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

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3134-o3135

doi:10.1107/S1600536809048600

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

Jia Hao Goh,^a ‡ Hoong-Kun Fun,^a ^*§ Adithya Adhikari ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 13 November 2009; accepted 16 November 2009; online 21 November 2009)

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].

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

Experimental

Crystal data

C₁₉H₁₄BrN₅O₂
M_r = 424.26
Triclinic, $[P \overline 1]$
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 (SADABS; 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[F² > 2σ(F²)] = 0.024
wR(F²) = 0.060
S = 1.05
3804 reflections
300 parameters
All H-atom parameters refined
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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

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 ).

Supporting information

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

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

checkCIF report

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).

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.

Footnotes

‡Thomson Reuters ResearcherID: C-7576-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

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