5-Bromo-2-[5-(4-nitro-phen-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]pyrimidine.

In the title pyrazoline compound, C(19)H(14)BrN(5)O(2), the essentially planar pyrazoline and pyrimidine rings [maximum deviations = 0.013 (1) and 0.009 (1) Å, respectively] are inclined slightly to one another, making a dihedral angle of 10.81 (10)°. The nitro-benzene unit is almost perpendicular to the attached pyrazoline ring, as indicated by the dihedral angle of 84.61 (8)°. In the crystal structure, inter-molecular C-H⋯N contacts link the mol-ecules into dimers in an anti-parallel manner. These dimers are further linked into one-dimensional chains along the b axis via C-H⋯O contacts. The crystal structure is consolidated by three different inter-molecular π-π inter-actions [range of centroid-centroid distances = 3.5160 (11)-3.6912 (11) Å].

Related literature

For general background to and applications of the title compound, see: Hegde et al. (2006 ▶); Kalluraya & Chimbalkar (2001 ▶); Kalluraya et al. (2001 ▶); Rai et al. (2008 ▶); Rathish et al. (2009 ▶); Tawab et al. (1960 ▶). For closely related structures, see: Goh et al. (2009 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C19H14BrN5O2

M = 424.26

Triclinic,

a = 6.9709 (1) Å

b = 11.6500 (2) Å

c = 12.4365 (2) Å

α = 114.969 (1)°

β = 103.303 (1)°

γ = 91.560 (1)°

V = 882.12 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.36 mm−1

T = 100 K

0.33 × 0.22 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.510, T max = 0.760

28197 measured reflections

3804 independent reflections

3431 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.060

S = 1.05

3804 reflections

300 parameters

All H-atom parameters refined

Δρmax = 0.49 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048600/tk2577sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048600/tk2577Isup2.hkl

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

C19H14BrN5O2	Z = 2
Mr = 424.26	F(000) = 428
Triclinic, P1	Dx = 1.597 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9709 (1) Å	Cell parameters from 9873 reflections
b = 11.6500 (2) Å	θ = 3.0–33.9°
c = 12.4365 (2) Å	µ = 2.36 mm−1
α = 114.969 (1)°	T = 100 K
β = 103.303 (1)°	Block, green
γ = 91.560 (1)°	0.33 × 0.22 × 0.12 mm
V = 882.12 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	3804 independent reflections
Radiation source: fine-focus sealed tube	3431 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.510, Tmax = 0.760	k = −14→14
28197 measured reflections	l = −15→15

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0288P)2 + 0.5594P] where P = (Fo2 + 2Fc2)/3
3804 reflections	(Δ/σ)max = 0.001
300 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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 > 2sigma(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
Br1	0.32778 (3)	0.891599 (17)	1.068122 (15)	0.02770 (7)
O1	−0.3115 (2)	0.02211 (12)	0.64236 (12)	0.0274 (3)
O2	−0.0404 (2)	−0.01117 (12)	0.74511 (11)	0.0258 (3)
N1	0.2287 (2)	0.49488 (13)	0.46957 (12)	0.0175 (3)
N2	0.2681 (2)	0.47661 (13)	0.57546 (12)	0.0177 (3)
N3	0.3203 (2)	0.54232 (13)	0.78176 (13)	0.0191 (3)
N4	0.2364 (2)	0.68890 (13)	0.69321 (13)	0.0182 (3)
N5	−0.1294 (2)	0.03714 (13)	0.68034 (13)	0.0205 (3)
C1	0.1859 (3)	0.48220 (17)	0.22862 (16)	0.0224 (4)
C2	0.1604 (3)	0.4683 (2)	0.10980 (17)	0.0282 (4)
C3	0.1682 (3)	0.3501 (2)	0.01564 (17)	0.0300 (4)
C4	0.2012 (3)	0.24641 (19)	0.04084 (17)	0.0275 (4)
C5	0.2323 (3)	0.26060 (18)	0.16071 (16)	0.0236 (4)
C6	0.2252 (2)	0.37903 (16)	0.25600 (15)	0.0201 (3)
C7	0.2607 (2)	0.39338 (15)	0.38231 (15)	0.0176 (3)
C8	0.3349 (3)	0.29328 (16)	0.42148 (17)	0.0228 (4)
C9	0.3406 (3)	0.35347 (16)	0.55889 (15)	0.0191 (3)
C10	0.2129 (3)	0.27153 (15)	0.59130 (14)	0.0175 (3)
C11	0.0070 (3)	0.24832 (16)	0.54497 (15)	0.0188 (3)
C12	−0.1072 (3)	0.17094 (16)	0.57339 (15)	0.0191 (3)
C13	−0.0101 (3)	0.11782 (15)	0.64817 (15)	0.0178 (3)
C14	0.1942 (3)	0.13677 (16)	0.69325 (16)	0.0211 (3)
C15	0.3060 (3)	0.21486 (16)	0.66433 (16)	0.0213 (3)
C16	0.2747 (2)	0.57397 (15)	0.68747 (15)	0.0165 (3)
C17	0.3326 (3)	0.63670 (17)	0.89244 (16)	0.0207 (3)
C18	0.2999 (3)	0.75881 (16)	0.90934 (15)	0.0204 (3)
C19	0.2496 (3)	0.78065 (16)	0.80562 (16)	0.0201 (3)
H1A	0.177 (3)	0.563 (2)	0.2909 (19)	0.025 (5)*
H2A	0.138 (4)	0.540 (2)	0.092 (2)	0.038 (6)*
H3A	0.154 (3)	0.340 (2)	−0.066 (2)	0.037 (6)*
H4A	0.206 (3)	0.169 (2)	−0.020 (2)	0.024 (5)*
H5A	0.257 (3)	0.190 (2)	0.178 (2)	0.028 (5)*
H8A	0.467 (3)	0.2771 (19)	0.4110 (19)	0.024 (5)*
H8B	0.250 (3)	0.214 (2)	0.378 (2)	0.031 (6)*
H9A	0.478 (3)	0.3691 (17)	0.6123 (17)	0.013 (4)*
H11A	−0.055 (3)	0.2853 (18)	0.4970 (18)	0.019 (5)*
H12A	−0.245 (3)	0.1549 (19)	0.5429 (19)	0.024 (5)*
H14A	0.258 (3)	0.0991 (19)	0.7416 (19)	0.025 (5)*
H15A	0.446 (3)	0.2291 (19)	0.6952 (19)	0.025 (5)*
H17A	0.372 (3)	0.6149 (19)	0.9598 (19)	0.022 (5)*
H19A	0.224 (3)	0.8658 (19)	0.8141 (18)	0.019 (5)*

	U11	U22	U33	U12	U13	U23
Br1	0.02884 (11)	0.02882 (11)	0.01659 (9)	0.00509 (7)	0.00679 (7)	0.00134 (7)
O1	0.0263 (7)	0.0275 (7)	0.0323 (7)	0.0020 (5)	0.0112 (6)	0.0154 (6)
O2	0.0386 (8)	0.0213 (6)	0.0223 (6)	0.0044 (5)	0.0086 (6)	0.0139 (5)
N1	0.0171 (7)	0.0197 (7)	0.0145 (6)	0.0012 (5)	0.0029 (5)	0.0070 (5)
N2	0.0231 (8)	0.0155 (6)	0.0160 (7)	0.0037 (5)	0.0070 (6)	0.0073 (5)
N3	0.0199 (7)	0.0202 (7)	0.0180 (7)	0.0023 (6)	0.0060 (6)	0.0087 (6)
N4	0.0185 (7)	0.0179 (7)	0.0174 (7)	0.0043 (5)	0.0047 (6)	0.0068 (6)
N5	0.0302 (9)	0.0147 (6)	0.0173 (7)	0.0036 (6)	0.0107 (6)	0.0055 (6)
C1	0.0190 (9)	0.0260 (9)	0.0173 (8)	0.0058 (7)	0.0023 (7)	0.0061 (7)
C2	0.0244 (10)	0.0390 (11)	0.0209 (9)	0.0122 (8)	0.0031 (7)	0.0140 (8)
C3	0.0235 (10)	0.0459 (12)	0.0152 (8)	0.0112 (8)	0.0028 (7)	0.0091 (8)
C4	0.0202 (9)	0.0321 (10)	0.0173 (8)	0.0036 (8)	0.0049 (7)	−0.0012 (8)
C5	0.0185 (9)	0.0247 (9)	0.0219 (9)	0.0023 (7)	0.0063 (7)	0.0045 (7)
C6	0.0137 (8)	0.0250 (9)	0.0169 (8)	0.0010 (6)	0.0040 (6)	0.0049 (7)
C7	0.0149 (8)	0.0172 (7)	0.0179 (8)	−0.0004 (6)	0.0050 (6)	0.0051 (6)
C8	0.0315 (10)	0.0164 (8)	0.0246 (9)	0.0043 (7)	0.0156 (8)	0.0086 (7)
C9	0.0212 (9)	0.0161 (7)	0.0209 (8)	0.0036 (6)	0.0081 (7)	0.0078 (6)
C10	0.0236 (9)	0.0140 (7)	0.0149 (7)	0.0033 (6)	0.0077 (6)	0.0050 (6)
C11	0.0225 (9)	0.0184 (8)	0.0179 (8)	0.0055 (7)	0.0056 (7)	0.0099 (7)
C12	0.0204 (9)	0.0187 (8)	0.0183 (8)	0.0046 (7)	0.0060 (7)	0.0075 (7)
C13	0.0252 (9)	0.0137 (7)	0.0153 (7)	0.0028 (6)	0.0085 (7)	0.0057 (6)
C14	0.0278 (10)	0.0197 (8)	0.0179 (8)	0.0066 (7)	0.0054 (7)	0.0103 (7)
C15	0.0194 (9)	0.0216 (8)	0.0212 (8)	0.0032 (7)	0.0030 (7)	0.0092 (7)
C16	0.0136 (8)	0.0174 (8)	0.0173 (8)	0.0013 (6)	0.0048 (6)	0.0064 (6)
C17	0.0191 (9)	0.0255 (9)	0.0180 (8)	0.0028 (7)	0.0059 (7)	0.0095 (7)
C18	0.0176 (8)	0.0222 (8)	0.0152 (8)	0.0020 (7)	0.0049 (6)	0.0023 (7)
C19	0.0187 (9)	0.0192 (8)	0.0204 (8)	0.0046 (7)	0.0051 (7)	0.0067 (7)

Br1—C18	1.8863 (16)	C5—H5A	0.94 (2)
O1—N5	1.228 (2)	C6—C7	1.468 (2)
O2—N5	1.2337 (19)	C7—C8	1.504 (2)
N1—C7	1.292 (2)	C8—C9	1.539 (2)
N1—N2	1.3886 (19)	C8—H8A	0.97 (2)
N2—C16	1.365 (2)	C8—H8B	0.95 (2)
N2—C9	1.481 (2)	C9—C10	1.519 (2)
N3—C17	1.332 (2)	C9—H9A	0.995 (19)
N3—C16	1.346 (2)	C10—C11	1.391 (2)
N4—C19	1.334 (2)	C10—C15	1.393 (2)
N4—C16	1.348 (2)	C11—C12	1.389 (2)
N5—C13	1.471 (2)	C11—H11A	0.91 (2)
C1—C2	1.384 (3)	C12—C13	1.387 (2)
C1—C6	1.399 (3)	C12—H12A	0.93 (2)
C1—H1A	0.95 (2)	C13—C14	1.379 (3)
C2—C3	1.394 (3)	C14—C15	1.390 (2)
C2—H2A	0.96 (2)	C14—H14A	0.93 (2)
C3—C4	1.383 (3)	C15—H15A	0.94 (2)
C3—H3A	0.95 (2)	C17—C18	1.381 (3)
C4—C5	1.392 (3)	C17—H17A	0.96 (2)
C4—H4A	0.91 (2)	C18—C19	1.388 (2)
C5—C6	1.400 (2)	C19—H19A	0.98 (2)
C7—N1—N2	107.71 (14)	N2—C9—C10	113.23 (14)
C16—N2—N1	121.50 (13)	N2—C9—C8	101.32 (13)
C16—N2—C9	123.73 (14)	C10—C9—C8	113.11 (14)
N1—N2—C9	113.65 (13)	N2—C9—H9A	110.2 (10)
C17—N3—C16	115.56 (15)	C10—C9—H9A	107.2 (10)
C19—N4—C16	115.45 (14)	C8—C9—H9A	111.9 (10)
O1—N5—O2	123.49 (14)	C11—C10—C15	119.99 (15)
O1—N5—C13	118.57 (14)	C11—C10—C9	121.01 (15)
O2—N5—C13	117.94 (15)	C15—C10—C9	118.95 (15)
C2—C1—C6	120.44 (17)	C12—C11—C10	120.27 (16)
C2—C1—H1A	118.6 (12)	C12—C11—H11A	119.2 (12)
C6—C1—H1A	121.0 (12)	C10—C11—H11A	120.5 (12)
C1—C2—C3	120.15 (19)	C13—C12—C11	118.28 (16)
C1—C2—H2A	120.0 (14)	C13—C12—H12A	120.8 (12)
C3—C2—H2A	119.8 (14)	C11—C12—H12A	121.0 (12)
C4—C3—C2	119.95 (17)	C14—C13—C12	122.77 (15)
C4—C3—H3A	119.4 (14)	C14—C13—N5	118.41 (15)
C2—C3—H3A	120.6 (14)	C12—C13—N5	118.82 (15)
C3—C4—C5	120.16 (17)	C13—C14—C15	118.17 (16)
C3—C4—H4A	120.9 (13)	C13—C14—H14A	122.0 (13)
C5—C4—H4A	118.9 (13)	C15—C14—H14A	119.8 (13)
C4—C5—C6	120.28 (18)	C14—C15—C10	120.49 (17)
C4—C5—H5A	120.2 (13)	C14—C15—H15A	119.0 (12)
C6—C5—H5A	119.5 (13)	C10—C15—H15A	120.5 (12)
C1—C6—C5	118.96 (16)	N3—C16—N4	127.09 (15)
C1—C6—C7	121.19 (15)	N3—C16—N2	114.49 (14)
C5—C6—C7	119.85 (16)	N4—C16—N2	118.43 (14)
N1—C7—C6	121.79 (16)	N3—C17—C18	122.24 (16)
N1—C7—C8	114.40 (15)	N3—C17—H17A	115.3 (12)
C6—C7—C8	123.81 (15)	C18—C17—H17A	122.4 (12)
C7—C8—C9	102.87 (13)	C17—C18—C19	117.58 (15)
C7—C8—H8A	112.2 (12)	C17—C18—Br1	121.08 (13)
C9—C8—H8A	110.4 (12)	C19—C18—Br1	121.33 (13)
C7—C8—H8B	112.8 (13)	N4—C19—C18	122.05 (16)
C9—C8—H8B	111.1 (13)	N4—C19—H19A	118.1 (11)
H8A—C8—H8B	107.5 (18)	C18—C19—H19A	119.8 (11)
C7—N1—N2—C16	170.72 (14)	C15—C10—C11—C12	1.4 (2)
C7—N1—N2—C9	2.42 (18)	C9—C10—C11—C12	178.62 (15)
C6—C1—C2—C3	1.8 (3)	C10—C11—C12—C13	−0.2 (2)
C1—C2—C3—C4	0.1 (3)	C11—C12—C13—C14	−1.2 (2)
C2—C3—C4—C5	−1.8 (3)	C11—C12—C13—N5	179.18 (14)
C3—C4—C5—C6	1.6 (3)	O1—N5—C13—C14	178.59 (15)
C2—C1—C6—C5	−1.9 (3)	O2—N5—C13—C14	−0.9 (2)
C2—C1—C6—C7	177.49 (16)	O1—N5—C13—C12	−1.8 (2)
C4—C5—C6—C1	0.2 (3)	O2—N5—C13—C12	178.73 (14)
C4—C5—C6—C7	−179.20 (16)	C12—C13—C14—C15	1.5 (3)
N2—N1—C7—C6	177.49 (14)	N5—C13—C14—C15	−178.92 (15)
N2—N1—C7—C8	−2.15 (19)	C13—C14—C15—C10	−0.3 (3)
C1—C6—C7—N1	10.4 (2)	C11—C10—C15—C14	−1.1 (2)
C5—C6—C7—N1	−170.23 (16)	C9—C10—C15—C14	−178.41 (15)
C1—C6—C7—C8	−170.01 (16)	C17—N3—C16—N4	−1.6 (2)
C5—C6—C7—C8	9.4 (2)	C17—N3—C16—N2	178.34 (14)
N1—C7—C8—C9	1.11 (19)	C19—N4—C16—N3	1.4 (2)
C6—C7—C8—C9	−178.52 (15)	C19—N4—C16—N2	−178.54 (14)
C16—N2—C9—C10	68.9 (2)	N1—N2—C16—N3	−178.10 (14)
N1—N2—C9—C10	−123.07 (15)	C9—N2—C16—N3	−11.0 (2)
C16—N2—C9—C8	−169.64 (15)	N1—N2—C16—N4	1.8 (2)
N1—N2—C9—C8	−1.64 (17)	C9—N2—C16—N4	168.92 (14)
C7—C8—C9—N2	0.35 (16)	C16—N3—C17—C18	0.3 (2)
C7—C8—C9—C10	121.86 (15)	N3—C17—C18—C19	1.0 (3)
N2—C9—C10—C11	49.0 (2)	N3—C17—C18—Br1	−177.75 (12)
C8—C9—C10—C11	−65.5 (2)	C16—N4—C19—C18	0.1 (2)
N2—C9—C10—C15	−133.70 (16)	C17—C18—C19—N4	−1.2 (3)
C8—C9—C10—C15	111.76 (18)	Br1—C18—C19—N4	177.53 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O2i	0.95 (2)	2.41 (2)	3.352 (2)	176.0 (17)
C11—H11A···N4ii	0.92 (2)	2.56 (2)	3.431 (2)	160.5 (18)
C19—H19A···O2iii	0.98 (2)	2.58 (2)	3.412 (3)	143.3 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O2i	0.95 (2)	2.41 (2)	3.352 (2)	176.0 (17)
C11—H11A⋯N4ii	0.92 (2)	2.56 (2)	3.431 (2)	160.5 (18)
C19—H19A⋯O2iii	0.98 (2)	2.58 (2)	3.412 (3)	143.3 (17)

Symmetry codes: (i) ; (ii) ; (iii) .