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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1339.
Published online 2009 May 20. doi:  10.1107/S1600536809017097
PMCID: PMC2969779

4-(4-Chloro­phen­yl)-6-hydr­oxy-5-(2-thienyl­carbonyl)-6-(trifluoro­meth­yl)-3,4,5,6-tetra­hydro­pyrimidin-2(1H)-one monohydrate

Abstract

The asymmetric unit of the title compound, C16H12ClF3N2O3S·H2O, contains two crystallographically independent organic mol­ecules and two water mol­ecules. The organic species are linked by an inter­molecular O—H(...)O hydrogen bond, while the water mol­ecules are connected to them through inter­molecular O—H(...)N hydrogen bonds. The thio­phene and phenyl rings are oriented at dihedral angles of 62.35 (4) in the first independent mol­ecule and 60.74 (5)° in the second, while the pyrimidine rings adopt twisted conformations in both molecules. Intra­molecular N—H(...)F inter­actions result in the formation of two five-membered rings having envelope conformations. In the crystal structure, further inter­molecular O—H(...)O and N—H(...)O hydrogen bonds link the mol­ecules into chains.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-o1339-scheme1.jpg

Experimental

Crystal data

  • C16H12ClF3N2O3S·H2O
  • M r = 422.81
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1339-efi1.jpg
  • 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 [triangle]) 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 [triangle]), 4326 Friedel pairs
  • Flack parameter: 0.18 (8)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The authors are grateful to Islamic Azad University, Yazd Branch, for financial support.

supplementary crystallographic information

Comment

In recent years, several modified and improved procedures for one-pot synthesis of dihydropyrimidine-2(1H)-ones have been reported (Paraskar et al., 2003; Peng & Deng, 2001). However, in spite of their potential utility, many of these methods suffer from drawback like longer reaction times, unsatisfactory yields and cumbersome product isolation procedures. We report herein the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules and two water molecules (Fig. 1 ), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (S1/C1–C4), C (C11–C16) and D (S2/C17–C20), F (C27–C32) are, of course, planar and they are oriented at dihedral angles of A/C = 62.35 (4)° and D/F = 60.74 (5)°. Rings B (N1/N2/C6/C7/C9/C10) and E (N3/N4/C22/C23/C25/C26) adopt twisted conformations. Intramolecular N—H···F interactions (Table 1) result in the formations of two five-membered rings G (N1/F3/C7/C8/H1A) and H (N3/F4/C23/C24/H3A) having envelope conformations with atoms C8 and C24 displaced by 0.594 (4) and -0.603 (5) Å from the planes of the other rings atoms. Intramolecular O—H···O hydrogen bond (Table 1) link the two molecules, while the water molecules are connected to them through the intramolecular N—H···O hydrogen bonds (Table 1).

In the crystal structure, intermolecular O—H···O and N—H···O hydrogen bonds (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, a mixture of 1-(2-thenoyl)-3,3,3-trifluoroacetone (0.222 g, 1 mmol), 4-chlorobenzaldehyde (0.141 g, 1 mmol), urea (0.18 g, 3 mmol) and ammonium chloride (0.005 g, 0.1 mmol) were heated at 373 K under stirring for 20 min. After cooling, the reaction mixture was poured onto crushed ice (20 g). The separated solid was filtered, washed with cold water (20 ml) and recrystallized from ethylacetate–hexane (1:3) to afford pure product (yield; 78%, 0.330 g).

Refinement

H atoms of water molecules and OH groups were located in difference Fourier map and refined isotropically. The remaining H atoms were positioned geometrically with N—H = 0.86 Å (for NH) and C—H = 0.93 and 0.98 Å, for aromatic and methine H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
A partial packing diagram of the title compound viewed down the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C16H12ClF3N2O3S·H2OF(000) = 1728
Mr = 422.81Dx = 1.577 Mg m3
Orthorhombic, Pbn21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2abCell parameters from 1879 reflections
a = 9.1156 (6) Åθ = 2.4–29.2°
b = 14.1582 (7) ŵ = 0.39 mm1
c = 27.6012 (17) ÅT = 298 K
V = 3562.2 (4) Å3Block, colourless
Z = 80.5 × 0.3 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer7478 reflections with I > 2σ(I)
[var phi] and ω scansRint = 0.032
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)θmax = 29.2°, θmin = 2.4°
Tmin = 0.860, Tmax = 0.923h = −11→12
19595 measured reflectionsk = −19→19
9251 independent reflectionsl = −37→36

Refinement

Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: fullw = 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) = 0.146Δρmax = 0.41 e Å3
S = 1.07Δρmin = −0.47 e Å3
9251 reflectionsAbsolute structure: Flack (1983), 4326 Friedel pairs
511 parametersFlack parameter: 0.18 (8)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl10.20863 (18)1.18591 (11)0.10132 (6)0.0800 (4)
Cl20.71737 (17)0.07620 (11)0.51510 (6)0.0829 (5)
S1−0.37400 (15)0.85338 (12)0.12927 (6)0.0797 (4)
S20.13318 (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)*
O30.3549 (3)0.69972 (17)0.28201 (10)0.0414 (6)
O40.2597 (3)0.4046 (3)0.39238 (14)0.0539 (8)
O50.4027 (3)0.54419 (17)0.33543 (9)0.0394 (5)
H50.396 (7)0.604 (4)0.318 (2)0.088 (18)*
O60.8546 (3)0.55885 (17)0.33323 (10)0.0413 (6)
O70.3736 (3)0.9773 (2)0.30044 (11)0.0433 (6)
H7A0.459 (8)0.964 (4)0.309 (2)0.09 (2)*
H7B0.321 (7)0.993 (4)0.325 (2)0.080 (18)*
O80.8726 (3)0.2819 (2)0.31572 (11)0.0423 (6)
H8A0.946 (6)0.278 (3)0.3038 (17)0.045 (13)*
H8B0.820 (6)0.283 (4)0.291 (2)0.066 (15)*
N10.1334 (3)0.66639 (19)0.24968 (11)0.0335 (6)
H1A0.15460.60740.2470.04*
N20.2184 (4)0.8206 (2)0.25512 (13)0.0408 (7)
H2A0.2910.85790.26050.049*
N30.6328 (3)0.59341 (18)0.36587 (10)0.0314 (5)
H3A0.65430.65240.36790.038*
N40.7153 (4)0.43923 (19)0.36029 (13)0.0385 (7)
H4A0.78640.40150.35350.046*
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)
F40.4222 (3)0.72493 (15)0.38632 (10)0.0572 (6)
F50.2705 (3)0.6231 (2)0.41348 (15)0.0686 (9)
F60.4700 (3)0.64863 (18)0.45092 (9)0.0618 (7)
C1−0.3412 (9)0.8435 (4)0.0706 (3)0.094 (2)
H1−0.41330.85060.0470.112*
C2−0.2010 (10)0.8242 (5)0.0601 (2)0.084 (2)
H2−0.16820.81610.02850.1*
C3−0.1067 (5)0.8169 (3)0.10026 (15)0.0440 (8)
H3−0.00630.80510.09940.053*
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)
H60.04970.77490.17880.034*
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)
C90.2396 (3)0.7281 (3)0.26401 (15)0.0311 (7)
C100.0830 (4)0.8633 (2)0.23712 (12)0.0314 (6)
H100.02410.88550.26460.038*
C110.1184 (3)0.9461 (2)0.20424 (12)0.0319 (6)
C120.2245 (5)0.9376 (3)0.1683 (2)0.0462 (9)
H120.27770.88180.16550.055*
C130.2516 (4)1.0109 (3)0.13683 (18)0.0466 (11)
H130.32361.00520.11310.056*
C140.1722 (4)1.0921 (3)0.14066 (14)0.0453 (8)
C150.0667 (5)1.1025 (3)0.17562 (15)0.0461 (9)
H150.01391.15860.1780.055*
C160.0395 (4)1.0292 (2)0.20716 (14)0.0397 (7)
H16−0.03281.03580.23070.048*
C170.1708 (9)0.4116 (5)0.5484 (3)0.088 (2)
H170.09970.40450.57230.105*
C180.3112 (9)0.4273 (4)0.5583 (2)0.0804 (18)
H180.34630.43080.58990.096*
C190.4056 (5)0.4386 (3)0.51657 (13)0.0444 (8)
H190.5060.45010.51670.053*
C200.3103 (4)0.4283 (3)0.47414 (15)0.0421 (8)
C210.3463 (4)0.4322 (2)0.42239 (14)0.0365 (7)
C220.4972 (3)0.4722 (2)0.40755 (11)0.0287 (6)
H220.55230.48710.43710.034*
C230.4852 (3)0.5625 (2)0.37684 (11)0.0285 (6)
C240.4120 (4)0.6412 (2)0.40686 (14)0.0386 (7)
C250.7380 (4)0.5309 (2)0.35238 (16)0.0331 (8)
C260.5819 (3)0.3969 (2)0.37927 (12)0.0307 (6)
H260.52150.37420.35230.037*
C270.6181 (3)0.3148 (2)0.41269 (12)0.0307 (6)
C280.5391 (4)0.2319 (2)0.40975 (14)0.0401 (7)
H280.46650.22530.38630.048*
C290.5675 (4)0.1575 (3)0.44180 (17)0.0499 (9)
H290.51380.10170.44020.06*
C300.6760 (4)0.1689 (3)0.47547 (15)0.0492 (10)
C310.7576 (5)0.2514 (3)0.4788 (2)0.0515 (12)
H310.83060.25750.50210.062*
C320.7287 (4)0.3237 (3)0.44722 (16)0.0398 (8)
H320.78330.37910.44880.048*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0826 (8)0.0777 (8)0.0797 (9)−0.0138 (7)0.0002 (8)0.0486 (7)
Cl20.0798 (8)0.0833 (8)0.0856 (10)0.0318 (7)0.0201 (8)0.0568 (8)
S10.0514 (6)0.0965 (10)0.0912 (11)0.0052 (7)−0.0265 (7)0.0229 (8)
S20.0571 (7)0.0907 (10)0.0937 (11)−0.0052 (7)0.0273 (8)0.0203 (8)
O10.0466 (16)0.0612 (18)0.054 (2)0.0213 (13)0.0096 (13)0.0121 (15)
O20.0436 (14)0.0339 (12)0.0427 (14)0.0050 (11)0.0152 (11)0.0097 (11)
O30.0324 (12)0.0356 (12)0.0561 (16)−0.0016 (9)−0.0148 (11)0.0126 (11)
O40.0398 (15)0.0719 (19)0.050 (2)−0.0212 (13)−0.0117 (12)0.0137 (15)
O50.0443 (13)0.0339 (12)0.0400 (13)−0.0061 (10)−0.0126 (11)0.0086 (10)
O60.0356 (12)0.0367 (12)0.0515 (15)0.0034 (10)0.0149 (11)0.0112 (11)
O70.0327 (13)0.0486 (15)0.0486 (16)−0.0070 (11)0.0040 (11)−0.0024 (12)
O80.0315 (13)0.0482 (15)0.0472 (15)0.0060 (11)−0.0037 (12)−0.0004 (12)
N10.0298 (12)0.0255 (12)0.0451 (17)0.0001 (10)−0.0053 (11)0.0014 (11)
N20.0395 (14)0.0272 (13)0.056 (2)−0.0045 (12)−0.0210 (15)0.0089 (12)
N30.0281 (12)0.0246 (11)0.0414 (15)−0.0004 (9)0.0072 (11)0.0021 (10)
N40.0399 (14)0.0280 (12)0.0475 (18)0.0089 (12)0.0166 (14)0.0047 (11)
F10.0750 (16)0.0529 (13)0.0443 (13)−0.0109 (12)−0.0044 (12)−0.0085 (11)
F20.0333 (11)0.0598 (15)0.112 (3)−0.0091 (11)−0.0239 (15)0.0002 (16)
F30.0688 (15)0.0297 (9)0.0674 (16)−0.0121 (10)−0.0203 (13)0.0055 (10)
F40.0739 (16)0.0313 (10)0.0664 (16)0.0138 (10)0.0233 (13)0.0062 (10)
F50.0312 (10)0.0600 (15)0.115 (3)0.0080 (10)0.0226 (15)−0.0060 (16)
F60.0785 (18)0.0637 (14)0.0433 (13)0.0138 (13)0.0042 (12)−0.0161 (11)
C10.115 (5)0.076 (4)0.090 (5)0.007 (4)−0.071 (4)0.007 (3)
C20.132 (6)0.077 (4)0.041 (3)0.015 (4)−0.022 (3)0.003 (2)
C30.053 (2)0.0481 (19)0.0310 (17)0.0122 (16)−0.0079 (16)0.0067 (15)
C40.0383 (18)0.0404 (17)0.049 (2)0.0002 (14)−0.0079 (15)0.0121 (16)
C50.0302 (15)0.0331 (15)0.0397 (18)0.0016 (12)0.0018 (12)0.0065 (13)
C60.0256 (13)0.0301 (13)0.0302 (15)−0.0005 (10)0.0013 (11)0.0037 (12)
C70.0250 (13)0.0266 (12)0.0348 (15)−0.0014 (10)−0.0003 (11)0.0006 (11)
C80.0340 (15)0.0332 (15)0.0427 (18)−0.0031 (12)−0.0074 (14)0.0016 (13)
C90.0307 (16)0.0329 (15)0.0297 (19)−0.0014 (12)−0.0019 (11)0.0048 (13)
C100.0381 (16)0.0238 (12)0.0322 (16)0.0010 (11)−0.0003 (12)0.0029 (11)
C110.0342 (15)0.0302 (14)0.0312 (15)−0.0020 (11)−0.0042 (12)0.0048 (12)
C120.0484 (19)0.0333 (17)0.057 (3)0.0017 (15)0.012 (2)−0.0047 (16)
C130.051 (3)0.051 (2)0.037 (3)−0.0155 (17)0.0098 (15)0.0014 (18)
C140.0478 (19)0.0446 (19)0.0435 (19)−0.0134 (16)−0.0069 (16)0.0182 (16)
C150.047 (2)0.0348 (16)0.056 (2)0.0060 (15)−0.0049 (17)0.0120 (16)
C160.0369 (16)0.0360 (16)0.0464 (19)0.0024 (13)0.0037 (15)0.0045 (15)
C170.106 (5)0.074 (4)0.083 (4)0.001 (3)0.059 (4)0.014 (3)
C180.122 (6)0.070 (3)0.050 (3)0.0003 (3)0.017 (3)0.015 (2)
C190.054 (2)0.052 (2)0.0271 (17)0.0350 (3)0.0152 (15)0.0050 (15)
C200.0339 (17)0.0429 (18)0.050 (2)0.0030 (14)0.0108 (15)0.0132 (15)
C210.0302 (15)0.0361 (15)0.0431 (18)−0.0016 (12)0.0007 (13)0.0118 (14)
C220.0261 (13)0.0304 (13)0.0297 (15)−0.0015 (10)−0.0009 (11)0.0030 (11)
C230.0252 (13)0.0282 (13)0.0321 (15)−0.0007 (10)−0.0010 (11)0.0027 (11)
C240.0289 (14)0.0389 (16)0.048 (2)0.0046 (12)0.0079 (14)0.0032 (14)
C250.0289 (16)0.0306 (15)0.040 (2)0.0029 (11)0.0083 (12)0.0042 (14)
C260.0335 (14)0.0278 (13)0.0309 (15)−0.0023 (11)0.0024 (12)0.0058 (11)
C270.0295 (13)0.0270 (13)0.0355 (16)0.0035 (11)0.0015 (12)0.0037 (12)
C280.0408 (16)0.0333 (15)0.046 (2)−0.0028 (13)0.0000 (15)0.0101 (14)
C290.047 (2)0.0364 (17)0.067 (3)−0.0020 (15)0.0094 (19)0.0194 (17)
C300.0469 (19)0.052 (2)0.049 (2)0.0184 (17)0.0188 (17)0.0210 (18)
C310.053 (3)0.055 (2)0.046 (3)0.0143 (18)−0.0053 (17)0.004 (2)
C320.0390 (17)0.0401 (17)0.040 (2)0.0013 (14)−0.0057 (15)0.0058 (15)

Geometric parameters (Å, °)

O2—H2B0.89 (4)C14—C151.370 (6)
O5—H50.99 (6)C14—Cl11.747 (4)
O7—H7A0.84 (7)C15—C161.377 (5)
O7—H7B0.87 (7)C15—H150.93
O8—H8A0.75 (5)C16—H160.93
O8—H8B0.84 (6)C17—C181.328 (11)
N1—H1A0.86C17—S21.652 (8)
N2—H2A0.86C17—H170.93
N3—H3A0.86C18—C191.448 (7)
N4—H4A0.86C18—H180.93
C1—C21.338 (11)C19—C201.465 (6)
C1—S11.653 (8)C19—H190.93
C1—H10.93C20—C211.467 (5)
C2—C31.407 (7)C20—S21.703 (4)
C2—H20.93C21—O41.209 (5)
C3—C41.490 (6)C21—C221.542 (4)
C3—H30.93C22—C261.530 (4)
C4—C51.449 (5)C22—C231.538 (4)
C4—S11.688 (4)C22—H220.98
C5—O11.221 (5)C23—O51.393 (4)
C5—C61.530 (4)C23—N31.447 (4)
C6—C101.533 (4)C23—C241.541 (4)
C6—C71.543 (4)C24—F41.317 (4)
C6—H60.98C24—F51.328 (4)
C7—O21.385 (4)C24—F61.330 (5)
C7—N11.448 (4)C25—O61.252 (4)
C7—C81.536 (4)C25—N41.332 (4)
C8—F31.319 (4)C25—N31.357 (4)
C8—F21.323 (4)C26—N41.453 (4)
C8—F11.340 (4)C26—C271.520 (4)
C9—O31.230 (4)C26—H260.98
C9—N21.347 (4)C27—C281.380 (5)
C9—N11.363 (4)C27—C321.393 (5)
C10—N21.461 (4)C28—C291.399 (5)
C10—C111.517 (4)C28—H280.93
C10—H100.98C29—C301.367 (6)
C11—C161.382 (5)C29—H290.93
C11—C121.391 (5)C30—C311.388 (7)
C12—C131.376 (6)C30—Cl21.750 (4)
C12—H120.93C31—C321.370 (6)
C13—C141.363 (6)C31—H310.93
C13—H130.93C32—H320.93
C1—S1—C493.2 (3)C13—C14—C15121.2 (4)
C17—S2—C2092.5 (3)C13—C14—Cl1119.5 (3)
C7—O2—H2B107 (3)C15—C14—Cl1119.3 (3)
C23—O5—H5106 (4)C14—C15—C16119.4 (3)
H7A—O7—H7B110 (6)C14—C15—H15120.3
H8A—O8—H8B99 (5)C16—C15—H15120.3
C7—N1—H1A119.1C15—C16—C11120.8 (3)
C9—N1—C7121.8 (3)C15—C16—H16119.6
C9—N1—H1A119.1C11—C16—H16119.6
C9—N2—C10125.9 (3)C18—C17—S2114.3 (4)
C9—N2—H2A117.1C18—C17—H17122.9
C10—N2—H2A117.1S2—C17—H17122.9
C23—N3—H3A119.4C17—C18—C19115.2 (5)
C25—N3—C23121.1 (3)C17—C18—H18122.4
C25—N3—H3A119.4C19—C18—H18122.4
C25—N4—C26126.2 (3)C18—C19—C20105.9 (4)
C25—N4—H4A116.9C18—C19—H19127.1
C26—N4—H4A116.9C20—C19—H19127.1
C2—C1—S1113.7 (4)C19—C20—C21130.0 (3)
C2—C1—H1123.2C19—C20—S2112.1 (3)
S1—C1—H1123.2C21—C20—S2117.9 (3)
C1—C2—C3115.4 (6)O4—C21—C20120.6 (3)
C1—C2—H2122.3O4—C21—C22121.3 (3)
C3—C2—H2122.3C20—C21—C22118.2 (3)
C2—C3—C4107.1 (4)C26—C22—C23109.5 (2)
C2—C3—H3126.5C26—C22—C21109.3 (2)
C4—C3—H3126.5C23—C22—C21112.8 (2)
C5—C4—C3129.0 (3)C26—C22—H22108.4
C5—C4—S1120.3 (3)C23—C22—H22108.4
C3—C4—S1110.7 (3)C21—C22—H22108.4
O1—C5—C4120.8 (3)O5—C23—N3112.8 (3)
O1—C5—C6119.5 (3)O5—C23—C22109.6 (2)
C4—C5—C6119.7 (3)N3—C23—C22107.5 (2)
C5—C6—C10109.6 (2)O5—C23—C24110.0 (3)
C5—C6—C7113.1 (2)N3—C23—C24107.3 (2)
C10—C6—C7109.5 (2)C22—C23—C24109.6 (2)
C5—C6—H6108.2F4—C24—F5107.6 (3)
C10—C6—H6108.2F4—C24—F6107.1 (3)
C7—C6—H6108.2F5—C24—F6106.0 (3)
O2—C7—N1112.9 (3)F4—C24—C23112.9 (3)
O2—C7—C8109.6 (3)F5—C24—C23110.8 (3)
N1—C7—C8107.5 (2)F6—C24—C23112.1 (3)
O2—C7—C6108.8 (2)O6—C25—N4120.6 (3)
N1—C7—C6108.0 (2)O6—C25—N3120.6 (3)
C8—C7—C6109.9 (2)N4—C25—N3118.8 (3)
F3—C8—F2108.2 (3)N4—C26—C27110.6 (3)
F3—C8—F1106.9 (3)N4—C26—C22108.6 (2)
F2—C8—F1106.0 (3)C27—C26—C22109.4 (3)
F3—C8—C7112.7 (3)N4—C26—H26109.4
F2—C8—C7111.0 (3)C27—C26—H26109.4
F1—C8—C7111.7 (3)C22—C26—H26109.4
O3—C9—N2120.9 (3)C28—C27—C32119.6 (3)
O3—C9—N1121.0 (3)C28—C27—C26120.1 (3)
N2—C9—N1118.0 (3)C32—C27—C26120.2 (3)
N2—C10—C11110.1 (3)C27—C28—C29120.5 (4)
N2—C10—C6109.1 (2)C27—C28—H28119.8
C11—C10—C6109.5 (3)C29—C28—H28119.8
N2—C10—H10109.4C30—C29—C28118.3 (4)
C11—C10—H10109.4C30—C29—H29120.8
C6—C10—H10109.4C28—C29—H29120.8
C16—C11—C12118.5 (3)C29—C30—C31122.2 (4)
C16—C11—C10120.8 (3)C29—C30—Cl2119.5 (3)
C12—C11—C10120.5 (3)C31—C30—Cl2118.3 (4)
C13—C12—C11120.6 (4)C32—C31—C30118.9 (4)
C13—C12—H12119.7C32—C31—H31120.6
C11—C12—H12119.7C30—C31—H31120.6
C14—C13—C12119.5 (4)C31—C32—C27120.5 (4)
C14—C13—H13120.3C31—C32—H32119.7
C12—C13—H13120.3C27—C32—H32119.7
S1—C1—C2—C3−0.8 (8)C26—C22—C23—O564.1 (3)
C1—C2—C3—C41.3 (7)C21—C22—C23—O5−57.8 (3)
C2—C3—C4—C5178.4 (5)C26—C22—C23—N3−58.8 (3)
C2—C3—C4—S1−1.2 (5)C21—C22—C23—N3179.3 (3)
C3—C4—C5—O1167.1 (4)C26—C22—C23—C24−175.1 (3)
S1—C4—C5—O1−13.2 (5)C21—C22—C23—C2463.0 (3)
C3—C4—C5—C6−12.8 (6)O5—C23—C24—F4−71.1 (3)
S1—C4—C5—C6166.8 (3)N3—C23—C24—F451.9 (4)
O1—C5—C6—C10−56.5 (4)C22—C23—C24—F4168.3 (3)
C4—C5—C6—C10123.4 (3)O5—C23—C24—F549.6 (4)
O1—C5—C6—C765.9 (4)N3—C23—C24—F5172.6 (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—F6167.8 (3)
C10—C6—C7—O265.5 (3)N3—C23—C24—F6−69.2 (3)
C5—C6—C7—N1−179.9 (3)C22—C23—C24—F647.2 (4)
C10—C6—C7—N1−57.4 (3)C23—C22—C26—N448.8 (3)
C5—C6—C7—C863.1 (3)C21—C22—C26—N4172.8 (3)
C10—C6—C7—C8−174.5 (3)C23—C22—C26—C27169.7 (2)
O2—C7—C8—F3−72.8 (4)C21—C22—C26—C27−66.3 (3)
N1—C7—C8—F350.3 (4)N4—C26—C27—C28−136.7 (3)
C6—C7—C8—F3167.7 (3)C22—C26—C27—C28103.7 (4)
O2—C7—C8—F248.7 (4)N4—C26—C27—C3244.8 (4)
N1—C7—C8—F2171.8 (3)C22—C26—C27—C32−74.8 (4)
C6—C7—C8—F2−70.8 (4)C32—C27—C28—C291.3 (6)
O2—C7—C8—F1166.9 (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—F147.3 (3)C28—C29—C30—C310.2 (6)
C5—C6—C10—N2173.3 (3)C28—C29—C30—Cl2−178.4 (3)
C7—C6—C10—N248.7 (3)C29—C30—C31—C32−0.2 (7)
C5—C6—C10—C11−66.2 (3)Cl2—C30—C31—C32178.4 (3)
C7—C6—C10—C11169.2 (3)C30—C31—C32—C270.8 (7)
N2—C10—C11—C16−137.7 (3)C28—C27—C32—C31−1.3 (6)
C6—C10—C11—C16102.4 (4)C26—C27—C32—C31177.2 (4)
N2—C10—C11—C1246.7 (4)O3—C9—N1—C7165.8 (4)
C6—C10—C11—C12−73.2 (4)N2—C9—N1—C7−18.2 (5)
C16—C11—C12—C131.0 (6)O2—C7—N1—C9−77.2 (4)
C10—C11—C12—C13176.7 (4)C8—C7—N1—C9161.8 (3)
C11—C12—C13—C14−0.9 (7)C6—C7—N1—C943.2 (4)
C12—C13—C14—C150.7 (7)O3—C9—N2—C10−175.4 (4)
C12—C13—C14—Cl1179.0 (4)N1—C9—N2—C108.6 (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—C110.7 (6)O6—C25—N3—C23164.7 (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—C191.3 (7)C22—C23—N3—C2543.0 (4)
C17—C18—C19—C20−0.1 (6)C24—C23—N3—C25160.8 (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—C264.8 (7)
C19—C20—C21—O4165.8 (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—C40.0 (6)
S2—C20—C21—C22167.8 (2)C5—C4—S1—C1−179.0 (4)
O4—C21—C22—C26−58.9 (4)C3—C4—S1—C10.8 (4)
C20—C21—C22—C26120.9 (3)C18—C17—S2—C20−1.7 (5)
O4—C21—C22—C2363.1 (4)C19—C20—S2—C171.6 (4)
C20—C21—C22—C23−117.0 (3)C21—C20—S2—C17−179.9 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···F30.862.382.719 (4)104
N1—H1A···O7i0.862.373.022 (4)132
N2—H2A···O70.862.152.914 (4)147
O2—H2B···O6ii0.89 (4)1.85 (4)2.694 (4)156 (3)
N3—H3A···F40.862.412.733 (4)103
N3—H3A···O8iii0.862.343.007 (4)134
N4—H4A···O80.862.142.921 (4)151
O5—H5···O30.98 (6)1.72 (6)2.686 (4)169 (6)
O7—H7A···O6iii0.84 (7)2.27 (7)2.879 (4)130 (5)
O7—H7B···O4iv0.86 (6)2.36 (6)2.996 (5)131 (5)
O7—H7B···O5iv0.86 (6)2.18 (6)2.859 (4)135 (5)
O8—H8A···O3v0.75 (5)2.21 (5)2.897 (4)153 (4)
O8—H8B···O1i0.83 (5)2.22 (6)2.968 (5)150 (5)
O8—H8B···O2i0.83 (5)2.27 (6)2.861 (4)128 (5)

Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) x−1, y, z; (iii) −x+3/2, y+1/2, z; (iv) −x+1/2, y+1/2, z; (v) −x+3/2, y−1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2682).

References

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  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Paraskar, A. S., Dewkar, G. K. & Sudalai, A. (2003). Tetrahedron Lett. 44, 3305–3308.
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  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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