Azole. 45. Über 2,4-Dinitrophenylhydrazone von Morpholinonitroimidazolderivaten

The three title compounds, namely (Z)-1-(4,5-di­nitro­imidazol-1-yl)-3-morpholinopropan-2-one 2,4-di­nitro­phenyl­hydrazone, C₁₆H₁₇N₉O₉, (IV), (Z)-3-morpholino-1-(4-morpholino-5-nitro­imidazol-1-yl)propan-2-one 2,4-di­nitro­phenyl­hydrazone, C₂₀H₂₅N₉O₈, (Va), and (E)-3-morpholino-1-(4-morpholino-5-nitro­imidazol-1-yl)propan-2-one 2,4-di­nitro­phenylhydra­zone tetra­hydro­furan solvate, C₂₀H₂₅N₉O₈·C₄H₈O, (Vb), have been prepared and their structures determined. In (IV), the C-4 nitro group is nearly perpendicular to the imidazole ring and the C-4-NO₂ bond length is comparable to the value for a normal single Csp²-NO₂ bond. In (IV), (Va) and (Vb), the C-­5 nitro group deviates insignificantly from the imidazole plane and the C-5-NO₂ bond length is far shorter in all three compounds than C-4-NO₂ in (IV). In consequence, the C-4 nitro group in (IV) is easily replaced by morpholine, while the C-5 nitro group in (IV), (Va) and (Vb) shows an extraordinary stability on treatment with the amine. The E configuration in (Vb) is stabilized by a three-centre hydrogen bond.

Computing details

For all compounds, data collection: KM-4 Software (Kuma Diffraction, 1991); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(IV) (Z)-1-(4,5-dinitroimidazol-1-yl)-3-morpholinopropan-2-one 2,4-dinitrophenylhydrazone

Crystal data

C16H17N9O9	F(000) = 992
Mr = 479.39	Dx = 1.551 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 9.0382 (7) Å	Cell parameters from 49 reflections
b = 19.2008 (13) Å	θ = 14.4–35.9°
c = 11.9087 (8) Å	µ = 1.12 mm^−1
β = 96.579 (6)°	T = 293 K
V = 2053.0 (3) Å^3	Prism, yellow
Z = 4	0.43 × 0.22 × 0.18 mm

Data collection

Kuma KM-4 diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 70.1°, θmin = 4.4°
Graphite monochromator	h = −11→10
ω/2θ scans	k = 0→23
4027 measured reflections	l = 0→14
3851 independent reflections	2 standard reflections every 100 reflections
3135 reflections with I > 2σ(I)	intensity decay: 3.7%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	All H-atom parameters refined
S = 1.08	Calculated w = 1/[σ^2(Fo^2) + (0.0674P)^2 + 0.5232P] where P = (Fo^2 + 2Fc^2)/3
3851 reflections	(Δ/σ)max < 0.001
375 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.25752 (15)	0.65795 (8)	1.11034 (11)	0.0415 (3)
C2	0.2022 (2)	0.71521 (11)	1.15519 (17)	0.0541 (5)
N3	0.2722 (2)	0.73276 (8)	1.25267 (15)	0.0578 (4)
C4	0.37949 (19)	0.68461 (9)	1.27170 (14)	0.0444 (4)
C5	0.37352 (18)	0.63746 (9)	1.18701 (13)	0.0393 (4)
C6	0.2061 (2)	0.62955 (12)	0.99913 (15)	0.0492 (4)
C7	0.29988 (17)	0.65246 (9)	0.90886 (14)	0.0394 (4)
C8	0.41305 (19)	0.70944 (9)	0.93221 (15)	0.0422 (4)
N9	0.28839 (15)	0.62582 (8)	0.81027 (12)	0.0439 (3)
N10	0.18812 (17)	0.57209 (8)	0.78763 (13)	0.0469 (4)
C11	0.19044 (17)	0.53541 (9)	0.69125 (13)	0.0410 (4)
C12	0.10082 (18)	0.47585 (9)	0.66530 (15)	0.0447 (4)
C13	0.1098 (2)	0.43736 (10)	0.56836 (16)	0.0489 (4)
C14	0.2066 (2)	0.45791 (10)	0.49539 (16)	0.0510 (4)
C15	0.2943 (2)	0.51690 (11)	0.51555 (17)	0.0529 (4)
C16	0.2867 (2)	0.55486 (10)	0.61103 (15)	0.0491 (4)
N17	−0.00566 (19)	0.45181 (10)	0.73865 (14)	0.0582 (4)
O18	−0.01693 (17)	0.48265 (9)	0.82804 (13)	0.0700 (4)
O19	−0.0826 (2)	0.40184 (12)	0.70885 (17)	0.1019 (7)
N20	0.2155 (2)	0.41769 (11)	0.39266 (17)	0.0718 (5)
O21	0.1312 (3)	0.36869 (11)	0.37305 (19)	0.1066 (7)
O22	0.3060 (3)	0.43594 (13)	0.33007 (18)	0.1137 (8)
N23	0.54698 (14)	0.68306 (7)	0.99897 (11)	0.0388 (3)
C24	0.6390 (2)	0.74094 (11)	1.04680 (18)	0.0517 (5)
C25	0.7778 (2)	0.71309 (16)	1.1134 (2)	0.0704 (7)
O26	0.86181 (15)	0.67108 (11)	1.04582 (16)	0.0840 (6)
C27	0.7726 (2)	0.61397 (15)	1.0000 (3)	0.0738 (7)
C28	0.6340 (2)	0.63977 (11)	0.92951 (18)	0.0494 (4)
N29	0.4856 (2)	0.68843 (10)	1.37304 (14)	0.0615 (5)
O30	0.4647 (3)	0.65756 (14)	1.45398 (16)	0.1131 (8)
O31	0.5875 (3)	0.72788 (17)	1.36971 (19)	0.1423 (12)
N32	0.4635 (2)	0.57824 (9)	1.17602 (15)	0.0572 (4)
O33	0.5700 (2)	0.57225 (12)	1.24768 (17)	0.1012 (7)
O34	0.4326 (2)	0.53839 (8)	1.09758 (16)	0.0814 (5)
H2A	0.121 (3)	0.7411 (13)	1.115 (2)	0.072 (7)*
H6A	0.206 (3)	0.5790 (13)	1.008 (2)	0.067 (7)*
H6B	0.104 (3)	0.6484 (13)	0.979 (2)	0.074 (7)*
H8A	0.371 (2)	0.7485 (10)	0.9772 (16)	0.046 (5)*
H8B	0.435 (2)	0.7302 (10)	0.8578 (17)	0.048 (5)*
H10A	0.130 (3)	0.5591 (11)	0.8327 (19)	0.057 (6)*
H13A	0.055 (3)	0.3988 (13)	0.5556 (18)	0.061 (6)*
H15A	0.360 (3)	0.5293 (13)	0.464 (2)	0.074 (7)*
H16A	0.351 (3)	0.5942 (12)	0.6306 (19)	0.062 (6)*
H24A	0.663 (2)	0.7742 (12)	0.9842 (19)	0.061 (6)*
H24B	0.586 (3)	0.7672 (12)	1.0971 (19)	0.062 (6)*
H25A	0.753 (3)	0.6824 (12)	1.180 (2)	0.066 (7)*
H25B	0.838 (3)	0.7492 (14)	1.147 (2)	0.077 (7)*
H27A	0.832 (3)	0.5897 (14)	0.945 (2)	0.087 (8)*
H27B	0.745 (3)	0.5818 (15)	1.063 (2)	0.093 (9)*
H28A	0.578 (2)	0.6009 (11)	0.9030 (17)	0.050 (5)*
H28B	0.650 (3)	0.6671 (11)	0.8631 (19)	0.060 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0341 (7)	0.0523 (8)	0.0387 (7)	−0.0024 (6)	0.0060 (5)	−0.0004 (6)
C2	0.0470 (10)	0.0615 (11)	0.0560 (11)	0.0128 (9)	0.0145 (9)	0.0004 (9)
N3	0.0651 (11)	0.0509 (9)	0.0599 (10)	0.0033 (8)	0.0177 (8)	−0.0078 (7)
C4	0.0433 (9)	0.0506 (9)	0.0402 (9)	−0.0126 (7)	0.0090 (7)	−0.0020 (7)
C5	0.0349 (8)	0.0435 (8)	0.0404 (8)	−0.0026 (6)	0.0076 (6)	0.0032 (7)
C6	0.0386 (9)	0.0691 (13)	0.0399 (9)	−0.0122 (8)	0.0041 (7)	−0.0012 (8)
C7	0.0304 (8)	0.0483 (9)	0.0389 (8)	−0.0004 (6)	0.0014 (6)	0.0029 (7)
C8	0.0394 (9)	0.0442 (9)	0.0428 (9)	−0.0026 (7)	0.0039 (7)	0.0032 (7)
N9	0.0369 (7)	0.0523 (8)	0.0420 (8)	−0.0064 (6)	0.0018 (6)	0.0002 (6)
N10	0.0387 (8)	0.0612 (9)	0.0411 (8)	−0.0117 (7)	0.0050 (6)	−0.0026 (7)
C11	0.0331 (8)	0.0495 (9)	0.0392 (8)	−0.0008 (7)	−0.0005 (6)	0.0042 (7)
C12	0.0357 (8)	0.0513 (9)	0.0459 (9)	−0.0035 (7)	−0.0008 (7)	0.0075 (8)
C13	0.0447 (10)	0.0440 (9)	0.0559 (11)	−0.0006 (8)	−0.0034 (8)	−0.0004 (8)
C14	0.0501 (10)	0.0506 (10)	0.0510 (10)	0.0072 (8)	0.0004 (8)	−0.0058 (8)
C15	0.0510 (10)	0.0599 (11)	0.0491 (10)	−0.0021 (9)	0.0116 (8)	−0.0002 (9)
C16	0.0480 (10)	0.0526 (10)	0.0472 (10)	−0.0100 (8)	0.0083 (8)	−0.0010 (8)
N17	0.0491 (9)	0.0713 (11)	0.0537 (10)	−0.0187 (8)	0.0030 (7)	0.0073 (8)
O18	0.0604 (9)	0.0886 (11)	0.0643 (9)	−0.0198 (8)	0.0209 (7)	0.0002 (8)
O19	0.1081 (15)	0.1161 (15)	0.0847 (12)	−0.0740 (13)	0.0247 (11)	−0.0094 (11)
N20	0.0758 (13)	0.0704 (12)	0.0702 (12)	0.0098 (10)	0.0124 (10)	−0.0212 (10)
O21	0.1185 (17)	0.0879 (13)	0.1162 (16)	−0.0206 (12)	0.0254 (13)	−0.0558 (12)
O22	0.1310 (19)	0.1294 (18)	0.0902 (14)	−0.0242 (15)	0.0531 (14)	−0.0446 (13)
N23	0.0305 (7)	0.0444 (7)	0.0420 (7)	−0.0035 (5)	0.0059 (5)	−0.0031 (6)
C24	0.0413 (10)	0.0582 (11)	0.0565 (11)	−0.0099 (8)	0.0095 (8)	−0.0160 (9)
C25	0.0376 (10)	0.0998 (18)	0.0722 (15)	−0.0066 (11)	−0.0003 (10)	−0.0290 (14)
O26	0.0305 (7)	0.1152 (14)	0.1062 (13)	−0.0015 (8)	0.0077 (7)	−0.0403 (11)
C27	0.0364 (10)	0.0844 (16)	0.1005 (19)	0.0095 (10)	0.0077 (11)	−0.0242 (15)
C28	0.0377 (9)	0.0535 (10)	0.0593 (11)	−0.0057 (8)	0.0148 (8)	−0.0127 (9)
N29	0.0585 (10)	0.0810 (12)	0.0448 (9)	−0.0250 (9)	0.0048 (7)	−0.0072 (8)
O30	0.1150 (16)	0.157 (2)	0.0605 (10)	−0.0520 (15)	−0.0173 (10)	0.0412 (12)
O31	0.1189 (18)	0.214 (3)	0.0881 (14)	−0.114 (2)	−0.0140 (13)	0.0025 (16)
N32	0.0602 (10)	0.0530 (9)	0.0595 (10)	0.0132 (8)	0.0116 (8)	0.0071 (8)
O33	0.0874 (13)	0.1199 (16)	0.0908 (13)	0.0512 (12)	−0.0141 (10)	0.0138 (12)
O34	0.1040 (13)	0.0529 (8)	0.0899 (12)	0.0110 (9)	0.0223 (10)	−0.0158 (8)

Geometric parameters (Å, º)

N1—C2	1.344 (2)	C14—N20	1.457 (3)
N1—C5	1.367 (2)	C15—C16	1.359 (3)
N1—C6	1.458 (2)	C15—H15A	0.93 (3)
C2—N3	1.301 (3)	C16—H16A	0.97 (2)
C2—H2A	0.97 (3)	N17—O19	1.214 (2)
N3—C4	1.340 (2)	N17—O18	1.233 (2)
C4—C5	1.352 (2)	N20—O21	1.216 (3)
C4—N29	1.455 (2)	N20—O22	1.220 (3)
C5—N32	1.413 (2)	N23—C24	1.464 (2)
C6—C7	1.509 (2)	N23—C28	1.464 (2)
C6—H6A	0.98 (2)	C24—C25	1.504 (3)
C6—H6B	0.99 (3)	C24—H24A	1.02 (2)
C7—N9	1.274 (2)	C24—H24B	0.96 (2)
C7—C8	1.502 (2)	C25—O26	1.420 (3)
C8—N23	1.461 (2)	C25—H25A	1.03 (2)
C8—H8A	1.02 (2)	C25—H25B	0.94 (3)
C8—H8B	1.01 (2)	O26—C27	1.432 (3)
N9—N10	1.379 (2)	C27—C28	1.509 (3)
N10—C11	1.349 (2)	C27—H27A	1.01 (3)
N10—H10A	0.83 (2)	C27—H27B	1.03 (3)
C11—C16	1.414 (2)	C28—H28A	0.94 (2)
C11—C12	1.415 (2)	C28—H28B	0.97 (2)
C12—C13	1.381 (3)	N29—O30	1.165 (2)
C12—N17	1.447 (2)	N29—O31	1.197 (2)
C13—C14	1.360 (3)	N32—O34	1.215 (2)
C13—H13A	0.90 (2)	N32—O33	1.217 (2)
C14—C15	1.388 (3)
C2—N1—C5	105.17 (15)	C16—C15—H15A	120.7 (15)
C2—N1—C6	124.94 (16)	C14—C15—H15A	119.3 (15)
C5—N1—C6	129.74 (15)	C15—C16—C11	121.17 (18)
N3—C2—N1	113.67 (18)	C15—C16—H16A	122.2 (13)
N3—C2—H2A	124.8 (14)	C11—C16—H16A	116.5 (13)
N1—C2—H2A	121.5 (14)	O19—N17—O18	122.07 (18)
C2—N3—C4	103.92 (16)	O19—N17—C12	118.29 (18)
N3—C4—C5	111.70 (16)	O18—N17—C12	119.63 (16)
N3—C4—N29	120.06 (17)	O21—N20—O22	123.7 (2)
C5—C4—N29	128.24 (17)	O21—N20—C14	118.5 (2)
C4—C5—N1	105.53 (15)	O22—N20—C14	117.8 (2)
C4—C5—N32	129.35 (16)	C8—N23—C24	110.30 (14)
N1—C5—N32	125.12 (15)	C8—N23—C28	110.78 (14)
N1—C6—C7	113.06 (14)	C24—N23—C28	109.45 (14)
N1—C6—H6A	105.8 (14)	N23—C24—C25	109.73 (18)
C7—C6—H6A	112.1 (14)	N23—C24—H24A	110.4 (13)
N1—C6—H6B	105.9 (14)	C25—C24—H24A	111.8 (13)
C7—C6—H6B	107.6 (14)	N23—C24—H24B	109.9 (14)
H6A—C6—H6B	112 (2)	C25—C24—H24B	107.9 (14)
N9—C7—C8	116.43 (15)	H24A—C24—H24B	107.0 (18)
N9—C7—C6	123.13 (15)	O26—C25—C24	111.80 (18)
C8—C7—C6	120.44 (15)	O26—C25—H25A	106.7 (14)
N23—C8—C7	110.64 (13)	C24—C25—H25A	111.3 (14)
N23—C8—H8A	107.8 (11)	O26—C25—H25B	109.6 (16)
C7—C8—H8A	110.1 (11)	C24—C25—H25B	111.8 (16)
N23—C8—H8B	112.5 (11)	H25A—C25—H25B	105 (2)
C7—C8—H8B	108.7 (11)	C25—O26—C27	109.66 (17)
H8A—C8—H8B	107.0 (15)	O26—C27—C28	110.8 (2)
C7—N9—N10	117.57 (14)	O26—C27—H27A	106.3 (16)
C11—N10—N9	118.88 (15)	C28—C27—H27A	105.0 (16)
C11—N10—H10A	117.8 (15)	O26—C27—H27B	110.6 (17)
N9—N10—H10A	123.2 (15)	C28—C27—H27B	110.7 (17)
N10—C11—C16	120.51 (16)	H27A—C27—H27B	113 (2)
N10—C11—C12	122.93 (16)	N23—C28—C27	109.71 (17)
C16—C11—C12	116.55 (16)	N23—C28—H28A	109.9 (12)
C13—C12—C11	121.89 (17)	C27—C28—H28A	107.8 (12)
C13—C12—N17	116.13 (17)	N23—C28—H28B	107.1 (13)
C11—C12—N17	121.98 (16)	C27—C28—H28B	115.8 (14)
C14—C13—C12	118.84 (18)	H28A—C28—H28B	106.4 (17)
C14—C13—H13A	121.2 (15)	O30—N29—O31	123.2 (2)
C12—C13—H13A	119.9 (15)	O30—N29—C4	120.43 (17)
C13—C14—C15	121.52 (18)	O31—N29—C4	116.18 (19)
C13—C14—N20	118.96 (19)	O34—N32—O33	124.97 (19)
C15—C14—N20	119.50 (19)	O34—N32—C5	119.62 (17)
C16—C15—C14	120.00 (19)	O33—N32—C5	115.39 (18)
C5—N1—C2—N3	0.0 (2)	C13—C14—C15—C16	1.3 (3)
C6—N1—C2—N3	−175.99 (17)	N20—C14—C15—C16	179.91 (19)
N1—C2—N3—C4	0.5 (2)	C14—C15—C16—C11	0.0 (3)
C2—N3—C4—C5	−0.8 (2)	N10—C11—C16—C15	177.54 (17)
C2—N3—C4—N29	178.02 (17)	C12—C11—C16—C15	−1.5 (3)
N3—C4—C5—N1	0.87 (19)	C13—C12—N17—O19	−2.6 (3)
N29—C4—C5—N1	−177.87 (16)	C11—C12—N17—O19	177.3 (2)
N3—C4—C5—N32	−178.40 (17)	C13—C12—N17—O18	178.20 (17)
N29—C4—C5—N32	2.9 (3)	C11—C12—N17—O18	−1.9 (3)
C2—N1—C5—C4	−0.52 (18)	C13—C14—N20—O21	3.2 (3)
C6—N1—C5—C4	175.22 (16)	C15—C14—N20—O21	−175.5 (2)
C2—N1—C5—N32	178.78 (17)	C13—C14—N20—O22	−178.0 (2)
C6—N1—C5—N32	−5.5 (3)	C15—C14—N20—O22	3.3 (3)
C2—N1—C6—C7	96.5 (2)	C7—C8—N23—C24	−164.91 (14)
C5—N1—C6—C7	−78.5 (2)	C7—C8—N23—C28	73.76 (18)
N1—C6—C7—N9	169.24 (16)	C8—N23—C24—C25	−178.91 (16)
N1—C6—C7—C8	−11.1 (2)	C28—N23—C24—C25	−56.8 (2)
N9—C7—C8—N23	−102.43 (17)	N23—C24—C25—O26	58.2 (3)
C6—C7—C8—N23	77.9 (2)	C24—C25—O26—C27	−58.8 (3)
C8—C7—N9—N10	178.28 (14)	C25—O26—C27—C28	58.9 (3)
C6—C7—N9—N10	−2.0 (2)	C8—N23—C28—C27	179.28 (17)
C7—N9—N10—C11	−169.32 (15)	C24—N23—C28—C27	57.4 (2)
N9—N10—C11—C16	−4.5 (2)	O26—C27—C28—N23	−58.9 (3)
N9—N10—C11—C12	174.50 (15)	N3—C4—N29—O30	94.2 (3)
N10—C11—C12—C13	−177.15 (16)	C5—C4—N29—O30	−87.2 (3)
C16—C11—C12—C13	1.9 (2)	N3—C4—N29—O31	−81.2 (3)
N10—C11—C12—N17	3.0 (3)	C5—C4—N29—O31	97.4 (3)
C16—C11—C12—N17	−178.03 (16)	C4—C5—N32—O34	173.61 (19)
C11—C12—C13—C14	−0.7 (3)	N1—C5—N32—O34	−5.5 (3)
N17—C12—C13—C14	179.20 (16)	C4—C5—N32—O33	−7.6 (3)
C12—C13—C14—C15	−0.9 (3)	N1—C5—N32—O33	173.31 (19)
C12—C13—C14—N20	−179.56 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10A···O18	0.83 (2)	1.98 (2)	2.611 (2)	133 (2)
C6—H6A···O34	0.98 (2)	2.33 (2)	2.842 (2)	112.0 (18)
C6—H6B···O26^i	0.99 (3)	2.46 (3)	3.320 (2)	145.4 (19)
C13—H13A···O19	0.90 (2)	2.32 (2)	2.637 (3)	100.6 (16)
C16—H16A···N9	0.98 (2)	2.36 (2)	2.735 (2)	102.5 (16)

Symmetry code: (i) x−1, y, z.

(Va) (Z)-1-(4-morpholino-5-nitroimidazol-1-yl)-3-morpholinopropan-2-one 2,4-dinitrophenylhydrazone

Crystal data

C20H25N9O8	Z = 2
Mr = 519.49	F(000) = 544
Triclinic, P1	Dx = 1.471 Mg m^−3
a = 8.0664 (6) Å	Cu Kα radiation, λ = 1.54178 Å
b = 12.3698 (10) Å	Cell parameters from 38 reflections
c = 13.2280 (13) Å	θ = 11.4–32.2°
α = 111.282 (8)°	µ = 0.99 mm^−1
β = 106.037 (7)°	T = 293 K
γ = 90.735 (6)°	Prism, orange-brown
V = 1172.55 (13) Å^3	0.52 × 0.22 × 0.16 mm

Data collection

Kuma KM-4 diffractometer	Rint = 0.006
Radiation source: fine-focus sealed tube	θmax = 70.1°, θmin = 3.8°
Graphite monochromator	h = −9→9
ω/2θ scans	k = −14→14
4407 measured reflections	l = −15→9
4205 independent reflections	2 standard reflections every 100 reflections
3575 reflections with I > 2σ(I)	intensity decay: 1.5%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	All H-atom parameters refined
S = 1.04	Calculated w = 1/[σ^2(Fo^2) + (0.0491P)^2 + 0.3977P] where P = (Fo^2 + 2Fc^2)/3
4205 reflections	(Δ/σ)max < 0.001
434 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.73219 (17)	1.07067 (11)	0.30647 (11)	0.0394 (3)
C2	0.6685 (2)	1.11499 (15)	0.22835 (15)	0.0463 (4)
N3	0.67492 (19)	1.22982 (12)	0.26953 (12)	0.0460 (3)
C4	0.75053 (19)	1.26521 (14)	0.38352 (13)	0.0389 (3)
C5	0.79154 (19)	1.16700 (14)	0.40960 (13)	0.0385 (3)
C6	0.7411 (2)	0.94624 (14)	0.28057 (15)	0.0422 (4)
C7	0.5930 (2)	0.88658 (14)	0.29834 (13)	0.0393 (3)
C8	0.4642 (2)	0.95597 (15)	0.34888 (14)	0.0425 (4)
N9	0.56507 (18)	0.77586 (12)	0.26820 (12)	0.0436 (3)
N10	0.67787 (19)	0.70925 (12)	0.21650 (12)	0.0440 (3)
C11	0.6358 (2)	0.59151 (14)	0.17102 (13)	0.0385 (3)
C12	0.7496 (2)	0.51144 (14)	0.13154 (13)	0.0401 (4)
C13	0.7023 (2)	0.39187 (15)	0.08657 (14)	0.0427 (4)
C14	0.5388 (2)	0.34943 (14)	0.07772 (13)	0.0417 (4)
C15	0.4218 (2)	0.42414 (15)	0.11317 (15)	0.0440 (4)
C16	0.4690 (2)	0.54187 (15)	0.15885 (15)	0.0430 (4)
N17	0.92190 (19)	0.55118 (14)	0.13470 (13)	0.0515 (4)
O18	0.9583 (2)	0.65417 (13)	0.15356 (15)	0.0784 (5)
O19	1.02297 (19)	0.47958 (15)	0.11587 (17)	0.0819 (5)
N20	0.4870 (2)	0.22401 (13)	0.02960 (12)	0.0509 (4)
O21	0.5888 (2)	0.15919 (12)	−0.00444 (13)	0.0696 (4)
O22	0.3422 (2)	0.18844 (13)	0.02456 (15)	0.0751 (4)
N23	0.34041 (16)	0.98898 (12)	0.26465 (12)	0.0418 (3)
C24	0.2622 (3)	1.09188 (16)	0.31848 (18)	0.0537 (5)
C25	0.1331 (3)	1.1214 (2)	0.2287 (2)	0.0688 (6)
O26	0.00152 (17)	1.02646 (14)	0.15767 (13)	0.0710 (4)
C27	0.0784 (3)	0.9277 (2)	0.1037 (2)	0.0696 (6)
C28	0.2033 (2)	0.89255 (17)	0.19029 (16)	0.0516 (4)
N29	0.77156 (18)	1.38129 (12)	0.45242 (12)	0.0429 (3)
C30	0.7001 (3)	1.45843 (15)	0.39385 (16)	0.0483 (4)
C31	0.7593 (3)	1.58446 (17)	0.47139 (19)	0.0587 (5)
O32	0.71433 (18)	1.61231 (11)	0.57372 (12)	0.0631 (4)
C33	0.7967 (3)	1.54175 (19)	0.63176 (18)	0.0642 (5)
C34	0.7386 (3)	1.41346 (18)	0.56284 (16)	0.0542 (5)
N35	0.88102 (17)	1.15388 (13)	0.50996 (12)	0.0458 (3)
O36	0.97978 (18)	1.23815 (13)	0.58793 (12)	0.0681 (4)
O37	0.85794 (18)	1.05837 (12)	0.51830 (11)	0.0586 (3)
H2A	0.621 (3)	1.0625 (18)	0.1504 (18)	0.060 (6)*
H6A	0.739 (2)	0.9113 (15)	0.2004 (16)	0.044 (5)*
H6B	0.854 (3)	0.9345 (17)	0.3272 (17)	0.055 (5)*
H8A	0.404 (2)	0.9072 (16)	0.3772 (15)	0.046 (5)*
H8B	0.525 (2)	1.0270 (16)	0.4113 (16)	0.044 (5)*
H10A	0.787 (3)	0.738 (2)	0.227 (2)	0.074 (7)*
H13A	0.784 (3)	0.3422 (16)	0.0594 (16)	0.052 (5)*
H15A	0.304 (3)	0.3929 (17)	0.1039 (17)	0.056 (5)*
H16A	0.392 (3)	0.5946 (17)	0.1850 (17)	0.057 (5)*
H24A	0.352 (3)	1.156 (2)	0.3630 (19)	0.070 (6)*
H24B	0.202 (3)	1.0778 (18)	0.3721 (18)	0.061 (6)*
H25A	0.192 (3)	1.140 (2)	0.183 (2)	0.084 (8)*
H25B	0.081 (4)	1.189 (2)	0.264 (2)	0.093 (8)*
H27A	0.144 (3)	0.950 (2)	0.062 (2)	0.071 (7)*
H27B	−0.018 (4)	0.864 (2)	0.057 (2)	0.093 (8)*
H28A	0.251 (3)	0.8224 (17)	0.1480 (17)	0.056 (5)*
H28B	0.141 (3)	0.8710 (18)	0.2378 (19)	0.065 (6)*
H30A	0.743 (3)	1.4382 (16)	0.3261 (17)	0.052 (5)*
H30B	0.573 (3)	1.4442 (17)	0.3670 (17)	0.058 (6)*
H31A	0.886 (3)	1.6000 (19)	0.4900 (19)	0.070 (6)*
H31B	0.697 (3)	1.6353 (19)	0.4332 (18)	0.066 (6)*
H33A	0.762 (3)	1.563 (2)	0.702 (2)	0.084 (7)*
H33B	0.926 (3)	1.557 (2)	0.653 (2)	0.075 (7)*
H34A	0.801 (3)	1.367 (2)	0.604 (2)	0.072 (7)*
H34B	0.609 (3)	1.3981 (18)	0.5514 (18)	0.064 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0435 (7)	0.0400 (7)	0.0372 (7)	0.0059 (5)	0.0123 (5)	0.0174 (6)
C2	0.0573 (10)	0.0452 (9)	0.0354 (9)	0.0050 (7)	0.0106 (7)	0.0170 (7)
N3	0.0575 (8)	0.0440 (8)	0.0363 (7)	0.0048 (6)	0.0102 (6)	0.0178 (6)
C4	0.0358 (7)	0.0434 (8)	0.0379 (8)	0.0017 (6)	0.0108 (6)	0.0164 (7)
C5	0.0356 (7)	0.0450 (8)	0.0354 (8)	0.0033 (6)	0.0086 (6)	0.0172 (7)
C6	0.0444 (9)	0.0408 (8)	0.0456 (9)	0.0090 (7)	0.0176 (7)	0.0181 (7)
C7	0.0410 (8)	0.0435 (8)	0.0356 (8)	0.0071 (6)	0.0112 (6)	0.0177 (7)
C8	0.0446 (9)	0.0464 (9)	0.0384 (8)	0.0052 (7)	0.0165 (7)	0.0154 (7)
N9	0.0449 (7)	0.0439 (8)	0.0454 (8)	0.0088 (6)	0.0167 (6)	0.0185 (6)
N10	0.0422 (7)	0.0410 (7)	0.0505 (8)	0.0076 (6)	0.0165 (6)	0.0173 (6)
C11	0.0409 (8)	0.0411 (8)	0.0366 (8)	0.0075 (6)	0.0101 (6)	0.0195 (7)
C12	0.0375 (8)	0.0486 (9)	0.0392 (8)	0.0075 (7)	0.0124 (6)	0.0218 (7)
C13	0.0467 (9)	0.0476 (9)	0.0389 (8)	0.0137 (7)	0.0148 (7)	0.0206 (7)
C14	0.0494 (9)	0.0407 (8)	0.0363 (8)	0.0056 (7)	0.0106 (7)	0.0181 (7)
C15	0.0399 (8)	0.0499 (9)	0.0451 (9)	0.0040 (7)	0.0119 (7)	0.0220 (7)
C16	0.0383 (8)	0.0468 (9)	0.0474 (9)	0.0098 (7)	0.0129 (7)	0.0217 (7)
N17	0.0441 (8)	0.0602 (9)	0.0523 (9)	0.0069 (7)	0.0198 (7)	0.0199 (7)
O18	0.0672 (9)	0.0561 (9)	0.1051 (12)	−0.0097 (7)	0.0485 (9)	0.0069 (8)
O19	0.0527 (8)	0.0879 (11)	0.1270 (15)	0.0280 (8)	0.0462 (9)	0.0510 (11)
N20	0.0656 (10)	0.0455 (8)	0.0416 (8)	0.0048 (7)	0.0150 (7)	0.0177 (6)
O21	0.0967 (11)	0.0471 (7)	0.0720 (9)	0.0164 (7)	0.0443 (8)	0.0165 (7)
O22	0.0630 (9)	0.0574 (8)	0.0946 (12)	−0.0102 (7)	0.0179 (8)	0.0222 (8)
N23	0.0370 (7)	0.0442 (7)	0.0451 (8)	0.0055 (5)	0.0150 (6)	0.0160 (6)
C24	0.0506 (10)	0.0420 (9)	0.0668 (12)	0.0087 (8)	0.0205 (9)	0.0167 (9)
C25	0.0559 (12)	0.0678 (14)	0.0952 (17)	0.0204 (10)	0.0273 (12)	0.0416 (13)
O26	0.0439 (7)	0.0884 (11)	0.0782 (10)	0.0206 (7)	0.0169 (7)	0.0298 (8)
C27	0.0469 (11)	0.0908 (17)	0.0578 (12)	0.0138 (11)	0.0102 (10)	0.0170 (12)
C28	0.0430 (9)	0.0516 (10)	0.0499 (10)	0.0029 (7)	0.0148 (8)	0.0073 (8)
N29	0.0458 (7)	0.0419 (7)	0.0400 (7)	0.0031 (6)	0.0123 (6)	0.0149 (6)
C30	0.0526 (10)	0.0452 (9)	0.0507 (10)	0.0074 (7)	0.0188 (8)	0.0200 (8)
C31	0.0596 (12)	0.0467 (10)	0.0700 (13)	0.0048 (9)	0.0245 (10)	0.0189 (9)
O32	0.0667 (9)	0.0500 (7)	0.0627 (8)	0.0102 (6)	0.0212 (7)	0.0089 (6)
C33	0.0677 (13)	0.0626 (12)	0.0475 (11)	0.0079 (10)	0.0132 (10)	0.0073 (9)
C34	0.0626 (12)	0.0568 (11)	0.0420 (10)	0.0067 (9)	0.0182 (8)	0.0157 (8)
N35	0.0375 (7)	0.0598 (9)	0.0413 (8)	0.0097 (6)	0.0097 (6)	0.0222 (7)
O36	0.0572 (8)	0.0793 (10)	0.0493 (8)	−0.0048 (7)	−0.0083 (6)	0.0218 (7)
O37	0.0674 (8)	0.0638 (8)	0.0559 (8)	0.0187 (6)	0.0174 (6)	0.0363 (7)

Geometric parameters (Å, º)

N1—C2	1.326 (2)	N20—O21	1.216 (2)
N1—C5	1.398 (2)	N20—O22	1.218 (2)
N1—C6	1.458 (2)	N23—C28	1.459 (2)
C2—N3	1.318 (2)	N23—C24	1.462 (2)
C2—H2A	0.96 (2)	C24—C25	1.507 (3)
N3—C4	1.358 (2)	C24—H24A	0.95 (2)
C4—N29	1.371 (2)	C24—H24B	1.02 (2)
C4—C5	1.398 (2)	C25—O26	1.416 (3)
C5—N35	1.393 (2)	C25—H25A	0.95 (3)
C6—C7	1.511 (2)	C25—H25B	0.97 (3)
C6—H6A	0.985 (19)	O26—C27	1.421 (3)
C6—H6B	1.00 (2)	C27—C28	1.500 (3)
C7—N9	1.277 (2)	C27—H27A	0.96 (2)
C7—C8	1.501 (2)	C27—H27B	0.99 (3)
C8—N23	1.460 (2)	C28—H28A	0.99 (2)
C8—H8A	0.997 (19)	C28—H28B	1.01 (2)
C8—H8B	0.966 (18)	N29—C30	1.465 (2)
N9—N10	1.3887 (19)	N29—C34	1.469 (2)
N10—C11	1.355 (2)	C30—C31	1.503 (3)
N10—H10A	0.90 (2)	C30—H30A	1.00 (2)
C11—C16	1.414 (2)	C30—H30B	0.98 (2)
C11—C12	1.418 (2)	C31—O32	1.421 (3)
C12—C13	1.382 (2)	C31—H31A	0.98 (2)
C12—N17	1.453 (2)	C31—H31B	1.00 (2)
C13—C14	1.372 (2)	O32—C33	1.419 (3)
C13—H13A	0.96 (2)	C33—C34	1.505 (3)
C14—C15	1.385 (2)	C33—H33A	0.99 (3)
C14—N20	1.451 (2)	C33—H33B	1.00 (2)
C15—C16	1.361 (2)	C34—H34A	0.98 (2)
C15—H15A	0.98 (2)	C34—H34B	1.02 (2)
C16—H16A	0.95 (2)	N35—O36	1.2366 (19)
N17—O19	1.217 (2)	N35—O37	1.2421 (19)
N17—O18	1.221 (2)
C2—N1—C5	105.40 (13)	C8—N23—C24	111.65 (14)
C2—N1—C6	123.78 (14)	N23—C24—C25	109.88 (18)
C5—N1—C6	130.74 (13)	N23—C24—H24A	108.8 (14)
N3—C2—N1	114.14 (15)	C25—C24—H24A	109.9 (13)
N3—C2—H2A	127.1 (12)	N23—C24—H24B	110.8 (12)
N1—C2—H2A	118.7 (12)	C25—C24—H24B	110.0 (12)
C2—N3—C4	105.76 (14)	H24A—C24—H24B	107.4 (18)
N3—C4—N29	120.30 (14)	O26—C25—C24	111.46 (18)
N3—C4—C5	108.80 (14)	O26—C25—H25A	108.7 (16)
N29—C4—C5	130.88 (15)	C24—C25—H25A	108.9 (16)
N35—C5—N1	121.31 (14)	O26—C25—H25B	109.6 (16)
N35—C5—C4	132.72 (15)	C24—C25—H25B	110.1 (16)
N1—C5—C4	105.85 (13)	H25A—C25—H25B	108 (2)
N1—C6—C7	113.23 (13)	C25—O26—C27	109.50 (17)
N1—C6—H6A	106.2 (10)	O26—C27—C28	110.72 (18)
C7—C6—H6A	110.2 (10)	O26—C27—H27A	108.0 (14)
N1—C6—H6B	110.0 (11)	C28—C27—H27A	107.2 (14)
C7—C6—H6B	109.8 (11)	O26—C27—H27B	106.2 (15)
H6A—C6—H6B	107.2 (15)	C28—C27—H27B	109.6 (16)
N9—C7—C8	115.96 (14)	H27A—C27—H27B	115 (2)
N9—C7—C6	123.18 (14)	N23—C28—C27	110.01 (18)
C8—C7—C6	120.80 (14)	N23—C28—H28A	111.7 (12)
N23—C8—C7	110.63 (13)	C27—C28—H28A	107.3 (11)
N23—C8—H8A	111.5 (11)	N23—C28—H28B	109.0 (12)
C7—C8—H8A	107.8 (10)	C27—C28—H28B	110.2 (12)
N23—C8—H8B	107.9 (11)	H28A—C28—H28B	108.5 (17)
C7—C8—H8B	109.1 (11)	C4—N29—C30	114.86 (14)
H8A—C8—H8B	110.0 (15)	C4—N29—C34	118.69 (14)
C7—N9—N10	117.09 (14)	C30—N29—C34	112.13 (15)
C11—N10—N9	117.25 (14)	N29—C30—C31	110.52 (16)
C11—N10—H10A	118.3 (15)	N29—C30—H30A	106.8 (11)
N9—N10—H10A	122.6 (15)	C31—C30—H30A	110.8 (11)
N10—C11—C16	120.13 (15)	N29—C30—H30B	110.7 (12)
N10—C11—C12	123.81 (15)	C31—C30—H30B	110.0 (12)
C16—C11—C12	116.05 (15)	H30A—C30—H30B	108.0 (16)
C13—C12—C11	122.04 (15)	O32—C31—C30	111.64 (16)
C13—C12—N17	116.41 (14)	O32—C31—H31A	109.2 (13)
C11—C12—N17	121.54 (15)	C30—C31—H31A	109.2 (13)
C14—C13—C12	118.94 (15)	O32—C31—H31B	105.8 (12)
C14—C13—H13A	122.9 (11)	C30—C31—H31B	109.0 (13)
C12—C13—H13A	118.1 (11)	H31A—C31—H31B	112.1 (18)
C13—C14—C15	121.17 (15)	C33—O32—C31	108.87 (16)
C13—C14—N20	119.44 (15)	O32—C33—C34	112.06 (17)
C15—C14—N20	119.39 (15)	O32—C33—H33A	106.4 (15)
C16—C15—C14	119.94 (16)	C34—C33—H33A	108.4 (15)
C16—C15—H15A	119.7 (12)	O32—C33—H33B	111.4 (13)
C14—C15—H15A	120.4 (12)	C34—C33—H33B	109.2 (13)
C15—C16—C11	121.83 (15)	H33A—C33—H33B	109 (2)
C15—C16—H16A	121.4 (12)	N29—C34—C33	109.72 (17)
C11—C16—H16A	116.8 (12)	N29—C34—H34A	109.7 (14)
O19—N17—O18	122.64 (16)	C33—C34—H34A	110.3 (14)
O19—N17—C12	118.43 (16)	N29—C34—H34B	110.3 (12)
O18—N17—C12	118.90 (15)	C33—C34—H34B	108.1 (12)
O21—N20—O22	122.90 (16)	H34A—C34—H34B	108.7 (18)
O21—N20—C14	118.91 (16)	O36—N35—O37	122.36 (15)
O22—N20—C14	118.19 (15)	O36—N35—C5	118.72 (15)
C28—N23—C8	110.78 (14)	O37—N35—C5	118.91 (14)
C28—N23—C24	109.26 (14)
C5—N1—C2—N3	−1.9 (2)	C12—C11—C16—C15	0.8 (2)
C6—N1—C2—N3	−179.00 (15)	C13—C12—N17—O19	−11.7 (2)
N1—C2—N3—C4	0.8 (2)	C11—C12—N17—O19	169.18 (17)
C2—N3—C4—N29	−177.97 (15)	C13—C12—N17—O18	166.65 (17)
C2—N3—C4—C5	0.67 (18)	C11—C12—N17—O18	−12.4 (3)
C2—N1—C5—N35	−174.39 (15)	C13—C14—N20—O21	−1.7 (2)
C6—N1—C5—N35	2.4 (2)	C15—C14—N20—O21	177.81 (16)
C2—N1—C5—C4	2.16 (17)	C13—C14—N20—O22	178.69 (16)
C6—N1—C5—C4	178.97 (15)	C15—C14—N20—O22	−1.8 (2)
N3—C4—C5—N35	174.22 (16)	C7—C8—N23—C28	81.26 (17)
N29—C4—C5—N35	−7.3 (3)	C7—C8—N23—C24	−156.72 (15)
N3—C4—C5—N1	−1.78 (17)	C28—N23—C24—C25	−56.0 (2)
N29—C4—C5—N1	176.67 (16)	C8—N23—C24—C25	−178.92 (16)
C2—N1—C6—C7	−98.34 (19)	N23—C24—C25—O26	57.9 (2)
C5—N1—C6—C7	85.4 (2)	C24—C25—O26—C27	−59.3 (3)
N1—C6—C7—N9	171.61 (15)	C25—O26—C27—C28	59.9 (3)
N1—C6—C7—C8	−5.6 (2)	C8—N23—C28—C27	−179.45 (15)
N9—C7—C8—N23	−100.75 (17)	C24—N23—C28—C27	57.1 (2)
C6—C7—C8—N23	76.68 (19)	O26—C27—C28—N23	−59.6 (2)
C8—C7—N9—N10	177.17 (14)	N3—C4—N29—C30	2.6 (2)
C6—C7—N9—N10	−0.2 (2)	C5—C4—N29—C30	−175.67 (16)
C7—N9—N10—C11	−171.55 (14)	N3—C4—N29—C34	139.26 (17)
N9—N10—C11—C16	11.3 (2)	C5—C4—N29—C34	−39.0 (3)
N9—N10—C11—C12	−169.78 (14)	C4—N29—C30—C31	−169.12 (15)
N10—C11—C12—C13	179.44 (15)	C34—N29—C30—C31	51.4 (2)
C16—C11—C12—C13	−1.6 (2)	N29—C30—C31—O32	−56.2 (2)
N10—C11—C12—N17	−1.5 (2)	C30—C31—O32—C33	60.7 (2)
C16—C11—C12—N17	177.38 (14)	C31—O32—C33—C34	−61.4 (2)
C11—C12—C13—C14	1.4 (2)	C4—N29—C34—C33	170.89 (16)
N17—C12—C13—C14	−177.71 (14)	C30—N29—C34—C33	−51.4 (2)
C12—C13—C14—C15	−0.1 (2)	O32—C33—C34—N29	56.8 (2)
C12—C13—C14—N20	179.41 (14)	N1—C5—N35—O36	155.78 (15)
C13—C14—C15—C16	−0.7 (3)	C4—C5—N35—O36	−19.7 (3)
N20—C14—C15—C16	179.73 (15)	N1—C5—N35—O37	−24.7 (2)
C14—C15—C16—C11	0.4 (3)	C4—C5—N35—O37	159.78 (17)
N10—C11—C16—C15	179.73 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10A···O18	0.90 (2)	2.00 (2)	2.635 (2)	127 (2)
N10—H10A···O36^i	0.90 (2)	2.56 (2)	3.087 (2)	118.6 (18)
C15—H15A···O19^ii	0.98 (2)	2.54 (2)	3.305 (2)	134.9 (15)
C27—H27B···O22^iii	0.99 (3)	2.51 (3)	3.373 (3)	146 (2)
C34—H34A···O36	0.98 (2)	2.16 (2)	2.979 (3)	140.7 (19)
C6—H6B···O37	1.00 (2)	2.425 (19))	2.804 (2)	101.8 (13)
C13—H13A···O19	0.96 (2)	2.315 (18)	2.662 (2)	100.4 (13)
C16—H16A···N9	0.95 (2)	2.339 (19)	2.712 (2)	102.8 (14)

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

(Vb) (E)-1-(4-morpholino-5-nitroimidazol-1-yl)-3-morpholinopropan-2-one 2,4-dinitrophenylhydrazone tetrahydrofuran solvate

Crystal data

C20H25N9O8·C4H8O	F(000) = 1248
Mr = 591.59	Dx = 1.384 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 7.2885 (6) Å	Cell parameters from 48 reflections
b = 27.686 (2) Å	θ = 10.2–28.2°
c = 14.3642 (11) Å	µ = 0.91 mm^−1
β = 101.707 (8)°	T = 293 K
V = 2838.2 (4) Å^3	Prism, yellow
Z = 4	0.48 × 0.22 × 0.16 mm

Data collection

Kuma KM-4 diffractometer	Rint = 0.041
Radiation source: fine-focus sealed tube	θmax = 70.1°, θmin = 3.2°
Graphite monochromator	h = −8→8
ω/2θ scans	k = 0→33
5307 measured reflections	l = 0→17
5120 independent reflections	2 standard reflections every 100 reflections
3957 reflections with I > 2σ(I)	intensity decay: 2.3%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.154	w = 1/[σ^2(Fo^2) + (0.0886P)^2 + 0.7418P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
5120 reflections	Δρmax = 0.29 e Å^−3
480 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0018 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.1121 (2)	0.69548 (6)	1.08522 (12)	0.0499 (4)
C2	0.0221 (3)	0.68264 (9)	1.15328 (17)	0.0602 (5)
H2A	−0.106 (4)	0.6812 (9)	1.1404 (17)	0.066 (7)*
N3	0.1319 (3)	0.67271 (7)	1.23545 (13)	0.0591 (5)
C4	0.3087 (3)	0.67921 (7)	1.22124 (14)	0.0470 (4)
C5	0.3001 (3)	0.69378 (7)	1.12786 (14)	0.0460 (4)
C6	0.0212 (3)	0.70581 (8)	0.98759 (16)	0.0555 (5)
H6A	0.069 (4)	0.7365 (11)	0.9698 (18)	0.076 (8)*
H6B	−0.121 (4)	0.7073 (9)	0.9868 (18)	0.071 (7)*
C7	0.0499 (3)	0.66694 (7)	0.91831 (14)	0.0465 (4)
C8	−0.0201 (3)	0.67836 (9)	0.81489 (16)	0.0579 (5)
H8A	−0.140 (4)	0.6584 (9)	0.7918 (18)	0.070 (7)*
H8B	−0.044 (4)	0.7121 (10)	0.8058 (18)	0.071 (7)*
N9	0.1215 (2)	0.62758 (5)	0.95407 (11)	0.0463 (4)
N10	0.1480 (2)	0.59195 (6)	0.89081 (12)	0.0484 (4)
H10A	0.138 (4)	0.6023 (9)	0.8235 (19)	0.074 (7)*
C11	0.2004 (3)	0.54785 (6)	0.92643 (13)	0.0440 (4)
C12	0.2437 (3)	0.50920 (7)	0.86987 (14)	0.0504 (5)
C13	0.2854 (3)	0.46356 (7)	0.90715 (16)	0.0546 (5)
H13A	0.315 (4)	0.4364 (10)	0.8647 (18)	0.071 (7)*
C14	0.2896 (3)	0.45574 (7)	1.00123 (16)	0.0540 (5)
C15	0.2543 (3)	0.49279 (8)	1.06065 (16)	0.0539 (5)
H15A	0.259 (4)	0.4873 (9)	1.1247 (18)	0.066 (7)*
C16	0.2098 (3)	0.53765 (7)	1.02363 (15)	0.0498 (5)
H16A	0.188 (3)	0.5630 (8)	1.0628 (16)	0.052 (6)*
N17	0.2525 (3)	0.51526 (7)	0.77067 (13)	0.0656 (5)
O18	0.2275 (3)	0.55514 (6)	0.73499 (12)	0.0806 (5)
O19	0.2858 (4)	0.48048 (7)	0.72570 (15)	0.1124 (9)
N20	0.3347 (3)	0.40767 (7)	1.03980 (17)	0.0691 (5)
O21	0.3558 (4)	0.37516 (7)	0.98588 (17)	0.1009 (7)
O22	0.3472 (3)	0.40182 (7)	1.12488 (16)	0.0962 (7)
N23	0.1065 (2)	0.66360 (6)	0.75425 (11)	0.0498 (4)
C24	0.2820 (3)	0.69039 (9)	0.77605 (16)	0.0610 (6)
H24A	0.345 (4)	0.6829 (9)	0.8402 (19)	0.069 (7)*
H24B	0.259 (3)	0.7271 (9)	0.7716 (17)	0.065 (7)*
C25	0.4054 (4)	0.67636 (13)	0.70876 (19)	0.0752 (7)
H25A	0.508 (5)	0.6950 (11)	0.722 (2)	0.084 (9)*
H25B	0.428 (3)	0.6430 (10)	0.7146 (17)	0.060 (7)*
O26	0.3173 (3)	0.68507 (7)	0.61315 (12)	0.0783 (5)
C27	0.1506 (5)	0.65728 (11)	0.59126 (18)	0.0759 (7)
H27A	0.181 (4)	0.6235 (10)	0.5974 (18)	0.070 (7)*
H27B	0.094 (4)	0.6639 (11)	0.529 (2)	0.092 (9)*
C28	0.0181 (4)	0.67064 (10)	0.65387 (16)	0.0654 (6)
H28A	−0.015 (4)	0.7043 (12)	0.648 (2)	0.092 (9)*
H28B	−0.088 (4)	0.6518 (10)	0.6421 (19)	0.077 (8)*
N29	0.4603 (2)	0.67297 (6)	1.29370 (11)	0.0510 (4)
C30	0.4251 (4)	0.66881 (11)	1.38966 (16)	0.0619 (6)
H30A	0.376 (4)	0.6374 (10)	1.3960 (18)	0.071 (7)*
H30B	0.338 (4)	0.6923 (9)	1.3949 (17)	0.065 (7)*
C31	0.6037 (4)	0.67689 (15)	1.45917 (19)	0.0862 (9)
H31A	0.640 (5)	0.7126 (13)	1.451 (2)	0.102 (11)*
H31B	0.598 (4)	0.6712 (11)	1.530 (2)	0.096 (9)*
O32	0.7439 (3)	0.64355 (10)	1.44543 (13)	0.1021 (8)
C33	0.7824 (4)	0.64937 (15)	1.35289 (19)	0.0880 (10)
H33A	0.879 (4)	0.6236 (11)	1.342 (2)	0.086 (8)*
H33B	0.819 (5)	0.6877 (12)	1.341 (2)	0.102 (11)*
C34	0.6102 (3)	0.64076 (9)	1.27819 (17)	0.0611 (6)
H34A	0.631 (3)	0.6454 (9)	1.2142 (19)	0.066 (7)*
H34B	0.577 (4)	0.6052 (11)	1.281 (2)	0.090 (9)*
N35	0.4393 (2)	0.71253 (6)	1.08388 (12)	0.0493 (4)
O36	0.5983 (2)	0.71781 (6)	1.13290 (12)	0.0645 (4)
O37	0.3992 (2)	0.72388 (6)	0.99953 (11)	0.0641 (4)
O38	0.1803 (5)	0.49375 (11)	0.2749 (2)	0.1338 (10)
C39	0.2463 (9)	0.45782 (18)	0.3413 (4)	0.1502 (19)
H39A	0.3779	0.4516	0.3429	0.180*
H39B	0.1769	0.4281	0.3246	0.180*
C40	0.2215 (16)	0.4744 (3)	0.4300 (4)	0.232 (4)
H40A	0.3293	0.4664	0.4792	0.278*
H40B	0.1107	0.4601	0.4463	0.278*
C41	0.1998 (14)	0.5275 (3)	0.4192 (5)	0.206 (3)
H41A	0.0809	0.5379	0.4328	0.247*
H41B	0.3003	0.5442	0.4617	0.247*
C42	0.2072 (9)	0.53680 (18)	0.3225 (5)	0.154 (2)
H42A	0.1102	0.5596	0.2951	0.185*
H42B	0.3279	0.5504	0.3183	0.185*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0459 (9)	0.0503 (9)	0.0543 (9)	0.0052 (7)	0.0117 (7)	−0.0074 (7)
C2	0.0452 (13)	0.0716 (14)	0.0667 (14)	−0.0008 (10)	0.0179 (10)	−0.0081 (11)
N3	0.0493 (11)	0.0713 (11)	0.0614 (11)	−0.0024 (8)	0.0223 (8)	−0.0028 (8)
C4	0.0461 (11)	0.0444 (9)	0.0537 (11)	0.0018 (8)	0.0176 (8)	−0.0058 (8)
C5	0.0438 (11)	0.0438 (9)	0.0523 (10)	0.0021 (7)	0.0144 (8)	−0.0046 (8)
C6	0.0557 (14)	0.0501 (11)	0.0591 (12)	0.0128 (9)	0.0075 (9)	−0.0009 (9)
C7	0.0431 (10)	0.0439 (9)	0.0519 (10)	0.0020 (7)	0.0079 (8)	0.0018 (8)
C8	0.0572 (14)	0.0581 (13)	0.0561 (12)	0.0106 (10)	0.0066 (10)	0.0064 (10)
N9	0.0481 (9)	0.0420 (8)	0.0485 (8)	0.0028 (6)	0.0092 (7)	−0.0014 (6)
N10	0.0582 (10)	0.0407 (8)	0.0462 (9)	0.0051 (7)	0.0104 (7)	−0.0007 (6)
C11	0.0385 (10)	0.0416 (9)	0.0508 (10)	−0.0007 (7)	0.0066 (7)	0.0012 (7)
C12	0.0509 (11)	0.0454 (10)	0.0554 (11)	0.0017 (8)	0.0116 (9)	−0.0017 (8)
C13	0.0485 (12)	0.0457 (10)	0.0688 (13)	0.0034 (8)	0.0102 (9)	−0.0025 (9)
C14	0.0426 (11)	0.0439 (10)	0.0732 (14)	0.0023 (8)	0.0060 (9)	0.0093 (9)
C15	0.0486 (12)	0.0555 (11)	0.0555 (12)	0.0003 (9)	0.0056 (9)	0.0099 (9)
C16	0.0474 (11)	0.0480 (10)	0.0535 (11)	0.0025 (8)	0.0092 (8)	0.0010 (9)
N17	0.0861 (14)	0.0543 (10)	0.0601 (11)	0.0103 (9)	0.0239 (10)	−0.0034 (8)
O18	0.1287 (16)	0.0575 (9)	0.0612 (10)	0.0091 (10)	0.0326 (10)	0.0039 (7)
O19	0.194 (3)	0.0744 (12)	0.0812 (13)	0.0399 (14)	0.0562 (16)	−0.0084 (10)
N20	0.0621 (12)	0.0528 (11)	0.0886 (15)	0.0045 (9)	0.0060 (10)	0.0163 (10)
O21	0.1301 (19)	0.0478 (10)	0.1218 (17)	0.0204 (10)	0.0187 (14)	0.0039 (10)
O22	0.1158 (17)	0.0744 (12)	0.0950 (15)	0.0190 (11)	0.0134 (12)	0.0337 (11)
N23	0.0550 (10)	0.0470 (8)	0.0459 (9)	−0.0009 (7)	0.0069 (7)	0.0054 (7)
C24	0.0654 (15)	0.0602 (13)	0.0552 (12)	−0.0113 (10)	0.0066 (10)	0.0078 (10)
C25	0.0704 (17)	0.091 (2)	0.0653 (15)	−0.0112 (15)	0.0169 (12)	0.0172 (14)
O26	0.0855 (13)	0.0919 (12)	0.0607 (10)	−0.0145 (10)	0.0226 (9)	0.0175 (9)
C27	0.098 (2)	0.0811 (18)	0.0488 (13)	−0.0124 (15)	0.0145 (13)	0.0059 (12)
C28	0.0709 (16)	0.0701 (15)	0.0508 (12)	−0.0077 (12)	0.0018 (11)	0.0101 (10)
N29	0.0491 (10)	0.0591 (10)	0.0475 (9)	0.0087 (7)	0.0163 (7)	−0.0043 (7)
C30	0.0630 (15)	0.0759 (16)	0.0508 (12)	0.0070 (12)	0.0213 (10)	−0.0050 (11)
C31	0.0678 (17)	0.138 (3)	0.0531 (14)	0.0227 (17)	0.0133 (12)	−0.0179 (16)
O32	0.0830 (13)	0.166 (2)	0.0564 (10)	0.0498 (14)	0.0132 (9)	0.0063 (12)
C33	0.0656 (17)	0.140 (3)	0.0602 (15)	0.0383 (18)	0.0159 (12)	0.0001 (16)
C34	0.0664 (15)	0.0659 (14)	0.0554 (12)	0.0229 (11)	0.0228 (10)	0.0012 (10)
N35	0.0501 (10)	0.0445 (8)	0.0566 (10)	0.0006 (7)	0.0182 (8)	−0.0027 (7)
O36	0.0452 (9)	0.0729 (10)	0.0777 (10)	−0.0012 (7)	0.0177 (7)	0.0041 (8)
O37	0.0783 (11)	0.0627 (9)	0.0546 (9)	−0.0101 (7)	0.0210 (8)	0.0021 (7)
O38	0.194 (3)	0.108 (2)	0.1058 (18)	−0.0040 (19)	0.045 (2)	0.0038 (16)
C39	0.206 (6)	0.108 (3)	0.139 (4)	0.021 (3)	0.043 (4)	0.015 (3)
C40	0.389 (14)	0.180 (7)	0.112 (4)	−0.050 (7)	0.017 (6)	0.027 (4)
C41	0.320 (11)	0.164 (6)	0.134 (5)	−0.022 (6)	0.046 (6)	−0.039 (4)
C42	0.202 (6)	0.101 (3)	0.174 (5)	−0.038 (3)	0.069 (4)	−0.018 (3)

Geometric parameters (Å, º)

N1—C2	1.331 (3)	C24—H24B	1.03 (3)
N1—C5	1.384 (3)	C25—O26	1.414 (3)
N1—C6	1.453 (3)	C25—H25A	0.90 (3)
C2—N3	1.314 (3)	C25—H25B	0.94 (3)
C2—H2A	0.91 (3)	O26—C27	1.419 (4)
N3—C4	1.357 (3)	C27—C28	1.493 (4)
C4—N29	1.367 (3)	C27—H27A	0.96 (3)
C4—C5	1.390 (3)	C27—H27B	0.92 (3)
C5—N35	1.399 (3)	C28—H28A	0.96 (3)
C6—C7	1.509 (3)	C28—H28B	0.92 (3)
C6—H6A	0.97 (3)	N29—C30	1.457 (3)
C6—H6B	1.04 (3)	N29—C34	1.462 (3)
C7—N9	1.271 (2)	C30—C31	1.488 (4)
C7—C8	1.503 (3)	C30—H30A	0.95 (3)
C8—N23	1.450 (3)	C30—H30B	0.92 (3)
C8—H8A	1.03 (3)	C31—O32	1.420 (4)
C8—H8B	0.95 (3)	C31—H31A	1.04 (3)
N9—N10	1.381 (2)	C31—H31B	1.03 (3)
N10—C11	1.349 (2)	O32—C33	1.422 (3)
N10—H10A	1.00 (3)	C33—C34	1.496 (4)
C11—C16	1.413 (3)	C33—H33A	1.03 (3)
C11—C12	1.417 (3)	C33—H33B	1.12 (3)
C12—C13	1.382 (3)	C34—H34A	0.97 (3)
C12—N17	1.449 (3)	C34—H34B	1.02 (3)
C13—C14	1.363 (3)	N35—O37	1.228 (2)
C13—H13A	1.02 (3)	N35—O36	1.237 (2)
C14—C15	1.391 (3)	O38—C42	1.369 (5)
C14—N20	1.453 (3)	O38—C39	1.395 (5)
C15—C16	1.364 (3)	C39—C40	1.400 (9)
C15—H15A	0.93 (2)	C39—H39A	0.9700
C16—H16A	0.93 (2)	C39—H39B	0.9700
N17—O19	1.211 (2)	C40—C41	1.484 (10)
N17—O18	1.215 (2)	C40—H40A	0.9700
N20—O21	1.217 (3)	C40—H40B	0.9700
N20—O22	1.218 (3)	C41—C42	1.423 (8)
N23—C24	1.457 (3)	C41—H41A	0.9700
N23—C28	1.468 (3)	C41—H41B	0.9700
C24—C25	1.499 (4)	C42—H42A	0.9700
C24—H24A	0.97 (3)	C42—H42B	0.9700
C2—N1—C5	104.89 (18)	H25A—C25—H25B	115 (3)
C2—N1—C6	124.4 (2)	C25—O26—C27	108.8 (2)
C5—N1—C6	130.59 (18)	O26—C27—C28	111.2 (2)
N3—C2—N1	114.5 (2)	O26—C27—H27A	109.7 (16)
N3—C2—H2A	125.7 (16)	C28—C27—H27A	110.6 (16)
N1—C2—H2A	119.8 (16)	O26—C27—H27B	108 (2)
C2—N3—C4	105.13 (18)	C28—C27—H27B	108 (2)
N3—C4—N29	120.97 (18)	H27A—C27—H27B	110 (2)
N3—C4—C5	109.00 (18)	N23—C28—C27	110.5 (2)
N29—C4—C5	129.98 (19)	N23—C28—H28A	105.6 (18)
N1—C5—C4	106.46 (17)	C27—C28—H28A	111.7 (18)
N1—C5—N35	122.09 (17)	N23—C28—H28B	106.8 (17)
C4—C5—N35	130.45 (18)	C27—C28—H28B	111.8 (17)
N1—C6—C7	113.54 (16)	H28A—C28—H28B	110 (3)
N1—C6—H6A	107.9 (16)	C4—N29—C30	117.38 (18)
C7—C6—H6A	110.2 (15)	C4—N29—C34	118.36 (17)
N1—C6—H6B	106.1 (14)	C30—N29—C34	112.13 (18)
C7—C6—H6B	107.1 (14)	N29—C30—C31	109.0 (2)
H6A—C6—H6B	112 (2)	N29—C30—H30A	107.8 (16)
N9—C7—C8	127.52 (18)	C31—C30—H30A	111.7 (16)
N9—C7—C6	116.46 (18)	N29—C30—H30B	106.1 (15)
C8—C7—C6	115.92 (17)	C31—C30—H30B	111.2 (16)
N23—C8—C7	113.86 (18)	H30A—C30—H30B	111 (2)
N23—C8—H8A	104.8 (14)	O32—C31—C30	111.4 (2)
C7—C8—H8A	107.5 (14)	O32—C31—H31A	113 (2)
N23—C8—H8B	108.3 (16)	C30—C31—H31A	105.9 (19)
C7—C8—H8B	110.9 (16)	O32—C31—H31B	102.1 (18)
H8A—C8—H8B	111 (2)	C30—C31—H31B	115.5 (19)
C7—N9—N10	116.58 (16)	H31A—C31—H31B	109 (2)
C11—N10—N9	117.62 (16)	C31—O32—C33	109.9 (2)
C11—N10—H10A	126.0 (15)	O32—C33—C34	110.9 (2)
N9—N10—H10A	116.1 (15)	O32—C33—H33A	109.0 (16)
N10—C11—C16	120.60 (17)	C34—C33—H33A	106.4 (17)
N10—C11—C12	123.02 (17)	O32—C33—H33B	110.6 (18)
C16—C11—C12	116.36 (17)	C34—C33—H33B	103.3 (18)
C13—C12—C11	121.70 (19)	H33A—C33—H33B	116 (3)
C13—C12—N17	115.88 (18)	N29—C34—C33	109.7 (2)
C11—C12—N17	122.39 (17)	N29—C34—H34A	109.1 (15)
C14—C13—C12	119.2 (2)	C33—C34—H34A	113.1 (15)
C14—C13—H13A	120.7 (15)	N29—C34—H34B	113.2 (18)
C12—C13—H13A	120.1 (15)	C33—C34—H34B	107.4 (17)
C13—C14—C15	121.43 (19)	H34A—C34—H34B	104 (2)
C13—C14—N20	118.8 (2)	O37—N35—O36	122.66 (17)
C15—C14—N20	119.8 (2)	O37—N35—C5	119.40 (18)
C16—C15—C14	119.4 (2)	O36—N35—C5	117.93 (17)
C16—C15—H15A	119.7 (15)	C42—O38—C39	106.5 (4)
C14—C15—H15A	120.9 (15)	O38—C39—C40	107.4 (5)
C15—C16—C11	121.8 (2)	O38—C39—H39A	110.2
C15—C16—H16A	120.4 (13)	C40—C39—H39A	110.2
C11—C16—H16A	117.8 (13)	O38—C39—H39B	110.2
O19—N17—O18	121.8 (2)	C40—C39—H39B	110.2
O19—N17—C12	119.09 (19)	H39A—C39—H39B	108.5
O18—N17—C12	119.14 (17)	C39—C40—C41	105.1 (5)
O21—N20—O22	123.1 (2)	C39—C40—H40A	110.7
O21—N20—C14	118.8 (2)	C41—C40—H40A	110.7
O22—N20—C14	118.0 (2)	C39—C40—H40B	110.7
C8—N23—C24	111.44 (18)	C41—C40—H40B	110.7
C8—N23—C28	110.28 (18)	H40A—C40—H40B	108.8
C24—N23—C28	109.55 (17)	C42—C41—C40	104.9 (5)
N23—C24—C25	110.2 (2)	C42—C41—H41A	110.8
N23—C24—H24A	108.7 (16)	C40—C41—H41A	110.8
C25—C24—H24A	109.3 (16)	C42—C41—H41B	110.8
N23—C24—H24B	111.5 (14)	C40—C41—H41B	110.8
C25—C24—H24B	109.1 (14)	H41A—C41—H41B	108.8
H24A—C24—H24B	108 (2)	O38—C42—C41	107.5 (4)
O26—C25—C24	111.6 (2)	O38—C42—H42A	110.2
O26—C25—H25A	107.9 (19)	C41—C42—H42A	110.2
C24—C25—H25A	107 (2)	O38—C42—H42B	110.2
O26—C25—H25B	106.9 (15)	C41—C42—H42B	110.2
C24—C25—H25B	108.3 (15)	H42A—C42—H42B	108.5
C5—N1—C2—N3	−0.1 (3)	C11—C12—N17—O19	−178.2 (3)
C6—N1—C2—N3	176.86 (19)	C13—C12—N17—O18	−176.0 (2)
N1—C2—N3—C4	−0.3 (3)	C11—C12—N17—O18	2.2 (3)
C2—N3—C4—N29	178.49 (19)	C13—C14—N20—O21	−4.6 (3)
C2—N3—C4—C5	0.5 (2)	C15—C14—N20—O21	176.4 (2)
C2—N1—C5—C4	0.4 (2)	C13—C14—N20—O22	176.3 (2)
C6—N1—C5—C4	−176.28 (18)	C15—C14—N20—O22	−2.8 (3)
C2—N1—C5—N35	−169.24 (18)	C7—C8—N23—C24	−65.0 (2)
C6—N1—C5—N35	14.1 (3)	C7—C8—N23—C28	173.15 (19)
N3—C4—C5—N1	−0.6 (2)	C8—N23—C24—C25	−176.84 (19)
N29—C4—C5—N1	−178.32 (18)	C28—N23—C24—C25	−54.5 (3)
N3—C4—C5—N35	167.88 (19)	N23—C24—C25—O26	58.6 (3)
N29—C4—C5—N35	−9.8 (3)	C24—C25—O26—C27	−60.4 (3)
C2—N1—C6—C7	−107.1 (2)	C25—O26—C27—C28	60.3 (3)
C5—N1—C6—C7	69.0 (3)	C8—N23—C28—C27	177.8 (2)
N1—C6—C7—N9	10.8 (3)	C24—N23—C28—C27	54.8 (3)
N1—C6—C7—C8	−172.62 (19)	O26—C27—C28—N23	−58.4 (3)
N9—C7—C8—N23	−45.9 (3)	N3—C4—N29—C30	−12.1 (3)
C6—C7—C8—N23	137.9 (2)	C5—C4—N29—C30	165.4 (2)
C8—C7—N9—N10	3.9 (3)	N3—C4—N29—C34	127.5 (2)
C6—C7—N9—N10	−179.97 (17)	C5—C4—N29—C34	−55.0 (3)
C7—N9—N10—C11	−171.47 (18)	C4—N29—C30—C31	−163.4 (2)
N9—N10—C11—C16	6.0 (3)	C34—N29—C30—C31	54.6 (3)
N9—N10—C11—C12	−175.82 (17)	N29—C30—C31—O32	−57.8 (4)
N10—C11—C12—C13	−175.83 (19)	C30—C31—O32—C33	61.1 (4)
C16—C11—C12—C13	2.4 (3)	C31—O32—C33—C34	−59.9 (4)
N10—C11—C12—N17	6.1 (3)	C4—N29—C34—C33	164.2 (2)
C16—C11—C12—N17	−175.6 (2)	C30—N29—C34—C33	−54.2 (3)
C11—C12—C13—C14	−1.6 (3)	O32—C33—C34—N29	56.2 (3)
N17—C12—C13—C14	176.6 (2)	N1—C5—N35—O37	−11.9 (3)
C12—C13—C14—C15	−0.6 (3)	C4—C5—N35—O37	−178.79 (19)
C12—C13—C14—N20	−179.67 (19)	N1—C5—N35—O36	166.79 (17)
C13—C14—C15—C16	1.8 (3)	C4—C5—N35—O36	−0.1 (3)
N20—C14—C15—C16	−179.17 (19)	C42—O38—C39—C40	29.8 (7)
C14—C15—C16—C11	−0.8 (3)	O38—C39—C40—C41	−19.1 (9)
N10—C11—C16—C15	177.07 (19)	C39—C40—C41—C42	2.1 (10)
C12—C11—C16—C15	−1.2 (3)	C39—O38—C42—C41	−28.2 (7)
C13—C12—N17—O19	3.6 (4)	C40—C41—C42—O38	15.9 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10A···O18	1.00 (3)	2.02 (3)	2.629 (2)	117.1 (19)
N10—H10A···N23	1.00 (3)	1.96 (3)	2.763 (2)	136 (2)
C2—H2A···O36^i	0.91 (3)	2.37 (3)	3.195 (3)	151 (2)
C15—H15A···O38^ii	0.93 (2)	2.35 (3)	3.230 (4)	159 (2)
C24—H24A···O37	0.97 (3)	2.51 (3)	3.284 (3)	136.8 (19)
C34—H34A···O36	0.97 (3)	2.31 (3)	2.973 (3)	125.1 (19)
C34—H34B···O19^iii	1.02 (3)	2.58 (3)	3.444 (3)	142 (2)
C6—H6A···O37	0.97 (3)	2.38 (3)	2.771 (3)	103.2 (19)
C16—H16A···N9	0.93 (2)	2.36 (2)	2.711 (2)	102.0 (15)

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