(Z)-1-(2-Chloro-phen-yl)-3-methyl-4-[2-(4-nitro-phen-yl)hydrazin-1-yl-idene]-1H-pyrazol-5(4H)-one.

There are two independent mol-ecules, A and B, in the asymmetric unit of the title compound, C(16)H(12)ClN(5)O(3). The relative orientations of the chloro-phenyl ring with respect to the pyrazole ring in the two crystallographically independent mol-ecules are different, and their corresponding dihedral angles are -53.3 (2) and 114.09 (18)° in mol-ecules A and B, respectively. There are two strong intramolecular N-H⋯O hydrogen bonds, and two weak intramolecular C-H⋯O and C-H⋯Cl hydrogen bonds. The crystal packing is constructed by weak C-H⋯O and N-H⋯O inter-actions, and two π-π stacking inter-actions [centroid-centroid distances = 3.7894 (9) and 3.5719 (10) Å], forming a mol-ecular ladder along the a axis.

Related literature

For synthesis and related literature, see: Abdel-Aziz et al. (2009 ▶); Bustos et al. (2006 ▶, 2007 ▶, 2009 ▶, 2012 ▶). For the biological activity of this class of compounds, see: Castagnolo et al. (2009 ▶); Chauhan et al. (1993 ▶); El-Hawash et al. (2006 ▶); Gunasekaran et al. (2011 ▶); Himly et al. (2003 ▶); Jolly et al. (1991 ▶); Kalluraya et al. (2007 ▶); Kawai et al. (1997 ▶); Moreau et al. (2008 ▶); Pasha et al. (2009 ▶); Radi et al. (2009 ▶); Singh (1991 ▶); Wu et al. (2002 ▶).

Experimental

Crystal data

C16H12ClN5O3

M = 357.76

Triclinic,

a = 7.2715 (6) Å

b = 14.7757 (12) Å

c = 15.7609 (12) Å

α = 75.408 (1)°

β = 86.943 (1)°

γ = 79.774 (1)°

V = 1612.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 150 K

0.24 × 0.22 × 0.10 mm

Data collection

Bruker D8 Discover diffractometer with SMART CCD area-detector

13022 measured reflections

6469 independent reflections

4430 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 0.91

6469 reflections

461 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.50 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-PC (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029790/ds2200sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029790/ds2200Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029790/ds2200Isup3.cml

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

C16H12ClN5O3	Z = 4
Mr = 357.76	F(000) = 736
Triclinic, P1	Dx = 1.474 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2715 (6) Å	Cell parameters from 999 reflections
b = 14.7757 (12) Å	θ = 1.7–26.3°
c = 15.7609 (12) Å	µ = 0.26 mm−1
α = 75.408 (1)°	T = 150 K
β = 86.943 (1)°	Polyhedron, orange
γ = 79.774 (1)°	0.24 × 0.22 × 0.10 mm
V = 1612.7 (2) Å3

Bruker D8 Discover diffractometer with SMART CCD area-detector	4430 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 26.3°, θmin = 1.7°
φ and ω scans	h = −9→9
13022 measured reflections	k = −18→18
6469 independent reflections	l = −19→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ2(Fo2) + (0.0531P)2] where P = (Fo2 + 2Fc2)/3
6469 reflections	(Δ/σ)max = 0.001
461 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl1	−0.01333 (8)	0.62030 (5)	1.02576 (4)	0.0783 (2)
O1	0.04690 (16)	0.71458 (8)	0.70638 (7)	0.0356 (4)
O2	0.39096 (19)	0.34058 (10)	0.33864 (9)	0.0506 (5)
O3	0.1869 (2)	0.45770 (10)	0.26804 (9)	0.0556 (5)
N1	0.3064 (2)	0.59306 (10)	0.89571 (9)	0.0348 (5)
N2	0.17363 (19)	0.66873 (10)	0.84708 (9)	0.0325 (5)
N3	0.2942 (2)	0.52887 (10)	0.69715 (9)	0.0337 (5)
N4	0.2057 (2)	0.57477 (11)	0.62260 (9)	0.0325 (5)
N5	0.2826 (2)	0.41611 (12)	0.33324 (11)	0.0427 (6)
C1	0.0966 (2)	0.74606 (13)	0.88317 (12)	0.0360 (6)
C2	0.1016 (3)	0.83741 (13)	0.83373 (15)	0.0472 (7)
C3	0.0258 (3)	0.91360 (16)	0.8665 (2)	0.0746 (10)
C4	−0.0534 (4)	0.8998 (2)	0.9486 (3)	0.0919 (14)
C5	−0.0606 (3)	0.8097 (2)	0.99852 (17)	0.0776 (10)
C6	0.0128 (3)	0.73186 (16)	0.96534 (13)	0.0509 (7)
C7	0.1476 (2)	0.65996 (12)	0.76493 (11)	0.0303 (6)
C8	0.2673 (2)	0.56924 (11)	0.76232 (11)	0.0303 (6)
C9	0.3580 (2)	0.53480 (12)	0.84638 (11)	0.0334 (6)
C10	0.4958 (3)	0.44607 (13)	0.87643 (13)	0.0461 (7)
C11	0.2284 (2)	0.53490 (12)	0.55094 (11)	0.0304 (6)
C12	0.1493 (2)	0.58808 (12)	0.47130 (11)	0.0345 (6)
C13	0.1677 (2)	0.54937 (13)	0.39973 (12)	0.0364 (6)
C14	0.2656 (2)	0.45854 (12)	0.40817 (11)	0.0337 (6)
C15	0.3460 (2)	0.40554 (12)	0.48640 (11)	0.0347 (6)
C16	0.3273 (2)	0.44349 (12)	0.55815 (11)	0.0328 (6)
Cl2	0.38569 (6)	0.19954 (3)	0.65477 (3)	0.0401 (2)
O4	0.14560 (16)	0.21654 (9)	0.47521 (7)	0.0372 (4)
O5	0.6349 (2)	0.07315 (9)	−0.02481 (8)	0.0530 (5)
O6	0.5293 (3)	0.22216 (11)	−0.05986 (9)	0.0832 (7)
N6	0.1295 (2)	0.08970 (10)	0.59660 (9)	0.0339 (5)
N7	0.16950 (19)	−0.01115 (10)	0.61679 (9)	0.0338 (5)
N8	0.31059 (18)	0.04899 (10)	0.39600 (9)	0.0291 (5)
N9	0.3055 (2)	0.13105 (11)	0.33806 (9)	0.0293 (5)
N10	0.5588 (2)	0.14595 (11)	−0.00578 (10)	0.0417 (6)
C17	0.0555 (2)	0.13690 (12)	0.66200 (11)	0.0338 (6)
C18	0.1585 (2)	0.19249 (12)	0.69232 (11)	0.0332 (6)
C19	0.0843 (3)	0.23988 (13)	0.75496 (12)	0.0417 (6)
C20	−0.0926 (3)	0.22971 (15)	0.78852 (12)	0.0495 (7)
C21	−0.1929 (3)	0.17270 (16)	0.76076 (12)	0.0503 (7)
C22	−0.1210 (3)	0.12697 (15)	0.69684 (12)	0.0443 (7)
C23	0.1699 (2)	0.13106 (13)	0.51121 (11)	0.0310 (6)
C24	0.2456 (2)	0.04932 (12)	0.47505 (10)	0.0284 (5)
C25	0.2384 (2)	−0.03413 (12)	0.54576 (11)	0.0303 (5)
C26	0.2990 (3)	−0.13494 (12)	0.54268 (12)	0.0379 (6)
C27	0.3760 (2)	0.13371 (12)	0.25320 (10)	0.0263 (5)
C28	0.3623 (2)	0.22144 (12)	0.19267 (11)	0.0306 (5)
C29	0.4246 (2)	0.22550 (12)	0.10800 (11)	0.0324 (6)
C30	0.4999 (2)	0.14203 (12)	0.08492 (11)	0.0306 (6)
C31	0.5177 (2)	0.05511 (12)	0.14479 (11)	0.0316 (6)
C32	0.4578 (2)	0.05063 (12)	0.22955 (11)	0.0302 (6)
H2	0.15770	0.84740	0.77700	0.0570*
H3	0.02820	0.97620	0.83220	0.0900*
H4	−0.10380	0.95290	0.97120	0.1100*
H5	−0.11540	0.80060	1.05550	0.0930*
H7	0.135 (2)	0.6333 (13)	0.6166 (11)	0.040 (5)*
H10A	0.53790	0.44200	0.93550	0.0690*
H10B	0.60330	0.44670	0.83620	0.0690*
H10C	0.43690	0.39110	0.87740	0.0690*
H12	0.08310	0.65070	0.46640	0.0410*
H13	0.11360	0.58480	0.34520	0.0440*
H15	0.41360	0.34340	0.49060	0.0420*
H16	0.38160	0.40760	0.61240	0.0390*
H8	0.252 (2)	0.1836 (13)	0.3497 (12)	0.040 (5)*
H19	0.15420	0.27900	0.77470	0.0500*
H20	−0.14490	0.26260	0.83110	0.0590*
H21	−0.31260	0.16450	0.78560	0.0600*
H22	−0.19250	0.08870	0.67670	0.0530*
H26A	0.27280	−0.17660	0.59930	0.0570*
H26B	0.43350	−0.14620	0.53010	0.0570*
H26C	0.23080	−0.14830	0.49650	0.0570*
H28	0.31030	0.27800	0.20970	0.0370*
H29	0.41610	0.28480	0.06590	0.0390*
H31	0.57090	−0.00110	0.12750	0.0380*
H32	0.47180	−0.00860	0.27180	0.0360*

	U11	U22	U33	U12	U13	U23
Cl1	0.0652 (4)	0.1022 (5)	0.0431 (3)	0.0082 (3)	0.0134 (3)	0.0083 (3)
O1	0.0404 (7)	0.0362 (7)	0.0283 (7)	−0.0009 (6)	−0.0055 (6)	−0.0072 (6)
O2	0.0640 (10)	0.0469 (9)	0.0502 (9)	−0.0167 (7)	0.0170 (7)	−0.0278 (7)
O3	0.0732 (10)	0.0675 (10)	0.0328 (8)	−0.0217 (8)	−0.0005 (7)	−0.0177 (7)
N1	0.0385 (9)	0.0318 (8)	0.0303 (8)	0.0003 (7)	−0.0039 (7)	−0.0042 (7)
N2	0.0385 (8)	0.0304 (8)	0.0274 (8)	0.0003 (6)	−0.0035 (7)	−0.0087 (6)
N3	0.0362 (8)	0.0349 (8)	0.0302 (8)	−0.0073 (7)	0.0034 (7)	−0.0083 (7)
N4	0.0374 (9)	0.0304 (9)	0.0294 (8)	−0.0020 (7)	0.0016 (7)	−0.0101 (7)
N5	0.0531 (11)	0.0469 (10)	0.0357 (10)	−0.0223 (9)	0.0117 (8)	−0.0168 (8)
C1	0.0342 (10)	0.0395 (11)	0.0364 (11)	0.0042 (8)	−0.0118 (8)	−0.0180 (9)
C2	0.0425 (12)	0.0357 (11)	0.0646 (14)	0.0002 (9)	−0.0204 (10)	−0.0152 (10)
C3	0.0645 (17)	0.0444 (14)	0.122 (2)	0.0115 (12)	−0.0504 (17)	−0.0375 (16)
C4	0.0711 (19)	0.093 (2)	0.129 (3)	0.0405 (16)	−0.0581 (19)	−0.085 (2)
C5	0.0541 (15)	0.123 (2)	0.0606 (16)	0.0365 (16)	−0.0269 (12)	−0.0621 (18)
C6	0.0436 (12)	0.0706 (15)	0.0355 (11)	0.0138 (10)	−0.0139 (9)	−0.0212 (11)
C7	0.0329 (10)	0.0316 (10)	0.0269 (9)	−0.0078 (8)	0.0020 (8)	−0.0071 (8)
C8	0.0337 (10)	0.0292 (9)	0.0286 (10)	−0.0057 (8)	0.0036 (7)	−0.0087 (8)
C9	0.0360 (10)	0.0316 (10)	0.0300 (10)	−0.0042 (8)	0.0028 (8)	−0.0046 (8)
C10	0.0519 (12)	0.0399 (11)	0.0392 (11)	0.0053 (9)	−0.0015 (9)	−0.0055 (9)
C11	0.0322 (10)	0.0320 (10)	0.0304 (10)	−0.0096 (8)	0.0061 (7)	−0.0122 (8)
C12	0.0350 (10)	0.0322 (10)	0.0359 (10)	−0.0047 (8)	0.0009 (8)	−0.0084 (8)
C13	0.0402 (11)	0.0401 (11)	0.0293 (10)	−0.0107 (9)	0.0024 (8)	−0.0072 (8)
C14	0.0390 (10)	0.0369 (10)	0.0307 (10)	−0.0154 (8)	0.0086 (8)	−0.0143 (8)
C15	0.0382 (10)	0.0291 (10)	0.0376 (11)	−0.0070 (8)	0.0085 (8)	−0.0107 (8)
C16	0.0364 (10)	0.0314 (10)	0.0303 (10)	−0.0061 (8)	0.0026 (8)	−0.0072 (8)
Cl2	0.0379 (3)	0.0390 (3)	0.0408 (3)	−0.0072 (2)	−0.0009 (2)	−0.0045 (2)
O4	0.0464 (8)	0.0364 (7)	0.0264 (7)	−0.0047 (6)	0.0047 (6)	−0.0062 (6)
O5	0.0758 (10)	0.0461 (8)	0.0401 (8)	−0.0067 (7)	0.0197 (7)	−0.0230 (7)
O6	0.1420 (16)	0.0506 (10)	0.0322 (9)	0.0191 (10)	0.0312 (9)	0.0043 (8)
N6	0.0407 (9)	0.0369 (9)	0.0240 (8)	−0.0084 (7)	0.0068 (7)	−0.0078 (7)
N7	0.0346 (8)	0.0387 (9)	0.0279 (8)	−0.0092 (7)	0.0018 (6)	−0.0063 (7)
N8	0.0271 (8)	0.0363 (8)	0.0240 (8)	−0.0066 (6)	−0.0010 (6)	−0.0068 (7)
N9	0.0341 (8)	0.0292 (8)	0.0238 (8)	−0.0014 (7)	0.0032 (6)	−0.0084 (7)
N10	0.0516 (10)	0.0410 (10)	0.0314 (9)	−0.0039 (8)	0.0125 (8)	−0.0125 (8)
C17	0.0376 (10)	0.0413 (11)	0.0204 (9)	−0.0029 (8)	0.0022 (7)	−0.0067 (8)
C18	0.0359 (10)	0.0345 (10)	0.0241 (9)	0.0012 (8)	−0.0012 (8)	−0.0028 (8)
C19	0.0504 (12)	0.0427 (11)	0.0298 (10)	0.0011 (9)	−0.0070 (9)	−0.0099 (9)
C20	0.0506 (13)	0.0653 (14)	0.0271 (11)	0.0139 (11)	−0.0031 (9)	−0.0173 (10)
C21	0.0360 (11)	0.0856 (16)	0.0260 (10)	−0.0011 (11)	0.0032 (8)	−0.0151 (11)
C22	0.0363 (11)	0.0712 (14)	0.0270 (10)	−0.0124 (10)	0.0019 (8)	−0.0134 (10)
C23	0.0306 (9)	0.0399 (11)	0.0225 (9)	−0.0065 (8)	0.0011 (7)	−0.0078 (8)
C24	0.0256 (9)	0.0367 (10)	0.0234 (9)	−0.0060 (7)	0.0007 (7)	−0.0083 (8)
C25	0.0267 (9)	0.0401 (10)	0.0253 (9)	−0.0106 (8)	−0.0007 (7)	−0.0067 (8)
C26	0.0420 (11)	0.0385 (11)	0.0329 (10)	−0.0102 (9)	0.0015 (8)	−0.0063 (9)
C27	0.0256 (9)	0.0338 (9)	0.0213 (9)	−0.0044 (7)	0.0009 (7)	−0.0107 (7)
C28	0.0361 (10)	0.0284 (9)	0.0273 (9)	−0.0013 (8)	0.0018 (8)	−0.0104 (8)
C29	0.0388 (10)	0.0298 (10)	0.0259 (9)	−0.0026 (8)	0.0034 (8)	−0.0050 (8)
C30	0.0347 (10)	0.0344 (10)	0.0234 (9)	−0.0057 (8)	0.0051 (7)	−0.0098 (8)
C31	0.0362 (10)	0.0293 (10)	0.0312 (10)	−0.0043 (8)	0.0060 (8)	−0.0133 (8)
C32	0.0344 (10)	0.0265 (9)	0.0286 (10)	−0.0044 (7)	0.0020 (7)	−0.0057 (8)

Cl1—C6	1.721 (2)	C14—C15	1.380 (2)
Cl2—C18	1.7367 (16)	C15—C16	1.374 (2)
O1—C7	1.235 (2)	C2—H2	0.9500
O2—N5	1.233 (2)	C3—H3	0.9500
O3—N5	1.235 (2)	C4—H4	0.9500
O4—C23	1.232 (2)	C5—H5	0.9500
O5—N10	1.219 (2)	C10—H10A	0.9800
O6—N10	1.221 (2)	C10—H10B	0.9800
N1—C9	1.295 (2)	C10—H10C	0.9800
N1—N2	1.426 (2)	C12—H12	0.9500
N2—C1	1.417 (2)	C13—H13	0.9500
N2—C7	1.360 (2)	C15—H15	0.9500
N3—C8	1.302 (2)	C16—H16	0.9500
N3—N4	1.334 (2)	C17—C22	1.386 (3)
N4—C11	1.390 (2)	C17—C18	1.385 (2)
N5—C14	1.461 (2)	C18—C19	1.383 (3)
N4—H7	0.910 (19)	C19—C20	1.383 (3)
N6—C23	1.371 (2)	C20—C21	1.368 (3)
N6—N7	1.423 (2)	C21—C22	1.381 (3)
N6—C17	1.417 (2)	C23—C24	1.471 (3)
N7—C25	1.300 (2)	C24—C25	1.446 (2)
N8—N9	1.317 (2)	C25—C26	1.489 (3)
N8—C24	1.310 (2)	C27—C32	1.396 (2)
N9—C27	1.400 (2)	C27—C28	1.393 (2)
N10—C30	1.460 (2)	C28—C29	1.376 (2)
N9—H8	0.863 (19)	C29—C30	1.385 (3)
C1—C6	1.385 (3)	C30—C31	1.378 (2)
C1—C2	1.384 (3)	C31—C32	1.372 (2)
C2—C3	1.371 (3)	C19—H19	0.9500
C3—C4	1.370 (5)	C20—H20	0.9500
C4—C5	1.374 (5)	C21—H21	0.9500
C5—C6	1.392 (4)	C22—H22	0.9500
C7—C8	1.472 (2)	C26—H26A	0.9800
C8—C9	1.443 (2)	C26—H26B	0.9800
C9—C10	1.490 (3)	C26—H26C	0.9800
C11—C16	1.393 (2)	C28—H28	0.9500
C11—C12	1.394 (2)	C29—H29	0.9500
C12—C13	1.378 (3)	C31—H31	0.9500
C13—C14	1.381 (3)	C32—H32	0.9500
Cl1···N1	3.0568 (16)	C12···C14iii	3.557 (2)
Cl1···N2	3.0352 (15)	C13···C12iii	3.557 (2)
Cl2···O4	3.3366 (12)	C13···C11iii	3.316 (2)
Cl2···N6	2.9917 (16)	C14···C12iii	3.557 (2)
Cl2···C15	3.4770 (18)	C15···O4	3.417 (2)
Cl2···C16	3.5002 (19)	C15···Cl2	3.4770 (18)
Cl2···C21i	3.481 (2)	C15···C11iv	3.348 (2)
Cl2···C22i	3.604 (2)	C15···C16iv	3.468 (2)
Cl2···C23	3.2713 (18)	C16···C16iv	3.451 (2)
Cl2···H15	2.9300	C16···Cl2	3.5002 (19)
Cl2···H16	2.9700	C16···C15iv	3.468 (2)
Cl2···H21i	2.9800	C18···O4	3.355 (2)
Cl2···H32ii	2.8000	C20···C5xiv	3.468 (3)
O1···C2	3.108 (2)	C21···Cl2xvi	3.481 (2)
O1···O3iii	3.2371 (19)	C22···Cl2xvi	3.604 (2)
O1···N3	3.0341 (19)	C23···C26xii	3.545 (3)
O1···N4	2.777 (2)	C23···Cl2	3.2713 (18)
O1···C28iii	3.396 (2)	C25···N8ii	3.407 (2)
O1···O4iii	3.1049 (16)	C26···C23xii	3.545 (3)
O1···N9iii	3.094 (2)	C28···O1iii	3.396 (2)
O2···N9	3.266 (2)	C28···C1iii	3.516 (2)
O2···C8iv	3.189 (2)	C28···O2	3.265 (2)
O2···C28	3.265 (2)	C29···C1iv	3.594 (2)
O2···O4	3.1526 (18)	C29···C2iv	3.514 (3)
O2···N3iv	3.188 (2)	C29···C6iii	3.341 (3)
O3···C10iv	3.392 (3)	C29···C5iii	3.391 (3)
O3···O1iii	3.2371 (19)	C30···C3iv	3.481 (3)
O3···C7iii	3.362 (2)	C30···C2iv	3.322 (3)
O4···C15	3.417 (2)	C30···C5iii	3.407 (3)
O4···O1iii	3.1049 (16)	C30···C4iii	3.502 (3)
O4···Cl2	3.3366 (12)	C31···O5v	3.343 (2)
O4···N8	3.077 (2)	C31···C3iv	3.421 (3)
O4···O2	3.1526 (18)	C31···C2iv	3.497 (3)
O4···C18	3.355 (2)	C5···H20xiv	3.0000
O4···N9	2.8647 (19)	C7···H7	2.476 (17)
O5···C31v	3.343 (2)	C7···H2	2.8400
O5···C4vi	3.202 (3)	C19···H13iii	2.8500
O5···O5v	3.102 (2)	C19···H5xiv	2.9100
O6···C10vii	3.175 (3)	C20···H13iii	2.9900
O1···H7	2.084 (18)	C20···H5xiv	2.8500
O1···H28iii	2.8500	C21···H3xi	3.0300
O1···H26Aviii	2.7200	C22···H3xi	2.7700
O1···H8iii	2.478 (17)	C23···H8	2.539 (18)
O1···H2	2.7400	C23···H26Cxii	2.8900
O2···H15	2.4200	C23···H26Bii	2.9600
O2···H8	2.654 (18)	C24···H26Bii	2.9300
O2···H28	2.5700	H2···O1	2.7400
O3···H10Biv	2.5200	H2···N7viii	2.8500
O3···H13	2.4500	H2···C7	2.8400
O4···H12iii	2.6500	H3···C21viii	3.0300
O4···H8	2.222 (18)	H3···C22viii	2.7700
O4···H7iii	2.876 (17)	H4···O5xiii	2.3700
O5···H4vi	2.3700	H4···H4xvii	2.5600
O5···H31	2.4300	H5···C19xiv	2.9100
O5···H31v	2.7700	H5···C20xiv	2.8500
O6···H10Cvii	2.4300	H5···H20xiv	2.5600
O6···H20ix	2.9100	H7···O1	2.084 (18)
O6···H21ix	2.8900	H7···O4iii	2.876 (17)
O6···H29	2.4400	H7···C7	2.476 (17)
N1···Cl1	3.0568 (16)	H7···H12	2.3600
N2···Cl1	3.0352 (15)	H8···O4	2.222 (18)
N3···O2iv	3.188 (2)	H8···O1iii	2.478 (17)
N3···O1	3.0341 (19)	H8···C23	2.539 (18)
N4···O1	2.777 (2)	H8···H28	2.3600
N6···Cl2	2.9917 (16)	H8···O2	2.654 (18)
N8···C25ii	3.407 (2)	H10A···N1x	2.8400
N8···O4	3.077 (2)	H10B···O3iv	2.5200
N9···O1iii	3.094 (2)	H10C···O6xv	2.4300
N9···O2	3.266 (2)	H12···H7	2.3600
N9···O4	2.8647 (19)	H12···O4iii	2.6500
N1···H10Ax	2.8400	H13···O3	2.4500
N3···H16	2.4700	H13···C19iii	2.8500
N7···H2xi	2.8500	H13···C20iii	2.9900
N8···H22xii	2.8400	H15···Cl2	2.9300
N8···H32	2.4800	H15···O2	2.4200
C1···C28iii	3.516 (2)	H16···Cl2	2.9700
C1···C29iv	3.594 (2)	H16···N3	2.4700
C2···O1	3.108 (2)	H20···O6xviii	2.9100
C2···C29iv	3.514 (3)	H20···C5xiv	3.0000
C2···C30iv	3.322 (3)	H20···H5xiv	2.5600
C2···C31iv	3.497 (3)	H21···Cl2xvi	2.9800
C3···C31iv	3.421 (3)	H21···O6xviii	2.8900
C3···C30iv	3.481 (3)	H22···N8xii	2.8400
C4···O5xiii	3.202 (3)	H22···H32xii	2.5300
C4···C30iii	3.502 (3)	H26A···O1xi	2.7200
C5···C29iii	3.391 (3)	H26B···C23ii	2.9600
C5···C20xiv	3.468 (3)	H26B···C24ii	2.9300
C5···C30iii	3.407 (3)	H26C···C23xii	2.8900
C6···C29iii	3.341 (3)	H28···O2	2.5700
C7···O3iii	3.362 (2)	H28···H8	2.3600
C8···O2iv	3.189 (2)	H28···O1iii	2.8500
C10···O6xv	3.175 (3)	H29···O6	2.4400
C10···O3iv	3.392 (3)	H31···O5	2.4300
C11···C15iv	3.348 (2)	H31···O5v	2.7700
C11···C13iii	3.316 (2)	H32···N8	2.4800
C12···C13iii	3.557 (2)	H32···Cl2ii	2.8000
C12···C12iii	3.594 (2)	H32···H22xii	2.5300
N2—N1—C9	106.83 (13)	H10A—C10—H10B	109.00
N1—N2—C1	119.93 (13)	H10A—C10—H10C	109.00
N1—N2—C7	112.75 (14)	C9—C10—H10A	110.00
C1—N2—C7	127.10 (15)	C11—C12—H12	120.00
N4—N3—C8	117.15 (15)	C13—C12—H12	120.00
N3—N4—C11	119.70 (15)	C14—C13—H13	120.00
O2—N5—O3	123.58 (17)	C12—C13—H13	120.00
O2—N5—C14	118.30 (15)	C14—C15—H15	120.00
O3—N5—C14	118.12 (16)	C16—C15—H15	120.00
C11—N4—H7	118.9 (11)	C11—C16—H16	120.00
N3—N4—H7	121.4 (11)	C15—C16—H16	120.00
C17—N6—C23	126.83 (15)	C18—C17—C22	119.34 (16)
N7—N6—C23	112.99 (14)	N6—C17—C22	119.98 (16)
N7—N6—C17	120.19 (13)	N6—C17—C18	120.68 (14)
N6—N7—C25	106.64 (13)	Cl2—C18—C17	120.02 (13)
N9—N8—C24	118.23 (15)	Cl2—C18—C19	119.47 (14)
N8—N9—C27	119.93 (15)	C17—C18—C19	120.47 (16)
O5—N10—O6	122.44 (16)	C18—C19—C20	119.38 (18)
O5—N10—C30	118.93 (15)	C19—C20—C21	120.46 (19)
O6—N10—C30	118.63 (16)	C20—C21—C22	120.3 (2)
N8—N9—H8	121.6 (12)	C17—C22—C21	120.0 (2)
C27—N9—H8	118.3 (12)	O4—C23—N6	127.09 (17)
C2—C1—C6	119.81 (19)	O4—C23—C24	129.70 (15)
N2—C1—C2	118.81 (16)	N6—C23—C24	103.21 (15)
N2—C1—C6	121.35 (18)	N8—C24—C23	128.65 (16)
C1—C2—C3	120.1 (2)	C23—C24—C25	106.06 (14)
C2—C3—C4	120.3 (3)	N8—C24—C25	125.28 (16)
C3—C4—C5	120.5 (3)	N7—C25—C26	121.74 (16)
C4—C5—C6	119.7 (3)	C24—C25—C26	127.17 (15)
C1—C6—C5	119.6 (2)	N7—C25—C24	111.09 (15)
Cl1—C6—C5	118.78 (17)	C28—C27—C32	120.65 (15)
Cl1—C6—C1	121.59 (17)	N9—C27—C28	118.40 (16)
O1—C7—C8	128.04 (16)	N9—C27—C32	120.95 (15)
O1—C7—N2	128.49 (16)	C27—C28—C29	119.44 (16)
N2—C7—C8	103.47 (14)	C28—C29—C30	119.11 (16)
C7—C8—C9	105.96 (14)	N10—C30—C31	119.01 (16)
N3—C8—C7	127.95 (15)	N10—C30—C29	119.11 (15)
N3—C8—C9	126.04 (15)	C29—C30—C31	121.87 (16)
N1—C9—C10	121.84 (15)	C30—C31—C32	119.33 (16)
C8—C9—C10	127.23 (16)	C27—C32—C31	119.53 (16)
N1—C9—C8	110.92 (15)	C18—C19—H19	120.00
N4—C11—C16	120.98 (15)	C20—C19—H19	120.00
C12—C11—C16	120.35 (16)	C19—C20—H20	120.00
N4—C11—C12	118.67 (16)	C21—C20—H20	120.00
C11—C12—C13	119.63 (16)	C20—C21—H21	120.00
C12—C13—C14	119.22 (16)	C22—C21—H21	120.00
N5—C14—C15	118.64 (16)	C17—C22—H22	120.00
C13—C14—C15	121.69 (16)	C21—C22—H22	120.00
N5—C14—C13	119.66 (15)	C25—C26—H26A	109.00
C14—C15—C16	119.39 (16)	C25—C26—H26B	109.00
C11—C16—C15	119.71 (16)	C25—C26—H26C	109.00
C1—C2—H2	120.00	H26A—C26—H26B	109.00
C3—C2—H2	120.00	H26A—C26—H26C	110.00
C4—C3—H3	120.00	H26B—C26—H26C	109.00
C2—C3—H3	120.00	C27—C28—H28	120.00
C5—C4—H4	120.00	C29—C28—H28	120.00
C3—C4—H4	120.00	C28—C29—H29	120.00
C4—C5—H5	120.00	C30—C29—H29	120.00
C6—C5—H5	120.00	C30—C31—H31	120.00
C9—C10—H10C	109.00	C32—C31—H31	120.00
C9—C10—H10B	109.00	C27—C32—H32	120.00
H10B—C10—H10C	110.00	C31—C32—H32	120.00
C9—N1—N2—C1	−177.60 (14)	C3—C4—C5—C6	−0.1 (4)
C9—N1—N2—C7	−2.68 (18)	C4—C5—C6—Cl1	−175.3 (2)
N2—N1—C9—C10	−179.42 (15)	C4—C5—C6—C1	1.6 (3)
N2—N1—C9—C8	1.49 (18)	N2—C7—C8—C9	−1.58 (16)
C7—N2—C1—C2	−45.7 (2)	N2—C7—C8—N3	−178.96 (16)
N1—N2—C1—C6	−53.3 (2)	O1—C7—C8—N3	1.4 (3)
C7—N2—C1—C6	132.57 (19)	O1—C7—C8—C9	178.79 (16)
C1—N2—C7—C8	177.05 (15)	N3—C8—C9—N1	177.47 (16)
N1—N2—C7—O1	−177.80 (16)	N3—C8—C9—C10	−1.6 (3)
C1—N2—C7—O1	−3.3 (3)	C7—C8—C9—C10	−179.01 (16)
N1—N2—C1—C2	128.42 (18)	C7—C8—C9—N1	0.03 (19)
N1—N2—C7—C8	2.58 (17)	N4—C11—C12—C13	−179.02 (15)
C8—N3—N4—C11	−179.70 (15)	N4—C11—C16—C15	179.38 (15)
N4—N3—C8—C7	1.0 (2)	C12—C11—C16—C15	−0.3 (2)
N4—N3—C8—C9	−175.90 (15)	C16—C11—C12—C13	0.7 (2)
N3—N4—C11—C16	6.4 (2)	C11—C12—C13—C14	−0.4 (2)
N3—N4—C11—C12	−173.89 (15)	C12—C13—C14—N5	178.73 (14)
O2—N5—C14—C15	−10.7 (2)	C12—C13—C14—C15	−0.2 (2)
O3—N5—C14—C13	−10.0 (2)	C13—C14—C15—C16	0.5 (2)
O2—N5—C14—C13	170.37 (15)	N5—C14—C15—C16	−178.37 (14)
O3—N5—C14—C15	168.98 (15)	C14—C15—C16—C11	−0.3 (2)
N7—N6—C17—C22	−65.3 (2)	C22—C17—C18—Cl2	175.76 (14)
C23—N6—C17—C18	−66.0 (2)	N6—C17—C18—Cl2	−3.7 (2)
C23—N6—C17—C22	114.6 (2)	C22—C17—C18—C19	−1.8 (3)
C17—N6—C23—C24	178.77 (15)	N6—C17—C18—C19	178.76 (16)
N7—N6—C17—C18	114.09 (18)	C18—C17—C22—C21	0.4 (3)
N7—N6—C23—O4	178.25 (15)	N6—C17—C22—C21	179.79 (18)
C17—N6—C23—O4	−1.7 (3)	C17—C18—C19—C20	1.3 (3)
N7—N6—C23—C24	−1.28 (17)	Cl2—C18—C19—C20	−176.25 (15)
C23—N6—N7—C25	1.31 (18)	C18—C19—C20—C21	0.6 (3)
C17—N6—N7—C25	−178.74 (14)	C19—C20—C21—C22	−2.1 (3)
N6—N7—C25—C24	−0.71 (17)	C20—C21—C22—C17	1.6 (3)
N6—N7—C25—C26	179.30 (15)	O4—C23—C24—N8	2.4 (3)
C24—N8—N9—C27	179.13 (14)	O4—C23—C24—C25	−178.71 (16)
N9—N8—C24—C25	179.09 (14)	N6—C23—C24—N8	−178.13 (16)
N9—N8—C24—C23	−2.2 (2)	N6—C23—C24—C25	0.80 (16)
N8—N9—C27—C28	177.73 (14)	N8—C24—C25—N7	178.93 (15)
N8—N9—C27—C32	−2.2 (2)	N8—C24—C25—C26	−1.1 (3)
O5—N10—C30—C31	−5.4 (2)	C23—C24—C25—N7	−0.05 (18)
O5—N10—C30—C29	175.80 (15)	C23—C24—C25—C26	179.94 (16)
O6—N10—C30—C29	−4.4 (2)	N9—C27—C28—C29	−177.71 (14)
O6—N10—C30—C31	174.38 (17)	C32—C27—C28—C29	2.2 (2)
N2—C1—C6—C5	179.79 (18)	N9—C27—C32—C31	176.99 (14)
C2—C1—C6—Cl1	174.84 (16)	C28—C27—C32—C31	−2.9 (2)
C6—C1—C2—C3	0.8 (3)	C27—C28—C29—C30	−0.1 (2)
C2—C1—C6—C5	−2.0 (3)	C28—C29—C30—N10	177.47 (14)
N2—C1—C6—Cl1	−3.4 (3)	C28—C29—C30—C31	−1.3 (2)
N2—C1—C2—C3	179.09 (19)	N10—C30—C31—C32	−178.19 (14)
C1—C2—C3—C4	0.7 (4)	C29—C30—C31—C32	0.6 (2)
C2—C3—C4—C5	−1.1 (4)	C30—C31—C32—C27	1.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H7···O1	0.910 (19)	2.084 (18)	2.777 (2)	132.1 (14)
N9—H8···O4	0.863 (19)	2.222 (18)	2.8647 (19)	131.2 (16)
C28—H28···O2	0.95	2.57	3.265 (2)	130
C15—H15···Cl2	0.95	2.93	3.4770 (18)	118
N9—H8···O2	0.86 (2)	2.654 (18)	3.266 (2)	129.0 (13)
N9—H8···O1iii	0.863 (19)	2.478 (17)	3.094 (2)	128.9 (14)
C4—H4···O5xiii	0.95	2.37	3.202 (3)	146
C10—H10B···O3iv	0.98	2.52	3.392 (3)	148
C10—H10C···O6xv	0.98	2.43	3.175 (3)	133
C32—H32···Cl2ii	0.95	2.80	3.6898 (18)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H7⋯O1	0.910 (19)	2.084 (18)	2.777 (2)	132.1 (14)
N9—H8⋯O4	0.863 (19)	2.222 (18)	2.8647 (19)	131.2 (16)
C28—H28⋯O2	0.95	2.57	3.265 (2)	130
C15—H15⋯Cl2	0.95	2.93	3.4770 (18)	118
N9—H8⋯O2	0.86 (2)	2.654 (18)	3.266 (2)	129.0 (13)
N9—H8⋯O1i	0.863 (19)	2.478 (17)	3.094 (2)	128.9 (14)
C4—H4⋯O5ii	0.95	2.37	3.202 (3)	146
C10—H10B⋯O3iii	0.98	2.52	3.392 (3)	148
C10—H10C⋯O6iv	0.98	2.43	3.175 (3)	133
C32—H32⋯Cl2v	0.95	2.80	3.6898 (18)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .