5-Benzoyl-N,4-diphenyl-4,5-dihydro-1H-pyrazole-3-carboxamide

He, L.

doi:10.1107/S1600536809034035

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2281

doi:10.1107/S1600536809034035

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5-Benzoyl-N,4-diphenyl-4,5-dihydro-1H-pyrazole-3-carboxamide

Long He ^a ^*

^aCollege of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: helongcwnu@yahoo.com.cn

(Received 28 July 2009; accepted 25 August 2009; online 29 August 2009)

The title compound, C₂₃H₁₉N₃O₂, was synthesized by the 1,3-dipolar cycloaddition reaction of N-phenyl-α-diazoacetamide and chalcone. In the molecule, the pyrazoline ring assumes an envelope conformation. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the 1,3-dipolar cycloaddition reaction, see: Grigg (1995 ). For applications of pyrazoline and its derivatives, see: Dhal et al. (1975 ); Lombardino & Ottemes (1981 ); Parmar et al. (1974 ); Rawal et al. (1963 ).

Experimental

Crystal data

C₂₃H₁₉N₃O₂
M_r = 369.41
Monoclinic, P 2₁ /n
a = 5.809 (3) Å
b = 10.717 (5) Å
c = 29.428 (7) Å
β = 92.753 (5)°
V = 1829.9 (13) Å³
Z = 4
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 293 K
0.36 × 0.24 × 0.20 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.786, T_max = 0.873
27720 measured reflections
2929 independent reflections
2390 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.066
S = 1.00
2929 reflections
261 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.93	2.56	3.468 (4)	166
C8—H8⋯O1ⁱ	0.98	2.50	3.475 (4)	173
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034035/xu2571sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034035/xu2571Isup2.hkl

checkCIF report

Comment top

The 1,3-dipolar cycloaddition reaction is one of the most efficient and widely used methods for the synthesis of nitrogen-containing five-membered heterocycles (Grigg, 1995). As important and useful five-membered heterocyclic compounds, pyrazoline and its derivatives were found to possess antifungal (Dhal et al., 1975), immunosuppressive (Lombardino et al.,1981), psychoanaleptic (Parmar et al. 1974), and antiviral (Rawal et al. 1963) activities. We report herein the crystal structure of the title compound.

The molecular structure of (I) is shown in Fig. 1. In the molecule the dihydropyrazole ring assumes an envelope conformation. The C6-benene ring and C15-benene ring make dihedral angles of 82.08 (7)° and 84.78 (7)° with respect to the C23-benene ring. The dihedral angle between the C6-benzene and C15-benene ring is 71.39 (7)°. Intermolecular weak C—H···O hydrogen bonding is present in the crystal structure (Table 1).

Related literature top

For the 1,3-dipolar cycloaddition reaction, see: Grigg et al. (1995). For applications of pyrazoline and its derivatives, see: Dhal et al. (1975); Lombardino et al. (1981); Parmar et al. (1974); Rawal et al. (1963).

Experimental top

N-Phenyl-alfa-diazoacetamide (0.035 g, 0.2 mmol) and chalcone (0.042 g, 0.2 mmol) and 1,4-diaza-bicyclo[2.2.2]octan (0.02 g, 0.2 mmol) were dissolved in toluene (2 mL). The solution was warmed to 323 K, and the solution was stirred for 2 h. After removal of solvent under reduced pressure, the residue was purified through column chromatography on silica gel to give target compound. Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from ethanol.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

5-Benzoyl-N,4-diphenyl-4,5-dihydro-1H-pyrazole-3-carboxamide top

Crystal data top

C₂₃H₁₉N₃O₂	F(000) = 776
M_r = 369.41	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 11458 reflections
a = 5.809 (3) Å	θ = 3.0–62.7°
b = 10.717 (5) Å	µ = 0.70 mm⁻¹
c = 29.428 (7) Å	T = 293 K
β = 92.753 (5)°	Block, colorless
V = 1829.9 (13) Å³	0.36 × 0.24 × 0.20 mm
Z = 4

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	2929 independent reflections
Radiation source: Ultra (Cu) X-ray Source	2390 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 15.9149 pixels mm^-1	θ_max = 62.7°, θ_min = 3.0°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −12→12
T_min = 0.786, T_max = 0.873	l = −33→33
27720 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0012P)² + 1.114P] where P = (F_o² + 2F_c²)/3
2929 reflections	(Δ/σ)_max = 0.001
261 parameters	Δρ_max = 0.16 e Å⁻³
2 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₃H₁₉N₃O₂	V = 1829.9 (13) Å³
M_r = 369.41	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 5.809 (3) Å	µ = 0.70 mm⁻¹
b = 10.717 (5) Å	T = 293 K
c = 29.428 (7) Å	0.36 × 0.24 × 0.20 mm
β = 92.753 (5)°

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	2929 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2390 reflections with I > 2σ(I)
T_min = 0.786, T_max = 0.873	R_int = 0.031
27720 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	2 restraints
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.16 e Å⁻³
2929 reflections	Δρ_min = −0.15 e Å⁻³
261 parameters

Special details top

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 > 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
O2	0.5592 (2)	0.44501 (12)	0.90247 (4)	0.0526 (3)
N1	0.9367 (3)	0.50816 (14)	0.90580 (5)	0.0445 (4)
N2	1.0040 (2)	0.35676 (13)	0.83258 (4)	0.0414 (3)
O1	0.7319 (2)	0.41770 (11)	0.74559 (4)	0.0547 (3)
C4	0.4434 (3)	0.27270 (15)	0.72408 (5)	0.0351 (4)
C18	0.9446 (3)	0.59203 (15)	0.94313 (5)	0.0397 (4)
N3	1.0026 (2)	0.26477 (14)	0.79899 (5)	0.0425 (4)
C9	0.6458 (3)	0.25420 (14)	0.83326 (5)	0.0325 (3)
H9	0.4906	0.2885	0.8277	0.039*
C10	0.6433 (3)	0.14494 (14)	0.86613 (5)	0.0336 (4)
C8	0.7622 (3)	0.22873 (15)	0.78770 (5)	0.0350 (4)
H8	0.7501	0.1407	0.7789	0.042*
C17	0.7560 (3)	0.43921 (15)	0.88959 (5)	0.0388 (4)
C3	0.3815 (3)	0.14837 (16)	0.71876 (6)	0.0474 (4)
H3	0.4705	0.0863	0.7330	0.057*
C16	0.8112 (3)	0.35355 (14)	0.85194 (5)	0.0357 (4)
C7	0.6522 (3)	0.31416 (15)	0.75101 (5)	0.0370 (4)
C15	0.8272 (3)	0.06224 (16)	0.87032 (6)	0.0436 (4)
H15	0.9505	0.0706	0.8515	0.052*
C23	0.7730 (3)	0.59886 (16)	0.97404 (6)	0.0461 (4)
H23	0.6404	0.5508	0.9699	0.055*
C14	0.8282 (3)	−0.03262 (17)	0.90231 (7)	0.0540 (5)
H14	0.9514	−0.0880	0.9047	0.065*
C20	1.1647 (4)	0.74369 (18)	0.98647 (6)	0.0554 (5)
H20	1.2964	0.7925	0.9906	0.067*
C21	0.9955 (4)	0.75011 (18)	1.01741 (6)	0.0540 (5)
H21	1.0125	0.8029	1.0424	0.065*
C6	0.1133 (3)	0.3315 (2)	0.67649 (6)	0.0572 (5)
H6	0.0228	0.3932	0.6624	0.069*
C11	0.4622 (3)	0.13108 (16)	0.89459 (6)	0.0447 (4)
H11	0.3377	0.1856	0.8921	0.054*
C5	0.3068 (3)	0.36379 (17)	0.70260 (6)	0.0471 (4)
H5	0.3467	0.4474	0.7059	0.056*
C19	1.1410 (3)	0.66527 (17)	0.94917 (6)	0.0493 (5)
H19	1.2560	0.6616	0.9283	0.059*
C22	0.8001 (3)	0.67782 (18)	1.01115 (6)	0.0524 (5)
H22	0.6854	0.6821	1.0321	0.063*
C2	0.1871 (3)	0.11665 (19)	0.69215 (7)	0.0597 (5)
H2	0.1468	0.0332	0.6884	0.072*
C13	0.6475 (4)	−0.04517 (19)	0.93055 (7)	0.0585 (5)
H13	0.6489	−0.1086	0.9521	0.070*
C1	0.0535 (3)	0.2077 (2)	0.67127 (7)	0.0588 (5)
H1	−0.0773	0.1858	0.6536	0.071*
C12	0.4647 (4)	0.03661 (19)	0.92674 (6)	0.0569 (5)
H12	0.3426	0.0284	0.9458	0.068*
H4	1.072 (2)	0.4961 (18)	0.8932 (6)	0.055 (6)*
H18	1.081 (3)	0.2914 (16)	0.7754 (5)	0.052 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0470 (8)	0.0564 (8)	0.0546 (8)	−0.0019 (6)	0.0049 (6)	−0.0169 (6)
N1	0.0482 (10)	0.0448 (9)	0.0408 (8)	−0.0093 (7)	0.0058 (7)	−0.0109 (7)
N2	0.0417 (9)	0.0438 (8)	0.0385 (8)	−0.0059 (7)	−0.0007 (7)	−0.0024 (6)
O1	0.0634 (9)	0.0401 (7)	0.0600 (8)	−0.0133 (6)	−0.0054 (6)	0.0091 (6)
C4	0.0389 (9)	0.0372 (9)	0.0296 (8)	0.0019 (7)	0.0045 (7)	0.0002 (7)
C18	0.0509 (11)	0.0331 (9)	0.0345 (9)	−0.0008 (8)	−0.0038 (8)	−0.0024 (7)
N3	0.0363 (8)	0.0521 (9)	0.0394 (8)	−0.0017 (7)	0.0055 (7)	−0.0060 (7)
C9	0.0314 (9)	0.0322 (8)	0.0340 (8)	0.0003 (7)	0.0005 (7)	−0.0013 (7)
C10	0.0373 (9)	0.0311 (8)	0.0320 (8)	−0.0046 (7)	−0.0033 (7)	−0.0025 (7)
C8	0.0362 (9)	0.0339 (9)	0.0347 (8)	−0.0004 (7)	0.0007 (7)	−0.0035 (7)
C17	0.0495 (11)	0.0323 (9)	0.0344 (9)	−0.0019 (8)	−0.0009 (8)	0.0007 (7)
C3	0.0482 (11)	0.0372 (10)	0.0557 (11)	0.0059 (8)	−0.0086 (9)	−0.0029 (8)
C16	0.0402 (10)	0.0318 (9)	0.0348 (9)	−0.0027 (7)	0.0000 (7)	0.0003 (7)
C7	0.0424 (10)	0.0350 (9)	0.0340 (9)	0.0003 (8)	0.0068 (7)	−0.0022 (7)
C15	0.0411 (10)	0.0415 (10)	0.0479 (10)	−0.0001 (8)	−0.0021 (8)	0.0024 (8)
C23	0.0501 (11)	0.0460 (10)	0.0420 (10)	−0.0053 (9)	0.0005 (8)	−0.0055 (8)
C14	0.0543 (12)	0.0438 (11)	0.0621 (12)	0.0029 (9)	−0.0148 (10)	0.0086 (9)
C20	0.0600 (13)	0.0489 (11)	0.0562 (12)	−0.0122 (10)	−0.0095 (10)	−0.0089 (9)
C21	0.0704 (14)	0.0464 (11)	0.0441 (10)	0.0033 (10)	−0.0085 (10)	−0.0125 (9)
C6	0.0568 (13)	0.0617 (13)	0.0520 (12)	0.0123 (10)	−0.0089 (10)	0.0111 (10)
C11	0.0454 (11)	0.0433 (10)	0.0456 (10)	−0.0008 (8)	0.0049 (8)	0.0025 (8)
C5	0.0542 (12)	0.0412 (10)	0.0457 (10)	0.0020 (9)	0.0014 (9)	0.0092 (8)
C19	0.0525 (12)	0.0487 (11)	0.0467 (10)	−0.0082 (9)	0.0028 (9)	−0.0064 (9)
C22	0.0597 (13)	0.0557 (12)	0.0419 (10)	0.0039 (10)	0.0030 (9)	−0.0082 (9)
C2	0.0556 (13)	0.0461 (11)	0.0758 (14)	0.0002 (10)	−0.0145 (11)	−0.0150 (10)
C13	0.0739 (15)	0.0499 (12)	0.0503 (11)	−0.0119 (11)	−0.0105 (10)	0.0170 (9)
C1	0.0491 (12)	0.0708 (14)	0.0549 (12)	0.0069 (10)	−0.0138 (9)	−0.0100 (10)
C12	0.0642 (14)	0.0582 (12)	0.0490 (11)	−0.0101 (11)	0.0111 (10)	0.0104 (10)

Geometric parameters (Å, º) top

O2—C17	1.223 (2)	C15—C14	1.385 (2)
N1—C17	1.352 (2)	C15—H15	0.9300
N1—C18	1.418 (2)	C23—C22	1.385 (2)
N1—H4	0.895 (9)	C23—H23	0.9300
N2—C16	1.281 (2)	C14—C13	1.376 (3)
N2—N3	1.3959 (19)	C14—H14	0.9300
O1—C7	1.216 (2)	C20—C21	1.373 (3)
C4—C3	1.387 (2)	C20—C19	1.384 (2)
C4—C5	1.391 (2)	C20—H20	0.9300
C4—C7	1.485 (2)	C21—C22	1.379 (3)
C18—C23	1.383 (2)	C21—H21	0.9300
C18—C19	1.390 (2)	C6—C5	1.375 (3)
N3—C8	1.471 (2)	C6—C1	1.379 (3)
N3—H18	0.896 (9)	C6—H6	0.9300
C9—C10	1.519 (2)	C11—C12	1.385 (2)
C9—C16	1.519 (2)	C11—H11	0.9300
C9—C8	1.555 (2)	C5—H5	0.9300
C9—H9	0.9800	C19—H19	0.9300
C10—C11	1.384 (2)	C22—H22	0.9300
C10—C15	1.389 (2)	C2—C1	1.373 (3)
C8—C7	1.532 (2)	C2—H2	0.9300
C8—H8	0.9800	C13—C12	1.377 (3)
C17—C16	1.486 (2)	C13—H13	0.9300
C3—C2	1.385 (3)	C1—H1	0.9300
C3—H3	0.9300	C12—H12	0.9300

C17—N1—C18	127.97 (16)	C14—C15—H15	119.8
C17—N1—H4	117.2 (12)	C10—C15—H15	119.8
C18—N1—H4	114.6 (13)	C18—C23—C22	119.52 (18)
C16—N2—N3	108.71 (13)	C18—C23—H23	120.2
C3—C4—C5	118.93 (16)	C22—C23—H23	120.2
C3—C4—C7	123.26 (15)	C13—C14—C15	120.24 (18)
C5—C4—C7	117.80 (15)	C13—C14—H14	119.9
C23—C18—C19	119.96 (16)	C15—C14—H14	119.9
C23—C18—N1	123.06 (16)	C21—C20—C19	120.62 (19)
C19—C18—N1	116.91 (16)	C21—C20—H20	119.7
N2—N3—C8	108.57 (13)	C19—C20—H20	119.7
N2—N3—H18	109.8 (12)	C20—C21—C22	119.59 (18)
C8—N3—H18	114.9 (12)	C20—C21—H21	120.2
C10—C9—C16	109.58 (13)	C22—C21—H21	120.2
C10—C9—C8	115.57 (13)	C5—C6—C1	119.95 (18)
C16—C9—C8	98.12 (12)	C5—C6—H6	120.0
C10—C9—H9	111.0	C1—C6—H6	120.0
C16—C9—H9	111.0	C10—C11—C12	120.56 (18)
C8—C9—H9	111.0	C10—C11—H11	119.7
C11—C10—C15	118.77 (16)	C12—C11—H11	119.7
C11—C10—C9	119.93 (15)	C6—C5—C4	120.72 (18)
C15—C10—C9	121.17 (15)	C6—C5—H5	119.6
N3—C8—C7	111.19 (13)	C4—C5—H5	119.6
N3—C8—C9	101.93 (12)	C20—C19—C18	119.61 (18)
C7—C8—C9	108.60 (13)	C20—C19—H19	120.2
N3—C8—H8	111.6	C18—C19—H19	120.2
C7—C8—H8	111.6	C21—C22—C23	120.70 (19)
C9—C8—H8	111.6	C21—C22—H22	119.6
O2—C17—N1	125.75 (16)	C23—C22—H22	119.6
O2—C17—C16	120.06 (15)	C1—C2—C3	120.43 (19)
N1—C17—C16	114.16 (16)	C1—C2—H2	119.8
C2—C3—C4	119.96 (17)	C3—C2—H2	119.8
C2—C3—H3	120.0	C14—C13—C12	119.73 (18)
C4—C3—H3	120.0	C14—C13—H13	120.1
N2—C16—C17	122.66 (15)	C12—C13—H13	120.1
N2—C16—C9	114.14 (14)	C2—C1—C6	120.00 (19)
C17—C16—C9	123.20 (15)	C2—C1—H1	120.0
O1—C7—C4	120.64 (15)	C6—C1—H1	120.0
O1—C7—C8	119.30 (15)	C13—C12—C11	120.24 (19)
C4—C7—C8	119.99 (14)	C13—C12—H12	119.9
C14—C15—C10	120.45 (18)	C11—C12—H12	119.9

C17—N1—C18—C23	11.9 (3)	C3—C4—C7—C8	−22.0 (2)
C17—N1—C18—C19	−171.13 (17)	C5—C4—C7—C8	159.26 (15)
C16—N2—N3—C8	18.98 (18)	N3—C8—C7—O1	−22.7 (2)
C16—C9—C10—C11	102.37 (17)	C9—C8—C7—O1	88.68 (18)
C8—C9—C10—C11	−147.97 (15)	N3—C8—C7—C4	160.37 (13)
C16—C9—C10—C15	−73.52 (19)	C9—C8—C7—C4	−88.26 (17)
C8—C9—C10—C15	36.1 (2)	C11—C10—C15—C14	0.3 (2)
N2—N3—C8—C7	86.75 (16)	C9—C10—C15—C14	176.24 (15)
N2—N3—C8—C9	−28.81 (16)	C19—C18—C23—C22	−0.8 (3)
C10—C9—C8—N3	−90.48 (15)	N1—C18—C23—C22	176.05 (17)
C16—C9—C8—N3	25.84 (14)	C10—C15—C14—C13	−0.6 (3)
C10—C9—C8—C7	152.07 (13)	C19—C20—C21—C22	−0.1 (3)
C16—C9—C8—C7	−91.60 (14)	C15—C10—C11—C12	0.2 (3)
C18—N1—C17—O2	6.2 (3)	C9—C10—C11—C12	−175.83 (16)
C18—N1—C17—C16	−175.71 (16)	C1—C6—C5—C4	−0.2 (3)
C5—C4—C3—C2	0.4 (3)	C3—C4—C5—C6	0.0 (3)
C7—C4—C3—C2	−178.35 (17)	C7—C4—C5—C6	178.84 (16)
N3—N2—C16—C17	179.69 (14)	C21—C20—C19—C18	−0.3 (3)
N3—N2—C16—C9	0.10 (19)	C23—C18—C19—C20	0.7 (3)
O2—C17—C16—N2	169.36 (16)	N1—C18—C19—C20	−176.31 (17)
N1—C17—C16—N2	−8.8 (2)	C20—C21—C22—C23	0.0 (3)
O2—C17—C16—C9	−11.1 (2)	C18—C23—C22—C21	0.4 (3)
N1—C17—C16—C9	170.74 (14)	C4—C3—C2—C1	−0.6 (3)
C10—C9—C16—N2	103.60 (16)	C15—C14—C13—C12	0.4 (3)
C8—C9—C16—N2	−17.29 (17)	C3—C2—C1—C6	0.4 (3)
C10—C9—C16—C17	−75.98 (19)	C5—C6—C1—C2	0.0 (3)
C8—C9—C16—C17	163.12 (14)	C14—C13—C12—C11	0.1 (3)
C3—C4—C7—O1	161.11 (17)	C10—C11—C12—C13	−0.4 (3)
C5—C4—C7—O1	−17.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.56	3.468 (4)	166
C8—H8···O1ⁱ	0.98	2.50	3.475 (4)	173

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉N₃O₂
M_r	369.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	5.809 (3), 10.717 (5), 29.428 (7)
β (°)	92.753 (5)
V (Å³)	1829.9 (13)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.36 × 0.24 × 0.20

Data collection
Diffractometer	Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.786, 0.873
No. of measured, independent and observed [I > 2σ(I)] reflections	27720, 2929, 2390
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.576

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.066, 1.00
No. of reflections	2929
No. of parameters	261
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.56	3.468 (4)	166
C8—H8···O1ⁱ	0.98	2.50	3.475 (4)	173

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.

Acknowledgements

The diffraction measurements were made at the Centre for Testing and Analysis, Chengdu Branch, Chinese Academy of Sciences. We acknowledge financial support from China West Normal University.

References

Dhal, P. N., Acharya, T. E. & Nayak, A. (1975). J. Indian Chem. Soc. 52, 1196–1200. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Grigg, R. (1995). Tetrahedron Asymmetry, 6, 2475–2486. CrossRef CAS Web of Science Google Scholar
Lombardino, G. & Ottemes, I. G. (1981). J. Med. Chem. 24, 830–834. CrossRef CAS PubMed Web of Science Google Scholar
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Parmar, S. S., Pandey, B. R., Dwivedi, C. & Harbison, R. D. (1974). J. Pharm. Sci. 63, 1152–1255. CrossRef CAS PubMed Web of Science Google Scholar
Rawal, A. A., Thakor, V. M. & Shah, N. M. (1963). J. Indian Chem. Soc. 40, 323–326. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar