1-[5-(3,4-Dichlorophenyl)-3-(2-naphthyl)-4,5-dihydropyrazol-1-yl]ethanone.

In the title compound, C(21)H(16)Cl(2)N(2)O, the central pyrazoline ring makes dihedral angles of 90.1 (3) and 7.8 (3)°, with the pendant benzene ring and naphthalene ring system, respectively. In the crystal structure, weak C-H⋯O inter-actions lead to chains of mol-ecules.

Related literature

For related literature, see: Lu et al. (2006 ▶).

Experimental

Crystal data

C21H16Cl2N2O

M = 383.26

Triclinic,

a = 6.2154 (12) Å

b = 9.3505 (19) Å

c = 16.319 (3) Å

α = 97.42 (3)°

β = 99.07 (3)°

γ = 104.12 (3)°

V = 894.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 113 (2) K

0.22 × 0.20 × 0.12 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2004 ▶) T min = 0.922, T max = 0.956

9131 measured reflections

3155 independent reflections

2709 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.04

3155 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026858/hb2778sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026858/hb2778Isup2.hkl

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

C21H16Cl2N2O	Z = 2
Mr = 383.26	F000 = 396
Triclinic, P1	Dx = 1.423 Mg m−3
Hall symbol: -P 1	Melting point: 515-516 K K
a = 6.2154 (12) Å	Mo Kα radiation λ = 0.71073 Å
b = 9.3505 (19) Å	Cell parameters from 2978 reflections
c = 16.319 (3) Å	θ = 2.3–27.5º
α = 97.42 (3)º	µ = 0.38 mm−1
β = 99.07 (3)º	T = 113 (2) K
γ = 104.12 (3)º	Slab, colourless
V = 894.2 (3) Å3	0.22 × 0.20 × 0.12 mm

Rigaku saturn diffractometer	3155 independent reflections
Radiation source: rotating anode	2709 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.037
T = 113(2) K	θmax = 25.0º
ω scans	θmin = 2.3º
Absorption correction: multi-scan(Crystalclear; Rigaku, 2004)	h = −7→7
Tmin = 0.922, Tmax = 0.956	k = −11→10
9131 measured reflections	l = −18→19

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0556P)2 + 0.0148P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
3155 reflections	Δρmax = 0.20 e Å−3
236 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	1.32350 (7)	0.97267 (5)	1.10751 (3)	0.02660 (14)
Cl2	1.68608 (7)	0.78933 (5)	1.08859 (3)	0.02684 (14)
O1	1.53261 (19)	0.68503 (13)	0.74819 (7)	0.0286 (3)
N1	0.9532 (2)	0.50512 (15)	0.67138 (8)	0.0198 (3)
N2	1.1666 (2)	0.55742 (15)	0.72303 (8)	0.0206 (3)
C1	0.4859 (3)	0.37150 (18)	0.59400 (10)	0.0215 (4)
H1	0.5670	0.4456	0.5692	0.026*
C2	0.2643 (3)	0.30298 (19)	0.55983 (11)	0.0239 (4)
H2	0.1959	0.3315	0.5120	0.029*
C3	0.1354 (3)	0.18853 (18)	0.59586 (10)	0.0215 (4)
C4	−0.0965 (3)	0.11843 (19)	0.56347 (11)	0.0266 (4)
H4	−0.1698	0.1478	0.5170	0.032*
C5	−0.2152 (3)	0.0078 (2)	0.59938 (12)	0.0298 (4)
H5	−0.3681	−0.0362	0.5775	0.036*
C6	−0.1072 (3)	−0.03961 (19)	0.66921 (11)	0.0265 (4)
H6	−0.1882	−0.1154	0.6930	0.032*
C7	0.1177 (3)	0.02613 (19)	0.70205 (11)	0.0238 (4)
H7	0.1885	−0.0064	0.7478	0.029*
C8	0.2442 (3)	0.14301 (18)	0.66739 (10)	0.0195 (4)
C9	0.4748 (3)	0.21678 (18)	0.70202 (10)	0.0202 (4)
H9	0.5469	0.1879	0.7490	0.024*
C10	0.5944 (3)	0.33057 (17)	0.66748 (10)	0.0194 (4)
C11	0.8300 (3)	0.40644 (18)	0.70550 (10)	0.0185 (4)
C12	0.9545 (3)	0.37641 (18)	0.78625 (10)	0.0210 (4)
H12A	0.9740	0.2760	0.7790	0.025*
H12B	0.8751	0.3893	0.8321	0.025*
C13	1.1838 (3)	0.49564 (18)	0.80228 (10)	0.0205 (4)
H13	1.3077	0.4475	0.8076	0.025*
C14	1.2205 (3)	0.61660 (17)	0.87818 (10)	0.0188 (4)
C15	1.4098 (3)	0.64529 (18)	0.94150 (10)	0.0198 (4)
H15	1.5156	0.5910	0.9367	0.024*
C16	1.4433 (3)	0.75409 (18)	1.01202 (10)	0.0197 (4)
C17	1.2860 (3)	0.83565 (17)	1.01969 (10)	0.0204 (4)
C18	1.0972 (3)	0.80925 (19)	0.95591 (11)	0.0245 (4)
H18	0.9926	0.8645	0.9605	0.029*
C19	1.0647 (3)	0.70084 (19)	0.88558 (11)	0.0243 (4)
H19	0.9384	0.6838	0.8429	0.029*
C20	1.3468 (3)	0.64765 (18)	0.70068 (11)	0.0220 (4)
C21	1.3033 (3)	0.6979 (2)	0.61719 (11)	0.0283 (4)
H21A	1.2530	0.7871	0.6245	0.042*
H21B	1.1888	0.6204	0.5783	0.042*
H21C	1.4403	0.7182	0.5954	0.042*

	U11	U22	U33	U12	U13	U23
Cl1	0.0326 (3)	0.0253 (3)	0.0227 (2)	0.01150 (19)	0.00395 (18)	0.00158 (18)
Cl2	0.0236 (2)	0.0309 (3)	0.0231 (2)	0.00903 (19)	−0.00383 (17)	0.00134 (18)
O1	0.0188 (6)	0.0310 (7)	0.0312 (7)	−0.0007 (5)	0.0034 (5)	0.0045 (6)
N1	0.0164 (7)	0.0214 (7)	0.0185 (7)	0.0017 (6)	0.0020 (6)	0.0008 (6)
N2	0.0166 (7)	0.0245 (8)	0.0178 (7)	0.0005 (6)	0.0022 (6)	0.0046 (6)
C1	0.0215 (9)	0.0208 (9)	0.0212 (9)	0.0025 (7)	0.0054 (7)	0.0044 (7)
C2	0.0237 (9)	0.0251 (10)	0.0217 (9)	0.0047 (7)	0.0029 (7)	0.0052 (7)
C3	0.0204 (9)	0.0199 (9)	0.0222 (9)	0.0031 (7)	0.0054 (7)	−0.0006 (7)
C4	0.0210 (9)	0.0267 (10)	0.0282 (9)	0.0022 (7)	0.0017 (7)	0.0033 (8)
C5	0.0190 (9)	0.0273 (10)	0.0362 (11)	−0.0026 (8)	0.0040 (8)	−0.0001 (8)
C6	0.0260 (9)	0.0194 (9)	0.0307 (10)	−0.0022 (7)	0.0109 (8)	0.0023 (8)
C7	0.0263 (9)	0.0209 (9)	0.0228 (9)	0.0029 (7)	0.0064 (7)	0.0029 (7)
C8	0.0202 (8)	0.0172 (8)	0.0198 (8)	0.0029 (7)	0.0075 (7)	−0.0015 (7)
C9	0.0219 (9)	0.0194 (9)	0.0185 (8)	0.0043 (7)	0.0041 (7)	0.0024 (7)
C10	0.0189 (8)	0.0190 (9)	0.0194 (8)	0.0040 (7)	0.0056 (7)	0.0000 (7)
C11	0.0183 (8)	0.0176 (9)	0.0200 (8)	0.0051 (7)	0.0064 (7)	0.0018 (7)
C12	0.0201 (8)	0.0205 (9)	0.0202 (8)	0.0022 (7)	0.0021 (7)	0.0038 (7)
C13	0.0179 (8)	0.0237 (9)	0.0201 (8)	0.0046 (7)	0.0034 (7)	0.0066 (7)
C14	0.0177 (8)	0.0184 (9)	0.0202 (8)	0.0029 (7)	0.0045 (7)	0.0060 (7)
C15	0.0184 (8)	0.0211 (9)	0.0228 (9)	0.0074 (7)	0.0057 (7)	0.0079 (7)
C16	0.0181 (8)	0.0212 (9)	0.0183 (8)	0.0029 (7)	0.0007 (7)	0.0067 (7)
C17	0.0257 (9)	0.0171 (9)	0.0189 (8)	0.0049 (7)	0.0063 (7)	0.0042 (7)
C18	0.0230 (9)	0.0266 (10)	0.0274 (9)	0.0124 (8)	0.0054 (7)	0.0064 (8)
C19	0.0183 (8)	0.0288 (10)	0.0246 (9)	0.0064 (7)	−0.0001 (7)	0.0057 (8)
C20	0.0196 (9)	0.0190 (9)	0.0255 (9)	0.0023 (7)	0.0056 (7)	0.0014 (7)
C21	0.0261 (10)	0.0289 (10)	0.0283 (9)	0.0004 (8)	0.0090 (8)	0.0086 (8)

Cl1—C17	1.7391 (17)	C9—C10	1.380 (2)
Cl2—C16	1.7329 (17)	C9—H9	0.9300
O1—C20	1.228 (2)	C10—C11	1.458 (2)
N1—C11	1.292 (2)	C11—C12	1.515 (2)
N1—N2	1.3905 (18)	C12—C13	1.541 (2)
N2—C20	1.359 (2)	C12—H12A	0.9700
N2—C13	1.482 (2)	C12—H12B	0.9700
C1—C2	1.361 (2)	C13—C14	1.513 (2)
C1—C10	1.424 (2)	C13—H13	0.9800
C1—H1	0.9300	C14—C15	1.384 (2)
C2—C3	1.423 (2)	C14—C19	1.399 (2)
C2—H2	0.9300	C15—C16	1.386 (2)
C3—C4	1.412 (2)	C15—H15	0.9300
C3—C8	1.422 (2)	C16—C17	1.390 (2)
C4—C5	1.370 (2)	C17—C18	1.389 (2)
C4—H4	0.9300	C18—C19	1.383 (2)
C5—C6	1.407 (2)	C18—H18	0.9300
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.370 (2)	C20—C21	1.504 (2)
C6—H6	0.9300	C21—H21A	0.9600
C7—C8	1.419 (2)	C21—H21B	0.9600
C7—H7	0.9300	C21—H21C	0.9600
C8—C9	1.418 (2)
C11—N1—N2	108.06 (13)	C11—C12—H12A	111.2
C20—N2—N1	123.49 (13)	C13—C12—H12A	111.2
C20—N2—C13	122.90 (14)	C11—C12—H12B	111.2
N1—N2—C13	113.44 (13)	C13—C12—H12B	111.2
C2—C1—C10	120.51 (16)	H12A—C12—H12B	109.1
C2—C1—H1	119.7	N2—C13—C14	111.22 (13)
C10—C1—H1	119.7	N2—C13—C12	101.19 (13)
C1—C2—C3	121.26 (16)	C14—C13—C12	114.05 (14)
C1—C2—H2	119.4	N2—C13—H13	110.0
C3—C2—H2	119.4	C14—C13—H13	110.0
C4—C3—C8	118.65 (15)	C12—C13—H13	110.0
C4—C3—C2	122.65 (16)	C15—C14—C19	119.04 (15)
C8—C3—C2	118.70 (15)	C15—C14—C13	120.14 (14)
C5—C4—C3	121.12 (17)	C19—C14—C13	120.82 (14)
C5—C4—H4	119.4	C14—C15—C16	120.68 (15)
C3—C4—H4	119.4	C14—C15—H15	119.7
C4—C5—C6	120.44 (16)	C16—C15—H15	119.7
C4—C5—H5	119.8	C15—C16—C17	120.00 (15)
C6—C5—H5	119.8	C15—C16—Cl2	119.11 (12)
C7—C6—C5	119.83 (16)	C17—C16—Cl2	120.87 (13)
C7—C6—H6	120.1	C18—C17—C16	119.75 (15)
C5—C6—H6	120.1	C18—C17—Cl1	119.24 (13)
C6—C7—C8	121.11 (16)	C16—C17—Cl1	121.01 (13)
C6—C7—H7	119.4	C19—C18—C17	120.04 (15)
C8—C7—H7	119.4	C19—C18—H18	120.0
C9—C8—C7	122.30 (16)	C17—C18—H18	120.0
C9—C8—C3	118.87 (15)	C18—C19—C14	120.47 (15)
C7—C8—C3	118.82 (15)	C18—C19—H19	119.8
C10—C9—C8	121.33 (15)	C14—C19—H19	119.8
C10—C9—H9	119.3	O1—C20—N2	119.98 (16)
C8—C9—H9	119.3	O1—C20—C21	123.45 (15)
C9—C10—C1	119.27 (15)	N2—C20—C21	116.56 (15)
C9—C10—C11	120.09 (15)	C20—C21—H21A	109.5
C1—C10—C11	120.64 (15)	C20—C21—H21B	109.5
N1—C11—C10	122.02 (15)	H21A—C21—H21B	109.5
N1—C11—C12	113.82 (14)	C20—C21—H21C	109.5
C10—C11—C12	124.16 (14)	H21A—C21—H21C	109.5
C11—C12—C13	102.71 (13)	H21B—C21—H21C	109.5
C11—N1—N2—C20	171.10 (14)	C10—C11—C12—C13	−174.36 (15)
C11—N1—N2—C13	−4.34 (17)	C20—N2—C13—C14	71.20 (19)
C10—C1—C2—C3	−0.4 (2)	N1—N2—C13—C14	−113.33 (15)
C1—C2—C3—C4	178.03 (16)	C20—N2—C13—C12	−167.31 (14)
C1—C2—C3—C8	−1.9 (2)	N1—N2—C13—C12	8.16 (16)
C8—C3—C4—C5	−0.5 (3)	C11—C12—C13—N2	−8.19 (14)
C2—C3—C4—C5	179.53 (16)	C11—C12—C13—C14	111.31 (15)
C3—C4—C5—C6	−0.7 (3)	N2—C13—C14—C15	−121.67 (16)
C4—C5—C6—C7	0.6 (3)	C12—C13—C14—C15	124.67 (16)
C5—C6—C7—C8	0.7 (3)	N2—C13—C14—C19	58.3 (2)
C6—C7—C8—C9	177.62 (15)	C12—C13—C14—C19	−55.3 (2)
C6—C7—C8—C3	−1.8 (2)	C19—C14—C15—C16	1.1 (2)
C4—C3—C8—C9	−177.73 (15)	C13—C14—C15—C16	−178.91 (14)
C2—C3—C8—C9	2.2 (2)	C14—C15—C16—C17	0.0 (2)
C4—C3—C8—C7	1.8 (2)	C14—C15—C16—Cl2	−178.49 (12)
C2—C3—C8—C7	−178.31 (15)	C15—C16—C17—C18	−1.0 (2)
C7—C8—C9—C10	−179.75 (15)	Cl2—C16—C17—C18	177.50 (13)
C3—C8—C9—C10	−0.3 (2)	C15—C16—C17—Cl1	179.93 (12)
C8—C9—C10—C1	−2.0 (2)	Cl2—C16—C17—Cl1	−1.6 (2)
C8—C9—C10—C11	178.74 (14)	C16—C17—C18—C19	0.8 (2)
C2—C1—C10—C9	2.3 (2)	Cl1—C17—C18—C19	179.94 (13)
C2—C1—C10—C11	−178.40 (15)	C17—C18—C19—C14	0.3 (3)
N2—N1—C11—C10	179.26 (13)	C15—C14—C19—C18	−1.2 (2)
N2—N1—C11—C12	−1.87 (18)	C13—C14—C19—C18	178.76 (14)
C9—C10—C11—N1	174.36 (14)	N1—N2—C20—O1	−177.25 (14)
C1—C10—C11—N1	−4.9 (2)	C13—N2—C20—O1	−2.2 (2)
C9—C10—C11—C12	−4.4 (2)	N1—N2—C20—C21	3.4 (2)
C1—C10—C11—C12	176.34 (14)	C13—N2—C20—C21	178.39 (14)
N1—C11—C12—C13	6.80 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.58	3.501 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.58	3.501 (2)	171

Symmetry code: (i) .