Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014468/fj2007sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014468/fj2007Isup2.hkl |
CCDC reference: 647202
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.004 Å
- R factor = 0.033
- wR factor = 0.087
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 8 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.33 Ratio PLAT431_ALERT_2_C Short Inter HL..A Contact Br .. Br .. 3.50 Ang.
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 1 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 1 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
Data collection: SMART (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus; program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTO (Meetsma, 2007) and PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
C10H9BrO2 | Z = 2 |
Mr = 241.08 | F(000) = 240 |
Triclinic, P1 | The final unit cell was obtained from the xyz centroids of
2400 reflections after integration using the SAINTPLUS
software package (Bruker, 2006). Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the final atomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988) Le Page, Y. (1987). J. Appl. Cryst. 20, 264–269. Le Page, Y. (1988). J. Appl. Cryst. 21, 983–984. Spek, A. L. (1988). J. Appl. Cryst. 21, 578–579. |
Hall symbol: -P 1 | Dx = 1.737 Mg m−3 |
a = 7.3202 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.1460 (13) Å | Cell parameters from 2400 reflections |
c = 9.0526 (14) Å | θ = 2.8–28.8° |
α = 114.431 (2)° | µ = 4.42 mm−1 |
β = 107.444 (2)° | T = 100 K |
γ = 92.065 (2)° | Block, colourless |
V = 460.85 (12) Å3 | 0.44 × 0.17 × 0.14 mm |
Bruker SMART APEX CCD area-detector diffractometer | 2129 independent reflections |
Radiation source: fine focus sealed Siemens Mo tube | 1932 reflections with I > 2σ(I) |
Parallel mounted graphite monochromator | Rint = 0.021 |
Detector resolution: 66.06 pixels mm-1 | θmax = 28.3°, θmin = 2.8° |
φ and ω scans | h = −7→9 |
Absorption correction: multi-scan (SADABS; Bruker, 2006) | k = −10→10 |
Tmin = 0.243, Tmax = 0.539 | l = −12→11 |
3745 measured reflections |
Refinement on F2 | Primary atom site location: heavy-atom method |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.087 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0621P)2] where P = (Fo2 + 2Fc2)/3 |
2129 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 1.14 e Å−3 |
0 restraints | Δρmin = −0.78 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | 0.19136 (4) | 0.40680 (3) | 0.08590 (3) | 0.0260 (1) | |
O1 | 1.2601 (3) | −0.0520 (2) | 0.3293 (2) | 0.0202 (5) | |
O2 | 1.4011 (3) | 0.1606 (2) | 0.6036 (2) | 0.0207 (5) | |
C1 | 0.6965 (4) | 0.1901 (3) | 0.0822 (3) | 0.0169 (6) | |
C2 | 0.5274 (4) | 0.2569 (3) | 0.0335 (3) | 0.0182 (7) | |
C3 | 0.4232 (4) | 0.3156 (3) | 0.1457 (3) | 0.0164 (6) | |
C4 | 0.4841 (4) | 0.3079 (3) | 0.3037 (3) | 0.0177 (7) | |
C5 | 0.6543 (4) | 0.2430 (3) | 0.3508 (3) | 0.0175 (7) | |
C6 | 0.7655 (4) | 0.1859 (3) | 0.2426 (3) | 0.0165 (6) | |
C7 | 0.9484 (4) | 0.1197 (3) | 0.2892 (3) | 0.0171 (6) | |
C8 | 1.0833 (3) | 0.1785 (3) | 0.4482 (3) | 0.0161 (6) | |
C9 | 1.2610 (4) | 0.0947 (3) | 0.4671 (3) | 0.0172 (7) | |
C10 | 1.0810 (4) | 0.3320 (3) | 0.6127 (3) | 0.0198 (7) | |
H1 | 0.766 (5) | 0.143 (4) | 0.009 (4) | 0.022 (7)* | |
H2 | 0.493 (5) | 0.263 (4) | −0.083 (4) | 0.030 (8)* | |
H4 | 0.410 (5) | 0.350 (4) | 0.377 (4) | 0.023 (7)* | |
H5 | 0.695 (5) | 0.230 (5) | 0.465 (5) | 0.040 (9)* | |
H7 | 0.978 (5) | 0.030 (4) | 0.189 (4) | 0.023 (8)* | |
H10 | 1.217 (4) | 0.410 (4) | 0.685 (3) | 0.012 (6)* | |
H10' | 1.028 (4) | 0.283 (4) | 0.680 (4) | 0.022 (7)* | |
H10" | 0.996 (5) | 0.410 (4) | 0.593 (4) | 0.027 (8)* | |
H11 | 1.363 (6) | −0.087 (5) | 0.352 (5) | 0.036 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.0216 (2) | 0.0353 (2) | 0.0243 (2) | 0.0151 (1) | 0.0071 (1) | 0.0159 (1) |
O1 | 0.0195 (10) | 0.0212 (8) | 0.0172 (8) | 0.0103 (7) | 0.0055 (7) | 0.0061 (7) |
O2 | 0.0182 (9) | 0.0237 (8) | 0.0163 (8) | 0.0076 (7) | 0.0037 (7) | 0.0065 (7) |
C1 | 0.0177 (12) | 0.0172 (10) | 0.0136 (10) | 0.0038 (9) | 0.0056 (10) | 0.0047 (8) |
C2 | 0.0188 (13) | 0.0204 (10) | 0.0146 (11) | 0.0046 (10) | 0.0041 (10) | 0.0082 (9) |
C3 | 0.0132 (12) | 0.0171 (10) | 0.0168 (11) | 0.0036 (9) | 0.0032 (9) | 0.0070 (8) |
C4 | 0.0175 (13) | 0.0185 (10) | 0.0148 (11) | 0.0033 (9) | 0.0051 (10) | 0.0057 (9) |
C5 | 0.0184 (12) | 0.0198 (11) | 0.0164 (11) | 0.0045 (9) | 0.0065 (9) | 0.0095 (9) |
C6 | 0.0181 (12) | 0.0146 (10) | 0.0153 (10) | 0.0038 (9) | 0.0049 (9) | 0.0057 (8) |
C7 | 0.0173 (12) | 0.0171 (10) | 0.0177 (11) | 0.0046 (9) | 0.0074 (10) | 0.0074 (9) |
C8 | 0.0165 (12) | 0.0171 (10) | 0.0170 (11) | 0.0042 (9) | 0.0064 (9) | 0.0091 (9) |
C9 | 0.0200 (13) | 0.0175 (10) | 0.0159 (11) | 0.0044 (9) | 0.0068 (10) | 0.0087 (9) |
C10 | 0.0205 (13) | 0.0182 (10) | 0.0178 (11) | 0.0051 (10) | 0.0054 (10) | 0.0062 (9) |
Br—C3 | 1.897 (3) | C7—C8 | 1.349 (3) |
O1—C9 | 1.321 (3) | C8—C9 | 1.488 (4) |
O2—C9 | 1.232 (3) | C8—C10 | 1.503 (3) |
O1—H11 | 0.81 (5) | C1—H1 | 0.92 (4) |
C1—C6 | 1.403 (3) | C2—H2 | 1.03 (3) |
C1—C2 | 1.394 (4) | C4—H4 | 0.95 (4) |
C2—C3 | 1.390 (4) | C5—H5 | 1.04 (4) |
C3—C4 | 1.394 (3) | C7—H7 | 0.99 (3) |
C4—C5 | 1.389 (4) | C10—H10 | 1.02 (3) |
C5—C6 | 1.402 (4) | C10—H10' | 1.01 (3) |
C6—C7 | 1.471 (4) | C10—H10" | 0.94 (4) |
Br···Bri | 3.4958 (7) | C9···H4xi | 2.82 (4) |
Br···H10'ii | 3.19 (3) | C9···H11iii | 2.77 (4) |
O1···O2iii | 2.646 (3) | C10···H5 | 2.67 (4) |
O2···O1iii | 2.646 (3) | H1···H7 | 2.40 (5) |
O2···C9iii | 3.327 (4) | H1···O1v | 2.78 (3) |
O2···O2iii | 3.210 (3) | H2···O2ii | 2.46 (3) |
O1···H5iv | 2.75 (4) | H4···C8ix | 3.09 (4) |
O1···H10'iv | 2.73 (3) | H4···C9ix | 2.82 (4) |
O1···H1v | 2.78 (3) | H4···C4viii | 2.93 (3) |
O1···H7 | 2.36 (4) | H4···H4viii | 2.49 (5) |
O2···H2vi | 2.46 (3) | H5···C8 | 2.93 (4) |
O2···H10 | 2.46 (3) | H5···C10 | 2.67 (4) |
O2···H11iii | 1.83 (5) | H5···H10' | 2.51 (5) |
C1···C2vii | 3.525 (4) | H5···H10" | 2.28 (5) |
C2···C1vii | 3.525 (4) | H5···O1iv | 2.75 (4) |
C2···C6vii | 3.554 (4) | H5···C9iv | 2.96 (4) |
C4···C4viii | 3.568 (4) | H5···H11iv | 2.50 (6) |
C4···C9ix | 3.353 (4) | H7···O1 | 2.36 (4) |
C5···C10 | 3.143 (4) | H7···H1 | 2.40 (5) |
C6···C10x | 3.598 (4) | H10···O2 | 2.46 (3) |
C6···C2vii | 3.554 (4) | H10···C1x | 2.97 (3) |
C9···O2iii | 3.327 (4) | H10···C2x | 2.90 (3) |
C9···C4xi | 3.353 (4) | H10···C3x | 2.93 (3) |
C10···C6x | 3.598 (4) | H10···C4x | 3.06 (3) |
C10···C5 | 3.143 (4) | H10···C6x | 3.07 (3) |
C1···H10x | 2.97 (3) | H10'···Brvi | 3.19 (3) |
C2···H10x | 2.90 (3) | H10'···H5 | 2.51 (5) |
C3···H10x | 2.93 (3) | H10'···O1iv | 2.73 (3) |
C4···H10x | 3.06 (3) | H10"···C5 | 2.63 (3) |
C4···H4viii | 2.93 (3) | H10"···C6 | 2.83 (3) |
C5···H10" | 2.63 (3) | H10"···H5 | 2.28 (5) |
C6···H10" | 2.83 (3) | H11···O2iii | 1.83 (5) |
C6···H10x | 3.07 (3) | H11···C9iii | 2.77 (4) |
C8···H5 | 2.93 (4) | H11···H5iv | 2.50 (6) |
C8···H4xi | 3.09 (4) | H11···H11iii | 2.58 (6) |
C9···H5iv | 2.96 (4) | ||
C9—O1—H11 | 109 (3) | O1—C9—O2 | 122.4 (3) |
C2—C1—C6 | 121.6 (3) | C2—C1—H1 | 122 (2) |
C1—C2—C3 | 118.6 (2) | C6—C1—H1 | 117 (2) |
Br—C3—C4 | 118.1 (2) | C1—C2—H2 | 116 (2) |
C2—C3—C4 | 121.4 (3) | C3—C2—H2 | 125 (2) |
Br—C3—C2 | 120.49 (19) | C3—C4—H4 | 119 (2) |
C3—C4—C5 | 119.1 (3) | C5—C4—H4 | 122 (2) |
C4—C5—C6 | 121.2 (2) | C4—C5—H5 | 119 (2) |
C1—C6—C7 | 119.1 (2) | C6—C5—H5 | 120 (2) |
C5—C6—C7 | 122.8 (2) | C6—C7—H7 | 114 (2) |
C1—C6—C5 | 118.1 (3) | C8—C7—H7 | 118 (2) |
C6—C7—C8 | 127.3 (2) | C8—C10—H10 | 110.5 (15) |
C7—C8—C10 | 126.6 (2) | C8—C10—H10' | 110.9 (19) |
C9—C8—C10 | 114.5 (2) | C8—C10—H10" | 112.8 (19) |
C7—C8—C9 | 118.8 (2) | H10—C10—H10' | 111 (2) |
O1—C9—C8 | 116.2 (2) | H10—C10—H10" | 108 (3) |
O2—C9—C8 | 121.4 (2) | H10'—C10—H10" | 103 (3) |
C6—C1—C2—C3 | −1.8 (4) | C4—C5—C6—C7 | 178.8 (3) |
C2—C1—C6—C5 | 3.0 (4) | C1—C6—C7—C8 | 146.2 (3) |
C2—C1—C6—C7 | −177.9 (3) | C5—C6—C7—C8 | −34.8 (4) |
C1—C2—C3—Br | −179.7 (2) | C6—C7—C8—C9 | −179.0 (3) |
C1—C2—C3—C4 | −0.3 (4) | C6—C7—C8—C10 | −3.2 (5) |
Br—C3—C4—C5 | −179.5 (2) | C7—C8—C9—O1 | −10.0 (4) |
C2—C3—C4—C5 | 1.1 (4) | C7—C8—C9—O2 | 169.3 (3) |
C3—C4—C5—C6 | 0.2 (4) | C10—C8—C9—O1 | 173.7 (2) |
C4—C5—C6—C1 | −2.2 (4) | C10—C8—C9—O2 | −7.1 (4) |
Symmetry codes: (i) −x, −y+1, −z; (ii) x−1, y, z−1; (iii) −x+3, −y, −z+1; (iv) −x+2, −y, −z+1; (v) −x+2, −y, −z; (vi) x+1, y, z+1; (vii) −x+1, −y, −z; (viii) −x+1, −y+1, −z+1; (ix) x−1, y, z; (x) −x+2, −y+1, −z+1; (xi) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H11···O2iii | 0.81 (5) | 1.83 (5) | 2.646 (3) | 177 (7) |
C2—H2···O2ii | 1.03 (3) | 2.46 (3) | 3.447 (3) | 160 (3) |
C7—H7···O1 | 0.99 (3) | 2.36 (4) | 2.729 (4) | 101 (2) |
Symmetry codes: (ii) x−1, y, z−1; (iii) −x+3, −y, −z+1. |