(2E)-2-[(3-Methyl-5-phen-oxy-1-phenyl-1H-pyrazol-4-yl)methyl-idene]hydrazinecarbothio-amide.

In the title compound, C(18)H(17)N(5)OS, the mean plane of the pyrazole ring [maximum deviation = 0.0031 (12) Å] forms dihedral angles of 19.6 (4) and 9.3 (5)° with the two disorder components of the N-bound benzene ring (with equal occupancies for the two orientations) and a dihedral angle of 72.58 (8)° with the C-O-bonded benzene ring. The mol-ecule exists in a trans conformation with respect to the N=C bond [1.2792 (19) Å]. The mol-ecular structure features an intra-molecular C-H⋯O hydrogen bond, forming an S(6) ring. In the crystal, N-H⋯N and N-H⋯S hydrogen bonds result in the formation of zigzag layers lying parallel to (10-1).

Related literature

For general background to and applications of the pyrazole derivatives, see: Rai et al. (2008 ▶); Isloor et al. (2009 ▶); Girisha et al. (2010 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2011a ▶,b ▶,c ▶).

Experimental

Crystal data

C18H17N5OS

M = 351.43

Monoclinic,

a = 8.8280 (1) Å

b = 10.8519 (2) Å

c = 17.7353 (2) Å

β = 94.379 (1)°

V = 1694.09 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.29 × 0.27 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.942, T max = 0.955

18467 measured reflections

4948 independent reflections

3879 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.113

S = 1.06

4948 reflections

294 parameters

216 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026931/hb6849sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026931/hb6849Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026931/hb6849Isup3.cml

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

C18H17N5OS	F(000) = 736
Mr = 351.43	Dx = 1.378 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5058 reflections
a = 8.8280 (1) Å	θ = 2.3–32.4°
b = 10.8519 (2) Å	µ = 0.21 mm−1
c = 17.7353 (2) Å	T = 100 K
β = 94.379 (1)°	Block, pink
V = 1694.09 (4) Å3	0.29 × 0.27 × 0.22 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4948 independent reflections
Radiation source: fine-focus sealed tube	3879 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.942, Tmax = 0.955	k = −15→15
18467 measured reflections	l = −22→24

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.7836P] where P = (Fo2 + 2Fc2)/3
4948 reflections	(Δ/σ)max = 0.001
294 parameters	Δρmax = 0.43 e Å−3
216 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
S1	1.02274 (4)	0.97510 (4)	1.12626 (2)	0.01906 (10)
O1	0.32416 (12)	0.80260 (10)	1.01785 (6)	0.0171 (2)
N1	0.75067 (17)	0.87882 (14)	1.14880 (8)	0.0208 (3)
N2	0.78833 (15)	0.93939 (12)	1.02818 (7)	0.0168 (3)
N3	0.64788 (14)	0.89082 (12)	1.00657 (7)	0.0169 (3)
N4	0.24554 (14)	0.73854 (11)	0.89336 (7)	0.0153 (2)
N5	0.29680 (15)	0.73976 (12)	0.82182 (7)	0.0182 (3)
C1	0.84379 (17)	0.92800 (13)	1.10068 (8)	0.0160 (3)
C2	0.61467 (17)	0.88237 (14)	0.93528 (9)	0.0179 (3)
H2A	0.6840	0.9127	0.9013	0.022*
C3	0.47312 (17)	0.82734 (14)	0.90555 (8)	0.0163 (3)
C4	0.35025 (17)	0.78988 (13)	0.94386 (8)	0.0151 (3)
C5	0.43228 (18)	0.79306 (14)	0.82963 (8)	0.0183 (3)
C6	0.40260 (17)	0.72594 (14)	1.07080 (8)	0.0155 (3)
C7	0.50846 (17)	0.63938 (14)	1.05158 (8)	0.0167 (3)
H7A	0.5306	0.6288	1.0004	0.020*
C8	0.58163 (19)	0.56845 (15)	1.10841 (9)	0.0207 (3)
H8A	0.6548	0.5090	1.0961	0.025*
C9	0.5488 (2)	0.58360 (16)	1.18318 (9)	0.0250 (4)
H9A	0.5994	0.5350	1.2219	0.030*
C10	0.4411 (2)	0.67053 (17)	1.20104 (9)	0.0269 (4)
H10A	0.4180	0.6807	1.2521	0.032*
C11	0.36739 (19)	0.74238 (16)	1.14485 (9)	0.0219 (3)
H11A	0.2941	0.8018	1.1570	0.026*
C12	0.1022 (18)	0.687 (2)	0.9077 (9)	0.0163 (15)	0.50 (2)
C13	0.0307 (13)	0.7157 (11)	0.9729 (7)	0.0168 (12)	0.50 (2)
H13A	0.0743	0.7740	1.0082	0.020*	0.50 (2)
C14	−0.1050 (15)	0.6578 (12)	0.9854 (7)	0.0217 (13)	0.50 (2)
H14A	−0.1526	0.6748	1.0305	0.026*	0.50 (2)
C15	−0.1725 (12)	0.5757 (10)	0.9335 (7)	0.0263 (15)	0.50 (2)
H15A	−0.2656	0.5368	0.9431	0.032*	0.50 (2)
C16	−0.1035 (11)	0.5501 (10)	0.8673 (6)	0.0301 (15)	0.50 (2)
H16A	−0.1515	0.4966	0.8304	0.036*	0.50 (2)
C17	0.0365 (12)	0.6033 (10)	0.8553 (6)	0.0248 (15)	0.50 (2)
H17A	0.0869	0.5825	0.8116	0.030*	0.50 (2)
C12X	0.0983 (19)	0.683 (2)	0.9013 (9)	0.0186 (16)	0.50 (2)
C13X	0.0278 (15)	0.6967 (13)	0.9686 (8)	0.0259 (17)	0.50 (2)
H13B	0.0763	0.7409	1.0099	0.031*	0.50 (2)
C14X	−0.1156 (15)	0.6440 (14)	0.9742 (8)	0.0276 (16)	0.50 (2)
H14B	−0.1636	0.6502	1.0202	0.033*	0.50 (2)
C15X	−0.1871 (12)	0.5835 (11)	0.9137 (7)	0.0286 (15)	0.50 (2)
H15B	−0.2846	0.5481	0.9177	0.034*	0.50 (2)
C16X	−0.1171 (11)	0.5744 (9)	0.8473 (7)	0.0304 (14)	0.50 (2)
H16B	−0.1681	0.5338	0.8052	0.036*	0.50 (2)
C17X	0.0263 (12)	0.6231 (11)	0.8405 (6)	0.0244 (15)	0.50 (2)
H17B	0.0741	0.6150	0.7946	0.029*	0.50 (2)
C18	0.5243 (2)	0.80836 (19)	0.76296 (10)	0.0300 (4)
H18A	0.4574	0.8316	0.7186	0.045*
H18B	0.5754	0.7305	0.7529	0.045*
H18C	0.6004	0.8730	0.7736	0.045*
H2N1	0.669 (2)	0.8510 (18)	1.1330 (11)	0.025 (5)*
H1N1	0.781 (2)	0.8649 (19)	1.1957 (12)	0.030 (5)*
H1N2	0.850 (2)	0.9640 (19)	0.9934 (12)	0.032 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.01562 (19)	0.0281 (2)	0.01348 (17)	−0.00380 (15)	0.00110 (13)	−0.00271 (14)
O1	0.0174 (5)	0.0224 (5)	0.0119 (5)	0.0045 (4)	0.0031 (4)	0.0019 (4)
N1	0.0161 (7)	0.0320 (8)	0.0139 (6)	−0.0047 (6)	−0.0007 (5)	0.0019 (5)
N2	0.0146 (6)	0.0214 (6)	0.0144 (6)	−0.0043 (5)	0.0004 (5)	0.0009 (5)
N3	0.0129 (6)	0.0199 (6)	0.0177 (6)	−0.0019 (5)	−0.0005 (5)	0.0006 (5)
N4	0.0130 (6)	0.0199 (6)	0.0133 (6)	−0.0011 (5)	0.0022 (5)	0.0012 (5)
N5	0.0162 (6)	0.0260 (7)	0.0125 (6)	−0.0030 (5)	0.0020 (5)	0.0012 (5)
C1	0.0166 (7)	0.0167 (7)	0.0147 (7)	0.0011 (6)	0.0020 (5)	−0.0023 (5)
C2	0.0147 (7)	0.0230 (7)	0.0164 (7)	−0.0027 (6)	0.0033 (6)	0.0012 (6)
C3	0.0150 (7)	0.0209 (7)	0.0129 (6)	−0.0018 (6)	−0.0002 (5)	0.0023 (5)
C4	0.0143 (7)	0.0176 (7)	0.0136 (6)	0.0018 (5)	0.0012 (5)	0.0020 (5)
C5	0.0164 (7)	0.0234 (7)	0.0149 (7)	−0.0034 (6)	0.0008 (6)	0.0021 (6)
C6	0.0149 (7)	0.0183 (7)	0.0135 (6)	−0.0019 (5)	0.0020 (5)	0.0035 (5)
C7	0.0165 (7)	0.0194 (7)	0.0148 (7)	−0.0020 (6)	0.0039 (6)	0.0013 (5)
C8	0.0187 (8)	0.0206 (7)	0.0229 (8)	0.0009 (6)	0.0024 (6)	0.0039 (6)
C9	0.0234 (8)	0.0315 (9)	0.0200 (8)	0.0017 (7)	0.0005 (6)	0.0102 (7)
C10	0.0271 (9)	0.0397 (10)	0.0146 (7)	0.0023 (7)	0.0054 (6)	0.0069 (7)
C11	0.0204 (8)	0.0300 (8)	0.0160 (7)	0.0036 (7)	0.0062 (6)	0.0018 (6)
C12	0.011 (2)	0.016 (2)	0.021 (3)	−0.001 (2)	−0.003 (2)	−0.002 (2)
C13	0.013 (2)	0.013 (3)	0.026 (2)	−0.0041 (17)	0.0103 (18)	−0.0068 (17)
C14	0.020 (2)	0.016 (2)	0.030 (3)	−0.0049 (17)	0.006 (2)	−0.0092 (19)
C15	0.020 (3)	0.023 (2)	0.038 (3)	−0.0064 (19)	0.015 (3)	−0.009 (3)
C16	0.023 (2)	0.031 (3)	0.038 (3)	−0.014 (2)	0.007 (2)	−0.012 (2)
C17	0.020 (2)	0.029 (3)	0.026 (3)	−0.004 (2)	0.010 (2)	−0.007 (2)
C12X	0.011 (3)	0.021 (3)	0.025 (3)	−0.001 (2)	0.008 (3)	0.003 (2)
C13X	0.025 (2)	0.024 (4)	0.028 (3)	−0.004 (2)	−0.001 (2)	−0.003 (2)
C14X	0.018 (3)	0.031 (4)	0.035 (3)	−0.005 (2)	0.013 (3)	−0.003 (3)
C15X	0.016 (2)	0.031 (2)	0.040 (4)	−0.0073 (18)	0.007 (3)	−0.006 (3)
C16X	0.024 (2)	0.031 (3)	0.036 (3)	−0.006 (2)	0.009 (2)	−0.011 (2)
C17X	0.017 (2)	0.030 (3)	0.026 (3)	−0.007 (2)	0.004 (2)	−0.005 (2)
C18	0.0265 (9)	0.0471 (11)	0.0170 (8)	−0.0129 (8)	0.0061 (7)	0.0001 (7)

S1—C1	1.6892 (16)	C10—C11	1.388 (2)
O1—C4	1.3566 (17)	C10—H10A	0.9500
O1—C6	1.3979 (17)	C11—H11A	0.9500
N1—C1	1.340 (2)	C12—C13	1.395 (9)
N1—H2N1	0.81 (2)	C12—C17	1.395 (10)
N1—H1N1	0.87 (2)	C13—C14	1.385 (9)
N2—C1	1.3461 (19)	C13—H13A	0.9500
N2—N3	1.3746 (18)	C14—C15	1.382 (8)
N2—H1N2	0.89 (2)	C14—H14A	0.9500
N3—C2	1.2792 (19)	C15—C16	1.393 (8)
N4—C4	1.3567 (19)	C15—H15A	0.9500
N4—N5	1.3793 (17)	C16—C17	1.395 (8)
N4—C12	1.423 (13)	C16—H16A	0.9500
N4—C12X	1.447 (12)	C17—H17A	0.9500
N5—C5	1.326 (2)	C12X—C17X	1.375 (10)
C2—C3	1.448 (2)	C12X—C13X	1.395 (10)
C2—H2A	0.9500	C13X—C14X	1.400 (9)
C3—C4	1.384 (2)	C13X—H13B	0.9500
C3—C5	1.417 (2)	C14X—C15X	1.370 (8)
C5—C18	1.494 (2)	C14X—H14B	0.9500
C6—C11	1.384 (2)	C15X—C16X	1.375 (8)
C6—C7	1.386 (2)	C15X—H15B	0.9500
C7—C8	1.388 (2)	C16X—C17X	1.386 (9)
C7—H7A	0.9500	C16X—H16B	0.9500
C8—C9	1.389 (2)	C17X—H17B	0.9500
C8—H8A	0.9500	C18—H18A	0.9800
C9—C10	1.393 (2)	C18—H18B	0.9800
C9—H9A	0.9500	C18—H18C	0.9800
C4—O1—C6	118.51 (11)	C6—C11—C10	118.82 (15)
C1—N1—H2N1	119.9 (14)	C6—C11—H11A	120.6
C1—N1—H1N1	121.4 (14)	C10—C11—H11A	120.6
H2N1—N1—H1N1	118 (2)	C13—C12—C17	120.4 (9)
C1—N2—N3	119.05 (13)	C13—C12—N4	121.8 (8)
C1—N2—H1N2	119.5 (14)	C17—C12—N4	117.8 (9)
N3—N2—H1N2	120.2 (14)	C14—C13—C12	118.9 (8)
C2—N3—N2	115.90 (13)	C14—C13—H13A	120.6
C4—N4—N5	110.39 (12)	C12—C13—H13A	120.6
C4—N4—C12	127.8 (6)	C15—C14—C13	121.4 (8)
N5—N4—C12	121.8 (5)	C15—C14—H14A	119.3
C4—N4—C12X	132.6 (6)	C13—C14—H14A	119.3
N5—N4—C12X	117.0 (6)	C14—C15—C16	119.7 (8)
C12—N4—C12X	4.8 (10)	C14—C15—H15A	120.1
C5—N5—N4	105.35 (12)	C16—C15—H15A	120.1
N1—C1—N2	116.66 (14)	C15—C16—C17	119.7 (7)
N1—C1—S1	123.78 (12)	C15—C16—H16A	120.1
N2—C1—S1	119.56 (12)	C17—C16—H16A	120.1
N3—C2—C3	121.06 (14)	C16—C17—C12	119.8 (8)
N3—C2—H2A	119.5	C16—C17—H17A	120.1
C3—C2—H2A	119.5	C12—C17—H17A	120.1
C4—C3—C5	103.72 (13)	C17X—C12X—C13X	120.6 (10)
C4—C3—C2	129.01 (14)	C17X—C12X—N4	119.1 (9)
C5—C3—C2	127.19 (14)	C13X—C12X—N4	120.3 (9)
O1—C4—N4	121.53 (13)	C12X—C13X—C14X	119.0 (9)
O1—C4—C3	129.96 (14)	C12X—C13X—H13B	120.5
N4—C4—C3	108.46 (13)	C14X—C13X—H13B	120.5
N5—C5—C3	112.08 (14)	C15X—C14X—C13X	120.3 (9)
N5—C5—C18	120.41 (14)	C15X—C14X—H14B	119.8
C3—C5—C18	127.50 (14)	C13X—C14X—H14B	119.8
C11—C6—C7	121.69 (14)	C14X—C15X—C16X	119.7 (8)
C11—C6—O1	115.15 (13)	C14X—C15X—H15B	120.1
C7—C6—O1	123.15 (13)	C16X—C15X—H15B	120.1
C6—C7—C8	118.85 (14)	C15X—C16X—C17X	121.3 (7)
C6—C7—H7A	120.6	C15X—C16X—H16B	119.4
C8—C7—H7A	120.6	C17X—C16X—H16B	119.4
C7—C8—C9	120.55 (15)	C12X—C17X—C16X	119.0 (8)
C7—C8—H8A	119.7	C12X—C17X—H17B	120.5
C9—C8—H8A	119.7	C16X—C17X—H17B	120.5
C8—C9—C10	119.56 (15)	C5—C18—H18A	109.5
C8—C9—H9A	120.2	C5—C18—H18B	109.5
C10—C9—H9A	120.2	H18A—C18—H18B	109.5
C11—C10—C9	120.53 (15)	C5—C18—H18C	109.5
C11—C10—H10A	119.7	H18A—C18—H18C	109.5
C9—C10—H10A	119.7	H18B—C18—H18C	109.5
C1—N2—N3—C2	−166.48 (14)	C8—C9—C10—C11	−0.4 (3)
C4—N4—N5—C5	−0.51 (16)	C7—C6—C11—C10	0.4 (2)
C12—N4—N5—C5	−179.7 (12)	O1—C6—C11—C10	−179.52 (15)
C12X—N4—N5—C5	−179.4 (12)	C9—C10—C11—C6	0.1 (3)
N3—N2—C1—N1	−5.8 (2)	C4—N4—C12—C13	20 (3)
N3—N2—C1—S1	174.23 (10)	N5—N4—C12—C13	−161.4 (14)
N2—N3—C2—C3	177.04 (13)	C12X—N4—C12—C13	−164 (27)
N3—C2—C3—C4	7.7 (3)	C4—N4—C12—C17	−158.3 (11)
N3—C2—C3—C5	−168.53 (16)	N5—N4—C12—C17	21 (2)
C6—O1—C4—N4	107.65 (16)	C12X—N4—C12—C17	18 (23)
C6—O1—C4—C3	−75.5 (2)	C17—C12—C13—C14	1 (3)
N5—N4—C4—O1	178.07 (12)	N4—C12—C13—C14	−176.7 (16)
C12—N4—C4—O1	−2.8 (13)	C12—C13—C14—C15	−2 (2)
C12X—N4—C4—O1	−3.3 (14)	C13—C14—C15—C16	0.0 (18)
N5—N4—C4—C3	0.62 (17)	C14—C15—C16—C17	2.8 (13)
C12—N4—C4—C3	179.7 (13)	C15—C16—C17—C12	−3.7 (16)
C12X—N4—C4—C3	179.3 (14)	C13—C12—C17—C16	2 (3)
C5—C3—C4—O1	−177.63 (15)	N4—C12—C17—C16	179.6 (13)
C2—C3—C4—O1	5.5 (3)	C4—N4—C12X—C17X	−171.0 (11)
C5—C3—C4—N4	−0.45 (16)	N5—N4—C12X—C17X	8 (2)
C2—C3—C4—N4	−177.34 (15)	C12—N4—C12X—C17X	−175 (27)
N4—N5—C5—C3	0.21 (17)	C4—N4—C12X—C13X	12 (3)
N4—N5—C5—C18	178.89 (15)	N5—N4—C12X—C13X	−169.3 (15)
C4—C3—C5—N5	0.15 (18)	C12—N4—C12X—C13X	8 (23)
C2—C3—C5—N5	177.11 (15)	C17X—C12X—C13X—C14X	2 (3)
C4—C3—C5—C18	−178.41 (16)	N4—C12X—C13X—C14X	179.0 (16)
C2—C3—C5—C18	−1.5 (3)	C12X—C13X—C14X—C15X	−2 (2)
C4—O1—C6—C11	−178.56 (14)	C13X—C14X—C15X—C16X	0.2 (19)
C4—O1—C6—C7	1.5 (2)	C14X—C15X—C16X—C17X	1.3 (14)
C11—C6—C7—C8	−0.6 (2)	C13X—C12X—C17X—C16X	−1 (3)
O1—C6—C7—C8	179.31 (14)	N4—C12X—C17X—C16X	−177.6 (14)
C6—C7—C8—C9	0.3 (2)	C15X—C16X—C17X—C12X	−1.0 (17)
C7—C8—C9—C10	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N5i	0.87 (2)	2.50 (2)	3.3237 (19)	158.1 (18)
N2—H1N2···S1ii	0.89 (2)	2.56 (2)	3.4414 (13)	167.7 (17)
C13—H13A···O1	0.95	2.22	2.814 (12)	120
C13—H13B···O1	0.79	2.28	2.814 (12)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N5i	0.87 (2)	2.50 (2)	3.3237 (19)	158.1 (18)
N2—H1N2⋯S1ii	0.89 (2)	2.56 (2)	3.4414 (13)	167.7 (17)
C13—H13A⋯O1	0.95	2.22	2.814 (12)	120
C13—H13B⋯O1	0.79	2.28	2.814 (12)	125

Symmetry codes: (i) ; (ii) .