
O2Y	0.079 (3)	0.076 (4)	0.041 (2)	0.036 (2)	−0.0130 (18)	−0.013 (2)
C1Y	0.039 (3)	0.041 (6)	0.026 (3)	−0.005 (4)	0.007 (2)	−0.003 (3)
C2Y	0.035 (5)	0.028 (4)	0.043 (5)	−0.006 (3)	0.001 (4)	0.012 (3)
C3Y	0.041 (6)	0.043 (7)	0.050 (6)	−0.010 (4)	−0.019 (6)	0.017 (4)
C4Y	0.055 (6)	0.056 (7)	0.035 (3)	−0.015 (4)	−0.014 (4)	0.008 (4)
C5Y	0.048 (4)	0.051 (4)	0.043 (4)	−0.009 (3)	−0.007 (3)	−0.005 (3)
C6Y	0.038 (4)	0.048 (4)	0.038 (4)	−0.006 (3)	−0.003 (3)	−0.001 (3)
C7Y	0.036 (2)	0.038 (3)	0.030 (2)	0.003 (2)	0.003 (2)	0.006 (2)
C8Y	0.051 (5)	0.038 (4)	0.057 (4)	0.000 (3)	−0.006 (3)	0.005 (3)
N1B	0.1027 (16)	0.0408 (9)	0.0424 (9)	−0.0261 (10)	−0.0321 (10)	0.0170 (8)
N2B	0.0629 (10)	0.0226 (7)	0.0299 (7)	0.0006 (7)	−0.0018 (7)	−0.0025 (6)
C9B	0.0741 (15)	0.0291 (9)	0.0593 (13)	−0.0019 (10)	−0.0184 (11)	0.0138 (9)
C10B	0.0703 (14)	0.0319 (9)	0.0407 (10)	−0.0148 (9)	0.0066 (9)	−0.0090 (8)
C11B	0.169 (4)	0.0512 (18)	0.0177 (12)	−0.050 (2)	0.000	0.000
C12B	0.0741 (19)	0.0317 (12)	0.0202 (10)	0.0039 (13)	0.000	0.000

Geometric parameters (Å, º) top

O1A—C7A	1.305 (2)	C3B—H3BA	0.9500
O1A—H1O1	0.868 (18)	C4B—C5B	1.393 (7)
O2A—C7A	1.211 (2)	C4B—H4BA	0.9500
N1A—C11A	1.4725 (19)	C5B—C6B	1.382 (6)
N1A—C10Aⁱ	1.478 (2)	C5B—H5BA	0.9500
N1A—C9A	1.480 (2)	C6B—H6BA	0.9500
N2A—C9A	1.455 (2)	C8B—H8BA	0.9800
N2A—C10A	1.459 (2)	C8B—H8BB	0.9800
N2A—C12A	1.4714 (19)	C8B—H8BC	0.9800
C1A—C2A	1.396 (3)	O1Y—C7Y	1.311 (6)
C1A—C6A	1.414 (3)	O1Y—H3O1	0.83 (2)
C1A—C7A	1.490 (2)	O2Y—C7Y	1.199 (7)
C2A—C3A	1.403 (3)	C1Y—C2Y	1.392 (14)
C2A—C8A	1.491 (3)	C1Y—C6Y	1.401 (11)
C3A—C4A	1.366 (3)	C1Y—C7Y	1.504 (9)
C3A—H3AA	0.9500	C2Y—C3Y	1.409 (15)
C4A—C5A	1.389 (3)	C2Y—C8Y	1.512 (19)
C4A—H4AA	0.9500	C3Y—C4Y	1.382 (13)
C5A—C6A	1.369 (3)	C3Y—H3YA	0.9500
C5A—H5AA	0.9500	C4Y—C5Y	1.378 (9)
C6A—H6AA	0.9500	C4Y—H4YA	0.9500
C8A—H8AA	0.9800	C5Y—C6Y	1.370 (8)
C8A—H8AB	0.9800	C5Y—H5YA	0.9500
C8A—H8AC	0.9800	C6Y—H6YA	0.9500
C9A—H9AA	0.9900	C8Y—H8YA	0.9800
C9A—H9AB	0.9900	C8Y—H8YB	0.9800
C10A—N1Aⁱ	1.478 (2)	C8Y—H8YC	0.9800
C10A—H10A	0.9900	N1B—C11B	1.469 (3)
C10A—H10B	0.9900	N1B—C9B	1.477 (3)
C11A—N1Aⁱ	1.4726 (19)	N1B—C10Bⁱⁱ	1.479 (2)
C11A—H11A	0.9493	N2B—C9B	1.453 (3)
C12A—N2Aⁱ	1.4714 (19)	N2B—C10B	1.455 (3)
C12A—H12A	0.9520	N2B—C12B	1.4693 (19)
O1B—C7B	1.309 (4)	C9B—H9BA	0.9900
O1B—H2O1	0.82 (2)	C9B—H9BB	0.9900
O2B—C7B	1.206 (5)	C10B—N1Bⁱⁱ	1.479 (2)
C1B—C6B	1.386 (7)	C10B—H10C	0.9900
C1B—C2B	1.408 (11)	C10B—H10D	0.9900
C1B—C7B	1.502 (6)	C11B—N1Bⁱⁱ	1.469 (3)
C2B—C3B	1.385 (11)	C11B—H11C	0.9492
C2B—C8B	1.511 (13)	C12B—N2Bⁱⁱ	1.4693 (19)
C3B—C4B	1.377 (9)	C12B—H12C	0.9520

C7A—O1A—H1O1	110 (2)	C6B—C5B—H5BA	120.7
C11A—N1A—C10Aⁱ	108.18 (12)	C4B—C5B—H5BA	120.7
C11A—N1A—C9A	108.15 (12)	C5B—C6B—C1B	121.8 (5)
C10Aⁱ—N1A—C9A	107.99 (13)	C5B—C6B—H6BA	119.1
C9A—N2A—C10A	108.29 (13)	C1B—C6B—H6BA	119.1
C9A—N2A—C12A	108.33 (12)	O2B—C7B—O1B	123.0 (4)
C10A—N2A—C12A	108.10 (12)	O2B—C7B—C1B	120.3 (5)
C2A—C1A—C6A	119.39 (17)	O1B—C7B—C1B	116.7 (4)
C2A—C1A—C7A	123.06 (17)	C2B—C8B—H8BA	109.5
C6A—C1A—C7A	117.50 (17)	C2B—C8B—H8BB	109.5
C1A—C2A—C3A	117.80 (18)	H8BA—C8B—H8BB	109.5
C1A—C2A—C8A	124.25 (18)	C2B—C8B—H8BC	109.5
C3A—C2A—C8A	117.94 (19)	H8BA—C8B—H8BC	109.5
C4A—C3A—C2A	121.9 (2)	H8BB—C8B—H8BC	109.5
C4A—C3A—H3AA	119.0	C7Y—O1Y—H3O1	111 (7)
C2A—C3A—H3AA	119.0	C2Y—C1Y—C6Y	120.1 (9)
C3A—C4A—C5A	120.52 (19)	C2Y—C1Y—C7Y	122.2 (10)
C3A—C4A—H4AA	119.7	C6Y—C1Y—C7Y	117.6 (9)
C5A—C4A—H4AA	119.7	C1Y—C2Y—C3Y	118.0 (14)
C6A—C5A—C4A	118.9 (2)	C1Y—C2Y—C8Y	123.5 (12)
C6A—C5A—H5AA	120.6	C3Y—C2Y—C8Y	118.3 (11)
C4A—C5A—H5AA	120.6	C4Y—C3Y—C2Y	120.5 (12)
C5A—C6A—C1A	121.47 (19)	C4Y—C3Y—H3YA	119.7
C5A—C6A—H6AA	119.3	C2Y—C3Y—H3YA	119.7
C1A—C6A—H6AA	119.3	C5Y—C4Y—C3Y	121.0 (8)
O2A—C7A—O1A	122.14 (18)	C5Y—C4Y—H4YA	119.5
O2A—C7A—C1A	123.84 (18)	C3Y—C4Y—H4YA	119.5
O1A—C7A—C1A	114.01 (17)	C6Y—C5Y—C4Y	119.2 (9)
C2A—C8A—H8AA	109.5	C6Y—C5Y—H5YA	120.4
C2A—C8A—H8AB	109.5	C4Y—C5Y—H5YA	120.4
H8AA—C8A—H8AB	109.5	C5Y—C6Y—C1Y	121.1 (9)
C2A—C8A—H8AC	109.5	C5Y—C6Y—H6YA	119.4
H8AA—C8A—H8AC	109.5	C1Y—C6Y—H6YA	119.4
H8AB—C8A—H8AC	109.5	O2Y—C7Y—O1Y	123.2 (5)
N2A—C9A—N1A	112.14 (13)	O2Y—C7Y—C1Y	123.5 (6)
N2A—C9A—H9AA	109.2	O1Y—C7Y—C1Y	113.4 (7)
N1A—C9A—H9AA	109.2	C2Y—C8Y—H8YA	109.5
N2A—C9A—H9AB	109.2	C2Y—C8Y—H8YB	109.5
N1A—C9A—H9AB	109.2	H8YA—C8Y—H8YB	109.5
H9AA—C9A—H9AB	107.9	C2Y—C8Y—H8YC	109.5
N2A—C10A—N1Aⁱ	112.15 (13)	H8YA—C8Y—H8YC	109.5
N2A—C10A—H10A	109.2	H8YB—C8Y—H8YC	109.5
N1Aⁱ—C10A—H10A	109.2	C11B—N1B—C9B	107.90 (17)
N2A—C10A—H10B	109.2	C11B—N1B—C10Bⁱⁱ	108.29 (18)
N1Aⁱ—C10A—H10B	109.2	C9B—N1B—C10Bⁱⁱ	108.64 (15)
H10A—C10A—H10B	107.9	C9B—N2B—C10B	108.71 (16)
N1A—C11A—N1Aⁱ	111.31 (18)	C9B—N2B—C12B	108.05 (14)
N1A—C11A—H11A	109.7	C10B—N2B—C12B	108.28 (14)
N1Aⁱ—C11A—H11A	109.3	N2B—C9B—N1B	111.91 (17)
N2Aⁱ—C12A—N2A	112.18 (18)	N2B—C9B—H9BA	109.2
N2Aⁱ—C12A—H12A	109.7	N1B—C9B—H9BA	109.2
N2A—C12A—H12A	108.8	N2B—C9B—H9BB	109.2
C7B—O1B—H2O1	111 (5)	N1B—C9B—H9BB	109.2
C6B—C1B—C2B	120.0 (6)	H9BA—C9B—H9BB	107.9
C6B—C1B—C7B	115.6 (5)	N2B—C10B—N1Bⁱⁱ	111.40 (16)
C2B—C1B—C7B	124.4 (7)	N2B—C10B—H10C	109.3
C3B—C2B—C1B	117.0 (9)	N1Bⁱⁱ—C10B—H10C	109.3
C3B—C2B—C8B	117.4 (8)	N2B—C10B—H10D	109.3
C1B—C2B—C8B	125.5 (8)	N1Bⁱⁱ—C10B—H10D	109.3
C4B—C3B—C2B	123.1 (10)	H10C—C10B—H10D	108.0
C4B—C3B—H3BA	118.5	N1B—C11B—N1Bⁱⁱ	111.4 (2)
C2B—C3B—H3BA	118.5	N1B—C11B—H11C	108.9
C3B—C4B—C5B	119.5 (7)	N1Bⁱⁱ—C11B—H11C	110.1
C3B—C4B—H4BA	120.3	N2B—C12B—N2Bⁱⁱ	112.47 (18)
C5B—C4B—H4BA	120.3	N2B—C12B—H12C	109.8
C6B—C5B—C4B	118.5 (6)	N2Bⁱⁱ—C12B—H12C	108.6

C6A—C1A—C2A—C3A	0.3 (3)	C4B—C5B—C6B—C1B	0.4 (12)
C7A—C1A—C2A—C3A	−177.09 (16)	C2B—C1B—C6B—C5B	−3 (2)
C6A—C1A—C2A—C8A	179.29 (18)	C7B—C1B—C6B—C5B	178.0 (7)
C7A—C1A—C2A—C8A	1.9 (3)	C6B—C1B—C7B—O2B	−19.8 (14)
C1A—C2A—C3A—C4A	−0.6 (3)	C2B—C1B—C7B—O2B	161.1 (17)
C8A—C2A—C3A—C4A	−179.60 (19)	C6B—C1B—C7B—O1B	161.0 (8)
C2A—C3A—C4A—C5A	0.2 (3)	C2B—C1B—C7B—O1B	−18 (2)
C3A—C4A—C5A—C6A	0.4 (3)	C6Y—C1Y—C2Y—C3Y	−3 (4)
C4A—C5A—C6A—C1A	−0.6 (3)	C7Y—C1Y—C2Y—C3Y	−178 (2)
C2A—C1A—C6A—C5A	0.3 (3)	C6Y—C1Y—C2Y—C8Y	−179 (2)
C7A—C1A—C6A—C5A	177.81 (18)	C7Y—C1Y—C2Y—C8Y	6 (5)
C2A—C1A—C7A—O2A	−7.5 (3)	C1Y—C2Y—C3Y—C4Y	3 (5)
C6A—C1A—C7A—O2A	175.1 (2)	C8Y—C2Y—C3Y—C4Y	179 (2)
C2A—C1A—C7A—O1A	171.51 (17)	C2Y—C3Y—C4Y—C5Y	−2 (4)
C6A—C1A—C7A—O1A	−5.9 (2)	C3Y—C4Y—C5Y—C6Y	1 (2)
C10A—N2A—C9A—N1A	58.73 (18)	C4Y—C5Y—C6Y—C1Y	−0.2 (17)
C12A—N2A—C9A—N1A	−58.28 (18)	C2Y—C1Y—C6Y—C5Y	2 (3)
C11A—N1A—C9A—N2A	−58.83 (18)	C7Y—C1Y—C6Y—C5Y	177.1 (10)
C10Aⁱ—N1A—C9A—N2A	58.02 (18)	C2Y—C1Y—C7Y—O2Y	−15 (3)
C9A—N2A—C10A—N1Aⁱ	−58.70 (18)	C6Y—C1Y—C7Y—O2Y	169.7 (11)
C12A—N2A—C10A—N1Aⁱ	58.46 (18)	C2Y—C1Y—C7Y—O1Y	165 (2)
C10Aⁱ—N1A—C11A—N1Aⁱ	−58.36 (9)	C6Y—C1Y—C7Y—O1Y	−10.5 (18)
C9A—N1A—C11A—N1Aⁱ	58.37 (10)	C10B—N2B—C9B—N1B	−59.3 (2)
C9A—N2A—C12A—N2Aⁱ	58.58 (10)	C12B—N2B—C9B—N1B	58.0 (2)
C10A—N2A—C12A—N2Aⁱ	−58.55 (10)	C11B—N1B—C9B—N2B	58.9 (2)
C6B—C1B—C2B—C3B	5 (3)	C10Bⁱⁱ—N1B—C9B—N2B	−58.3 (3)
C7B—C1B—C2B—C3B	−176.3 (18)	C9B—N2B—C10B—N1Bⁱⁱ	58.9 (2)
C6B—C1B—C2B—C8B	−178.4 (17)	C12B—N2B—C10B—N1Bⁱⁱ	−58.2 (2)
C7B—C1B—C2B—C8B	1 (3)	C9B—N1B—C11B—N1Bⁱⁱ	−58.61 (11)
C1B—C2B—C3B—C4B	−4 (4)	C10Bⁱⁱ—N1B—C11B—N1Bⁱⁱ	58.81 (11)
C8B—C2B—C3B—C4B	178.4 (18)	C9B—N2B—C12B—N2Bⁱⁱ	−58.63 (13)
C2B—C3B—C4B—C5B	2 (3)	C10B—N2B—C12B—N2Bⁱⁱ	58.94 (11)
C3B—C4B—C5B—C6B	−0.1 (16)

Symmetry codes: (i) −x+3/2, −y+3/2, z; (ii) −x+3/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O1···N1A	0.87 (2)	1.82 (2)	2.671 (2)	168 (3)
O1B—H2O1···N1B	0.82 (5)	2.01 (5)	2.818 (4)	167 (6)
C6A—H6AA···O1A	0.95	2.33	2.678 (2)	101
C10A—H10B···O2B	0.99	2.58	3.065 (4)	110
C12A—H12A···O2Aⁱⁱⁱ	0.95	2.43	3.375 (2)	172
C12B—H12C···O2B^iv	0.95	2.38	3.321 (4)	169
C8B—H8BA···O1B	0.98	2.47	2.809 (8)	100

Symmetry codes: (iii) x, −y+3/2, z−1/2; (iv) −x+3/2, y, z−1/2.

(170K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top

Crystal data top

C₆H₁₂N₄·2C₈H₈O₂	D_x = 1.313 Mg m⁻³
M_r = 412.48	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pccn	Cell parameters from 9951 reflections
a = 31.0259 (15) Å	θ = 2.3–26.6°
b = 9.3706 (4) Å	µ = 0.09 mm⁻¹
c = 14.3567 (7) Å	T = 170 K
V = 4173.9 (3) Å³	Block, colourless
Z = 8	0.43 × 0.17 × 0.15 mm
F(000) = 1760

Data collection top

Bruker APEX DUO CCD area detector diffractometer	5043 independent reflections
Radiation source: fine-focus sealed tube	3967 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 28.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −40→40
T_min = 0.925, T_max = 0.963	k = −12→12
61851 measured reflections	l = −18→18

Refinement top

Refinement on F²	387 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.161	w = 1/[σ²(F_o²) + (0.062P)² + 2.6644P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
5043 reflections	Δρ_max = 0.40 e Å⁻³
379 parameters	Δρ_min = −0.39 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1A	0.63539 (5)	0.8144 (2)	0.52413 (11)	0.0606 (4)
H1O1	0.6613 (7)	0.797 (4)	0.504 (2)	0.123 (13)*
O2A	0.65797 (5)	0.6901 (2)	0.64482 (13)	0.0724 (5)
N1A	0.71130 (4)	0.77061 (15)	0.44124 (10)	0.0328 (3)
N2A	0.74368 (5)	0.62144 (14)	0.32121 (9)	0.0346 (3)
C1A	0.58331 (5)	0.75010 (19)	0.63498 (12)	0.0342 (4)
C2A	0.56869 (6)	0.67060 (19)	0.71091 (13)	0.0396 (4)
C3A	0.52453 (6)	0.6755 (2)	0.73182 (14)	0.0458 (5)
H3AA	0.5139	0.6216	0.7830	0.055*
C4A	0.49632 (6)	0.7558 (2)	0.68068 (15)	0.0476 (5)
H4AA	0.4666	0.7568	0.6968	0.057*
C5A	0.51075 (6)	0.8358 (2)	0.60535 (15)	0.0492 (5)
H5AA	0.4912	0.8922	0.5701	0.059*
C6A	0.55364 (6)	0.8319 (2)	0.58289 (14)	0.0426 (4)
H6AA	0.5637	0.8855	0.5311	0.051*
C7A	0.62903 (6)	0.7484 (2)	0.60308 (13)	0.0396 (4)
C8A	0.59678 (7)	0.5791 (2)	0.77010 (16)	0.0533 (5)
H8AA	0.5790	0.5270	0.8151	0.080*
H8AB	0.6175	0.6391	0.8035	0.080*
H8AC	0.6123	0.5110	0.7307	0.080*
C9A	0.70635 (6)	0.64386 (19)	0.38054 (13)	0.0378 (4)
H9AA	0.7019	0.5583	0.4199	0.045*
H9AB	0.6804	0.6561	0.3411	0.045*
C10A	0.78141 (6)	0.60396 (17)	0.38066 (12)	0.0356 (4)
H10A	0.8071	0.5887	0.3411	0.043*
H10B	0.7776	0.5181	0.4200	0.043*
C11A	0.7500	0.7500	0.49906 (16)	0.0349 (5)
H11A	0.7462	0.6693	0.5382	0.042*
C12A	0.7500	0.7500	0.26388 (16)	0.0394 (6)
H12A	0.7255	0.7624	0.2247	0.047*
O1B	0.86500 (11)	0.1712 (5)	0.2842 (3)	0.0537 (10)	0.563 (7)
H2O1	0.8455 (16)	0.193 (7)	0.248 (4)	0.11 (2)*	0.563 (7)
O2B	0.83470 (9)	0.3280 (4)	0.3782 (3)	0.0586 (10)	0.563 (7)
C1B	0.8940 (4)	0.2001 (12)	0.4371 (7)	0.0292 (14)	0.563 (7)
C2B	0.9188 (8)	0.0751 (19)	0.4371 (12)	0.032 (2)	0.563 (7)
C3B	0.9449 (6)	0.0524 (15)	0.5140 (10)	0.0388 (17)	0.563 (7)
H3BA	0.9600	−0.0356	0.5184	0.047*	0.563 (7)
C4B	0.9502 (3)	0.1502 (9)	0.5844 (6)	0.0417 (15)	0.563 (7)
H4BA	0.9695	0.1315	0.6343	0.050*	0.563 (7)
C5B	0.9268 (2)	0.2774 (7)	0.5818 (4)	0.0399 (12)	0.563 (7)
H5BA	0.9299	0.3467	0.6297	0.048*	0.563 (7)
C6B	0.8991 (2)	0.3002 (7)	0.5080 (5)	0.0350 (12)	0.563 (7)
H6BA	0.8831	0.3865	0.5054	0.042*	0.563 (7)
C7B	0.86201 (12)	0.2397 (5)	0.3635 (3)	0.0349 (9)	0.563 (7)
C8B	0.9173 (2)	−0.0403 (7)	0.3638 (5)	0.0423 (12)	0.563 (7)
H8BA	0.8873	−0.0600	0.3473	0.063*	0.563 (7)
H8BB	0.9307	−0.1273	0.3883	0.063*	0.563 (7)
H8BC	0.9330	−0.0085	0.3084	0.063*	0.563 (7)
O1Y	0.83516 (13)	0.2635 (6)	0.3359 (3)	0.0544 (13)	0.437 (7)
H3O1	0.820 (2)	0.250 (10)	0.289 (4)	0.12 (3)*	0.437 (7)
O2Y	0.87172 (15)	0.0857 (7)	0.2734 (3)	0.0665 (15)	0.437 (7)
C1Y	0.8932 (6)	0.1721 (17)	0.4228 (10)	0.037 (2)	0.437 (7)
C2Y	0.9203 (11)	0.059 (3)	0.4472 (17)	0.035 (3)	0.437 (7)
C3Y	0.9440 (8)	0.070 (2)	0.5307 (13)	0.046 (3)	0.437 (7)
H3YA	0.9643	−0.0019	0.5466	0.056*	0.437 (7)
C4Y	0.9376 (4)	0.1845 (13)	0.5895 (7)	0.050 (2)	0.437 (7)
H4YA	0.9528	0.1883	0.6470	0.060*	0.437 (7)
C5Y	0.9099 (3)	0.2934 (10)	0.5664 (7)	0.0493 (19)	0.437 (7)
H5YA	0.9060	0.3723	0.6071	0.059*	0.437 (7)
C6Y	0.8879 (3)	0.2859 (11)	0.4836 (7)	0.0425 (18)	0.437 (7)
H6YA	0.8685	0.3605	0.4675	0.051*	0.437 (7)
C7Y	0.86614 (14)	0.1683 (7)	0.3363 (4)	0.0350 (12)	0.437 (7)
C8Y	0.9289 (3)	−0.0678 (10)	0.3845 (7)	0.0490 (17)	0.437 (7)
H8YA	0.9516	−0.1272	0.4120	0.073*	0.437 (7)
H8YB	0.9382	−0.0340	0.3232	0.073*	0.437 (7)
H8YC	0.9025	−0.1242	0.3779	0.073*	0.437 (7)
N1B	0.78894 (7)	0.23790 (19)	0.18616 (12)	0.0623 (6)
N2B	0.74620 (6)	0.12017 (15)	0.06713 (10)	0.0395 (4)
C9B	0.78416 (8)	0.1110 (2)	0.12613 (16)	0.0552 (6)
H9BA	0.8101	0.1012	0.0865	0.066*
H9BB	0.7821	0.0248	0.1657	0.066*
C10B	0.70825 (7)	0.1340 (2)	0.12605 (14)	0.0483 (5)
H10C	0.7054	0.0479	0.1656	0.058*
H10D	0.6822	0.1407	0.0864	0.058*
C11B	0.7500	0.2500	0.24373 (18)	0.0787 (13)
H11C	0.7526	0.3313	0.2828	0.094*
C12B	0.7500	0.2500	0.01011 (16)	0.0429 (6)
H12C	0.7254	0.2590	−0.0291	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0469 (9)	0.0788 (11)	0.0560 (9)	0.0107 (8)	0.0142 (7)	0.0158 (8)
O2A	0.0363 (8)	0.0970 (14)	0.0839 (12)	0.0123 (8)	0.0015 (8)	0.0264 (11)
N1A	0.0330 (7)	0.0304 (7)	0.0350 (7)	0.0000 (6)	0.0073 (6)	−0.0006 (6)
N2A	0.0449 (8)	0.0268 (7)	0.0322 (7)	0.0004 (6)	−0.0024 (6)	−0.0064 (5)
C1A	0.0323 (8)	0.0305 (8)	0.0398 (9)	−0.0025 (7)	0.0011 (7)	−0.0092 (7)
C2A	0.0402 (9)	0.0365 (9)	0.0421 (9)	−0.0038 (7)	−0.0014 (7)	−0.0071 (8)
C3A	0.0370 (10)	0.0501 (11)	0.0504 (11)	−0.0085 (8)	0.0061 (8)	−0.0147 (9)
C4A	0.0353 (9)	0.0553 (12)	0.0523 (11)	−0.0042 (9)	0.0031 (8)	−0.0147 (10)
C5A	0.0410 (10)	0.0503 (12)	0.0563 (12)	0.0110 (9)	−0.0076 (9)	−0.0096 (10)
C6A	0.0422 (10)	0.0378 (10)	0.0478 (10)	0.0026 (8)	−0.0006 (8)	−0.0049 (8)
C7A	0.0371 (9)	0.0349 (9)	0.0467 (10)	−0.0020 (8)	0.0037 (8)	−0.0060 (8)
C8A	0.0509 (12)	0.0540 (12)	0.0550 (12)	−0.0009 (10)	−0.0037 (10)	0.0056 (10)
C9A	0.0359 (9)	0.0315 (8)	0.0461 (10)	−0.0091 (7)	−0.0016 (7)	−0.0030 (7)
C10A	0.0422 (9)	0.0251 (8)	0.0396 (9)	0.0083 (7)	−0.0009 (7)	−0.0010 (7)
C11A	0.0505 (14)	0.0305 (11)	0.0236 (10)	−0.0022 (10)	0.000	0.000
C12A	0.0564 (15)	0.0388 (13)	0.0230 (10)	0.0046 (12)	0.000	0.000
O1B	0.0642 (19)	0.058 (2)	0.0391 (17)	0.0288 (16)	−0.0113 (15)	−0.0089 (17)
O2B	0.0540 (16)	0.0534 (19)	0.069 (2)	0.0276 (13)	−0.0203 (14)	−0.0202 (17)
C1B	0.028 (2)	0.030 (3)	0.030 (3)	0.004 (2)	0.002 (2)	0.002 (2)
C2B	0.032 (3)	0.030 (4)	0.035 (4)	−0.003 (3)	0.005 (2)	0.003 (4)
C3B	0.041 (4)	0.027 (2)	0.048 (4)	0.000 (2)	0.001 (3)	0.006 (2)
C4B	0.047 (4)	0.038 (3)	0.040 (2)	−0.001 (2)	−0.007 (2)	0.009 (2)
C5B	0.044 (3)	0.040 (2)	0.036 (2)	−0.003 (3)	−0.002 (2)	−0.0044 (18)
C6B	0.035 (3)	0.032 (2)	0.038 (3)	0.004 (2)	0.001 (2)	−0.004 (2)
C7B	0.0316 (18)	0.0301 (19)	0.0428 (19)	0.0011 (14)	0.0013 (15)	−0.0005 (16)
C8B	0.040 (3)	0.031 (3)	0.055 (3)	0.0034 (19)	0.001 (2)	−0.004 (2)
O1Y	0.048 (2)	0.062 (3)	0.053 (2)	0.0177 (18)	−0.0178 (18)	−0.013 (2)
O2Y	0.080 (3)	0.079 (4)	0.0408 (19)	0.036 (2)	−0.0135 (17)	−0.015 (2)
C1Y	0.038 (3)	0.044 (6)	0.028 (3)	−0.005 (4)	0.007 (3)	0.000 (3)
C2Y	0.033 (5)	0.030 (4)	0.041 (5)	−0.007 (3)	0.001 (4)	0.012 (3)
C3Y	0.043 (6)	0.047 (7)	0.049 (6)	−0.011 (4)	−0.020 (6)	0.017 (4)
C4Y	0.055 (6)	0.058 (7)	0.036 (3)	−0.016 (4)	−0.012 (4)	0.007 (4)
C5Y	0.049 (4)	0.055 (4)	0.044 (4)	−0.013 (4)	−0.004 (4)	−0.008 (3)
C6Y	0.039 (4)	0.051 (4)	0.038 (4)	−0.006 (3)	−0.002 (3)	0.001 (3)
C7Y	0.035 (2)	0.041 (3)	0.029 (2)	0.003 (2)	0.0028 (19)	0.007 (2)
C8Y	0.052 (5)	0.039 (4)	0.056 (4)	−0.003 (3)	−0.004 (3)	0.005 (3)
N1B	0.1021 (16)	0.0423 (9)	0.0426 (9)	−0.0262 (10)	−0.0318 (10)	0.0166 (8)
N2B	0.0649 (10)	0.0235 (6)	0.0300 (7)	0.0002 (7)	−0.0011 (7)	−0.0023 (5)
C9B	0.0752 (15)	0.0299 (9)	0.0605 (13)	−0.0017 (9)	−0.0188 (11)	0.0133 (9)
C10B	0.0715 (14)	0.0323 (9)	0.0411 (10)	−0.0152 (9)	0.0069 (9)	−0.0089 (8)
C11B	0.167 (4)	0.0514 (18)	0.0181 (11)	−0.048 (2)	0.000	0.000
C12B	0.0759 (19)	0.0316 (12)	0.0211 (10)	0.0036 (13)	0.000	0.000

Geometric parameters (Å, º) top

O1A—C7A	1.306 (2)	C3B—H3BA	0.9500
O1A—H1O1	0.870 (18)	C4B—C5B	1.395 (7)
O2A—C7A	1.210 (2)	C4B—H4BA	0.9500
N1A—C11A	1.4725 (19)	C5B—C6B	1.382 (6)
N1A—C10Aⁱ	1.480 (2)	C5B—H5BA	0.9500
N1A—C9A	1.481 (2)	C6B—H6BA	0.9500
N2A—C9A	1.453 (2)	C8B—H8BA	0.9800
N2A—C10A	1.458 (2)	C8B—H8BB	0.9800
N2A—C12A	1.4721 (19)	C8B—H8BC	0.9800
C1A—C2A	1.396 (3)	O1Y—C7Y	1.312 (6)
C1A—C6A	1.412 (3)	O1Y—H3O1	0.83 (2)
C1A—C7A	1.491 (2)	O2Y—C7Y	1.202 (7)
C2A—C3A	1.403 (3)	C1Y—C6Y	1.388 (11)
C2A—C8A	1.489 (3)	C1Y—C2Y	1.398 (15)
C3A—C4A	1.368 (3)	C1Y—C7Y	1.500 (9)
C3A—H3AA	0.9500	C2Y—C3Y	1.409 (14)
C4A—C5A	1.390 (3)	C2Y—C8Y	1.514 (19)
C4A—H4AA	0.9500	C3Y—C4Y	1.380 (13)
C5A—C6A	1.370 (3)	C3Y—H3YA	0.9500
C5A—H5AA	0.9500	C4Y—C5Y	1.375 (10)
C6A—H6AA	0.9500	C4Y—H4YA	0.9500
C8A—H8AA	0.9800	C5Y—C6Y	1.373 (8)
C8A—H8AB	0.9800	C5Y—H5YA	0.9500
C8A—H8AC	0.9800	C6Y—H6YA	0.9500
C9A—H9AA	0.9900	C8Y—H8YA	0.9800
C9A—H9AB	0.9900	C8Y—H8YB	0.9800
C10A—N1Aⁱ	1.480 (2)	C8Y—H8YC	0.9800
C10A—H10A	0.9900	N1B—C11B	1.468 (3)
C10A—H10B	0.9900	N1B—C9B	1.476 (3)
C11A—N1Aⁱ	1.4726 (19)	N1B—C10Bⁱⁱ	1.481 (2)
C11A—H11A	0.9497	N2B—C9B	1.453 (3)
C12A—N2Aⁱ	1.4720 (19)	N2B—C10B	1.455 (3)
C12A—H12A	0.9523	N2B—C12B	1.4710 (18)
O1B—C7B	1.310 (4)	C9B—H9BA	0.9900
O1B—H2O1	0.82 (2)	C9B—H9BB	0.9900
O2B—C7B	1.204 (5)	C10B—N1Bⁱⁱ	1.481 (2)
C1B—C6B	1.392 (8)	C10B—H10C	0.9900
C1B—C2B	1.402 (11)	C10B—H10D	0.9900
C1B—C7B	1.498 (7)	C11B—N1Bⁱⁱ	1.468 (3)
C2B—C3B	1.385 (11)	C11B—H11C	0.9496
C2B—C8B	1.510 (14)	C12B—N2Bⁱⁱ	1.4710 (18)
C3B—C4B	1.374 (9)	C12B—H12C	0.9523

C7A—O1A—H1O1	110 (2)	C6B—C5B—H5BA	120.8
C11A—N1A—C10Aⁱ	108.11 (12)	C4B—C5B—H5BA	120.8
C11A—N1A—C9A	108.13 (12)	C5B—C6B—C1B	121.7 (5)
C10Aⁱ—N1A—C9A	107.88 (13)	C5B—C6B—H6BA	119.1
C9A—N2A—C10A	108.25 (13)	C1B—C6B—H6BA	119.1
C9A—N2A—C12A	108.39 (12)	O2B—C7B—O1B	122.7 (4)
C10A—N2A—C12A	108.20 (12)	O2B—C7B—C1B	120.8 (5)
C2A—C1A—C6A	119.44 (16)	O1B—C7B—C1B	116.5 (5)
C2A—C1A—C7A	122.90 (17)	C2B—C8B—H8BA	109.5
C6A—C1A—C7A	117.60 (17)	C2B—C8B—H8BB	109.5
C1A—C2A—C3A	117.82 (18)	H8BA—C8B—H8BB	109.5
C1A—C2A—C8A	124.25 (17)	C2B—C8B—H8BC	109.5
C3A—C2A—C8A	117.92 (18)	H8BA—C8B—H8BC	109.5
C4A—C3A—C2A	121.9 (2)	H8BB—C8B—H8BC	109.5
C4A—C3A—H3AA	119.1	C7Y—O1Y—H3O1	108 (7)
C2A—C3A—H3AA	119.1	C6Y—C1Y—C2Y	119.8 (10)
C3A—C4A—C5A	120.56 (18)	C6Y—C1Y—C7Y	118.2 (9)
C3A—C4A—H4AA	119.7	C2Y—C1Y—C7Y	121.8 (11)
C5A—C4A—H4AA	119.7	C1Y—C2Y—C3Y	118.1 (14)
C6A—C5A—C4A	118.78 (19)	C1Y—C2Y—C8Y	123.5 (12)
C6A—C5A—H5AA	120.6	C3Y—C2Y—C8Y	118.1 (11)
C4A—C5A—H5AA	120.6	C4Y—C3Y—C2Y	120.2 (13)
C5A—C6A—C1A	121.54 (19)	C4Y—C3Y—H3YA	119.9
C5A—C6A—H6AA	119.2	C2Y—C3Y—H3YA	119.9
C1A—C6A—H6AA	119.2	C5Y—C4Y—C3Y	121.3 (9)
O2A—C7A—O1A	122.11 (18)	C5Y—C4Y—H4YA	119.4
O2A—C7A—C1A	123.98 (18)	C3Y—C4Y—H4YA	119.4
O1A—C7A—C1A	113.90 (17)	C6Y—C5Y—C4Y	118.8 (9)
C2A—C8A—H8AA	109.5	C6Y—C5Y—H5YA	120.6
C2A—C8A—H8AB	109.5	C4Y—C5Y—H5YA	120.6
H8AA—C8A—H8AB	109.5	C5Y—C6Y—C1Y	121.6 (9)
C2A—C8A—H8AC	109.5	C5Y—C6Y—H6YA	119.2
H8AA—C8A—H8AC	109.5	C1Y—C6Y—H6YA	119.2
H8AB—C8A—H8AC	109.5	O2Y—C7Y—O1Y	122.7 (5)
N2A—C9A—N1A	112.22 (13)	O2Y—C7Y—C1Y	123.8 (7)
N2A—C9A—H9AA	109.2	O1Y—C7Y—C1Y	113.5 (7)
N1A—C9A—H9AA	109.2	C2Y—C8Y—H8YA	109.5
N2A—C9A—H9AB	109.2	C2Y—C8Y—H8YB	109.5
N1A—C9A—H9AB	109.2	H8YA—C8Y—H8YB	109.5
H9AA—C9A—H9AB	107.9	C2Y—C8Y—H8YC	109.5
N2A—C10A—N1Aⁱ	112.19 (13)	H8YA—C8Y—H8YC	109.5
N2A—C10A—H10A	109.2	H8YB—C8Y—H8YC	109.5
N1Aⁱ—C10A—H10A	109.2	C11B—N1B—C9B	107.96 (16)
N2A—C10A—H10B	109.2	C11B—N1B—C10Bⁱⁱ	108.29 (17)
N1Aⁱ—C10A—H10B	109.2	C9B—N1B—C10Bⁱⁱ	108.57 (15)
H10A—C10A—H10B	107.9	C9B—N2B—C10B	108.79 (16)
N1A—C11A—N1Aⁱ	111.37 (17)	C9B—N2B—C12B	107.94 (14)
N1A—C11A—H11A	109.7	C10B—N2B—C12B	108.33 (13)
N1Aⁱ—C11A—H11A	109.3	N2B—C9B—N1B	111.97 (17)
N2Aⁱ—C12A—N2A	112.02 (18)	N2B—C9B—H9BA	109.2
N2Aⁱ—C12A—H12A	109.7	N1B—C9B—H9BA	109.2
N2A—C12A—H12A	108.9	N2B—C9B—H9BB	109.2
C7B—O1B—H2O1	112 (5)	N1B—C9B—H9BB	109.2
C6B—C1B—C2B	120.1 (7)	H9BA—C9B—H9BB	107.9
C6B—C1B—C7B	115.1 (6)	N2B—C10B—N1Bⁱⁱ	111.32 (16)
C2B—C1B—C7B	124.8 (7)	N2B—C10B—H10C	109.4
C3B—C2B—C1B	116.7 (10)	N1Bⁱⁱ—C10B—H10C	109.4
C3B—C2B—C8B	117.6 (8)	N2B—C10B—H10D	109.4
C1B—C2B—C8B	125.6 (9)	N1Bⁱⁱ—C10B—H10D	109.4
C4B—C3B—C2B	123.5 (10)	H10C—C10B—H10D	108.0
C4B—C3B—H3BA	118.2	N1B—C11B—N1Bⁱⁱ	111.5 (2)
C2B—C3B—H3BA	118.2	N1B—C11B—H11C	108.9
C3B—C4B—C5B	119.3 (7)	N1Bⁱⁱ—C11B—H11C	110.0
C3B—C4B—H4BA	120.3	N2B—C12B—N2Bⁱⁱ	112.38 (18)
C5B—C4B—H4BA	120.3	N2B—C12B—H12C	109.7
C6B—C5B—C4B	118.4 (6)	N2Bⁱⁱ—C12B—H12C	108.7

C6A—C1A—C2A—C3A	0.3 (3)	C4B—C5B—C6B—C1B	0.1 (13)
C7A—C1A—C2A—C3A	−177.09 (16)	C2B—C1B—C6B—C5B	−3 (2)
C6A—C1A—C2A—C8A	179.21 (18)	C7B—C1B—C6B—C5B	178.6 (8)
C7A—C1A—C2A—C8A	1.8 (3)	C6B—C1B—C7B—O2B	−20.1 (16)
C1A—C2A—C3A—C4A	−0.5 (3)	C2B—C1B—C7B—O2B	161.6 (18)
C8A—C2A—C3A—C4A	−179.46 (18)	C6B—C1B—C7B—O1B	161.2 (9)
C2A—C3A—C4A—C5A	0.1 (3)	C2B—C1B—C7B—O1B	−17 (2)
C3A—C4A—C5A—C6A	0.5 (3)	C6Y—C1Y—C2Y—C3Y	−5 (5)
C4A—C5A—C6A—C1A	−0.7 (3)	C7Y—C1Y—C2Y—C3Y	−179 (3)
C2A—C1A—C6A—C5A	0.3 (3)	C6Y—C1Y—C2Y—C8Y	−179 (2)
C7A—C1A—C6A—C5A	177.82 (17)	C7Y—C1Y—C2Y—C8Y	8 (5)
C2A—C1A—C7A—O2A	−7.5 (3)	C1Y—C2Y—C3Y—C4Y	5 (5)
C6A—C1A—C7A—O2A	175.1 (2)	C8Y—C2Y—C3Y—C4Y	179 (2)
C2A—C1A—C7A—O1A	171.52 (17)	C2Y—C3Y—C4Y—C5Y	−3 (4)
C6A—C1A—C7A—O1A	−5.9 (2)	C3Y—C4Y—C5Y—C6Y	1 (2)
C10A—N2A—C9A—N1A	58.75 (18)	C4Y—C5Y—C6Y—C1Y	−0.5 (18)
C12A—N2A—C9A—N1A	−58.39 (18)	C2Y—C1Y—C6Y—C5Y	3 (3)
C11A—N1A—C9A—N2A	−58.76 (17)	C7Y—C1Y—C6Y—C5Y	176.7 (12)
C10Aⁱ—N1A—C9A—N2A	57.94 (18)	C6Y—C1Y—C7Y—O2Y	170.2 (12)
C9A—N2A—C10A—N1Aⁱ	−58.78 (18)	C2Y—C1Y—C7Y—O2Y	−16 (3)
C12A—N2A—C10A—N1Aⁱ	58.49 (17)	C6Y—C1Y—C7Y—O1Y	−10 (2)
C10Aⁱ—N1A—C11A—N1Aⁱ	−58.29 (9)	C2Y—C1Y—C7Y—O1Y	164 (2)
C9A—N1A—C11A—N1Aⁱ	58.25 (10)	C10B—N2B—C9B—N1B	−59.1 (2)
C9A—N2A—C12A—N2Aⁱ	58.61 (10)	C12B—N2B—C9B—N1B	58.2 (2)
C10A—N2A—C12A—N2Aⁱ	−58.56 (9)	C11B—N1B—C9B—N2B	58.7 (2)
C6B—C1B—C2B—C3B	6 (3)	C10Bⁱⁱ—N1B—C9B—N2B	−58.5 (2)
C7B—C1B—C2B—C3B	−176.2 (19)	C9B—N2B—C10B—N1Bⁱⁱ	58.8 (2)
C6B—C1B—C2B—C8B	−178.6 (18)	C12B—N2B—C10B—N1Bⁱⁱ	−58.3 (2)
C7B—C1B—C2B—C8B	0 (4)	C9B—N1B—C11B—N1Bⁱⁱ	−58.53 (11)
C1B—C2B—C3B—C4B	−6 (4)	C10Bⁱⁱ—N1B—C11B—N1Bⁱⁱ	58.83 (11)
C8B—C2B—C3B—C4B	178.1 (18)	C9B—N2B—C12B—N2Bⁱⁱ	−58.64 (12)
C2B—C3B—C4B—C5B	3 (3)	C10B—N2B—C12B—N2Bⁱⁱ	59.00 (11)
C3B—C4B—C5B—C6B	0.0 (15)

Symmetry codes: (i) −x+3/2, −y+3/2, z; (ii) −x+3/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O1···N1A	0.87 (2)	1.81 (2)	2.671 (2)	169 (3)
O1B—H2O1···N1B	0.82 (5)	2.01 (5)	2.818 (4)	166 (6)
C6A—H6AA···O1A	0.95	2.32	2.678 (2)	101
C10A—H10B···O2B	0.99	2.58	3.070 (4)	110
C12A—H12A···O2Aⁱⁱⁱ	0.95	2.43	3.375 (2)	172
C12B—H12C···O2B^iv	0.95	2.38	3.321 (4)	169
C8B—H8BA···O1B	0.98	2.45	2.805 (8)	101

Symmetry codes: (iii) x, −y+3/2, z−1/2; (iv) −x+3/2, y, z−1/2.

(300K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top

Crystal data top

C₆H₁₂N₄·2C₈H₈O₂	D_x = 1.274 Mg m⁻³
M_r = 412.48	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pccn	Cell parameters from 9216 reflections
a = 31.3604 (17) Å	θ = 2.2–27.3°
b = 9.5095 (5) Å	µ = 0.09 mm⁻¹
c = 14.4182 (8) Å	T = 300 K
V = 4299.8 (4) Å³	Block, colourless
Z = 8	0.61 × 0.54 × 0.30 mm
F(000) = 1760

Data collection top

Bruker APEX DUO CCD area detector diffractometer	5201 independent reflections
Radiation source: fine-focus sealed tube	4046 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 28.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −41→41
T_min = 0.879, T_max = 0.926	k = −12→12
59046 measured reflections	l = −19→19

Refinement top

Refinement on F²	384 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.069	H-atom parameters constrained
wR(F²) = 0.219	w = 1/[σ²(F_o²) + (0.1121P)² + 1.1305P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
5201 reflections	Δρ_max = 0.38 e Å⁻³
367 parameters	Δρ_min = −0.31 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1A	0.63559 (5)	0.8094 (2)	0.52543 (13)	0.1025 (6)
H1O1	0.6605	0.7934	0.5013	0.154*
O2A	0.65813 (6)	0.6914 (3)	0.64485 (17)	0.1285 (9)
N1A	0.71165 (4)	0.76912 (15)	0.44286 (10)	0.0530 (3)
N2A	0.74420 (5)	0.62308 (15)	0.32399 (9)	0.0555 (4)
C1A	0.58417 (5)	0.7482 (2)	0.63533 (13)	0.0584 (4)
C2A	0.56954 (7)	0.6720 (2)	0.71057 (14)	0.0689 (5)
C3A	0.52554 (7)	0.6792 (3)	0.73113 (17)	0.0801 (6)
H3AA	0.5151	0.6282	0.7813	0.096*
C4A	0.49811 (7)	0.7576 (3)	0.68045 (18)	0.0845 (7)
H4AA	0.4694	0.7596	0.6963	0.101*
C5A	0.51244 (7)	0.8348 (3)	0.60530 (19)	0.0848 (7)
H5AA	0.4936	0.8893	0.5707	0.102*
C6A	0.55475 (7)	0.8296 (2)	0.58294 (16)	0.0736 (6)
H6AA	0.5645	0.8805	0.5322	0.088*
C7A	0.62941 (6)	0.7471 (2)	0.60342 (15)	0.0654 (5)
C8A	0.59686 (9)	0.5834 (3)	0.7697 (2)	0.0973 (8)
H8AA	0.5795	0.5349	0.8143	0.146*
H8AB	0.6172	0.6414	0.8015	0.146*
H8AC	0.6116	0.5161	0.7319	0.146*
C9A	0.70723 (6)	0.64414 (19)	0.38277 (14)	0.0612 (4)
H9AA	0.7032	0.5616	0.4213	0.073*
H9AB	0.6821	0.6549	0.3441	0.073*
C10A	0.78155 (6)	0.60722 (18)	0.38300 (13)	0.0584 (4)
H10A	0.8065	0.5932	0.3444	0.070*
H10B	0.7781	0.5244	0.4215	0.070*
C11A	0.7500	0.7500	0.50026 (15)	0.0561 (6)
H11A	0.7462	0.6693	0.5394	0.067*
C12A	0.7500	0.7500	0.26702 (16)	0.0633 (6)
H12A	0.7255	0.7624	0.2278	0.076*
O1B	0.86126 (15)	0.1700 (5)	0.2877 (3)	0.1018 (14)	0.627 (9)
H2O1	0.8359	0.2089	0.2533	0.153*	0.627 (9)
O2B	0.83471 (10)	0.3303 (4)	0.3782 (4)	0.1038 (14)	0.627 (9)
C1B	0.8933 (4)	0.2026 (12)	0.4360 (7)	0.0513 (14)	0.627 (9)
C2B	0.9185 (6)	0.0800 (13)	0.4354 (10)	0.057 (2)	0.627 (9)
C3B	0.9454 (5)	0.0551 (12)	0.5112 (8)	0.0715 (19)	0.627 (9)
H3BA	0.9608	−0.0284	0.5137	0.086*	0.627 (9)
C4B	0.9495 (2)	0.1505 (9)	0.5814 (5)	0.0763 (17)	0.627 (9)
H4BA	0.9683	0.1328	0.6297	0.092*	0.627 (9)
C5B	0.9259 (2)	0.2727 (8)	0.5813 (5)	0.0748 (16)	0.627 (9)
H5BA	0.9285	0.3372	0.6294	0.090*	0.627 (9)
C6B	0.8982 (2)	0.2979 (7)	0.5081 (5)	0.0635 (14)	0.627 (9)
H6BA	0.8825	0.3809	0.5073	0.076*	0.627 (9)
C7B	0.86081 (12)	0.2398 (5)	0.3644 (3)	0.0569 (9)	0.627 (9)
C8B	0.9159 (2)	−0.0325 (7)	0.3629 (7)	0.0798 (16)	0.627 (9)
H8BA	0.8866	−0.0580	0.3534	0.120*	0.627 (9)
H8BB	0.9317	−0.1134	0.3830	0.120*	0.627 (9)
H8BC	0.9277	0.0019	0.3058	0.120*	0.627 (9)
O1Y	0.83589 (19)	0.2654 (10)	0.3363 (5)	0.103 (2)	0.373 (9)
H3O1	0.8188	0.2410	0.2797	0.155*	0.373 (9)
O2Y	0.8723 (3)	0.0960 (13)	0.2739 (4)	0.127 (3)	0.373 (9)
C1Y	0.8928 (7)	0.176 (2)	0.4232 (12)	0.057 (3)	0.373 (9)
C2Y	0.9181 (10)	0.062 (2)	0.4468 (17)	0.060 (3)	0.373 (9)
C3Y	0.9407 (7)	0.076 (2)	0.5305 (13)	0.076 (3)	0.373 (9)
H3YA	0.9597	0.0049	0.5472	0.092*	0.373 (9)
C4Y	0.9360 (4)	0.1879 (17)	0.5880 (9)	0.082 (3)	0.373 (9)
H4YA	0.9505	0.1893	0.6444	0.098*	0.373 (9)
C5Y	0.9106 (4)	0.2980 (13)	0.5646 (8)	0.077 (3)	0.373 (9)
H5YA	0.9084	0.3762	0.6031	0.092*	0.373 (9)
C6Y	0.8879 (4)	0.2915 (16)	0.4826 (9)	0.069 (2)	0.373 (9)
H6YA	0.8694	0.3640	0.4666	0.083*	0.373 (9)
C7Y	0.8668 (2)	0.1742 (10)	0.3365 (5)	0.0633 (19)	0.373 (9)
C8Y	0.9276 (5)	−0.0620 (15)	0.3821 (12)	0.090 (3)	0.373 (9)
H8YA	0.9482	−0.1229	0.4107	0.134*	0.373 (9)
H8YB	0.9388	−0.0275	0.3244	0.134*	0.373 (9)
H8YC	0.9018	−0.1135	0.3705	0.134*	0.373 (9)
N1B	0.78857 (6)	0.23691 (19)	0.18809 (11)	0.0733 (5)
N2B	0.74583 (6)	0.12254 (15)	0.06999 (10)	0.0640 (4)
C9B	0.78319 (8)	0.1123 (2)	0.12838 (16)	0.0748 (6)
H9BA	0.8083	0.1016	0.0896	0.090*
H9BB	0.7809	0.0292	0.1670	0.090*
C10B	0.70848 (7)	0.1372 (2)	0.12840 (14)	0.0703 (5)
H10C	0.7056	0.0542	0.1670	0.084*
H10D	0.6833	0.1441	0.0897	0.084*
C11B	0.7500	0.2500	0.24551 (17)	0.0816 (10)
H11C	0.7526	0.3313	0.2846	0.098*
C12B	0.7500	0.2500	0.01332 (16)	0.0703 (8)
H12C	0.7254	0.2590	−0.0259	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0724 (10)	0.1427 (16)	0.0924 (11)	0.0248 (10)	0.0287 (9)	0.0279 (11)
O2A	0.0585 (9)	0.190 (2)	0.1365 (17)	0.0187 (12)	0.0010 (10)	0.0504 (17)
N1A	0.0498 (7)	0.0559 (8)	0.0533 (7)	0.0019 (6)	0.0122 (6)	−0.0003 (6)
N2A	0.0672 (9)	0.0486 (7)	0.0507 (7)	0.0000 (6)	−0.0019 (6)	−0.0128 (6)
C1A	0.0513 (9)	0.0615 (10)	0.0625 (10)	−0.0038 (7)	0.0026 (7)	−0.0146 (8)
C2A	0.0654 (11)	0.0730 (12)	0.0684 (11)	−0.0061 (9)	−0.0009 (9)	−0.0105 (9)
C3A	0.0588 (11)	0.0960 (16)	0.0854 (14)	−0.0157 (11)	0.0124 (10)	−0.0230 (12)
C4A	0.0560 (11)	0.1088 (18)	0.0887 (16)	−0.0082 (11)	0.0067 (10)	−0.0239 (14)
C5A	0.0621 (12)	0.0962 (17)	0.0961 (16)	0.0172 (11)	−0.0114 (11)	−0.0148 (14)
C6A	0.0648 (11)	0.0748 (13)	0.0811 (13)	0.0058 (9)	0.0042 (10)	−0.0091 (10)
C7A	0.0534 (9)	0.0698 (11)	0.0731 (12)	−0.0007 (8)	0.0066 (9)	−0.0077 (9)
C8A	0.0937 (17)	0.1052 (19)	0.0929 (17)	0.0002 (15)	−0.0100 (14)	0.0130 (15)
C9A	0.0548 (9)	0.0571 (10)	0.0716 (11)	−0.0146 (8)	−0.0023 (8)	−0.0055 (8)
C10A	0.0635 (10)	0.0493 (9)	0.0624 (10)	0.0148 (7)	0.0015 (8)	−0.0011 (7)
C11A	0.0758 (15)	0.0561 (13)	0.0365 (10)	0.0009 (11)	0.000	0.000
C12A	0.0770 (16)	0.0765 (17)	0.0365 (10)	0.0070 (13)	0.000	0.000
O1B	0.113 (3)	0.122 (3)	0.071 (2)	0.061 (2)	−0.0262 (19)	−0.023 (2)
O2B	0.0902 (19)	0.102 (2)	0.119 (3)	0.0489 (17)	−0.0337 (18)	−0.033 (2)
C1B	0.045 (2)	0.054 (3)	0.055 (3)	0.001 (2)	0.0039 (18)	0.004 (2)
C2B	0.054 (3)	0.050 (3)	0.069 (4)	−0.004 (3)	0.006 (3)	0.009 (3)
C3B	0.064 (3)	0.063 (3)	0.088 (5)	0.008 (2)	−0.001 (3)	0.012 (3)
C4B	0.075 (4)	0.084 (4)	0.070 (3)	0.003 (2)	−0.017 (3)	0.015 (2)
C5B	0.079 (4)	0.083 (4)	0.062 (3)	0.003 (3)	−0.013 (2)	−0.007 (3)
C6B	0.059 (3)	0.067 (2)	0.065 (4)	0.006 (2)	−0.001 (2)	−0.005 (2)
C7B	0.0502 (17)	0.0530 (19)	0.067 (2)	0.0037 (14)	−0.0001 (15)	−0.0008 (16)
C8B	0.066 (3)	0.058 (3)	0.115 (5)	0.011 (2)	0.000 (3)	−0.010 (3)
O1Y	0.088 (3)	0.128 (6)	0.093 (4)	0.041 (3)	−0.036 (3)	−0.033 (4)
O2Y	0.140 (5)	0.176 (8)	0.066 (3)	0.076 (5)	−0.021 (3)	−0.029 (4)
C1Y	0.053 (4)	0.067 (7)	0.050 (4)	−0.011 (4)	0.006 (3)	0.010 (3)
C2Y	0.050 (5)	0.065 (6)	0.065 (5)	−0.011 (4)	0.008 (3)	0.022 (4)
C3Y	0.069 (8)	0.083 (8)	0.077 (7)	−0.012 (5)	−0.021 (7)	0.030 (4)
C4Y	0.077 (8)	0.097 (8)	0.071 (4)	−0.012 (6)	−0.022 (5)	0.017 (5)
C5Y	0.083 (7)	0.086 (5)	0.061 (5)	−0.013 (5)	−0.011 (5)	0.003 (4)
C6Y	0.061 (5)	0.092 (5)	0.055 (5)	−0.008 (4)	−0.002 (3)	0.007 (4)
C7Y	0.066 (3)	0.074 (5)	0.049 (3)	0.006 (3)	0.003 (3)	0.007 (3)
C8Y	0.089 (8)	0.072 (6)	0.108 (7)	0.009 (5)	0.002 (5)	−0.001 (5)
N1B	0.0959 (13)	0.0685 (10)	0.0553 (9)	−0.0144 (9)	−0.0211 (8)	0.0133 (7)
N2B	0.0987 (12)	0.0440 (7)	0.0493 (7)	0.0007 (7)	0.0004 (7)	−0.0081 (6)
C9B	0.0955 (15)	0.0514 (10)	0.0774 (12)	0.0098 (10)	−0.0039 (11)	0.0108 (9)
C10B	0.0900 (14)	0.0579 (10)	0.0631 (10)	−0.0185 (10)	0.0004 (10)	−0.0085 (9)
C11B	0.136 (3)	0.0752 (18)	0.0335 (11)	−0.0291 (18)	0.000	0.000
C12B	0.114 (2)	0.0630 (15)	0.0342 (10)	0.0048 (15)	0.000	0.000

Geometric parameters (Å, º) top

O1A—C7A	1.286 (3)	C3B—H3BA	0.9300
O1A—H1O1	0.8689	C4B—C5B	1.377 (7)
O2A—C7A	1.203 (3)	C4B—H4BA	0.9300
N1A—C11A	1.4712 (19)	C5B—C6B	1.387 (7)
N1A—C10Aⁱ	1.474 (2)	C5B—H5BA	0.9300
N1A—C9A	1.477 (2)	C6B—H6BA	0.9300
N2A—C9A	1.450 (2)	C8B—H8BA	0.9600
N2A—C10A	1.456 (2)	C8B—H8BB	0.9600
N2A—C12A	1.4712 (19)	C8B—H8BC	0.9600
C1A—C2A	1.383 (3)	O1Y—C7Y	1.302 (8)
C1A—C6A	1.421 (3)	O1Y—H3O1	1.0041
C1A—C7A	1.492 (2)	O2Y—C7Y	1.182 (9)
C2A—C3A	1.413 (3)	C1Y—C2Y	1.381 (16)
C2A—C8A	1.474 (3)	C1Y—C6Y	1.403 (15)
C3A—C4A	1.353 (4)	C1Y—C7Y	1.491 (10)
C3A—H3AA	0.9300	C2Y—C3Y	1.407 (16)
C4A—C5A	1.384 (4)	C2Y—C8Y	1.54 (2)
C4A—H4AA	0.9300	C3Y—C4Y	1.359 (15)
C5A—C6A	1.366 (3)	C3Y—H3YA	0.9300
C5A—H5AA	0.9300	C4Y—C5Y	1.360 (12)
C6A—H6AA	0.9300	C4Y—H4YA	0.9300
C8A—H8AA	0.9600	C5Y—C6Y	1.381 (10)
C8A—H8AB	0.9600	C5Y—H5YA	0.9300
C8A—H8AC	0.9600	C6Y—H6YA	0.9300
C9A—H9AA	0.9700	C8Y—H8YA	0.9600
C9A—H9AB	0.9700	C8Y—H8YB	0.9600
C10A—N1Aⁱ	1.474 (2)	C8Y—H8YC	0.9600
C10A—H10A	0.9700	N1B—C11B	1.471 (2)
C10A—H10B	0.9700	N1B—C9B	1.474 (3)
C11A—N1Aⁱ	1.4713 (19)	N1B—C10Bⁱⁱ	1.477 (2)
C11A—H11A	0.9602	N2B—C9B	1.446 (3)
C12A—N2Aⁱ	1.4712 (19)	N2B—C10B	1.449 (3)
C12A—H12A	0.9605	N2B—C12B	1.4677 (19)
O1B—C7B	1.290 (4)	C9B—H9BA	0.9700
O1B—H2O1	1.0088	C9B—H9BB	0.9700
O2B—C7B	1.204 (5)	C10B—N1Bⁱⁱ	1.477 (2)
C1B—C6B	1.388 (8)	C10B—H10C	0.9700
C1B—C2B	1.409 (10)	C10B—H10D	0.9700
C1B—C7B	1.493 (6)	C11B—N1Bⁱⁱ	1.471 (2)
C2B—C3B	1.400 (10)	C11B—H11C	0.9601
C2B—C8B	1.497 (12)	C12B—N2Bⁱⁱ	1.4677 (19)
C3B—C4B	1.365 (9)	C12B—H12C	0.9604

C7A—O1A—H1O1	113.9	C4B—C5B—H5BA	120.6
C11A—N1A—C10Aⁱ	108.04 (12)	C6B—C5B—H5BA	120.6
C11A—N1A—C9A	107.89 (12)	C5B—C6B—C1B	121.7 (6)
C10Aⁱ—N1A—C9A	108.17 (13)	C5B—C6B—H6BA	119.1
C9A—N2A—C10A	108.42 (14)	C1B—C6B—H6BA	119.1
C9A—N2A—C12A	108.18 (13)	O2B—C7B—O1B	121.1 (4)
C10A—N2A—C12A	108.17 (13)	O2B—C7B—C1B	121.3 (5)
C2A—C1A—C6A	119.12 (18)	O1B—C7B—C1B	117.6 (4)
C2A—C1A—C7A	123.62 (19)	C2B—C8B—H8BA	109.5
C6A—C1A—C7A	117.23 (18)	C2B—C8B—H8BB	109.5
C1A—C2A—C3A	117.6 (2)	H8BA—C8B—H8BB	109.5
C1A—C2A—C8A	124.1 (2)	C2B—C8B—H8BC	109.5
C3A—C2A—C8A	118.3 (2)	H8BA—C8B—H8BC	109.5
C4A—C3A—C2A	122.3 (2)	H8BB—C8B—H8BC	109.5
C4A—C3A—H3AA	118.9	C7Y—O1Y—H3O1	104.3
C2A—C3A—H3AA	118.9	C2Y—C1Y—C6Y	121.6 (11)
C3A—C4A—C5A	120.6 (2)	C2Y—C1Y—C7Y	120.8 (12)
C3A—C4A—H4AA	119.7	C6Y—C1Y—C7Y	117.4 (11)
C5A—C4A—H4AA	119.7	C1Y—C2Y—C3Y	115.6 (15)
C6A—C5A—C4A	118.7 (2)	C1Y—C2Y—C8Y	124.3 (14)
C6A—C5A—H5AA	120.6	C3Y—C2Y—C8Y	119.5 (13)
C4A—C5A—H5AA	120.6	C4Y—C3Y—C2Y	122.6 (13)
C5A—C6A—C1A	121.7 (2)	C4Y—C3Y—H3YA	118.7
C5A—C6A—H6AA	119.2	C2Y—C3Y—H3YA	118.7
C1A—C6A—H6AA	119.2	C3Y—C4Y—C5Y	121.2 (10)
O2A—C7A—O1A	121.61 (19)	C3Y—C4Y—H4YA	119.4
O2A—C7A—C1A	124.2 (2)	C5Y—C4Y—H4YA	119.4
O1A—C7A—C1A	114.18 (18)	C4Y—C5Y—C6Y	118.7 (12)
C2A—C8A—H8AA	109.5	C4Y—C5Y—H5YA	120.7
C2A—C8A—H8AB	109.5	C6Y—C5Y—H5YA	120.7
H8AA—C8A—H8AB	109.5	C5Y—C6Y—C1Y	120.1 (11)
C2A—C8A—H8AC	109.5	C5Y—C6Y—H6YA	119.9
H8AA—C8A—H8AC	109.5	C1Y—C6Y—H6YA	119.9
H8AB—C8A—H8AC	109.5	O2Y—C7Y—O1Y	121.7 (7)
N2A—C9A—N1A	112.27 (13)	O2Y—C7Y—C1Y	124.6 (8)
N2A—C9A—H9AA	109.2	O1Y—C7Y—C1Y	113.7 (9)
N1A—C9A—H9AA	109.2	C2Y—C8Y—H8YA	109.5
N2A—C9A—H9AB	109.2	C2Y—C8Y—H8YB	109.5
N1A—C9A—H9AB	109.2	H8YA—C8Y—H8YB	109.5
H9AA—C9A—H9AB	107.9	C2Y—C8Y—H8YC	109.5
N2A—C10A—N1Aⁱ	112.09 (13)	H8YA—C8Y—H8YC	109.5
N2A—C10A—H10A	109.2	H8YB—C8Y—H8YC	109.5
N1Aⁱ—C10A—H10A	109.2	C11B—N1B—C9B	107.61 (15)
N2A—C10A—H10B	109.2	C11B—N1B—C10Bⁱⁱ	108.10 (16)
N1Aⁱ—C10A—H10B	109.2	C9B—N1B—C10Bⁱⁱ	108.55 (15)
H10A—C10A—H10B	107.9	C9B—N2B—C10B	108.85 (16)
N1A—C11A—N1Aⁱ	111.54 (17)	C9B—N2B—C12B	107.90 (14)
N1A—C11A—H11A	109.1	C10B—N2B—C12B	108.43 (14)
N1Aⁱ—C11A—H11A	109.5	N2B—C9B—N1B	112.25 (16)
N2A—C12A—N2Aⁱ	112.12 (18)	N2B—C9B—H9BA	109.2
N2A—C12A—H12A	109.3	N1B—C9B—H9BA	109.2
N2Aⁱ—C12A—H12A	109.1	N2B—C9B—H9BB	109.2
C7B—O1B—H2O1	103.0	N1B—C9B—H9BB	109.2
C6B—C1B—C2B	118.9 (6)	H9BA—C9B—H9BB	107.9
C6B—C1B—C7B	116.0 (6)	N2B—C10B—N1Bⁱⁱ	111.46 (15)
C2B—C1B—C7B	125.1 (6)	N2B—C10B—H10C	109.3
C3B—C2B—C1B	118.2 (8)	N1Bⁱⁱ—C10B—H10C	109.3
C3B—C2B—C8B	117.2 (7)	N2B—C10B—H10D	109.3
C1B—C2B—C8B	124.4 (7)	N1Bⁱⁱ—C10B—H10D	109.3
C4B—C3B—C2B	121.5 (8)	H10C—C10B—H10D	108.0
C4B—C3B—H3BA	119.3	N1B—C11B—N1Bⁱⁱ	111.51 (19)
C2B—C3B—H3BA	119.3	N1B—C11B—H11C	109.1
C3B—C4B—C5B	120.7 (6)	N1Bⁱⁱ—C11B—H11C	109.5
C3B—C4B—H4BA	119.7	N2B—C12B—N2Bⁱⁱ	112.34 (18)
C5B—C4B—H4BA	119.7	N2B—C12B—H12C	109.2
C4B—C5B—C6B	118.9 (6)	N2Bⁱⁱ—C12B—H12C	109.0

C6A—C1A—C2A—C3A	0.2 (3)	C4B—C5B—C6B—C1B	0.9 (14)
C7A—C1A—C2A—C3A	−177.87 (18)	C2B—C1B—C6B—C5B	−3 (2)
C6A—C1A—C2A—C8A	179.6 (2)	C7B—C1B—C6B—C5B	177.0 (9)
C7A—C1A—C2A—C8A	1.6 (3)	C6B—C1B—C7B—O2B	−14.7 (16)
C1A—C2A—C3A—C4A	−0.4 (3)	C2B—C1B—C7B—O2B	165.1 (15)
C8A—C2A—C3A—C4A	−179.8 (2)	C6B—C1B—C7B—O1B	166.3 (9)
C2A—C3A—C4A—C5A	0.1 (4)	C2B—C1B—C7B—O1B	−14 (2)
C3A—C4A—C5A—C6A	0.4 (4)	C6Y—C1Y—C2Y—C3Y	−4 (5)
C4A—C5A—C6A—C1A	−0.6 (4)	C7Y—C1Y—C2Y—C3Y	−179 (2)
C2A—C1A—C6A—C5A	0.3 (3)	C6Y—C1Y—C2Y—C8Y	−175 (2)
C7A—C1A—C6A—C5A	178.5 (2)	C7Y—C1Y—C2Y—C8Y	10 (5)
C2A—C1A—C7A—O2A	−7.6 (3)	C1Y—C2Y—C3Y—C4Y	4 (5)
C6A—C1A—C7A—O2A	174.3 (2)	C8Y—C2Y—C3Y—C4Y	175 (2)
C2A—C1A—C7A—O1A	171.2 (2)	C2Y—C3Y—C4Y—C5Y	−4 (4)
C6A—C1A—C7A—O1A	−6.9 (3)	C3Y—C4Y—C5Y—C6Y	3 (2)
C10A—N2A—C9A—N1A	58.81 (19)	C4Y—C5Y—C6Y—C1Y	−3 (2)
C12A—N2A—C9A—N1A	−58.27 (18)	C2Y—C1Y—C6Y—C5Y	4 (4)
C11A—N1A—C9A—N2A	−58.65 (18)	C7Y—C1Y—C6Y—C5Y	179.0 (15)
C10Aⁱ—N1A—C9A—N2A	58.00 (18)	C2Y—C1Y—C7Y—O2Y	−17 (3)
C9A—N2A—C10A—N1Aⁱ	−58.80 (19)	C6Y—C1Y—C7Y—O2Y	167.7 (15)
C12A—N2A—C10A—N1Aⁱ	58.29 (18)	C2Y—C1Y—C7Y—O1Y	161 (2)
C10Aⁱ—N1A—C11A—N1Aⁱ	−58.45 (9)	C6Y—C1Y—C7Y—O1Y	−14 (3)
C9A—N1A—C11A—N1Aⁱ	58.28 (10)	C10B—N2B—C9B—N1B	−59.4 (2)
C9A—N2A—C12A—N2Aⁱ	58.63 (10)	C12B—N2B—C9B—N1B	58.1 (2)
C10A—N2A—C12A—N2Aⁱ	−58.62 (9)	C11B—N1B—C9B—N2B	58.6 (2)
C6B—C1B—C2B—C3B	4 (3)	C10Bⁱⁱ—N1B—C9B—N2B	−58.1 (2)
C7B—C1B—C2B—C3B	−175.4 (15)	C9B—N2B—C10B—N1Bⁱⁱ	59.0 (2)
C6B—C1B—C2B—C8B	178.8 (15)	C12B—N2B—C10B—N1Bⁱⁱ	−58.1 (2)
C7B—C1B—C2B—C8B	−1 (3)	C9B—N1B—C11B—N1Bⁱⁱ	−58.32 (11)
C1B—C2B—C3B—C4B	−4 (3)	C10Bⁱⁱ—N1B—C11B—N1Bⁱⁱ	58.74 (11)
C8B—C2B—C3B—C4B	−179.1 (14)	C9B—N2B—C12B—N2Bⁱⁱ	−58.67 (12)
C2B—C3B—C4B—C5B	2 (2)	C10B—N2B—C12B—N2Bⁱⁱ	59.07 (11)
C3B—C4B—C5B—C6B	−0.6 (14)

Symmetry codes: (i) −x+3/2, −y+3/2, z; (ii) −x+3/2, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O1···N1A	0.87	1.83	2.693 (2)	175
O1B—H2O1···N1B	1.01	1.78	2.768 (5)	167
C6A—H6AA···O1A	0.93	2.33	2.674 (3)	101
C12A—H12A···O2Aⁱⁱⁱ	0.96	2.47	3.423 (2)	173
C12B—H12C···O2B^iv	0.96	2.43	3.382 (4)	169
C6B—H6BA···O2B	0.93	2.44	2.751 (8)	100

Symmetry codes: (iii) x, −y+3/2, z−1/2; (iv) −x+3/2, y, z−1/2.

C—N_alpha bond lengths of HMTA and their average in (I) at different temperatures and other reported salts (represented by their CSD refcodes) top

Compound	C—N_alpha bond lengths (Å)			Average (Å)
(I) at 100 K	1.485 (3)	1.485 (4)	1.486 (4)	1.485 (4)
	1.474 (4)	1.485 (4)	1.485 (3)	1.481 (4)
	1.474 (4)	1.485 (4)	1.488 (4)	1.482 (4)
	1.474 (4)	1.480 (4)	1.487 (4)	1.480 (4)
(I) at 150 K	1.475 (4)	1.477 (4)	1.485 (4)	1.479 (4)
	1.472 (4)	1.480 (4)	1.484 (4)	1.479 (4)
	1.469 (4)	1.479 (3)	1.482 (3)	1.477 (3)
	1.470 (4)	1.478 (3)	1.482 (3)	1.477 (3)
(I) at 170 K	1.4725 (19)	1.480 (2)	1.481 (2)	1.478 (2)
	1.468 (3)	1.476 (3)	1.481 (2)	1.475 (3)
BERPUK (Chantrapromma et al., 2006)	1.516 (4)	1.487 (5)	1.509 (4)	1.504 (4)
	1.501 (4)	1.508 (4)	1.497 (5)	1.502 (4)
BERPUK01 (Chantrapromma et al., 2006)	1.511 (5)	1.515 (4)	1.519 (4)	1.515 (4)
DIBZAQ (Fun et al., 2007)	1.501 (2)	1.505 (2)	1.5059 (19)	1.504 (2)
DIBZAQ01 (Fun et al., 2007)	1.5117 (9)	1.5145 (8)	1.5155 (9)	1.5139 (9)
	1.5146 (9)	1.5152 (9)	1.5188 (10)	1.5162 (9)
VATSOA (Quah et al., 2012)	1.493 (6)	1.495 (5)	1.497 (6)	1.495 (6)
	1.496 (6)	1.502 (6)	1.513 (5)	1.504 (6)
	1.500 (6)	1.507 (6)	1.511 (5)	1.506 (6)
	1.490 (6)	1.496 (6)	1.505 (5)	1.497 (6)
VATSOA01 (Quah et al., 2012)	1.482 (5)	1.482 (5)	1.486 (5)	1.483 (5)
VATSOA02 (Quah et al., 2012)	1.481 (6)	1.484 (5)	1.501 (4)	1.489 (5)
MEVXIU (Usman et al., 2001)	1.514 (3)	1.516 (3)	1.526 (3)	1.519 (3)
MEVXIU01 (Usman et al., 2001)	1.510 (2)	1.510 (2)	1.519 (3)	1.513 (2)

Puckering parameters of HMTA molecules at different temperatures top

Definitions for six-membered rings: ring 1 is formed from atoms N1/C33/N2/C34/N3/C35, ring 2 from N1/C33/N2/C37/N4/C36, ring 3 from N1/C35/N3/C38/N4/C36, ring 4 from N2/C34/N3/C38/N4/C37, ring 5 from N5/C39/N6/C40/N7/C41, ring 6 from N5/C39/N6/C43/N8/C42, ring 7 from N5/C41/N7/C44/N8/C42, ring 8 from N6/C40/N7/C44/N8/C43, ring 9 from N1A/C9A/N2A/C10A/N1Aⁱ/C11A, ring 10 from N1A/C9A/N2A/C12A/N2Aⁱ/C10Aⁱ, ring 11 from N1A/C11A/N1Aⁱ/C9Aⁱ/N2Aⁱ/C10Aⁱ, ring 12 from N2A/C10A/N1Aⁱ/C9Aⁱ/N2Aⁱ/C12A, ring 13 from N1B/C9B/N2B/C10B/N1Bⁱⁱ/C11B, ring 14 from N1B/C9B/N2B/C12B/N2Bⁱⁱ/C10Bⁱⁱ, ring 15 from N1B/C11B/N1Bⁱⁱ/C9Bⁱⁱ/N2Bⁱⁱ/C10Bⁱⁱ and ring 16 from N2B/C10B/N1Bⁱⁱ/C9Bⁱⁱ/N2Bⁱⁱ/C12B.

Symmetry codes: (i) -x+3/2, -y+3/2, z; (ii) -x+3/2, -y+1/2, z.

	Puckering amplitude, Q (Å)	θ (°)	φ (°)
100 K
1	0.584 (3)	180.0 (3)	139 (52)
2	0.588 (3)	0.0 (3)	34 (18)
3	0.589 (3)	180.0 (3)	150 (32)
4	0.581 (3)	0.0 (3)	221 (35)
5	0.581 (3)	178.8 (3)	210 (81)
6	0.586 (3)	0.0 (3)	83 (32)
7	0.588 (3)	177.8 (3)	30 (81)
8	0.579 (3)	0.0 (3)	106 (39)

150 K
1	0.581 (4)	180.0 (4)	101 (53)
2	0.585 (4)	0.0 (4)	44 (34)
3	0.583 (5)	178.5 (5)	150 (135)
4	0.579 (5)	0.0 (5)	194 (65)
5	0.582 (3)	179.6 (3)	300 (134)
6	0.581 (3)	0.0 (3)	81 (28)
7	0.581 (3)	180.0 (3)	143 (62)
8	0.579 (3)	0.0 (3)	159 (28)

170 K
9	0.5824 (16)	0.00 (16)	296 (25)
10	0.5791 (16)	180.00 (16)	44 (44)
11	0.5824 (16)	0.00 (16)	56 (25)
12	0.5790 (16)	180.00 (17)	164 (42)
13	0.584 (2)	178.4 (2)	98 (29)
14	0.5806 (19)	0.6 (2)	270 (54)
15	0.584 (2)	178.4 (2)	218 (28)
16	0.5806 (19)	0.6 (2)	30 (55)

Hydrogen-bond geometry (Å, °) in the asymmetric unit of (I) (symmetry code: x, y, z) top

D—H···A	D—H	H···A	D···A	D—H···A
100 K
O1—H1O1···N1	0.85 (3)	1.80 (3)	2.637 (4)	168 (4)
O3—H1O3···N2	0.84 (4)	1.85 (4)	2.691 (3)	174 (4)
O5—H1O5···N5	0.84 (5)	1.85 (5)	2.689 (4)	170 (7)
O7—H1O7···N6	0.86 (3)	1.83 (4)	2.666 (4)	166 (6)

150 K
O1—H1O1···N1	0.83 (3)	1.80 (3)	2.631 (4)	173 (5)
O3—H1O3···N2	0.84 (4)	1.84 (4)	2.679 (5)	175 (3)
O5—H1O5···N5	0.86 (3)	1.85 (4)	2.680 (3)	162 (5)
O7—H1O7···N6	0.86 (3)	1.80 (3)	2.657 (3)	171 (4)

170 K
O1A—H1O1···N1A	0.87 (2)	1.81 (2)	2.671 (2)	169 (3)
O1B—H2O1···N1B	0.82 (5)	2.01 (5)	2.818 (4)	166 (6)

Refined site-occupancies for the disordered moieties and fractional volume contributions of the minor twin domains top

	Refined site-occupancies ratio			Fractional contribution of minor twin component
LTP (K)	(O1/O2/C1–C8):(O1X/O2X/C1X–C8X)	(O3/O4/C9–C16):(O3X/O4X/C9X–C16X)	(N1–N4/C33–C38):(N1X–N4X/C33X–C38X)
100				0.338 (1)
150	0.803 (6):0.197 (6)	0.900 (4):0.100 (4)	0.867 (11):0.133 (11)	0.259 (2)
160	0.674 (6):0.326 (6)	0.808 (5):0.192 (5)	0.754 (11):0.246 (11)	0.318 (2)
163	0.602 (7):0.398 (7)	0.743 (6):0.257 (6)	0.675 (11):0.325 (11)	0.336 (2)
164	0.553 (7):0.447 (7)	0.701 (6):0.299 (6)	0.633 (13):0.367 (13)	0.341 (3)

HTP (K)	(O1B/O2B/C1B–C8B):(O1Y/O2Y/C1Y–C8Y)
165	0.567 (7):0.433 (7)
166	0.562 (6):0.438 (6)
170	0.563 (7):0.437 (7)
300	0.627 (9):0.373 (9)

Summary of structure refinement variable-temperature data using space group Pccn top

Temperature (K)	Systematic absence violations	R(int)	R(sigma)	R[F²> 2σ(F²)]	wR(F²)
100	963	0.1093	0.0376	0.1686	0.3422
150	774	0.1250	0.0480	0.1308	0.2698
160	697	0.0782	0.0302	0.0948	0.1984
163	530	0.0601	0.0218	0.0756	0.1875
164	347	0.0530	0.0216	0.0686	0.1614
165	85	0.0381	0.0239	0.0600	0.1667
166	75	0.0367	0.0158	0.0616	0.1588
170	26	0.0356	0.0166	0.0609	0.1613
300	67	0.0213	0.0095	0.0693	0.2189

Summary of structure refinement of variable-temperature data using the space group P2₁/c top

Temperature (K)	R_int	R(sigma)	R[F²> 2σ(F²)]	wR(F²)	ADDSYM	TwinRotMat
100	0.0466	0.0331	0.0600	0.1600	Negative	Positive
150	0.0587	0.0436	0.0662	0.1967	Negative	Positive
160	0.0406	0.0316	0.0540	0.1508	Negative	Positive
163	0.0360	0.0252	0.0529	0.1502	Negative	Positive
164	0.0362	0.0261	0.0542	0.1458	Positive	Positive
165	0.0308	0.0343	0.0534	0.1525	Positive	Positive
166	0.0344	0.0231	0.0614	0.1572	Positive	Negative
170	0.0345	0.0240	0.0591	0.1559	Positive	Negative
300	0.0209	0.0130	0.0671	0.2138	Positive	Negative

The aggregate angle (°) and dihedral angle (°) between rings at different temperatures top

The aggregate angle is the angle between two vectors made from the centroid of HMTA molecules to the centroids of adjacent phenyl rings. Ring definitions: A C1–C6, A' C1X–C6X, B C9–C14, B' C9X–C14X, C C17–C22, D C25–C30, E C1A–C6A, F C1B–C6B, F' C1Y–C6Y.

The asterisk (*) and double asterisk (**) indicate molecules generated from the symmetry codes (-x+3/2, -y+3/2, z) and (-x+3/2, -y+1/2, z), respectively.

	Aggregate angles A and B		Dihedral angle between rings
LTP (K)			A/B	A/B'	A'/B	A'/B'	C/D
100	116.89	87.30	57.39 (15)	–	–	–	73.95 (15)
150	117.18	87.58	57.7 (3)	54.2 (14)	60.0 (9)	56.6 (16)	74.13 (14)
160	117.26	87.71	57.6 (3)	54.5 (8)	60.3 (6)	57.1 (10)	74.17 (13)
163	117.30	87.75	58.0 (4)	54.8 (7)	60.0 (5)	56.8 (8)	74.25 (13)
164	117.32	87.73	57.5 (4)	55.1 (7)	60.1 (5)	57.7 (7)	74.26 (14)

HTP (K)			F/F'*	F'/F'*	F/F*	F'/F*	E/E**
165	117.33	87.81	57.6 (6)	53.9 (7)	61.2 (5)	57.6 (6)	74.33 (5)
166	117.34	87.83	57.7 (6)	55.3 (7)	60.1 (5)	57.7 (6)	74.30 (5)
170	117.36	87.86	57.7 (6)	55.0 (7)	60.4 (5)	57.7 (6)	74.31 (5)
300	117.83	88.46	57.7 (6)	55.8 (7)	59.5 (4)	57.7 (6)	73.41 (5)

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Monoclinic-to-ortho­rhom­bic phase transition of the hexa­methyl­ene­tetra­mine–2-methyl­benzoic acid (1/2) cocrystal with temperature-dependent dynamic mol­ecular disorder

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Monoclinic-to-orthorhombic phase transition of the hexamethylenetetramine–2-methylbenzoic acid (1/2) cocrystal with temperature-dependent dynamic molecular disorder