4-(2,3-Dichloro­benzyl­ideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

The title Schiff base compound, C₁₈H₁₅Cl₂N₃O, was synthesized by the reaction of 4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one and 2,3-dichloro­benzaldehyde in MeOH solution. There are two molecules in the asymmetric unit. As expected, the compound adopts a trans configuration about the central C=N bond. In the crystal structure, mol­ecules are linked through weak C—H...O hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• R factor = 0.057
• wR factor = 0.134
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2002); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

4-(2,3-Dichlorobenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Crystal data

C18H15Cl2N3O	F(000) = 2976
Mr = 360.23	Dx = 1.392 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6442 reflections
a = 18.9602 (8) Å	θ = 2.2–22.9°
b = 7.1044 (3) Å	µ = 0.39 mm^−1
c = 51.387 (2) Å	T = 295 K
β = 96.529 (1)°	Prism, yellow
V = 6877.0 (5) Å^3	0.35 × 0.08 × 0.07 mm
Z = 16

Data collection

Bruker APEX area-detector diffractometer	7114 independent reflections
Radiation source: fine-focus sealed tube	5532 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 26.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.956, Tmax = 0.973	k = −8→8
35938 measured reflections	l = −64→64

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0478P)^2 + 7.688P] where P = (Fo^2 + 2Fc^2)/3
7114 reflections	(Δ/σ)max = 0.001
437 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.35 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
Cl1	0.55293 (4)	0.26083 (10)	0.116299 (17)	0.0701 (3)
Cl2	0.66956 (4)	0.23148 (11)	0.077987 (15)	0.0651 (2)
O1	0.43058 (11)	0.5140 (3)	0.17670 (4)	0.0598 (5)
N1	0.41610 (11)	0.7618 (3)	0.20490 (4)	0.0452 (5)
N2	0.45366 (12)	0.9274 (3)	0.21218 (4)	0.0457 (5)
N3	0.54767 (11)	0.7834 (3)	0.15919 (4)	0.0461 (5)
C1	0.32109 (15)	0.5575 (4)	0.21376 (6)	0.0534 (7)
H1	0.3055	0.5578	0.1959	0.064*
C2	0.28635 (17)	0.4504 (5)	0.23083 (7)	0.0684 (9)
H2	0.2478	0.3763	0.2244	0.082*
C3	0.3084 (2)	0.4529 (5)	0.25708 (7)	0.0744 (10)
H3	0.2847	0.3810	0.2685	0.089*
C4	0.36512 (18)	0.5609 (5)	0.26664 (6)	0.0717 (9)
H4	0.3797	0.5625	0.2845	0.086*
C5	0.40110 (15)	0.6682 (4)	0.24986 (5)	0.0555 (7)
H5	0.4396	0.7421	0.2564	0.067*
C6	0.37912 (13)	0.6638 (4)	0.22342 (5)	0.0437 (6)
C7	0.44721 (14)	0.6721 (4)	0.18480 (5)	0.0444 (6)
C8	0.50006 (14)	0.8021 (3)	0.17781 (5)	0.0420 (6)
C9	0.50072 (14)	0.9528 (4)	0.19415 (5)	0.0456 (6)
C10	0.54334 (19)	1.1281 (4)	0.19379 (6)	0.0687 (9)
H10A	0.5785	1.1131	0.1819	0.103*
H10B	0.5663	1.1529	0.2111	0.103*
H10C	0.5127	1.2314	0.1882	0.103*
C11	0.41219 (17)	1.0827 (4)	0.22160 (6)	0.0616 (8)
H11A	0.4433	1.1851	0.2271	0.092*
H11B	0.3886	1.0401	0.2361	0.092*
H11C	0.3775	1.1242	0.2077	0.092*
C12	0.54534 (13)	0.6405 (4)	0.14425 (5)	0.0452 (6)
H12	0.5112	0.5480	0.1455	0.054*
C13	0.59681 (13)	0.6213 (4)	0.12500 (5)	0.0415 (6)
C14	0.60530 (13)	0.4538 (4)	0.11141 (5)	0.0433 (6)
C15	0.65691 (14)	0.4400 (4)	0.09442 (5)	0.0437 (6)
C16	0.69984 (14)	0.5901 (4)	0.09035 (5)	0.0490 (6)
H16	0.7345	0.5794	0.0790	0.059*
C17	0.69114 (14)	0.7564 (4)	0.10323 (5)	0.0523 (7)
H17	0.7197	0.8591	0.1004	0.063*
C18	0.64046 (14)	0.7720 (4)	0.12029 (5)	0.0478 (6)
H18	0.6353	0.8857	0.1288	0.057*
Cl3	0.25248 (4)	0.64909 (11)	0.143342 (13)	0.0583 (2)
Cl4	0.23014 (5)	0.99750 (14)	0.178557 (15)	0.0763 (3)
O2	0.31708 (11)	0.3620 (3)	0.07082 (4)	0.0662 (6)
N4	0.40425 (12)	0.3307 (3)	0.04347 (4)	0.0526 (6)
N5	0.45955 (11)	0.4450 (3)	0.03600 (4)	0.0516 (6)
N6	0.40656 (11)	0.7227 (3)	0.08800 (4)	0.0477 (5)
C19	0.35006 (17)	0.2526 (5)	−0.00039 (6)	0.0721 (9)
H19	0.3543	0.3770	−0.0056	0.087*
C20	0.32156 (19)	0.1161 (8)	−0.01809 (7)	0.0907 (13)
H20	0.3075	0.1489	−0.0354	0.109*
C21	0.3142 (2)	−0.0650 (7)	−0.01013 (9)	0.0992 (15)
H21	0.2954	−0.1557	−0.0220	0.119*
C22	0.3344 (2)	−0.1121 (6)	0.01507 (9)	0.0962 (13)
H22	0.3284	−0.2355	0.0204	0.115*
C23	0.36350 (18)	0.0172 (5)	0.03292 (7)	0.0703 (9)
H23	0.3774	−0.0178	0.0502	0.084*
C24	0.37168 (14)	0.1989 (4)	0.02494 (5)	0.0500 (7)
C25	0.37179 (14)	0.4180 (4)	0.06310 (5)	0.0478 (6)
C26	0.41562 (13)	0.5815 (4)	0.07008 (5)	0.0451 (6)
C27	0.46719 (13)	0.5892 (4)	0.05380 (5)	0.0479 (6)
C28	0.52484 (15)	0.7318 (5)	0.05331 (6)	0.0648 (8)
H28A	0.5195	0.8272	0.0662	0.097*
H28B	0.5219	0.7883	0.0363	0.097*
H28C	0.5701	0.6715	0.0572	0.097*
C29	0.52048 (16)	0.3390 (5)	0.02875 (7)	0.0732 (9)
H29A	0.5546	0.4246	0.0229	0.110*
H29B	0.5050	0.2527	0.0149	0.110*
H29C	0.5419	0.2702	0.0437	0.110*
C30	0.36197 (14)	0.7055 (4)	0.10466 (5)	0.0465 (6)
H30	0.3361	0.5947	0.1054	0.056*
C31	0.35154 (13)	0.8601 (4)	0.12256 (5)	0.0439 (6)
C32	0.30227 (13)	0.8506 (4)	0.14076 (5)	0.0432 (6)
C33	0.29228 (15)	1.0041 (4)	0.15655 (5)	0.0507 (7)
C34	0.33134 (17)	1.1664 (4)	0.15476 (6)	0.0603 (8)
H34	0.3245	1.2689	0.1654	0.072*
C35	0.38016 (17)	1.1756 (4)	0.13717 (6)	0.0639 (8)
H35	0.4069	1.2844	0.1361	0.077*
C36	0.38997 (15)	1.0265 (4)	0.12123 (6)	0.0562 (7)
H36	0.4230	1.0361	0.1092	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0764 (5)	0.0466 (4)	0.0940 (6)	−0.0204 (4)	0.0383 (5)	−0.0137 (4)
Cl2	0.0797 (5)	0.0608 (5)	0.0569 (4)	0.0085 (4)	0.0166 (4)	−0.0150 (4)
O1	0.0724 (13)	0.0468 (11)	0.0659 (12)	−0.0177 (10)	0.0322 (10)	−0.0218 (10)
N1	0.0545 (13)	0.0417 (12)	0.0414 (11)	−0.0069 (10)	0.0146 (10)	−0.0099 (9)
N2	0.0579 (14)	0.0382 (11)	0.0421 (11)	0.0032 (10)	0.0106 (10)	−0.0052 (9)
N3	0.0529 (13)	0.0410 (12)	0.0464 (12)	−0.0039 (10)	0.0136 (10)	−0.0014 (10)
C1	0.0576 (17)	0.0543 (17)	0.0502 (15)	−0.0021 (14)	0.0149 (13)	−0.0109 (13)
C2	0.066 (2)	0.065 (2)	0.079 (2)	−0.0172 (16)	0.0323 (17)	−0.0181 (17)
C3	0.091 (3)	0.072 (2)	0.069 (2)	−0.0111 (19)	0.0446 (19)	0.0006 (18)
C4	0.078 (2)	0.093 (3)	0.0476 (17)	−0.004 (2)	0.0215 (16)	0.0031 (17)
C5	0.0501 (16)	0.0691 (19)	0.0489 (15)	−0.0040 (14)	0.0121 (13)	−0.0057 (14)
C6	0.0459 (15)	0.0425 (14)	0.0452 (14)	0.0045 (12)	0.0166 (11)	−0.0041 (11)
C7	0.0516 (15)	0.0403 (14)	0.0430 (14)	−0.0003 (12)	0.0121 (12)	−0.0059 (11)
C8	0.0509 (15)	0.0371 (13)	0.0392 (13)	−0.0002 (11)	0.0096 (11)	−0.0024 (11)
C9	0.0575 (16)	0.0368 (13)	0.0425 (14)	−0.0023 (12)	0.0059 (12)	0.0013 (11)
C10	0.094 (2)	0.0503 (18)	0.0640 (19)	−0.0190 (17)	0.0189 (17)	−0.0101 (15)
C11	0.077 (2)	0.0498 (17)	0.0584 (17)	0.0109 (15)	0.0101 (15)	−0.0148 (14)
C12	0.0465 (15)	0.0432 (14)	0.0478 (14)	−0.0068 (12)	0.0142 (12)	−0.0026 (12)
C13	0.0420 (14)	0.0419 (14)	0.0417 (13)	−0.0032 (11)	0.0097 (11)	−0.0001 (11)
C14	0.0468 (15)	0.0392 (14)	0.0452 (14)	−0.0060 (11)	0.0102 (11)	0.0018 (11)
C15	0.0481 (15)	0.0450 (14)	0.0384 (13)	0.0029 (12)	0.0070 (11)	0.0017 (11)
C16	0.0444 (15)	0.0607 (17)	0.0440 (14)	−0.0025 (13)	0.0143 (11)	0.0024 (13)
C17	0.0503 (16)	0.0521 (16)	0.0568 (16)	−0.0101 (13)	0.0160 (13)	0.0031 (13)
C18	0.0520 (16)	0.0399 (14)	0.0534 (15)	−0.0065 (12)	0.0147 (12)	−0.0025 (12)
Cl3	0.0682 (5)	0.0619 (4)	0.0465 (4)	−0.0197 (4)	0.0142 (3)	−0.0035 (3)
Cl4	0.0845 (6)	0.0935 (6)	0.0552 (4)	0.0083 (5)	0.0275 (4)	−0.0113 (4)
O2	0.0703 (13)	0.0747 (14)	0.0603 (12)	−0.0309 (11)	0.0359 (10)	−0.0214 (11)
N4	0.0546 (14)	0.0606 (15)	0.0459 (12)	−0.0166 (11)	0.0199 (10)	−0.0111 (11)
N5	0.0432 (12)	0.0679 (15)	0.0467 (12)	−0.0105 (11)	0.0187 (10)	−0.0078 (11)
N6	0.0493 (13)	0.0532 (13)	0.0417 (12)	−0.0100 (11)	0.0095 (10)	−0.0052 (10)
C19	0.070 (2)	0.095 (3)	0.0527 (18)	−0.0213 (19)	0.0152 (16)	0.0014 (18)
C20	0.076 (2)	0.153 (4)	0.0458 (18)	−0.039 (3)	0.0159 (16)	−0.019 (2)
C21	0.082 (3)	0.133 (4)	0.087 (3)	−0.040 (3)	0.026 (2)	−0.061 (3)
C22	0.099 (3)	0.071 (3)	0.118 (4)	−0.014 (2)	0.010 (3)	−0.029 (2)
C23	0.078 (2)	0.060 (2)	0.072 (2)	−0.0059 (17)	0.0014 (17)	−0.0070 (17)
C24	0.0469 (15)	0.0605 (17)	0.0454 (15)	−0.0062 (13)	0.0177 (12)	−0.0131 (13)
C25	0.0529 (16)	0.0545 (16)	0.0384 (13)	−0.0094 (13)	0.0162 (12)	−0.0061 (12)
C26	0.0463 (15)	0.0508 (15)	0.0392 (13)	−0.0071 (12)	0.0094 (11)	−0.0024 (12)
C27	0.0407 (14)	0.0620 (17)	0.0421 (14)	−0.0070 (13)	0.0087 (11)	−0.0018 (13)
C28	0.0489 (17)	0.084 (2)	0.0631 (18)	−0.0193 (16)	0.0155 (14)	−0.0042 (17)
C29	0.0502 (18)	0.093 (3)	0.079 (2)	−0.0001 (17)	0.0200 (16)	−0.0169 (19)
C30	0.0495 (15)	0.0480 (15)	0.0423 (14)	−0.0099 (12)	0.0063 (12)	−0.0064 (12)
C31	0.0448 (14)	0.0464 (15)	0.0397 (13)	−0.0059 (12)	0.0016 (11)	−0.0050 (11)
C32	0.0465 (14)	0.0479 (15)	0.0342 (12)	−0.0040 (12)	0.0005 (11)	−0.0017 (11)
C33	0.0574 (17)	0.0593 (18)	0.0352 (13)	0.0097 (14)	0.0038 (12)	−0.0027 (12)
C34	0.081 (2)	0.0454 (16)	0.0532 (17)	0.0020 (16)	0.0015 (15)	−0.0146 (13)
C35	0.075 (2)	0.0501 (17)	0.0663 (19)	−0.0169 (16)	0.0094 (16)	−0.0145 (15)
C36	0.0567 (17)	0.0537 (17)	0.0595 (17)	−0.0137 (14)	0.0130 (14)	−0.0090 (14)

Geometric parameters (Å, º)

Cl1—C14	1.728 (3)	Cl3—C32	1.728 (3)
Cl2—C15	1.735 (3)	Cl4—C33	1.724 (3)
O1—C7	1.226 (3)	O2—C25	1.219 (3)
N1—C7	1.400 (3)	N4—C25	1.386 (3)
N1—N2	1.404 (3)	N4—N5	1.413 (3)
N1—C6	1.426 (3)	N4—C24	1.425 (3)
N2—C9	1.369 (3)	N5—C27	1.370 (3)
N2—C11	1.469 (3)	N5—C29	1.462 (4)
N3—C12	1.270 (3)	N6—C30	1.276 (3)
N3—C8	1.394 (3)	N6—C26	1.386 (3)
C1—C6	1.380 (4)	C19—C24	1.374 (4)
C1—C2	1.383 (4)	C19—C20	1.396 (5)
C1—H1	0.9300	C19—H19	0.9300
C2—C3	1.366 (5)	C20—C21	1.361 (6)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.366 (5)	C21—C22	1.350 (6)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.387 (4)	C22—C23	1.369 (5)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.375 (4)	C23—C24	1.368 (4)
C5—H5	0.9300	C23—H23	0.9300
C7—C8	1.438 (4)	C25—C26	1.449 (4)
C8—C9	1.360 (3)	C26—C27	1.358 (3)
C9—C10	1.486 (4)	C27—C28	1.492 (4)
C10—H10A	0.9600	C28—H28A	0.9600
C10—H10B	0.9600	C28—H28B	0.9600
C10—H10C	0.9600	C28—H28C	0.9600
C11—H11A	0.9600	C29—H29A	0.9600
C11—H11B	0.9600	C29—H29B	0.9600
C11—H11C	0.9600	C29—H29C	0.9600
C12—C13	1.473 (3)	C30—C31	1.460 (4)
C12—H12	0.9300	C30—H30	0.9300
C13—C18	1.391 (3)	C31—C36	1.395 (4)
C13—C14	1.399 (3)	C31—C32	1.397 (3)
C14—C15	1.387 (3)	C32—C33	1.386 (4)
C15—C16	1.372 (4)	C33—C34	1.379 (4)
C16—C17	1.373 (4)	C34—C35	1.367 (4)
C16—H16	0.9300	C34—H34	0.9300
C17—C18	1.377 (4)	C35—C36	1.364 (4)
C17—H17	0.9300	C35—H35	0.9300
C18—H18	0.9300	C36—H36	0.9300
C7—N1—N2	109.53 (19)	C25—N4—N5	110.2 (2)
C7—N1—C6	123.4 (2)	C25—N4—C24	125.8 (2)
N2—N1—C6	120.28 (19)	N5—N4—C24	118.3 (2)
C9—N2—N1	106.27 (19)	C27—N5—N4	105.89 (19)
C9—N2—C11	122.6 (2)	C27—N5—C29	121.9 (2)
N1—N2—C11	116.3 (2)	N4—N5—C29	113.9 (2)
C12—N3—C8	120.7 (2)	C30—N6—C26	121.2 (2)
C6—C1—C2	119.4 (3)	C24—C19—C20	118.4 (4)
C6—C1—H1	120.3	C24—C19—H19	120.8
C2—C1—H1	120.3	C20—C19—H19	120.8
C3—C2—C1	120.3 (3)	C21—C20—C19	120.4 (4)
C3—C2—H2	119.9	C21—C20—H20	119.8
C1—C2—H2	119.9	C19—C20—H20	119.8
C2—C3—C4	120.2 (3)	C22—C21—C20	119.7 (4)
C2—C3—H3	119.9	C22—C21—H21	120.2
C4—C3—H3	119.9	C20—C21—H21	120.2
C3—C4—C5	120.5 (3)	C21—C22—C23	121.6 (4)
C3—C4—H4	119.8	C21—C22—H22	119.2
C5—C4—H4	119.8	C23—C22—H22	119.2
C6—C5—C4	119.1 (3)	C24—C23—C22	118.9 (4)
C6—C5—H5	120.4	C24—C23—H23	120.6
C4—C5—H5	120.4	C22—C23—H23	120.6
C5—C6—C1	120.5 (2)	C23—C24—C19	120.9 (3)
C5—C6—N1	122.1 (2)	C23—C24—N4	118.4 (3)
C1—C6—N1	117.3 (2)	C19—C24—N4	120.7 (3)
O1—C7—N1	123.6 (2)	O2—C25—N4	123.7 (2)
O1—C7—C8	131.5 (2)	O2—C25—C26	131.8 (2)
N1—C7—C8	104.8 (2)	N4—C25—C26	104.4 (2)
C9—C8—N3	122.5 (2)	C27—C26—N6	122.1 (2)
C9—C8—C7	108.0 (2)	C27—C26—C25	108.2 (2)
N3—C8—C7	129.3 (2)	N6—C26—C25	129.3 (2)
C8—C9—N2	110.7 (2)	C26—C27—N5	110.6 (2)
C8—C9—C10	128.2 (2)	C26—C27—C28	128.2 (3)
N2—C9—C10	121.1 (2)	N5—C27—C28	121.2 (2)
C9—C10—H10A	109.5	C27—C28—H28A	109.5
C9—C10—H10B	109.5	C27—C28—H28B	109.5
H10A—C10—H10B	109.5	H28A—C28—H28B	109.5
C9—C10—H10C	109.5	C27—C28—H28C	109.5
H10A—C10—H10C	109.5	H28A—C28—H28C	109.5
H10B—C10—H10C	109.5	H28B—C28—H28C	109.5
N2—C11—H11A	109.5	N5—C29—H29A	109.5
N2—C11—H11B	109.5	N5—C29—H29B	109.5
H11A—C11—H11B	109.5	H29A—C29—H29B	109.5
N2—C11—H11C	109.5	N5—C29—H29C	109.5
H11A—C11—H11C	109.5	H29A—C29—H29C	109.5
H11B—C11—H11C	109.5	H29B—C29—H29C	109.5
N3—C12—C13	120.0 (2)	N6—C30—C31	119.9 (2)
N3—C12—H12	120.0	N6—C30—H30	120.1
C13—C12—H12	120.0	C31—C30—H30	120.1
C18—C13—C14	117.6 (2)	C36—C31—C32	117.8 (2)
C18—C13—C12	119.9 (2)	C36—C31—C30	119.9 (2)
C14—C13—C12	122.5 (2)	C32—C31—C30	122.3 (2)
C15—C14—C13	120.3 (2)	C33—C32—C31	120.0 (2)
C15—C14—Cl1	119.6 (2)	C33—C32—Cl3	119.7 (2)
C13—C14—Cl1	120.14 (19)	C31—C32—Cl3	120.3 (2)
C16—C15—C14	120.9 (2)	C34—C33—C32	120.6 (3)
C16—C15—Cl2	118.2 (2)	C34—C33—Cl4	118.6 (2)
C14—C15—Cl2	120.9 (2)	C32—C33—Cl4	120.8 (2)
C15—C16—C17	119.3 (2)	C35—C34—C33	119.6 (3)
C15—C16—H16	120.4	C35—C34—H34	120.2
C17—C16—H16	120.4	C33—C34—H34	120.2
C16—C17—C18	120.5 (2)	C36—C35—C34	120.6 (3)
C16—C17—H17	119.8	C36—C35—H35	119.7
C18—C17—H17	119.8	C34—C35—H35	119.7
C17—C18—C13	121.4 (2)	C35—C36—C31	121.4 (3)
C17—C18—H18	119.3	C35—C36—H36	119.3
C13—C18—H18	119.3	C31—C36—H36	119.3
C7—N1—N2—C9	8.6 (3)	C25—N4—N5—C27	8.5 (3)
C6—N1—N2—C9	160.7 (2)	C24—N4—N5—C27	163.6 (2)
C7—N1—N2—C11	148.9 (2)	C25—N4—N5—C29	145.2 (3)
C6—N1—N2—C11	−59.0 (3)	C24—N4—N5—C29	−59.7 (3)
C6—C1—C2—C3	1.4 (5)	C24—C19—C20—C21	1.3 (5)
C1—C2—C3—C4	−0.2 (5)	C19—C20—C21—C22	0.2 (6)
C2—C3—C4—C5	−0.3 (5)	C20—C21—C22—C23	−1.2 (7)
C3—C4—C5—C6	−0.3 (5)	C21—C22—C23—C24	0.5 (6)
C4—C5—C6—C1	1.4 (4)	C22—C23—C24—C19	1.2 (5)
C4—C5—C6—N1	−176.3 (3)	C22—C23—C24—N4	−177.9 (3)
C2—C1—C6—C5	−2.0 (4)	C20—C19—C24—C23	−2.1 (5)
C2—C1—C6—N1	175.8 (3)	C20—C19—C24—N4	177.0 (3)
C7—N1—C6—C5	118.8 (3)	C25—N4—C24—C23	−77.9 (4)
N2—N1—C6—C5	−29.3 (4)	N5—N4—C24—C23	131.2 (3)
C7—N1—C6—C1	−59.0 (3)	C25—N4—C24—C19	103.0 (3)
N2—N1—C6—C1	152.9 (2)	N5—N4—C24—C19	−47.8 (4)
N2—N1—C7—O1	171.3 (2)	N5—N4—C25—O2	170.4 (3)
C6—N1—C7—O1	20.3 (4)	C24—N4—C25—O2	17.6 (5)
N2—N1—C7—C8	−7.0 (3)	N5—N4—C25—C26	−7.5 (3)
C6—N1—C7—C8	−158.1 (2)	C24—N4—C25—C26	−160.2 (3)
C12—N3—C8—C9	−179.9 (3)	C30—N6—C26—C27	−173.8 (3)
C12—N3—C8—C7	4.7 (4)	C30—N6—C26—C25	13.1 (4)
O1—C7—C8—C9	−175.3 (3)	O2—C25—C26—C27	−173.9 (3)
N1—C7—C8—C9	2.9 (3)	N4—C25—C26—C27	3.6 (3)
O1—C7—C8—N3	0.6 (5)	O2—C25—C26—N6	−0.1 (5)
N1—C7—C8—N3	178.8 (2)	N4—C25—C26—N6	177.4 (3)
N3—C8—C9—N2	−173.8 (2)	N6—C26—C27—N5	−172.7 (2)
C7—C8—C9—N2	2.4 (3)	C25—C26—C27—N5	1.6 (3)
N3—C8—C9—C10	7.3 (5)	N6—C26—C27—C28	5.6 (5)
C7—C8—C9—C10	−176.5 (3)	C25—C26—C27—C28	179.9 (3)
N1—N2—C9—C8	−6.7 (3)	N4—N5—C27—C26	−6.1 (3)
C11—N2—C9—C8	−143.9 (2)	C29—N5—C27—C26	−138.5 (3)
N1—N2—C9—C10	172.3 (2)	N4—N5—C27—C28	175.5 (3)
C11—N2—C9—C10	35.0 (4)	C29—N5—C27—C28	43.1 (4)
C8—N3—C12—C13	−178.9 (2)	C26—N6—C30—C31	−177.5 (2)
N3—C12—C13—C18	−10.1 (4)	N6—C30—C31—C36	0.5 (4)
N3—C12—C13—C14	168.2 (3)	N6—C30—C31—C32	178.5 (2)
C18—C13—C14—C15	1.5 (4)	C36—C31—C32—C33	0.7 (4)
C12—C13—C14—C15	−176.9 (2)	C30—C31—C32—C33	−177.3 (2)
C18—C13—C14—Cl1	180.0 (2)	C36—C31—C32—Cl3	179.7 (2)
C12—C13—C14—Cl1	1.6 (4)	C30—C31—C32—Cl3	1.7 (4)
C13—C14—C15—C16	−0.8 (4)	C31—C32—C33—C34	−0.9 (4)
Cl1—C14—C15—C16	−179.3 (2)	Cl3—C32—C33—C34	−179.8 (2)
C13—C14—C15—Cl2	178.5 (2)	C31—C32—C33—Cl4	178.3 (2)
Cl1—C14—C15—Cl2	0.0 (3)	Cl3—C32—C33—Cl4	−0.6 (3)
C14—C15—C16—C17	−0.4 (4)	C32—C33—C34—C35	0.2 (4)
Cl2—C15—C16—C17	−179.6 (2)	Cl4—C33—C34—C35	−179.1 (2)
C15—C16—C17—C18	0.8 (4)	C33—C34—C35—C36	0.7 (5)
C16—C17—C18—C13	0.0 (4)	C34—C35—C36—C31	−0.9 (5)
C14—C13—C18—C17	−1.1 (4)	C32—C31—C36—C35	0.2 (4)
C12—C13—C18—C17	177.3 (3)	C30—C31—C36—C35	178.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2^i	0.93	2.52	3.153 (4)	125
C12—H12···Cl1	0.93	2.70	3.067 (3)	104
C12—H12···O1	0.93	2.35	3.025 (3)	129
C35—H35···O1^ii	0.93	2.65	3.221 (3)	121
C30—H30···Cl3	0.93	2.68	3.059 (3)	105
C30—H30···O2	0.93	2.42	3.061 (3)	126

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