Structures of cyclic dipeptides: an X-ray and computational study of cis- and trans-cyclo(Pip-Phe), cyclo(Pro-Phe) and their N-methyl derivatives

Budesinsky, M.; Cisarova, I.; Podlaha, J.; Borremans, F.; Martins, J.C.; Waroquier, M.; Pauwels, E.

doi:10.1107/S0108768110040243

Structures of cyclic dipeptides: an X-ray and computational study of cis- and trans-cyclo(Pip-Phe), cyclo(Pro-Phe) and their N-methyl derivatives

M. Budesinsky, I. Cisarova, J. Podlaha, F. Borremans, J. C. Martins, M. Waroquier and E. Pauwels

The crystal structures of eight cyclodipeptides are determined, incorporating pipecolic acid or proline and phenylalanine or N-methyl phenylalanine. This set of structures allows the evaluation of the effects on molecular conformation and crystal packing of imino acid ring-size, relative configuration of the two amino acids, and N-methylation. In the non-methylated compounds, hydrogen-bonding interactions form one-dimensional motifs that dominate the packing arrangement. Three compounds have more than one symmetry-independent molecule in the asymmetric unit (Z′ > 1), indicative of a broad and shallow molecular energy minimum. Density functional theory calculations reveal the interplay between inter- and intramolecular factors in the crystals. Only for the N-methylated compounds do simulations of the molecules in the isolated state succeed to reproduce the observed crystallographic conformations. Puckering of the diketopiperazine ring and the deviation from planarity of the amide bonds are not reproduced in the remaining compounds. Cluster in vacuo calculations with a central cyclodipeptide molecule surrounded by hydrogen-bound molecules establish that hydrogen bonding is of major importance but that other intermolecular interactions must also contribute substantially to the crystal structure. More advanced periodic calculations, incorporating the crystallographic environment to the full extent, are necessary to correctly describe all the conformational features of these cyclodipeptide crystals.

Keywords: cyclic dipeptides; cluster in vacuo; periodic approach.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768110040243/so5040sup1.cif Contains datablocks 1a, 1a-room, 1b, 2a, 2b, 9a, 9b, 9b-room, 10a, 10b, 10b-room
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50401asup2.hkl Contains datablock 1a
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50401asup3.hkl Contains datablock 1a
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50401a-roomsup4.hkl Contains datablock 1a-room
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50401bsup5.hkl Contains datablock 1b
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50402asup6.hkl Contains datablock 2a
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50402bsup7.hkl Contains datablock 2b
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50409asup8.hkl Contains datablock 9a
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50409bsup9.hkl Contains datablock 9b
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50409b-roomsup10.hkl Contains datablock 9b-room
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so504010asup11.hkl Contains datablock 10a
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so504010bsup12.hkl Contains datablock 10b
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so504010b-roomsup13.hkl Contains datablock 10b-room
	Portable Document Format (PDF) file https://doi.org/10.1107/S0108768110040243/so5040sup14.pdf Extra tables and figures

CCDC references: 755931; 755932; 755933; 755934; 755935; 755936; 755937; 755938; 810883; 810884; 810885

Computing details top

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997) for (1a), 1a-room, (1b), (2a), (2b), (9a), (9b), (10a), (10b); Enraf-Nonius CAD4 Version 5.0 for 9b-room, 10b-room. Cell refinement: COLLECT and DENZO for (1a), 1a-room, (1b), (2a), (2b), (9a), (9b), (10a), (10b); Enraf-Nonius CAD4 Version 5.0 for 9b-room, 10b-room. Data reduction: COLLECT and DENZO for (1a), 1a-room, (1b), (2a), (2b), (9a), (9b), (10a), (10b); JANA2006, (Petricek,2006) for 9b-room, 10b-room. Program(s) used to solve structure: SIR92 (Altomare et al., 1994) for (1a), 1a-room, (1b), (2a), (2b), (9a), (9b), (10a), (10b); SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79) for 9b-room, 10b-room. For all structures, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(1a) top

Crystal data top

2(C₁₅H₁₈N₄O₄)·H₂O	F(000) = 1144
M_r = 534.64	D_x = 1.269 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2yb	Cell parameters from 25066 reflections
a = 8.4202 (2) Å	θ = 1–25.0°
b = 24.7788 (4) Å	µ = 0.09 mm⁻¹
c = 13.4204 (3) Å	T = 150 K
β = 91.6730 (11)°	Plate, colourless
V = 2798.87 (10) Å³	0.3 × 0.25 × 0.25 mm
Z = 4

Data collection top

Nonius KappaCCD area detector diffractometer	8038 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.060
Graphite monochromator	θ_max = 25.0°, θ_min = 1.5°
Detector resolution: 9.091 pixels mm^-1	h = −10→9
φ and ω scans to fill the Ewald sphere	k = −29→27
31329 measured reflections	l = −15→15
9713 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.054	w = 1/[σ²(F_o²) + (0.077P)² + 0.7105P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.137	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.32 e Å⁻³
9713 reflections	Δρ_min = −0.23 e Å⁻³
736 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0273 (18)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.2 (10)

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
N11	0.6263 (3)	0.26408 (10)	0.41438 (18)	0.0328 (6)
C12	0.7683 (4)	0.25815 (12)	0.3764 (2)	0.0310 (7)
O12	0.8290 (3)	0.21328 (8)	0.35927 (17)	0.0396 (5)
C13	0.8666 (3)	0.30768 (11)	0.3543 (2)	0.0332 (7)
H13	0.9055	0.3037	0.2866	0.040*
N14	0.7782 (3)	0.35798 (10)	0.35732 (19)	0.0317 (6)
C15	0.6330 (4)	0.36411 (12)	0.3895 (2)	0.0317 (7)
O15	0.5649 (3)	0.40899 (9)	0.39059 (17)	0.0433 (6)
C16	0.5454 (3)	0.31581 (12)	0.4283 (2)	0.0330 (7)
H16	0.4442	0.3138	0.3905	0.040*
C17	0.5055 (4)	0.32292 (13)	0.5372 (3)	0.0438 (8)
H17A	0.4448	0.3558	0.5450	0.053*
H17B	0.6029	0.3262	0.5771	0.053*
C18	0.4099 (4)	0.27523 (14)	0.5742 (3)	0.0467 (9)
H18A	0.3949	0.2790	0.6452	0.056*
H18B	0.3059	0.2752	0.5411	0.056*
C19	0.4927 (4)	0.22198 (13)	0.5542 (2)	0.0393 (7)
H19A	0.5896	0.2197	0.5949	0.047*
H19B	0.4242	0.1923	0.5724	0.047*
C110	0.5323 (4)	0.21735 (13)	0.4450 (3)	0.0416 (8)
H11A	0.5919	0.1845	0.4343	0.050*
H11B	0.4348	0.2155	0.4048	0.050*
C111	1.0139 (3)	0.30983 (13)	0.4264 (3)	0.0390 (7)
H11C	1.0784	0.2780	0.4162	0.047*
H11D	1.0774	0.3411	0.4103	0.047*
C112	0.9711 (4)	0.31271 (13)	0.5343 (2)	0.0379 (7)
C113	0.9509 (4)	0.36186 (14)	0.5808 (3)	0.0504 (9)
H113	0.9652	0.3936	0.5453	0.060*
C114	0.9096 (6)	0.36432 (16)	0.6797 (3)	0.0668 (12)
H114	0.8968	0.3977	0.7100	0.080*
C115	0.8870 (6)	0.31763 (16)	0.7338 (3)	0.0663 (12)
H115	0.8596	0.3194	0.8003	0.080*
C116	0.9057 (5)	0.26840 (14)	0.6876 (3)	0.0551 (10)
H116	0.8890	0.2367	0.7229	0.066*
C117	0.9491 (4)	0.26592 (13)	0.5895 (2)	0.0426 (8)
H117	0.9639	0.2325	0.5597	0.051*
N21	0.7543 (3)	0.05767 (10)	0.62446 (19)	0.0332 (6)
C22	0.8586 (4)	0.09464 (12)	0.6568 (2)	0.0343 (7)
O22	0.8274 (3)	0.14345 (9)	0.65905 (19)	0.0484 (6)
C23	1.0233 (4)	0.07749 (12)	0.6882 (2)	0.0352 (7)
H23	1.0459	0.0932	0.7541	0.042*
N24	1.0421 (3)	0.01897 (10)	0.69821 (19)	0.0342 (6)
C25	0.9404 (4)	−0.01779 (12)	0.6630 (2)	0.0326 (7)
O25	0.9698 (3)	−0.06727 (8)	0.67021 (17)	0.0410 (5)
C26	0.7863 (4)	−0.00055 (11)	0.6152 (2)	0.0313 (7)
H26	0.7014	−0.0198	0.6487	0.038*
C27	0.7778 (4)	−0.01700 (13)	0.5046 (2)	0.0360 (7)
H27A	0.8675	−0.0016	0.4709	0.043*
H27B	0.7849	−0.0560	0.4995	0.043*
C28	0.6241 (4)	0.00206 (13)	0.4533 (3)	0.0425 (8)
H28A	0.5357	−0.0184	0.4787	0.051*
H28B	0.6289	−0.0048	0.3823	0.051*
C29	0.5956 (4)	0.06199 (14)	0.4703 (3)	0.0427 (8)
H29A	0.6766	0.0829	0.4377	0.051*
H29B	0.4929	0.0722	0.4416	0.051*
C210	0.6006 (4)	0.07401 (13)	0.5809 (3)	0.0401 (8)
H21A	0.5846	0.1123	0.5915	0.048*
H21B	0.5161	0.0546	0.6129	0.048*
C211	1.1458 (4)	0.10086 (13)	0.6171 (2)	0.0372 (7)
H21C	1.1351	0.1398	0.6155	0.045*
H21D	1.2518	0.0925	0.6428	0.045*
C212	1.1267 (4)	0.07916 (12)	0.5124 (2)	0.0342 (7)
C213	1.0324 (4)	0.10571 (13)	0.4414 (2)	0.0399 (8)
H213	0.9834	0.1379	0.4583	0.048*
C214	1.0098 (5)	0.08536 (15)	0.3467 (3)	0.0518 (9)
H214	0.9455	0.1036	0.3003	0.062*
C215	1.0833 (5)	0.03748 (16)	0.3208 (3)	0.0521 (10)
H215	1.0688	0.0236	0.2568	0.063*
C216	1.1777 (4)	0.01056 (15)	0.3898 (3)	0.0477 (9)
H216	1.2278	−0.0214	0.3723	0.057*
C217	1.1983 (4)	0.03100 (13)	0.4855 (2)	0.0382 (7)
H217	1.2607	0.0123	0.5322	0.046*
N31	0.7141 (3)	0.14447 (10)	0.12665 (19)	0.0346 (6)
C32	0.6162 (4)	0.10629 (12)	0.1599 (2)	0.0347 (7)
O32	0.6514 (3)	0.05793 (9)	0.1602 (2)	0.0494 (6)
C33	0.4556 (4)	0.12232 (12)	0.1940 (2)	0.0363 (7)
H33	0.4420	0.1056	0.2594	0.044*
N34	0.4338 (3)	0.18010 (10)	0.20695 (19)	0.0344 (6)
C35	0.5299 (4)	0.21839 (13)	0.1754 (2)	0.0340 (7)
O35	0.5002 (3)	0.26704 (8)	0.18591 (17)	0.0431 (6)
C36	0.6795 (4)	0.20251 (12)	0.1239 (2)	0.0331 (7)
H36	0.7682	0.2210	0.1584	0.040*
C37	0.6745 (4)	0.22241 (13)	0.0153 (2)	0.0382 (7)
H37A	0.5817	0.2075	−0.0192	0.046*
H37B	0.6646	0.2614	0.0146	0.046*
C38	0.8220 (4)	0.20624 (15)	−0.0391 (3)	0.0477 (9)
H38A	0.9127	0.2258	−0.0114	0.057*
H38B	0.8093	0.2160	−0.1089	0.057*
C39	0.8533 (4)	0.14563 (14)	−0.0306 (3)	0.0458 (8)
H39A	0.7689	0.1259	−0.0651	0.055*
H39B	0.9528	0.1368	−0.0614	0.055*
C310	0.8611 (4)	0.12945 (14)	0.0789 (3)	0.0449 (8)
H31A	0.8771	0.0908	0.0845	0.054*
H31B	0.9503	0.1473	0.1123	0.054*
C311	0.3264 (4)	0.09830 (13)	0.1230 (2)	0.0382 (7)
H31C	0.3389	0.0594	0.1209	0.046*
H31D	0.2227	0.1060	0.1493	0.046*
C312	0.3328 (4)	0.12018 (13)	0.0188 (2)	0.0369 (7)
C313	0.2558 (4)	0.16822 (13)	−0.0067 (3)	0.0402 (8)
H313	0.1980	0.1864	0.0409	0.048*
C314	0.2643 (4)	0.18934 (15)	−0.1020 (3)	0.0484 (9)
H314	0.2106	0.2210	−0.1187	0.058*
C315	0.3535 (5)	0.16292 (16)	−0.1724 (3)	0.0552 (10)
H315	0.3601	0.1771	−0.2363	0.066*
C316	0.4319 (5)	0.11594 (16)	−0.1484 (3)	0.0560 (10)
H316	0.4930	0.0987	−0.1954	0.067*
C317	0.4198 (4)	0.09419 (14)	−0.0537 (3)	0.0451 (8)
H317	0.4706	0.0618	−0.0384	0.054*
N41	0.8721 (3)	−0.05542 (9)	−0.09715 (18)	0.0316 (6)
C42	0.7229 (4)	−0.05342 (12)	−0.1329 (2)	0.0321 (7)
O42	0.6501 (3)	−0.01000 (8)	−0.14541 (17)	0.0391 (5)
C43	0.6360 (3)	−0.10471 (11)	−0.1565 (2)	0.0316 (7)
H43	0.5869	−0.1009	−0.2233	0.038*
N44	0.7371 (3)	−0.15279 (10)	−0.15730 (19)	0.0329 (6)
C45	0.8872 (4)	−0.15539 (12)	−0.1268 (2)	0.0333 (7)
O45	0.9653 (3)	−0.19805 (8)	−0.12731 (17)	0.0433 (6)
C46	0.9698 (3)	−0.10473 (12)	−0.0897 (2)	0.0330 (7)
H46	1.0615	−0.0991	−0.1318	0.040*
C47	1.0348 (4)	−0.11212 (13)	0.0169 (2)	0.0400 (7)
H47A	0.9478	−0.1203	0.0603	0.048*
H47B	1.1078	−0.1424	0.0191	0.048*
C48	1.1201 (4)	−0.06187 (15)	0.0543 (3)	0.0458 (8)
H48A	1.1517	−0.0666	0.1239	0.055*
H48B	1.2154	−0.0564	0.0167	0.055*
C49	1.0142 (4)	−0.01272 (13)	0.0437 (2)	0.0396 (7)
H49A	0.9245	−0.0165	0.0869	0.048*
H49B	1.0733	0.0192	0.0642	0.048*
C410	0.9547 (4)	−0.00611 (12)	−0.0625 (3)	0.0398 (7)
H41A	0.8824	0.0243	−0.0670	0.048*
H41B	1.0435	0.0012	−0.1049	0.048*
C411	0.5012 (4)	−0.11192 (14)	−0.0822 (2)	0.0389 (7)
H41C	0.4272	−0.0821	−0.0900	0.047*
H41D	0.4439	−0.1449	−0.0983	0.047*
C412	0.5592 (4)	−0.11436 (13)	0.0244 (2)	0.0370 (7)
C413	0.5732 (4)	−0.06755 (13)	0.0821 (3)	0.0433 (8)
H413	0.5421	−0.0346	0.0545	0.052*
C414	0.6318 (5)	−0.06906 (14)	0.1786 (3)	0.0518 (10)
H414	0.6409	−0.0374	0.2154	0.062*
C415	0.6774 (5)	−0.11759 (15)	0.2210 (3)	0.0561 (10)
H415	0.7155	−0.1189	0.2867	0.067*
C416	0.6659 (6)	−0.16415 (15)	0.1649 (3)	0.0585 (11)
H416	0.6986	−0.1969	0.1926	0.070*
C417	0.6065 (5)	−0.16256 (13)	0.0688 (3)	0.0455 (8)
H417	0.5977	−0.1945	0.0326	0.055*
O1W	0.1138 (3)	0.21200 (10)	0.2438 (2)	0.0475 (6)
O2W	1.3586 (3)	−0.01206 (11)	0.7449 (2)	0.0517 (7)
H14	0.835 (5)	0.3870 (18)	0.336 (3)	0.062 (12)*
H24	1.156 (4)	0.0089 (12)	0.717 (2)	0.031 (8)*
H34	0.324 (4)	0.1929 (13)	0.232 (2)	0.037 (8)*
H44	0.677 (4)	−0.1838 (16)	−0.162 (3)	0.044 (9)*
H11W	0.025 (5)	0.2084 (17)	0.286 (3)	0.066 (12)*
H12W	0.092 (5)	0.242 (2)	0.199 (4)	0.076 (13)*
H21W	1.474 (5)	−0.0106 (16)	0.769 (3)	0.063 (11)*
H22W	1.383 (4)	−0.0330 (16)	0.706 (3)	0.041 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.0381 (14)	0.0275 (13)	0.0331 (14)	0.0009 (11)	0.0061 (11)	−0.0001 (11)
C12	0.0410 (17)	0.0277 (16)	0.0242 (15)	0.0022 (13)	0.0000 (12)	0.0001 (13)
O12	0.0519 (13)	0.0252 (12)	0.0423 (13)	0.0072 (10)	0.0123 (10)	0.0002 (9)
C13	0.0395 (16)	0.0254 (16)	0.0351 (17)	0.0025 (13)	0.0066 (13)	0.0041 (13)
N14	0.0397 (15)	0.0220 (13)	0.0336 (14)	0.0003 (11)	0.0041 (11)	0.0039 (11)
C15	0.0414 (18)	0.0265 (16)	0.0271 (16)	0.0067 (13)	−0.0038 (13)	0.0060 (12)
O15	0.0547 (13)	0.0335 (13)	0.0418 (14)	0.0137 (11)	0.0032 (10)	0.0057 (10)
C16	0.0329 (15)	0.0324 (16)	0.0336 (17)	0.0047 (13)	0.0022 (12)	0.0009 (13)
C17	0.054 (2)	0.0356 (18)	0.042 (2)	0.0099 (15)	0.0158 (16)	−0.0002 (14)
C18	0.051 (2)	0.045 (2)	0.045 (2)	0.0091 (16)	0.0189 (16)	0.0046 (16)
C19	0.0440 (18)	0.0363 (18)	0.0381 (19)	−0.0009 (14)	0.0077 (14)	0.0022 (14)
C110	0.0482 (19)	0.0356 (18)	0.0414 (19)	−0.0080 (15)	0.0089 (15)	−0.0024 (15)
C111	0.0341 (16)	0.0305 (17)	0.052 (2)	0.0040 (13)	0.0042 (14)	0.0057 (15)
C112	0.0381 (16)	0.0330 (17)	0.0421 (19)	−0.0014 (14)	−0.0081 (13)	0.0014 (15)
C113	0.071 (2)	0.0338 (19)	0.046 (2)	−0.0078 (17)	−0.0122 (18)	0.0038 (16)
C114	0.122 (4)	0.036 (2)	0.041 (2)	−0.006 (2)	−0.010 (2)	−0.0109 (17)
C115	0.119 (4)	0.045 (2)	0.034 (2)	−0.006 (2)	−0.013 (2)	−0.0031 (17)
C116	0.093 (3)	0.033 (2)	0.038 (2)	−0.0109 (18)	−0.0127 (19)	0.0029 (15)
C117	0.059 (2)	0.0296 (17)	0.039 (2)	0.0015 (15)	−0.0085 (15)	0.0000 (14)
N21	0.0359 (13)	0.0282 (14)	0.0353 (15)	0.0047 (11)	−0.0003 (11)	−0.0017 (11)
C22	0.0442 (18)	0.0241 (17)	0.0347 (17)	0.0020 (13)	0.0021 (14)	−0.0047 (13)
O22	0.0514 (14)	0.0256 (13)	0.0679 (17)	0.0047 (10)	−0.0014 (12)	−0.0053 (11)
C23	0.0453 (18)	0.0286 (16)	0.0315 (17)	−0.0019 (13)	−0.0018 (13)	−0.0077 (13)
N24	0.0424 (15)	0.0271 (14)	0.0331 (15)	0.0052 (12)	0.0003 (12)	0.0042 (11)
C25	0.0416 (17)	0.0283 (17)	0.0281 (16)	0.0019 (14)	0.0051 (13)	−0.0034 (13)
O25	0.0558 (14)	0.0248 (12)	0.0427 (14)	0.0062 (10)	0.0031 (10)	0.0037 (9)
C26	0.0401 (16)	0.0201 (15)	0.0340 (17)	0.0027 (12)	0.0057 (13)	−0.0004 (12)
C27	0.0381 (17)	0.0385 (18)	0.0316 (17)	−0.0030 (14)	0.0022 (13)	−0.0061 (14)
C28	0.0409 (18)	0.049 (2)	0.0378 (19)	−0.0058 (15)	−0.0003 (14)	−0.0008 (15)
C29	0.0357 (17)	0.044 (2)	0.048 (2)	−0.0039 (14)	−0.0012 (15)	0.0110 (16)
C210	0.0376 (17)	0.0290 (17)	0.054 (2)	0.0050 (13)	−0.0002 (15)	0.0042 (14)
C211	0.0383 (17)	0.0298 (17)	0.0431 (19)	0.0000 (13)	−0.0048 (14)	−0.0031 (14)
C212	0.0359 (16)	0.0327 (17)	0.0341 (17)	−0.0082 (13)	0.0017 (13)	0.0006 (13)
C213	0.0492 (19)	0.0329 (17)	0.0377 (19)	−0.0047 (14)	0.0024 (15)	0.0099 (14)
C214	0.065 (2)	0.049 (2)	0.042 (2)	−0.0084 (18)	−0.0021 (17)	0.0171 (17)
C215	0.068 (2)	0.058 (2)	0.0313 (19)	−0.0199 (19)	0.0087 (17)	−0.0038 (17)
C216	0.051 (2)	0.047 (2)	0.046 (2)	−0.0070 (16)	0.0137 (17)	−0.0113 (17)
C217	0.0325 (16)	0.0402 (19)	0.042 (2)	−0.0019 (14)	0.0033 (14)	0.0013 (15)
N31	0.0365 (14)	0.0270 (14)	0.0404 (16)	0.0046 (11)	0.0012 (11)	−0.0020 (11)
C32	0.0409 (17)	0.0276 (18)	0.0352 (18)	−0.0009 (14)	−0.0057 (13)	0.0014 (13)
O32	0.0543 (14)	0.0278 (13)	0.0658 (17)	0.0050 (10)	−0.0007 (12)	0.0034 (11)
C33	0.0464 (18)	0.0318 (17)	0.0305 (17)	−0.0005 (14)	−0.0008 (14)	0.0055 (13)
N34	0.0414 (15)	0.0327 (15)	0.0292 (14)	0.0042 (12)	0.0012 (11)	−0.0025 (11)
C35	0.0430 (17)	0.0312 (18)	0.0275 (17)	0.0035 (14)	−0.0059 (13)	−0.0018 (13)
O35	0.0544 (14)	0.0278 (13)	0.0471 (14)	0.0090 (10)	0.0004 (10)	−0.0033 (10)
C36	0.0363 (16)	0.0244 (16)	0.0382 (18)	−0.0006 (12)	−0.0034 (13)	−0.0015 (13)
C37	0.0392 (17)	0.0355 (18)	0.0400 (19)	−0.0023 (14)	0.0002 (14)	0.0064 (14)
C38	0.0416 (19)	0.058 (2)	0.044 (2)	−0.0074 (16)	0.0063 (15)	0.0058 (17)
C39	0.0376 (18)	0.051 (2)	0.049 (2)	−0.0028 (15)	0.0070 (15)	−0.0127 (17)
C310	0.0352 (17)	0.0398 (19)	0.060 (2)	0.0023 (14)	−0.0008 (15)	−0.0017 (16)
C311	0.0366 (16)	0.0347 (18)	0.0435 (19)	−0.0030 (13)	0.0052 (14)	0.0040 (14)
C312	0.0367 (17)	0.0344 (18)	0.0393 (19)	−0.0082 (14)	−0.0030 (14)	−0.0044 (14)
C313	0.0361 (17)	0.0415 (19)	0.043 (2)	−0.0023 (14)	−0.0015 (14)	−0.0010 (15)
C314	0.052 (2)	0.048 (2)	0.044 (2)	−0.0095 (17)	−0.0123 (16)	0.0079 (17)
C315	0.076 (3)	0.059 (3)	0.0304 (19)	−0.024 (2)	−0.0071 (18)	−0.0001 (17)
C316	0.079 (3)	0.056 (2)	0.034 (2)	−0.013 (2)	0.0008 (18)	−0.0128 (18)
C317	0.058 (2)	0.0396 (19)	0.037 (2)	−0.0040 (16)	−0.0004 (16)	−0.0100 (15)
N41	0.0393 (14)	0.0228 (12)	0.0325 (14)	0.0031 (10)	−0.0041 (11)	−0.0023 (10)
C42	0.0413 (17)	0.0297 (17)	0.0253 (16)	0.0019 (14)	−0.0004 (12)	0.0024 (13)
O42	0.0513 (13)	0.0267 (12)	0.0388 (13)	0.0068 (10)	−0.0082 (10)	−0.0011 (9)
C43	0.0396 (16)	0.0264 (16)	0.0286 (16)	0.0027 (13)	−0.0039 (12)	−0.0036 (12)
N44	0.0390 (15)	0.0227 (14)	0.0370 (15)	0.0012 (11)	0.0003 (11)	−0.0028 (11)
C45	0.0420 (18)	0.0298 (17)	0.0282 (17)	0.0065 (13)	0.0037 (13)	−0.0015 (12)
O45	0.0526 (13)	0.0331 (13)	0.0442 (14)	0.0135 (11)	0.0010 (10)	−0.0051 (10)
C46	0.0331 (15)	0.0357 (18)	0.0300 (16)	0.0060 (13)	0.0012 (12)	−0.0007 (13)
C47	0.0453 (18)	0.0398 (18)	0.0344 (18)	0.0098 (15)	−0.0045 (14)	−0.0018 (14)
C48	0.0411 (18)	0.060 (2)	0.0359 (19)	0.0015 (16)	−0.0052 (14)	−0.0064 (17)
C49	0.0400 (17)	0.0430 (19)	0.0358 (18)	−0.0045 (14)	0.0024 (13)	−0.0082 (14)
C410	0.0433 (18)	0.0317 (17)	0.044 (2)	−0.0063 (14)	−0.0043 (14)	−0.0067 (14)
C411	0.0380 (17)	0.0355 (18)	0.0434 (19)	0.0040 (14)	0.0021 (14)	−0.0067 (15)
C412	0.0352 (16)	0.0346 (17)	0.0416 (19)	−0.0045 (13)	0.0089 (13)	−0.0029 (15)
C413	0.054 (2)	0.0346 (19)	0.042 (2)	0.0011 (15)	0.0099 (16)	−0.0018 (15)
C414	0.087 (3)	0.034 (2)	0.034 (2)	−0.0045 (18)	0.0135 (18)	−0.0034 (15)
C415	0.090 (3)	0.047 (2)	0.032 (2)	−0.002 (2)	0.0076 (18)	0.0041 (17)
C416	0.105 (3)	0.034 (2)	0.037 (2)	−0.0002 (19)	0.011 (2)	0.0049 (15)
C417	0.069 (2)	0.0292 (18)	0.039 (2)	−0.0040 (15)	0.0113 (17)	−0.0004 (14)
O1W	0.0531 (15)	0.0352 (13)	0.0556 (16)	0.0082 (11)	0.0228 (12)	0.0060 (11)
O2W	0.0529 (16)	0.0472 (15)	0.0538 (17)	0.0161 (12)	−0.0180 (12)	−0.0162 (13)

Geometric parameters (Å, º) top

N11—C12	1.321 (4)	N31—C36	1.467 (4)
N11—C16	1.466 (4)	C32—O32	1.234 (4)
N11—C110	1.468 (4)	C32—C33	1.494 (5)
C12—O12	1.248 (4)	C33—N34	1.455 (4)
C12—C13	1.515 (4)	C33—C311	1.544 (5)
C13—N14	1.453 (4)	C33—H33	0.9800
C13—C111	1.551 (4)	N34—C35	1.325 (4)
C13—H13	0.9800	N34—H34	1.04 (3)
N14—C15	1.317 (4)	C35—O35	1.240 (4)
N14—H14	0.92 (4)	C35—C36	1.507 (5)
C15—O15	1.252 (4)	C36—C37	1.538 (4)
C15—C16	1.506 (4)	C36—H36	0.9800
C16—C17	1.520 (4)	C37—C38	1.513 (5)
C16—H16	0.9800	C37—H37A	0.9700
C17—C18	1.521 (5)	C37—H37B	0.9700
C17—H17A	0.9700	C38—C39	1.528 (5)
C17—H17B	0.9700	C38—H38A	0.9700
C18—C19	1.520 (5)	C38—H38B	0.9700
C18—H18A	0.9700	C39—C310	1.523 (5)
C18—H18B	0.9700	C39—H39A	0.9700
C19—C110	1.517 (4)	C39—H39B	0.9700
C19—H19A	0.9700	C310—H31A	0.9700
C19—H19B	0.9700	C310—H31B	0.9700
C110—H11A	0.9700	C311—C312	1.502 (5)
C110—H11B	0.9700	C311—H31C	0.9700
C111—C112	1.505 (5)	C311—H31D	0.9700
C111—H11C	0.9700	C312—C317	1.393 (5)
C111—H11D	0.9700	C312—C313	1.393 (5)
C112—C113	1.381 (5)	C313—C314	1.386 (5)
C112—C117	1.391 (5)	C313—H313	0.9300
C113—C114	1.382 (6)	C314—C315	1.388 (6)
C113—H113	0.9300	C314—H314	0.9300
C114—C115	1.382 (6)	C315—C316	1.372 (6)
C114—H114	0.9300	C315—H315	0.9300
C115—C116	1.379 (5)	C316—C317	1.386 (5)
C115—H115	0.9300	C316—H316	0.9300
C116—C117	1.378 (5)	C317—H317	0.9300
C116—H116	0.9300	N41—C42	1.333 (4)
C117—H117	0.9300	N41—C410	1.475 (4)
N21—C22	1.333 (4)	N41—C46	1.475 (4)
N21—C210	1.462 (4)	C42—O42	1.247 (4)
N21—C26	1.474 (4)	C42—C43	1.496 (4)
C22—O22	1.238 (4)	C43—N44	1.464 (4)
C22—C23	1.499 (5)	C43—C411	1.544 (4)
C23—N24	1.464 (4)	C43—H43	0.9800
C23—C211	1.538 (5)	N44—C45	1.318 (4)
C23—H23	0.9800	N44—H44	0.92 (4)
N24—C25	1.328 (4)	C45—O45	1.245 (4)
N24—H24	1.01 (3)	C45—C46	1.513 (4)
C25—O25	1.254 (4)	C46—C47	1.527 (4)
C25—C26	1.493 (4)	C46—H46	0.9800
C26—C27	1.539 (4)	C47—C48	1.516 (5)
C26—H26	0.9800	C47—H47A	0.9700
C27—C28	1.522 (5)	C47—H47B	0.9700
C27—H27A	0.9700	C48—C49	1.514 (5)
C27—H27B	0.9700	C48—H48A	0.9700
C28—C29	1.523 (5)	C48—H48B	0.9700
C28—H28A	0.9700	C49—C410	1.505 (5)
C28—H28B	0.9700	C49—H49A	0.9700
C29—C210	1.513 (5)	C49—H49B	0.9700
C29—H29A	0.9700	C410—H41A	0.9700
C29—H29B	0.9700	C410—H41B	0.9700
C210—H21A	0.9700	C411—C412	1.499 (5)
C210—H21B	0.9700	C411—H41C	0.9700
C211—C212	1.510 (4)	C411—H41D	0.9700
C211—H21C	0.9700	C412—C417	1.388 (5)
C211—H21D	0.9700	C412—C413	1.397 (5)
C212—C213	1.388 (5)	C413—C414	1.373 (5)
C212—C217	1.389 (5)	C413—H413	0.9300
C213—C214	1.375 (5)	C414—C415	1.380 (5)
C213—H213	0.9300	C414—H414	0.9300
C214—C215	1.387 (5)	C415—C416	1.379 (5)
C214—H214	0.9300	C415—H415	0.9300
C215—C216	1.376 (5)	C416—C417	1.370 (6)
C215—H215	0.9300	C416—H416	0.9300
C216—C217	1.387 (5)	C417—H417	0.9300
C216—H216	0.9300	O1W—H11W	0.95 (5)
C217—H217	0.9300	O1W—H12W	0.97 (5)
N31—C32	1.340 (4)	O2W—H21W	1.02 (5)
N31—C310	1.459 (4)	O2W—H22W	0.77 (4)

C12—N11—C16	125.1 (2)	C32—N31—C36	125.3 (3)
C12—N11—C110	121.4 (3)	C310—N31—C36	114.2 (3)
C16—N11—C110	113.4 (2)	O32—C32—N31	122.5 (3)
O12—C12—N11	123.4 (3)	O32—C32—C33	118.4 (3)
O12—C12—C13	117.1 (3)	N31—C32—C33	119.0 (3)
N11—C12—C13	119.4 (3)	N34—C33—C32	114.6 (3)
N14—C13—C12	114.0 (2)	N34—C33—C311	111.3 (3)
N14—C13—C111	110.7 (2)	C32—C33—C311	109.6 (3)
C12—C13—C111	109.7 (2)	N34—C33—H33	106.9
N14—C13—H13	107.4	C32—C33—H33	106.9
C12—C13—H13	107.4	C311—C33—H33	106.9
C111—C13—H13	107.4	C35—N34—C33	125.9 (3)
C15—N14—C13	126.1 (3)	C35—N34—H34	116.1 (18)
C15—N14—H14	121 (3)	C33—N34—H34	117.1 (17)
C13—N14—H14	113 (3)	O35—C35—N34	122.2 (3)
O15—C15—N14	122.4 (3)	O35—C35—C36	118.7 (3)
O15—C15—C16	118.2 (3)	N34—C35—C36	119.1 (3)
N14—C15—C16	119.3 (3)	N31—C36—C35	114.3 (3)
N11—C16—C15	114.6 (2)	N31—C36—C37	109.8 (3)
N11—C16—C17	109.9 (2)	C35—C36—C37	110.5 (2)
C15—C16—C17	111.4 (3)	N31—C36—H36	107.3
N11—C16—H16	106.8	C35—C36—H36	107.3
C15—C16—H16	106.8	C37—C36—H36	107.3
C17—C16—H16	106.8	C38—C37—C36	111.8 (3)
C16—C17—C18	111.0 (3)	C38—C37—H37A	109.2
C16—C17—H17A	109.4	C36—C37—H37A	109.2
C18—C17—H17A	109.4	C38—C37—H37B	109.2
C16—C17—H17B	109.4	C36—C37—H37B	109.2
C18—C17—H17B	109.4	H37A—C37—H37B	107.9
H17A—C17—H17B	108.0	C37—C38—C39	111.5 (3)
C19—C18—C17	111.5 (3)	C37—C38—H38A	109.3
C19—C18—H18A	109.3	C39—C38—H38A	109.3
C17—C18—H18A	109.3	C37—C38—H38B	109.3
C19—C18—H18B	109.3	C39—C38—H38B	109.3
C17—C18—H18B	109.3	H38A—C38—H38B	108.0
H18A—C18—H18B	108.0	C310—C39—C38	109.5 (3)
C110—C19—C18	110.5 (3)	C310—C39—H39A	109.8
C110—C19—H19A	109.5	C38—C39—H39A	109.8
C18—C19—H19A	109.5	C310—C39—H39B	109.8
C110—C19—H19B	109.5	C38—C39—H39B	109.8
C18—C19—H19B	109.5	H39A—C39—H39B	108.2
H19A—C19—H19B	108.1	N31—C310—C39	110.1 (3)
N11—C110—C19	110.3 (3)	N31—C310—H31A	109.6
N11—C110—H11A	109.6	C39—C310—H31A	109.6
C19—C110—H11A	109.6	N31—C310—H31B	109.6
N11—C110—H11B	109.6	C39—C310—H31B	109.6
C19—C110—H11B	109.6	H31A—C310—H31B	108.2
H11A—C110—H11B	108.1	C312—C311—C33	113.1 (3)
C112—C111—C13	113.1 (2)	C312—C311—H31C	109.0
C112—C111—H11C	109.0	C33—C311—H31C	109.0
C13—C111—H11C	109.0	C312—C311—H31D	109.0
C112—C111—H11D	109.0	C33—C311—H31D	109.0
C13—C111—H11D	109.0	H31C—C311—H31D	107.8
H11C—C111—H11D	107.8	C317—C312—C313	118.3 (3)
C113—C112—C117	118.3 (3)	C317—C312—C311	121.2 (3)
C113—C112—C111	120.9 (3)	C313—C312—C311	120.5 (3)
C117—C112—C111	120.8 (3)	C314—C313—C312	120.8 (3)
C112—C113—C114	120.7 (3)	C314—C313—H313	119.6
C112—C113—H113	119.7	C312—C313—H313	119.6
C114—C113—H113	119.7	C313—C314—C315	119.6 (4)
C115—C114—C113	120.6 (4)	C313—C314—H314	120.2
C115—C114—H114	119.7	C315—C314—H314	120.2
C113—C114—H114	119.7	C316—C315—C314	120.4 (4)
C116—C115—C114	119.0 (4)	C316—C315—H315	119.8
C116—C115—H115	120.5	C314—C315—H315	119.8
C114—C115—H115	120.5	C315—C316—C317	119.9 (4)
C117—C116—C115	120.4 (3)	C315—C316—H316	120.1
C117—C116—H116	119.8	C317—C316—H316	120.1
C115—C116—H116	119.8	C316—C317—C312	120.9 (3)
C116—C117—C112	120.9 (3)	C316—C317—H317	119.5
C116—C117—H117	119.5	C312—C317—H317	119.5
C112—C117—H117	119.5	C42—N41—C410	120.9 (2)
C22—N21—C210	120.5 (2)	C42—N41—C46	125.0 (2)
C22—N21—C26	125.4 (2)	C410—N41—C46	114.0 (2)
C210—N21—C26	113.5 (2)	O42—C42—N41	122.3 (3)
O22—C22—N21	122.7 (3)	O42—C42—C43	118.0 (3)
O22—C22—C23	117.7 (3)	N41—C42—C43	119.7 (3)
N21—C22—C23	119.5 (3)	N44—C43—C42	114.3 (2)
N24—C23—C22	113.7 (3)	N44—C43—C411	110.4 (2)
N24—C23—C211	110.9 (3)	C42—C43—C411	109.0 (2)
C22—C23—C211	110.5 (3)	N44—C43—H43	107.6
N24—C23—H23	107.1	C42—C43—H43	107.6
C22—C23—H23	107.1	C411—C43—H43	107.6
C211—C23—H23	107.1	C45—N44—C43	126.1 (3)
C25—N24—C23	125.5 (3)	C45—N44—H44	120 (2)
C25—N24—H24	121.0 (17)	C43—N44—H44	111 (2)
C23—N24—H24	111.4 (17)	O45—C45—N44	122.8 (3)
O25—C25—N24	121.3 (3)	O45—C45—C46	117.9 (3)
O25—C25—C26	118.7 (3)	N44—C45—C46	119.3 (3)
N24—C25—C26	120.0 (3)	N41—C46—C45	114.5 (2)
N21—C26—C25	113.7 (2)	N41—C46—C47	110.3 (2)
N21—C26—C27	109.7 (2)	C45—C46—C47	111.0 (3)
C25—C26—C27	110.8 (2)	N41—C46—H46	106.9
N21—C26—H26	107.5	C45—C46—H46	106.9
C25—C26—H26	107.5	C47—C46—H46	106.9
C27—C26—H26	107.5	C48—C47—C46	111.4 (3)
C28—C27—C26	111.7 (3)	C48—C47—H47A	109.3
C28—C27—H27A	109.3	C46—C47—H47A	109.3
C26—C27—H27A	109.3	C48—C47—H47B	109.3
C28—C27—H27B	109.3	C46—C47—H47B	109.3
C26—C27—H27B	109.3	H47A—C47—H47B	108.0
H27A—C27—H27B	107.9	C49—C48—C47	110.9 (3)
C27—C28—C29	111.7 (3)	C49—C48—H48A	109.5
C27—C28—H28A	109.3	C47—C48—H48A	109.5
C29—C28—H28A	109.3	C49—C48—H48B	109.5
C27—C28—H28B	109.3	C47—C48—H48B	109.5
C29—C28—H28B	109.3	H48A—C48—H48B	108.0
H28A—C28—H28B	107.9	C410—C49—C48	110.8 (3)
C210—C29—C28	109.8 (3)	C410—C49—H49A	109.5
C210—C29—H29A	109.7	C48—C49—H49A	109.5
C28—C29—H29A	109.7	C410—C49—H49B	109.5
C210—C29—H29B	109.7	C48—C49—H49B	109.5
C28—C29—H29B	109.7	H49A—C49—H49B	108.1
H29A—C29—H29B	108.2	N41—C410—C49	110.4 (3)
N21—C210—C29	109.7 (3)	N41—C410—H41A	109.6
N21—C210—H21A	109.7	C49—C410—H41A	109.6
C29—C210—H21A	109.7	N41—C410—H41B	109.6
N21—C210—H21B	109.7	C49—C410—H41B	109.6
C29—C210—H21B	109.7	H41A—C410—H41B	108.1
H21A—C210—H21B	108.2	C412—C411—C43	113.3 (3)
C212—C211—C23	112.9 (2)	C412—C411—H41C	108.9
C212—C211—H21C	109.0	C43—C411—H41C	108.9
C23—C211—H21C	109.0	C412—C411—H41D	108.9
C212—C211—H21D	109.0	C43—C411—H41D	108.9
C23—C211—H21D	109.0	H41C—C411—H41D	107.7
H21C—C211—H21D	107.8	C417—C412—C413	117.2 (3)
C213—C212—C217	118.2 (3)	C417—C412—C411	121.7 (3)
C213—C212—C211	120.9 (3)	C413—C412—C411	121.0 (3)
C217—C212—C211	120.8 (3)	C414—C413—C412	121.5 (3)
C214—C213—C212	121.4 (3)	C414—C413—H413	119.3
C214—C213—H213	119.3	C412—C413—H413	119.3
C212—C213—H213	119.3	C413—C414—C415	120.0 (3)
C213—C214—C215	119.6 (3)	C413—C414—H414	120.0
C213—C214—H214	120.2	C415—C414—H414	120.0
C215—C214—H214	120.2	C416—C415—C414	119.3 (4)
C216—C215—C214	119.9 (3)	C416—C415—H415	120.3
C216—C215—H215	120.0	C414—C415—H415	120.3
C214—C215—H215	120.0	C417—C416—C415	120.5 (3)
C215—C216—C217	120.1 (3)	C417—C416—H416	119.8
C215—C216—H216	120.0	C415—C416—H416	119.8
C217—C216—H216	120.0	C416—C417—C412	121.4 (3)
C216—C217—C212	120.7 (3)	C416—C417—H417	119.3
C216—C217—H217	119.6	C412—C417—H417	119.3
C212—C217—H217	119.6	H11W—O1W—H12W	107 (4)
C32—N31—C310	120.3 (3)	H21W—O2W—H22W	89 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···O25ⁱ	0.92 (4)	2.00 (4)	2.848 (3)	154 (4)
N24—H24···O2W	1.01 (3)	1.82 (3)	2.826 (4)	176 (3)
N34—H34···O1W	1.04 (3)	1.84 (4)	2.864 (4)	166 (3)
N44—H44···O35ⁱⁱ	0.92 (4)	1.94 (4)	2.836 (3)	162 (3)
O1W—H11W···O12ⁱⁱⁱ	0.95 (5)	1.95 (5)	2.893 (3)	169 (4)
O1W—H12W···O45^iv	0.97 (5)	1.82 (5)	2.792 (3)	173 (4)
O2W—H21W···O42^v	1.02 (5)	1.85 (5)	2.826 (3)	161 (4)
O2W—H22W···O15^vi	0.77 (4)	1.99 (4)	2.760 (4)	176 (4)

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

(1a-room) top

Crystal data top

2(C₁₅H₁₈N₂O₂)·H₂O	F(000) = 1144
M_r = 534.64	D_x = 1.236 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3230 reflections
a = 8.5217 (1) Å	θ = 1–26.0°
b = 25.0552 (3) Å	µ = 0.09 mm⁻¹
c = 13.4521 (2) Å	T = 297 K
V = 2872.20 (6) Å³	Prism, colourless
Z = 4	0.4 × 0.4 × 0.3 mm

Data collection top

Nonius KappaCCD area detector diffractometer	4670 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 26.0°, θ_min = 2.9°
Detector resolution: 9.091 pixels mm^-1	h = −10→10
φ and ω scans to fill the Ewald sphere	k = −30→30
50418 measured reflections	l = −16→16
5656 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0538P)² + 0.1118P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.002
5656 reflections	Δρ_max = 0.09 e Å⁻³
368 parameters	Δρ_min = −0.12 e Å⁻³
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.0 (8)

Special details top

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

	x	y	z	U_iso*/U_eq
N11	0.63236 (14)	0.83973 (4)	0.84175 (9)	0.0579 (3)
C12	0.77696 (18)	0.84296 (5)	0.87773 (10)	0.0553 (3)
O12	0.84440 (14)	0.88591 (4)	0.89221 (9)	0.0720 (3)
C13	0.86689 (18)	0.79218 (5)	0.89793 (11)	0.0589 (3)
H13	0.9119	0.7953	0.9647	0.071*
N14	0.77031 (16)	0.74429 (5)	0.89675 (10)	0.0610 (3)
C15	0.62316 (19)	0.74101 (6)	0.86763 (11)	0.0604 (4)
O15	0.54895 (16)	0.69850 (5)	0.86889 (10)	0.0844 (4)
C16	0.54071 (18)	0.79064 (6)	0.83340 (11)	0.0609 (4)
H16	0.4478	0.7950	0.8756	0.073*
C17	0.4824 (2)	0.78427 (7)	0.72644 (14)	0.0818 (5)
H17A	0.5712	0.7779	0.6829	0.098*
H17B	0.4134	0.7536	0.7225	0.098*
C18	0.3947 (2)	0.83366 (8)	0.69159 (16)	0.0919 (6)
H18A	0.3682	0.8298	0.6218	0.110*
H18B	0.2978	0.8371	0.7288	0.110*
C19	0.4926 (2)	0.88315 (7)	0.70573 (14)	0.0737 (4)
H19A	0.5831	0.8817	0.6621	0.088*
H19B	0.4312	0.9143	0.6880	0.088*
C110	0.5467 (2)	0.88809 (6)	0.81155 (14)	0.0752 (5)
H11A	0.6146	0.9190	0.8181	0.090*
H11B	0.4568	0.8932	0.8547	0.090*
C111	1.00439 (19)	0.78751 (7)	0.82460 (15)	0.0767 (5)
H11C	1.0741	0.8177	0.8341	0.092*
H11D	1.0631	0.7553	0.8396	0.092*
C112	0.9539 (2)	0.78585 (6)	0.71764 (14)	0.0735 (5)
C113	0.9171 (3)	0.73810 (7)	0.67201 (16)	0.1061 (8)
H113	0.9285	0.7064	0.7071	0.127*
C114	0.8636 (5)	0.73664 (8)	0.57504 (18)	0.1467 (14)
H114	0.8364	0.7042	0.5460	0.176*
C115	0.8506 (5)	0.78322 (10)	0.52162 (17)	0.1411 (12)
H115	0.8185	0.7824	0.4556	0.169*
C116	0.8854 (4)	0.83097 (8)	0.56638 (16)	0.1141 (9)
H116	0.8738	0.8626	0.5310	0.137*
C117	0.9373 (3)	0.83237 (7)	0.66291 (14)	0.0858 (5)
H117	0.9616	0.8650	0.6920	0.103*
N21	0.77816 (15)	1.04333 (5)	0.62535 (10)	0.0614 (3)
C22	0.8780 (2)	1.00617 (6)	0.59378 (12)	0.0633 (4)
O22	0.84629 (16)	0.95843 (4)	0.59176 (12)	0.0929 (4)
C23	1.0399 (2)	1.02300 (6)	0.56222 (12)	0.0638 (4)
H23	1.0594	1.0071	0.4968	0.077*
N24	1.05910 (18)	1.08021 (5)	0.55155 (10)	0.0653 (3)
C25	0.9599 (2)	1.11740 (6)	0.58351 (11)	0.0602 (4)
O25	0.98891 (15)	1.16573 (4)	0.57477 (10)	0.0789 (3)
C26	0.80946 (17)	1.10054 (5)	0.63188 (11)	0.0567 (3)
H26	0.7243	1.1187	0.5966	0.068*
C27	0.8033 (2)	1.11915 (7)	0.73919 (13)	0.0688 (4)
H27A	0.8106	1.1578	0.7413	0.083*
H27B	0.8922	1.1046	0.7752	0.083*
C28	0.6516 (2)	1.10147 (8)	0.78946 (15)	0.0844 (5)
H28A	0.6564	1.1101	0.8597	0.101*
H28B	0.5640	1.1208	0.7608	0.101*
C29	0.6249 (2)	1.04195 (7)	0.77724 (15)	0.0824 (5)
H29A	0.7061	1.0224	0.8122	0.099*
H29B	0.5243	1.0322	0.8058	0.099*
C210	0.6276 (2)	1.02739 (7)	0.66901 (15)	0.0780 (5)
H21A	0.6133	0.9892	0.6616	0.094*
H21B	0.5425	1.0453	0.6347	0.094*
C211	1.16240 (19)	0.99973 (6)	0.63384 (13)	0.0697 (4)
H21C	1.1520	0.9612	0.6347	0.084*
H21D	1.2664	1.0081	0.6091	0.084*
C212	1.14780 (18)	1.02024 (6)	0.73819 (12)	0.0642 (4)
C213	1.0564 (2)	0.99376 (7)	0.80807 (14)	0.0795 (5)
H213	1.0075	0.9619	0.7907	0.095*
C214	1.0373 (3)	1.01363 (10)	0.90161 (16)	0.1046 (7)
H214	0.9751	0.9955	0.9473	0.126*
C215	1.1103 (4)	1.06074 (11)	0.92851 (16)	0.1113 (8)
H215	1.0969	1.0745	0.9922	0.134*
C216	1.2039 (3)	1.08747 (10)	0.85996 (18)	0.0975 (6)
H216	1.2553	1.1187	0.8782	0.117*
C217	1.2200 (2)	1.06777 (7)	0.76604 (14)	0.0766 (5)
H217	1.2802	1.0864	0.7199	0.092*
O1W	1.37246 (19)	1.11314 (6)	0.50808 (13)	0.0964 (5)
H1W	1.457 (3)	1.1103 (8)	0.4690 (19)	0.106 (7)*
H2W	1.396 (3)	1.1395 (8)	0.5503 (17)	0.094 (7)*
H14	0.824 (2)	0.7136 (8)	0.9122 (14)	0.078 (5)*
H24	1.152 (3)	1.0946 (8)	0.5249 (16)	0.096 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.0667 (7)	0.0527 (6)	0.0542 (7)	−0.0026 (6)	−0.0086 (6)	0.0017 (5)
C12	0.0704 (8)	0.0504 (7)	0.0451 (7)	−0.0057 (7)	−0.0064 (7)	0.0001 (6)
O12	0.0902 (8)	0.0507 (5)	0.0751 (7)	−0.0113 (5)	−0.0250 (6)	0.0012 (5)
C13	0.0671 (8)	0.0527 (7)	0.0568 (8)	−0.0077 (7)	−0.0107 (7)	0.0062 (6)
N14	0.0726 (8)	0.0483 (6)	0.0621 (8)	−0.0050 (6)	−0.0024 (6)	0.0062 (6)
C15	0.0744 (9)	0.0580 (8)	0.0487 (8)	−0.0151 (7)	0.0021 (7)	0.0033 (6)
O15	0.0993 (8)	0.0676 (7)	0.0863 (9)	−0.0333 (6)	−0.0051 (7)	0.0125 (6)
C16	0.0603 (8)	0.0678 (8)	0.0546 (8)	−0.0140 (7)	0.0000 (7)	0.0063 (7)
C17	0.0985 (12)	0.0798 (10)	0.0672 (11)	−0.0273 (10)	−0.0253 (10)	0.0030 (9)
C18	0.0882 (12)	0.1103 (15)	0.0772 (12)	−0.0160 (11)	−0.0295 (10)	0.0142 (11)
C19	0.0723 (10)	0.0803 (10)	0.0686 (10)	0.0025 (8)	−0.0104 (8)	0.0149 (8)
C110	0.0845 (11)	0.0647 (9)	0.0764 (11)	0.0116 (8)	−0.0162 (9)	0.0016 (8)
C111	0.0656 (9)	0.0655 (9)	0.0991 (14)	−0.0016 (8)	0.0049 (9)	0.0155 (9)
C112	0.0842 (10)	0.0580 (8)	0.0782 (11)	0.0065 (8)	0.0266 (9)	0.0057 (8)
C113	0.180 (2)	0.0575 (10)	0.0805 (14)	0.0161 (12)	0.0307 (15)	0.0031 (9)
C114	0.298 (4)	0.0696 (12)	0.0722 (14)	0.0027 (18)	0.027 (2)	−0.0147 (10)
C115	0.268 (4)	0.0950 (15)	0.0607 (12)	0.013 (2)	0.0222 (18)	−0.0067 (11)
C116	0.202 (3)	0.0740 (12)	0.0658 (12)	0.0190 (15)	0.0353 (15)	0.0061 (9)
C117	0.1235 (15)	0.0598 (9)	0.0742 (12)	0.0031 (9)	0.0265 (11)	0.0060 (8)
N21	0.0626 (7)	0.0530 (6)	0.0685 (8)	−0.0087 (5)	−0.0032 (6)	0.0028 (6)
C22	0.0743 (9)	0.0512 (8)	0.0643 (9)	−0.0053 (7)	−0.0064 (8)	−0.0035 (7)
O22	0.0978 (9)	0.0527 (6)	0.1282 (11)	−0.0118 (6)	−0.0003 (9)	−0.0102 (7)
C23	0.0796 (10)	0.0576 (8)	0.0544 (8)	−0.0013 (8)	0.0065 (8)	−0.0065 (7)
N24	0.0738 (8)	0.0646 (7)	0.0574 (8)	−0.0072 (7)	0.0083 (7)	0.0049 (6)
C25	0.0747 (9)	0.0557 (8)	0.0503 (8)	−0.0092 (7)	−0.0063 (7)	0.0050 (6)
O25	0.0970 (8)	0.0546 (6)	0.0851 (8)	−0.0149 (6)	0.0012 (7)	0.0095 (5)
C26	0.0620 (8)	0.0474 (7)	0.0608 (9)	−0.0020 (6)	−0.0101 (7)	0.0052 (6)
C27	0.0706 (9)	0.0707 (9)	0.0650 (10)	−0.0005 (8)	0.0003 (8)	−0.0074 (7)
C28	0.0716 (11)	0.1056 (14)	0.0760 (12)	0.0059 (10)	0.0121 (9)	−0.0068 (10)
C29	0.0624 (9)	0.0927 (12)	0.0921 (14)	0.0037 (9)	0.0112 (10)	0.0239 (10)
C210	0.0611 (9)	0.0682 (10)	0.1045 (15)	−0.0126 (8)	−0.0011 (10)	0.0090 (9)
C211	0.0662 (9)	0.0649 (9)	0.0781 (11)	0.0076 (7)	0.0108 (8)	−0.0057 (8)
C212	0.0588 (8)	0.0639 (8)	0.0699 (10)	0.0127 (7)	−0.0063 (8)	0.0041 (7)
C213	0.0947 (12)	0.0742 (10)	0.0696 (11)	0.0077 (9)	−0.0050 (10)	0.0195 (8)
C214	0.1396 (19)	0.1120 (16)	0.0621 (12)	0.0286 (15)	0.0025 (13)	0.0226 (12)
C215	0.150 (2)	0.1270 (19)	0.0565 (12)	0.0504 (17)	−0.0271 (14)	−0.0073 (12)
C216	0.1014 (14)	0.1002 (14)	0.0909 (16)	0.0190 (12)	−0.0348 (13)	−0.0210 (12)
C217	0.0617 (9)	0.0824 (11)	0.0857 (13)	0.0038 (8)	−0.0091 (9)	−0.0022 (9)
O1W	0.0936 (9)	0.0821 (8)	0.1135 (12)	−0.0221 (7)	0.0506 (9)	−0.0231 (8)

Geometric parameters (Å, º) top

N11—C12	1.3264 (19)	N21—C26	1.4606 (17)
N11—C16	1.4612 (18)	N21—C210	1.466 (2)
N11—C110	1.4715 (19)	C22—O22	1.2267 (16)
C12—O12	1.2355 (16)	C22—C23	1.504 (2)
C12—C13	1.510 (2)	C23—N24	1.450 (2)
C13—N14	1.4552 (18)	C23—C211	1.535 (2)
C13—C111	1.536 (2)	C23—H23	0.9800
C13—H13	0.9800	N24—C25	1.329 (2)
N14—C15	1.316 (2)	N24—H24	0.94 (2)
N14—H14	0.918 (19)	C25—O25	1.2415 (17)
C15—O15	1.2388 (17)	C25—C26	1.499 (2)
C15—C16	1.501 (2)	C26—C27	1.518 (2)
C16—C17	1.531 (2)	C26—H26	0.9800
C16—H16	0.9800	C27—C28	1.524 (3)
C17—C18	1.519 (3)	C27—H27A	0.9700
C17—H17A	0.9700	C27—H27B	0.9700
C17—H17B	0.9700	C28—C29	1.518 (3)
C18—C19	1.507 (2)	C28—H28A	0.9700
C18—H18A	0.9700	C28—H28B	0.9700
C18—H18B	0.9700	C29—C210	1.501 (3)
C19—C110	1.501 (3)	C29—H29A	0.9700
C19—H19A	0.9700	C29—H29B	0.9700
C19—H19B	0.9700	C210—H21A	0.9700
C110—H11A	0.9700	C210—H21B	0.9700
C110—H11B	0.9700	C211—C212	1.500 (2)
C111—C112	1.502 (3)	C211—H21C	0.9700
C111—H11C	0.9700	C211—H21D	0.9700
C111—H11D	0.9700	C212—C213	1.389 (3)
C112—C113	1.381 (3)	C212—C217	1.392 (2)
C112—C117	1.386 (2)	C213—C214	1.363 (3)
C113—C114	1.382 (4)	C213—H213	0.9300
C113—H113	0.9300	C214—C215	1.382 (3)
C114—C115	1.375 (3)	C214—H214	0.9300
C114—H114	0.9300	C215—C216	1.391 (4)
C115—C116	1.372 (3)	C215—H215	0.9300
C115—H115	0.9300	C216—C217	1.363 (3)
C116—C117	1.372 (3)	C216—H216	0.9300
C116—H116	0.9300	C217—H217	0.9300
C117—H117	0.9300	O1W—H1W	0.89 (3)
N21—C22	1.331 (2)	O1W—H2W	0.89 (2)

C12—N11—C16	125.16 (12)	C22—N21—C210	119.78 (13)
C12—N11—C110	120.74 (12)	C26—N21—C210	113.76 (13)
C16—N11—C110	114.01 (12)	O22—C22—N21	123.24 (16)
O12—C12—N11	122.87 (13)	O22—C22—C23	117.99 (15)
O12—C12—C13	118.00 (13)	N21—C22—C23	118.73 (12)
N11—C12—C13	119.07 (12)	N24—C23—C22	114.10 (14)
N14—C13—C12	113.94 (13)	N24—C23—C211	111.16 (13)
N14—C13—C111	111.19 (13)	C22—C23—C211	109.88 (13)
C12—C13—C111	109.62 (12)	N24—C23—H23	107.1
N14—C13—H13	107.3	C22—C23—H23	107.1
C12—C13—H13	107.3	C211—C23—H23	107.1
C111—C13—H13	107.3	C25—N24—C23	126.11 (14)
C15—N14—C13	126.41 (13)	C25—N24—H24	112.9 (12)
C15—N14—H14	119.2 (11)	C23—N24—H24	120.7 (12)
C13—N14—H14	114.1 (11)	O25—C25—N24	121.77 (15)
O15—C15—N14	122.41 (15)	O25—C25—C26	119.10 (15)
O15—C15—C16	118.53 (14)	N24—C25—C26	119.13 (13)
N14—C15—C16	119.05 (12)	N21—C26—C25	114.00 (12)
N11—C16—C15	115.07 (12)	N21—C26—C27	110.63 (12)
N11—C16—C17	109.49 (12)	C25—C26—C27	110.86 (12)
C15—C16—C17	110.74 (14)	N21—C26—H26	107.0
N11—C16—H16	107.1	C25—C26—H26	107.0
C15—C16—H16	107.1	C27—C26—H26	107.0
C17—C16—H16	107.1	C26—C27—C28	111.22 (14)
C18—C17—C16	111.39 (16)	C26—C27—H27A	109.4
C18—C17—H17A	109.3	C28—C27—H27A	109.4
C16—C17—H17A	109.3	C26—C27—H27B	109.4
C18—C17—H17B	109.3	C28—C27—H27B	109.4
C16—C17—H17B	109.3	H27A—C27—H27B	108.0
H17A—C17—H17B	108.0	C29—C28—C27	111.41 (15)
C19—C18—C17	111.05 (15)	C29—C28—H28A	109.3
C19—C18—H18A	109.4	C27—C28—H28A	109.3
C17—C18—H18A	109.4	C29—C28—H28B	109.3
C19—C18—H18B	109.4	C27—C28—H28B	109.3
C17—C18—H18B	109.4	H28A—C28—H28B	108.0
H18A—C18—H18B	108.0	C210—C29—C28	109.97 (15)
C110—C19—C18	110.95 (15)	C210—C29—H29A	109.7
C110—C19—H19A	109.4	C28—C29—H29A	109.7
C18—C19—H19A	109.4	C210—C29—H29B	109.7
C110—C19—H19B	109.4	C28—C29—H29B	109.7
C18—C19—H19B	109.4	H29A—C29—H29B	108.2
H19A—C19—H19B	108.0	N21—C210—C29	109.64 (15)
N11—C110—C19	110.26 (14)	N21—C210—H21A	109.7
N11—C110—H11A	109.6	C29—C210—H21A	109.7
C19—C110—H11A	109.6	N21—C210—H21B	109.7
N11—C110—H11B	109.6	C29—C210—H21B	109.7
C19—C110—H11B	109.6	H21A—C210—H21B	108.2
H11A—C110—H11B	108.1	C212—C211—C23	113.63 (13)
C112—C111—C13	113.50 (14)	C212—C211—H21C	108.8
C112—C111—H11C	108.9	C23—C211—H21C	108.8
C13—C111—H11C	108.9	C212—C211—H21D	108.8
C112—C111—H11D	108.9	C23—C211—H21D	108.8
C13—C111—H11D	108.9	H21C—C211—H21D	107.7
H11C—C111—H11D	107.7	C213—C212—C217	118.31 (17)
C113—C112—C117	117.99 (19)	C213—C212—C211	121.07 (16)
C113—C112—C111	120.99 (16)	C217—C212—C211	120.55 (16)
C117—C112—C111	120.98 (17)	C214—C213—C212	121.2 (2)
C112—C113—C114	121.16 (18)	C214—C213—H213	119.4
C112—C113—H113	119.4	C212—C213—H213	119.4
C114—C113—H113	119.4	C213—C214—C215	120.0 (2)
C115—C114—C113	119.8 (2)	C213—C214—H214	120.0
C115—C114—H114	120.1	C215—C214—H214	120.0
C113—C114—H114	120.1	C214—C215—C216	119.7 (2)
C116—C115—C114	119.6 (2)	C214—C215—H215	120.1
C116—C115—H115	120.2	C216—C215—H215	120.1
C114—C115—H115	120.2	C217—C216—C215	119.9 (2)
C115—C116—C117	120.5 (2)	C217—C216—H216	120.1
C115—C116—H116	119.8	C215—C216—H216	120.1
C117—C116—H116	119.8	C216—C217—C212	121.0 (2)
C116—C117—C112	120.94 (18)	C216—C217—H217	119.5
C116—C117—H117	119.5	C212—C217—H217	119.5
C112—C117—H117	119.5	H1W—O1W—H2W	105 (2)
C22—N21—C26	126.08 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O12ⁱ	0.89 (3)	1.99 (3)	2.8726 (18)	171 (2)
O1W—H2W···O15ⁱⁱ	0.89 (2)	1.89 (2)	2.786 (2)	176 (2)
N14—H14···O25ⁱⁱⁱ	0.918 (19)	2.004 (19)	2.8690 (18)	156.5 (15)
N24—H24···O1W	0.94 (2)	1.95 (2)	2.855 (2)	161.3 (19)

Symmetry codes: (i) −x+5/2, −y+2, z−1/2; (ii) −x+2, y+1/2, −z+3/2; (iii) −x+2, y−1/2, −z+3/2.

(1b) top

Crystal data top

C₁₅H₁₈N₂O₂	F(000) = 1656
M_r = 258.31	D_x = 1.235 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2yb	Cell parameters from 62657 reflections
a = 22.1154 (7) Å	θ = 1–25°
b = 6.3963 (2) Å	µ = 0.08 mm⁻¹
c = 29.5771 (7) Å	T = 150 K
β = 95.2660 (18)°	Prism, colourless
V = 4166.2 (2) Å³	0.35 × 0.35 × 0.2 mm
Z = 12

Data collection top

Nonius KappaCCD area detector diffractometer	9326 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 25.1°, θ_min = 1.2°
Detector resolution: 9.091 pixels mm^-1	h = −26→26
φ and ω scans to fill the Ewald sphere	k = −7→7
64641 measured reflections	l = −34→35
14267 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.144	w = 1/[σ²(F_o²) + (0.0145P)² + 2.6049P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.004
14267 reflections	Δρ_max = 0.19 e Å⁻³
1051 parameters	Δρ_min = −0.23 e Å⁻³
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.1 (11)

Special details top

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

	x	y	z	U_iso*/U_eq
N11	−0.18810 (13)	0.4965 (5)	0.85758 (8)	0.0257 (7)
C12	−0.18332 (15)	0.3068 (6)	0.87631 (11)	0.0266 (8)
C13	−0.20288 (15)	0.2767 (6)	0.92324 (11)	0.0294 (8)
H13	−0.2279	0.1501	0.9224	0.035*
N14	−0.23990 (13)	0.4468 (5)	0.93812 (9)	0.0261 (7)
C15	−0.24115 (15)	0.6423 (6)	0.92199 (10)	0.0224 (8)
C16	−0.21632 (15)	0.6804 (5)	0.87695 (10)	0.0226 (8)
H16	−0.1851	0.7891	0.8815	0.027*
C17	−0.26619 (16)	0.7631 (6)	0.84289 (10)	0.0316 (9)
H17A	−0.2813	0.8938	0.8541	0.038*
H17B	−0.2996	0.6641	0.8403	0.038*
C18	−0.24460 (18)	0.7995 (7)	0.79582 (10)	0.0389 (10)
H18A	−0.2791	0.8352	0.7745	0.047*
H18B	−0.2164	0.9159	0.7971	0.047*
C19	−0.21369 (17)	0.6048 (6)	0.77938 (10)	0.0334 (9)
H19A	−0.2432	0.4931	0.7744	0.040*
H19B	−0.1972	0.6343	0.7508	0.040*
C110	−0.16345 (16)	0.5370 (6)	0.81404 (10)	0.0342 (9)
H11A	−0.1445	0.4112	0.8037	0.041*
H11B	−0.1328	0.6455	0.8178	0.041*
C111	−0.14745 (17)	0.2368 (6)	0.95717 (12)	0.0358 (10)
H11C	−0.1609	0.1986	0.9863	0.043*
H11D	−0.1242	0.1209	0.9466	0.043*
C112	−0.10734 (17)	0.4284 (6)	0.96277 (11)	0.0316 (9)
C113	−0.11505 (18)	0.5732 (6)	0.99712 (11)	0.0362 (10)
H113	−0.1440	0.5490	1.0174	0.043*
C114	−0.07991 (19)	0.7526 (7)	1.00123 (13)	0.0452 (11)
H114	−0.0856	0.8481	1.0242	0.054*
C115	−0.03683 (18)	0.7906 (8)	0.97175 (13)	0.0479 (11)
H115	−0.0135	0.9116	0.9749	0.057*
C116	−0.02788 (19)	0.6531 (7)	0.93795 (14)	0.0449 (11)
H116	0.0019	0.6786	0.9184	0.054*
C117	−0.06381 (17)	0.4729 (6)	0.93275 (12)	0.0362 (9)
H117	−0.0586	0.3814	0.9090	0.043*
O12	−0.16021 (12)	0.1581 (4)	0.85792 (8)	0.0409 (7)
O15	−0.26457 (11)	0.7900 (4)	0.94108 (7)	0.0331 (6)
N21	0.29507 (15)	0.4846 (5)	0.87566 (9)	0.0348 (8)
C22	0.30010 (17)	0.2900 (6)	0.89185 (12)	0.0348 (9)
C23	0.29341 (17)	0.2573 (6)	0.94162 (11)	0.0358 (9)
H23	0.2670	0.1361	0.9448	0.043*
N24	0.26790 (14)	0.4365 (5)	0.96412 (10)	0.0303 (7)
C25	0.26370 (16)	0.6314 (6)	0.94829 (11)	0.0295 (9)
C26	0.27089 (17)	0.6661 (6)	0.89841 (10)	0.0301 (9)
H26	0.2997	0.7814	0.8963	0.036*
C27	0.21073 (19)	0.7328 (7)	0.87301 (12)	0.0459 (11)
H27A	0.1808	0.6234	0.8755	0.055*
H27B	0.1961	0.8581	0.8870	0.055*
C28	0.2173 (2)	0.7755 (8)	0.82307 (12)	0.0520 (11)
H28A	0.2413	0.9011	0.8203	0.062*
H28B	0.1775	0.7995	0.8073	0.062*
C29	0.2479 (2)	0.5920 (8)	0.80068 (12)	0.0520 (12)
H29A	0.2204	0.4736	0.7981	0.062*
H29B	0.2567	0.6318	0.7703	0.062*
C210	0.3064 (2)	0.5295 (7)	0.82815 (11)	0.0491 (12)
H21A	0.3231	0.4063	0.8148	0.059*
H21B	0.3358	0.6417	0.8275	0.059*
C211	0.35748 (18)	0.2066 (6)	0.96520 (13)	0.0415 (10)
H21C	0.3544	0.1856	0.9974	0.050*
H21D	0.3718	0.0771	0.9529	0.050*
C212	0.40331 (17)	0.3767 (6)	0.95916 (12)	0.0357 (9)
C213	0.41134 (18)	0.5452 (7)	0.98971 (13)	0.0431 (11)
H213	0.3894	0.5476	1.0150	0.052*
C214	0.45009 (18)	0.7039 (7)	0.98330 (15)	0.0496 (12)
H214	0.4556	0.8099	1.0048	0.060*
C215	0.4813 (2)	0.7095 (8)	0.94532 (15)	0.0545 (12)
H215	0.5065	0.8219	0.9403	0.065*
C216	0.47507 (18)	0.5480 (8)	0.91497 (15)	0.0504 (12)
H216	0.4969	0.5498	0.8896	0.061*
C217	0.43610 (18)	0.3795 (7)	0.92158 (13)	0.0425 (10)
H217	0.4324	0.2703	0.9007	0.051*
O22	0.31394 (14)	0.1389 (4)	0.86910 (8)	0.0468 (7)
O25	0.25042 (12)	0.7827 (4)	0.97130 (8)	0.0419 (7)
N31	0.01837 (13)	−0.0103 (5)	0.80175 (9)	0.0286 (7)
C32	0.01465 (16)	−0.2023 (6)	0.78399 (11)	0.0320 (9)
C33	0.03689 (17)	−0.2353 (6)	0.73809 (11)	0.0346 (9)
H33	0.0618	−0.3622	0.7392	0.042*
N34	0.07276 (13)	−0.0620 (5)	0.72206 (11)	0.0337 (8)
C35	0.07335 (17)	0.1319 (7)	0.73811 (13)	0.0355 (9)
C36	0.04788 (17)	0.1700 (6)	0.78317 (12)	0.0333 (9)
H36	0.0175	0.2813	0.7786	0.040*
C37	0.09855 (19)	0.2501 (7)	0.81675 (13)	0.0501 (11)
H37A	0.1138	0.3810	0.8058	0.060*
H37B	0.1317	0.1501	0.8191	0.060*
C38	0.0763 (2)	0.2841 (8)	0.86376 (13)	0.0578 (12)
H38A	0.1107	0.3182	0.8852	0.069*
H38B	0.0486	0.4020	0.8624	0.069*
C39	0.04443 (19)	0.0939 (7)	0.88052 (12)	0.0452 (11)
H39A	0.0278	0.1260	0.9090	0.054*
H39B	0.0732	−0.0199	0.8858	0.054*
C310	−0.00622 (16)	0.0289 (7)	0.84539 (11)	0.0352 (9)
H31A	−0.0256	−0.0969	0.8554	0.042*
H31B	−0.0366	0.1385	0.8418	0.042*
C311	−0.01982 (17)	−0.2709 (6)	0.70407 (13)	0.0391 (10)
H31C	−0.0066	−0.3152	0.6752	0.047*
H31D	−0.0439	−0.3831	0.7153	0.047*
C312	−0.05872 (16)	−0.0815 (6)	0.69664 (12)	0.0327 (9)
C313	−0.04975 (17)	0.0589 (7)	0.66217 (11)	0.0368 (10)
H313	−0.0204	0.0314	0.6424	0.044*
C314	−0.08438 (17)	0.2415 (7)	0.65687 (12)	0.0414 (10)
H314	−0.0780	0.3334	0.6334	0.050*
C315	−0.12875 (17)	0.2883 (7)	0.68645 (12)	0.0404 (10)
H315	−0.1515	0.4105	0.6833	0.049*
C316	−0.13721 (17)	0.1448 (7)	0.72049 (13)	0.0420 (11)
H316	−0.1667	0.1706	0.7403	0.050*
C317	−0.10342 (16)	−0.0330 (7)	0.72566 (12)	0.0353 (9)
H317	−0.1102	−0.1246	0.7491	0.042*
O32	−0.00871 (12)	−0.3519 (4)	0.80245 (9)	0.0451 (7)
O35	0.09600 (12)	0.2802 (5)	0.71901 (9)	0.0472 (7)
N41	0.14268 (17)	0.4798 (5)	0.54158 (10)	0.0427 (9)
C42	0.1474 (2)	0.2896 (7)	0.55880 (12)	0.0455 (11)
C43	0.13511 (18)	0.2563 (6)	0.60750 (12)	0.0381 (10)
H43	0.1088	0.1335	0.6086	0.046*
N44	0.10430 (16)	0.4312 (6)	0.62625 (13)	0.0458 (9)
C45	0.10235 (17)	0.6251 (7)	0.61046 (13)	0.0382 (10)
C46	0.11788 (18)	0.6616 (6)	0.56288 (12)	0.0377 (10)
H46	0.1481	0.7739	0.5635	0.045*
C47	0.0613 (2)	0.7334 (9)	0.53346 (18)	0.0833 (18)
H47A	0.0463	0.8620	0.5458	0.100*
H47B	0.0298	0.6282	0.5342	0.100*
C48	0.0752 (3)	0.7704 (10)	0.48347 (15)	0.107 (2)
H48A	0.0375	0.7977	0.4649	0.129*
H48B	0.1010	0.8925	0.4821	0.129*
C49	0.1065 (3)	0.5826 (9)	0.46458 (15)	0.094 (2)
H49A	0.0786	0.4656	0.4614	0.113*
H49B	0.1188	0.6158	0.4348	0.113*
C410	0.1612 (2)	0.5239 (7)	0.49581 (12)	0.0606 (14)
H41A	0.1804	0.4012	0.4842	0.073*
H41B	0.1904	0.6375	0.4974	0.073*
C411	0.19496 (19)	0.2079 (7)	0.63580 (12)	0.0445 (11)
H41C	0.1869	0.1772	0.6668	0.053*
H41D	0.2135	0.0854	0.6236	0.053*
C412	0.2383 (2)	0.3910 (7)	0.63552 (13)	0.0484 (11)
C413	0.2380 (2)	0.5455 (8)	0.66754 (17)	0.0698 (15)
H413	0.2127	0.5331	0.6908	0.084*
C414	0.2749 (4)	0.7205 (11)	0.6657 (3)	0.116 (3)
H414	0.2750	0.8251	0.6876	0.139*
C415	0.3115 (4)	0.7337 (17)	0.6304 (4)	0.169 (7)
H415	0.3369	0.8489	0.6287	0.203*
C416	0.3115 (3)	0.5898 (17)	0.5993 (4)	0.148 (5)
H416	0.3361	0.6064	0.5757	0.178*
C417	0.2758 (2)	0.4127 (9)	0.60053 (17)	0.0686 (15)
H417	0.2769	0.3099	0.5784	0.082*
O42	0.16481 (18)	0.1379 (5)	0.53748 (9)	0.0724 (11)
O45	0.08605 (13)	0.7761 (5)	0.63259 (10)	0.0534 (8)
N51	0.54685 (14)	0.9973 (5)	0.79982 (9)	0.0297 (7)
C52	0.54046 (16)	0.8034 (6)	0.78274 (11)	0.0314 (9)
C53	0.54674 (17)	0.7714 (6)	0.73256 (11)	0.0350 (9)
H53	0.5731	0.6497	0.7298	0.042*
N54	0.57468 (15)	0.9463 (5)	0.71134 (11)	0.0356 (8)
C55	0.57920 (16)	1.1377 (6)	0.72726 (12)	0.0300 (8)
C56	0.56963 (15)	1.1772 (6)	0.77658 (11)	0.0269 (8)
H56	0.5398	1.2900	0.7776	0.032*
C57	0.62886 (16)	1.2506 (6)	0.80293 (11)	0.0363 (9)
H57A	0.6427	1.3777	0.7892	0.044*
H57B	0.6599	1.1447	0.8009	0.044*
C58	0.62001 (18)	1.2922 (8)	0.85343 (11)	0.0430 (10)
H58A	0.6593	1.3175	0.8700	0.052*
H58B	0.5955	1.4169	0.8557	0.052*
C59	0.58940 (18)	1.1099 (7)	0.87504 (12)	0.0446 (10)
H59A	0.6174	0.9930	0.8786	0.053*
H59B	0.5789	1.1502	0.9050	0.053*
C510	0.53255 (17)	1.0430 (6)	0.84632 (11)	0.0345 (9)
H51A	0.5157	0.9194	0.8594	0.041*
H51B	0.5025	1.1535	0.8458	0.041*
C511	0.48428 (18)	0.7169 (6)	0.70839 (12)	0.0404 (10)
H51C	0.4882	0.6930	0.6764	0.048*
H51D	0.4694	0.5891	0.7211	0.048*
C512	0.43946 (17)	0.8907 (6)	0.71351 (11)	0.0342 (9)
C513	0.40434 (17)	0.8918 (7)	0.75043 (12)	0.0438 (11)
H513	0.4077	0.7808	0.7708	0.053*
C514	0.3651 (2)	1.0517 (9)	0.75742 (14)	0.0564 (13)
H514	0.3422	1.0491	0.7822	0.068*
C515	0.3598 (2)	1.2195 (8)	0.72680 (15)	0.0630 (15)
H515	0.3330	1.3281	0.7311	0.076*
C516	0.3948 (2)	1.2231 (7)	0.69007 (13)	0.0521 (12)
H516	0.3922	1.3355	0.6700	0.063*
C517	0.43388 (18)	1.0568 (7)	0.68354 (12)	0.0407 (10)
H517	0.4566	1.0577	0.6586	0.049*
O52	0.52535 (13)	0.6539 (4)	0.80549 (8)	0.0442 (7)
O55	0.59400 (11)	1.2887 (4)	0.70393 (7)	0.0374 (6)
N61	0.63307 (16)	1.5006 (5)	0.52701 (10)	0.0417 (9)
C62	0.6388 (2)	1.3085 (6)	0.54377 (12)	0.0399 (10)
C63	0.62485 (17)	1.2716 (6)	0.59232 (10)	0.0334 (9)
H63	0.5997	1.1458	0.5932	0.040*
N64	0.59291 (13)	1.4456 (5)	0.61204 (10)	0.0289 (7)
C65	0.58960 (17)	1.6417 (6)	0.59598 (11)	0.0305 (9)
C66	0.6057 (2)	1.6791 (6)	0.54838 (11)	0.0412 (10)
H66	0.6358	1.7920	0.5500	0.049*
C67	0.5504 (2)	1.7574 (8)	0.51850 (12)	0.0595 (13)
H67A	0.5181	1.6548	0.5185	0.071*
H67B	0.5360	1.8863	0.5311	0.071*
C68	0.5648 (3)	1.7964 (9)	0.46969 (13)	0.0777 (17)
H68A	0.5274	1.8249	0.4510	0.093*
H68B	0.5905	1.9190	0.4689	0.093*
C69	0.5967 (3)	1.6107 (8)	0.44989 (13)	0.0708 (16)
H69A	0.5686	1.4944	0.4457	0.085*
H69B	0.6094	1.6484	0.4205	0.085*
C610	0.6515 (2)	1.5452 (8)	0.48114 (12)	0.0605 (14)
H61A	0.6696	1.4214	0.4691	0.073*
H61B	0.6815	1.6561	0.4829	0.073*
C611	0.68619 (17)	1.2310 (6)	0.62093 (11)	0.0346 (9)
H61C	0.6782	1.1936	0.6516	0.042*
H61D	0.7063	1.1133	0.6081	0.042*
C612	0.72766 (16)	1.4161 (7)	0.62273 (12)	0.0359 (10)
C613	0.72413 (17)	1.5683 (7)	0.65572 (14)	0.0414 (10)
H613	0.6962	1.5535	0.6772	0.050*
C614	0.7611 (2)	1.7403 (8)	0.65714 (16)	0.0583 (13)
H614	0.7594	1.8382	0.6802	0.070*
C615	0.8011 (2)	1.7688 (9)	0.62438 (19)	0.0697 (15)
H615	0.8250	1.8884	0.6245	0.084*
C616	0.80500 (19)	1.6173 (10)	0.59150 (18)	0.0635 (15)
H616	0.8325	1.6336	0.5698	0.076*
C617	0.76855 (18)	1.4424 (8)	0.59059 (14)	0.0497 (12)
H617	0.7715	1.3416	0.5682	0.060*
O62	0.65854 (16)	1.1591 (5)	0.52299 (9)	0.0589 (9)
O65	0.57063 (11)	1.7889 (4)	0.61750 (8)	0.0388 (6)
H14	−0.2546 (19)	0.457 (7)	0.9612 (14)	0.061 (15)*
H24	0.262 (2)	0.412 (7)	0.9929 (15)	0.072 (15)*
H34	0.0930 (16)	−0.086 (6)	0.6935 (12)	0.043 (11)*
H44	0.0995 (15)	0.418 (6)	0.6525 (11)	0.021 (10)*
H54	0.5730 (13)	0.935 (5)	0.6824 (11)	0.015 (8)*
H64	0.5802 (16)	1.415 (6)	0.6415 (12)	0.041 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.0336 (17)	0.0269 (19)	0.0173 (13)	0.0006 (13)	0.0063 (12)	−0.0015 (13)
C12	0.030 (2)	0.023 (2)	0.0271 (17)	−0.0046 (17)	0.0023 (15)	−0.0051 (18)
C13	0.0276 (19)	0.021 (2)	0.0406 (19)	−0.0085 (17)	0.0071 (15)	0.0066 (18)
N14	0.0359 (18)	0.0274 (19)	0.0166 (14)	0.0040 (14)	0.0103 (13)	0.0020 (14)
C15	0.0253 (19)	0.023 (2)	0.0186 (15)	−0.0022 (16)	0.0007 (14)	−0.0020 (17)
C16	0.0274 (19)	0.0177 (19)	0.0242 (16)	−0.0038 (14)	0.0101 (14)	−0.0021 (14)
C17	0.046 (2)	0.030 (2)	0.0202 (16)	0.0072 (19)	0.0102 (15)	0.0038 (17)
C18	0.061 (3)	0.035 (2)	0.0209 (16)	0.006 (2)	0.0087 (17)	0.0076 (18)
C19	0.049 (2)	0.035 (2)	0.0180 (16)	−0.0077 (18)	0.0158 (16)	0.0013 (16)
C110	0.042 (2)	0.038 (2)	0.0243 (17)	−0.0003 (19)	0.0162 (16)	−0.0009 (17)
C111	0.041 (2)	0.032 (3)	0.0353 (19)	0.0059 (18)	0.0072 (17)	0.0075 (18)
C112	0.041 (2)	0.027 (2)	0.0250 (17)	0.0083 (18)	−0.0049 (17)	0.0048 (17)
C113	0.046 (2)	0.036 (3)	0.0253 (18)	0.006 (2)	−0.0058 (17)	0.0080 (18)
C114	0.057 (3)	0.031 (3)	0.043 (2)	0.008 (2)	−0.021 (2)	−0.003 (2)
C115	0.043 (3)	0.042 (3)	0.054 (2)	−0.009 (2)	−0.025 (2)	0.000 (2)
C116	0.044 (3)	0.042 (3)	0.047 (2)	−0.003 (2)	−0.0067 (19)	0.008 (2)
C117	0.039 (2)	0.037 (2)	0.0311 (19)	0.0028 (18)	−0.0020 (17)	0.0055 (18)
O12	0.0527 (17)	0.0271 (17)	0.0448 (15)	0.0018 (13)	0.0152 (13)	−0.0057 (13)
O15	0.0523 (16)	0.0254 (15)	0.0233 (11)	0.0076 (13)	0.0123 (11)	−0.0063 (12)
N21	0.058 (2)	0.028 (2)	0.0207 (14)	−0.0016 (15)	0.0147 (15)	0.0016 (14)
C22	0.052 (2)	0.016 (2)	0.0375 (19)	−0.0100 (19)	0.0129 (18)	−0.0058 (19)
C23	0.046 (2)	0.029 (2)	0.0350 (19)	0.0035 (19)	0.0157 (17)	0.0021 (19)
N24	0.0455 (19)	0.0272 (19)	0.0203 (14)	0.0005 (15)	0.0143 (14)	0.0033 (15)
C25	0.043 (2)	0.024 (2)	0.0236 (17)	−0.0101 (18)	0.0160 (16)	−0.0018 (18)
C26	0.048 (2)	0.020 (2)	0.0234 (17)	−0.0043 (17)	0.0125 (16)	0.0004 (16)
C27	0.060 (3)	0.042 (3)	0.036 (2)	−0.002 (2)	0.0054 (19)	−0.0008 (19)
C28	0.067 (3)	0.051 (3)	0.035 (2)	−0.002 (3)	−0.010 (2)	0.008 (2)
C29	0.080 (3)	0.051 (3)	0.0240 (19)	−0.016 (3)	0.002 (2)	−0.002 (2)
C210	0.084 (3)	0.043 (3)	0.0230 (19)	−0.013 (2)	0.023 (2)	0.0018 (19)
C211	0.060 (3)	0.028 (2)	0.039 (2)	0.009 (2)	0.017 (2)	0.0040 (18)
C212	0.039 (2)	0.035 (2)	0.035 (2)	0.0063 (18)	0.0116 (17)	0.0075 (18)
C213	0.046 (2)	0.049 (3)	0.036 (2)	0.013 (2)	0.0130 (19)	−0.005 (2)
C214	0.038 (2)	0.052 (3)	0.060 (3)	0.007 (2)	0.006 (2)	−0.013 (2)
C215	0.053 (3)	0.050 (3)	0.061 (3)	−0.004 (2)	0.009 (2)	0.005 (2)
C216	0.037 (2)	0.058 (3)	0.059 (3)	−0.007 (2)	0.022 (2)	0.006 (3)
C217	0.047 (2)	0.038 (3)	0.045 (2)	0.008 (2)	0.016 (2)	−0.0025 (19)
O22	0.079 (2)	0.0249 (17)	0.0393 (14)	−0.0095 (15)	0.0217 (14)	−0.0061 (14)
O25	0.0658 (19)	0.0308 (16)	0.0323 (12)	−0.0026 (15)	0.0222 (13)	−0.0038 (14)
N31	0.0276 (16)	0.028 (2)	0.0316 (15)	−0.0001 (13)	0.0127 (13)	0.0003 (14)
C32	0.038 (2)	0.021 (2)	0.0390 (19)	0.0016 (18)	0.0145 (17)	0.0040 (19)
C33	0.044 (2)	0.025 (2)	0.0375 (19)	−0.0019 (18)	0.0192 (17)	0.0098 (19)
N34	0.0303 (17)	0.026 (2)	0.0472 (19)	0.0038 (14)	0.0173 (15)	0.0011 (16)
C35	0.036 (2)	0.027 (2)	0.046 (2)	0.0055 (18)	0.0205 (18)	0.001 (2)
C36	0.041 (2)	0.022 (2)	0.039 (2)	0.0016 (17)	0.0133 (17)	0.0004 (17)
C37	0.050 (3)	0.042 (3)	0.058 (2)	−0.016 (2)	0.007 (2)	0.004 (2)
C38	0.069 (3)	0.048 (3)	0.054 (2)	−0.015 (3)	−0.008 (2)	−0.007 (3)
C39	0.054 (3)	0.041 (3)	0.038 (2)	−0.003 (2)	−0.0073 (19)	−0.001 (2)
C310	0.036 (2)	0.038 (2)	0.0330 (19)	−0.0001 (18)	0.0102 (17)	0.0001 (18)
C311	0.042 (2)	0.030 (2)	0.047 (2)	−0.0076 (19)	0.0128 (19)	−0.0076 (19)
C312	0.031 (2)	0.034 (2)	0.0334 (19)	−0.0048 (18)	0.0032 (16)	−0.0045 (18)
C313	0.039 (2)	0.048 (3)	0.0257 (18)	−0.005 (2)	0.0100 (16)	−0.0024 (18)
C314	0.047 (2)	0.048 (3)	0.0271 (18)	−0.004 (2)	−0.0050 (17)	0.0035 (19)
C315	0.039 (2)	0.038 (2)	0.044 (2)	0.005 (2)	−0.0006 (18)	−0.012 (2)
C316	0.029 (2)	0.056 (3)	0.041 (2)	0.005 (2)	0.0072 (18)	−0.010 (2)
C317	0.036 (2)	0.042 (3)	0.0290 (18)	−0.0082 (19)	0.0101 (17)	−0.0039 (18)
O32	0.0569 (18)	0.0293 (18)	0.0527 (16)	−0.0037 (14)	0.0244 (14)	0.0087 (14)
O35	0.0563 (18)	0.0285 (16)	0.0619 (16)	−0.0023 (14)	0.0329 (14)	0.0032 (15)
N41	0.067 (2)	0.030 (2)	0.0298 (17)	−0.0014 (17)	0.0001 (16)	−0.0032 (16)
C42	0.069 (3)	0.032 (3)	0.035 (2)	−0.002 (2)	0.001 (2)	−0.011 (2)
C43	0.052 (3)	0.014 (2)	0.049 (2)	−0.0072 (18)	0.0129 (19)	−0.0053 (19)
N44	0.057 (2)	0.032 (2)	0.053 (2)	−0.0024 (18)	0.0297 (19)	−0.0016 (19)
C45	0.032 (2)	0.029 (2)	0.056 (2)	0.0019 (18)	0.0108 (19)	−0.005 (2)
C46	0.047 (2)	0.028 (2)	0.037 (2)	−0.0032 (19)	−0.0032 (18)	−0.0071 (18)
C47	0.083 (4)	0.057 (4)	0.101 (4)	0.019 (3)	−0.041 (3)	−0.015 (3)
C48	0.184 (7)	0.081 (5)	0.046 (3)	0.043 (5)	−0.049 (4)	−0.005 (3)
C49	0.165 (6)	0.064 (4)	0.043 (3)	0.019 (4)	−0.044 (3)	−0.013 (3)
C410	0.117 (4)	0.039 (3)	0.025 (2)	0.003 (3)	0.002 (2)	−0.0079 (19)
C411	0.071 (3)	0.031 (2)	0.035 (2)	0.009 (2)	0.022 (2)	0.0112 (18)
C412	0.058 (3)	0.051 (3)	0.035 (2)	0.008 (2)	−0.006 (2)	0.020 (2)
C413	0.084 (4)	0.055 (3)	0.062 (3)	−0.010 (3)	−0.036 (3)	0.019 (3)
C414	0.151 (7)	0.056 (4)	0.120 (6)	−0.025 (5)	−0.102 (5)	0.017 (4)
C415	0.081 (6)	0.116 (9)	0.287 (17)	−0.046 (7)	−0.112 (9)	0.116 (10)
C416	0.048 (4)	0.182 (11)	0.215 (11)	0.001 (6)	0.009 (6)	0.162 (10)
C417	0.047 (3)	0.081 (4)	0.079 (3)	0.008 (3)	0.014 (3)	0.041 (3)
O42	0.142 (3)	0.033 (2)	0.0448 (17)	0.006 (2)	0.0237 (19)	−0.0101 (16)
O45	0.066 (2)	0.0289 (17)	0.0708 (18)	0.0030 (16)	0.0346 (16)	−0.0087 (16)
N51	0.0410 (18)	0.0219 (18)	0.0279 (15)	0.0000 (14)	0.0117 (14)	0.0024 (14)
C52	0.030 (2)	0.032 (2)	0.0329 (18)	0.0034 (18)	0.0053 (16)	0.0058 (19)
C53	0.048 (2)	0.017 (2)	0.0417 (19)	0.0066 (18)	0.0178 (18)	0.0043 (18)
N54	0.050 (2)	0.028 (2)	0.0324 (18)	0.0020 (15)	0.0209 (16)	0.0022 (16)
C55	0.030 (2)	0.022 (2)	0.039 (2)	0.0029 (17)	0.0113 (16)	0.0025 (19)
C56	0.0253 (19)	0.023 (2)	0.0323 (18)	0.0016 (15)	0.0036 (15)	0.0069 (16)
C57	0.029 (2)	0.037 (2)	0.043 (2)	0.0009 (18)	0.0045 (16)	0.005 (2)
C58	0.041 (2)	0.056 (3)	0.0314 (18)	−0.006 (2)	−0.0014 (17)	0.007 (2)
C59	0.054 (3)	0.046 (3)	0.0342 (19)	0.012 (2)	0.0035 (19)	0.004 (2)
C510	0.046 (2)	0.033 (2)	0.0270 (18)	−0.0071 (19)	0.0145 (17)	0.0019 (17)
C511	0.053 (3)	0.033 (2)	0.038 (2)	−0.006 (2)	0.0176 (19)	−0.0031 (18)
C512	0.038 (2)	0.037 (2)	0.0272 (18)	−0.0061 (19)	−0.0015 (17)	−0.0029 (18)
C513	0.043 (2)	0.055 (3)	0.033 (2)	0.001 (2)	0.0069 (18)	0.000 (2)
C514	0.050 (3)	0.081 (4)	0.039 (2)	0.014 (3)	0.005 (2)	−0.007 (3)
C515	0.055 (3)	0.073 (4)	0.058 (3)	0.031 (3)	−0.014 (2)	−0.021 (3)
C516	0.068 (3)	0.048 (3)	0.034 (2)	0.007 (2)	−0.027 (2)	−0.003 (2)
C517	0.053 (3)	0.044 (3)	0.0235 (18)	0.003 (2)	−0.0071 (18)	−0.0014 (19)
O52	0.0659 (19)	0.0272 (17)	0.0411 (14)	−0.0045 (14)	0.0143 (14)	0.0114 (13)
O55	0.0509 (16)	0.0302 (16)	0.0335 (12)	−0.0017 (14)	0.0170 (12)	0.0064 (13)
N61	0.067 (2)	0.032 (2)	0.0253 (16)	0.0008 (17)	0.0017 (16)	0.0001 (15)
C62	0.072 (3)	0.018 (2)	0.0308 (19)	−0.008 (2)	0.0083 (19)	−0.0063 (19)
C63	0.055 (2)	0.021 (2)	0.0234 (16)	0.0068 (19)	−0.0004 (16)	−0.0079 (18)
N64	0.0312 (17)	0.0276 (19)	0.0272 (15)	−0.0035 (14)	−0.0010 (13)	0.0018 (15)
C65	0.037 (2)	0.029 (2)	0.0230 (17)	−0.0081 (18)	−0.0089 (16)	−0.0002 (18)
C66	0.071 (3)	0.027 (2)	0.0231 (18)	−0.003 (2)	−0.0095 (18)	0.0013 (17)
C67	0.087 (3)	0.048 (3)	0.038 (2)	0.013 (3)	−0.025 (2)	−0.007 (2)
C68	0.130 (5)	0.054 (3)	0.041 (2)	0.007 (3)	−0.035 (3)	0.001 (3)
C69	0.127 (5)	0.054 (3)	0.028 (2)	−0.017 (3)	−0.015 (3)	0.001 (2)
C610	0.105 (4)	0.056 (3)	0.0213 (19)	−0.016 (3)	0.010 (2)	0.003 (2)
C611	0.049 (2)	0.026 (2)	0.0296 (18)	0.0122 (18)	0.0102 (17)	0.0094 (17)
C612	0.030 (2)	0.043 (3)	0.035 (2)	0.0088 (19)	0.0088 (17)	0.020 (2)
C613	0.032 (2)	0.040 (3)	0.052 (2)	0.0085 (19)	0.0002 (19)	0.003 (2)
C614	0.048 (3)	0.049 (3)	0.074 (3)	−0.006 (2)	−0.016 (2)	0.012 (3)
C615	0.051 (3)	0.049 (3)	0.106 (4)	0.001 (3)	−0.012 (3)	0.040 (4)
C616	0.034 (3)	0.074 (4)	0.084 (3)	0.001 (3)	0.014 (2)	0.049 (3)
C617	0.044 (3)	0.056 (3)	0.052 (2)	0.014 (2)	0.017 (2)	0.021 (2)
O62	0.111 (3)	0.0301 (19)	0.0383 (15)	−0.0023 (17)	0.0189 (16)	−0.0095 (14)
O65	0.0482 (16)	0.0299 (16)	0.0381 (13)	0.0007 (14)	0.0030 (12)	0.0001 (14)

Geometric parameters (Å, º) top

N11—C12	1.334 (5)	N41—C42	1.319 (5)
N11—C110	1.467 (4)	N41—C46	1.454 (5)
N11—C16	1.472 (4)	N41—C410	1.478 (5)
C12—O12	1.230 (4)	C42—O42	1.237 (5)
C12—C13	1.504 (4)	C42—C43	1.505 (5)
C13—N14	1.454 (5)	C43—N44	1.447 (5)
C13—C111	1.533 (5)	C43—C411	1.531 (5)
C13—H13	0.9800	C43—H43	0.9800
N14—C15	1.338 (5)	N44—C45	1.324 (5)
N14—H14	0.79 (4)	N44—H44	0.80 (3)
C15—O15	1.238 (4)	C45—O45	1.239 (5)
C15—C16	1.507 (4)	C45—C46	1.497 (5)
C16—C17	1.519 (5)	C46—C47	1.529 (6)
C16—H16	0.9800	C46—H46	0.9800
C17—C18	1.531 (4)	C47—C48	1.556 (7)
C17—H17A	0.9700	C47—H47A	0.9700
C17—H17B	0.9700	C47—H47B	0.9700
C18—C19	1.522 (5)	C48—C49	1.519 (7)
C18—H18A	0.9700	C48—H48A	0.9700
C18—H18B	0.9700	C48—H48B	0.9700
C19—C110	1.505 (5)	C49—C410	1.501 (7)
C19—H19A	0.9700	C49—H49A	0.9700
C19—H19B	0.9700	C49—H49B	0.9700
C110—H11A	0.9700	C410—H41A	0.9700
C110—H11B	0.9700	C410—H41B	0.9700
C111—C112	1.513 (5)	C411—C412	1.515 (6)
C111—H11C	0.9700	C411—H41C	0.9700
C111—H11D	0.9700	C411—H41D	0.9700
C112—C113	1.397 (5)	C412—C413	1.369 (7)
C112—C117	1.397 (5)	C412—C417	1.391 (6)
C113—C114	1.385 (6)	C413—C414	1.389 (8)
C113—H113	0.9300	C413—H413	0.9300
C114—C115	1.371 (6)	C414—C415	1.383 (13)
C114—H114	0.9300	C414—H414	0.9300
C115—C116	1.360 (6)	C415—C416	1.300 (15)
C115—H115	0.9300	C415—H415	0.9300
C116—C117	1.401 (6)	C416—C417	1.383 (10)
C116—H116	0.9300	C416—H416	0.9300
C117—H117	0.9300	C417—H417	0.9300
N21—C22	1.335 (5)	N51—C52	1.342 (5)
N21—C26	1.467 (4)	N51—C56	1.454 (4)
N21—C210	1.478 (4)	N51—C510	1.469 (4)
C22—O22	1.232 (4)	C52—O52	1.233 (4)
C22—C23	1.507 (5)	C52—C53	1.517 (5)
C23—N24	1.464 (5)	C53—N54	1.448 (5)
C23—C211	1.555 (5)	C53—C511	1.536 (5)
C23—H23	0.9800	C53—H53	0.9800
N24—C25	1.332 (5)	N54—C55	1.312 (5)
N24—H24	0.89 (4)	N54—H54	0.86 (3)
C25—O25	1.234 (4)	C55—O55	1.249 (4)
C25—C26	1.515 (4)	C55—C56	1.514 (5)
C26—C27	1.527 (5)	C56—C57	1.535 (5)
C26—H26	0.9800	C56—H56	0.9800
C27—C28	1.522 (5)	C57—C58	1.547 (5)
C27—H27A	0.9700	C57—H57A	0.9700
C27—H27B	0.9700	C57—H57B	0.9700
C28—C29	1.535 (6)	C58—C59	1.518 (6)
C28—H28A	0.9700	C58—H58A	0.9700
C28—H28B	0.9700	C58—H58B	0.9700
C29—C210	1.516 (6)	C59—C510	1.513 (5)
C29—H29A	0.9700	C59—H59A	0.9700
C29—H29B	0.9700	C59—H59B	0.9700
C210—H21A	0.9700	C510—H51A	0.9700
C210—H21B	0.9700	C510—H51B	0.9700
C211—C212	1.509 (6)	C511—C512	1.506 (5)
C211—H21C	0.9700	C511—H51C	0.9700
C211—H21D	0.9700	C511—H51D	0.9700
C212—C217	1.382 (5)	C512—C517	1.382 (5)
C212—C213	1.407 (6)	C512—C513	1.397 (5)
C213—C214	1.353 (6)	C513—C514	1.369 (6)
C213—H213	0.9300	C513—H513	0.9300
C214—C215	1.372 (6)	C514—C515	1.402 (7)
C214—H214	0.9300	C514—H514	0.9300
C215—C216	1.367 (6)	C515—C516	1.390 (6)
C215—H215	0.9300	C515—H515	0.9300
C216—C217	1.405 (6)	C516—C517	1.395 (6)
C216—H216	0.9300	C516—H516	0.9300
C217—H217	0.9300	C517—H517	0.9300
N31—C32	1.335 (5)	N61—C62	1.327 (5)
N31—C36	1.457 (4)	N61—C66	1.462 (5)
N31—C310	1.467 (4)	N61—C610	1.480 (5)
C32—O32	1.238 (4)	C62—O62	1.238 (5)
C32—C33	1.501 (5)	C62—C63	1.514 (5)
C33—N34	1.466 (5)	C63—N64	1.467 (5)
C33—C311	1.551 (5)	C63—C611	1.553 (5)
C33—H33	0.9800	C63—H63	0.9800
N34—C35	1.328 (5)	N64—C65	1.341 (5)
N34—H34	1.00 (4)	N64—H64	0.96 (4)
C35—O35	1.234 (5)	C65—O65	1.232 (4)
C35—C36	1.514 (5)	C65—C66	1.503 (5)
C36—C37	1.516 (5)	C66—C67	1.527 (6)
C36—H36	0.9800	C66—H66	0.9800
C37—C38	1.533 (5)	C67—C68	1.527 (6)
C37—H37A	0.9700	C67—H67A	0.9700
C37—H37B	0.9700	C67—H67B	0.9700
C38—C39	1.512 (6)	C68—C69	1.525 (7)
C38—H38A	0.9700	C68—H68A	0.9700
C38—H38B	0.9700	C68—H68B	0.9700
C39—C310	1.515 (5)	C69—C610	1.514 (7)
C39—H39A	0.9700	C69—H69A	0.9700
C39—H39B	0.9700	C69—H69B	0.9700
C310—H31A	0.9700	C610—H61A	0.9700
C310—H31B	0.9700	C610—H61B	0.9700
C311—C312	1.490 (5)	C611—C612	1.496 (6)
C311—H31C	0.9700	C611—H61C	0.9700
C311—H31D	0.9700	C611—H61D	0.9700
C312—C313	1.387 (5)	C612—C617	1.381 (5)
C312—C317	1.402 (5)	C612—C613	1.386 (6)
C313—C314	1.397 (6)	C613—C614	1.369 (6)
C313—H313	0.9300	C613—H613	0.9300
C314—C315	1.406 (5)	C614—C615	1.382 (7)
C314—H314	0.9300	C614—H614	0.9300
C315—C316	1.388 (6)	C615—C616	1.381 (7)
C315—H315	0.9300	C615—H615	0.9300
C316—C317	1.361 (6)	C616—C617	1.378 (7)
C316—H316	0.9300	C616—H616	0.9300
C317—H317	0.9300	C617—H617	0.9300

C12—N11—C110	120.2 (3)	C42—N41—C46	126.2 (3)
C12—N11—C16	125.8 (3)	C42—N41—C410	120.7 (3)
C110—N11—C16	113.9 (3)	C46—N41—C410	113.1 (3)
O12—C12—N11	122.7 (3)	O42—C42—N41	122.9 (4)
O12—C12—C13	118.4 (3)	O42—C42—C43	118.0 (4)
N11—C12—C13	118.8 (3)	N41—C42—C43	119.0 (4)
N14—C13—C12	113.7 (3)	N44—C43—C42	113.0 (4)
N14—C13—C111	111.4 (3)	N44—C43—C411	111.1 (3)
C12—C13—C111	110.2 (3)	C42—C43—C411	109.2 (3)
N14—C13—H13	107.1	N44—C43—H43	107.8
C12—C13—H13	107.1	C42—C43—H43	107.8
C111—C13—H13	107.1	C411—C43—H43	107.8
C15—N14—C13	125.8 (3)	C45—N44—C43	126.2 (3)
C15—N14—H14	104 (4)	C45—N44—H44	116 (3)
C13—N14—H14	128 (3)	C43—N44—H44	113 (3)
O15—C15—N14	123.1 (3)	O45—C45—N44	123.1 (4)
O15—C15—C16	118.8 (3)	O45—C45—C46	118.5 (4)
N14—C15—C16	118.0 (3)	N44—C45—C46	118.3 (4)
N11—C16—C15	114.6 (3)	N41—C46—C45	114.3 (3)
N11—C16—C17	109.2 (3)	N41—C46—C47	108.4 (3)
C15—C16—C17	110.0 (3)	C45—C46—C47	109.6 (4)
N11—C16—H16	107.6	N41—C46—H46	108.1
C15—C16—H16	107.6	C45—C46—H46	108.1
C17—C16—H16	107.6	C47—C46—H46	108.1
C16—C17—C18	112.8 (3)	C46—C47—C48	111.3 (5)
C16—C17—H17A	109.0	C46—C47—H47A	109.4
C18—C17—H17A	109.0	C48—C47—H47A	109.4
C16—C17—H17B	109.0	C46—C47—H47B	109.4
C18—C17—H17B	109.0	C48—C47—H47B	109.4
H17A—C17—H17B	107.8	H47A—C47—H47B	108.0
C19—C18—C17	110.7 (3)	C49—C48—C47	111.5 (5)
C19—C18—H18A	109.5	C49—C48—H48A	109.3
C17—C18—H18A	109.5	C47—C48—H48A	109.3
C19—C18—H18B	109.5	C49—C48—H48B	109.3
C17—C18—H18B	109.5	C47—C48—H48B	109.3
H18A—C18—H18B	108.1	H48A—C48—H48B	108.0
C110—C19—C18	110.1 (3)	C410—C49—C48	109.9 (4)
C110—C19—H19A	109.6	C410—C49—H49A	109.7
C18—C19—H19A	109.6	C48—C49—H49A	109.7
C110—C19—H19B	109.6	C410—C49—H49B	109.7
C18—C19—H19B	109.6	C48—C49—H49B	109.7
H19A—C19—H19B	108.2	H49A—C49—H49B	108.2
N11—C110—C19	109.8 (3)	N41—C410—C49	109.6 (4)
N11—C110—H11A	109.7	N41—C410—H41A	109.7
C19—C110—H11A	109.7	C49—C410—H41A	109.7
N11—C110—H11B	109.7	N41—C410—H41B	109.7
C19—C110—H11B	109.7	C49—C410—H41B	109.7
H11A—C110—H11B	108.2	H41A—C410—H41B	108.2
C112—C111—C13	111.3 (3)	C412—C411—C43	110.9 (3)
C112—C111—H11C	109.4	C412—C411—H41C	109.5
C13—C111—H11C	109.4	C43—C411—H41C	109.5
C112—C111—H11D	109.4	C412—C411—H41D	109.5
C13—C111—H11D	109.4	C43—C411—H41D	109.5
H11C—C111—H11D	108.0	H41C—C411—H41D	108.0
C113—C112—C117	117.7 (4)	C413—C412—C417	119.0 (5)
C113—C112—C111	120.5 (3)	C413—C412—C411	120.7 (4)
C117—C112—C111	121.8 (3)	C417—C412—C411	120.1 (5)
C114—C113—C112	120.6 (4)	C412—C413—C414	121.0 (6)
C114—C113—H113	119.7	C412—C413—H413	119.5
C112—C113—H113	119.7	C414—C413—H413	119.5
C115—C114—C113	120.6 (4)	C415—C414—C413	117.7 (8)
C115—C114—H114	119.7	C415—C414—H414	121.1
C113—C114—H114	119.7	C413—C414—H414	121.1
C116—C115—C114	120.6 (4)	C416—C415—C414	121.9 (10)
C116—C115—H115	119.7	C416—C415—H415	119.1
C114—C115—H115	119.7	C414—C415—H415	119.1
C115—C116—C117	119.6 (4)	C415—C416—C417	121.7 (10)
C115—C116—H116	120.2	C415—C416—H416	119.1
C117—C116—H116	120.2	C417—C416—H416	119.1
C112—C117—C116	121.0 (4)	C416—C417—C412	118.7 (7)
C112—C117—H117	119.5	C416—C417—H417	120.6
C116—C117—H117	119.5	C412—C417—H417	120.6
C22—N21—C26	126.5 (3)	C52—N51—C56	125.6 (3)
C22—N21—C210	120.4 (3)	C52—N51—C510	120.8 (3)
C26—N21—C210	112.5 (3)	C56—N51—C510	113.5 (3)
O22—C22—N21	123.5 (3)	O52—C52—N51	122.4 (3)
O22—C22—C23	118.4 (4)	O52—C52—C53	118.9 (4)
N21—C22—C23	117.8 (3)	N51—C52—C53	118.5 (3)
N24—C23—C22	114.3 (3)	N54—C53—C52	113.6 (3)
N24—C23—C211	109.4 (3)	N54—C53—C511	112.0 (3)
C22—C23—C211	107.5 (3)	C52—C53—C511	109.1 (3)
N24—C23—H23	108.5	N54—C53—H53	107.3
C22—C23—H23	108.5	C52—C53—H53	107.3
C211—C23—H23	108.5	C511—C53—H53	107.3
C25—N24—C23	126.2 (3)	C55—N54—C53	125.9 (3)
C25—N24—H24	120 (3)	C55—N54—H54	115 (2)
C23—N24—H24	113 (3)	C53—N54—H54	113 (2)
O25—C25—N24	123.6 (3)	O55—C55—N54	122.6 (3)
O25—C25—C26	118.3 (3)	O55—C55—C56	118.0 (3)
N24—C25—C26	118.0 (3)	N54—C55—C56	119.3 (3)
N21—C26—C25	113.9 (3)	N51—C56—C55	114.1 (3)
N21—C26—C27	109.4 (3)	N51—C56—C57	108.6 (3)
C25—C26—C27	110.8 (3)	C55—C56—C57	110.6 (3)
N21—C26—H26	107.4	N51—C56—H56	107.8
C25—C26—H26	107.4	C55—C56—H56	107.8
C27—C26—H26	107.4	C57—C56—H56	107.8
C28—C27—C26	111.8 (3)	C56—C57—C58	111.4 (3)
C28—C27—H27A	109.3	C56—C57—H57A	109.3
C26—C27—H27A	109.3	C58—C57—H57A	109.3
C28—C27—H27B	109.3	C56—C57—H57B	109.3
C26—C27—H27B	109.3	C58—C57—H57B	109.3
H27A—C27—H27B	107.9	H57A—C57—H57B	108.0
C27—C28—C29	111.5 (4)	C59—C58—C57	112.0 (4)
C27—C28—H28A	109.3	C59—C58—H58A	109.2
C29—C28—H28A	109.3	C57—C58—H58A	109.2
C27—C28—H28B	109.3	C59—C58—H58B	109.2
C29—C28—H28B	109.3	C57—C58—H58B	109.2
H28A—C28—H28B	108.0	H58A—C58—H58B	107.9
C210—C29—C28	111.0 (3)	C510—C59—C58	111.1 (3)
C210—C29—H29A	109.4	C510—C59—H59A	109.4
C28—C29—H29A	109.4	C58—C59—H59A	109.4
C210—C29—H29B	109.4	C510—C59—H59B	109.4
C28—C29—H29B	109.4	C58—C59—H59B	109.4
H29A—C29—H29B	108.0	H59A—C59—H59B	108.0
N21—C210—C29	110.5 (3)	N51—C510—C59	110.1 (3)
N21—C210—H21A	109.5	N51—C510—H51A	109.7
C29—C210—H21A	109.5	C59—C510—H51A	109.7
N21—C210—H21B	109.5	N51—C510—H51B	109.7
C29—C210—H21B	109.5	C59—C510—H51B	109.7
H21A—C210—H21B	108.1	H51A—C510—H51B	108.2
C212—C211—C23	113.0 (3)	C512—C511—C53	111.0 (3)
C212—C211—H21C	109.0	C512—C511—H51C	109.4
C23—C211—H21C	109.0	C53—C511—H51C	109.4
C212—C211—H21D	109.0	C512—C511—H51D	109.4
C23—C211—H21D	109.0	C53—C511—H51D	109.4
H21C—C211—H21D	107.8	H51C—C511—H51D	108.0
C217—C212—C213	117.5 (4)	C517—C512—C513	118.3 (4)
C217—C212—C211	120.8 (4)	C517—C512—C511	121.6 (3)
C213—C212—C211	121.5 (3)	C513—C512—C511	120.0 (4)
C214—C213—C212	121.9 (4)	C514—C513—C512	121.8 (4)
C214—C213—H213	119.0	C514—C513—H513	119.1
C212—C213—H213	119.0	C512—C513—H513	119.1
C213—C214—C215	120.5 (4)	C513—C514—C515	119.4 (4)
C213—C214—H214	119.8	C513—C514—H514	120.3
C215—C214—H214	119.8	C515—C514—H514	120.3
C216—C215—C214	119.3 (4)	C516—C515—C514	119.9 (4)
C216—C215—H215	120.3	C516—C515—H515	120.1
C214—C215—H215	120.3	C514—C515—H515	120.1
C215—C216—C217	121.0 (4)	C515—C516—C517	119.4 (4)
C215—C216—H216	119.5	C515—C516—H516	120.3
C217—C216—H216	119.5	C517—C516—H516	120.3
C212—C217—C216	119.7 (4)	C512—C517—C516	121.1 (4)
C212—C217—H217	120.1	C512—C517—H517	119.4
C216—C217—H217	120.1	C516—C517—H517	119.4
C32—N31—C36	126.4 (3)	C62—N61—C66	126.2 (3)
C32—N31—C310	119.2 (3)	C62—N61—C610	119.8 (4)
C36—N31—C310	114.3 (3)	C66—N61—C610	113.9 (3)
O32—C32—N31	123.4 (3)	O62—C62—N61	123.7 (3)
O32—C32—C33	118.4 (4)	O62—C62—C63	117.5 (4)
N31—C32—C33	118.1 (3)	N61—C62—C63	118.6 (3)
N34—C33—C32	114.7 (3)	N64—C63—C62	113.9 (3)
N34—C33—C311	109.3 (3)	N64—C63—C611	109.8 (3)
C32—C33—C311	107.1 (3)	C62—C63—C611	107.4 (3)
N34—C33—H33	108.5	N64—C63—H63	108.5
C32—C33—H33	108.5	C62—C63—H63	108.5
C311—C33—H33	108.5	C611—C63—H63	108.5
C35—N34—C33	125.3 (3)	C65—N64—C63	125.5 (3)
C35—N34—H34	117 (2)	C65—N64—H64	120 (2)
C33—N34—H34	117 (2)	C63—N64—H64	113 (2)
O35—C35—N34	123.1 (3)	O65—C65—N64	122.8 (3)
O35—C35—C36	118.6 (4)	O65—C65—C66	118.9 (3)
N34—C35—C36	118.2 (3)	N64—C65—C66	118.1 (3)
N31—C36—C35	114.8 (3)	N61—C66—C65	115.1 (3)
N31—C36—C37	110.5 (3)	N61—C66—C67	110.3 (3)
C35—C36—C37	108.6 (3)	C65—C66—C67	110.3 (4)
N31—C36—H36	107.6	N61—C66—H66	106.9
C35—C36—H36	107.6	C65—C66—H66	106.9
C37—C36—H36	107.6	C67—C66—H66	106.9
C36—C37—C38	111.3 (3)	C68—C67—C66	112.0 (4)
C36—C37—H37A	109.4	C68—C67—H67A	109.2
C38—C37—H37A	109.4	C66—C67—H67A	109.2
C36—C37—H37B	109.4	C68—C67—H67B	109.2
C38—C37—H37B	109.4	C66—C67—H67B	109.2
H37A—C37—H37B	108.0	H67A—C67—H67B	107.9
C39—C38—C37	112.4 (4)	C69—C68—C67	112.3 (4)
C39—C38—H38A	109.1	C69—C68—H68A	109.1
C37—C38—H38A	109.1	C67—C68—H68A	109.1
C39—C38—H38B	109.1	C69—C68—H68B	109.1
C37—C38—H38B	109.1	C67—C68—H68B	109.1
H38A—C38—H38B	107.9	H68A—C68—H68B	107.9
C38—C39—C310	109.5 (3)	C610—C69—C68	110.7 (4)
C38—C39—H39A	109.8	C610—C69—H69A	109.5
C310—C39—H39A	109.8	C68—C69—H69A	109.5
C38—C39—H39B	109.8	C610—C69—H69B	109.5
C310—C39—H39B	109.8	C68—C69—H69B	109.5
H39A—C39—H39B	108.2	H69A—C69—H69B	108.1
N31—C310—C39	109.9 (3)	N61—C610—C69	109.9 (4)
N31—C310—H31A	109.7	N61—C610—H61A	109.7
C39—C310—H31A	109.7	C69—C610—H61A	109.7
N31—C310—H31B	109.7	N61—C610—H61B	109.7
C39—C310—H31B	109.7	C69—C610—H61B	109.7
H31A—C310—H31B	108.2	H61A—C610—H61B	108.2
C312—C311—C33	113.4 (3)	C612—C611—C63	112.9 (3)
C312—C311—H31C	108.9	C612—C611—H61C	109.0
C33—C311—H31C	108.9	C63—C611—H61C	109.0
C312—C311—H31D	108.9	C612—C611—H61D	109.0
C33—C311—H31D	108.9	C63—C611—H61D	109.0
H31C—C311—H31D	107.7	H61C—C611—H61D	107.8
C313—C312—C317	117.6 (4)	C617—C612—C613	118.8 (4)
C313—C312—C311	121.0 (3)	C617—C612—C611	120.7 (4)
C317—C312—C311	121.3 (4)	C613—C612—C611	120.5 (3)
C312—C313—C314	120.7 (3)	C614—C613—C612	120.9 (4)
C312—C313—H313	119.7	C614—C613—H613	119.5
C314—C313—H313	119.7	C612—C613—H613	119.5
C313—C314—C315	121.0 (4)	C613—C614—C615	120.2 (5)
C313—C314—H314	119.5	C613—C614—H614	119.9
C315—C314—H314	119.5	C615—C614—H614	119.9
C316—C315—C314	117.3 (4)	C616—C615—C614	119.1 (5)
C316—C315—H315	121.3	C616—C615—H615	120.4
C314—C315—H315	121.3	C614—C615—H615	120.4
C317—C316—C315	121.7 (4)	C617—C616—C615	120.6 (4)
C317—C316—H316	119.2	C617—C616—H616	119.7
C315—C316—H316	119.2	C615—C616—H616	119.7
C316—C317—C312	121.8 (4)	C616—C617—C612	120.3 (5)
C316—C317—H317	119.1	C616—C617—H617	119.9
C312—C317—H317	119.1	C612—C617—H617	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···O25ⁱ	0.79 (4)	2.28 (4)	2.906 (4)	137 (4)
N24—H24···O15ⁱ	0.89 (4)	2.10 (5)	2.964 (4)	165 (4)
N34—H34···O45ⁱⁱ	1.00 (4)	2.00 (4)	2.881 (4)	145 (3)
N44—H44···O35	0.80 (3)	2.16 (3)	2.930 (5)	162 (4)
N54—H54···O65ⁱⁱ	0.86 (3)	2.13 (3)	2.946 (4)	159 (3)
N64—H64···O55	0.96 (4)	2.01 (4)	2.895 (4)	152 (3)

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

(2a) top

Crystal data top

C₁₆H₂₀N₂O₂	Z = 2
M_r = 272.34	F(000) = 292
Triclinic, P1	D_x = 1.304 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71070 Å
a = 7.4277 (2) Å	Cell parameters from 10488 reflections
b = 7.4388 (3) Å	θ = 1–27°
c = 13.5369 (5) Å	µ = 0.09 mm⁻¹
α = 90.176 (2)°	T = 150 K
β = 79.737 (2)°	Irregular, colourless
γ = 70.800 (2)°	0.5 × 0.35 × 0.25 mm
V = 693.52 (4) Å³

Data collection top

Nonius KappaCCD area detector diffractometer	4906 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.070
Graphite monochromator	θ_max = 27.2°, θ_min = 2.9°
Detector resolution: 9.091 pixels mm^-1	h = −9→9
φ and ω scans to fill the Ewald sphere	k = −9→9
11078 measured reflections	l = −17→15
5078 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0539P)² + 0.1346P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
5078 reflections	Δρ_max = 0.28 e Å⁻³
363 parameters	Δρ_min = −0.24 e Å⁻³
3 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.2 (9)

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.6311 (2)	0.2315 (2)	0.08112 (11)	0.0226 (3)
C2	0.6909 (2)	0.0720 (2)	0.02033 (13)	0.0228 (3)
O2	0.59020 (18)	−0.0293 (2)	0.01480 (10)	0.0322 (3)
C3	0.8911 (2)	0.0123 (2)	−0.04502 (13)	0.0219 (3)
H3	0.8750	−0.0082	−0.1140	0.026*
N4	0.9873 (2)	0.1559 (2)	−0.04707 (11)	0.0227 (3)
C4	1.1665 (3)	0.1208 (3)	−0.12202 (15)	0.0293 (4)
H4A	1.1761	0.2402	−0.1443	0.044*
H4B	1.1640	0.0436	−0.1784	0.044*
H4C	1.2764	0.0555	−0.0923	0.044*
C5	0.9445 (2)	0.2951 (2)	0.02569 (13)	0.0237 (3)
O5	1.0476 (2)	0.39306 (19)	0.03084 (11)	0.0350 (3)
C6	0.7544 (2)	0.3399 (2)	0.10051 (13)	0.0230 (3)
H6	0.6809	0.4744	0.0950	0.028*
C7	0.7881 (3)	0.3218 (3)	0.20922 (13)	0.0267 (4)
H7A	0.8645	0.1912	0.2179	0.032*
H7B	0.8602	0.4036	0.2230	0.032*
C8	0.5947 (3)	0.3783 (3)	0.28314 (15)	0.0341 (4)
H8A	0.6188	0.3525	0.3507	0.041*
H8B	0.5278	0.5142	0.2820	0.041*
C9	0.4668 (3)	0.2697 (3)	0.25712 (15)	0.0350 (4)
H9A	0.3411	0.3168	0.3016	0.042*
H9B	0.5254	0.1355	0.2673	0.042*
C10	0.4398 (2)	0.2920 (3)	0.14862 (14)	0.0294 (4)
H10A	0.3650	0.2147	0.1323	0.035*
H10B	0.3692	0.4242	0.1397	0.035*
C11	1.0179 (3)	−0.1816 (2)	−0.01458 (14)	0.0254 (4)
H11A	0.9570	−0.2761	−0.0234	0.030*
H11B	1.1433	−0.2212	−0.0595	0.030*
C12	1.0488 (2)	−0.1780 (2)	0.09209 (14)	0.0236 (4)
C13	0.9193 (3)	−0.2164 (2)	0.16938 (14)	0.0262 (4)
H13	0.8146	−0.2464	0.1545	0.031*
C14	0.9434 (3)	−0.2110 (3)	0.26848 (15)	0.0310 (4)
H14	0.8561	−0.2382	0.3194	0.037*
C15	1.0985 (3)	−0.1646 (3)	0.29140 (15)	0.0353 (5)
H15	1.1139	−0.1585	0.3579	0.042*
C16	1.2297 (3)	−0.1275 (3)	0.21547 (17)	0.0356 (5)
H16	1.3347	−0.0984	0.2306	0.043*
C17	1.2047 (3)	−0.1337 (3)	0.11608 (16)	0.0304 (4)
H17	1.2931	−0.1079	0.0652	0.036*
N21	0.4899 (2)	0.8958 (2)	0.67886 (10)	0.0215 (3)
C22	0.6232 (2)	0.8630 (2)	0.73778 (13)	0.0228 (3)
O22	0.7237 (2)	0.96498 (19)	0.74289 (10)	0.0323 (3)
C23	0.6511 (2)	0.6939 (2)	0.80252 (13)	0.0224 (3)
H23	0.6387	0.7431	0.8715	0.027*
N24	0.50558 (19)	0.6001 (2)	0.80523 (11)	0.0218 (3)
C24	0.5026 (3)	0.4597 (3)	0.88025 (14)	0.0293 (4)
H24A	0.3717	0.4618	0.9024	0.044*
H24B	0.5519	0.4903	0.9367	0.044*
H24C	0.5822	0.3349	0.8510	0.044*
C25	0.4023 (2)	0.6079 (2)	0.73241 (13)	0.0229 (3)
O25	0.30625 (19)	0.50239 (19)	0.72680 (11)	0.0347 (3)
C26	0.3921 (2)	0.7623 (2)	0.65851 (13)	0.0223 (3)
H26	0.2544	0.8377	0.6646	0.027*
C27	0.4637 (3)	0.6798 (3)	0.54885 (13)	0.0260 (4)
H27A	0.5994	0.6009	0.5394	0.031*
H27B	0.3902	0.6001	0.5341	0.031*
C28	0.4401 (3)	0.8393 (3)	0.47708 (14)	0.0330 (4)
H28A	0.3029	0.9052	0.4791	0.040*
H28B	0.4985	0.7848	0.4090	0.040*
C29	0.5342 (3)	0.9824 (3)	0.50395 (14)	0.0324 (4)
H29A	0.6741	0.9214	0.4926	0.039*
H29B	0.5053	1.0882	0.4609	0.039*
C210	0.4591 (3)	1.0569 (2)	0.61376 (14)	0.0278 (4)
H21A	0.5269	1.1401	0.6313	0.033*
H21B	0.3217	1.1302	0.6237	0.033*
C211	0.8604 (2)	0.5522 (3)	0.77144 (14)	0.0257 (4)
H21C	0.9509	0.6181	0.7785	0.031*
H21D	0.8794	0.4504	0.8172	0.031*
C212	0.9070 (2)	0.4656 (2)	0.66521 (13)	0.0233 (4)
C213	0.8709 (3)	0.2984 (3)	0.64377 (15)	0.0283 (4)
H213	0.8182	0.2386	0.6958	0.034*
C214	0.9128 (3)	0.2204 (3)	0.54578 (17)	0.0344 (4)
H214	0.8883	0.1087	0.5327	0.041*
C215	0.9904 (3)	0.3074 (3)	0.46757 (15)	0.0336 (4)
H215	1.0168	0.2557	0.4018	0.040*
C216	1.0287 (3)	0.4728 (3)	0.48791 (14)	0.0310 (4)
H216	1.0831	0.5312	0.4358	0.037*
C217	0.9859 (2)	0.5512 (3)	0.58620 (14)	0.0264 (4)
H217	1.0106	0.6629	0.5991	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0209 (7)	0.0233 (7)	0.0218 (7)	−0.0066 (6)	−0.0011 (5)	−0.0020 (6)
C2	0.0234 (8)	0.0240 (8)	0.0222 (9)	−0.0089 (7)	−0.0058 (7)	0.0011 (7)
O2	0.0298 (7)	0.0336 (7)	0.0358 (7)	−0.0159 (6)	−0.0029 (6)	−0.0062 (6)
C3	0.0256 (8)	0.0196 (8)	0.0206 (8)	−0.0082 (7)	−0.0030 (6)	−0.0027 (6)
N4	0.0238 (7)	0.0197 (7)	0.0235 (7)	−0.0081 (6)	−0.0005 (5)	0.0000 (6)
C4	0.0262 (9)	0.0278 (9)	0.0297 (9)	−0.0075 (7)	0.0028 (7)	0.0010 (7)
C5	0.0264 (8)	0.0179 (8)	0.0256 (9)	−0.0054 (7)	−0.0056 (7)	0.0019 (6)
O5	0.0371 (7)	0.0276 (7)	0.0439 (8)	−0.0172 (6)	−0.0049 (6)	−0.0016 (6)
C6	0.0276 (9)	0.0153 (7)	0.0256 (9)	−0.0057 (7)	−0.0063 (7)	0.0002 (6)
C7	0.0333 (9)	0.0220 (8)	0.0244 (9)	−0.0080 (7)	−0.0070 (7)	−0.0027 (7)
C8	0.0388 (10)	0.0343 (10)	0.0228 (9)	−0.0059 (8)	−0.0017 (8)	−0.0065 (8)
C9	0.0310 (10)	0.0402 (11)	0.0270 (10)	−0.0085 (9)	0.0055 (8)	−0.0041 (8)
C10	0.0200 (8)	0.0317 (10)	0.0312 (10)	−0.0041 (7)	0.0001 (7)	−0.0045 (8)
C11	0.0286 (9)	0.0184 (8)	0.0262 (9)	−0.0061 (7)	−0.0010 (7)	−0.0034 (7)
C12	0.0251 (8)	0.0142 (7)	0.0289 (9)	−0.0031 (6)	−0.0053 (7)	0.0008 (6)
C13	0.0283 (9)	0.0184 (8)	0.0325 (9)	−0.0081 (7)	−0.0069 (7)	−0.0003 (7)
C14	0.0373 (10)	0.0260 (9)	0.0283 (9)	−0.0099 (8)	−0.0038 (8)	0.0032 (7)
C15	0.0490 (12)	0.0286 (10)	0.0324 (11)	−0.0124 (9)	−0.0193 (9)	0.0053 (8)
C16	0.0375 (10)	0.0297 (10)	0.0489 (12)	−0.0158 (8)	−0.0232 (9)	0.0088 (9)
C17	0.0272 (9)	0.0233 (9)	0.0411 (11)	−0.0074 (7)	−0.0098 (8)	0.0089 (8)
N21	0.0246 (7)	0.0194 (7)	0.0209 (7)	−0.0077 (6)	−0.0047 (6)	0.0005 (5)
C22	0.0247 (8)	0.0215 (8)	0.0225 (8)	−0.0084 (7)	−0.0035 (7)	−0.0026 (6)
O22	0.0394 (7)	0.0313 (7)	0.0358 (7)	−0.0208 (6)	−0.0147 (6)	0.0060 (6)
C23	0.0226 (8)	0.0254 (8)	0.0213 (8)	−0.0102 (7)	−0.0052 (6)	0.0008 (7)
N24	0.0206 (7)	0.0211 (7)	0.0235 (7)	−0.0073 (6)	−0.0030 (5)	0.0022 (5)
C24	0.0275 (9)	0.0273 (9)	0.0313 (10)	−0.0080 (7)	−0.0035 (7)	0.0068 (7)
C25	0.0153 (7)	0.0233 (8)	0.0290 (9)	−0.0059 (6)	−0.0022 (6)	−0.0013 (7)
O25	0.0307 (7)	0.0344 (7)	0.0452 (8)	−0.0177 (6)	−0.0103 (6)	0.0031 (6)
C26	0.0179 (7)	0.0229 (8)	0.0253 (8)	−0.0055 (6)	−0.0046 (6)	−0.0031 (7)
C27	0.0235 (8)	0.0288 (9)	0.0257 (9)	−0.0085 (7)	−0.0055 (7)	−0.0053 (7)
C28	0.0382 (11)	0.0363 (10)	0.0229 (9)	−0.0077 (9)	−0.0108 (8)	−0.0007 (8)
C29	0.0421 (11)	0.0321 (10)	0.0230 (9)	−0.0119 (9)	−0.0070 (8)	0.0057 (8)
C210	0.0342 (10)	0.0202 (8)	0.0280 (9)	−0.0059 (7)	−0.0094 (7)	0.0041 (7)
C211	0.0208 (8)	0.0300 (9)	0.0265 (9)	−0.0071 (7)	−0.0072 (7)	0.0037 (7)
C212	0.0165 (7)	0.0236 (8)	0.0283 (9)	−0.0044 (7)	−0.0054 (7)	0.0004 (7)
C213	0.0233 (9)	0.0240 (8)	0.0355 (10)	−0.0082 (7)	0.0004 (7)	0.0006 (7)
C214	0.0282 (9)	0.0274 (9)	0.0462 (12)	−0.0100 (8)	−0.0024 (8)	−0.0090 (8)
C215	0.0279 (9)	0.0347 (10)	0.0319 (10)	−0.0040 (8)	−0.0025 (8)	−0.0110 (8)
C216	0.0266 (9)	0.0344 (10)	0.0280 (10)	−0.0071 (8)	−0.0012 (7)	0.0033 (8)
C217	0.0212 (8)	0.0246 (8)	0.0335 (10)	−0.0074 (7)	−0.0056 (7)	0.0015 (7)

Geometric parameters (Å, º) top

N1—C2	1.342 (2)	N21—C22	1.342 (2)
N1—C6	1.459 (2)	N21—C26	1.460 (2)
N1—C10	1.473 (2)	N21—C210	1.471 (2)
C2—O2	1.234 (2)	C22—O22	1.236 (2)
C2—C3	1.512 (2)	C22—C23	1.514 (2)
C3—N4	1.466 (2)	C23—N24	1.462 (2)
C3—C11	1.544 (2)	C23—C211	1.546 (2)
C3—H3	0.9800	C23—H23	0.9800
N4—C5	1.345 (2)	N24—C25	1.343 (2)
N4—C4	1.469 (2)	N24—C24	1.462 (2)
C4—H4A	0.9600	C24—H24A	0.9600
C4—H4B	0.9600	C24—H24B	0.9600
C4—H4C	0.9600	C24—H24C	0.9600
C5—O5	1.228 (2)	C25—O25	1.232 (2)
C5—C6	1.520 (2)	C25—C26	1.518 (3)
C6—C7	1.535 (2)	C26—C27	1.537 (2)
C6—H6	0.9800	C26—H26	0.9800
C7—C8	1.526 (3)	C27—C28	1.521 (3)
C7—H7A	0.9700	C27—H27A	0.9700
C7—H7B	0.9700	C27—H27B	0.9700
C8—C9	1.517 (3)	C28—C29	1.527 (3)
C8—H8A	0.9700	C28—H28A	0.9700
C8—H8B	0.9700	C28—H28B	0.9700
C9—C10	1.520 (3)	C29—C210	1.525 (3)
C9—H9A	0.9700	C29—H29A	0.9700
C9—H9B	0.9700	C29—H29B	0.9700
C10—H10A	0.9700	C210—H21A	0.9700
C10—H10B	0.9700	C210—H21B	0.9700
C11—C12	1.504 (3)	C211—C212	1.508 (2)
C11—H11A	0.9700	C211—H21C	0.9700
C11—H11B	0.9700	C211—H21D	0.9700
C12—C13	1.388 (3)	C212—C217	1.385 (3)
C12—C17	1.393 (2)	C212—C213	1.396 (2)
C13—C14	1.387 (3)	C213—C214	1.386 (3)
C13—H13	0.9300	C213—H213	0.9300
C14—C15	1.390 (3)	C214—C215	1.380 (3)
C14—H14	0.9300	C214—H214	0.9300
C15—C16	1.379 (3)	C215—C216	1.388 (3)
C15—H15	0.9300	C215—H215	0.9300
C16—C17	1.393 (3)	C216—C217	1.391 (3)
C16—H16	0.9300	C216—H216	0.9300
C17—H17	0.9300	C217—H217	0.9300

C2—N1—C6	124.78 (14)	C22—N21—C26	124.54 (15)
C2—N1—C10	120.78 (14)	C22—N21—C210	120.64 (14)
C6—N1—C10	113.58 (13)	C26—N21—C210	113.85 (13)
O2—C2—N1	123.22 (15)	O22—C22—N21	123.37 (16)
O2—C2—C3	117.96 (14)	O22—C22—C23	118.02 (15)
N1—C2—C3	118.82 (14)	N21—C22—C23	118.60 (14)
N4—C3—C2	114.35 (13)	N24—C23—C22	114.55 (13)
N4—C3—C11	111.80 (14)	N24—C23—C211	112.15 (14)
C2—C3—C11	109.80 (14)	C22—C23—C211	109.77 (14)
N4—C3—H3	106.8	N24—C23—H23	106.6
C2—C3—H3	106.8	C22—C23—H23	106.6
C11—C3—H3	106.8	C211—C23—H23	106.6
C5—N4—C3	124.19 (14)	C25—N24—C24	117.94 (14)
C5—N4—C4	117.67 (14)	C25—N24—C23	123.74 (14)
C3—N4—C4	116.88 (14)	C24—N24—C23	117.07 (14)
N4—C4—H4A	109.5	N24—C24—H24A	109.5
N4—C4—H4B	109.5	N24—C24—H24B	109.5
H4A—C4—H4B	109.5	H24A—C24—H24B	109.5
N4—C4—H4C	109.5	N24—C24—H24C	109.5
H4A—C4—H4C	109.5	H24A—C24—H24C	109.5
H4B—C4—H4C	109.5	H24B—C24—H24C	109.5
O5—C5—N4	122.71 (16)	O25—C25—N24	122.71 (16)
O5—C5—C6	118.97 (15)	O25—C25—C26	118.64 (15)
N4—C5—C6	118.21 (15)	N24—C25—C26	118.50 (14)
N1—C6—C5	114.98 (13)	N21—C26—C25	114.78 (14)
N1—C6—C7	110.40 (14)	N21—C26—C27	109.97 (14)
C5—C6—C7	111.53 (14)	C25—C26—C27	112.28 (14)
N1—C6—H6	106.4	N21—C26—H26	106.4
C5—C6—H6	106.4	C25—C26—H26	106.4
C7—C6—H6	106.4	C27—C26—H26	106.4
C8—C7—C6	110.53 (15)	C28—C27—C26	110.57 (14)
C8—C7—H7A	109.5	C28—C27—H27A	109.5
C6—C7—H7A	109.5	C26—C27—H27A	109.5
C8—C7—H7B	109.5	C28—C27—H27B	109.5
C6—C7—H7B	109.5	C26—C27—H27B	109.5
H7A—C7—H7B	108.1	H27A—C27—H27B	108.1
C9—C8—C7	111.44 (15)	C27—C28—C29	111.93 (15)
C9—C8—H8A	109.3	C27—C28—H28A	109.2
C7—C8—H8A	109.3	C29—C28—H28A	109.2
C9—C8—H8B	109.3	C27—C28—H28B	109.2
C7—C8—H8B	109.3	C29—C28—H28B	109.2
H8A—C8—H8B	108.0	H28A—C28—H28B	107.9
C8—C9—C10	111.17 (16)	C210—C29—C28	110.50 (16)
C8—C9—H9A	109.4	C210—C29—H29A	109.5
C10—C9—H9A	109.4	C28—C29—H29A	109.5
C8—C9—H9B	109.4	C210—C29—H29B	109.5
C10—C9—H9B	109.4	C28—C29—H29B	109.5
H9A—C9—H9B	108.0	H29A—C29—H29B	108.1
N1—C10—C9	109.56 (14)	N21—C210—C29	109.72 (14)
N1—C10—H10A	109.8	N21—C210—H21A	109.7
C9—C10—H10A	109.8	C29—C210—H21A	109.7
N1—C10—H10B	109.8	N21—C210—H21B	109.7
C9—C10—H10B	109.8	C29—C210—H21B	109.7
H10A—C10—H10B	108.2	H21A—C210—H21B	108.2
C12—C11—C3	113.82 (13)	C212—C211—C23	113.88 (14)
C12—C11—H11A	108.8	C212—C211—H21C	108.8
C3—C11—H11A	108.8	C23—C211—H21C	108.8
C12—C11—H11B	108.8	C212—C211—H21D	108.8
C3—C11—H11B	108.8	C23—C211—H21D	108.8
H11A—C11—H11B	107.7	H21C—C211—H21D	107.7
C13—C12—C17	118.49 (17)	C217—C212—C213	118.33 (16)
C13—C12—C11	120.18 (16)	C217—C212—C211	120.61 (15)
C17—C12—C11	121.32 (16)	C213—C212—C211	121.06 (16)
C14—C13—C12	121.14 (17)	C214—C213—C212	120.71 (17)
C14—C13—H13	119.4	C214—C213—H213	119.6
C12—C13—H13	119.4	C212—C213—H213	119.6
C13—C14—C15	119.73 (18)	C215—C214—C213	120.48 (18)
C13—C14—H14	120.1	C215—C214—H214	119.8
C15—C14—H14	120.1	C213—C214—H214	119.8
C16—C15—C14	119.96 (17)	C214—C215—C216	119.42 (17)
C16—C15—H15	120.0	C214—C215—H215	120.3
C14—C15—H15	120.0	C216—C215—H215	120.3
C15—C16—C17	119.96 (17)	C215—C216—C217	120.01 (18)
C15—C16—H16	120.0	C215—C216—H216	120.0
C17—C16—H16	120.0	C217—C216—H216	120.0
C12—C17—C16	120.72 (18)	C212—C217—C216	121.04 (17)
C12—C17—H17	119.6	C212—C217—H217	119.5
C16—C17—H17	119.6	C216—C217—H217	119.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O22ⁱ	0.98	2.44	3.386 (2)	161
C11—H11A···O5ⁱⁱ	0.97	2.48	3.169 (2)	128
C17—H17···O2ⁱⁱⁱ	0.93	2.45	3.279 (2)	149
C211—H21C···O25ⁱⁱⁱ	0.97	2.46	3.154 (2)	129
C23—H23···O2^iv	0.98	2.47	3.405 (2)	160
C213—H213···O22ⁱⁱ	0.93	2.41	3.229 (2)	146

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

(2b) top

Crystal data top

C₁₆H₂₀N₂O₂	F(000) = 584
M_r = 272.34	D_x = 1.245 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1930 reflections
a = 10.0530 (3) Å	θ = 1–27.5°
b = 10.8372 (2) Å	µ = 0.08 mm⁻¹
c = 13.3352 (5) Å	T = 150 K
V = 1452.82 (7) Å³	Prism, colourless
Z = 4	0.35 × 0.35 × 0.2 mm

Data collection top

Nonius KappaCCD area detector diffractometer	3001 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 27.5°, θ_min = 2.4°
Detector resolution: 9.091 pixels mm^-1	h = −13→13
φ and ω scans to fill the Ewald sphere	k = −14→14
19589 measured reflections	l = −17→17
3329 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0412P)² + 0.1777P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3329 reflections	Δρ_max = 0.11 e Å⁻³
182 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.0 (10)

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.76966 (11)	0.78748 (9)	0.10030 (8)	0.0309 (2)
C2	0.71461 (13)	0.88638 (11)	0.14480 (10)	0.0318 (3)
C3	0.63673 (12)	0.86737 (11)	0.24015 (10)	0.0307 (3)
H3	0.5556	0.9170	0.2348	0.037*
N4	0.59584 (9)	0.74034 (9)	0.25791 (8)	0.0272 (2)
C5	0.65930 (11)	0.64213 (11)	0.22008 (9)	0.0254 (2)
C6	0.76476 (12)	0.66229 (10)	0.14093 (9)	0.0269 (2)
H6	0.8514	0.6445	0.1714	0.032*
C7	0.74331 (15)	0.57026 (12)	0.05532 (10)	0.0388 (3)
H7A	0.7484	0.4869	0.0815	0.047*
H7B	0.6551	0.5819	0.0273	0.047*
C8	0.8463 (2)	0.58622 (16)	−0.02691 (13)	0.0584 (5)
H8A	0.9339	0.5667	−0.0009	0.070*
H8B	0.8272	0.5299	−0.0816	0.070*
C9	0.8446 (2)	0.71804 (16)	−0.06530 (12)	0.0554 (4)
H9A	0.9137	0.7287	−0.1154	0.066*
H9B	0.7595	0.7352	−0.0967	0.066*
C10	0.86717 (16)	0.80670 (15)	0.01999 (12)	0.0469 (4)
H10A	0.9562	0.7952	0.0465	0.056*
H10B	0.8603	0.8907	−0.0046	0.056*
C11	0.71812 (14)	0.91938 (12)	0.32945 (11)	0.0356 (3)
H11A	0.7317	1.0072	0.3197	0.043*
H11B	0.6678	0.9084	0.3909	0.043*
C12	0.85125 (13)	0.85690 (11)	0.34014 (10)	0.0316 (3)
C13	0.96202 (14)	0.90234 (12)	0.29004 (12)	0.0379 (3)
H13	0.9553	0.9753	0.2537	0.046*
C14	1.08261 (14)	0.84019 (14)	0.29353 (13)	0.0438 (4)
H14	1.1561	0.8717	0.2598	0.053*
C15	1.09351 (15)	0.73154 (14)	0.34716 (13)	0.0460 (4)
H15	1.1740	0.6893	0.3491	0.055*
C16	0.98416 (16)	0.68598 (13)	0.39784 (13)	0.0442 (4)
H16	0.9913	0.6130	0.4341	0.053*
C17	0.86397 (14)	0.74835 (12)	0.39499 (11)	0.0365 (3)
H17	0.7912	0.7174	0.4300	0.044*
C18	0.49168 (14)	0.72095 (14)	0.33300 (11)	0.0393 (3)
H18A	0.4422	0.6479	0.3166	0.059*
H18B	0.4329	0.7908	0.3336	0.059*
H18C	0.5316	0.7115	0.3979	0.059*
O2	0.72732 (11)	0.99202 (9)	0.11236 (9)	0.0460 (3)
O5	0.63248 (9)	0.53580 (8)	0.24505 (7)	0.0360 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0321 (5)	0.0303 (5)	0.0305 (5)	−0.0033 (4)	0.0036 (5)	0.0031 (4)
C2	0.0271 (6)	0.0284 (6)	0.0400 (7)	−0.0032 (5)	−0.0070 (5)	0.0034 (5)
C3	0.0257 (6)	0.0241 (6)	0.0424 (7)	0.0033 (5)	−0.0017 (5)	−0.0031 (5)
N4	0.0233 (4)	0.0267 (5)	0.0315 (5)	−0.0007 (4)	0.0033 (4)	−0.0012 (4)
C5	0.0226 (5)	0.0260 (6)	0.0276 (6)	0.0009 (5)	−0.0026 (5)	0.0006 (5)
C6	0.0235 (5)	0.0282 (6)	0.0288 (6)	0.0016 (5)	0.0009 (5)	0.0013 (5)
C7	0.0503 (9)	0.0337 (7)	0.0324 (7)	0.0060 (6)	0.0028 (6)	−0.0066 (5)
C8	0.0748 (12)	0.0610 (10)	0.0395 (9)	0.0158 (9)	0.0208 (9)	−0.0068 (8)
C9	0.0637 (10)	0.0679 (11)	0.0346 (8)	0.0045 (9)	0.0180 (8)	0.0050 (7)
C10	0.0422 (8)	0.0568 (9)	0.0418 (8)	−0.0049 (7)	0.0136 (7)	0.0108 (7)
C11	0.0342 (7)	0.0294 (6)	0.0431 (8)	0.0024 (5)	−0.0012 (6)	−0.0106 (6)
C12	0.0326 (6)	0.0285 (6)	0.0338 (7)	0.0003 (5)	−0.0059 (6)	−0.0094 (5)
C13	0.0348 (7)	0.0316 (7)	0.0474 (8)	−0.0046 (5)	−0.0057 (6)	−0.0022 (6)
C14	0.0302 (7)	0.0446 (8)	0.0564 (9)	−0.0030 (6)	−0.0012 (7)	−0.0104 (7)
C15	0.0347 (7)	0.0410 (8)	0.0623 (10)	0.0069 (6)	−0.0142 (7)	−0.0143 (7)
C16	0.0502 (9)	0.0345 (7)	0.0479 (9)	0.0035 (6)	−0.0172 (7)	−0.0003 (7)
C17	0.0394 (7)	0.0383 (7)	0.0320 (7)	−0.0031 (6)	−0.0047 (6)	−0.0025 (6)
C18	0.0315 (7)	0.0449 (8)	0.0414 (8)	−0.0004 (6)	0.0107 (6)	−0.0037 (6)
O2	0.0470 (6)	0.0285 (5)	0.0624 (7)	−0.0050 (4)	−0.0031 (6)	0.0122 (4)
O5	0.0362 (5)	0.0273 (4)	0.0444 (5)	−0.0022 (4)	0.0080 (4)	0.0046 (4)

Geometric parameters (Å, º) top

N1—C2	1.3442 (17)	C9—H9A	0.9700
N1—C6	1.4618 (15)	C9—H9B	0.9700
N1—C10	1.4667 (17)	C10—H10A	0.9700
C2—O2	1.2305 (15)	C10—H10B	0.9700
C2—C3	1.5074 (19)	C11—C12	1.5067 (18)
C3—N4	1.4561 (15)	C11—H11A	0.9700
C3—C11	1.5509 (19)	C11—H11B	0.9700
C3—H3	0.9800	C12—C13	1.3887 (19)
N4—C5	1.3396 (15)	C12—C17	1.3912 (19)
N4—C18	1.4640 (16)	C13—C14	1.388 (2)
C5—O5	1.2294 (14)	C13—H13	0.9300
C5—C6	1.5118 (17)	C14—C15	1.382 (2)
C6—C7	1.5312 (17)	C14—H14	0.9300
C6—H6	0.9800	C15—C16	1.382 (2)
C7—C8	1.518 (2)	C15—H15	0.9300
C7—H7A	0.9700	C16—C17	1.385 (2)
C7—H7B	0.9700	C16—H16	0.9300
C8—C9	1.518 (2)	C17—H17	0.9300
C8—H8A	0.9700	C18—H18A	0.9600
C8—H8B	0.9700	C18—H18B	0.9600
C9—C10	1.506 (2)	C18—H18C	0.9600

C2—N1—C6	124.22 (11)	C10—C9—H9B	109.6
C2—N1—C10	118.97 (11)	C8—C9—H9B	109.6
C6—N1—C10	115.15 (11)	H9A—C9—H9B	108.1
O2—C2—N1	122.94 (13)	N1—C10—C9	111.11 (13)
O2—C2—C3	118.53 (12)	N1—C10—H10A	109.4
N1—C2—C3	118.51 (11)	C9—C10—H10A	109.4
N4—C3—C2	114.39 (10)	N1—C10—H10B	109.4
N4—C3—C11	111.58 (11)	C9—C10—H10B	109.4
C2—C3—C11	108.91 (10)	H10A—C10—H10B	108.0
N4—C3—H3	107.2	C12—C11—C3	112.21 (10)
C2—C3—H3	107.2	C12—C11—H11A	109.2
C11—C3—H3	107.2	C3—C11—H11A	109.2
C5—N4—C3	123.75 (10)	C12—C11—H11B	109.2
C5—N4—C18	118.96 (10)	C3—C11—H11B	109.2
C3—N4—C18	116.67 (10)	H11A—C11—H11B	107.9
O5—C5—N4	122.57 (11)	C13—C12—C17	118.62 (13)
O5—C5—C6	118.58 (10)	C13—C12—C11	120.49 (12)
N4—C5—C6	118.82 (10)	C17—C12—C11	120.76 (12)
N1—C6—C5	114.62 (10)	C14—C13—C12	120.82 (13)
N1—C6—C7	109.45 (10)	C14—C13—H13	119.6
C5—C6—C7	109.13 (10)	C12—C13—H13	119.6
N1—C6—H6	107.8	C15—C14—C13	120.01 (14)
C5—C6—H6	107.8	C15—C14—H14	120.0
C7—C6—H6	107.8	C13—C14—H14	120.0
C8—C7—C6	111.61 (12)	C16—C15—C14	119.64 (14)
C8—C7—H7A	109.3	C16—C15—H15	120.2
C6—C7—H7A	109.3	C14—C15—H15	120.2
C8—C7—H7B	109.3	C15—C16—C17	120.41 (14)
C6—C7—H7B	109.3	C15—C16—H16	119.8
H7A—C7—H7B	108.0	C17—C16—H16	119.8
C9—C8—C7	110.07 (13)	C16—C17—C12	120.48 (14)
C9—C8—H8A	109.6	C16—C17—H17	119.8
C7—C8—H8A	109.6	C12—C17—H17	119.8
C9—C8—H8B	109.6	N4—C18—H18A	109.5
C7—C8—H8B	109.6	N4—C18—H18B	109.5
H8A—C8—H8B	108.2	H18A—C18—H18B	109.5
C10—C9—C8	110.13 (14)	N4—C18—H18C	109.5
C10—C9—H9A	109.6	H18A—C18—H18C	109.5
C8—C9—H9A	109.6	H18B—C18—H18C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O5ⁱ	0.98	2.30	3.2703 (14)	169
C8—H8B···O5ⁱⁱ	0.97	2.45	3.3228 (19)	149
C15—H15···O2ⁱⁱⁱ	0.93	2.41	3.2053 (17)	143
C18—H18A···O2^iv	0.96	2.58	3.3961 (17)	143

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

(9a) top

Crystal data top

C₁₄H₁₆N₂O₂	F(000) = 260
M_r = 244.29	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1446 reflections
a = 5.6190 (2) Å	θ = 1–27.5°
b = 10.0392 (3) Å	µ = 0.09 mm⁻¹
c = 10.7068 (2) Å	T = 150 K
β = 92.4862 (15)°	Prism, colourless
V = 603.40 (3) Å³	0.4 × 0.3 × 0.25 mm
Z = 2

Data collection top

Nonius KappaCCD area detector diffractometer	2686 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 27.5°, θ_min = 2.8°
Detector resolution: 9.091 pixels mm^-1	h = −7→7
φ and ω scans to fill the Ewald sphere	k = −12→12
9184 measured reflections	l = −13→13
2749 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.0353P)² + 0.0914P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2749 reflections	Δρ_max = 0.17 e Å⁻³
167 parameters	Δρ_min = −0.14 e Å⁻³
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.2 (8)

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.47099 (17)	0.40434 (9)	0.63512 (9)	0.0209 (2)
C2	0.3039 (2)	0.44530 (11)	0.55118 (10)	0.0199 (2)
C3	0.27201 (19)	0.34395 (10)	0.44400 (10)	0.0191 (2)
H3	0.4207	0.3426	0.3995	0.023*
N4	0.24194 (17)	0.21113 (9)	0.49905 (9)	0.02125 (19)
C5	0.39540 (19)	0.16963 (11)	0.59163 (10)	0.0196 (2)
C6	0.58621 (18)	0.27321 (10)	0.62341 (10)	0.0188 (2)
H6	0.6988	0.2767	0.5561	0.023*
C7	0.7233 (2)	0.25498 (11)	0.74796 (10)	0.0242 (2)
H7A	0.8687	0.2048	0.7377	0.029*
H7B	0.6271	0.2095	0.8078	0.029*
C8	0.7782 (2)	0.39800 (12)	0.78970 (11)	0.0262 (2)
H8A	0.9171	0.4321	0.7495	0.031*
H8B	0.8061	0.4027	0.8796	0.031*
C9	0.5543 (2)	0.47610 (12)	0.74836 (10)	0.0240 (2)
H9A	0.4363	0.4737	0.8118	0.029*
H9B	0.5920	0.5681	0.7298	0.029*
C10	0.0722 (2)	0.37830 (12)	0.34892 (10)	0.0231 (2)
H10A	−0.0782	0.3488	0.3805	0.028*
H10B	0.0646	0.4743	0.3390	0.028*
C11	0.10575 (19)	0.31493 (11)	0.22284 (10)	0.0211 (2)
C12	−0.0579 (2)	0.22343 (12)	0.17195 (11)	0.0257 (2)
H12	−0.1924	0.2018	0.2153	0.031*
C13	−0.0217 (2)	0.16398 (13)	0.05655 (12)	0.0312 (3)
H13	−0.1327	0.1035	0.0234	0.037*
C14	0.1776 (2)	0.19435 (14)	−0.00865 (11)	0.0326 (3)
H14	0.2024	0.1536	−0.0850	0.039*
C15	0.3411 (2)	0.28627 (15)	0.04063 (11)	0.0316 (3)
H15	0.4753	0.3075	−0.0033	0.038*
C16	0.3055 (2)	0.34645 (12)	0.15475 (11)	0.0258 (2)
H16	0.4153	0.4084	0.1865	0.031*
O2	0.19509 (14)	0.55179 (8)	0.55813 (7)	0.02473 (18)
O5	0.38324 (14)	0.06290 (8)	0.64613 (8)	0.02643 (19)
H4	0.112 (3)	0.1635 (17)	0.4789 (14)	0.033 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0259 (5)	0.0164 (4)	0.0203 (4)	0.0022 (3)	−0.0001 (4)	−0.0014 (3)
C2	0.0222 (5)	0.0185 (5)	0.0194 (5)	0.0000 (4)	0.0038 (4)	0.0025 (4)
C3	0.0210 (5)	0.0168 (5)	0.0196 (5)	0.0022 (4)	0.0018 (4)	0.0012 (4)
N4	0.0214 (4)	0.0172 (4)	0.0250 (5)	−0.0016 (4)	−0.0016 (3)	0.0011 (3)
C5	0.0197 (5)	0.0178 (5)	0.0215 (5)	0.0011 (4)	0.0028 (4)	−0.0009 (4)
C6	0.0191 (5)	0.0167 (5)	0.0207 (5)	0.0014 (4)	0.0016 (4)	0.0003 (4)
C7	0.0255 (5)	0.0216 (5)	0.0250 (5)	0.0018 (4)	−0.0047 (4)	−0.0002 (4)
C8	0.0269 (5)	0.0249 (6)	0.0263 (6)	−0.0025 (5)	−0.0033 (5)	−0.0027 (5)
C9	0.0292 (6)	0.0198 (5)	0.0228 (5)	−0.0002 (4)	−0.0005 (4)	−0.0035 (4)
C10	0.0228 (5)	0.0252 (6)	0.0214 (5)	0.0042 (4)	−0.0002 (4)	0.0028 (4)
C11	0.0211 (5)	0.0210 (5)	0.0211 (5)	0.0038 (4)	−0.0012 (4)	0.0047 (4)
C12	0.0229 (5)	0.0263 (6)	0.0273 (6)	−0.0009 (4)	−0.0034 (4)	0.0050 (4)
C13	0.0349 (6)	0.0277 (6)	0.0300 (6)	−0.0004 (5)	−0.0111 (5)	−0.0006 (5)
C14	0.0393 (6)	0.0374 (7)	0.0205 (5)	0.0086 (6)	−0.0058 (5)	−0.0028 (5)
C15	0.0288 (6)	0.0438 (7)	0.0223 (6)	0.0027 (5)	0.0031 (5)	0.0033 (5)
C16	0.0249 (5)	0.0294 (6)	0.0229 (5)	−0.0037 (4)	−0.0004 (4)	0.0032 (5)
O2	0.0286 (4)	0.0187 (4)	0.0270 (4)	0.0059 (3)	0.0021 (3)	0.0000 (3)
O5	0.0269 (4)	0.0189 (4)	0.0333 (4)	−0.0013 (3)	−0.0009 (3)	0.0059 (3)

Geometric parameters (Å, º) top

N1—C2	1.3358 (14)	C8—H8A	0.9700
N1—C9	1.4693 (14)	C8—H8B	0.9700
N1—C6	1.4747 (13)	C9—H9A	0.9700
C2—O2	1.2355 (13)	C9—H9B	0.9700
C2—C3	1.5384 (15)	C10—C11	1.5115 (15)
C3—N4	1.4706 (13)	C10—H10A	0.9700
C3—C10	1.5219 (15)	C10—H10B	0.9700
C3—H3	0.9800	C11—C12	1.3937 (16)
N4—C5	1.3511 (14)	C11—C16	1.4008 (15)
N4—H4	0.890 (17)	C12—C13	1.3949 (18)
C5—O5	1.2235 (14)	C12—H12	0.9300
C5—C6	1.5215 (15)	C13—C14	1.379 (2)
C6—C7	1.5218 (14)	C13—H13	0.9300
C6—H6	0.9800	C14—C15	1.390 (2)
C7—C8	1.5312 (16)	C14—H14	0.9300
C7—H7A	0.9700	C15—C16	1.3854 (17)
C7—H7B	0.9700	C15—H15	0.9300
C8—C9	1.5313 (16)	C16—H16	0.9300

C2—N1—C9	126.41 (10)	C7—C8—H8B	110.9
C2—N1—C6	121.06 (9)	C9—C8—H8B	110.9
C9—N1—C6	112.48 (9)	H8A—C8—H8B	109.0
O2—C2—N1	124.13 (10)	N1—C9—C8	102.47 (9)
O2—C2—C3	125.11 (10)	N1—C9—H9A	111.3
N1—C2—C3	110.73 (9)	C8—C9—H9A	111.3
N4—C3—C10	112.29 (9)	N1—C9—H9B	111.3
N4—C3—C2	108.21 (8)	C8—C9—H9B	111.3
C10—C3—C2	114.07 (9)	H9A—C9—H9B	109.2
N4—C3—H3	107.3	C11—C10—C3	112.66 (9)
C10—C3—H3	107.3	C11—C10—H10A	109.1
C2—C3—H3	107.3	C3—C10—H10A	109.1
C5—N4—C3	119.52 (9)	C11—C10—H10B	109.1
C5—N4—H4	120.1 (10)	C3—C10—H10B	109.1
C3—N4—H4	119.8 (10)	H10A—C10—H10B	107.8
O5—C5—N4	124.95 (10)	C12—C11—C16	118.37 (11)
O5—C5—C6	123.04 (10)	C12—C11—C10	121.40 (10)
N4—C5—C6	112.00 (9)	C16—C11—C10	120.22 (10)
N1—C6—C5	108.75 (8)	C11—C12—C13	120.62 (11)
N1—C6—C7	103.90 (8)	C11—C12—H12	119.7
C5—C6—C7	116.03 (9)	C13—C12—H12	119.7
N1—C6—H6	109.3	C14—C13—C12	120.42 (12)
C5—C6—H6	109.3	C14—C13—H13	119.8
C7—C6—H6	109.3	C12—C13—H13	119.8
C6—C7—C8	103.35 (9)	C13—C14—C15	119.51 (12)
C6—C7—H7A	111.1	C13—C14—H14	120.2
C8—C7—H7A	111.1	C15—C14—H14	120.2
C6—C7—H7B	111.1	C16—C15—C14	120.37 (12)
C8—C7—H7B	111.1	C16—C15—H15	119.8
H7A—C7—H7B	109.1	C14—C15—H15	119.8
C7—C8—C9	104.08 (9)	C15—C16—C11	120.68 (11)
C7—C8—H8A	110.9	C15—C16—H16	119.7
C9—C8—H8A	110.9	C11—C16—H16	119.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2ⁱ	0.890 (17)	2.083 (17)	2.9721 (12)	176.9 (14)

Symmetry code: (i) −x, y−1/2, −z+1.

(9b) top

Crystal data top

C₁₄H₁₆N₂O₂	F(000) = 260
M_r = 244.29	D_x = 1.308 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1507 reflections
a = 7.8134 (3) Å	θ = 1–27.5°
b = 6.5487 (2) Å	µ = 0.09 mm⁻¹
c = 12.1725 (4) Å	T = 150 K
β = 95.0641 (17)°	Bar, colourless
V = 620.41 (4) Å³	0.4 × 0.2 × 0.12 mm
Z = 2

Data collection top

Nonius KappaCCD area detector diffractometer	2604 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 27.5°, θ_min = 1.7°
Detector resolution: 9.091 pixels mm^-1	h = −10→10
φ and ω scans to fill the Ewald sphere	k = −8→8
9305 measured reflections	l = −15→15
2831 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0464P)² + 0.0425P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2831 reflections	Δρ_max = 0.29 e Å⁻³
167 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.1 (9)

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.97376 (13)	0.81471 (15)	0.69098 (9)	0.0240 (2)
C2	0.90364 (15)	0.62961 (18)	0.69766 (10)	0.0234 (3)
C3	0.71426 (16)	0.60791 (18)	0.66012 (10)	0.0253 (3)
H3	0.7024	0.4848	0.6115	0.030*
N4	0.64478 (14)	0.78083 (17)	0.59458 (9)	0.0276 (2)
H4	0.546 (2)	0.758 (2)	0.5541 (13)	0.036 (4)*
C5	0.71573 (16)	0.96488 (19)	0.58671 (10)	0.0269 (3)
C6	0.88671 (16)	1.00140 (18)	0.65147 (10)	0.0241 (3)
H6	0.8679	1.0895	0.7164	0.029*
C7	1.02259 (16)	1.10166 (19)	0.58637 (10)	0.0278 (3)
H7A	1.0241	1.0400	0.5122	0.033*
H7B	1.0028	1.2505	0.5786	0.033*
C8	1.18849 (17)	1.0567 (2)	0.65766 (12)	0.0321 (3)
H8A	1.2090	1.1605	0.7165	0.038*
H8B	1.2878	1.0553	0.6125	0.038*
C9	1.16081 (17)	0.8448 (2)	0.70737 (13)	0.0341 (3)
H9A	1.2221	0.7382	0.6686	0.041*
H9B	1.2013	0.8418	0.7867	0.041*
C11	0.61265 (16)	0.5635 (2)	0.76089 (11)	0.0293 (3)
H11A	0.4881	0.5731	0.7380	0.035*
H11B	0.6371	0.4220	0.7863	0.035*
C12	0.65652 (16)	0.7087 (2)	0.85585 (11)	0.0277 (3)
C13	0.77677 (17)	0.6517 (2)	0.94119 (11)	0.0351 (3)
H13	0.8276	0.5200	0.9406	0.042*
C14	0.8234 (2)	0.7843 (3)	1.02710 (12)	0.0440 (4)
H14	0.9065	0.7441	1.0847	0.053*
C15	0.7487 (2)	0.9758 (3)	1.02894 (13)	0.0459 (4)
H15	0.7799	1.0665	1.0882	0.055*
C16	0.6291 (2)	1.0352 (2)	0.94499 (13)	0.0399 (4)
H16	0.5780	1.1667	0.9464	0.048*
C17	0.58358 (18)	0.9024 (2)	0.85844 (12)	0.0314 (3)
H17	0.5018	0.9441	0.8004	0.038*
O2	0.98647 (12)	0.47946 (13)	0.73194 (8)	0.0295 (2)
O5	0.64784 (13)	1.10497 (15)	0.53046 (9)	0.0401 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0217 (5)	0.0224 (5)	0.0273 (6)	0.0021 (4)	−0.0017 (4)	0.0036 (4)
C2	0.0278 (6)	0.0234 (6)	0.0189 (6)	0.0012 (5)	0.0021 (5)	−0.0018 (5)
C3	0.0281 (6)	0.0216 (6)	0.0253 (6)	−0.0012 (5)	−0.0031 (5)	−0.0034 (5)
N4	0.0252 (5)	0.0304 (6)	0.0256 (6)	0.0005 (4)	−0.0067 (5)	−0.0018 (5)
C5	0.0277 (6)	0.0269 (6)	0.0252 (6)	0.0059 (5)	−0.0027 (5)	−0.0024 (5)
C6	0.0278 (6)	0.0209 (6)	0.0228 (6)	0.0036 (5)	−0.0017 (5)	0.0005 (5)
C7	0.0365 (7)	0.0217 (6)	0.0253 (7)	−0.0014 (5)	0.0026 (5)	0.0017 (5)
C8	0.0298 (6)	0.0303 (7)	0.0363 (8)	−0.0040 (5)	0.0045 (5)	0.0030 (5)
C9	0.0233 (6)	0.0344 (7)	0.0435 (8)	−0.0009 (5)	−0.0021 (6)	0.0101 (6)
C11	0.0276 (6)	0.0279 (6)	0.0323 (7)	−0.0060 (5)	0.0015 (5)	−0.0012 (5)
C12	0.0229 (6)	0.0349 (7)	0.0261 (6)	−0.0046 (5)	0.0069 (5)	0.0002 (5)
C13	0.0311 (7)	0.0451 (8)	0.0293 (7)	0.0005 (6)	0.0037 (6)	0.0014 (6)
C14	0.0364 (8)	0.0668 (11)	0.0280 (7)	−0.0022 (7)	−0.0021 (6)	−0.0033 (7)
C15	0.0450 (8)	0.0606 (10)	0.0326 (7)	−0.0106 (8)	0.0073 (7)	−0.0183 (8)
C16	0.0384 (8)	0.0416 (8)	0.0416 (9)	−0.0040 (6)	0.0137 (7)	−0.0119 (6)
C17	0.0246 (6)	0.0383 (7)	0.0318 (7)	−0.0016 (5)	0.0057 (5)	−0.0002 (6)
O2	0.0329 (5)	0.0232 (5)	0.0320 (5)	0.0046 (4)	−0.0006 (4)	0.0022 (4)
O5	0.0388 (5)	0.0359 (5)	0.0428 (6)	0.0078 (4)	−0.0116 (5)	0.0085 (5)

Geometric parameters (Å, º) top

N1—C2	1.3357 (16)	C8—H8A	0.9900
N1—C6	1.4597 (15)	C8—H8B	0.9900
N1—C9	1.4707 (17)	C9—H9A	0.9900
C2—O2	1.2297 (15)	C9—H9B	0.9900
C2—C3	1.5163 (17)	C11—C12	1.5128 (18)
C3—N4	1.4619 (16)	C11—H11A	0.9900
C3—C11	1.5465 (17)	C11—H11B	0.9900
C3—H3	1.0000	C12—C13	1.3889 (19)
N4—C5	1.3336 (17)	C12—C17	1.392 (2)
N4—H4	0.894 (17)	C13—C14	1.383 (2)
C5—O5	1.2360 (16)	C13—H13	0.9500
C5—C6	1.5090 (17)	C14—C15	1.384 (3)
C6—C7	1.5280 (17)	C14—H14	0.9500
C6—H6	1.0000	C15—C16	1.378 (2)
C7—C8	1.5236 (19)	C15—H15	0.9500
C7—H7A	0.9900	C16—C17	1.388 (2)
C7—H7B	0.9900	C16—H16	0.9500
C8—C9	1.5367 (19)	C17—H17	0.9500

C2—N1—C6	126.76 (10)	C7—C8—H8B	110.8
C2—N1—C9	121.42 (10)	C9—C8—H8B	110.8
C6—N1—C9	111.17 (10)	H8A—C8—H8B	108.8
O2—C2—N1	122.68 (11)	N1—C9—C8	103.90 (11)
O2—C2—C3	119.85 (11)	N1—C9—H9A	111.0
N1—C2—C3	117.47 (10)	C8—C9—H9A	111.0
N4—C3—C2	113.41 (10)	N1—C9—H9B	111.0
N4—C3—C11	112.75 (10)	C8—C9—H9B	111.0
C2—C3—C11	109.53 (10)	H9A—C9—H9B	109.0
N4—C3—H3	106.9	C12—C11—C3	112.97 (10)
C2—C3—H3	106.9	C12—C11—H11A	109.0
C11—C3—H3	106.9	C3—C11—H11A	109.0
C5—N4—C3	127.05 (11)	C12—C11—H11B	109.0
C5—N4—H4	117.4 (10)	C3—C11—H11B	109.0
C3—N4—H4	115.5 (10)	H11A—C11—H11B	107.8
O5—C5—N4	123.35 (12)	C13—C12—C17	118.65 (13)
O5—C5—C6	119.25 (12)	C13—C12—C11	119.67 (12)
N4—C5—C6	117.40 (11)	C17—C12—C11	121.64 (13)
N1—C6—C5	113.87 (10)	C14—C13—C12	120.80 (15)
N1—C6—C7	101.88 (9)	C14—C13—H13	119.6
C5—C6—C7	114.89 (10)	C12—C13—H13	119.6
N1—C6—H6	108.6	C13—C14—C15	119.87 (15)
C5—C6—H6	108.6	C13—C14—H14	120.1
C7—C6—H6	108.6	C15—C14—H14	120.1
C8—C7—C6	102.52 (10)	C16—C15—C14	120.20 (15)
C8—C7—H7A	111.3	C16—C15—H15	119.9
C6—C7—H7A	111.3	C14—C15—H15	119.9
C8—C7—H7B	111.3	C15—C16—C17	119.82 (15)
C6—C7—H7B	111.3	C15—C16—H16	120.1
H7A—C7—H7B	109.2	C17—C16—H16	120.1
C7—C8—C9	104.87 (11)	C16—C17—C12	120.67 (14)
C7—C8—H8A	110.8	C16—C17—H17	119.7
C9—C8—H8A	110.8	C12—C17—H17	119.7

C6—N1—C2—O2	179.90 (11)	N4—C5—C6—C7	132.51 (12)
C9—N1—C2—O2	10.02 (19)	N1—C6—C7—C8	−39.00 (12)
C6—N1—C2—C3	0.34 (17)	C5—C6—C7—C8	−162.60 (10)
C9—N1—C2—C3	−169.54 (12)	C6—C7—C8—C9	34.65 (13)
O2—C2—C3—N4	−164.18 (11)	C2—N1—C9—C8	162.72 (11)
N1—C2—C3—N4	15.39 (15)	C6—N1—C9—C8	−8.59 (15)
O2—C2—C3—C11	68.90 (14)	C7—C8—C9—N1	−16.79 (14)
N1—C2—C3—C11	−111.53 (12)	N4—C3—C11—C12	−78.26 (14)
C2—C3—N4—C5	−16.20 (17)	C2—C3—C11—C12	49.04 (14)
C11—C3—N4—C5	109.01 (14)	C3—C11—C12—C13	−96.46 (14)
C3—N4—C5—O5	−179.00 (12)	C3—C11—C12—C17	81.32 (14)
C3—N4—C5—C6	0.30 (18)	C17—C12—C13—C14	−0.02 (18)
C2—N1—C6—C5	−16.31 (16)	C11—C12—C13—C14	177.83 (12)
C9—N1—C6—C5	154.43 (11)	C12—C13—C14—C15	0.5 (2)
C2—N1—C6—C7	−140.60 (12)	C13—C14—C15—C16	−0.5 (2)
C9—N1—C6—C7	30.14 (13)	C14—C15—C16—C17	0.0 (2)
O5—C5—C6—N1	−165.12 (11)	C15—C16—C17—C12	0.5 (2)
N4—C5—C6—N1	15.54 (15)	C13—C12—C17—C16	−0.48 (18)
O5—C5—C6—C7	−48.16 (16)	C11—C12—C17—C16	−178.28 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5ⁱ	0.894 (17)	2.017 (17)	2.8733 (15)	160.1 (15)
C7—H7B···O2ⁱⁱ	0.99	2.41	3.0707 (15)	124

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

(9b-room) top

Crystal data top

C₁₄H₁₆N₂O₂	F(000) = 260
M_r = 244.29	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 8.0807 (7) Å	θ = 12–14°
b = 6.6311 (6) Å	µ = 0.09 mm⁻¹
c = 12.0895 (9) Å	T = 293 K
β = 96.428 (7)°	Bar, colourless
V = 643.73 (9) Å³	0.6 × 0.3 × 0.1 mm
Z = 2

Data collection top

CAD4-MACHIII diffractometer	R_int = 0.028
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 1.7°
Graphite monochromator	h = −9→9
θ–2θ scan	k = −7→7
2263 measured reflections	l = 0→14
2212 independent reflections	3 standard reflections every 3600 min
1942 reflections with I > 2σ(I)	intensity decay: 3%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0756P)² + 0.0177P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2212 reflections	Δρ_max = 0.19 e Å⁻³
167 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.2 (15)

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.46304 (19)	0.2001 (2)	0.69014 (13)	0.0442 (4)
C2	0.3958 (2)	0.0168 (3)	0.69721 (14)	0.0437 (4)
C3	0.2122 (2)	−0.0042 (3)	0.65991 (16)	0.0489 (4)
H3	0.1987	−0.1250	0.6130	0.059*
N4	0.1441 (2)	0.1635 (3)	0.59236 (14)	0.0541 (5)
H4	0.043 (3)	0.136 (4)	0.5508 (19)	0.065 (7)*
C5	0.2102 (3)	0.3463 (3)	0.58604 (16)	0.0518 (5)
C6	0.3757 (3)	0.3834 (3)	0.65098 (14)	0.0450 (4)
H6	0.3593	0.4675	0.7155	0.054*
C7	0.5048 (3)	0.4841 (3)	0.58651 (17)	0.0562 (5)
H7A	0.5024	0.4275	0.5124	0.067*
H7B	0.4860	0.6283	0.5806	0.067*
C8	0.6675 (3)	0.4381 (4)	0.6557 (2)	0.0676 (6)
H8A	0.6933	0.5408	0.7122	0.081*
H8B	0.7578	0.4317	0.6093	0.081*
C9	0.6419 (3)	0.2341 (4)	0.7092 (2)	0.0627 (6)
H9A	0.7018	0.1291	0.6745	0.075*
H9B	0.6796	0.2372	0.7882	0.075*
C11	0.1176 (3)	−0.0429 (3)	0.76061 (19)	0.0600 (5)
H11A	−0.0010	−0.0409	0.7364	0.072*
H11B	0.1455	−0.1766	0.7894	0.072*
C12	0.1543 (2)	0.1078 (4)	0.85303 (16)	0.0529 (5)
C13	0.2761 (3)	0.0674 (5)	0.93905 (18)	0.0725 (7)
H13	0.3314	−0.0557	0.9410	0.087*
C14	0.3170 (4)	0.2047 (8)	1.0213 (2)	0.1006 (12)
H14	0.4005	0.1752	1.0783	0.121*
C15	0.2361 (5)	0.3852 (8)	1.0204 (3)	0.1084 (13)
H15	0.2642	0.4785	1.0768	0.130*
C16	0.1145 (4)	0.4285 (5)	0.9371 (3)	0.0943 (10)
H16	0.0589	0.5513	0.9369	0.113*
C17	0.0727 (3)	0.2904 (4)	0.8521 (2)	0.0657 (6)
H17	−0.0101	0.3211	0.7949	0.079*
O2	0.4772 (2)	−0.12931 (19)	0.73232 (12)	0.0591 (4)
O5	0.1418 (2)	0.4838 (3)	0.52975 (16)	0.0819 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0435 (8)	0.0363 (8)	0.0513 (9)	0.0044 (7)	−0.0019 (7)	0.0065 (6)
C2	0.0554 (11)	0.0367 (10)	0.0386 (9)	0.0036 (9)	0.0032 (7)	−0.0015 (7)
C3	0.0587 (11)	0.0373 (10)	0.0481 (10)	−0.0029 (9)	−0.0051 (8)	−0.0074 (8)
N4	0.0519 (10)	0.0540 (12)	0.0517 (9)	−0.0017 (8)	−0.0146 (8)	−0.0062 (8)
C5	0.0574 (12)	0.0458 (12)	0.0490 (10)	0.0112 (10)	−0.0084 (9)	−0.0002 (9)
C6	0.0587 (11)	0.0320 (9)	0.0432 (9)	0.0069 (8)	0.0008 (8)	−0.0026 (7)
C7	0.0806 (14)	0.0353 (10)	0.0535 (11)	0.0012 (10)	0.0109 (10)	0.0042 (9)
C8	0.0623 (13)	0.0623 (15)	0.0800 (15)	−0.0093 (11)	0.0159 (11)	0.0093 (11)
C9	0.0465 (11)	0.0591 (14)	0.0805 (15)	−0.0010 (9)	−0.0018 (10)	0.0131 (11)
C11	0.0577 (11)	0.0524 (12)	0.0698 (13)	−0.0158 (10)	0.0065 (10)	−0.0032 (11)
C12	0.0446 (9)	0.0644 (13)	0.0515 (10)	−0.0107 (10)	0.0130 (8)	−0.0024 (10)
C13	0.0609 (13)	0.103 (2)	0.0532 (12)	0.0040 (14)	0.0068 (10)	0.0009 (13)
C14	0.0798 (19)	0.163 (4)	0.0577 (15)	−0.020 (2)	0.0042 (13)	−0.0201 (19)
C15	0.112 (3)	0.143 (4)	0.0742 (19)	−0.044 (3)	0.0256 (19)	−0.054 (2)
C16	0.103 (2)	0.084 (2)	0.107 (2)	−0.0099 (16)	0.057 (2)	−0.0282 (17)
C17	0.0541 (12)	0.0740 (16)	0.0720 (14)	−0.0040 (11)	0.0195 (11)	−0.0029 (12)
O2	0.0734 (10)	0.0379 (8)	0.0644 (9)	0.0124 (7)	0.0003 (7)	0.0059 (7)
O5	0.0813 (11)	0.0648 (11)	0.0911 (12)	0.0179 (9)	−0.0278 (9)	0.0201 (10)

Geometric parameters (Å, º) top

N1—C2	1.338 (2)	C8—H8A	0.9700
N1—C9	1.455 (3)	C8—H8B	0.9700
N1—C6	1.458 (2)	C9—H9A	0.9700
C2—O2	1.220 (2)	C9—H9B	0.9700
C2—C3	1.508 (3)	C11—C12	1.504 (3)
C3—N4	1.451 (3)	C11—H11A	0.9700
C3—C11	1.530 (3)	C11—H11B	0.9700
C3—H3	0.9800	C12—C13	1.376 (3)
N4—C5	1.330 (3)	C12—C17	1.378 (4)
N4—H4	0.93 (3)	C13—C14	1.361 (5)
C5—O5	1.231 (3)	C13—H13	0.9300
C5—C6	1.494 (3)	C14—C15	1.364 (6)
C6—C7	1.524 (3)	C14—H14	0.9300
C6—H6	0.9800	C15—C16	1.356 (6)
C7—C8	1.509 (4)	C15—H15	0.9300
C7—H7A	0.9700	C16—C17	1.390 (4)
C7—H7B	0.9700	C16—H16	0.9300
C8—C9	1.524 (3)	C17—H17	0.9300

C2—N1—C9	122.25 (16)	C7—C8—H8B	110.7
C2—N1—C6	126.37 (15)	C9—C8—H8B	110.7
C9—N1—C6	111.00 (16)	H8A—C8—H8B	108.8
O2—C2—N1	122.44 (17)	N1—C9—C8	104.50 (17)
O2—C2—C3	120.31 (17)	N1—C9—H9A	110.9
N1—C2—C3	117.25 (15)	C8—C9—H9A	110.9
N4—C3—C2	113.31 (17)	N1—C9—H9B	110.9
N4—C3—C11	112.60 (18)	C8—C9—H9B	110.9
C2—C3—C11	109.89 (16)	H9A—C9—H9B	108.9
N4—C3—H3	106.9	C12—C11—C3	113.89 (17)
C2—C3—H3	106.9	C12—C11—H11A	108.8
C11—C3—H3	106.9	C3—C11—H11A	108.8
C5—N4—C3	126.96 (17)	C12—C11—H11B	108.8
C5—N4—H4	118.9 (17)	C3—C11—H11B	108.8
C3—N4—H4	114.2 (17)	H11A—C11—H11B	107.7
O5—C5—N4	123.26 (19)	C13—C12—C17	118.6 (2)
O5—C5—C6	119.2 (2)	C13—C12—C11	119.8 (2)
N4—C5—C6	117.51 (17)	C17—C12—C11	121.6 (2)
N1—C6—C5	113.93 (16)	C14—C13—C12	121.1 (3)
N1—C6—C7	101.38 (16)	C14—C13—H13	119.4
C5—C6—C7	115.29 (16)	C12—C13—H13	119.4
N1—C6—H6	108.6	C13—C14—C15	120.3 (3)
C5—C6—H6	108.6	C13—C14—H14	119.9
C7—C6—H6	108.6	C15—C14—H14	119.9
C8—C7—C6	103.41 (16)	C16—C15—C14	119.9 (3)
C8—C7—H7A	111.1	C16—C15—H15	120.1
C6—C7—H7A	111.1	C14—C15—H15	120.1
C8—C7—H7B	111.1	C15—C16—C17	120.3 (4)
C6—C7—H7B	111.1	C15—C16—H16	119.8
H7A—C7—H7B	109.0	C17—C16—H16	119.8
C7—C8—C9	105.24 (18)	C12—C17—C16	119.8 (3)
C7—C8—H8A	110.7	C12—C17—H17	120.1
C9—C8—H8A	110.7	C16—C17—H17	120.1

C9—N1—C2—O2	8.7 (3)	N4—C5—C6—C7	131.7 (2)
C6—N1—C2—O2	−179.07 (17)	N1—C6—C7—C8	−37.70 (19)
C9—N1—C2—C3	−171.49 (19)	C5—C6—C7—C8	−161.25 (18)
C6—N1—C2—C3	0.8 (3)	C6—C7—C8—C9	31.5 (2)
O2—C2—C3—N4	−163.51 (17)	C2—N1—C9—C8	161.35 (19)
N1—C2—C3—N4	16.6 (2)	C6—N1—C9—C8	−12.0 (2)
O2—C2—C3—C11	69.6 (2)	C7—C8—C9—N1	−12.8 (2)
N1—C2—C3—C11	−110.3 (2)	N4—C3—C11—C12	−75.2 (2)
C2—C3—N4—C5	−19.2 (3)	C2—C3—C11—C12	52.2 (2)
C11—C3—N4—C5	106.3 (2)	C3—C11—C12—C13	−93.9 (3)
C3—N4—C5—O5	−177.2 (2)	C3—C11—C12—C17	83.8 (3)
C3—N4—C5—C6	2.9 (3)	C17—C12—C13—C14	−0.6 (4)
C2—N1—C6—C5	−17.2 (3)	C11—C12—C13—C14	177.1 (2)
C9—N1—C6—C5	155.78 (18)	C12—C13—C14—C15	0.7 (5)
C2—N1—C6—C7	−141.70 (18)	C13—C14—C15—C16	−0.2 (5)
C9—N1—C6—C7	31.3 (2)	C14—C15—C16—C17	−0.4 (5)
O5—C5—C6—N1	−164.9 (2)	C13—C12—C17—C16	0.0 (3)
N4—C5—C6—N1	15.0 (3)	C11—C12—C17—C16	−177.7 (2)
O5—C5—C6—C7	−48.3 (3)	C15—C16—C17—C12	0.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O5ⁱ	0.93 (3)	1.97 (3)	2.859 (2)	161 (2)
C7—H7B···O2ⁱⁱ	0.97	2.45	3.133 (2)	128

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

(10a) top

Crystal data top

C₁₅H₁₈N₂O₂	D_x = 1.306 Mg m⁻³
M_r = 258.31	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₃2₁2	Cell parameters from 3032 reflections
Hall symbol: P 4nw 2abw	θ = 3–27.5°
a = 7.8284 (2) Å	µ = 0.09 mm⁻¹
c = 42.8636 (9) Å	T = 150 K
V = 2626.85 (11) Å³	Prism, colourless
Z = 8	0.4 × 0.3 × 0.1 mm
F(000) = 1104

Data collection top

Nonius KappaCCD area detector diffractometer	2402 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.055
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
Detector resolution: 9.091 pixels mm^-1	h = −10→10
φ and ω scans to fill the Ewald sphere	k = −7→7
24574 measured reflections	l = −55→55
2994 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0388P)² + 0.3491P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2994 reflections	Δρ_max = 0.14 e Å⁻³
173 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 1.5 (14)

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.52102 (16)	0.89914 (16)	0.77171 (3)	0.0303 (3)
C2	0.3547 (2)	0.9272 (2)	0.77700 (3)	0.0288 (3)
C3	0.2535 (2)	0.78621 (19)	0.79282 (3)	0.0285 (3)
H3	0.1491	0.7688	0.7806	0.034*
N4	0.34033 (16)	0.62127 (16)	0.79491 (3)	0.0291 (3)
C5	0.5122 (2)	0.6021 (2)	0.79406 (4)	0.0312 (4)
C6	0.61582 (19)	0.7460 (2)	0.78063 (3)	0.0303 (4)
H6	0.6708	0.7024	0.7617	0.036*
C7	0.7568 (2)	0.8180 (2)	0.80133 (4)	0.0348 (4)
H7A	0.8555	0.7432	0.8016	0.042*
H7B	0.7167	0.8349	0.8225	0.042*
C8	0.7992 (2)	0.9893 (2)	0.78562 (4)	0.0393 (4)
H8A	0.8249	1.0753	0.8012	0.047*
H8B	0.8974	0.9770	0.7720	0.047*
C9	0.6419 (2)	1.0407 (2)	0.76683 (4)	0.0407 (4)
H9A	0.5948	1.1475	0.7744	0.049*
H9B	0.6697	1.0531	0.7449	0.049*
C10	0.19918 (19)	0.8534 (2)	0.82535 (3)	0.0315 (4)
H10A	0.1315	0.9561	0.8226	0.038*
H10B	0.1272	0.7685	0.8353	0.038*
C11	0.3475 (2)	0.8930 (2)	0.84658 (3)	0.0295 (3)
C12	0.4206 (2)	1.0551 (2)	0.84702 (4)	0.0352 (4)
H12	0.3784	1.1396	0.8339	0.042*
C13	0.5551 (2)	1.0918 (3)	0.86676 (4)	0.0441 (4)
H13	0.6024	1.2007	0.8668	0.053*
C14	0.6198 (2)	0.9688 (3)	0.88642 (4)	0.0470 (5)
H14	0.7096	0.9946	0.8998	0.056*
C15	0.5501 (2)	0.8069 (3)	0.88607 (4)	0.0427 (4)
H15	0.5938	0.7229	0.8992	0.051*
C16	0.4154 (2)	0.7692 (2)	0.86631 (3)	0.0337 (4)
H16	0.3696	0.6595	0.8662	0.040*
C17	0.2369 (2)	0.4768 (2)	0.80538 (4)	0.0380 (4)
H17A	0.2429	0.4681	0.8277	0.057*
H17B	0.2795	0.3734	0.7962	0.057*
H17C	0.1203	0.4939	0.7992	0.057*
O2	0.28202 (15)	1.06203 (14)	0.77088 (3)	0.0387 (3)
O5	0.58386 (16)	0.46897 (15)	0.80183 (3)	0.0437 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0288 (7)	0.0315 (7)	0.0307 (6)	−0.0035 (6)	−0.0019 (5)	0.0043 (6)
C2	0.0285 (8)	0.0329 (9)	0.0249 (7)	−0.0029 (7)	−0.0042 (6)	0.0022 (6)
C3	0.0252 (8)	0.0319 (8)	0.0283 (7)	−0.0019 (7)	−0.0032 (6)	0.0030 (6)
N4	0.0292 (7)	0.0276 (7)	0.0305 (6)	−0.0032 (5)	0.0008 (5)	0.0020 (5)
C5	0.0330 (9)	0.0322 (9)	0.0284 (8)	0.0029 (7)	−0.0014 (6)	−0.0012 (7)
C6	0.0275 (8)	0.0334 (9)	0.0301 (7)	0.0035 (7)	0.0017 (6)	0.0005 (7)
C7	0.0266 (8)	0.0450 (10)	0.0329 (8)	−0.0013 (7)	−0.0015 (7)	0.0006 (7)
C8	0.0313 (9)	0.0452 (10)	0.0414 (9)	−0.0082 (8)	0.0008 (7)	−0.0010 (8)
C9	0.0352 (10)	0.0438 (11)	0.0431 (9)	−0.0131 (8)	−0.0014 (8)	0.0090 (8)
C10	0.0251 (8)	0.0390 (10)	0.0303 (8)	0.0006 (7)	0.0004 (6)	0.0020 (7)
C11	0.0243 (8)	0.0368 (9)	0.0273 (7)	0.0019 (7)	0.0038 (6)	−0.0033 (7)
C12	0.0312 (9)	0.0362 (9)	0.0380 (9)	0.0022 (8)	0.0028 (7)	−0.0060 (7)
C13	0.0318 (10)	0.0469 (11)	0.0537 (10)	−0.0047 (8)	0.0045 (8)	−0.0218 (9)
C14	0.0292 (9)	0.0750 (14)	0.0367 (9)	−0.0001 (9)	−0.0030 (7)	−0.0204 (10)
C15	0.0354 (10)	0.0649 (13)	0.0278 (8)	0.0099 (9)	−0.0001 (7)	0.0001 (8)
C16	0.0302 (8)	0.0430 (10)	0.0280 (7)	0.0024 (8)	0.0037 (6)	0.0000 (7)
C17	0.0417 (10)	0.0345 (9)	0.0380 (8)	−0.0104 (8)	0.0002 (8)	0.0033 (7)
O2	0.0355 (7)	0.0359 (7)	0.0447 (6)	0.0015 (5)	−0.0061 (5)	0.0103 (6)
O5	0.0424 (7)	0.0347 (7)	0.0539 (7)	0.0057 (6)	−0.0038 (6)	0.0045 (6)

Geometric parameters (Å, º) top

N1—C2	1.340 (2)	C9—H9A	0.9700
N1—C6	1.4607 (19)	C9—H9B	0.9700
N1—C9	1.472 (2)	C10—C11	1.507 (2)
C2—O2	1.2275 (18)	C10—H10A	0.9700
C2—C3	1.518 (2)	C10—H10B	0.9700
C3—N4	1.4618 (19)	C11—C12	1.392 (2)
C3—C10	1.550 (2)	C11—C16	1.392 (2)
C3—H3	0.9800	C12—C13	1.381 (2)
N4—C5	1.354 (2)	C12—H12	0.9300
N4—C17	1.462 (2)	C13—C14	1.376 (3)
C5—O5	1.2295 (19)	C13—H13	0.9300
C5—C6	1.503 (2)	C14—C15	1.380 (3)
C6—C7	1.524 (2)	C14—H14	0.9300
C6—H6	0.9800	C15—C16	1.385 (2)
C7—C8	1.537 (2)	C15—H15	0.9300
C7—H7A	0.9700	C16—H16	0.9300
C7—H7B	0.9700	C17—H17A	0.9600
C8—C9	1.526 (2)	C17—H17B	0.9600
C8—H8A	0.9700	C17—H17C	0.9600
C8—H8B	0.9700

C2—N1—C6	125.73 (13)	N1—C9—C8	104.18 (13)
C2—N1—C9	121.68 (14)	N1—C9—H9A	110.9
C6—N1—C9	109.18 (12)	C8—C9—H9A	110.9
O2—C2—N1	123.72 (14)	N1—C9—H9B	110.9
O2—C2—C3	118.61 (14)	C8—C9—H9B	110.9
N1—C2—C3	117.61 (14)	H9A—C9—H9B	108.9
N4—C3—C2	115.28 (13)	C11—C10—C3	113.67 (13)
N4—C3—C10	111.84 (12)	C11—C10—H10A	108.8
C2—C3—C10	107.37 (13)	C3—C10—H10A	108.8
N4—C3—H3	107.3	C11—C10—H10B	108.8
C2—C3—H3	107.3	C3—C10—H10B	108.8
C10—C3—H3	107.3	H10A—C10—H10B	107.7
C5—N4—C3	123.93 (13)	C12—C11—C16	118.00 (15)
C5—N4—C17	118.21 (14)	C12—C11—C10	120.84 (15)
C3—N4—C17	116.42 (13)	C16—C11—C10	121.16 (15)
O5—C5—N4	122.70 (16)	C13—C12—C11	120.76 (17)
O5—C5—C6	119.51 (15)	C13—C12—H12	119.6
N4—C5—C6	117.61 (14)	C11—C12—H12	119.6
N1—C6—C5	116.17 (12)	C14—C13—C12	120.70 (18)
N1—C6—C7	102.52 (13)	C14—C13—H13	119.7
C5—C6—C7	116.44 (13)	C12—C13—H13	119.7
N1—C6—H6	107.0	C13—C14—C15	119.36 (17)
C5—C6—H6	107.0	C13—C14—H14	120.3
C7—C6—H6	107.0	C15—C14—H14	120.3
C6—C7—C8	102.94 (13)	C14—C15—C16	120.26 (17)
C6—C7—H7A	111.2	C14—C15—H15	119.9
C8—C7—H7A	111.2	C16—C15—H15	119.9
C6—C7—H7B	111.2	C15—C16—C11	120.92 (17)
C8—C7—H7B	111.2	C15—C16—H16	119.5
H7A—C7—H7B	109.1	C11—C16—H16	119.5
C9—C8—C7	106.69 (13)	N4—C17—H17A	109.5
C9—C8—H8A	110.4	N4—C17—H17B	109.5
C7—C8—H8A	110.4	H17A—C17—H17B	109.5
C9—C8—H8B	110.4	N4—C17—H17C	109.5
C7—C8—H8B	110.4	H17A—C17—H17C	109.5
H8A—C8—H8B	108.6	H17B—C17—H17C	109.5

(10b) top

Crystal data top

C₁₅H₁₈N₂O₂	F(000) = 552
M_r = 258.31	D_x = 1.277 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1784 reflections
a = 10.1348 (4) Å	θ = 1–27.5°
b = 10.9014 (3) Å	µ = 0.09 mm⁻¹
c = 12.1599 (4) Å	T = 150 K
V = 1343.47 (8) Å³	Prism, colourless
Z = 4	0.35 × 0.3 × 0.25 mm

Data collection top

Nonius KappaCCD area detector diffractometer	2577 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 27.5°, θ_min = 2.5°
Detector resolution: 9.091 pixels mm^-1	h = −13→13
φ and ω scans to fill the Ewald sphere	k = −14→14
11846 measured reflections	l = −15→15
3071 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0503P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3071 reflections	Δρ_max = 0.13 e Å⁻³
173 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.0 (10)

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.22471 (12)	0.77530 (9)	0.07886 (8)	0.0280 (3)
C2	0.28151 (14)	0.87308 (11)	0.12512 (10)	0.0268 (3)
C3	0.35221 (13)	0.85174 (11)	0.23322 (10)	0.0259 (3)
H3	0.4328	0.9047	0.2318	0.031*
N4	0.39891 (11)	0.72480 (10)	0.24597 (8)	0.0257 (2)
C5	0.34112 (13)	0.62720 (11)	0.19868 (10)	0.0265 (3)
C6	0.22360 (14)	0.65206 (11)	0.12583 (10)	0.0266 (3)
H6	0.1413	0.6416	0.1702	0.032*
C7	0.21393 (16)	0.57201 (12)	0.02345 (11)	0.0352 (3)
H7A	0.1770	0.4902	0.0409	0.042*
H7B	0.3010	0.5618	−0.0122	0.042*
C8	0.11994 (16)	0.64638 (14)	−0.04848 (11)	0.0406 (4)
H8A	0.0272	0.6337	−0.0256	0.049*
H8B	0.1292	0.6233	−0.1268	0.049*
C9	0.16223 (17)	0.77920 (14)	−0.02988 (11)	0.0405 (4)
H9A	0.2255	0.8063	−0.0869	0.049*
H9B	0.0851	0.8350	−0.0301	0.049*
C10	0.50917 (15)	0.70452 (14)	0.32134 (12)	0.0382 (4)
H10A	0.4756	0.6731	0.3915	0.057*
H10B	0.5556	0.7821	0.3338	0.057*
H10C	0.5702	0.6447	0.2892	0.057*
C11	0.26810 (14)	0.89624 (12)	0.33153 (10)	0.0299 (3)
H11A	0.3186	0.8833	0.4003	0.036*
H11B	0.2524	0.9854	0.3237	0.036*
C12	0.13761 (13)	0.83217 (12)	0.34128 (10)	0.0275 (3)
C13	0.02642 (14)	0.87856 (12)	0.28909 (12)	0.0341 (3)
H13	0.0324	0.9535	0.2496	0.041*
C14	−0.09319 (16)	0.81719 (15)	0.29372 (13)	0.0418 (4)
H14	−0.1683	0.8500	0.2574	0.050*
C15	−0.10320 (16)	0.70808 (13)	0.35133 (12)	0.0402 (4)
H15	−0.1851	0.6658	0.3548	0.048*
C16	0.00629 (15)	0.66102 (13)	0.40370 (12)	0.0380 (3)
H16	−0.0001	0.5858	0.4427	0.046*
C17	0.12553 (14)	0.72285 (12)	0.39969 (10)	0.0319 (3)
H17	0.1999	0.6903	0.4372	0.038*
O2	0.27815 (11)	0.97623 (8)	0.08400 (8)	0.0371 (3)
O5	0.37901 (10)	0.52100 (8)	0.21342 (8)	0.0388 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0315 (6)	0.0263 (5)	0.0262 (5)	0.0022 (5)	−0.0049 (5)	0.0002 (4)
C2	0.0261 (7)	0.0257 (7)	0.0285 (6)	0.0039 (6)	0.0044 (5)	−0.0013 (5)
C3	0.0253 (7)	0.0230 (6)	0.0293 (6)	−0.0022 (6)	0.0005 (5)	−0.0023 (5)
N4	0.0239 (6)	0.0272 (5)	0.0260 (5)	0.0018 (5)	−0.0042 (5)	−0.0018 (4)
C5	0.0273 (7)	0.0260 (6)	0.0262 (6)	−0.0003 (6)	−0.0005 (6)	0.0001 (5)
C6	0.0267 (7)	0.0246 (6)	0.0284 (6)	−0.0003 (6)	−0.0008 (5)	−0.0004 (5)
C7	0.0397 (8)	0.0320 (7)	0.0338 (7)	−0.0016 (7)	−0.0036 (6)	−0.0063 (6)
C8	0.0412 (9)	0.0493 (9)	0.0314 (7)	−0.0028 (8)	−0.0096 (6)	−0.0074 (6)
C9	0.0470 (9)	0.0418 (8)	0.0328 (8)	0.0086 (7)	−0.0149 (7)	−0.0006 (6)
C10	0.0324 (9)	0.0427 (8)	0.0396 (8)	0.0008 (7)	−0.0104 (6)	0.0009 (7)
C11	0.0290 (8)	0.0313 (7)	0.0296 (7)	−0.0011 (6)	0.0021 (6)	−0.0069 (5)
C12	0.0286 (7)	0.0282 (6)	0.0258 (6)	0.0007 (6)	0.0045 (5)	−0.0072 (5)
C13	0.0319 (8)	0.0285 (7)	0.0418 (8)	0.0029 (6)	0.0032 (7)	0.0019 (6)
C14	0.0293 (8)	0.0445 (9)	0.0515 (9)	0.0031 (7)	−0.0035 (7)	−0.0032 (7)
C15	0.0337 (9)	0.0362 (8)	0.0506 (9)	−0.0062 (7)	0.0090 (7)	−0.0098 (7)
C16	0.0452 (9)	0.0300 (7)	0.0389 (7)	−0.0029 (7)	0.0141 (7)	0.0003 (6)
C17	0.0340 (8)	0.0337 (7)	0.0281 (6)	0.0028 (6)	0.0033 (6)	0.0005 (6)
O2	0.0453 (6)	0.0256 (5)	0.0404 (6)	0.0037 (5)	−0.0013 (5)	0.0057 (4)
O5	0.0415 (6)	0.0249 (5)	0.0499 (6)	0.0039 (4)	−0.0122 (5)	0.0033 (4)

Geometric parameters (Å, º) top

N1—C2	1.3357 (16)	C9—H9A	0.9900
N1—C6	1.4598 (16)	C9—H9B	0.9900
N1—C9	1.4667 (17)	C10—H10A	0.9800
C2—O2	1.2311 (15)	C10—H10B	0.9800
C2—C3	1.5151 (18)	C10—H10C	0.9800
C3—N4	1.4707 (16)	C11—C12	1.500 (2)
C3—C11	1.5463 (18)	C11—H11A	0.9900
C3—H3	1.0000	C11—H11B	0.9900
N4—C5	1.3437 (16)	C12—C13	1.3887 (19)
N4—C10	1.4621 (17)	C12—C17	1.3928 (19)
C5—O5	1.2328 (15)	C13—C14	1.386 (2)
C5—C6	1.5089 (18)	C13—H13	0.9500
C6—C7	1.5235 (17)	C14—C15	1.384 (2)
C6—H6	1.0000	C14—H14	0.9500
C7—C8	1.526 (2)	C15—C16	1.378 (2)
C7—H7A	0.9900	C15—H15	0.9500
C7—H7B	0.9900	C16—C17	1.385 (2)
C8—C9	1.527 (2)	C16—H16	0.9500
C8—H8A	0.9900	C17—H17	0.9500
C8—H8B	0.9900

C2—N1—C6	124.96 (10)	N1—C9—C8	103.13 (11)
C2—N1—C9	122.86 (11)	N1—C9—H9A	111.1
C6—N1—C9	112.09 (10)	C8—C9—H9A	111.1
O2—C2—N1	123.09 (12)	N1—C9—H9B	111.1
O2—C2—C3	120.38 (11)	C8—C9—H9B	111.1
N1—C2—C3	116.53 (11)	H9A—C9—H9B	109.1
N4—C3—C2	112.84 (10)	N4—C10—H10A	109.5
N4—C3—C11	113.03 (10)	N4—C10—H10B	109.5
C2—C3—C11	111.21 (11)	H10A—C10—H10B	109.5
N4—C3—H3	106.4	N4—C10—H10C	109.5
C2—C3—H3	106.4	H10A—C10—H10C	109.5
C11—C3—H3	106.4	H10B—C10—H10C	109.5
C5—N4—C10	118.79 (11)	C12—C11—C3	113.64 (10)
C5—N4—C3	124.03 (10)	C12—C11—H11A	108.8
C10—N4—C3	117.02 (10)	C3—C11—H11A	108.8
O5—C5—N4	123.06 (12)	C12—C11—H11B	108.8
O5—C5—C6	119.99 (11)	C3—C11—H11B	108.8
N4—C5—C6	116.94 (11)	H11A—C11—H11B	107.7
N1—C6—C5	112.88 (11)	C13—C12—C17	118.25 (13)
N1—C6—C7	102.00 (10)	C13—C12—C11	120.64 (12)
C5—C6—C7	115.31 (11)	C17—C12—C11	121.08 (12)
N1—C6—H6	108.8	C14—C13—C12	121.03 (13)
C5—C6—H6	108.8	C14—C13—H13	119.5
C7—C6—H6	108.8	C12—C13—H13	119.5
C6—C7—C8	101.78 (11)	C15—C14—C13	119.97 (15)
C6—C7—H7A	111.4	C15—C14—H14	120.0
C8—C7—H7A	111.4	C13—C14—H14	120.0
C6—C7—H7B	111.4	C16—C15—C14	119.64 (14)
C8—C7—H7B	111.4	C16—C15—H15	120.2
H7A—C7—H7B	109.3	C14—C15—H15	120.2
C7—C8—C9	104.10 (11)	C15—C16—C17	120.34 (13)
C7—C8—H8A	110.9	C15—C16—H16	119.8
C9—C8—H8A	110.9	C17—C16—H16	119.8
C7—C8—H8B	110.9	C16—C17—C12	120.75 (13)
C9—C8—H8B	110.9	C16—C17—H17	119.6
H8A—C8—H8B	109.0	C12—C17—H17	119.6

C6—N1—C2—O2	−178.52 (12)	N4—C5—C6—N1	25.59 (16)
C9—N1—C2—O2	5.2 (2)	O5—C5—C6—C7	−38.49 (18)
C6—N1—C2—C3	1.45 (19)	N4—C5—C6—C7	142.29 (12)
C9—N1—C2—C3	−174.81 (13)	N1—C6—C7—C8	−38.38 (14)
O2—C2—C3—N4	−154.04 (12)	C5—C6—C7—C8	−161.09 (11)
N1—C2—C3—N4	25.99 (17)	C6—C7—C8—C9	39.55 (15)
O2—C2—C3—C11	77.73 (15)	C2—N1—C9—C8	176.95 (13)
N1—C2—C3—C11	−102.23 (13)	C6—N1—C9—C8	0.26 (16)
C2—C3—N4—C5	−28.21 (17)	C7—C8—C9—N1	−24.88 (15)
C11—C3—N4—C5	99.06 (14)	N4—C3—C11—C12	−67.73 (14)
C2—C3—N4—C10	156.38 (11)	C2—C3—C11—C12	60.39 (14)
C11—C3—N4—C10	−76.35 (14)	C3—C11—C12—C13	−90.29 (15)
C10—N4—C5—O5	−2.08 (19)	C3—C11—C12—C17	87.61 (15)
C3—N4—C5—O5	−177.40 (12)	C17—C12—C13—C14	−0.8 (2)
C10—N4—C5—C6	177.12 (11)	C11—C12—C13—C14	177.19 (12)
C3—N4—C5—C6	1.79 (17)	C12—C13—C14—C15	0.2 (2)
C2—N1—C6—C5	−27.96 (18)	C13—C14—C15—C16	−0.1 (2)
C9—N1—C6—C5	148.65 (12)	C14—C15—C16—C17	0.6 (2)
C2—N1—C6—C7	−152.31 (13)	C15—C16—C17—C12	−1.1 (2)
C9—N1—C6—C7	24.30 (15)	C13—C12—C17—C16	1.2 (2)
O5—C5—C6—N1	−155.19 (12)	C11—C12—C17—C16	−176.72 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O5ⁱ	1.00	2.39	3.3536 (16)	163
C8—H8B···O5ⁱⁱ	0.99	2.50	3.4224 (17)	155
C15—H15···O2ⁱⁱⁱ	0.95	2.39	3.1859 (18)	141

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

(10b-room) top

Crystal data top

C₁₅H₁₈N₂O₂	F(000) = 552
M_r = 258.31	D_x = 1.255 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 10.1490 (5) Å	θ = 13–14°
b = 10.939 (1) Å	µ = 0.08 mm⁻¹
c = 12.310 (1) Å	T = 293 K
V = 1366.66 (18) Å³	Prism, colourless
Z = 4	0.5 × 0.4 × 0.3 mm

Data collection top

CAD4-MACHIII diffractometer	R_int = 0.0000
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.5°
Graphite monochromator	h = 0→12
θ–2θ scan	k = 0→12
1386 measured reflections	l = 0→14
1386 independent reflections	3 standard reflections every 3600 min
1179 reflections with I > 2σ(I)	intensity decay: 9%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.035	w = 1/[σ²(F_o²) + (0.0678P)² + 0.0829P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.101	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.13 e Å⁻³
1386 reflections	Δρ_min = −0.17 e Å⁻³
174 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.028 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: −3 (2)

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.7752 (2)	0.22607 (17)	0.08058 (15)	0.0458 (5)
C2	0.7183 (2)	0.1294 (2)	0.12611 (18)	0.0436 (5)
C3	0.6482 (2)	0.1502 (2)	0.23244 (17)	0.0407 (5)
H3	0.5692	0.0987	0.2307	0.049*
N4	0.60164 (18)	0.27640 (17)	0.24587 (15)	0.0414 (5)
C5	0.6589 (2)	0.37307 (19)	0.19856 (17)	0.0426 (5)
C6	0.7752 (2)	0.3487 (2)	0.12667 (17)	0.0418 (5)
H6	0.8558	0.3593	0.1695	0.050*
C7	0.7849 (3)	0.4282 (3)	0.0261 (2)	0.0617 (7)
H7A	0.8218	0.5077	0.0430	0.074*
H7B	0.6995	0.4388	−0.0080	0.074*
C8	0.8772 (3)	0.3541 (3)	−0.0454 (2)	0.0749 (9)
H8A	0.8658	0.3756	−0.1213	0.090*
H8B	0.9683	0.3679	−0.0251	0.090*
C9	0.8384 (4)	0.2230 (3)	−0.0256 (2)	0.0712 (9)
H9A	0.7777	0.1945	−0.0809	0.085*
H9B	0.9152	0.1702	−0.0248	0.085*
C10	0.4911 (3)	0.2955 (3)	0.3195 (2)	0.0633 (8)
H10A	0.5231	0.3261	0.3876	0.095*
H10B	0.4461	0.2194	0.3310	0.095*
H10C	0.4313	0.3537	0.2882	0.095*
C11	0.7314 (3)	0.1047 (2)	0.32916 (19)	0.0496 (6)
H11A	0.6816	0.1164	0.3956	0.060*
H11B	0.7470	0.0178	0.3207	0.060*
C12	0.8618 (2)	0.1688 (2)	0.34005 (17)	0.0428 (5)
C13	0.9728 (3)	0.1243 (2)	0.2894 (2)	0.0592 (7)
H13	0.9678	0.0516	0.2505	0.071*
C14	1.0913 (3)	0.1855 (3)	0.2953 (3)	0.0720 (9)
H14	1.1651	0.1544	0.2601	0.086*
C15	1.1002 (3)	0.2922 (3)	0.3531 (3)	0.0705 (9)
H15	1.1801	0.3336	0.3574	0.085*
C16	0.9924 (3)	0.3370 (3)	0.4039 (3)	0.0643 (8)
H16	0.9984	0.4098	0.4427	0.077*
C17	0.8738 (3)	0.2763 (2)	0.3988 (2)	0.0525 (6)
H17	0.8010	0.3078	0.4351	0.063*
O2	0.7219 (2)	0.02684 (15)	0.08536 (16)	0.0649 (5)
O5	0.6212 (2)	0.47820 (15)	0.21331 (18)	0.0678 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0551 (11)	0.0403 (10)	0.0422 (9)	0.0052 (10)	0.0092 (10)	−0.0014 (8)
C2	0.0438 (12)	0.0370 (12)	0.0500 (12)	0.0052 (10)	−0.0078 (11)	−0.0004 (10)
C3	0.0386 (11)	0.0344 (11)	0.0493 (12)	−0.0036 (10)	−0.0003 (10)	0.0044 (10)
N4	0.0394 (10)	0.0392 (10)	0.0455 (9)	0.0018 (8)	0.0081 (9)	0.0032 (8)
C5	0.0456 (12)	0.0356 (11)	0.0467 (11)	0.0023 (10)	0.0037 (11)	−0.0012 (10)
C6	0.0440 (11)	0.0365 (11)	0.0448 (11)	−0.0015 (10)	0.0016 (10)	0.0024 (9)
C7	0.0732 (17)	0.0535 (16)	0.0585 (14)	−0.0039 (15)	0.0090 (14)	0.0137 (13)
C8	0.080 (2)	0.091 (2)	0.0539 (14)	−0.0059 (19)	0.0225 (15)	0.0140 (16)
C9	0.087 (2)	0.0691 (18)	0.0576 (16)	0.0122 (17)	0.0285 (16)	0.0005 (14)
C10	0.0540 (16)	0.0665 (18)	0.0693 (16)	0.0024 (13)	0.0202 (14)	0.0009 (15)
C11	0.0515 (14)	0.0445 (13)	0.0529 (13)	−0.0043 (12)	−0.0023 (12)	0.0141 (11)
C12	0.0469 (13)	0.0400 (11)	0.0414 (11)	0.0015 (11)	−0.0083 (10)	0.0122 (10)
C13	0.0546 (15)	0.0444 (13)	0.0786 (18)	0.0057 (12)	−0.0073 (14)	−0.0042 (14)
C14	0.0474 (15)	0.073 (2)	0.096 (2)	0.0067 (14)	0.0045 (16)	0.0058 (18)
C15	0.0549 (16)	0.0633 (19)	0.093 (2)	−0.0131 (15)	−0.0182 (17)	0.0205 (17)
C16	0.0744 (19)	0.0496 (14)	0.0690 (16)	−0.0070 (15)	−0.0271 (16)	−0.0015 (14)
C17	0.0577 (15)	0.0536 (13)	0.0463 (12)	0.0067 (12)	−0.0066 (12)	−0.0011 (11)
O2	0.0840 (13)	0.0387 (10)	0.0720 (12)	0.0076 (9)	0.0027 (12)	−0.0119 (9)
O5	0.0770 (13)	0.0369 (9)	0.0896 (13)	0.0088 (9)	0.0252 (12)	−0.0036 (9)

Geometric parameters (Å, º) top

N1—C2	1.329 (3)	C9—H9A	0.9700
N1—C9	1.456 (3)	C9—H9B	0.9700
N1—C6	1.457 (3)	C10—H10A	0.9600
C2—O2	1.230 (3)	C10—H10B	0.9600
C2—C3	1.507 (3)	C10—H10C	0.9600
C3—N4	1.469 (3)	C11—C12	1.503 (3)
C3—C11	1.542 (3)	C11—H11A	0.9700
C3—H3	0.9800	C11—H11B	0.9700
N4—C5	1.340 (3)	C12—C13	1.377 (4)
N4—C10	1.457 (3)	C12—C17	1.386 (3)
C5—O5	1.225 (3)	C13—C14	1.378 (4)
C5—C6	1.499 (3)	C13—H13	0.9300
C6—C7	1.515 (3)	C14—C15	1.370 (5)
C6—H6	0.9800	C14—H14	0.9300
C7—C8	1.519 (4)	C15—C16	1.352 (4)
C7—H7A	0.9700	C15—H15	0.9300
C7—H7B	0.9700	C16—C17	1.376 (4)
C8—C9	1.508 (5)	C16—H16	0.9300
C8—H8A	0.9700	C17—H17	0.9300
C8—H8B	0.9700

C2—N1—C9	123.5 (2)	N1—C9—C8	103.8 (2)
C2—N1—C6	124.66 (18)	N1—C9—H9A	111.0
C9—N1—C6	111.8 (2)	C8—C9—H9A	111.0
O2—C2—N1	122.7 (2)	N1—C9—H9B	111.0
O2—C2—C3	120.4 (2)	C8—C9—H9B	111.0
N1—C2—C3	116.83 (19)	H9A—C9—H9B	109.0
N4—C3—C2	113.05 (17)	N4—C10—H10A	109.5
N4—C3—C11	113.11 (18)	N4—C10—H10B	109.5
C2—C3—C11	111.32 (19)	H10A—C10—H10B	109.5
N4—C3—H3	106.2	N4—C10—H10C	109.5
C2—C3—H3	106.2	H10A—C10—H10C	109.5
C11—C3—H3	106.2	H10B—C10—H10C	109.5
C5—N4—C10	119.4 (2)	C12—C11—C3	113.63 (18)
C5—N4—C3	123.59 (18)	C12—C11—H11A	108.8
C10—N4—C3	116.93 (19)	C3—C11—H11A	108.8
O5—C5—N4	122.7 (2)	C12—C11—H11B	108.8
O5—C5—C6	120.0 (2)	C3—C11—H11B	108.8
N4—C5—C6	117.26 (19)	H11A—C11—H11B	107.7
N1—C6—C5	113.16 (19)	C13—C12—C17	117.7 (2)
N1—C6—C7	102.12 (18)	C13—C12—C11	121.0 (2)
C5—C6—C7	115.6 (2)	C17—C12—C11	121.3 (2)
N1—C6—H6	108.6	C12—C13—C14	121.2 (3)
C5—C6—H6	108.6	C12—C13—H13	119.4
C7—C6—H6	108.6	C14—C13—H13	119.4
C6—C7—C8	102.0 (2)	C15—C14—C13	119.9 (3)
C6—C7—H7A	111.4	C15—C14—H14	120.0
C8—C7—H7A	111.4	C13—C14—H14	120.0
C6—C7—H7B	111.4	C16—C15—C14	119.7 (3)
C8—C7—H7B	111.4	C16—C15—H15	120.2
H7A—C7—H7B	109.2	C14—C15—H15	120.2
C9—C8—C7	104.6 (2)	C15—C16—C17	120.8 (3)
C9—C8—H8A	110.8	C15—C16—H16	119.6
C7—C8—H8A	110.8	C17—C16—H16	119.6
C9—C8—H8B	110.8	C16—C17—C12	120.7 (3)
C7—C8—H8B	110.8	C16—C17—H17	119.7
H8A—C8—H8B	108.9	C12—C17—H17	119.7

C9—N1—C2—O2	5.0 (4)	N4—C5—C6—N1	25.5 (3)
C6—N1—C2—O2	−179.0 (2)	O5—C5—C6—C7	−38.4 (3)
C9—N1—C2—C3	−175.4 (2)	N4—C5—C6—C7	142.7 (2)
C6—N1—C2—C3	0.6 (3)	N1—C6—C7—C8	−37.4 (3)
O2—C2—C3—N4	−154.3 (2)	C5—C6—C7—C8	−160.6 (2)
N1—C2—C3—N4	26.1 (3)	C6—C7—C8—C9	37.9 (3)
O2—C2—C3—C11	77.1 (3)	C2—N1—C9—C8	175.5 (2)
N1—C2—C3—C11	−102.5 (2)	C6—N1—C9—C8	−1.0 (3)
C2—C3—N4—C5	−27.5 (3)	C7—C8—C9—N1	−23.1 (3)
C11—C3—N4—C5	100.2 (3)	N4—C3—C11—C12	−67.5 (3)
C2—C3—N4—C10	155.7 (2)	C2—C3—C11—C12	61.0 (3)
C11—C3—N4—C10	−76.6 (3)	C3—C11—C12—C13	−90.4 (3)
C10—N4—C5—O5	−1.0 (4)	C3—C11—C12—C17	87.7 (3)
C3—N4—C5—O5	−177.7 (2)	C17—C12—C13—C14	−1.0 (4)
C10—N4—C5—C6	177.9 (2)	C11—C12—C13—C14	177.2 (2)
C3—N4—C5—C6	1.2 (3)	C12—C13—C14—C15	0.5 (5)
C2—N1—C6—C5	−27.0 (3)	C13—C14—C15—C16	−0.2 (5)
C9—N1—C6—C5	149.4 (2)	C14—C15—C16—C17	0.4 (5)
C2—N1—C6—C7	−151.9 (2)	C15—C16—C17—C12	−1.0 (4)
C9—N1—C6—C7	24.5 (3)	C13—C12—C17—C16	1.3 (4)
O5—C5—C6—N1	−155.6 (2)	C11—C12—C17—C16	−176.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O5ⁱ	0.98	2.44	3.386 (3)	162
C8—H8A···O5ⁱⁱ	0.97	2.59	3.491 (4)	154
C15—H15···O2ⁱⁱⁱ	0.93	2.44	3.228 (4)	143

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

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Format		BIBTeX
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		Plain Text