3-{2-[2-(3-Hy-droxy-benzyl-idene)hydrazin-1-yl]-1,3-thia-zol-4-yl}-2H-chromen-2-one hemihydrate.

In the title compound, C(19)H(13)N(3)O(3)S·0.5H(2)O, both organic mol-ecules (A and B) exist in E configurations with respect to the acyclic C=N bond and have similar overall conformations. In mol-ecule A, the essentially planar thia-zole ring [maximum deviation = 0.010 (2) Å] is inclined at inter-planar angles of 11.44 (10) and 32.50 (12)°, with the 2H-chromene ring system and the benzene ring, respectively. The equivalent values for mol-ecule B are 0.002 (2) Å, 7.71 (9) and 12.51 (12)°. In the crystal structure, neighbouring mol-ecules are inter-connected into infinite layers lying parallel to (010) by O-H⋯O, O-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds. Further stabilization of the crystal structure is provided by weak inter-molecular C-H⋯π and π-π [centroid-centroid distance = 3.6380 (19) Å] inter-actions.

Related literature

For general background to and applications of amino­thia­zoles, see: Anderson et al. (2002 ▶); Finn et al. (2004 ▶); Gursoy & Karah (2000 ▶); Habib & Khalil (1984 ▶); Hiremath et al. (1992 ▶); Hofmanová et al. (1998 ▶); Jayashree et al. (2005 ▶); Karah et al. (1998 ▶); Kimura et al. (1985 ▶); Laffitte et al. (2002 ▶); Mitscher (2002 ▶); Moffett (1964 ▶); Ohkuba et al. (1995 ▶); Patt et al. (1992 ▶); Tassies et al. (2002 ▶); Wattenberg et al. (1979 ▶); Weber et al. (1998 ▶). For the preparation of the title compound, see: Lv et al. (2010 ▶); Siddiqui et al. (2009 ▶). For related structures, see: Arshad et al. (2010 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C19H13N3O3S·0.5H2O

M = 372.39

Monoclinic,

a = 8.012 (3) Å

b = 32.775 (11) Å

c = 12.619 (4) Å

β = 93.034 (7)°

V = 3309 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 100 K

0.34 × 0.14 × 0.05 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.928, T max = 0.990

31194 measured reflections

7564 independent reflections

5266 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.128

S = 1.06

7564 reflections

480 parameters

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019653/hb5467sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019653/hb5467Isup2.hkl

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

C19H13N3O3S·0.5H2O	F(000) = 1544
Mr = 372.39	Dx = 1.495 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3134 reflections
a = 8.012 (3) Å	θ = 2.5–27.6°
b = 32.775 (11) Å	µ = 0.23 mm−1
c = 12.619 (4) Å	T = 100 K
β = 93.034 (7)°	Plate, yellow
V = 3309 (2) Å3	0.34 × 0.14 × 0.05 mm
Z = 8

Bruker APEXII DUO CCD diffractometer	7564 independent reflections
Radiation source: fine-focus sealed tube	5266 reflections with I > 2σ(I)
graphite	Rint = 0.073
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.928, Tmax = 0.990	k = −42→42
31194 measured reflections	l = −16→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0407P)2 + 2.6662P] where P = (Fo2 + 2Fc2)/3
7564 reflections	(Δ/σ)max < 0.001
480 parameters	Δρmax = 0.94 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1A	−0.04957 (8)	0.042270 (18)	0.83927 (5)	0.01871 (15)
O1A	−0.0143 (2)	−0.12215 (5)	0.63046 (14)	0.0206 (4)
O2A	−0.1831 (2)	−0.07185 (5)	0.65803 (15)	0.0254 (4)
O3A	−0.0075 (3)	0.22741 (6)	0.90542 (17)	0.0346 (5)
H3OA	−0.0231	0.2112	0.8563	0.052*
N1A	0.1639 (2)	−0.01536 (6)	0.87974 (16)	0.0154 (4)
N2A	0.2018 (3)	0.04304 (6)	0.98605 (16)	0.0170 (4)
H2NA	0.2795	0.0332	1.0306	0.020*
N3A	0.1505 (3)	0.08281 (6)	0.99354 (17)	0.0175 (4)
C1A	−0.0463 (3)	−0.08587 (7)	0.6792 (2)	0.0203 (5)
C2A	0.1305 (3)	−0.14405 (7)	0.6527 (2)	0.0185 (5)
C3A	0.1447 (3)	−0.18124 (8)	0.6037 (2)	0.0231 (6)
H3A	0.0598	−0.1910	0.5573	0.028*
C4A	0.2874 (3)	−0.20371 (8)	0.6249 (2)	0.0242 (6)
H4A	0.2986	−0.2291	0.5933	0.029*
C5A	0.4147 (3)	−0.18901 (8)	0.6929 (2)	0.0242 (6)
H5A	0.5118	−0.2042	0.7052	0.029*
C6A	0.3980 (3)	−0.15206 (7)	0.7422 (2)	0.0203 (5)
H6A	0.4832	−0.1425	0.7886	0.024*
C7A	0.2529 (3)	−0.12857 (7)	0.7231 (2)	0.0175 (5)
C8A	0.2251 (3)	−0.08987 (7)	0.7713 (2)	0.0181 (5)
H8A	0.3072	−0.0791	0.8180	0.022*
C9A	0.0829 (3)	−0.06862 (7)	0.75075 (19)	0.0159 (5)
C10A	0.0537 (3)	−0.02896 (7)	0.79832 (19)	0.0153 (5)
C11A	−0.0693 (3)	−0.00203 (7)	0.7687 (2)	0.0182 (5)
H11A	−0.1532	−0.0071	0.7166	0.022*
C12A	0.1223 (3)	0.02122 (7)	0.90784 (19)	0.0167 (5)
C13A	0.2049 (3)	0.10343 (7)	1.0744 (2)	0.0183 (5)
H13A	0.2727	0.0914	1.1278	0.022*
C14A	0.1576 (3)	0.14634 (7)	1.0806 (2)	0.0182 (5)
C15A	0.1798 (3)	0.16766 (8)	1.1748 (2)	0.0220 (6)
H15A	0.2258	0.1548	1.2352	0.026*
C16A	0.1327 (3)	0.20862 (8)	1.1787 (2)	0.0286 (6)
H16A	0.1441	0.2228	1.2424	0.034*
C17A	0.0696 (3)	0.22810 (8)	1.0886 (2)	0.0277 (6)
H17A	0.0395	0.2555	1.0914	0.033*
C18A	0.0509 (3)	0.20689 (8)	0.9942 (2)	0.0256 (6)
C19A	0.0919 (3)	0.16639 (7)	0.9902 (2)	0.0207 (5)
H19A	0.0759	0.1521	0.9267	0.025*
S1B	0.78931 (7)	0.008872 (18)	0.47478 (5)	0.01707 (14)
O1B	0.7053 (2)	−0.14603 (5)	0.21875 (14)	0.0202 (4)
O2B	0.8716 (2)	−0.11627 (5)	0.33656 (15)	0.0234 (4)
O3B	0.9374 (2)	0.18069 (5)	0.72037 (16)	0.0260 (4)
H3OB	0.9854	0.1590	0.7115	0.039*
N1B	0.5592 (2)	−0.00941 (6)	0.33149 (16)	0.0159 (4)
N2B	0.5221 (3)	0.05370 (6)	0.41319 (16)	0.0174 (4)
H2NB	0.4267	0.0584	0.3851	0.021*
N3B	0.5912 (3)	0.08171 (6)	0.48285 (16)	0.0162 (4)
C1B	0.7465 (3)	−0.11277 (7)	0.2789 (2)	0.0182 (5)
C2B	0.5703 (3)	−0.14700 (7)	0.14717 (19)	0.0175 (5)
C3B	0.5399 (3)	−0.18320 (8)	0.0931 (2)	0.0224 (6)
H3B	0.6058	−0.2061	0.1073	0.027*
C4B	0.4100 (3)	−0.18436 (8)	0.0180 (2)	0.0241 (6)
H4B	0.3878	−0.2084	−0.0195	0.029*
C5B	0.3109 (3)	−0.15024 (8)	−0.0028 (2)	0.0219 (6)
H5B	0.2235	−0.1515	−0.0543	0.026*
C6B	0.3415 (3)	−0.11466 (8)	0.0523 (2)	0.0214 (5)
H6B	0.2751	−0.0919	0.0379	0.026*
C7B	0.4727 (3)	−0.11258 (7)	0.13051 (19)	0.0174 (5)
C8B	0.5100 (3)	−0.07779 (7)	0.19488 (19)	0.0177 (5)
H8B	0.4432	−0.0547	0.1860	0.021*
C9B	0.6387 (3)	−0.07698 (7)	0.26843 (19)	0.0153 (5)
C10B	0.6726 (3)	−0.04195 (7)	0.33772 (19)	0.0156 (5)
C11B	0.8019 (3)	−0.03722 (7)	0.4095 (2)	0.0176 (5)
H11B	0.8866	−0.0563	0.4222	0.021*
C12B	0.6075 (3)	0.01856 (7)	0.39946 (19)	0.0152 (5)
C13B	0.4999 (3)	0.11281 (7)	0.50071 (19)	0.0171 (5)
H13B	0.3917	0.1141	0.4703	0.021*
C14B	0.5629 (3)	0.14618 (7)	0.56794 (19)	0.0165 (5)
C15B	0.4627 (3)	0.18039 (7)	0.5765 (2)	0.0201 (5)
H15B	0.3557	0.1808	0.5441	0.024*
C16B	0.5224 (3)	0.21406 (7)	0.6334 (2)	0.0215 (5)
H16B	0.4549	0.2369	0.6400	0.026*
C17B	0.6821 (3)	0.21366 (7)	0.6802 (2)	0.0212 (5)
H17B	0.7234	0.2365	0.7166	0.025*
C18B	0.7808 (3)	0.17906 (7)	0.6729 (2)	0.0187 (5)
C19B	0.7216 (3)	0.14544 (7)	0.61789 (19)	0.0174 (5)
H19B	0.7877	0.1222	0.6141	0.021*
O1W	0.5255 (2)	0.97623 (5)	0.87645 (14)	0.0220 (4)
H1W1	0.5231	0.9845	0.8111	0.033*
H2W1	0.4267	0.9713	0.9003	0.033*

	U11	U22	U33	U12	U13	U23
S1A	0.0181 (3)	0.0184 (3)	0.0194 (3)	0.0046 (2)	−0.0013 (2)	−0.0010 (2)
O1A	0.0233 (10)	0.0184 (9)	0.0196 (9)	−0.0026 (7)	−0.0022 (8)	−0.0040 (7)
O2A	0.0188 (9)	0.0264 (10)	0.0299 (11)	0.0018 (8)	−0.0097 (8)	−0.0033 (8)
O3A	0.0465 (13)	0.0223 (10)	0.0337 (12)	0.0053 (9)	−0.0083 (10)	0.0015 (9)
N1A	0.0152 (10)	0.0162 (10)	0.0148 (10)	−0.0007 (8)	−0.0002 (8)	0.0012 (8)
N2A	0.0190 (11)	0.0142 (10)	0.0173 (10)	0.0047 (8)	−0.0035 (8)	−0.0021 (8)
N3A	0.0172 (10)	0.0142 (10)	0.0212 (11)	0.0028 (8)	0.0017 (9)	−0.0015 (8)
C1A	0.0241 (14)	0.0181 (12)	0.0184 (12)	−0.0017 (10)	−0.0003 (11)	0.0006 (10)
C2A	0.0226 (13)	0.0169 (12)	0.0164 (12)	0.0000 (10)	0.0046 (10)	0.0026 (10)
C3A	0.0300 (15)	0.0210 (13)	0.0184 (13)	−0.0081 (11)	0.0033 (11)	−0.0020 (11)
C4A	0.0351 (16)	0.0155 (12)	0.0228 (14)	−0.0028 (11)	0.0088 (12)	−0.0023 (11)
C5A	0.0290 (15)	0.0182 (12)	0.0259 (14)	0.0053 (11)	0.0062 (12)	0.0032 (11)
C6A	0.0224 (13)	0.0185 (12)	0.0202 (13)	0.0024 (10)	0.0016 (11)	0.0008 (10)
C7A	0.0221 (13)	0.0148 (11)	0.0158 (12)	−0.0014 (10)	0.0019 (10)	0.0019 (10)
C8A	0.0181 (12)	0.0184 (12)	0.0176 (12)	−0.0014 (10)	−0.0019 (10)	−0.0005 (10)
C9A	0.0166 (12)	0.0169 (11)	0.0143 (11)	−0.0018 (10)	−0.0001 (10)	0.0032 (9)
C10A	0.0134 (12)	0.0181 (11)	0.0146 (11)	−0.0010 (9)	0.0022 (9)	0.0010 (10)
C11A	0.0171 (12)	0.0192 (12)	0.0180 (12)	−0.0002 (10)	−0.0011 (10)	−0.0010 (10)
C12A	0.0143 (12)	0.0184 (12)	0.0174 (12)	0.0005 (9)	0.0016 (10)	0.0021 (10)
C13A	0.0184 (13)	0.0177 (12)	0.0188 (13)	0.0010 (10)	0.0022 (10)	0.0006 (10)
C14A	0.0141 (12)	0.0158 (12)	0.0249 (13)	−0.0017 (9)	0.0035 (10)	0.0005 (10)
C15A	0.0214 (13)	0.0231 (13)	0.0217 (13)	−0.0028 (11)	0.0037 (11)	−0.0009 (11)
C16A	0.0296 (15)	0.0244 (14)	0.0328 (16)	−0.0067 (12)	0.0102 (13)	−0.0140 (12)
C17A	0.0278 (15)	0.0157 (12)	0.0400 (17)	0.0044 (11)	0.0050 (13)	−0.0044 (12)
C18A	0.0220 (14)	0.0204 (13)	0.0341 (16)	0.0018 (11)	−0.0020 (12)	0.0007 (12)
C19A	0.0155 (12)	0.0197 (12)	0.0270 (14)	−0.0026 (10)	0.0004 (11)	0.0017 (11)
S1B	0.0155 (3)	0.0181 (3)	0.0173 (3)	0.0001 (2)	−0.0027 (2)	−0.0011 (2)
O1B	0.0229 (9)	0.0144 (8)	0.0230 (9)	0.0012 (7)	−0.0023 (8)	−0.0020 (7)
O2B	0.0223 (10)	0.0209 (9)	0.0263 (10)	0.0016 (8)	−0.0055 (8)	0.0001 (8)
O3B	0.0257 (10)	0.0202 (9)	0.0310 (11)	0.0042 (8)	−0.0091 (9)	−0.0059 (8)
N1B	0.0148 (10)	0.0161 (10)	0.0168 (10)	0.0014 (8)	0.0012 (8)	−0.0015 (8)
N2B	0.0154 (10)	0.0160 (10)	0.0202 (11)	0.0025 (8)	−0.0029 (9)	−0.0037 (8)
N3B	0.0194 (11)	0.0148 (10)	0.0143 (10)	−0.0030 (8)	0.0005 (8)	−0.0020 (8)
C1B	0.0208 (13)	0.0160 (12)	0.0180 (12)	−0.0020 (10)	0.0025 (10)	0.0013 (10)
C2B	0.0159 (12)	0.0210 (12)	0.0158 (12)	−0.0048 (10)	0.0032 (10)	−0.0002 (10)
C3B	0.0275 (14)	0.0176 (12)	0.0227 (13)	−0.0019 (11)	0.0050 (11)	−0.0016 (11)
C4B	0.0288 (15)	0.0220 (13)	0.0221 (13)	−0.0077 (11)	0.0071 (12)	−0.0047 (11)
C5B	0.0184 (13)	0.0276 (13)	0.0200 (13)	−0.0049 (11)	0.0031 (11)	−0.0068 (11)
C6B	0.0181 (13)	0.0264 (13)	0.0199 (13)	−0.0010 (11)	0.0015 (10)	−0.0018 (11)
C7B	0.0166 (12)	0.0183 (12)	0.0178 (12)	−0.0024 (10)	0.0040 (10)	0.0000 (10)
C8B	0.0182 (12)	0.0162 (11)	0.0189 (12)	0.0013 (10)	0.0012 (10)	0.0000 (10)
C9B	0.0145 (12)	0.0145 (11)	0.0174 (12)	−0.0010 (9)	0.0035 (10)	0.0005 (9)
C10B	0.0169 (12)	0.0147 (11)	0.0151 (12)	−0.0006 (9)	0.0016 (10)	0.0000 (9)
C11B	0.0159 (12)	0.0161 (11)	0.0206 (12)	0.0010 (10)	0.0005 (10)	0.0013 (10)
C12B	0.0136 (11)	0.0162 (11)	0.0158 (12)	−0.0013 (9)	0.0010 (9)	0.0017 (9)
C13B	0.0149 (12)	0.0180 (12)	0.0183 (12)	−0.0016 (10)	0.0000 (10)	0.0025 (10)
C14B	0.0209 (12)	0.0141 (11)	0.0148 (12)	−0.0024 (10)	0.0043 (10)	0.0028 (9)
C15B	0.0193 (13)	0.0187 (12)	0.0226 (13)	−0.0006 (10)	0.0029 (11)	0.0004 (10)
C16B	0.0239 (13)	0.0153 (12)	0.0258 (14)	0.0030 (10)	0.0059 (11)	−0.0011 (10)
C17B	0.0265 (14)	0.0143 (12)	0.0229 (13)	−0.0011 (10)	0.0028 (11)	−0.0014 (10)
C18B	0.0208 (13)	0.0179 (12)	0.0170 (12)	−0.0006 (10)	−0.0030 (10)	0.0009 (10)
C19B	0.0209 (13)	0.0137 (11)	0.0179 (12)	0.0015 (10)	0.0029 (10)	0.0018 (10)
O1W	0.0188 (9)	0.0284 (10)	0.0186 (9)	0.0012 (8)	−0.0019 (7)	0.0033 (8)

S1A—C11A	1.706 (2)	S1B—C12B	1.726 (2)
S1A—C12A	1.730 (2)	O1B—C1B	1.359 (3)
O1A—C1A	1.369 (3)	O1B—C2B	1.372 (3)
O1A—C2A	1.380 (3)	O2B—C1B	1.212 (3)
O2A—C1A	1.206 (3)	O3B—C18B	1.362 (3)
O3A—C18A	1.367 (3)	O3B—H3OB	0.8200
O3A—H3OA	0.8200	N1B—C12B	1.300 (3)
N1A—C12A	1.299 (3)	N1B—C10B	1.400 (3)
N1A—C10A	1.392 (3)	N2B—C12B	1.355 (3)
N2A—C12A	1.351 (3)	N2B—N3B	1.367 (3)
N2A—N3A	1.372 (3)	N2B—H2NB	0.8398
N2A—H2NA	0.8779	N3B—C13B	1.281 (3)
N3A—C13A	1.281 (3)	C1B—C9B	1.459 (3)
C1A—C9A	1.452 (3)	C2B—C7B	1.382 (3)
C2A—C3A	1.374 (3)	C2B—C3B	1.384 (3)
C2A—C7A	1.385 (4)	C3B—C4B	1.371 (4)
C3A—C4A	1.375 (4)	C3B—H3B	0.9300
C3A—H3A	0.9300	C4B—C5B	1.389 (4)
C4A—C5A	1.384 (4)	C4B—H4B	0.9300
C4A—H4A	0.9300	C5B—C6B	1.374 (3)
C5A—C6A	1.371 (3)	C5B—H5B	0.9300
C5A—H5A	0.9300	C6B—C7B	1.404 (4)
C6A—C7A	1.404 (3)	C6B—H6B	0.9300
C6A—H6A	0.9300	C7B—C8B	1.423 (3)
C7A—C8A	1.429 (3)	C8B—C9B	1.350 (3)
C8A—C9A	1.348 (3)	C8B—H8B	0.9300
C8A—H8A	0.9300	C9B—C10B	1.460 (3)
C9A—C10A	1.456 (3)	C10B—C11B	1.348 (3)
C10A—C11A	1.361 (3)	C11B—H11B	0.9300
C11A—H11A	0.9300	C13B—C14B	1.458 (3)
C13A—C14A	1.460 (3)	C13B—H13B	0.9300
C13A—H13A	0.9300	C14B—C15B	1.386 (3)
C14A—C15A	1.383 (4)	C14B—C19B	1.389 (3)
C14A—C19A	1.395 (4)	C15B—C16B	1.388 (3)
C15A—C16A	1.396 (4)	C15B—H15B	0.9300
C15A—H15A	0.9300	C16B—C17B	1.380 (4)
C16A—C17A	1.376 (4)	C16B—H16B	0.9300
C16A—H16A	0.9300	C17B—C18B	1.389 (3)
C17A—C18A	1.381 (4)	C17B—H17B	0.9300
C17A—H17A	0.9300	C18B—C19B	1.373 (3)
C18A—C19A	1.369 (3)	C19B—H19B	0.9300
C19A—H19A	0.9300	O1W—H1W1	0.8672
S1B—C11B	1.726 (2)	O1W—H2W1	0.8763
C11A—S1A—C12A	88.33 (12)	C1B—O1B—C2B	123.10 (19)
C1A—O1A—C2A	122.4 (2)	C18B—O3B—H3OB	109.5
C18A—O3A—H3OA	109.5	C12B—N1B—C10B	109.3 (2)
C12A—N1A—C10A	109.6 (2)	C12B—N2B—N3B	117.6 (2)
C12A—N2A—N3A	114.9 (2)	C12B—N2B—H2NB	123.8
C12A—N2A—H2NA	124.4	N3B—N2B—H2NB	118.5
N3A—N2A—H2NA	120.7	C13B—N3B—N2B	115.6 (2)
C13A—N3A—N2A	117.7 (2)	O2B—C1B—O1B	115.4 (2)
O2A—C1A—O1A	114.9 (2)	O2B—C1B—C9B	126.6 (2)
O2A—C1A—C9A	126.8 (2)	O1B—C1B—C9B	118.0 (2)
O1A—C1A—C9A	118.3 (2)	O1B—C2B—C7B	120.1 (2)
C3A—C2A—O1A	117.3 (2)	O1B—C2B—C3B	117.2 (2)
C3A—C2A—C7A	122.7 (2)	C7B—C2B—C3B	122.8 (2)
O1A—C2A—C7A	119.9 (2)	C4B—C3B—C2B	118.2 (2)
C2A—C3A—C4A	118.4 (2)	C4B—C3B—H3B	120.9
C2A—C3A—H3A	120.8	C2B—C3B—H3B	120.9
C4A—C3A—H3A	120.8	C3B—C4B—C5B	121.0 (2)
C3A—C4A—C5A	120.8 (2)	C3B—C4B—H4B	119.5
C3A—C4A—H4A	119.6	C5B—C4B—H4B	119.5
C5A—C4A—H4A	119.6	C6B—C5B—C4B	120.2 (3)
C6A—C5A—C4A	120.1 (2)	C6B—C5B—H5B	119.9
C6A—C5A—H5A	119.9	C4B—C5B—H5B	119.9
C4A—C5A—H5A	119.9	C5B—C6B—C7B	120.3 (2)
C5A—C6A—C7A	120.4 (2)	C5B—C6B—H6B	119.9
C5A—C6A—H6A	119.8	C7B—C6B—H6B	119.9
C7A—C6A—H6A	119.8	C2B—C7B—C6B	117.6 (2)
C2A—C7A—C6A	117.5 (2)	C2B—C7B—C8B	117.8 (2)
C2A—C7A—C8A	118.5 (2)	C6B—C7B—C8B	124.5 (2)
C6A—C7A—C8A	124.0 (2)	C9B—C8B—C7B	122.5 (2)
C9A—C8A—C7A	121.7 (2)	C9B—C8B—H8B	118.7
C9A—C8A—H8A	119.1	C7B—C8B—H8B	118.7
C7A—C8A—H8A	119.1	C8B—C9B—C1B	118.2 (2)
C8A—C9A—C1A	119.0 (2)	C8B—C9B—C10B	122.6 (2)
C8A—C9A—C10A	122.3 (2)	C1B—C9B—C10B	119.2 (2)
C1A—C9A—C10A	118.7 (2)	C11B—C10B—N1B	115.0 (2)
C11A—C10A—N1A	114.6 (2)	C11B—C10B—C9B	127.2 (2)
C11A—C10A—C9A	126.6 (2)	N1B—C10B—C9B	117.7 (2)
N1A—C10A—C9A	118.7 (2)	C10B—C11B—S1B	111.06 (18)
C10A—C11A—S1A	111.28 (19)	C10B—C11B—H11B	124.5
C10A—C11A—H11A	124.4	S1B—C11B—H11B	124.5
S1A—C11A—H11A	124.4	N1B—C12B—N2B	123.3 (2)
N1A—C12A—N2A	124.7 (2)	N1B—C12B—S1B	116.50 (18)
N1A—C12A—S1A	116.15 (18)	N2B—C12B—S1B	120.19 (18)
N2A—C12A—S1A	119.10 (18)	N3B—C13B—C14B	121.1 (2)
N3A—C13A—C14A	118.2 (2)	N3B—C13B—H13B	119.5
N3A—C13A—H13A	120.9	C14B—C13B—H13B	119.5
C14A—C13A—H13A	120.9	C15B—C14B—C19B	119.9 (2)
C15A—C14A—C19A	119.4 (2)	C15B—C14B—C13B	117.9 (2)
C15A—C14A—C13A	120.7 (2)	C19B—C14B—C13B	122.1 (2)
C19A—C14A—C13A	119.9 (2)	C14B—C15B—C16B	119.9 (2)
C14A—C15A—C16A	119.6 (3)	C14B—C15B—H15B	120.1
C14A—C15A—H15A	120.2	C16B—C15B—H15B	120.1
C16A—C15A—H15A	120.2	C17B—C16B—C15B	120.0 (2)
C17A—C16A—C15A	120.4 (3)	C17B—C16B—H16B	120.0
C17A—C16A—H16A	119.8	C15B—C16B—H16B	120.0
C15A—C16A—H16A	119.8	C16B—C17B—C18B	119.8 (2)
C16A—C17A—C18A	119.8 (2)	C16B—C17B—H17B	120.1
C16A—C17A—H17A	120.1	C18B—C17B—H17B	120.1
C18A—C17A—H17A	120.1	O3B—C18B—C19B	122.6 (2)
O3A—C18A—C19A	121.3 (3)	O3B—C18B—C17B	117.0 (2)
O3A—C18A—C17A	118.4 (2)	C19B—C18B—C17B	120.4 (2)
C19A—C18A—C17A	120.3 (3)	C18B—C19B—C14B	119.9 (2)
C18A—C19A—C14A	120.5 (3)	C18B—C19B—H19B	120.0
C18A—C19A—H19A	119.7	C14B—C19B—H19B	120.0
C14A—C19A—H19A	119.7	H1W1—O1W—H2W1	114.1
C11B—S1B—C12B	88.11 (12)
C12A—N2A—N3A—C13A	170.9 (2)	C12B—N2B—N3B—C13B	−174.0 (2)
C2A—O1A—C1A—O2A	−174.4 (2)	C2B—O1B—C1B—O2B	−178.3 (2)
C2A—O1A—C1A—C9A	4.7 (3)	C2B—O1B—C1B—C9B	1.8 (3)
C1A—O1A—C2A—C3A	176.2 (2)	C1B—O1B—C2B—C7B	2.5 (3)
C1A—O1A—C2A—C7A	−2.9 (3)	C1B—O1B—C2B—C3B	−178.3 (2)
O1A—C2A—C3A—C4A	−179.7 (2)	O1B—C2B—C3B—C4B	−177.3 (2)
C7A—C2A—C3A—C4A	−0.7 (4)	C7B—C2B—C3B—C4B	1.8 (4)
C2A—C3A—C4A—C5A	−0.9 (4)	C2B—C3B—C4B—C5B	−0.4 (4)
C3A—C4A—C5A—C6A	1.6 (4)	C3B—C4B—C5B—C6B	−0.3 (4)
C4A—C5A—C6A—C7A	−0.9 (4)	C4B—C5B—C6B—C7B	−0.3 (4)
C3A—C2A—C7A—C6A	1.3 (4)	O1B—C2B—C7B—C6B	176.7 (2)
O1A—C2A—C7A—C6A	−179.7 (2)	C3B—C2B—C7B—C6B	−2.4 (4)
C3A—C2A—C7A—C8A	−179.0 (2)	O1B—C2B—C7B—C8B	−4.4 (3)
O1A—C2A—C7A—C8A	0.1 (4)	C3B—C2B—C7B—C8B	176.6 (2)
C5A—C6A—C7A—C2A	−0.5 (4)	C5B—C6B—C7B—C2B	1.6 (4)
C5A—C6A—C7A—C8A	179.8 (2)	C5B—C6B—C7B—C8B	−177.3 (2)
C2A—C7A—C8A—C9A	0.8 (4)	C2B—C7B—C8B—C9B	1.9 (4)
C6A—C7A—C8A—C9A	−179.5 (2)	C6B—C7B—C8B—C9B	−179.3 (2)
C7A—C8A—C9A—C1A	1.1 (4)	C7B—C8B—C9B—C1B	2.3 (4)
C7A—C8A—C9A—C10A	−179.3 (2)	C7B—C8B—C9B—C10B	−177.2 (2)
O2A—C1A—C9A—C8A	175.3 (3)	O2B—C1B—C9B—C8B	175.9 (2)
O1A—C1A—C9A—C8A	−3.7 (3)	O1B—C1B—C9B—C8B	−4.2 (3)
O2A—C1A—C9A—C10A	−4.4 (4)	O2B—C1B—C9B—C10B	−4.5 (4)
O1A—C1A—C9A—C10A	176.6 (2)	O1B—C1B—C9B—C10B	175.4 (2)
C12A—N1A—C10A—C11A	−0.7 (3)	C12B—N1B—C10B—C11B	−0.3 (3)
C12A—N1A—C10A—C9A	176.8 (2)	C12B—N1B—C10B—C9B	179.0 (2)
C8A—C9A—C10A—C11A	167.1 (2)	C8B—C9B—C10B—C11B	−176.3 (2)
C1A—C9A—C10A—C11A	−13.3 (4)	C1B—C9B—C10B—C11B	4.1 (4)
C8A—C9A—C10A—N1A	−10.1 (4)	C8B—C9B—C10B—N1B	4.5 (3)
C1A—C9A—C10A—N1A	169.6 (2)	C1B—C9B—C10B—N1B	−175.1 (2)
N1A—C10A—C11A—S1A	1.5 (3)	N1B—C10B—C11B—S1B	0.1 (3)
C9A—C10A—C11A—S1A	−175.7 (2)	C9B—C10B—C11B—S1B	−179.1 (2)
C12A—S1A—C11A—C10A	−1.42 (19)	C12B—S1B—C11B—C10B	0.09 (19)
C10A—N1A—C12A—N2A	178.9 (2)	C10B—N1B—C12B—N2B	−179.2 (2)
C10A—N1A—C12A—S1A	−0.4 (3)	C10B—N1B—C12B—S1B	0.4 (3)
N3A—N2A—C12A—N1A	172.1 (2)	N3B—N2B—C12B—N1B	−176.3 (2)
N3A—N2A—C12A—S1A	−8.7 (3)	N3B—N2B—C12B—S1B	4.2 (3)
C11A—S1A—C12A—N1A	1.1 (2)	C11B—S1B—C12B—N1B	−0.3 (2)
C11A—S1A—C12A—N2A	−178.2 (2)	C11B—S1B—C12B—N2B	179.3 (2)
N2A—N3A—C13A—C14A	177.0 (2)	N2B—N3B—C13B—C14B	−176.0 (2)
N3A—C13A—C14A—C15A	165.4 (2)	N3B—C13B—C14B—C15B	174.6 (2)
N3A—C13A—C14A—C19A	−15.7 (3)	N3B—C13B—C14B—C19B	−1.8 (4)
C19A—C14A—C15A—C16A	1.4 (4)	C19B—C14B—C15B—C16B	1.1 (4)
C13A—C14A—C15A—C16A	−179.7 (2)	C13B—C14B—C15B—C16B	−175.4 (2)
C14A—C15A—C16A—C17A	−2.1 (4)	C14B—C15B—C16B—C17B	0.9 (4)
C15A—C16A—C17A—C18A	0.7 (4)	C15B—C16B—C17B—C18B	−1.9 (4)
C16A—C17A—C18A—O3A	−178.1 (3)	C16B—C17B—C18B—O3B	179.7 (2)
C16A—C17A—C18A—C19A	1.2 (4)	C16B—C17B—C18B—C19B	1.1 (4)
O3A—C18A—C19A—C14A	177.4 (2)	O3B—C18B—C19B—C14B	−177.7 (2)
C17A—C18A—C19A—C14A	−1.9 (4)	C17B—C18B—C19B—C14B	0.9 (4)
C15A—C14A—C19A—C18A	0.5 (4)	C15B—C14B—C19B—C18B	−2.0 (4)
C13A—C14A—C19A—C18A	−178.4 (2)	C13B—C14B—C19B—C18B	174.4 (2)

Cg1 is the centroid of C14A–C19A benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3A—H3OA···O3Bi	0.82	2.00	2.808 (3)	170
N2A—H2NA···O1Wii	0.88	1.93	2.790 (3)	167
O3B—H3OB···O2Biii	0.82	1.93	2.726 (3)	165
N2B—H2NB···O2Aiv	0.84	2.05	2.878 (3)	170
O1W—H1W1···N1Bv	0.87	2.05	2.888 (3)	161
O1W—H2W1···N1Avi	0.88	2.15	2.913 (3)	145
C8A—H8A···O1Wvii	0.93	2.60	3.451 (3)	153
C5B—H5B···Cg1iv	0.93	2.95	3.708 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C14A–C19A benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3A—H3OA⋯O3Bi	0.82	2.00	2.808 (3)	170
N2A—H2NA⋯O1Wii	0.88	1.93	2.790 (3)	167
O3B—H3OB⋯O2Biii	0.82	1.93	2.726 (3)	165
N2B—H2NB⋯O2Aiv	0.84	2.05	2.878 (3)	170
O1W—H1W1⋯N1Bv	0.87	2.05	2.888 (3)	161
O1W—H2W1⋯N1Avi	0.88	2.15	2.913 (3)	145
C8A—H8A⋯O1Wvii	0.93	2.60	3.451 (3)	153
C5B—H5B⋯Cg1iv	0.93	2.95	3.708 (3)	139

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