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

Goh, J.H.; Fun, H.-K.; Adhikari, A.; Kalluraya, B.

doi:10.1107/S1600536809048600

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

J. H. Goh, H.-K. Fun, A. Adhikari and B. Kalluraya

In the title pyrazoline compound, C₁₉H₁₄BrN₅O₂, 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 nitrobenzene unit is almost perpendicular to the attached pyrazoline ring, as indicated by the dihedral angle of 84.61 (8)°. In the crystal structure, intermolecular C—H

N contacts link the molecules into dimers in an antiparallel 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 intermolecular π–π interactions [range of centroid–centroid distances = 3.5160 (11)–3.6912 (11) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809048600/tk2577sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809048600/tk2577Isup2.hkl Contains datablock I

CCDC reference: 758331

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Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.024
wR factor = 0.060
Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         16
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         23

Alert level G
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT164_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct.         14
PLAT793_ALERT_4_G The Model has Chirality at C9      (Verify) ....          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Pyrazoles and pyrazoline derivatives are an important class of heterocyclic compounds (Rai et al., 2008; Hegde et al., 2006). The addition of aliphatic diazo compounds to olefins leads to pyrazolines. Also, the addition of hydrazine or its derivatives to α, β-unsaturated aldehydes or ketones yields pyrazoline (Kalluraya & Chimbalkar, 2001). Pyrazoline derivatives have been found to possess potential anti-pyretic, analgesic (Tawab et al., 1960), anti-inflammatory (Rathish et al., 2009), and anti-microbial (Kalluraya et al., 2001) properties. In the present work, an X-ray crystal structure analysis has been undertaken in order to determine the 3D chemical structure and also the crystal packing of the molecules. We herein report the synthesis and crystal structure of the title compound, (I).

In (I), Fig. 1, the pyrazoline (C7-C9/N1/N2) and pyrimidine (C16-C19/N3/N4) rings are essentially planar, with maximum deviations of 0.013 (1) and 0.009 (1) Å, respectively, for atoms N1 and C16. These two rings are slightly inclined to one another, making a dihedral angle of 10.81 (10)°. The nitrobenzene moiety is almost perpendicular to the attached pyrazoline ring, as indicated by the dihedral angle formed between the mean plane through C10-C15/N5/O1/O2 and the pyrazoline ring of 84.61 (8)°. The bond lengths and angles are consistent with those closely related structures (Goh et al., 2009a,b).

In the crystal structure (Fig. 2), intermolecular C11—H11A···N4 contacts (Table 1) link the molecules into dimers in an anti-parallel manner. These dimers are further linked into a 1-D chain along the b axis by intermolecular C8—H8B···O2 and C19—H19A···O2 contacts (Table 1). The crystal structure is consolidated by three different weak π–π interactions involving the pyrazoline (Cg1), pyrimidine (Cg2) and C1-C6 benzene (Cg3) rings [Cg1···Cg1^iv = 3.5160 (11) Å, Cg2···Cg3ⁱⁱ = 3.6912 (11) Å and Cg2···Cg3^iv = 3.5779 (11) Å, respectively; (ii) -x, 1-y, 1-z and (iv) 1-x, 1-y, 1-z].

Related literature top

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. (2009a,b). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 5-bromo-2-hydrazinopyrimidine (0.01 mol) and 3-(4-nitrophenyl)-1-phenyl-prop-2-en-1-one (0.01 mol) was taken in acetic acid (20 ml), and two drops of concentrated H₂SO₄ added. The mixture was refluxed for 4 h. The precipitated solids were filtered, dried and recrystallized from ethanol. The single crystals were obtained from a mixture of ethanol and DMF by slow evaporation.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
	Fig. 2. Part of the crystal structure of (I), viewed along the a axis, showing the dimers being linked into a 1-D chain along the b axis. Intermolecular contacts are shown as dashed lines.

5-Bromo-2-[5-(4-nitrophenyl)-3-phenyl-4,5-dihydro-1H- pyrazol-1-yl]pyrimidine top

Crystal data top

C₁₉H₁₄BrN₅O₂	Z = 2
M_r = 424.26	F(000) = 428
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.060	All H-atom parameters refined
S = 1.05	w = 1/[σ²(F_o²) + (0.0288P)² + 0.5594P] where P = (F_o² + 2F_c²)/3
3804 reflections	(Δ/σ)_max = 0.001
300 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₉H₁₄BrN₅O₂	γ = 91.560 (1)°
M_r = 424.26	V = 882.12 (2) Å³
Triclinic, P1	Z = 2
a = 6.9709 (1) Å	Mo Kα radiation
b = 11.6500 (2) Å	µ = 2.36 mm⁻¹
c = 12.4365 (2) Å	T = 100 K
α = 114.969 (1)°	0.33 × 0.22 × 0.12 mm
β = 103.303 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3804 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3431 reflections with I > 2σ(I)
T_min = 0.510, T_max = 0.760	R_int = 0.026
28197 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.060	All H-atom parameters refined
S = 1.05	Δρ_max = 0.49 e Å⁻³
3804 reflections	Δρ_min = −0.30 e Å⁻³
300 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z+1; (ii) −x, −y+1, −z+1; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄BrN₅O₂
M_r	424.26
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.9709 (1), 11.6500 (2), 12.4365 (2)
α, β, γ (°)	114.969 (1), 103.303 (1), 91.560 (1)
V (Å³)	882.12 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.36
Crystal size (mm)	0.33 × 0.22 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.510, 0.760
No. of measured, independent and observed [I > 2σ(I)] reflections	28197, 3804, 3431
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.060, 1.05
No. of reflections	3804
No. of parameters	300
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.30

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).