4-{[2-(2,4-Dinitro-phen-yl)hydrazinyl-idene](phen-yl)meth-yl}-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one ethanol monosolvate.

In the title compound, C23H18N6O5·C2H6O, all three benzene rings lie in an approximate plane [maximum deviation = 0.2688 (16) Å] that makes an angle of 53.56 (3)° with the plane of the pyrazolone ring. Intra-molecular N-H⋯O hydrogen bonds occur. In the crystal, the ethanol solvent mol-ecule links adjacent mol-ecules through N-H⋯O-H⋯O hydrogen bonds, leading to an infinite chain along the c-axis direction. The ethyl group of the ethanol solvent mol-ecule is disordered over two set of sites in a 0.762 (5):0.238 (5) ratio.

Related literature

For a related structure, see: Idemudia et al. (2012 ▶).

Experimental

Crystal data

C23H18N6O5·C2H6O

M = 504.50

Monoclinic,

a = 12.8289 (4) Å

b = 14.3247 (4) Å

c = 14.4213 (4) Å

β = 111.347 (1)°

V = 2468.38 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.61 × 0.43 × 0.39 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: numerical (SADABS; Bruker, 2008 ▶) T min = 0.89, T max = 0.96

23873 measured reflections

6124 independent reflections

5136 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.04

6124 reflections

368 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and SHELXLE (Hübschle et al., 2011 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044935/ng5294sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044935/ng5294Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044935/ng5294Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044935/ng5294Isup4.cml

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

C23H18N6O5·C2H6O	Dx = 1.358 Mg m−3
Mr = 504.50	Melting point: 507 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.8289 (4) Å	Cell parameters from 94 reflections
b = 14.3247 (4) Å	θ = 2.9–28.9°
c = 14.4213 (4) Å	µ = 0.10 mm−1
β = 111.347 (1)°	T = 200 K
V = 2468.38 (12) Å3	Block, red
Z = 4	0.61 × 0.43 × 0.39 mm
F(000) = 1056

Bruker APEXII CCD diffractometer	6124 independent reflections
Graphite monochromator	5136 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm-1	Rint = 0.014
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: numerical (SADABS; Bruker, 2008)	h = −16→17
Tmin = 0.89, Tmax = 0.96	k = −13→19
23873 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.8241P] where P = (Fo2 + 2Fc2)/3
6124 reflections	(Δ/σ)max < 0.001
368 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.14776 (8)	0.69594 (6)	0.47229 (6)	0.0383 (2)
O2	−0.07049 (9)	0.77842 (7)	0.42852 (9)	0.0543 (3)
O3	−0.22537 (11)	0.83873 (7)	0.42516 (10)	0.0588 (3)
O4	−0.53149 (10)	0.65498 (10)	0.42226 (12)	0.0730 (4)
O5	−0.53782 (10)	0.50904 (11)	0.38432 (14)	0.0876 (5)
O6	0.30397 (9)	0.73560 (9)	0.64059 (8)	0.0517 (3)
N1	0.20431 (9)	0.73686 (7)	0.34187 (7)	0.0317 (2)
N2	0.20240 (9)	0.69518 (7)	0.25557 (8)	0.0341 (2)
N3	−0.01147 (8)	0.51321 (7)	0.38324 (8)	0.0325 (2)
N4	−0.05711 (9)	0.59824 (7)	0.39281 (8)	0.0328 (2)
N5	−0.16820 (10)	0.77102 (7)	0.42199 (8)	0.0399 (2)
N6	−0.48924 (10)	0.58418 (10)	0.40330 (11)	0.0553 (3)
C1	0.15772 (9)	0.67707 (8)	0.39078 (8)	0.0299 (2)
C2	0.12604 (9)	0.59567 (8)	0.33014 (8)	0.0294 (2)
C3	0.15677 (10)	0.61039 (8)	0.24838 (9)	0.0321 (2)
C4	0.14119 (14)	0.55220 (10)	0.15841 (10)	0.0466 (3)
H4A	0.1162	0.5919	0.099	0.07*
H4B	0.0848	0.504	0.1522	0.07*
H4C	0.2123	0.5225	0.1649	0.07*
C5	0.07256 (9)	0.51282 (8)	0.35381 (8)	0.0292 (2)
C11	0.24261 (10)	0.82994 (8)	0.36714 (9)	0.0322 (2)
C12	0.17815 (12)	0.89102 (9)	0.39821 (11)	0.0424 (3)
H12	0.1083	0.8716	0.4005	0.051*
C13	0.21730 (15)	0.98106 (10)	0.42595 (12)	0.0514 (4)
H13	0.1746	1.0234	0.4484	0.062*
C14	0.31808 (15)	1.00912 (10)	0.42101 (12)	0.0532 (4)
H14	0.3447	1.0706	0.4406	0.064*
C15	0.38033 (14)	0.94861 (11)	0.38782 (12)	0.0520 (4)
H15	0.4485	0.9691	0.3828	0.062*
C16	0.34373 (11)	0.85755 (9)	0.36157 (10)	0.0410 (3)
H16	0.3873	0.8151	0.3402	0.049*
C21	0.11659 (10)	0.41870 (8)	0.34431 (8)	0.0304 (2)
C22	0.05139 (11)	0.33871 (9)	0.33661 (10)	0.0375 (3)
H22	−0.0221	0.3442	0.3374	0.045*
C23	0.09362 (13)	0.25170 (9)	0.32782 (11)	0.0453 (3)
H23	0.0489	0.1977	0.3227	0.054*
C24	0.20034 (13)	0.24258 (10)	0.32641 (10)	0.0461 (3)
H24	0.2282	0.1827	0.3189	0.055*
C25	0.26619 (12)	0.32073 (10)	0.33591 (11)	0.0455 (3)
H25	0.34	0.3147	0.3361	0.055*
C26	0.22459 (11)	0.40835 (9)	0.34526 (10)	0.0379 (3)
H26	0.2706	0.4618	0.3524	0.045*
C31	−0.16063 (10)	0.59744 (8)	0.39772 (8)	0.0302 (2)
C32	−0.21772 (10)	0.67863 (8)	0.41052 (9)	0.0322 (2)
C33	−0.32476 (11)	0.67409 (9)	0.41267 (9)	0.0364 (3)
H33	−0.3614	0.7291	0.4215	0.044*
C34	−0.37698 (10)	0.58920 (10)	0.40188 (10)	0.0393 (3)
C35	−0.32465 (11)	0.50752 (10)	0.38895 (11)	0.0422 (3)
H35	−0.3622	0.4493	0.3817	0.051*
C36	−0.21948 (11)	0.51165 (9)	0.38672 (10)	0.0378 (3)
H36	−0.1846	0.4557	0.3776	0.045*
H2N	0.2371 (14)	0.7212 (12)	0.2146 (13)	0.054 (5)*
H4N	−0.0119 (14)	0.6495 (12)	0.4120 (12)	0.050 (4)*
H6	0.2561 (18)	0.7277 (14)	0.5787 (17)	0.072 (6)*
C6A	0.41626 (18)	0.74427 (15)	0.64338 (17)	0.0497 (6)	0.762 (5)
H6AA	0.4222	0.7136	0.584	0.06*	0.762 (5)
H6AB	0.4678	0.7119	0.7031	0.06*	0.762 (5)
C7A	0.4500 (3)	0.8432 (2)	0.64576 (19)	0.0669 (9)	0.762 (5)
H7AA	0.4044	0.8737	0.5833	0.1*	0.762 (5)
H7AB	0.5292	0.8467	0.6539	0.1*	0.762 (5)
H7AC	0.4389	0.8749	0.7017	0.1*	0.762 (5)
C6B	0.3762 (6)	0.8194 (5)	0.6360 (5)	0.053 (2)	0.238 (5)
H6BA	0.3433	0.8529	0.5719	0.064*	0.238 (5)
H6BB	0.3852	0.8636	0.6913	0.064*	0.238 (5)
C7B	0.4832 (8)	0.7761 (8)	0.6459 (10)	0.091 (4)	0.238 (5)
H7BA	0.4727	0.7356	0.5885	0.136*	0.238 (5)
H7BB	0.5105	0.7389	0.7071	0.136*	0.238 (5)
H7BC	0.5379	0.8248	0.6488	0.136*	0.238 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0441 (5)	0.0430 (5)	0.0328 (4)	−0.0148 (4)	0.0199 (4)	−0.0091 (4)
O2	0.0559 (6)	0.0345 (5)	0.0824 (8)	−0.0116 (4)	0.0368 (6)	−0.0076 (5)
O3	0.0760 (8)	0.0300 (5)	0.0843 (8)	0.0055 (5)	0.0457 (7)	−0.0046 (5)
O4	0.0488 (6)	0.0734 (8)	0.1089 (11)	0.0175 (6)	0.0432 (7)	0.0078 (8)
O5	0.0437 (7)	0.0796 (10)	0.1479 (15)	−0.0183 (6)	0.0448 (8)	−0.0171 (9)
O6	0.0405 (5)	0.0805 (8)	0.0385 (5)	−0.0101 (5)	0.0197 (4)	−0.0182 (5)
N1	0.0401 (5)	0.0269 (5)	0.0327 (5)	−0.0068 (4)	0.0186 (4)	−0.0038 (4)
N2	0.0466 (6)	0.0290 (5)	0.0335 (5)	−0.0046 (4)	0.0229 (4)	−0.0024 (4)
N3	0.0329 (5)	0.0267 (5)	0.0399 (5)	−0.0011 (4)	0.0154 (4)	−0.0001 (4)
N4	0.0347 (5)	0.0252 (5)	0.0423 (5)	−0.0032 (4)	0.0185 (4)	−0.0012 (4)
N5	0.0526 (7)	0.0289 (5)	0.0443 (6)	−0.0025 (5)	0.0249 (5)	−0.0027 (4)
N6	0.0333 (6)	0.0630 (9)	0.0725 (9)	0.0017 (6)	0.0227 (6)	0.0030 (7)
C1	0.0308 (5)	0.0297 (5)	0.0305 (5)	−0.0050 (4)	0.0129 (4)	−0.0017 (4)
C2	0.0323 (5)	0.0259 (5)	0.0314 (5)	−0.0024 (4)	0.0134 (4)	−0.0012 (4)
C3	0.0383 (6)	0.0267 (5)	0.0338 (6)	−0.0006 (4)	0.0162 (5)	−0.0015 (4)
C4	0.0689 (9)	0.0375 (7)	0.0414 (7)	−0.0057 (6)	0.0297 (7)	−0.0093 (5)
C5	0.0296 (5)	0.0269 (5)	0.0302 (5)	−0.0041 (4)	0.0098 (4)	−0.0006 (4)
C11	0.0394 (6)	0.0254 (5)	0.0311 (5)	−0.0054 (4)	0.0119 (5)	−0.0003 (4)
C12	0.0466 (7)	0.0338 (6)	0.0478 (7)	−0.0022 (5)	0.0182 (6)	−0.0054 (5)
C13	0.0679 (10)	0.0303 (7)	0.0527 (8)	0.0016 (6)	0.0181 (7)	−0.0058 (6)
C14	0.0717 (10)	0.0267 (6)	0.0499 (8)	−0.0124 (6)	0.0089 (7)	0.0011 (6)
C15	0.0540 (8)	0.0406 (8)	0.0571 (9)	−0.0187 (7)	0.0151 (7)	0.0049 (6)
C16	0.0425 (7)	0.0354 (6)	0.0466 (7)	−0.0072 (5)	0.0181 (6)	0.0018 (5)
C21	0.0328 (6)	0.0273 (5)	0.0298 (5)	−0.0020 (4)	0.0098 (4)	−0.0001 (4)
C22	0.0366 (6)	0.0318 (6)	0.0414 (6)	−0.0067 (5)	0.0108 (5)	−0.0041 (5)
C23	0.0542 (8)	0.0294 (6)	0.0461 (7)	−0.0078 (6)	0.0110 (6)	−0.0064 (5)
C24	0.0596 (9)	0.0319 (6)	0.0423 (7)	0.0098 (6)	0.0132 (6)	−0.0015 (5)
C25	0.0431 (7)	0.0435 (7)	0.0509 (8)	0.0108 (6)	0.0184 (6)	0.0043 (6)
C26	0.0348 (6)	0.0330 (6)	0.0465 (7)	−0.0002 (5)	0.0155 (5)	0.0034 (5)
C31	0.0317 (5)	0.0293 (5)	0.0306 (5)	−0.0022 (4)	0.0124 (4)	−0.0004 (4)
C32	0.0384 (6)	0.0280 (6)	0.0317 (5)	−0.0011 (5)	0.0145 (5)	−0.0002 (4)
C33	0.0375 (6)	0.0374 (6)	0.0354 (6)	0.0061 (5)	0.0147 (5)	0.0016 (5)
C34	0.0284 (6)	0.0458 (7)	0.0442 (7)	0.0004 (5)	0.0137 (5)	0.0007 (5)
C35	0.0341 (6)	0.0367 (7)	0.0555 (8)	−0.0072 (5)	0.0159 (6)	−0.0049 (6)
C36	0.0342 (6)	0.0295 (6)	0.0511 (7)	−0.0033 (5)	0.0172 (5)	−0.0050 (5)
C6A	0.0436 (12)	0.0495 (12)	0.0643 (13)	−0.0020 (9)	0.0296 (9)	−0.0051 (9)
C7A	0.072 (2)	0.0563 (16)	0.0620 (14)	−0.0192 (13)	0.0121 (12)	0.0037 (11)
C6B	0.044 (4)	0.060 (5)	0.049 (4)	−0.006 (3)	0.008 (3)	0.001 (3)
C7B	0.052 (5)	0.074 (7)	0.150 (10)	0.005 (4)	0.041 (6)	0.025 (6)

O1—C1	1.2572 (14)	C15—C16	1.3913 (19)
O2—N5	1.2270 (15)	C15—H15	0.95
O3—N5	1.2269 (15)	C16—H16	0.95
O4—N6	1.2268 (18)	C21—C26	1.3886 (17)
O5—N6	1.2238 (19)	C21—C22	1.3991 (16)
O6—C6A	1.432 (2)	C22—C23	1.3831 (19)
O6—C6B	1.533 (8)	C22—H22	0.95
O6—H6	0.89 (2)	C23—C24	1.383 (2)
N1—N2	1.3725 (13)	C23—H23	0.95
N1—C1	1.3767 (14)	C24—C25	1.379 (2)
N1—C11	1.4218 (14)	C24—H24	0.95
N2—C3	1.3358 (15)	C25—C26	1.3895 (18)
N2—H2N	0.936 (18)	C25—H25	0.95
N3—C5	1.2942 (15)	C26—H26	0.95
N3—N4	1.3801 (14)	C31—C36	1.4206 (16)
N4—C31	1.3554 (15)	C31—C32	1.4219 (16)
N4—H4N	0.915 (17)	C32—C33	1.3864 (17)
N5—C32	1.4512 (15)	C33—C34	1.3696 (19)
N6—C34	1.4496 (17)	C33—H33	0.95
C1—C2	1.4251 (15)	C34—C35	1.3948 (19)
C2—C3	1.3888 (16)	C35—C36	1.3626 (18)
C2—C5	1.4718 (15)	C35—H35	0.95
C3—C4	1.4931 (17)	C36—H36	0.95
C4—H4A	0.98	C6A—C7A	1.479 (3)
C4—H4B	0.98	C6A—H6AA	0.99
C4—H4C	0.98	C6A—H6AB	0.99
C5—C21	1.4873 (16)	C7A—H7AA	0.98
C11—C12	1.3856 (18)	C7A—H7AB	0.98
C11—C16	1.3863 (18)	C7A—H7AC	0.98
C12—C13	1.3891 (19)	C6B—C7B	1.466 (13)
C12—H12	0.95	C6B—H6BA	0.99
C13—C14	1.380 (2)	C6B—H6BB	0.99
C13—H13	0.95	C7B—H7BA	0.98
C14—C15	1.377 (2)	C7B—H7BB	0.98
C14—H14	0.95	C7B—H7BC	0.98
C6A—O6—H6	111.1 (13)	C26—C21—C22	118.61 (11)
C6B—O6—H6	105.4 (13)	C26—C21—C5	120.47 (10)
N2—N1—C1	109.04 (9)	C22—C21—C5	120.91 (11)
N2—N1—C11	122.07 (9)	C23—C22—C21	120.16 (12)
C1—N1—C11	128.75 (10)	C23—C22—H22	119.9
C3—N2—N1	109.19 (9)	C21—C22—H22	119.9
C3—N2—H2N	127.5 (11)	C24—C23—C22	120.63 (13)
N1—N2—H2N	122.9 (11)	C24—C23—H23	119.7
C5—N3—N4	118.09 (10)	C22—C23—H23	119.7
C31—N4—N3	117.20 (10)	C25—C24—C23	119.72 (13)
C31—N4—H4N	121.1 (10)	C25—C24—H24	120.1
N3—N4—H4N	119.6 (10)	C23—C24—H24	120.1
O3—N5—O2	122.46 (11)	C24—C25—C26	120.00 (13)
O3—N5—C32	118.84 (11)	C24—C25—H25	120.0
O2—N5—C32	118.70 (10)	C26—C25—H25	120.0
O5—N6—O4	123.14 (13)	C21—C26—C25	120.84 (12)
O5—N6—C34	117.91 (13)	C21—C26—H26	119.6
O4—N6—C34	118.95 (13)	C25—C26—H26	119.6
O1—C1—N1	123.79 (10)	N4—C31—C36	119.51 (11)
O1—C1—C2	130.26 (10)	N4—C31—C32	124.10 (10)
N1—C1—C2	105.94 (9)	C36—C31—C32	116.37 (10)
C3—C2—C1	106.92 (10)	C33—C32—C31	121.72 (11)
C3—C2—C5	128.31 (10)	C33—C32—N5	115.87 (11)
C1—C2—C5	124.77 (10)	C31—C32—N5	122.41 (11)
N2—C3—C2	108.91 (10)	C34—C33—C32	119.12 (11)
N2—C3—C4	119.43 (11)	C34—C33—H33	120.4
C2—C3—C4	131.56 (11)	C32—C33—H33	120.4
C3—C4—H4A	109.5	C33—C34—C35	121.37 (11)
C3—C4—H4B	109.5	C33—C34—N6	119.33 (12)
H4A—C4—H4B	109.5	C35—C34—N6	119.30 (12)
C3—C4—H4C	109.5	C36—C35—C34	119.71 (12)
H4A—C4—H4C	109.5	C36—C35—H35	120.1
H4B—C4—H4C	109.5	C34—C35—H35	120.1
N3—C5—C2	125.94 (10)	C35—C36—C31	121.70 (12)
N3—C5—C21	115.07 (10)	C35—C36—H36	119.1
C2—C5—C21	119.00 (10)	C31—C36—H36	119.1
C12—C11—C16	121.32 (12)	O6—C6A—C7A	111.5 (2)
C12—C11—N1	118.94 (11)	O6—C6A—H6AA	109.3
C16—C11—N1	119.74 (11)	C7A—C6A—H6AA	109.3
C11—C12—C13	118.93 (13)	O6—C6A—H6AB	109.3
C11—C12—H12	120.5	C7A—C6A—H6AB	109.3
C13—C12—H12	120.5	H6AA—C6A—H6AB	108.0
C14—C13—C12	120.18 (14)	C7B—C6B—O6	102.9 (6)
C14—C13—H13	119.9	C7B—C6B—H6BA	111.2
C12—C13—H13	119.9	O6—C6B—H6BA	111.2
C15—C14—C13	120.48 (13)	C7B—C6B—H6BB	111.2
C15—C14—H14	119.8	O6—C6B—H6BB	111.2
C13—C14—H14	119.8	H6BA—C6B—H6BB	109.1
C14—C15—C16	120.25 (14)	C6B—C7B—H7BA	109.5
C14—C15—H15	119.9	C6B—C7B—H7BB	109.5
C16—C15—H15	119.9	H7BA—C7B—H7BB	109.5
C11—C16—C15	118.82 (13)	C6B—C7B—H7BC	109.5
C11—C16—H16	120.6	H7BA—C7B—H7BC	109.5
C15—C16—H16	120.6	H7BB—C7B—H7BC	109.5
C1—N1—N2—C3	−0.45 (14)	N3—C5—C21—C26	−159.14 (11)
C11—N1—N2—C3	−176.44 (11)	C2—C5—C21—C26	20.72 (16)
C5—N3—N4—C31	163.07 (11)	N3—C5—C21—C22	19.34 (16)
N2—N1—C1—O1	−179.97 (11)	C2—C5—C21—C22	−160.80 (11)
C11—N1—C1—O1	−4.3 (2)	C26—C21—C22—C23	−1.49 (19)
N2—N1—C1—C2	−0.23 (13)	C5—C21—C22—C23	180.00 (12)
C11—N1—C1—C2	175.41 (11)	C21—C22—C23—C24	−0.1 (2)
O1—C1—C2—C3	−179.48 (13)	C22—C23—C24—C25	1.3 (2)
N1—C1—C2—C3	0.80 (13)	C23—C24—C25—C26	−1.0 (2)
O1—C1—C2—C5	−0.3 (2)	C22—C21—C26—C25	1.82 (19)
N1—C1—C2—C5	179.97 (11)	C5—C21—C26—C25	−179.67 (12)
N1—N2—C3—C2	0.97 (14)	C24—C25—C26—C21	−0.6 (2)
N1—N2—C3—C4	177.64 (12)	N3—N4—C31—C36	−3.89 (17)
C1—C2—C3—N2	−1.10 (14)	N3—N4—C31—C32	178.08 (11)
C5—C2—C3—N2	179.77 (11)	N4—C31—C32—C33	178.43 (11)
C1—C2—C3—C4	−177.22 (14)	C36—C31—C32—C33	0.34 (17)
C5—C2—C3—C4	3.6 (2)	N4—C31—C32—N5	−1.50 (18)
N4—N3—C5—C2	0.72 (17)	C36—C31—C32—N5	−179.59 (11)
N4—N3—C5—C21	−179.44 (10)	O3—N5—C32—C33	−5.39 (17)
C3—C2—C5—N3	−134.04 (14)	O2—N5—C32—C33	174.35 (12)
C1—C2—C5—N3	46.97 (18)	O3—N5—C32—C31	174.54 (12)
C3—C2—C5—C21	46.12 (17)	O2—N5—C32—C31	−5.72 (18)
C1—C2—C5—C21	−132.87 (12)	C31—C32—C33—C34	−0.20 (18)
N2—N1—C11—C12	131.90 (13)	N5—C32—C33—C34	179.73 (11)
C1—N1—C11—C12	−43.23 (18)	C32—C33—C34—C35	0.1 (2)
N2—N1—C11—C16	−48.92 (17)	C32—C33—C34—N6	−179.53 (12)
C1—N1—C11—C16	135.95 (13)	O5—N6—C34—C33	173.35 (16)
C16—C11—C12—C13	−1.2 (2)	O4—N6—C34—C33	−5.9 (2)
N1—C11—C12—C13	177.96 (12)	O5—N6—C34—C35	−6.3 (2)
C11—C12—C13—C14	1.0 (2)	O4—N6—C34—C35	174.49 (15)
C12—C13—C14—C15	0.6 (2)	C33—C34—C35—C36	−0.1 (2)
C13—C14—C15—C16	−1.8 (2)	N6—C34—C35—C36	179.48 (13)
C12—C11—C16—C15	−0.1 (2)	C34—C35—C36—C31	0.3 (2)
N1—C11—C16—C15	−179.21 (12)	N4—C31—C36—C35	−178.57 (12)
C14—C15—C16—C11	1.6 (2)	C32—C31—C36—C35	−0.39 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···O1	0.915 (17)	2.023 (17)	2.8261 (13)	145.6 (14)
N4—H4N···O2	0.915 (17)	2.040 (17)	2.6497 (14)	122.8 (13)
N2—H2N···O6i	0.936 (18)	1.711 (18)	2.6464 (14)	177.4 (16)
O6—H6···O1	0.89 (2)	1.72 (2)	2.5863 (14)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4N⋯O1	0.915 (17)	2.023 (17)	2.8261 (13)	145.6 (14)
N4—H4N⋯O2	0.915 (17)	2.040 (17)	2.6497 (14)	122.8 (13)
N2—H2N⋯O6i	0.936 (18)	1.711 (18)	2.6464 (14)	177.4 (16)
O6—H6⋯O1	0.89 (2)	1.72 (2)	2.5863 (14)	167 (2)

Symmetry code: (i) .