1-[3-(2-Nitro-phen-yl)-5-phenyl-2-pyrazolin-1-yl]ethanone.

The title compound, C(17)H(15)N(3)O(3), was prepared from 1-(2-nitro-phen-yl)-3-phenyl-prop-2-en-1-one and hydrazine. The dihedral angle between the benzene and phenyl rings is 74.55 (2)°. The pyrazoline ring is in a slight envelope conformation with the C atom bonded to the phenyl ring forming the flap. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds connect mol-ecules into chains along [100].

Related literature

For the biological activity of pyrazoline and its derivatives, see: Rawal et al. (1963 ▶); Dhal et al. (1975 ▶); Lombardino & Ottemes (1981 ▶); Manna et al. (2002 ▶). For related structures, see: Guo et al. (2006 ▶); Fahrni et al. (2003 ▶); Kimura et al. (1977 ▶).

Experimental

Crystal data

C17H15N3O3

M = 309.32

Monoclinic,

a = 6.5064 (13) Å

b = 12.385 (3) Å

c = 18.752 (4) Å

β = 98.26 (3)°

V = 1495.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

7203 measured reflections

1710 independent reflections

1354 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.087

S = 1.13

1710 reflections

208 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020611/lh5050sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020611/lh5050Isup2.hkl

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

C17H15N3O3	F(000) = 648
Mr = 309.32	Dx = 1.374 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1354 reflections
a = 6.5064 (13) Å	θ = 3.3–27.3°
b = 12.385 (3) Å	µ = 0.10 mm−1
c = 18.752 (4) Å	T = 293 K
β = 98.26 (3)°	Bar, colourless
V = 1495.4 (5) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	1354 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 27.5°, θmin = 3.3°
φ and ω scans	h = −8→7
7203 measured reflections	k = −16→16
1710 independent reflections	l = −24→24

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0483P)2 + 0.1147P] where P = (Fo2 + 2Fc2)/3
1710 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.20 e Å−3
2 restraints	Δρmin = −0.13 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
C7	0.1900 (3)	0.67920 (17)	0.28552 (12)	0.0384 (5)
N1	−0.1077 (3)	0.79477 (16)	0.27976 (10)	0.0373 (4)
C12	0.2478 (3)	0.68202 (17)	0.36067 (13)	0.0381 (5)
N2	−0.2744 (3)	0.82918 (16)	0.23108 (10)	0.0410 (4)
O3	−0.5900 (3)	0.90449 (18)	0.20896 (11)	0.0596 (5)
C15	0.0046 (3)	0.73132 (18)	0.24741 (12)	0.0376 (5)
C8	0.3234 (4)	0.6223 (2)	0.24684 (14)	0.0455 (5)
H8A	0.2919	0.6180	0.1970	0.055*
N3	0.1191 (3)	0.73560 (17)	0.40852 (11)	0.0455 (5)
O2	−0.0409 (3)	0.69121 (17)	0.41903 (11)	0.0593 (5)
C17	−0.4397 (4)	0.8805 (2)	0.25303 (13)	0.0408 (5)
C16	−0.4249 (4)	0.9042 (2)	0.33180 (14)	0.0485 (6)
H16A	−0.5493	0.9399	0.3411	0.073*
H16B	−0.3075	0.9502	0.3464	0.073*
H16C	−0.4083	0.8379	0.3585	0.073*
C9	0.5016 (4)	0.5720 (2)	0.28093 (17)	0.0520 (6)
H9A	0.5873	0.5345	0.2539	0.062*
C13	−0.2630 (4)	0.7933 (2)	0.15621 (12)	0.0438 (5)
H13A	−0.3902	0.7543	0.1372	0.053*
C1	−0.2353 (4)	0.8890 (2)	0.10825 (11)	0.0427 (5)
C2	−0.4070 (4)	0.9335 (2)	0.06620 (13)	0.0505 (6)
H2A	−0.5363	0.9012	0.0652	0.061*
O1	0.1846 (4)	0.8190 (2)	0.43697 (15)	0.0842 (8)
C11	0.4254 (4)	0.6332 (2)	0.39490 (15)	0.0483 (6)
H11A	0.4595	0.6379	0.4447	0.058*
C10	0.5517 (4)	0.5776 (2)	0.35494 (18)	0.0557 (7)
H10A	0.6709	0.5437	0.3777	0.067*
C14	−0.0785 (5)	0.7133 (2)	0.16914 (13)	0.0533 (6)
H14A	−0.1249	0.6394	0.1605	0.064*
H14B	0.0254	0.7300	0.1385	0.064*
C6	−0.0422 (4)	0.9367 (2)	0.10715 (13)	0.0503 (6)
H6A	0.0754	0.9071	0.1342	0.060*
C5	−0.0242 (5)	1.0285 (3)	0.06587 (15)	0.0595 (7)
H5A	0.1052	1.0603	0.0657	0.071*
C3	−0.3884 (5)	1.0259 (3)	0.02551 (14)	0.0614 (7)
H3A	−0.5054	1.0560	−0.0015	0.074*
C4	−0.1966 (5)	1.0726 (3)	0.02533 (14)	0.0633 (8)
H4A	−0.1836	1.1340	−0.0022	0.076*

	U11	U22	U33	U12	U13	U23
C7	0.0380 (11)	0.0305 (11)	0.0467 (12)	0.0000 (9)	0.0063 (10)	0.0020 (9)
N1	0.0378 (10)	0.0350 (10)	0.0380 (9)	0.0039 (8)	0.0018 (8)	0.0045 (7)
C12	0.0385 (12)	0.0295 (11)	0.0452 (11)	−0.0034 (9)	0.0027 (10)	−0.0010 (9)
N2	0.0412 (10)	0.0440 (11)	0.0367 (9)	0.0071 (9)	0.0013 (8)	0.0042 (8)
O3	0.0403 (10)	0.0773 (14)	0.0593 (10)	0.0098 (9)	0.0003 (9)	0.0081 (9)
C15	0.0407 (12)	0.0329 (12)	0.0389 (11)	0.0003 (9)	0.0044 (10)	0.0005 (9)
C8	0.0484 (13)	0.0356 (13)	0.0532 (13)	0.0031 (10)	0.0097 (11)	0.0009 (10)
N3	0.0442 (11)	0.0482 (12)	0.0426 (10)	−0.0021 (10)	0.0008 (9)	−0.0013 (9)
O2	0.0479 (10)	0.0729 (13)	0.0590 (11)	−0.0043 (9)	0.0140 (9)	0.0091 (9)
C17	0.0342 (11)	0.0398 (13)	0.0484 (12)	−0.0009 (9)	0.0063 (10)	0.0061 (10)
C16	0.0465 (13)	0.0472 (14)	0.0542 (14)	0.0025 (11)	0.0153 (11)	0.0020 (12)
C9	0.0420 (13)	0.0403 (14)	0.0751 (18)	0.0055 (11)	0.0128 (13)	−0.0027 (12)
C13	0.0474 (14)	0.0434 (13)	0.0381 (12)	0.0024 (10)	−0.0030 (10)	−0.0042 (10)
C1	0.0454 (13)	0.0489 (14)	0.0321 (10)	0.0046 (10)	−0.0006 (10)	−0.0062 (9)
C2	0.0465 (13)	0.0651 (17)	0.0378 (11)	0.0047 (12)	−0.0015 (10)	0.0027 (11)
O1	0.0747 (14)	0.0793 (16)	0.1018 (18)	−0.0201 (12)	0.0239 (13)	−0.0516 (14)
C11	0.0477 (14)	0.0379 (13)	0.0553 (14)	−0.0013 (11)	−0.0065 (11)	0.0005 (11)
C10	0.0402 (13)	0.0409 (14)	0.0829 (19)	0.0066 (12)	−0.0018 (13)	0.0042 (13)
C14	0.0695 (17)	0.0472 (15)	0.0409 (12)	0.0148 (13)	−0.0004 (12)	−0.0066 (10)
C6	0.0459 (14)	0.0654 (17)	0.0372 (12)	0.0006 (13)	−0.0026 (10)	−0.0036 (11)
C5	0.0654 (17)	0.0661 (18)	0.0475 (13)	−0.0154 (15)	0.0103 (13)	−0.0063 (13)
C3	0.0671 (18)	0.074 (2)	0.0427 (13)	0.0159 (16)	0.0055 (12)	0.0105 (13)
C4	0.086 (2)	0.0612 (19)	0.0443 (14)	−0.0036 (16)	0.0155 (15)	0.0074 (12)

C7—C8	1.399 (3)	C9—H9A	0.9300
C7—C12	1.406 (3)	C13—C1	1.514 (4)
C7—C15	1.461 (3)	C13—C14	1.548 (4)
N1—C15	1.283 (3)	C13—H13A	0.9800
N1—N2	1.381 (3)	C1—C2	1.386 (3)
C12—C11	1.378 (3)	C1—C6	1.392 (4)
C12—N3	1.471 (3)	C2—C3	1.390 (4)
N2—C17	1.363 (3)	C2—H2A	0.9300
N2—C13	1.484 (3)	C11—C10	1.375 (4)
O3—C17	1.223 (3)	C11—H11A	0.9300
C15—C14	1.506 (3)	C10—H10A	0.9300
C8—C9	1.388 (4)	C14—H14A	0.9700
C8—H8A	0.9300	C14—H14B	0.9700
N3—O1	1.212 (3)	C6—C5	1.390 (4)
N3—O2	1.218 (3)	C6—H6A	0.9300
C17—C16	1.496 (3)	C5—C4	1.374 (4)
C16—H16A	0.9600	C5—H5A	0.9300
C16—H16B	0.9600	C3—C4	1.376 (5)
C16—H16C	0.9600	C3—H3A	0.9300
C9—C10	1.381 (4)	C4—H4A	0.9300
C8—C7—C12	115.8 (2)	N2—C13—H13A	109.7
C8—C7—C15	120.0 (2)	C1—C13—H13A	109.7
C12—C7—C15	124.2 (2)	C14—C13—H13A	109.7
C15—N1—N2	108.84 (18)	C2—C1—C6	118.6 (2)
C11—C12—C7	122.8 (2)	C2—C1—C13	119.7 (2)
C11—C12—N3	115.2 (2)	C6—C1—C13	121.7 (2)
C7—C12—N3	121.9 (2)	C1—C2—C3	120.9 (3)
C17—N2—N1	121.55 (18)	C1—C2—H2A	119.5
C17—N2—C13	125.0 (2)	C3—C2—H2A	119.5
N1—N2—C13	113.05 (17)	C10—C11—C12	119.5 (2)
N1—C15—C7	121.70 (19)	C10—C11—H11A	120.2
N1—C15—C14	113.7 (2)	C12—C11—H11A	120.2
C7—C15—C14	124.5 (2)	C11—C10—C9	120.0 (2)
C9—C8—C7	121.8 (3)	C11—C10—H10A	120.0
C9—C8—H8A	119.1	C9—C10—H10A	120.0
C7—C8—H8A	119.1	C15—C14—C13	102.69 (19)
O1—N3—O2	124.6 (2)	C15—C14—H14A	111.2
O1—N3—C12	117.3 (2)	C13—C14—H14A	111.2
O2—N3—C12	118.0 (2)	C15—C14—H14B	111.2
O3—C17—N2	119.9 (2)	C13—C14—H14B	111.2
O3—C17—C16	123.5 (2)	H14A—C14—H14B	109.1
N2—C17—C16	116.6 (2)	C5—C6—C1	120.3 (2)
C17—C16—H16A	109.5	C5—C6—H6A	119.9
C17—C16—H16B	109.5	C1—C6—H6A	119.9
H16A—C16—H16B	109.5	C4—C5—C6	120.4 (3)
C17—C16—H16C	109.5	C4—C5—H5A	119.8
H16A—C16—H16C	109.5	C6—C5—H5A	119.8
H16B—C16—H16C	109.5	C4—C3—C2	119.9 (3)
C10—C9—C8	120.1 (2)	C4—C3—H3A	120.1
C10—C9—H9A	120.0	C2—C3—H3A	120.1
C8—C9—H9A	120.0	C5—C4—C3	120.0 (3)
N2—C13—C1	110.74 (19)	C5—C4—H4A	120.0
N2—C13—C14	100.74 (17)	C3—C4—H4A	120.0
C1—C13—C14	116.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O3i	0.93	2.41	3.293 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O3i	0.93	2.41	3.293 (4)	157

Symmetry code: (i) .