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

The title compound, C(23)H(19)N(3)O(2), was synthesized by the 1,3-dipolar cyclo-addition reaction of N-phenyl-α-diazo-acetamide and chalcone. In the mol-ecule, the pyrazoline ring assumes an envelope conformation. Weak inter-molecular 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 = 369.41

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.066

S = 1.00

2929 reflections

261 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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.

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

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

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

C23H19N3O2	F(000) = 776
Mr = 369.41	Dx = 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

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

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(Fo2) + (0.0012P)2 + 1.114P] where P = (Fo2 + 2Fc2)/3
2929 reflections	(Δ/σ)max = 0.001
261 parameters	Δρmax = 0.16 e Å−3
2 restraints	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) .