3-Methyl-1-(3-nitro-phen-yl)-5-phenyl-4,5-dihydro-1H-pyrazole.

In the title compound, C(16)H(15)N(3)O(2), the planar [maximum deviation 0.156 (2) Å] pyrazoline ring is nearly coplanar with the 3-nitro-phenyl group and is approximately perpendicular to the phenyl ring, making dihedral angles of 3.80 (8) and 80.58 (10)°, respectively. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of pyrazoline derivatives, see: Hatheway et al. (1978 ▶); Mahajan et al. (1991 ▶); Sobczak & Pawlaczyk (1998 ▶).

Experimental

Crystal data

C16H15N3O2

M = 281.31

Monoclinic,

a = 12.0173 (4) Å

b = 7.9324 (2) Å

c = 15.4944 (5) Å

β = 99.160 (2)°

V = 1458.18 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.36 × 0.18 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

10272 measured reflections

3014 independent reflections

1648 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.128

S = 1.00

3014 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT (Bruker, 1998 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031390/xu2579sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031390/xu2579Isup2.hkl

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

C16H15N3O2	F(000) = 592
Mr = 281.31	Dx = 1.281 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1824 reflections
a = 12.0173 (4) Å	θ = 2.6–26.5°
b = 7.9324 (2) Å	µ = 0.09 mm−1
c = 15.4944 (5) Å	T = 296 K
β = 99.160 (2)°	Plate, red
V = 1458.18 (8) Å3	0.36 × 0.18 × 0.07 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1648 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
graphite	θmax = 26.5°, θmin = 2.0°
ω scans	h = −14→15
10272 measured reflections	k = −9→8
3014 independent reflections	l = −18→19

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0621P)2] where P = (Fo2 + 2Fc2)/3
3014 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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
C11	0.40009 (13)	0.17187 (19)	0.06087 (10)	0.0433 (4)
N2	0.29773 (12)	0.18897 (16)	0.00749 (10)	0.0578 (4)
C15	0.54447 (14)	0.00161 (19)	0.13960 (10)	0.0454 (4)
C7	0.24060 (14)	0.3481 (2)	−0.02008 (11)	0.0535 (5)
H7A	0.2879	0.4156	−0.0529	0.064*
C16	0.44095 (13)	0.01314 (19)	0.08743 (10)	0.0425 (4)
H16A	0.3991	−0.0832	0.0703	0.051*
N1	0.23515 (12)	0.04742 (18)	−0.02230 (9)	0.0548 (4)
C12	0.46581 (14)	0.3125 (2)	0.08824 (11)	0.0519 (5)
H4A	0.4395	0.4197	0.0714	0.062*
C6	0.21138 (13)	0.4493 (2)	0.05545 (11)	0.0472 (4)
C13	0.56934 (14)	0.2941 (2)	0.13993 (12)	0.0561 (5)
H13A	0.6121	0.3895	0.1572	0.067*
N3	0.58488 (14)	−0.1672 (2)	0.16800 (11)	0.0619 (4)
C1	0.21969 (14)	0.6221 (2)	0.05691 (13)	0.0584 (5)
H1B	0.2456	0.6777	0.0111	0.070*
O1	0.67543 (13)	−0.17917 (18)	0.21576 (11)	0.0990 (6)
C14	0.61085 (14)	0.1383 (2)	0.16652 (11)	0.0536 (5)
H14A	0.6809	0.1259	0.2013	0.064*
O2	0.52813 (13)	−0.28871 (17)	0.14279 (11)	0.0905 (5)
C5	0.17261 (15)	0.3710 (3)	0.12393 (13)	0.0650 (5)
H5A	0.1664	0.2542	0.1241	0.078*
C8	0.13676 (16)	0.2830 (2)	−0.08217 (13)	0.0684 (6)
H8A	0.0675	0.3240	−0.0649	0.082*
H8B	0.1391	0.3168	−0.1420	0.082*
C9	0.14648 (15)	0.0972 (2)	−0.07219 (12)	0.0591 (5)
C4	0.14288 (17)	0.4619 (3)	0.19199 (14)	0.0777 (6)
H12A	0.1166	0.4065	0.2377	0.093*
C2	0.19016 (16)	0.7141 (3)	0.12524 (16)	0.0729 (6)
H2A	0.1963	0.8310	0.1255	0.088*
C3	0.15175 (17)	0.6329 (4)	0.19279 (14)	0.0777 (6)
H3A	0.1318	0.6945	0.2391	0.093*
C10	0.06227 (18)	−0.0247 (3)	−0.11675 (16)	0.0957 (8)
H10A	0.0856	−0.1375	−0.1002	0.144*
H10B	0.0567	−0.0124	−0.1789	0.144*
H10C	−0.0098	−0.0029	−0.0999	0.144*

	U11	U22	U33	U12	U13	U23
C11	0.0398 (10)	0.0436 (10)	0.0470 (10)	0.0024 (8)	0.0079 (8)	−0.0019 (8)
N2	0.0495 (9)	0.0418 (8)	0.0756 (11)	0.0045 (7)	−0.0098 (8)	−0.0003 (7)
C15	0.0460 (10)	0.0452 (10)	0.0457 (10)	0.0054 (8)	0.0097 (8)	0.0021 (8)
C7	0.0505 (11)	0.0526 (11)	0.0567 (11)	0.0095 (9)	0.0057 (9)	0.0079 (9)
C16	0.0402 (10)	0.0422 (10)	0.0451 (10)	−0.0005 (7)	0.0066 (8)	−0.0016 (7)
N1	0.0486 (9)	0.0553 (9)	0.0586 (10)	−0.0003 (7)	0.0028 (8)	−0.0044 (7)
C12	0.0524 (11)	0.0414 (10)	0.0613 (12)	0.0019 (8)	0.0072 (9)	−0.0004 (8)
C6	0.0393 (10)	0.0503 (11)	0.0509 (11)	0.0056 (8)	0.0044 (8)	0.0076 (8)
C13	0.0483 (11)	0.0520 (11)	0.0669 (13)	−0.0111 (9)	0.0059 (10)	−0.0090 (9)
N3	0.0575 (10)	0.0596 (11)	0.0673 (11)	0.0122 (9)	0.0054 (9)	0.0115 (9)
C1	0.0515 (11)	0.0548 (12)	0.0698 (13)	0.0035 (9)	0.0127 (10)	0.0041 (10)
O1	0.0680 (10)	0.0945 (12)	0.1213 (13)	0.0163 (8)	−0.0254 (10)	0.0320 (9)
C14	0.0414 (10)	0.0600 (12)	0.0576 (12)	0.0024 (9)	0.0020 (9)	−0.0024 (9)
O2	0.0924 (11)	0.0471 (8)	0.1237 (14)	0.0038 (8)	−0.0081 (10)	0.0076 (8)
C5	0.0650 (13)	0.0650 (12)	0.0661 (13)	0.0024 (10)	0.0139 (11)	0.0113 (11)
C8	0.0642 (13)	0.0779 (14)	0.0579 (13)	0.0157 (11)	−0.0064 (10)	−0.0013 (10)
C9	0.0494 (11)	0.0694 (13)	0.0555 (12)	0.0051 (10)	−0.0012 (10)	−0.0062 (10)
C4	0.0732 (15)	0.1004 (19)	0.0631 (15)	0.0073 (13)	0.0215 (12)	0.0091 (13)
C2	0.0633 (13)	0.0636 (13)	0.0913 (17)	0.0054 (11)	0.0102 (13)	−0.0148 (12)
C3	0.0609 (13)	0.1077 (19)	0.0644 (15)	0.0120 (13)	0.0094 (11)	−0.0195 (14)
C10	0.0690 (15)	0.1000 (18)	0.1050 (19)	−0.0036 (12)	−0.0269 (13)	−0.0190 (14)

C11—N2	1.375 (2)	N3—O2	1.2093 (18)
C11—C16	1.390 (2)	N3—O1	1.2185 (19)
C11—C12	1.393 (2)	C1—C2	1.378 (3)
N2—N1	1.3888 (18)	C1—H1B	0.9300
N2—C7	1.4678 (19)	C14—H14A	0.9300
C15—C14	1.371 (2)	C5—C4	1.371 (3)
C15—C16	1.374 (2)	C5—H5A	0.9300
C15—N3	1.468 (2)	C8—C9	1.485 (3)
C7—C6	1.506 (2)	C8—H8A	0.9700
C7—C8	1.539 (2)	C8—H8B	0.9700
C7—H7A	0.9800	C9—C10	1.488 (3)
C16—H16A	0.9300	C4—C3	1.360 (3)
N1—C9	1.275 (2)	C4—H12A	0.9300
C12—C13	1.376 (2)	C2—C3	1.370 (3)
C12—H4A	0.9300	C2—H2A	0.9300
C6—C5	1.373 (2)	C3—H3A	0.9300
C6—C1	1.374 (2)	C10—H10A	0.9600
C13—C14	1.371 (2)	C10—H10B	0.9600
C13—H13A	0.9300	C10—H10C	0.9600
N2—C11—C16	120.49 (14)	C6—C1—H1B	119.5
N2—C11—C12	120.89 (14)	C2—C1—H1B	119.5
C16—C11—C12	118.61 (15)	C15—C14—C13	117.08 (16)
C11—N2—N1	120.35 (13)	C15—C14—H14A	121.5
C11—N2—C7	126.29 (14)	C13—C14—H14A	121.5
N1—N2—C7	113.28 (13)	C4—C5—C6	121.3 (2)
C14—C15—C16	123.67 (15)	C4—C5—H5A	119.4
C14—C15—N3	118.79 (15)	C6—C5—H5A	119.4
C16—C15—N3	117.54 (15)	C9—C8—C7	103.05 (14)
N2—C7—C6	112.85 (14)	C9—C8—H8A	111.2
N2—C7—C8	100.85 (13)	C7—C8—H8A	111.2
C6—C7—C8	113.49 (13)	C9—C8—H8B	111.2
N2—C7—H7A	109.8	C7—C8—H8B	111.2
C6—C7—H7A	109.8	H8A—C8—H8B	109.1
C8—C7—H7A	109.8	N1—C9—C8	114.49 (16)
C15—C16—C11	118.59 (15)	N1—C9—C10	121.42 (18)
C15—C16—H16A	120.7	C8—C9—C10	124.09 (17)
C11—C16—H16A	120.7	C3—C4—C5	120.1 (2)
C9—N1—N2	107.90 (15)	C3—C4—H12A	120.0
C13—C12—C11	120.57 (15)	C5—C4—H12A	120.0
C13—C12—H4A	119.7	C3—C2—C1	119.8 (2)
C11—C12—H4A	119.7	C3—C2—H2A	120.1
C5—C6—C1	118.09 (17)	C1—C2—H2A	120.1
C5—C6—C7	120.62 (16)	C4—C3—C2	119.8 (2)
C1—C6—C7	121.27 (16)	C4—C3—H3A	120.1
C14—C13—C12	121.49 (16)	C2—C3—H3A	120.1
C14—C13—H13A	119.3	C9—C10—H10A	109.5
C12—C13—H13A	119.3	C9—C10—H10B	109.5
O2—N3—O1	122.49 (16)	H10A—C10—H10B	109.5
O2—N3—C15	119.20 (15)	C9—C10—H10C	109.5
O1—N3—C15	118.31 (16)	H10A—C10—H10C	109.5
C6—C1—C2	120.93 (19)	H10B—C10—H10C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1i	0.93	2.51	3.245 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O1i	0.93	2.51	3.245 (2)	136

Symmetry code: (i) .