Diphenyl-methyl isothio-cyanate.

The asymmetric unit of the title compound, C(14)H(11)NS, contains two mol-ecules in which the dihedral angles between the phenyl rings are 77.23 (7) and 86.30 (7)°. No aromatic π-π stacking inter-actions are observed.

Related literature

For the synthetic applications of isothio­cyanates, see: Fernandez et al. (1995 ▶); Mukerjee & Ashare (1991 ▶); Stephensen & Zaragosa (1997 ▶).

Experimental

Crystal data

C14H11NS

M = 225.30

Triclinic,

a = 9.635 (5) Å

b = 10.222 (6) Å

c = 11.974 (7) Å

α = 98.491 (13)°

β = 95.296 (15)°

γ = 93.573 (6)°

V = 1157.9 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 113 K

0.24 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.943, T max = 0.957

12035 measured reflections

5430 independent reflections

3169 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.079

S = 0.89

5430 reflections

289 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000888/hb6596sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000888/hb6596Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000888/hb6596Isup3.cml

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

C14H11NS	Z = 4
Mr = 225.30	F(000) = 472
Triclinic, P1	Dx = 1.292 Mg m−3
a = 9.635 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.222 (6) Å	Cell parameters from 3900 reflections
c = 11.974 (7) Å	θ = 1.7–28.0°
α = 98.491 (13)°	µ = 0.25 mm−1
β = 95.296 (15)°	T = 113 K
γ = 93.573 (6)°	Prism, colorless
V = 1157.9 (11) Å3	0.24 × 0.20 × 0.18 mm

Rigaku Saturn724 CCD diffractometer	5430 independent reflections
Radiation source: rotating anode	3169 reflections with I > 2σ(I)
multilayer	Rint = 0.042
Detector resolution: 14.22 pixels mm-1	θmax = 27.9°, θmin = 1.7°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −13→13
Tmin = 0.943, Tmax = 0.957	l = −15→12
12035 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 0.89	w = 1/[σ2(Fo2) + (0.0253P)2] where P = (Fo2 + 2Fc2)/3
5430 reflections	(Δ/σ)max = 0.003
289 parameters	Δρmax = 0.20 e Å−3
2 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.10665 (4)	0.73024 (4)	0.96006 (4)	0.03299 (12)
S2	0.11876 (4)	1.01973 (4)	0.18909 (4)	0.03186 (12)
N1	0.10403 (14)	0.46640 (15)	0.86731 (12)	0.0375 (4)
N2	0.27245 (15)	0.85453 (13)	0.30434 (11)	0.0353 (4)
C1	0.14265 (15)	0.41926 (16)	0.63396 (13)	0.0266 (4)
H1	0.1367	0.5072	0.6711	0.032*
C2	0.15692 (15)	0.39629 (17)	0.51813 (14)	0.0298 (4)
H2	0.1605	0.4686	0.4766	0.036*
C3	0.16580 (15)	0.26911 (17)	0.46354 (13)	0.0286 (4)
H3	0.1770	0.2538	0.3848	0.034*
C4	0.15828 (15)	0.16335 (16)	0.52411 (13)	0.0292 (4)
H4	0.1623	0.0754	0.4863	0.035*
C5	0.14493 (15)	0.18588 (15)	0.63921 (13)	0.0267 (4)
H5	0.1411	0.1133	0.6803	0.032*
C6	0.13704 (14)	0.31449 (15)	0.69539 (12)	0.0216 (3)
C7	0.12841 (16)	0.33178 (15)	0.82319 (12)	0.0254 (4)
H7	0.0469	0.2731	0.8372	0.030*
C8	0.25897 (15)	0.28997 (15)	0.88646 (12)	0.0233 (3)
C9	0.38754 (16)	0.36001 (17)	0.88849 (13)	0.0309 (4)
H9	0.3937	0.4374	0.8534	0.037*
C10	0.50688 (16)	0.31767 (18)	0.94139 (13)	0.0352 (4)
H10	0.5947	0.3656	0.9421	0.042*
C11	0.49818 (16)	0.20569 (17)	0.99316 (13)	0.0324 (4)
H11	0.5800	0.1768	1.0296	0.039*
C12	0.37035 (17)	0.13574 (16)	0.99191 (13)	0.0309 (4)
H12	0.3645	0.0585	1.0272	0.037*
C13	0.25053 (16)	0.17819 (15)	0.93923 (12)	0.0259 (4)
H13	0.1627	0.1306	0.9393	0.031*
C14	0.10830 (15)	0.57794 (17)	0.90672 (13)	0.0262 (4)
C15	0.25922 (15)	0.57519 (16)	0.25156 (13)	0.0269 (4)
H15	0.1838	0.6219	0.2249	0.032*
C16	0.26212 (16)	0.44037 (16)	0.21331 (13)	0.0305 (4)
H16	0.1888	0.3949	0.1607	0.037*
C17	0.37235 (16)	0.37218 (16)	0.25209 (13)	0.0284 (4)
H17	0.3748	0.2801	0.2256	0.034*
C18	0.47868 (16)	0.43822 (15)	0.32921 (13)	0.0260 (4)
H18	0.5539	0.3914	0.3560	0.031*
C19	0.47557 (15)	0.57276 (15)	0.36751 (12)	0.0241 (3)
H19	0.5486	0.6178	0.4206	0.029*
C20	0.36602 (15)	0.64199 (14)	0.32856 (12)	0.0208 (3)
C21	0.37093 (15)	0.79000 (14)	0.37246 (12)	0.0242 (4)
H21	0.4669	0.8293	0.3656	0.029*
C22	0.34411 (15)	0.81973 (14)	0.49715 (13)	0.0215 (3)
C23	0.45057 (16)	0.87830 (14)	0.57871 (13)	0.0249 (4)
H23	0.5404	0.9000	0.5567	0.030*
C24	0.42671 (16)	0.90538 (15)	0.69248 (13)	0.0280 (4)
H24	0.4997	0.9462	0.7478	0.034*
C25	0.29602 (16)	0.87249 (15)	0.72478 (13)	0.0277 (4)
H25	0.2791	0.8911	0.8022	0.033*
C26	0.19007 (16)	0.81236 (15)	0.64359 (13)	0.0279 (4)
H26	0.1009	0.7890	0.6659	0.034*
C27	0.21326 (15)	0.78614 (15)	0.53047 (13)	0.0249 (4)
H27	0.1401	0.7452	0.4754	0.030*
C28	0.20928 (15)	0.92584 (15)	0.25600 (12)	0.0226 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0286 (2)	0.0308 (3)	0.0386 (3)	0.00210 (18)	0.00829 (19)	−0.0008 (2)
S2	0.0346 (2)	0.0281 (2)	0.0330 (3)	0.00572 (18)	−0.00353 (19)	0.0080 (2)
N1	0.0422 (9)	0.0355 (9)	0.0344 (9)	0.0162 (7)	0.0031 (7)	−0.0012 (7)
N2	0.0481 (9)	0.0309 (8)	0.0290 (8)	0.0109 (7)	0.0020 (7)	0.0090 (7)
C1	0.0235 (8)	0.0244 (9)	0.0313 (10)	0.0030 (7)	0.0002 (7)	0.0029 (8)
C2	0.0246 (9)	0.0332 (10)	0.0326 (10)	−0.0012 (7)	−0.0005 (7)	0.0120 (8)
C3	0.0204 (8)	0.0427 (11)	0.0220 (9)	−0.0013 (7)	0.0023 (7)	0.0047 (8)
C4	0.0292 (9)	0.0283 (9)	0.0285 (10)	0.0042 (7)	0.0036 (7)	−0.0023 (8)
C5	0.0292 (9)	0.0250 (9)	0.0271 (9)	0.0066 (7)	0.0025 (7)	0.0064 (8)
C6	0.0167 (8)	0.0251 (9)	0.0228 (9)	0.0050 (6)	0.0004 (6)	0.0031 (7)
C7	0.0245 (8)	0.0270 (9)	0.0247 (9)	0.0053 (7)	0.0034 (7)	0.0020 (7)
C8	0.0232 (8)	0.0298 (9)	0.0163 (8)	0.0047 (7)	0.0023 (6)	0.0006 (7)
C9	0.0312 (9)	0.0410 (11)	0.0218 (9)	−0.0020 (8)	0.0031 (7)	0.0106 (8)
C10	0.0230 (9)	0.0561 (12)	0.0264 (10)	−0.0036 (8)	0.0018 (7)	0.0096 (9)
C11	0.0275 (9)	0.0463 (12)	0.0230 (9)	0.0102 (8)	−0.0007 (7)	0.0032 (8)
C12	0.0380 (10)	0.0300 (10)	0.0250 (9)	0.0085 (8)	0.0008 (8)	0.0045 (8)
C13	0.0253 (9)	0.0283 (9)	0.0225 (9)	0.0002 (7)	0.0027 (7)	−0.0003 (7)
C14	0.0200 (8)	0.0382 (11)	0.0218 (9)	0.0081 (7)	0.0047 (6)	0.0052 (8)
C15	0.0214 (8)	0.0314 (10)	0.0277 (9)	0.0040 (7)	0.0001 (7)	0.0048 (8)
C16	0.0281 (9)	0.0335 (10)	0.0259 (9)	−0.0053 (7)	−0.0013 (7)	−0.0030 (8)
C17	0.0340 (10)	0.0224 (9)	0.0289 (10)	0.0028 (7)	0.0084 (8)	0.0006 (8)
C18	0.0254 (9)	0.0264 (9)	0.0277 (9)	0.0076 (7)	0.0042 (7)	0.0057 (8)
C19	0.0210 (8)	0.0278 (9)	0.0225 (9)	0.0008 (6)	0.0004 (6)	0.0023 (7)
C20	0.0204 (8)	0.0226 (8)	0.0201 (8)	0.0015 (6)	0.0045 (6)	0.0043 (7)
C21	0.0235 (8)	0.0235 (9)	0.0271 (9)	0.0035 (7)	0.0026 (7)	0.0084 (7)
C22	0.0252 (8)	0.0152 (8)	0.0253 (9)	0.0055 (6)	0.0020 (7)	0.0051 (7)
C23	0.0231 (8)	0.0196 (8)	0.0324 (10)	−0.0002 (6)	0.0011 (7)	0.0071 (7)
C24	0.0311 (9)	0.0229 (9)	0.0278 (10)	−0.0020 (7)	−0.0067 (7)	0.0044 (7)
C25	0.0352 (10)	0.0242 (9)	0.0243 (9)	0.0071 (7)	0.0035 (7)	0.0032 (7)
C26	0.0258 (9)	0.0276 (9)	0.0309 (10)	0.0054 (7)	0.0046 (7)	0.0039 (8)
C27	0.0216 (8)	0.0256 (9)	0.0261 (9)	0.0026 (7)	−0.0016 (7)	0.0013 (7)
C28	0.0255 (8)	0.0212 (8)	0.0203 (9)	−0.0005 (6)	0.0029 (6)	0.0015 (7)

S1—C14	1.5947 (19)	C12—C13	1.388 (2)
S2—C28	1.5893 (16)	C12—H12	0.9500
N1—C14	1.164 (2)	C13—H13	0.9500
N1—C7	1.441 (2)	C15—C20	1.388 (2)
N2—C28	1.1626 (18)	C15—C16	1.389 (2)
N2—C21	1.4473 (19)	C15—H15	0.9500
C1—C6	1.387 (2)	C16—C17	1.388 (2)
C1—C2	1.393 (2)	C16—H16	0.9500
C1—H1	0.9500	C17—C18	1.383 (2)
C2—C3	1.378 (2)	C17—H17	0.9500
C2—H2	0.9500	C18—C19	1.387 (2)
C3—C4	1.390 (2)	C18—H18	0.9500
C3—H3	0.9500	C19—C20	1.390 (2)
C4—C5	1.383 (2)	C19—H19	0.9500
C4—H4	0.9500	C20—C21	1.523 (2)
C5—C6	1.395 (2)	C21—C22	1.528 (2)
C5—H5	0.9500	C21—H21	1.0000
C6—C7	1.525 (2)	C22—C23	1.389 (2)
C7—C8	1.525 (2)	C22—C27	1.3949 (19)
C7—H7	1.0000	C23—C24	1.393 (2)
C8—C13	1.387 (2)	C23—H23	0.9500
C8—C9	1.388 (2)	C24—C25	1.387 (2)
C9—C10	1.385 (2)	C24—H24	0.9500
C9—H9	0.9500	C25—C26	1.388 (2)
C10—C11	1.381 (2)	C25—H25	0.9500
C10—H10	0.9500	C26—C27	1.383 (2)
C11—C12	1.383 (2)	C26—H26	0.9500
C11—H11	0.9500	C27—H27	0.9500
C14—N1—C7	168.64 (16)	N1—C14—S1	177.42 (15)
C28—N2—C21	168.05 (17)	C20—C15—C16	120.28 (14)
C6—C1—C2	120.40 (15)	C20—C15—H15	119.9
C6—C1—H1	119.8	C16—C15—H15	119.9
C2—C1—H1	119.8	C17—C16—C15	119.89 (15)
C3—C2—C1	120.23 (15)	C17—C16—H16	120.1
C3—C2—H2	119.9	C15—C16—H16	120.1
C1—C2—H2	119.9	C18—C17—C16	120.02 (15)
C2—C3—C4	119.74 (15)	C18—C17—H17	120.0
C2—C3—H3	120.1	C16—C17—H17	120.0
C4—C3—H3	120.1	C17—C18—C19	120.05 (14)
C5—C4—C3	120.16 (15)	C17—C18—H18	120.0
C5—C4—H4	119.9	C19—C18—H18	120.0
C3—C4—H4	119.9	C18—C19—C20	120.31 (15)
C4—C5—C6	120.48 (15)	C18—C19—H19	119.8
C4—C5—H5	119.8	C20—C19—H19	119.8
C6—C5—H5	119.8	C15—C20—C19	119.45 (15)
C1—C6—C5	118.97 (14)	C15—C20—C21	123.10 (14)
C1—C6—C7	123.65 (14)	C19—C20—C21	117.44 (14)
C5—C6—C7	117.33 (13)	N2—C21—C20	111.07 (13)
N1—C7—C6	111.17 (13)	N2—C21—C22	109.58 (12)
N1—C7—C8	110.31 (13)	C20—C21—C22	112.88 (12)
C6—C7—C8	111.92 (12)	N2—C21—H21	107.7
N1—C7—H7	107.8	C20—C21—H21	107.7
C6—C7—H7	107.8	C22—C21—H21	107.7
C8—C7—H7	107.8	C23—C22—C27	119.35 (14)
C13—C8—C9	119.46 (14)	C23—C22—C21	120.30 (14)
C13—C8—C7	119.84 (14)	C27—C22—C21	120.33 (14)
C9—C8—C7	120.67 (14)	C22—C23—C24	120.52 (14)
C10—C9—C8	120.35 (16)	C22—C23—H23	119.7
C10—C9—H9	119.8	C24—C23—H23	119.7
C8—C9—H9	119.8	C25—C24—C23	119.76 (15)
C11—C10—C9	120.00 (16)	C25—C24—H24	120.1
C11—C10—H10	120.0	C23—C24—H24	120.1
C9—C10—H10	120.0	C24—C25—C26	119.79 (15)
C10—C11—C12	119.96 (15)	C24—C25—H25	120.1
C10—C11—H11	120.0	C26—C25—H25	120.1
C12—C11—H11	120.0	C27—C26—C25	120.56 (15)
C11—C12—C13	120.14 (16)	C27—C26—H26	119.7
C11—C12—H12	119.9	C25—C26—H26	119.7
C13—C12—H12	119.9	C26—C27—C22	120.02 (15)
C8—C13—C12	120.07 (15)	C26—C27—H27	120.0
C8—C13—H13	120.0	C22—C27—H27	120.0
C12—C13—H13	120.0	N2—C28—S2	178.13 (15)
C6—C1—C2—C3	−0.1 (2)	C20—C15—C16—C17	−0.1 (2)
C1—C2—C3—C4	1.0 (2)	C15—C16—C17—C18	0.4 (2)
C2—C3—C4—C5	−1.4 (2)	C16—C17—C18—C19	−0.3 (2)
C3—C4—C5—C6	0.8 (2)	C17—C18—C19—C20	−0.1 (2)
C2—C1—C6—C5	−0.4 (2)	C16—C15—C20—C19	−0.3 (2)
C2—C1—C6—C7	177.04 (14)	C16—C15—C20—C21	178.89 (13)
C4—C5—C6—C1	0.1 (2)	C18—C19—C20—C15	0.4 (2)
C4—C5—C6—C7	−177.57 (13)	C18—C19—C20—C21	−178.82 (12)
C14—N1—C7—C6	−94.4 (8)	C28—N2—C21—C20	−153.8 (7)
C14—N1—C7—C8	30.4 (8)	C28—N2—C21—C22	80.8 (7)
C1—C6—C7—N1	9.4 (2)	C15—C20—C21—N2	−13.98 (19)
C5—C6—C7—N1	−173.10 (13)	C19—C20—C21—N2	165.23 (12)
C1—C6—C7—C8	−114.46 (16)	C15—C20—C21—C22	109.54 (16)
C5—C6—C7—C8	63.05 (18)	C19—C20—C21—C22	−71.24 (17)
N1—C7—C8—C13	123.86 (15)	N2—C21—C22—C23	−123.47 (15)
C6—C7—C8—C13	−111.81 (15)	C20—C21—C22—C23	112.18 (15)
N1—C7—C8—C9	−58.43 (18)	N2—C21—C22—C27	57.70 (18)
C6—C7—C8—C9	65.90 (19)	C20—C21—C22—C27	−66.65 (17)
C13—C8—C9—C10	0.9 (2)	C27—C22—C23—C24	−1.0 (2)
C7—C8—C9—C10	−176.82 (14)	C21—C22—C23—C24	−179.89 (13)
C8—C9—C10—C11	−0.4 (2)	C22—C23—C24—C25	0.6 (2)
C9—C10—C11—C12	0.1 (2)	C23—C24—C25—C26	0.2 (2)
C10—C11—C12—C13	−0.3 (2)	C24—C25—C26—C27	−0.7 (2)
C9—C8—C13—C12	−1.1 (2)	C25—C26—C27—C22	0.2 (2)
C7—C8—C13—C12	176.66 (13)	C23—C22—C27—C26	0.6 (2)
C11—C12—C13—C8	0.8 (2)	C21—C22—C27—C26	179.47 (13)
C7—N1—C14—S1	−176 (100)	C21—N2—C28—S2	−168 (4)