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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616016831/eg3207sup1.cif
Contains datablocks 100K, 150K, 160K, 163K, 164K, 165K, 166K, 170K, 300K, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207100Ksup20.hkl
Contains datablock 100K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207150Ksup21.hkl
Contains datablock 150K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207160Ksup22.hkl
Contains datablock 160K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207163Ksup23.hkl
Contains datablock 163K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207164Ksup24.hkl
Contains datablock 164K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207165Ksup25.hkl
Contains datablock 165K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207166Ksup26.hkl
Contains datablock 166K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016831/eg3207170Ksup27.hkl
Contains datablock 170K

hkl

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
C6H12N4·2C8H8O2F(000) = 1760
Mr = 412.48Dx = 1.323 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 30.904 (5) ÅCell parameters from 9953 reflections
b = 9.3351 (16) Åθ = 2.3–29.1°
c = 14.353 (2) ŵ = 0.09 mm1
β = 90.222 (3)°T = 100 K
V = 4140.7 (11) Å3Block, colourless
Z = 80.39 × 0.33 × 0.26 mm
Data collection top
Bruker APEX DUO CCD area detector
diffractometer
8099 independent reflections
Radiation source: fine-focus sealed tube7204 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
φ and ω scansθmax = 26.0°, θmin = 0.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 3837
Tmin = 0.810, Tmax = 0.947k = 1111
54203 measured reflectionsl = 1717
Refinement top
Refinement on F24 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.060H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.160 w = 1/[σ2(Fo2) + (0.0773P)2 + 4.1888P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
8099 reflectionsΔρmax = 0.64 e Å3
562 parametersΔρmin = 0.23 e Å3
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
xyzUiso*/Ueq
O10.16429 (8)0.2381 (3)0.33462 (19)0.0406 (6)
H1O10.1784 (12)0.246 (4)0.2839 (19)0.049 (12)*
O20.12836 (9)0.4229 (3)0.27456 (16)0.0439 (6)
O30.36626 (7)0.1744 (2)0.28027 (15)0.0312 (5)
H1O30.3453 (11)0.195 (5)0.245 (3)0.062 (14)*
O40.33504 (7)0.3309 (2)0.37521 (17)0.0358 (5)
O50.13407 (9)0.8279 (3)0.52668 (19)0.0448 (6)
H1O50.1575 (15)0.802 (8)0.502 (5)0.15 (3)*
O60.15604 (8)0.6793 (3)0.6378 (2)0.0492 (7)
O70.36420 (8)0.6942 (3)0.51812 (18)0.0400 (6)
H1O70.3382 (9)0.712 (6)0.501 (4)0.077 (17)*
O80.33995 (8)0.7980 (3)0.6463 (2)0.0486 (7)
N10.21740 (8)0.2517 (2)0.19156 (17)0.0216 (5)
N20.29592 (8)0.2296 (2)0.17519 (17)0.0217 (5)
N30.24672 (8)0.1153 (2)0.06219 (17)0.0224 (5)
N40.25374 (8)0.3772 (2)0.06589 (16)0.0220 (5)
N50.20935 (8)0.7764 (2)0.43961 (18)0.0223 (5)
N60.28718 (8)0.7342 (2)0.43796 (18)0.0226 (5)
N70.24047 (8)0.6228 (2)0.32030 (16)0.0217 (5)
N80.25341 (8)0.8813 (2)0.31670 (17)0.0227 (5)
C10.10787 (9)0.3302 (3)0.4244 (2)0.0242 (6)
C20.07828 (10)0.4407 (3)0.4460 (2)0.0281 (7)
C30.05609 (11)0.4302 (4)0.5292 (2)0.0353 (8)
H3A0.03620.50350.54550.042*
C40.06208 (12)0.3159 (4)0.5895 (2)0.0418 (9)
H4A0.04660.31270.64650.050*
C50.09058 (12)0.2060 (4)0.5674 (2)0.0383 (8)
H5A0.09460.12710.60830.046*
C60.11286 (10)0.2145 (3)0.4849 (2)0.0292 (7)
H6A0.13220.13940.46870.035*
C70.13352 (10)0.3367 (3)0.3367 (2)0.0279 (6)
C80.06932 (11)0.5691 (3)0.3850 (3)0.0357 (8)
H8A0.05910.53680.32380.054*
H8B0.09590.62480.37750.054*
H8C0.04710.62900.41420.054*
C90.39527 (9)0.2020 (3)0.4344 (2)0.0196 (6)
C100.41867 (9)0.0726 (3)0.4376 (2)0.0209 (6)
C110.44576 (10)0.0493 (3)0.5151 (2)0.0262 (6)
H11A0.46150.03790.51900.031*
C120.45028 (10)0.1487 (3)0.5857 (2)0.0301 (7)
H12A0.46910.12940.63670.036*
C130.42751 (10)0.2764 (3)0.5824 (2)0.0293 (7)
H13A0.43050.34510.63080.035*
C140.40033 (10)0.3023 (3)0.5073 (2)0.0239 (6)
H14A0.38470.38980.50470.029*
C150.36291 (9)0.2421 (3)0.3609 (2)0.0208 (6)
C160.41711 (10)0.0412 (3)0.3634 (2)0.0278 (6)
H16A0.38690.06020.34630.042*
H16B0.43040.12930.38720.042*
H16C0.43300.00820.30840.042*
C170.08182 (9)0.7499 (3)0.6339 (2)0.0251 (6)
C180.06742 (11)0.6690 (3)0.7095 (2)0.0320 (7)
C190.02328 (10)0.6728 (4)0.7311 (3)0.0366 (8)
H19A0.01290.61920.78270.044*
C200.00563 (11)0.7533 (4)0.6788 (3)0.0384 (8)
H20A0.03540.75320.69480.046*
C210.00832 (11)0.8344 (4)0.6032 (3)0.0380 (8)
H21A0.01160.88970.56760.046*
C220.05122 (11)0.8323 (3)0.5817 (3)0.0338 (7)
H22A0.06110.88730.53030.041*
C230.12698 (10)0.7495 (3)0.6005 (2)0.0314 (7)
C240.09609 (12)0.5781 (4)0.7694 (3)0.0416 (8)
H24A0.07860.52880.81630.062*
H24B0.11760.63880.80060.062*
H24C0.11090.50710.73060.062*
C250.41586 (9)0.7485 (3)0.6351 (2)0.0227 (6)
C260.43051 (10)0.8278 (3)0.7111 (2)0.0267 (6)
C270.47509 (10)0.8216 (3)0.7337 (2)0.0310 (7)
H27A0.48560.87490.78540.037*
C280.50350 (10)0.7411 (3)0.6829 (2)0.0319 (7)
H28A0.53330.73920.69970.038*
C290.48885 (11)0.6614 (3)0.6064 (2)0.0317 (7)
H29A0.50850.60470.57150.038*
C300.44569 (10)0.6658 (3)0.5820 (2)0.0272 (7)
H30A0.43570.61340.52930.033*
C310.36989 (10)0.7496 (3)0.6010 (2)0.0253 (6)
C320.40246 (11)0.9198 (4)0.7693 (2)0.0357 (7)
H32A0.42040.97520.81270.054*
H32B0.38230.85980.80450.054*
H32C0.38610.98550.72920.054*
C330.25954 (9)0.2388 (3)0.24103 (19)0.0216 (6)
H33A0.26370.32300.28210.026*
H33B0.25920.15210.28070.026*
C340.28807 (10)0.1046 (3)0.1134 (2)0.0236 (6)
H34A0.31200.09700.06820.028*
H34B0.28800.01620.15150.028*
C350.21168 (10)0.1256 (3)0.1296 (2)0.0225 (6)
H35A0.21090.03730.16780.027*
H35B0.18370.13370.09610.027*
C360.21844 (10)0.3830 (3)0.1331 (2)0.0235 (6)
H36A0.19060.39310.09960.028*
H36B0.22220.46800.17370.028*
C370.29503 (10)0.3608 (3)0.1167 (2)0.0235 (6)
H37A0.29970.44570.15690.028*
H37B0.31910.35680.07130.028*
C380.24733 (11)0.2484 (3)0.00687 (18)0.0241 (6)
H38A0.21960.25750.02750.029*
H38B0.27090.24280.03940.029*
C390.24873 (10)0.7575 (3)0.49655 (18)0.0238 (6)
H39A0.24490.67440.53860.029*
H39B0.25330.84360.53560.029*
C400.27919 (10)0.6067 (3)0.3790 (2)0.0242 (6)
H40A0.30460.59020.33880.029*
H40B0.27570.52170.41950.029*
C410.20344 (10)0.6471 (3)0.3803 (2)0.0245 (6)
H41A0.19920.56240.42070.029*
H41B0.17720.65900.34140.029*
C420.21598 (10)0.9010 (3)0.3770 (2)0.0236 (6)
H42A0.18980.91490.33800.028*
H42B0.22010.98850.41500.028*
C430.29158 (10)0.8604 (3)0.3755 (2)0.0262 (6)
H43A0.29630.94720.41380.031*
H43B0.31730.84730.33540.031*
C440.24618 (11)0.7498 (3)0.26074 (19)0.0261 (6)
H44A0.22010.76260.22130.031*
H44B0.27120.73450.21910.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0366 (13)0.0444 (14)0.0410 (15)0.0105 (11)0.0137 (11)0.0071 (11)
O20.0523 (15)0.0502 (15)0.0293 (12)0.0141 (12)0.0077 (11)0.0083 (11)
O30.0304 (12)0.0352 (12)0.0279 (11)0.0116 (10)0.0038 (10)0.0041 (9)
O40.0316 (12)0.0318 (12)0.0440 (13)0.0155 (10)0.0100 (10)0.0129 (10)
O50.0409 (15)0.0492 (15)0.0443 (15)0.0019 (12)0.0110 (12)0.0066 (12)
O60.0229 (12)0.0493 (15)0.075 (2)0.0089 (11)0.0036 (13)0.0094 (14)
O70.0332 (13)0.0494 (15)0.0373 (13)0.0057 (11)0.0069 (11)0.0089 (11)
O80.0271 (12)0.0605 (16)0.0581 (17)0.0082 (12)0.0022 (12)0.0152 (14)
N10.0275 (12)0.0187 (11)0.0185 (12)0.0008 (10)0.0019 (10)0.0030 (9)
N20.0262 (12)0.0175 (11)0.0215 (12)0.0000 (9)0.0018 (10)0.0019 (9)
N30.0331 (14)0.0132 (10)0.0209 (12)0.0007 (9)0.0016 (11)0.0007 (9)
N40.0351 (14)0.0131 (10)0.0177 (12)0.0003 (9)0.0016 (11)0.0004 (9)
N50.0225 (12)0.0180 (11)0.0266 (13)0.0014 (9)0.0073 (11)0.0019 (10)
N60.0226 (12)0.0176 (11)0.0277 (13)0.0004 (9)0.0053 (11)0.0017 (10)
N70.0308 (13)0.0150 (11)0.0194 (12)0.0000 (10)0.0008 (10)0.0026 (9)
N80.0290 (13)0.0169 (11)0.0222 (12)0.0004 (10)0.0020 (10)0.0039 (9)
C10.0214 (14)0.0281 (15)0.0231 (14)0.0035 (11)0.0012 (12)0.0054 (12)
C20.0277 (15)0.0270 (15)0.0297 (16)0.0076 (12)0.0001 (13)0.0056 (12)
C30.0318 (17)0.0376 (18)0.0367 (18)0.0066 (14)0.0115 (15)0.0150 (15)
C40.046 (2)0.054 (2)0.0253 (17)0.0248 (17)0.0137 (15)0.0138 (16)
C50.048 (2)0.0378 (17)0.0292 (17)0.0180 (16)0.0028 (16)0.0061 (14)
C60.0268 (15)0.0324 (16)0.0283 (16)0.0022 (13)0.0063 (13)0.0030 (13)
C70.0251 (15)0.0272 (14)0.0314 (16)0.0019 (12)0.0006 (13)0.0051 (13)
C80.0353 (17)0.0260 (15)0.046 (2)0.0028 (13)0.0019 (15)0.0004 (14)
C90.0164 (13)0.0191 (12)0.0232 (14)0.0021 (10)0.0026 (11)0.0025 (11)
C100.0181 (13)0.0197 (13)0.0250 (14)0.0030 (10)0.0052 (12)0.0019 (11)
C110.0236 (14)0.0211 (13)0.0341 (16)0.0007 (12)0.0034 (13)0.0071 (12)
C120.0343 (17)0.0274 (15)0.0287 (17)0.0081 (13)0.0037 (14)0.0076 (13)
C130.0376 (17)0.0297 (15)0.0208 (15)0.0072 (13)0.0027 (13)0.0037 (12)
C140.0253 (15)0.0201 (13)0.0263 (15)0.0003 (11)0.0054 (12)0.0002 (11)
C150.0204 (13)0.0171 (12)0.0249 (14)0.0020 (11)0.0001 (11)0.0013 (11)
C160.0254 (15)0.0193 (13)0.0387 (17)0.0030 (11)0.0020 (13)0.0026 (12)
C170.0217 (14)0.0238 (13)0.0298 (16)0.0020 (12)0.0018 (13)0.0088 (12)
C180.0313 (17)0.0301 (16)0.0345 (17)0.0029 (13)0.0006 (14)0.0067 (13)
C190.0259 (16)0.0442 (19)0.0396 (19)0.0100 (14)0.0073 (14)0.0186 (16)
C200.0314 (17)0.0460 (19)0.0377 (19)0.0064 (16)0.0044 (15)0.0141 (16)
C210.0286 (17)0.0420 (19)0.043 (2)0.0110 (15)0.0093 (15)0.0112 (16)
C220.0332 (17)0.0310 (16)0.0371 (18)0.0012 (14)0.0003 (15)0.0062 (14)
C230.0280 (16)0.0278 (15)0.0386 (19)0.0055 (14)0.0040 (15)0.0098 (14)
C240.046 (2)0.0392 (19)0.040 (2)0.0005 (16)0.0031 (17)0.0007 (15)
C250.0246 (14)0.0187 (12)0.0248 (15)0.0033 (11)0.0009 (12)0.0064 (11)
C260.0334 (16)0.0224 (14)0.0242 (15)0.0046 (12)0.0025 (13)0.0067 (12)
C270.0288 (16)0.0287 (16)0.0355 (18)0.0064 (13)0.0042 (14)0.0138 (14)
C280.0296 (16)0.0319 (16)0.0342 (18)0.0069 (14)0.0028 (14)0.0103 (13)
C290.0308 (16)0.0263 (15)0.0382 (18)0.0046 (13)0.0084 (14)0.0058 (13)
C300.0301 (16)0.0232 (14)0.0283 (16)0.0005 (12)0.0014 (13)0.0025 (12)
C310.0252 (15)0.0174 (12)0.0331 (17)0.0020 (12)0.0038 (13)0.0039 (12)
C320.0398 (19)0.0306 (16)0.0369 (18)0.0002 (14)0.0070 (15)0.0012 (14)
C330.0298 (15)0.0202 (13)0.0146 (13)0.0013 (12)0.0010 (11)0.0009 (11)
C340.0304 (16)0.0168 (12)0.0235 (14)0.0011 (11)0.0013 (12)0.0013 (11)
C350.0305 (15)0.0151 (12)0.0219 (14)0.0043 (11)0.0003 (12)0.0008 (11)
C360.0312 (16)0.0153 (13)0.0238 (15)0.0032 (11)0.0032 (13)0.0051 (11)
C370.0304 (16)0.0163 (12)0.0238 (15)0.0040 (11)0.0014 (12)0.0015 (11)
C380.0395 (16)0.0183 (12)0.0146 (12)0.0020 (11)0.0014 (13)0.0002 (12)
C390.0370 (15)0.0157 (12)0.0185 (13)0.0008 (11)0.0020 (14)0.0023 (11)
C400.0271 (15)0.0161 (13)0.0293 (15)0.0072 (11)0.0012 (12)0.0008 (12)
C410.0258 (15)0.0158 (12)0.0317 (16)0.0081 (11)0.0005 (13)0.0029 (12)
C420.0274 (15)0.0138 (12)0.0297 (16)0.0050 (11)0.0033 (13)0.0009 (12)
C430.0211 (14)0.0214 (13)0.0361 (17)0.0055 (11)0.0023 (13)0.0009 (13)
C440.0404 (17)0.0212 (13)0.0168 (13)0.0012 (12)0.0004 (14)0.0017 (12)
Geometric parameters (Å, º) top
O1—C71.324 (4)C13—C141.385 (4)
O1—H1O10.853 (19)C13—H13A0.9500
O2—C71.211 (4)C14—H14A0.9500
O3—C151.323 (4)C16—H16A0.9800
O3—H1O30.845 (19)C16—H16B0.9800
O4—C151.213 (3)C16—H16C0.9800
O5—C231.307 (4)C17—C181.396 (5)
O5—H1O50.85 (2)C17—C221.429 (5)
O6—C231.232 (4)C17—C231.478 (4)
O7—C311.308 (4)C18—C191.401 (5)
O7—H1O70.854 (19)C18—C241.496 (5)
O8—C311.220 (4)C19—C201.386 (5)
N1—C351.485 (3)C19—H19A0.9500
N1—C361.485 (4)C20—C211.393 (6)
N1—C331.486 (4)C20—H20A0.9500
N2—C331.474 (4)C21—C221.363 (5)
N2—C341.485 (4)C21—H21A0.9500
N2—C371.485 (3)C22—H22A0.9500
N3—C351.458 (4)C24—H24A0.9800
N3—C381.475 (4)C24—H24B0.9800
N3—C341.475 (4)C24—H24C0.9800
N4—C361.461 (4)C25—C261.392 (4)
N4—C371.475 (4)C25—C301.426 (4)
N4—C381.484 (4)C25—C311.501 (4)
N5—C391.474 (4)C26—C271.415 (4)
N5—C421.485 (4)C26—C321.481 (4)
N5—C411.488 (4)C27—C281.368 (5)
N6—C391.474 (4)C27—H27A0.9500
N6—C401.480 (4)C28—C291.401 (5)
N6—C431.487 (4)C28—H28A0.9500
N7—C411.453 (4)C29—C301.378 (5)
N7—C401.469 (4)C29—H29A0.9500
N7—C441.473 (4)C30—H30A0.9500
N8—C421.459 (4)C32—H32A0.9800
N8—C431.461 (4)C32—H32B0.9800
N8—C441.483 (4)C32—H32C0.9800
C1—C61.395 (4)C33—H33A0.9900
C1—C21.414 (4)C33—H33B0.9900
C1—C71.491 (4)C34—H34A0.9900
C2—C31.383 (5)C34—H34B0.9900
C2—C81.509 (4)C35—H35A0.9900
C3—C41.386 (5)C35—H35B0.9900
C3—H3A0.9500C36—H36A0.9900
C4—C51.389 (5)C36—H36B0.9900
C4—H4A0.9500C37—H37A0.9900
C5—C61.374 (5)C37—H37B0.9900
C5—H5A0.9500C38—H38A0.9900
C6—H6A0.9500C38—H38B0.9900
C8—H8A0.9800C39—H39A0.9900
C8—H8B0.9800C39—H39B0.9900
C8—H8C0.9800C40—H40A0.9900
C9—C101.408 (4)C40—H40B0.9900
C9—C141.412 (4)C41—H41A0.9900
C9—C151.499 (4)C41—H41B0.9900
C10—C111.406 (4)C42—H42A0.9900
C10—C161.506 (4)C42—H42B0.9900
C11—C121.380 (4)C43—H43A0.9900
C11—H11A0.9500C43—H43B0.9900
C12—C131.385 (5)C44—H44A0.9900
C12—H12A0.9500C44—H44B0.9900
C7—O1—H1O1109 (3)C18—C24—H24B109.5
C15—O3—H1O3111 (3)H24A—C24—H24B109.5
C23—O5—H1O5109 (6)C18—C24—H24C109.5
C31—O7—H1O7108 (4)H24A—C24—H24C109.5
C35—N1—C36108.6 (2)H24B—C24—H24C109.5
C35—N1—C33108.9 (2)C26—C25—C30119.9 (3)
C36—N1—C33108.4 (2)C26—C25—C31123.8 (3)
C33—N2—C34107.8 (2)C30—C25—C31116.2 (3)
C33—N2—C37107.6 (2)C25—C26—C27118.1 (3)
C34—N2—C37107.9 (2)C25—C26—C32124.1 (3)
C35—N3—C38108.2 (2)C27—C26—C32117.8 (3)
C35—N3—C34108.5 (2)C28—C27—C26121.8 (3)
C38—N3—C34108.2 (2)C28—C27—H27A119.1
C36—N4—C37108.9 (2)C26—C27—H27A119.1
C36—N4—C38108.0 (2)C27—C28—C29120.2 (3)
C37—N4—C38108.2 (2)C27—C28—H28A119.9
C39—N5—C42108.3 (2)C29—C28—H28A119.9
C39—N5—C41108.6 (2)C30—C29—C28119.5 (3)
C42—N5—C41107.8 (2)C30—C29—H29A120.2
C39—N6—C40108.2 (2)C28—C29—H29A120.2
C39—N6—C43107.6 (2)C29—C30—C25120.5 (3)
C40—N6—C43107.9 (2)C29—C30—H30A119.8
C41—N7—C40108.5 (2)C25—C30—H30A119.8
C41—N7—C44108.3 (2)O8—C31—O7122.1 (3)
C40—N7—C44108.5 (2)O8—C31—C25123.2 (3)
C42—N8—C43108.3 (2)O7—C31—C25114.7 (3)
C42—N8—C44107.9 (2)C26—C32—H32A109.5
C43—N8—C44108.8 (2)C26—C32—H32B109.5
C6—C1—C2119.9 (3)H32A—C32—H32B109.5
C6—C1—C7120.0 (3)C26—C32—H32C109.5
C2—C1—C7120.1 (3)H32A—C32—H32C109.5
C3—C2—C1117.5 (3)H32B—C32—H32C109.5
C3—C2—C8117.8 (3)N2—C33—N1111.6 (2)
C1—C2—C8124.8 (3)N2—C33—H33A109.3
C2—C3—C4121.9 (3)N1—C33—H33A109.3
C2—C3—H3A119.1N2—C33—H33B109.3
C4—C3—H3A119.1N1—C33—H33B109.3
C3—C4—C5120.6 (3)H33A—C33—H33B108.0
C3—C4—H4A119.7N3—C34—N2112.6 (2)
C5—C4—H4A119.7N3—C34—H34A109.1
C6—C5—C4118.3 (3)N2—C34—H34A109.1
C6—C5—H5A120.8N3—C34—H34B109.1
C4—C5—H5A120.8N2—C34—H34B109.1
C5—C6—C1121.8 (3)H34A—C34—H34B107.8
C5—C6—H6A119.1N3—C35—N1111.3 (2)
C1—C6—H6A119.1N3—C35—H35A109.4
O2—C7—O1122.5 (3)N1—C35—H35A109.4
O2—C7—C1125.4 (3)N3—C35—H35B109.4
O1—C7—C1112.0 (3)N1—C35—H35B109.4
C2—C8—H8A109.5H35A—C35—H35B108.0
C2—C8—H8B109.5N4—C36—N1111.1 (2)
H8A—C8—H8B109.5N4—C36—H36A109.4
C2—C8—H8C109.5N1—C36—H36A109.4
H8A—C8—H8C109.5N4—C36—H36B109.4
H8B—C8—H8C109.5N1—C36—H36B109.4
C10—C9—C14119.2 (3)H36A—C36—H36B108.0
C10—C9—C15125.4 (3)N4—C37—N2112.3 (2)
C14—C9—C15115.3 (2)N4—C37—H37A109.2
C11—C10—C9117.6 (3)N2—C37—H37A109.2
C11—C10—C16117.9 (2)N4—C37—H37B109.2
C9—C10—C16124.5 (3)N2—C37—H37B109.2
C12—C11—C10122.3 (3)H37A—C37—H37B107.9
C12—C11—H11A118.8N3—C38—N4112.2 (2)
C10—C11—H11A118.8N3—C38—H38A109.2
C11—C12—C13120.2 (3)N4—C38—H38A109.2
C11—C12—H12A119.9N3—C38—H38B109.2
C13—C12—H12A119.9N4—C38—H38B109.2
C12—C13—C14118.9 (3)H38A—C38—H38B107.9
C12—C13—H13A120.5N5—C39—N6111.5 (2)
C14—C13—H13A120.5N5—C39—H39A109.3
C13—C14—C9121.7 (3)N6—C39—H39A109.3
C13—C14—H14A119.1N5—C39—H39B109.3
C9—C14—H14A119.1N6—C39—H39B109.3
O4—C15—O3122.2 (3)H39A—C39—H39B108.0
O4—C15—C9121.5 (3)N7—C40—N6112.3 (2)
O3—C15—C9116.2 (2)N7—C40—H40A109.1
C10—C16—H16A109.5N6—C40—H40A109.1
C10—C16—H16B109.5N7—C40—H40B109.1
H16A—C16—H16B109.5N6—C40—H40B109.1
C10—C16—H16C109.5H40A—C40—H40B107.9
H16A—C16—H16C109.5N7—C41—N5111.8 (2)
H16B—C16—H16C109.5N7—C41—H41A109.3
C18—C17—C22119.1 (3)N5—C41—H41A109.3
C18—C17—C23123.7 (3)N7—C41—H41B109.3
C22—C17—C23117.0 (3)N5—C41—H41B109.3
C17—C18—C19118.2 (3)H41A—C41—H41B107.9
C17—C18—C24124.3 (3)N8—C42—N5111.8 (2)
C19—C18—C24117.5 (3)N8—C42—H42A109.3
C20—C19—C18121.3 (3)N5—C42—H42A109.3
C20—C19—H19A119.3N8—C42—H42B109.3
C18—C19—H19A119.3N5—C42—H42B109.3
C19—C20—C21121.1 (3)H42A—C42—H42B107.9
C19—C20—H20A119.5N8—C43—N6112.3 (2)
C21—C20—H20A119.5N8—C43—H43A109.2
C22—C21—C20118.2 (3)N6—C43—H43A109.2
C22—C21—H21A120.9N8—C43—H43B109.2
C20—C21—H21A120.9N6—C43—H43B109.2
C21—C22—C17122.1 (3)H43A—C43—H43B107.9
C21—C22—H22A119.0N7—C44—N8111.7 (2)
C17—C22—H22A119.0N7—C44—H44A109.3
O6—C23—O5121.7 (3)N8—C44—H44A109.3
O6—C23—C17123.2 (3)N7—C44—H44B109.3
O5—C23—C17115.0 (3)N8—C44—H44B109.3
C18—C24—H24A109.5H44A—C44—H44B107.9
C6—C1—C2—C31.7 (4)C26—C25—C30—C291.3 (4)
C7—C1—C2—C3178.7 (3)C31—C25—C30—C29178.3 (3)
C6—C1—C2—C8178.5 (3)C26—C25—C31—O814.1 (5)
C7—C1—C2—C81.1 (4)C30—C25—C31—O8169.1 (3)
C1—C2—C3—C40.4 (5)C26—C25—C31—O7165.9 (3)
C8—C2—C3—C4179.8 (3)C30—C25—C31—O710.9 (4)
C2—C3—C4—C50.7 (5)C34—N2—C33—N157.6 (3)
C3—C4—C5—C60.6 (5)C37—N2—C33—N158.6 (3)
C4—C5—C6—C10.7 (5)C35—N1—C33—N258.5 (3)
C2—C1—C6—C51.9 (4)C36—N1—C33—N259.5 (3)
C7—C1—C6—C5178.5 (3)C35—N3—C34—N259.1 (3)
C6—C1—C7—O2171.3 (3)C38—N3—C34—N258.1 (3)
C2—C1—C7—O28.3 (5)C33—N2—C34—N358.2 (3)
C6—C1—C7—O110.5 (4)C37—N2—C34—N357.7 (3)
C2—C1—C7—O1169.9 (3)C38—N3—C35—N158.6 (3)
C14—C9—C10—C110.8 (4)C34—N3—C35—N158.6 (3)
C15—C9—C10—C11176.1 (3)C36—N1—C35—N359.1 (3)
C14—C9—C10—C16178.3 (3)C33—N1—C35—N358.8 (3)
C15—C9—C10—C164.8 (4)C37—N4—C36—N158.6 (3)
C9—C10—C11—C120.9 (4)C38—N4—C36—N158.7 (3)
C16—C10—C11—C12178.3 (3)C35—N1—C36—N459.2 (3)
C10—C11—C12—C130.5 (4)C33—N1—C36—N459.0 (3)
C11—C12—C13—C140.1 (4)C36—N4—C37—N258.8 (3)
C12—C13—C14—C90.1 (4)C38—N4—C37—N258.3 (3)
C10—C9—C14—C130.5 (4)C33—N2—C37—N458.3 (3)
C15—C9—C14—C13176.8 (3)C34—N2—C37—N457.8 (3)
C10—C9—C15—O4157.5 (3)C35—N3—C38—N459.0 (3)
C14—C9—C15—O419.6 (4)C34—N3—C38—N458.4 (3)
C10—C9—C15—O321.9 (4)C36—N4—C38—N359.1 (3)
C14—C9—C15—O3161.0 (3)C37—N4—C38—N358.6 (3)
C22—C17—C18—C190.3 (4)C42—N5—C39—N658.7 (3)
C23—C17—C18—C19176.6 (3)C41—N5—C39—N658.1 (3)
C22—C17—C18—C24179.8 (3)C40—N6—C39—N557.9 (3)
C23—C17—C18—C243.5 (5)C43—N6—C39—N558.5 (3)
C17—C18—C19—C200.6 (5)C41—N7—C40—N658.8 (3)
C24—C18—C19—C20179.5 (3)C44—N7—C40—N658.7 (3)
C18—C19—C20—C210.6 (5)C39—N6—C40—N758.3 (3)
C19—C20—C21—C220.2 (5)C43—N6—C40—N757.9 (3)
C20—C21—C22—C170.1 (5)C40—N7—C41—N558.4 (3)
C18—C17—C22—C210.0 (5)C44—N7—C41—N559.1 (3)
C23—C17—C22—C21176.5 (3)C39—N5—C41—N758.6 (3)
C18—C17—C23—O61.4 (5)C42—N5—C41—N758.6 (3)
C22—C17—C23—O6177.7 (3)C43—N8—C42—N558.7 (3)
C18—C17—C23—O5177.6 (3)C44—N8—C42—N559.0 (3)
C22—C17—C23—O51.2 (4)C39—N5—C42—N858.7 (3)
C30—C25—C26—C270.8 (4)C41—N5—C42—N858.6 (3)
C31—C25—C26—C27177.4 (3)C42—N8—C43—N659.1 (3)
C30—C25—C26—C32178.4 (3)C44—N8—C43—N657.9 (3)
C31—C25—C26—C321.7 (4)C39—N6—C43—N858.9 (3)
C25—C26—C27—C280.2 (4)C40—N6—C43—N857.6 (3)
C32—C26—C27—C28179.0 (3)C41—N7—C44—N859.4 (3)
C26—C27—C28—C290.1 (5)C40—N7—C44—N858.2 (3)
C27—C28—C29—C300.6 (5)C42—N8—C44—N759.2 (3)
C28—C29—C30—C251.3 (5)C43—N8—C44—N758.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N10.85 (3)1.80 (3)2.637 (4)168 (4)
O3—H1O3···N20.84 (4)1.85 (4)2.691 (3)174 (4)
O5—H1O5···N50.84 (5)1.85 (5)2.689 (4)170 (7)
O7—H1O7···N60.86 (3)1.83 (4)2.666 (4)166 (6)
C6—H6A···O10.952.362.693 (4)100
C16—H16A···O30.982.472.816 (4)100
C22—H22A···O50.952.322.683 (4)102
C30—H30A···O70.952.342.690 (4)101
C33—H33A···O40.992.573.140 (4)116
C33—H33B···N8i0.992.593.515 (3)156
C36—H36B···N70.992.613.561 (4)160
C38—H38B···O4ii0.992.433.392 (4)163
C40—H40B···N3iii0.992.583.498 (4)155
C44—H44A···O6iv0.992.373.358 (4)173
C44—H44B···O8iv0.992.393.366 (4)169
Symmetry codes: (i) x, y1, z; (ii) x, y+1/2, z1/2; (iii) x, y+1/2, z+1/2; (iv) x, y+3/2, z1/2.
(150K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top
Crystal data top
C6H12N4·2C8H8O2F(000) = 1760
Mr = 412.48Dx = 1.323 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 30.920 (3) ÅCell parameters from 9985 reflections
b = 9.3363 (9) Åθ = 2.3–26.6°
c = 14.3462 (14) ŵ = 0.09 mm1
β = 90.314 (2)°T = 150 K
V = 4141.4 (7) Å3Block, colourless
Z = 80.43 × 0.17 × 0.15 mm
Data collection top
Bruker APEX DUO CCD area detector
diffractometer
9989 independent reflections
Radiation source: fine-focus sealed tube7832 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
φ and ω scansθmax = 28.0°, θmin = 0.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 4040
Tmin = 0.769, Tmax = 0.963k = 1212
65004 measured reflectionsl = 1818
Refinement top
Refinement on F21222 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.197 w = 1/[σ2(Fo2) + (0.1018P)2 + 2.4093P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
9989 reflectionsΔρmax = 0.43 e Å3
837 parametersΔρmin = 0.24 e Å3
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
xyzUiso*/UeqOcc. (<1)
O10.16458 (10)0.2389 (4)0.3356 (2)0.0453 (8)0.803 (6)
H1O10.1813 (13)0.250 (5)0.291 (2)0.054 (14)*0.803 (6)
O20.12827 (12)0.4205 (5)0.2743 (2)0.0547 (9)0.803 (6)
C70.13377 (12)0.3353 (4)0.3370 (3)0.0306 (8)0.803 (6)
C10.10771 (18)0.3308 (5)0.4241 (3)0.0284 (8)0.803 (6)
C20.0784 (3)0.4407 (6)0.4467 (4)0.0324 (9)0.803 (6)
C30.0562 (3)0.4293 (7)0.5308 (4)0.0405 (12)0.803 (6)
H3A0.03640.50240.54770.049*0.803 (6)
C40.06230 (18)0.3153 (6)0.5898 (3)0.0435 (11)0.803 (6)
H4A0.04700.31130.64700.052*0.803 (6)
C50.09044 (18)0.2066 (5)0.5668 (3)0.0412 (10)0.803 (6)
H5A0.09430.12730.60750.049*0.803 (6)
C60.11288 (14)0.2137 (5)0.4845 (3)0.0325 (8)0.803 (6)
H6A0.13210.13850.46830.039*0.803 (6)
C80.06987 (17)0.5688 (5)0.3856 (4)0.0400 (11)0.803 (6)
H8A0.09680.62230.37690.060*0.803 (6)
H8B0.04840.63080.41520.060*0.803 (6)
H8C0.05890.53670.32490.060*0.803 (6)
O1X0.1334 (5)0.3388 (18)0.2842 (10)0.056 (3)0.197 (6)
H2O10.15200.31180.24540.084*0.197 (6)
O2X0.1648 (4)0.1732 (16)0.3752 (11)0.058 (3)0.197 (6)
C7X0.1373 (5)0.2632 (18)0.3608 (10)0.036 (2)0.197 (6)
C1X0.1061 (9)0.300 (2)0.4369 (14)0.031 (2)0.197 (6)
C2X0.0822 (13)0.427 (3)0.436 (2)0.034 (2)0.197 (6)
C3X0.0550 (11)0.447 (3)0.5112 (18)0.036 (2)0.197 (6)
H3XA0.03850.53290.51300.043*0.197 (6)
C4X0.0505 (7)0.353 (2)0.5830 (15)0.039 (2)0.197 (6)
H4XA0.03180.37460.63340.047*0.197 (6)
C5X0.0733 (7)0.225 (2)0.5822 (12)0.037 (2)0.197 (6)
H5XA0.06950.15610.63000.044*0.197 (6)
C6X0.1012 (6)0.2017 (19)0.5108 (13)0.034 (2)0.197 (6)
H6XA0.11800.11640.51080.041*0.197 (6)
C8X0.0817 (8)0.542 (2)0.3619 (14)0.041 (4)0.197 (6)
H8XA0.10450.61260.37560.062*0.197 (6)
H8XB0.05350.59030.36170.062*0.197 (6)
H8XC0.08690.49960.30060.062*0.197 (6)
O30.36593 (9)0.1747 (3)0.28202 (17)0.0422 (6)0.900 (4)
H1O30.3433 (11)0.188 (6)0.251 (3)0.081 (16)*0.900 (4)
O40.33475 (8)0.3294 (3)0.3771 (2)0.0469 (7)0.900 (4)
C150.36249 (10)0.2416 (3)0.3621 (2)0.0293 (6)0.900 (4)
C90.39507 (12)0.2020 (3)0.4356 (2)0.0251 (6)0.900 (4)
C100.4184 (2)0.0731 (6)0.4380 (4)0.0266 (6)0.900 (4)
C110.44569 (16)0.0493 (4)0.5148 (3)0.0326 (7)0.900 (4)
H11A0.46130.03810.51860.039*0.900 (4)
C120.45049 (13)0.1496 (4)0.5852 (2)0.0363 (8)0.900 (4)
H12A0.46970.13140.63580.044*0.900 (4)
C130.42739 (13)0.2761 (4)0.5820 (2)0.0356 (7)0.900 (4)
H13A0.43030.34480.63050.043*0.900 (4)
C140.40008 (11)0.3016 (3)0.5076 (3)0.0303 (7)0.900 (4)
H14A0.38430.38890.50520.036*0.900 (4)
C160.41689 (13)0.0414 (3)0.3644 (3)0.0352 (8)0.900 (4)
H16A0.38680.05780.34520.053*0.900 (4)
H16B0.42910.13030.38960.053*0.900 (4)
H16C0.43380.01080.31040.053*0.900 (4)
O3X0.3342 (6)0.263 (2)0.3362 (17)0.041 (4)0.100 (4)
H2O30.32010.25670.28610.061*0.100 (4)
O4X0.3724 (7)0.087 (3)0.2731 (13)0.044 (4)0.100 (4)
C15X0.3654 (8)0.168 (3)0.3366 (16)0.031 (3)0.100 (4)
C9X0.3938 (12)0.166 (3)0.423 (2)0.029 (2)0.100 (4)
C10X0.424 (2)0.059 (6)0.446 (4)0.030 (2)0.100 (4)
C11X0.4451 (16)0.078 (4)0.531 (2)0.032 (3)0.100 (4)
H11B0.46700.01140.54860.039*0.100 (4)
C12X0.4359 (11)0.189 (4)0.5921 (19)0.033 (2)0.100 (4)
H12B0.44850.18980.65260.039*0.100 (4)
C13X0.4089 (11)0.298 (3)0.565 (2)0.032 (2)0.100 (4)
H13B0.40440.37900.60400.038*0.100 (4)
C14X0.3887 (10)0.284 (3)0.481 (2)0.031 (2)0.100 (4)
H14B0.37020.35960.46120.037*0.100 (4)
C16X0.4323 (12)0.069 (3)0.384 (2)0.036 (5)0.100 (4)
H16D0.45500.12880.41180.054*0.100 (4)
H16E0.44190.03580.32230.054*0.100 (4)
H16F0.40580.12550.37650.054*0.100 (4)
O50.13451 (8)0.8236 (3)0.52665 (18)0.0538 (6)
H1O50.1600 (9)0.799 (6)0.510 (4)0.105 (19)*
O60.15657 (8)0.6816 (3)0.6407 (2)0.0614 (7)
O70.36404 (8)0.6928 (3)0.52055 (17)0.0520 (6)
H1O70.3380 (8)0.705 (5)0.500 (3)0.075 (14)*
O80.34069 (8)0.8009 (3)0.6472 (2)0.0641 (7)
N50.20988 (7)0.7751 (2)0.44080 (16)0.0296 (5)
N60.28740 (7)0.7330 (2)0.44014 (16)0.0294 (5)
N70.24123 (8)0.6228 (2)0.32180 (15)0.0299 (5)
N80.25407 (7)0.8806 (2)0.31915 (15)0.0303 (5)
C170.08235 (9)0.7497 (3)0.6344 (2)0.0313 (6)
C180.06768 (10)0.6693 (3)0.7096 (2)0.0382 (6)
C190.02389 (10)0.6739 (4)0.7308 (2)0.0433 (7)
H19A0.01350.62020.78230.052*
C200.00495 (10)0.7543 (4)0.6791 (2)0.0458 (8)
H20A0.03470.75450.69510.055*
C210.00916 (11)0.8349 (4)0.6040 (2)0.0454 (8)
H21A0.01060.89110.56860.054*
C220.05226 (10)0.8317 (3)0.5821 (2)0.0403 (7)
H22A0.06220.88600.53050.048*
C230.12775 (10)0.7481 (3)0.6022 (2)0.0374 (6)
C240.09651 (12)0.5783 (4)0.7695 (2)0.0503 (8)
H24A0.07910.52920.81660.075*
H24B0.11810.63900.80040.075*
H24C0.11120.50720.73060.075*
C250.41597 (9)0.7483 (3)0.63499 (19)0.0301 (5)
C260.43075 (10)0.8279 (3)0.7114 (2)0.0339 (6)
C270.47511 (10)0.8220 (3)0.7329 (2)0.0377 (6)
H27A0.48570.87560.78450.045*
C280.50337 (10)0.7420 (3)0.6822 (2)0.0400 (7)
H28A0.53320.74060.69860.048*
C290.48874 (10)0.6624 (3)0.6066 (2)0.0394 (7)
H29A0.50830.60560.57170.047*
C300.44564 (10)0.6667 (3)0.5829 (2)0.0349 (6)
H30A0.43570.61370.53050.042*
C310.37001 (9)0.7499 (3)0.6025 (2)0.0336 (6)
C320.40265 (11)0.9200 (4)0.7698 (2)0.0456 (7)
H32A0.42060.97480.81370.068*
H32B0.38240.85980.80460.068*
H32C0.38640.98620.72980.068*
N10.21757 (13)0.2511 (3)0.1930 (2)0.0265 (7)0.867 (11)
N20.29590 (14)0.2293 (3)0.1772 (2)0.0268 (7)0.867 (11)
N30.24768 (13)0.1163 (5)0.0639 (3)0.0275 (7)0.867 (11)
N40.25464 (14)0.3768 (5)0.0682 (3)0.0304 (8)0.867 (11)
C330.25936 (17)0.2382 (4)0.2423 (2)0.0267 (8)0.867 (11)
H33A0.26340.32220.28360.032*0.867 (11)
H33B0.25900.15140.28190.032*0.867 (11)
C340.28840 (15)0.1051 (4)0.1152 (3)0.0309 (8)0.867 (11)
H34A0.31250.09780.07030.037*0.867 (11)
H34B0.28820.01640.15300.037*0.867 (11)
C350.21243 (15)0.1254 (4)0.1304 (3)0.0286 (8)0.867 (11)
H35A0.21170.03680.16830.034*0.867 (11)
H35B0.18460.13310.09630.034*0.867 (11)
C360.21907 (14)0.3819 (4)0.1351 (3)0.0306 (8)0.867 (11)
H36A0.19130.39260.10110.037*0.867 (11)
H36B0.22270.46650.17610.037*0.867 (11)
C370.29518 (15)0.3608 (4)0.1191 (3)0.0308 (8)0.867 (11)
H37A0.29960.44540.15960.037*0.867 (11)
H37B0.31940.35720.07420.037*0.867 (11)
C380.2486 (2)0.2487 (7)0.0091 (3)0.0330 (9)0.867 (11)
H38A0.22110.25790.02620.040*0.867 (11)
H38B0.27240.24330.03660.040*0.867 (11)
N1X0.2021 (8)0.278 (2)0.1822 (14)0.030 (2)0.133 (11)
N2X0.2807 (8)0.245 (2)0.1924 (15)0.0285 (19)0.133 (11)
N3X0.2378 (8)0.122 (3)0.0709 (19)0.029 (2)0.133 (11)
N4X0.2475 (9)0.382 (4)0.065 (2)0.030 (2)0.133 (11)
C33X0.2401 (9)0.263 (2)0.2427 (13)0.027 (2)0.133 (11)
H33C0.24240.34840.28310.032*0.133 (11)
H33D0.23590.17850.28360.032*0.133 (11)
C34X0.2758 (8)0.116 (2)0.1317 (18)0.030 (2)0.133 (11)
H34C0.30190.10640.09270.036*0.133 (11)
H34D0.27380.03020.17160.036*0.133 (11)
C35X0.1990 (8)0.144 (2)0.1262 (18)0.029 (2)0.133 (11)
H35C0.19490.06170.16850.034*0.133 (11)
H35D0.17350.14990.08430.034*0.133 (11)
C36X0.2080 (9)0.399 (2)0.1185 (19)0.030 (2)0.133 (11)
H36C0.18280.40450.07550.036*0.133 (11)
H36D0.20940.48880.15460.036*0.133 (11)
C37X0.2840 (9)0.370 (3)0.126 (2)0.030 (2)0.133 (11)
H37C0.28660.45960.16310.036*0.133 (11)
H37D0.31060.35970.08900.036*0.133 (11)
C38X0.2426 (14)0.248 (4)0.0098 (19)0.031 (2)0.133 (11)
H38C0.21680.25620.03120.037*0.133 (11)
H38D0.26820.23510.03030.037*0.133 (11)
C390.24894 (10)0.7556 (3)0.49808 (15)0.0308 (5)
H39A0.24500.67210.53970.037*
H39B0.25330.84140.53760.037*
C400.27945 (10)0.6057 (3)0.38076 (19)0.0313 (6)
H40A0.30500.58900.34090.038*
H40B0.27570.52050.42100.038*
C410.20427 (9)0.6466 (3)0.3813 (2)0.0331 (6)
H41A0.20000.56160.42140.040*
H41B0.17810.65850.34210.040*
C420.21668 (9)0.8994 (3)0.3788 (2)0.0316 (6)
H42A0.19060.91350.33940.038*
H42B0.22070.98660.41710.038*
C430.29197 (9)0.8587 (3)0.3784 (2)0.0339 (6)
H43A0.29670.94530.41690.041*
H43B0.31770.84550.33850.041*
C440.24732 (11)0.7496 (3)0.26304 (16)0.0346 (6)
H44A0.22160.76250.22260.041*
H44B0.27270.73460.22230.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0479 (17)0.0485 (18)0.0396 (16)0.0164 (14)0.0163 (13)0.0130 (14)
O20.074 (2)0.055 (2)0.0352 (14)0.0250 (17)0.0121 (14)0.0127 (14)
C70.0388 (17)0.0292 (19)0.0238 (16)0.0001 (14)0.0016 (14)0.0021 (15)
C10.0311 (16)0.028 (2)0.0260 (17)0.0042 (17)0.0004 (13)0.0028 (13)
C20.038 (2)0.0293 (19)0.030 (2)0.0057 (15)0.0020 (16)0.0097 (16)
C30.044 (2)0.040 (2)0.038 (3)0.0067 (19)0.012 (2)0.0129 (19)
C40.050 (3)0.048 (3)0.0326 (18)0.012 (2)0.0105 (19)0.0067 (18)
C50.048 (3)0.044 (2)0.031 (2)0.0134 (19)0.0031 (19)0.0053 (16)
C60.035 (2)0.0355 (17)0.0274 (19)0.0041 (15)0.0010 (14)0.0001 (14)
C80.041 (3)0.030 (2)0.049 (3)0.0017 (18)0.0053 (19)0.0028 (18)
O1X0.083 (7)0.046 (7)0.039 (5)0.020 (6)0.019 (6)0.005 (6)
O2X0.059 (7)0.052 (7)0.062 (7)0.024 (5)0.011 (6)0.005 (6)
C7X0.040 (4)0.035 (4)0.031 (4)0.003 (4)0.002 (4)0.001 (4)
C1X0.035 (4)0.030 (4)0.027 (4)0.001 (4)0.001 (3)0.006 (3)
C2X0.039 (4)0.032 (4)0.031 (4)0.005 (4)0.003 (4)0.003 (4)
C3X0.042 (4)0.033 (4)0.033 (5)0.004 (4)0.002 (4)0.003 (4)
C4X0.046 (5)0.039 (5)0.032 (4)0.002 (4)0.004 (4)0.004 (4)
C5X0.043 (5)0.039 (4)0.027 (4)0.002 (4)0.004 (4)0.001 (4)
C6X0.039 (4)0.034 (4)0.029 (4)0.001 (4)0.004 (4)0.001 (4)
C8X0.046 (9)0.034 (7)0.043 (8)0.003 (7)0.003 (7)0.001 (6)
O30.0470 (14)0.0465 (16)0.0330 (13)0.0167 (12)0.0043 (11)0.0066 (11)
O40.0488 (15)0.0379 (14)0.0539 (15)0.0203 (11)0.0127 (12)0.0149 (12)
C150.0288 (14)0.0232 (14)0.0359 (14)0.0013 (12)0.0003 (11)0.0007 (11)
C90.0271 (13)0.0194 (15)0.0287 (14)0.0010 (13)0.0026 (11)0.0010 (11)
C100.026 (2)0.0201 (16)0.0339 (16)0.0014 (11)0.0031 (12)0.0028 (14)
C110.0376 (15)0.0191 (17)0.0412 (19)0.0001 (14)0.0004 (15)0.0055 (12)
C120.046 (2)0.0303 (17)0.0326 (15)0.0032 (14)0.0050 (14)0.0053 (13)
C130.0433 (19)0.0329 (17)0.0308 (15)0.0035 (15)0.0005 (13)0.0034 (13)
C140.0345 (17)0.0247 (13)0.0319 (17)0.0016 (12)0.0019 (12)0.0015 (12)
C160.0352 (19)0.0209 (14)0.049 (2)0.0044 (13)0.0006 (15)0.0045 (13)
O3X0.038 (7)0.035 (8)0.049 (8)0.004 (6)0.015 (7)0.016 (7)
O4X0.046 (9)0.052 (9)0.035 (7)0.022 (8)0.009 (7)0.009 (7)
C15X0.033 (5)0.029 (5)0.031 (5)0.005 (5)0.001 (4)0.001 (5)
C9X0.031 (4)0.025 (4)0.031 (4)0.004 (4)0.001 (4)0.001 (4)
C10X0.032 (5)0.022 (4)0.035 (4)0.000 (4)0.001 (4)0.002 (4)
C11X0.037 (5)0.026 (5)0.035 (4)0.000 (4)0.003 (4)0.003 (4)
C12X0.040 (4)0.027 (4)0.032 (4)0.002 (4)0.004 (4)0.000 (4)
C13X0.038 (5)0.027 (4)0.031 (4)0.000 (4)0.004 (5)0.001 (4)
C14X0.035 (4)0.025 (4)0.032 (4)0.003 (4)0.003 (4)0.001 (4)
C16X0.039 (11)0.030 (9)0.038 (9)0.005 (8)0.012 (9)0.000 (7)
O50.0484 (15)0.0605 (15)0.0527 (13)0.0073 (12)0.0152 (11)0.0113 (12)
O60.0342 (12)0.0663 (16)0.0835 (19)0.0099 (11)0.0025 (12)0.0190 (15)
O70.0433 (13)0.0664 (16)0.0460 (12)0.0090 (12)0.0117 (10)0.0125 (12)
O80.0393 (13)0.0851 (19)0.0679 (17)0.0113 (13)0.0008 (12)0.0225 (15)
N50.0333 (12)0.0231 (10)0.0326 (11)0.0018 (9)0.0057 (9)0.0015 (9)
N60.0343 (12)0.0239 (10)0.0301 (11)0.0018 (9)0.0066 (9)0.0006 (9)
N70.0455 (13)0.0186 (10)0.0256 (10)0.0001 (9)0.0025 (9)0.0043 (8)
N80.0406 (13)0.0214 (10)0.0288 (11)0.0009 (9)0.0001 (9)0.0068 (8)
C170.0301 (13)0.0266 (12)0.0373 (14)0.0024 (11)0.0015 (11)0.0089 (11)
C180.0440 (17)0.0310 (14)0.0395 (15)0.0049 (12)0.0003 (13)0.0082 (12)
C190.0356 (16)0.0491 (18)0.0451 (17)0.0077 (14)0.0037 (13)0.0163 (15)
C200.0368 (16)0.0563 (19)0.0442 (17)0.0038 (15)0.0023 (13)0.0188 (15)
C210.0384 (17)0.0499 (18)0.0477 (17)0.0116 (14)0.0061 (14)0.0117 (15)
C220.0435 (17)0.0337 (15)0.0437 (16)0.0025 (13)0.0011 (13)0.0059 (12)
C230.0368 (15)0.0312 (14)0.0442 (16)0.0040 (13)0.0065 (13)0.0102 (12)
C240.056 (2)0.0470 (18)0.0481 (18)0.0010 (16)0.0028 (16)0.0044 (15)
C250.0329 (13)0.0236 (12)0.0337 (13)0.0022 (11)0.0010 (11)0.0086 (10)
C260.0420 (16)0.0252 (13)0.0343 (13)0.0042 (11)0.0012 (12)0.0054 (11)
C270.0393 (16)0.0344 (15)0.0394 (15)0.0075 (12)0.0057 (12)0.0099 (12)
C280.0379 (15)0.0395 (16)0.0426 (16)0.0038 (13)0.0038 (13)0.0115 (13)
C290.0407 (16)0.0323 (14)0.0454 (16)0.0062 (12)0.0071 (13)0.0053 (12)
C300.0408 (16)0.0271 (13)0.0369 (14)0.0008 (12)0.0018 (12)0.0037 (11)
C310.0341 (14)0.0263 (12)0.0404 (15)0.0000 (12)0.0034 (12)0.0035 (11)
C320.0512 (19)0.0407 (17)0.0450 (17)0.0005 (14)0.0050 (14)0.0038 (14)
N10.0308 (17)0.0224 (13)0.0262 (12)0.0022 (12)0.0011 (12)0.0031 (10)
N20.0334 (17)0.0229 (12)0.0242 (12)0.0027 (12)0.0007 (12)0.0016 (10)
N30.043 (2)0.0161 (11)0.0238 (12)0.0026 (13)0.0021 (13)0.0033 (10)
N40.050 (2)0.0163 (12)0.0248 (12)0.0011 (14)0.0029 (14)0.0029 (10)
C330.037 (2)0.0254 (14)0.0181 (11)0.0015 (15)0.0012 (12)0.0012 (10)
C340.040 (2)0.0208 (13)0.0313 (16)0.0072 (13)0.0027 (14)0.0012 (12)
C350.035 (2)0.0195 (14)0.0313 (14)0.0019 (13)0.0000 (15)0.0040 (12)
C360.040 (2)0.0194 (14)0.0322 (17)0.0087 (13)0.0072 (14)0.0047 (12)
C370.039 (2)0.0207 (14)0.0324 (16)0.0041 (14)0.0010 (15)0.0012 (12)
C380.056 (3)0.0240 (13)0.0190 (12)0.0017 (15)0.0018 (15)0.0005 (12)
N1X0.038 (4)0.021 (4)0.030 (4)0.005 (4)0.002 (4)0.003 (4)
N2X0.037 (4)0.024 (3)0.025 (3)0.004 (4)0.002 (3)0.001 (3)
N3X0.043 (4)0.018 (4)0.025 (4)0.003 (4)0.001 (4)0.001 (3)
N4X0.045 (4)0.021 (4)0.026 (4)0.001 (4)0.006 (3)0.001 (3)
C33X0.034 (4)0.025 (4)0.022 (4)0.006 (4)0.001 (4)0.000 (4)
C34X0.040 (4)0.023 (4)0.027 (4)0.004 (4)0.005 (4)0.001 (4)
C35X0.039 (4)0.021 (4)0.026 (4)0.003 (4)0.001 (4)0.002 (4)
C36X0.042 (4)0.020 (4)0.029 (4)0.005 (4)0.006 (4)0.001 (4)
C37X0.040 (4)0.023 (4)0.028 (4)0.001 (4)0.005 (4)0.004 (4)
C38X0.048 (5)0.020 (4)0.024 (4)0.002 (4)0.001 (4)0.001 (4)
C390.0501 (15)0.0215 (10)0.0209 (9)0.0010 (10)0.0008 (12)0.0008 (10)
C400.0415 (15)0.0206 (12)0.0319 (13)0.0089 (11)0.0003 (11)0.0010 (10)
C410.0360 (14)0.0230 (12)0.0403 (14)0.0082 (11)0.0012 (12)0.0046 (11)
C420.0383 (14)0.0199 (11)0.0368 (13)0.0070 (11)0.0023 (11)0.0005 (10)
C430.0346 (14)0.0242 (12)0.0429 (15)0.0088 (11)0.0017 (12)0.0036 (11)
C440.0534 (16)0.0293 (12)0.0210 (10)0.0041 (11)0.0004 (12)0.0015 (11)
Geometric parameters (Å, º) top
O1—C71.311 (5)C17—C181.393 (4)
O1—H1O10.830 (19)C17—C221.416 (4)
O2—C71.212 (5)C17—C231.481 (4)
C7—C11.491 (5)C18—C191.390 (4)
C1—C61.403 (5)C18—C241.499 (5)
C1—C21.408 (5)C19—C201.378 (5)
C2—C31.394 (5)C19—H19A0.9500
C2—C81.505 (5)C20—C211.387 (5)
C3—C41.372 (7)C20—H20A0.9500
C3—H3A0.9500C21—C221.371 (5)
C4—C51.378 (7)C21—H21A0.9500
C4—H4A0.9500C22—H22A0.9500
C5—C61.375 (5)C24—H24A0.9800
C5—H5A0.9500C24—H24B0.9800
C6—H6A0.9500C24—H24C0.9800
C8—H8A0.9800C25—C261.399 (4)
C8—H8B0.9800C25—C301.410 (4)
C8—H8C0.9800C25—C311.493 (4)
O1X—C7X1.311 (14)C26—C271.405 (4)
O1X—H2O10.8400C26—C321.485 (4)
O2X—C7X1.211 (14)C27—C281.363 (5)
C7X—C1X1.503 (14)C27—H27A0.9500
C1X—C2X1.393 (15)C28—C291.388 (5)
C1X—C6X1.411 (15)C28—H28A0.9500
C2X—C3X1.391 (16)C29—C301.374 (4)
C2X—C8X1.512 (15)C29—H29A0.9500
C3X—C4X1.363 (16)C30—H30A0.9500
C3X—H3XA0.9500C32—H32A0.9800
C4X—C5X1.383 (16)C32—H32B0.9800
C4X—H4XA0.9500C32—H32C0.9800
C5X—C6X1.361 (16)N1—C331.475 (4)
C5X—H5XA0.9500N1—C361.477 (4)
C6X—H6XA0.9500N1—C351.485 (4)
C8X—H8XA0.9800N2—C331.472 (4)
C8X—H8XB0.9800N2—C341.480 (4)
C8X—H8XC0.9800N2—C371.484 (4)
O3—C151.313 (4)N3—C351.455 (4)
O3—H1O30.84 (2)N3—C341.459 (4)
O4—C151.207 (4)N3—C381.465 (4)
C15—C91.501 (4)N4—C371.455 (4)
C9—C141.399 (4)N4—C361.465 (5)
C9—C101.402 (4)N4—C381.477 (4)
C10—C111.403 (4)C33—H33A0.9900
C10—C161.503 (4)C33—H33B0.9900
C11—C121.386 (5)C34—H34A0.9900
C11—H11A0.9500C34—H34B0.9900
C12—C131.381 (5)C35—H35A0.9900
C12—H12A0.9500C35—H35B0.9900
C13—C141.378 (5)C36—H36A0.9900
C13—H13A0.9500C36—H36B0.9900
C14—H14A0.9500C37—H37A0.9900
C16—H16A0.9800C37—H37B0.9900
C16—H16B0.9800C38—H38A0.9900
C16—H16C0.9800C38—H38B0.9900
O3X—C15X1.314 (17)N1X—C36X1.460 (17)
O3X—H2O30.8400N1X—C33X1.466 (17)
O4X—C15X1.204 (17)N1X—C35X1.489 (16)
C15X—C9X1.517 (17)N2X—C33X1.460 (17)
C9X—C14X1.393 (17)N2X—C34X1.494 (16)
C9X—C10X1.397 (17)N2X—C37X1.505 (17)
C10X—C11X1.403 (17)N3X—C35X1.457 (17)
C10X—C16X1.518 (17)N3X—C34X1.459 (17)
C11X—C12X1.383 (18)N3X—C38X1.474 (17)
C11X—H11B0.9500N4X—C37X1.437 (17)
C12X—C13X1.368 (19)N4X—C36X1.458 (17)
C12X—H12B0.9500N4X—C38X1.482 (17)
C13X—C14X1.362 (18)C33X—H33C0.9900
C13X—H13B0.9500C33X—H33D0.9900
C14X—H14B0.9500C34X—H34C0.9900
C16X—H16D0.9800C34X—H34D0.9900
C16X—H16E0.9800C35X—H35C0.9900
C16X—H16F0.9800C35X—H35D0.9900
O5—C231.310 (4)C36X—H36C0.9900
O5—H1O50.85 (2)C36X—H36D0.9900
O6—C231.217 (4)C37X—H37C0.9900
O7—C311.303 (4)C37X—H37D0.9900
O7—H1O70.861 (19)C38X—H38C0.9900
O8—C311.211 (4)C38X—H38D0.9900
N5—C391.469 (4)C39—H39A0.9900
N5—C421.479 (3)C39—H39B0.9900
N5—C411.482 (3)C40—H40A0.9900
N6—C391.470 (4)C40—H40B0.9900
N6—C431.478 (3)C41—H41A0.9900
N6—C401.482 (3)C41—H41B0.9900
N7—C411.447 (4)C42—H42A0.9900
N7—C401.458 (4)C42—H42B0.9900
N7—C441.466 (3)C43—H43A0.9900
N8—C421.452 (4)C43—H43B0.9900
N8—C431.458 (4)C44—H44A0.9900
N8—C441.478 (4)C44—H44B0.9900
C7—O1—H1O1113 (3)C25—C26—C27117.8 (3)
O2—C7—O1122.5 (4)C25—C26—C32124.1 (3)
O2—C7—C1124.5 (3)C27—C26—C32118.2 (3)
O1—C7—C1112.9 (4)C28—C27—C26122.1 (3)
C6—C1—C2119.8 (4)C28—C27—H27A118.9
C6—C1—C7118.6 (4)C26—C27—H27A118.9
C2—C1—C7121.6 (4)C27—C28—C29120.2 (3)
C3—C2—C1117.6 (4)C27—C28—H28A119.9
C3—C2—C8118.7 (4)C29—C28—H28A119.9
C1—C2—C8123.7 (4)C30—C29—C28119.3 (3)
C4—C3—C2121.8 (5)C30—C29—H29A120.3
C4—C3—H3A119.1C28—C29—H29A120.3
C2—C3—H3A119.1C29—C30—C25121.1 (3)
C3—C4—C5120.6 (4)C29—C30—H30A119.4
C3—C4—H4A119.7C25—C30—H30A119.4
C5—C4—H4A119.7O8—C31—O7122.4 (3)
C6—C5—C4119.5 (4)O8—C31—C25123.6 (3)
C6—C5—H5A120.3O7—C31—C25114.0 (3)
C4—C5—H5A120.3C26—C32—H32A109.5
C5—C6—C1120.8 (4)C26—C32—H32B109.5
C5—C6—H6A119.6H32A—C32—H32B109.5
C1—C6—H6A119.6C26—C32—H32C109.5
C2—C8—H8A109.5H32A—C32—H32C109.5
C2—C8—H8B109.5H32B—C32—H32C109.5
H8A—C8—H8B109.5C33—N1—C36107.9 (2)
C2—C8—H8C109.5C33—N1—C35108.4 (2)
H8A—C8—H8C109.5C36—N1—C35108.5 (3)
H8B—C8—H8C109.5C33—N2—C34107.9 (2)
C7X—O1X—H2O1109.5C33—N2—C37107.5 (2)
O2X—C7X—O1X125.3 (15)C34—N2—C37108.0 (3)
O2X—C7X—C1X119.2 (14)C35—N3—C34108.7 (3)
O1X—C7X—C1X115.4 (12)C35—N3—C38108.6 (3)
C2X—C1X—C6X120.3 (13)C34—N3—C38108.2 (3)
C2X—C1X—C7X121.8 (14)C37—N4—C36108.8 (3)
C6X—C1X—C7X117.9 (13)C37—N4—C38108.1 (3)
C3X—C2X—C1X115.4 (15)C36—N4—C38108.0 (3)
C3X—C2X—C8X116.3 (15)N2—C33—N1111.9 (2)
C1X—C2X—C8X128.3 (16)N2—C33—H33A109.2
C4X—C3X—C2X124.5 (18)N1—C33—H33A109.2
C4X—C3X—H3XA117.8N2—C33—H33B109.2
C2X—C3X—H3XA117.8N1—C33—H33B109.2
C3X—C4X—C5X119.7 (17)H33A—C33—H33B107.9
C3X—C4X—H4XA120.1N3—C34—N2112.3 (3)
C5X—C4X—H4XA120.1N3—C34—H34A109.1
C6X—C5X—C4X118.1 (15)N2—C34—H34A109.1
C6X—C5X—H5XA120.9N3—C34—H34B109.1
C4X—C5X—H5XA120.9N2—C34—H34B109.1
C5X—C6X—C1X122.0 (14)H34A—C34—H34B107.9
C5X—C6X—H6XA119.0N3—C35—N1111.4 (3)
C1X—C6X—H6XA119.0N3—C35—H35A109.4
C2X—C8X—H8XA109.5N1—C35—H35A109.4
C2X—C8X—H8XB109.5N3—C35—H35B109.4
H8XA—C8X—H8XB109.5N1—C35—H35B109.4
C2X—C8X—H8XC109.5H35A—C35—H35B108.0
H8XA—C8X—H8XC109.5N4—C36—N1111.5 (3)
H8XB—C8X—H8XC109.5N4—C36—H36A109.3
C15—O3—H1O3109 (4)N1—C36—H36A109.3
O4—C15—O3122.8 (3)N4—C36—H36B109.3
O4—C15—C9121.1 (3)N1—C36—H36B109.3
O3—C15—C9116.1 (3)H36A—C36—H36B108.0
C14—C9—C10119.9 (3)N4—C37—N2112.2 (3)
C14—C9—C15115.2 (3)N4—C37—H37A109.2
C10—C9—C15124.9 (3)N2—C37—H37A109.2
C9—C10—C11117.5 (3)N4—C37—H37B109.2
C9—C10—C16125.4 (3)N2—C37—H37B109.2
C11—C10—C16117.0 (3)H37A—C37—H37B107.9
C12—C11—C10121.8 (3)N3—C38—N4112.2 (3)
C12—C11—H11A119.1N3—C38—H38A109.2
C10—C11—H11A119.1N4—C38—H38A109.2
C13—C12—C11120.1 (3)N3—C38—H38B109.2
C13—C12—H12A120.0N4—C38—H38B109.2
C11—C12—H12A120.0H38A—C38—H38B107.9
C14—C13—C12119.2 (3)C36X—N1X—C33X110.1 (15)
C14—C13—H13A120.4C36X—N1X—C35X108.4 (16)
C12—C13—H13A120.4C33X—N1X—C35X106.6 (15)
C13—C14—C9121.5 (3)C33X—N2X—C34X107.0 (15)
C13—C14—H14A119.3C33X—N2X—C37X106.7 (15)
C9—C14—H14A119.3C34X—N2X—C37X105.3 (17)
C10—C16—H16A109.5C35X—N3X—C34X110.0 (18)
C10—C16—H16B109.5C35X—N3X—C38X107.2 (19)
H16A—C16—H16B109.5C34X—N3X—C38X107.6 (19)
C10—C16—H16C109.5C37X—N4X—C36X109.9 (19)
H16A—C16—H16C109.5C37X—N4X—C38X110 (2)
H16B—C16—H16C109.5C36X—N4X—C38X107 (2)
C15X—O3X—H2O3109.5N2X—C33X—N1X114.1 (14)
O4X—C15X—O3X124 (2)N2X—C33X—H33C108.7
O4X—C15X—C9X120.6 (17)N1X—C33X—H33C108.7
O3X—C15X—C9X115.6 (17)N2X—C33X—H33D108.7
C14X—C9X—C10X120.3 (17)N1X—C33X—H33D108.7
C14X—C9X—C15X114.5 (17)H33C—C33X—H33D107.6
C10X—C9X—C15X125.2 (17)N3X—C34X—N2X113.4 (16)
C9X—C10X—C11X114.9 (18)N3X—C34X—H34C108.9
C9X—C10X—C16X123 (2)N2X—C34X—H34C108.9
C11X—C10X—C16X122.0 (19)N3X—C34X—H34D108.9
C12X—C11X—C10X123 (2)N2X—C34X—H34D108.9
C12X—C11X—H11B118.4H34C—C34X—H34D107.7
C10X—C11X—H11B118.4N3X—C35X—N1X111.2 (16)
C13X—C12X—C11X121 (2)N3X—C35X—H35C109.4
C13X—C12X—H12B119.7N1X—C35X—H35C109.4
C11X—C12X—H12B119.7N3X—C35X—H35D109.4
C14X—C13X—C12X117 (2)N1X—C35X—H35D109.4
C14X—C13X—H13B121.4H35C—C35X—H35D108.0
C12X—C13X—H13B121.4N4X—C36X—N1X110.9 (16)
C13X—C14X—C9X123 (2)N4X—C36X—H36C109.5
C13X—C14X—H14B118.3N1X—C36X—H36C109.5
C9X—C14X—H14B118.3N4X—C36X—H36D109.5
C10X—C16X—H16D109.5N1X—C36X—H36D109.5
C10X—C16X—H16E109.5H36C—C36X—H36D108.0
H16D—C16X—H16E109.5N4X—C37X—N2X113.0 (17)
C10X—C16X—H16F109.5N4X—C37X—H37C109.0
H16D—C16X—H16F109.5N2X—C37X—H37C109.0
H16E—C16X—H16F109.5N4X—C37X—H37D109.0
C23—O5—H1O5104 (4)N2X—C37X—H37D109.0
C31—O7—H1O7112 (3)H37C—C37X—H37D107.8
C39—N5—C42108.3 (2)N3X—C38X—N4X111.5 (18)
C39—N5—C41108.4 (2)N3X—C38X—H38C109.3
C42—N5—C41107.8 (2)N4X—C38X—H38C109.3
C39—N6—C43107.8 (2)N3X—C38X—H38D109.3
C39—N6—C40108.0 (2)N4X—C38X—H38D109.3
C43—N6—C40107.9 (2)H38C—C38X—H38D108.0
C41—N7—C40108.4 (2)N5—C39—N6111.52 (18)
C41—N7—C44108.6 (2)N5—C39—H39A109.3
C40—N7—C44108.4 (2)N6—C39—H39A109.3
C42—N8—C43108.3 (2)N5—C39—H39B109.3
C42—N8—C44108.1 (2)N6—C39—H39B109.3
C43—N8—C44108.2 (2)H39A—C39—H39B108.0
C18—C17—C22119.1 (3)N7—C40—N6112.1 (2)
C18—C17—C23123.4 (3)N7—C40—H40A109.2
C22—C17—C23117.5 (3)N6—C40—H40A109.2
C19—C18—C17118.3 (3)N7—C40—H40B109.2
C19—C18—C24118.0 (3)N6—C40—H40B109.2
C17—C18—C24123.7 (3)H40A—C40—H40B107.9
C20—C19—C18121.8 (3)N7—C41—N5112.0 (2)
C20—C19—H19A119.1N7—C41—H41A109.2
C18—C19—H19A119.1N5—C41—H41A109.2
C19—C20—C21120.5 (3)N7—C41—H41B109.2
C19—C20—H20A119.7N5—C41—H41B109.2
C21—C20—H20A119.7H41A—C41—H41B107.9
C22—C21—C20118.4 (3)N8—C42—N5112.1 (2)
C22—C21—H21A120.8N8—C42—H42A109.2
C20—C21—H21A120.8N5—C42—H42A109.2
C21—C22—C17121.8 (3)N8—C42—H42B109.2
C21—C22—H22A119.1N5—C42—H42B109.2
C17—C22—H22A119.1H42A—C42—H42B107.9
O6—C23—O5122.0 (3)N8—C43—N6112.4 (2)
O6—C23—C17123.9 (3)N8—C43—H43A109.1
O5—C23—C17114.1 (3)N6—C43—H43A109.1
C18—C24—H24A109.5N8—C43—H43B109.1
C18—C24—H24B109.5N6—C43—H43B109.1
H24A—C24—H24B109.5H43A—C43—H43B107.8
C18—C24—H24C109.5N7—C44—N8111.92 (18)
H24A—C24—H24C109.5N7—C44—H44A109.2
H24B—C24—H24C109.5N8—C44—H44A109.2
C26—C25—C30119.5 (3)N7—C44—H44B109.2
C26—C25—C31123.1 (3)N8—C44—H44B109.2
C30—C25—C31117.4 (3)H44A—C44—H44B107.9
O2—C7—C1—C6170.3 (5)C26—C27—C28—C290.1 (4)
O1—C7—C1—C611.5 (6)C27—C28—C29—C300.8 (4)
O2—C7—C1—C29.8 (9)C28—C29—C30—C251.1 (4)
O1—C7—C1—C2168.5 (7)C26—C25—C30—C290.9 (4)
C6—C1—C2—C31.6 (12)C31—C25—C30—C29178.3 (3)
C7—C1—C2—C3178.4 (7)C26—C25—C31—O812.0 (4)
C6—C1—C2—C8178.7 (7)C30—C25—C31—O8170.6 (3)
C7—C1—C2—C81.4 (12)C26—C25—C31—O7167.1 (3)
C1—C2—C3—C40.4 (13)C30—C25—C31—O710.3 (4)
C8—C2—C3—C4179.9 (7)C34—N2—C33—N157.6 (3)
C2—C3—C4—C50.8 (11)C37—N2—C33—N158.7 (3)
C3—C4—C5—C60.7 (8)C36—N1—C33—N259.3 (3)
C4—C5—C6—C10.5 (7)C35—N1—C33—N258.0 (3)
C2—C1—C6—C51.7 (9)C35—N3—C34—N259.4 (4)
C7—C1—C6—C5178.3 (4)C38—N3—C34—N258.4 (4)
O2X—C7X—C1X—C2X162 (3)C33—N2—C34—N358.2 (3)
O1X—C7X—C1X—C2X15 (4)C37—N2—C34—N357.7 (4)
O2X—C7X—C1X—C6X19 (3)C34—N3—C35—N159.0 (4)
O1X—C7X—C1X—C6X165 (2)C38—N3—C35—N158.5 (4)
C6X—C1X—C2X—C3X1 (6)C33—N1—C35—N358.4 (3)
C7X—C1X—C2X—C3X179 (3)C36—N1—C35—N358.5 (3)
C6X—C1X—C2X—C8X178 (3)C37—N4—C36—N158.9 (4)
C7X—C1X—C2X—C8X2 (6)C38—N4—C36—N158.3 (4)
C1X—C2X—C3X—C4X1 (6)C33—N1—C36—N458.8 (4)
C8X—C2X—C3X—C4X178 (3)C35—N1—C36—N458.5 (4)
C2X—C3X—C4X—C5X1 (5)C36—N4—C37—N258.8 (4)
C3X—C4X—C5X—C6X3 (4)C38—N4—C37—N258.2 (4)
C4X—C5X—C6X—C1X3 (3)C33—N2—C37—N458.4 (4)
C2X—C1X—C6X—C5X1 (4)C34—N2—C37—N457.8 (4)
C7X—C1X—C6X—C5X179 (2)C35—N3—C38—N459.0 (5)
O4—C15—C9—C1419.8 (5)C34—N3—C38—N458.8 (5)
O3—C15—C9—C14160.7 (3)C37—N4—C38—N358.9 (5)
O4—C15—C9—C10157.4 (6)C36—N4—C38—N358.6 (5)
O3—C15—C9—C1022.1 (7)C34X—N2X—C33X—N1X58 (2)
C14—C9—C10—C110.8 (10)C37X—N2X—C33X—N1X54 (2)
C15—C9—C10—C11176.2 (5)C36X—N1X—C33X—N2X56 (2)
C14—C9—C10—C16178.5 (5)C35X—N1X—C33X—N2X61 (2)
C15—C9—C10—C164.5 (11)C35X—N3X—C34X—N2X56 (2)
C9—C10—C11—C121.3 (10)C38X—N3X—C34X—N2X61 (2)
C16—C10—C11—C12178.1 (5)C33X—N2X—C34X—N3X54 (2)
C10—C11—C12—C131.3 (8)C37X—N2X—C34X—N3X59 (2)
C11—C12—C13—C140.8 (6)C34X—N3X—C35X—N1X58 (2)
C12—C13—C14—C90.3 (5)C38X—N3X—C35X—N1X59 (2)
C10—C9—C14—C130.4 (7)C36X—N1X—C35X—N3X59 (2)
C15—C9—C14—C13177.0 (3)C33X—N1X—C35X—N3X59 (2)
O4X—C15X—C9X—C14X166 (4)C37X—N4X—C36X—N1X58 (2)
O3X—C15X—C9X—C14X13 (5)C38X—N4X—C36X—N1X61 (2)
O4X—C15X—C9X—C10X13 (8)C33X—N1X—C36X—N4X56 (2)
O3X—C15X—C9X—C10X168 (6)C35X—N1X—C36X—N4X60 (2)
C14X—C9X—C10X—C11X3 (10)C36X—N4X—C37X—N2X59 (3)
C15X—C9X—C10X—C11X178 (5)C38X—N4X—C37X—N2X58 (3)
C14X—C9X—C10X—C16X177 (6)C33X—N2X—C37X—N4X56 (2)
C15X—C9X—C10X—C16X2 (11)C34X—N2X—C37X—N4X57 (2)
C9X—C10X—C11X—C12X4 (11)C35X—N3X—C38X—N4X61 (3)
C16X—C10X—C11X—C12X176 (6)C34X—N3X—C38X—N4X58 (3)
C10X—C11X—C12X—C13X9 (9)C37X—N4X—C38X—N3X57 (3)
C11X—C12X—C13X—C14X6 (6)C36X—N4X—C38X—N3X62 (3)
C12X—C13X—C14X—C9X1 (6)C42—N5—C39—N658.5 (3)
C10X—C9X—C14X—C13X6 (8)C41—N5—C39—N658.2 (3)
C15X—C9X—C14X—C13X175 (3)C43—N6—C39—N558.4 (3)
C22—C17—C18—C190.5 (4)C40—N6—C39—N558.0 (3)
C23—C17—C18—C19176.9 (3)C41—N7—C40—N659.1 (3)
C22—C17—C18—C24179.7 (3)C44—N7—C40—N658.6 (3)
C23—C17—C18—C243.3 (4)C39—N6—C40—N758.6 (3)
C17—C18—C19—C200.5 (4)C43—N6—C40—N757.7 (3)
C24—C18—C19—C20179.7 (3)C40—N7—C41—N558.9 (3)
C18—C19—C20—C210.5 (5)C44—N7—C41—N558.7 (3)
C19—C20—C21—C220.5 (5)C39—N5—C41—N758.7 (3)
C20—C21—C22—C170.5 (5)C42—N5—C41—N758.3 (3)
C18—C17—C22—C210.5 (4)C43—N8—C42—N558.3 (3)
C23—C17—C22—C21177.1 (3)C44—N8—C42—N558.6 (3)
C18—C17—C23—O63.3 (5)C39—N5—C42—N858.6 (3)
C22—C17—C23—O6179.7 (3)C41—N5—C42—N858.5 (3)
C18—C17—C23—O5175.7 (3)C42—N8—C43—N658.7 (3)
C22—C17—C23—O50.7 (4)C44—N8—C43—N658.2 (3)
C30—C25—C26—C270.2 (4)C39—N6—C43—N858.7 (3)
C31—C25—C26—C27177.5 (2)C40—N6—C43—N857.7 (3)
C30—C25—C26—C32178.6 (3)C41—N7—C44—N858.6 (3)
C31—C25—C26—C321.3 (4)C40—N7—C44—N858.9 (3)
C25—C26—C27—C280.2 (4)C42—N8—C44—N758.4 (3)
C32—C26—C27—C28179.0 (3)C43—N8—C44—N758.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N10.83 (3)1.80 (3)2.631 (4)173 (5)
O3—H1O3···N20.84 (4)1.84 (4)2.679 (5)175 (3)
O5—H1O5···N50.86 (3)1.85 (4)2.680 (3)162 (5)
O7—H1O7···N60.86 (3)1.80 (3)2.657 (3)171 (4)
C6—H6A···O10.952.352.685 (5)100
C16—H16A···O30.982.442.816 (4)102
C22—H22A···O50.952.312.670 (4)102
C30—H30A···O70.952.342.683 (4)101
C33—H33A···O40.992.583.138 (5)116
C33—H33B···N8i0.992.593.520 (4)157
C36—H36B···N70.992.613.561 (5)161
C38—H38B···O4ii0.992.403.357 (6)164
C40—H40B···N3iii0.992.573.492 (5)155
C44—H44A···O6iv0.992.383.363 (4)172
C44—H44B···O8iv0.992.393.372 (4)171
Symmetry codes: (i) x, y1, z; (ii) x, y+1/2, z1/2; (iii) x, y+1/2, z+1/2; (iv) x, y+3/2, z1/2.
(160K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top
Crystal data top
C6H12N4·2C8H8O2F(000) = 1760
Mr = 412.48Dx = 1.318 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 30.975 (2) ÅCell parameters from 9990 reflections
b = 9.3542 (7) Åθ = 2.2–27.2°
c = 14.3524 (10) ŵ = 0.09 mm1
β = 90.1490 (14)°T = 160 K
V = 4158.5 (5) Å3Block, colourless
Z = 80.43 × 0.17 × 0.15 mm
Data collection top
Bruker APEX DUO CCD area detector
diffractometer
10026 independent reflections
Radiation source: fine-focus sealed tube7762 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 28.0°, θmin = 0.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 3640
Tmin = 0.879, Tmax = 0.963k = 1212
65634 measured reflectionsl = 1818
Refinement top
Refinement on F21222 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.0691P)2 + 1.5753P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
10026 reflectionsΔρmax = 0.43 e Å3
837 parametersΔρmin = 0.19 e Å3
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
xyzUiso*/UeqOcc. (<1)
O10.16460 (10)0.2389 (4)0.3352 (2)0.0479 (9)0.674 (6)
H1O10.1796 (14)0.248 (5)0.287 (2)0.071 (15)*0.674 (6)
O20.12825 (12)0.4193 (5)0.2741 (2)0.0582 (10)0.674 (6)
C70.13364 (12)0.3346 (5)0.3365 (3)0.0315 (8)0.674 (6)
C10.1076 (3)0.3297 (7)0.4233 (4)0.0321 (10)0.674 (6)
C20.0784 (4)0.4398 (10)0.4470 (6)0.0342 (12)0.674 (6)
C30.0566 (3)0.4287 (9)0.5317 (5)0.0414 (14)0.674 (6)
H3A0.03730.50250.54940.050*0.674 (6)
C40.06240 (19)0.3139 (7)0.5904 (4)0.0442 (13)0.674 (6)
H4A0.04700.30920.64740.053*0.674 (6)
C50.09058 (19)0.2052 (6)0.5665 (4)0.0438 (11)0.674 (6)
H5A0.09450.12550.60670.053*0.674 (6)
C60.11282 (16)0.2143 (6)0.4838 (4)0.0359 (10)0.674 (6)
H6A0.13230.13990.46750.043*0.674 (6)
C80.0704 (2)0.5680 (7)0.3862 (5)0.0444 (13)0.674 (6)
H8A0.09760.61850.37550.067*0.674 (6)
H8B0.05000.63240.41720.067*0.674 (6)
H8C0.05830.53680.32640.067*0.674 (6)
O1X0.1342 (3)0.3366 (10)0.2843 (6)0.062 (2)0.326 (6)
H2O10.15290.30830.24630.092*0.326 (6)
O2X0.1652 (2)0.1740 (9)0.3765 (7)0.062 (2)0.326 (6)
C7X0.1376 (3)0.2638 (11)0.3619 (6)0.0386 (16)0.326 (6)
C1X0.1068 (6)0.3027 (15)0.4375 (10)0.0309 (17)0.326 (6)
C2X0.0817 (9)0.427 (2)0.4364 (14)0.034 (2)0.326 (6)
C3X0.0542 (6)0.4473 (18)0.5117 (10)0.037 (2)0.326 (6)
H3XA0.03720.53160.51370.044*0.326 (6)
C4X0.0506 (4)0.3508 (13)0.5834 (9)0.039 (2)0.326 (6)
H4XA0.03180.37000.63400.047*0.326 (6)
C5X0.0744 (4)0.2253 (13)0.5817 (7)0.0374 (18)0.326 (6)
H5XA0.07180.15720.63050.045*0.326 (6)
C6X0.1018 (4)0.2009 (11)0.5086 (8)0.0350 (17)0.326 (6)
H6XA0.11760.11410.50590.042*0.326 (6)
C8X0.0813 (5)0.5426 (14)0.3628 (9)0.044 (3)0.326 (6)
H8XA0.11030.58370.35710.067*0.326 (6)
H8XB0.06090.61770.38060.067*0.326 (6)
H8XC0.07260.50130.30300.067*0.326 (6)
O30.36553 (9)0.1741 (3)0.28273 (19)0.0467 (7)0.808 (5)
H1O30.3429 (11)0.188 (5)0.251 (3)0.096 (16)*0.808 (5)
O40.33478 (8)0.3290 (3)0.3775 (2)0.0526 (7)0.808 (5)
C150.36227 (9)0.2410 (3)0.3628 (2)0.0311 (6)0.808 (5)
C90.39495 (15)0.2026 (4)0.4358 (3)0.0264 (7)0.808 (5)
C100.4180 (3)0.0731 (7)0.4382 (5)0.0288 (8)0.808 (5)
C110.44583 (18)0.0499 (5)0.5142 (3)0.0342 (9)0.808 (5)
H11A0.46200.03630.51730.041*0.808 (5)
C120.45020 (13)0.1496 (4)0.5849 (3)0.0374 (8)0.808 (5)
H12A0.46910.13110.63560.045*0.808 (5)
C130.42726 (14)0.2756 (4)0.5820 (3)0.0385 (8)0.808 (5)
H13A0.43030.34400.63060.046*0.808 (5)
C140.39981 (13)0.3017 (4)0.5080 (3)0.0341 (8)0.808 (5)
H14A0.38390.38850.50610.041*0.808 (5)
C160.41693 (14)0.0407 (4)0.3645 (3)0.0393 (9)0.808 (5)
H16A0.38700.05850.34590.059*0.808 (5)
H16B0.42960.12890.38940.059*0.808 (5)
H16C0.43350.00900.31030.059*0.808 (5)
O3X0.3346 (3)0.2636 (13)0.3362 (9)0.050 (3)0.192 (5)
H2O30.32060.25740.28620.076*0.192 (5)
O4X0.3723 (4)0.0870 (16)0.2730 (7)0.057 (3)0.192 (5)
C15X0.3659 (4)0.1692 (15)0.3361 (9)0.033 (2)0.192 (5)
C9X0.3933 (7)0.168 (2)0.4246 (13)0.032 (2)0.192 (5)
C10X0.4230 (13)0.060 (3)0.446 (2)0.032 (2)0.192 (5)
C11X0.4427 (9)0.073 (2)0.5334 (14)0.035 (2)0.192 (5)
H11B0.46070.00300.55410.042*0.192 (5)
C12X0.4372 (6)0.188 (2)0.5910 (11)0.036 (2)0.192 (5)
H12B0.45240.19210.64850.044*0.192 (5)
C13X0.4101 (6)0.2965 (17)0.5663 (12)0.037 (2)0.192 (5)
H13B0.40600.37680.60580.045*0.192 (5)
C14X0.3893 (6)0.2858 (19)0.4829 (12)0.035 (2)0.192 (5)
H14B0.37120.36250.46370.042*0.192 (5)
C16X0.4292 (7)0.0692 (19)0.3837 (13)0.042 (4)0.192 (5)
H16D0.45600.11800.40100.063*0.192 (5)
H16E0.43070.03870.31850.063*0.192 (5)
H16F0.40480.13470.39170.063*0.192 (5)
O50.13483 (7)0.8207 (2)0.52603 (15)0.0583 (6)
H1O50.1601 (8)0.795 (4)0.506 (3)0.099 (14)*
O60.15701 (6)0.6838 (3)0.64232 (18)0.0661 (6)
O70.36416 (7)0.6911 (2)0.52179 (15)0.0565 (5)
H1O70.3381 (8)0.706 (5)0.501 (3)0.111 (16)*
O80.34103 (6)0.8033 (3)0.64657 (17)0.0695 (7)
N50.21031 (6)0.7734 (2)0.44106 (14)0.0314 (4)
N60.28772 (6)0.7318 (2)0.44058 (13)0.0312 (4)
N70.24204 (6)0.6224 (2)0.32186 (13)0.0323 (4)
N80.25475 (6)0.8797 (2)0.31999 (13)0.0323 (4)
C170.08270 (7)0.7497 (2)0.63474 (17)0.0332 (5)
C180.06809 (8)0.6694 (3)0.71020 (18)0.0396 (6)
C190.02397 (8)0.6743 (3)0.7314 (2)0.0465 (7)
H19A0.01350.62050.78270.056*
C200.00436 (8)0.7547 (3)0.6801 (2)0.0478 (6)
H20A0.03410.75550.69630.057*
C210.00971 (9)0.8351 (3)0.6046 (2)0.0476 (6)
H21A0.01000.89100.56920.057*
C220.05274 (8)0.8316 (3)0.5826 (2)0.0426 (6)
H22A0.06270.88570.53090.051*
C230.12816 (8)0.7482 (3)0.60258 (19)0.0391 (5)
C240.09662 (10)0.5787 (3)0.7700 (2)0.0529 (7)
H24A0.07910.53000.81710.079*
H24B0.11820.63910.80090.079*
H24C0.11120.50740.73120.079*
C250.41607 (7)0.7488 (2)0.63496 (16)0.0320 (5)
C260.43092 (8)0.8279 (2)0.71130 (17)0.0365 (5)
C270.47515 (8)0.8225 (3)0.73245 (18)0.0405 (6)
H27A0.48580.87600.78390.049*
C280.50336 (8)0.7428 (3)0.6816 (2)0.0431 (6)
H28A0.53310.74160.69770.052*
C290.48867 (9)0.6633 (3)0.6061 (2)0.0441 (6)
H29A0.50820.60680.57090.053*
C300.44575 (8)0.6670 (3)0.58300 (18)0.0383 (5)
H30A0.43580.61340.53100.046*
C310.37034 (7)0.7506 (3)0.60273 (18)0.0363 (5)
C320.40293 (10)0.9203 (3)0.7700 (2)0.0505 (7)
H32A0.42090.97450.81390.076*
H32B0.38260.86060.80470.076*
H32C0.38690.98690.73010.076*
N10.21767 (14)0.2508 (4)0.1936 (3)0.0283 (7)0.754 (11)
N20.29591 (14)0.2284 (4)0.1776 (3)0.0298 (7)0.754 (11)
N30.24781 (18)0.1184 (8)0.0638 (4)0.0330 (9)0.754 (11)
N40.2546 (2)0.3785 (8)0.0700 (4)0.0346 (9)0.754 (11)
C330.25947 (18)0.2377 (4)0.2431 (2)0.0288 (8)0.754 (11)
H33A0.26350.32160.28430.035*0.754 (11)
H33B0.25900.15110.28280.035*0.754 (11)
C340.28840 (16)0.1054 (5)0.1155 (3)0.0341 (9)0.754 (11)
H34A0.31260.09780.07090.041*0.754 (11)
H34B0.28780.01660.15310.041*0.754 (11)
C350.21258 (17)0.1256 (5)0.1313 (4)0.0334 (10)0.754 (11)
H35A0.21220.03700.16900.040*0.754 (11)
H35B0.18470.13260.09770.040*0.754 (11)
C360.21917 (17)0.3826 (5)0.1365 (4)0.0347 (9)0.754 (11)
H36A0.19150.39350.10240.042*0.754 (11)
H36B0.22270.46640.17790.042*0.754 (11)
C370.29536 (17)0.3599 (5)0.1196 (4)0.0334 (10)0.754 (11)
H37A0.30040.44400.16010.040*0.754 (11)
H37B0.31920.35520.07390.040*0.754 (11)
C380.2478 (3)0.2524 (8)0.0098 (5)0.0375 (10)0.754 (11)
H38A0.21990.26220.02330.045*0.754 (11)
H38B0.27100.24830.03760.045*0.754 (11)
N1X0.2035 (4)0.2748 (12)0.1787 (8)0.0328 (17)0.246 (11)
N2X0.2820 (4)0.2476 (13)0.1937 (8)0.0305 (16)0.246 (11)
N3X0.2418 (6)0.118 (2)0.0718 (13)0.0334 (19)0.246 (11)
N4X0.2512 (6)0.376 (2)0.0611 (13)0.0336 (19)0.246 (11)
C33X0.2407 (5)0.2619 (13)0.2421 (7)0.0292 (18)0.246 (11)
H33C0.24190.34740.28270.035*0.246 (11)
H33D0.23650.17740.28260.035*0.246 (11)
C34X0.2788 (5)0.1158 (16)0.1357 (11)0.036 (2)0.246 (11)
H34C0.30570.10510.09910.043*0.246 (11)
H34D0.27630.03170.17720.043*0.246 (11)
C35X0.2021 (5)0.1424 (17)0.1228 (13)0.034 (2)0.246 (11)
H35C0.19680.06010.16460.040*0.246 (11)
H35D0.17780.14810.07810.040*0.246 (11)
C36X0.2115 (5)0.3937 (16)0.1142 (11)0.031 (2)0.246 (11)
H36C0.18690.40180.07040.037*0.246 (11)
H36D0.21330.48390.15010.037*0.246 (11)
C37X0.2862 (6)0.3738 (18)0.1293 (13)0.035 (2)0.246 (11)
H37C0.28550.46320.16620.042*0.246 (11)
H37D0.31420.36900.09660.042*0.246 (11)
C38X0.2502 (10)0.240 (2)0.0094 (14)0.036 (2)0.246 (11)
H38C0.27820.22580.02240.043*0.246 (11)
H38D0.22730.24440.03880.043*0.246 (11)
C390.24924 (9)0.7536 (3)0.49864 (11)0.0328 (4)
H39A0.25350.83890.53850.039*
H39B0.24520.66990.53990.039*
C400.28017 (8)0.6056 (2)0.38094 (17)0.0331 (5)
H40A0.30580.58970.34110.040*
H40B0.27650.52010.42080.040*
C410.20489 (8)0.6454 (2)0.38152 (18)0.0351 (5)
H41A0.20070.56040.42160.042*
H41B0.17880.65700.34240.042*
C420.21719 (8)0.8982 (2)0.37966 (17)0.0338 (5)
H42A0.19120.91260.34030.041*
H42B0.22120.98480.41840.041*
C430.29240 (8)0.8579 (2)0.37922 (18)0.0360 (5)
H43A0.29700.94400.41810.043*
H43B0.31820.84520.33950.043*
C440.24807 (10)0.7497 (3)0.26333 (12)0.0367 (4)
H44A0.22240.76280.22310.044*
H44B0.27340.73520.22240.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0478 (17)0.054 (2)0.0418 (17)0.0200 (14)0.0182 (13)0.0151 (15)
O20.074 (2)0.060 (2)0.0407 (15)0.0275 (18)0.0134 (15)0.0145 (16)
C70.0358 (17)0.034 (2)0.0247 (17)0.0008 (15)0.0010 (15)0.0007 (17)
C10.0339 (18)0.036 (2)0.027 (2)0.0049 (19)0.0031 (16)0.0012 (15)
C20.035 (3)0.033 (2)0.035 (3)0.0060 (17)0.0009 (19)0.009 (2)
C30.044 (2)0.044 (3)0.036 (3)0.005 (2)0.012 (2)0.013 (2)
C40.048 (3)0.050 (3)0.0341 (19)0.009 (2)0.011 (2)0.006 (2)
C50.048 (3)0.048 (2)0.036 (2)0.010 (2)0.006 (2)0.0038 (18)
C60.035 (2)0.044 (2)0.028 (2)0.0045 (17)0.0025 (15)0.0008 (17)
C80.046 (3)0.037 (3)0.050 (3)0.001 (2)0.006 (2)0.003 (2)
O1X0.091 (5)0.054 (5)0.040 (4)0.025 (4)0.020 (4)0.005 (4)
O2X0.055 (4)0.059 (4)0.071 (5)0.027 (3)0.015 (3)0.010 (4)
C7X0.039 (3)0.041 (4)0.035 (3)0.001 (3)0.001 (3)0.002 (3)
C1X0.030 (3)0.035 (4)0.028 (3)0.003 (3)0.002 (3)0.005 (3)
C2X0.037 (4)0.035 (4)0.031 (4)0.005 (3)0.000 (3)0.003 (3)
C3X0.041 (3)0.031 (3)0.038 (4)0.001 (3)0.001 (4)0.001 (3)
C4X0.047 (4)0.036 (4)0.034 (3)0.005 (3)0.002 (3)0.004 (3)
C5X0.043 (4)0.039 (3)0.030 (3)0.004 (4)0.003 (3)0.004 (3)
C6X0.038 (4)0.036 (3)0.031 (4)0.005 (3)0.004 (3)0.002 (3)
C8X0.049 (7)0.035 (5)0.049 (6)0.004 (4)0.002 (5)0.004 (4)
O30.0499 (14)0.0536 (17)0.0365 (14)0.0202 (12)0.0062 (12)0.0084 (13)
O40.0506 (14)0.0459 (15)0.0612 (17)0.0233 (11)0.0153 (12)0.0167 (13)
C150.0282 (13)0.0267 (14)0.0384 (15)0.0001 (12)0.0020 (12)0.0004 (12)
C90.0269 (13)0.0212 (17)0.0313 (15)0.0000 (14)0.0038 (11)0.0028 (13)
C100.026 (2)0.0248 (18)0.0358 (18)0.0013 (12)0.0036 (13)0.0028 (15)
C110.0368 (16)0.0247 (17)0.041 (2)0.0013 (13)0.0016 (17)0.0057 (13)
C120.044 (2)0.0317 (19)0.0362 (15)0.0003 (14)0.0042 (15)0.0054 (14)
C130.044 (2)0.0387 (19)0.0326 (15)0.0024 (17)0.0009 (14)0.0035 (14)
C140.0390 (19)0.0278 (14)0.036 (2)0.0008 (13)0.0036 (14)0.0024 (14)
C160.037 (2)0.0268 (17)0.054 (2)0.0057 (14)0.0005 (17)0.0043 (16)
O3X0.043 (5)0.050 (6)0.058 (6)0.011 (4)0.016 (5)0.015 (5)
O4X0.068 (6)0.070 (7)0.033 (4)0.034 (5)0.012 (4)0.012 (5)
C15X0.037 (4)0.035 (4)0.029 (4)0.009 (4)0.001 (4)0.000 (4)
C9X0.032 (4)0.031 (4)0.032 (3)0.006 (4)0.003 (3)0.004 (3)
C10X0.033 (4)0.026 (4)0.037 (4)0.000 (4)0.002 (4)0.005 (4)
C11X0.037 (4)0.030 (4)0.037 (4)0.001 (4)0.004 (4)0.007 (4)
C12X0.044 (4)0.034 (4)0.031 (4)0.002 (4)0.005 (4)0.002 (4)
C13X0.042 (5)0.032 (4)0.037 (4)0.001 (4)0.005 (4)0.003 (4)
C14X0.037 (4)0.033 (4)0.035 (4)0.005 (4)0.001 (4)0.000 (3)
C16X0.047 (9)0.039 (7)0.041 (7)0.007 (6)0.009 (6)0.006 (5)
O50.0490 (12)0.0709 (14)0.0551 (12)0.0087 (10)0.0158 (10)0.0139 (11)
O60.0337 (10)0.0780 (15)0.0865 (16)0.0104 (10)0.0053 (11)0.0234 (13)
O70.0441 (11)0.0731 (14)0.0521 (11)0.0104 (10)0.0122 (9)0.0147 (10)
O80.0386 (10)0.0950 (17)0.0750 (15)0.0109 (11)0.0018 (11)0.0250 (14)
N50.0328 (9)0.0271 (9)0.0344 (10)0.0003 (8)0.0070 (8)0.0016 (8)
N60.0334 (9)0.0284 (9)0.0319 (9)0.0013 (8)0.0068 (8)0.0006 (8)
N70.0446 (11)0.0237 (9)0.0287 (9)0.0003 (8)0.0019 (8)0.0050 (7)
N80.0424 (11)0.0243 (9)0.0303 (10)0.0017 (8)0.0013 (8)0.0067 (7)
C170.0323 (11)0.0288 (11)0.0385 (12)0.0026 (10)0.0014 (10)0.0093 (10)
C180.0432 (14)0.0364 (13)0.0394 (13)0.0051 (10)0.0003 (11)0.0090 (10)
C190.0354 (13)0.0537 (16)0.0504 (15)0.0092 (12)0.0063 (12)0.0177 (13)
C200.0375 (13)0.0569 (16)0.0490 (15)0.0032 (13)0.0034 (12)0.0179 (13)
C210.0379 (13)0.0518 (16)0.0530 (15)0.0120 (12)0.0050 (12)0.0109 (13)
C220.0443 (14)0.0366 (13)0.0470 (14)0.0026 (11)0.0000 (12)0.0056 (11)
C230.0373 (12)0.0350 (12)0.0448 (14)0.0031 (11)0.0058 (11)0.0075 (11)
C240.0536 (16)0.0532 (17)0.0520 (16)0.0004 (13)0.0024 (14)0.0031 (14)
C250.0326 (11)0.0270 (10)0.0363 (11)0.0024 (9)0.0006 (9)0.0076 (9)
C260.0396 (13)0.0317 (12)0.0383 (12)0.0030 (10)0.0030 (10)0.0080 (10)
C270.0390 (13)0.0393 (13)0.0431 (14)0.0071 (10)0.0051 (11)0.0108 (11)
C280.0359 (12)0.0464 (14)0.0471 (14)0.0051 (12)0.0042 (11)0.0125 (12)
C290.0415 (13)0.0411 (14)0.0498 (15)0.0079 (11)0.0089 (12)0.0073 (12)
C300.0399 (13)0.0328 (12)0.0421 (13)0.0018 (10)0.0004 (11)0.0036 (10)
C310.0346 (12)0.0311 (11)0.0433 (13)0.0010 (11)0.0027 (10)0.0038 (10)
C320.0553 (16)0.0477 (15)0.0485 (15)0.0008 (13)0.0063 (13)0.0057 (13)
N10.0328 (17)0.0259 (14)0.0262 (14)0.0003 (13)0.0010 (13)0.0011 (11)
N20.0365 (18)0.0275 (14)0.0253 (14)0.0047 (12)0.0028 (12)0.0000 (11)
N30.051 (2)0.0224 (14)0.0258 (16)0.0000 (15)0.0034 (14)0.0026 (13)
N40.060 (2)0.0196 (14)0.0244 (18)0.0001 (15)0.0013 (16)0.0011 (13)
C330.036 (2)0.0298 (16)0.0207 (13)0.0015 (15)0.0009 (14)0.0019 (11)
C340.048 (2)0.0235 (15)0.0304 (19)0.0052 (14)0.0051 (15)0.0011 (14)
C350.042 (2)0.0242 (17)0.0342 (18)0.0040 (16)0.0026 (17)0.0041 (15)
C360.048 (2)0.0274 (17)0.029 (2)0.0081 (15)0.0097 (15)0.0065 (15)
C370.042 (2)0.0237 (16)0.0344 (19)0.0030 (15)0.0028 (16)0.0026 (14)
C380.068 (2)0.026 (2)0.0188 (14)0.0044 (18)0.0007 (17)0.0028 (15)
N1X0.044 (4)0.026 (3)0.029 (3)0.005 (3)0.005 (3)0.000 (3)
N2X0.039 (3)0.027 (3)0.025 (3)0.004 (3)0.002 (3)0.002 (3)
N3X0.054 (4)0.021 (3)0.025 (3)0.001 (3)0.000 (3)0.001 (3)
N4X0.050 (3)0.027 (3)0.024 (3)0.003 (3)0.008 (3)0.003 (3)
C33X0.037 (4)0.030 (4)0.020 (3)0.005 (3)0.002 (3)0.005 (3)
C34X0.050 (4)0.027 (3)0.031 (4)0.008 (4)0.009 (4)0.004 (3)
C35X0.044 (4)0.027 (4)0.029 (4)0.001 (4)0.003 (4)0.003 (3)
C36X0.049 (4)0.019 (3)0.026 (4)0.004 (3)0.007 (4)0.003 (3)
C37X0.047 (4)0.030 (4)0.028 (4)0.003 (4)0.006 (4)0.008 (3)
C38X0.062 (4)0.025 (4)0.022 (4)0.002 (4)0.000 (4)0.006 (3)
C390.0500 (11)0.0261 (8)0.0223 (7)0.0010 (7)0.0001 (11)0.0013 (10)
C400.0392 (12)0.0246 (11)0.0356 (11)0.0070 (9)0.0009 (10)0.0006 (9)
C410.0366 (12)0.0267 (11)0.0419 (13)0.0087 (9)0.0001 (10)0.0032 (10)
C420.0406 (12)0.0224 (10)0.0385 (12)0.0082 (9)0.0007 (10)0.0012 (9)
C430.0341 (12)0.0297 (11)0.0443 (13)0.0086 (9)0.0038 (10)0.0038 (10)
C440.0533 (12)0.0353 (9)0.0216 (8)0.0044 (8)0.0003 (12)0.0009 (11)
Geometric parameters (Å, º) top
O1—C71.313 (5)C17—C181.394 (4)
O1—H1O10.83 (2)C17—C221.416 (4)
O2—C71.207 (5)C17—C231.483 (3)
C7—C11.488 (6)C18—C191.402 (3)
C1—C61.395 (6)C18—C241.495 (4)
C1—C21.411 (6)C19—C201.369 (4)
C2—C31.396 (6)C19—H19A0.9500
C2—C81.504 (7)C20—C211.390 (4)
C3—C41.376 (7)C20—H20A0.9500
C3—H3A0.9500C21—C221.371 (4)
C4—C51.383 (7)C21—H21A0.9500
C4—H4A0.9500C22—H22A0.9500
C5—C61.377 (6)C24—H24A0.9800
C5—H5A0.9500C24—H24B0.9800
C6—H6A0.9500C24—H24C0.9800
C8—H8A0.9800C25—C261.399 (3)
C8—H8B0.9800C25—C301.411 (3)
C8—H8C0.9800C25—C311.489 (3)
O1X—C7X1.310 (9)C26—C271.403 (3)
O1X—H2O10.8400C26—C321.487 (4)
O2X—C7X1.215 (10)C27—C281.362 (4)
C7X—C1X1.492 (11)C27—H27A0.9500
C1X—C2X1.401 (12)C28—C291.389 (4)
C1X—C6X1.404 (11)C28—H28A0.9500
C2X—C3X1.390 (13)C29—C301.370 (4)
C2X—C8X1.509 (12)C29—H29A0.9500
C3X—C4X1.373 (12)C30—H30A0.9500
C3X—H3XA0.9500C32—H32A0.9800
C4X—C5X1.386 (11)C32—H32B0.9800
C4X—H4XA0.9500C32—H32C0.9800
C5X—C6X1.370 (11)N1—C331.481 (4)
C5X—H5XA0.9500N1—C361.481 (5)
C6X—H6XA0.9500N1—C351.481 (5)
C8X—H8XA0.9800N2—C331.473 (4)
C8X—H8XB0.9800N2—C341.474 (5)
C8X—H8XC0.9800N2—C371.485 (5)
O3—C151.313 (4)N3—C351.462 (5)
O3—H1O30.844 (19)N3—C341.463 (5)
O4—C151.203 (4)N3—C381.474 (6)
C15—C91.498 (4)N4—C361.457 (6)
C9—C141.398 (4)N4—C371.458 (6)
C9—C101.407 (4)N4—C381.477 (6)
C10—C111.405 (5)C33—H33A0.9900
C10—C161.501 (5)C33—H33B0.9900
C11—C121.384 (5)C34—H34A0.9900
C11—H11A0.9500C34—H34B0.9900
C12—C131.377 (5)C35—H35A0.9900
C12—H12A0.9500C35—H35B0.9900
C13—C141.381 (5)C36—H36A0.9900
C13—H13A0.9500C36—H36B0.9900
C14—H14A0.9500C37—H37A0.9900
C16—H16A0.9800C37—H37B0.9900
C16—H16B0.9800C38—H38A0.9900
C16—H16C0.9800C38—H38B0.9900
O3X—C15X1.311 (13)N1X—C36X1.470 (13)
O3X—H2O30.8400N1X—C33X1.473 (11)
O4X—C15X1.206 (13)N1X—C35X1.476 (13)
C15X—C9X1.524 (14)N2X—C33X1.462 (11)
C9X—C14X1.388 (14)N2X—C34X1.490 (13)
C9X—C10X1.397 (15)N2X—C37X1.505 (13)
C10X—C11X1.404 (15)N3X—C35X1.451 (14)
C10X—C16X1.515 (15)N3X—C34X1.464 (14)
C11X—C12X1.368 (15)N3X—C38X1.474 (15)
C11X—H11B0.9500N4X—C36X1.457 (15)
C12X—C13X1.364 (15)N4X—C37X1.458 (15)
C12X—H12B0.9500N4X—C38X1.470 (15)
C13X—C14X1.362 (15)C33X—H33C0.9900
C13X—H13B0.9500C33X—H33D0.9900
C14X—H14B0.9500C34X—H34C0.9900
C16X—H16D0.9800C34X—H34D0.9900
C16X—H16E0.9800C35X—H35C0.9900
C16X—H16F0.9800C35X—H35D0.9900
O5—C231.308 (3)C36X—H36C0.9900
O5—H1O50.870 (19)C36X—H36D0.9900
O6—C231.218 (3)C37X—H37C0.9900
O7—C311.302 (3)C37X—H37D0.9900
O7—H1O70.869 (19)C38X—H38C0.9900
O8—C311.211 (3)C38X—H38D0.9900
N5—C391.472 (3)C39—H39A0.9900
N5—C421.478 (3)C39—H39B0.9900
N5—C411.481 (3)C40—H40A0.9900
N6—C391.470 (3)C40—H40B0.9900
N6—C401.477 (3)C41—H41A0.9900
N6—C431.479 (3)C41—H41B0.9900
N7—C411.452 (3)C42—H42A0.9900
N7—C401.461 (3)C42—H42B0.9900
N7—C441.469 (3)C43—H43A0.9900
N8—C431.456 (3)C43—H43B0.9900
N8—C421.457 (3)C44—H44A0.9900
N8—C441.477 (3)C44—H44B0.9900
C7—O1—H1O1111 (3)C25—C26—C27118.0 (2)
O2—C7—O1122.5 (4)C25—C26—C32124.1 (2)
O2—C7—C1124.6 (4)C27—C26—C32117.9 (2)
O1—C7—C1112.9 (4)C28—C27—C26122.1 (3)
C6—C1—C2119.2 (5)C28—C27—H27A119.0
C6—C1—C7118.9 (5)C26—C27—H27A119.0
C2—C1—C7121.9 (5)C27—C28—C29120.1 (2)
C3—C2—C1117.8 (6)C27—C28—H28A119.9
C3—C2—C8119.0 (5)C29—C28—H28A119.9
C1—C2—C8123.2 (5)C30—C29—C28119.4 (2)
C4—C3—C2121.9 (6)C30—C29—H29A120.3
C4—C3—H3A119.0C28—C29—H29A120.3
C2—C3—H3A119.0C29—C30—C25121.3 (2)
C3—C4—C5120.2 (5)C29—C30—H30A119.4
C3—C4—H4A119.9C25—C30—H30A119.4
C5—C4—H4A119.9O8—C31—O7121.9 (2)
C6—C5—C4119.0 (5)O8—C31—C25123.9 (2)
C6—C5—H5A120.5O7—C31—C25114.2 (2)
C4—C5—H5A120.5C26—C32—H32A109.5
C5—C6—C1121.8 (5)C26—C32—H32B109.5
C5—C6—H6A119.1H32A—C32—H32B109.5
C1—C6—H6A119.1C26—C32—H32C109.5
C2—C8—H8A109.5H32A—C32—H32C109.5
C2—C8—H8B109.5H32B—C32—H32C109.5
H8A—C8—H8B109.5C33—N1—C36107.8 (3)
C2—C8—H8C109.5C33—N1—C35108.4 (3)
H8A—C8—H8C109.5C36—N1—C35109.1 (3)
H8B—C8—H8C109.5C33—N2—C34108.2 (3)
C7X—O1X—H2O1109.5C33—N2—C37107.5 (3)
O2X—C7X—O1X124.1 (9)C34—N2—C37107.8 (3)
O2X—C7X—C1X119.6 (9)C35—N3—C34108.1 (4)
O1X—C7X—C1X116.2 (8)C35—N3—C38108.1 (5)
C2X—C1X—C6X120.7 (10)C34—N3—C38109.6 (5)
C2X—C1X—C7X123.5 (10)C36—N4—C37109.6 (4)
C6X—C1X—C7X115.8 (9)C36—N4—C38107.3 (5)
C3X—C2X—C1X116.3 (11)C37—N4—C38108.2 (6)
C3X—C2X—C8X116.4 (10)N2—C33—N1111.6 (3)
C1X—C2X—C8X127.2 (11)N2—C33—H33A109.3
C4X—C3X—C2X123.1 (13)N1—C33—H33A109.3
C4X—C3X—H3XA118.5N2—C33—H33B109.3
C2X—C3X—H3XA118.5N1—C33—H33B109.3
C3X—C4X—C5X119.9 (11)H33A—C33—H33B108.0
C3X—C4X—H4XA120.0N3—C34—N2112.1 (4)
C5X—C4X—H4XA120.0N3—C34—H34A109.2
C6X—C5X—C4X119.0 (10)N2—C34—H34A109.2
C6X—C5X—H5XA120.5N3—C34—H34B109.2
C4X—C5X—H5XA120.5N2—C34—H34B109.2
C5X—C6X—C1X120.9 (9)H34A—C34—H34B107.9
C5X—C6X—H6XA119.6N3—C35—N1111.0 (4)
C1X—C6X—H6XA119.6N3—C35—H35A109.4
C2X—C8X—H8XA109.5N1—C35—H35A109.4
C2X—C8X—H8XB109.5N3—C35—H35B109.4
H8XA—C8X—H8XB109.5N1—C35—H35B109.4
C2X—C8X—H8XC109.5H35A—C35—H35B108.0
H8XA—C8X—H8XC109.5N4—C36—N1111.4 (4)
H8XB—C8X—H8XC109.5N4—C36—H36A109.3
C15—O3—H1O3109 (3)N1—C36—H36A109.3
O4—C15—O3122.4 (3)N4—C36—H36B109.3
O4—C15—C9121.2 (3)N1—C36—H36B109.3
O3—C15—C9116.4 (3)H36A—C36—H36B108.0
C14—C9—C10119.9 (3)N4—C37—N2112.4 (4)
C14—C9—C15115.5 (3)N4—C37—H37A109.1
C10—C9—C15124.5 (3)N2—C37—H37A109.1
C11—C10—C9117.6 (4)N4—C37—H37B109.1
C11—C10—C16116.7 (3)N2—C37—H37B109.1
C9—C10—C16125.6 (3)H37A—C37—H37B107.8
C12—C11—C10121.5 (4)N3—C38—N4111.8 (5)
C12—C11—H11A119.2N3—C38—H38A109.3
C10—C11—H11A119.2N4—C38—H38A109.3
C13—C12—C11120.4 (3)N3—C38—H38B109.3
C13—C12—H12A119.8N4—C38—H38B109.3
C11—C12—H12A119.8H38A—C38—H38B107.9
C12—C13—C14119.4 (3)C36X—N1X—C33X108.5 (9)
C12—C13—H13A120.3C36X—N1X—C35X107.3 (11)
C14—C13—H13A120.3C33X—N1X—C35X106.7 (9)
C13—C14—C9121.2 (3)C33X—N2X—C34X106.5 (9)
C13—C14—H14A119.4C33X—N2X—C37X107.3 (9)
C9—C14—H14A119.4C34X—N2X—C37X108.1 (11)
C10—C16—H16A109.5C35X—N3X—C34X110.4 (13)
C10—C16—H16B109.5C35X—N3X—C38X109.6 (16)
H16A—C16—H16B109.5C34X—N3X—C38X104.7 (15)
C10—C16—H16C109.5C36X—N4X—C37X106.0 (14)
H16A—C16—H16C109.5C36X—N4X—C38X110.3 (16)
H16B—C16—H16C109.5C37X—N4X—C38X110.1 (17)
C15X—O3X—H2O3109.5N2X—C33X—N1X113.5 (8)
O4X—C15X—O3X123.5 (12)N2X—C33X—H33C108.9
O4X—C15X—C9X122.1 (11)N1X—C33X—H33C108.9
O3X—C15X—C9X114.4 (12)N2X—C33X—H33D108.9
C14X—C9X—C10X120.1 (13)N1X—C33X—H33D108.9
C14X—C9X—C15X116.6 (13)H33C—C33X—H33D107.7
C10X—C9X—C15X123.3 (13)N3X—C34X—N2X112.9 (11)
C9X—C10X—C11X114.7 (15)N3X—C34X—H34C109.0
C9X—C10X—C16X122.4 (14)N2X—C34X—H34C109.0
C11X—C10X—C16X122.5 (15)N3X—C34X—H34D109.0
C12X—C11X—C10X123.6 (16)N2X—C34X—H34D109.0
C12X—C11X—H11B118.2H34C—C34X—H34D107.8
C10X—C11X—H11B118.2N3X—C35X—N1X112.5 (12)
C13X—C12X—C11X120.4 (14)N3X—C35X—H35C109.1
C13X—C12X—H12B119.8N1X—C35X—H35C109.1
C11X—C12X—H12B119.8N3X—C35X—H35D109.1
C14X—C13X—C12X117.6 (14)N1X—C35X—H35D109.1
C14X—C13X—H13B121.2H35C—C35X—H35D107.8
C12X—C13X—H13B121.2N4X—C36X—N1X112.7 (12)
C13X—C14X—C9X123.1 (15)N4X—C36X—H36C109.0
C13X—C14X—H14B118.5N1X—C36X—H36C109.0
C9X—C14X—H14B118.5N4X—C36X—H36D109.0
C10X—C16X—H16D109.5N1X—C36X—H36D109.0
C10X—C16X—H16E109.5H36C—C36X—H36D107.8
H16D—C16X—H16E109.5N4X—C37X—N2X110.9 (13)
C10X—C16X—H16F109.5N4X—C37X—H37C109.5
H16D—C16X—H16F109.5N2X—C37X—H37C109.5
H16E—C16X—H16F109.5N4X—C37X—H37D109.5
C23—O5—H1O5106 (3)N2X—C37X—H37D109.5
C31—O7—H1O7112 (3)H37C—C37X—H37D108.1
C39—N5—C42108.35 (18)N4X—C38X—N3X111.4 (15)
C39—N5—C41108.29 (18)N4X—C38X—H38C109.3
C42—N5—C41108.12 (18)N3X—C38X—H38C109.3
C39—N6—C40108.19 (18)N4X—C38X—H38D109.3
C39—N6—C43107.92 (18)N3X—C38X—H38D109.3
C40—N6—C43107.94 (18)H38C—C38X—H38D108.0
C41—N7—C40108.33 (18)N6—C39—N5111.30 (13)
C41—N7—C44108.64 (18)N6—C39—H39A109.4
C40—N7—C44108.39 (19)N5—C39—H39A109.4
C43—N8—C42108.25 (19)N6—C39—H39B109.4
C43—N8—C44108.47 (18)N5—C39—H39B109.4
C42—N8—C44108.10 (18)H39A—C39—H39B108.0
C18—C17—C22119.2 (2)N7—C40—N6112.13 (17)
C18—C17—C23123.2 (2)N7—C40—H40A109.2
C22—C17—C23117.5 (2)N6—C40—H40A109.2
C17—C18—C19118.0 (3)N7—C40—H40B109.2
C17—C18—C24124.0 (2)N6—C40—H40B109.2
C19—C18—C24118.0 (3)H40A—C40—H40B107.9
C20—C19—C18121.7 (3)N7—C41—N5111.78 (17)
C20—C19—H19A119.2N7—C41—H41A109.3
C18—C19—H19A119.2N5—C41—H41A109.3
C19—C20—C21121.0 (2)N7—C41—H41B109.3
C19—C20—H20A119.5N5—C41—H41B109.3
C21—C20—H20A119.5H41A—C41—H41B107.9
C22—C21—C20118.3 (3)N8—C42—N5111.92 (17)
C22—C21—H21A120.9N8—C42—H42A109.2
C20—C21—H21A120.9N5—C42—H42A109.2
C21—C22—C17121.8 (3)N8—C42—H42B109.2
C21—C22—H22A119.1N5—C42—H42B109.2
C17—C22—H22A119.1H42A—C42—H42B107.9
O6—C23—O5122.2 (2)N8—C43—N6112.32 (18)
O6—C23—C17123.7 (2)N8—C43—H43A109.1
O5—C23—C17114.1 (2)N6—C43—H43A109.1
C18—C24—H24A109.5N8—C43—H43B109.1
C18—C24—H24B109.5N6—C43—H43B109.1
H24A—C24—H24B109.5H43A—C43—H43B107.9
C18—C24—H24C109.5N7—C44—N8111.72 (13)
H24A—C24—H24C109.5N7—C44—H44A109.3
H24B—C24—H24C109.5N8—C44—H44A109.3
C26—C25—C30119.2 (2)N7—C44—H44B109.3
C26—C25—C31123.2 (2)N8—C44—H44B109.3
C30—C25—C31117.5 (2)H44A—C44—H44B107.9
O2—C7—C1—C6170.8 (6)C26—C27—C28—C290.1 (4)
O1—C7—C1—C611.1 (9)C27—C28—C29—C300.6 (4)
O2—C7—C1—C210.7 (13)C28—C29—C30—C250.7 (4)
O1—C7—C1—C2167.4 (10)C26—C25—C30—C290.2 (4)
C6—C1—C2—C31.0 (17)C31—C25—C30—C29177.9 (2)
C7—C1—C2—C3177.5 (9)C26—C25—C31—O810.9 (4)
C6—C1—C2—C8179.7 (9)C30—C25—C31—O8171.5 (3)
C7—C1—C2—C81.8 (18)C26—C25—C31—O7168.5 (2)
C1—C2—C3—C41.0 (18)C30—C25—C31—O79.0 (3)
C8—C2—C3—C4179.7 (9)C34—N2—C33—N157.3 (4)
C2—C3—C4—C50.3 (13)C37—N2—C33—N158.9 (4)
C3—C4—C5—C60.4 (9)C36—N1—C33—N260.0 (4)
C4—C5—C6—C10.3 (8)C35—N1—C33—N258.0 (4)
C2—C1—C6—C50.4 (12)C35—N3—C34—N260.3 (5)
C7—C1—C6—C5178.1 (6)C38—N3—C34—N257.2 (5)
O2X—C7X—C1X—C2X163 (2)C33—N2—C34—N358.7 (4)
O1X—C7X—C1X—C2X13 (3)C37—N2—C34—N357.3 (4)
O2X—C7X—C1X—C6X21 (2)C34—N3—C35—N160.2 (5)
O1X—C7X—C1X—C6X162.3 (13)C38—N3—C35—N158.4 (6)
C6X—C1X—C2X—C3X4 (4)C33—N1—C35—N359.3 (5)
C7X—C1X—C2X—C3X179 (2)C36—N1—C35—N357.9 (5)
C6X—C1X—C2X—C8X176 (2)C37—N4—C36—N158.0 (5)
C7X—C1X—C2X—C8X1 (4)C38—N4—C36—N159.2 (5)
C1X—C2X—C3X—C4X1 (4)C33—N1—C36—N458.8 (4)
C8X—C2X—C3X—C4X179 (2)C35—N1—C36—N458.7 (4)
C2X—C3X—C4X—C5X1 (3)C36—N4—C37—N257.6 (6)
C3X—C4X—C5X—C6X1.0 (19)C38—N4—C37—N259.1 (6)
C4X—C5X—C6X—C1X1.8 (18)C33—N2—C37—N457.5 (5)
C2X—C1X—C6X—C5X4 (3)C34—N2—C37—N458.9 (5)
C7X—C1X—C6X—C5X179.9 (12)C35—N3—C38—N460.6 (7)
O4—C15—C9—C1418.6 (5)C34—N3—C38—N457.0 (7)
O3—C15—C9—C14161.2 (4)C36—N4—C38—N360.7 (7)
O4—C15—C9—C10157.5 (7)C37—N4—C38—N357.5 (7)
O3—C15—C9—C1022.8 (8)C34X—N2X—C33X—N1X59.9 (12)
C14—C9—C10—C110.6 (12)C37X—N2X—C33X—N1X55.7 (13)
C15—C9—C10—C11176.5 (6)C36X—N1X—C33X—N2X54.3 (12)
C14—C9—C10—C16178.2 (7)C35X—N1X—C33X—N2X61.0 (12)
C15—C9—C10—C165.9 (13)C35X—N3X—C34X—N2X55.2 (18)
C9—C10—C11—C120.5 (12)C38X—N3X—C34X—N2X62.6 (16)
C16—C10—C11—C12178.3 (6)C33X—N2X—C34X—N3X55.8 (14)
C10—C11—C12—C130.2 (9)C37X—N2X—C34X—N3X59.3 (14)
C11—C12—C13—C140.0 (6)C34X—N3X—C35X—N1X56.1 (18)
C12—C13—C14—C90.1 (6)C38X—N3X—C35X—N1X58.7 (18)
C10—C9—C14—C130.5 (8)C36X—N1X—C35X—N3X58.7 (15)
C15—C9—C14—C13176.7 (3)C33X—N1X—C35X—N3X57.5 (15)
O4X—C15X—C9X—C14X166.4 (18)C37X—N4X—C36X—N1X62.3 (17)
O3X—C15X—C9X—C14X15 (3)C38X—N4X—C36X—N1X56.8 (17)
O4X—C15X—C9X—C10X10 (4)C33X—N1X—C36X—N4X57.5 (15)
O3X—C15X—C9X—C10X168 (3)C35X—N1X—C36X—N4X57.4 (15)
C14X—C9X—C10X—C11X8 (6)C36X—N4X—C37X—N2X63.4 (18)
C15X—C9X—C10X—C11X175 (3)C38X—N4X—C37X—N2X55.9 (18)
C14X—C9X—C10X—C16X179 (3)C33X—N2X—C37X—N4X60.7 (15)
C15X—C9X—C10X—C16X3 (6)C34X—N2X—C37X—N4X53.8 (16)
C9X—C10X—C11X—C12X7 (6)C36X—N4X—C38X—N3X55 (2)
C16X—C10X—C11X—C12X179 (3)C37X—N4X—C38X—N3X62 (2)
C10X—C11X—C12X—C13X3 (5)C35X—N3X—C38X—N4X56 (2)
C11X—C12X—C13X—C14X0 (3)C34X—N3X—C38X—N4X63 (2)
C12X—C13X—C14X—C9X2 (3)C40—N6—C39—N558.2 (3)
C10X—C9X—C14X—C13X7 (4)C43—N6—C39—N558.4 (3)
C15X—C9X—C14X—C13X176.8 (18)C42—N5—C39—N658.6 (3)
C22—C17—C18—C190.3 (3)C41—N5—C39—N658.5 (3)
C23—C17—C18—C19177.0 (2)C41—N7—C40—N658.9 (2)
C22—C17—C18—C24179.8 (2)C44—N7—C40—N658.8 (2)
C23—C17—C18—C243.1 (4)C39—N6—C40—N758.6 (2)
C17—C18—C19—C200.1 (4)C43—N6—C40—N758.0 (2)
C24—C18—C19—C20179.9 (2)C40—N7—C41—N559.0 (2)
C18—C19—C20—C210.1 (4)C44—N7—C41—N558.6 (2)
C19—C20—C21—C220.2 (4)C39—N5—C41—N759.1 (2)
C20—C21—C22—C170.4 (4)C42—N5—C41—N758.1 (2)
C18—C17—C22—C210.4 (4)C43—N8—C42—N558.6 (2)
C23—C17—C22—C21177.3 (2)C44—N8—C42—N558.7 (2)
C18—C17—C23—O64.5 (4)C39—N5—C42—N858.8 (2)
C22—C17—C23—O6178.8 (3)C41—N5—C42—N858.4 (2)
C18—C17—C23—O5174.4 (2)C42—N8—C43—N658.9 (2)
C22—C17—C23—O52.3 (3)C44—N8—C43—N658.2 (2)
C30—C25—C26—C270.3 (3)C39—N6—C43—N858.9 (2)
C31—C25—C26—C27177.2 (2)C40—N6—C43—N857.8 (2)
C30—C25—C26—C32178.7 (2)C41—N7—C44—N858.9 (3)
C31—C25—C26—C321.2 (4)C40—N7—C44—N858.6 (3)
C25—C26—C27—C280.4 (4)C43—N8—C44—N758.4 (3)
C32—C26—C27—C28178.8 (2)C42—N8—C44—N758.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N10.84 (3)1.79 (4)2.620 (5)171 (4)
O3—H1O3···N20.85 (4)1.83 (4)2.677 (5)176 (3)
O5—H1O5···N50.87 (3)1.83 (3)2.677 (3)166 (4)
O7—H1O7···N60.87 (3)1.80 (3)2.664 (3)171 (4)
C6—H6A···O10.952.342.682 (6)101
C16—H16A···O30.982.452.818 (5)102
C22—H22A···O50.952.322.673 (3)101
C30—H30A···O70.952.342.683 (3)101
C33—H33A···O40.992.583.141 (5)116
C33—H33B···N8i0.992.603.529 (4)157
C36—H36B···N70.992.603.550 (6)161
C38—H38B···O4ii0.992.433.387 (9)161
C40—H40B···N3iii0.992.593.507 (7)155
C44—H44A···O6iv0.992.383.367 (4)172
C44—H44B···O8iv0.992.393.372 (3)171
Symmetry codes: (i) x, y1, z; (ii) x, y+1/2, z1/2; (iii) x, y+1/2, z+1/2; (iv) x, y+3/2, z1/2.
(163K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top
Crystal data top
C6H12N4·2C8H8O2F(000) = 1760
Mr = 412.48Dx = 1.315 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 30.9991 (17) ÅCell parameters from 9880 reflections
b = 9.3611 (5) Åθ = 2.2–27.1°
c = 14.3546 (8) ŵ = 0.09 mm1
β = 90.0906 (12)°T = 163 K
V = 4165.5 (4) Å3Block, colourless
Z = 80.43 × 0.17 × 0.15 mm
Data collection top
Bruker APEX DUO CCD area detector
diffractometer
10040 independent reflections
Radiation source: fine-focus sealed tube7515 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 28.0°, θmin = 0.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 3640
Tmin = 0.915, Tmax = 0.963k = 1212
66066 measured reflectionsl = 1818
Refinement top
Refinement on F21222 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.150 w = 1/[σ2(Fo2) + (0.0704P)2 + 1.4929P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
10040 reflectionsΔρmax = 0.46 e Å3
837 parametersΔρmin = 0.19 e Å3
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
xyzUiso*/UeqOcc. (<1)
O10.16463 (12)0.2382 (5)0.3350 (3)0.0500 (10)0.602 (7)
H1O10.1784 (14)0.250 (5)0.286 (2)0.064 (15)*0.602 (7)
O20.12826 (14)0.4183 (6)0.2738 (3)0.0601 (12)0.602 (7)
C70.13364 (15)0.3336 (6)0.3363 (4)0.0333 (10)0.602 (7)
C10.1077 (3)0.3295 (8)0.4233 (5)0.0326 (12)0.602 (7)
C20.0784 (5)0.4393 (11)0.4473 (8)0.0347 (14)0.602 (7)
C30.0564 (4)0.4281 (10)0.5315 (6)0.0425 (15)0.602 (7)
H3A0.03690.50160.54890.051*0.602 (7)
C40.0622 (2)0.3137 (8)0.5901 (5)0.0448 (14)0.602 (7)
H4A0.04690.30920.64730.054*0.602 (7)
C50.0901 (2)0.2053 (7)0.5661 (5)0.0432 (13)0.602 (7)
H5A0.09370.12500.60580.052*0.602 (7)
C60.11278 (19)0.2145 (7)0.4839 (4)0.0371 (11)0.602 (7)
H6A0.13240.14040.46810.044*0.602 (7)
C80.0708 (3)0.5682 (8)0.3862 (6)0.0478 (16)0.602 (7)
H8A0.09830.61570.37360.072*0.602 (7)
H8B0.05140.63480.41800.072*0.602 (7)
H8C0.05770.53770.32730.072*0.602 (7)
O1X0.1346 (2)0.3338 (8)0.2843 (5)0.0570 (17)0.398 (7)
H2O10.15340.30480.24690.085*0.398 (7)
O2X0.16553 (18)0.1741 (7)0.3768 (5)0.0601 (18)0.398 (7)
C7X0.1376 (2)0.2623 (9)0.3623 (5)0.0381 (14)0.398 (7)
C1X0.1062 (5)0.3008 (12)0.4371 (8)0.0310 (16)0.398 (7)
C2X0.0817 (7)0.4269 (18)0.4368 (12)0.0345 (18)0.398 (7)
C3X0.0548 (6)0.4492 (15)0.5126 (9)0.0359 (18)0.398 (7)
H3XA0.03860.53510.51540.043*0.398 (7)
C4X0.0507 (3)0.3516 (11)0.5841 (8)0.0387 (18)0.398 (7)
H4XA0.03190.37140.63470.046*0.398 (7)
C5X0.0739 (3)0.2250 (10)0.5824 (6)0.0384 (17)0.398 (7)
H5XA0.07090.15660.63080.046*0.398 (7)
C6X0.1014 (3)0.2006 (10)0.5082 (7)0.0350 (16)0.398 (7)
H6XA0.11730.11400.50560.042*0.398 (7)
C8X0.0814 (4)0.5416 (12)0.3626 (8)0.044 (2)0.398 (7)
H8XA0.11050.58110.35560.065*0.398 (7)
H8XB0.06140.61790.38080.065*0.398 (7)
H8XC0.07200.50030.30320.065*0.398 (7)
O30.36536 (10)0.1735 (4)0.2832 (2)0.0507 (8)0.743 (6)
H1O30.3429 (12)0.190 (6)0.252 (4)0.106 (19)*0.743 (6)
O40.33481 (9)0.3290 (3)0.3777 (3)0.0550 (9)0.743 (6)
C150.36216 (11)0.2404 (4)0.3630 (3)0.0328 (8)0.743 (6)
C90.39463 (19)0.2023 (5)0.4360 (3)0.0271 (9)0.743 (6)
C100.4180 (3)0.0734 (8)0.4381 (5)0.0291 (9)0.743 (6)
C110.4460 (2)0.0506 (6)0.5142 (4)0.0343 (10)0.743 (6)
H11A0.46230.03510.51700.041*0.743 (6)
C120.45015 (16)0.1496 (5)0.5844 (3)0.0390 (10)0.743 (6)
H12A0.46910.13110.63500.047*0.743 (6)
C130.42712 (16)0.2752 (5)0.5822 (3)0.0392 (9)0.743 (6)
H13A0.43010.34320.63090.047*0.743 (6)
C140.39956 (15)0.3015 (5)0.5082 (3)0.0344 (9)0.743 (6)
H14A0.38370.38830.50630.041*0.743 (6)
C160.41691 (16)0.0406 (5)0.3648 (4)0.0384 (11)0.743 (6)
H16A0.38710.05590.34450.058*0.743 (6)
H16B0.42850.12970.39060.058*0.743 (6)
H16C0.43440.01080.31150.058*0.743 (6)
O3X0.3347 (3)0.2631 (10)0.3371 (7)0.050 (2)0.257 (6)
H2O30.32060.25730.28730.074*0.257 (6)
O4X0.3723 (3)0.0866 (13)0.2726 (6)0.061 (3)0.257 (6)
C15X0.3659 (3)0.1679 (12)0.3366 (8)0.0339 (19)0.257 (6)
C9X0.3936 (6)0.1691 (17)0.4239 (11)0.0324 (19)0.257 (6)
C10X0.4223 (11)0.059 (3)0.4462 (17)0.032 (2)0.257 (6)
C11X0.4425 (7)0.0711 (19)0.5337 (11)0.037 (2)0.257 (6)
H11B0.46050.00470.55420.044*0.257 (6)
C12X0.4373 (5)0.1866 (17)0.5904 (10)0.039 (2)0.257 (6)
H12B0.45280.19100.64750.047*0.257 (6)
C13X0.4102 (5)0.2972 (14)0.5665 (10)0.041 (2)0.257 (6)
H13B0.40640.37770.60600.049*0.257 (6)
C14X0.3888 (5)0.2860 (16)0.4829 (10)0.0372 (19)0.257 (6)
H14B0.37000.36100.46460.045*0.257 (6)
C16X0.4297 (5)0.0691 (15)0.3843 (10)0.041 (3)0.257 (6)
H16D0.45520.12140.40600.062*0.257 (6)
H16E0.43430.03710.32000.062*0.257 (6)
H16F0.40450.13200.38670.062*0.257 (6)
O50.13505 (7)0.8190 (3)0.52576 (16)0.0593 (6)
H1O50.1598 (10)0.791 (5)0.505 (4)0.13 (2)*
O60.15736 (6)0.6856 (3)0.64314 (19)0.0681 (7)
O70.36434 (7)0.6897 (2)0.52239 (15)0.0574 (6)
H1O70.3380 (7)0.703 (4)0.501 (3)0.081 (12)*
O80.34134 (7)0.8053 (3)0.64595 (18)0.0719 (7)
N50.21061 (6)0.7725 (2)0.44110 (14)0.0321 (4)
N60.28804 (6)0.7312 (2)0.44080 (14)0.0316 (4)
N70.24257 (7)0.6222 (2)0.32184 (14)0.0328 (4)
N80.25518 (6)0.8794 (2)0.32030 (14)0.0334 (5)
C170.08288 (7)0.7498 (3)0.63494 (18)0.0336 (5)
C180.06827 (9)0.6695 (3)0.7105 (2)0.0406 (6)
C190.02412 (8)0.6747 (3)0.7313 (2)0.0463 (7)
H19A0.01360.62090.78250.056*
C200.00433 (8)0.7550 (3)0.6800 (2)0.0486 (7)
H20A0.03400.75570.69610.058*
C210.01005 (9)0.8351 (3)0.6048 (2)0.0479 (7)
H21A0.00950.89130.56930.057*
C220.05288 (9)0.8314 (3)0.5830 (2)0.0432 (6)
H22A0.06290.88530.53130.052*
C230.12847 (8)0.7480 (3)0.6029 (2)0.0394 (6)
C240.09667 (10)0.5784 (3)0.7700 (2)0.0538 (7)
H24A0.07910.52940.81690.081*
H24B0.11820.63850.80120.081*
H24C0.11130.50750.73110.081*
C250.41632 (7)0.7494 (3)0.63504 (17)0.0325 (5)
C260.43104 (8)0.8284 (3)0.71115 (18)0.0370 (6)
C270.47513 (8)0.8230 (3)0.7323 (2)0.0419 (6)
H27A0.48570.87670.78370.050*
C280.50328 (8)0.7432 (3)0.6815 (2)0.0444 (6)
H28A0.53300.74200.69780.053*
C290.48886 (9)0.6636 (3)0.6060 (2)0.0459 (6)
H29A0.50850.60740.57080.055*
C300.44577 (8)0.6672 (3)0.58292 (19)0.0393 (6)
H30A0.43570.61350.53110.047*
C310.37056 (8)0.7507 (3)0.60274 (19)0.0375 (5)
C320.40299 (10)0.9204 (3)0.7700 (2)0.0505 (7)
H32A0.42090.97370.81440.076*
H32B0.38250.86050.80410.076*
H32C0.38720.98760.73030.076*
N10.21773 (17)0.2511 (5)0.1932 (3)0.0301 (8)0.675 (11)
N20.29601 (17)0.2286 (5)0.1778 (3)0.0307 (9)0.675 (11)
N30.2481 (2)0.1196 (9)0.0635 (5)0.0337 (11)0.675 (11)
N40.2553 (3)0.3795 (9)0.0699 (5)0.0347 (11)0.675 (11)
C330.2596 (2)0.2378 (5)0.2433 (3)0.0287 (9)0.675 (11)
H33A0.26370.32160.28440.034*0.675 (11)
H33B0.25910.15110.28280.034*0.675 (11)
C340.2886 (2)0.1058 (6)0.1149 (4)0.0347 (11)0.675 (11)
H34A0.31280.09890.07020.042*0.675 (11)
H34B0.28810.01670.15200.042*0.675 (11)
C350.2128 (2)0.1254 (7)0.1312 (5)0.0345 (12)0.675 (11)
H35A0.21280.03700.16910.041*0.675 (11)
H35B0.18490.13130.09790.041*0.675 (11)
C360.2197 (2)0.3825 (7)0.1366 (4)0.0359 (11)0.675 (11)
H36A0.19220.39430.10240.043*0.675 (11)
H36B0.22330.46590.17830.043*0.675 (11)
C370.2957 (2)0.3596 (7)0.1199 (5)0.0351 (12)0.675 (11)
H37A0.30090.44350.16050.042*0.675 (11)
H37B0.31970.35460.07450.042*0.675 (11)
C380.2488 (4)0.2534 (10)0.0097 (6)0.0390 (12)0.675 (11)
H38A0.22110.26380.02420.047*0.675 (11)
H38B0.27220.24890.03690.047*0.675 (11)
N1X0.2035 (4)0.2742 (10)0.1791 (7)0.0338 (16)0.325 (11)
N2X0.2819 (4)0.2475 (11)0.1941 (7)0.0304 (15)0.325 (11)
N3X0.2425 (5)0.1176 (19)0.0720 (11)0.0338 (18)0.325 (11)
N4X0.2509 (5)0.376 (2)0.0625 (12)0.0351 (18)0.325 (11)
C33X0.2409 (4)0.2618 (10)0.2431 (6)0.0290 (16)0.325 (11)
H33C0.24210.34760.28330.035*0.325 (11)
H33D0.23680.17770.28380.035*0.325 (11)
C34X0.2795 (4)0.1142 (14)0.1363 (9)0.0356 (19)0.325 (11)
H34C0.30650.10390.10010.043*0.325 (11)
H34D0.27690.03020.17780.043*0.325 (11)
C35X0.2027 (4)0.1419 (15)0.1231 (11)0.034 (2)0.325 (11)
H35C0.19740.05960.16480.040*0.325 (11)
H35D0.17840.14710.07830.040*0.325 (11)
C36X0.2114 (4)0.3940 (14)0.1163 (9)0.0343 (19)0.325 (11)
H36C0.21340.48310.15320.041*0.325 (11)
H36D0.18670.40380.07300.041*0.325 (11)
C37X0.2865 (5)0.3718 (16)0.1291 (11)0.036 (2)0.325 (11)
H37C0.28700.46170.16540.043*0.325 (11)
H37D0.31420.36400.09510.043*0.325 (11)
C38X0.2492 (8)0.241 (2)0.0104 (13)0.037 (2)0.325 (11)
H38C0.22540.24510.03560.045*0.325 (11)
H38D0.27650.22780.02430.045*0.325 (11)
C390.24947 (9)0.7532 (3)0.49880 (11)0.0334 (4)
H39A0.24550.66960.54020.040*
H39B0.25370.83850.53850.040*
C400.28060 (8)0.6051 (2)0.38089 (18)0.0343 (5)
H40A0.30620.58950.34110.041*
H40B0.27690.51950.42060.041*
C410.20532 (8)0.6449 (3)0.38142 (19)0.0363 (5)
H41A0.20100.55980.42130.044*
H41B0.17930.65660.34220.044*
C420.21762 (8)0.8975 (2)0.37986 (18)0.0343 (5)
H42A0.19180.91220.34050.041*
H42B0.22150.98390.41870.041*
C430.29271 (8)0.8572 (3)0.37947 (19)0.0370 (6)
H43A0.29730.94320.41830.044*
H43B0.31850.84450.33980.044*
C440.24879 (10)0.7495 (3)0.26355 (11)0.0376 (4)
H44A0.22320.76250.22290.045*
H44B0.27420.73510.22300.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.049 (2)0.059 (2)0.042 (2)0.0198 (18)0.0177 (16)0.0162 (18)
O20.075 (2)0.066 (3)0.0398 (18)0.029 (2)0.0127 (17)0.0141 (19)
C70.0362 (19)0.039 (2)0.025 (2)0.0024 (18)0.0030 (17)0.001 (2)
C10.033 (2)0.037 (3)0.029 (2)0.005 (2)0.0056 (18)0.0007 (18)
C20.034 (3)0.032 (2)0.038 (3)0.006 (2)0.001 (2)0.009 (2)
C30.044 (3)0.044 (3)0.040 (3)0.005 (3)0.015 (3)0.012 (2)
C40.050 (3)0.048 (3)0.036 (2)0.010 (3)0.011 (2)0.006 (2)
C50.044 (3)0.048 (3)0.037 (3)0.007 (2)0.005 (2)0.004 (2)
C60.036 (2)0.046 (2)0.030 (2)0.005 (2)0.0034 (18)0.0019 (19)
C80.049 (4)0.041 (3)0.053 (4)0.002 (3)0.005 (3)0.004 (3)
O1X0.078 (4)0.054 (4)0.039 (3)0.027 (3)0.015 (3)0.007 (3)
O2X0.051 (3)0.064 (4)0.065 (4)0.027 (3)0.012 (3)0.012 (3)
C7X0.036 (3)0.042 (3)0.037 (3)0.002 (3)0.002 (2)0.003 (3)
C1X0.029 (3)0.036 (3)0.029 (3)0.002 (3)0.002 (3)0.006 (3)
C2X0.035 (4)0.036 (3)0.033 (3)0.005 (3)0.002 (3)0.003 (3)
C3X0.041 (3)0.028 (3)0.039 (4)0.002 (3)0.000 (3)0.001 (3)
C4X0.046 (4)0.035 (4)0.036 (3)0.006 (3)0.004 (3)0.004 (3)
C5X0.044 (4)0.039 (3)0.033 (3)0.005 (3)0.004 (3)0.001 (3)
C6X0.036 (4)0.035 (3)0.033 (3)0.002 (3)0.001 (3)0.002 (3)
C8X0.045 (6)0.038 (5)0.048 (5)0.003 (4)0.001 (4)0.002 (4)
O30.0529 (17)0.060 (2)0.0394 (17)0.0222 (15)0.0065 (14)0.0092 (16)
O40.0534 (17)0.0462 (17)0.065 (2)0.0264 (13)0.0183 (15)0.0185 (15)
C150.0299 (16)0.0275 (17)0.0411 (17)0.0005 (14)0.0016 (14)0.0021 (14)
C90.0274 (15)0.023 (2)0.0314 (18)0.0019 (16)0.0035 (14)0.0025 (15)
C100.024 (2)0.028 (2)0.036 (2)0.0008 (15)0.0024 (15)0.0031 (18)
C110.0347 (19)0.028 (2)0.040 (2)0.0021 (15)0.0023 (19)0.0061 (16)
C120.045 (2)0.033 (2)0.0387 (18)0.0012 (16)0.0047 (17)0.0069 (16)
C130.045 (2)0.038 (2)0.0344 (18)0.0017 (19)0.0027 (16)0.0032 (16)
C140.037 (2)0.0280 (16)0.038 (2)0.0015 (15)0.0002 (16)0.0035 (16)
C160.034 (3)0.0263 (19)0.055 (3)0.0054 (16)0.0007 (19)0.0038 (19)
O3X0.044 (4)0.045 (5)0.060 (5)0.013 (4)0.016 (4)0.015 (4)
O4X0.072 (5)0.075 (6)0.035 (4)0.034 (5)0.014 (4)0.014 (4)
C15X0.037 (4)0.034 (4)0.031 (4)0.008 (3)0.001 (3)0.002 (4)
C9X0.033 (3)0.032 (4)0.033 (3)0.007 (3)0.002 (3)0.003 (3)
C10X0.031 (4)0.027 (4)0.039 (4)0.000 (3)0.001 (3)0.004 (3)
C11X0.036 (4)0.034 (4)0.041 (4)0.004 (4)0.005 (4)0.006 (3)
C12X0.044 (4)0.039 (4)0.034 (3)0.002 (4)0.007 (3)0.000 (3)
C13X0.045 (4)0.036 (4)0.040 (4)0.000 (4)0.008 (4)0.001 (4)
C14X0.041 (4)0.034 (4)0.037 (4)0.004 (3)0.002 (3)0.000 (3)
C16X0.040 (7)0.038 (6)0.044 (6)0.003 (5)0.010 (5)0.007 (5)
O50.0488 (13)0.0734 (15)0.0558 (13)0.0082 (11)0.0138 (11)0.0151 (11)
O60.0337 (10)0.0845 (16)0.0862 (17)0.0117 (10)0.0044 (11)0.0247 (14)
O70.0425 (11)0.0771 (15)0.0525 (12)0.0112 (10)0.0141 (10)0.0145 (11)
O80.0380 (11)0.0984 (18)0.0793 (16)0.0120 (11)0.0014 (11)0.0268 (15)
N50.0324 (10)0.0289 (10)0.0350 (11)0.0000 (8)0.0064 (9)0.0004 (9)
N60.0331 (10)0.0296 (10)0.0319 (10)0.0005 (8)0.0074 (9)0.0012 (8)
N70.0446 (11)0.0246 (10)0.0290 (10)0.0005 (8)0.0035 (9)0.0054 (8)
N80.0428 (11)0.0259 (10)0.0316 (11)0.0021 (8)0.0005 (9)0.0073 (8)
C170.0312 (11)0.0307 (11)0.0390 (13)0.0024 (10)0.0001 (10)0.0098 (10)
C180.0420 (14)0.0381 (14)0.0417 (14)0.0040 (11)0.0007 (12)0.0091 (11)
C190.0350 (13)0.0532 (16)0.0509 (16)0.0091 (12)0.0057 (13)0.0177 (14)
C200.0350 (13)0.0589 (17)0.0519 (16)0.0014 (14)0.0008 (13)0.0169 (14)
C210.0373 (14)0.0526 (17)0.0538 (16)0.0120 (12)0.0069 (13)0.0116 (14)
C220.0435 (15)0.0370 (14)0.0490 (16)0.0033 (11)0.0018 (13)0.0056 (12)
C230.0373 (13)0.0352 (13)0.0458 (15)0.0042 (12)0.0040 (12)0.0075 (12)
C240.0547 (17)0.0542 (17)0.0525 (17)0.0008 (14)0.0051 (15)0.0054 (14)
C250.0323 (11)0.0284 (11)0.0369 (12)0.0015 (10)0.0016 (10)0.0064 (10)
C260.0403 (14)0.0316 (13)0.0390 (13)0.0034 (10)0.0024 (11)0.0063 (11)
C270.0380 (13)0.0430 (14)0.0447 (15)0.0066 (11)0.0074 (12)0.0109 (12)
C280.0366 (13)0.0486 (15)0.0481 (15)0.0057 (13)0.0058 (12)0.0137 (13)
C290.0428 (14)0.0446 (15)0.0505 (16)0.0080 (12)0.0078 (13)0.0077 (13)
C300.0406 (14)0.0353 (13)0.0422 (14)0.0009 (11)0.0017 (12)0.0033 (11)
C310.0345 (12)0.0348 (13)0.0431 (14)0.0018 (12)0.0035 (11)0.0050 (11)
C320.0510 (16)0.0495 (16)0.0510 (16)0.0005 (13)0.0036 (14)0.0049 (14)
N10.0343 (19)0.0280 (17)0.0280 (17)0.0014 (15)0.0006 (16)0.0020 (13)
N20.037 (2)0.0303 (17)0.0249 (16)0.0053 (15)0.0030 (15)0.0000 (13)
N30.051 (2)0.0240 (17)0.026 (2)0.0013 (17)0.0031 (16)0.0028 (16)
N40.060 (3)0.0195 (16)0.024 (2)0.0007 (18)0.0018 (19)0.0009 (16)
C330.035 (2)0.0304 (18)0.0205 (15)0.0034 (17)0.0007 (18)0.0000 (13)
C340.050 (3)0.0246 (17)0.030 (2)0.0044 (17)0.0042 (18)0.0006 (17)
C350.041 (3)0.026 (2)0.036 (2)0.0027 (19)0.003 (2)0.0055 (17)
C360.047 (3)0.0273 (19)0.033 (2)0.0087 (18)0.0108 (19)0.0057 (18)
C370.043 (3)0.0258 (19)0.037 (2)0.0049 (18)0.0036 (19)0.0025 (17)
C380.070 (2)0.026 (2)0.0208 (19)0.004 (2)0.002 (2)0.0049 (19)
N1X0.044 (3)0.026 (3)0.032 (3)0.004 (3)0.005 (3)0.000 (2)
N2X0.038 (3)0.030 (3)0.023 (3)0.001 (3)0.001 (3)0.003 (2)
N3X0.055 (4)0.023 (3)0.024 (3)0.001 (3)0.000 (3)0.002 (3)
N4X0.051 (3)0.027 (3)0.027 (3)0.001 (3)0.009 (3)0.004 (3)
C33X0.033 (3)0.031 (3)0.023 (3)0.004 (3)0.001 (3)0.003 (2)
C34X0.046 (4)0.031 (3)0.029 (4)0.007 (3)0.009 (3)0.003 (3)
C35X0.041 (4)0.027 (3)0.032 (3)0.000 (3)0.003 (3)0.001 (3)
C36X0.051 (4)0.021 (3)0.031 (4)0.005 (3)0.010 (3)0.002 (3)
C37X0.046 (4)0.030 (3)0.031 (3)0.004 (3)0.005 (3)0.007 (3)
C38X0.065 (4)0.025 (4)0.022 (4)0.002 (4)0.001 (3)0.007 (3)
C390.0488 (10)0.0284 (8)0.0231 (7)0.0009 (7)0.0005 (13)0.0013 (11)
C400.0393 (13)0.0270 (12)0.0368 (13)0.0089 (10)0.0005 (11)0.0004 (10)
C410.0350 (13)0.0298 (12)0.0440 (14)0.0088 (10)0.0007 (11)0.0033 (11)
C420.0408 (13)0.0230 (11)0.0390 (13)0.0076 (10)0.0004 (11)0.0006 (10)
C430.0359 (13)0.0316 (12)0.0435 (14)0.0092 (10)0.0032 (11)0.0032 (11)
C440.0540 (11)0.0373 (9)0.0217 (7)0.0045 (8)0.0002 (13)0.0007 (12)
Geometric parameters (Å, º) top
O1—C71.312 (6)C17—C181.395 (4)
O1—H1O10.83 (2)C17—C221.415 (4)
O2—C71.208 (6)C17—C231.487 (3)
C7—C11.486 (7)C18—C191.402 (4)
C1—C61.393 (7)C18—C241.494 (4)
C1—C21.415 (8)C19—C201.372 (4)
C2—C31.392 (8)C19—H19A0.9500
C2—C81.511 (8)C20—C211.389 (5)
C3—C41.373 (8)C20—H20A0.9500
C3—H3A0.9500C21—C221.365 (4)
C4—C51.379 (7)C21—H21A0.9500
C4—H4A0.9500C22—H22A0.9500
C5—C61.375 (7)C24—H24A0.9800
C5—H5A0.9500C24—H24B0.9800
C6—H6A0.9500C24—H24C0.9800
C8—H8A0.9800C25—C261.395 (4)
C8—H8B0.9800C25—C301.410 (4)
C8—H8C0.9800C25—C311.492 (3)
O1X—C7X1.308 (8)C26—C271.401 (4)
O1X—H2O10.8400C26—C321.488 (4)
O2X—C7X1.214 (8)C27—C281.361 (4)
C7X—C1X1.495 (10)C27—H27A0.9500
C1X—C6X1.394 (10)C28—C291.389 (4)
C1X—C2X1.403 (11)C28—H28A0.9500
C2X—C3X1.388 (12)C29—C301.376 (4)
C2X—C8X1.512 (11)C29—H29A0.9500
C3X—C4X1.379 (10)C30—H30A0.9500
C3X—H3XA0.9500C32—H32A0.9800
C4X—C5X1.386 (9)C32—H32B0.9800
C4X—H4XA0.9500C32—H32C0.9800
C5X—C6X1.385 (10)N1—C361.476 (6)
C5X—H5XA0.9500N1—C351.483 (6)
C6X—H6XA0.9500N1—C331.489 (5)
C8X—H8XA0.9800N2—C331.472 (5)
C8X—H8XB0.9800N2—C341.479 (6)
C8X—H8XC0.9800N2—C371.482 (6)
O3—C151.309 (5)N3—C341.462 (7)
O3—H1O30.84 (2)N3—C351.466 (7)
O4—C151.205 (4)N3—C381.472 (7)
C15—C91.495 (5)N4—C371.454 (7)
C9—C141.399 (5)N4—C361.462 (7)
C9—C101.408 (5)N4—C381.476 (7)
C10—C111.408 (6)C33—H33A0.9900
C10—C161.499 (5)C33—H33B0.9900
C11—C121.375 (6)C34—H34A0.9900
C11—H11A0.9500C34—H34B0.9900
C12—C131.376 (5)C35—H35A0.9900
C12—H12A0.9500C35—H35B0.9900
C13—C141.384 (6)C36—H36A0.9900
C13—H13A0.9500C36—H36B0.9900
C14—H14A0.9500C37—H37A0.9900
C16—H16A0.9800C37—H37B0.9900
C16—H16B0.9800C38—H38A0.9900
C16—H16C0.9800C38—H38B0.9900
O3X—C15X1.316 (11)N1X—C36X1.460 (11)
O3X—H2O30.8400N1X—C35X1.477 (12)
O4X—C15X1.211 (12)N1X—C33X1.483 (10)
C15X—C9X1.519 (13)N2X—C33X1.458 (9)
C9X—C14X1.391 (13)N2X—C37X1.499 (12)
C9X—C10X1.397 (13)N2X—C34X1.501 (11)
C10X—C11X1.407 (14)N3X—C35X1.456 (13)
C10X—C16X1.511 (14)N3X—C38X1.467 (13)
C11X—C12X1.363 (14)N3X—C34X1.470 (13)
C11X—H11B0.9500N4X—C37X1.458 (13)
C12X—C13X1.378 (13)N4X—C36X1.461 (13)
C12X—H12B0.9500N4X—C38X1.470 (13)
C13X—C14X1.374 (13)C33X—H33C0.9900
C13X—H13B0.9500C33X—H33D0.9900
C14X—H14B0.9500C34X—H34C0.9900
C16X—H16D0.9800C34X—H34D0.9900
C16X—H16E0.9800C35X—H35C0.9900
C16X—H16F0.9800C35X—H35D0.9900
O5—C231.308 (4)C36X—H36C0.9900
O5—H1O50.865 (19)C36X—H36D0.9900
O6—C231.214 (3)C37X—H37C0.9900
O7—C311.301 (3)C37X—H37D0.9900
O7—H1O70.882 (18)C38X—H38C0.9900
O8—C311.212 (3)C38X—H38D0.9900
N5—C391.472 (3)C39—H39A0.9900
N5—C411.479 (3)C39—H39B0.9900
N5—C421.480 (3)C40—H40A0.9900
N6—C391.472 (3)C40—H40B0.9900
N6—C401.479 (3)C41—H41A0.9900
N6—C431.479 (3)C41—H41B0.9900
N7—C411.454 (3)C42—H42A0.9900
N7—C401.460 (3)C42—H42B0.9900
N7—C441.469 (3)C43—H43A0.9900
N8—C431.454 (3)C43—H43B0.9900
N8—C421.455 (3)C44—H44A0.9900
N8—C441.477 (3)C44—H44B0.9900
C7—O1—H1O1107 (4)C25—C26—C27117.9 (2)
O2—C7—O1122.4 (5)C25—C26—C32124.1 (2)
O2—C7—C1124.5 (5)C27—C26—C32117.9 (3)
O1—C7—C1113.1 (5)C28—C27—C26122.0 (3)
C6—C1—C2118.7 (6)C28—C27—H27A119.0
C6—C1—C7119.0 (5)C26—C27—H27A119.0
C2—C1—C7122.3 (6)C27—C28—C29120.4 (2)
C3—C2—C1118.2 (7)C27—C28—H28A119.8
C3—C2—C8119.2 (6)C29—C28—H28A119.8
C1—C2—C8122.6 (6)C30—C29—C28119.1 (3)
C4—C3—C2121.8 (7)C30—C29—H29A120.5
C4—C3—H3A119.1C28—C29—H29A120.5
C2—C3—H3A119.1C29—C30—C25121.0 (3)
C3—C4—C5120.1 (6)C29—C30—H30A119.5
C3—C4—H4A119.9C25—C30—H30A119.5
C5—C4—H4A119.9O8—C31—O7121.9 (3)
C6—C5—C4119.4 (6)O8—C31—C25123.8 (3)
C6—C5—H5A120.3O7—C31—C25114.3 (2)
C4—C5—H5A120.3C26—C32—H32A109.5
C5—C6—C1121.8 (6)C26—C32—H32B109.5
C5—C6—H6A119.1H32A—C32—H32B109.5
C1—C6—H6A119.1C26—C32—H32C109.5
C2—C8—H8A109.5H32A—C32—H32C109.5
C2—C8—H8B109.5H32B—C32—H32C109.5
H8A—C8—H8B109.5C36—N1—C35109.6 (4)
C2—C8—H8C109.5C36—N1—C33107.4 (3)
H8A—C8—H8C109.5C35—N1—C33108.1 (3)
H8B—C8—H8C109.5C33—N2—C34108.5 (3)
C7X—O1X—H2O1109.5C33—N2—C37107.8 (3)
O2X—C7X—O1X123.0 (7)C34—N2—C37107.5 (4)
O2X—C7X—C1X120.4 (8)C34—N3—C35108.0 (5)
O1X—C7X—C1X116.4 (7)C34—N3—C38109.1 (6)
C6X—C1X—C2X120.7 (9)C35—N3—C38109.1 (7)
C6X—C1X—C7X115.6 (8)C37—N4—C36109.3 (5)
C2X—C1X—C7X123.6 (9)C37—N4—C38107.8 (7)
C3X—C2X—C1X116.7 (10)C36—N4—C38107.1 (6)
C3X—C2X—C8X116.2 (9)N2—C33—N1111.4 (3)
C1X—C2X—C8X127.1 (10)N2—C33—H33A109.3
C4X—C3X—C2X122.7 (11)N1—C33—H33A109.3
C4X—C3X—H3XA118.7N2—C33—H33B109.3
C2X—C3X—H3XA118.7N1—C33—H33B109.3
C3X—C4X—C5X120.3 (10)H33A—C33—H33B108.0
C3X—C4X—H4XA119.9N3—C34—N2111.8 (5)
C5X—C4X—H4XA119.9N3—C34—H34A109.3
C6X—C5X—C4X118.3 (8)N2—C34—H34A109.3
C6X—C5X—H5XA120.8N3—C34—H34B109.3
C4X—C5X—H5XA120.8N2—C34—H34B109.3
C5X—C6X—C1X121.2 (8)H34A—C34—H34B107.9
C5X—C6X—H6XA119.4N3—C35—N1110.6 (5)
C1X—C6X—H6XA119.4N3—C35—H35A109.5
C2X—C8X—H8XA109.5N1—C35—H35A109.5
C2X—C8X—H8XB109.5N3—C35—H35B109.5
H8XA—C8X—H8XB109.5N1—C35—H35B109.5
C2X—C8X—H8XC109.5H35A—C35—H35B108.1
H8XA—C8X—H8XC109.5N4—C36—N1112.1 (5)
H8XB—C8X—H8XC109.5N4—C36—H36A109.2
C15—O3—H1O3108 (4)N1—C36—H36A109.2
O4—C15—O3122.5 (4)N4—C36—H36B109.2
O4—C15—C9121.0 (4)N1—C36—H36B109.2
O3—C15—C9116.5 (3)H36A—C36—H36B107.9
C14—C9—C10119.8 (4)N4—C37—N2112.7 (5)
C14—C9—C15115.7 (3)N4—C37—H37A109.0
C10—C9—C15124.5 (4)N2—C37—H37A109.0
C9—C10—C11117.6 (4)N4—C37—H37B109.0
C9—C10—C16125.7 (4)N2—C37—H37B109.0
C11—C10—C16116.7 (4)H37A—C37—H37B107.8
C12—C11—C10121.6 (5)N3—C38—N4112.0 (6)
C12—C11—H11A119.2N3—C38—H38A109.2
C10—C11—H11A119.2N4—C38—H38A109.2
C11—C12—C13120.7 (4)N3—C38—H38B109.2
C11—C12—H12A119.7N4—C38—H38B109.2
C13—C12—H12A119.7H38A—C38—H38B107.9
C12—C13—C14119.3 (4)C36X—N1X—C35X108.1 (9)
C12—C13—H13A120.3C36X—N1X—C33X108.1 (7)
C14—C13—H13A120.3C35X—N1X—C33X106.6 (7)
C13—C14—C9121.1 (4)C33X—N2X—C37X108.2 (8)
C13—C14—H14A119.4C33X—N2X—C34X107.5 (7)
C9—C14—H14A119.4C37X—N2X—C34X107.8 (9)
C10—C16—H16A109.5C35X—N3X—C38X107.6 (14)
C10—C16—H16B109.5C35X—N3X—C34X110.4 (11)
H16A—C16—H16B109.5C38X—N3X—C34X106.6 (13)
C10—C16—H16C109.5C37X—N4X—C36X106.9 (12)
H16A—C16—H16C109.5C37X—N4X—C38X109.9 (15)
H16B—C16—H16C109.5C36X—N4X—C38X109.9 (14)
C15X—O3X—H2O3109.5N2X—C33X—N1X113.0 (7)
O4X—C15X—O3X123.5 (10)N2X—C33X—H33C109.0
O4X—C15X—C9X122.5 (9)N1X—C33X—H33C109.0
O3X—C15X—C9X114.0 (10)N2X—C33X—H33D109.0
C14X—C9X—C10X120.6 (11)N1X—C33X—H33D109.0
C14X—C9X—C15X116.5 (11)H33C—C33X—H33D107.8
C10X—C9X—C15X122.9 (11)N3X—C34X—N2X111.5 (10)
C9X—C10X—C11X115.3 (13)N3X—C34X—H34C109.3
C9X—C10X—C16X123.3 (12)N2X—C34X—H34C109.3
C11X—C10X—C16X121.4 (12)N3X—C34X—H34D109.3
C12X—C11X—C10X122.9 (14)N2X—C34X—H34D109.3
C12X—C11X—H11B118.5H34C—C34X—H34D108.0
C10X—C11X—H11B118.5N3X—C35X—N1X113.0 (10)
C11X—C12X—C13X121.3 (12)N3X—C35X—H35C109.0
C11X—C12X—H12B119.3N1X—C35X—H35C109.0
C13X—C12X—H12B119.3N3X—C35X—H35D109.0
C14X—C13X—C12X117.0 (12)N1X—C35X—H35D109.0
C14X—C13X—H13B121.5H35C—C35X—H35D107.8
C12X—C13X—H13B121.5N1X—C36X—N4X112.2 (10)
C13X—C14X—C9X122.6 (12)N1X—C36X—H36C109.2
C13X—C14X—H14B118.7N4X—C36X—H36C109.2
C9X—C14X—H14B118.7N1X—C36X—H36D109.2
C10X—C16X—H16D109.5N4X—C36X—H36D109.2
C10X—C16X—H16E109.5H36C—C36X—H36D107.9
H16D—C16X—H16E109.5N4X—C37X—N2X110.7 (11)
C10X—C16X—H16F109.5N4X—C37X—H37C109.5
H16D—C16X—H16F109.5N2X—C37X—H37C109.5
H16E—C16X—H16F109.5N4X—C37X—H37D109.5
C23—O5—H1O5106 (4)N2X—C37X—H37D109.5
C31—O7—H1O7113 (3)H37C—C37X—H37D108.1
C39—N5—C41108.4 (2)N3X—C38X—N4X111.9 (13)
C39—N5—C42108.09 (19)N3X—C38X—H38C109.2
C41—N5—C42108.11 (18)N4X—C38X—H38C109.2
C39—N6—C40108.31 (19)N3X—C38X—H38D109.2
C39—N6—C43107.80 (19)N4X—C38X—H38D109.2
C40—N6—C43107.81 (19)H38C—C38X—H38D107.9
C41—N7—C40108.43 (19)N5—C39—N6111.33 (12)
C41—N7—C44108.7 (2)N5—C39—H39A109.4
C40—N7—C44108.3 (2)N6—C39—H39A109.4
C43—N8—C42108.3 (2)N5—C39—H39B109.4
C43—N8—C44108.11 (19)N6—C39—H39B109.4
C42—N8—C44108.3 (2)H39A—C39—H39B108.0
C18—C17—C22119.1 (2)N7—C40—N6112.04 (18)
C18—C17—C23123.0 (2)N7—C40—H40A109.2
C22—C17—C23117.9 (2)N6—C40—H40A109.2
C17—C18—C19117.7 (3)N7—C40—H40B109.2
C17—C18—C24124.1 (2)N6—C40—H40B109.2
C19—C18—C24118.2 (3)H40A—C40—H40B107.9
C20—C19—C18122.1 (3)N7—C41—N5111.81 (18)
C20—C19—H19A118.9N7—C41—H41A109.3
C18—C19—H19A118.9N5—C41—H41A109.3
C19—C20—C21120.4 (3)N7—C41—H41B109.3
C19—C20—H20A119.8N5—C41—H41B109.3
C21—C20—H20A119.8H41A—C41—H41B107.9
C22—C21—C20118.6 (3)N8—C42—N5112.04 (17)
C22—C21—H21A120.7N8—C42—H42A109.2
C20—C21—H21A120.7N5—C42—H42A109.2
C21—C22—C17122.1 (3)N8—C42—H42B109.2
C21—C22—H22A118.9N5—C42—H42B109.2
C17—C22—H22A118.9H42A—C42—H42B107.9
O6—C23—O5122.1 (3)N8—C43—N6112.50 (19)
O6—C23—C17124.0 (3)N8—C43—H43A109.1
O5—C23—C17113.9 (2)N6—C43—H43A109.1
C18—C24—H24A109.5N8—C43—H43B109.1
C18—C24—H24B109.5N6—C43—H43B109.1
H24A—C24—H24B109.5H43A—C43—H43B107.8
C18—C24—H24C109.5N7—C44—N8111.80 (12)
H24A—C24—H24C109.5N7—C44—H44A109.3
H24B—C24—H24C109.5N8—C44—H44A109.3
C26—C25—C30119.6 (2)N7—C44—H44B109.3
C26—C25—C31123.3 (2)N8—C44—H44B109.3
C30—C25—C31117.1 (2)H44A—C44—H44B107.9
O2—C7—C1—C6170.7 (7)C26—C27—C28—C290.0 (4)
O1—C7—C1—C611.7 (10)C27—C28—C29—C300.4 (4)
O2—C7—C1—C210.1 (15)C28—C29—C30—C250.4 (4)
O1—C7—C1—C2167.5 (11)C26—C25—C30—C290.0 (4)
C6—C1—C2—C31 (2)C31—C25—C30—C29177.9 (2)
C7—C1—C2—C3178.2 (11)C26—C25—C31—O89.6 (4)
C6—C1—C2—C8179.9 (11)C30—C25—C31—O8172.6 (3)
C7—C1—C2—C81 (2)C26—C25—C31—O7169.3 (2)
C1—C2—C3—C41 (2)C30—C25—C31—O78.5 (3)
C8—C2—C3—C4179.7 (11)C34—N2—C33—N157.1 (4)
C2—C3—C4—C50.4 (16)C37—N2—C33—N159.0 (5)
C3—C4—C5—C61.3 (10)C36—N1—C33—N259.9 (4)
C4—C5—C6—C11.1 (10)C35—N1—C33—N258.3 (5)
C2—C1—C6—C50.1 (14)C35—N3—C34—N260.6 (7)
C7—C1—C6—C5179.2 (7)C38—N3—C34—N257.9 (7)
O2X—C7X—C1X—C6X20.9 (16)C33—N2—C34—N358.6 (5)
O1X—C7X—C1X—C6X162.7 (10)C37—N2—C34—N357.8 (5)
O2X—C7X—C1X—C2X160.7 (18)C34—N3—C35—N161.2 (7)
O1X—C7X—C1X—C2X16 (2)C38—N3—C35—N157.3 (7)
C6X—C1X—C2X—C3X3 (3)C36—N1—C35—N356.7 (6)
C7X—C1X—C2X—C3X178.2 (17)C33—N1—C35—N360.1 (6)
C6X—C1X—C2X—C8X176.5 (18)C37—N4—C36—N157.9 (7)
C7X—C1X—C2X—C8X2 (4)C38—N4—C36—N158.7 (7)
C1X—C2X—C3X—C4X2 (3)C35—N1—C36—N458.4 (5)
C8X—C2X—C3X—C4X177.8 (17)C33—N1—C36—N458.9 (5)
C2X—C3X—C4X—C5X0 (3)C36—N4—C37—N257.0 (7)
C3X—C4X—C5X—C6X0.9 (16)C38—N4—C37—N259.1 (7)
C4X—C5X—C6X—C1X0.5 (15)C33—N2—C37—N457.6 (6)
C2X—C1X—C6X—C5X3 (2)C34—N2—C37—N459.2 (6)
C7X—C1X—C6X—C5X178.8 (10)C34—N3—C38—N457.8 (9)
O4—C15—C9—C1418.4 (7)C35—N3—C38—N460.0 (10)
O3—C15—C9—C14161.2 (4)C37—N4—C38—N357.9 (9)
O4—C15—C9—C10158.4 (8)C36—N4—C38—N359.6 (9)
O3—C15—C9—C1022.0 (10)C37X—N2X—C33X—N1X55.7 (10)
C14—C9—C10—C110.3 (14)C34X—N2X—C33X—N1X60.4 (10)
C15—C9—C10—C11177.0 (7)C36X—N1X—C33X—N2X55.6 (10)
C14—C9—C10—C16178.3 (8)C35X—N1X—C33X—N2X60.4 (10)
C15—C9—C10—C165.0 (15)C35X—N3X—C34X—N2X55.4 (15)
C9—C10—C11—C120.5 (15)C38X—N3X—C34X—N2X61.2 (14)
C16—C10—C11—C12178.7 (7)C33X—N2X—C34X—N3X56.6 (11)
C10—C11—C12—C130.3 (11)C37X—N2X—C34X—N3X59.9 (12)
C11—C12—C13—C140.1 (7)C38X—N3X—C35X—N1X59.2 (15)
C12—C13—C14—C90.3 (7)C34X—N3X—C35X—N1X56.8 (15)
C10—C9—C14—C130.1 (10)C36X—N1X—C35X—N3X58.6 (13)
C15—C9—C14—C13176.9 (4)C33X—N1X—C35X—N3X57.3 (13)
O4X—C15X—C9X—C14X166.7 (15)C35X—N1X—C36X—N4X56.2 (12)
O3X—C15X—C9X—C14X13 (2)C33X—N1X—C36X—N4X58.8 (12)
O4X—C15X—C9X—C10X14 (3)C37X—N4X—C36X—N1X62.7 (15)
O3X—C15X—C9X—C10X166 (3)C38X—N4X—C36X—N1X56.5 (15)
C14X—C9X—C10X—C11X5 (5)C36X—N4X—C37X—N2X61.8 (15)
C15X—C9X—C10X—C11X174 (2)C38X—N4X—C37X—N2X57.4 (16)
C14X—C9X—C10X—C16X179 (3)C33X—N2X—C37X—N4X59.1 (13)
C15X—C9X—C10X—C16X2 (5)C34X—N2X—C37X—N4X56.8 (13)
C9X—C10X—C11X—C12X5 (5)C35X—N3X—C38X—N4X57.7 (19)
C16X—C10X—C11X—C12X178 (2)C34X—N3X—C38X—N4X60.7 (19)
C10X—C11X—C12X—C13X3 (4)C37X—N4X—C38X—N3X60.2 (19)
C11X—C12X—C13X—C14X0 (2)C36X—N4X—C38X—N3X57.2 (19)
C12X—C13X—C14X—C9X0 (2)C41—N5—C39—N658.2 (3)
C10X—C9X—C14X—C13X3 (3)C42—N5—C39—N658.8 (3)
C15X—C9X—C14X—C13X176.5 (14)C40—N6—C39—N557.9 (3)
C22—C17—C18—C190.2 (4)C43—N6—C39—N558.5 (3)
C23—C17—C18—C19176.9 (2)C41—N7—C40—N658.9 (2)
C22—C17—C18—C24179.5 (2)C44—N7—C40—N658.9 (3)
C23—C17—C18—C242.8 (4)C39—N6—C40—N758.4 (2)
C17—C18—C19—C200.1 (4)C43—N6—C40—N758.0 (3)
C24—C18—C19—C20179.7 (3)C40—N7—C41—N559.0 (3)
C18—C19—C20—C210.1 (4)C44—N7—C41—N558.5 (2)
C19—C20—C21—C220.3 (4)C39—N5—C41—N758.9 (2)
C20—C21—C22—C170.5 (4)C42—N5—C41—N758.1 (3)
C18—C17—C22—C210.5 (4)C43—N8—C42—N558.5 (2)
C23—C17—C22—C21177.4 (2)C44—N8—C42—N558.4 (2)
C18—C17—C23—O65.6 (4)C39—N5—C42—N858.9 (2)
C22—C17—C23—O6177.7 (3)C41—N5—C42—N858.3 (2)
C18—C17—C23—O5173.7 (2)C42—N8—C43—N658.7 (3)
C22—C17—C23—O53.1 (3)C44—N8—C43—N658.4 (3)
C30—C25—C26—C270.4 (4)C39—N6—C43—N858.7 (3)
C31—C25—C26—C27177.4 (2)C40—N6—C43—N858.0 (3)
C30—C25—C26—C32179.0 (2)C41—N7—C44—N858.6 (3)
C31—C25—C26—C321.3 (4)C40—N7—C44—N859.0 (3)
C25—C26—C27—C280.4 (4)C43—N8—C44—N758.7 (3)
C32—C26—C27—C28179.2 (2)C42—N8—C44—N758.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N10.83 (3)1.81 (4)2.623 (6)167 (4)
O3—H1O3···N20.84 (4)1.84 (5)2.677 (6)177 (6)
O5—H1O5···N50.86 (4)1.83 (4)2.676 (3)165 (5)
O7—H1O7···N60.88 (3)1.79 (3)2.666 (3)172 (4)
C6—H6A···O10.952.342.686 (7)101
C16—H16A···O30.982.422.817 (6)104
C22—H22A···O50.952.322.680 (4)102
C30—H30A···O70.952.332.677 (3)101
C33—H33A···O40.992.583.142 (6)116
C33—H33B···N8i0.992.603.535 (5)157
C36—H36B···N70.992.603.550 (6)162
C38—H38B···O4ii0.992.413.366 (12)162
C40—H40B···N3iii0.992.593.510 (8)155
C44—H44A···O6iv0.992.393.373 (4)172
C44—H44B···O8iv0.992.393.371 (4)172
Symmetry codes: (i) x, y1, z; (ii) x, y+1/2, z1/2; (iii) x, y+1/2, z+1/2; (iv) x, y+3/2, z1/2.
(164K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top
Crystal data top
C6H12N4·2C8H8O2F(000) = 1760
Mr = 412.48Dx = 1.315 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 31.0071 (16) ÅCell parameters from 9956 reflections
b = 9.3634 (5) Åθ = 2.2–27.2°
c = 14.3544 (7) ŵ = 0.09 mm1
β = 90.0656 (10)°T = 164 K
V = 4167.5 (4) Å3Block, colourless
Z = 80.43 × 0.17 × 0.15 mm
Data collection top
Bruker APEX DUO CCD area detector
diffractometer
10052 independent reflections
Radiation source: fine-focus sealed tube7429 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 28.0°, θmin = 0.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 4040
Tmin = 0.918, Tmax = 0.963k = 1212
66182 measured reflectionsl = 1818
Refinement top
Refinement on F21216 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.146 w = 1/[σ2(Fo2) + (0.0609P)2 + 1.6705P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.003
10052 reflectionsΔρmax = 0.43 e Å3
837 parametersΔρmin = 0.23 e Å3
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
xyzUiso*/UeqOcc. (<1)
O10.16467 (14)0.2381 (6)0.3349 (3)0.0497 (12)0.553 (7)
H1O10.1798 (16)0.247 (6)0.288 (3)0.067 (18)*0.553 (7)
O20.12823 (16)0.4183 (7)0.2737 (3)0.0610 (14)0.553 (7)
C70.13364 (17)0.3336 (7)0.3360 (4)0.0331 (11)0.553 (7)
C10.1074 (4)0.3295 (9)0.4231 (6)0.0331 (13)0.553 (7)
C20.0787 (5)0.4399 (13)0.4470 (9)0.0346 (15)0.553 (7)
C30.0569 (4)0.4286 (12)0.5318 (7)0.0429 (17)0.553 (7)
H3A0.03760.50230.54970.052*0.553 (7)
C40.0627 (3)0.3140 (9)0.5899 (6)0.0460 (16)0.553 (7)
H4A0.04740.30980.64710.055*0.553 (7)
C50.0904 (2)0.2055 (8)0.5665 (5)0.0440 (14)0.553 (7)
H5A0.09410.12550.60650.053*0.553 (7)
C60.1128 (2)0.2149 (8)0.4838 (5)0.0372 (13)0.553 (7)
H6A0.13240.14100.46780.045*0.553 (7)
C80.0706 (3)0.5676 (10)0.3848 (7)0.048 (2)0.553 (7)
H8A0.09710.62420.37960.071*0.553 (7)
H8B0.04770.62660.41170.071*0.553 (7)
H8C0.06180.53470.32280.071*0.553 (7)
O1X0.1344 (2)0.3327 (8)0.2840 (5)0.0587 (17)0.447 (7)
H2O10.15330.30340.24670.088*0.447 (7)
O2X0.16546 (17)0.1734 (7)0.3771 (5)0.0613 (18)0.447 (7)
C7X0.1376 (2)0.2626 (8)0.3624 (5)0.0394 (14)0.447 (7)
C1X0.1063 (5)0.3015 (12)0.4369 (8)0.0319 (16)0.447 (7)
C2X0.0812 (7)0.4251 (17)0.4374 (11)0.0351 (18)0.447 (7)
C3X0.0541 (5)0.4480 (14)0.5134 (8)0.0384 (18)0.447 (7)
H3XA0.03780.53380.51620.046*0.447 (7)
C4X0.0502 (3)0.3499 (10)0.5848 (7)0.0386 (17)0.447 (7)
H4XA0.03160.36870.63580.046*0.447 (7)
C5X0.0736 (3)0.2243 (10)0.5816 (6)0.0386 (16)0.447 (7)
H5XA0.07060.15500.62950.046*0.447 (7)
C6X0.1013 (3)0.2004 (9)0.5079 (7)0.0355 (16)0.447 (7)
H6XA0.11720.11390.50550.043*0.447 (7)
C8X0.0824 (4)0.5415 (12)0.3644 (8)0.047 (2)0.447 (7)
H8XA0.11210.57590.35730.070*0.447 (7)
H8XB0.06380.62070.38390.070*0.447 (7)
H8XC0.07210.50340.30480.070*0.447 (7)
O30.36527 (12)0.1727 (5)0.2834 (3)0.0500 (10)0.701 (6)
H1O30.3422 (13)0.188 (7)0.255 (5)0.14 (3)*0.701 (6)
O40.33484 (11)0.3284 (4)0.3778 (3)0.0562 (10)0.701 (6)
C150.36205 (13)0.2401 (5)0.3631 (3)0.0327 (9)0.701 (6)
C90.3946 (2)0.2022 (5)0.4361 (4)0.0274 (10)0.701 (6)
C100.4180 (4)0.0736 (9)0.4378 (6)0.0298 (11)0.701 (6)
C110.4457 (3)0.0504 (7)0.5138 (4)0.0343 (11)0.701 (6)
H11A0.46190.03560.51650.041*0.701 (6)
C120.45004 (18)0.1491 (5)0.5845 (4)0.0376 (11)0.701 (6)
H12A0.46900.13040.63500.045*0.701 (6)
C130.42687 (18)0.2753 (6)0.5821 (4)0.0399 (11)0.701 (6)
H13A0.42980.34340.63080.048*0.701 (6)
C140.39952 (17)0.3011 (5)0.5084 (4)0.0341 (10)0.701 (6)
H14A0.38360.38790.50670.041*0.701 (6)
C160.41716 (19)0.0404 (6)0.3644 (4)0.0385 (12)0.701 (6)
H16A0.38750.05410.34260.058*0.701 (6)
H16B0.42800.13010.39070.058*0.701 (6)
H16C0.43540.01160.31200.058*0.701 (6)
O3X0.3348 (2)0.2633 (10)0.3362 (7)0.051 (2)0.299 (6)
H2O30.32080.25700.28630.076*0.299 (6)
O4X0.3721 (3)0.0864 (11)0.2729 (5)0.062 (2)0.299 (6)
C15X0.3656 (3)0.1681 (11)0.3365 (7)0.0334 (18)0.299 (6)
C9X0.3935 (6)0.1699 (15)0.4238 (10)0.0324 (18)0.299 (6)
C10X0.4215 (10)0.059 (2)0.4473 (16)0.032 (2)0.299 (6)
C11X0.4429 (7)0.0728 (18)0.5332 (11)0.038 (2)0.299 (6)
H11B0.46180.00140.55260.045*0.299 (6)
C12X0.4378 (4)0.1888 (15)0.5901 (9)0.039 (2)0.299 (6)
H12B0.45360.19440.64680.047*0.299 (6)
C13X0.4102 (4)0.2966 (13)0.5664 (10)0.042 (2)0.299 (6)
H13B0.40620.37630.60640.050*0.299 (6)
C14X0.3884 (4)0.2868 (14)0.4827 (9)0.0373 (19)0.299 (6)
H14B0.36950.36180.46490.045*0.299 (6)
C16X0.4293 (5)0.0695 (13)0.3850 (10)0.044 (3)0.299 (6)
H16D0.44890.13620.41630.065*0.299 (6)
H16E0.44230.03770.32630.065*0.299 (6)
H16F0.40180.11730.37200.065*0.299 (6)
O50.13515 (8)0.8180 (3)0.52528 (17)0.0600 (6)
H1O50.1590 (16)0.783 (9)0.510 (7)0.30 (5)*
O60.15757 (7)0.6868 (3)0.6437 (2)0.0694 (7)
O70.36445 (7)0.6891 (3)0.52275 (16)0.0580 (6)
H1O70.3376 (6)0.701 (3)0.502 (2)0.051 (8)*
O80.34157 (7)0.8063 (3)0.6456 (2)0.0721 (8)
N50.21074 (6)0.7721 (2)0.44119 (15)0.0322 (5)
N60.28816 (6)0.7308 (2)0.44074 (15)0.0318 (5)
N70.24280 (7)0.6218 (2)0.32166 (15)0.0328 (5)
N80.25541 (7)0.8792 (2)0.32050 (15)0.0335 (5)
C170.08298 (7)0.7497 (3)0.63491 (19)0.0335 (6)
C180.06833 (9)0.6696 (3)0.7104 (2)0.0405 (6)
C190.02424 (9)0.6746 (3)0.7315 (2)0.0466 (7)
H19A0.01370.62080.78270.056*
C200.00413 (9)0.7551 (4)0.6801 (2)0.0484 (7)
H20A0.03380.75600.69620.058*
C210.01014 (10)0.8352 (3)0.6048 (2)0.0484 (7)
H21A0.00940.89140.56930.058*
C220.05305 (9)0.8312 (3)0.5831 (2)0.0439 (7)
H22A0.06310.88510.53130.053*
C230.12862 (9)0.7482 (3)0.6029 (2)0.0399 (6)
C240.09664 (11)0.5788 (3)0.7701 (2)0.0539 (8)
H24A0.07910.53010.81710.081*
H24B0.11820.63900.80110.081*
H24C0.11130.50770.73130.081*
C250.41644 (7)0.7495 (3)0.63496 (19)0.0330 (5)
C260.43100 (9)0.8284 (3)0.7112 (2)0.0378 (6)
C270.47530 (9)0.8233 (3)0.7322 (2)0.0420 (7)
H27A0.48590.87740.78330.050*
C280.50335 (9)0.7435 (3)0.6815 (2)0.0451 (7)
H28A0.53300.74210.69780.054*
C290.48888 (10)0.6636 (3)0.6058 (2)0.0469 (7)
H29A0.50850.60740.57060.056*
C300.44592 (9)0.6673 (3)0.5830 (2)0.0394 (6)
H30A0.43590.61350.53120.047*
C310.37072 (8)0.7510 (3)0.6027 (2)0.0376 (6)
C320.40309 (10)0.9208 (3)0.7701 (2)0.0511 (8)
H32A0.42110.97460.81400.077*
H32B0.38270.86120.80470.077*
H32C0.38720.98760.73030.077*
N10.2177 (2)0.2512 (6)0.1937 (4)0.0300 (10)0.633 (13)
N20.2960 (2)0.2281 (6)0.1778 (4)0.0311 (10)0.633 (13)
N30.2483 (3)0.1200 (11)0.0633 (6)0.0347 (12)0.633 (13)
N40.2556 (3)0.3799 (10)0.0705 (6)0.0351 (12)0.633 (13)
C330.2596 (3)0.2375 (5)0.2431 (4)0.0300 (10)0.633 (13)
H33A0.26370.32110.28430.036*0.633 (13)
H33B0.25910.15090.28260.036*0.633 (13)
C340.2887 (2)0.1052 (7)0.1150 (5)0.0347 (12)0.633 (13)
H34A0.31300.09810.07050.042*0.633 (13)
H34B0.28800.01610.15210.042*0.633 (13)
C350.2128 (3)0.1257 (8)0.1311 (6)0.0360 (14)0.633 (13)
H35A0.21270.03700.16870.043*0.633 (13)
H35B0.18500.13200.09770.043*0.633 (13)
C360.2200 (2)0.3822 (8)0.1366 (5)0.0364 (13)0.633 (13)
H36A0.19260.39370.10210.044*0.633 (13)
H36B0.22340.46580.17830.044*0.633 (13)
C370.2958 (2)0.3590 (8)0.1200 (6)0.0353 (14)0.633 (13)
H37A0.30110.44270.16050.042*0.633 (13)
H37B0.31960.35360.07440.042*0.633 (13)
C380.2493 (5)0.2546 (11)0.0099 (7)0.0402 (13)0.633 (13)
H38A0.27310.25030.03610.048*0.633 (13)
H38B0.22190.26540.02480.048*0.633 (13)
N1X0.2038 (4)0.2737 (10)0.1784 (7)0.0342 (15)0.367 (13)
N2X0.2823 (4)0.2485 (11)0.1938 (7)0.0321 (15)0.367 (13)
N3X0.2428 (5)0.1170 (18)0.0716 (11)0.0345 (17)0.367 (13)
N4X0.2509 (5)0.3760 (19)0.0625 (11)0.0356 (17)0.367 (13)
C33X0.2410 (4)0.2628 (10)0.2435 (6)0.0290 (15)0.367 (13)
H33C0.24200.34910.28330.035*0.367 (13)
H33D0.23700.17890.28460.035*0.367 (13)
C34X0.2795 (4)0.1157 (13)0.1361 (9)0.0375 (19)0.367 (13)
H34C0.30640.10480.10000.045*0.367 (13)
H34D0.27680.03210.17790.045*0.367 (13)
C35X0.2027 (4)0.1408 (14)0.1231 (10)0.0348 (19)0.367 (13)
H35C0.19760.05880.16520.042*0.367 (13)
H35D0.17840.14540.07850.042*0.367 (13)
C36X0.2114 (4)0.3948 (13)0.1167 (9)0.0344 (18)0.367 (13)
H36C0.21370.48320.15420.041*0.367 (13)
H36D0.18670.40560.07370.041*0.367 (13)
C37X0.2864 (5)0.3726 (15)0.1291 (10)0.0355 (19)0.367 (13)
H37C0.28650.46230.16550.043*0.367 (13)
H37D0.31400.36600.09510.043*0.367 (13)
C38X0.2487 (8)0.2411 (18)0.0102 (12)0.0383 (19)0.367 (13)
H38C0.22450.24570.03450.046*0.367 (13)
H38D0.27570.22880.02580.046*0.367 (13)
C390.24965 (10)0.7525 (4)0.49886 (11)0.0335 (4)
H39A0.25390.83760.53870.040*
H39B0.24570.66870.54010.040*
C400.28079 (9)0.6048 (3)0.3808 (2)0.0345 (6)
H40A0.30640.58920.34110.041*
H40B0.27710.51920.42060.041*
C410.20552 (9)0.6445 (3)0.3811 (2)0.0361 (6)
H41A0.20120.55930.42080.043*
H41B0.17950.65640.34180.043*
C420.21791 (9)0.8971 (3)0.3801 (2)0.0348 (6)
H42A0.19210.91200.34070.042*
H42B0.22190.98330.41910.042*
C430.29284 (9)0.8573 (3)0.3799 (2)0.0380 (6)
H43A0.29720.94310.41910.046*
H43B0.31870.84540.34040.046*
C440.24907 (12)0.7491 (4)0.26356 (11)0.0382 (4)
H44A0.22360.76220.22280.046*
H44B0.27460.73480.22310.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.050 (2)0.057 (3)0.043 (2)0.019 (2)0.0175 (19)0.016 (2)
O20.076 (3)0.066 (3)0.041 (2)0.029 (2)0.010 (2)0.014 (2)
C70.036 (2)0.038 (3)0.025 (2)0.003 (2)0.005 (2)0.002 (2)
C10.033 (2)0.037 (3)0.029 (3)0.003 (2)0.005 (2)0.002 (2)
C20.034 (3)0.032 (3)0.037 (3)0.005 (2)0.002 (2)0.010 (2)
C30.044 (3)0.045 (3)0.040 (3)0.004 (3)0.012 (3)0.015 (3)
C40.049 (3)0.050 (4)0.039 (2)0.007 (3)0.011 (3)0.009 (3)
C50.044 (3)0.049 (3)0.039 (3)0.009 (3)0.004 (3)0.003 (2)
C60.035 (3)0.047 (3)0.030 (3)0.004 (2)0.004 (2)0.000 (2)
C80.043 (5)0.045 (4)0.056 (4)0.002 (3)0.003 (3)0.001 (3)
O1X0.076 (4)0.059 (4)0.041 (3)0.026 (3)0.014 (3)0.006 (3)
O2X0.052 (3)0.061 (4)0.071 (4)0.027 (3)0.015 (3)0.010 (3)
C7X0.037 (3)0.041 (3)0.040 (3)0.002 (3)0.003 (2)0.003 (3)
C1X0.029 (3)0.037 (3)0.030 (3)0.002 (3)0.002 (2)0.004 (3)
C2X0.034 (3)0.036 (4)0.035 (3)0.005 (3)0.002 (3)0.000 (3)
C3X0.039 (3)0.035 (3)0.042 (4)0.000 (3)0.002 (3)0.004 (3)
C4X0.040 (4)0.040 (4)0.036 (3)0.004 (3)0.006 (3)0.004 (3)
C5X0.042 (4)0.040 (3)0.034 (3)0.003 (3)0.004 (3)0.002 (3)
C6X0.036 (3)0.037 (3)0.034 (3)0.001 (3)0.000 (3)0.001 (3)
C8X0.045 (6)0.038 (5)0.058 (5)0.003 (4)0.003 (4)0.005 (4)
O30.0538 (19)0.057 (2)0.0388 (19)0.0237 (17)0.0081 (17)0.0105 (18)
O40.0538 (19)0.048 (2)0.067 (2)0.0258 (15)0.0208 (17)0.0218 (18)
C150.0307 (18)0.0265 (18)0.0408 (19)0.0003 (16)0.0002 (16)0.0022 (16)
C90.0285 (17)0.022 (2)0.032 (2)0.0017 (18)0.0020 (16)0.0029 (16)
C100.025 (2)0.028 (2)0.037 (2)0.0028 (18)0.0026 (17)0.005 (2)
C110.036 (2)0.023 (2)0.044 (3)0.0018 (17)0.002 (2)0.0038 (17)
C120.047 (3)0.028 (2)0.038 (2)0.0015 (17)0.0064 (19)0.0070 (18)
C130.044 (3)0.040 (2)0.036 (2)0.002 (2)0.0029 (19)0.0053 (19)
C140.036 (2)0.0279 (18)0.038 (2)0.0032 (17)0.0013 (18)0.0037 (18)
C160.036 (3)0.025 (2)0.054 (3)0.0064 (18)0.001 (2)0.004 (2)
O3X0.039 (4)0.057 (5)0.056 (5)0.013 (3)0.017 (3)0.011 (4)
O4X0.078 (5)0.073 (6)0.034 (4)0.038 (4)0.016 (4)0.018 (4)
C15X0.035 (3)0.035 (4)0.030 (4)0.006 (3)0.001 (3)0.000 (4)
C9X0.032 (3)0.033 (4)0.032 (3)0.007 (3)0.002 (3)0.002 (3)
C10X0.030 (4)0.026 (4)0.040 (4)0.001 (3)0.002 (3)0.007 (3)
C11X0.037 (4)0.034 (4)0.042 (4)0.004 (4)0.008 (4)0.007 (3)
C12X0.045 (4)0.038 (4)0.034 (3)0.000 (4)0.009 (3)0.000 (3)
C13X0.046 (4)0.040 (4)0.039 (4)0.002 (4)0.006 (4)0.002 (3)
C14X0.039 (4)0.037 (3)0.036 (4)0.006 (3)0.003 (3)0.000 (3)
C16X0.047 (8)0.034 (5)0.049 (6)0.002 (5)0.010 (5)0.010 (4)
O50.0514 (13)0.0737 (16)0.0548 (14)0.0074 (12)0.0131 (12)0.0148 (12)
O60.0328 (11)0.0881 (18)0.0874 (19)0.0106 (11)0.0036 (12)0.0254 (16)
O70.0398 (12)0.0792 (17)0.0550 (13)0.0122 (11)0.0149 (11)0.0159 (12)
O80.0381 (12)0.099 (2)0.0788 (18)0.0127 (12)0.0000 (13)0.0271 (16)
N50.0333 (11)0.0292 (11)0.0342 (11)0.0004 (9)0.0051 (10)0.0011 (9)
N60.0322 (10)0.0302 (11)0.0330 (11)0.0005 (9)0.0086 (9)0.0005 (9)
N70.0436 (12)0.0249 (11)0.0299 (11)0.0007 (9)0.0050 (10)0.0050 (9)
N80.0435 (13)0.0259 (11)0.0311 (12)0.0020 (9)0.0000 (10)0.0066 (9)
C170.0306 (12)0.0300 (12)0.0398 (14)0.0020 (11)0.0011 (11)0.0089 (11)
C180.0422 (16)0.0372 (15)0.0423 (15)0.0036 (12)0.0012 (13)0.0095 (12)
C190.0352 (15)0.0537 (18)0.0509 (18)0.0096 (13)0.0054 (14)0.0183 (15)
C200.0369 (14)0.0578 (18)0.0505 (17)0.0020 (15)0.0008 (14)0.0165 (15)
C210.0376 (15)0.0534 (18)0.0544 (18)0.0117 (14)0.0066 (14)0.0106 (15)
C220.0438 (16)0.0395 (15)0.0484 (17)0.0034 (13)0.0008 (14)0.0057 (13)
C230.0376 (14)0.0357 (14)0.0463 (16)0.0034 (13)0.0037 (13)0.0081 (13)
C240.0550 (19)0.0525 (18)0.0542 (19)0.0002 (15)0.0066 (17)0.0055 (16)
C250.0327 (12)0.0285 (12)0.0377 (14)0.0030 (11)0.0026 (11)0.0078 (11)
C260.0405 (15)0.0337 (14)0.0391 (15)0.0040 (12)0.0021 (12)0.0071 (12)
C270.0371 (15)0.0428 (16)0.0461 (16)0.0058 (12)0.0061 (13)0.0105 (14)
C280.0339 (14)0.0509 (17)0.0506 (17)0.0063 (14)0.0055 (14)0.0137 (14)
C290.0421 (16)0.0443 (16)0.0542 (18)0.0084 (13)0.0081 (14)0.0086 (14)
C300.0394 (15)0.0334 (14)0.0454 (16)0.0017 (12)0.0014 (13)0.0038 (12)
C310.0351 (13)0.0339 (13)0.0438 (15)0.0016 (13)0.0036 (12)0.0045 (12)
C320.0509 (18)0.0508 (17)0.0516 (18)0.0014 (14)0.0035 (16)0.0047 (15)
N10.036 (2)0.0266 (18)0.028 (2)0.0016 (17)0.0014 (18)0.0012 (15)
N20.040 (2)0.0288 (19)0.0241 (19)0.0062 (17)0.0011 (17)0.0008 (15)
N30.053 (3)0.0243 (19)0.027 (2)0.0018 (19)0.0033 (19)0.0021 (18)
N40.060 (3)0.0201 (18)0.025 (2)0.000 (2)0.001 (2)0.0010 (17)
C330.039 (3)0.029 (2)0.0216 (18)0.0040 (19)0.003 (2)0.0001 (15)
C340.050 (3)0.0232 (19)0.031 (3)0.0061 (19)0.004 (2)0.0006 (18)
C350.045 (3)0.027 (2)0.036 (2)0.005 (2)0.004 (2)0.0042 (19)
C360.047 (3)0.028 (2)0.034 (3)0.011 (2)0.011 (2)0.006 (2)
C370.044 (3)0.025 (2)0.037 (2)0.003 (2)0.001 (2)0.0024 (19)
C380.071 (3)0.028 (3)0.021 (2)0.004 (2)0.003 (2)0.005 (2)
N1X0.044 (3)0.029 (3)0.029 (3)0.003 (3)0.003 (3)0.000 (2)
N2X0.041 (3)0.031 (3)0.024 (3)0.001 (3)0.002 (3)0.003 (2)
N3X0.057 (4)0.023 (3)0.023 (3)0.001 (3)0.001 (3)0.001 (3)
N4X0.052 (3)0.026 (3)0.029 (3)0.000 (3)0.008 (3)0.004 (3)
C33X0.036 (3)0.031 (3)0.020 (3)0.004 (3)0.002 (3)0.003 (2)
C34X0.050 (4)0.032 (3)0.031 (4)0.010 (3)0.012 (3)0.003 (3)
C35X0.044 (4)0.029 (3)0.032 (3)0.002 (3)0.001 (3)0.001 (3)
C36X0.052 (4)0.022 (3)0.029 (4)0.005 (3)0.007 (3)0.001 (3)
C37X0.045 (4)0.030 (3)0.032 (3)0.004 (3)0.009 (3)0.009 (3)
C38X0.068 (4)0.025 (4)0.022 (3)0.000 (3)0.001 (3)0.008 (3)
C390.0495 (10)0.0280 (8)0.0231 (7)0.0016 (7)0.0005 (14)0.0008 (13)
C400.0412 (15)0.0251 (12)0.0371 (14)0.0082 (11)0.0000 (12)0.0003 (11)
C410.0351 (14)0.0292 (13)0.0441 (15)0.0088 (11)0.0011 (12)0.0027 (12)
C420.0412 (15)0.0248 (12)0.0384 (14)0.0075 (11)0.0003 (12)0.0016 (11)
C430.0371 (14)0.0329 (13)0.0441 (15)0.0099 (11)0.0035 (12)0.0041 (12)
C440.0542 (11)0.0375 (9)0.0228 (7)0.0051 (8)0.0017 (15)0.0017 (14)
Geometric parameters (Å, º) top
O1—C71.313 (6)C17—C181.394 (4)
O1—H1O10.83 (2)C17—C221.413 (4)
O2—C71.208 (7)C17—C231.489 (4)
C7—C11.492 (8)C18—C191.401 (4)
C1—C61.392 (8)C18—C241.492 (4)
C1—C21.408 (8)C19—C201.373 (4)
C2—C31.397 (9)C19—H19A0.9500
C2—C81.513 (9)C20—C211.389 (5)
C3—C41.370 (9)C20—H20A0.9500
C3—H3A0.9500C21—C221.367 (4)
C4—C51.372 (8)C21—H21A0.9500
C4—H4A0.9500C22—H22A0.9500
C5—C61.379 (8)C24—H24A0.9800
C5—H5A0.9500C24—H24B0.9800
C6—H6A0.9500C24—H24C0.9800
C8—H8A0.9800C25—C261.395 (4)
C8—H8B0.9800C25—C301.410 (4)
C8—H8C0.9800C25—C311.491 (3)
O1X—C7X1.306 (8)C26—C271.407 (4)
O1X—H2O10.8400C26—C321.488 (4)
O2X—C7X1.220 (8)C27—C281.359 (4)
C7X—C1X1.489 (10)C27—H27A0.9500
C1X—C2X1.395 (10)C28—C291.393 (5)
C1X—C6X1.400 (10)C28—H28A0.9500
C2X—C3X1.395 (11)C29—C301.372 (4)
C2X—C8X1.513 (10)C29—H29A0.9500
C3X—C4X1.381 (10)C30—H30A0.9500
C3X—H3XA0.9500C32—H32A0.9800
C4X—C5X1.383 (9)C32—H32B0.9800
C4X—H4XA0.9500C32—H32C0.9800
C5X—C6X1.381 (9)N1—C361.477 (6)
C5X—H5XA0.9500N1—C331.483 (5)
C6X—H6XA0.9500N1—C351.487 (7)
C8X—H8XA0.9800N2—C331.469 (6)
C8X—H8XB0.9800N2—C341.478 (6)
C8X—H8XC0.9800N2—C371.481 (7)
O3—C151.311 (5)N3—C341.463 (7)
O3—H1O30.84 (2)N3—C351.470 (7)
O4—C151.201 (5)N3—C381.476 (8)
C15—C91.497 (6)N4—C371.446 (7)
C9—C141.400 (6)N4—C361.457 (8)
C9—C101.406 (6)N4—C381.473 (8)
C10—C111.404 (7)C33—H33A0.9900
C10—C161.500 (6)C33—H33B0.9900
C11—C121.379 (6)C34—H34A0.9900
C11—H11A0.9500C34—H34B0.9900
C12—C131.383 (6)C35—H35A0.9900
C12—H12A0.9500C35—H35B0.9900
C13—C141.376 (6)C36—H36A0.9900
C13—H13A0.9500C36—H36B0.9900
C14—H14A0.9500C37—H37A0.9900
C16—H16A0.9800C37—H37B0.9900
C16—H16B0.9800C38—H38A0.9900
C16—H16C0.9800C38—H38B0.9900
O3X—C15X1.307 (10)N1X—C36X1.459 (10)
O3X—H2O30.8400N1X—C35X1.477 (11)
O4X—C15X1.208 (11)N1X—C33X1.488 (9)
C15X—C9X1.520 (12)N2X—C33X1.471 (9)
C9X—C14X1.392 (12)N2X—C37X1.493 (11)
C9X—C10X1.397 (13)N2X—C34X1.496 (11)
C10X—C11X1.406 (13)N3X—C35X1.464 (12)
C10X—C16X1.516 (13)N3X—C34X1.465 (12)
C11X—C12X1.369 (13)N3X—C38X1.470 (13)
C11X—H11B0.9500N4X—C37X1.456 (12)
C12X—C13X1.365 (12)N4X—C36X1.462 (12)
C12X—H12B0.9500N4X—C38X1.470 (13)
C13X—C14X1.381 (12)C33X—H33C0.9900
C13X—H13B0.9500C33X—H33D0.9900
C14X—H14B0.9500C34X—H34C0.9900
C16X—H16D0.9800C34X—H34D0.9900
C16X—H16E0.9800C35X—H35C0.9900
C16X—H16F0.9800C35X—H35D0.9900
O5—C231.308 (4)C36X—H36C0.9900
O5—H1O50.84 (2)C36X—H36D0.9900
O6—C231.216 (4)C37X—H37C0.9900
O7—C311.301 (4)C37X—H37D0.9900
O7—H1O70.889 (17)C38X—H38C0.9900
O8—C311.210 (3)C38X—H38D0.9900
N5—C391.474 (3)C39—H39A0.9900
N5—C421.479 (3)C39—H39B0.9900
N5—C411.482 (3)C40—H40A0.9900
N6—C391.471 (3)C40—H40B0.9900
N6—C401.478 (3)C41—H41A0.9900
N6—C431.479 (3)C41—H41B0.9900
N7—C411.453 (3)C42—H42A0.9900
N7—C401.460 (3)C42—H42B0.9900
N7—C441.468 (4)C43—H43A0.9900
N8—C431.454 (3)C43—H43B0.9900
N8—C421.454 (3)C44—H44A0.9900
N8—C441.480 (4)C44—H44B0.9900
C7—O1—H1O1111 (4)C25—C26—C27117.7 (3)
O2—C7—O1122.6 (5)C25—C26—C32124.5 (3)
O2—C7—C1124.2 (5)C27—C26—C32117.8 (3)
O1—C7—C1113.1 (6)C28—C27—C26122.0 (3)
C6—C1—C2119.2 (7)C28—C27—H27A119.0
C6—C1—C7118.7 (6)C26—C27—H27A119.0
C2—C1—C7122.1 (6)C27—C28—C29120.5 (3)
C3—C2—C1117.6 (8)C27—C28—H28A119.8
C3—C2—C8119.6 (7)C29—C28—H28A119.8
C1—C2—C8122.8 (7)C30—C29—C28119.0 (3)
C4—C3—C2121.7 (8)C30—C29—H29A120.5
C4—C3—H3A119.1C28—C29—H29A120.5
C2—C3—H3A119.1C29—C30—C25121.1 (3)
C3—C4—C5120.9 (7)C29—C30—H30A119.4
C3—C4—H4A119.6C25—C30—H30A119.4
C5—C4—H4A119.6O8—C31—O7121.9 (3)
C4—C5—C6118.6 (7)O8—C31—C25123.8 (3)
C4—C5—H5A120.7O7—C31—C25114.3 (3)
C6—C5—H5A120.7C26—C32—H32A109.5
C5—C6—C1122.0 (7)C26—C32—H32B109.5
C5—C6—H6A119.0H32A—C32—H32B109.5
C1—C6—H6A119.0C26—C32—H32C109.5
C2—C8—H8A109.5H32A—C32—H32C109.5
C2—C8—H8B109.5H32B—C32—H32C109.5
H8A—C8—H8B109.5C36—N1—C33107.1 (4)
C2—C8—H8C109.5C36—N1—C35109.1 (5)
H8A—C8—H8C109.5C33—N1—C35108.0 (4)
H8B—C8—H8C109.5C33—N2—C34108.6 (4)
C7X—O1X—H2O1109.5C33—N2—C37107.8 (4)
O2X—C7X—O1X123.1 (7)C34—N2—C37107.6 (5)
O2X—C7X—C1X120.3 (7)C34—N3—C35108.0 (6)
O1X—C7X—C1X116.6 (7)C34—N3—C38109.0 (7)
C2X—C1X—C6X119.6 (8)C35—N3—C38109.3 (8)
C2X—C1X—C7X124.8 (8)C37—N4—C36109.5 (6)
C6X—C1X—C7X115.5 (7)C37—N4—C38107.2 (8)
C3X—C2X—C1X118.0 (9)C36—N4—C38107.3 (7)
C3X—C2X—C8X116.5 (9)N2—C33—N1111.8 (4)
C1X—C2X—C8X125.5 (9)N2—C33—H33A109.2
C4X—C3X—C2X122.0 (10)N1—C33—H33A109.2
C4X—C3X—H3XA119.0N2—C33—H33B109.2
C2X—C3X—H3XA119.0N1—C33—H33B109.2
C3X—C4X—C5X119.7 (9)H33A—C33—H33B107.9
C3X—C4X—H4XA120.2N3—C34—N2111.4 (5)
C5X—C4X—H4XA120.2N3—C34—H34A109.3
C6X—C5X—C4X119.3 (8)N2—C34—H34A109.3
C6X—C5X—H5XA120.4N3—C34—H34B109.3
C4X—C5X—H5XA120.4N2—C34—H34B109.3
C5X—C6X—C1X121.2 (7)H34A—C34—H34B108.0
C5X—C6X—H6XA119.4N3—C35—N1110.6 (6)
C1X—C6X—H6XA119.4N3—C35—H35A109.5
C2X—C8X—H8XA109.5N1—C35—H35A109.5
C2X—C8X—H8XB109.5N3—C35—H35B109.5
H8XA—C8X—H8XB109.5N1—C35—H35B109.5
C2X—C8X—H8XC109.5H35A—C35—H35B108.1
H8XA—C8X—H8XC109.5N4—C36—N1112.7 (5)
H8XB—C8X—H8XC109.5N4—C36—H36A109.1
C15—O3—H1O3106 (5)N1—C36—H36A109.1
O4—C15—O3122.6 (4)N4—C36—H36B109.1
O4—C15—C9120.9 (4)N1—C36—H36B109.1
O3—C15—C9116.4 (4)H36A—C36—H36B107.8
C14—C9—C10119.8 (5)N4—C37—N2112.9 (6)
C14—C9—C15115.8 (4)N4—C37—H37A109.0
C10—C9—C15124.3 (4)N2—C37—H37A109.0
C11—C10—C9117.5 (5)N4—C37—H37B109.0
C11—C10—C16116.5 (5)N2—C37—H37B109.0
C9—C10—C16126.0 (5)H37A—C37—H37B107.8
C12—C11—C10121.8 (5)N4—C38—N3112.1 (7)
C12—C11—H11A119.1N4—C38—H38A109.2
C10—C11—H11A119.1N3—C38—H38A109.2
C11—C12—C13120.3 (5)N4—C38—H38B109.2
C11—C12—H12A119.9N3—C38—H38B109.2
C13—C12—H12A119.9H38A—C38—H38B107.9
C14—C13—C12119.3 (4)C36X—N1X—C35X109.4 (9)
C14—C13—H13A120.4C36X—N1X—C33X107.9 (7)
C12—C13—H13A120.4C35X—N1X—C33X107.3 (7)
C13—C14—C9121.3 (4)C33X—N2X—C37X107.7 (7)
C13—C14—H14A119.3C33X—N2X—C34X107.0 (7)
C9—C14—H14A119.3C37X—N2X—C34X107.9 (9)
C10—C16—H16A109.5C35X—N3X—C34X110.0 (10)
C10—C16—H16B109.5C35X—N3X—C38X106.8 (13)
H16A—C16—H16B109.5C34X—N3X—C38X106.7 (12)
C10—C16—H16C109.5C37X—N4X—C36X106.5 (11)
H16A—C16—H16C109.5C37X—N4X—C38X110.5 (14)
H16B—C16—H16C109.5C36X—N4X—C38X109.7 (13)
C15X—O3X—H2O3109.5N2X—C33X—N1X112.1 (7)
O4X—C15X—O3X123.5 (10)N2X—C33X—H33C109.2
O4X—C15X—C9X122.3 (9)N1X—C33X—H33C109.2
O3X—C15X—C9X114.2 (10)N2X—C33X—H33D109.2
C14X—C9X—C10X120.7 (11)N1X—C33X—H33D109.2
C14X—C9X—C15X116.4 (10)H33C—C33X—H33D107.9
C10X—C9X—C15X122.8 (11)N3X—C34X—N2X112.8 (9)
C9X—C10X—C11X115.7 (12)N3X—C34X—H34C109.0
C9X—C10X—C16X123.2 (12)N2X—C34X—H34C109.0
C11X—C10X—C16X121.1 (11)N3X—C34X—H34D109.0
C12X—C11X—C10X123.0 (13)N2X—C34X—H34D109.0
C12X—C11X—H11B118.5H34C—C34X—H34D107.8
C10X—C11X—H11B118.5N3X—C35X—N1X112.4 (10)
C13X—C12X—C11X120.7 (11)N3X—C35X—H35C109.1
C13X—C12X—H12B119.7N1X—C35X—H35C109.1
C11X—C12X—H12B119.7N3X—C35X—H35D109.1
C12X—C13X—C14X118.3 (11)N1X—C35X—H35D109.1
C12X—C13X—H13B120.9H35C—C35X—H35D107.9
C14X—C13X—H13B120.9N1X—C36X—N4X111.5 (10)
C13X—C14X—C9X121.7 (12)N1X—C36X—H36C109.3
C13X—C14X—H14B119.2N4X—C36X—H36C109.3
C9X—C14X—H14B119.2N1X—C36X—H36D109.3
C10X—C16X—H16D109.5N4X—C36X—H36D109.3
C10X—C16X—H16E109.5H36C—C36X—H36D108.0
H16D—C16X—H16E109.5N4X—C37X—N2X111.2 (10)
C10X—C16X—H16F109.5N4X—C37X—H37C109.4
H16D—C16X—H16F109.5N2X—C37X—H37C109.4
H16E—C16X—H16F109.5N4X—C37X—H37D109.4
C23—O5—H1O5100 (7)N2X—C37X—H37D109.4
C31—O7—H1O7112.2 (19)H37C—C37X—H37D108.0
C39—N5—C42108.0 (2)N3X—C38X—N4X112.3 (12)
C39—N5—C41108.4 (2)N3X—C38X—H38C109.1
C42—N5—C41108.0 (2)N4X—C38X—H38C109.1
C39—N6—C40108.4 (2)N3X—C38X—H38D109.1
C39—N6—C43107.7 (2)N4X—C38X—H38D109.1
C40—N6—C43108.1 (2)H38C—C38X—H38D107.9
C41—N7—C40108.4 (2)N6—C39—N5111.29 (12)
C41—N7—C44108.7 (2)N6—C39—H39A109.4
C40—N7—C44108.2 (2)N5—C39—H39A109.4
C43—N8—C42108.0 (2)N6—C39—H39B109.4
C43—N8—C44108.3 (2)N5—C39—H39B109.4
C42—N8—C44108.3 (2)H39A—C39—H39B108.0
C18—C17—C22119.1 (2)N7—C40—N6112.03 (19)
C18—C17—C23123.0 (3)N7—C40—H40A109.2
C22—C17—C23117.8 (3)N6—C40—H40A109.2
C17—C18—C19117.9 (3)N7—C40—H40B109.2
C17—C18—C24124.1 (3)N6—C40—H40B109.2
C19—C18—C24117.9 (3)H40A—C40—H40B107.9
C20—C19—C18121.8 (3)N7—C41—N5111.9 (2)
C20—C19—H19A119.1N7—C41—H41A109.2
C18—C19—H19A119.1N5—C41—H41A109.2
C19—C20—C21120.7 (3)N7—C41—H41B109.2
C19—C20—H20A119.7N5—C41—H41B109.2
C21—C20—H20A119.7H41A—C41—H41B107.9
C22—C21—C20118.3 (3)N8—C42—N5112.25 (19)
C22—C21—H21A120.9N8—C42—H42A109.2
C20—C21—H21A120.9N5—C42—H42A109.2
C21—C22—C17122.2 (3)N8—C42—H42B109.2
C21—C22—H22A118.9N5—C42—H42B109.2
C17—C22—H22A118.9H42A—C42—H42B107.9
O6—C23—O5122.1 (3)N8—C43—N6112.3 (2)
O6—C23—C17123.9 (3)N8—C43—H43A109.1
O5—C23—C17114.0 (3)N6—C43—H43A109.1
C18—C24—H24A109.5N8—C43—H43B109.1
C18—C24—H24B109.5N6—C43—H43B109.1
H24A—C24—H24B109.5H43A—C43—H43B107.9
C18—C24—H24C109.5N7—C44—N8111.84 (12)
H24A—C24—H24C109.5N7—C44—H44A109.2
H24B—C24—H24C109.5N8—C44—H44A109.2
C26—C25—C30119.7 (2)N7—C44—H44B109.2
C26—C25—C31123.0 (3)N8—C44—H44B109.2
C30—C25—C31117.2 (2)H44A—C44—H44B107.9
O2—C7—C1—C6171.2 (8)C26—C27—C28—C290.3 (4)
O1—C7—C1—C611.2 (12)C27—C28—C29—C300.3 (4)
O2—C7—C1—C211.0 (17)C28—C29—C30—C250.4 (4)
O1—C7—C1—C2166.7 (13)C26—C25—C30—C290.2 (4)
C6—C1—C2—C30 (2)C31—C25—C30—C29177.8 (3)
C7—C1—C2—C3177.6 (13)C26—C25—C31—O89.1 (4)
C6—C1—C2—C8179.4 (13)C30—C25—C31—O8173.0 (3)
C7—C1—C2—C83 (2)C26—C25—C31—O7170.0 (2)
C1—C2—C3—C41 (2)C30—C25—C31—O78.0 (4)
C8—C2—C3—C4179.1 (13)C34—N2—C33—N157.3 (5)
C2—C3—C4—C50.0 (19)C37—N2—C33—N158.9 (5)
C3—C4—C5—C60.9 (12)C36—N1—C33—N259.4 (5)
C4—C5—C6—C11.2 (11)C35—N1—C33—N257.9 (5)
C2—C1—C6—C50.6 (17)C35—N3—C34—N260.8 (8)
C7—C1—C6—C5178.5 (8)C38—N3—C34—N257.8 (8)
O2X—C7X—C1X—C2X162.0 (17)C33—N2—C34—N358.8 (6)
O1X—C7X—C1X—C2X15 (2)C37—N2—C34—N357.6 (6)
O2X—C7X—C1X—C6X21.1 (16)C34—N3—C35—N161.3 (8)
O1X—C7X—C1X—C6X161.7 (10)C38—N3—C35—N157.1 (8)
C6X—C1X—C2X—C3X5 (3)C36—N1—C35—N356.5 (7)
C7X—C1X—C2X—C3X178.5 (17)C33—N1—C35—N359.6 (7)
C6X—C1X—C2X—C8X178.6 (17)C37—N4—C36—N157.1 (8)
C7X—C1X—C2X—C8X2 (3)C38—N4—C36—N158.9 (8)
C1X—C2X—C3X—C4X3 (3)C33—N1—C36—N458.0 (6)
C8X—C2X—C3X—C4X179.9 (15)C35—N1—C36—N458.6 (6)
C2X—C3X—C4X—C5X0 (2)C36—N4—C37—N256.4 (8)
C3X—C4X—C5X—C6X1.5 (14)C38—N4—C37—N259.7 (8)
C4X—C5X—C6X—C1X0.4 (14)C33—N2—C37—N457.2 (7)
C2X—C1X—C6X—C5X4 (2)C34—N2—C37—N459.8 (7)
C7X—C1X—C6X—C5X179.4 (9)C37—N4—C38—N358.5 (10)
O4—C15—C9—C1418.0 (8)C36—N4—C38—N359.1 (10)
O3—C15—C9—C14161.5 (5)C34—N3—C38—N458.4 (10)
O4—C15—C9—C10158.7 (9)C35—N3—C38—N459.4 (11)
O3—C15—C9—C1021.8 (11)C37X—N2X—C33X—N1X56.0 (10)
C14—C9—C10—C110.1 (16)C34X—N2X—C33X—N1X59.8 (9)
C15—C9—C10—C11176.5 (9)C36X—N1X—C33X—N2X56.9 (9)
C14—C9—C10—C16178.2 (9)C35X—N1X—C33X—N2X60.9 (10)
C15—C9—C10—C165.2 (18)C35X—N3X—C34X—N2X55.7 (14)
C9—C10—C11—C120.0 (17)C38X—N3X—C34X—N2X59.8 (13)
C16—C10—C11—C12178.5 (8)C33X—N2X—C34X—N3X56.8 (11)
C10—C11—C12—C130.1 (12)C37X—N2X—C34X—N3X58.9 (11)
C11—C12—C13—C140.0 (8)C34X—N3X—C35X—N1X56.5 (14)
C12—C13—C14—C90.1 (8)C38X—N3X—C35X—N1X59.0 (14)
C10—C9—C14—C130.2 (11)C36X—N1X—C35X—N3X58.7 (12)
C15—C9—C14—C13176.7 (5)C33X—N1X—C35X—N3X58.2 (12)
O4X—C15X—C9X—C14X167.2 (14)C35X—N1X—C36X—N4X56.0 (11)
O3X—C15X—C9X—C14X12 (2)C33X—N1X—C36X—N4X60.4 (11)
O4X—C15X—C9X—C10X16 (3)C37X—N4X—C36X—N1X63.5 (14)
O3X—C15X—C9X—C10X165 (2)C38X—N4X—C36X—N1X56.1 (14)
C14X—C9X—C10X—C11X1 (4)C36X—N4X—C37X—N2X62.5 (14)
C15X—C9X—C10X—C11X176 (2)C38X—N4X—C37X—N2X56.5 (15)
C14X—C9X—C10X—C16X178 (2)C33X—N2X—C37X—N4X59.6 (13)
C15X—C9X—C10X—C16X5 (4)C34X—N2X—C37X—N4X55.7 (12)
C9X—C10X—C11X—C12X1 (4)C35X—N3X—C38X—N4X58.8 (17)
C16X—C10X—C11X—C12X178 (2)C34X—N3X—C38X—N4X58.8 (17)
C10X—C11X—C12X—C13X2 (3)C37X—N4X—C38X—N3X58.8 (18)
C11X—C12X—C13X—C14X1 (2)C36X—N4X—C38X—N3X58.3 (18)
C12X—C13X—C14X—C9X1 (2)C40—N6—C39—N558.1 (3)
C10X—C9X—C14X—C13X1 (3)C43—N6—C39—N558.7 (3)
C15X—C9X—C14X—C13X176.5 (13)C42—N5—C39—N658.6 (3)
C22—C17—C18—C190.3 (4)C41—N5—C39—N658.1 (3)
C23—C17—C18—C19177.1 (3)C41—N7—C40—N658.9 (3)
C22—C17—C18—C24179.7 (3)C44—N7—C40—N658.9 (3)
C23—C17—C18—C242.9 (4)C39—N6—C40—N758.6 (3)
C17—C18—C19—C200.1 (4)C43—N6—C40—N757.9 (3)
C24—C18—C19—C20179.9 (3)C40—N7—C41—N558.8 (3)
C18—C19—C20—C210.1 (5)C44—N7—C41—N558.6 (3)
C19—C20—C21—C220.3 (5)C39—N5—C41—N758.7 (3)
C20—C21—C22—C170.5 (4)C42—N5—C41—N758.0 (3)
C18—C17—C22—C210.6 (4)C43—N8—C42—N558.8 (3)
C23—C17—C22—C21177.5 (3)C44—N8—C42—N558.3 (3)
C18—C17—C23—O66.1 (5)C39—N5—C42—N858.8 (3)
C22—C17—C23—O6177.0 (3)C41—N5—C42—N858.1 (3)
C18—C17—C23—O5173.0 (3)C42—N8—C43—N659.1 (3)
C22—C17—C23—O53.8 (4)C44—N8—C43—N658.0 (3)
C30—C25—C26—C270.8 (4)C39—N6—C43—N859.2 (3)
C31—C25—C26—C27177.1 (2)C40—N6—C43—N857.7 (3)
C30—C25—C26—C32178.9 (3)C41—N7—C44—N858.5 (3)
C31—C25—C26—C321.0 (4)C40—N7—C44—N859.0 (3)
C25—C26—C27—C280.9 (4)C43—N8—C44—N758.7 (3)
C32—C26—C27—C28179.1 (3)C42—N8—C44—N758.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N10.83 (5)1.79 (5)2.614 (7)172 (5)
O3—H1O3···N20.84 (5)1.85 (6)2.678 (7)172 (6)
O5—H1O5···N50.84 (6)1.89 (7)2.672 (3)155 (9)
O7—H1O7···N60.89 (2)1.79 (2)2.670 (3)170 (3)
C6—H6A···O10.952.342.685 (8)101
C8—H8C···O20.982.442.774 (11)100
C16—H16A···O30.982.392.814 (7)106
C22—H22A···O50.952.322.681 (4)102
C30—H30A···O70.952.332.677 (4)101
C33—H33A···O40.992.583.146 (9)116
C33—H33B···N8i0.992.603.537 (5)157
C36—H36B···N70.992.593.548 (8)162
C38—H38A···O4ii0.992.403.354 (14)162
C40—H40B···N3iii0.992.593.509 (10)155
C44—H44A···O6iv0.992.393.370 (4)171
C44—H44B···O8iv0.992.393.373 (4)172
Symmetry codes: (i) x, y1, z; (ii) x, y+1/2, z1/2; (iii) x, y+1/2, z+1/2; (iv) x, y+3/2, z1/2.
(165K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top
Crystal data top
C6H12N4·2C8H8O2Dx = 1.314 Mg m3
Mr = 412.48Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PccnCell parameters from 5919 reflections
a = 31.0109 (19) Åθ = 2.3–26.6°
b = 9.3651 (6) ŵ = 0.09 mm1
c = 14.3551 (9) ÅT = 165 K
V = 4169.0 (5) Å3Block, colourless
Z = 80.43 × 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 tube3743 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 28.0°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 4034
Tmin = 0.919, Tmax = 0.963k = 1212
30982 measured reflectionsl = 1818
Refinement top
Refinement on F2387 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.060H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.167 w = 1/[σ2(Fo2) + (0.0679P)2 + 2.5402P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
5032 reflectionsΔρmax = 0.43 e Å3
379 parametersΔρmin = 0.37 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A0.63532 (5)0.8145 (2)0.52416 (12)0.0600 (5)
H1O10.6610 (7)0.798 (4)0.504 (2)0.110 (12)*
O2A0.65799 (5)0.6901 (2)0.64468 (13)0.0711 (5)
N1A0.71130 (5)0.77065 (15)0.44111 (10)0.0326 (3)
N2A0.74366 (5)0.62130 (15)0.32109 (10)0.0342 (3)
C1A0.58337 (6)0.75012 (19)0.63499 (13)0.0339 (4)
C2A0.56865 (6)0.6705 (2)0.71097 (13)0.0394 (4)
C3A0.52458 (6)0.6755 (2)0.73178 (15)0.0453 (5)
H3AA0.51400.62150.78290.054*
C4A0.49627 (7)0.7558 (2)0.68068 (15)0.0473 (5)
H4AA0.46660.75690.69680.057*
C5A0.51067 (7)0.8359 (2)0.60536 (16)0.0479 (5)
H5AA0.49110.89210.57010.057*
C6A0.55357 (6)0.8323 (2)0.58287 (15)0.0421 (4)
H6AA0.56360.88610.53110.051*
C7A0.62893 (6)0.7486 (2)0.60296 (14)0.0395 (4)
C8A0.59679 (7)0.5792 (2)0.76997 (16)0.0528 (5)
H8AA0.57900.52680.81500.079*
H8AB0.61750.63930.80340.079*
H8AC0.61240.51120.73050.079*
C9A0.70630 (6)0.6439 (2)0.38057 (14)0.0382 (4)
H9AA0.70190.55840.41990.046*
H9AB0.68040.65610.34110.046*
C10A0.78144 (6)0.60384 (18)0.38056 (13)0.0353 (4)
H10A0.80720.58860.34100.042*
H10B0.77760.51800.41990.042*
C11A0.75000.75000.49884 (16)0.0342 (5)
H11A0.74620.66930.53800.041*
C12A0.75000.75000.26379 (17)0.0394 (6)
H12A0.72550.76240.22460.047*
O1B0.86517 (12)0.1709 (5)0.2839 (3)0.0540 (10)0.567 (7)
H2O10.8453 (16)0.197 (7)0.250 (4)0.11 (2)*0.567 (7)
O2B0.83472 (9)0.3280 (4)0.3777 (3)0.0582 (11)0.567 (7)
C1B0.8940 (4)0.2010 (10)0.4375 (6)0.0277 (14)0.567 (7)
C2B0.9181 (7)0.0740 (16)0.4388 (12)0.0308 (18)0.567 (7)
C3B0.9453 (6)0.0517 (15)0.5144 (9)0.0370 (17)0.567 (7)
H3BA0.96110.03510.51800.044*0.567 (7)
C4B0.9502 (2)0.1512 (10)0.5842 (6)0.0405 (15)0.567 (7)
H4BA0.96970.13340.63400.049*0.567 (7)
C5B0.9268 (2)0.2773 (8)0.5822 (4)0.0396 (12)0.567 (7)
H5BA0.92960.34570.63060.048*0.567 (7)
C6B0.8991 (2)0.3014 (6)0.5078 (5)0.0334 (12)0.567 (7)
H6BA0.88340.38840.50490.040*0.567 (7)
C7B0.86225 (12)0.2392 (5)0.3629 (3)0.0352 (9)0.567 (7)
C8B0.9175 (2)0.0409 (6)0.3643 (5)0.0404 (12)0.567 (7)
H8BA0.88760.06300.34760.061*0.567 (7)
H8BB0.93160.12720.38810.061*0.567 (7)
H8BC0.93290.00680.30900.061*0.567 (7)
O1Y0.83517 (13)0.2629 (6)0.3356 (3)0.0514 (13)0.433 (7)
H3O10.820 (3)0.252 (12)0.289 (5)0.16 (4)*0.433 (7)
O2Y0.87182 (15)0.0848 (7)0.2732 (3)0.0648 (15)0.433 (7)
C1Y0.8934 (5)0.1700 (14)0.4221 (8)0.034 (2)0.433 (7)
C2Y0.9216 (9)0.059 (2)0.4455 (16)0.037 (3)0.433 (7)
C3Y0.9435 (8)0.072 (2)0.5312 (12)0.047 (3)0.433 (7)
H3YA0.96320.00110.54870.056*0.433 (7)
C4Y0.9373 (3)0.1844 (13)0.5899 (7)0.048 (2)0.433 (7)
H4YA0.95210.18750.64780.057*0.433 (7)
C5Y0.9098 (3)0.2935 (10)0.5661 (7)0.0469 (19)0.433 (7)
H5YA0.90610.37350.60590.056*0.433 (7)
C6Y0.8877 (3)0.2841 (11)0.4832 (7)0.0415 (18)0.433 (7)
H6YA0.86790.35760.46720.050*0.433 (7)
C7Y0.86596 (15)0.1669 (7)0.3360 (4)0.0343 (12)0.433 (7)
C8Y0.9294 (3)0.0685 (10)0.3851 (7)0.0497 (18)0.433 (7)
H8YA0.95160.12890.41350.075*0.433 (7)
H8YB0.93920.03710.32350.075*0.433 (7)
H8YC0.90260.12290.37870.075*0.433 (7)
N1B0.78896 (8)0.2381 (2)0.18589 (12)0.0621 (6)
N2B0.74629 (6)0.12017 (15)0.06696 (10)0.0387 (4)
C9B0.78427 (8)0.1110 (2)0.12596 (17)0.0545 (6)
H9BA0.81020.10120.08630.065*
H9BB0.78220.02480.16560.065*
C10B0.70825 (8)0.1340 (2)0.12585 (14)0.0481 (5)
H10C0.70540.04780.16530.058*
H10D0.68220.14070.08620.058*
C11B0.75000.25000.24366 (19)0.0788 (14)
H11C0.75260.33130.28280.095*
C12B0.75000.25000.00997 (17)0.0425 (6)
H12C0.72540.25900.02920.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0455 (9)0.0794 (12)0.0551 (9)0.0093 (8)0.0144 (7)0.0161 (9)
O2A0.0355 (8)0.0950 (14)0.0828 (12)0.0119 (8)0.0006 (8)0.0248 (11)
N1A0.0329 (8)0.0312 (8)0.0337 (7)0.0007 (6)0.0070 (6)0.0004 (6)
N2A0.0446 (9)0.0268 (7)0.0311 (7)0.0002 (6)0.0027 (6)0.0067 (6)
C1A0.0334 (9)0.0308 (8)0.0375 (9)0.0021 (7)0.0008 (7)0.0086 (7)
C2A0.0409 (10)0.0375 (10)0.0398 (9)0.0047 (8)0.0022 (8)0.0070 (8)
C3A0.0356 (10)0.0504 (12)0.0498 (11)0.0083 (9)0.0051 (9)0.0153 (10)
C4A0.0360 (10)0.0553 (12)0.0506 (12)0.0028 (9)0.0030 (9)0.0151 (10)
C5A0.0400 (11)0.0501 (12)0.0535 (12)0.0106 (9)0.0080 (9)0.0099 (10)
C6A0.0412 (10)0.0380 (10)0.0472 (11)0.0026 (8)0.0005 (8)0.0052 (8)
C7A0.0365 (10)0.0362 (9)0.0458 (10)0.0021 (8)0.0032 (8)0.0068 (8)
C8A0.0513 (12)0.0538 (13)0.0533 (12)0.0004 (10)0.0044 (10)0.0065 (10)
C9A0.0362 (9)0.0335 (9)0.0448 (10)0.0090 (7)0.0022 (8)0.0035 (8)
C10A0.0411 (10)0.0266 (8)0.0381 (9)0.0083 (7)0.0006 (8)0.0010 (7)
C11A0.0492 (15)0.0295 (12)0.0237 (10)0.0026 (11)0.0000.000
C12A0.0552 (16)0.0397 (14)0.0232 (11)0.0038 (12)0.0000.000
O1B0.063 (2)0.060 (3)0.0385 (18)0.0279 (17)0.0100 (16)0.0097 (18)
O2B0.0516 (17)0.055 (2)0.068 (2)0.0275 (14)0.0198 (14)0.0187 (18)
C1B0.029 (2)0.028 (3)0.026 (3)0.007 (2)0.001 (2)0.000 (2)
C2B0.029 (4)0.027 (3)0.037 (3)0.002 (2)0.001 (2)0.000 (3)
C3B0.037 (3)0.029 (3)0.044 (4)0.003 (2)0.001 (3)0.005 (2)
C4B0.043 (4)0.040 (3)0.039 (2)0.001 (2)0.005 (2)0.007 (2)
C5B0.045 (3)0.040 (3)0.034 (3)0.003 (3)0.002 (2)0.006 (2)
C6B0.034 (3)0.0280 (19)0.038 (3)0.0013 (19)0.002 (2)0.007 (2)
C7B0.0317 (19)0.031 (2)0.043 (2)0.0016 (15)0.0004 (15)0.0001 (17)
C8B0.038 (3)0.029 (2)0.054 (3)0.0026 (19)0.000 (2)0.005 (2)
O1Y0.048 (2)0.056 (3)0.051 (2)0.0176 (18)0.0148 (19)0.013 (2)
O2Y0.079 (3)0.078 (4)0.0378 (19)0.038 (3)0.0137 (18)0.015 (2)
C1Y0.037 (3)0.040 (5)0.025 (3)0.006 (4)0.009 (3)0.002 (3)
C2Y0.029 (5)0.038 (5)0.045 (5)0.002 (3)0.005 (4)0.011 (3)
C3Y0.044 (7)0.047 (7)0.049 (6)0.011 (4)0.018 (6)0.019 (4)
C4Y0.048 (6)0.060 (7)0.034 (3)0.016 (4)0.010 (4)0.006 (4)
C5Y0.049 (5)0.054 (4)0.037 (4)0.012 (4)0.005 (4)0.005 (3)
C6Y0.039 (4)0.050 (4)0.035 (4)0.011 (3)0.004 (3)0.002 (3)
C7Y0.039 (2)0.036 (3)0.028 (2)0.002 (2)0.003 (2)0.003 (2)
C8Y0.052 (5)0.041 (4)0.057 (4)0.001 (3)0.008 (3)0.007 (3)
N1B0.1025 (17)0.0425 (10)0.0412 (9)0.0271 (10)0.0320 (10)0.0172 (8)
N2B0.0634 (10)0.0239 (7)0.0289 (7)0.0003 (7)0.0015 (7)0.0014 (6)
C9B0.0735 (15)0.0317 (10)0.0583 (13)0.0015 (10)0.0178 (11)0.0133 (9)
C10B0.0707 (14)0.0330 (10)0.0405 (10)0.0159 (9)0.0073 (10)0.0093 (8)
C11B0.167 (4)0.0519 (19)0.0172 (12)0.052 (2)0.0000.000
C12B0.0737 (19)0.0334 (13)0.0202 (11)0.0029 (13)0.0000.000
Geometric parameters (Å, º) top
O1A—C7A1.304 (3)C3B—H3BA0.9500
O1A—H1O10.862 (18)C4B—C5B1.388 (7)
O2A—C7A1.213 (2)C4B—H4BA0.9500
N1A—C11A1.4713 (19)C5B—C6B1.388 (7)
N1A—C9A1.479 (2)C5B—H5BA0.9500
N1A—C10Ai1.479 (2)C6B—H6BA0.9500
N2A—C9A1.455 (2)C8B—H8BA0.9800
N2A—C10A1.459 (2)C8B—H8BB0.9800
N2A—C12A1.4724 (19)C8B—H8BC0.9800
C1A—C2A1.398 (3)O1Y—C7Y1.311 (6)
C1A—C6A1.416 (3)O1Y—H3O10.83 (2)
C1A—C7A1.486 (3)O2Y—C7Y1.198 (7)
C2A—C3A1.400 (3)C1Y—C6Y1.394 (10)
C2A—C8A1.487 (3)C1Y—C2Y1.399 (14)
C3A—C4A1.369 (3)C1Y—C7Y1.501 (9)
C3A—H3AA0.9500C2Y—C3Y1.408 (15)
C4A—C5A1.389 (3)C2Y—C8Y1.497 (18)
C4A—H4AA0.9500C3Y—C4Y1.365 (13)
C5A—C6A1.369 (3)C3Y—H3YA0.9500
C5A—H5AA0.9500C4Y—C5Y1.374 (10)
C6A—H6AA0.9500C4Y—H4YA0.9500
C8A—H8AA0.9800C5Y—C6Y1.375 (8)
C8A—H8AB0.9800C5Y—H5YA0.9500
C8A—H8AC0.9800C6Y—H6YA0.9500
C9A—H9AA0.9900C8Y—H8YA0.9800
C9A—H9AB0.9900C8Y—H8YB0.9800
C10A—N1Ai1.479 (2)C8Y—H8YC0.9800
C10A—H10A0.9900N1B—C11B1.470 (3)
C10A—H10B0.9900N1B—C9B1.475 (3)
C11A—N1Ai1.4713 (19)N1B—C10Bii1.479 (2)
C11A—H11A0.9493N2B—C9B1.453 (3)
C12A—N2Ai1.4723 (19)N2B—C10B1.457 (3)
C12A—H12A0.9520N2B—C12B1.4700 (19)
O1B—C7B1.305 (5)C9B—H9BA0.9900
O1B—H2O10.82 (2)C9B—H9BB0.9900
O2B—C7B1.211 (5)C10B—N1Bii1.479 (2)
C1B—C6B1.389 (7)C10B—H10C0.9900
C1B—C2B1.405 (10)C10B—H10D0.9900
C1B—C7B1.498 (7)C11B—N1Bii1.470 (3)
C2B—C3B1.391 (11)C11B—H11C0.9492
C2B—C8B1.518 (12)C12B—N2Bii1.4700 (19)
C3B—C4B1.377 (9)C12B—H12C0.9519
C7A—O1A—H1O1111 (2)C4B—C5B—H5BA120.7
C11A—N1A—C9A108.12 (12)C6B—C5B—H5BA120.7
C11A—N1A—C10Ai108.12 (12)C5B—C6B—C1B121.3 (5)
C9A—N1A—C10Ai107.95 (13)C5B—C6B—H6BA119.3
C9A—N2A—C10A108.20 (14)C1B—C6B—H6BA119.3
C9A—N2A—C12A108.37 (13)O2B—C7B—O1B122.5 (4)
C10A—N2A—C12A108.14 (13)O2B—C7B—C1B120.2 (5)
C2A—C1A—C6A119.26 (17)O1B—C7B—C1B117.3 (4)
C2A—C1A—C7A123.15 (17)C2B—C8B—H8BA109.5
C6A—C1A—C7A117.54 (17)C2B—C8B—H8BB109.5
C1A—C2A—C3A117.87 (19)H8BA—C8B—H8BB109.5
C1A—C2A—C8A124.03 (18)C2B—C8B—H8BC109.5
C3A—C2A—C8A118.09 (19)H8BA—C8B—H8BC109.5
C4A—C3A—C2A122.0 (2)H8BB—C8B—H8BC109.5
C4A—C3A—H3AA119.0C7Y—O1Y—H3O1110 (8)
C2A—C3A—H3AA119.0C6Y—C1Y—C2Y119.8 (9)
C3A—C4A—C5A120.47 (19)C6Y—C1Y—C7Y117.5 (9)
C3A—C4A—H4AA119.8C2Y—C1Y—C7Y122.6 (10)
C5A—C4A—H4AA119.8C1Y—C2Y—C3Y116.7 (13)
C6A—C5A—C4A118.8 (2)C1Y—C2Y—C8Y123.6 (12)
C6A—C5A—H5AA120.6C3Y—C2Y—C8Y119.6 (11)
C4A—C5A—H5AA120.6C4Y—C3Y—C2Y122.4 (12)
C5A—C6A—C1A121.5 (2)C4Y—C3Y—H3YA118.8
C5A—C6A—H6AA119.2C2Y—C3Y—H3YA118.8
C1A—C6A—H6AA119.2C3Y—C4Y—C5Y120.6 (9)
O2A—C7A—O1A121.97 (19)C3Y—C4Y—H4YA119.7
O2A—C7A—C1A123.93 (19)C5Y—C4Y—H4YA119.7
O1A—C7A—C1A114.10 (18)C4Y—C5Y—C6Y118.5 (9)
C2A—C8A—H8AA109.5C4Y—C5Y—H5YA120.8
C2A—C8A—H8AB109.5C6Y—C5Y—H5YA120.8
H8AA—C8A—H8AB109.5C5Y—C6Y—C1Y122.0 (9)
C2A—C8A—H8AC109.5C5Y—C6Y—H6YA119.0
H8AA—C8A—H8AC109.5C1Y—C6Y—H6YA119.0
H8AB—C8A—H8AC109.5O2Y—C7Y—O1Y123.2 (5)
N2A—C9A—N1A112.23 (14)O2Y—C7Y—C1Y123.1 (6)
N2A—C9A—H9AA109.2O1Y—C7Y—C1Y113.8 (7)
N1A—C9A—H9AA109.2C2Y—C8Y—H8YA109.5
N2A—C9A—H9AB109.2C2Y—C8Y—H8YB109.5
N1A—C9A—H9AB109.2H8YA—C8Y—H8YB109.5
H9AA—C9A—H9AB107.9C2Y—C8Y—H8YC109.5
N2A—C10A—N1Ai112.16 (13)H8YA—C8Y—H8YC109.5
N2A—C10A—H10A109.2H8YB—C8Y—H8YC109.5
N1Ai—C10A—H10A109.2C11B—N1B—C9B108.01 (17)
N2A—C10A—H10B109.2C11B—N1B—C10Bii108.38 (18)
N1Ai—C10A—H10B109.2C9B—N1B—C10Bii108.63 (16)
H10A—C10A—H10B107.9C9B—N2B—C10B108.86 (16)
N1A—C11A—N1Ai111.44 (18)C9B—N2B—C12B108.04 (14)
N1A—C11A—H11A109.7C10B—N2B—C12B108.23 (14)
N1Ai—C11A—H11A109.3N2B—C9B—N1B111.86 (18)
N2Ai—C12A—N2A112.08 (18)N2B—C9B—H9BA109.2
N2Ai—C12A—H12A109.7N1B—C9B—H9BA109.2
N2A—C12A—H12A108.9N2B—C9B—H9BB109.2
C7B—O1B—H2O1108 (5)N1B—C9B—H9BB109.2
C6B—C1B—C2B120.2 (6)H9BA—C9B—H9BB107.9
C6B—C1B—C7B115.6 (5)N2B—C10B—N1Bii111.27 (16)
C2B—C1B—C7B124.2 (6)N2B—C10B—H10C109.4
C3B—C2B—C1B117.5 (9)N1Bii—C10B—H10C109.4
C3B—C2B—C8B116.8 (8)N2B—C10B—H10D109.4
C1B—C2B—C8B125.7 (8)N1Bii—C10B—H10D109.4
C4B—C3B—C2B122.2 (9)H10C—C10B—H10D108.0
C4B—C3B—H3BA118.9N1Bii—C11B—N1B111.3 (2)
C2B—C3B—H3BA118.9N1Bii—C11B—H11C110.1
C3B—C4B—C5B120.2 (7)N1B—C11B—H11C108.9
C3B—C4B—H4BA119.9N2Bii—C12B—N2B112.37 (19)
C5B—C4B—H4BA119.9N2Bii—C12B—H12C108.6
C4B—C5B—C6B118.6 (6)N2B—C12B—H12C109.8
C6A—C1A—C2A—C3A0.3 (3)C4B—C5B—C6B—C1B1.5 (12)
C7A—C1A—C2A—C3A177.04 (17)C2B—C1B—C6B—C5B2 (2)
C6A—C1A—C2A—C8A179.25 (18)C7B—C1B—C6B—C5B178.4 (7)
C7A—C1A—C2A—C8A1.9 (3)C6B—C1B—C7B—O2B20.6 (13)
C1A—C2A—C3A—C4A0.4 (3)C2B—C1B—C7B—O2B160.1 (16)
C8A—C2A—C3A—C4A179.47 (19)C6B—C1B—C7B—O1B160.8 (8)
C2A—C3A—C4A—C5A0.1 (3)C2B—C1B—C7B—O1B18 (2)
C3A—C4A—C5A—C6A0.4 (3)C6Y—C1Y—C2Y—C3Y1 (4)
C4A—C5A—C6A—C1A0.5 (3)C7Y—C1Y—C2Y—C3Y176 (2)
C2A—C1A—C6A—C5A0.2 (3)C6Y—C1Y—C2Y—C8Y179 (2)
C7A—C1A—C6A—C5A177.67 (18)C7Y—C1Y—C2Y—C8Y4 (4)
C2A—C1A—C7A—O2A7.5 (3)C1Y—C2Y—C3Y—C4Y1 (5)
C6A—C1A—C7A—O2A175.1 (2)C8Y—C2Y—C3Y—C4Y179 (2)
C2A—C1A—C7A—O1A171.50 (18)C2Y—C3Y—C4Y—C5Y2 (4)
C6A—C1A—C7A—O1A5.9 (2)C3Y—C4Y—C5Y—C6Y2 (2)
C10A—N2A—C9A—N1A58.75 (19)C4Y—C5Y—C6Y—C1Y2.0 (16)
C12A—N2A—C9A—N1A58.29 (18)C2Y—C1Y—C6Y—C5Y1 (3)
C11A—N1A—C9A—N2A58.79 (18)C7Y—C1Y—C6Y—C5Y176.9 (10)
C10Ai—N1A—C9A—N2A57.95 (19)C6Y—C1Y—C7Y—O2Y170.2 (10)
C9A—N2A—C10A—N1Ai58.69 (18)C2Y—C1Y—C7Y—O2Y14 (3)
C12A—N2A—C10A—N1Ai58.49 (18)C6Y—C1Y—C7Y—O1Y9.4 (17)
C9A—N1A—C11A—N1Ai58.32 (10)C2Y—C1Y—C7Y—O1Y166 (2)
C10Ai—N1A—C11A—N1Ai58.32 (10)C10B—N2B—C9B—N1B59.2 (2)
C9A—N2A—C12A—N2Ai58.53 (10)C12B—N2B—C9B—N1B58.2 (2)
C10A—N2A—C12A—N2Ai58.54 (10)C11B—N1B—C9B—N2B58.8 (2)
C6B—C1B—C2B—C3B3 (3)C10Bii—N1B—C9B—N2B58.5 (3)
C7B—C1B—C2B—C3B178.0 (17)C9B—N2B—C10B—N1Bii58.8 (2)
C6B—C1B—C2B—C8B176.6 (16)C12B—N2B—C10B—N1Bii58.4 (2)
C7B—C1B—C2B—C8B3 (3)C9B—N1B—C11B—N1Bii58.64 (11)
C1B—C2B—C3B—C4B2 (3)C10Bii—N1B—C11B—N1Bii58.88 (11)
C8B—C2B—C3B—C4B176.9 (17)C9B—N2B—C12B—N2Bii58.69 (13)
C2B—C3B—C4B—C5B2 (3)C10B—N2B—C12B—N2Bii59.04 (11)
C3B—C4B—C5B—C6B1.1 (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···AD—HH···AD···AD—H···A
O1A—H1O1···N1A0.86 (2)1.82 (2)2.672 (2)170 (3)
O1B—H2O1···N1B0.82 (5)2.01 (5)2.822 (5)168 (6)
C6A—H6AA···O1A0.952.332.677 (2)101
C10A—H10B···O2B0.992.583.067 (4)110
C12A—H12A···O2Aiii0.952.433.373 (2)172
C12B—H12C···O2Biv0.952.383.323 (4)169
C8B—H8BA···O1B0.982.472.811 (7)100
Symmetry codes: (iii) x, y+3/2, z1/2; (iv) x+3/2, y, z1/2.
(166K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top
Crystal data top
C6H12N4·2C8H8O2Dx = 1.314 Mg m3
Mr = 412.48Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PccnCell parameters from 9951 reflections
a = 31.0133 (15) Åθ = 2.2–26.6°
b = 9.3657 (5) ŵ = 0.09 mm1
c = 14.3540 (7) ÅT = 166 K
V = 4169.3 (4) Å3Block, colourless
Z = 80.43 × 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 tube3971 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scansθmax = 28.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 4040
Tmin = 0.921, Tmax = 0.963k = 1212
61779 measured reflectionsl = 1818
Refinement top
Refinement on F2387 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.062H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.159 w = 1/[σ2(Fo2) + (0.0582P)2 + 3.0812P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
5038 reflectionsΔρmax = 0.48 e Å3
379 parametersΔρmin = 0.41 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A0.63536 (5)0.8145 (2)0.52402 (11)0.0596 (4)
H1O10.6614 (7)0.799 (4)0.505 (2)0.111 (12)*
O2A0.65797 (5)0.6902 (2)0.64472 (13)0.0709 (5)
N1A0.71130 (4)0.77067 (15)0.44104 (10)0.0323 (3)
N2A0.74367 (5)0.62131 (15)0.32111 (10)0.0339 (3)
C1A0.58330 (5)0.75008 (19)0.63496 (12)0.0333 (4)
C2A0.56865 (6)0.6706 (2)0.71089 (13)0.0389 (4)
C3A0.52448 (6)0.6757 (2)0.73172 (15)0.0446 (5)
H3AA0.51390.62160.78280.054*
C4A0.49630 (6)0.7560 (2)0.68069 (15)0.0471 (5)
H4AA0.46660.75720.69680.057*
C5A0.51073 (7)0.8359 (2)0.60537 (15)0.0483 (5)
H5AA0.49120.89220.57010.058*
C6A0.55360 (6)0.8321 (2)0.58284 (14)0.0415 (4)
H6AA0.56360.88580.53100.050*
C7A0.62901 (6)0.7486 (2)0.60292 (13)0.0390 (4)
C8A0.59677 (7)0.5790 (2)0.77028 (16)0.0526 (5)
H8AA0.57890.52640.81490.079*
H8AB0.61740.63920.80410.079*
H8AC0.61250.51130.73090.079*
C9A0.70628 (6)0.64386 (19)0.38051 (13)0.0373 (4)
H9AA0.70180.55840.41990.045*
H9AB0.68040.65610.34100.045*
C10A0.78146 (6)0.60390 (18)0.38054 (13)0.0351 (4)
H10A0.80720.58870.34100.042*
H10B0.77760.51800.41990.042*
C11A0.75000.75000.49893 (16)0.0343 (5)
H11A0.74620.66930.53810.041*
C12A0.75000.75000.26392 (16)0.0396 (6)
H12A0.72550.76240.22470.047*
O1B0.86512 (11)0.1713 (5)0.2838 (3)0.0529 (10)0.562 (6)
H2O10.8456 (16)0.194 (7)0.248 (4)0.11 (2)*0.562 (6)
O2B0.83470 (9)0.3282 (4)0.3781 (3)0.0576 (10)0.562 (6)
C1B0.8941 (4)0.2011 (10)0.4372 (6)0.0269 (14)0.562 (6)
C2B0.9188 (7)0.0748 (19)0.4377 (12)0.031 (2)0.562 (6)
C3B0.9451 (6)0.0518 (16)0.5142 (10)0.0382 (17)0.562 (6)
H3BA0.96040.03580.51820.046*0.562 (6)
C4B0.9500 (3)0.1500 (9)0.5848 (6)0.0410 (15)0.562 (6)
H4BA0.96920.13130.63490.049*0.562 (6)
C5B0.9267 (2)0.2771 (7)0.5820 (4)0.0379 (12)0.562 (6)
H5BA0.92960.34620.63010.046*0.562 (6)
C6B0.8992 (2)0.3005 (6)0.5078 (5)0.0339 (12)0.562 (6)
H6BA0.88330.38720.50520.041*0.562 (6)
C7B0.86200 (12)0.2395 (5)0.3630 (3)0.0341 (9)0.562 (6)
C8B0.9173 (2)0.0406 (7)0.3642 (5)0.0407 (12)0.562 (6)
H8BA0.88720.06180.34840.061*0.562 (6)
H8BB0.93130.12710.38810.061*0.562 (6)
H8BC0.93260.00790.30830.061*0.562 (6)
O1Y0.83519 (13)0.2633 (6)0.3357 (3)0.0534 (13)0.438 (6)
H3O10.818 (2)0.250 (10)0.292 (4)0.12 (3)*0.438 (6)
O2Y0.87177 (15)0.0850 (7)0.2733 (3)0.0653 (15)0.438 (6)
C1Y0.8931 (6)0.1705 (15)0.4228 (9)0.035 (2)0.438 (6)
C2Y0.9206 (10)0.059 (3)0.4468 (17)0.035 (3)0.438 (6)
C3Y0.9439 (8)0.070 (2)0.5307 (13)0.045 (3)0.438 (6)
H3YA0.96410.00190.54700.054*0.438 (6)
C4Y0.9377 (4)0.1853 (13)0.5894 (7)0.049 (2)0.438 (6)
H4YA0.95300.18970.64670.058*0.438 (6)
C5Y0.9098 (3)0.2939 (10)0.5660 (6)0.0475 (18)0.438 (6)
H5YA0.90590.37300.60650.057*0.438 (6)
C6Y0.8876 (3)0.2862 (11)0.4835 (7)0.0412 (17)0.438 (6)
H6YA0.86820.36060.46720.049*0.438 (6)
C7Y0.86598 (15)0.1673 (7)0.3360 (4)0.0343 (12)0.438 (6)
C8Y0.9292 (3)0.0681 (9)0.3845 (7)0.0487 (17)0.438 (6)
H8YA0.95160.12820.41260.073*0.438 (6)
H8YB0.93900.03470.32330.073*0.438 (6)
H8YC0.90260.12370.37720.073*0.438 (6)
N1B0.78896 (8)0.2380 (2)0.18602 (12)0.0620 (6)
N2B0.74625 (6)0.12017 (15)0.06701 (10)0.0384 (4)
C9B0.78417 (8)0.1109 (2)0.12608 (16)0.0542 (6)
H9BA0.81010.10080.08650.065*
H9BB0.78200.02470.16570.065*
C10B0.70831 (8)0.1340 (2)0.12595 (14)0.0477 (5)
H10C0.70550.04790.16550.057*
H10D0.68230.14060.08630.057*
C11B0.75000.25000.24375 (19)0.0792 (14)
H11C0.75260.33130.28290.095*
C12B0.75000.25000.01012 (16)0.0420 (6)
H12C0.72540.25900.02910.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0452 (9)0.0787 (11)0.0548 (9)0.0094 (8)0.0141 (7)0.0158 (8)
O2A0.0355 (8)0.0938 (13)0.0834 (12)0.0125 (8)0.0016 (8)0.0264 (11)
N1A0.0331 (7)0.0298 (7)0.0341 (7)0.0001 (6)0.0070 (6)0.0005 (6)
N2A0.0443 (8)0.0256 (7)0.0319 (7)0.0006 (6)0.0022 (6)0.0068 (6)
C1A0.0322 (8)0.0289 (8)0.0387 (9)0.0024 (7)0.0010 (7)0.0084 (7)
C2A0.0402 (10)0.0349 (9)0.0414 (9)0.0036 (8)0.0023 (8)0.0069 (8)
C3A0.0355 (10)0.0495 (11)0.0490 (11)0.0083 (8)0.0051 (8)0.0142 (9)
C4A0.0355 (9)0.0543 (12)0.0516 (11)0.0035 (9)0.0026 (8)0.0152 (10)
C5A0.0404 (10)0.0497 (12)0.0547 (12)0.0102 (9)0.0070 (9)0.0098 (10)
C6A0.0416 (10)0.0366 (10)0.0465 (10)0.0025 (8)0.0005 (8)0.0048 (8)
C7A0.0362 (9)0.0348 (9)0.0459 (10)0.0017 (8)0.0044 (8)0.0062 (8)
C8A0.0524 (12)0.0521 (12)0.0534 (12)0.0003 (10)0.0035 (10)0.0064 (10)
C9A0.0359 (9)0.0308 (9)0.0451 (10)0.0090 (7)0.0021 (8)0.0030 (7)
C10A0.0412 (9)0.0251 (8)0.0389 (9)0.0081 (7)0.0008 (7)0.0007 (7)
C11A0.0488 (14)0.0300 (11)0.0241 (10)0.0020 (11)0.0000.000
C12A0.0578 (16)0.0389 (13)0.0220 (10)0.0042 (12)0.0000.000
O1B0.063 (2)0.058 (2)0.0373 (17)0.0275 (16)0.0110 (15)0.0076 (17)
O2B0.0524 (17)0.0523 (19)0.068 (2)0.0275 (13)0.0192 (14)0.0201 (17)
C1B0.025 (2)0.026 (3)0.030 (3)0.004 (2)0.001 (2)0.003 (2)
C2B0.029 (3)0.029 (4)0.035 (3)0.002 (3)0.003 (3)0.002 (4)
C3B0.040 (4)0.029 (3)0.046 (4)0.000 (3)0.000 (3)0.006 (2)
C4B0.047 (4)0.035 (3)0.041 (2)0.000 (2)0.008 (2)0.009 (2)
C5B0.042 (3)0.038 (2)0.033 (2)0.002 (3)0.003 (2)0.0041 (18)
C6B0.034 (3)0.030 (2)0.037 (3)0.003 (2)0.000 (2)0.003 (2)
C7B0.0315 (18)0.0294 (19)0.0415 (19)0.0013 (15)0.0006 (15)0.0006 (16)
C8B0.037 (3)0.030 (2)0.056 (3)0.0034 (19)0.000 (2)0.004 (2)
O1Y0.047 (2)0.059 (3)0.054 (2)0.0187 (18)0.0166 (19)0.012 (2)
O2Y0.079 (3)0.076 (4)0.041 (2)0.036 (2)0.0130 (18)0.013 (2)
C1Y0.039 (3)0.041 (6)0.026 (3)0.005 (4)0.007 (2)0.003 (3)
C2Y0.035 (5)0.028 (4)0.043 (5)0.006 (3)0.001 (4)0.012 (3)
C3Y0.041 (6)0.043 (7)0.050 (6)0.010 (4)0.019 (6)0.017 (4)
C4Y0.055 (6)0.056 (7)0.035 (3)0.015 (4)0.014 (4)0.008 (4)
C5Y0.048 (4)0.051 (4)0.043 (4)0.009 (3)0.007 (3)0.005 (3)
C6Y0.038 (4)0.048 (4)0.038 (4)0.006 (3)0.003 (3)0.001 (3)
C7Y0.036 (2)0.038 (3)0.030 (2)0.003 (2)0.003 (2)0.006 (2)
C8Y0.051 (5)0.038 (4)0.057 (4)0.000 (3)0.006 (3)0.005 (3)
N1B0.1027 (16)0.0408 (9)0.0424 (9)0.0261 (10)0.0321 (10)0.0170 (8)
N2B0.0629 (10)0.0226 (7)0.0299 (7)0.0006 (7)0.0018 (7)0.0025 (6)
C9B0.0741 (15)0.0291 (9)0.0593 (13)0.0019 (10)0.0184 (11)0.0138 (9)
C10B0.0703 (14)0.0319 (9)0.0407 (10)0.0148 (9)0.0066 (9)0.0090 (8)
C11B0.169 (4)0.0512 (18)0.0177 (12)0.050 (2)0.0000.000
C12B0.0741 (19)0.0317 (12)0.0202 (10)0.0039 (13)0.0000.000
Geometric parameters (Å, º) top
O1A—C7A1.305 (2)C3B—H3BA0.9500
O1A—H1O10.868 (18)C4B—C5B1.393 (7)
O2A—C7A1.211 (2)C4B—H4BA0.9500
N1A—C11A1.4725 (19)C5B—C6B1.382 (6)
N1A—C10Ai1.478 (2)C5B—H5BA0.9500
N1A—C9A1.480 (2)C6B—H6BA0.9500
N2A—C9A1.455 (2)C8B—H8BA0.9800
N2A—C10A1.459 (2)C8B—H8BB0.9800
N2A—C12A1.4714 (19)C8B—H8BC0.9800
C1A—C2A1.396 (3)O1Y—C7Y1.311 (6)
C1A—C6A1.414 (3)O1Y—H3O10.83 (2)
C1A—C7A1.490 (2)O2Y—C7Y1.199 (7)
C2A—C3A1.403 (3)C1Y—C2Y1.392 (14)
C2A—C8A1.491 (3)C1Y—C6Y1.401 (11)
C3A—C4A1.366 (3)C1Y—C7Y1.504 (9)
C3A—H3AA0.9500C2Y—C3Y1.409 (15)
C4A—C5A1.389 (3)C2Y—C8Y1.512 (19)
C4A—H4AA0.9500C3Y—C4Y1.382 (13)
C5A—C6A1.369 (3)C3Y—H3YA0.9500
C5A—H5AA0.9500C4Y—C5Y1.378 (9)
C6A—H6AA0.9500C4Y—H4YA0.9500
C8A—H8AA0.9800C5Y—C6Y1.370 (8)
C8A—H8AB0.9800C5Y—H5YA0.9500
C8A—H8AC0.9800C6Y—H6YA0.9500
C9A—H9AA0.9900C8Y—H8YA0.9800
C9A—H9AB0.9900C8Y—H8YB0.9800
C10A—N1Ai1.478 (2)C8Y—H8YC0.9800
C10A—H10A0.9900N1B—C11B1.469 (3)
C10A—H10B0.9900N1B—C9B1.477 (3)
C11A—N1Ai1.4726 (19)N1B—C10Bii1.479 (2)
C11A—H11A0.9493N2B—C9B1.453 (3)
C12A—N2Ai1.4714 (19)N2B—C10B1.455 (3)
C12A—H12A0.9520N2B—C12B1.4693 (19)
O1B—C7B1.309 (4)C9B—H9BA0.9900
O1B—H2O10.82 (2)C9B—H9BB0.9900
O2B—C7B1.206 (5)C10B—N1Bii1.479 (2)
C1B—C6B1.386 (7)C10B—H10C0.9900
C1B—C2B1.408 (11)C10B—H10D0.9900
C1B—C7B1.502 (6)C11B—N1Bii1.469 (3)
C2B—C3B1.385 (11)C11B—H11C0.9492
C2B—C8B1.511 (13)C12B—N2Bii1.4693 (19)
C3B—C4B1.377 (9)C12B—H12C0.9520
C7A—O1A—H1O1110 (2)C6B—C5B—H5BA120.7
C11A—N1A—C10Ai108.18 (12)C4B—C5B—H5BA120.7
C11A—N1A—C9A108.15 (12)C5B—C6B—C1B121.8 (5)
C10Ai—N1A—C9A107.99 (13)C5B—C6B—H6BA119.1
C9A—N2A—C10A108.29 (13)C1B—C6B—H6BA119.1
C9A—N2A—C12A108.33 (12)O2B—C7B—O1B123.0 (4)
C10A—N2A—C12A108.10 (12)O2B—C7B—C1B120.3 (5)
C2A—C1A—C6A119.39 (17)O1B—C7B—C1B116.7 (4)
C2A—C1A—C7A123.06 (17)C2B—C8B—H8BA109.5
C6A—C1A—C7A117.50 (17)C2B—C8B—H8BB109.5
C1A—C2A—C3A117.80 (18)H8BA—C8B—H8BB109.5
C1A—C2A—C8A124.25 (18)C2B—C8B—H8BC109.5
C3A—C2A—C8A117.94 (19)H8BA—C8B—H8BC109.5
C4A—C3A—C2A121.9 (2)H8BB—C8B—H8BC109.5
C4A—C3A—H3AA119.0C7Y—O1Y—H3O1111 (7)
C2A—C3A—H3AA119.0C2Y—C1Y—C6Y120.1 (9)
C3A—C4A—C5A120.52 (19)C2Y—C1Y—C7Y122.2 (10)
C3A—C4A—H4AA119.7C6Y—C1Y—C7Y117.6 (9)
C5A—C4A—H4AA119.7C1Y—C2Y—C3Y118.0 (14)
C6A—C5A—C4A118.9 (2)C1Y—C2Y—C8Y123.5 (12)
C6A—C5A—H5AA120.6C3Y—C2Y—C8Y118.3 (11)
C4A—C5A—H5AA120.6C4Y—C3Y—C2Y120.5 (12)
C5A—C6A—C1A121.47 (19)C4Y—C3Y—H3YA119.7
C5A—C6A—H6AA119.3C2Y—C3Y—H3YA119.7
C1A—C6A—H6AA119.3C5Y—C4Y—C3Y121.0 (8)
O2A—C7A—O1A122.14 (18)C5Y—C4Y—H4YA119.5
O2A—C7A—C1A123.84 (18)C3Y—C4Y—H4YA119.5
O1A—C7A—C1A114.01 (17)C6Y—C5Y—C4Y119.2 (9)
C2A—C8A—H8AA109.5C6Y—C5Y—H5YA120.4
C2A—C8A—H8AB109.5C4Y—C5Y—H5YA120.4
H8AA—C8A—H8AB109.5C5Y—C6Y—C1Y121.1 (9)
C2A—C8A—H8AC109.5C5Y—C6Y—H6YA119.4
H8AA—C8A—H8AC109.5C1Y—C6Y—H6YA119.4
H8AB—C8A—H8AC109.5O2Y—C7Y—O1Y123.2 (5)
N2A—C9A—N1A112.14 (13)O2Y—C7Y—C1Y123.5 (6)
N2A—C9A—H9AA109.2O1Y—C7Y—C1Y113.4 (7)
N1A—C9A—H9AA109.2C2Y—C8Y—H8YA109.5
N2A—C9A—H9AB109.2C2Y—C8Y—H8YB109.5
N1A—C9A—H9AB109.2H8YA—C8Y—H8YB109.5
H9AA—C9A—H9AB107.9C2Y—C8Y—H8YC109.5
N2A—C10A—N1Ai112.15 (13)H8YA—C8Y—H8YC109.5
N2A—C10A—H10A109.2H8YB—C8Y—H8YC109.5
N1Ai—C10A—H10A109.2C11B—N1B—C9B107.90 (17)
N2A—C10A—H10B109.2C11B—N1B—C10Bii108.29 (18)
N1Ai—C10A—H10B109.2C9B—N1B—C10Bii108.64 (15)
H10A—C10A—H10B107.9C9B—N2B—C10B108.71 (16)
N1A—C11A—N1Ai111.31 (18)C9B—N2B—C12B108.05 (14)
N1A—C11A—H11A109.7C10B—N2B—C12B108.28 (14)
N1Ai—C11A—H11A109.3N2B—C9B—N1B111.91 (17)
N2Ai—C12A—N2A112.18 (18)N2B—C9B—H9BA109.2
N2Ai—C12A—H12A109.7N1B—C9B—H9BA109.2
N2A—C12A—H12A108.8N2B—C9B—H9BB109.2
C7B—O1B—H2O1111 (5)N1B—C9B—H9BB109.2
C6B—C1B—C2B120.0 (6)H9BA—C9B—H9BB107.9
C6B—C1B—C7B115.6 (5)N2B—C10B—N1Bii111.40 (16)
C2B—C1B—C7B124.4 (7)N2B—C10B—H10C109.3
C3B—C2B—C1B117.0 (9)N1Bii—C10B—H10C109.3
C3B—C2B—C8B117.4 (8)N2B—C10B—H10D109.3
C1B—C2B—C8B125.5 (8)N1Bii—C10B—H10D109.3
C4B—C3B—C2B123.1 (10)H10C—C10B—H10D108.0
C4B—C3B—H3BA118.5N1B—C11B—N1Bii111.4 (2)
C2B—C3B—H3BA118.5N1B—C11B—H11C108.9
C3B—C4B—C5B119.5 (7)N1Bii—C11B—H11C110.1
C3B—C4B—H4BA120.3N2B—C12B—N2Bii112.47 (18)
C5B—C4B—H4BA120.3N2B—C12B—H12C109.8
C6B—C5B—C4B118.5 (6)N2Bii—C12B—H12C108.6
C6A—C1A—C2A—C3A0.3 (3)C4B—C5B—C6B—C1B0.4 (12)
C7A—C1A—C2A—C3A177.09 (16)C2B—C1B—C6B—C5B3 (2)
C6A—C1A—C2A—C8A179.29 (18)C7B—C1B—C6B—C5B178.0 (7)
C7A—C1A—C2A—C8A1.9 (3)C6B—C1B—C7B—O2B19.8 (14)
C1A—C2A—C3A—C4A0.6 (3)C2B—C1B—C7B—O2B161.1 (17)
C8A—C2A—C3A—C4A179.60 (19)C6B—C1B—C7B—O1B161.0 (8)
C2A—C3A—C4A—C5A0.2 (3)C2B—C1B—C7B—O1B18 (2)
C3A—C4A—C5A—C6A0.4 (3)C6Y—C1Y—C2Y—C3Y3 (4)
C4A—C5A—C6A—C1A0.6 (3)C7Y—C1Y—C2Y—C3Y178 (2)
C2A—C1A—C6A—C5A0.3 (3)C6Y—C1Y—C2Y—C8Y179 (2)
C7A—C1A—C6A—C5A177.81 (18)C7Y—C1Y—C2Y—C8Y6 (5)
C2A—C1A—C7A—O2A7.5 (3)C1Y—C2Y—C3Y—C4Y3 (5)
C6A—C1A—C7A—O2A175.1 (2)C8Y—C2Y—C3Y—C4Y179 (2)
C2A—C1A—C7A—O1A171.51 (17)C2Y—C3Y—C4Y—C5Y2 (4)
C6A—C1A—C7A—O1A5.9 (2)C3Y—C4Y—C5Y—C6Y1 (2)
C10A—N2A—C9A—N1A58.73 (18)C4Y—C5Y—C6Y—C1Y0.2 (17)
C12A—N2A—C9A—N1A58.28 (18)C2Y—C1Y—C6Y—C5Y2 (3)
C11A—N1A—C9A—N2A58.83 (18)C7Y—C1Y—C6Y—C5Y177.1 (10)
C10Ai—N1A—C9A—N2A58.02 (18)C2Y—C1Y—C7Y—O2Y15 (3)
C9A—N2A—C10A—N1Ai58.70 (18)C6Y—C1Y—C7Y—O2Y169.7 (11)
C12A—N2A—C10A—N1Ai58.46 (18)C2Y—C1Y—C7Y—O1Y165 (2)
C10Ai—N1A—C11A—N1Ai58.36 (9)C6Y—C1Y—C7Y—O1Y10.5 (18)
C9A—N1A—C11A—N1Ai58.37 (10)C10B—N2B—C9B—N1B59.3 (2)
C9A—N2A—C12A—N2Ai58.58 (10)C12B—N2B—C9B—N1B58.0 (2)
C10A—N2A—C12A—N2Ai58.55 (10)C11B—N1B—C9B—N2B58.9 (2)
C6B—C1B—C2B—C3B5 (3)C10Bii—N1B—C9B—N2B58.3 (3)
C7B—C1B—C2B—C3B176.3 (18)C9B—N2B—C10B—N1Bii58.9 (2)
C6B—C1B—C2B—C8B178.4 (17)C12B—N2B—C10B—N1Bii58.2 (2)
C7B—C1B—C2B—C8B1 (3)C9B—N1B—C11B—N1Bii58.61 (11)
C1B—C2B—C3B—C4B4 (4)C10Bii—N1B—C11B—N1Bii58.81 (11)
C8B—C2B—C3B—C4B178.4 (18)C9B—N2B—C12B—N2Bii58.63 (13)
C2B—C3B—C4B—C5B2 (3)C10B—N2B—C12B—N2Bii58.94 (11)
C3B—C4B—C5B—C6B0.1 (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···AD—HH···AD···AD—H···A
O1A—H1O1···N1A0.87 (2)1.82 (2)2.671 (2)168 (3)
O1B—H2O1···N1B0.82 (5)2.01 (5)2.818 (4)167 (6)
C6A—H6AA···O1A0.952.332.678 (2)101
C10A—H10B···O2B0.992.583.065 (4)110
C12A—H12A···O2Aiii0.952.433.375 (2)172
C12B—H12C···O2Biv0.952.383.321 (4)169
C8B—H8BA···O1B0.982.472.809 (8)100
Symmetry codes: (iii) x, y+3/2, z1/2; (iv) x+3/2, y, z1/2.
(170K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top
Crystal data top
C6H12N4·2C8H8O2Dx = 1.313 Mg m3
Mr = 412.48Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PccnCell parameters from 9951 reflections
a = 31.0259 (15) Åθ = 2.3–26.6°
b = 9.3706 (4) ŵ = 0.09 mm1
c = 14.3567 (7) ÅT = 170 K
V = 4173.9 (3) Å3Block, colourless
Z = 80.43 × 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 tube3967 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 28.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 4040
Tmin = 0.925, Tmax = 0.963k = 1212
61851 measured reflectionsl = 1818
Refinement top
Refinement on F2387 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.061H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.161 w = 1/[σ2(Fo2) + (0.062P)2 + 2.6644P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
5043 reflectionsΔρmax = 0.40 e Å3
379 parametersΔρmin = 0.39 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A0.63539 (5)0.8144 (2)0.52413 (11)0.0606 (4)
H1O10.6613 (7)0.797 (4)0.504 (2)0.123 (13)*
O2A0.65797 (5)0.6901 (2)0.64482 (13)0.0724 (5)
N1A0.71130 (4)0.77061 (15)0.44124 (10)0.0328 (3)
N2A0.74368 (5)0.62144 (14)0.32121 (9)0.0346 (3)
C1A0.58331 (5)0.75010 (19)0.63498 (12)0.0342 (4)
C2A0.56869 (6)0.67060 (19)0.71091 (13)0.0396 (4)
C3A0.52453 (6)0.6755 (2)0.73182 (14)0.0458 (5)
H3AA0.51390.62160.78300.055*
C4A0.49632 (6)0.7558 (2)0.68068 (15)0.0476 (5)
H4AA0.46660.75680.69680.057*
C5A0.51075 (6)0.8358 (2)0.60535 (15)0.0492 (5)
H5AA0.49120.89220.57010.059*
C6A0.55364 (6)0.8319 (2)0.58289 (14)0.0426 (4)
H6AA0.56370.88550.53110.051*
C7A0.62903 (6)0.7484 (2)0.60308 (13)0.0396 (4)
C8A0.59678 (7)0.5791 (2)0.77010 (16)0.0533 (5)
H8AA0.57900.52700.81510.080*
H8AB0.61750.63910.80350.080*
H8AC0.61230.51100.73070.080*
C9A0.70635 (6)0.64386 (19)0.38054 (13)0.0378 (4)
H9AA0.70190.55830.41990.045*
H9AB0.68040.65610.34110.045*
C10A0.78141 (6)0.60396 (17)0.38066 (12)0.0356 (4)
H10A0.80710.58870.34110.043*
H10B0.77760.51810.42000.043*
C11A0.75000.75000.49906 (16)0.0349 (5)
H11A0.74620.66930.53820.042*
C12A0.75000.75000.26388 (16)0.0394 (6)
H12A0.72550.76240.22470.047*
O1B0.86500 (11)0.1712 (5)0.2842 (3)0.0537 (10)0.563 (7)
H2O10.8455 (16)0.193 (7)0.248 (4)0.11 (2)*0.563 (7)
O2B0.83470 (9)0.3280 (4)0.3782 (3)0.0586 (10)0.563 (7)
C1B0.8940 (4)0.2001 (12)0.4371 (7)0.0292 (14)0.563 (7)
C2B0.9188 (8)0.0751 (19)0.4371 (12)0.032 (2)0.563 (7)
C3B0.9449 (6)0.0524 (15)0.5140 (10)0.0388 (17)0.563 (7)
H3BA0.96000.03560.51840.047*0.563 (7)
C4B0.9502 (3)0.1502 (9)0.5844 (6)0.0417 (15)0.563 (7)
H4BA0.96950.13150.63430.050*0.563 (7)
C5B0.9268 (2)0.2774 (7)0.5818 (4)0.0399 (12)0.563 (7)
H5BA0.92990.34670.62970.048*0.563 (7)
C6B0.8991 (2)0.3002 (7)0.5080 (5)0.0350 (12)0.563 (7)
H6BA0.88310.38650.50540.042*0.563 (7)
C7B0.86201 (12)0.2397 (5)0.3635 (3)0.0349 (9)0.563 (7)
C8B0.9173 (2)0.0403 (7)0.3638 (5)0.0423 (12)0.563 (7)
H8BA0.88730.06000.34730.063*0.563 (7)
H8BB0.93070.12730.38830.063*0.563 (7)
H8BC0.93300.00850.30840.063*0.563 (7)
O1Y0.83516 (13)0.2635 (6)0.3359 (3)0.0544 (13)0.437 (7)
H3O10.820 (2)0.250 (10)0.289 (4)0.12 (3)*0.437 (7)
O2Y0.87172 (15)0.0857 (7)0.2734 (3)0.0665 (15)0.437 (7)
C1Y0.8932 (6)0.1721 (17)0.4228 (10)0.037 (2)0.437 (7)
C2Y0.9203 (11)0.059 (3)0.4472 (17)0.035 (3)0.437 (7)
C3Y0.9440 (8)0.070 (2)0.5307 (13)0.046 (3)0.437 (7)
H3YA0.96430.00190.54660.056*0.437 (7)
C4Y0.9376 (4)0.1845 (13)0.5895 (7)0.050 (2)0.437 (7)
H4YA0.95280.18830.64700.060*0.437 (7)
C5Y0.9099 (3)0.2934 (10)0.5664 (7)0.0493 (19)0.437 (7)
H5YA0.90600.37230.60710.059*0.437 (7)
C6Y0.8879 (3)0.2859 (11)0.4836 (7)0.0425 (18)0.437 (7)
H6YA0.86850.36050.46750.051*0.437 (7)
C7Y0.86614 (14)0.1683 (7)0.3363 (4)0.0350 (12)0.437 (7)
C8Y0.9289 (3)0.0678 (10)0.3845 (7)0.0490 (17)0.437 (7)
H8YA0.95160.12720.41200.073*0.437 (7)
H8YB0.93820.03400.32320.073*0.437 (7)
H8YC0.90250.12420.37790.073*0.437 (7)
N1B0.78894 (7)0.23790 (19)0.18616 (12)0.0623 (6)
N2B0.74620 (6)0.12017 (15)0.06713 (10)0.0395 (4)
C9B0.78416 (8)0.1110 (2)0.12613 (16)0.0552 (6)
H9BA0.81010.10120.08650.066*
H9BB0.78210.02480.16570.066*
C10B0.70825 (7)0.1340 (2)0.12605 (14)0.0483 (5)
H10C0.70540.04790.16560.058*
H10D0.68220.14070.08640.058*
C11B0.75000.25000.24373 (18)0.0787 (13)
H11C0.75260.33130.28280.094*
C12B0.75000.25000.01011 (16)0.0429 (6)
H12C0.72540.25900.02910.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0469 (9)0.0788 (11)0.0560 (9)0.0107 (8)0.0142 (7)0.0158 (8)
O2A0.0363 (8)0.0970 (14)0.0839 (12)0.0123 (8)0.0015 (8)0.0264 (11)
N1A0.0330 (7)0.0304 (7)0.0350 (7)0.0000 (6)0.0073 (6)0.0006 (6)
N2A0.0449 (8)0.0268 (7)0.0322 (7)0.0004 (6)0.0024 (6)0.0064 (5)
C1A0.0323 (8)0.0305 (8)0.0398 (9)0.0025 (7)0.0011 (7)0.0092 (7)
C2A0.0402 (9)0.0365 (9)0.0421 (9)0.0038 (7)0.0014 (7)0.0071 (8)
C3A0.0370 (10)0.0501 (11)0.0504 (11)0.0085 (8)0.0061 (8)0.0147 (9)
C4A0.0353 (9)0.0553 (12)0.0523 (11)0.0042 (9)0.0031 (8)0.0147 (10)
C5A0.0410 (10)0.0503 (12)0.0563 (12)0.0110 (9)0.0076 (9)0.0096 (10)
C6A0.0422 (10)0.0378 (10)0.0478 (10)0.0026 (8)0.0006 (8)0.0049 (8)
C7A0.0371 (9)0.0349 (9)0.0467 (10)0.0020 (8)0.0037 (8)0.0060 (8)
C8A0.0509 (12)0.0540 (12)0.0550 (12)0.0009 (10)0.0037 (10)0.0056 (10)
C9A0.0359 (9)0.0315 (8)0.0461 (10)0.0091 (7)0.0016 (7)0.0030 (7)
C10A0.0422 (9)0.0251 (8)0.0396 (9)0.0083 (7)0.0009 (7)0.0010 (7)
C11A0.0505 (14)0.0305 (11)0.0236 (10)0.0022 (10)0.0000.000
C12A0.0564 (15)0.0388 (13)0.0230 (10)0.0046 (12)0.0000.000
O1B0.0642 (19)0.058 (2)0.0391 (17)0.0288 (16)0.0113 (15)0.0089 (17)
O2B0.0540 (16)0.0534 (19)0.069 (2)0.0276 (13)0.0203 (14)0.0202 (17)
C1B0.028 (2)0.030 (3)0.030 (3)0.004 (2)0.002 (2)0.002 (2)
C2B0.032 (3)0.030 (4)0.035 (4)0.003 (3)0.005 (2)0.003 (4)
C3B0.041 (4)0.027 (2)0.048 (4)0.000 (2)0.001 (3)0.006 (2)
C4B0.047 (4)0.038 (3)0.040 (2)0.001 (2)0.007 (2)0.009 (2)
C5B0.044 (3)0.040 (2)0.036 (2)0.003 (3)0.002 (2)0.0044 (18)
C6B0.035 (3)0.032 (2)0.038 (3)0.004 (2)0.001 (2)0.004 (2)
C7B0.0316 (18)0.0301 (19)0.0428 (19)0.0011 (14)0.0013 (15)0.0005 (16)
C8B0.040 (3)0.031 (3)0.055 (3)0.0034 (19)0.001 (2)0.004 (2)
O1Y0.048 (2)0.062 (3)0.053 (2)0.0177 (18)0.0178 (18)0.013 (2)
O2Y0.080 (3)0.079 (4)0.0408 (19)0.036 (2)0.0135 (17)0.015 (2)
C1Y0.038 (3)0.044 (6)0.028 (3)0.005 (4)0.007 (3)0.000 (3)
C2Y0.033 (5)0.030 (4)0.041 (5)0.007 (3)0.001 (4)0.012 (3)
C3Y0.043 (6)0.047 (7)0.049 (6)0.011 (4)0.020 (6)0.017 (4)
C4Y0.055 (6)0.058 (7)0.036 (3)0.016 (4)0.012 (4)0.007 (4)
C5Y0.049 (4)0.055 (4)0.044 (4)0.013 (4)0.004 (4)0.008 (3)
C6Y0.039 (4)0.051 (4)0.038 (4)0.006 (3)0.002 (3)0.001 (3)
C7Y0.035 (2)0.041 (3)0.029 (2)0.003 (2)0.0028 (19)0.007 (2)
C8Y0.052 (5)0.039 (4)0.056 (4)0.003 (3)0.004 (3)0.005 (3)
N1B0.1021 (16)0.0423 (9)0.0426 (9)0.0262 (10)0.0318 (10)0.0166 (8)
N2B0.0649 (10)0.0235 (6)0.0300 (7)0.0002 (7)0.0011 (7)0.0023 (5)
C9B0.0752 (15)0.0299 (9)0.0605 (13)0.0017 (9)0.0188 (11)0.0133 (9)
C10B0.0715 (14)0.0323 (9)0.0411 (10)0.0152 (9)0.0069 (9)0.0089 (8)
C11B0.167 (4)0.0514 (18)0.0181 (11)0.048 (2)0.0000.000
C12B0.0759 (19)0.0316 (12)0.0211 (10)0.0036 (13)0.0000.000
Geometric parameters (Å, º) top
O1A—C7A1.306 (2)C3B—H3BA0.9500
O1A—H1O10.870 (18)C4B—C5B1.395 (7)
O2A—C7A1.210 (2)C4B—H4BA0.9500
N1A—C11A1.4725 (19)C5B—C6B1.382 (6)
N1A—C10Ai1.480 (2)C5B—H5BA0.9500
N1A—C9A1.481 (2)C6B—H6BA0.9500
N2A—C9A1.453 (2)C8B—H8BA0.9800
N2A—C10A1.458 (2)C8B—H8BB0.9800
N2A—C12A1.4721 (19)C8B—H8BC0.9800
C1A—C2A1.396 (3)O1Y—C7Y1.312 (6)
C1A—C6A1.412 (3)O1Y—H3O10.83 (2)
C1A—C7A1.491 (2)O2Y—C7Y1.202 (7)
C2A—C3A1.403 (3)C1Y—C6Y1.388 (11)
C2A—C8A1.489 (3)C1Y—C2Y1.398 (15)
C3A—C4A1.368 (3)C1Y—C7Y1.500 (9)
C3A—H3AA0.9500C2Y—C3Y1.409 (14)
C4A—C5A1.390 (3)C2Y—C8Y1.514 (19)
C4A—H4AA0.9500C3Y—C4Y1.380 (13)
C5A—C6A1.370 (3)C3Y—H3YA0.9500
C5A—H5AA0.9500C4Y—C5Y1.375 (10)
C6A—H6AA0.9500C4Y—H4YA0.9500
C8A—H8AA0.9800C5Y—C6Y1.373 (8)
C8A—H8AB0.9800C5Y—H5YA0.9500
C8A—H8AC0.9800C6Y—H6YA0.9500
C9A—H9AA0.9900C8Y—H8YA0.9800
C9A—H9AB0.9900C8Y—H8YB0.9800
C10A—N1Ai1.480 (2)C8Y—H8YC0.9800
C10A—H10A0.9900N1B—C11B1.468 (3)
C10A—H10B0.9900N1B—C9B1.476 (3)
C11A—N1Ai1.4726 (19)N1B—C10Bii1.481 (2)
C11A—H11A0.9497N2B—C9B1.453 (3)
C12A—N2Ai1.4720 (19)N2B—C10B1.455 (3)
C12A—H12A0.9523N2B—C12B1.4710 (18)
O1B—C7B1.310 (4)C9B—H9BA0.9900
O1B—H2O10.82 (2)C9B—H9BB0.9900
O2B—C7B1.204 (5)C10B—N1Bii1.481 (2)
C1B—C6B1.392 (8)C10B—H10C0.9900
C1B—C2B1.402 (11)C10B—H10D0.9900
C1B—C7B1.498 (7)C11B—N1Bii1.468 (3)
C2B—C3B1.385 (11)C11B—H11C0.9496
C2B—C8B1.510 (14)C12B—N2Bii1.4710 (18)
C3B—C4B1.374 (9)C12B—H12C0.9523
C7A—O1A—H1O1110 (2)C6B—C5B—H5BA120.8
C11A—N1A—C10Ai108.11 (12)C4B—C5B—H5BA120.8
C11A—N1A—C9A108.13 (12)C5B—C6B—C1B121.7 (5)
C10Ai—N1A—C9A107.88 (13)C5B—C6B—H6BA119.1
C9A—N2A—C10A108.25 (13)C1B—C6B—H6BA119.1
C9A—N2A—C12A108.39 (12)O2B—C7B—O1B122.7 (4)
C10A—N2A—C12A108.20 (12)O2B—C7B—C1B120.8 (5)
C2A—C1A—C6A119.44 (16)O1B—C7B—C1B116.5 (5)
C2A—C1A—C7A122.90 (17)C2B—C8B—H8BA109.5
C6A—C1A—C7A117.60 (17)C2B—C8B—H8BB109.5
C1A—C2A—C3A117.82 (18)H8BA—C8B—H8BB109.5
C1A—C2A—C8A124.25 (17)C2B—C8B—H8BC109.5
C3A—C2A—C8A117.92 (18)H8BA—C8B—H8BC109.5
C4A—C3A—C2A121.9 (2)H8BB—C8B—H8BC109.5
C4A—C3A—H3AA119.1C7Y—O1Y—H3O1108 (7)
C2A—C3A—H3AA119.1C6Y—C1Y—C2Y119.8 (10)
C3A—C4A—C5A120.56 (18)C6Y—C1Y—C7Y118.2 (9)
C3A—C4A—H4AA119.7C2Y—C1Y—C7Y121.8 (11)
C5A—C4A—H4AA119.7C1Y—C2Y—C3Y118.1 (14)
C6A—C5A—C4A118.78 (19)C1Y—C2Y—C8Y123.5 (12)
C6A—C5A—H5AA120.6C3Y—C2Y—C8Y118.1 (11)
C4A—C5A—H5AA120.6C4Y—C3Y—C2Y120.2 (13)
C5A—C6A—C1A121.54 (19)C4Y—C3Y—H3YA119.9
C5A—C6A—H6AA119.2C2Y—C3Y—H3YA119.9
C1A—C6A—H6AA119.2C5Y—C4Y—C3Y121.3 (9)
O2A—C7A—O1A122.11 (18)C5Y—C4Y—H4YA119.4
O2A—C7A—C1A123.98 (18)C3Y—C4Y—H4YA119.4
O1A—C7A—C1A113.90 (17)C6Y—C5Y—C4Y118.8 (9)
C2A—C8A—H8AA109.5C6Y—C5Y—H5YA120.6
C2A—C8A—H8AB109.5C4Y—C5Y—H5YA120.6
H8AA—C8A—H8AB109.5C5Y—C6Y—C1Y121.6 (9)
C2A—C8A—H8AC109.5C5Y—C6Y—H6YA119.2
H8AA—C8A—H8AC109.5C1Y—C6Y—H6YA119.2
H8AB—C8A—H8AC109.5O2Y—C7Y—O1Y122.7 (5)
N2A—C9A—N1A112.22 (13)O2Y—C7Y—C1Y123.8 (7)
N2A—C9A—H9AA109.2O1Y—C7Y—C1Y113.5 (7)
N1A—C9A—H9AA109.2C2Y—C8Y—H8YA109.5
N2A—C9A—H9AB109.2C2Y—C8Y—H8YB109.5
N1A—C9A—H9AB109.2H8YA—C8Y—H8YB109.5
H9AA—C9A—H9AB107.9C2Y—C8Y—H8YC109.5
N2A—C10A—N1Ai112.19 (13)H8YA—C8Y—H8YC109.5
N2A—C10A—H10A109.2H8YB—C8Y—H8YC109.5
N1Ai—C10A—H10A109.2C11B—N1B—C9B107.96 (16)
N2A—C10A—H10B109.2C11B—N1B—C10Bii108.29 (17)
N1Ai—C10A—H10B109.2C9B—N1B—C10Bii108.57 (15)
H10A—C10A—H10B107.9C9B—N2B—C10B108.79 (16)
N1A—C11A—N1Ai111.37 (17)C9B—N2B—C12B107.94 (14)
N1A—C11A—H11A109.7C10B—N2B—C12B108.33 (13)
N1Ai—C11A—H11A109.3N2B—C9B—N1B111.97 (17)
N2Ai—C12A—N2A112.02 (18)N2B—C9B—H9BA109.2
N2Ai—C12A—H12A109.7N1B—C9B—H9BA109.2
N2A—C12A—H12A108.9N2B—C9B—H9BB109.2
C7B—O1B—H2O1112 (5)N1B—C9B—H9BB109.2
C6B—C1B—C2B120.1 (7)H9BA—C9B—H9BB107.9
C6B—C1B—C7B115.1 (6)N2B—C10B—N1Bii111.32 (16)
C2B—C1B—C7B124.8 (7)N2B—C10B—H10C109.4
C3B—C2B—C1B116.7 (10)N1Bii—C10B—H10C109.4
C3B—C2B—C8B117.6 (8)N2B—C10B—H10D109.4
C1B—C2B—C8B125.6 (9)N1Bii—C10B—H10D109.4
C4B—C3B—C2B123.5 (10)H10C—C10B—H10D108.0
C4B—C3B—H3BA118.2N1B—C11B—N1Bii111.5 (2)
C2B—C3B—H3BA118.2N1B—C11B—H11C108.9
C3B—C4B—C5B119.3 (7)N1Bii—C11B—H11C110.0
C3B—C4B—H4BA120.3N2B—C12B—N2Bii112.38 (18)
C5B—C4B—H4BA120.3N2B—C12B—H12C109.7
C6B—C5B—C4B118.4 (6)N2Bii—C12B—H12C108.7
C6A—C1A—C2A—C3A0.3 (3)C4B—C5B—C6B—C1B0.1 (13)
C7A—C1A—C2A—C3A177.09 (16)C2B—C1B—C6B—C5B3 (2)
C6A—C1A—C2A—C8A179.21 (18)C7B—C1B—C6B—C5B178.6 (8)
C7A—C1A—C2A—C8A1.8 (3)C6B—C1B—C7B—O2B20.1 (16)
C1A—C2A—C3A—C4A0.5 (3)C2B—C1B—C7B—O2B161.6 (18)
C8A—C2A—C3A—C4A179.46 (18)C6B—C1B—C7B—O1B161.2 (9)
C2A—C3A—C4A—C5A0.1 (3)C2B—C1B—C7B—O1B17 (2)
C3A—C4A—C5A—C6A0.5 (3)C6Y—C1Y—C2Y—C3Y5 (5)
C4A—C5A—C6A—C1A0.7 (3)C7Y—C1Y—C2Y—C3Y179 (3)
C2A—C1A—C6A—C5A0.3 (3)C6Y—C1Y—C2Y—C8Y179 (2)
C7A—C1A—C6A—C5A177.82 (17)C7Y—C1Y—C2Y—C8Y8 (5)
C2A—C1A—C7A—O2A7.5 (3)C1Y—C2Y—C3Y—C4Y5 (5)
C6A—C1A—C7A—O2A175.1 (2)C8Y—C2Y—C3Y—C4Y179 (2)
C2A—C1A—C7A—O1A171.52 (17)C2Y—C3Y—C4Y—C5Y3 (4)
C6A—C1A—C7A—O1A5.9 (2)C3Y—C4Y—C5Y—C6Y1 (2)
C10A—N2A—C9A—N1A58.75 (18)C4Y—C5Y—C6Y—C1Y0.5 (18)
C12A—N2A—C9A—N1A58.39 (18)C2Y—C1Y—C6Y—C5Y3 (3)
C11A—N1A—C9A—N2A58.76 (17)C7Y—C1Y—C6Y—C5Y176.7 (12)
C10Ai—N1A—C9A—N2A57.94 (18)C6Y—C1Y—C7Y—O2Y170.2 (12)
C9A—N2A—C10A—N1Ai58.78 (18)C2Y—C1Y—C7Y—O2Y16 (3)
C12A—N2A—C10A—N1Ai58.49 (17)C6Y—C1Y—C7Y—O1Y10 (2)
C10Ai—N1A—C11A—N1Ai58.29 (9)C2Y—C1Y—C7Y—O1Y164 (2)
C9A—N1A—C11A—N1Ai58.25 (10)C10B—N2B—C9B—N1B59.1 (2)
C9A—N2A—C12A—N2Ai58.61 (10)C12B—N2B—C9B—N1B58.2 (2)
C10A—N2A—C12A—N2Ai58.56 (9)C11B—N1B—C9B—N2B58.7 (2)
C6B—C1B—C2B—C3B6 (3)C10Bii—N1B—C9B—N2B58.5 (2)
C7B—C1B—C2B—C3B176.2 (19)C9B—N2B—C10B—N1Bii58.8 (2)
C6B—C1B—C2B—C8B178.6 (18)C12B—N2B—C10B—N1Bii58.3 (2)
C7B—C1B—C2B—C8B0 (4)C9B—N1B—C11B—N1Bii58.53 (11)
C1B—C2B—C3B—C4B6 (4)C10Bii—N1B—C11B—N1Bii58.83 (11)
C8B—C2B—C3B—C4B178.1 (18)C9B—N2B—C12B—N2Bii58.64 (12)
C2B—C3B—C4B—C5B3 (3)C10B—N2B—C12B—N2Bii59.00 (11)
C3B—C4B—C5B—C6B0.0 (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···AD—HH···AD···AD—H···A
O1A—H1O1···N1A0.87 (2)1.81 (2)2.671 (2)169 (3)
O1B—H2O1···N1B0.82 (5)2.01 (5)2.818 (4)166 (6)
C6A—H6AA···O1A0.952.322.678 (2)101
C10A—H10B···O2B0.992.583.070 (4)110
C12A—H12A···O2Aiii0.952.433.375 (2)172
C12B—H12C···O2Biv0.952.383.321 (4)169
C8B—H8BA···O1B0.982.452.805 (8)101
Symmetry codes: (iii) x, y+3/2, z1/2; (iv) x+3/2, y, z1/2.
(300K) Hexamethylenetetramine–2-methylbenzoic acid (1/2) top
Crystal data top
C6H12N4·2C8H8O2Dx = 1.274 Mg m3
Mr = 41