N'-(Adamantan-2-yl-idene)thio-phene-2-carbohydrazide.

In the title mol-ecule, C(15)H(18)N(2)OS, a small twist is noted, with the dihedral angle between the central carbohydrazone residue (r.m.s. deviation = 0.029 Å) and the thio-phene 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 inter-actions. The thio-phene 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 = 274.37

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.087

S = 1.04

2849 reflections

189 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.39 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044758/hg5127sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811044758/hg5127Isup3.cml

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

C15H18N2OS	F(000) = 1168
Mr = 274.37	Dx = 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

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	Rint = 0.015
Detector resolution: 10.4041 pixels mm-1	θmax = 76.5°, θmin = 4.4°
ω scan	h = −20→21
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −15→15
Tmin = 0.584, Tmax = 0.690	l = −16→11
5687 measured reflections

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(Fo2) + (0.0511P)2 + 1.8544P] where P = (Fo2 + 2Fc2)/3
2849 reflections	(Δ/σ)max = 0.001
189 parameters	Δρmax = 0.38 e Å−3
10 restraints	Δρmin = −0.39 e Å−3

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

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) ; (ii) ; (iii) .