Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035441/hk2298sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035441/hk2298Isup2.hkl |
CCDC reference: 657839
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.028
- wR factor = 0.073
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. N2 .. 3.28 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C15 H12 Br N3 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For a related structure, see: Wan et al. (2006). For bond-length data, see: Allen et al. (1987).
The title compound was prepared according to the literature method (Wan et al., 2006). Single crystals suitable for X-ray diffracion were obtained by slow evaporation of a dichloromethane-cyclohexane (1:2 v/v) solution at room temperature over a period of one week.
H atoms were located in difference syntheses with C—H = 0.9294–0.9301 Å and 0.9690–1.0155 Å, for aromatic and methylene H atoms, and constrained to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(C).
Recently we have reported the strucure of 3-(1H-benzotriazol-1-yl)-1-(4-chloro- phenyl)-propan-1-one (Wan et al., 2006). As part of a search for new benzo- triazole compounds with higher bioactivity, the title compound, (I), was synthesized and its structure is presented here.
In the molecule of the title compound, (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 0.35 (1)° between the A (N1—N3/C10/C11) and B (C10—C15) rings. The mean planes of the benzotriazole ring system and the C (C1—C6) benzene ring make a dihedral angle of 19.0 (1)°.
The crystal packing is stabilized by π-π interactions involving the benzotriazole rings, with Cg1···Cg3i [symmetry code: (i) -x, -2 - y, 1 - z] and Cg2···Cg2ii [symmetry code: (ii) 1 - x, -1 - y, -z] distances of 3.729 and 3.690 Å, where Cg1, Cg2 and Cg3 denote the centroids of the A, C and B rings, respectively.
For a related structure, see: Wan et al. (2006). For bond-length data, see: Allen et al. (1987).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C15H12BrN3O | Z = 2 |
Mr = 330.18 | F(000) = 332 |
Triclinic, P1 | Dx = 1.631 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2310 (8) Å | Cell parameters from 2068 reflections |
b = 8.1517 (9) Å | θ = 3.0–26.0° |
c = 12.5240 (14) Å | µ = 3.06 mm−1 |
α = 101.671 (2)° | T = 298 K |
β = 101.197 (1)° | Block, colourless |
γ = 105.443 (2)° | 0.29 × 0.22 × 0.19 mm |
V = 672.37 (13) Å3 |
Siemens SMART 1000 CCD area-detector diffractometer | 2563 independent reflections |
Radiation source: fine-focus sealed tube | 2232 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.011 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 1.7° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −9→10 |
Tmin = 0.443, Tmax = 0.559 | l = −15→11 |
3771 measured reflections |
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.073 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.042P)2 + 0.1157P] where P = (Fo2 + 2Fc2)/3 |
2563 reflections | (Δ/σ)max < 0.001 |
193 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C15H12BrN3O | γ = 105.443 (2)° |
Mr = 330.18 | V = 672.37 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.2310 (8) Å | Mo Kα radiation |
b = 8.1517 (9) Å | µ = 3.06 mm−1 |
c = 12.5240 (14) Å | T = 298 K |
α = 101.671 (2)° | 0.29 × 0.22 × 0.19 mm |
β = 101.197 (1)° |
Siemens SMART 1000 CCD area-detector diffractometer | 2563 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2232 reflections with I > 2σ(I) |
Tmin = 0.443, Tmax = 0.559 | Rint = 0.011 |
3771 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.073 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.27 e Å−3 |
2563 reflections | Δρmin = −0.29 e Å−3 |
193 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 | ||
Br1 | 0.28029 (3) | −0.23329 (3) | −0.11369 (2) | 0.05799 (11) | |
O2 | 0.3769 (3) | −0.6149 (2) | 0.32203 (14) | 0.0613 (4) | |
N1 | 0.0217 (3) | −0.9405 (2) | 0.32633 (15) | 0.0457 (4) | |
N2 | −0.1692 (3) | −1.0275 (3) | 0.26609 (17) | 0.0558 (5) | |
N3 | −0.2874 (3) | −0.9779 (3) | 0.32235 (18) | 0.0589 (5) | |
C1 | 0.2135 (3) | −0.6601 (3) | 0.0221 (2) | 0.0503 (5) | |
H1A | 0.1607 | −0.7824 | −0.0050 | 0.073 (8)* | |
C2 | 0.2099 (3) | −0.5576 (3) | −0.05288 (19) | 0.0514 (5) | |
H2A | 0.1554 | −0.6106 | −0.1299 | 0.077 (9)* | |
C3 | 0.2880 (3) | −0.3772 (3) | −0.01208 (18) | 0.0430 (5) | |
C4 | 0.3753 (3) | −0.2969 (3) | 0.10188 (19) | 0.0471 (5) | |
H4A | 0.4315 | −0.1748 | 0.1282 | 0.055 (7)* | |
C5 | 0.3773 (3) | −0.4006 (3) | 0.17583 (19) | 0.0448 (5) | |
H5A | 0.4350 | −0.3473 | 0.2525 | 0.056 (7)* | |
C6 | 0.2948 (3) | −0.5835 (3) | 0.13774 (18) | 0.0411 (5) | |
C7 | 0.2992 (3) | −0.6880 (3) | 0.22262 (19) | 0.0446 (5) | |
C8 | 0.2046 (4) | −0.8864 (3) | 0.1827 (2) | 0.0505 (5) | |
H8A | 0.2851 | −0.9369 | 0.1410 | 0.057 (7)* | |
H8B | 0.0746 | −0.9146 | 0.1316 | 0.059 (7)* | |
C9 | 0.1821 (4) | −0.9721 (3) | 0.2790 (2) | 0.0524 (5) | |
H9A | 0.1653 | −1.0996 | 0.2524 | 0.067 (8)* | |
H9B | 0.3119 | −0.9249 | 0.3407 | 0.052 (7)* | |
C10 | 0.0277 (3) | −0.8309 (3) | 0.42539 (18) | 0.0423 (5) | |
C11 | −0.1714 (3) | −0.8559 (3) | 0.42249 (19) | 0.0482 (5) | |
C12 | −0.2241 (4) | −0.7626 (4) | 0.5121 (2) | 0.0611 (6) | |
H12A | −0.3564 | −0.7784 | 0.5115 | 0.061 (7)* | |
C13 | −0.0732 (4) | −0.6475 (4) | 0.6006 (2) | 0.0613 (6) | |
H13A | −0.1040 | −0.5826 | 0.6608 | 0.073 (8)* | |
C14 | 0.1265 (4) | −0.6244 (3) | 0.6022 (2) | 0.0581 (6) | |
H14A | 0.2248 | −0.5461 | 0.6646 | 0.070 (8)* | |
C15 | 0.1821 (3) | −0.7127 (3) | 0.51643 (19) | 0.0507 (5) | |
H15A | 0.3150 | −0.6956 | 0.5179 | 0.063 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.05417 (16) | 0.06219 (18) | 0.06435 (18) | 0.01952 (12) | 0.01661 (12) | 0.02925 (12) |
O2 | 0.0661 (11) | 0.0559 (10) | 0.0493 (10) | 0.0036 (8) | 0.0094 (8) | 0.0133 (8) |
N1 | 0.0457 (10) | 0.0418 (9) | 0.0487 (10) | 0.0109 (8) | 0.0123 (8) | 0.0144 (8) |
N2 | 0.0493 (11) | 0.0533 (11) | 0.0540 (11) | 0.0051 (9) | 0.0076 (9) | 0.0117 (9) |
N3 | 0.0442 (11) | 0.0648 (13) | 0.0596 (13) | 0.0081 (10) | 0.0077 (10) | 0.0173 (10) |
C1 | 0.0532 (13) | 0.0382 (11) | 0.0496 (13) | 0.0046 (10) | 0.0132 (10) | 0.0035 (9) |
C2 | 0.0534 (13) | 0.0493 (13) | 0.0418 (12) | 0.0064 (10) | 0.0098 (10) | 0.0067 (10) |
C3 | 0.0366 (10) | 0.0483 (12) | 0.0481 (12) | 0.0152 (9) | 0.0150 (9) | 0.0158 (9) |
C4 | 0.0458 (12) | 0.0379 (11) | 0.0543 (13) | 0.0114 (9) | 0.0133 (10) | 0.0072 (9) |
C5 | 0.0420 (11) | 0.0440 (11) | 0.0432 (12) | 0.0120 (9) | 0.0104 (9) | 0.0039 (9) |
C6 | 0.0349 (10) | 0.0437 (11) | 0.0455 (12) | 0.0129 (9) | 0.0151 (9) | 0.0088 (9) |
C7 | 0.0383 (11) | 0.0465 (12) | 0.0487 (13) | 0.0113 (9) | 0.0162 (9) | 0.0102 (10) |
C8 | 0.0562 (14) | 0.0446 (12) | 0.0559 (13) | 0.0191 (11) | 0.0224 (11) | 0.0131 (10) |
C9 | 0.0576 (14) | 0.0461 (12) | 0.0626 (14) | 0.0225 (11) | 0.0230 (12) | 0.0194 (11) |
C10 | 0.0434 (11) | 0.0423 (11) | 0.0452 (12) | 0.0134 (9) | 0.0118 (9) | 0.0205 (9) |
C11 | 0.0426 (11) | 0.0540 (13) | 0.0516 (13) | 0.0152 (10) | 0.0120 (10) | 0.0229 (10) |
C12 | 0.0511 (14) | 0.0776 (17) | 0.0674 (16) | 0.0289 (13) | 0.0230 (12) | 0.0287 (14) |
C13 | 0.0735 (17) | 0.0673 (16) | 0.0539 (14) | 0.0326 (14) | 0.0254 (13) | 0.0181 (12) |
C14 | 0.0617 (15) | 0.0608 (15) | 0.0455 (13) | 0.0138 (12) | 0.0087 (11) | 0.0133 (11) |
C15 | 0.0423 (12) | 0.0592 (14) | 0.0475 (13) | 0.0124 (10) | 0.0068 (10) | 0.0172 (11) |
Br1—C3 | 1.900 (2) | C6—C7 | 1.491 (3) |
O2—C7 | 1.213 (3) | C7—C8 | 1.512 (3) |
N1—N2 | 1.355 (3) | C8—C9 | 1.524 (3) |
N1—C10 | 1.360 (3) | C8—H8A | 0.9691 |
N1—C9 | 1.458 (3) | C8—H8B | 0.9690 |
N2—N3 | 1.301 (3) | C9—H9A | 0.9915 |
N3—C11 | 1.381 (3) | C9—H9B | 1.0155 |
C1—C2 | 1.379 (3) | C10—C11 | 1.391 (3) |
C1—C6 | 1.393 (3) | C10—C15 | 1.401 (3) |
C1—H1A | 0.9296 | C11—C12 | 1.399 (4) |
C2—C3 | 1.373 (3) | C12—C13 | 1.365 (4) |
C2—H2A | 0.9301 | C12—H12A | 0.9294 |
C3—C4 | 1.384 (3) | C13—C14 | 1.402 (4) |
C4—C5 | 1.375 (3) | C13—H13A | 0.9298 |
C4—H4A | 0.9301 | C14—C15 | 1.357 (3) |
C5—C6 | 1.391 (3) | C14—H14A | 0.9296 |
C5—H5A | 0.9298 | C15—H15A | 0.9295 |
N2—N1—C10 | 110.28 (18) | C9—C8—H8A | 108.7 |
N2—N1—C9 | 119.08 (19) | C7—C8—H8B | 109.1 |
C10—N1—C9 | 130.63 (19) | C9—C8—H8B | 108.9 |
N3—N2—N1 | 109.04 (18) | H8A—C8—H8B | 107.7 |
N2—N3—C11 | 107.97 (19) | N1—C9—C8 | 111.96 (19) |
C2—C1—C6 | 121.1 (2) | N1—C9—H9A | 112.6 |
C2—C1—H1A | 119.5 | C8—C9—H9A | 109.3 |
C6—C1—H1A | 119.5 | N1—C9—H9B | 109.6 |
C3—C2—C1 | 119.0 (2) | C8—C9—H9B | 109.6 |
C3—C2—H2A | 120.9 | H9A—C9—H9B | 103.3 |
C1—C2—H2A | 120.1 | N1—C10—C11 | 104.11 (19) |
C2—C3—C4 | 121.4 (2) | N1—C10—C15 | 133.9 (2) |
C2—C3—Br1 | 119.67 (17) | C11—C10—C15 | 122.0 (2) |
C4—C3—Br1 | 118.90 (16) | N3—C11—C10 | 108.6 (2) |
C5—C4—C3 | 119.0 (2) | N3—C11—C12 | 131.0 (2) |
C5—C4—H4A | 120.4 | C10—C11—C12 | 120.4 (2) |
C3—C4—H4A | 120.7 | C13—C12—C11 | 117.4 (2) |
C4—C5—C6 | 121.1 (2) | C13—C12—H12A | 121.2 |
C4—C5—H5A | 119.3 | C11—C12—H12A | 121.4 |
C6—C5—H5A | 119.6 | C12—C13—C14 | 121.4 (2) |
C5—C6—C1 | 118.4 (2) | C12—C13—H13A | 119.2 |
C5—C6—C7 | 118.38 (19) | C14—C13—H13A | 119.4 |
C1—C6—C7 | 123.24 (19) | C15—C14—C13 | 122.5 (2) |
O2—C7—C6 | 120.5 (2) | C15—C14—H14A | 118.7 |
O2—C7—C8 | 120.5 (2) | C13—C14—H14A | 118.7 |
C6—C7—C8 | 118.92 (19) | C14—C15—C10 | 116.2 (2) |
C7—C8—C9 | 113.2 (2) | C14—C15—H15A | 121.9 |
C7—C8—H8A | 109.1 | C10—C15—H15A | 121.9 |
C10—N1—N2—N3 | 0.2 (2) | C10—N1—C9—C8 | −105.7 (3) |
C9—N1—N2—N3 | −178.81 (19) | C7—C8—C9—N1 | 74.2 (3) |
N1—N2—N3—C11 | −0.3 (3) | N2—N1—C10—C11 | 0.0 (2) |
C6—C1—C2—C3 | 0.0 (4) | C9—N1—C10—C11 | 178.9 (2) |
C1—C2—C3—C4 | 2.0 (3) | N2—N1—C10—C15 | −179.5 (2) |
C1—C2—C3—Br1 | −178.90 (17) | C9—N1—C10—C15 | −0.6 (4) |
C2—C3—C4—C5 | −2.2 (3) | N2—N3—C11—C10 | 0.4 (3) |
Br1—C3—C4—C5 | 178.65 (16) | N2—N3—C11—C12 | 179.9 (3) |
C3—C4—C5—C6 | 0.5 (3) | N1—C10—C11—N3 | −0.2 (2) |
C4—C5—C6—C1 | 1.4 (3) | C15—C10—C11—N3 | 179.3 (2) |
C4—C5—C6—C7 | −179.08 (19) | N1—C10—C11—C12 | −179.8 (2) |
C2—C1—C6—C5 | −1.6 (3) | C15—C10—C11—C12 | −0.2 (3) |
C2—C1—C6—C7 | 178.9 (2) | N3—C11—C12—C13 | −179.3 (3) |
C5—C6—C7—O2 | −1.6 (3) | C10—C11—C12—C13 | 0.2 (4) |
C1—C6—C7—O2 | 177.9 (2) | C11—C12—C13—C14 | −0.3 (4) |
C5—C6—C7—C8 | 178.20 (19) | C12—C13—C14—C15 | 0.6 (4) |
C1—C6—C7—C8 | −2.3 (3) | C13—C14—C15—C10 | −0.6 (4) |
O2—C7—C8—C9 | 11.6 (3) | N1—C10—C15—C14 | 179.8 (2) |
C6—C7—C8—C9 | −168.27 (19) | C11—C10—C15—C14 | 0.4 (3) |
N2—N1—C9—C8 | 73.1 (3) |
Experimental details
Crystal data | |
Chemical formula | C15H12BrN3O |
Mr | 330.18 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 7.2310 (8), 8.1517 (9), 12.5240 (14) |
α, β, γ (°) | 101.671 (2), 101.197 (1), 105.443 (2) |
V (Å3) | 672.37 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 3.06 |
Crystal size (mm) | 0.29 × 0.22 × 0.19 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.443, 0.559 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3771, 2563, 2232 |
Rint | 0.011 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.073, 1.06 |
No. of reflections | 2563 |
No. of parameters | 193 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.29 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
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Recently we have reported the strucure of 3-(1H-benzotriazol-1-yl)-1-(4-chloro- phenyl)-propan-1-one (Wan et al., 2006). As part of a search for new benzo- triazole compounds with higher bioactivity, the title compound, (I), was synthesized and its structure is presented here.
In the molecule of the title compound, (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 0.35 (1)° between the A (N1—N3/C10/C11) and B (C10—C15) rings. The mean planes of the benzotriazole ring system and the C (C1—C6) benzene ring make a dihedral angle of 19.0 (1)°.
The crystal packing is stabilized by π-π interactions involving the benzotriazole rings, with Cg1···Cg3i [symmetry code: (i) -x, -2 - y, 1 - z] and Cg2···Cg2ii [symmetry code: (ii) 1 - x, -1 - y, -z] distances of 3.729 and 3.690 Å, where Cg1, Cg2 and Cg3 denote the centroids of the A, C and B rings, respectively.