Ethyl 3-(4-chloro-phen-yl)-1-(2-oxo-2-phenyl-eth-yl)-1H-pyrazole-5-carboxyl-ate.

In the title compound, C(20)H(17)ClN(2)O(3), the dihedral angles between the pyrazole ring and the substituted and unsubstituted benzene rings are 3.64 (13) and 81.15 (17)°, respectively. Mol-ecules are connected via three pairs of weak hydrogen bonds into a centrosymmetric dimer. The crystal structure is stabilized by inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For applications of pyrazoles, see: Kosuge & Kamiya (1962 ▶); Ganesan (1996 ▶); Farag et al. (2010 ▶); Boschi et al. (2011 ▶); Kasımoğullan et al. (2010 ▶); Christodoulou et al. (2010 ▶); Scanio et al. (2010 ▶); Da Sliva et al. (2010 ▶). For related structures, see: Xie et al. (2009 ▶); Arban et al. (2010 ▶). For the synthesis of ethyl 3-(4-chloro­phen­yl)-1-(2-oxo-2-phenyl­eth­yl)-1H-pyrazole-5-carboxyl­ate, see: Zheng et al. (2010 ▶).

Experimental

Crystal data

C20H17ClN2O3

M = 368.81

Triclinic,

a = 7.7238 (10) Å

b = 8.382 (1) Å

c = 15.8143 (18) Å

α = 98.667 (2)°

β = 93.828 (2)°

γ = 113.849 (2)°

V = 916.44 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.12 × 0.10 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.973, T max = 0.986

4894 measured reflections

3216 independent reflections

2079 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.123

S = 1.04

3216 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811025918/vm2105sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025918/vm2105Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025918/vm2105Isup3.cml

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

C20H17ClN2O3	Z = 2
Mr = 368.81	F(000) = 384
Triclinic, P1	Dx = 1.337 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7238 (10) Å	Cell parameters from 1101 reflections
b = 8.382 (1) Å	θ = 2.7–22.0°
c = 15.8143 (18) Å	µ = 0.23 mm−1
α = 98.667 (2)°	T = 296 K
β = 93.828 (2)°	Block, colorless
γ = 113.849 (2)°	0.12 × 0.10 × 0.06 mm
V = 916.44 (19) Å3

Bruker APEXII CCD area-detector diffractometer	3216 independent reflections
Radiation source: fine-focus sealed tube	2079 reflections with I > 2σ(I)
graphite	Rint = 0.018
phi and ω scans	θmax = 25.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→8
Tmin = 0.973, Tmax = 0.986	k = −9→9
4894 measured reflections	l = −18→10

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0468P)2 + 0.1653P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3216 reflections	Δρmax = 0.17 e Å−3
237 parameters	Δρmin = −0.18 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: 0.008 (2)

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	1.39705 (12)	0.55340 (11)	0.24320 (5)	0.0857 (3)
O1	0.4703 (3)	0.6797 (3)	0.61211 (13)	0.0882 (7)
O2	0.6629 (2)	0.8989 (2)	0.71892 (11)	0.0689 (5)
O3	1.0787 (3)	0.9089 (2)	0.79687 (11)	0.0765 (6)
N1	0.9783 (3)	0.9370 (2)	0.63117 (12)	0.0502 (5)
N2	1.1032 (3)	0.9166 (2)	0.58057 (12)	0.0516 (5)
C1	0.5722 (5)	1.0065 (5)	0.8478 (2)	0.1137 (13)
H1A	0.6625	0.9790	0.8802	0.171*
H1B	0.4675	0.9957	0.8795	0.171*
H1C	0.6337	1.1260	0.8382	0.171*
C2	0.4997 (4)	0.8818 (4)	0.7639 (2)	0.0894 (10)
H2A	0.4340	0.7609	0.7728	0.107*
H2B	0.4103	0.9101	0.7300	0.107*
C3	0.6271 (4)	0.7888 (3)	0.64366 (16)	0.0583 (7)
C4	0.7978 (3)	0.8102 (3)	0.60278 (14)	0.0490 (6)
C5	0.8081 (3)	0.7040 (3)	0.53051 (15)	0.0510 (6)
H5	0.7078	0.6056	0.4964	0.061*
C6	0.9993 (3)	0.7733 (3)	0.51840 (14)	0.0470 (6)
C7	1.0940 (3)	0.7141 (3)	0.45134 (14)	0.0474 (6)
C8	0.9962 (4)	0.5635 (3)	0.38749 (15)	0.0532 (6)
H8	0.8667	0.4953	0.3875	0.064*
C9	1.0887 (4)	0.5136 (3)	0.32388 (15)	0.0571 (7)
H9	1.0221	0.4119	0.2816	0.069*
C10	1.2795 (4)	0.6148 (3)	0.32337 (16)	0.0591 (7)
C11	1.3793 (4)	0.7624 (4)	0.38583 (17)	0.0725 (8)
H11	1.5090	0.8297	0.3856	0.087*
C12	1.2863 (4)	0.8106 (4)	0.44906 (17)	0.0697 (8)
H12	1.3550	0.9113	0.4916	0.084*
C13	1.0477 (3)	1.0912 (3)	0.70068 (14)	0.0530 (6)
H13A	0.9535	1.1403	0.7030	0.064*
H13B	1.1641	1.1808	0.6876	0.064*
C14	1.0880 (3)	1.0536 (3)	0.78837 (15)	0.0530 (6)
C15	1.1408 (3)	1.2016 (3)	0.86377 (16)	0.0556 (7)
C16	1.1626 (4)	1.3698 (4)	0.85486 (18)	0.0757 (9)
H16	1.1464	1.3938	0.8001	0.091*
C17	1.2085 (5)	1.5024 (4)	0.9269 (2)	0.1021 (12)
H17	1.2223	1.6153	0.9205	0.122*
C18	1.2337 (6)	1.4687 (5)	1.0071 (2)	0.1132 (13)
H18	1.2645	1.5583	1.0555	0.136*
C19	1.2139 (6)	1.3030 (5)	1.0166 (2)	0.1131 (13)
H19	1.2313	1.2801	1.0715	0.136*
C20	1.1684 (5)	1.1703 (4)	0.94532 (18)	0.0823 (9)
H20	1.1561	1.0582	0.9523	0.099*

	U11	U22	U33	U12	U13	U23
Cl1	0.0942 (6)	0.0923 (6)	0.0644 (5)	0.0382 (5)	0.0278 (4)	−0.0068 (4)
O1	0.0441 (11)	0.1021 (15)	0.0846 (15)	0.0121 (11)	0.0016 (10)	−0.0234 (12)
O2	0.0548 (11)	0.0744 (12)	0.0650 (12)	0.0223 (9)	0.0134 (9)	−0.0112 (10)
O3	0.1026 (16)	0.0619 (12)	0.0619 (13)	0.0395 (11)	−0.0061 (10)	−0.0036 (9)
N1	0.0477 (12)	0.0485 (11)	0.0419 (11)	0.0137 (10)	0.0032 (9)	−0.0072 (9)
N2	0.0477 (12)	0.0529 (12)	0.0432 (12)	0.0146 (10)	0.0045 (9)	−0.0031 (9)
C1	0.105 (3)	0.139 (3)	0.091 (3)	0.057 (3)	0.031 (2)	−0.017 (2)
C2	0.064 (2)	0.111 (3)	0.086 (2)	0.0386 (18)	0.0236 (17)	−0.0116 (19)
C3	0.0511 (17)	0.0620 (16)	0.0549 (17)	0.0217 (14)	0.0052 (13)	−0.0024 (13)
C4	0.0445 (14)	0.0495 (14)	0.0456 (14)	0.0162 (11)	0.0006 (11)	0.0006 (11)
C5	0.0455 (14)	0.0508 (14)	0.0458 (14)	0.0141 (11)	0.0000 (11)	−0.0020 (11)
C6	0.0460 (14)	0.0478 (13)	0.0395 (13)	0.0148 (11)	0.0011 (11)	0.0025 (11)
C7	0.0476 (14)	0.0473 (13)	0.0397 (13)	0.0152 (11)	0.0025 (10)	0.0016 (10)
C8	0.0516 (15)	0.0459 (13)	0.0523 (15)	0.0147 (12)	0.0016 (12)	0.0004 (11)
C9	0.0685 (18)	0.0459 (14)	0.0469 (15)	0.0202 (13)	−0.0006 (12)	−0.0052 (11)
C10	0.0642 (18)	0.0605 (16)	0.0469 (15)	0.0238 (14)	0.0112 (12)	−0.0006 (12)
C11	0.0555 (17)	0.0782 (19)	0.0575 (17)	0.0099 (14)	0.0136 (13)	−0.0126 (14)
C12	0.0553 (17)	0.0687 (17)	0.0556 (17)	0.0071 (14)	0.0071 (13)	−0.0184 (13)
C13	0.0524 (15)	0.0494 (14)	0.0453 (15)	0.0143 (12)	0.0044 (11)	−0.0038 (11)
C14	0.0453 (15)	0.0537 (15)	0.0508 (16)	0.0166 (12)	0.0034 (11)	−0.0033 (12)
C15	0.0529 (16)	0.0596 (16)	0.0472 (16)	0.0225 (13)	0.0028 (12)	−0.0047 (12)
C16	0.096 (2)	0.0646 (18)	0.0563 (18)	0.0314 (16)	0.0044 (15)	−0.0087 (14)
C17	0.146 (3)	0.069 (2)	0.077 (3)	0.042 (2)	0.009 (2)	−0.0134 (18)
C18	0.161 (4)	0.097 (3)	0.065 (2)	0.055 (3)	0.002 (2)	−0.028 (2)
C19	0.167 (4)	0.112 (3)	0.052 (2)	0.063 (3)	−0.005 (2)	−0.010 (2)
C20	0.111 (3)	0.080 (2)	0.0514 (18)	0.0417 (19)	0.0006 (16)	−0.0029 (15)

Cl1—C10	1.741 (2)	C8—H8	0.9300
O1—C3	1.199 (3)	C9—C10	1.373 (3)
O2—C3	1.328 (3)	C9—H9	0.9300
O2—C2	1.456 (3)	C10—C11	1.363 (3)
O3—C14	1.214 (3)	C11—C12	1.374 (3)
N1—N2	1.340 (2)	C11—H11	0.9300
N1—C4	1.360 (3)	C12—H12	0.9300
N1—C13	1.449 (3)	C13—C14	1.508 (3)
N2—C6	1.346 (3)	C13—H13A	0.9700
C1—C2	1.475 (4)	C13—H13B	0.9700
C1—H1A	0.9600	C14—C15	1.486 (3)
C1—H1B	0.9600	C15—C20	1.374 (4)
C1—H1C	0.9600	C15—C16	1.381 (4)
C2—H2A	0.9700	C16—C17	1.380 (4)
C2—H2B	0.9700	C16—H16	0.9300
C3—C4	1.465 (3)	C17—C18	1.358 (5)
C4—C5	1.367 (3)	C17—H17	0.9300
C5—C6	1.390 (3)	C18—C19	1.368 (5)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.464 (3)	C19—C20	1.373 (4)
C7—C12	1.381 (3)	C19—H19	0.9300
C7—C8	1.388 (3)	C20—H20	0.9300
C8—C9	1.381 (3)
C3—O2—C2	116.6 (2)	C8—C9—H9	120.2
N2—N1—C4	111.60 (17)	C11—C10—C9	120.7 (2)
N2—N1—C13	117.93 (18)	C11—C10—Cl1	119.4 (2)
C4—N1—C13	130.3 (2)	C9—C10—Cl1	119.94 (19)
N1—N2—C6	105.50 (18)	C10—C11—C12	119.3 (2)
C2—C1—H1A	109.5	C10—C11—H11	120.4
C2—C1—H1B	109.5	C12—C11—H11	120.4
H1A—C1—H1B	109.5	C11—C12—C7	122.0 (2)
C2—C1—H1C	109.5	C11—C12—H12	119.0
H1A—C1—H1C	109.5	C7—C12—H12	119.0
H1B—C1—H1C	109.5	N1—C13—C14	114.3 (2)
O2—C2—C1	107.8 (2)	N1—C13—H13A	108.7
O2—C2—H2A	110.2	C14—C13—H13A	108.7
C1—C2—H2A	110.2	N1—C13—H13B	108.7
O2—C2—H2B	110.2	C14—C13—H13B	108.7
C1—C2—H2B	110.2	H13A—C13—H13B	107.6
H2A—C2—H2B	108.5	O3—C14—C15	121.5 (2)
O1—C3—O2	123.5 (2)	O3—C14—C13	121.4 (2)
O1—C3—C4	122.6 (2)	C15—C14—C13	117.1 (2)
O2—C3—C4	113.8 (2)	C20—C15—C16	118.7 (2)
N1—C4—C5	106.7 (2)	C20—C15—C14	119.0 (2)
N1—C4—C3	126.4 (2)	C16—C15—C14	122.3 (2)
C5—C4—C3	126.8 (2)	C17—C16—C15	120.3 (3)
C4—C5—C6	105.9 (2)	C17—C16—H16	119.9
C4—C5—H5	127.1	C15—C16—H16	119.9
C6—C5—H5	127.1	C18—C17—C16	120.2 (3)
N2—C6—C5	110.3 (2)	C18—C17—H17	119.9
N2—C6—C7	119.5 (2)	C16—C17—H17	119.9
C5—C6—C7	130.1 (2)	C17—C18—C19	120.0 (3)
C12—C7—C8	117.6 (2)	C17—C18—H18	120.0
C12—C7—C6	120.2 (2)	C19—C18—H18	120.0
C8—C7—C6	122.3 (2)	C18—C19—C20	120.2 (3)
C9—C8—C7	120.8 (2)	C18—C19—H19	119.9
C9—C8—H8	119.6	C20—C19—H19	119.9
C7—C8—H8	119.6	C19—C20—C15	120.7 (3)
C10—C9—C8	119.6 (2)	C19—C20—H20	119.7
C10—C9—H9	120.2	C15—C20—H20	119.7
C4—N1—N2—C6	0.1 (3)	C7—C8—C9—C10	−0.5 (4)
C13—N1—N2—C6	−175.2 (2)	C8—C9—C10—C11	1.1 (4)
C3—O2—C2—C1	176.2 (3)	C8—C9—C10—Cl1	−179.8 (2)
C2—O2—C3—O1	0.3 (4)	C9—C10—C11—C12	−0.9 (5)
C2—O2—C3—C4	−178.7 (2)	Cl1—C10—C11—C12	−180.0 (2)
N2—N1—C4—C5	−0.1 (3)	C10—C11—C12—C7	−0.1 (5)
C13—N1—C4—C5	174.5 (2)	C8—C7—C12—C11	0.7 (4)
N2—N1—C4—C3	178.1 (2)	C6—C7—C12—C11	−178.2 (3)
C13—N1—C4—C3	−7.4 (4)	N2—N1—C13—C14	−100.5 (2)
O1—C3—C4—N1	175.6 (3)	C4—N1—C13—C14	85.2 (3)
O2—C3—C4—N1	−5.4 (4)	N1—C13—C14—O3	6.4 (3)
O1—C3—C4—C5	−6.6 (4)	N1—C13—C14—C15	−174.04 (19)
O2—C3—C4—C5	172.4 (2)	O3—C14—C15—C20	−4.0 (4)
N1—C4—C5—C6	0.1 (3)	C13—C14—C15—C20	176.4 (2)
C3—C4—C5—C6	−178.1 (2)	O3—C14—C15—C16	176.2 (3)
N1—N2—C6—C5	0.0 (3)	C13—C14—C15—C16	−3.4 (4)
N1—N2—C6—C7	179.9 (2)	C20—C15—C16—C17	−0.9 (5)
C4—C5—C6—N2	0.0 (3)	C14—C15—C16—C17	178.8 (3)
C4—C5—C6—C7	−179.9 (2)	C15—C16—C17—C18	0.4 (5)
N2—C6—C7—C12	−3.7 (4)	C16—C17—C18—C19	0.1 (6)
C5—C6—C7—C12	176.1 (3)	C17—C18—C19—C20	0.0 (7)
N2—C6—C7—C8	177.5 (2)	C18—C19—C20—C15	−0.5 (6)
C5—C6—C7—C8	−2.7 (4)	C16—C15—C20—C19	1.0 (5)
C12—C7—C8—C9	−0.4 (4)	C14—C15—C20—C19	−178.8 (3)
C6—C7—C8—C9	178.4 (2)

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.93	2.52	3.410 (3)	161
C8—H8···O1i	0.93	2.42	3.348 (4)	180
C9—H9···O3ii	0.93	2.56	3.434 (3)	157
C13—H13A···Cg1iii	0.97	2.80	3.605 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.93	2.52	3.410 (3)	161
C8—H8⋯O1i	0.93	2.42	3.348 (4)	180
C9—H9⋯O3ii	0.93	2.56	3.434 (3)	157
C13—H13A⋯Cg1iii	0.97	2.80	3.605 (3)	140

Symmetry codes: (i) ; (ii) ; (iii) .