2-Bromo-1-[1-(4-bromo-phen-yl)-5-methyl-1H-1,2,3-triazol-4-yl]ethanone.

The asymmetric unit of the title compound, C11H9Br2N3O, contains two crystallographically independent mol-ecules with similar geometries; the Br-C-C=O torsion angles are 1.2 (4) and -2.8 (4)°, and the benzene and triazole rings are inclined o one another by 51.90 (16) and 51.88 (16)°. The two molecules are related by a pseudo-screw 21 axis directed along [100]. In the crystal, mol-ecules are linked into a three-dimensional network by weak C-H⋯O and C-H⋯N hydrogen bonds and secondary Br⋯Br [3.5991 (8) and 3.6503 (9) Å] inter-actions.

Related literature

For applications of 1,2,3-triazoles, see recent reviews by Agalave et al. (2011 ▶); Thirumurugan et al. (2013 ▶). For the crystal structures of related compounds, see: Danence et al. (2011 ▶); Zeghada et al. (2011 ▶); Abdel-Wahab, Abdel-Latif et al. (2013 ▶); Abdel-Wahab, Mohamed et al. (2013 ▶).

Experimental

Crystal data

C11H9Br2N3O

M = 359.03

Monoclinic,

a = 3.9699 (10) Å

b = 19.437 (5) Å

c = 15.402 (4) Å

β = 90.908 (3)°

V = 1188.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 6.81 mm−1

T = 100 K

0.30 × 0.03 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.235, T max = 0.822

18272 measured reflections

6924 independent reflections

6426 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.067

S = 1.04

6924 reflections

309 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.59 e Å−3

Absolute structure: Flack (1983 ▶), 3428 Friedel pairs

Absolute structure parameter: 0.032 (7)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814014603/cv5467sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014603/cv5467Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814014603/cv5467Isup3.cml

CCDC reference: 1009335

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H9Br2N3O	F(000) = 696
Mr = 359.03	Dx = 2.007 Mg m−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 9920 reflections
a = 3.9699 (10) Å	θ = 2.5–32.2°
b = 19.437 (5) Å	µ = 6.81 mm−1
c = 15.402 (4) Å	T = 100 K
β = 90.908 (3)°	Needle, colourless
V = 1188.3 (5) Å3	0.30 × 0.03 × 0.03 mm
Z = 4

Bruker APEXII CCD diffractometer	6924 independent reflections
Radiation source: fine-focus sealed tube	6426 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −5→5
Tmin = 0.235, Tmax = 0.822	k = −26→27
18272 measured reflections	l = −21→21

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)] = 0.028	H-atom parameters constrained
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.0221P)2 + 0.4369P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
6924 reflections	Δρmax = 0.72 e Å−3
309 parameters	Δρmin = −0.59 e Å−3
2 restraints	Absolute structure: Flack (1983), 3428 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.032 (7)

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	1.07896 (7)	0.863924 (17)	1.13454 (2)	0.02912 (7)
Br2	0.64876 (8)	0.877518 (19)	0.33776 (2)	0.03474 (8)
O1	0.8585 (6)	0.94649 (11)	0.50458 (14)	0.0356 (5)
N1	0.7274 (6)	0.85632 (12)	0.75006 (16)	0.0257 (5)
N2	0.5627 (7)	0.79965 (16)	0.71724 (18)	0.0297 (6)
N3	0.5412 (7)	0.80839 (14)	0.63358 (19)	0.0281 (5)
C4	0.6933 (8)	0.86928 (14)	0.61085 (19)	0.0251 (5)
C5	0.8151 (7)	0.90045 (14)	0.68650 (18)	0.0250 (5)
C6	0.8065 (7)	0.85860 (15)	0.84105 (19)	0.0257 (5)
C7	0.9625 (7)	0.80248 (15)	0.87919 (18)	0.0270 (6)
H7	1.0134	0.7630	0.8454	0.032*
C8	1.0442 (8)	0.80396 (16)	0.9666 (2)	0.0290 (6)
H8	1.1526	0.7658	0.9936	0.035*
C9	0.9654 (7)	0.86206 (14)	1.01434 (18)	0.0243 (5)
C10	0.8081 (8)	0.91854 (15)	0.97703 (19)	0.0282 (6)
H10	0.7562	0.9578	1.0111	0.034*
C11	0.7278 (8)	0.91690 (15)	0.8897 (2)	0.0281 (6)
H11	0.6197	0.9551	0.8627	0.034*
C12	0.7233 (7)	0.89258 (15)	0.52097 (19)	0.0258 (5)
C13	0.5797 (8)	0.84371 (17)	0.4533 (2)	0.0270 (6)
H13A	0.3354	0.8377	0.4627	0.032*
H13B	0.6890	0.7982	0.4598	0.032*
C14	1.0031 (8)	0.96530 (16)	0.7007 (2)	0.0304 (6)
H14A	1.1297	0.9626	0.7557	0.046*
H14B	0.8445	1.0039	0.7027	0.046*
H14C	1.1598	0.9724	0.6530	0.046*
Br3	0.55988 (7)	0.633881 (18)	−0.03542 (2)	0.03091 (8)
Br4	0.09749 (12)	0.62103 (2)	0.75847 (3)	0.04919 (11)
O2	0.3422 (6)	0.55351 (11)	0.59535 (15)	0.0374 (5)
N4	0.2428 (7)	0.64530 (13)	0.34827 (17)	0.0287 (5)
N5	0.0796 (7)	0.70220 (15)	0.3795 (2)	0.0320 (6)
N6	0.0522 (7)	0.69383 (14)	0.46281 (19)	0.0304 (5)
C15	0.2015 (8)	0.63260 (15)	0.4854 (2)	0.0264 (6)
C16	0.3230 (8)	0.60064 (15)	0.41271 (19)	0.0268 (5)
C17	0.3215 (7)	0.64193 (15)	0.2580 (2)	0.0274 (6)
C18	0.4783 (8)	0.69686 (15)	0.21998 (19)	0.0281 (6)
H18	0.5373	0.7362	0.2535	0.034*
C19	0.5504 (8)	0.69455 (16)	0.1318 (2)	0.0274 (6)
H19	0.6588	0.7321	0.1044	0.033*
C20	0.4609 (7)	0.63628 (15)	0.08477 (19)	0.0261 (6)
C21	0.3038 (7)	0.58060 (15)	0.12237 (19)	0.0278 (6)
H21	0.2471	0.5412	0.0888	0.033*
C22	0.2301 (8)	0.58320 (15)	0.21009 (19)	0.0272 (6)
H22	0.1196	0.5458	0.2373	0.033*
C23	0.2154 (8)	0.60812 (15)	0.5765 (2)	0.0286 (6)
C24	0.0729 (9)	0.65717 (17)	0.6432 (2)	0.0287 (6)
H24A	−0.1653	0.6671	0.6279	0.034*
H24B	0.1990	0.7011	0.6412	0.034*
C25	0.5068 (8)	0.53557 (16)	0.4007 (2)	0.0300 (6)
H25A	0.6422	0.5385	0.3482	0.045*
H25B	0.3455	0.4976	0.3949	0.045*
H25C	0.6551	0.5273	0.4511	0.045*

	U11	U22	U33	U12	U13	U23
Br1	0.03673 (15)	0.02734 (16)	0.02318 (14)	−0.00060 (12)	−0.00311 (11)	−0.00161 (13)
Br2	0.04801 (19)	0.03298 (17)	0.02315 (15)	−0.00318 (14)	−0.00196 (12)	0.00142 (13)
O1	0.0514 (14)	0.0268 (11)	0.0287 (11)	−0.0091 (10)	−0.0011 (10)	0.0018 (8)
N1	0.0319 (12)	0.0221 (11)	0.0229 (11)	−0.0024 (9)	0.0001 (9)	−0.0005 (9)
N2	0.0389 (14)	0.0273 (15)	0.0229 (13)	−0.0062 (11)	−0.0002 (10)	−0.0017 (11)
N3	0.0363 (13)	0.0253 (13)	0.0226 (11)	−0.0035 (11)	−0.0004 (9)	−0.0014 (11)
C4	0.0283 (13)	0.0211 (13)	0.0257 (13)	0.0016 (10)	−0.0003 (11)	−0.0007 (10)
C5	0.0290 (13)	0.0198 (12)	0.0261 (13)	−0.0008 (10)	−0.0028 (10)	−0.0014 (10)
C6	0.0297 (13)	0.0254 (13)	0.0220 (12)	0.0005 (11)	−0.0024 (11)	−0.0008 (10)
C7	0.0344 (15)	0.0219 (13)	0.0247 (13)	0.0007 (11)	0.0026 (11)	−0.0026 (10)
C8	0.0351 (14)	0.0228 (14)	0.0291 (15)	0.0025 (12)	0.0024 (11)	0.0005 (13)
C9	0.0293 (14)	0.0223 (13)	0.0213 (12)	−0.0028 (10)	−0.0010 (10)	−0.0015 (10)
C10	0.0336 (15)	0.0216 (13)	0.0293 (14)	0.0007 (11)	−0.0020 (12)	−0.0028 (11)
C11	0.0320 (14)	0.0233 (13)	0.0291 (14)	0.0050 (11)	−0.0009 (11)	0.0005 (11)
C12	0.0301 (13)	0.0233 (13)	0.0239 (13)	0.0005 (10)	−0.0027 (10)	−0.0004 (10)
C13	0.0317 (15)	0.0263 (16)	0.0230 (15)	0.0013 (12)	0.0022 (12)	−0.0030 (13)
C14	0.0377 (16)	0.0213 (14)	0.0321 (15)	−0.0044 (12)	−0.0067 (13)	0.0017 (11)
Br3	0.03856 (16)	0.02766 (17)	0.02664 (16)	0.00068 (13)	0.00437 (12)	−0.00241 (13)
Br4	0.0812 (3)	0.0374 (2)	0.02920 (19)	0.00705 (19)	0.00878 (18)	0.00159 (15)
O2	0.0526 (14)	0.0267 (11)	0.0331 (12)	0.0070 (10)	0.0034 (10)	0.0033 (9)
N4	0.0356 (13)	0.0220 (11)	0.0284 (12)	0.0018 (9)	−0.0011 (10)	−0.0014 (9)
N5	0.0417 (15)	0.0234 (14)	0.0309 (15)	0.0055 (11)	−0.0008 (11)	−0.0035 (12)
N6	0.0375 (13)	0.0245 (13)	0.0291 (13)	0.0048 (11)	−0.0032 (10)	−0.0029 (11)
C15	0.0299 (14)	0.0241 (14)	0.0252 (13)	−0.0010 (11)	0.0035 (12)	−0.0016 (10)
C16	0.0305 (14)	0.0222 (13)	0.0279 (13)	−0.0015 (11)	0.0034 (11)	0.0000 (11)
C17	0.0275 (14)	0.0255 (14)	0.0292 (14)	0.0026 (11)	−0.0005 (11)	−0.0028 (11)
C18	0.0335 (15)	0.0225 (13)	0.0282 (14)	−0.0024 (11)	−0.0031 (11)	−0.0016 (11)
C19	0.0340 (14)	0.0202 (13)	0.0279 (14)	−0.0024 (12)	−0.0035 (11)	0.0025 (13)
C20	0.0278 (14)	0.0250 (14)	0.0253 (13)	0.0018 (10)	−0.0006 (11)	−0.0027 (10)
C21	0.0336 (15)	0.0228 (13)	0.0269 (13)	−0.0001 (11)	−0.0003 (11)	−0.0062 (10)
C22	0.0318 (14)	0.0240 (13)	0.0258 (13)	−0.0060 (11)	−0.0002 (11)	−0.0021 (11)
C23	0.0332 (14)	0.0227 (13)	0.0300 (14)	−0.0027 (11)	0.0014 (12)	−0.0037 (11)
C24	0.0369 (15)	0.0241 (15)	0.0251 (15)	−0.0011 (13)	0.0013 (12)	0.0015 (13)
C25	0.0358 (16)	0.0249 (15)	0.0294 (14)	0.0001 (12)	0.0040 (12)	0.0007 (11)

Br1—C9	1.899 (3)	Br3—C20	1.899 (3)
Br2—C13	1.920 (3)	Br4—C24	1.911 (3)
O1—C12	1.206 (4)	O2—C23	1.208 (4)
N1—C5	1.351 (4)	N4—C16	1.353 (4)
N1—N2	1.373 (4)	N4—N5	1.373 (4)
N1—C6	1.432 (4)	N4—C17	1.432 (4)
N2—N3	1.301 (4)	N5—N6	1.299 (4)
N3—C4	1.376 (4)	N6—C15	1.372 (4)
C4—C5	1.393 (4)	C15—C16	1.375 (4)
C4—C12	1.463 (4)	C15—C23	1.482 (4)
C5—C14	1.479 (4)	C16—C25	1.473 (4)
C6—C7	1.381 (4)	C17—C18	1.372 (4)
C6—C11	1.396 (4)	C17—C22	1.404 (4)
C7—C8	1.380 (4)	C18—C19	1.393 (5)
C7—H7	0.9500	C18—H18	0.9500
C8—C9	1.386 (4)	C19—C20	1.388 (4)
C8—H8	0.9500	C19—H19	0.9500
C9—C10	1.384 (4)	C20—C21	1.381 (4)
C10—C11	1.378 (4)	C21—C22	1.388 (4)
C10—H10	0.9500	C21—H21	0.9500
C11—H11	0.9500	C22—H22	0.9500
C12—C13	1.515 (4)	C23—C24	1.516 (4)
C13—H13A	0.9900	C24—H24A	0.9900
C13—H13B	0.9900	C24—H24B	0.9900
C14—H14A	0.9800	C25—H25A	0.9800
C14—H14B	0.9800	C25—H25B	0.9800
C14—H14C	0.9800	C25—H25C	0.9800
C5—N1—N2	111.7 (2)	C16—N4—N5	111.5 (3)
C5—N1—C6	129.4 (2)	C16—N4—C17	129.1 (3)
N2—N1—C6	118.7 (2)	N5—N4—C17	119.3 (3)
N3—N2—N1	106.5 (3)	N6—N5—N4	107.0 (3)
N2—N3—C4	110.0 (3)	N5—N6—C15	108.5 (3)
N3—C4—C5	108.0 (3)	N6—C15—C16	109.9 (3)
N3—C4—C12	123.3 (3)	N6—C15—C23	121.9 (3)
C5—C4—C12	128.6 (3)	C16—C15—C23	128.2 (3)
N1—C5—C4	103.9 (2)	N4—C16—C15	103.1 (3)
N1—C5—C14	124.7 (3)	N4—C16—C25	124.8 (3)
C4—C5—C14	131.4 (3)	C15—C16—C25	132.1 (3)
C7—C6—C11	121.0 (3)	C18—C17—C22	121.6 (3)
C7—C6—N1	118.8 (3)	C18—C17—N4	119.1 (3)
C11—C6—N1	120.2 (3)	C22—C17—N4	119.3 (3)
C8—C7—C6	119.7 (3)	C17—C18—C19	119.5 (3)
C8—C7—H7	120.2	C17—C18—H18	120.2
C6—C7—H7	120.2	C19—C18—H18	120.2
C7—C8—C9	118.9 (3)	C20—C19—C18	118.7 (3)
C7—C8—H8	120.6	C20—C19—H19	120.6
C9—C8—H8	120.6	C18—C19—H19	120.6
C10—C9—C8	122.0 (3)	C21—C20—C19	122.3 (3)
C10—C9—Br1	119.2 (2)	C21—C20—Br3	119.4 (2)
C8—C9—Br1	118.7 (2)	C19—C20—Br3	118.3 (2)
C11—C10—C9	118.9 (3)	C20—C21—C22	118.9 (3)
C11—C10—H10	120.6	C20—C21—H21	120.6
C9—C10—H10	120.6	C22—C21—H21	120.6
C10—C11—C6	119.5 (3)	C21—C22—C17	119.0 (3)
C10—C11—H11	120.3	C21—C22—H22	120.5
C6—C11—H11	120.3	C17—C22—H22	120.5
O1—C12—C4	120.7 (3)	O2—C23—C15	121.2 (3)
O1—C12—C13	124.4 (3)	O2—C23—C24	123.3 (3)
C4—C12—C13	114.9 (3)	C15—C23—C24	115.5 (3)
C12—C13—Br2	111.4 (2)	C23—C24—Br4	112.6 (2)
C12—C13—H13A	109.3	C23—C24—H24A	109.1
Br2—C13—H13A	109.3	Br4—C24—H24A	109.1
C12—C13—H13B	109.3	C23—C24—H24B	109.1
Br2—C13—H13B	109.3	Br4—C24—H24B	109.1
H13A—C13—H13B	108.0	H24A—C24—H24B	107.8
C5—C14—H14A	109.5	C16—C25—H25A	109.5
C5—C14—H14B	109.5	C16—C25—H25B	109.5
H14A—C14—H14B	109.5	H25A—C25—H25B	109.5
C5—C14—H14C	109.5	C16—C25—H25C	109.5
H14A—C14—H14C	109.5	H25A—C25—H25C	109.5
H14B—C14—H14C	109.5	H25B—C25—H25C	109.5
C5—N1—N2—N3	−1.0 (4)	C16—N4—N5—N6	−0.7 (4)
C6—N1—N2—N3	−176.0 (3)	C17—N4—N5—N6	−177.2 (3)
N1—N2—N3—C4	0.9 (4)	N4—N5—N6—C15	1.0 (4)
N2—N3—C4—C5	−0.5 (4)	N5—N6—C15—C16	−1.0 (4)
N2—N3—C4—C12	177.5 (3)	N5—N6—C15—C23	179.5 (3)
N2—N1—C5—C4	0.7 (3)	N5—N4—C16—C15	0.0 (3)
C6—N1—C5—C4	175.0 (3)	C17—N4—C16—C15	176.2 (3)
N2—N1—C5—C14	−178.3 (3)	N5—N4—C16—C25	−178.4 (3)
C6—N1—C5—C14	−4.0 (5)	C17—N4—C16—C25	−2.2 (5)
N3—C4—C5—N1	−0.2 (3)	N6—C15—C16—N4	0.6 (3)
C12—C4—C5—N1	−178.0 (3)	C23—C15—C16—N4	180.0 (3)
N3—C4—C5—C14	178.8 (3)	N6—C15—C16—C25	178.8 (3)
C12—C4—C5—C14	1.0 (5)	C23—C15—C16—C25	−1.8 (6)
C5—N1—C6—C7	−124.6 (3)	C16—N4—C17—C18	−126.4 (3)
N2—N1—C6—C7	49.3 (4)	N5—N4—C17—C18	49.5 (4)
C5—N1—C6—C11	55.1 (4)	C16—N4—C17—C22	54.9 (4)
N2—N1—C6—C11	−131.0 (3)	N5—N4—C17—C22	−129.2 (3)
C11—C6—C7—C8	−0.4 (5)	C22—C17—C18—C19	−0.2 (5)
N1—C6—C7—C8	179.3 (3)	N4—C17—C18—C19	−178.8 (3)
C6—C7—C8—C9	0.3 (5)	C17—C18—C19—C20	0.0 (5)
C7—C8—C9—C10	−0.1 (5)	C18—C19—C20—C21	−0.2 (5)
C7—C8—C9—Br1	−179.9 (2)	C18—C19—C20—Br3	179.9 (2)
C8—C9—C10—C11	−0.1 (5)	C19—C20—C21—C22	0.6 (5)
Br1—C9—C10—C11	179.7 (2)	Br3—C20—C21—C22	−179.4 (2)
C9—C10—C11—C6	0.0 (5)	C20—C21—C22—C17	−0.8 (4)
C7—C6—C11—C10	0.2 (5)	C18—C17—C22—C21	0.7 (5)
N1—C6—C11—C10	−179.5 (3)	N4—C17—C22—C21	179.3 (3)
N3—C4—C12—O1	179.9 (3)	N6—C15—C23—O2	178.6 (3)
C5—C4—C12—O1	−2.6 (5)	C16—C15—C23—O2	−0.7 (5)
N3—C4—C12—C13	−1.2 (4)	N6—C15—C23—C24	−3.5 (4)
C5—C4—C12—C13	176.3 (3)	C16—C15—C23—C24	177.1 (3)
O1—C12—C13—Br2	1.2 (4)	O2—C23—C24—Br4	−2.8 (4)
C4—C12—C13—Br2	−177.6 (2)	C15—C23—C24—Br4	179.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1i	0.95	2.44	3.205 (4)	137
C13—H13B···N6ii	0.99	2.49	3.467 (4)	170
C21—H21···O2iii	0.95	2.45	3.210 (4)	137
C24—H24B···N3	0.99	2.49	3.482 (4)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O1i	0.95	2.44	3.205 (4)	137
C13—H13B⋯N6ii	0.99	2.49	3.467 (4)	170
C21—H21⋯O2iii	0.95	2.45	3.210 (4)	137
C24—H24B⋯N3	0.99	2.49	3.482 (4)	177

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