4-Chloro-2-[(4-phenyl­thia­zol-2-yl)hydrazonometh­yl]­phenol: a polymorph with Z′ = 2

The title compound, β-C₁₆H₁₂ClN₃OS, crystallizes with two independent mol­ecules in the asymmetric unit, both of which show a similar twisted conformation. It is polymorphic with α-C₁₆H₁₂ClN₃OS [Çaliskan, Daĝ, Yüksektepe, Cukurovali & Murat (2006). Acta Cryst. E62, o4889–o4890]; both forms crystallize in the same space group. The two independent mol­ecules in β-C₁₆H₁₂ClN₃OS are linked into dimers by pairs of N—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.123
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-Chloro-2-[(4-phenylthiazol-2-yl)hydrazonomethyl]phenol

Crystal data

C16H12ClN3OS	F(000) = 1360
Mr = 329.80	Dx = 1.427 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 35261 reflections
a = 10.8757 (4) Å	θ = 1.2–25.1°
b = 8.2302 (5) Å	µ = 0.39 mm^−1
c = 34.9645 (13) Å	T = 296 K
β = 101.144 (3)°	Prism, pale yellow
V = 3070.6 (2) Å^3	0.60 × 0.51 × 0.31 mm
Z = 8

Data collection

Stoe IPDS-2 diffractometer	5398 independent reflections
Radiation source: fine-focus sealed tube	3603 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
Detector resolution: 6.67 pixels mm^-1	θmax = 25.0°, θmin = 1.9°
ω scans	h = −12→12
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.765, Tmax = 0.904	l = −41→41
36136 measured reflections

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-atom parameters constrained
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0772P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
5398 reflections	Δρmax = 0.75 e Å^−3
398 parameters	Δρmin = −0.70 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0204 (13)

Special details

Experimental. Characteristic IR bands: 3280 cm-1 ν(O—H), 3120 cm-1 ν (N—H), 1614 cm-1 ν(C=N azomethine), 1604 cm-1 ν(C=N thiazole), 676 cm-1 ν(C—S—C thiazole). Characteristic 1H NMR shifts (CDCl3,δ, p.p.m.): 6.96 (s, 1H, thiazole), 7.20–7.89 (m, 8H, aromatics), 8.31 (s, 1H, azomethine), 10.40 (s,1H, –NH–), 12.20 (s, 1H, –OH)·Characteristic 13 C NMR shifts (CDCl3,δ, p.p.m.): 125.05 (C1),156.41 (C2), 119.74 (C3), 131.57 (C4), 123.93(C5), 130.39 (C6),139.38 (C7), 169.69 (C8), 105.31 (C9), 152.2 (C10), 136.22 (C11),126.69 (C12), 127.33 (C13), 129.37 (C14).

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	0.48293 (8)	0.31249 (13)	−0.25553 (2)	0.1076 (3)
Cl2	1.02569 (7)	−0.03209 (12)	0.237484 (19)	0.1012 (3)
S1	0.40166 (6)	0.19980 (13)	−0.008081 (19)	0.0956 (3)
S2	1.09624 (5)	0.23121 (10)	−0.003219 (19)	0.0780 (2)
O1	0.27872 (14)	0.2209 (2)	−0.11398 (5)	0.0804 (5)
H1	0.3336	0.2271	−0.0943	0.121*
O2	1.20688 (14)	0.0333 (2)	0.09098 (5)	0.0789 (5)
H2B	1.1505	0.0591	0.0729	0.118*
N1	0.62516 (16)	0.2710 (3)	0.02769 (5)	0.0652 (5)
N2	0.59798 (18)	0.2772 (3)	−0.04051 (5)	0.0813 (7)
H2A	0.6755	0.2967	−0.0407	0.098*
N3	0.51048 (17)	0.2654 (3)	−0.07403 (5)	0.0701 (5)
N4	0.87225 (16)	0.3234 (2)	−0.03283 (5)	0.0598 (5)
N5	0.89425 (17)	0.2068 (3)	0.02955 (5)	0.0696 (5)
H5A	0.8160	0.2134	0.0305	0.084*
N6	0.98007 (16)	0.1451 (2)	0.05974 (5)	0.0625 (5)
C1	0.6116 (2)	0.2498 (3)	0.09768 (6)	0.0626 (6)
C2	0.5679 (2)	0.1542 (3)	0.12479 (7)	0.0751 (7)
H2	0.5028	0.0815	0.1164	0.090*
C3	0.6190 (3)	0.1650 (4)	0.16386 (7)	0.0856 (8)
H3	0.5884	0.0999	0.1816	0.103*
C4	0.7143 (3)	0.2706 (4)	0.17657 (8)	0.0903 (9)
H4	0.7483	0.2787	0.2030	0.108*
C5	0.7603 (3)	0.3658 (4)	0.15005 (9)	0.0901 (8)
H5	0.8261	0.4372	0.1587	0.108*
C6	0.7090 (2)	0.3556 (3)	0.11072 (8)	0.0764 (7)
H6	0.7403	0.4203	0.0930	0.092*
C7	0.5539 (2)	0.2376 (3)	0.05605 (6)	0.0652 (6)
C8	0.4336 (2)	0.1974 (4)	0.04172 (7)	0.0864 (8)
H8	0.3753	0.1716	0.0570	0.104*
C9	0.5555 (2)	0.2564 (3)	−0.00672 (7)	0.0690 (6)
C10	0.5470 (2)	0.2799 (3)	−0.10660 (6)	0.0666 (6)
H10	0.6318	0.2942	−0.1066	0.080*
C11	0.4586 (2)	0.2743 (3)	−0.14335 (6)	0.0610 (5)
C12	0.3300 (2)	0.2452 (3)	−0.14614 (7)	0.0635 (6)
C13	0.2512 (2)	0.2399 (3)	−0.18198 (7)	0.0730 (6)
H13	0.1660	0.2214	−0.1834	0.088*
C14	0.2967 (2)	0.2615 (3)	−0.21569 (7)	0.0748 (7)
H14	0.2429	0.2575	−0.2398	0.090*
C15	0.4236 (2)	0.2894 (3)	−0.21321 (7)	0.0716 (6)
C16	0.5031 (2)	0.2968 (3)	−0.17782 (6)	0.0663 (6)
H16	0.5878	0.3170	−0.1767	0.080*
C17	0.8912 (2)	0.4328 (3)	−0.09760 (6)	0.0615 (5)
C18	0.7902 (2)	0.5375 (3)	−0.10074 (7)	0.0729 (6)
H18	0.7572	0.5620	−0.0788	0.087*
C19	0.7379 (3)	0.6058 (4)	−0.13615 (9)	0.0892 (8)
H19	0.6696	0.6753	−0.1380	0.107*
C20	0.7863 (3)	0.5716 (4)	−0.16881 (9)	0.0970 (9)
H20	0.7507	0.6175	−0.1927	0.116*
C21	0.8868 (3)	0.4701 (4)	−0.16594 (8)	0.0936 (9)
H21	0.9200	0.4475	−0.1880	0.112*
C22	0.9394 (3)	0.4008 (3)	−0.13080 (7)	0.0777 (7)
H22	1.0080	0.3319	−0.1293	0.093*
C23	0.94659 (19)	0.3567 (3)	−0.06019 (6)	0.0592 (5)
C24	1.0675 (2)	0.3143 (4)	−0.04898 (7)	0.0770 (7)
H24	1.1281	0.3283	−0.0642	0.092*
C25	0.93961 (19)	0.2572 (3)	−0.00200 (6)	0.0584 (5)
C26	0.94424 (19)	0.1056 (3)	0.09130 (6)	0.0635 (6)
H26	0.8598	0.1123	0.0926	0.076*
C27	1.03403 (19)	0.0506 (3)	0.12507 (6)	0.0588 (5)
C28	0.9942 (2)	0.0333 (3)	0.16048 (6)	0.0660 (6)
H28	0.9108	0.0524	0.1617	0.079*
C29	1.0778 (2)	−0.0118 (3)	0.19357 (6)	0.0691 (6)
C30	1.2017 (2)	−0.0399 (3)	0.19244 (7)	0.0763 (7)
H30	1.2576	−0.0705	0.2149	0.092*
C31	1.2419 (2)	−0.0225 (3)	0.15797 (8)	0.0749 (7)
H31	1.3259	−0.0396	0.1573	0.090*
C32	1.1601 (2)	0.0201 (3)	0.12418 (7)	0.0636 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1008 (5)	0.1665 (8)	0.0589 (4)	0.0036 (5)	0.0234 (4)	0.0175 (4)
Cl2	0.0955 (5)	0.1498 (7)	0.0565 (4)	−0.0171 (5)	0.0097 (3)	0.0076 (4)
S1	0.0442 (3)	0.1791 (8)	0.0633 (4)	−0.0053 (4)	0.0097 (3)	0.0085 (4)
S2	0.0468 (3)	0.1183 (6)	0.0699 (4)	0.0089 (3)	0.0135 (3)	0.0166 (4)
O1	0.0527 (9)	0.1257 (15)	0.0641 (10)	−0.0042 (9)	0.0146 (7)	0.0056 (9)
O2	0.0577 (9)	0.1095 (14)	0.0718 (10)	0.0092 (9)	0.0184 (8)	0.0069 (9)
N1	0.0500 (10)	0.0940 (14)	0.0522 (10)	−0.0007 (9)	0.0112 (8)	0.0053 (9)
N2	0.0477 (10)	0.142 (2)	0.0530 (11)	−0.0086 (11)	0.0076 (8)	0.0105 (12)
N3	0.0500 (10)	0.1067 (16)	0.0523 (10)	−0.0003 (10)	0.0063 (8)	0.0065 (10)
N4	0.0490 (9)	0.0764 (12)	0.0545 (10)	0.0013 (9)	0.0114 (8)	0.0043 (9)
N5	0.0467 (10)	0.1040 (15)	0.0584 (11)	0.0050 (10)	0.0105 (8)	0.0151 (10)
N6	0.0485 (9)	0.0810 (13)	0.0560 (10)	0.0019 (9)	0.0049 (8)	0.0067 (9)
C1	0.0562 (12)	0.0764 (15)	0.0578 (12)	0.0085 (11)	0.0173 (10)	−0.0024 (11)
C2	0.0749 (15)	0.0945 (18)	0.0597 (14)	−0.0037 (14)	0.0228 (12)	−0.0029 (13)
C3	0.098 (2)	0.106 (2)	0.0576 (15)	0.0049 (17)	0.0258 (14)	−0.0006 (14)
C4	0.100 (2)	0.110 (2)	0.0581 (15)	0.0161 (19)	0.0106 (14)	−0.0133 (15)
C5	0.0869 (18)	0.095 (2)	0.083 (2)	−0.0042 (16)	0.0045 (15)	−0.0233 (16)
C6	0.0763 (16)	0.0806 (17)	0.0738 (16)	−0.0033 (13)	0.0183 (13)	−0.0010 (13)
C7	0.0500 (12)	0.0915 (17)	0.0562 (12)	0.0034 (11)	0.0158 (10)	0.0028 (11)
C8	0.0508 (13)	0.146 (3)	0.0658 (15)	0.0008 (14)	0.0200 (11)	0.0093 (16)
C9	0.0468 (11)	0.1028 (19)	0.0575 (13)	0.0045 (12)	0.0108 (10)	0.0084 (13)
C10	0.0493 (12)	0.0920 (17)	0.0591 (13)	−0.0039 (11)	0.0121 (10)	0.0049 (12)
C11	0.0527 (12)	0.0753 (15)	0.0546 (12)	0.0009 (11)	0.0089 (9)	0.0045 (10)
C12	0.0529 (12)	0.0787 (15)	0.0598 (13)	0.0017 (11)	0.0132 (10)	0.0015 (11)
C13	0.0545 (13)	0.0946 (18)	0.0668 (15)	0.0002 (12)	0.0038 (11)	0.0007 (13)
C14	0.0708 (15)	0.0895 (18)	0.0596 (14)	0.0047 (13)	0.0014 (11)	−0.0009 (12)
C15	0.0744 (15)	0.0858 (17)	0.0552 (13)	0.0060 (13)	0.0140 (11)	0.0095 (12)
C16	0.0581 (13)	0.0833 (16)	0.0586 (13)	0.0009 (12)	0.0142 (10)	0.0074 (11)
C17	0.0594 (12)	0.0664 (14)	0.0597 (13)	−0.0074 (11)	0.0139 (10)	0.0047 (11)
C18	0.0694 (14)	0.0745 (16)	0.0743 (15)	0.0001 (12)	0.0125 (12)	0.0046 (12)
C19	0.0804 (17)	0.0830 (18)	0.097 (2)	0.0015 (15)	−0.0010 (15)	0.0217 (16)
C20	0.107 (2)	0.101 (2)	0.0775 (19)	−0.0149 (19)	0.0022 (16)	0.0299 (17)
C21	0.112 (2)	0.106 (2)	0.0653 (16)	−0.012 (2)	0.0218 (15)	0.0155 (15)
C22	0.0837 (16)	0.0845 (17)	0.0681 (15)	−0.0011 (14)	0.0229 (12)	0.0083 (13)
C23	0.0517 (12)	0.0686 (14)	0.0587 (13)	−0.0013 (10)	0.0139 (9)	0.0006 (10)
C24	0.0547 (13)	0.108 (2)	0.0728 (15)	0.0022 (13)	0.0227 (11)	0.0146 (14)
C25	0.0456 (11)	0.0741 (14)	0.0553 (12)	−0.0003 (10)	0.0096 (9)	0.0015 (10)
C26	0.0486 (11)	0.0836 (16)	0.0578 (13)	−0.0002 (11)	0.0090 (9)	0.0053 (11)
C27	0.0533 (11)	0.0661 (13)	0.0562 (12)	−0.0024 (10)	0.0082 (9)	0.0020 (10)
C28	0.0572 (12)	0.0793 (16)	0.0611 (13)	−0.0010 (11)	0.0106 (10)	0.0039 (11)
C29	0.0710 (15)	0.0798 (16)	0.0536 (13)	−0.0084 (12)	0.0047 (11)	0.0031 (11)
C30	0.0687 (15)	0.0857 (18)	0.0671 (15)	−0.0026 (13)	−0.0052 (12)	0.0096 (13)
C31	0.0554 (13)	0.0857 (17)	0.0799 (16)	0.0058 (12)	0.0041 (12)	0.0095 (13)
C32	0.0549 (12)	0.0704 (15)	0.0658 (14)	0.0007 (10)	0.0123 (10)	0.0029 (11)

Geometric parameters (Å, º)

Cl1—C15	1.735 (2)	C10—C11	1.449 (3)
Cl2—C29	1.744 (2)	C10—H10	0.9300
S1—C8	1.709 (3)	C11—C16	1.395 (3)
S1—C9	1.729 (2)	C11—C12	1.403 (3)
S2—C24	1.712 (3)	C12—C13	1.376 (3)
S2—C25	1.725 (2)	C13—C14	1.375 (3)
O1—C12	1.363 (3)	C13—H13	0.9300
O1—H1	0.8200	C14—C15	1.386 (3)
O2—C32	1.359 (3)	C14—H14	0.9300
O2—H2B	0.8200	C15—C16	1.367 (3)
N1—C9	1.298 (3)	C16—H16	0.9300
N1—C7	1.398 (3)	C17—C18	1.384 (3)
N2—C9	1.360 (3)	C17—C22	1.388 (3)
N2—N3	1.363 (3)	C17—C23	1.470 (3)
N2—H2A	0.8600	C18—C19	1.378 (4)
N3—C10	1.282 (3)	C18—H18	0.9300
N4—C25	1.300 (3)	C19—C20	1.376 (4)
N4—C23	1.394 (3)	C19—H19	0.9300
N5—C25	1.358 (3)	C20—C21	1.364 (4)
N5—N6	1.365 (2)	C20—H20	0.9300
N5—H5A	0.8600	C21—C22	1.375 (4)
N6—C26	1.281 (3)	C21—H21	0.9300
C1—C6	1.379 (4)	C22—H22	0.9300
C1—C2	1.385 (3)	C23—C24	1.344 (3)
C1—C7	1.473 (3)	C24—H24	0.9300
C2—C3	1.374 (4)	C26—C27	1.451 (3)
C2—H2	0.9300	C26—H26	0.9300
C3—C4	1.360 (4)	C27—C28	1.396 (3)
C3—H3	0.9300	C27—C32	1.400 (3)
C4—C5	1.379 (4)	C28—C29	1.377 (3)
C4—H4	0.9300	C28—H28	0.9300
C5—C6	1.383 (4)	C29—C30	1.376 (3)
C5—H5	0.9300	C30—C31	1.366 (3)
C6—H6	0.9300	C30—H30	0.9300
C7—C8	1.349 (3)	C31—C32	1.380 (3)
C8—H8	0.9300	C31—H31	0.9300
C8—S1—C9	88.29 (11)	C15—C14—H14	120.4
C24—S2—C25	88.34 (11)	C16—C15—C14	120.8 (2)
C12—O1—H1	109.5	C16—C15—Cl1	119.53 (19)
C32—O2—H2B	109.5	C14—C15—Cl1	119.67 (19)
C9—N1—C7	109.58 (18)	C15—C16—C11	120.8 (2)
C9—N2—N3	116.11 (18)	C15—C16—H16	119.6
C9—N2—H2A	121.9	C11—C16—H16	119.6
N3—N2—H2A	121.9	C18—C17—C22	118.3 (2)
C10—N3—N2	118.20 (19)	C18—C17—C23	121.2 (2)
C25—N4—C23	110.05 (17)	C22—C17—C23	120.5 (2)
C25—N5—N6	116.14 (17)	C19—C18—C17	120.6 (2)
C25—N5—H5A	121.9	C19—C18—H18	119.7
N6—N5—H5A	121.9	C17—C18—H18	119.7
C26—N6—N5	118.96 (17)	C20—C19—C18	120.3 (3)
C6—C1—C2	118.4 (2)	C20—C19—H19	119.8
C6—C1—C7	121.5 (2)	C18—C19—H19	119.8
C2—C1—C7	120.1 (2)	C21—C20—C19	119.6 (3)
C3—C2—C1	121.1 (3)	C21—C20—H20	120.2
C3—C2—H2	119.4	C19—C20—H20	120.2
C1—C2—H2	119.4	C20—C21—C22	120.6 (3)
C4—C3—C2	120.2 (3)	C20—C21—H21	119.7
C4—C3—H3	119.9	C22—C21—H21	119.7
C2—C3—H3	119.9	C21—C22—C17	120.6 (3)
C3—C4—C5	119.7 (3)	C21—C22—H22	119.7
C3—C4—H4	120.1	C17—C22—H22	119.7
C5—C4—H4	120.1	C24—C23—N4	114.4 (2)
C4—C5—C6	120.3 (3)	C24—C23—C17	125.4 (2)
C4—C5—H5	119.8	N4—C23—C17	120.14 (18)
C6—C5—H5	119.8	C23—C24—S2	111.56 (17)
C1—C6—C5	120.2 (3)	C23—C24—H24	124.2
C1—C6—H6	119.9	S2—C24—H24	124.2
C5—C6—H6	119.9	N4—C25—N5	124.53 (19)
C8—C7—N1	114.6 (2)	N4—C25—S2	115.62 (15)
C8—C7—C1	125.5 (2)	N5—C25—S2	119.85 (16)
N1—C7—C1	119.91 (19)	N6—C26—C27	120.72 (19)
C7—C8—S1	111.53 (18)	N6—C26—H26	119.6
C7—C8—H8	124.2	C27—C26—H26	119.6
S1—C8—H8	124.2	C28—C27—C32	118.30 (19)
N1—C9—N2	123.9 (2)	C28—C27—C26	118.57 (19)
N1—C9—S1	116.04 (16)	C32—C27—C26	123.08 (19)
N2—C9—S1	119.97 (17)	C29—C28—C27	120.4 (2)
N3—C10—C11	121.2 (2)	C29—C28—H28	119.8
N3—C10—H10	119.4	C27—C28—H28	119.8
C11—C10—H10	119.4	C30—C29—C28	120.8 (2)
C16—C11—C12	118.0 (2)	C30—C29—Cl2	119.73 (18)
C16—C11—C10	118.7 (2)	C28—C29—Cl2	119.46 (18)
C12—C11—C10	123.26 (19)	C31—C30—C29	119.3 (2)
O1—C12—C13	117.7 (2)	C31—C30—H30	120.3
O1—C12—C11	121.9 (2)	C29—C30—H30	120.3
C13—C12—C11	120.4 (2)	C30—C31—C32	121.3 (2)
C14—C13—C12	120.8 (2)	C30—C31—H31	119.4
C14—C13—H13	119.6	C32—C31—H31	119.4
C12—C13—H13	119.6	O2—C32—C31	117.8 (2)
C13—C14—C15	119.2 (2)	O2—C32—C27	122.32 (19)
C13—C14—H14	120.4	C31—C32—C27	119.9 (2)
C9—N2—N3—C10	−178.1 (2)	C10—C11—C16—C15	178.7 (2)
C25—N5—N6—C26	175.4 (2)	C22—C17—C18—C19	1.0 (4)
C6—C1—C2—C3	0.6 (4)	C23—C17—C18—C19	−178.9 (2)
C7—C1—C2—C3	−179.1 (2)	C17—C18—C19—C20	−0.5 (4)
C1—C2—C3—C4	0.0 (4)	C18—C19—C20—C21	−0.3 (4)
C2—C3—C4—C5	−0.7 (4)	C19—C20—C21—C22	0.5 (5)
C3—C4—C5—C6	0.8 (4)	C20—C21—C22—C17	0.1 (4)
C2—C1—C6—C5	−0.5 (4)	C18—C17—C22—C21	−0.8 (4)
C7—C1—C6—C5	179.2 (2)	C23—C17—C22—C21	179.1 (2)
C4—C5—C6—C1	−0.2 (4)	C25—N4—C23—C24	0.1 (3)
C9—N1—C7—C8	0.7 (3)	C25—N4—C23—C17	−179.7 (2)
C9—N1—C7—C1	−178.6 (2)	C18—C17—C23—C24	−149.7 (3)
C6—C1—C7—C8	−150.2 (3)	C22—C17—C23—C24	30.3 (4)
C2—C1—C7—C8	29.5 (4)	C18—C17—C23—N4	30.0 (3)
C6—C1—C7—N1	29.0 (3)	C22—C17—C23—N4	−149.9 (2)
C2—C1—C7—N1	−151.3 (2)	N4—C23—C24—S2	−0.5 (3)
N1—C7—C8—S1	−0.3 (3)	C17—C23—C24—S2	179.29 (19)
C1—C7—C8—S1	179.0 (2)	C25—S2—C24—C23	0.6 (2)
C9—S1—C8—C7	−0.1 (2)	C23—N4—C25—N5	−178.4 (2)
C7—N1—C9—N2	−178.4 (2)	C23—N4—C25—S2	0.4 (2)
C7—N1—C9—S1	−0.8 (3)	N6—N5—C25—N4	−177.9 (2)
N3—N2—C9—N1	−176.8 (2)	N6—N5—C25—S2	3.4 (3)
N3—N2—C9—S1	5.7 (3)	C24—S2—C25—N4	−0.6 (2)
C8—S1—C9—N1	0.5 (2)	C24—S2—C25—N5	178.3 (2)
C8—S1—C9—N2	178.2 (2)	N5—N6—C26—C27	−175.5 (2)
N2—N3—C10—C11	−177.8 (2)	N6—C26—C27—C28	170.1 (2)
N3—C10—C11—C16	177.6 (2)	N6—C26—C27—C32	−7.3 (4)
N3—C10—C11—C12	−3.2 (4)	C32—C27—C28—C29	0.4 (4)
C16—C11—C12—O1	179.6 (2)	C26—C27—C28—C29	−177.2 (2)
C10—C11—C12—O1	0.4 (4)	C27—C28—C29—C30	0.3 (4)
C16—C11—C12—C13	−0.2 (4)	C27—C28—C29—Cl2	179.86 (19)
C10—C11—C12—C13	−179.4 (2)	C28—C29—C30—C31	0.1 (4)
O1—C12—C13—C14	−179.3 (2)	Cl2—C29—C30—C31	−179.5 (2)
C11—C12—C13—C14	0.5 (4)	C29—C30—C31—C32	−1.1 (4)
C12—C13—C14—C15	−0.2 (4)	C30—C31—C32—O2	−179.3 (2)
C13—C14—C15—C16	−0.5 (4)	C30—C31—C32—C27	1.8 (4)
C13—C14—C15—Cl1	178.6 (2)	C28—C27—C32—O2	179.8 (2)
C14—C15—C16—C11	0.8 (4)	C26—C27—C32—O2	−2.8 (4)
Cl1—C15—C16—C11	−178.25 (19)	C28—C27—C32—C31	−1.4 (3)
C12—C11—C16—C15	−0.5 (4)	C26—C27—C32—C31	176.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N4	0.86	2.11	2.967 (3)	171
N5—H5A···N1	0.86	2.11	2.962 (3)	170
O1—H1···N3	0.82	1.94	2.661 (2)	146
O2—H2B···N6	0.82	1.95	2.661 (2)	144