4-(4-Chloro-phen-yl)-6-hydr-oxy-5-(2-thienyl-carbonyl)-6-(trifluoro-meth-yl)-3,4,5,6-tetra-hydro-pyrimidin-2(1H)-one monohydrate.

The asymmetric unit of the title compound, C(16)H(12)ClF(3)N(2)O(3)S·H(2)O, contains two crystallographically independent organic mol-ecules and two water mol-ecules. The organic species are linked by an inter-molecular O-H⋯O hydrogen bond, while the water mol-ecules are connected to them through inter-molecular O-H⋯N hydrogen bonds. The thio-phene and phenyl rings are oriented at dihedral angles of 62.35 (4) in the first independent mol-ecule and 60.74 (5)° in the second, while the pyrimidine rings adopt twisted conformations in both molecules. Intra-molecular N-H⋯F inter-actions result in the formation of two five-membered rings having envelope conformations. In the crystal structure, further inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into chains.

Related literature

For related structures, see: Paraskar et al. (2003 ▶); Peng & Deng (2001 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H12ClF3N2O3S·H2O

M = 422.81

Orthorhombic,

a = 9.1156 (6) Å

b = 14.1582 (7) Å

c = 27.6012 (17) Å

V = 3562.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.39 mm−1

T = 298 K

0.5 × 0.3 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.860, T max = 0.923

19595 measured reflections

9251 independent reflections

7478 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.146

S = 1.07

9251 reflections

511 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 4326 Friedel pairs

Flack parameter: 0.18 (8)

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017097/hk2682sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017097/hk2682Isup2.hkl

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

C16H12ClF3N2O3S·H2O	F(000) = 1728
Mr = 422.81	Dx = 1.577 Mg m−3
Orthorhombic, Pbn21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ab	Cell parameters from 1879 reflections
a = 9.1156 (6) Å	θ = 2.4–29.2°
b = 14.1582 (7) Å	µ = 0.39 mm−1
c = 27.6012 (17) Å	T = 298 K
V = 3562.2 (4) Å3	Block, colourless
Z = 8	0.5 × 0.3 × 0.2 mm

Bruker SMART CCD area-detector diffractometer	7478 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.032
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	θmax = 29.2°, θmin = 2.4°
Tmin = 0.860, Tmax = 0.923	h = −11→12
19595 measured reflections	k = −19→19
9251 independent reflections	l = −37→36

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0679P)2 + 1.8489P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.055	(Δ/σ)max = 0.012
wR(F2) = 0.146	Δρmax = 0.41 e Å−3
S = 1.07	Δρmin = −0.47 e Å−3
9251 reflections	Absolute structure: Flack (1983), 4326 Friedel pairs
511 parameters	Flack parameter: 0.18 (8)

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.

	x	y	z	Uiso*/Ueq
Cl1	0.20863 (18)	1.18591 (11)	0.10132 (6)	0.0800 (4)
Cl2	0.71737 (17)	0.07620 (11)	0.51510 (6)	0.0829 (5)
S1	−0.37400 (15)	0.85338 (12)	0.12927 (6)	0.0797 (4)
S2	0.13318 (16)	0.40572 (12)	0.48988 (7)	0.0805 (4)
O1	−0.2355 (3)	0.8588 (2)	0.22653 (14)	0.0540 (8)
O2	−0.0969 (3)	0.71519 (19)	0.27993 (10)	0.0401 (6)
H2B	−0.086 (4)	0.665 (3)	0.2992 (15)	0.028 (10)*
O3	0.3549 (3)	0.69972 (17)	0.28201 (10)	0.0414 (6)
O4	0.2597 (3)	0.4046 (3)	0.39238 (14)	0.0539 (8)
O5	0.4027 (3)	0.54419 (17)	0.33543 (9)	0.0394 (5)
H5	0.396 (7)	0.604 (4)	0.318 (2)	0.088 (18)*
O6	0.8546 (3)	0.55885 (17)	0.33323 (10)	0.0413 (6)
O7	0.3736 (3)	0.9773 (2)	0.30044 (11)	0.0433 (6)
H7A	0.459 (8)	0.964 (4)	0.309 (2)	0.09 (2)*
H7B	0.321 (7)	0.993 (4)	0.325 (2)	0.080 (18)*
O8	0.8726 (3)	0.2819 (2)	0.31572 (11)	0.0423 (6)
H8A	0.946 (6)	0.278 (3)	0.3038 (17)	0.045 (13)*
H8B	0.820 (6)	0.283 (4)	0.291 (2)	0.066 (15)*
N1	0.1334 (3)	0.66639 (19)	0.24968 (11)	0.0335 (6)
H1A	0.1546	0.6074	0.247	0.04*
N2	0.2184 (4)	0.8206 (2)	0.25512 (13)	0.0408 (7)
H2A	0.291	0.8579	0.2605	0.049*
N3	0.6328 (3)	0.59341 (18)	0.36587 (10)	0.0314 (5)
H3A	0.6543	0.6524	0.3679	0.038*
N4	0.7153 (4)	0.43923 (19)	0.36029 (13)	0.0385 (7)
H4A	0.7864	0.4015	0.3535	0.046*
F1	−0.0306 (3)	0.61345 (17)	0.16413 (9)	0.0574 (6)
F2	−0.2295 (3)	0.6369 (2)	0.20268 (16)	0.0684 (9)
F3	−0.0748 (3)	0.53514 (14)	0.22866 (10)	0.0553 (6)
F4	0.4222 (3)	0.72493 (15)	0.38632 (10)	0.0572 (6)
F5	0.2705 (3)	0.6231 (2)	0.41348 (15)	0.0686 (9)
F6	0.4700 (3)	0.64863 (18)	0.45092 (9)	0.0618 (7)
C1	−0.3412 (9)	0.8435 (4)	0.0706 (3)	0.094 (2)
H1	−0.4133	0.8506	0.047	0.112*
C2	−0.2010 (10)	0.8242 (5)	0.0601 (2)	0.084 (2)
H2	−0.1682	0.8161	0.0285	0.1*
C3	−0.1067 (5)	0.8169 (3)	0.10026 (15)	0.0440 (8)
H3	−0.0063	0.8051	0.0994	0.053*
C4	−0.1978 (4)	0.8318 (3)	0.14442 (15)	0.0426 (8)
C5	−0.1541 (4)	0.8292 (2)	0.19488 (13)	0.0343 (7)
C6	−0.0040 (3)	0.7890 (2)	0.20871 (12)	0.0286 (6)
H6	0.0497	0.7749	0.1788	0.034*
C7	−0.0144 (3)	0.6974 (2)	0.23879 (11)	0.0288 (6)
C8	−0.0881 (4)	0.6194 (2)	0.20873 (13)	0.0366 (7)
C9	0.2396 (3)	0.7281 (3)	0.26401 (15)	0.0311 (7)
C10	0.0830 (4)	0.8633 (2)	0.23712 (12)	0.0314 (6)
H10	0.0241	0.8855	0.2646	0.038*
C11	0.1184 (3)	0.9461 (2)	0.20424 (12)	0.0319 (6)
C12	0.2245 (5)	0.9376 (3)	0.1683 (2)	0.0462 (9)
H12	0.2777	0.8818	0.1655	0.055*
C13	0.2516 (4)	1.0109 (3)	0.13683 (18)	0.0466 (11)
H13	0.3236	1.0052	0.1131	0.056*
C14	0.1722 (4)	1.0921 (3)	0.14066 (14)	0.0453 (8)
C15	0.0667 (5)	1.1025 (3)	0.17562 (15)	0.0461 (9)
H15	0.0139	1.1586	0.178	0.055*
C16	0.0395 (4)	1.0292 (2)	0.20716 (14)	0.0397 (7)
H16	−0.0328	1.0358	0.2307	0.048*
C17	0.1708 (9)	0.4116 (5)	0.5484 (3)	0.088 (2)
H17	0.0997	0.4045	0.5723	0.105*
C18	0.3112 (9)	0.4273 (4)	0.5583 (2)	0.0804 (18)
H18	0.3463	0.4308	0.5899	0.096*
C19	0.4056 (5)	0.4386 (3)	0.51657 (13)	0.0444 (8)
H19	0.506	0.4501	0.5167	0.053*
C20	0.3103 (4)	0.4283 (3)	0.47414 (15)	0.0421 (8)
C21	0.3463 (4)	0.4322 (2)	0.42239 (14)	0.0365 (7)
C22	0.4972 (3)	0.4722 (2)	0.40755 (11)	0.0287 (6)
H22	0.5523	0.4871	0.4371	0.034*
C23	0.4852 (3)	0.5625 (2)	0.37684 (11)	0.0285 (6)
C24	0.4120 (4)	0.6412 (2)	0.40686 (14)	0.0386 (7)
C25	0.7380 (4)	0.5309 (2)	0.35238 (16)	0.0331 (8)
C26	0.5819 (3)	0.3969 (2)	0.37927 (12)	0.0307 (6)
H26	0.5215	0.3742	0.3523	0.037*
C27	0.6181 (3)	0.3148 (2)	0.41269 (12)	0.0307 (6)
C28	0.5391 (4)	0.2319 (2)	0.40975 (14)	0.0401 (7)
H28	0.4665	0.2253	0.3863	0.048*
C29	0.5675 (4)	0.1575 (3)	0.44180 (17)	0.0499 (9)
H29	0.5138	0.1017	0.4402	0.06*
C30	0.6760 (4)	0.1689 (3)	0.47547 (15)	0.0492 (10)
C31	0.7576 (5)	0.2514 (3)	0.4788 (2)	0.0515 (12)
H31	0.8306	0.2575	0.5021	0.062*
C32	0.7287 (4)	0.3237 (3)	0.44722 (16)	0.0398 (8)
H32	0.7833	0.3791	0.4488	0.048*

	U11	U22	U33	U12	U13	U23
Cl1	0.0826 (8)	0.0777 (8)	0.0797 (9)	−0.0138 (7)	0.0002 (8)	0.0486 (7)
Cl2	0.0798 (8)	0.0833 (8)	0.0856 (10)	0.0318 (7)	0.0201 (8)	0.0568 (8)
S1	0.0514 (6)	0.0965 (10)	0.0912 (11)	0.0052 (7)	−0.0265 (7)	0.0229 (8)
S2	0.0571 (7)	0.0907 (10)	0.0937 (11)	−0.0052 (7)	0.0273 (8)	0.0203 (8)
O1	0.0466 (16)	0.0612 (18)	0.054 (2)	0.0213 (13)	0.0096 (13)	0.0121 (15)
O2	0.0436 (14)	0.0339 (12)	0.0427 (14)	0.0050 (11)	0.0152 (11)	0.0097 (11)
O3	0.0324 (12)	0.0356 (12)	0.0561 (16)	−0.0016 (9)	−0.0148 (11)	0.0126 (11)
O4	0.0398 (15)	0.0719 (19)	0.050 (2)	−0.0212 (13)	−0.0117 (12)	0.0137 (15)
O5	0.0443 (13)	0.0339 (12)	0.0400 (13)	−0.0061 (10)	−0.0126 (11)	0.0086 (10)
O6	0.0356 (12)	0.0367 (12)	0.0515 (15)	0.0034 (10)	0.0149 (11)	0.0112 (11)
O7	0.0327 (13)	0.0486 (15)	0.0486 (16)	−0.0070 (11)	0.0040 (11)	−0.0024 (12)
O8	0.0315 (13)	0.0482 (15)	0.0472 (15)	0.0060 (11)	−0.0037 (12)	−0.0004 (12)
N1	0.0298 (12)	0.0255 (12)	0.0451 (17)	0.0001 (10)	−0.0053 (11)	0.0014 (11)
N2	0.0395 (14)	0.0272 (13)	0.056 (2)	−0.0045 (12)	−0.0210 (15)	0.0089 (12)
N3	0.0281 (12)	0.0246 (11)	0.0414 (15)	−0.0004 (9)	0.0072 (11)	0.0021 (10)
N4	0.0399 (14)	0.0280 (12)	0.0475 (18)	0.0089 (12)	0.0166 (14)	0.0047 (11)
F1	0.0750 (16)	0.0529 (13)	0.0443 (13)	−0.0109 (12)	−0.0044 (12)	−0.0085 (11)
F2	0.0333 (11)	0.0598 (15)	0.112 (3)	−0.0091 (11)	−0.0239 (15)	0.0002 (16)
F3	0.0688 (15)	0.0297 (9)	0.0674 (16)	−0.0121 (10)	−0.0203 (13)	0.0055 (10)
F4	0.0739 (16)	0.0313 (10)	0.0664 (16)	0.0138 (10)	0.0233 (13)	0.0062 (10)
F5	0.0312 (10)	0.0600 (15)	0.115 (3)	0.0080 (10)	0.0226 (15)	−0.0060 (16)
F6	0.0785 (18)	0.0637 (14)	0.0433 (13)	0.0138 (13)	0.0042 (12)	−0.0161 (11)
C1	0.115 (5)	0.076 (4)	0.090 (5)	0.007 (4)	−0.071 (4)	0.007 (3)
C2	0.132 (6)	0.077 (4)	0.041 (3)	0.015 (4)	−0.022 (3)	0.003 (2)
C3	0.053 (2)	0.0481 (19)	0.0310 (17)	0.0122 (16)	−0.0079 (16)	0.0067 (15)
C4	0.0383 (18)	0.0404 (17)	0.049 (2)	0.0002 (14)	−0.0079 (15)	0.0121 (16)
C5	0.0302 (15)	0.0331 (15)	0.0397 (18)	0.0016 (12)	0.0018 (12)	0.0065 (13)
C6	0.0256 (13)	0.0301 (13)	0.0302 (15)	−0.0005 (10)	0.0013 (11)	0.0037 (12)
C7	0.0250 (13)	0.0266 (12)	0.0348 (15)	−0.0014 (10)	−0.0003 (11)	0.0006 (11)
C8	0.0340 (15)	0.0332 (15)	0.0427 (18)	−0.0031 (12)	−0.0074 (14)	0.0016 (13)
C9	0.0307 (16)	0.0329 (15)	0.0297 (19)	−0.0014 (12)	−0.0019 (11)	0.0048 (13)
C10	0.0381 (16)	0.0238 (12)	0.0322 (16)	0.0010 (11)	−0.0003 (12)	0.0029 (11)
C11	0.0342 (15)	0.0302 (14)	0.0312 (15)	−0.0020 (11)	−0.0042 (12)	0.0048 (12)
C12	0.0484 (19)	0.0333 (17)	0.057 (3)	0.0017 (15)	0.012 (2)	−0.0047 (16)
C13	0.051 (3)	0.051 (2)	0.037 (3)	−0.0155 (17)	0.0098 (15)	0.0014 (18)
C14	0.0478 (19)	0.0446 (19)	0.0435 (19)	−0.0134 (16)	−0.0069 (16)	0.0182 (16)
C15	0.047 (2)	0.0348 (16)	0.056 (2)	0.0060 (15)	−0.0049 (17)	0.0120 (16)
C16	0.0369 (16)	0.0360 (16)	0.0464 (19)	0.0024 (13)	0.0037 (15)	0.0045 (15)
C17	0.106 (5)	0.074 (4)	0.083 (4)	0.001 (3)	0.059 (4)	0.014 (3)
C18	0.122 (6)	0.070 (3)	0.050 (3)	0.0003 (3)	0.017 (3)	0.015 (2)
C19	0.054 (2)	0.052 (2)	0.0271 (17)	0.0350 (3)	0.0152 (15)	0.0050 (15)
C20	0.0339 (17)	0.0429 (18)	0.050 (2)	0.0030 (14)	0.0108 (15)	0.0132 (15)
C21	0.0302 (15)	0.0361 (15)	0.0431 (18)	−0.0016 (12)	0.0007 (13)	0.0118 (14)
C22	0.0261 (13)	0.0304 (13)	0.0297 (15)	−0.0015 (10)	−0.0009 (11)	0.0030 (11)
C23	0.0252 (13)	0.0282 (13)	0.0321 (15)	−0.0007 (10)	−0.0010 (11)	0.0027 (11)
C24	0.0289 (14)	0.0389 (16)	0.048 (2)	0.0046 (12)	0.0079 (14)	0.0032 (14)
C25	0.0289 (16)	0.0306 (15)	0.040 (2)	0.0029 (11)	0.0083 (12)	0.0042 (14)
C26	0.0335 (14)	0.0278 (13)	0.0309 (15)	−0.0023 (11)	0.0024 (12)	0.0058 (11)
C27	0.0295 (13)	0.0270 (13)	0.0355 (16)	0.0035 (11)	0.0015 (12)	0.0037 (12)
C28	0.0408 (16)	0.0333 (15)	0.046 (2)	−0.0028 (13)	0.0000 (15)	0.0101 (14)
C29	0.047 (2)	0.0364 (17)	0.067 (3)	−0.0020 (15)	0.0094 (19)	0.0194 (17)
C30	0.0469 (19)	0.052 (2)	0.049 (2)	0.0184 (17)	0.0188 (17)	0.0210 (18)
C31	0.053 (3)	0.055 (2)	0.046 (3)	0.0143 (18)	−0.0053 (17)	0.004 (2)
C32	0.0390 (17)	0.0401 (17)	0.040 (2)	0.0013 (14)	−0.0057 (15)	0.0058 (15)

O2—H2B	0.89 (4)	C14—C15	1.370 (6)
O5—H5	0.99 (6)	C14—Cl1	1.747 (4)
O7—H7A	0.84 (7)	C15—C16	1.377 (5)
O7—H7B	0.87 (7)	C15—H15	0.93
O8—H8A	0.75 (5)	C16—H16	0.93
O8—H8B	0.84 (6)	C17—C18	1.328 (11)
N1—H1A	0.86	C17—S2	1.652 (8)
N2—H2A	0.86	C17—H17	0.93
N3—H3A	0.86	C18—C19	1.448 (7)
N4—H4A	0.86	C18—H18	0.93
C1—C2	1.338 (11)	C19—C20	1.465 (6)
C1—S1	1.653 (8)	C19—H19	0.93
C1—H1	0.93	C20—C21	1.467 (5)
C2—C3	1.407 (7)	C20—S2	1.703 (4)
C2—H2	0.93	C21—O4	1.209 (5)
C3—C4	1.490 (6)	C21—C22	1.542 (4)
C3—H3	0.93	C22—C26	1.530 (4)
C4—C5	1.449 (5)	C22—C23	1.538 (4)
C4—S1	1.688 (4)	C22—H22	0.98
C5—O1	1.221 (5)	C23—O5	1.393 (4)
C5—C6	1.530 (4)	C23—N3	1.447 (4)
C6—C10	1.533 (4)	C23—C24	1.541 (4)
C6—C7	1.543 (4)	C24—F4	1.317 (4)
C6—H6	0.98	C24—F5	1.328 (4)
C7—O2	1.385 (4)	C24—F6	1.330 (5)
C7—N1	1.448 (4)	C25—O6	1.252 (4)
C7—C8	1.536 (4)	C25—N4	1.332 (4)
C8—F3	1.319 (4)	C25—N3	1.357 (4)
C8—F2	1.323 (4)	C26—N4	1.453 (4)
C8—F1	1.340 (4)	C26—C27	1.520 (4)
C9—O3	1.230 (4)	C26—H26	0.98
C9—N2	1.347 (4)	C27—C28	1.380 (5)
C9—N1	1.363 (4)	C27—C32	1.393 (5)
C10—N2	1.461 (4)	C28—C29	1.399 (5)
C10—C11	1.517 (4)	C28—H28	0.93
C10—H10	0.98	C29—C30	1.367 (6)
C11—C16	1.382 (5)	C29—H29	0.93
C11—C12	1.391 (5)	C30—C31	1.388 (7)
C12—C13	1.376 (6)	C30—Cl2	1.750 (4)
C12—H12	0.93	C31—C32	1.370 (6)
C13—C14	1.363 (6)	C31—H31	0.93
C13—H13	0.93	C32—H32	0.93
C1—S1—C4	93.2 (3)	C13—C14—C15	121.2 (4)
C17—S2—C20	92.5 (3)	C13—C14—Cl1	119.5 (3)
C7—O2—H2B	107 (3)	C15—C14—Cl1	119.3 (3)
C23—O5—H5	106 (4)	C14—C15—C16	119.4 (3)
H7A—O7—H7B	110 (6)	C14—C15—H15	120.3
H8A—O8—H8B	99 (5)	C16—C15—H15	120.3
C7—N1—H1A	119.1	C15—C16—C11	120.8 (3)
C9—N1—C7	121.8 (3)	C15—C16—H16	119.6
C9—N1—H1A	119.1	C11—C16—H16	119.6
C9—N2—C10	125.9 (3)	C18—C17—S2	114.3 (4)
C9—N2—H2A	117.1	C18—C17—H17	122.9
C10—N2—H2A	117.1	S2—C17—H17	122.9
C23—N3—H3A	119.4	C17—C18—C19	115.2 (5)
C25—N3—C23	121.1 (3)	C17—C18—H18	122.4
C25—N3—H3A	119.4	C19—C18—H18	122.4
C25—N4—C26	126.2 (3)	C18—C19—C20	105.9 (4)
C25—N4—H4A	116.9	C18—C19—H19	127.1
C26—N4—H4A	116.9	C20—C19—H19	127.1
C2—C1—S1	113.7 (4)	C19—C20—C21	130.0 (3)
C2—C1—H1	123.2	C19—C20—S2	112.1 (3)
S1—C1—H1	123.2	C21—C20—S2	117.9 (3)
C1—C2—C3	115.4 (6)	O4—C21—C20	120.6 (3)
C1—C2—H2	122.3	O4—C21—C22	121.3 (3)
C3—C2—H2	122.3	C20—C21—C22	118.2 (3)
C2—C3—C4	107.1 (4)	C26—C22—C23	109.5 (2)
C2—C3—H3	126.5	C26—C22—C21	109.3 (2)
C4—C3—H3	126.5	C23—C22—C21	112.8 (2)
C5—C4—C3	129.0 (3)	C26—C22—H22	108.4
C5—C4—S1	120.3 (3)	C23—C22—H22	108.4
C3—C4—S1	110.7 (3)	C21—C22—H22	108.4
O1—C5—C4	120.8 (3)	O5—C23—N3	112.8 (3)
O1—C5—C6	119.5 (3)	O5—C23—C22	109.6 (2)
C4—C5—C6	119.7 (3)	N3—C23—C22	107.5 (2)
C5—C6—C10	109.6 (2)	O5—C23—C24	110.0 (3)
C5—C6—C7	113.1 (2)	N3—C23—C24	107.3 (2)
C10—C6—C7	109.5 (2)	C22—C23—C24	109.6 (2)
C5—C6—H6	108.2	F4—C24—F5	107.6 (3)
C10—C6—H6	108.2	F4—C24—F6	107.1 (3)
C7—C6—H6	108.2	F5—C24—F6	106.0 (3)
O2—C7—N1	112.9 (3)	F4—C24—C23	112.9 (3)
O2—C7—C8	109.6 (3)	F5—C24—C23	110.8 (3)
N1—C7—C8	107.5 (2)	F6—C24—C23	112.1 (3)
O2—C7—C6	108.8 (2)	O6—C25—N4	120.6 (3)
N1—C7—C6	108.0 (2)	O6—C25—N3	120.6 (3)
C8—C7—C6	109.9 (2)	N4—C25—N3	118.8 (3)
F3—C8—F2	108.2 (3)	N4—C26—C27	110.6 (3)
F3—C8—F1	106.9 (3)	N4—C26—C22	108.6 (2)
F2—C8—F1	106.0 (3)	C27—C26—C22	109.4 (3)
F3—C8—C7	112.7 (3)	N4—C26—H26	109.4
F2—C8—C7	111.0 (3)	C27—C26—H26	109.4
F1—C8—C7	111.7 (3)	C22—C26—H26	109.4
O3—C9—N2	120.9 (3)	C28—C27—C32	119.6 (3)
O3—C9—N1	121.0 (3)	C28—C27—C26	120.1 (3)
N2—C9—N1	118.0 (3)	C32—C27—C26	120.2 (3)
N2—C10—C11	110.1 (3)	C27—C28—C29	120.5 (4)
N2—C10—C6	109.1 (2)	C27—C28—H28	119.8
C11—C10—C6	109.5 (3)	C29—C28—H28	119.8
N2—C10—H10	109.4	C30—C29—C28	118.3 (4)
C11—C10—H10	109.4	C30—C29—H29	120.8
C6—C10—H10	109.4	C28—C29—H29	120.8
C16—C11—C12	118.5 (3)	C29—C30—C31	122.2 (4)
C16—C11—C10	120.8 (3)	C29—C30—Cl2	119.5 (3)
C12—C11—C10	120.5 (3)	C31—C30—Cl2	118.3 (4)
C13—C12—C11	120.6 (4)	C32—C31—C30	118.9 (4)
C13—C12—H12	119.7	C32—C31—H31	120.6
C11—C12—H12	119.7	C30—C31—H31	120.6
C14—C13—C12	119.5 (4)	C31—C32—C27	120.5 (4)
C14—C13—H13	120.3	C31—C32—H32	119.7
C12—C13—H13	120.3	C27—C32—H32	119.7
S1—C1—C2—C3	−0.8 (8)	C26—C22—C23—O5	64.1 (3)
C1—C2—C3—C4	1.3 (7)	C21—C22—C23—O5	−57.8 (3)
C2—C3—C4—C5	178.4 (5)	C26—C22—C23—N3	−58.8 (3)
C2—C3—C4—S1	−1.2 (5)	C21—C22—C23—N3	179.3 (3)
C3—C4—C5—O1	167.1 (4)	C26—C22—C23—C24	−175.1 (3)
S1—C4—C5—O1	−13.2 (5)	C21—C22—C23—C24	63.0 (3)
C3—C4—C5—C6	−12.8 (6)	O5—C23—C24—F4	−71.1 (3)
S1—C4—C5—C6	166.8 (3)	N3—C23—C24—F4	51.9 (4)
O1—C5—C6—C10	−56.5 (4)	C22—C23—C24—F4	168.3 (3)
C4—C5—C6—C10	123.4 (3)	O5—C23—C24—F5	49.6 (4)
O1—C5—C6—C7	65.9 (4)	N3—C23—C24—F5	172.6 (3)
C4—C5—C6—C7	−114.1 (3)	C22—C23—C24—F5	−71.0 (4)
C5—C6—C7—O2	−57.0 (3)	O5—C23—C24—F6	167.8 (3)
C10—C6—C7—O2	65.5 (3)	N3—C23—C24—F6	−69.2 (3)
C5—C6—C7—N1	−179.9 (3)	C22—C23—C24—F6	47.2 (4)
C10—C6—C7—N1	−57.4 (3)	C23—C22—C26—N4	48.8 (3)
C5—C6—C7—C8	63.1 (3)	C21—C22—C26—N4	172.8 (3)
C10—C6—C7—C8	−174.5 (3)	C23—C22—C26—C27	169.7 (2)
O2—C7—C8—F3	−72.8 (4)	C21—C22—C26—C27	−66.3 (3)
N1—C7—C8—F3	50.3 (4)	N4—C26—C27—C28	−136.7 (3)
C6—C7—C8—F3	167.7 (3)	C22—C26—C27—C28	103.7 (4)
O2—C7—C8—F2	48.7 (4)	N4—C26—C27—C32	44.8 (4)
N1—C7—C8—F2	171.8 (3)	C22—C26—C27—C32	−74.8 (4)
C6—C7—C8—F2	−70.8 (4)	C32—C27—C28—C29	1.3 (6)
O2—C7—C8—F1	166.9 (3)	C26—C27—C28—C29	−177.2 (3)
N1—C7—C8—F1	−70.0 (3)	C27—C28—C29—C30	−0.7 (6)
C6—C7—C8—F1	47.3 (3)	C28—C29—C30—C31	0.2 (6)
C5—C6—C10—N2	173.3 (3)	C28—C29—C30—Cl2	−178.4 (3)
C7—C6—C10—N2	48.7 (3)	C29—C30—C31—C32	−0.2 (7)
C5—C6—C10—C11	−66.2 (3)	Cl2—C30—C31—C32	178.4 (3)
C7—C6—C10—C11	169.2 (3)	C30—C31—C32—C27	0.8 (7)
N2—C10—C11—C16	−137.7 (3)	C28—C27—C32—C31	−1.3 (6)
C6—C10—C11—C16	102.4 (4)	C26—C27—C32—C31	177.2 (4)
N2—C10—C11—C12	46.7 (4)	O3—C9—N1—C7	165.8 (4)
C6—C10—C11—C12	−73.2 (4)	N2—C9—N1—C7	−18.2 (5)
C16—C11—C12—C13	1.0 (6)	O2—C7—N1—C9	−77.2 (4)
C10—C11—C12—C13	176.7 (4)	C8—C7—N1—C9	161.8 (3)
C11—C12—C13—C14	−0.9 (7)	C6—C7—N1—C9	43.2 (4)
C12—C13—C14—C15	0.7 (7)	O3—C9—N2—C10	−175.4 (4)
C12—C13—C14—Cl1	179.0 (4)	N1—C9—N2—C10	8.6 (6)
C13—C14—C15—C16	−0.6 (6)	C11—C10—N2—C9	−145.7 (4)
Cl1—C14—C15—C16	−179.0 (3)	C6—C10—N2—C9	−25.5 (5)
C14—C15—C16—C11	0.7 (6)	O6—C25—N3—C23	164.7 (4)
C12—C11—C16—C15	−0.9 (6)	N4—C25—N3—C23	−15.9 (6)
C10—C11—C16—C15	−176.6 (3)	O5—C23—N3—C25	−77.9 (4)
S2—C17—C18—C19	1.3 (7)	C22—C23—N3—C25	43.0 (4)
C17—C18—C19—C20	−0.1 (6)	C24—C23—N3—C25	160.8 (3)
C18—C19—C20—C21	−179.4 (4)	O6—C25—N4—C26	−175.8 (4)
C18—C19—C20—S2	−1.1 (4)	N3—C25—N4—C26	4.8 (7)
C19—C20—C21—O4	165.8 (4)	C27—C26—N4—C25	−142.9 (4)
S2—C20—C21—O4	−12.3 (5)	C22—C26—N4—C25	−22.8 (5)
C19—C20—C21—C22	−14.0 (6)	C2—C1—S1—C4	0.0 (6)
S2—C20—C21—C22	167.8 (2)	C5—C4—S1—C1	−179.0 (4)
O4—C21—C22—C26	−58.9 (4)	C3—C4—S1—C1	0.8 (4)
C20—C21—C22—C26	120.9 (3)	C18—C17—S2—C20	−1.7 (5)
O4—C21—C22—C23	63.1 (4)	C19—C20—S2—C17	1.6 (4)
C20—C21—C22—C23	−117.0 (3)	C21—C20—S2—C17	−179.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···F3	0.86	2.38	2.719 (4)	104
N1—H1A···O7i	0.86	2.37	3.022 (4)	132
N2—H2A···O7	0.86	2.15	2.914 (4)	147
O2—H2B···O6ii	0.89 (4)	1.85 (4)	2.694 (4)	156 (3)
N3—H3A···F4	0.86	2.41	2.733 (4)	103
N3—H3A···O8iii	0.86	2.34	3.007 (4)	134
N4—H4A···O8	0.86	2.14	2.921 (4)	151
O5—H5···O3	0.98 (6)	1.72 (6)	2.686 (4)	169 (6)
O7—H7A···O6iii	0.84 (7)	2.27 (7)	2.879 (4)	130 (5)
O7—H7B···O4iv	0.86 (6)	2.36 (6)	2.996 (5)	131 (5)
O7—H7B···O5iv	0.86 (6)	2.18 (6)	2.859 (4)	135 (5)
O8—H8A···O3v	0.75 (5)	2.21 (5)	2.897 (4)	153 (4)
O8—H8B···O1i	0.83 (5)	2.22 (6)	2.968 (5)	150 (5)
O8—H8B···O2i	0.83 (5)	2.27 (6)	2.861 (4)	128 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯F3	0.86	2.38	2.719 (4)	104
N1—H1A⋯O7i	0.86	2.37	3.022 (4)	132
N2—H2A⋯O7	0.86	2.15	2.914 (4)	147
O2—H2B⋯O6ii	0.89 (4)	1.85 (4)	2.694 (4)	156 (3)
N3—H3A⋯F4	0.86	2.41	2.733 (4)	103
N3—H3A⋯O8iii	0.86	2.34	3.007 (4)	134
N4—H4A⋯O8	0.86	2.14	2.921 (4)	151
O5—H5⋯O3	0.98 (6)	1.72 (6)	2.686 (4)	169 (6)
O7—H7A⋯O6iii	0.84 (7)	2.27 (7)	2.879 (4)	130 (5)
O7—H7B⋯O4iv	0.86 (6)	2.36 (6)	2.996 (5)	131 (5)
O7—H7B⋯O5iv	0.86 (6)	2.18 (6)	2.859 (4)	135 (5)
O8—H8A⋯O3v	0.75 (5)	2.21 (5)	2.897 (4)	153 (4)
O8—H8B⋯O1i	0.83 (5)	2.22 (6)	2.968 (5)	150 (5)
O8—H8B⋯O2i	0.83 (5)	2.27 (6)	2.861 (4)	128 (5)

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