Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048180/lh2517sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048180/lh2517Isup2.hkl |
CCDC reference: 669133
To a mixture of 1-bromo-2-(trifluoromethyl)benzene (75 g, 0.33 mol) and concentrated sulfonic acid (37 ml) was added a mixture of concentrated HNO~3 (15 mL) and concentrated H~2SO~4 (24 ml) and cooled with ice-water. The reaction mixture was stirred at room temperature for 2 h. Then the solution was poured into 500 ml ice-water and a solid appeared which was collected through filtration and recrystalized with ethnaol. 50 mg was dissolved in 20 ml me thanol and the solution was kept at room temperature for 10 d; natural evaporation gave colorless single crystals of suitable for X-ray analysis.
H atoms were positioned geometrically, with C—H = 0.95 Å refined in a riding-model approximation, with Uiso(H)=1.2Ueq.
Substituted trifluoromethylindolo[2,3-b]quinoxaline is useful as a immunomodulating agent (Alaimo, 1983). Herein we report the crystal structure of the starting material 1-bromo-4-nitro-2-(trifluoromethyl)benzene (Fig. 1) obtained from 1-bromo-2-(trifluoromethyl)benzene through nitration. There are two and a half molecules in the asymmetric unit. In each molecule the C—C(F3) bond length reflects the expected lack of delocalization of electrons from the benzene ring.
For related literature, see: Alaimo (1983).
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalClear (Rigaku, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).
Fig. 1. The molecular structure of one of the independent molecules in the asymmetric unit drawn with 30% probability ellipsoids. |
C7H3BrF3NO2 | Dx = 2.098 Mg m−3 |
Mr = 270.01 | Melting point = 167–169 K |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 7636 reflections |
a = 9.775 (2) Å | θ = 2.6–25.0° |
b = 34.665 (7) Å | µ = 4.83 mm−1 |
c = 12.615 (3) Å | T = 113 K |
V = 4274.8 (15) Å3 | Platelet, colorless |
Z = 20 | 0.32 × 0.28 × 0.10 mm |
F(000) = 2600 |
Rigaku Saturn diffractometer | 3814 independent reflections |
Radiation source: rotating anode | 3342 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.054 |
Detector resolution: 14.63 pixels mm-1 | θmax = 25.0°, θmin = 1.7° |
ω scans | h = −11→11 |
Absorption correction: numerical (NUMABS; Rigaku, 2005) | k = −41→41 |
Tmin = 0.307, Tmax = 0.644 | l = −10→15 |
19894 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.23 | w = 1/[σ2(Fo2) + (0.0242P)2 + 5.9058P] where P = (Fo2 + 2Fc2)/3 |
3814 reflections | (Δ/σ)max = 0.002 |
334 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
C7H3BrF3NO2 | V = 4274.8 (15) Å3 |
Mr = 270.01 | Z = 20 |
Orthorhombic, Pnma | Mo Kα radiation |
a = 9.775 (2) Å | µ = 4.83 mm−1 |
b = 34.665 (7) Å | T = 113 K |
c = 12.615 (3) Å | 0.32 × 0.28 × 0.10 mm |
Rigaku Saturn diffractometer | 3814 independent reflections |
Absorption correction: numerical (NUMABS; Rigaku, 2005) | 3342 reflections with I > 2σ(I) |
Tmin = 0.307, Tmax = 0.644 | Rint = 0.054 |
19894 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.23 | Δρmax = 0.43 e Å−3 |
3814 reflections | Δρmin = −0.60 e Å−3 |
334 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 | 0.71785 (6) | 0.7500 | 0.49590 (5) | 0.02333 (17) | |
Br2 | −0.10592 (4) | 0.551368 (12) | 0.49280 (3) | 0.02231 (14) | |
Br3 | 0.51998 (5) | 0.645799 (12) | 0.50253 (3) | 0.02508 (14) | |
F1 | 0.5706 (3) | 0.71904 (7) | 0.28711 (19) | 0.0329 (6) | |
F2 | 0.3915 (4) | 0.7500 | 0.2374 (3) | 0.0441 (11) | |
F3 | 0.0436 (3) | 0.57794 (7) | 0.27940 (19) | 0.0336 (6) | |
F4 | 0.2229 (3) | 0.54607 (9) | 0.23590 (19) | 0.0419 (8) | |
F5 | 0.0439 (3) | 0.51612 (7) | 0.28866 (19) | 0.0343 (7) | |
F6 | 0.6698 (3) | 0.61994 (8) | 0.71395 (19) | 0.0357 (7) | |
F7 | 0.8453 (3) | 0.65256 (9) | 0.76192 (19) | 0.0428 (8) | |
F8 | 0.6631 (3) | 0.68178 (7) | 0.71057 (18) | 0.0340 (6) | |
N1 | 0.1000 (5) | 0.7500 | 0.5521 (4) | 0.0237 (12) | |
N2 | 0.5125 (4) | 0.54562 (10) | 0.5514 (3) | 0.0238 (8) | |
N3 | 1.1380 (4) | 0.65554 (10) | 0.4493 (3) | 0.0247 (8) | |
O1 | 0.0275 (5) | 0.7500 | 0.4712 (3) | 0.0394 (12) | |
O2 | 0.0532 (5) | 0.7500 | 0.6412 (3) | 0.0401 (13) | |
O3 | 0.5832 (3) | 0.54160 (9) | 0.4723 (2) | 0.0292 (7) | |
O4 | 0.5569 (3) | 0.54644 (9) | 0.6419 (2) | 0.0314 (8) | |
O5 | 1.2087 (3) | 0.65726 (10) | 0.5286 (3) | 0.0381 (9) | |
O6 | 1.1842 (3) | 0.65564 (10) | 0.3590 (2) | 0.0371 (9) | |
C1 | 0.5243 (6) | 0.7500 | 0.5085 (4) | 0.0188 (13) | |
C2 | 0.4383 (6) | 0.7500 | 0.4201 (4) | 0.0189 (13) | |
C3 | 0.2988 (6) | 0.7500 | 0.4362 (5) | 0.0242 (15) | |
H3 | 0.2382 | 0.7500 | 0.3773 | 0.029* | |
C4 | 0.2480 (6) | 0.7500 | 0.5372 (5) | 0.0200 (13) | |
C5 | 0.3315 (6) | 0.7500 | 0.6263 (4) | 0.0234 (14) | |
H5 | 0.2937 | 0.7500 | 0.6957 | 0.028* | |
C6 | 0.4716 (6) | 0.7500 | 0.6105 (5) | 0.0219 (14) | |
H6 | 0.5318 | 0.7500 | 0.6697 | 0.026* | |
C7 | 0.4938 (6) | 0.7500 | 0.3082 (5) | 0.0256 (14) | |
C8 | 0.0869 (4) | 0.55219 (11) | 0.5058 (3) | 0.0182 (9) | |
C9 | 0.1733 (4) | 0.54956 (11) | 0.4182 (3) | 0.0205 (9) | |
C10 | 0.3136 (4) | 0.54771 (11) | 0.4334 (3) | 0.0203 (10) | |
H10 | 0.3745 | 0.5457 | 0.3749 | 0.024* | |
C11 | 0.3622 (4) | 0.54888 (12) | 0.5362 (3) | 0.0209 (9) | |
C12 | 0.2802 (4) | 0.55240 (12) | 0.6238 (3) | 0.0225 (10) | |
H12 | 0.3181 | 0.5537 | 0.6931 | 0.027* | |
C13 | 0.1405 (5) | 0.55405 (12) | 0.6077 (3) | 0.0242 (10) | |
H13 | 0.0806 | 0.5565 | 0.6667 | 0.029* | |
C14 | 0.1212 (4) | 0.54739 (13) | 0.3056 (3) | 0.0260 (10) | |
C15 | 0.7127 (4) | 0.64767 (12) | 0.4907 (3) | 0.0210 (10) | |
C16 | 0.7981 (4) | 0.65073 (12) | 0.5794 (3) | 0.0201 (10) | |
C17 | 0.9380 (4) | 0.65353 (12) | 0.5639 (3) | 0.0213 (10) | |
H17 | 0.9981 | 0.6554 | 0.6229 | 0.026* | |
C18 | 0.9892 (4) | 0.65353 (12) | 0.4621 (3) | 0.0211 (9) | |
C19 | 0.9059 (4) | 0.65096 (12) | 0.3741 (3) | 0.0226 (10) | |
H19 | 0.9440 | 0.6512 | 0.3048 | 0.027* | |
C20 | 0.7655 (4) | 0.64801 (12) | 0.3885 (3) | 0.0225 (10) | |
H20 | 0.7061 | 0.6462 | 0.3291 | 0.027* | |
C21 | 0.7434 (5) | 0.65155 (13) | 0.6910 (3) | 0.0268 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0202 (3) | 0.0245 (3) | 0.0253 (4) | 0.000 | −0.0005 (3) | 0.000 |
Br2 | 0.0167 (2) | 0.0241 (3) | 0.0261 (3) | 0.00012 (18) | 0.00066 (19) | 0.00021 (18) |
Br3 | 0.0192 (3) | 0.0269 (3) | 0.0291 (3) | −0.00023 (18) | −0.00128 (19) | 0.00139 (18) |
F1 | 0.0358 (16) | 0.0361 (15) | 0.0268 (14) | 0.0032 (13) | 0.0095 (12) | −0.0070 (11) |
F2 | 0.028 (2) | 0.091 (3) | 0.0139 (19) | 0.000 | −0.0012 (17) | 0.000 |
F3 | 0.0398 (16) | 0.0340 (15) | 0.0270 (14) | 0.0056 (13) | −0.0095 (12) | 0.0045 (11) |
F4 | 0.0253 (15) | 0.082 (2) | 0.0183 (14) | 0.0028 (15) | −0.0004 (12) | −0.0042 (14) |
F5 | 0.0393 (16) | 0.0343 (16) | 0.0294 (15) | −0.0051 (13) | −0.0098 (12) | −0.0076 (12) |
F6 | 0.0423 (17) | 0.0352 (16) | 0.0295 (15) | −0.0059 (13) | 0.0083 (13) | 0.0103 (12) |
F7 | 0.0294 (16) | 0.083 (2) | 0.0160 (13) | 0.0012 (16) | −0.0023 (12) | −0.0010 (13) |
F8 | 0.0410 (17) | 0.0352 (16) | 0.0259 (14) | 0.0061 (13) | 0.0098 (12) | −0.0043 (11) |
N1 | 0.022 (3) | 0.030 (3) | 0.019 (3) | 0.000 | −0.002 (2) | 0.000 |
N2 | 0.021 (2) | 0.024 (2) | 0.026 (2) | −0.0008 (16) | −0.0073 (18) | 0.0009 (16) |
N3 | 0.026 (2) | 0.026 (2) | 0.022 (2) | 0.0000 (17) | 0.0018 (18) | 0.0019 (16) |
O1 | 0.026 (3) | 0.069 (4) | 0.023 (2) | 0.000 | −0.007 (2) | 0.000 |
O2 | 0.025 (3) | 0.079 (4) | 0.016 (2) | 0.000 | 0.006 (2) | 0.000 |
O3 | 0.0215 (18) | 0.042 (2) | 0.0239 (17) | 0.0042 (15) | 0.0010 (14) | −0.0009 (15) |
O4 | 0.0261 (18) | 0.045 (2) | 0.0229 (17) | −0.0038 (15) | −0.0078 (14) | −0.0005 (14) |
O5 | 0.0189 (18) | 0.071 (3) | 0.0250 (18) | −0.0058 (17) | −0.0026 (15) | −0.0014 (17) |
O6 | 0.027 (2) | 0.062 (2) | 0.0224 (18) | −0.0043 (17) | 0.0091 (15) | −0.0014 (16) |
C1 | 0.023 (3) | 0.012 (3) | 0.021 (3) | 0.000 | −0.004 (3) | 0.000 |
C2 | 0.022 (3) | 0.021 (3) | 0.014 (3) | 0.000 | 0.001 (3) | 0.000 |
C3 | 0.027 (4) | 0.027 (4) | 0.018 (3) | 0.000 | −0.004 (3) | 0.000 |
C4 | 0.021 (3) | 0.020 (3) | 0.019 (3) | 0.000 | 0.007 (3) | 0.000 |
C5 | 0.028 (4) | 0.030 (4) | 0.013 (3) | 0.000 | 0.001 (3) | 0.000 |
C6 | 0.027 (4) | 0.018 (3) | 0.021 (3) | 0.000 | −0.001 (3) | 0.000 |
C7 | 0.017 (3) | 0.037 (4) | 0.022 (3) | 0.000 | 0.002 (3) | 0.000 |
C8 | 0.015 (2) | 0.018 (2) | 0.021 (2) | −0.0001 (17) | −0.0026 (18) | −0.0025 (17) |
C9 | 0.025 (3) | 0.017 (2) | 0.020 (2) | 0.0034 (18) | −0.0015 (19) | −0.0004 (17) |
C10 | 0.022 (3) | 0.022 (2) | 0.017 (2) | −0.0043 (19) | 0.0026 (18) | 0.0014 (17) |
C11 | 0.020 (2) | 0.021 (2) | 0.022 (2) | 0.0007 (18) | 0.0051 (19) | −0.0002 (18) |
C12 | 0.025 (3) | 0.026 (3) | 0.016 (2) | 0.000 (2) | −0.0023 (18) | −0.0028 (18) |
C13 | 0.027 (3) | 0.025 (2) | 0.021 (2) | −0.002 (2) | 0.0072 (19) | −0.0026 (18) |
C14 | 0.019 (2) | 0.036 (3) | 0.023 (2) | 0.002 (2) | −0.002 (2) | 0.000 (2) |
C15 | 0.019 (2) | 0.020 (2) | 0.024 (2) | 0.0037 (18) | −0.0014 (19) | 0.0005 (18) |
C16 | 0.022 (3) | 0.019 (2) | 0.019 (2) | −0.0017 (18) | 0.0005 (19) | 0.0011 (18) |
C17 | 0.023 (3) | 0.020 (2) | 0.021 (2) | −0.0019 (19) | −0.0009 (19) | −0.0011 (18) |
C18 | 0.021 (2) | 0.020 (2) | 0.022 (2) | −0.0031 (19) | 0.002 (2) | −0.0022 (18) |
C19 | 0.027 (3) | 0.025 (2) | 0.016 (2) | 0.001 (2) | 0.0038 (19) | 0.0008 (18) |
C20 | 0.024 (3) | 0.021 (2) | 0.022 (2) | 0.002 (2) | −0.0046 (19) | 0.0008 (18) |
C21 | 0.025 (3) | 0.036 (3) | 0.019 (2) | 0.003 (2) | 0.000 (2) | 0.003 (2) |
Br1—C1 | 1.898 (6) | C4—C5 | 1.388 (8) |
Br2—C8 | 1.892 (4) | C5—C6 | 1.385 (8) |
Br3—C15 | 1.891 (4) | C5—H5 | 0.9500 |
F1—C7 | 1.336 (4) | C6—H6 | 0.9500 |
F2—C7 | 1.342 (7) | C7—F1i | 1.336 (4) |
F3—C14 | 1.343 (5) | C8—C13 | 1.389 (5) |
F4—C14 | 1.328 (5) | C8—C9 | 1.394 (6) |
F5—C14 | 1.338 (5) | C9—C10 | 1.386 (6) |
F6—C21 | 1.342 (5) | C9—C14 | 1.511 (6) |
F7—C21 | 1.339 (5) | C10—C11 | 1.382 (6) |
F8—C21 | 1.333 (5) | C10—H10 | 0.9500 |
N1—O2 | 1.213 (6) | C11—C12 | 1.370 (6) |
N1—O1 | 1.242 (6) | C12—C13 | 1.382 (6) |
N1—C4 | 1.459 (8) | C12—H12 | 0.9500 |
N2—O4 | 1.221 (4) | C13—H13 | 0.9500 |
N2—O3 | 1.222 (4) | C15—C20 | 1.388 (6) |
N2—C11 | 1.486 (6) | C15—C16 | 1.400 (6) |
N3—O5 | 1.217 (4) | C16—C17 | 1.385 (6) |
N3—O6 | 1.225 (4) | C16—C21 | 1.507 (6) |
N3—C18 | 1.466 (5) | C17—C18 | 1.378 (6) |
C1—C6 | 1.387 (8) | C17—H17 | 0.9500 |
C1—C2 | 1.397 (8) | C18—C19 | 1.379 (6) |
C2—C3 | 1.378 (8) | C19—C20 | 1.389 (6) |
C2—C7 | 1.511 (8) | C19—H19 | 0.9500 |
C3—C4 | 1.368 (8) | C20—H20 | 0.9500 |
C3—H3 | 0.9500 | ||
O2—N1—O1 | 123.1 (5) | C9—C10—H10 | 121.0 |
O2—N1—C4 | 119.5 (5) | C12—C11—C10 | 123.9 (4) |
O1—N1—C4 | 117.4 (5) | C12—C11—N2 | 118.8 (4) |
O4—N2—O3 | 124.4 (4) | C10—C11—N2 | 117.3 (4) |
O4—N2—C11 | 118.0 (4) | C11—C12—C13 | 117.6 (4) |
O3—N2—C11 | 117.6 (3) | C11—C12—H12 | 121.2 |
O5—N3—O6 | 123.7 (4) | C13—C12—H12 | 121.2 |
O5—N3—C18 | 118.4 (4) | C12—C13—C8 | 120.4 (4) |
O6—N3—C18 | 117.9 (4) | C12—C13—H13 | 119.8 |
C6—C1—C2 | 121.2 (6) | C8—C13—H13 | 119.8 |
C6—C1—Br1 | 116.6 (4) | F4—C14—F5 | 106.8 (4) |
C2—C1—Br1 | 122.2 (4) | F4—C14—F3 | 106.7 (4) |
C3—C2—C1 | 118.5 (5) | F5—C14—F3 | 106.3 (3) |
C3—C2—C7 | 119.5 (5) | F4—C14—C9 | 111.8 (4) |
C1—C2—C7 | 121.9 (5) | F5—C14—C9 | 112.4 (4) |
C4—C3—C2 | 119.8 (6) | F3—C14—C9 | 112.5 (4) |
C4—C3—H3 | 120.1 | C20—C15—C16 | 121.3 (4) |
C2—C3—H3 | 120.1 | C20—C15—Br3 | 116.4 (3) |
C3—C4—C5 | 122.7 (6) | C16—C15—Br3 | 122.2 (3) |
C3—C4—N1 | 118.7 (5) | C17—C16—C15 | 118.8 (4) |
C5—C4—N1 | 118.6 (5) | C17—C16—C21 | 118.7 (4) |
C6—C5—C4 | 117.7 (5) | C15—C16—C21 | 122.5 (4) |
C6—C5—H5 | 121.1 | C18—C17—C16 | 119.3 (4) |
C4—C5—H5 | 121.1 | C18—C17—H17 | 120.3 |
C5—C6—C1 | 120.1 (6) | C16—C17—H17 | 120.3 |
C5—C6—H6 | 120.0 | C17—C18—C19 | 122.4 (4) |
C1—C6—H6 | 120.0 | C17—C18—N3 | 117.6 (4) |
F1i—C7—F1 | 106.9 (5) | C19—C18—N3 | 120.0 (4) |
F1i—C7—F2 | 106.6 (3) | C18—C19—C20 | 118.8 (4) |
F1—C7—F2 | 106.6 (3) | C18—C19—H19 | 120.6 |
F1i—C7—C2 | 112.8 (3) | C20—C19—H19 | 120.6 |
F1—C7—C2 | 112.8 (3) | C15—C20—C19 | 119.4 (4) |
F2—C7—C2 | 110.7 (5) | C15—C20—H20 | 120.3 |
C13—C8—C9 | 120.5 (4) | C19—C20—H20 | 120.3 |
C13—C8—Br2 | 117.2 (3) | F8—C21—F7 | 107.1 (4) |
C9—C8—Br2 | 122.3 (3) | F8—C21—F6 | 106.7 (3) |
C10—C9—C8 | 119.6 (4) | F7—C21—F6 | 106.0 (3) |
C10—C9—C14 | 117.5 (4) | F8—C21—C16 | 113.4 (4) |
C8—C9—C14 | 123.0 (4) | F7—C21—C16 | 111.1 (4) |
C11—C10—C9 | 117.9 (4) | F6—C21—C16 | 112.1 (4) |
C11—C10—H10 | 121.0 | ||
C6—C1—C2—C3 | 0.000 (1) | C10—C11—C12—C13 | 1.4 (7) |
Br1—C1—C2—C3 | 180.0 | N2—C11—C12—C13 | −177.8 (4) |
C6—C1—C2—C7 | 180.000 (2) | C11—C12—C13—C8 | 0.0 (6) |
Br1—C1—C2—C7 | 0.000 (2) | C9—C8—C13—C12 | −1.5 (6) |
C1—C2—C3—C4 | 0.000 (1) | Br2—C8—C13—C12 | 176.1 (3) |
C7—C2—C3—C4 | 180.000 (1) | C10—C9—C14—F4 | −3.5 (6) |
C2—C3—C4—C5 | 0.000 (1) | C8—C9—C14—F4 | 178.4 (4) |
C2—C3—C4—N1 | 180.0 | C10—C9—C14—F5 | 116.6 (4) |
O2—N1—C4—C3 | 180.000 (1) | C8—C9—C14—F5 | −61.6 (5) |
O1—N1—C4—C3 | 0.000 (1) | C10—C9—C14—F3 | −123.5 (4) |
O2—N1—C4—C5 | 0.000 (1) | C8—C9—C14—F3 | 58.4 (5) |
O1—N1—C4—C5 | 180.000 (1) | C20—C15—C16—C17 | −1.0 (6) |
C3—C4—C5—C6 | 0.000 (1) | Br3—C15—C16—C17 | −177.4 (3) |
N1—C4—C5—C6 | 180.000 (1) | C20—C15—C16—C21 | 178.3 (4) |
C4—C5—C6—C1 | 0.000 (1) | Br3—C15—C16—C21 | 1.9 (6) |
C2—C1—C6—C5 | 0.000 (1) | C15—C16—C17—C18 | 0.5 (6) |
Br1—C1—C6—C5 | 180.000 (1) | C21—C16—C17—C18 | −178.8 (4) |
C3—C2—C7—F1i | 119.4 (4) | C16—C17—C18—C19 | 0.2 (6) |
C1—C2—C7—F1i | −60.6 (4) | C16—C17—C18—N3 | −178.5 (4) |
C3—C2—C7—F1 | −119.4 (4) | O5—N3—C18—C17 | −0.3 (6) |
C1—C2—C7—F1 | 60.6 (4) | O6—N3—C18—C17 | −179.8 (4) |
C3—C2—C7—F2 | 0.000 (1) | O5—N3—C18—C19 | −179.0 (4) |
C1—C2—C7—F2 | 180.0 | O6—N3—C18—C19 | 1.4 (6) |
C13—C8—C9—C10 | 1.8 (6) | C17—C18—C19—C20 | −0.5 (7) |
Br2—C8—C9—C10 | −175.7 (3) | N3—C18—C19—C20 | 178.2 (4) |
C13—C8—C9—C14 | 179.9 (4) | C16—C15—C20—C19 | 0.8 (6) |
Br2—C8—C9—C14 | 2.4 (6) | Br3—C15—C20—C19 | 177.4 (3) |
C8—C9—C10—C11 | −0.5 (6) | C18—C19—C20—C15 | −0.1 (6) |
C14—C9—C10—C11 | −178.7 (4) | C17—C16—C21—F8 | 116.7 (4) |
C9—C10—C11—C12 | −1.1 (6) | C15—C16—C21—F8 | −62.6 (6) |
C9—C10—C11—N2 | 178.1 (4) | C17—C16—C21—F7 | −4.0 (6) |
O4—N2—C11—C12 | −0.4 (6) | C15—C16—C21—F7 | 176.7 (4) |
O3—N2—C11—C12 | 178.3 (4) | C17—C16—C21—F6 | −122.4 (4) |
O4—N2—C11—C10 | −179.7 (4) | C15—C16—C21—F6 | 58.3 (6) |
O3—N2—C11—C10 | −0.9 (6) |
Symmetry code: (i) x, −y+3/2, z. |
Experimental details
Crystal data | |
Chemical formula | C7H3BrF3NO2 |
Mr | 270.01 |
Crystal system, space group | Orthorhombic, Pnma |
Temperature (K) | 113 |
a, b, c (Å) | 9.775 (2), 34.665 (7), 12.615 (3) |
V (Å3) | 4274.8 (15) |
Z | 20 |
Radiation type | Mo Kα |
µ (mm−1) | 4.83 |
Crystal size (mm) | 0.32 × 0.28 × 0.10 |
Data collection | |
Diffractometer | Rigaku Saturn |
Absorption correction | Numerical (NUMABS; Rigaku, 2005) |
Tmin, Tmax | 0.307, 0.644 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19894, 3814, 3342 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.093, 1.23 |
No. of reflections | 3814 |
No. of parameters | 334 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.60 |
Computer programs: CrystalClear (Rigaku, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), CrystalStructure (Rigaku/MSC, 2005).
Substituted trifluoromethylindolo[2,3-b]quinoxaline is useful as a immunomodulating agent (Alaimo, 1983). Herein we report the crystal structure of the starting material 1-bromo-4-nitro-2-(trifluoromethyl)benzene (Fig. 1) obtained from 1-bromo-2-(trifluoromethyl)benzene through nitration. There are two and a half molecules in the asymmetric unit. In each molecule the C—C(F3) bond length reflects the expected lack of delocalization of electrons from the benzene ring.