Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007002/cv6465sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007002/cv6465Isup2.hkl |
CCDC reference: 270286
Key indicators
- Single-crystal X-ray study
- T = 122 K
- Mean (C-C) = 0.002 Å
- R factor = 0.024
- wR factor = 0.057
- Data-to-parameter ratio = 22.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) ....... ?
Alert level G ABSTY01_ALERT_1_G Extra text has been found in the _exptl_absorpt_correction_type field, which should be only a single keyword. A literature citation should be included in the _exptl_absorpt_process_details field. REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 31.00 From the CIF: _reflns_number_total 5137 Count of symmetry unique reflns 2723 Completeness (_total/calc) 188.65% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2414 Fraction of Friedel pairs measured 0.887 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
C22H15BrN2 | F(000) = 784 |
Mr = 387.27 | Dx = 1.589 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 26555 reflections |
a = 6.0163 (4) Å | θ = 2.3–31.0° |
b = 29.332 (3) Å | µ = 2.55 mm−1 |
c = 9.1726 (8) Å | T = 122 K |
V = 1618.7 (2) Å3 | Plate, pale yellow |
Z = 4 | 0.55 × 0.46 × 0.08 mm |
Nonius KappaCCD diffractometer | 5137 independent reflections |
Radiation source: fine-focus sealed tube | 4771 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
ω and φ scans | θmax = 31.0°, θmin = 2.3° |
Absorption correction: gaussian integration (Coppens, 1970) | h = −8→8 |
Tmin = 0.365, Tmax = 0.903 | k = −42→42 |
36851 measured reflections | l = −13→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.057 | w = 1/[σ2(Fo2) + (0.0299P)2 + 0.9474P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max = 0.001 |
5137 reflections | Δρmax = 0.45 e Å−3 |
226 parameters | Δρmin = −0.34 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2414 Friedel reflections |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.009 (6) |
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 | ||
Br | −0.65262 (2) | −0.079703 (4) | 0.66608 (2) | 0.02019 (4) | |
C1 | 0.2810 (3) | 0.12851 (5) | 0.63824 (16) | 0.0147 (3) | |
C2 | 0.4766 (2) | 0.15389 (5) | 0.6796 (2) | 0.0160 (3) | |
C3 | 0.5778 (3) | 0.15164 (6) | 0.8179 (2) | 0.0205 (3) | |
H3 | 0.5160 | 0.1325 | 0.8911 | 0.025* | |
C4 | 0.7664 (3) | 0.17701 (7) | 0.8485 (2) | 0.0232 (3) | |
H4 | 0.8322 | 0.1753 | 0.9425 | 0.028* | |
C5 | 0.8605 (3) | 0.20499 (7) | 0.7421 (2) | 0.0233 (4) | |
H5 | 0.9890 | 0.2225 | 0.7638 | 0.028* | |
C6 | 0.7662 (3) | 0.20704 (6) | 0.6052 (2) | 0.0205 (3) | |
H6 | 0.8327 | 0.2259 | 0.5332 | 0.025* | |
C7 | 0.5733 (3) | 0.18192 (5) | 0.56891 (19) | 0.0161 (3) | |
C8 | 0.4785 (3) | 0.18403 (5) | 0.42141 (18) | 0.0155 (3) | |
C9 | 0.5761 (3) | 0.20979 (5) | 0.30803 (19) | 0.0196 (3) | |
H9 | 0.7085 | 0.2265 | 0.3268 | 0.023* | |
C10 | 0.4831 (3) | 0.21123 (5) | 0.1706 (3) | 0.0205 (3) | |
H10 | 0.5533 | 0.2284 | 0.0958 | 0.025* | |
C11 | 0.2855 (3) | 0.18750 (5) | 0.14049 (17) | 0.0191 (3) | |
H11 | 0.2208 | 0.1890 | 0.0461 | 0.023* | |
C12 | 0.1862 (3) | 0.16206 (5) | 0.24821 (18) | 0.0172 (3) | |
H12 | 0.0522 | 0.1461 | 0.2282 | 0.021* | |
C13 | 0.2816 (3) | 0.15951 (5) | 0.38757 (18) | 0.0145 (3) | |
C14 | 0.1904 (3) | 0.13112 (5) | 0.49977 (17) | 0.0144 (3) | |
N15 | 0.0150 (2) | 0.10129 (5) | 0.48414 (15) | 0.0153 (2) | |
C16 | −0.0005 (3) | 0.08081 (5) | 0.61194 (19) | 0.0155 (3) | |
N17 | 0.1543 (2) | 0.09612 (5) | 0.71083 (15) | 0.0160 (3) | |
C18 | 0.1628 (3) | 0.08460 (6) | 0.86542 (19) | 0.0225 (3) | |
H18A | 0.1791 | 0.1126 | 0.9230 | 0.034* | |
H18B | 0.2897 | 0.0645 | 0.8837 | 0.034* | |
H18C | 0.0251 | 0.0690 | 0.8934 | 0.034* | |
C19 | −0.1581 (3) | 0.04300 (5) | 0.63613 (15) | 0.0148 (3) | |
C20 | −0.3628 (3) | 0.04461 (5) | 0.56351 (18) | 0.0160 (3) | |
H20 | −0.4002 | 0.0707 | 0.5071 | 0.019* | |
C21 | −0.5119 (3) | 0.00851 (5) | 0.57303 (18) | 0.0163 (3) | |
H21 | −0.6514 | 0.0098 | 0.5247 | 0.020* | |
C22 | −0.4530 (2) | −0.02955 (5) | 0.6546 (2) | 0.0153 (3) | |
C23 | −0.2506 (3) | −0.03255 (5) | 0.72577 (18) | 0.0165 (3) | |
H23 | −0.2126 | −0.0591 | 0.7798 | 0.020* | |
C24 | −0.1033 (3) | 0.00418 (6) | 0.71667 (19) | 0.0173 (3) | |
H24 | 0.0356 | 0.0027 | 0.7658 | 0.021* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.01858 (7) | 0.01718 (6) | 0.02480 (7) | −0.00343 (5) | 0.00294 (9) | 0.00021 (8) |
C1 | 0.0141 (6) | 0.0144 (6) | 0.0157 (9) | 0.0021 (5) | 0.0018 (5) | −0.0014 (5) |
C2 | 0.0138 (6) | 0.0164 (5) | 0.0179 (8) | 0.0026 (4) | 0.0026 (7) | −0.0019 (7) |
C3 | 0.0185 (8) | 0.0236 (7) | 0.0193 (8) | 0.0008 (6) | −0.0016 (6) | 0.0007 (6) |
C4 | 0.0178 (8) | 0.0305 (8) | 0.0212 (8) | 0.0012 (7) | −0.0045 (7) | −0.0034 (7) |
C5 | 0.0166 (9) | 0.0263 (8) | 0.0271 (9) | −0.0021 (7) | −0.0042 (7) | −0.0051 (7) |
C6 | 0.0165 (8) | 0.0200 (8) | 0.0250 (8) | −0.0020 (6) | 0.0015 (7) | −0.0013 (7) |
C7 | 0.0144 (7) | 0.0151 (6) | 0.0188 (7) | 0.0009 (5) | 0.0005 (6) | −0.0019 (6) |
C8 | 0.0158 (7) | 0.0129 (6) | 0.0178 (7) | 0.0012 (5) | 0.0012 (6) | −0.0021 (5) |
C9 | 0.0201 (8) | 0.0169 (7) | 0.0217 (8) | −0.0035 (6) | 0.0025 (6) | −0.0011 (6) |
C10 | 0.0261 (7) | 0.0177 (6) | 0.0177 (6) | −0.0024 (5) | 0.0046 (9) | −0.0011 (8) |
C11 | 0.0260 (7) | 0.0157 (6) | 0.0157 (9) | 0.0021 (6) | −0.0003 (6) | −0.0008 (5) |
C12 | 0.0196 (8) | 0.0141 (6) | 0.0180 (7) | 0.0003 (5) | −0.0011 (6) | −0.0007 (6) |
C13 | 0.0151 (7) | 0.0121 (6) | 0.0162 (7) | 0.0017 (5) | 0.0009 (6) | −0.0021 (5) |
C14 | 0.0145 (7) | 0.0139 (6) | 0.0147 (7) | 0.0019 (5) | 0.0007 (5) | −0.0017 (5) |
N15 | 0.0148 (6) | 0.0148 (6) | 0.0164 (6) | 0.0000 (5) | 0.0006 (5) | 0.0000 (5) |
C16 | 0.0146 (7) | 0.0143 (6) | 0.0176 (6) | 0.0012 (5) | 0.0008 (6) | −0.0003 (5) |
N17 | 0.0161 (6) | 0.0166 (6) | 0.0153 (6) | −0.0003 (5) | 0.0005 (5) | 0.0003 (5) |
C18 | 0.0281 (9) | 0.0246 (8) | 0.0146 (7) | −0.0039 (7) | −0.0019 (7) | 0.0013 (6) |
C19 | 0.0146 (6) | 0.0151 (6) | 0.0147 (8) | 0.0000 (5) | 0.0027 (5) | 0.0005 (5) |
C20 | 0.0163 (7) | 0.0151 (6) | 0.0167 (7) | 0.0021 (5) | 0.0013 (6) | 0.0017 (6) |
C21 | 0.0146 (7) | 0.0192 (7) | 0.0152 (7) | 0.0018 (6) | 0.0006 (6) | 0.0014 (6) |
C22 | 0.0157 (6) | 0.0155 (5) | 0.0147 (7) | −0.0012 (5) | 0.0023 (7) | −0.0021 (7) |
C23 | 0.0184 (7) | 0.0151 (6) | 0.0160 (7) | 0.0029 (6) | 0.0005 (6) | 0.0024 (6) |
C24 | 0.0163 (7) | 0.0186 (7) | 0.0169 (6) | 0.0019 (6) | −0.0004 (6) | 0.0013 (6) |
Br—C22 | 1.9020 (14) | C11—H11 | 0.9500 |
C1—C14 | 1.384 (2) | C12—C13 | 1.403 (2) |
C1—N17 | 1.388 (2) | C12—H12 | 0.9500 |
C1—C2 | 1.443 (2) | C13—C14 | 1.433 (2) |
C2—C3 | 1.409 (3) | C14—N15 | 1.378 (2) |
C2—C7 | 1.430 (2) | N15—C16 | 1.320 (2) |
C3—C4 | 1.386 (3) | C16—N17 | 1.376 (2) |
C3—H3 | 0.9500 | C16—C19 | 1.476 (2) |
C4—C5 | 1.395 (3) | N17—C18 | 1.459 (2) |
C4—H4 | 0.9500 | C18—H18A | 0.9800 |
C5—C6 | 1.379 (3) | C18—H18B | 0.9800 |
C5—H5 | 0.9500 | C18—H18C | 0.9800 |
C6—C7 | 1.414 (2) | C19—C24 | 1.397 (2) |
C6—H6 | 0.9500 | C19—C20 | 1.401 (2) |
C7—C8 | 1.470 (2) | C20—C21 | 1.391 (2) |
C8—C9 | 1.413 (2) | C20—H20 | 0.9500 |
C8—C13 | 1.420 (2) | C21—C22 | 1.390 (2) |
C9—C10 | 1.380 (3) | C21—H21 | 0.9500 |
C9—H9 | 0.9500 | C22—C23 | 1.384 (2) |
C10—C11 | 1.405 (2) | C23—C24 | 1.398 (2) |
C10—H10 | 0.9500 | C23—H23 | 0.9500 |
C11—C12 | 1.375 (2) | C24—H24 | 0.9500 |
C14—C1—N17 | 105.17 (13) | C12—C13—C14 | 121.92 (15) |
C14—C1—C2 | 122.25 (15) | C8—C13—C14 | 117.17 (14) |
N17—C1—C2 | 132.43 (15) | N15—C14—C1 | 111.21 (14) |
C3—C2—C7 | 119.37 (14) | N15—C14—C13 | 125.97 (14) |
C3—C2—C1 | 124.38 (16) | C1—C14—C13 | 122.70 (15) |
C7—C2—C1 | 116.22 (16) | C16—N15—C14 | 104.51 (13) |
C4—C3—C2 | 120.70 (17) | N15—C16—N17 | 112.90 (14) |
C4—C3—H3 | 119.6 | N15—C16—C19 | 121.37 (15) |
C2—C3—H3 | 119.6 | N17—C16—C19 | 125.54 (14) |
C3—C4—C5 | 120.45 (17) | C16—N17—C1 | 106.19 (13) |
C3—C4—H4 | 119.8 | C16—N17—C18 | 126.09 (14) |
C5—C4—H4 | 119.8 | C1—N17—C18 | 127.28 (14) |
C6—C5—C4 | 119.72 (17) | N17—C18—H18A | 109.5 |
C6—C5—H5 | 120.1 | N17—C18—H18B | 109.5 |
C4—C5—H5 | 120.1 | H18A—C18—H18B | 109.5 |
C5—C6—C7 | 121.95 (17) | N17—C18—H18C | 109.5 |
C5—C6—H6 | 119.0 | H18A—C18—H18C | 109.5 |
C7—C6—H6 | 119.0 | H18B—C18—H18C | 109.5 |
C6—C7—C2 | 117.79 (16) | C24—C19—C20 | 119.10 (14) |
C6—C7—C8 | 120.88 (15) | C24—C19—C16 | 122.71 (14) |
C2—C7—C8 | 121.32 (15) | C20—C19—C16 | 117.91 (14) |
C9—C8—C13 | 117.17 (15) | C21—C20—C19 | 120.77 (15) |
C9—C8—C7 | 122.59 (15) | C21—C20—H20 | 119.6 |
C13—C8—C7 | 120.24 (14) | C19—C20—H20 | 119.6 |
C10—C9—C8 | 121.34 (16) | C22—C21—C20 | 118.74 (15) |
C10—C9—H9 | 119.3 | C22—C21—H21 | 120.6 |
C8—C9—H9 | 119.3 | C20—C21—H21 | 120.6 |
C9—C10—C11 | 120.49 (17) | C23—C22—C21 | 121.96 (14) |
C9—C10—H10 | 119.8 | C23—C22—Br | 118.70 (12) |
C11—C10—H10 | 119.8 | C21—C22—Br | 119.33 (12) |
C12—C11—C10 | 119.70 (16) | C22—C23—C24 | 118.73 (15) |
C12—C11—H11 | 120.1 | C22—C23—H23 | 120.6 |
C10—C11—H11 | 120.1 | C24—C23—H23 | 120.6 |
C11—C12—C13 | 120.39 (16) | C19—C24—C23 | 120.69 (15) |
C11—C12—H12 | 119.8 | C19—C24—H24 | 119.7 |
C13—C12—H12 | 119.8 | C23—C24—H24 | 119.7 |
C12—C13—C8 | 120.88 (15) | ||
C14—C1—C2—C3 | −178.57 (15) | N17—C1—C14—C13 | −176.96 (14) |
N17—C1—C2—C3 | −3.6 (3) | C2—C1—C14—C13 | −0.8 (2) |
C14—C1—C2—C7 | −0.3 (2) | C12—C13—C14—N15 | 4.9 (2) |
N17—C1—C2—C7 | 174.70 (15) | C8—C13—C14—N15 | −172.98 (14) |
C7—C2—C3—C4 | 1.4 (2) | C12—C13—C14—C1 | −179.37 (15) |
C1—C2—C3—C4 | 179.63 (16) | C8—C13—C14—C1 | 2.7 (2) |
C2—C3—C4—C5 | −0.5 (3) | C1—C14—N15—C16 | 0.01 (17) |
C3—C4—C5—C6 | −0.6 (3) | C13—C14—N15—C16 | 176.15 (15) |
C4—C5—C6—C7 | 0.8 (3) | C14—N15—C16—N17 | 0.69 (17) |
C5—C6—C7—C2 | 0.1 (3) | C14—N15—C16—C19 | −174.58 (14) |
C5—C6—C7—C8 | −178.83 (16) | N15—C16—N17—C1 | −1.12 (18) |
C3—C2—C7—C6 | −1.2 (2) | C19—C16—N17—C1 | 173.92 (14) |
C1—C2—C7—C6 | −179.55 (14) | N15—C16—N17—C18 | 171.76 (15) |
C3—C2—C7—C8 | 177.71 (15) | C19—C16—N17—C18 | −13.2 (3) |
C1—C2—C7—C8 | −0.6 (2) | C14—C1—N17—C16 | 1.03 (16) |
C6—C7—C8—C9 | 1.8 (2) | C2—C1—N17—C16 | −174.61 (16) |
C2—C7—C8—C9 | −177.07 (15) | C14—C1—N17—C18 | −171.74 (15) |
C6—C7—C8—C13 | −178.42 (15) | C2—C1—N17—C18 | 12.6 (3) |
C2—C7—C8—C13 | 2.7 (2) | N15—C16—C19—C24 | 139.03 (16) |
C13—C8—C9—C10 | 0.4 (2) | N17—C16—C19—C24 | −35.6 (2) |
C7—C8—C9—C10 | −179.86 (15) | N15—C16—C19—C20 | −34.9 (2) |
C8—C9—C10—C11 | 1.0 (2) | N17—C16—C19—C20 | 150.48 (15) |
C9—C10—C11—C12 | −1.1 (2) | C24—C19—C20—C21 | 1.1 (2) |
C10—C11—C12—C13 | −0.3 (2) | C16—C19—C20—C21 | 175.22 (15) |
C11—C12—C13—C8 | 1.7 (2) | C19—C20—C21—C22 | −0.8 (2) |
C11—C12—C13—C14 | −176.06 (15) | C20—C21—C22—C23 | −0.2 (3) |
C9—C8—C13—C12 | −1.7 (2) | C20—C21—C22—Br | −178.91 (13) |
C7—C8—C13—C12 | 178.48 (15) | C21—C22—C23—C24 | 1.0 (3) |
C9—C8—C13—C14 | 176.16 (14) | Br—C22—C23—C24 | 179.63 (12) |
C7—C8—C13—C14 | −3.6 (2) | C20—C19—C24—C23 | −0.4 (2) |
N17—C1—C14—N15 | −0.67 (17) | C16—C19—C24—C23 | −174.20 (15) |
C2—C1—C14—N15 | 175.53 (13) | C22—C23—C24—C19 | −0.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···N15i | 0.95 | 2.54 | 3.419 (2) | 154 |
Symmetry code: (i) −x, −y, z+1/2. |
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