A 1:2 adduct of 3-(piperidin-1-yl)propionic acid and triphenyl­tin chloride

3-(Piperidin-1-yl)propionic acid, C₈H₁₅NO₂, forms a 1:2 adduct, bis-chlorotriphenyl[3-(piperidinium-1-yl)propionato]tin(IV (C₈H₁₅NO₂)[Sn(C₆H₅)₃Cl]₂, with triphenyl­tin chloride, [Sn(C₆H₅)₃Cl]. The acidic H atom is transferred to the imine N atom and an N—H...O intra­molecular hydrogen bond is formed. The carboxylate group bridges the two Sn atoms.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.022
• wR factor = 0.025
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C3      ..       5.04 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Sn1    -   Cl1     ..       5.37 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1997) and KRYSTAL (Hazell, 1995); program(s) used to refine structure: modified ORFLS (Busing et al., 1962) and KRYSTAL; molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and KRYSTAL; software used to prepare material for publication: KRYSTAL.

3-(Piperidin-1-yl)propionic acid–triphenyltin chloride (1/2)

Crystal data

(C8H15NO2)[Sn(C6H5)3Cl]2	F(000) = 1864
Mr = 928.13	Dx = 1.538 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6353 reflections
a = 13.223 (3) Å	θ = 2.0–29.8°
b = 15.779 (3) Å	µ = 1.42 mm^−1
c = 19.574 (4) Å	T = 120 K
β = 101.065 (4)°	Block, colourless
V = 4008 (1) Å^3	0.36 × 0.22 × 0.17 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	10724 independent reflections
Radiation source: x-ray tube	7497 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.041
ω scans	θmax = 29.5°, θmin = 2.0°
Absorption correction: integration (XPREP; Siemens, 1995)	h = −18→17
Tmin = 0.683, Tmax = 0.802	k = −18→22
27396 measured reflections	l = −27→23

Refinement

Refinement on F	0 constraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.022	w = 1/{[σcs(F^2) + 1.03F^2]^1/2-|F|}^2
wR(F^2) = 0.025	(Δ/σ)max = 0.003
S = 0.81	Δρmax = 0.81 (7) e Å^−3
7497 reflections	Δρmin = −0.65 (7) e Å^−3
465 parameters	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
0 restraints	Extinction coefficient: 24 (5)

Special details

Refinement. Sfls: F calc weight full matrix

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.36449 (1)	0.03856 (1)	0.66912 (1)	0.0182 (1)
Sn2	0.04048 (1)	0.07856 (1)	0.81628 (1)	0.0174 (1)
Cl1	0.50796 (5)	−0.06834 (4)	0.67486 (3)	0.0302 (3)
Cl2	−0.04250 (5)	0.08458 (4)	0.92033 (3)	0.0292 (3)
O1	0.2367 (1)	0.1461 (1)	0.6630 (1)	0.020 (1)
O2	0.1352 (1)	0.0769 (1)	0.7229 (1)	0.020 (1)
N	0.1996 (1)	0.3224 (1)	0.6449 (1)	0.022 (1)
C1	0.1542 (2)	0.1381 (1)	0.6870 (1)	0.019 (1)
C2	0.0748 (2)	0.2083 (1)	0.6670 (1)	0.024 (1)
C3	0.1159 (2)	0.2970 (2)	0.6835 (1)	0.027 (1)
C4	0.2568 (2)	0.3982 (1)	0.6803 (1)	0.029 (1)
C5	0.3405 (2)	0.4278 (2)	0.6435 (1)	0.031 (1)
C6	0.2994 (2)	0.4447 (2)	0.5672 (1)	0.036 (2)
C7	0.2447 (2)	0.3664 (2)	0.5328 (1)	0.039 (2)
C8	0.1584 (2)	0.3400 (2)	0.5691 (1)	0.033 (1)
C11	0.4307 (2)	0.1252 (1)	0.6067 (1)	0.022 (1)
C12	0.4495 (2)	0.1000 (2)	0.5419 (1)	0.031 (1)
C13	0.5044 (2)	0.1521 (2)	0.5045 (1)	0.040 (2)
C14	0.5428 (2)	0.2286 (2)	0.5318 (2)	0.040 (2)
C15	0.5228 (2)	0.2557 (2)	0.5944 (1)	0.034 (2)
C16	0.4664 (2)	0.2051 (1)	0.6311 (1)	0.026 (1)
C21	0.4049 (2)	0.0549 (1)	0.7788 (1)	0.019 (1)
C22	0.3712 (2)	−0.0018 (1)	0.8243 (1)	0.023 (1)
C23	0.4000 (2)	0.0082 (2)	0.8960 (1)	0.026 (1)
C24	0.4642 (2)	0.0744 (2)	0.9233 (1)	0.028 (1)
C25	0.5000 (2)	0.1301 (2)	0.8788 (1)	0.027 (1)
C26	0.4703 (2)	0.1209 (1)	0.8072 (1)	0.023 (1)
C31	0.2521 (2)	−0.0495 (1)	0.6176 (1)	0.023 (1)
C32	0.2657 (2)	−0.1361 (2)	0.6297 (1)	0.031 (1)
C33	0.1967 (2)	−0.1948 (2)	0.5932 (2)	0.038 (2)
C34	0.1145 (2)	−0.1681 (2)	0.5442 (1)	0.039 (2)
C35	0.0996 (2)	−0.0824 (2)	0.5314 (2)	0.041 (2)
C36	0.1678 (2)	−0.0232 (2)	0.5684 (1)	0.032 (1)
C41	0.1053 (2)	−0.0444 (1)	0.8384 (1)	0.021 (1)
C42	0.1213 (2)	−0.0981 (1)	0.7847 (1)	0.026 (1)
C43	0.1618 (2)	−0.1786 (2)	0.7996 (2)	0.033 (2)
C44	0.1873 (2)	−0.2066 (2)	0.8672 (2)	0.039 (2)
C45	0.1712 (2)	−0.1544 (2)	0.9209 (2)	0.038 (2)
C46	0.1295 (2)	−0.0734 (1)	0.9067 (1)	0.028 (1)
C51	−0.1013 (2)	0.0813 (1)	0.7421 (1)	0.021 (1)
C52	−0.1934 (2)	0.1033 (2)	0.7629 (1)	0.029 (1)
C53	−0.2869 (2)	0.1006 (2)	0.7158 (2)	0.036 (2)
C54	−0.2908 (2)	0.0763 (2)	0.6479 (2)	0.035 (2)
C55	−0.2003 (2)	0.0554 (2)	0.6264 (1)	0.031 (1)
C56	−0.1062 (2)	0.0570 (1)	0.6734 (1)	0.025 (1)
C61	0.1256 (2)	0.1919 (1)	0.8457 (1)	0.020 (1)
C62	0.0755 (2)	0.2631 (2)	0.8652 (1)	0.029 (1)
C63	0.1307 (2)	0.3374 (2)	0.8853 (2)	0.038 (2)
C64	0.2351 (2)	0.3415 (2)	0.8857 (2)	0.038 (2)
C65	0.2863 (2)	0.2711 (2)	0.8667 (1)	0.032 (1)
C66	0.2314 (2)	0.1967 (1)	0.8468 (1)	0.025 (1)
H1N	0.244 (2)	0.274 (2)	0.647 (1)	0.041 (8)*
H2A	0.0201	0.1990	0.6913	0.029*
H2B	0.0491	0.2048	0.6183	0.029*
H3A	0.0604	0.3358	0.6717	0.033*
H3B	0.1430	0.3003	0.7320	0.033*
H4A	0.2870	0.3832	0.7267	0.035*
H4B	0.2092	0.4432	0.6809	0.035*
H5A	0.3923	0.3854	0.6476	0.038*
H5B	0.3697	0.4786	0.6648	0.038*
H6A	0.3550	0.4587	0.5450	0.043*
H6B	0.2521	0.4906	0.5628	0.043*
H7A	0.2928	0.3213	0.5352	0.047*
H7B	0.2168	0.3787	0.4854	0.047*
H8A	0.1089	0.3842	0.5652	0.040*
H8B	0.1266	0.2902	0.5477	0.040*
H12	0.4246	0.0468	0.5231	0.038*
H13	0.5154	0.1347	0.4600	0.048*
H14	0.5831	0.2627	0.5072	0.048*
H15	0.5476	0.3092	0.6126	0.041*
H16	0.4516	0.2252	0.6739	0.032*
H22	0.3281	−0.0479	0.8060	0.027*
H23	0.3757	−0.0305	0.9264	0.031*
H24	0.4834	0.0815	0.9722	0.033*
H25	0.5452	0.1748	0.8973	0.033*
H26	0.4947	0.1600	0.7772	0.028*
H32	0.3227	−0.1555	0.6633	0.037*
H33	0.2067	−0.2536	0.6024	0.045*
H34	0.0681	−0.2082	0.5192	0.047*
H35	0.0429	−0.0636	0.4974	0.049*
H36	0.1562	0.0356	0.5598	0.038*
H42	0.1043	−0.0794	0.7377	0.031*
H43	0.1721	−0.2147	0.7627	0.040*
H44	0.2158	−0.2615	0.8770	0.047*
H45	0.1885	−0.1737	0.9676	0.045*
H46	0.1177	−0.0382	0.9437	0.034*
H52	−0.1922	0.1202	0.8096	0.034*
H53	−0.3487	0.1157	0.7308	0.043*
H54	−0.3549	0.0740	0.6162	0.042*
H55	−0.2020	0.0398	0.5793	0.037*
H56	−0.0449	0.0412	0.6581	0.030*
H62	0.0036	0.2611	0.8648	0.034*
H63	0.0961	0.3856	0.8988	0.045*
H64	0.2719	0.3924	0.8990	0.046*
H65	0.3582	0.2735	0.8673	0.038*
H66	0.2665	0.1485	0.8339	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.01610 (8)	0.01943 (8)	0.01838 (8)	−0.00024 (6)	0.00178 (6)	−0.00330 (6)
Sn2	0.01639 (8)	0.01617 (8)	0.01955 (9)	−0.00007 (6)	0.00360 (6)	0.00101 (6)
Cl1	0.0252 (3)	0.0302 (3)	0.0340 (4)	0.0077 (2)	0.0023 (3)	−0.0067 (3)
Cl2	0.0332 (3)	0.0320 (3)	0.0254 (3)	0.0021 (3)	0.0131 (3)	0.0028 (2)
O1	0.016 (1)	0.021 (1)	0.024 (1)	0.001 (1)	0.006 (1)	0.001 (1)
O2	0.021 (1)	0.018 (1)	0.023 (1)	0.000 (1)	0.005 (1)	0.000 (1)
N	0.020 (1)	0.021 (1)	0.026 (1)	0.001 (1)	0.006 (1)	0.004 (1)
C1	0.016 (1)	0.020 (1)	0.020 (1)	−0.001 (1)	0.001 (1)	−0.004 (1)
C2	0.016 (1)	0.024 (1)	0.033 (1)	0.000 (1)	0.006 (1)	0.007 (1)
C3	0.024 (1)	0.027 (1)	0.033 (1)	0.005 (1)	0.010 (1)	0.008 (1)
C4	0.037 (1)	0.025 (1)	0.026 (1)	−0.003 (1)	0.008 (1)	−0.002 (1)
C5	0.030 (1)	0.030 (1)	0.033 (2)	−0.010 (1)	0.005 (1)	−0.004 (1)
C6	0.032 (1)	0.044 (2)	0.034 (2)	−0.007 (1)	0.011 (1)	0.011 (1)
C7	0.038 (2)	0.058 (2)	0.021 (1)	−0.007 (1)	0.005 (1)	0.004 (1)
C8	0.028 (1)	0.043 (2)	0.026 (1)	−0.006 (1)	−0.003 (1)	0.003 (1)
C11	0.014 (1)	0.030 (1)	0.021 (1)	0.005 (1)	0.001 (1)	0.002 (1)
C12	0.025 (1)	0.043 (2)	0.024 (1)	0.007 (1)	−0.002 (1)	0.001 (1)
C13	0.039 (2)	0.064 (2)	0.019 (1)	0.014 (1)	0.009 (1)	0.013 (1)
C14	0.032 (2)	0.051 (2)	0.037 (2)	0.008 (1)	0.010 (1)	0.024 (1)
C15	0.029 (1)	0.033 (1)	0.040 (2)	0.002 (1)	0.004 (1)	0.015 (1)
C16	0.024 (1)	0.028 (1)	0.028 (1)	0.004 (1)	0.007 (1)	0.005 (1)
C21	0.016 (1)	0.020 (1)	0.022 (1)	0.004 (1)	0.003 (1)	−0.002 (1)
C22	0.020 (1)	0.021 (1)	0.027 (1)	0.003 (1)	0.003 (1)	−0.002 (1)
C23	0.026 (1)	0.027 (1)	0.025 (1)	0.005 (1)	0.006 (1)	0.004 (1)
C24	0.027 (1)	0.034 (1)	0.020 (1)	0.006 (1)	0.000 (1)	−0.003 (1)
C25	0.027 (1)	0.028 (1)	0.026 (1)	−0.003 (1)	0.002 (1)	−0.008 (1)
C26	0.023 (1)	0.024 (1)	0.024 (1)	−0.001 (1)	0.004 (1)	−0.002 (1)
C31	0.024 (1)	0.026 (1)	0.020 (1)	−0.004 (1)	0.006 (1)	−0.007 (1)
C32	0.033 (1)	0.028 (1)	0.030 (1)	−0.006 (1)	0.003 (1)	−0.002 (1)
C33	0.049 (2)	0.029 (1)	0.038 (2)	−0.013 (1)	0.013 (1)	−0.005 (1)
C34	0.036 (2)	0.046 (2)	0.036 (2)	−0.019 (1)	0.010 (1)	−0.018 (1)
C35	0.032 (1)	0.047 (2)	0.040 (2)	−0.006 (1)	−0.005 (1)	−0.014 (1)
C36	0.029 (1)	0.032 (1)	0.033 (2)	−0.001 (1)	−0.001 (1)	−0.009 (1)
C41	0.016 (1)	0.018 (1)	0.028 (1)	−0.002 (1)	0.004 (1)	0.004 (1)
C42	0.024 (1)	0.023 (1)	0.032 (1)	−0.004 (1)	0.009 (1)	0.000 (1)
C43	0.030 (1)	0.020 (1)	0.053 (2)	−0.003 (1)	0.016 (1)	−0.004 (1)
C44	0.030 (1)	0.019 (1)	0.066 (2)	0.003 (1)	0.008 (1)	0.009 (1)
C45	0.036 (2)	0.032 (1)	0.043 (2)	0.002 (1)	0.000 (1)	0.017 (1)
C46	0.027 (1)	0.025 (1)	0.031 (1)	−0.001 (1)	0.003 (1)	0.003 (1)
C51	0.016 (1)	0.017 (1)	0.029 (1)	−0.001 (1)	0.004 (1)	0.004 (1)
C52	0.027 (1)	0.026 (1)	0.035 (2)	0.003 (1)	0.011 (1)	0.010 (1)
C53	0.020 (1)	0.039 (2)	0.049 (2)	0.007 (1)	0.007 (1)	0.018 (1)
C54	0.020 (1)	0.031 (1)	0.049 (2)	−0.006 (1)	−0.006 (1)	0.017 (1)
C55	0.031 (1)	0.026 (1)	0.032 (1)	−0.005 (1)	−0.003 (1)	0.001 (1)
C56	0.020 (1)	0.023 (1)	0.032 (1)	−0.003 (1)	0.002 (1)	−0.001 (1)
C61	0.022 (1)	0.018 (1)	0.019 (1)	0.002 (1)	0.001 (1)	0.002 (1)
C62	0.023 (1)	0.025 (1)	0.038 (2)	0.003 (1)	0.007 (1)	−0.002 (1)
C63	0.033 (1)	0.019 (1)	0.061 (2)	0.004 (1)	0.008 (1)	−0.009 (1)
C64	0.032 (1)	0.022 (1)	0.056 (2)	−0.003 (1)	−0.003 (1)	−0.009 (1)
C65	0.021 (1)	0.026 (1)	0.045 (2)	−0.001 (1)	−0.002 (1)	−0.003 (1)
C66	0.022 (1)	0.019 (1)	0.032 (1)	0.002 (1)	0.000 (1)	−0.002 (1)

Geometric parameters (Å, º)

Sn1—Cl1	2.525 (1)	C61—C62	1.392 (3)
Sn1—O1	2.382 (2)	C61—C66	1.397 (3)
Sn1—C11	2.131 (2)	C62—C63	1.398 (3)
Sn1—C21	2.126 (2)	C63—C64	1.380 (4)
Sn1—C31	2.140 (2)	C64—C65	1.388 (4)
Sn2—Cl2	2.494 (1)	C65—C66	1.396 (3)
Sn2—O2	2.406 (2)	N—H1N	0.96 (3)
Sn2—C41	2.131 (2)	C2—H2A	0.950
Sn2—C51	2.140 (2)	C2—H2B	0.950
Sn2—C61	2.133 (2)	C3—H3A	0.950
C1—O1	1.274 (3)	C3—H3B	0.950
C1—O2	1.249 (3)	C4—H4A	0.950
N—C8	1.504 (3)	C4—H4B	0.950
N—C3	1.509 (3)	C5—H5A	0.950
N—C4	1.511 (3)	C5—H5B	0.950
C1—C2	1.524 (3)	C6—H6A	0.950
C2—C3	1.515 (3)	C6—H6B	0.950
C4—C5	1.507 (4)	C7—H7A	0.950
C5—C6	1.511 (4)	C7—H7B	0.950
C6—C7	1.523 (4)	C8—H8A	0.950
C7—C8	1.514 (4)	C8—H8B	0.950
C11—C12	1.395 (3)	C12—H12	0.950
C11—C16	1.399 (3)	C13—H13	0.950
C12—C13	1.394 (4)	C14—H14	0.950
C13—C14	1.378 (4)	C15—H15	0.950
C14—C15	1.371 (4)	C16—H16	0.950
C15—C16	1.383 (3)	C22—H22	0.950
C21—C22	1.394 (3)	C23—H23	0.950
C21—C26	1.400 (3)	C24—H24	0.950
C22—C23	1.391 (3)	C25—H25	0.950
C23—C24	1.387 (4)	C26—H26	0.950
C24—C25	1.383 (3)	C32—H32	0.950
C25—C26	1.388 (3)	C33—H33	0.950
C31—C36	1.389 (3)	C34—H34	0.950
C31—C32	1.393 (3)	C35—H35	0.950
C32—C33	1.397 (4)	C36—H36	0.950
C33—C34	1.370 (4)	C42—H42	0.950
C34—C35	1.382 (4)	C43—H43	0.950
C35—C36	1.399 (4)	C44—H44	0.950
C41—C46	1.392 (3)	C45—H45	0.950
C41—C42	1.397 (3)	C46—H46	0.950
C42—C43	1.388 (3)	C52—H52	0.950
C43—C44	1.374 (4)	C53—H53	0.950
C44—C45	1.383 (4)	C54—H54	0.950
C45—C46	1.399 (3)	C55—H55	0.950
C51—C56	1.388 (3)	C56—H56	0.950
C51—C52	1.400 (3)	C62—H62	0.950
C52—C53	1.393 (4)	C63—H63	0.950
C53—C54	1.375 (4)	C64—H64	0.950
C54—C55	1.383 (4)	C65—H65	0.950
C55—C56	1.398 (3)	C66—H66	0.950
Cl1—Sn1—O1	176.43 (6)	C1—C2—H2B	108.2
Cl1—Sn1—C11	93.79 (6)	H3A—C3—H3B	109.5
Cl1—Sn1—C21	89.72 (6)	N—C3—H3A	108.3
Cl1—Sn1—C31	92.03 (7)	C2—C3—H3A	108.3
O1—Sn1—C11	83.10 (7)	N—C3—H3B	108.3
O1—Sn1—C21	90.14 (7)	C2—C3—H3B	108.3
O1—Sn1—C31	90.98 (7)	H4A—C4—H4B	109.5
C11—Sn1—C21	116.76 (9)	C5—C4—H4A	108.8
C11—Sn1—C31	118.06 (9)	N—C4—H4A	108.8
C21—Sn1—C31	124.89 (9)	C5—C4—H4B	108.8
Cl2—Sn2—O2	174.63 (5)	N—C4—H4B	108.8
Cl2—Sn2—C41	95.28 (6)	H5A—C5—H5B	109.5
Cl2—Sn2—C51	95.05 (6)	C4—C5—H5A	108.9
Cl2—Sn2—C61	92.24 (6)	C6—C5—H5A	108.9
O2—Sn2—C41	84.03 (7)	C4—C5—H5B	108.9
O2—Sn2—C51	90.06 (7)	C6—C5—H5B	108.9
O2—Sn2—C61	83.68 (7)	H6A—C6—H6B	109.5
C41—Sn2—C51	114.97 (8)	C5—C6—H6A	109.3
C41—Sn2—C61	122.53 (9)	C7—C6—H6A	109.3
C51—Sn2—C61	120.95 (8)	C5—C6—H6B	109.3
Sn1—O1—C1	124.1 (1)	C7—C6—H6B	109.3
Sn2—O2—C1	127.5 (1)	H7A—C7—H7B	109.5
Sn1—C11—C12	120.2 (2)	C8—C7—H7A	109.2
Sn1—C11—C16	122.1 (2)	C6—C7—H7A	109.2
Sn1—C21—C22	121.2 (2)	C8—C7—H7B	109.2
Sn1—C21—C26	120.5 (2)	C6—C7—H7B	109.2
Sn1—C31—C32	120.0 (2)	H8A—C8—H8B	109.5
Sn1—C31—C36	121.7 (2)	N—C8—H8A	109.2
Sn2—C41—C42	120.8 (2)	C7—C8—H8A	109.2
Sn2—C41—C46	120.3 (2)	N—C8—H8B	109.2
Sn2—C51—C52	120.4 (2)	C7—C8—H8B	109.2
Sn2—C51—C56	121.6 (2)	C13—C12—H12	119.6
Sn2—C61—C62	119.8 (2)	C11—C12—H12	119.6
Sn2—C61—C66	121.6 (2)	C14—C13—H13	119.9
C3—N—C8	112.4 (2)	C12—C13—H13	119.9
C4—N—C8	111.2 (2)	C15—C14—H14	120.0
C3—N—C4	109.3 (2)	C13—C14—H14	120.0
O1—C1—O2	124.2 (2)	C14—C15—H15	120.0
O1—C1—C2	115.4 (2)	C16—C15—H15	120.0
O2—C1—C2	120.3 (2)	C15—C16—H16	119.3
O2—C1—C2	120.3 (2)	C11—C16—H16	119.3
C1—C2—C3	114.5 (2)	C23—C22—H22	119.6
N—C3—C2	114.0 (2)	C21—C22—H22	119.6
N—C4—C5	112.0 (2)	C24—C23—H23	119.9
C4—C5—C6	111.6 (2)	C22—C23—H23	119.9
C5—C6—C7	110.2 (2)	C25—C24—H24	120.2
C6—C7—C8	110.6 (2)	C23—C24—H24	120.2
N—C8—C7	110.5 (2)	C24—C25—H25	119.8
C12—C11—C16	117.4 (2)	C26—C25—H25	119.8
C11—C12—C13	120.7 (3)	C25—C26—H26	119.6
C12—C13—C14	120.2 (3)	C21—C26—H26	119.6
C13—C14—C15	120.0 (3)	C31—C32—H32	119.6
C14—C15—C16	120.0 (3)	C33—C32—H32	119.6
C11—C16—C15	121.5 (2)	C34—C33—H33	119.8
C22—C21—C26	118.2 (2)	C32—C33—H33	119.8
C21—C22—C23	120.8 (2)	C33—C34—H34	120.2
C22—C23—C24	120.2 (2)	C35—C34—H34	120.2
C23—C24—C25	119.6 (2)	C34—C35—H35	119.9
C24—C25—C26	120.3 (2)	C36—C35—H35	119.9
C21—C26—C25	120.8 (2)	C31—C36—H36	119.6
C32—C31—C36	118.1 (2)	C35—C36—H36	119.6
C31—C32—C33	120.8 (3)	C43—C42—H42	119.9
C32—C33—C34	120.4 (3)	C41—C42—H42	119.9
C33—C34—C35	119.6 (2)	C44—C43—H43	119.6
C34—C35—C36	120.2 (3)	C42—C43—H43	119.6
C31—C36—C35	120.8 (2)	C43—C44—H44	120.2
C42—C41—C46	118.9 (2)	C45—C44—H44	120.2
C41—C42—C43	120.3 (2)	C44—C45—H45	119.8
C42—C43—C44	120.7 (2)	C46—C45—H45	119.8
C43—C44—C45	119.6 (2)	C41—C46—H46	120.0
C44—C45—C46	120.4 (3)	C45—C46—H46	120.0
C41—C46—C45	120.0 (2)	C53—C52—H52	119.6
C52—C51—C56	117.9 (2)	C51—C52—H52	119.6
C51—C52—C53	120.8 (2)	C54—C53—H53	119.6
C52—C53—C54	120.8 (2)	C52—C53—H53	119.6
C53—C54—C55	119.1 (2)	C53—C54—H54	120.4
C54—C55—C56	120.5 (2)	C55—C54—H54	120.4
C51—C56—C55	120.9 (2)	C54—C55—H55	119.7
C62—C61—C66	118.7 (2)	C56—C55—H55	119.7
C61—C62—C63	120.3 (2)	C51—C56—H56	119.6
C62—C63—C64	120.5 (2)	C55—C56—H56	119.6
C63—C64—C65	120.0 (2)	C61—C62—H62	119.9
C64—C65—C66	119.6 (2)	C63—C62—H62	119.9
C61—C66—C65	121.0 (2)	C64—C63—H63	119.8
C3—N—H1N	106 (2)	C62—C63—H63	119.8
C4—N—H1N	111 (2)	C63—C64—H64	120.0
C8—N—H1N	107 (2)	C65—C64—H64	120.0
H2A—C2—H2B	109.5	C64—C65—H65	120.2
C3—C2—H2A	108.2	C66—C65—H65	120.2
C1—C2—H2A	108.2	C65—C66—H66	119.5
C3—C2—H2B	108.2	C61—C66—H66	119.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H1N···O1	0.96 (3)	2.05 (3)	2.835 (3)	138 (2)