Ethyl 1-(4-tert-butyl­benz­yl)-3-(4-chloro­phen­yl)-1H-pyrazole-5-carboxyl­ate

Xia, Y.; Dong, W.-L.; Ding, X.-L.; Zhao, B.-X.

doi:10.1107/S1600536807028814

Ethyl 1-(4-tert-butylbenzyl)-3-(4-chlorophenyl)-1H-pyrazole-5-carboxylate

Y. Xia, W.-L. Dong, X.-L. Ding and B.-X. Zhao

In the title structure, C₂₃H₂₅ClN₂O₂, there are weak intramolecular C—H

N and C—H

O hydrogen bonds. There is a C=O

Cg interaction (Cg is the centroid of the pyrazole ring) and the distance between the centroids of the ring and the C=O bond is 3.017 (3) Å. The angle between the pyrazole ring and the chlorophenyl ring is 12.85 (13)°. The crystal packing is stabilized mainly by van der Waals forces.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028814/fb2052sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028814/fb2052Isup2.hkl Contains datablock I

CCDC reference: 654995

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.059
wR factor = 0.198
Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C20

Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          5
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C20    -   C21     ..       6.48 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C20    -   C23     ..       6.10 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C11    -   C12    ...       1.43 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Pyrazole nucleus has pronounced pharmacological applications in antibacterial (Finn et al., 2003), anti-anxiety (Wustrow et al., 1998) antipyretic, analgesic and anti-inflammatory drugs (Menozzi et al., 1997). Due to the easy preparation and rich biological activity the pyrazole framework represents an interesting template for combinatorial as well as for medicinal chemistry (Regan et al., 2002; Pevarello et al., 2004).

Related literature top

For related literature, see: Finn et al. (2003); Menozzi et al. (1997); Pevarello et al. (2004); Regan et al. (2002); Wustrow et al. (1998); Xia et al. (2007).

Experimental top

The title compound has been synthesized according to Xia et al. (2007): A mixture of ethyl 3-(4-chlorophenyl)-1H-pyrazole-5-carboxylate (0.01 mol), 1-tert-butyl-4-(chloromethyl)benzene (0.01 mol) and potassium carbonate (0.01 mol) in acetonitrile (20 ml) was heated to reflux for 5 h. The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate (30 ml). The organic phase was washed with brine and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, a solid was obtained with a yield equal to 75%. The solid was dissolved in ethyl acetate/petroleum ether (1:2 v/v). The crystals of the title compound were obtained by evaporation of the solution at room temperature over a period of one week.

Structure description top

For related literature, see: Finn et al. (2003); Menozzi et al. (1997); Pevarello et al. (2004); Regan et al. (2002); Wustrow et al. (1998); Xia et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The structure of the title molecule showing displacement ellipsoids drawn at the 50% probability level. The H atoms are depicted as spheres of arbitrary radii.

Ethyl 1-(4-tert-butylbenzyl)-3-(4-chlorophenyl)-1H-pyrazole-5- carboxylate top

Crystal data top

C₂₃H₂₅ClN₂O₂	Z = 2
M_r = 396.90	F(000) = 420
Triclinic, P1	D_x = 1.238 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9351 (1) Å	Cell parameters from 4831 reflections
b = 11.9430 (2) Å	θ = 2.7–24.0°
c = 12.6558 (2) Å	µ = 0.20 mm⁻¹
α = 70.432 (1)°	T = 293 K
β = 79.340 (1)°	Block, colourless
γ = 71.023 (1)°	0.44 × 0.35 × 0.32 mm
V = 1064.78 (3) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	4824 independent reflections
Radiation source: fine-focus sealed tube	3237 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (APEX2; Bruker, 2005)	h = −10→10
T_min = 0.841, T_max = 0.939	k = −14→15
15955 measured reflections	l = −16→16

Refinement top

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)] = 0.059	Hydrogen site location: difference Fourier map
wR(F²) = 0.198	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.098P)² + 0.2242P] where P = (F_o² + 2F_c²)/3
4824 reflections	(Δ/σ)_max < 0.001
257 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³
96 constraints

Crystal data top

C₂₃H₂₅ClN₂O₂	γ = 71.023 (1)°
M_r = 396.90	V = 1064.78 (3) Å³
Triclinic, P1	Z = 2
a = 7.9351 (1) Å	Mo Kα radiation
b = 11.9430 (2) Å	µ = 0.20 mm⁻¹
c = 12.6558 (2) Å	T = 293 K
α = 70.432 (1)°	0.44 × 0.35 × 0.32 mm
β = 79.340 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4824 independent reflections
Absorption correction: multi-scan (APEX2; Bruker, 2005)	3237 reflections with I > 2σ(I)
T_min = 0.841, T_max = 0.939	R_int = 0.021
15955 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.198	H-atom parameters constrained
S = 1.07	Δρ_max = 0.39 e Å⁻³
4824 reflections	Δρ_min = −0.29 e Å⁻³
257 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
C1	0.8400 (3)	0.1190 (3)	−0.2742 (2)	0.0733 (6)
C2	0.9389 (4)	0.0694 (2)	−0.1824 (2)	0.0757 (6)
H2	1.0090	−0.0127	−0.1645	0.091*
C3	0.9325 (3)	0.1431 (2)	−0.1173 (2)	0.0693 (6)
H3	1.0011	0.1101	−0.0560	0.083*
C4	0.8268 (3)	0.26521 (19)	−0.14063 (17)	0.0581 (5)
C5	0.7294 (3)	0.3124 (2)	−0.2340 (2)	0.0731 (6)
H5	0.6578	0.3941	−0.2520	0.088*
C6	0.7373 (3)	0.2398 (3)	−0.3006 (2)	0.0818 (7)
H6	0.6726	0.2731	−0.3637	0.098*
C7	0.8169 (3)	0.34127 (18)	−0.06786 (17)	0.0570 (5)
C8	0.7448 (3)	0.46923 (19)	−0.08634 (18)	0.0615 (5)
H8	0.6916	0.5274	−0.1497	0.074*
C9	0.7694 (3)	0.4904 (2)	0.00879 (18)	0.0613 (5)
C10	0.7236 (3)	0.6070 (2)	0.0386 (2)	0.0695 (6)
C11	0.6048 (5)	0.8229 (3)	−0.0261 (3)	0.1026 (10)
H11A	0.5388	0.8196	0.0469	0.123*
H11B	0.7125	0.8451	−0.0270	0.123*
C12	0.4977 (6)	0.9139 (3)	−0.1125 (4)	0.1328 (14)
H12A	0.5684	0.9241	−0.1835	0.199*
H12B	0.4550	0.9915	−0.0954	0.199*
H12C	0.3978	0.8873	−0.1165	0.199*
C13	0.8939 (3)	0.3461 (2)	0.19562 (19)	0.0672 (6)
H13A	0.9302	0.4120	0.2050	0.081*
H13B	0.9930	0.2710	0.2119	0.081*
C14	0.7343 (3)	0.32618 (18)	0.27736 (17)	0.0570 (5)
C15	0.6616 (4)	0.2337 (2)	0.2844 (2)	0.0899 (9)
H15	0.7122	0.1827	0.2384	0.108*
C16	0.5160 (4)	0.2151 (2)	0.3581 (2)	0.0894 (9)
H16	0.4705	0.1517	0.3603	0.107*
C17	0.4343 (3)	0.28730 (17)	0.42923 (16)	0.0550 (5)
C18	0.5076 (3)	0.37929 (19)	0.42172 (18)	0.0625 (5)
H18	0.4575	0.4300	0.4681	0.075*
C19	0.6542 (3)	0.3991 (2)	0.34712 (19)	0.0649 (5)
H19	0.6991	0.4630	0.3442	0.078*
C20	0.2712 (3)	0.2639 (2)	0.50910 (19)	0.0656 (5)
C21	0.3156 (5)	0.1280 (3)	0.5793 (3)	0.1250 (13)
H21A	0.3416	0.0766	0.5306	0.188*
H21B	0.2153	0.1137	0.6319	0.188*
H21C	0.4179	0.1081	0.6196	0.188*
C22	0.2155 (5)	0.3413 (4)	0.5903 (3)	0.1224 (13)
H22A	0.3128	0.3224	0.6344	0.184*
H22B	0.1139	0.3227	0.6391	0.184*
H22C	0.1846	0.4277	0.5486	0.184*
C23	0.1175 (4)	0.2919 (4)	0.4406 (3)	0.1135 (11)
H23A	0.0880	0.3775	0.3967	0.170*
H23B	0.0155	0.2754	0.4902	0.170*
H23C	0.1515	0.2405	0.3915	0.170*
Cl1	0.85235 (12)	0.02856 (9)	−0.35989 (7)	0.1085 (3)
N1	0.8817 (2)	0.28689 (16)	0.03336 (14)	0.0599 (4)
N2	0.8527 (2)	0.37855 (16)	0.07868 (14)	0.0608 (4)
O1	0.6522 (3)	0.70272 (15)	−0.04525 (16)	0.0877 (5)
O2	0.7491 (3)	0.61609 (18)	0.12555 (17)	0.0940 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0674 (14)	0.0919 (16)	0.0694 (14)	−0.0270 (12)	0.0013 (11)	−0.0345 (13)
C2	0.0834 (16)	0.0710 (14)	0.0694 (15)	−0.0120 (11)	−0.0080 (12)	−0.0254 (11)
C3	0.0754 (14)	0.0671 (12)	0.0588 (12)	−0.0090 (10)	−0.0143 (10)	−0.0166 (10)
C4	0.0538 (11)	0.0643 (11)	0.0507 (11)	−0.0168 (9)	−0.0002 (8)	−0.0125 (9)
C5	0.0651 (13)	0.0763 (14)	0.0687 (14)	−0.0062 (11)	−0.0145 (11)	−0.0185 (11)
C6	0.0742 (15)	0.1045 (19)	0.0702 (15)	−0.0202 (14)	−0.0202 (12)	−0.0279 (14)
C7	0.0513 (10)	0.0613 (11)	0.0526 (11)	−0.0147 (8)	0.0003 (8)	−0.0131 (9)
C8	0.0615 (12)	0.0595 (11)	0.0563 (12)	−0.0159 (9)	−0.0030 (9)	−0.0103 (9)
C9	0.0567 (11)	0.0627 (11)	0.0608 (12)	−0.0207 (9)	0.0039 (9)	−0.0147 (9)
C10	0.0684 (14)	0.0683 (13)	0.0700 (15)	−0.0245 (10)	0.0044 (11)	−0.0187 (11)
C11	0.128 (3)	0.0693 (16)	0.114 (2)	−0.0187 (16)	−0.021 (2)	−0.0345 (16)
C12	0.190 (4)	0.0763 (19)	0.129 (3)	−0.015 (2)	−0.047 (3)	−0.031 (2)
C13	0.0619 (13)	0.0826 (14)	0.0589 (12)	−0.0215 (10)	−0.0065 (10)	−0.0215 (11)
C14	0.0607 (11)	0.0599 (11)	0.0504 (10)	−0.0151 (9)	−0.0077 (8)	−0.0167 (8)
C15	0.110 (2)	0.0854 (16)	0.0934 (19)	−0.0455 (15)	0.0363 (16)	−0.0576 (15)
C16	0.109 (2)	0.0850 (16)	0.0991 (19)	−0.0534 (15)	0.0329 (16)	−0.0563 (15)
C17	0.0585 (11)	0.0550 (10)	0.0524 (11)	−0.0129 (8)	−0.0085 (8)	−0.0182 (8)
C18	0.0717 (13)	0.0629 (11)	0.0592 (12)	−0.0157 (10)	−0.0041 (10)	−0.0300 (10)
C19	0.0761 (14)	0.0671 (12)	0.0645 (13)	−0.0285 (10)	−0.0059 (10)	−0.0281 (10)
C20	0.0584 (12)	0.0759 (13)	0.0676 (13)	−0.0196 (10)	−0.0026 (10)	−0.0285 (11)
C21	0.102 (2)	0.116 (2)	0.112 (3)	−0.0306 (19)	0.0248 (19)	0.005 (2)
C22	0.108 (2)	0.179 (4)	0.122 (3)	−0.072 (2)	0.043 (2)	−0.095 (3)
C23	0.0793 (19)	0.162 (3)	0.105 (2)	−0.0364 (19)	−0.0122 (17)	−0.042 (2)
Cl1	0.1159 (6)	0.1348 (7)	0.1051 (6)	−0.0420 (5)	−0.0072 (5)	−0.0687 (5)
N1	0.0590 (10)	0.0627 (10)	0.0534 (10)	−0.0146 (7)	−0.0020 (7)	−0.0155 (8)
N2	0.0589 (10)	0.0675 (10)	0.0535 (10)	−0.0187 (8)	−0.0008 (7)	−0.0160 (8)
O1	0.1104 (14)	0.0619 (9)	0.0899 (13)	−0.0174 (9)	−0.0180 (10)	−0.0233 (9)
O2	0.1237 (16)	0.0853 (12)	0.0800 (12)	−0.0315 (11)	−0.0052 (11)	−0.0333 (10)

Geometric parameters (Å, º) top

C1—C6	1.367 (4)	C13—C14	1.509 (3)
C1—C2	1.376 (4)	C13—H13A	0.9700
C1—Cl1	1.741 (3)	C13—H13B	0.9700
C2—C3	1.377 (3)	C14—C19	1.375 (3)
C2—H2	0.9300	C14—C15	1.375 (3)
C3—C4	1.388 (3)	C15—C16	1.372 (4)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.386 (3)	C16—C17	1.384 (3)
C4—C7	1.472 (3)	C16—H16	0.9300
C5—C6	1.378 (4)	C17—C18	1.371 (3)
C5—H5	0.9300	C17—C20	1.529 (3)
C6—H6	0.9300	C18—C19	1.386 (3)
C7—N1	1.340 (3)	C18—H18	0.9300
C7—C8	1.400 (3)	C19—H19	0.9300
C8—C9	1.369 (3)	C20—C23	1.510 (4)
C8—H8	0.9300	C20—C22	1.519 (4)
C9—N2	1.361 (3)	C20—C21	1.525 (4)
C9—C10	1.479 (3)	C21—H21A	0.9600
C10—O2	1.200 (3)	C21—H21B	0.9600
C10—O1	1.320 (3)	C21—H21C	0.9600
C11—C12	1.430 (5)	C22—H22A	0.9600
C11—O1	1.452 (3)	C22—H22B	0.9600
C11—H11A	0.9700	C22—H22C	0.9600
C11—H11B	0.9700	C23—H23A	0.9600
C12—H12A	0.9600	C23—H23B	0.9600
C12—H12B	0.9600	C23—H23C	0.9600
C12—H12C	0.9600	N1—N2	1.337 (2)
C13—N2	1.470 (3)

C6—C1—C2	120.5 (2)	C19—C14—C15	116.9 (2)
C6—C1—Cl1	120.0 (2)	C19—C14—C13	122.20 (19)
C2—C1—Cl1	119.5 (2)	C15—C14—C13	120.86 (19)
C1—C2—C3	119.0 (2)	C16—C15—C14	121.4 (2)
C1—C2—H2	120.5	C16—C15—H15	119.3
C3—C2—H2	120.5	C14—C15—H15	119.3
C2—C3—C4	121.9 (2)	C15—C16—C17	122.4 (2)
C2—C3—H3	119.1	C15—C16—H16	118.8
C4—C3—H3	119.1	C17—C16—H16	118.8
C5—C4—C3	117.6 (2)	C18—C17—C16	115.9 (2)
C5—C4—C7	121.28 (19)	C18—C17—C20	123.57 (18)
C3—C4—C7	121.12 (19)	C16—C17—C20	120.53 (19)
C6—C5—C4	120.8 (2)	C17—C18—C19	122.06 (18)
C6—C5—H5	119.6	C17—C18—H18	119.0
C4—C5—H5	119.6	C19—C18—H18	119.0
C1—C6—C5	120.2 (2)	C14—C19—C18	121.34 (19)
C1—C6—H6	119.9	C14—C19—H19	119.3
C5—C6—H6	119.9	C18—C19—H19	119.3
N1—C7—C8	110.64 (19)	C23—C20—C22	109.6 (2)
N1—C7—C4	119.66 (18)	C23—C20—C21	108.9 (3)
C8—C7—C4	129.70 (19)	C22—C20—C21	107.4 (3)
C9—C8—C7	105.23 (19)	C23—C20—C17	109.0 (2)
C9—C8—H8	127.4	C22—C20—C17	112.5 (2)
C7—C8—H8	127.4	C21—C20—C17	109.21 (19)
N2—C9—C8	106.89 (19)	C20—C21—H21A	109.5
N2—C9—C10	122.4 (2)	C20—C21—H21B	109.5
C8—C9—C10	130.7 (2)	H21A—C21—H21B	109.5
O2—C10—O1	123.6 (2)	C20—C21—H21C	109.5
O2—C10—C9	125.8 (2)	H21A—C21—H21C	109.5
O1—C10—C9	110.6 (2)	H21B—C21—H21C	109.5
C12—C11—O1	109.3 (3)	C20—C22—H22A	109.5
C12—C11—H11A	109.8	C20—C22—H22B	109.5
O1—C11—H11A	109.8	H22A—C22—H22B	109.5
C12—C11—H11B	109.8	C20—C22—H22C	109.5
O1—C11—H11B	109.8	H22A—C22—H22C	109.5
H11A—C11—H11B	108.3	H22B—C22—H22C	109.5
C11—C12—H12A	109.5	C20—C23—H23A	109.5
C11—C12—H12B	109.5	C20—C23—H23B	109.5
H12A—C12—H12B	109.5	H23A—C23—H23B	109.5
C11—C12—H12C	109.5	C20—C23—H23C	109.5
H12A—C12—H12C	109.5	H23A—C23—H23C	109.5
H12B—C12—H12C	109.5	H23B—C23—H23C	109.5
N2—C13—C14	111.33 (17)	N2—N1—C7	105.59 (16)
N2—C13—H13A	109.4	N1—N2—C9	111.65 (17)
C14—C13—H13A	109.4	N1—N2—C13	118.38 (17)
N2—C13—H13B	109.4	C9—N2—C13	129.60 (19)
C14—C13—H13B	109.4	C10—O1—C11	115.5 (2)
H13A—C13—H13B	108.0

C6—C1—C2—C3	0.2 (4)	C15—C16—C17—C18	0.1 (4)
Cl1—C1—C2—C3	177.90 (19)	C15—C16—C17—C20	179.4 (3)
C1—C2—C3—C4	1.2 (4)	C16—C17—C18—C19	0.2 (3)
C2—C3—C4—C5	−1.4 (4)	C20—C17—C18—C19	−179.0 (2)
C2—C3—C4—C7	177.9 (2)	C15—C14—C19—C18	0.5 (3)
C3—C4—C5—C6	0.3 (4)	C13—C14—C19—C18	−180.0 (2)
C7—C4—C5—C6	−178.9 (2)	C17—C18—C19—C14	−0.6 (3)
C2—C1—C6—C5	−1.2 (4)	C18—C17—C20—C23	113.9 (3)
Cl1—C1—C6—C5	−178.9 (2)	C16—C17—C20—C23	−65.4 (3)
C4—C5—C6—C1	1.0 (4)	C18—C17—C20—C22	−8.0 (3)
C5—C4—C7—N1	166.2 (2)	C16—C17—C20—C22	172.7 (3)
C3—C4—C7—N1	−13.0 (3)	C18—C17—C20—C21	−127.2 (3)
C5—C4—C7—C8	−12.9 (3)	C16—C17—C20—C21	53.5 (3)
C3—C4—C7—C8	167.9 (2)	C8—C7—N1—N2	−0.4 (2)
N1—C7—C8—C9	0.2 (2)	C4—C7—N1—N2	−179.63 (17)
C4—C7—C8—C9	179.34 (19)	C7—N1—N2—C9	0.4 (2)
C7—C8—C9—N2	0.1 (2)	C7—N1—N2—C13	174.07 (17)
C7—C8—C9—C10	179.0 (2)	C8—C9—N2—N1	−0.3 (2)
N2—C9—C10—O2	−2.0 (4)	C10—C9—N2—N1	−179.39 (18)
C8—C9—C10—O2	179.1 (2)	C8—C9—N2—C13	−173.1 (2)
N2—C9—C10—O1	176.88 (19)	C10—C9—N2—C13	7.9 (3)
C8—C9—C10—O1	−1.9 (3)	C14—C13—N2—N1	−89.9 (2)
N2—C13—C14—C19	−117.6 (2)	C14—C13—N2—C9	82.4 (3)
N2—C13—C14—C15	61.9 (3)	O2—C10—O1—C11	0.1 (4)
C19—C14—C15—C16	−0.2 (4)	C9—C10—O1—C11	−178.9 (2)
C13—C14—C15—C16	−179.7 (3)	C12—C11—O1—C10	−168.5 (3)
C14—C15—C16—C17	−0.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1	0.93	2.56	2.865 (3)	100
C13—H13A···O2	0.97	2.37	2.925 (3)	116

Experimental details

Crystal data
Chemical formula	C₂₃H₂₅ClN₂O₂
M_r	396.90
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.9351 (1), 11.9430 (2), 12.6558 (2)
α, β, γ (°)	70.432 (1), 79.340 (1), 71.023 (1)
V (Å³)	1064.78 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.44 × 0.35 × 0.32

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (APEX2; Bruker, 2005)
T_min, T_max	0.841, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	15955, 4824, 3237
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.198, 1.07
No. of reflections	4824
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.29

Computer programs: APEX2 (Bruker, 2005), APEX2, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), WinGX (Farrugia, 1999).