7-(4-Bromo-phen-yl)-9-phenyl-7H-pyrrolo[3,2-e]tetra-zolo[1,5-c]pyrimidine.

In the title compound, C(18)H(11)BrN(6), the phenyl ring is almost coplanar [dihedral angle 7.2 (1)°] with the planar (r.m.s. deviation 0.039 Å) tricyclic ring system while the 4-bromo-phenyl ring makes a dihedral angle of 33.98 (6)° with the ring system. Weak inter-molecular C-H⋯N and C-H⋯Br hydrogen-bonding inter-actions and π-π stacking [centroid-centroid distances = 3.7971 (17) and 3.5599 (16) Å] stabilize the crystal packing. A comparison of the structure to a MOPAC PM3 geometry optimization calculation in vacuo supports these observations.

Related literature

For anti­cancer relationships, see: Hiedo & Yasuo (1960 ▶, 1961 ▶). For the synthesis of derivative compounds, see: Dave & Shukla (1997 ▶); Dave & Shah (1998 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For MOPAC PM3 calculations, see: Schmidt & Polik (2007 ▶).

Experimental

Crystal data

C18H11BrN6

M = 391.24

Monoclinic,

a = 12.0173 (5) Å

b = 17.4007 (7) Å

c = 7.4201 (4) Å

β = 91.004 (4)°

V = 1551.37 (12) Å3

Z = 4

Mo Kα radiation

μ = 2.66 mm−1

T = 200 K

0.47 × 0.39 × 0.22 mm

Data collection

Oxford Diffraction Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.494, T max = 1.000

13458 measured reflections

5032 independent reflections

2606 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 1.14

5032 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.71 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 I. DOI: 10.1107/S1600536810004368/bt5188sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004368/bt5188Isup2.hkl

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

C18H11BrN6	F(000) = 784
Mr = 391.24	Dx = 1.675 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4168 reflections
a = 12.0173 (5) Å	θ = 4.8–32.4°
b = 17.4007 (7) Å	µ = 2.66 mm−1
c = 7.4201 (4) Å	T = 200 K
β = 91.004 (4)°	Plate, colorless
V = 1551.37 (12) Å3	0.47 × 0.39 × 0.22 mm
Z = 4

Oxford Diffraction Gemini diffractometer	5032 independent reflections
Radiation source: fine-focus sealed tube	2606 reflections with I > 2σ(I)
graphite	Rint = 0.050
Detector resolution: 10.5081 pixels mm-1	θmax = 32.5°, θmin = 4.8°
φ and ω scans	h = −16→18
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −25→26
Tmin = 0.494, Tmax = 1.000	l = −11→11
13458 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0295P)2] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
5032 reflections	Δρmax = 0.72 e Å−3
227 parameters	Δρmin = −0.71 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (4)

Experimental. (CrysAlis RED; Oxford Diffraction, 2007)

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 > 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
Br	−0.01667 (2)	0.226033 (17)	0.00063 (4)	0.03758 (11)
N1	0.35315 (14)	0.45391 (11)	0.1749 (3)	0.0245 (5)
N2	0.24838 (15)	0.57000 (12)	0.2186 (3)	0.0300 (5)
N3	0.35441 (16)	0.67017 (11)	0.3359 (3)	0.0292 (5)
N4	0.3685 (2)	0.74165 (13)	0.4080 (3)	0.0406 (6)
N5	0.4737 (2)	0.74487 (13)	0.4525 (4)	0.0432 (7)
N6	0.52928 (17)	0.67915 (12)	0.4136 (3)	0.0359 (6)
C1	0.34572 (18)	0.52985 (14)	0.2224 (3)	0.0235 (5)
C2	0.45169 (18)	0.55548 (13)	0.2756 (3)	0.0219 (5)
C3	0.52682 (19)	0.49222 (13)	0.2569 (3)	0.0230 (5)
C4	0.46260 (17)	0.43241 (14)	0.1955 (4)	0.0245 (6)
H4	0.4902	0.3825	0.1703	0.029*
C5	0.2555 (2)	0.63991 (16)	0.2741 (4)	0.0338 (7)
H5	0.1908	0.6713	0.2722	0.041*
C6	0.45368 (19)	0.63216 (14)	0.3404 (4)	0.0263 (6)
C7	0.64817 (18)	0.48691 (13)	0.2913 (3)	0.0225 (5)
C8	0.70547 (19)	0.42147 (14)	0.2367 (4)	0.0277 (6)
H8	0.6659	0.3814	0.1769	0.033*
C9	0.8188 (2)	0.41373 (15)	0.2680 (4)	0.0344 (7)
H9	0.8560	0.3687	0.2289	0.041*
C10	0.8778 (2)	0.47079 (17)	0.3551 (4)	0.0351 (7)
H10	0.9556	0.4654	0.3767	0.042*
C11	0.82296 (19)	0.53569 (16)	0.4107 (4)	0.0344 (7)
H11	0.8634	0.5752	0.4713	0.041*
C12	0.70894 (18)	0.54451 (14)	0.3794 (4)	0.0283 (6)
H12	0.6725	0.5899	0.4181	0.034*
C13	0.26457 (18)	0.40147 (14)	0.1343 (3)	0.0238 (6)
C14	0.16953 (19)	0.42519 (15)	0.0414 (4)	0.0301 (6)
H14	0.1623	0.4771	0.0035	0.036*
C15	0.08552 (19)	0.37323 (16)	0.0039 (4)	0.0308 (6)
H15	0.0195	0.3894	−0.0574	0.037*
C16	0.09811 (19)	0.29777 (15)	0.0561 (4)	0.0282 (6)
C17	0.19254 (19)	0.27285 (15)	0.1480 (4)	0.0294 (6)
H17	0.2005	0.2205	0.1822	0.035*
C18	0.27530 (18)	0.32577 (15)	0.1893 (4)	0.0293 (6)
H18	0.3397	0.3100	0.2556	0.035*

	U11	U22	U33	U12	U13	U23
Br	0.03221 (15)	0.04452 (19)	0.03605 (18)	−0.01798 (12)	0.00207 (11)	−0.00499 (15)
N1	0.0192 (9)	0.0240 (11)	0.0302 (13)	−0.0015 (8)	−0.0006 (9)	−0.0010 (10)
N2	0.0265 (11)	0.0277 (12)	0.0361 (15)	0.0033 (9)	0.0021 (10)	−0.0018 (11)
N3	0.0332 (11)	0.0193 (11)	0.0354 (14)	0.0034 (9)	0.0050 (10)	−0.0002 (10)
N4	0.0478 (14)	0.0232 (13)	0.0509 (17)	0.0014 (10)	0.0049 (12)	−0.0054 (12)
N5	0.0527 (15)	0.0195 (12)	0.057 (2)	−0.0027 (10)	0.0016 (13)	−0.0071 (12)
N6	0.0398 (12)	0.0205 (12)	0.0473 (16)	−0.0030 (9)	−0.0007 (11)	−0.0038 (11)
C1	0.0236 (11)	0.0220 (12)	0.0250 (15)	−0.0031 (10)	0.0021 (10)	−0.0002 (11)
C2	0.0249 (12)	0.0186 (12)	0.0222 (15)	−0.0019 (9)	0.0009 (10)	0.0026 (11)
C3	0.0279 (13)	0.0211 (13)	0.0199 (13)	−0.0029 (9)	−0.0028 (10)	0.0028 (11)
C4	0.0215 (11)	0.0226 (13)	0.0295 (16)	0.0015 (9)	0.0001 (10)	−0.0001 (12)
C5	0.0281 (13)	0.0334 (16)	0.0399 (18)	0.0067 (11)	0.0029 (12)	−0.0003 (14)
C6	0.0299 (13)	0.0198 (13)	0.0294 (16)	−0.0005 (10)	0.0044 (11)	0.0061 (12)
C7	0.0206 (12)	0.0232 (13)	0.0237 (14)	−0.0020 (9)	−0.0001 (10)	0.0048 (11)
C8	0.0274 (12)	0.0210 (13)	0.0343 (17)	−0.0041 (10)	−0.0050 (11)	0.0037 (12)
C9	0.0342 (14)	0.0269 (15)	0.0418 (19)	0.0075 (11)	−0.0035 (13)	0.0054 (13)
C10	0.0237 (13)	0.0426 (16)	0.0388 (19)	0.0004 (12)	−0.0085 (12)	0.0022 (14)
C11	0.0291 (13)	0.0352 (15)	0.0387 (19)	−0.0065 (12)	−0.0077 (12)	−0.0027 (14)
C12	0.0261 (12)	0.0242 (14)	0.0346 (17)	−0.0022 (10)	−0.0022 (11)	−0.0011 (12)
C13	0.0243 (12)	0.0256 (13)	0.0216 (15)	−0.0063 (10)	0.0034 (10)	−0.0033 (11)
C14	0.0275 (12)	0.0294 (14)	0.0334 (17)	−0.0039 (10)	0.0003 (12)	0.0052 (13)
C15	0.0251 (13)	0.0369 (16)	0.0304 (16)	−0.0043 (11)	−0.0025 (11)	0.0022 (13)
C16	0.0255 (12)	0.0331 (15)	0.0263 (16)	−0.0093 (10)	0.0075 (11)	−0.0060 (12)
C17	0.0291 (13)	0.0252 (13)	0.0341 (16)	−0.0027 (11)	0.0036 (11)	0.0019 (13)
C18	0.0213 (12)	0.0313 (15)	0.0352 (17)	−0.0008 (10)	−0.0010 (11)	0.0036 (13)

Br—C16	1.900 (2)	C7—C12	1.396 (3)
N1—C1	1.371 (3)	C8—C9	1.383 (3)
N1—C4	1.373 (3)	C8—H8	0.9500
N1—C13	1.430 (3)	C9—C10	1.375 (4)
N2—C5	1.287 (3)	C9—H9	0.9500
N2—C1	1.362 (3)	C10—C11	1.374 (4)
N3—N4	1.363 (3)	C10—H10	0.9500
N3—C6	1.364 (3)	C11—C12	1.394 (3)
N3—C5	1.371 (3)	C11—H11	0.9500
N4—N5	1.301 (3)	C12—H12	0.9500
N5—N6	1.358 (3)	C13—C18	1.384 (3)
N6—C6	1.331 (3)	C13—C14	1.387 (3)
C1—C2	1.400 (3)	C14—C15	1.380 (3)
C2—C6	1.418 (3)	C14—H14	0.9500
C2—C3	1.432 (3)	C15—C16	1.377 (4)
C3—C4	1.369 (3)	C15—H15	0.9500
C3—C7	1.479 (3)	C16—C17	1.383 (3)
C4—H4	0.9500	C17—C18	1.386 (3)
C5—H5	0.9500	C17—H17	0.9500
C7—C8	1.394 (3)	C18—H18	0.9500
C1—N1—C4	107.48 (18)	C9—C8—H8	119.3
C1—N1—C13	128.14 (18)	C7—C8—H8	119.3
C4—N1—C13	123.9 (2)	C10—C9—C8	120.4 (2)
C5—N2—C1	115.2 (2)	C10—C9—H9	119.8
N4—N3—C6	109.3 (2)	C8—C9—H9	119.8
N4—N3—C5	125.7 (2)	C11—C10—C9	119.2 (2)
C6—N3—C5	125.1 (2)	C11—C10—H10	120.4
N5—N4—N3	104.6 (2)	C9—C10—H10	120.4
N4—N5—N6	112.9 (2)	C10—C11—C12	121.0 (2)
C6—N6—N5	105.6 (2)	C10—C11—H11	119.5
N2—C1—N1	123.28 (19)	C12—C11—H11	119.5
N2—C1—C2	128.2 (2)	C11—C12—C7	120.2 (2)
N1—C1—C2	108.47 (19)	C11—C12—H12	119.9
C1—C2—C6	113.9 (2)	C7—C12—H12	119.9
C1—C2—C3	107.4 (2)	C18—C13—C14	120.1 (2)
C6—C2—C3	138.5 (2)	C18—C13—N1	118.7 (2)
C4—C3—C2	105.3 (2)	C14—C13—N1	121.2 (2)
C4—C3—C7	123.9 (2)	C15—C14—C13	119.9 (2)
C2—C3—C7	130.7 (2)	C15—C14—H14	120.1
C3—C4—N1	111.3 (2)	C13—C14—H14	120.1
C3—C4—H4	124.3	C14—C15—C16	119.5 (2)
N1—C4—H4	124.3	C14—C15—H15	120.3
N2—C5—N3	121.5 (2)	C16—C15—H15	120.3
N2—C5—H5	119.2	C15—C16—C17	121.5 (2)
N3—C5—H5	119.2	C15—C16—Br	119.33 (19)
N6—C6—N3	107.6 (2)	C17—C16—Br	119.1 (2)
N6—C6—C2	136.3 (2)	C16—C17—C18	118.7 (2)
N3—C6—C2	116.0 (2)	C16—C17—H17	120.7
C8—C7—C12	117.7 (2)	C18—C17—H17	120.7
C8—C7—C3	119.4 (2)	C17—C18—C13	120.3 (2)
C12—C7—C3	122.8 (2)	C17—C18—H18	119.9
C9—C8—C7	121.4 (2)	C13—C18—H18	119.9
C6—N3—N4—N5	0.2 (3)	C1—C2—C6—N6	175.2 (3)
C5—N3—N4—N5	178.1 (3)	C3—C2—C6—N6	0.1 (6)
N3—N4—N5—N6	−0.1 (3)	C1—C2—C6—N3	−2.1 (3)
N4—N5—N6—C6	−0.1 (3)	C3—C2—C6—N3	−177.2 (3)
C5—N2—C1—N1	177.5 (2)	C4—C3—C7—C8	9.1 (4)
C5—N2—C1—C2	−1.3 (4)	C2—C3—C7—C8	−170.4 (3)
C4—N1—C1—N2	−179.8 (2)	C4—C3—C7—C12	−169.9 (3)
C13—N1—C1—N2	−7.7 (4)	C2—C3—C7—C12	10.6 (4)
C4—N1—C1—C2	−0.8 (3)	C12—C7—C8—C9	−0.2 (4)
C13—N1—C1—C2	171.3 (2)	C3—C7—C8—C9	−179.3 (2)
N2—C1—C2—C6	3.1 (4)	C7—C8—C9—C10	0.3 (4)
N1—C1—C2—C6	−175.8 (2)	C8—C9—C10—C11	−0.1 (4)
N2—C1—C2—C3	179.7 (2)	C9—C10—C11—C12	−0.2 (4)
N1—C1—C2—C3	0.8 (3)	C10—C11—C12—C7	0.3 (4)
C1—C2—C3—C4	−0.5 (3)	C8—C7—C12—C11	−0.1 (4)
C6—C2—C3—C4	174.9 (3)	C3—C7—C12—C11	178.9 (2)
C1—C2—C3—C7	179.1 (2)	C1—N1—C13—C18	−143.0 (3)
C6—C2—C3—C7	−5.6 (5)	C4—N1—C13—C18	27.9 (4)
C2—C3—C4—N1	0.0 (3)	C1—N1—C13—C14	37.2 (4)
C7—C3—C4—N1	−179.6 (2)	C4—N1—C13—C14	−151.9 (2)
C1—N1—C4—C3	0.5 (3)	C18—C13—C14—C15	0.1 (4)
C13—N1—C4—C3	−172.0 (2)	N1—C13—C14—C15	179.9 (2)
C1—N2—C5—N3	−1.4 (4)	C13—C14—C15—C16	−1.4 (4)
N4—N3—C5—N2	−175.5 (3)	C14—C15—C16—C17	1.0 (4)
C6—N3—C5—N2	2.1 (4)	C14—C15—C16—Br	−178.9 (2)
N5—N6—C6—N3	0.2 (3)	C15—C16—C17—C18	0.7 (4)
N5—N6—C6—C2	−177.2 (3)	Br—C16—C17—C18	−179.4 (2)
N4—N3—C6—N6	−0.3 (3)	C16—C17—C18—C13	−2.0 (4)
C5—N3—C6—N6	−178.2 (2)	C14—C13—C18—C17	1.6 (4)
N4—N3—C6—C2	177.8 (2)	N1—C13—C18—C17	−178.2 (2)
C5—N3—C6—C2	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N4i	0.95	2.54	3.421 (3)	154
C4—H4···N5i	0.95	2.60	3.532 (3)	166
C5—H5···Brii	0.95	2.87	3.667 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯N4i	0.95	2.54	3.421 (3)	154
C4—H4⋯N5i	0.95	2.60	3.532 (3)	166
C5—H5⋯Brii	0.95	2.87	3.667 (3)	142

Symmetry codes: (i) ; (ii) .