1-(Adamantan-1-ylcarbon­yl)-3-(2,6-difluoro-4-hy­droxy­phen­yl)thio­urea

Mohamed, S.K.; Jaber, A.-A.M.; Saeed, S.; Ahmad, K.S.; Wong, W.-T.

doi:10.1107/S1600536812018806

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1597

doi:10.1107/S1600536812018806

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1-(Adamantan-1-ylcarbonyl)-3-(2,6-difluoro-4-hydroxyphenyl)thiourea

Shaaban K. Mohamed,^a Abdel-Aal M. Jaber,^b Sohail Saeed,^c ^* Khuram Shahzad Ahmad ^c and Wing-Tak Wong ^d

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bChemistry Department, Faculty of Science, Assiut University, Assiut, Egypt, ^cDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan, and ^dDepartment of Chemistry, The University of Hong Kong, Pokfulam Road, Pokfulam, Hong Kong SAR, People's Republic of China
^*Correspondence e-mail: sohail262001@yahoo.com

(Received 13 April 2012; accepted 26 April 2012; online 2 May 2012)

In the title molecule, C₁₈H₂₀F₂N₂O₂S, the 2,6-difluoro-4-hydroxyphenyl ring and the carbonylthiourea group are each essentially planar, with maximum deviations of atoms from their mean planes of 0.0113 (14) and 0.1017 (15) Å, respectively; the dihedral angle between these two planes is 71.03 (6)°. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, N—H⋯O and O—H⋯S hydrogen bonds connect the molecules into chains running diagonally across the bc plane. C—H⋯S and C—H⋯F contacts are also observed.

Related literature

For background studies of thiourea derivatives, see: Saeed et al. (2011 ). For a related structure, see: Saeed et al. (2010 ).

Experimental

Crystal data

C₁₈H₂₀F₂N₂O₂S
M_r = 366.42
Triclinic, $[P \overline 1]$
a = 7.3985 (9) Å
b = 10.4953 (13) Å
c = 12.4094 (15) Å
α = 65.554 (2)°
β = 79.372 (2)°
γ = 89.766 (2)°
V = 859.34 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.38 × 0.36 × 0.08 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.920, T_max = 0.982
4824 measured reflections
2976 independent reflections
2399 reflections with I > 2σ(I)
R_int = 0.010

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.100
S = 1.04
2976 reflections
238 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.79 (2)	2.09 (2)	2.692 (2)	133 (2)
N1—H1⋯O2ⁱ	0.79 (2)	2.52 (2)	3.185 (3)	142 (2)
O1—H1O⋯S1ⁱⁱ	0.87 (3)	2.36 (3)	3.212 (2)	169 (3)
C14—H14A⋯S1ⁱⁱⁱ	0.97	2.84	3.761 (2)	159
C14—H14B⋯F1^iv	0.97	2.45	3.354 (3)	155
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+2, -y, -z+2; (iii) -x+2, -y, -z+1; (iv) x-1, y, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 2006 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018806/pv2537sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018806/pv2537Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018806/pv2537Isup3.cml

checkCIF report

Comment top

In continuation of our studies on structural chemistry of N,N'-disubstituted thiourea (Saeed, et al., 2011), the structure of the title compound is described in this article.

In the title molecule (Fig. 1), the 2,6-difluoro-4-hydroxy-phenyl ring (C1–C6/O1/F1/F2) and the carbonyl thiourea group (S1/N1/N2/O2/C7/C8) are individually more or less planar, with maximum deviations of atoms from their mean planes being 0.0113 (14) Å for O1 and 0.1017 (15) Å for N2, respectively; the dihedral angle between these two planes is 71.03 (6)°.

Hydrogen bonding interactions were observed in the crystal lattice which connect the molecules into 1-D chains running diagonally across the b-c-plane (Table 1 and Fig. 2).

Related literature top

For background studies of thiourea derivatives, see: Saeed et al. (2011). For a related structure, see: Saeed et al. (2010).

Experimental top

A mixture of adamantane-1-carbonyl chloride (199 mg, 1 mmol), 4-amino-3,5-difluorophenol (145 mg, 1 mmol) and potassium thiocyanate (100 mg) was heated for 30 minutes in ethanol (5 ml) at 351 K. The reaction mixture was left overnight to cool down at room temperature to afford a solid product which was filtered off, washed and recrystallized from ethanol. Colorless crystals suitable for X-ray crystallographic studies were collected and dried (yield = 82%; m. p. = 455-456 K).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the N—H···O and O—H···S hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity.

1-(Adamantan-1-ylcarbonyl)-3-(2,6-difluoro-4-hydroxyphenyl)thiourea top

Crystal data top

C₁₈H₂₀F₂N₂O₂S	Z = 2
M_r = 366.42	F(000) = 384
Triclinic, P1	D_x = 1.416 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3985 (9) Å	Cell parameters from 4824 reflections
b = 10.4953 (13) Å	θ = 2.8–25.0°
c = 12.4094 (15) Å	µ = 0.22 mm⁻¹
α = 65.554 (2)°	T = 296 K
β = 79.372 (2)°	Plate, colourless
γ = 89.766 (2)°	0.38 × 0.36 × 0.08 mm
V = 859.34 (18) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	2976 independent reflections
Radiation source: fine-focus sealed tube	2399 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.010
ω & ϕ scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→8
T_min = 0.920, T_max = 0.982	k = −9→12
4824 measured reflections	l = −14→14

Refinement top

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0409P)² + 0.3498P] where P = (F_o² + 2F_c²)/3
2976 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₈H₂₀F₂N₂O₂S	γ = 89.766 (2)°
M_r = 366.42	V = 859.34 (18) Å³
Triclinic, P1	Z = 2
a = 7.3985 (9) Å	Mo Kα radiation
b = 10.4953 (13) Å	µ = 0.22 mm⁻¹
c = 12.4094 (15) Å	T = 296 K
α = 65.554 (2)°	0.38 × 0.36 × 0.08 mm
β = 79.372 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	2976 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2399 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.982	R_int = 0.010
4824 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.17 e Å⁻³
2976 reflections	Δρ_min = −0.18 e Å⁻³
238 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.98449 (8)	−0.02031 (6)	0.68281 (5)	0.05290 (18)
F1	1.3675 (2)	0.16253 (18)	0.66290 (12)	0.0801 (5)
F2	0.81301 (19)	0.25665 (16)	0.85556 (13)	0.0769 (4)
O1	1.2972 (3)	0.08462 (19)	1.06720 (15)	0.0659 (5)
H1O	1.212 (4)	0.076 (3)	1.128 (3)	0.095 (11)*
O2	0.8566 (3)	0.42734 (17)	0.47025 (18)	0.0918 (7)
N1	1.0107 (3)	0.2470 (2)	0.64901 (16)	0.0533 (5)
H1	0.993 (3)	0.327 (3)	0.613 (2)	0.061 (7)*
N2	0.8692 (3)	0.19619 (19)	0.51851 (15)	0.0481 (4)
H2	0.838 (3)	0.132 (2)	0.5017 (18)	0.046 (6)*
C1	1.0863 (3)	0.2106 (2)	0.75458 (17)	0.0465 (5)
C2	1.2611 (3)	0.1657 (2)	0.76211 (18)	0.0508 (5)
C3	1.3321 (3)	0.1234 (2)	0.86477 (18)	0.0521 (5)
H3	1.4501	0.0926	0.8662	0.063*
C4	1.2233 (3)	0.1278 (2)	0.96622 (17)	0.0467 (5)
C5	1.0489 (3)	0.1751 (2)	0.96344 (18)	0.0491 (5)
H5	0.9768	0.1803	1.0311	0.059*
C6	0.9851 (3)	0.2141 (2)	0.85798 (19)	0.0484 (5)
C7	0.9559 (3)	0.1514 (2)	0.61553 (16)	0.0433 (5)
C8	0.8121 (3)	0.3264 (2)	0.45461 (19)	0.0517 (5)
C9	0.6926 (3)	0.3338 (2)	0.36480 (16)	0.0417 (4)
C10	0.5468 (3)	0.4380 (2)	0.3671 (2)	0.0615 (6)
H10A	0.4691	0.4041	0.4471	0.074*
H10B	0.6072	0.5285	0.3488	0.074*
C11	0.4287 (4)	0.4539 (3)	0.2740 (3)	0.0733 (8)
H11	0.3357	0.5200	0.2761	0.088*
C12	0.3332 (3)	0.3132 (3)	0.3014 (3)	0.0759 (8)
H12A	0.2537	0.2768	0.3810	0.091*
H12B	0.2573	0.3246	0.2426	0.091*
C13	0.4766 (3)	0.2112 (2)	0.2971 (2)	0.0541 (5)
H13	0.4143	0.1204	0.3151	0.065*
C14	0.5933 (3)	0.1922 (2)	0.39204 (18)	0.0457 (5)
H14A	0.6834	0.1251	0.3912	0.055*
H14B	0.5145	0.1559	0.4718	0.055*
C15	0.8154 (3)	0.3888 (3)	0.23861 (19)	0.0575 (6)
H15A	0.9072	0.3232	0.2363	0.069*
H15B	0.8793	0.4783	0.2197	0.069*
C16	0.6960 (4)	0.4067 (3)	0.1452 (2)	0.0684 (7)
H16	0.7744	0.4432	0.0643	0.082*
C17	0.6014 (3)	0.2650 (3)	0.1738 (2)	0.0631 (6)
H17A	0.5297	0.2744	0.1133	0.076*
H17B	0.6932	0.1990	0.1728	0.076*
C18	0.5517 (4)	0.5102 (3)	0.1499 (2)	0.0811 (9)
H18A	0.6129	0.6003	0.1320	0.097*
H18B	0.4778	0.5238	0.0896	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0726 (4)	0.0439 (3)	0.0474 (3)	0.0169 (3)	−0.0265 (3)	−0.0185 (2)
F1	0.0762 (10)	0.1176 (13)	0.0479 (8)	0.0208 (9)	−0.0104 (7)	−0.0372 (8)
F2	0.0675 (9)	0.0973 (11)	0.0828 (10)	0.0420 (8)	−0.0378 (8)	−0.0454 (9)
O1	0.0662 (11)	0.0889 (13)	0.0456 (9)	0.0123 (9)	−0.0283 (8)	−0.0240 (9)
O2	0.1500 (18)	0.0459 (10)	0.1119 (15)	0.0241 (10)	−0.0993 (14)	−0.0348 (10)
N1	0.0806 (14)	0.0408 (10)	0.0478 (10)	0.0158 (10)	−0.0380 (10)	−0.0175 (9)
N2	0.0674 (12)	0.0421 (10)	0.0468 (10)	0.0137 (9)	−0.0317 (9)	−0.0221 (8)
C1	0.0626 (13)	0.0406 (11)	0.0417 (11)	0.0084 (10)	−0.0255 (10)	−0.0165 (9)
C2	0.0556 (13)	0.0596 (13)	0.0379 (11)	0.0067 (10)	−0.0114 (9)	−0.0203 (10)
C3	0.0463 (12)	0.0630 (14)	0.0465 (12)	0.0087 (10)	−0.0163 (9)	−0.0194 (10)
C4	0.0523 (12)	0.0483 (12)	0.0398 (11)	0.0010 (9)	−0.0199 (9)	−0.0142 (9)
C5	0.0561 (13)	0.0529 (12)	0.0414 (11)	0.0070 (10)	−0.0134 (9)	−0.0214 (10)
C6	0.0515 (12)	0.0458 (11)	0.0549 (12)	0.0139 (9)	−0.0240 (10)	−0.0226 (10)
C7	0.0497 (11)	0.0473 (11)	0.0370 (10)	0.0114 (9)	−0.0172 (9)	−0.0183 (9)
C8	0.0689 (14)	0.0439 (12)	0.0497 (12)	0.0104 (10)	−0.0311 (11)	−0.0192 (10)
C9	0.0494 (11)	0.0394 (10)	0.0394 (10)	0.0077 (9)	−0.0197 (9)	−0.0152 (9)
C10	0.0797 (16)	0.0561 (14)	0.0650 (14)	0.0285 (12)	−0.0339 (12)	−0.0335 (12)
C11	0.0812 (18)	0.0689 (17)	0.0902 (19)	0.0416 (14)	−0.0524 (16)	−0.0393 (15)
C12	0.0513 (14)	0.090 (2)	0.096 (2)	0.0159 (13)	−0.0330 (14)	−0.0404 (16)
C13	0.0497 (12)	0.0524 (13)	0.0647 (14)	0.0012 (10)	−0.0258 (11)	−0.0232 (11)
C14	0.0472 (11)	0.0448 (11)	0.0428 (11)	0.0029 (9)	−0.0128 (9)	−0.0145 (9)
C15	0.0553 (13)	0.0594 (14)	0.0500 (12)	−0.0110 (11)	−0.0106 (10)	−0.0152 (11)
C16	0.0849 (18)	0.0748 (17)	0.0357 (11)	−0.0125 (14)	−0.0149 (11)	−0.0124 (11)
C17	0.0784 (16)	0.0709 (16)	0.0530 (13)	0.0091 (13)	−0.0310 (12)	−0.0314 (12)
C18	0.124 (2)	0.0520 (14)	0.0721 (17)	0.0101 (15)	−0.0662 (17)	−0.0112 (13)

Geometric parameters (Å, º) top

S1—C7	1.675 (2)	C10—C11	1.529 (3)
F1—C2	1.346 (2)	C10—H10A	0.9700
F2—C6	1.349 (2)	C10—H10B	0.9700
O1—C4	1.362 (2)	C11—C18	1.512 (4)
O1—H1O	0.87 (3)	C11—C12	1.517 (4)
O2—C8	1.211 (2)	C11—H11	0.9800
N1—C7	1.325 (3)	C12—C13	1.514 (3)
N1—C1	1.425 (2)	C12—H12A	0.9700
N1—H1	0.79 (2)	C12—H12B	0.9700
N2—C7	1.377 (2)	C13—C17	1.510 (3)
N2—C8	1.377 (3)	C13—C14	1.534 (3)
N2—H2	0.83 (2)	C13—H13	0.9800
C1—C6	1.376 (3)	C14—H14A	0.9700
C1—C2	1.380 (3)	C14—H14B	0.9700
C2—C3	1.369 (3)	C15—C16	1.535 (3)
C3—C4	1.382 (3)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.382 (3)	C16—C17	1.519 (3)
C5—C6	1.373 (3)	C16—C18	1.531 (4)
C5—H5	0.9300	C16—H16	0.9800
C8—C9	1.523 (2)	C17—H17A	0.9700
C9—C15	1.531 (3)	C17—H17B	0.9700
C9—C10	1.538 (3)	C18—H18A	0.9700
C9—C14	1.538 (3)	C18—H18B	0.9700

C4—O1—H1O	109 (2)	C18—C11—H11	109.4
C7—N1—C1	122.30 (17)	C12—C11—H11	109.4
C7—N1—H1	119.5 (17)	C10—C11—H11	109.4
C1—N1—H1	118.0 (17)	C13—C12—C11	109.5 (2)
C7—N2—C8	129.89 (18)	C13—C12—H12A	109.8
C7—N2—H2	113.5 (14)	C11—C12—H12A	109.8
C8—N2—H2	116.3 (14)	C13—C12—H12B	109.8
C6—C1—C2	115.57 (17)	C11—C12—H12B	109.8
C6—C1—N1	121.27 (19)	H12A—C12—H12B	108.2
C2—C1—N1	123.14 (19)	C17—C13—C12	110.9 (2)
F1—C2—C3	118.07 (19)	C17—C13—C14	109.09 (17)
F1—C2—C1	118.10 (17)	C12—C13—C14	109.23 (19)
C3—C2—C1	123.83 (19)	C17—C13—H13	109.2
C2—C3—C4	118.00 (19)	C12—C13—H13	109.2
C2—C3—H3	121.0	C14—C13—H13	109.2
C4—C3—H3	121.0	C13—C14—C9	109.91 (16)
O1—C4—C5	122.39 (19)	C13—C14—H14A	109.7
O1—C4—C3	116.74 (19)	C9—C14—H14A	109.7
C5—C4—C3	120.87 (17)	C13—C14—H14B	109.7
C6—C5—C4	118.13 (19)	C9—C14—H14B	109.7
C6—C5—H5	120.9	H14A—C14—H14B	108.2
C4—C5—H5	120.9	C9—C15—C16	109.42 (18)
F2—C6—C5	118.48 (19)	C9—C15—H15A	109.8
F2—C6—C1	117.93 (17)	C16—C15—H15A	109.8
C5—C6—C1	123.58 (19)	C9—C15—H15B	109.8
N1—C7—N2	117.75 (17)	C16—C15—H15B	109.8
N1—C7—S1	124.67 (14)	H15A—C15—H15B	108.2
N2—C7—S1	117.59 (15)	C17—C16—C18	110.1 (2)
O2—C8—N2	120.81 (18)	C17—C16—C15	109.17 (19)
O2—C8—C9	123.18 (18)	C18—C16—C15	109.3 (2)
N2—C8—C9	116.01 (17)	C17—C16—H16	109.4
C8—C9—C15	108.41 (17)	C18—C16—H16	109.4
C8—C9—C10	107.81 (16)	C15—C16—H16	109.4
C15—C9—C10	109.33 (17)	C13—C17—C16	109.20 (19)
C8—C9—C14	114.03 (15)	C13—C17—H17A	109.8
C15—C9—C14	108.57 (16)	C16—C17—H17A	109.8
C10—C9—C14	108.62 (17)	C13—C17—H17B	109.8
C11—C10—C9	109.65 (17)	C16—C17—H17B	109.8
C11—C10—H10A	109.7	H17A—C17—H17B	108.3
C9—C10—H10A	109.7	C11—C18—C16	109.77 (19)
C11—C10—H10B	109.7	C11—C18—H18A	109.7
C9—C10—H10B	109.7	C16—C18—H18A	109.7
H10A—C10—H10B	108.2	C11—C18—H18B	109.7
C18—C11—C12	109.5 (2)	C16—C18—H18B	109.7
C18—C11—C10	108.9 (2)	H18A—C18—H18B	108.2
C12—C11—C10	110.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.79 (2)	2.09 (2)	2.692 (2)	133 (2)
N1—H1···O2ⁱ	0.79 (2)	2.52 (2)	3.185 (3)	142 (2)
O1—H1O···S1ⁱⁱ	0.87 (3)	2.36 (3)	3.212 (2)	169 (3)
C14—H14A···S1ⁱⁱⁱ	0.97	2.84	3.761 (2)	159
C14—H14B···F1^iv	0.97	2.45	3.354 (3)	155

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀F₂N₂O₂S
M_r	366.42
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.3985 (9), 10.4953 (13), 12.4094 (15)
α, β, γ (°)	65.554 (2), 79.372 (2), 89.766 (2)
V (Å³)	859.34 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.38 × 0.36 × 0.08

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.920, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	4824, 2976, 2399
R_int	0.010
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.100, 1.04
No. of reflections	2976
No. of parameters	238
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.79 (2)	2.09 (2)	2.692 (2)	133 (2)
N1—H1···O2ⁱ	0.79 (2)	2.52 (2)	3.185 (3)	142 (2)
O1—H1O···S1ⁱⁱ	0.87 (3)	2.36 (3)	3.212 (2)	169 (3)
C14—H14A···S1ⁱⁱⁱ	0.97	2.84	3.761 (2)	159
C14—H14B···F1^iv	0.97	2.45	3.354 (3)	155

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

Acknowledgements

SS is thankful to the University of Hong Kong for providing the facility for crystallographic studies.

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2006). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Saeed, S., Rashid, N., Bhatti, M. H. & Jones, P. G. (2010). Turk. J. Chem. 34, 761–770. CAS Google Scholar
Saeed, S., Rashid, N., Hussain, R. & Jones, P. G. (2011). Eur. J. Chem. 2, 77–82. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar