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

In the title compound, C(20)H(21)ClN(2)O(2), the benzene rings form dihedral angles of 6.35 (5) and 81.82 (5)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.145 Å). This latter ring adopts an envelope conformation with the CH grouping as the flap. The dihedral angle between the benzene rings is 75.63 (4)°. In the crystal, mol-ecules are linked by C-H⋯Cl and C-H⋯O hydrogen bonds into chains along [-201]. The crystal structure also features C-H⋯π inter-actions.

Related literature

For a related structure, see: Fun et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H21ClN2O2

M = 356.84

Triclinic,

a = 6.7918 (3) Å

b = 10.8822 (4) Å

c = 13.2576 (5) Å

α = 109.202 (1)°

β = 91.396 (1)°

γ = 105.087 (1)°

V = 886.93 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 100 K

0.43 × 0.17 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.908, T max = 0.968

17324 measured reflections

6403 independent reflections

5492 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.104

S = 1.04

6403 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.30 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/S1600536812009105/hb6658sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009105/hb6658Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009105/hb6658Isup3.cml

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

C20H21ClN2O2	Z = 2
Mr = 356.84	F(000) = 376
Triclinic, P1	Dx = 1.336 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7918 (3) Å	Cell parameters from 8526 reflections
b = 10.8822 (4) Å	θ = 3.1–32.7°
c = 13.2576 (5) Å	µ = 0.23 mm−1
α = 109.202 (1)°	T = 100 K
β = 91.396 (1)°	Block, colourless
γ = 105.087 (1)°	0.43 × 0.17 × 0.14 mm
V = 886.93 (6) Å3

Bruker SMART APEXII DUO CCD diffractometer	6403 independent reflections
Radiation source: fine-focus sealed tube	5492 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 32.7°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→9
Tmin = 0.908, Tmax = 0.968	k = −16→16
17324 measured reflections	l = −20→20

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0556P)2 + 0.2279P] where P = (Fo2 + 2Fc2)/3
6403 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.30 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	0.89607 (4)	0.72819 (3)	0.48730 (2)	0.02770 (7)
O1	−0.64280 (11)	0.12922 (7)	0.66911 (6)	0.02244 (14)
O2	−0.24411 (10)	0.75836 (7)	0.97896 (5)	0.01753 (13)
N1	0.11361 (11)	0.74489 (7)	0.79068 (6)	0.01296 (12)
N2	−0.00821 (11)	0.71541 (7)	0.86691 (6)	0.01292 (12)
C1	0.42153 (13)	0.77985 (9)	0.65141 (7)	0.01642 (15)
H1A	0.3354	0.8358	0.6629	0.020*
C2	0.57466 (14)	0.79372 (10)	0.58516 (7)	0.01864 (16)
H2A	0.5930	0.8594	0.5530	0.022*
C3	0.70038 (13)	0.70779 (10)	0.56759 (7)	0.01822 (16)
C4	0.67516 (13)	0.60834 (9)	0.61348 (7)	0.01807 (16)
H4A	0.7585	0.5505	0.5995	0.022*
C5	0.52253 (13)	0.59623 (9)	0.68109 (7)	0.01569 (15)
H5A	0.5051	0.5304	0.7130	0.019*
C6	0.39554 (12)	0.68211 (8)	0.70129 (6)	0.01347 (14)
C7	0.24252 (12)	0.67322 (8)	0.77666 (6)	0.01296 (14)
C8	0.22791 (12)	0.59223 (8)	0.85087 (7)	0.01436 (14)
H8A	0.3390	0.6342	0.9095	0.017*
H8B	0.2293	0.4998	0.8123	0.017*
C9	0.01915 (12)	0.59689 (8)	0.89181 (6)	0.01294 (14)
H9A	0.0297	0.6161	0.9696	0.016*
C10	−0.15764 (12)	0.47169 (8)	0.83447 (6)	0.01292 (14)
C11	−0.15456 (14)	0.38856 (9)	0.72900 (7)	0.01689 (15)
H11A	−0.0403	0.4090	0.6939	0.020*
C12	−0.31873 (14)	0.27611 (9)	0.67577 (7)	0.01846 (16)
H12A	−0.3135	0.2218	0.6057	0.022*
C13	−0.49209 (13)	0.24412 (9)	0.72721 (7)	0.01629 (15)
C14	−0.49940 (13)	0.32638 (9)	0.83207 (7)	0.01572 (15)
H14A	−0.6146	0.3067	0.8668	0.019*
C15	−0.33179 (13)	0.43875 (8)	0.88443 (7)	0.01423 (14)
H15A	−0.3366	0.4930	0.9546	0.017*
C16	−0.82621 (16)	0.09749 (11)	0.71737 (10)	0.0288 (2)
H16A	−0.9211	0.0160	0.6690	0.043*
H16B	−0.8873	0.1709	0.7324	0.043*
H16C	−0.7935	0.0843	0.7832	0.043*
C17	−0.14102 (12)	0.78735 (8)	0.91064 (6)	0.01265 (14)
C18	−0.14900 (12)	0.90227 (8)	0.87211 (6)	0.01306 (14)
H18A	−0.1800	0.8672	0.7944	0.016*
H18B	−0.0151	0.9688	0.8905	0.016*
C19	−0.30931 (13)	0.97135 (8)	0.92125 (7)	0.01505 (14)
H19A	−0.2782	1.0069	0.9990	0.018*
H19B	−0.4434	0.9050	0.9030	0.018*
C20	−0.31538 (16)	1.08654 (9)	0.88125 (8)	0.02108 (17)
H20A	−0.4138	1.1302	0.9160	0.032*
H20B	−0.3541	1.0508	0.8048	0.032*
H20C	−0.1820	1.1513	0.8977	0.032*

	U11	U22	U33	U12	U13	U23
Cl1	0.02295 (12)	0.03579 (14)	0.02385 (12)	0.00841 (9)	0.01502 (9)	0.00879 (9)
O1	0.0177 (3)	0.0192 (3)	0.0253 (3)	−0.0002 (2)	0.0032 (2)	0.0053 (3)
O2	0.0185 (3)	0.0192 (3)	0.0194 (3)	0.0091 (2)	0.0097 (2)	0.0092 (2)
N1	0.0110 (3)	0.0152 (3)	0.0140 (3)	0.0049 (2)	0.0047 (2)	0.0057 (2)
N2	0.0127 (3)	0.0142 (3)	0.0155 (3)	0.0067 (2)	0.0061 (2)	0.0074 (2)
C1	0.0142 (3)	0.0208 (4)	0.0165 (3)	0.0072 (3)	0.0039 (3)	0.0075 (3)
C2	0.0175 (4)	0.0238 (4)	0.0162 (4)	0.0058 (3)	0.0050 (3)	0.0088 (3)
C3	0.0136 (3)	0.0243 (4)	0.0136 (3)	0.0046 (3)	0.0052 (3)	0.0030 (3)
C4	0.0143 (4)	0.0214 (4)	0.0175 (4)	0.0078 (3)	0.0053 (3)	0.0031 (3)
C5	0.0133 (3)	0.0176 (3)	0.0163 (3)	0.0064 (3)	0.0041 (3)	0.0043 (3)
C6	0.0105 (3)	0.0168 (3)	0.0130 (3)	0.0049 (3)	0.0027 (2)	0.0042 (3)
C7	0.0103 (3)	0.0150 (3)	0.0140 (3)	0.0044 (3)	0.0025 (2)	0.0050 (3)
C8	0.0120 (3)	0.0169 (3)	0.0178 (3)	0.0069 (3)	0.0042 (3)	0.0083 (3)
C9	0.0130 (3)	0.0143 (3)	0.0144 (3)	0.0065 (3)	0.0041 (3)	0.0065 (3)
C10	0.0130 (3)	0.0142 (3)	0.0144 (3)	0.0062 (3)	0.0047 (3)	0.0066 (3)
C11	0.0159 (4)	0.0189 (4)	0.0159 (3)	0.0053 (3)	0.0071 (3)	0.0055 (3)
C12	0.0185 (4)	0.0191 (4)	0.0160 (3)	0.0048 (3)	0.0054 (3)	0.0038 (3)
C13	0.0151 (3)	0.0153 (3)	0.0192 (4)	0.0039 (3)	0.0028 (3)	0.0071 (3)
C14	0.0144 (3)	0.0170 (3)	0.0197 (4)	0.0060 (3)	0.0070 (3)	0.0098 (3)
C15	0.0157 (3)	0.0156 (3)	0.0150 (3)	0.0074 (3)	0.0061 (3)	0.0074 (3)
C16	0.0190 (4)	0.0264 (5)	0.0360 (5)	−0.0015 (4)	0.0059 (4)	0.0101 (4)
C17	0.0113 (3)	0.0130 (3)	0.0137 (3)	0.0050 (2)	0.0024 (2)	0.0035 (3)
C18	0.0122 (3)	0.0136 (3)	0.0150 (3)	0.0056 (3)	0.0033 (3)	0.0054 (3)
C19	0.0141 (3)	0.0148 (3)	0.0174 (3)	0.0073 (3)	0.0025 (3)	0.0045 (3)
C20	0.0252 (4)	0.0186 (4)	0.0230 (4)	0.0121 (3)	0.0016 (3)	0.0073 (3)

Cl1—C3	1.7377 (9)	C9—H9A	0.9800
O1—C13	1.3661 (11)	C10—C15	1.3928 (11)
O1—C16	1.4285 (13)	C10—C11	1.3976 (11)
O2—C17	1.2305 (10)	C11—C12	1.3864 (12)
N1—C7	1.2952 (10)	C11—H11A	0.9300
N1—N2	1.3874 (9)	C12—C13	1.3981 (12)
N2—C17	1.3628 (10)	C12—H12A	0.9300
N2—C9	1.4862 (10)	C13—C14	1.3944 (12)
C1—C2	1.3878 (12)	C14—C15	1.3970 (12)
C1—C6	1.4036 (12)	C14—H14A	0.9300
C1—H1A	0.9300	C15—H15A	0.9300
C2—C3	1.3928 (13)	C16—H16A	0.9600
C2—H2A	0.9300	C16—H16B	0.9600
C3—C4	1.3829 (13)	C16—H16C	0.9600
C4—C5	1.3955 (12)	C17—C18	1.5106 (11)
C4—H4A	0.9300	C18—C19	1.5210 (11)
C5—C6	1.3983 (11)	C18—H18A	0.9700
C5—H5A	0.9300	C18—H18B	0.9700
C6—C7	1.4662 (11)	C19—C20	1.5222 (12)
C7—C8	1.5114 (11)	C19—H19A	0.9700
C8—C9	1.5376 (11)	C19—H19B	0.9700
C8—H8A	0.9700	C20—H20A	0.9600
C8—H8B	0.9700	C20—H20B	0.9600
C9—C10	1.5161 (11)	C20—H20C	0.9600
C13—O1—C16	116.96 (8)	C12—C11—H11A	119.4
C7—N1—N2	107.57 (7)	C10—C11—H11A	119.4
C17—N2—N1	122.26 (7)	C11—C12—C13	120.15 (8)
C17—N2—C9	124.98 (7)	C11—C12—H12A	119.9
N1—N2—C9	112.74 (6)	C13—C12—H12A	119.9
C2—C1—C6	120.57 (8)	O1—C13—C14	124.71 (8)
C2—C1—H1A	119.7	O1—C13—C12	115.63 (8)
C6—C1—H1A	119.7	C14—C13—C12	119.63 (8)
C1—C2—C3	118.99 (8)	C13—C14—C15	119.28 (8)
C1—C2—H2A	120.5	C13—C14—H14A	120.4
C3—C2—H2A	120.5	C15—C14—H14A	120.4
C4—C3—C2	121.74 (8)	C10—C15—C14	121.80 (8)
C4—C3—Cl1	119.37 (7)	C10—C15—H15A	119.1
C2—C3—Cl1	118.87 (7)	C14—C15—H15A	119.1
C3—C4—C5	118.89 (8)	O1—C16—H16A	109.5
C3—C4—H4A	120.6	O1—C16—H16B	109.5
C5—C4—H4A	120.6	H16A—C16—H16B	109.5
C4—C5—C6	120.66 (8)	O1—C16—H16C	109.5
C4—C5—H5A	119.7	H16A—C16—H16C	109.5
C6—C5—H5A	119.7	H16B—C16—H16C	109.5
C5—C6—C1	119.12 (8)	O2—C17—N2	119.86 (7)
C5—C6—C7	120.28 (7)	O2—C17—C18	123.61 (7)
C1—C6—C7	120.57 (7)	N2—C17—C18	116.52 (7)
N1—C7—C6	121.23 (7)	C17—C18—C19	112.44 (7)
N1—C7—C8	113.34 (7)	C17—C18—H18A	109.1
C6—C7—C8	125.25 (7)	C19—C18—H18A	109.1
C7—C8—C9	101.98 (6)	C17—C18—H18B	109.1
C7—C8—H8A	111.4	C19—C18—H18B	109.1
C9—C8—H8A	111.4	H18A—C18—H18B	107.8
C7—C8—H8B	111.4	C18—C19—C20	111.65 (7)
C9—C8—H8B	111.4	C18—C19—H19A	109.3
H8A—C8—H8B	109.2	C20—C19—H19A	109.3
N2—C9—C10	110.38 (6)	C18—C19—H19B	109.3
N2—C9—C8	99.94 (6)	C20—C19—H19B	109.3
C10—C9—C8	114.84 (7)	H19A—C19—H19B	108.0
N2—C9—H9A	110.4	C19—C20—H20A	109.5
C10—C9—H9A	110.4	C19—C20—H20B	109.5
C8—C9—H9A	110.4	H20A—C20—H20B	109.5
C15—C10—C11	117.92 (8)	C19—C20—H20C	109.5
C15—C10—C9	120.71 (7)	H20A—C20—H20C	109.5
C11—C10—C9	121.33 (7)	H20B—C20—H20C	109.5
C12—C11—C10	121.22 (8)
C7—N1—N2—C17	170.91 (8)	C7—C8—C9—C10	98.74 (7)
C7—N1—N2—C9	−10.65 (9)	N2—C9—C10—C15	−91.37 (9)
C6—C1—C2—C3	0.94 (13)	C8—C9—C10—C15	156.62 (7)
C1—C2—C3—C4	0.68 (14)	N2—C9—C10—C11	86.38 (9)
C1—C2—C3—Cl1	−178.41 (7)	C8—C9—C10—C11	−25.64 (11)
C2—C3—C4—C5	−1.50 (14)	C15—C10—C11—C12	−0.50 (13)
Cl1—C3—C4—C5	177.60 (7)	C9—C10—C11—C12	−178.30 (8)
C3—C4—C5—C6	0.70 (13)	C10—C11—C12—C13	0.25 (14)
C4—C5—C6—C1	0.87 (13)	C16—O1—C13—C14	4.58 (13)
C4—C5—C6—C7	−176.92 (8)	C16—O1—C13—C12	−176.96 (8)
C2—C1—C6—C5	−1.70 (13)	C11—C12—C13—O1	−178.16 (8)
C2—C1—C6—C7	176.08 (8)	C11—C12—C13—C14	0.38 (13)
N2—N1—C7—C6	−179.36 (7)	O1—C13—C14—C15	177.66 (8)
N2—N1—C7—C8	−4.00 (9)	C12—C13—C14—C15	−0.74 (13)
C5—C6—C7—N1	−174.99 (8)	C11—C10—C15—C14	0.12 (12)
C1—C6—C7—N1	7.25 (12)	C9—C10—C15—C14	177.94 (7)
C5—C6—C7—C8	10.22 (12)	C13—C14—C15—C10	0.49 (12)
C1—C6—C7—C8	−167.54 (8)	N1—N2—C17—O2	−179.14 (7)
N1—C7—C8—C9	15.87 (9)	C9—N2—C17—O2	2.62 (12)
C6—C7—C8—C9	−168.98 (7)	N1—N2—C17—C18	−0.20 (11)
C17—N2—C9—C10	76.57 (10)	C9—N2—C17—C18	−178.45 (7)
N1—N2—C9—C10	−101.82 (8)	O2—C17—C18—C19	−4.07 (11)
C17—N2—C9—C8	−162.10 (8)	N2—C17—C18—C19	177.04 (7)
N1—N2—C9—C8	19.52 (8)	C17—C18—C19—C20	−179.85 (7)
C7—C8—C9—N2	−19.34 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···Cl1i	0.93	2.73	3.4539 (10)	135
C14—H14A···O2ii	0.93	2.51	3.3253 (12)	147
C18—H18A···Cg1iii	0.97	2.62	3.4514 (9)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯Cl1i	0.93	2.73	3.4539 (10)	135
C14—H14A⋯O2ii	0.93	2.51	3.3253 (12)	147
C18—H18A⋯Cg1iii	0.97	2.62	3.4514 (9)	144

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