1-[3-(4-Chloro-phen-yl)-5-(4-meth-oxy-phen-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone.

In the title compound, C(18)H(17)ClN(2)O(2), the benzene rings form dihedral angles of 6.69 (6) and 74.88 (5)° with the 4,5-dihydro-1H-pyrazole ring. The benzene rings form a dihedral angle of 76.67 (5)° with each other. In the crystal, mol-ecules are linked via bifurcated (C,C)-H⋯O hydrogen bonds into chains along [010]. The crystal structure is further consolidated by C-H⋯π inter-actions.

Related literature

For general background to and the biological activity of the title compound, see: Samshuddin et al. (2011 ▶); Sarojini et al. (2010 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the the data collection, see: Cosier & Glazer (1986 ▶). For a related structure, see: Fun et al. (2010 ▶).

Experimental

Crystal data

C18H17ClN2O2

M = 328.79

Monoclinic,

a = 9.3473 (4) Å

b = 9.4418 (4) Å

c = 19.7840 (7) Å

β = 113.830 (2)°

V = 1597.19 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 100 K

0.39 × 0.25 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.908, T max = 0.958

21450 measured reflections

5715 independent reflections

4900 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.109

S = 1.08

5715 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.48 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/S1600536812009439/bv2200sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009439/bv2200Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009439/bv2200Isup3.cml

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

C18H17ClN2O2	F(000) = 688
Mr = 328.79	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9967 reflections
a = 9.3473 (4) Å	θ = 2.4–32.5°
b = 9.4418 (4) Å	µ = 0.25 mm−1
c = 19.7840 (7) Å	T = 100 K
β = 113.830 (2)°	Block, colourless
V = 1597.19 (11) Å3	0.39 × 0.25 × 0.17 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	5715 independent reflections
Radiation source: fine-focus sealed tube	4900 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 32.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.908, Tmax = 0.958	k = −14→14
21450 measured reflections	l = −28→30

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0578P)2 + 0.4018P] where P = (Fo2 + 2Fc2)/3
5715 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.48 e Å−3
0 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
Cl1	0.39017 (3)	0.39544 (3)	−0.167559 (12)	0.02538 (8)
O1	0.79766 (9)	0.66995 (8)	0.45133 (4)	0.02433 (16)
O2	0.91233 (9)	0.03965 (8)	0.36842 (4)	0.02099 (15)
N1	0.71059 (10)	0.14269 (8)	0.18233 (4)	0.01673 (15)
N2	0.81942 (10)	0.13711 (8)	0.25551 (4)	0.01686 (15)
C1	0.52427 (13)	0.20907 (12)	0.02990 (5)	0.02301 (19)
H1A	0.4856	0.1381	0.0522	0.028*
C2	0.44026 (13)	0.24407 (12)	−0.04388 (5)	0.0241 (2)
H2A	0.3442	0.1979	−0.0721	0.029*
C3	0.49847 (12)	0.34738 (10)	−0.07580 (5)	0.01920 (18)
C4	0.63933 (13)	0.41499 (11)	−0.03629 (5)	0.02137 (19)
H4A	0.6787	0.4838	−0.0594	0.026*
C5	0.72232 (12)	0.38032 (10)	0.03796 (5)	0.01943 (18)
H5A	0.8182	0.4269	0.0659	0.023*
C6	0.66539 (11)	0.27739 (10)	0.07168 (5)	0.01637 (16)
C7	0.75373 (11)	0.24300 (9)	0.14994 (5)	0.01598 (16)
C8	0.90463 (11)	0.31439 (10)	0.19905 (5)	0.01772 (17)
H8A	0.8937	0.4188	0.1971	0.021*
H8B	0.9915	0.2874	0.1852	0.021*
C9	0.93042 (11)	0.25651 (9)	0.27597 (5)	0.01613 (16)
H9A	1.0400	0.2209	0.3019	0.019*
C10	0.89448 (11)	0.36484 (10)	0.32356 (5)	0.01551 (16)
C11	1.00985 (11)	0.46168 (10)	0.36358 (5)	0.01698 (16)
H11A	1.1092	0.4567	0.3612	0.020*
C12	0.98297 (11)	0.56594 (10)	0.40712 (5)	0.01733 (16)
H12A	1.0633	0.6309	0.4343	0.021*
C13	0.83702 (12)	0.57364 (10)	0.41030 (5)	0.01832 (17)
C14	0.71987 (12)	0.47712 (12)	0.37019 (6)	0.0233 (2)
H14A	0.6203	0.4822	0.3723	0.028*
C15	0.74886 (12)	0.37390 (11)	0.32730 (5)	0.02067 (18)
H15A	0.6687	0.3088	0.3002	0.025*
C16	0.91421 (13)	0.77111 (10)	0.49274 (5)	0.02186 (19)
H16A	0.8761	0.8270	0.5238	0.033*
H16B	0.9360	0.8341	0.4587	0.033*
H16C	1.0103	0.7214	0.5240	0.033*
C17	0.81439 (11)	0.03714 (10)	0.30430 (5)	0.01726 (17)
C18	0.68751 (13)	−0.07237 (11)	0.27532 (6)	0.02370 (19)
H18A	0.7054	−0.1461	0.3127	0.036*
H18B	0.6885	−0.1149	0.2303	0.036*
H18C	0.5858	−0.0276	0.2640	0.036*

	U11	U22	U33	U12	U13	U23
Cl1	0.02990 (14)	0.02625 (13)	0.01582 (11)	−0.00074 (9)	0.00491 (9)	0.00026 (8)
O1	0.0228 (4)	0.0255 (3)	0.0257 (3)	−0.0018 (3)	0.0108 (3)	−0.0105 (3)
O2	0.0233 (4)	0.0204 (3)	0.0170 (3)	0.0018 (3)	0.0058 (3)	0.0015 (2)
N1	0.0169 (4)	0.0175 (3)	0.0150 (3)	0.0008 (3)	0.0056 (3)	0.0001 (3)
N2	0.0181 (4)	0.0164 (3)	0.0146 (3)	−0.0012 (3)	0.0051 (3)	−0.0002 (2)
C1	0.0202 (5)	0.0271 (5)	0.0207 (4)	−0.0054 (4)	0.0071 (4)	0.0032 (3)
C2	0.0200 (5)	0.0292 (5)	0.0198 (4)	−0.0060 (4)	0.0047 (4)	0.0012 (3)
C3	0.0215 (5)	0.0202 (4)	0.0153 (4)	0.0008 (3)	0.0068 (3)	−0.0005 (3)
C4	0.0254 (5)	0.0214 (4)	0.0176 (4)	−0.0040 (4)	0.0090 (4)	0.0008 (3)
C5	0.0201 (4)	0.0203 (4)	0.0180 (4)	−0.0038 (3)	0.0078 (3)	−0.0005 (3)
C6	0.0166 (4)	0.0176 (4)	0.0159 (3)	0.0003 (3)	0.0076 (3)	0.0000 (3)
C7	0.0157 (4)	0.0169 (4)	0.0163 (3)	0.0006 (3)	0.0074 (3)	−0.0010 (3)
C8	0.0177 (4)	0.0199 (4)	0.0168 (4)	−0.0027 (3)	0.0083 (3)	−0.0015 (3)
C9	0.0153 (4)	0.0161 (4)	0.0167 (3)	−0.0002 (3)	0.0061 (3)	−0.0010 (3)
C10	0.0157 (4)	0.0165 (4)	0.0135 (3)	0.0008 (3)	0.0050 (3)	0.0006 (3)
C11	0.0165 (4)	0.0173 (4)	0.0182 (4)	−0.0014 (3)	0.0081 (3)	0.0002 (3)
C12	0.0179 (4)	0.0164 (4)	0.0172 (4)	−0.0030 (3)	0.0066 (3)	−0.0008 (3)
C13	0.0194 (4)	0.0190 (4)	0.0165 (4)	0.0009 (3)	0.0072 (3)	−0.0022 (3)
C14	0.0156 (4)	0.0286 (5)	0.0261 (4)	−0.0016 (4)	0.0089 (4)	−0.0089 (4)
C15	0.0150 (4)	0.0241 (4)	0.0215 (4)	−0.0018 (3)	0.0058 (3)	−0.0068 (3)
C16	0.0276 (5)	0.0175 (4)	0.0183 (4)	−0.0010 (4)	0.0070 (4)	−0.0021 (3)
C17	0.0188 (4)	0.0153 (4)	0.0185 (4)	0.0024 (3)	0.0085 (3)	0.0005 (3)
C18	0.0255 (5)	0.0211 (4)	0.0227 (4)	−0.0043 (4)	0.0079 (4)	0.0014 (3)

Cl1—C3	1.7440 (10)	C8—H8A	0.9900
O1—C13	1.3647 (11)	C8—H8B	0.9900
O1—C16	1.4314 (12)	C9—C10	1.5171 (12)
O2—C17	1.2286 (11)	C9—H9A	1.0000
N1—C7	1.2957 (12)	C10—C11	1.3913 (13)
N1—N2	1.3942 (11)	C10—C15	1.3952 (13)
N2—C17	1.3644 (12)	C11—C12	1.3962 (13)
N2—C9	1.4738 (12)	C11—H11A	0.9500
C1—C2	1.3894 (14)	C12—C13	1.3927 (14)
C1—C6	1.3994 (14)	C12—H12A	0.9500
C1—H1A	0.9500	C13—C14	1.3990 (14)
C2—C3	1.3870 (14)	C14—C15	1.3890 (13)
C2—H2A	0.9500	C14—H14A	0.9500
C3—C4	1.3857 (14)	C15—H15A	0.9500
C4—C5	1.3951 (13)	C16—H16A	0.9800
C4—H4A	0.9500	C16—H16B	0.9800
C5—C6	1.3998 (13)	C16—H16C	0.9800
C5—H5A	0.9500	C17—C18	1.5017 (14)
C6—C7	1.4668 (12)	C18—H18A	0.9800
C7—C8	1.5102 (13)	C18—H18B	0.9800
C8—C9	1.5414 (12)	C18—H18C	0.9800
C13—O1—C16	117.34 (8)	C10—C9—H9A	110.2
C7—N1—N2	107.39 (8)	C8—C9—H9A	110.2
C17—N2—N1	122.80 (8)	C11—C10—C15	118.56 (8)
C17—N2—C9	123.82 (8)	C11—C10—C9	118.76 (8)
N1—N2—C9	113.18 (7)	C15—C10—C9	122.66 (8)
C2—C1—C6	120.58 (9)	C10—C11—C12	121.53 (9)
C2—C1—H1A	119.7	C10—C11—H11A	119.2
C6—C1—H1A	119.7	C12—C11—H11A	119.2
C3—C2—C1	119.10 (9)	C13—C12—C11	119.24 (8)
C3—C2—H2A	120.4	C13—C12—H12A	120.4
C1—C2—H2A	120.4	C11—C12—H12A	120.4
C4—C3—C2	121.69 (9)	O1—C13—C12	124.47 (9)
C4—C3—Cl1	119.14 (7)	O1—C13—C14	115.73 (9)
C2—C3—Cl1	119.17 (8)	C12—C13—C14	119.79 (9)
C3—C4—C5	118.89 (9)	C15—C14—C13	120.16 (9)
C3—C4—H4A	120.6	C15—C14—H14A	119.9
C5—C4—H4A	120.6	C13—C14—H14A	119.9
C4—C5—C6	120.53 (9)	C14—C15—C10	120.71 (9)
C4—C5—H5A	119.7	C14—C15—H15A	119.6
C6—C5—H5A	119.7	C10—C15—H15A	119.6
C1—C6—C5	119.19 (8)	O1—C16—H16A	109.5
C1—C6—C7	121.05 (8)	O1—C16—H16B	109.5
C5—C6—C7	119.77 (8)	H16A—C16—H16B	109.5
N1—C7—C6	121.93 (8)	O1—C16—H16C	109.5
N1—C7—C8	113.87 (8)	H16A—C16—H16C	109.5
C6—C7—C8	124.15 (8)	H16B—C16—H16C	109.5
C7—C8—C9	102.11 (7)	O2—C17—N2	119.53 (9)
C7—C8—H8A	111.3	O2—C17—C18	123.48 (9)
C9—C8—H8A	111.3	N2—C17—C18	116.99 (8)
C7—C8—H8B	111.3	C17—C18—H18A	109.5
C9—C8—H8B	111.3	C17—C18—H18B	109.5
H8A—C8—H8B	109.2	H18A—C18—H18B	109.5
N2—C9—C10	112.23 (8)	C17—C18—H18C	109.5
N2—C9—C8	100.85 (7)	H18A—C18—H18C	109.5
C10—C9—C8	112.84 (7)	H18B—C18—H18C	109.5
N2—C9—H9A	110.2
C7—N1—N2—C17	−175.94 (8)	N1—N2—C9—C8	−15.47 (9)
C7—N1—N2—C9	9.10 (10)	C7—C8—C9—N2	14.77 (9)
C6—C1—C2—C3	0.28 (17)	C7—C8—C9—C10	−105.14 (8)
C1—C2—C3—C4	0.99 (16)	N2—C9—C10—C11	162.70 (8)
C1—C2—C3—Cl1	−177.99 (8)	C8—C9—C10—C11	−84.18 (10)
C2—C3—C4—C5	−1.61 (16)	N2—C9—C10—C15	−19.12 (12)
Cl1—C3—C4—C5	177.37 (8)	C8—C9—C10—C15	94.01 (11)
C3—C4—C5—C6	0.97 (15)	C15—C10—C11—C12	0.32 (14)
C2—C1—C6—C5	−0.89 (16)	C9—C10—C11—C12	178.58 (8)
C2—C1—C6—C7	178.96 (10)	C10—C11—C12—C13	−0.32 (14)
C4—C5—C6—C1	0.25 (15)	C16—O1—C13—C12	1.13 (14)
C4—C5—C6—C7	−179.59 (9)	C16—O1—C13—C14	−179.58 (9)
N2—N1—C7—C6	179.53 (8)	C11—C12—C13—O1	179.42 (9)
N2—N1—C7—C8	2.14 (10)	C11—C12—C13—C14	0.16 (14)
C1—C6—C7—N1	4.38 (14)	O1—C13—C14—C15	−179.34 (9)
C5—C6—C7—N1	−175.78 (9)	C12—C13—C14—C15	−0.01 (16)
C1—C6—C7—C8	−178.50 (9)	C13—C14—C15—C10	0.02 (16)
C5—C6—C7—C8	1.34 (14)	C11—C10—C15—C14	−0.17 (15)
N1—C7—C8—C9	−11.45 (10)	C9—C10—C15—C14	−178.36 (9)
C6—C7—C8—C9	171.22 (8)	N1—N2—C17—O2	−178.73 (8)
C17—N2—C9—C10	−70.02 (11)	C9—N2—C17—O2	−4.31 (14)
N1—N2—C9—C10	104.88 (8)	N1—N2—C17—C18	1.89 (13)
C17—N2—C9—C8	169.63 (9)	C9—N2—C17—C18	176.31 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O2i	0.95	2.55	3.4993 (14)	174
C16—H16B···O2ii	0.98	2.59	3.5275 (12)	161
C16—H16C···Cg1iii	0.98	2.69	3.5333 (10)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C10–C15 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O2i	0.95	2.55	3.4993 (14)	174
C16—H16B⋯O2ii	0.98	2.59	3.5275 (12)	161
C16—H16C⋯Cg1iii	0.98	2.69	3.5333 (10)	145

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