N′-(Adamantan-2-yl­idene)thio­phene-2-carbohydrazide

Kadi, A.A.; Alanzi, A.M.; El-Emam, A.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811044758

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3127

doi:10.1107/S1600536811044758

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N′-(Adamantan-2-ylidene)thiophene-2-carbohydrazide

Adnan A. Kadi,^a Amer M. Alanzi,^a Ali A. El-Emam,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 26 October 2011; accepted 26 October 2011; online 29 October 2011)

In the title molecule, C₁₅H₁₈N₂OS, a small twist is noted, with the dihedral angle between the central carbohydrazone residue (r.m.s. deviation = 0.029 Å) and the thiophene ring being 12.47 (10)°. The syn arrangement of the amide H and carbonyl O atoms allows for the formation of centrosymmetric dimers via N—H⋯O hydrogen bonds. These are linked in the three-dimensional structure by C—H⋯π interactions. The thiophene ring is disordered over two co-planar orientations, the major component having a site-occupancy factor of 0.833 (2).

Related literature

For the biological activity of adamantane derivatives see: Vernier et al. (1969 ); El-Emam et al. (2004 ). For background to our work into the biological activity of adamantane derivatives, see: Kadi et al. (2010 ); Al-Omar et al. (2010 ). For a related structure, see: Al-Tamimi et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₈N₂OS
M_r = 274.37
Monoclinic, C 2/c
a = 16.7262 (2) Å
b = 12.5663 (1) Å
c = 13.5562 (2) Å
β = 102.473 (1)°
V = 2782.08 (6) Å³
Z = 8
Cu Kα radiation
μ = 2.01 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.584, T_max = 0.690
5687 measured reflections
2849 independent reflections
2671 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.087
S = 1.04
2849 reflections
189 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1,C1–C4 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.93 (2)	1.92 (2)	2.844 (1)	173 (2)
C13—H13⋯Cg1ⁱⁱ	1.00	2.61	3.5791 (16)	163
C15—H15a⋯Cg1ⁱⁱⁱ	0.99	2.69	3.5683 (16)	148
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{3\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811044758/hg5127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044758/hg5127Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811044758/hg5127Isup3.cml

checkCIF report

Comment top

Derivatives of adamantane have long been known for their diverse biological activities including anti-viral activity against the influenza (Vernier et al., 1969) and HIV viruses (El-Emam et al., 2004). In continuation of our interest in the chemical and pharmacological properties of adamantane derivatives (Kadi et al., 2010; Al-Omar et al., 2010; Al-Tamimi et al., 2010), we synthesized the title compound, N'-(2-thienylcarbonyl)-2-adamantanone hydrazone, (I), as a potential chemotherapeutic agent. Herein, the crystal and molecular structures are described.

A small twist is noted in the molecule of (I), Fig. 1, as seen in the value of the dihedral between the thiophene ring and the central carbohydrazone residue (O1,N1,N2,C4,C5; r.m.s. deviation = 0.029 Å) being 12.47 (10)°. In the major component of the disordered molecule, the thiophene-S atom is proximate to the hydrazone-N atom, S1···N1 = 2.7797 (11) Å, whereas in the minor component, the C3'—H3' atom is 2.29 Å from N2. The amide-H and carbonyl-O atoms are syn. This arrangement allows for the formation of centrosymmetric dimers, Fig. 2 and Table 1, and eight-membered {···HNCO}₂ synthons. The dimers thus formed are consolidated in the crystal packing by C—H···π interactions, Fig. 3 and Table 1.

Related literature top

For the biological activity of adamantane derivatives see: Vernier et al. (1969); El-Emam et al. (2004). For background to our work into the biological activity of adamantane derivatives, see: Kadi et al. (2010); Al-Omar et al. (2010). For a related structure, see: Al-Tamimi et al. (2010).

Experimental top

Thiophene-2-carbohydrazide (1.42 g, 0.01 mol) and 2-adamantanone (1.5 g, 0.01 mol) were heated in ethanol (10 ml) for 4 h. The solid that separated upon cooling was collected and recrystallized from ethanol to yield 2.44 g (98%) of C₁₅H₁₈N₂OS as colourless crystals, M.pt. 464–467 K. The formulation was established by solution NMR spectroscopy. ¹H-NMR (CDCl₃): δ 1.91–2.05 (m, 14 adamantyl-H), 7.12 (s, 1 thienyl H), 7.60–7.63 (m, 1 thienyl H), 8.17 (s, 1 thienyl H), 10.04 (s, 1 amino H) p.p.m.. ¹³C-NMR: 27.78, 30.86, 36.38, 37.81, 39.21, 163.32 (adamantyl), 129.25, 133.78,134.30, 134.90 (thienyl)), 164.15 (carbonyl) p.p.m..

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. Only the major component of the disordered thiophene ring is shown for reasons of clarity.
	Fig. 2. Centrosymmetric dimer in (I) sustained by N—H···O hydrogen bonds shown as blue dashed lines.
	Fig. 3. Unit-cell contents for (I) shown in projection down the b axis. The N—H···O hydrogen bonds and C—H···π interactions are shown as blue and purple dashed lines, respectively.

N'-(Adamantan-2-ylidene)thiophene-2-carbohydrazide top

Crystal data top

C₁₅H₁₈N₂OS	F(000) = 1168
M_r = 274.37	D_x = 1.310 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 4116 reflections
a = 16.7262 (2) Å	θ = 3.3–76.3°
b = 12.5663 (1) Å	µ = 2.01 mm⁻¹
c = 13.5562 (2) Å	T = 100 K
β = 102.473 (1)°	Prism, colourless
V = 2782.08 (6) Å³	0.30 × 0.25 × 0.20 mm
Z = 8

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2849 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2671 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.015
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.5°, θ_min = 4.4°
ω scan	h = −20→21
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −15→15
T_min = 0.584, T_max = 0.690	l = −16→11
5687 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0511P)² + 1.8544P] where P = (F_o² + 2F_c²)/3
2849 reflections	(Δ/σ)_max = 0.001
189 parameters	Δρ_max = 0.38 e Å⁻³
10 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₅H₁₈N₂OS	V = 2782.08 (6) Å³
M_r = 274.37	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 16.7262 (2) Å	µ = 2.01 mm⁻¹
b = 12.5663 (1) Å	T = 100 K
c = 13.5562 (2) Å	0.30 × 0.25 × 0.20 mm
β = 102.473 (1)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2849 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2671 reflections with I > 2σ(I)
T_min = 0.584, T_max = 0.690	R_int = 0.015
5687 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	10 restraints
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.38 e Å⁻³
2849 reflections	Δρ_min = −0.39 e Å⁻³
189 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.32529 (2)	0.46310 (4)	0.24150 (3)	0.01360 (14)	0.833 (2)
C1	0.26341 (15)	0.55387 (19)	0.1659 (2)	0.0172 (5)	0.833 (2)
H1A	0.2777	0.5884	0.1098	0.021*	0.833 (2)
C2	0.1909 (2)	0.5709 (3)	0.1958 (2)	0.0187 (4)	0.833 (2)
H2	0.1493	0.6191	0.1646	0.022*	0.833 (2)
C3	0.18762 (10)	0.5073 (2)	0.2781 (2)	0.0223 (5)	0.833 (2)
H3	0.1417	0.5081	0.3088	0.027*	0.833 (2)
S1'	0.16790 (19)	0.5096 (3)	0.2790 (2)	0.01360 (14)	0.167 (2)
C1'	0.2016 (12)	0.5693 (15)	0.1820 (12)	0.0172 (5)	0.167 (2)
H1'	0.1703	0.6204	0.1384	0.021*	0.167 (2)
C2'	0.2765 (11)	0.5375 (13)	0.1731 (14)	0.0187 (4)	0.167 (2)
H2'	0.3044	0.5617	0.1234	0.022*	0.167 (2)
C3'	0.3071 (7)	0.4624 (12)	0.2493 (10)	0.0223 (5)	0.167 (2)
H3'	0.3588	0.4285	0.2565	0.027*	0.167 (2)
O1	0.19394 (5)	0.34953 (7)	0.42862 (7)	0.0180 (2)
N1	0.32838 (6)	0.32219 (8)	0.44331 (8)	0.0143 (2)
H1	0.3254 (10)	0.2681 (13)	0.4887 (12)	0.023 (4)*
N2	0.39858 (6)	0.33902 (8)	0.40601 (7)	0.0147 (2)
C4	0.25352 (7)	0.44346 (9)	0.31283 (8)	0.0135 (2)
C5	0.25708 (7)	0.36818 (9)	0.39748 (9)	0.0137 (2)
C6	0.46677 (7)	0.30469 (9)	0.45855 (9)	0.0137 (2)
C7	0.54146 (7)	0.31718 (10)	0.41432 (9)	0.0172 (3)
H7	0.5274	0.3575	0.3493	0.021*
C8	0.57170 (8)	0.20454 (11)	0.39590 (10)	0.0216 (3)
H8A	0.5290	0.1666	0.3464	0.026*
H8B	0.6214	0.2095	0.3676	0.026*
C9	0.59118 (7)	0.14246 (10)	0.49565 (10)	0.0194 (3)
H9	0.6107	0.0694	0.4835	0.023*
C10	0.51402 (7)	0.13459 (10)	0.53943 (10)	0.0195 (3)
H10A	0.5265	0.0941	0.6035	0.023*
H10B	0.4706	0.0962	0.4914	0.023*
C11	0.48369 (7)	0.24706 (10)	0.55881 (9)	0.0147 (2)
H11	0.4329	0.2428	0.5862	0.018*
C12	0.55174 (7)	0.30665 (11)	0.63301 (9)	0.0193 (3)
H12A	0.5328	0.3792	0.6449	0.023*
H12B	0.5644	0.2687	0.6985	0.023*
C13	0.62905 (7)	0.31363 (10)	0.58972 (9)	0.0177 (3)
H13	0.6731	0.3514	0.6388	0.021*
C14	0.60877 (7)	0.37598 (10)	0.49038 (10)	0.0196 (3)
H14A	0.6585	0.3830	0.4623	0.024*
H14B	0.5897	0.4483	0.5028	0.024*
C15	0.65806 (7)	0.20126 (10)	0.57098 (9)	0.0184 (3)
H15A	0.6712	0.1615	0.6355	0.022*
H15B	0.7084	0.2056	0.5439	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0146 (3)	0.0164 (2)	0.0113 (2)	−0.00024 (18)	0.00607 (15)	0.00223 (12)
C1	0.0211 (13)	0.0172 (11)	0.0118 (8)	0.0019 (8)	0.0004 (8)	0.0070 (7)
C2	0.0190 (12)	0.0181 (7)	0.0184 (12)	0.0026 (7)	0.0026 (6)	0.0013 (8)
C3	0.0147 (11)	0.0256 (8)	0.0287 (8)	−0.0040 (10)	0.0096 (9)	−0.0030 (7)
S1'	0.0146 (3)	0.0164 (2)	0.0113 (2)	−0.00024 (18)	0.00607 (15)	0.00223 (12)
C1'	0.0211 (13)	0.0172 (11)	0.0118 (8)	0.0019 (8)	0.0004 (8)	0.0070 (7)
C2'	0.0190 (12)	0.0181 (7)	0.0184 (12)	0.0026 (7)	0.0026 (6)	0.0013 (8)
C3'	0.0147 (11)	0.0256 (8)	0.0287 (8)	−0.0040 (10)	0.0096 (9)	−0.0030 (7)
O1	0.0134 (4)	0.0194 (4)	0.0217 (4)	0.0002 (3)	0.0053 (3)	0.0062 (3)
N1	0.0125 (5)	0.0153 (5)	0.0153 (5)	0.0001 (4)	0.0036 (4)	0.0035 (4)
N2	0.0139 (5)	0.0153 (5)	0.0159 (5)	0.0005 (4)	0.0052 (4)	0.0016 (4)
C4	0.0149 (5)	0.0128 (5)	0.0125 (5)	−0.0014 (4)	0.0024 (4)	−0.0010 (4)
C5	0.0141 (5)	0.0118 (5)	0.0147 (5)	−0.0010 (4)	0.0021 (4)	−0.0015 (4)
C6	0.0149 (5)	0.0128 (5)	0.0138 (5)	0.0000 (4)	0.0041 (4)	0.0006 (4)
C7	0.0160 (6)	0.0213 (6)	0.0160 (6)	0.0026 (4)	0.0068 (4)	0.0059 (5)
C8	0.0214 (6)	0.0266 (7)	0.0176 (6)	0.0041 (5)	0.0062 (5)	−0.0034 (5)
C9	0.0187 (6)	0.0145 (6)	0.0249 (6)	0.0031 (4)	0.0045 (5)	0.0001 (5)
C10	0.0167 (6)	0.0152 (6)	0.0251 (6)	−0.0025 (4)	0.0009 (5)	0.0059 (5)
C11	0.0115 (5)	0.0189 (6)	0.0141 (5)	−0.0009 (4)	0.0035 (4)	0.0040 (4)
C12	0.0155 (6)	0.0274 (7)	0.0148 (6)	−0.0014 (5)	0.0029 (5)	−0.0027 (5)
C13	0.0130 (5)	0.0202 (6)	0.0196 (6)	−0.0035 (4)	0.0028 (4)	−0.0011 (5)
C14	0.0153 (5)	0.0161 (6)	0.0289 (7)	−0.0009 (4)	0.0081 (5)	0.0051 (5)
C15	0.0132 (5)	0.0204 (6)	0.0215 (6)	0.0012 (4)	0.0037 (5)	0.0060 (5)

Geometric parameters (Å, º) top

S1—C4	1.7142 (12)	C7—C8	1.5415 (18)
S1—C1	1.7215 (15)	C7—C14	1.5412 (17)
C1—C2	1.377 (2)	C7—H7	1.0000
C1—H1A	0.9500	C8—C9	1.5340 (18)
C2—C3	1.382 (3)	C8—H8A	0.9900
C2—H2	0.9500	C8—H8B	0.9900
C3—C4	1.362 (2)	C9—C15	1.5319 (17)
C3—H3	0.9500	C9—C10	1.5358 (17)
S1'—C4	1.634 (3)	C9—H9	1.0000
S1'—C1'	1.712 (9)	C10—C11	1.5432 (17)
C1'—C2'	1.344 (9)	C10—H10A	0.9900
C1'—H1'	0.9500	C10—H10B	0.9900
C2'—C3'	1.411 (10)	C11—C12	1.5406 (16)
C2'—H2'	0.9500	C11—H11	1.0000
C3'—C4	1.391 (8)	C12—C13	1.5336 (16)
C3'—H3'	0.9500	C12—H12A	0.9900
O1—C5	1.2414 (14)	C12—H12B	0.9900
N1—C5	1.3499 (15)	C13—C14	1.5313 (17)
N1—N2	1.3912 (13)	C13—C15	1.5321 (17)
N1—H1	0.926 (17)	C13—H13	1.0000
N2—C6	1.2820 (15)	C14—H14A	0.9900
C4—C5	1.4784 (16)	C14—H14B	0.9900
C6—C7	1.5062 (15)	C15—H15A	0.9900
C6—C11	1.5118 (15)	C15—H15B	0.9900

C4—S1—C1	91.53 (11)	C7—C8—H8A	109.7
C2—C1—S1	112.5 (3)	C9—C8—H8B	109.7
C2—C1—H1A	123.7	C7—C8—H8B	109.7
S1—C1—H1A	123.7	H8A—C8—H8B	108.2
C1—C2—C3	109.8 (3)	C15—C9—C8	109.14 (10)
C1—C2—H2	125.1	C15—C9—C10	109.09 (10)
C3—C2—H2	125.1	C8—C9—C10	109.70 (10)
C4—C3—C2	116.73 (19)	C15—C9—H9	109.6
C4—C3—H3	121.6	C8—C9—H9	109.6
C2—C3—H3	121.6	C10—C9—H9	109.6
C4—S1'—C1'	91.4 (7)	C9—C10—C11	109.97 (10)
C2'—C1'—S1'	114.0 (15)	C9—C10—H10A	109.7
C2'—C1'—H1'	123.0	C11—C10—H10A	109.7
S1'—C1'—H1'	123.0	C9—C10—H10B	109.7
C1'—C2'—C3'	109.4 (17)	C11—C10—H10B	109.7
C1'—C2'—H2'	125.3	H10A—C10—H10B	108.2
C3'—C2'—H2'	125.3	C6—C11—C12	108.82 (10)
C4—C3'—C2'	112.8 (12)	C6—C11—C10	106.87 (10)
C4—C3'—H3'	123.6	C12—C11—C10	109.43 (10)
C2'—C3'—H3'	123.6	C6—C11—H11	110.5
C5—N1—N2	119.91 (10)	C12—C11—H11	110.5
C5—N1—H1	116.8 (10)	C10—C11—H11	110.5
N2—N1—H1	121.6 (10)	C13—C12—C11	110.07 (10)
C6—N2—N1	117.79 (10)	C13—C12—H12A	109.6
C3—C4—C3'	105.5 (6)	C11—C12—H12A	109.6
C3—C4—C5	122.63 (13)	C13—C12—H12B	109.6
C3'—C4—C5	131.8 (6)	C11—C12—H12B	109.6
C3'—C4—S1'	112.5 (6)	H12A—C12—H12B	108.2
C5—C4—S1'	115.42 (13)	C14—C13—C15	110.10 (10)
C3—C4—S1	109.44 (12)	C14—C13—C12	108.72 (10)
C5—C4—S1	127.90 (9)	C15—C13—C12	109.52 (10)
S1'—C4—S1	116.54 (13)	C14—C13—H13	109.5
O1—C5—N1	119.64 (10)	C15—C13—H13	109.5
O1—C5—C4	119.35 (10)	C12—C13—H13	109.5
N1—C5—C4	120.98 (10)	C13—C14—C7	109.52 (10)
N2—C6—C7	117.30 (10)	C13—C14—H14A	109.8
N2—C6—C11	129.20 (11)	C7—C14—H14A	109.8
C7—C6—C11	113.42 (9)	C13—C14—H14B	109.8
C6—C7—C8	107.35 (10)	C7—C14—H14B	109.8
C6—C7—C14	109.42 (10)	H14A—C14—H14B	108.2
C8—C7—C14	109.31 (10)	C13—C15—C9	110.08 (10)
C6—C7—H7	110.2	C13—C15—H15A	109.6
C8—C7—H7	110.2	C9—C15—H15A	109.6
C14—C7—H7	110.2	C13—C15—H15B	109.6
C9—C8—C7	109.81 (10)	C9—C15—H15B	109.6
C9—C8—H8A	109.7	H15A—C15—H15B	108.2

C4—S1—C1—C2	1.5 (2)	S1—C4—C5—N1	15.62 (17)
S1—C1—C2—C3	−1.4 (3)	N1—N2—C6—C7	176.23 (10)
C1—C2—C3—C4	0.4 (4)	N1—N2—C6—C11	−0.37 (18)
C4—S1'—C1'—C2'	1.7 (16)	N2—C6—C7—C8	−115.56 (12)
S1'—C1'—C2'—C3'	−1 (2)	C11—C6—C7—C8	61.57 (13)
C1'—C2'—C3'—C4	−1 (2)	N2—C6—C7—C14	125.92 (11)
C5—N1—N2—C6	171.74 (11)	C11—C6—C7—C14	−56.95 (13)
C2—C3—C4—C3'	−0.8 (7)	C6—C7—C8—C9	−58.56 (13)
C2—C3—C4—C5	−177.5 (2)	C14—C7—C8—C9	60.04 (13)
C2—C3—C4—S1'	−161 (2)	C7—C8—C9—C15	−60.03 (13)
C2—C3—C4—S1	0.8 (3)	C7—C8—C9—C10	59.45 (13)
C2'—C3'—C4—C3	−0.4 (14)	C15—C9—C10—C11	59.76 (12)
C2'—C3'—C4—C5	175.8 (10)	C8—C9—C10—C11	−59.75 (13)
C2'—C3'—C4—S1'	2.4 (16)	N2—C6—C11—C12	−126.71 (13)
C2'—C3'—C4—S1	−160 (10)	C7—C6—C11—C12	56.58 (13)
C1'—S1'—C4—C3	18.8 (18)	N2—C6—C11—C10	115.21 (13)
C1'—S1'—C4—C3'	−2.3 (11)	C7—C6—C11—C10	−61.49 (12)
C1'—S1'—C4—C5	−176.8 (7)	C9—C10—C11—C6	58.68 (12)
C1'—S1'—C4—S1	−0.8 (7)	C9—C10—C11—C12	−58.99 (13)
C1—S1—C4—C3	−1.28 (18)	C6—C11—C12—C13	−57.90 (13)
C1—S1—C4—C3'	19 (9)	C10—C11—C12—C13	58.55 (13)
C1—S1—C4—C5	176.83 (14)	C11—C12—C13—C14	61.27 (13)
C1—S1—C4—S1'	1.40 (18)	C11—C12—C13—C15	−59.07 (13)
N2—N1—C5—O1	177.15 (10)	C15—C13—C14—C7	59.00 (12)
N2—N1—C5—C4	−4.97 (16)	C12—C13—C14—C7	−60.97 (13)
C3—C4—C5—O1	11.4 (2)	C6—C7—C14—C13	58.13 (13)
C3'—C4—C5—O1	−164.3 (9)	C8—C7—C14—C13	−59.16 (13)
S1'—C4—C5—O1	9.0 (2)	C14—C13—C15—C9	−59.43 (12)
S1—C4—C5—O1	−166.49 (9)	C12—C13—C15—C9	60.06 (13)
C3—C4—C5—N1	−166.50 (17)	C8—C9—C15—C13	59.55 (13)
C3'—C4—C5—N1	17.8 (9)	C10—C9—C15—C13	−60.30 (13)
S1'—C4—C5—N1	−168.90 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the S1,C1–C4 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.93 (2)	1.92 (2)	2.844 (1)	173 (2)
C13—H13···Cg1ⁱⁱ	1.00	2.61	3.5791 (16)	163
C15—H15a···Cg1ⁱⁱⁱ	0.99	2.69	3.5683 (16)	148

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₈N₂OS
M_r	274.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	16.7262 (2), 12.5663 (1), 13.5562 (2)
β (°)	102.473 (1)
V (Å³)	2782.08 (6)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	2.01
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.584, 0.690
No. of measured, independent and observed [I > 2σ(I)] reflections	5687, 2849, 2671
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.087, 1.04
No. of reflections	2849
No. of parameters	189
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.39

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the S1,C1–C4 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.93 (2)	1.92 (2)	2.844 (1)	173 (2)
C13—H13···Cg1ⁱⁱ	1.00	2.61	3.5791 (16)	163
C15—H15a···Cg1ⁱⁱⁱ	0.99	2.69	3.5683 (16)	148

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

Footnotes

‡Additional correspondence author, e-mail: elemam5@hotmail.com.

Acknowledgements

We thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, and the University of Malaya for supporting this study.

References

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Volume 67| Part 11| November 2011| Page o3127

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