Unexpected molecular structure from laboratory powder diffraction data

In the framework of a thorough study of the reactions of C-(2,4,6-tri­nitro­phenyl)­azo­methines with various nucleophiles, the crystal and molecular structures of three compounds, namely 2,4-dinitro-N-phenyl-6-(phenyl­azo)­benzamide, (I), N-(2-methoxy­phenyl)-2-(2-methoxy­phenylazo)-4,6-dinitro­benzamide, (II), and N-methyl-2,4-dinitro-N-phenyl-6-(phenylazo)­benzamide, (III), were determined from low-resolution laboratory powder diffraction data. The crystal structure determination of (I), starting from erroneous two-dimensional structures, produced the correct solution as a result of the use of a combination of a systematic grid search and bond-restrained Rietveld refinement. The obtained molecular structure of (I) was quite unexpected. Based on the correct molecular structure of (I), the crystal structures of (II) and (III) were routinely solved by the grid search technique.

Computing details

For all compounds, data collection: local program; cell refinement: LSPAID (Visser, 1986); program(s) used to solve structure: MRIA (Zlokazov & Chernyshev, 1992); program(s) used to refine structure: MRIA (Zlokazov & Chernyshev, 1992); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: PARST (Nardelli, 1983).

Figures

(I) 2,4-dinitro-N-phenyl-6-(phenyldiazenyl)-benzamide

Crystal data

C19H13N5O5	Z = 2
Mr = 391.34	F(000) = 404
Monoclinic, P21	Dx = 1.474 Mg m^−3
a = 11.720 (6) Å	Cu Kα radiation, λ = 1.5418 Å
b = 6.831 (4) Å	T = 295 K
c = 11.045 (6) Å	Particle morphology: needles
β = 94.38 (2)°	yellow
V = 881.7 (8) Å^3	flat_sheet, 25 × 25 mm

Data collection

DRON-3M diffractometer (Burevestnik, Russia)	Data collection mode: reflection
Radiation source: X-ray sealed tube	Scan method: step
Ni filtered monochromator	2θmin = 6.00°, 2θmax = 70.0°, 2θstep = 0.02°
Specimen mounting: pressed as a thin layer in the specimen holder

Refinement

Refinement on Inet	138 parameters
Least-squares matrix: full with fixed elements per cycle	51 restraints
Rp = 0.065	1 constraint
Rwp = 0.083	H-atom parameters not refined
Rexp = 0.021	Weighting scheme based on measured s.u.'s
χ^2 = 16.322	(Δ/σ)max = 0.01
3201 data points	Background function: Chebyshev polynomial up to the 5th order
Profile function: split-type pseudo-Voigt (Toraya, 1986)	Preferred orientation correction: Spherical harmonics expansion (Ahtee et al., 1989) up to the 6th order.

Special details

Experimental. specimen was rotated in its plane

Refinement. Hydrogen atoms were placed in calculated positions. The planarity of the aromatic rings and nitrogroups was restrained. The only common atomic displacement parameter was refined for all non-H atoms.

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

	x	y	z	Uiso*/Ueq
C1	0.5482 (8)	0.0401	0.3273 (8)	0.060 (2)*
C2	0.6418 (10)	0.059 (5)	0.2580 (8)	0.060*
C3	0.7541 (8)	0.033 (5)	0.3112 (9)	0.060*
C4	0.7654 (8)	0.004 (5)	0.4382 (8)	0.060*
C5	0.6719 (8)	−0.021 (5)	0.5098 (10)	0.060*
C6	0.5622 (10)	0.011 (5)	0.4553 (8)	0.060*
C7	0.4304 (10)	0.068 (4)	0.2728 (8)	0.060*
N8	0.6246 (6)	0.090 (4)	0.1224 (7)	0.060*
O9	0.5280 (6)	0.110 (3)	0.0801 (5)	0.060*
O10	0.7054 (6)	0.081 (3)	0.0621 (6)	0.060*
N11	0.8817 (6)	−0.019 (3)	0.4993 (7)	0.060*
O12	0.9648 (7)	0.001 (3)	0.4413 (6)	0.060*
O13	0.8902 (6)	−0.068 (3)	0.6054 (6)	0.060*
N14	0.4620 (8)	0.000 (5)	0.5186 (8)	0.060*
N15	0.4706 (7)	0.053 (3)	0.6259 (6)	0.060*
C16	0.3748 (10)	0.042 (5)	0.6957 (8)	0.060*
C17	0.3897 (8)	0.022 (5)	0.8243 (8)	0.060*
C18	0.2933 (9)	0.006 (5)	0.8919 (8)	0.060*
C19	0.1831 (8)	0.015 (5)	0.8357 (8)	0.060*
C20	0.1675 (10)	0.031 (5)	0.7098 (8)	0.060*
C21	0.2614 (8)	0.047 (5)	0.6407 (8)	0.060*
N22	0.3707 (8)	−0.105 (3)	0.2581 (7)	0.060*
C23	0.2564 (8)	−0.109 (4)	0.2098 (9)	0.060*
C24	0.1849 (10)	0.056 (5)	0.2099 (10)	0.060*
C25	0.0712 (10)	0.042 (5)	0.1622 (9)	0.060*
C26	0.0271 (11)	−0.134 (4)	0.1144 (10)	0.060*
C27	0.0974 (11)	−0.297 (3)	0.1132 (10)	0.060*
C28	0.2100 (11)	−0.285 (4)	0.1603 (11)	0.060*
O29	0.4013 (7)	0.236 (3)	0.2419 (6)	0.060*
H30	0.6861	−0.0338	0.5936	0.051*
H31	0.8179	0.0461	0.2661	0.051*
H32	0.4628	0.0182	0.8618	0.051*
H33	0.3042	−0.0042	0.9773	0.051*
H34	0.1189	0.0052	0.8820	0.051*
H35	0.0924	0.0369	0.6718	0.051*
H36	0.2518	0.0593	0.5558	0.051*
H37	0.4058	−0.2158	0.2764	0.051*
H38	0.2133	0.1742	0.2427	0.051*
H39	0.0234	0.1532	0.1632	0.051*
H40	−0.0493	−0.1404	0.0804	0.051*
H41	0.0681	−0.4179	0.0809	0.051*
H42	0.2580	−0.3968	0.1616	0.051*

Geometric parameters (Å, º)

C1—C2	1.39 (2)	C17—C18	1.41 (1)
C1—C6	1.42 (1)	C17—H32	0.92
C1—C7	1.48 (1)	C18—C19	1.39 (1)
C2—C3	1.41 (2)	C18—H33	0.94
C2—N8	1.51 (1)	C19—C20	1.39 (1)
C3—C4	1.41 (1)	C19—H34	0.94
C3—H31	0.93	C20—C21	1.39 (2)
C4—C5	1.41 (2)	C20—H35	0.95
C4—N11	1.48 (1)	C21—H36	0.94
C5—C6	1.39 (2)	N22—C23	1.40 (1)
C5—H30	0.93	N22—H37	0.88
C6—N14	1.41 (2)	C23—C24	1.41 (3)
C7—O29	1.24 (3)	C23—C28	1.41 (3)
C7—N22	1.38 (3)	C24—C25	1.40 (2)
N8—O9	1.20 (1)	C24—H38	0.93
N8—O10	1.20 (1)	C25—C26	1.40 (4)
N11—O12	1.21 (1)	C25—H39	0.95
N11—O13	1.22 (1)	C26—C27	1.39 (3)
N14—N15	1.24 (2)	C26—H40	0.95
N15—C16	1.41 (1)	C27—C28	1.38 (2)
C16—C21	1.42 (1)	C27—H41	0.95
C16—C17	1.42 (1)	C28—H42	0.95
C2—C1—C6	121.5 (5)	C16—C17—H32	119.3
C2—C1—C7	121.1 (8)	C19—C18—C17	121.1 (9)
C6—C1—C7	117.1 (6)	C19—C18—H33	119.9
C1—C2—C3	120.6 (9)	C17—C18—H33	118.9
C1—C2—N8	120.5 (7)	C18—C19—C20	119.7 (9)
C3—C2—N8	118.7 (8)	C18—C19—H34	120.5
C2—C3—C4	116.4 (9)	C20—C19—H34	119.8
C2—C3—H31	121.6	C21—C20—C19	120.3 (8)
C4—C3—H31	121.7	C21—C20—H35	120.1
C5—C4—C3	123.8 (9)	C19—C20—H35	119.5
C5—C4—N11	117.4 (8)	C20—C21—C16	121 (1)
C3—C4—N11	118.7 (8)	C20—C21—H36	121.0
C6—C5—C4	118.1 (9)	C16—C21—H36	117.8
C6—C5—H30	122.2	C7—N22—C23	121 (1)
C4—C5—H30	118.8	C7—N22—H37	119.1
C5—C6—N14	124 (1)	C23—N22—H37	119.4
C5—C6—C1	118.9 (8)	N22—C23—C24	123 (1)
N14—C6—C1	117.5 (7)	N22—C23—C28	119 (1)
O29—C7—N22	130 (2)	C24—C23—C28	118 (2)
O29—C7—C1	117 (1)	C25—C24—C23	120 (1)
N22—C7—C1	113.0 (9)	C25—C24—H38	120.5
O9—N8—O10	123.5 (8)	C23—C24—H38	119.9
O9—N8—C2	116.9 (7)	C26—C25—C24	121 (1)
O10—N8—C2	119.4 (7)	C26—C25—H39	119.7
O12—N11—O13	122.0 (8)	C24—C25—H39	119.1
O12—N11—C4	119.7 (8)	C27—C26—C25	119 (2)
O13—N11—C4	118.2 (7)	C27—C26—H40	120.5
N15—N14—C6	116.7 (8)	C25—C26—H40	120.0
N14—N15—C16	119.8 (8)	C28—C27—C26	120 (1)
N15—C16—C21	122 (1)	C28—C27—H41	119.9
N15—C16—C17	120.5 (8)	C26—C27—H41	120.1
C21—C16—C17	118.0 (8)	C27—C28—C23	122 (1)
C18—C17—C16	119.7 (8)	C27—C28—H42	120.4
C18—C17—H32	121.0	C23—C28—H42	118.0

(II) N-(2-methoxyphenyl-2-(methoxyphenyldiazenyl)-4,6-dinitrobenzamide

Crystal data

C21H17N5O7	F(000) = 936
Mr = 451.40	Dx = 1.461 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.5418 Å
a = 22.788 (8) Å	T = 295 K
b = 13.018 (6) Å	Particle morphology: needles
c = 6.920 (3) Å	yellow
V = 2052.8 (15) Å^3	flat_sheet, 25 × 25 mm
Z = 4

Data collection

DRON-3M diffractometer (Burevestnik, Russia)	Data collection mode: reflection
Radiation source: X-ray sealed tube	Scan method: step
Ni filtered monochromator	2θmin = 6.00°, 2θmax = 70.0°, 2θstep = 0.02°
Specimen mounting: pressed as a thin layer in the specimen holder

Refinement

Refinement on Inet	144 parameters
Least-squares matrix: full with fixed elements per cycle	63 restraints
Rp = 0.057	1 constraint
Rwp = 0.080	H-atom parameters not refined
Rexp = 0.019	Weighting scheme based on measured s.u.'s
χ^2 = 17.140	(Δ/σ)max = 0.01
3201 data points	Background function: Chebyshev polynomial up to the 5th order
Profile function: split-type pseudo-Voigt (Toraya, 1986)	Preferred orientation correction: Spherical harmonics expansion (Ahtee et al., 1989) up to the 6th order.

Special details

Experimental. specimen was rotated in its plane

Refinement. Hydrogen atoms were placed in calculated positions. The planarity of the aromatic rings and nitrogroups was restrained. The only common atomic displacement parameter was refined for all non-H atoms.

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

	x	y	z	Uiso*/Ueq
C1	0.3077 (4)	0.1227 (8)	0.065 (3)	0.035 (1)*
C2	0.3655 (4)	0.1415 (9)	0.067 (3)	0.035*
C3	0.4090 (4)	0.0624 (7)	0.057 (3)	0.035*
C4	0.3872 (4)	−0.0383 (7)	0.041 (3)	0.035*
C5	0.3268 (4)	−0.0607 (8)	0.037 (3)	0.035*
C6	0.2868 (4)	0.0149 (8)	0.047 (3)	0.035*
C7	0.2573 (5)	0.1913 (9)	0.070 (3)	0.035*
N8	0.3892 (4)	0.2508 (8)	0.083 (3)	0.035*
O9	0.3527 (3)	0.3163 (6)	0.105 (2)	0.035*
O10	0.4401 (3)	0.2632 (5)	0.059 (2)	0.035*
N11	0.4282 (3)	−0.1255 (7)	0.030 (3)	0.035*
O12	0.4783 (2)	−0.1019 (6)	0.042 (2)	0.035*
O13	0.4114 (3)	−0.2128 (5)	0.002 (2)	0.035*
N14	0.2250 (4)	0.0116 (8)	0.045 (3)	0.035*
N15	0.2009 (3)	−0.0681 (7)	0.102 (3)	0.035*
C16	0.1394 (3)	−0.0749 (8)	0.074 (3)	0.035*
C17	0.1130 (4)	−0.1735 (8)	0.094 (3)	0.035*
C18	0.0528 (4)	−0.1805 (7)	0.066 (3)	0.035*
C19	0.0194 (3)	−0.0946 (9)	0.022 (3)	0.035*
C20	0.0452 (4)	0.0021 (7)	0.005 (3)	0.035*
C21	0.1050 (4)	0.0117 (7)	0.032 (3)	0.035*
N22	0.2415 (4)	0.2398 (6)	−0.098 (2)	0.035*
C23	0.1927 (4)	0.3052 (8)	−0.117 (3)	0.035*
C24	0.1449 (4)	0.2997 (8)	0.012 (3)	0.035*
C25	0.0962 (4)	0.3634 (9)	−0.004 (3)	0.035*
C26	0.0935 (4)	0.4342 (9)	−0.153 (3)	0.035*
C27	0.1390 (4)	0.4398 (9)	−0.287 (3)	0.035*
C28	0.1885 (4)	0.3766 (9)	−0.271 (3)	0.035*
O29	0.2347 (3)	0.3838 (6)	−0.405 (2)	0.035*
O30	0.1482 (3)	−0.2562 (5)	0.136 (2)	0.035*
C31	0.2186 (4)	0.4368 (9)	−0.574 (3)	0.035*
O32	0.2361 (3)	0.2095 (6)	0.2347 (17)	0.035*
C33	0.1198 (5)	−0.352 (1)	0.118 (3)	0.035*
H34	0.3148	−0.1302	0.0271	0.051*
H35	0.4488	0.0765	0.0599	0.051*
H36	0.0344	−0.2443	0.0768	0.051*
H37	−0.0209	−0.1017	0.0053	0.051*
H38	0.0224	0.0595	−0.0230	0.051*
H39	0.1228	0.0757	0.0199	0.051*
H40	0.2689	0.2432	−0.1850	0.051*
H41	0.1475	0.2535	0.1142	0.051*
H42	0.0657	0.3579	0.0846	0.051*
H43	0.0605	0.4756	−0.1664	0.051*
H44	0.1367	0.4867	−0.3868	0.051*
H45	0.2498	0.4342	−0.6663	0.051*
H46	0.2100	0.5072	−0.5416	0.051*
H47	0.1838	0.4059	−0.6281	0.051*
H48	0.1467	−0.4059	0.1515	0.051*
H49	0.1072	−0.3610	−0.0136	0.051*
H50	0.0864	−0.3541	0.2018	0.051*

Geometric parameters (Å, º)

C1—C2	1.34 (1)	C19—C20	1.39 (1)
C1—C7	1.46 (2)	C19—H37	0.93
C1—C6	1.49 (2)	C20—C21	1.38 (1)
C2—C3	1.43 (1)	C20—H38	0.93
C2—N8	1.53 (1)	C21—H39	0.93
C3—C4	1.41 (1)	N22—C23	1.41 (1)
C3—H35	0.93	N22—H40	0.87
C4—C5	1.41 (1)	C23—C24	1.41 (2)
C4—N11	1.47 (1)	C23—C28	1.42 (2)
C5—C6	1.34 (1)	C24—C25	1.39 (1)
C5—H34	0.95	C24—H41	0.93
C6—N14	1.41 (1)	C25—C26	1.38 (2)
C7—O32	1.26 (2)	C25—H42	0.93
C7—N22	1.37 (2)	C26—C27	1.39 (2)
N8—O10	1.18 (1)	C26—H43	0.93
N8—O9	1.20 (1)	C27—C28	1.40 (1)
N11—O12	1.185 (9)	C27—H44	0.93
N11—O13	1.22 (1)	C28—O29	1.41 (2)
N14—N15	1.24 (2)	O29—C31	1.41 (2)
N15—C16	1.42 (1)	O30—C33	1.41 (1)
C16—C21	1.40 (1)	C31—H45	0.96
C16—C17	1.42 (1)	C31—H46	0.96
C17—O30	1.37 (1)	C31—H47	0.96
C17—C18	1.39 (1)	C33—H48	0.96
C18—C19	1.39 (1)	C33—H49	0.96
C18—H36	0.93	C33—H50	0.96
C2—C1—C7	131.6 (9)	C21—C20—C19	119.1 (8)
C2—C1—C6	119.2 (9)	C21—C20—H38	120.4
C7—C1—C6	109.2 (9)	C19—C20—H38	120.5
C1—C2—C3	123.3 (9)	C20—C21—C16	120.4 (8)
C1—C2—N8	121.3 (9)	C20—C21—H39	120.0
C3—C2—N8	115.4 (9)	C16—C21—H39	119.6
C4—C3—C2	115.5 (9)	C7—N22—C23	124 (1)
C4—C3—H35	122.2	C7—N22—H40	115.0
C2—C3—H35	122.4	C23—N22—H40	118.2
C3—C4—C5	122.7 (8)	N22—C23—C24	121.4 (9)
C3—C4—N11	119.9 (8)	N22—C23—C28	121 (1)
C5—C4—N11	117.4 (8)	C24—C23—C28	117 (1)
C6—C5—C4	120.7 (9)	C25—C24—C23	122.4 (9)
C6—C5—H34	120.5	C25—C24—H41	119.8
C4—C5—H34	118.8	C23—C24—H41	117.7
C5—C6—N14	130.9 (9)	C26—C25—C24	120 (1)
C5—C6—C1	119 (1)	C26—C25—H42	120.6
N14—C6—C1	110.5 (8)	C24—C25—H42	119.9
O32—C7—N22	125 (2)	C25—C26—C27	120 (1)
O32—C7—C1	116 (1)	C25—C26—H43	120.0
N22—C7—C1	118 (1)	C27—C26—H43	120.2
O10—N8—O9	126.9 (9)	C26—C27—C28	121.2 (9)
O10—N8—C2	117.7 (9)	C26—C27—H44	119.4
O9—N8—C2	115.2 (9)	C28—C27—H44	119.4
O12—N11—O13	123.9 (8)	C27—C28—O29	121 (1)
O12—N11—C4	114.1 (7)	C27—C28—C23	120 (1)
O13—N11—C4	122.0 (8)	O29—C28—C23	119 (1)
N15—N14—C6	117.7 (9)	C31—O29—C28	113 (1)
N14—N15—C16	116.4 (8)	C17—O30—C33	113.9 (8)
C21—C16—N15	122.1 (7)	O29—C31—H45	110.1
C21—C16—C17	120.6 (9)	O29—C31—H46	109.0
N15—C16—C17	117.4 (7)	H45—C31—H46	109.9
O30—C17—C18	123.7 (8)	O29—C31—H47	109.4
O30—C17—C16	118.7 (9)	H45—C31—H47	109.8
C18—C17—C16	117.5 (8)	H46—C31—H47	108.7
C19—C18—C17	121.3 (8)	O30—C33—H48	109.3
C19—C18—H36	119.3	O30—C33—H49	109.3
C17—C18—H36	119.4	H48—C33—H49	109.4
C18—C19—C20	121 (1)	O30—C33—H50	109.5
C18—C19—H37	119.3	H48—C33—H50	109.7
C20—C19—H37	119.7	H49—C33—H50	109.5

(III) N-methyl-2,4-dinitro-N-phenyl-6-(phenyldiazenyl)-benzamide

Crystal data

C20H15N5O5	Z = 4
Mr = 405.37	F(000) = 840
Monoclinic, P21/c	Dx = 1.382 Mg m^−3
a = 8.676 (4) Å	Cu Kα radiation, λ = 1.5418 Å
b = 18.560 (7) Å	T = 295 K
c = 12.098 (6) Å	Particle morphology: needles
β = 90.38 (2)°	yellow
V = 1948.1 (15) Å^3	flat_sheet, 25 × 25 mm

Data collection

DRON-3M diffractometer (Burevestnik, Russia)	Data collection mode: reflection
Radiation source: X-ray sealed tube	Scan method: step
Ni filtered monochromator	2θmin = 8.00°, 2θmax = 72.0°, 2θstep = 0.02°
Specimen mounting: pressed as a thin layer in the specimen holder

Refinement

Refinement on Inet	142 parameters
Least-squares matrix: full with fixed elements per cycle	53 restraints
Rp = 0.050	1 constraint
Rwp = 0.066	H-atom parameters not refined
Rexp = 0.022	Weighting scheme based on measured s.u.'s
χ^2 = 9.364	(Δ/σ)max = 0.01
3201 data points	Background function: Chebyshev polynomial up to the 5th order
Profile function: split-type pseudo-Voigt (Toraya, 1986)	Preferred orientation correction: Spherical harmonics expansion (Ahtee et al., 1989) up to the 6th order.

Special details

Experimental. specimen was rotated in its plane

Refinement. Hydrogen atoms were placed in calculated positions. The planarity of the aromatic rings and nitrogroups was restrained. The only common atomic displacement parameter was refined for all non-H atoms.

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

	x	y	z	Uiso*/Ueq
C1	0.078 (2)	0.4394 (6)	0.3423 (8)	0.073 (1)*
C2	0.038 (2)	0.3678 (7)	0.3334 (9)	0.073*
C3	0.091 (2)	0.3160 (6)	0.4124 (9)	0.073*
C4	0.1790 (18)	0.3409 (6)	0.5018 (9)	0.073*
C5	0.2190 (19)	0.4133 (6)	0.5128 (9)	0.073*
C6	0.167 (2)	0.4635 (7)	0.4352 (9)	0.073*
C7	0.022 (2)	0.4981 (6)	0.2654 (8)	0.073*
N8	0.2353 (19)	0.2899 (7)	0.5882 (10)	0.073*
O9	0.2047 (14)	0.2294 (4)	0.5706 (6)	0.073*
O10	0.2975 (17)	0.3172 (6)	0.6674 (8)	0.073*
N11	−0.0542 (18)	0.3403 (6)	0.2374 (8)	0.073*
O12	−0.0791 (17)	0.2774 (5)	0.2353 (7)	0.073*
O13	−0.0820 (14)	0.3863 (4)	0.1676 (6)	0.073*
N14	0.2048 (14)	0.5381 (5)	0.4432 (6)	0.073*
N15	0.2882 (14)	0.5530 (5)	0.5234 (6)	0.073*
C16	0.3310 (18)	0.6248 (6)	0.5423 (9)	0.073*
C17	0.434 (2)	0.6415 (6)	0.6296 (9)	0.073*
C18	0.477 (2)	0.7123 (6)	0.6476 (9)	0.073*
C19	0.419 (2)	0.7671 (5)	0.5785 (9)	0.073*
C20	0.320 (2)	0.7505 (6)	0.4913 (9)	0.073*
C21	0.2761 (18)	0.6807 (6)	0.4729 (9)	0.073*
N22	0.1203 (16)	0.5315 (5)	0.1918 (7)	0.073*
O23	−0.1139 (13)	0.5184 (4)	0.2799 (5)	0.073*
C24	0.2722 (19)	0.5111 (6)	0.1767 (8)	0.073*
C25	0.393 (2)	0.5578 (6)	0.2091 (8)	0.073*
C26	0.5455 (19)	0.5371 (6)	0.1916 (8)	0.073*
C27	0.5776 (19)	0.4707 (6)	0.1437 (8)	0.073*
C28	0.460 (2)	0.4237 (6)	0.1126 (8)	0.073*
C29	0.3063 (19)	0.4434 (6)	0.1285 (8)	0.073*
C30	0.070 (3)	0.5933 (10)	0.1248 (13)	0.073*
H31	0.2791	0.4283	0.5732	0.051*
H32	0.0648	0.2681	0.4044	0.051*
H33	0.4728	0.6050	0.6746	0.051*
H34	0.5441	0.7238	0.7051	0.051*
H35	0.4469	0.8148	0.5912	0.051*
H36	0.2827	0.7870	0.4461	0.051*
H37	0.2102	0.6696	0.4144	0.051*
H38	0.3707	0.6031	0.2383	0.051*
H39	0.6254	0.5675	0.2126	0.051*
H40	0.6798	0.4572	0.1326	0.051*
H41	0.4831	0.3794	0.0806	0.051*
H42	0.2268	0.4128	0.1070	0.051*
H43	−0.0360	0.6034	0.1405	0.051*
H44	0.0851	0.5837	0.0491	0.051*
H45	0.1322	0.6346	0.1474	0.051*

Geometric parameters (Å, º)

C1—C2	1.38 (2)	C18—C19	1.41 (2)
C1—C6	1.43 (2)	C18—H34	0.93
C1—C7	1.51 (2)	C19—C20	1.39 (2)
C2—C3	1.43 (2)	C19—H35	0.93
C2—N11	1.50 (2)	C20—C21	1.37 (2)
C3—C4	1.40 (2)	C20—H36	0.93
C3—H32	0.92	C21—H37	0.93
C4—C5	1.39 (2)	N22—C24	1.38 (2)
C4—N8	1.49 (2)	N22—C30	1.47 (2)
C5—C6	1.40 (2)	C24—C25	1.41 (2)
C5—H31	0.94	C24—C29	1.42 (2)
C6—N14	1.43 (2)	C25—C26	1.40 (2)
C7—O23	1.25 (2)	C25—H38	0.93
C7—N22	1.38 (2)	C26—C27	1.39 (2)
N8—O9	1.17 (2)	C26—H39	0.93
N8—O10	1.21 (2)	C27—C28	1.39 (2)
N11—O12	1.19 (1)	C27—H40	0.93
N11—O13	1.22 (1)	C28—C29	1.39 (3)
N14—N15	1.24 (1)	C28—H41	0.93
N15—C16	1.40 (1)	C29—H42	0.93
C16—C17	1.41 (2)	C30—H43	0.95
C16—C21	1.42 (2)	C30—H44	0.94
C17—C18	1.38 (2)	C30—H45	0.98
C17—H33	0.93
C2—C1—C6	120 (1)	C19—C18—H34	120
C2—C1—C7	125 (1)	C20—C19—C18	120 (1)
C6—C1—C7	115 (1)	C20—C19—H35	120
C1—C2—C3	121 (1)	C18—C19—H35	120
C1—C2—N11	122 (1)	C21—C20—C19	120 (1)
C3—C2—N11	117 (1)	C21—C20—H36	120
C4—C3—C2	118 (1)	C19—C20—H36	120
C4—C3—H32	122	C20—C21—C16	120 (1)
C2—C3—H32	120	C20—C21—H37	120
C5—C4—C3	122 (1)	C16—C21—H37	120
C5—C4—N8	118 (1)	C7—N22—C24	124 (1)
C3—C4—N8	121 (1)	C7—N22—C30	121 (1)
C4—C5—C6	120 (1)	C24—N22—C30	115 (1)
C4—C5—H31	120	N22—C24—C25	120 (1)
C6—C5—H31	120	N22—C24—C29	120 (1)
C5—C6—N14	122 (1)	C25—C24—C29	120 (1)
C5—C6—C1	119 (1)	C26—C25—C24	119 (1)
N14—C6—C1	119 (1)	C26—C25—H38	120
O23—C7—N22	123 (1)	C24—C25—H38	120
O23—C7—C1	115 (1)	C27—C26—C25	120 (1)
N22—C7—C1	121.5 (9)	C27—C26—H39	120
O9—N8—O10	130 (1)	C25—C26—H39	120
O9—N8—C4	114 (1)	C26—C27—C28	121 (1)
O10—N8—C4	116 (1)	C26—C27—H40	119
O12—N11—O13	130 (1)	C28—C27—H40	119
O12—N11—C2	117 (1)	C27—C28—C29	120 (1)
O13—N11—C2	113.6 (9)	C27—C28—H41	120
N15—N14—C6	113.9 (9)	C29—C28—H41	120
N14—N15—C16	119.5 (9)	C28—C29—C24	119 (1)
N15—C16—C17	120 (1)	C28—C29—H42	121
N15—C16—C21	121 (1)	C24—C29—H42	120
C17—C16—C21	119 (1)	N22—C30—H43	109
C18—C17—C16	120 (1)	N22—C30—H44	110
C18—C17—H33	120	H43—C30—H44	112
C16—C17—H33	120	N22—C30—H45	107
C17—C18—C19	120 (1)	H43—C30—H45	109
C17—C18—H34	120	H44—C30—H45	110