1-Adamantylmethyl 2-amino-benzoate.

The asymmetric unit of the title compound, C(18)H(23)NO(2), consists of two crystallographically independent mol-ecules bearing an adamantane cage consisting of three fused cyclo-hexane rings in almost ideal chair conformations, with C-C-C angles in the range 108.47 (16)-110.59 (15)°. Both aryl rings are essentially planar, the maximum deviation from the best plane being 0.0125 (19) Å. One conformer forms chains parallel to the b axis via N-H⋯O hydrogen bonds, whereas the second exhibits only an intra-molecular N-H⋯O hydrogen bond. The crystal structure is stabilized by further weak N-H⋯O and N-H⋯N inter-actions.

Related literature

For some important biologically active compounds bearing the adamantane moiety, see: Jia et al. (2005 ▶); van der Schyf & Geldenhuys (2009) ▶. For the synthesis, see: Vícha et al. (2009 ▶).

Experimental

Crystal data

C18H23NO2

M = 285.37

Monoclinic,

a = 25.8665 (19) Å

b = 6.4575 (4) Å

c = 38.6173 (8) Å

β = 106.904 (7)°

V = 6171.7 (6) Å3

Z = 16

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.40 × 0.30 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.849, T max = 1.000

23009 measured reflections

5431 independent reflections

2752 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.061

S = 1.04

5431 reflections

395 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047276/nk2072sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047276/nk2072Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H23NO2	F(000) = 2464
Mr = 285.37	Dx = 1.229 Mg m−3
Monoclinic, C2/c	Melting point = 366–362 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 25.8665 (19) Å	Cell parameters from 4567 reflections
b = 6.4575 (4) Å	θ = 2.7–27.3°
c = 38.6173 (8) Å	µ = 0.08 mm−1
β = 106.904 (7)°	T = 120 K
V = 6171.7 (6) Å3	Block, yellow
Z = 16	0.40 × 0.30 × 0.30 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 detector	5431 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2752 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 8.4353 pixels mm-1	θmax = 25.0°, θmin = 3.2°
ω scan	h = −30→30
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −7→7
Tmin = 0.849, Tmax = 1.000	l = −38→45
23009 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.015P)2] where P = (Fo2 + 2Fc2)/3
5431 reflections	(Δ/σ)max < 0.001
395 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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 > 2σ(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.

	x	y	z	Uiso*/Ueq
O1	0.27207 (5)	0.3902 (2)	0.21497 (4)	0.0515 (4)
N1	0.29950 (7)	0.0010 (4)	0.24145 (5)	0.0430 (5)
C1	0.33939 (7)	0.0205 (3)	0.22478 (5)	0.0301 (5)
C2	0.37972 (8)	−0.1306 (3)	0.23019 (5)	0.0372 (5)
H2	0.3797	−0.2432	0.2460	0.045*
C3	0.41922 (8)	−0.1190 (3)	0.21309 (5)	0.0422 (6)
H3	0.4464	−0.2227	0.2175	0.051*
C4	0.42012 (8)	0.0413 (3)	0.18949 (5)	0.0429 (6)
H4	0.4476	0.0488	0.1777	0.052*
C5	0.38052 (7)	0.1888 (3)	0.18354 (5)	0.0338 (5)
H5	0.3805	0.2978	0.1670	0.041*
C6	0.34023 (7)	0.1848 (3)	0.20085 (5)	0.0251 (5)
C7	0.30047 (8)	0.3546 (3)	0.19566 (5)	0.0318 (5)
O8	0.29882 (4)	0.4694 (2)	0.16652 (3)	0.0386 (4)
C9	0.26212 (7)	0.6481 (3)	0.15911 (5)	0.0394 (6)
H9A	0.2807	0.7712	0.1723	0.047*
H9B	0.2300	0.6187	0.1674	0.047*
C10	0.24490 (7)	0.6899 (3)	0.11885 (5)	0.0272 (5)
C11	0.21169 (7)	0.5078 (3)	0.09824 (4)	0.0294 (5)
H11A	0.2343	0.3814	0.1021	0.035*
H11B	0.1805	0.4813	0.1076	0.035*
C12	0.19154 (7)	0.5575 (3)	0.05766 (5)	0.0323 (5)
H12	0.1700	0.4379	0.0445	0.039*
C13	0.15625 (7)	0.7498 (3)	0.05152 (5)	0.0380 (5)
H13A	0.1244	0.7253	0.0603	0.046*
H13B	0.1432	0.7813	0.0253	0.046*
C14	0.18892 (7)	0.9333 (3)	0.07187 (5)	0.0350 (5)
H14	0.1656	1.0598	0.0679	0.042*
C15	0.23731 (7)	0.9710 (3)	0.05761 (5)	0.0387 (5)
H15A	0.2246	1.0045	0.0315	0.046*
H15B	0.2586	1.0898	0.0705	0.046*
C16	0.27263 (7)	0.7773 (3)	0.06352 (5)	0.0338 (5)
H16	0.3043	0.8024	0.0541	0.041*
C17	0.29290 (7)	0.7285 (3)	0.10409 (5)	0.0345 (5)
H17A	0.3163	0.6043	0.1081	0.041*
H17B	0.3146	0.8460	0.1171	0.041*
C18	0.20872 (7)	0.8839 (3)	0.11237 (5)	0.0336 (5)
H18A	0.1774	0.8598	0.1217	0.040*
H18B	0.2294	1.0030	0.1256	0.040*
C19	0.23996 (7)	0.5952 (3)	0.04336 (5)	0.0357 (5)
H19A	0.2629	0.4697	0.0470	0.043*
H19B	0.2273	0.6256	0.0171	0.043*
O21	0.63002 (5)	0.95579 (19)	0.15600 (3)	0.0426 (4)
N21	0.67083 (8)	0.6087 (4)	0.19276 (5)	0.0466 (6)
C21	0.61810 (8)	0.5686 (3)	0.19077 (5)	0.0310 (5)
C22	0.60638 (8)	0.3934 (3)	0.20847 (5)	0.0376 (5)
H22	0.6347	0.3006	0.2199	0.045*
C23	0.55515 (9)	0.3530 (3)	0.20973 (5)	0.0409 (6)
H23	0.5486	0.2347	0.2225	0.049*
C24	0.51230 (8)	0.4830 (3)	0.19257 (5)	0.0391 (5)
H24	0.4767	0.4554	0.1936	0.047*
C25	0.52287 (7)	0.6526 (3)	0.17406 (5)	0.0321 (5)
H25	0.4938	0.7398	0.1616	0.039*
C26	0.57499 (7)	0.6995 (3)	0.17309 (5)	0.0255 (5)
C27	0.58532 (8)	0.8871 (3)	0.15428 (5)	0.0300 (5)
O28	0.53969 (4)	0.97894 (19)	0.13458 (3)	0.0327 (3)
C29	0.54562 (7)	1.1712 (3)	0.11641 (5)	0.0317 (5)
H29A	0.5767	1.1605	0.1064	0.038*
H29B	0.5525	1.2873	0.1339	0.038*
C30	0.49414 (7)	1.2116 (3)	0.08609 (5)	0.0244 (5)
C31	0.48638 (7)	1.0487 (3)	0.05613 (4)	0.0301 (5)
H31A	0.5183	1.0480	0.0469	0.036*
H31B	0.4831	0.9098	0.0661	0.036*
C32	0.43554 (7)	1.0966 (3)	0.02513 (5)	0.0310 (5)
H32	0.4308	0.9889	0.0059	0.037*
C33	0.38650 (7)	1.0953 (3)	0.03946 (5)	0.0374 (6)
H33A	0.3825	0.9568	0.0494	0.045*
H33B	0.3535	1.1249	0.0195	0.045*
C34	0.39332 (7)	1.2585 (3)	0.06906 (5)	0.0343 (5)
H34	0.3611	1.2570	0.0784	0.041*
C35	0.39899 (7)	1.4717 (3)	0.05345 (5)	0.0368 (5)
H35A	0.4035	1.5783	0.0725	0.044*
H35B	0.3659	1.5047	0.0337	0.044*
C36	0.44816 (7)	1.4731 (3)	0.03881 (5)	0.0308 (5)
H36	0.4518	1.6128	0.0286	0.037*
C37	0.49895 (7)	1.4253 (3)	0.06989 (4)	0.0286 (5)
H37A	0.5038	1.5326	0.0889	0.034*
H37B	0.5310	1.4280	0.0608	0.034*
C38	0.44432 (6)	1.2112 (3)	0.09989 (4)	0.0306 (5)
H38A	0.4407	1.0740	0.1104	0.037*
H38B	0.4488	1.3165	0.1192	0.037*
C39	0.44104 (7)	1.3093 (3)	0.00931 (5)	0.0346 (5)
H39A	0.4727	1.3104	−0.0002	0.041*
H39B	0.4083	1.3401	−0.0109	0.041*
H1B	0.2805 (7)	0.125 (3)	0.2443 (5)	0.054 (7)*
H21B	0.6966 (9)	0.517 (3)	0.2037 (6)	0.094 (10)*
H1A	0.3045 (8)	−0.098 (3)	0.2590 (5)	0.073 (9)*
H21A	0.6781 (7)	0.722 (3)	0.1807 (5)	0.058 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0435 (9)	0.0695 (12)	0.0492 (10)	0.0164 (8)	0.0257 (8)	0.0112 (8)
N1	0.0432 (12)	0.0529 (16)	0.0355 (13)	−0.0100 (12)	0.0158 (10)	0.0053 (12)
C1	0.0284 (12)	0.0392 (14)	0.0219 (12)	−0.0115 (11)	0.0062 (10)	−0.0021 (11)
C2	0.0480 (14)	0.0317 (14)	0.0287 (13)	−0.0019 (12)	0.0061 (12)	0.0079 (11)
C3	0.0460 (14)	0.0404 (15)	0.0404 (14)	0.0098 (11)	0.0127 (12)	0.0029 (12)
C4	0.0452 (14)	0.0486 (16)	0.0421 (15)	0.0107 (12)	0.0240 (11)	0.0114 (13)
C5	0.0370 (13)	0.0396 (15)	0.0274 (13)	0.0035 (11)	0.0133 (11)	0.0069 (11)
C6	0.0211 (11)	0.0283 (13)	0.0240 (12)	−0.0006 (10)	0.0035 (10)	0.0013 (10)
C7	0.0334 (13)	0.0379 (14)	0.0240 (13)	−0.0071 (11)	0.0083 (11)	0.0017 (12)
O8	0.0392 (8)	0.0427 (9)	0.0329 (9)	0.0116 (7)	0.0091 (7)	0.0055 (8)
C9	0.0362 (12)	0.0390 (14)	0.0389 (14)	0.0087 (11)	0.0042 (11)	−0.0053 (11)
C10	0.0303 (12)	0.0310 (13)	0.0191 (12)	−0.0015 (10)	0.0051 (10)	0.0010 (10)
C11	0.0352 (11)	0.0279 (12)	0.0277 (12)	−0.0031 (10)	0.0131 (9)	−0.0019 (10)
C12	0.0372 (12)	0.0319 (14)	0.0252 (13)	−0.0100 (10)	0.0050 (10)	−0.0052 (10)
C13	0.0366 (12)	0.0472 (15)	0.0293 (13)	−0.0004 (12)	0.0083 (10)	0.0025 (12)
C14	0.0384 (13)	0.0295 (14)	0.0361 (14)	0.0084 (10)	0.0092 (11)	0.0024 (11)
C15	0.0450 (13)	0.0280 (13)	0.0428 (14)	−0.0057 (11)	0.0123 (11)	0.0031 (11)
C16	0.0337 (12)	0.0318 (13)	0.0392 (14)	−0.0045 (11)	0.0160 (11)	0.0013 (11)
C17	0.0271 (11)	0.0305 (13)	0.0439 (15)	0.0009 (10)	0.0070 (11)	−0.0006 (11)
C18	0.0416 (12)	0.0302 (13)	0.0296 (13)	0.0076 (10)	0.0114 (10)	0.0003 (10)
C19	0.0480 (13)	0.0329 (13)	0.0283 (13)	0.0034 (11)	0.0146 (11)	0.0038 (11)
O21	0.0267 (8)	0.0497 (10)	0.0507 (10)	−0.0001 (8)	0.0104 (7)	0.0114 (8)
N21	0.0338 (13)	0.0507 (15)	0.0521 (14)	0.0090 (12)	0.0077 (11)	0.0114 (12)
C21	0.0349 (13)	0.0371 (14)	0.0206 (12)	0.0017 (11)	0.0077 (10)	−0.0049 (11)
C22	0.0454 (14)	0.0353 (14)	0.0266 (13)	0.0074 (12)	0.0016 (11)	0.0000 (11)
C23	0.0613 (16)	0.0279 (14)	0.0324 (14)	−0.0001 (12)	0.0122 (13)	0.0038 (11)
C24	0.0408 (13)	0.0379 (14)	0.0427 (14)	−0.0015 (12)	0.0186 (11)	0.0032 (12)
C25	0.0354 (13)	0.0299 (13)	0.0298 (13)	0.0041 (10)	0.0073 (10)	0.0020 (11)
C26	0.0280 (12)	0.0264 (13)	0.0221 (12)	0.0030 (10)	0.0072 (10)	0.0013 (10)
C27	0.0255 (12)	0.0394 (14)	0.0240 (12)	0.0069 (11)	0.0055 (11)	−0.0005 (11)
O28	0.0267 (7)	0.0332 (9)	0.0345 (8)	−0.0012 (7)	0.0032 (6)	0.0119 (7)
C29	0.0330 (12)	0.0282 (13)	0.0311 (13)	−0.0032 (10)	0.0049 (10)	0.0056 (11)
C30	0.0262 (11)	0.0238 (12)	0.0217 (12)	−0.0007 (9)	0.0046 (10)	0.0022 (10)
C31	0.0364 (12)	0.0224 (12)	0.0313 (12)	−0.0003 (10)	0.0095 (10)	0.0026 (10)
C32	0.0429 (13)	0.0259 (13)	0.0221 (12)	−0.0067 (10)	0.0063 (11)	−0.0050 (10)
C33	0.0316 (12)	0.0385 (14)	0.0341 (13)	−0.0098 (10)	−0.0030 (11)	0.0100 (11)
C34	0.0256 (12)	0.0456 (15)	0.0324 (13)	0.0023 (10)	0.0095 (10)	0.0097 (12)
C35	0.0359 (12)	0.0401 (15)	0.0310 (13)	0.0075 (11)	0.0044 (10)	0.0030 (11)
C36	0.0384 (12)	0.0232 (12)	0.0299 (13)	−0.0018 (10)	0.0086 (10)	0.0068 (11)
C37	0.0327 (11)	0.0248 (13)	0.0272 (12)	−0.0028 (10)	0.0071 (10)	0.0006 (10)
C38	0.0354 (12)	0.0332 (13)	0.0240 (12)	−0.0009 (10)	0.0099 (10)	0.0031 (10)
C39	0.0357 (12)	0.0363 (14)	0.0290 (13)	−0.0015 (10)	0.0051 (10)	0.0043 (11)

O1—C7	1.211 (2)	O21—C27	1.2222 (19)
N1—C1	1.372 (2)	N21—C21	1.368 (2)
N1—H1B	0.961 (17)	N21—H21B	0.90 (2)
N1—H1A	0.913 (19)	N21—H21A	0.912 (18)
C1—C2	1.399 (2)	C21—C22	1.400 (2)
C1—C6	1.412 (2)	C21—C26	1.408 (2)
C2—C3	1.370 (2)	C22—C23	1.365 (2)
C2—H2	0.9500	C22—H22	0.9500
C3—C4	1.384 (2)	C23—C24	1.395 (2)
C3—H3	0.9500	C23—H23	0.9500
C4—C5	1.368 (2)	C24—C25	1.378 (2)
C4—H4	0.9500	C24—H24	0.9500
C5—C6	1.392 (2)	C25—C26	1.393 (2)
C5—H5	0.9500	C25—H25	0.9500
C6—C7	1.476 (2)	C26—C27	1.476 (2)
C7—O8	1.3379 (19)	C27—O28	1.3422 (19)
O8—C9	1.4688 (18)	O28—C29	1.4562 (18)
C9—C10	1.512 (2)	C29—C30	1.518 (2)
C9—H9A	0.9900	C29—H29A	0.9900
C9—H9B	0.9900	C29—H29B	0.9900
C10—C17	1.530 (2)	C30—C38	1.531 (2)
C10—C11	1.535 (2)	C30—C31	1.533 (2)
C10—C18	1.540 (2)	C30—C37	1.535 (2)
C11—C12	1.535 (2)	C31—C32	1.531 (2)
C11—H11A	0.9900	C31—H31A	0.9900
C11—H11B	0.9900	C31—H31B	0.9900
C12—C13	1.519 (2)	C32—C33	1.524 (2)
C12—C19	1.528 (2)	C32—C39	1.526 (2)
C12—H12	1.0000	C32—H32	1.0000
C13—C14	1.533 (2)	C33—C34	1.527 (2)
C13—H13A	0.9900	C33—H33A	0.9900
C13—H13B	0.9900	C33—H33B	0.9900
C14—C15	1.526 (2)	C34—C35	1.527 (2)
C14—C18	1.531 (2)	C34—C38	1.529 (2)
C14—H14	1.0000	C34—H34	1.0000
C15—C16	1.526 (2)	C35—C36	1.535 (2)
C15—H15A	0.9900	C35—H35A	0.9900
C15—H15B	0.9900	C35—H35B	0.9900
C16—C19	1.523 (2)	C36—C39	1.526 (2)
C16—C17	1.534 (2)	C36—C37	1.531 (2)
C16—H16	1.0000	C36—H36	1.0000
C17—H17A	0.9900	C37—H37A	0.9900
C17—H17B	0.9900	C37—H37B	0.9900
C18—H18A	0.9900	C38—H38A	0.9900
C18—H18B	0.9900	C38—H38B	0.9900
C19—H19A	0.9900	C39—H39A	0.9900
C19—H19B	0.9900	C39—H39B	0.9900
C1—N1—H1B	117.1 (11)	C21—N21—H21B	119.5 (14)
C1—N1—H1A	116.6 (13)	C21—N21—H21A	118.2 (12)
H1B—N1—H1A	117.9 (18)	H21B—N21—H21A	122.0 (18)
N1—C1—C2	119.7 (2)	N21—C21—C22	118.7 (2)
N1—C1—C6	122.2 (2)	N21—C21—C26	123.3 (2)
C2—C1—C6	117.99 (18)	C22—C21—C26	117.94 (19)
C3—C2—C1	121.22 (19)	C23—C22—C21	121.48 (19)
C3—C2—H2	119.4	C23—C22—H22	119.3
C1—C2—H2	119.4	C21—C22—H22	119.3
C2—C3—C4	121.0 (2)	C22—C23—C24	120.88 (19)
C2—C3—H3	119.5	C22—C23—H23	119.6
C4—C3—H3	119.5	C24—C23—H23	119.6
C5—C4—C3	118.41 (19)	C25—C24—C23	118.35 (18)
C5—C4—H4	120.8	C25—C24—H24	120.8
C3—C4—H4	120.8	C23—C24—H24	120.8
C4—C5—C6	122.36 (19)	C24—C25—C26	121.76 (18)
C4—C5—H5	118.8	C24—C25—H25	119.1
C6—C5—H5	118.8	C26—C25—H25	119.1
C5—C6—C1	118.95 (18)	C25—C26—C21	119.53 (18)
C5—C6—C7	120.69 (18)	C25—C26—C27	120.45 (17)
C1—C6—C7	120.29 (18)	C21—C26—C27	120.00 (18)
O1—C7—O8	122.43 (19)	O21—C27—O28	122.17 (18)
O1—C7—C6	125.50 (19)	O21—C27—C26	125.10 (18)
O8—C7—C6	112.08 (18)	O28—C27—C26	112.73 (17)
C7—O8—C9	117.37 (15)	C27—O28—C29	116.84 (14)
O8—C9—C10	108.72 (15)	O28—C29—C30	109.06 (14)
O8—C9—H9A	109.9	O28—C29—H29A	109.9
C10—C9—H9A	109.9	C30—C29—H29A	109.9
O8—C9—H9B	109.9	O28—C29—H29B	109.9
C10—C9—H9B	109.9	C30—C29—H29B	109.9
H9A—C9—H9B	108.3	H29A—C29—H29B	108.3
C9—C10—C17	112.57 (15)	C29—C30—C38	111.68 (14)
C9—C10—C11	110.47 (15)	C29—C30—C31	110.92 (14)
C17—C10—C11	108.91 (15)	C38—C30—C31	108.83 (14)
C9—C10—C18	107.19 (15)	C29—C30—C37	108.17 (14)
C17—C10—C18	109.11 (15)	C38—C30—C37	108.64 (14)
C11—C10—C18	108.48 (14)	C31—C30—C37	108.53 (14)
C12—C11—C10	110.00 (14)	C32—C31—C30	110.24 (14)
C12—C11—H11A	109.7	C32—C31—H31A	109.6
C10—C11—H11A	109.7	C30—C31—H31A	109.6
C12—C11—H11B	109.7	C32—C31—H31B	109.6
C10—C11—H11B	109.7	C30—C31—H31B	109.6
H11A—C11—H11B	108.2	H31A—C31—H31B	108.1
C13—C12—C19	109.38 (16)	C33—C32—C39	109.54 (15)
C13—C12—C11	109.92 (15)	C33—C32—C31	109.36 (15)
C19—C12—C11	109.37 (14)	C39—C32—C31	109.63 (15)
C13—C12—H12	109.4	C33—C32—H32	109.4
C19—C12—H12	109.4	C39—C32—H32	109.4
C11—C12—H12	109.4	C31—C32—H32	109.4
C12—C13—C14	109.60 (14)	C32—C33—C34	109.93 (15)
C12—C13—H13A	109.7	C32—C33—H33A	109.7
C14—C13—H13A	109.7	C34—C33—H33A	109.7
C12—C13—H13B	109.7	C32—C33—H33B	109.7
C14—C13—H13B	109.8	C34—C33—H33B	109.7
H13A—C13—H13B	108.2	H33A—C33—H33B	108.2
C15—C14—C18	109.61 (15)	C33—C34—C35	109.28 (15)
C15—C14—C13	109.02 (15)	C33—C34—C38	109.33 (15)
C18—C14—C13	109.49 (15)	C35—C34—C38	109.11 (15)
C15—C14—H14	109.6	C33—C34—H34	109.7
C18—C14—H14	109.6	C35—C34—H34	109.7
C13—C14—H14	109.6	C38—C34—H34	109.7
C16—C15—C14	109.49 (15)	C34—C35—C36	109.62 (15)
C16—C15—H15A	109.8	C34—C35—H35A	109.7
C14—C15—H15A	109.8	C36—C35—H35A	109.7
C16—C15—H15B	109.8	C34—C35—H35B	109.7
C14—C15—H15B	109.8	C36—C35—H35B	109.7
H15A—C15—H15B	108.2	H35A—C35—H35B	108.2
C19—C16—C15	109.71 (15)	C39—C36—C37	109.59 (15)
C19—C16—C17	109.71 (15)	C39—C36—C35	109.73 (15)
C15—C16—C17	109.45 (15)	C37—C36—C35	108.90 (14)
C19—C16—H16	109.3	C39—C36—H36	109.5
C15—C16—H16	109.3	C37—C36—H36	109.5
C17—C16—H16	109.3	C35—C36—H36	109.5
C10—C17—C16	109.93 (14)	C36—C37—C30	110.36 (14)
C10—C17—H17A	109.7	C36—C37—H37A	109.6
C16—C17—H17A	109.7	C30—C37—H37A	109.6
C10—C17—H17B	109.7	C36—C37—H37B	109.6
C16—C17—H17B	109.7	C30—C37—H37B	109.6
H17A—C17—H17B	108.2	H37A—C37—H37B	108.1
C14—C18—C10	110.02 (14)	C34—C38—C30	110.57 (14)
C14—C18—H18A	109.7	C34—C38—H38A	109.5
C10—C18—H18A	109.7	C30—C38—H38A	109.5
C14—C18—H18B	109.7	C34—C38—H38B	109.5
C10—C18—H18B	109.7	C30—C38—H38B	109.5
H18A—C18—H18B	108.2	H38A—C38—H38B	108.1
C16—C19—C12	109.24 (15)	C36—C39—C32	109.27 (15)
C16—C19—H19A	109.8	C36—C39—H39A	109.8
C12—C19—H19A	109.8	C32—C39—H39A	109.8
C16—C19—H19B	109.8	C36—C39—H39B	109.8
C12—C19—H19B	109.8	C32—C39—H39B	109.8
H19A—C19—H19B	108.3	H39A—C39—H39B	108.3

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1	0.961 (17)	2.030 (18)	2.729 (3)	128.0 (14)
N21—H21B···N1i	0.90 (2)	2.64 (2)	3.385 (3)	140.9 (17)
N1—H1A···O1ii	0.913 (19)	2.47 (2)	2.930 (2)	111.4 (15)
N1—H1A···N21iii	0.913 (19)	2.60 (2)	3.511 (3)	173.4 (17)
N21—H21A···O21	0.912 (18)	2.014 (19)	2.698 (3)	130.6 (16)
N21—H21A···O1i	0.912 (18)	2.641 (18)	3.097 (2)	111.8 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1	0.961 (17)	2.030 (18)	2.729 (3)	128.0 (14)
N21—H21B⋯N1i	0.90 (2)	2.64 (2)	3.385 (3)	140.9 (17)
N1—H1A⋯O1ii	0.913 (19)	2.47 (2)	2.930 (2)	111.4 (15)
N1—H1A⋯N21iii	0.913 (19)	2.60 (2)	3.511 (3)	173.4 (17)
N21—H21A⋯O21	0.912 (18)	2.014 (19)	2.698 (3)	130.6 (16)
N21—H21A⋯O1i	0.912 (18)	2.641 (18)	3.097 (2)	111.8 (14)

Symmetry codes: (i) ; (ii) ; (iii) .