Ethyl 3-(4-chloro­phen­yl)-1-(2-oxo-2-phenyl­eth­yl)-1H-pyrazole-5-carboxyl­ate

Zheng, L.-W.; Liu, Y.-R.; Zhao, B.-X.

doi:10.1107/S1600536811025918

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages o1910-o1911

doi:10.1107/S1600536811025918

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Ethyl 3-(4-chlorophenyl)-1-(2-oxo-2-phenylethyl)-1H-pyrazole-5-carboxylate

Liang-Wen Zheng,^a Yin-Rui Liu ^a and Bao-Xiang Zhao ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
^*Correspondence e-mail: bxzhao@sdu.edu.cn

(Received 17 June 2011; accepted 30 June 2011; online 6 July 2011)

In the title compound, C₂₀H₁₇ClN₂O₃, the dihedral angles between the pyrazole ring and the substituted and unsubstituted benzene rings are 3.64 (13) and 81.15 (17)°, respectively. Molecules are connected via three pairs of weak hydrogen bonds into a centrosymmetric dimer. The crystal structure is stabilized by intermolecular C—H⋯O and C—H⋯π interactions.

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_r = 368.81
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.123
S = 1.04
3216 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1; (iii) -x+2, -y+2, -z+1.

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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811025918/vm2105sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811025918/vm2105Isup3.cml

checkCIF report

Comment top

Pyrazoles form an important class of analogues, which occupy a special role in natural and synthetic compounds (Kosuge et al., 1962; Ganesan et al., 1996). Pyrazole derivatives have been the subject of much research because of their importance in various applications and their widespread potential biological and pharmacological activities, such as antitumor (Farag et al., 2010), antimicrobial (Boschi et al., 2011), antiglaucoma (Kasımoğullan et al., 2010), anti-angiogenic (Christodoulou et al., 2010), antinociceptive (Scanio et al., 2010) and anti-inflammatory (Da Sliva et al., 2010).

One chlorine substituted benzene group, an ethyl carboxylate moiety and a 2-oxo-2-phenylethyl moiety are bonded to core pyrazole ring in the title molecule at C6, C4, N1 as showed in Fig. 1. Torsion angle N1—C4—C3—O1 of 175.6 (2)° illustrates that O1 in the ethyl carboxylate moiety adopts a antiperiplanar conformation with respect to the N1 atom of the pyrazole ring. The pyrazole core structure and the chlorine substituted benzene are approximately coplanar with a dihedral angle of 3.65 (7)°. A S(6) pseudo-ring closed by a C13—H13A···O2 intramolecular interaction is observed. The carbonyl O1 atom of the ethyl formate moiety interacts with the pyrazole H atom of the adjacent molecules through a pair of linear C5—H5···O1 hydrogen bonds to form a ten-membered ring motif. Moreover, some other C–H···O and C—H···π interactions (Table 1) may supply further coulombic stabilization and take part in formation of the three-dimensional structure.

Related literature top

For applications of pyrazoles, see: Kosuge & Kamiya (1962); Ganesan et al. (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 top

To dried acetonitrile (50 ml), ethyl 3-(4-chlorophenyl)-1H-pyrazole-5-carboxylate (2.50 g, 10 mmol), 2-bromo-1-phenylethanone (2.00 g, 10 mmol) and potassium carbonate (2.76 g, 20 mmol) were added. The mixture was heated to reflux for 1 h, until TLC indicated the end of reaction. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography using ethyl acetate/petroleum ether (v/v = 1:4) as eluant to afford compound ethyl 3-(4-chlorophenyl)-1-(2-oxo-2-phenylethyl)-1H-pyrazole-5-carboxylate (I) in 70% yield. Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in ethyl acetate at room temperature for 7 days.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. ORTEP view of compound (I), showing 25% probability displacement ellipsoids.
	Fig. 2. Packing diagram of compound (I). Short contacts and C—H···π are shown as dashed lines.

Ethyl 3-(4-chlorophenyl)-1-(2-oxo-2-phenylethyl)-1H-pyrazole-5-carboxylate top

Crystal data top

C₂₀H₁₇ClN₂O₃	Z = 2
M_r = 368.81	F(000) = 384
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0468P)² + 0.1653P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3216 reflections	Δρ_max = 0.17 e Å⁻³
237 parameters	Δρ_min = −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)

Crystal data top

C₂₀H₁₇ClN₂O₃	γ = 113.849 (2)°
M_r = 368.81	V = 916.44 (19) Å³
Triclinic, P1	Z = 2
a = 7.7238 (10) Å	Mo Kα radiation
b = 8.382 (1) Å	µ = 0.23 mm⁻¹
c = 15.8143 (18) Å	T = 296 K
α = 98.667 (2)°	0.12 × 0.10 × 0.06 mm
β = 93.828 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3216 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2079 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.986	R_int = 0.018
4894 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.04	Δρ_max = 0.17 e Å⁻³
3216 reflections	Δρ_min = −0.18 e Å⁻³
237 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇ClN₂O₃
M_r	368.81
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.7238 (10), 8.382 (1), 15.8143 (18)
α, β, γ (°)	98.667 (2), 93.828 (2), 113.849 (2)
V (Å³)	916.44 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.973, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	4894, 3216, 2079
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.123, 1.04
No. of reflections	3216
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+2, −y+2, −z+1.

Acknowledgements

Thanks are due to the Science and Technology Developmental Project of Shandong Province (2008 GG10002034) and the National Natural Science Foundation of China (90813022) for financial support.

References

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Volume 67| Part 8| August 2011| Pages o1910-o1911

doi:10.1107/S1600536811025918

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