Ethyl 1-(4-chloro-benz-yl)-3-phenyl-1H-pyrazole-5-carboxyl-ate.

In the title compound, C(19)H(17)ClN(2)O(2), the pyrazole ring makes dihedral angles of 6.97 (5) and 79.25 (1)°, respectively, with the phenyl and chlorophenyl rings, respectively. In the crystal, C-H⋯O hydrogen bonds are observed.

Related literature

For background to the title compound, see: Ge et al. (2007 ▶, 2009 ▶, 2011 ▶). For a related compound, see: Xia et al. (2007 ▶).

Experimental

Crystal data

C19H17ClN2O2

M = 340.80

Triclinic,

a = 8.1815 (10) Å

b = 10.4039 (12) Å

c = 11.0969 (13) Å

α = 109.981 (2)°

β = 90.107 (2)°

γ = 104.046 (2)°

V = 857.43 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 298 K

0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.941, T max = 0.954

4495 measured reflections

3008 independent reflections

2554 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.107

S = 1.03

3008 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007428/zj2059sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007428/zj2059Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007428/zj2059Isup3.cml

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

C19H17ClN2O2	Z = 2
Mr = 340.80	F(000) = 356
Triclinic, P1	Dx = 1.320 Mg m−3
a = 8.1815 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4039 (12) Å	Cell parameters from 2727 reflections
c = 11.0969 (13) Å	θ = 2.4–28.2°
α = 109.981 (2)°	µ = 0.24 mm−1
β = 90.107 (2)°	T = 298 K
γ = 104.046 (2)°	Block, white
V = 857.43 (18) Å3	0.26 × 0.24 × 0.20 mm

Bruker SMART CCD diffractometer	3008 independent reflections
Radiation source: fine-focus sealed tube	2554 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
Tmin = 0.941, Tmax = 0.954	k = −11→12
4495 measured reflections	l = −11→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.2205P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3008 reflections	Δρmax = 0.25 e Å−3
218 parameters	Δρmin = −0.30 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.082 (5)

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
Cl1	1.50815 (7)	0.95990 (7)	0.77388 (6)	0.0839 (2)
O1	0.84683 (18)	0.38892 (14)	0.64732 (11)	0.0665 (4)
O2	0.85747 (17)	0.25171 (13)	0.76392 (11)	0.0598 (3)
N1	0.75907 (17)	0.58814 (15)	0.87794 (13)	0.0492 (3)
N2	0.71786 (18)	0.65423 (15)	0.99660 (13)	0.0514 (4)
C1	0.7812 (2)	0.6630 (2)	0.78600 (17)	0.0561 (4)
H1A	0.7167	0.7334	0.8091	0.067*
H1B	0.7367	0.5960	0.7006	0.067*
C2	0.9642 (2)	0.73491 (18)	0.78307 (15)	0.0501 (4)
C3	1.0607 (3)	0.8300 (2)	0.89533 (17)	0.0650 (5)
H3	1.0125	0.8475	0.9733	0.078*
C4	1.2266 (3)	0.8989 (2)	0.89318 (18)	0.0707 (5)
H4	1.2900	0.9625	0.9689	0.085*
C5	1.2976 (2)	0.8726 (2)	0.77783 (18)	0.0584 (5)
C6	1.2062 (2)	0.77923 (19)	0.66533 (16)	0.0563 (4)
H6	1.2553	0.7623	0.5878	0.068*
C7	1.0400 (2)	0.71053 (19)	0.66882 (16)	0.0546 (4)
H7	0.9778	0.6465	0.5928	0.066*
C8	0.78772 (19)	0.46120 (17)	0.86693 (15)	0.0462 (4)
C9	0.8332 (2)	0.36663 (18)	0.74715 (15)	0.0491 (4)
C10	0.9062 (3)	0.1503 (2)	0.65285 (18)	0.0641 (5)
H10A	1.0026	0.1973	0.6190	0.077*
H10B	0.8133	0.1060	0.5855	0.077*
C11	0.9509 (3)	0.0421 (2)	0.6971 (2)	0.0779 (6)
H11A	1.0399	0.0877	0.7659	0.117*
H11B	0.9883	−0.0249	0.6267	0.117*
H11C	0.8533	−0.0063	0.7270	0.117*
C12	0.7612 (2)	0.44406 (18)	0.98320 (15)	0.0479 (4)
H12	0.7698	0.3673	1.0054	0.058*
C13	0.71823 (19)	0.56638 (17)	1.06121 (15)	0.0457 (4)
C14	0.67851 (19)	0.60557 (18)	1.19642 (15)	0.0473 (4)
C15	0.6985 (2)	0.5232 (2)	1.26854 (16)	0.0564 (4)
H15	0.7340	0.4412	1.2303	0.068*
C16	0.6660 (3)	0.5621 (2)	1.39691 (18)	0.0656 (5)
H16	0.6798	0.5062	1.4441	0.079*
C17	0.6135 (3)	0.6829 (2)	1.45453 (18)	0.0676 (5)
H17	0.5926	0.7095	1.5408	0.081*
C18	0.5921 (2)	0.7646 (2)	1.38374 (19)	0.0678 (5)
H18	0.5561	0.8462	1.4226	0.081*
C19	0.6235 (2)	0.7266 (2)	1.25547 (17)	0.0573 (4)
H19	0.6077	0.7823	1.2086	0.069*

	U11	U22	U33	U12	U13	U23
Cl1	0.0670 (3)	0.0917 (4)	0.0892 (4)	0.0145 (3)	0.0093 (3)	0.0313 (3)
O1	0.0907 (10)	0.0682 (8)	0.0420 (7)	0.0261 (7)	0.0127 (6)	0.0173 (6)
O2	0.0781 (8)	0.0569 (7)	0.0473 (7)	0.0281 (6)	0.0168 (6)	0.0146 (6)
N1	0.0541 (8)	0.0561 (8)	0.0408 (7)	0.0195 (6)	0.0075 (6)	0.0175 (6)
N2	0.0560 (8)	0.0559 (8)	0.0444 (8)	0.0206 (7)	0.0092 (6)	0.0162 (7)
C1	0.0677 (11)	0.0640 (11)	0.0460 (9)	0.0263 (9)	0.0052 (8)	0.0247 (8)
C2	0.0668 (11)	0.0502 (9)	0.0394 (8)	0.0232 (8)	0.0059 (7)	0.0179 (7)
C3	0.0789 (13)	0.0709 (12)	0.0386 (9)	0.0173 (10)	0.0123 (9)	0.0126 (9)
C4	0.0802 (14)	0.0731 (13)	0.0436 (10)	0.0107 (11)	−0.0019 (9)	0.0078 (9)
C5	0.0652 (11)	0.0596 (11)	0.0548 (10)	0.0218 (9)	0.0074 (8)	0.0217 (9)
C6	0.0716 (12)	0.0619 (11)	0.0425 (9)	0.0280 (9)	0.0133 (8)	0.0199 (8)
C7	0.0735 (12)	0.0567 (10)	0.0353 (8)	0.0233 (9)	0.0027 (8)	0.0138 (7)
C8	0.0446 (8)	0.0502 (9)	0.0416 (8)	0.0130 (7)	0.0028 (7)	0.0129 (7)
C9	0.0480 (9)	0.0523 (10)	0.0413 (9)	0.0101 (7)	0.0031 (7)	0.0116 (7)
C10	0.0764 (13)	0.0584 (11)	0.0516 (10)	0.0247 (10)	0.0141 (9)	0.0070 (9)
C11	0.0853 (15)	0.0660 (13)	0.0883 (16)	0.0333 (11)	0.0253 (12)	0.0252 (12)
C12	0.0499 (9)	0.0502 (9)	0.0439 (9)	0.0142 (7)	0.0049 (7)	0.0158 (7)
C13	0.0419 (8)	0.0513 (9)	0.0419 (8)	0.0117 (7)	0.0034 (6)	0.0144 (7)
C14	0.0408 (8)	0.0534 (9)	0.0426 (9)	0.0100 (7)	0.0042 (6)	0.0121 (7)
C15	0.0632 (11)	0.0588 (10)	0.0461 (9)	0.0171 (9)	0.0082 (8)	0.0161 (8)
C16	0.0717 (12)	0.0778 (13)	0.0475 (10)	0.0166 (10)	0.0096 (9)	0.0242 (10)
C17	0.0681 (12)	0.0852 (14)	0.0425 (10)	0.0185 (10)	0.0140 (8)	0.0149 (10)
C18	0.0641 (12)	0.0720 (13)	0.0585 (11)	0.0247 (10)	0.0132 (9)	0.0070 (10)
C19	0.0573 (10)	0.0629 (11)	0.0513 (10)	0.0220 (9)	0.0094 (8)	0.0151 (9)

Cl1—C5	1.750 (2)	C8—C9	1.469 (2)
O1—C9	1.207 (2)	C10—C11	1.490 (3)
O2—C9	1.331 (2)	C10—H10A	0.9700
O2—C10	1.452 (2)	C10—H10B	0.9700
N1—N2	1.3475 (19)	C11—H11A	0.9600
N1—C8	1.362 (2)	C11—H11B	0.9600
N1—C1	1.468 (2)	C11—H11C	0.9600
N2—C13	1.341 (2)	C12—C13	1.399 (2)
C1—C2	1.508 (3)	C12—H12	0.9300
C1—H1A	0.9700	C13—C14	1.473 (2)
C1—H1B	0.9700	C14—C19	1.389 (2)
C2—C7	1.384 (2)	C14—C15	1.392 (2)
C2—C3	1.389 (3)	C15—C16	1.387 (2)
C3—C4	1.377 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.374 (3)
C4—C5	1.375 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.377 (3)
C5—C6	1.370 (3)	C17—H17	0.9300
C6—C7	1.381 (3)	C18—C19	1.384 (3)
C6—H6	0.9300	C18—H18	0.9300
C7—H7	0.9300	C19—H19	0.9300
C8—C12	1.372 (2)
C9—O2—C10	115.81 (13)	O2—C10—H10A	110.3
N2—N1—C8	111.51 (13)	C11—C10—H10A	110.3
N2—N1—C1	118.60 (14)	O2—C10—H10B	110.3
C8—N1—C1	129.64 (14)	C11—C10—H10B	110.3
C13—N2—N1	105.49 (13)	H10A—C10—H10B	108.6
N1—C1—C2	112.37 (13)	C10—C11—H11A	109.5
N1—C1—H1A	109.1	C10—C11—H11B	109.5
C2—C1—H1A	109.1	H11A—C11—H11B	109.5
N1—C1—H1B	109.1	C10—C11—H11C	109.5
C2—C1—H1B	109.1	H11A—C11—H11C	109.5
H1A—C1—H1B	107.9	H11B—C11—H11C	109.5
C7—C2—C3	118.03 (17)	C8—C12—C13	105.44 (15)
C7—C2—C1	121.30 (16)	C8—C12—H12	127.3
C3—C2—C1	120.66 (15)	C13—C12—H12	127.3
C4—C3—C2	121.10 (17)	N2—C13—C12	110.70 (14)
C4—C3—H3	119.5	N2—C13—C14	120.36 (14)
C2—C3—H3	119.5	C12—C13—C14	128.93 (15)
C5—C4—C3	119.29 (18)	C19—C14—C15	118.53 (16)
C5—C4—H4	120.4	C19—C14—C13	120.92 (15)
C3—C4—H4	120.4	C15—C14—C13	120.54 (15)
C6—C5—C4	121.16 (18)	C16—C15—C14	120.64 (17)
C6—C5—Cl1	119.15 (14)	C16—C15—H15	119.7
C4—C5—Cl1	119.69 (15)	C14—C15—H15	119.7
C5—C6—C7	118.99 (16)	C17—C16—C15	120.21 (19)
C5—C6—H6	120.5	C17—C16—H16	119.9
C7—C6—H6	120.5	C15—C16—H16	119.9
C6—C7—C2	121.43 (16)	C16—C17—C18	119.58 (18)
C6—C7—H7	119.3	C16—C17—H17	120.2
C2—C7—H7	119.3	C18—C17—H17	120.2
N1—C8—C12	106.85 (14)	C17—C18—C19	120.77 (18)
N1—C8—C9	122.81 (14)	C17—C18—H18	119.6
C12—C8—C9	130.33 (15)	C19—C18—H18	119.6
O1—C9—O2	124.39 (15)	C18—C19—C14	120.25 (18)
O1—C9—C8	125.32 (16)	C18—C19—H19	119.9
O2—C9—C8	110.29 (14)	C14—C19—H19	119.9
O2—C10—C11	107.06 (16)
C8—N1—N2—C13	−0.84 (18)	C12—C8—C9—O1	176.62 (18)
C1—N1—N2—C13	−175.68 (14)	N1—C8—C9—O2	178.64 (14)
N2—N1—C1—C2	96.41 (17)	C12—C8—C9—O2	−3.3 (2)
C8—N1—C1—C2	−77.4 (2)	C9—O2—C10—C11	171.93 (16)
N1—C1—C2—C7	126.30 (17)	N1—C8—C12—C13	−0.64 (17)
N1—C1—C2—C3	−55.0 (2)	C9—C8—C12—C13	−178.92 (16)
C7—C2—C3—C4	0.4 (3)	N1—N2—C13—C12	0.41 (18)
C1—C2—C3—C4	−178.33 (18)	N1—N2—C13—C14	179.81 (13)
C2—C3—C4—C5	−0.1 (3)	C8—C12—C13—N2	0.15 (18)
C3—C4—C5—C6	−0.1 (3)	C8—C12—C13—C14	−179.18 (15)
C3—C4—C5—Cl1	179.85 (16)	N2—C13—C14—C19	6.6 (2)
C4—C5—C6—C7	−0.1 (3)	C12—C13—C14—C19	−174.15 (17)
Cl1—C5—C6—C7	179.98 (13)	N2—C13—C14—C15	−172.21 (15)
C5—C6—C7—C2	0.5 (3)	C12—C13—C14—C15	7.1 (3)
C3—C2—C7—C6	−0.6 (3)	C19—C14—C15—C16	−0.7 (3)
C1—C2—C7—C6	178.15 (15)	C13—C14—C15—C16	178.08 (16)
N2—N1—C8—C12	0.95 (18)	C14—C15—C16—C17	0.0 (3)
C1—N1—C8—C12	175.06 (16)	C15—C16—C17—C18	0.5 (3)
N2—N1—C8—C9	179.39 (14)	C16—C17—C18—C19	−0.3 (3)
C1—N1—C8—C9	−6.5 (3)	C17—C18—C19—C14	−0.5 (3)
C10—O2—C9—O1	1.1 (3)	C15—C14—C19—C18	1.0 (3)
C10—O2—C9—C8	−178.97 (14)	C13—C14—C19—C18	−177.83 (16)
N1—C8—C9—O1	−1.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.56	3.281 (2)	135
C1—H1B···O1	0.97	2.42	2.921 (2)	111

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.56	3.281 (2)	135
C1—H1B⋯O1	0.97	2.42	2.921 (2)	111

Symmetry code: (i) .