1,3-Propane­di­ammonium bis(3'-nitro-trans-cinnamate) and trans-1,2-cyclo­hexane­di­ammonium bis(3'-nitro-trans-cinnamate)

In the title two adducts, C₃H₁₂N₂²⁺·2C₉H₆NO₄^-, (I), and C₆H₁₆N₂²⁺·2C₉H₆NO₄^-, (II), hydrogen bonds between the di­ammonium and carboxyl­ate ions form a two-dimensional network parallel to the ab plane in (I) and one-dimensional chains along the c axis in (II). The cyclo­hexane­di­ammonium ion in (II) has a crystallographic twofold axis.

Computing details

For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(I) propane-1,3-diammonium bis[(E)-3-(3-nitrophenyl)propenoate]

Crystal data

C3H12N2^2+·2C9H6NO4^−	Dx = 1.392 Mg m^−3
Mr = 460.44	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 25 reflections
Hall symbol: -P 2ac 2ab	θ = 12.3–14.8°
a = 7.136 (3) Å	µ = 0.11 mm^−1
b = 23.710 (3) Å	T = 298 K
c = 25.964 (4) Å	Prism, pale yellow
V = 4393.0 (18) Å^3	0.7 × 0.4 × 0.4 mm
Z = 8

Data collection

Rigaku AFC-7R diffractometer	θmax = 27.5°, θmin = 2.5°
ω scans	h = 0→9
5308 measured reflections	k = −11→31
5040 independent reflections	l = 0→34
3317 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
Rint = 0.011	intensity decay: 1.5%

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.056	w = 1/[σ^2(Fo^2) + (0.0829P)^2 + 1.575P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.167	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.54 e Å^−3
5040 reflections	Δρmin = −0.27 e Å^−3
322 parameters

Special details

Refinement. Refinement was based on F² against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F², and conventional R-factor (R) was calculated on F, with F set to zero for negative F². The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt).

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

	x	y	z	Uiso*/Ueq
O1	0.7685 (3)	0.60955 (6)	0.10519 (5)	0.0584 (5)
O2	0.8838 (3)	0.54097 (6)	0.05626 (6)	0.0560 (4)
O3	0.7878 (4)	0.5742 (1)	0.37654 (8)	0.0943 (7)
O4	0.8114 (4)	0.4955 (1)	0.41604 (7)	0.1070 (9)
O5	0.5076 (2)	0.35244 (6)	0.40834 (6)	0.0568 (4)
O6	0.4939 (2)	0.27819 (6)	0.46020 (5)	0.0519 (4)
O7	0.5328 (3)	0.32718 (9)	0.13686 (7)	0.0796 (6)
O8	0.5148 (4)	0.2496 (1)	0.09443 (6)	0.0921 (7)
N9	0.7978 (3)	0.5234 (1)	0.37682 (8)	0.0682 (6)
N10	0.5161 (3)	0.2763 (1)	0.13454 (7)	0.0590 (5)
N11	0.8656 (3)	0.42929 (8)	0.02374 (8)	0.0445 (4)
N12	0.2876 (3)	0.32104 (8)	−0.02145 (7)	0.0394 (4)
C13	0.8198 (3)	0.56004 (8)	0.09756 (8)	0.0432 (5)
C14	0.8109 (3)	0.51834 (8)	0.14136 (8)	0.0488 (5)
C15	0.7773 (3)	0.53429 (8)	0.18830 (8)	0.0471 (5)
C16	0.7762 (3)	0.49815 (9)	0.23542 (8)	0.0436 (5)
C17	0.7908 (3)	0.52460 (8)	0.28273 (8)	0.0464 (5)
C18	0.7856 (3)	0.4928 (1)	0.32723 (8)	0.0468 (5)
C19	0.7660 (3)	0.4355 (1)	0.32726 (8)	0.0529 (6)
C20	0.7530 (3)	0.40880 (9)	0.2800 (1)	0.0556 (6)
C21	0.7576 (3)	0.4397 (1)	0.23429 (8)	0.0499 (5)
C22	0.4985 (3)	0.30082 (9)	0.41634 (8)	0.0418 (4)
C23	0.4953 (3)	0.26128 (8)	0.37088 (8)	0.0468 (5)
C24	0.4851 (3)	0.27994 (8)	0.32347 (7)	0.0425 (5)
C25	0.4830 (3)	0.24642 (9)	0.27551 (7)	0.0391 (4)
C26	0.5000 (3)	0.27481 (8)	0.22891 (8)	0.0430 (5)
C27	0.4971 (3)	0.24429 (9)	0.18313 (7)	0.0445 (5)
C28	0.4789 (3)	0.1868 (1)	0.18207 (8)	0.0515 (5)
C29	0.4626 (4)	0.15882 (9)	0.22832 (9)	0.0550 (6)
C30	0.4642 (3)	0.18779 (9)	0.27492 (8)	0.0470 (5)
C31	0.6597 (3)	0.42152 (8)	0.02746 (8)	0.0480 (5)
C32	0.5874 (3)	0.37048 (8)	−0.00108 (7)	0.0435 (5)
C33	0.3837 (3)	0.36166 (8)	0.01305 (7)	0.0421 (5)
H11A	0.895 (4)	0.461 (1)	0.0390 (9)	0.05732 (9)*
H11B	0.935 (4)	0.400 (1)	0.043 (1)	0.06619 (10)*
H11C	0.905 (3)	0.4284 (9)	−0.0068 (10)	0.04702 (8)*
H12A	0.180 (4)	0.3093 (9)	−0.0068 (9)	0.05057 (8)*
H12B	0.355 (3)	0.294 (1)	−0.0273 (9)	0.05095 (9)*
H12C	0.258 (3)	0.339 (1)	−0.0544 (10)	0.06132 (9)*
H14	0.8357	0.4787	0.1353	0.0533*
H15	0.7497	0.5738	0.1948	0.0495*
H17	0.8047	0.5651	0.2843	0.0477*
H19	0.7593	0.4132	0.3574	0.0575*
H20	0.7427	0.3683	0.2770	0.0572*
H21	0.7469	0.4207	0.2017	0.0526*
H23	0.5012	0.2215	0.3769	0.0481*
H24	0.4796	0.3201	0.3183	0.0433*
H26	0.5142	0.3154	0.2285	0.0432*
H28	0.4782	0.1656	0.1514	0.0559*
H29	0.4453	0.1183	0.2290	0.0584*
H30	0.4575	0.1668	0.3068	0.0495*
H31A	0.6272	0.4179	0.0632	0.0490*
H31B	0.5994	0.4546	0.0135	0.0490*
H32A	0.6594	0.3377	0.0087	0.0446*
H32B	0.5997	0.3761	−0.0377	0.0446*
H33A	0.3185	0.3975	0.0105	0.0431*
H33B	0.3748	0.3483	0.0478	0.0431*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.089 (1)	0.0476 (9)	0.0384 (8)	0.0030 (8)	−0.0096 (8)	0.0022 (7)
O2	0.072 (1)	0.0485 (8)	0.0477 (9)	−0.0089 (8)	0.0118 (8)	0.0012 (7)
O3	0.128 (2)	0.085 (2)	0.070 (1)	0.003 (1)	−0.015 (1)	−0.018 (1)
O4	0.141 (2)	0.141 (2)	0.0385 (10)	0.050 (2)	−0.009 (1)	0.011 (1)
O5	0.076 (1)	0.0480 (9)	0.0459 (8)	−0.0122 (8)	0.0064 (8)	−0.0044 (7)
O6	0.063 (1)	0.0569 (9)	0.0361 (7)	−0.0159 (8)	−0.0031 (7)	−0.0006 (7)
O7	0.114 (2)	0.072 (1)	0.053 (1)	0.016 (1)	0.003 (1)	0.0116 (9)
O8	0.134 (2)	0.108 (2)	0.0344 (9)	0.023 (1)	0.003 (1)	−0.0113 (9)
N9	0.064 (1)	0.091 (2)	0.049 (1)	0.017 (1)	−0.005 (1)	−0.002 (1)
N10	0.061 (1)	0.076 (1)	0.0395 (10)	0.018 (1)	0.0018 (9)	−0.0009 (10)
N11	0.048 (1)	0.0394 (10)	0.046 (1)	−0.0069 (8)	0.0104 (9)	0.0003 (8)
N12	0.042 (1)	0.0395 (9)	0.0363 (9)	0.0013 (8)	0.0014 (8)	0.0028 (7)
C13	0.049 (1)	0.043 (1)	0.037 (1)	−0.0086 (9)	−0.0066 (9)	0.0073 (8)
C14	0.054 (1)	0.049 (1)	0.044 (1)	−0.002 (1)	−0.0002 (10)	0.0075 (9)
C15	0.052 (1)	0.046 (1)	0.044 (1)	−0.0008 (10)	−0.0017 (10)	0.0034 (9)
C16	0.035 (1)	0.055 (1)	0.040 (1)	−0.0008 (9)	−0.0008 (8)	0.0109 (9)
C17	0.044 (1)	0.050 (1)	0.045 (1)	0.0005 (9)	−0.0039 (9)	0.0103 (9)
C18	0.041 (1)	0.064 (1)	0.036 (1)	0.009 (1)	−0.0003 (8)	0.0076 (9)
C19	0.049 (1)	0.061 (1)	0.048 (1)	0.008 (1)	0.005 (1)	0.023 (1)
C20	0.051 (1)	0.045 (1)	0.070 (2)	0.001 (1)	0.005 (1)	0.010 (1)
C21	0.043 (1)	0.061 (1)	0.045 (1)	0.000 (1)	0.0007 (10)	0.0014 (10)
C22	0.041 (1)	0.048 (1)	0.0365 (10)	−0.0082 (9)	0.0010 (8)	−0.0053 (8)
C23	0.056 (1)	0.045 (1)	0.039 (1)	−0.0022 (10)	0.0007 (10)	−0.0028 (9)
C24	0.046 (1)	0.043 (1)	0.039 (1)	−0.0046 (9)	0.0022 (9)	−0.0035 (8)
C25	0.0330 (9)	0.049 (1)	0.0352 (10)	0.0002 (9)	0.0000 (8)	−0.0060 (8)
C26	0.041 (1)	0.047 (1)	0.040 (1)	0.0041 (9)	−0.0003 (9)	−0.0052 (9)
C27	0.038 (1)	0.061 (1)	0.0339 (10)	0.0082 (10)	0.0005 (8)	−0.0050 (9)
C28	0.051 (1)	0.061 (1)	0.043 (1)	0.005 (1)	−0.0017 (10)	−0.0184 (10)
C29	0.059 (1)	0.046 (1)	0.059 (1)	−0.004 (1)	0.002 (1)	−0.011 (1)
C30	0.048 (1)	0.051 (1)	0.042 (1)	−0.0034 (10)	0.0019 (9)	−0.0019 (9)
C31	0.046 (1)	0.045 (1)	0.052 (1)	0.0001 (9)	0.0060 (10)	−0.0025 (9)
C32	0.046 (1)	0.044 (1)	0.041 (1)	0.0001 (9)	0.0060 (9)	0.0012 (8)
C33	0.044 (1)	0.049 (1)	0.0329 (10)	0.0022 (9)	−0.0003 (8)	−0.0001 (8)

Geometric parameters (Å, º)

O1—C13	1.245 (2)	C19—C20	1.383 (3)
O2—C13	1.250 (3)	C19—H19	0.95
O3—N9	1.205 (4)	C20—C21	1.396 (3)
O4—N9	1.219 (3)	C20—H20	0.97
O5—C22	1.243 (3)	C21—H21	0.96
O6—C22	1.259 (3)	C22—C23	1.508 (3)
O7—N10	1.213 (3)	C23—C24	1.310 (3)
O8—N10	1.219 (3)	C23—H23	0.96
N9—C18	1.481 (3)	C24—C25	1.477 (3)
N10—C27	1.479 (3)	C24—H24	0.96
N11—C31	1.484 (3)	C25—C26	1.390 (3)
N11—H11A	0.87 (3)	C25—C30	1.397 (3)
N11—H11B	0.99 (3)	C26—C27	1.392 (3)
N11—H11C	0.84 (3)	C26—H26	0.97
N12—C33	1.483 (3)	C27—C28	1.369 (3)
N12—H12A	0.90 (2)	C28—C29	1.377 (3)
N12—H12B	0.83 (2)	C28—H28	0.94
N12—H12C	0.98 (2)	C29—C30	1.391 (3)
C13—C14	1.508 (3)	C29—H29	0.97
C14—C15	1.298 (3)	C30—H30	0.97
C14—H14	0.97	C31—C32	1.510 (3)
C15—C16	1.494 (3)	C31—H31A	0.96
C15—H15	0.97	C31—H31B	0.97
C16—C17	1.383 (3)	C32—C33	1.514 (3)
C16—C21	1.392 (3)	C32—H32A	0.97
C17—C18	1.380 (3)	C32—H32B	0.96
C17—H17	0.97	C33—H33A	0.97
C18—C19	1.367 (3)	C33—H33B	0.96
O3—N9—O4	123.6 (2)	O5—C22—O6	124.9 (2)
O3—N9—C18	118.8 (2)	O5—C22—C23	118.8 (2)
O4—N9—C18	117.6 (3)	O6—C22—C23	116.3 (2)
O7—N10—O8	124.1 (2)	C22—C23—C24	121.8 (2)
O7—N10—C27	118.5 (2)	C22—C23—H23	119
O8—N10—C27	117.4 (2)	C24—C23—H23	119
C31—N11—H11A	109 (2)	C23—C24—C25	127.7 (2)
C31—N11—H11B	112 (2)	C23—C24—H24	118
C31—N11—H11C	113 (2)	C25—C24—H24	114
H11A—N11—H11B	104 (2)	C24—C25—C26	118.2 (2)
H11A—N11—H11C	112 (2)	C24—C25—C30	123.1 (2)
H11B—N11—H11C	108 (2)	C26—C25—C30	118.7 (2)
C33—N12—H12A	110 (1)	C25—C26—C27	119.4 (2)
C33—N12—H12B	111 (2)	C25—C26—H26	120
C33—N12—H12C	110 (1)	C27—C26—H26	121
H12A—N12—H12B	109 (2)	N10—C27—C26	117.4 (2)
H12A—N12—H12C	109 (2)	N10—C27—C28	120.2 (2)
H12B—N12—H12C	108 (2)	C26—C27—C28	122.4 (2)
O1—C13—O2	125.8 (2)	C27—C28—C29	118.1 (2)
O1—C13—C14	119.0 (2)	C27—C28—H28	123
O2—C13—C14	115.2 (2)	C29—C28—H28	119
C13—C14—C15	121.6 (2)	C28—C29—C30	121.3 (2)
C13—C14—H14	120	C28—C29—H29	120
C15—C14—H14	118	C30—C29—H29	118
C14—C15—C16	127.1 (2)	C25—C30—C29	120.1 (2)
C14—C15—H15	119	C25—C30—H30	121
C16—C15—H15	114	C29—C30—H30	119
C15—C16—C17	117.8 (2)	N11—C31—C32	113.9 (2)
C15—C16—C21	123.7 (2)	N11—C31—H31A	108
C17—C16—C21	118.5 (2)	N11—C31—H31B	108
C16—C17—C18	119.6 (2)	C32—C31—H31A	109
C16—C17—H17	120	C32—C31—H31B	108
C18—C17—H17	121	H31A—C31—H31B	109
N9—C18—C17	117.3 (2)	C31—C32—C33	108.7 (2)
N9—C18—C19	119.6 (2)	C31—C32—H32A	110
C17—C18—C19	123.1 (2)	C31—C32—H32B	110
C18—C19—C20	117.4 (2)	C33—C32—H32A	110
C18—C19—H19	124	C33—C32—H32B	110
C20—C19—H19	118	H32A—C32—H32B	109
C19—C20—C21	120.8 (2)	N12—C33—C32	112.8 (2)
C19—C20—H20	122	N12—C33—H33A	108
C21—C20—H20	117	N12—C33—H33B	109
C16—C21—C20	120.5 (2)	C32—C33—H33A	109
C16—C21—H21	120	C32—C33—H33B	110
C20—C21—H21	120	H33A—C33—H33B	109

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11A···O2	0.87 (3)	1.96 (3)	2.782 (2)	158 (2)
N11—H11B···O5^i	0.99 (3)	1.77 (3)	2.731 (3)	164 (2)
N11—H11C···O2^ii	0.84 (3)	2.11 (2)	2.830 (3)	144 (2)
N12—H12A···O6^iii	0.90 (2)	1.94 (2)	2.820 (3)	164 (2)
N12—H12B···O6^iv	0.83 (2)	1.99 (2)	2.816 (2)	174 (2)
N12—H12C···O1^v	0.98 (2)	1.80 (2)	2.756 (2)	163 (2)

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

(II) trans-cyclohexane-1,2-diammonium bis[(E)-3-(3-nitrophenyl)propenoate]

Crystal data

C6H16N2^2+·2C9H6NO4^−	Dx = 1.363 Mg m^−3
Mr = 500.51	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 25 reflections
Hall symbol: -P 2n 2ab	θ = 12.2–14.6°
a = 26.919 (4) Å	µ = 0.10 mm^−1
b = 7.572 (3) Å	T = 298 K
c = 11.966 (3) Å	Prism, colourless
V = 2439.1 (10) Å^3	0.7 × 0.3 × 0.3 mm
Z = 4

Data collection

Rigaku AFC-7R diffractometer	θmax = 27.5°, θmin = 2.5°
ω scans	h = 0→35
2942 measured reflections	k = −10→3
2798 independent reflections	l = 0→16
1507 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
Rint = 0.018	intensity decay: 0.7%

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.074	w = 1/[σ^2(Fo^2) + (0.05P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.190	(Δ/σ)max = 0.001
S = 1.77	Δρmax = 0.44 e Å^−3
2798 reflections	Δρmin = −0.28 e Å^−3
183 parameters

Special details

Refinement. Refinement was based on F² against all reflections. The weighted R-factor (wR) and goodness of fit (S) were based on F², and conventional R-factor (R) was calculated on F, with F set to zero for negative F². The threshold expression of I > 2σ(I) was used only for calculating R-factor(gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.10530 (6)	0.0501 (4)	0.2810 (2)	0.0859 (8)
O2	0.05685 (6)	0.1001 (3)	0.4259 (2)	0.0607 (5)
O3	0.3644 (1)	0.1033 (6)	0.3552 (3)	0.165 (2)
O4	0.40302 (8)	0.1785 (4)	0.5033 (3)	0.121 (1)
N5	0.3657 (1)	0.1378 (4)	0.4536 (3)	0.0903 (9)
N6	0.0292 (1)	0.0621 (3)	0.6489 (2)	0.0472 (6)
C7	0.09833 (9)	0.0852 (4)	0.3803 (3)	0.0540 (7)
C8	0.1397 (1)	0.1127 (5)	0.4635 (3)	0.055 (1)	0.768 (9)
C8*	0.1564 (5)	0.100 (2)	0.410 (1)	0.05422 (5)*	0.232 (9)
C9	0.1867 (1)	0.0853 (5)	0.4349 (2)	0.053 (1)	0.768 (9)
C9*	0.1695 (5)	0.118 (2)	0.5084 (9)	0.06496 (6)*	0.232 (9)
C10	0.2305 (1)	0.1130 (4)	0.5083 (3)	0.0668 (8)
C11	0.2750 (1)	0.1120 (4)	0.4557 (2)	0.0724 (9)
C12	0.31802 (9)	0.1371 (4)	0.5157 (3)	0.0626 (8)
C13	0.31886 (9)	0.1628 (4)	0.6286 (3)	0.0677 (9)
C14	0.2731 (1)	0.1626 (5)	0.6848 (2)	0.0773 (9)
C15	0.22908 (9)	0.1375 (4)	0.6228 (3)	0.0747 (9)
C16	0.0069 (1)	0.2262 (4)	0.6912 (2)	0.0638 (8)
C17	0.03225 (9)	0.3881 (4)	0.6521 (2)	0.0620 (7)
C18	0.0092 (1)	0.5554 (4)	0.6927 (3)	0.093 (1)
H6A	0.053 (1)	0.004 (5)	0.694 (3)	0.1027 (1)*
H6B	0.0416 (10)	0.080 (4)	0.580 (3)	0.0642 (1)*
H6C	0.0093 (10)	−0.005 (4)	0.643 (2)	0.0490 (1)*
H8	0.1319	0.1507	0.5379	0.0655*	0.768 (9)
H8*	0.1810	0.0941	0.3517	0.0662*	0.232 (9)
H9	0.1930	0.0438	0.3604	0.0637*	0.768 (9)
H9*	0.1481	0.1326	0.5721	0.0773*	0.232 (9)
H11	0.2766	0.0941	0.3763	0.0867*
H13	0.3495	0.1801	0.6679	0.0812*
H14	0.2718	0.1792	0.7642	0.0928*
H15	0.1977	0.1374	0.6605	0.0898*
H16	−0.0251	0.2307	0.6534	0.0760*
H17A	0.0318	0.3893	0.5719	0.0743*
H17B	0.0659	0.3838	0.6780	0.0743*
H18A	0.0338	0.6465	0.6873	0.1115*
H18B	−0.0182	0.5823	0.6446	0.1115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.048 (1)	0.142 (2)	0.068 (1)	−0.029 (1)	0.0088 (10)	−0.018 (1)
O2	0.053 (1)	0.075 (1)	0.055 (1)	−0.0056 (10)	0.0026 (8)	−0.004 (1)
O3	0.132 (3)	0.237 (5)	0.125 (3)	−0.041 (3)	0.045 (2)	−0.025 (3)
O4	0.049 (1)	0.162 (3)	0.151 (3)	0.000 (2)	−0.001 (2)	0.049 (2)
N5	0.072 (2)	0.092 (2)	0.107 (3)	0.001 (2)	0.009 (2)	0.019 (2)
N6	0.047 (1)	0.051 (1)	0.044 (1)	0.000 (1)	0.005 (1)	0.000 (1)
C7	0.043 (1)	0.055 (2)	0.064 (2)	−0.007 (1)	−0.014 (1)	−0.001 (1)
C8	0.036 (2)	0.081 (3)	0.046 (2)	−0.001 (2)	−0.004 (2)	−0.009 (2)
C9	0.038 (2)	0.074 (3)	0.047 (2)	−0.005 (2)	−0.002 (1)	−0.002 (2)
C10	0.058 (2)	0.060 (2)	0.082 (2)	−0.008 (1)	−0.024 (2)	0.015 (2)
C11	0.058 (2)	0.083 (2)	0.077 (2)	−0.012 (2)	−0.014 (2)	0.012 (2)
C12	0.045 (1)	0.062 (2)	0.081 (2)	−0.003 (1)	−0.007 (1)	0.015 (2)
C13	0.047 (2)	0.075 (2)	0.081 (2)	−0.009 (1)	−0.023 (1)	0.012 (2)
C14	0.068 (2)	0.090 (3)	0.074 (2)	−0.005 (2)	−0.005 (2)	−0.001 (2)
C15	0.039 (1)	0.071 (2)	0.115 (3)	−0.005 (1)	0.006 (2)	0.010 (2)
C16	0.082 (2)	0.045 (2)	0.065 (2)	0.003 (1)	0.020 (2)	0.004 (1)
C17	0.071 (2)	0.051 (2)	0.065 (2)	−0.003 (1)	0.006 (1)	0.006 (1)
C18	0.122 (3)	0.049 (2)	0.107 (3)	−0.003 (2)	0.024 (2)	0.012 (2)

Geometric parameters (Å, º)

O1—C7	1.233 (4)	C10—C11	1.354 (4)
O2—C7	1.248 (3)	C10—C15	1.382 (5)
O3—N5	1.207 (6)	C11—C12	1.376 (4)
O4—N5	1.207 (4)	C11—H11	0.96
N5—C12	1.484 (4)	C12—C13	1.365 (5)
N6—C16	1.470 (4)	C13—C14	1.403 (4)
N6—H6A	0.95 (3)	C13—H13	0.96
N6—H6B	0.90 (3)	C14—C15	1.412 (4)
N6—H6C	0.74 (3)	C14—H14	0.96
C7—C8	1.508 (4)	C15—H15	0.96
C7—C8*	1.608 (13)	C16—C16^i	1.455 (5)
C8—C9	1.329 (5)	C16—C17	1.480 (4)
C8—H8	0.96	C16—H16	0.97
C8*—C9*	1.234 (16)	C17—C18	1.492 (4)
C8*—H8*	0.97	C17—H17A	0.96
C9—C10	1.484 (5)	C17—H17B	0.96
C9—H9	0.96	C18—C18^i	1.458 (7)
C9*—C10	1.642 (13)	C18—H18A	0.96
C9*—H9*	0.96	C18—H18B	0.96
O3—N5—O4	124.1 (3)	C10—C11—H11	120
O3—N5—C12	117.6 (3)	C12—C11—H11	120
O4—N5—C12	118.2 (3)	N5—C12—C11	117.8 (3)
C16—N6—H6A	118 (2)	N5—C12—C13	118.8 (3)
C16—N6—H6B	110 (2)	C11—C12—C13	123.4 (2)
C16—N6—H6C	109 (2)	C12—C13—C14	117.4 (2)
H6A—N6—H6B	110 (3)	C12—C13—H13	121
H6A—N6—H6C	104 (3)	C14—C13—H13	121
H6B—N6—H6C	106 (3)	C13—C14—C15	119.0 (3)
O1—C7—O2	125.3 (2)	C13—C14—H14	121
O1—C7—C8	123.6 (2)	C15—C14—H14	121
O1—C7—C8*	94.7 (5)	C10—C15—C14	121.1 (3)
O2—C7—C8	111.1 (3)	C10—C15—H15	119
O2—C7—C8*	140.1 (5)	C14—C15—H15	120
C7—C8—C9	120.8 (3)	N6—C16—C16^i	115.9 (2)
C7—C8—H8	120	N6—C16—C17	113.7 (2)
C9—C8—H8	120	N6—C16—H16	103
C7—C8*—C9*	119.8 (11)	C16^i—C16—C17	115.0 (2)
C7—C8*—H8*	120	C16^i—C16—H16	103
C9*—C8*—H8*	120	C17—C16—H16	103
C8—C9—C10	125.6 (3)	C16—C17—C18	114.1 (2)
C8—C9—H9	117	C16—C17—H17A	109
C10—C9—H9	117	C16—C17—H17B	108
C8*—C9*—C10	106.3 (10)	C18—C17—H17A	108
C8*—C9*—H9*	127	C18—C17—H17B	109
C10—C9*—H9*	127	H17A—C17—H17B	110
C9—C10—C11	115.2 (3)	C17—C18—C18^i	116.6 (2)
C9—C10—C15	125.7 (3)	C17—C18—H18A	108
C9*—C10—C11	152.3 (5)	C17—C18—H18B	108
C9*—C10—C15	88.2 (4)	C18^i—C18—H18A	107
C11—C10—C15	119.0 (3)	C18^i—C18—H18B	108
C10—C11—C12	120.1 (3)	H18A—C18—H18B	110

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O1^ii	0.95 (3)	1.80 (3)	2.723 (3)	166 (3)
N6—H6B···O2	0.90 (3)	1.89 (3)	2.786 (3)	170 (2)
N6—H6C···O2^iii	0.74 (3)	2.09 (3)	2.771 (3)	153 (3)

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