Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804006993/cv6286sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804006993/cv6286Isup2.hkl |
CCDC reference: 238833
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.101
- Data-to-parameter ratio = 21.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Version 1.07; Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C21H19BrN2O5 | Z = 2 |
Mr = 459.29 | F(000) = 468 |
Triclinic, P1 | Dx = 1.570 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5238 (2) Å | Cell parameters from 29442 reflections |
b = 10.2817 (2) Å | θ = 2.0–30.0° |
c = 13.8084 (2) Å | µ = 2.15 mm−1 |
α = 69.467 (1)° | T = 160 K |
β = 79.837 (1)° | Prism, yellow |
γ = 77.741 (1)° | 0.30 × 0.23 × 0.20 mm |
V = 971.42 (3) Å3 |
Nonius KappaCCD diffractometer | 5684 independent reflections |
Radiation source: Nonius FR590 sealed-tube generator | 4679 reflections with I > 2σ(I) |
Horizontally mounted graphite crystal monochromator | Rint = 0.068 |
Detector resolution: 9 pixels mm-1 | θmax = 30.0°, θmin = 2.1° |
φ and ω scans with κ offsets | h = −10→10 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −14→14 |
Tmin = 0.542, Tmax = 0.641 | l = −19→18 |
25900 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0525P)2 + 0.3259P] where P = (Fo2 + 2Fc2)/3 |
5684 reflections | (Δ/σ)max = 0.001 |
266 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.66 e Å−3 |
Experimental. Solvent used: ethyl acetate Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.520 (1) Frames collected: 593 Seconds exposure per frame: 18 Degrees rotation per frame: 1.2 Crystal-Detector distance (mm): 30.0 |
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 | 0.58377 (3) | −0.051668 (19) | 0.373158 (14) | 0.03668 (8) | |
O10 | 0.09686 (19) | 0.99154 (14) | 0.31954 (10) | 0.0293 (3) | |
O11 | 0.1975 (2) | 0.77072 (14) | 0.41945 (10) | 0.0312 (3) | |
O12 | 0.51632 (19) | 0.51669 (15) | 0.37150 (10) | 0.0317 (3) | |
O13 | 0.21565 (18) | 0.50813 (13) | 0.38664 (10) | 0.0276 (3) | |
O14 | 0.61471 (18) | 0.60190 (14) | 0.02307 (10) | 0.0277 (3) | |
N4 | 0.3463 (2) | 0.82034 (15) | 0.07670 (11) | 0.0202 (3) | |
N21 | 0.1129 (2) | 1.22963 (16) | −0.07832 (12) | 0.0284 (3) | |
C1 | 0.2424 (2) | 0.81898 (18) | 0.24074 (13) | 0.0210 (3) | |
C2 | 0.3326 (2) | 0.68335 (18) | 0.24416 (13) | 0.0209 (3) | |
C3 | 0.3976 (2) | 0.68229 (17) | 0.14341 (13) | 0.0210 (3) | |
C5 | 0.3770 (2) | 0.87474 (19) | −0.02974 (13) | 0.0230 (3) | |
H5 | 0.4497 | 0.8177 | −0.0680 | 0.028* | |
C6 | 0.3045 (2) | 1.00881 (19) | −0.08045 (14) | 0.0247 (3) | |
H6 | 0.3277 | 1.0447 | −0.1541 | 0.030* | |
C7 | 0.1933 (2) | 1.09806 (18) | −0.02550 (13) | 0.0228 (3) | |
C8 | 0.1706 (2) | 1.04302 (18) | 0.08353 (13) | 0.0223 (3) | |
H8 | 0.1030 | 1.1002 | 0.1230 | 0.027* | |
C9 | 0.2470 (2) | 0.90457 (18) | 0.13394 (13) | 0.0206 (3) | |
C10 | 0.1700 (2) | 0.87137 (18) | 0.32741 (13) | 0.0228 (3) | |
C11 | 0.1380 (4) | 0.8130 (2) | 0.51078 (15) | 0.0400 (5) | |
H111 | 0.2033 | 0.8877 | 0.5073 | 0.060* | |
H112 | 0.1643 | 0.7320 | 0.5731 | 0.060* | |
H113 | 0.0061 | 0.8479 | 0.5140 | 0.060* | |
C12 | 0.3685 (2) | 0.56121 (18) | 0.34096 (13) | 0.0226 (3) | |
C13 | 0.2368 (3) | 0.3929 (2) | 0.48331 (16) | 0.0387 (5) | |
H131 | 0.3149 | 0.3109 | 0.4690 | 0.058* | |
H132 | 0.1165 | 0.3687 | 0.5164 | 0.058* | |
H133 | 0.2934 | 0.4211 | 0.5300 | 0.058* | |
C14 | 0.5185 (2) | 0.57440 (18) | 0.10753 (13) | 0.0221 (3) | |
C15 | 0.5284 (2) | 0.42445 (18) | 0.17739 (13) | 0.0222 (3) | |
C16 | 0.3726 (3) | 0.36162 (19) | 0.21736 (14) | 0.0256 (3) | |
H16 | 0.2551 | 0.4164 | 0.2047 | 0.031* | |
C17 | 0.3874 (3) | 0.21930 (19) | 0.27563 (15) | 0.0273 (4) | |
H17 | 0.2816 | 0.1757 | 0.3021 | 0.033* | |
C18 | 0.5603 (3) | 0.14307 (19) | 0.29405 (14) | 0.0273 (4) | |
C19 | 0.7172 (3) | 0.2029 (2) | 0.25631 (14) | 0.0277 (4) | |
H19 | 0.8343 | 0.1485 | 0.2708 | 0.033* | |
C20 | 0.6999 (3) | 0.34424 (19) | 0.19684 (14) | 0.0259 (3) | |
H20 | 0.8064 | 0.3867 | 0.1691 | 0.031* | |
C22 | 0.1458 (3) | 1.2877 (2) | −0.19118 (14) | 0.0312 (4) | |
H221 | 0.2760 | 1.2940 | −0.2118 | 0.047* | |
H222 | 0.0730 | 1.3819 | −0.2151 | 0.047* | |
H223 | 0.1105 | 1.2264 | −0.2227 | 0.047* | |
C23 | 0.0005 (3) | 1.3181 (2) | −0.02136 (15) | 0.0301 (4) | |
H231 | −0.0953 | 1.2683 | 0.0255 | 0.045* | |
H232 | −0.0562 | 1.4055 | −0.0705 | 0.045* | |
H233 | 0.0769 | 1.3404 | 0.0194 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.05351 (15) | 0.02046 (11) | 0.02760 (11) | 0.00215 (8) | −0.00390 (8) | −0.00248 (7) |
O10 | 0.0333 (7) | 0.0256 (7) | 0.0278 (7) | 0.0020 (5) | −0.0040 (5) | −0.0110 (5) |
O11 | 0.0501 (8) | 0.0241 (7) | 0.0180 (6) | −0.0030 (6) | −0.0023 (5) | −0.0076 (5) |
O12 | 0.0313 (7) | 0.0354 (8) | 0.0247 (6) | 0.0007 (6) | −0.0081 (5) | −0.0063 (6) |
O13 | 0.0330 (7) | 0.0219 (6) | 0.0239 (6) | −0.0062 (5) | −0.0022 (5) | −0.0020 (5) |
O14 | 0.0303 (7) | 0.0248 (6) | 0.0253 (6) | −0.0035 (5) | 0.0015 (5) | −0.0078 (5) |
N4 | 0.0236 (7) | 0.0179 (7) | 0.0189 (6) | −0.0030 (5) | −0.0040 (5) | −0.0053 (5) |
N21 | 0.0372 (9) | 0.0207 (7) | 0.0230 (7) | −0.0014 (6) | −0.0061 (6) | −0.0024 (6) |
C1 | 0.0236 (8) | 0.0195 (8) | 0.0190 (7) | −0.0032 (6) | −0.0034 (6) | −0.0051 (6) |
C2 | 0.0215 (8) | 0.0206 (8) | 0.0199 (7) | −0.0034 (6) | −0.0038 (6) | −0.0053 (6) |
C3 | 0.0241 (8) | 0.0180 (7) | 0.0206 (8) | −0.0035 (6) | −0.0040 (6) | −0.0052 (6) |
C5 | 0.0273 (9) | 0.0239 (8) | 0.0185 (7) | −0.0046 (7) | −0.0019 (6) | −0.0078 (6) |
C6 | 0.0284 (9) | 0.0247 (8) | 0.0205 (8) | −0.0052 (7) | −0.0030 (6) | −0.0060 (6) |
C7 | 0.0254 (8) | 0.0196 (8) | 0.0233 (8) | −0.0051 (6) | −0.0055 (6) | −0.0047 (6) |
C8 | 0.0242 (8) | 0.0210 (8) | 0.0217 (8) | −0.0027 (6) | −0.0035 (6) | −0.0072 (6) |
C9 | 0.0223 (8) | 0.0202 (8) | 0.0198 (7) | −0.0041 (6) | −0.0022 (6) | −0.0070 (6) |
C10 | 0.0232 (8) | 0.0231 (8) | 0.0231 (8) | −0.0049 (7) | −0.0026 (6) | −0.0080 (6) |
C11 | 0.0641 (15) | 0.0358 (11) | 0.0206 (9) | −0.0095 (10) | 0.0018 (9) | −0.0121 (8) |
C12 | 0.0279 (9) | 0.0201 (8) | 0.0195 (8) | −0.0016 (6) | −0.0028 (6) | −0.0074 (6) |
C13 | 0.0524 (13) | 0.0293 (10) | 0.0261 (9) | −0.0109 (9) | −0.0007 (8) | 0.0018 (8) |
C14 | 0.0219 (8) | 0.0227 (8) | 0.0236 (8) | −0.0032 (6) | −0.0050 (6) | −0.0090 (6) |
C15 | 0.0254 (8) | 0.0211 (8) | 0.0208 (8) | −0.0007 (6) | −0.0030 (6) | −0.0092 (6) |
C16 | 0.0268 (9) | 0.0226 (8) | 0.0269 (9) | −0.0009 (7) | −0.0055 (7) | −0.0081 (7) |
C17 | 0.0312 (10) | 0.0227 (9) | 0.0269 (9) | −0.0045 (7) | −0.0031 (7) | −0.0068 (7) |
C18 | 0.0412 (11) | 0.0184 (8) | 0.0200 (8) | 0.0011 (7) | −0.0045 (7) | −0.0065 (6) |
C19 | 0.0290 (9) | 0.0263 (9) | 0.0255 (9) | 0.0053 (7) | −0.0058 (7) | −0.0100 (7) |
C20 | 0.0250 (9) | 0.0256 (9) | 0.0264 (8) | 0.0000 (7) | −0.0029 (6) | −0.0097 (7) |
C22 | 0.0360 (10) | 0.0286 (9) | 0.0239 (9) | −0.0050 (8) | −0.0067 (7) | −0.0009 (7) |
C23 | 0.0327 (10) | 0.0220 (8) | 0.0324 (10) | 0.0002 (7) | −0.0066 (7) | −0.0062 (7) |
Br—C18 | 1.9019 (18) | C8—C9 | 1.393 (2) |
O10—C10 | 1.216 (2) | C8—H8 | 0.9500 |
O11—C10 | 1.345 (2) | C11—H111 | 0.9800 |
O11—C11 | 1.443 (2) | C11—H112 | 0.9800 |
O12—C12 | 1.199 (2) | C11—H113 | 0.9800 |
O13—C12 | 1.337 (2) | C13—H131 | 0.9800 |
O13—C13 | 1.448 (2) | C13—H132 | 0.9800 |
O14—C14 | 1.234 (2) | C13—H133 | 0.9800 |
N4—C5 | 1.373 (2) | C14—C15 | 1.499 (2) |
N4—C9 | 1.389 (2) | C15—C20 | 1.390 (3) |
N4—C3 | 1.410 (2) | C15—C16 | 1.393 (3) |
N21—C7 | 1.358 (2) | C16—C17 | 1.392 (3) |
N21—C23 | 1.450 (2) | C16—H16 | 0.9500 |
N21—C22 | 1.456 (2) | C17—C18 | 1.384 (3) |
C1—C2 | 1.404 (2) | C17—H17 | 0.9500 |
C1—C9 | 1.426 (2) | C18—C19 | 1.383 (3) |
C1—C10 | 1.455 (2) | C19—C20 | 1.387 (3) |
C2—C3 | 1.394 (2) | C19—H19 | 0.9500 |
C2—C12 | 1.497 (2) | C20—H20 | 0.9500 |
C3—C14 | 1.450 (2) | C22—H221 | 0.9800 |
C5—C6 | 1.351 (3) | C22—H222 | 0.9800 |
C5—H5 | 0.9500 | C22—H223 | 0.9800 |
C6—C7 | 1.434 (3) | C23—H231 | 0.9800 |
C6—H6 | 0.9500 | C23—H232 | 0.9800 |
C7—C8 | 1.403 (2) | C23—H233 | 0.9800 |
C10—O11—C11 | 116.29 (15) | O12—C12—C2 | 123.77 (16) |
C12—O13—C13 | 114.59 (15) | O13—C12—C2 | 111.02 (15) |
C5—N4—C9 | 120.26 (14) | O13—C13—H131 | 109.5 |
C5—N4—C3 | 129.56 (15) | O13—C13—H132 | 109.5 |
C9—N4—C3 | 110.15 (13) | H131—C13—H132 | 109.5 |
C7—N21—C23 | 119.66 (15) | O13—C13—H133 | 109.5 |
C7—N21—C22 | 121.45 (16) | H131—C13—H133 | 109.5 |
C23—N21—C22 | 118.79 (16) | H132—C13—H133 | 109.5 |
C2—C1—C9 | 107.35 (14) | O14—C14—C3 | 122.50 (16) |
C2—C1—C10 | 128.19 (15) | O14—C14—C15 | 119.31 (15) |
C9—C1—C10 | 124.25 (15) | C3—C14—C15 | 118.17 (15) |
C3—C2—C1 | 109.49 (15) | C20—C15—C16 | 119.52 (16) |
C3—C2—C12 | 124.69 (15) | C20—C15—C14 | 118.38 (16) |
C1—C2—C12 | 125.63 (15) | C16—C15—C14 | 121.96 (15) |
C2—C3—N4 | 106.30 (14) | C17—C16—C15 | 120.57 (17) |
C2—C3—C14 | 130.27 (16) | C17—C16—H16 | 119.7 |
N4—C3—C14 | 122.78 (15) | C15—C16—H16 | 119.7 |
C6—C5—N4 | 120.52 (16) | C18—C17—C16 | 118.27 (17) |
C6—C5—H5 | 119.7 | C18—C17—H17 | 120.9 |
N4—C5—H5 | 119.7 | C16—C17—H17 | 120.9 |
C5—C6—C7 | 121.43 (16) | C19—C18—C17 | 122.44 (17) |
C5—C6—H6 | 119.3 | C19—C18—Br | 118.59 (14) |
C7—C6—H6 | 119.3 | C17—C18—Br | 118.97 (14) |
N21—C7—C8 | 122.24 (16) | C18—C19—C20 | 118.45 (17) |
N21—C7—C6 | 120.48 (15) | C18—C19—H19 | 120.8 |
C8—C7—C6 | 117.27 (16) | C20—C19—H19 | 120.8 |
C9—C8—C7 | 120.09 (16) | C19—C20—C15 | 120.73 (17) |
C9—C8—H8 | 120.0 | C19—C20—H20 | 119.6 |
C7—C8—H8 | 120.0 | C15—C20—H20 | 119.6 |
N4—C9—C8 | 120.27 (15) | N21—C22—H221 | 109.5 |
N4—C9—C1 | 106.64 (14) | N21—C22—H222 | 109.5 |
C8—C9—C1 | 133.05 (16) | H221—C22—H222 | 109.5 |
O10—C10—O11 | 123.07 (16) | N21—C22—H223 | 109.5 |
O10—C10—C1 | 125.27 (16) | H221—C22—H223 | 109.5 |
O11—C10—C1 | 111.64 (15) | H222—C22—H223 | 109.5 |
O11—C11—H111 | 109.5 | N21—C23—H231 | 109.5 |
O11—C11—H112 | 109.5 | N21—C23—H232 | 109.5 |
H111—C11—H112 | 109.5 | H231—C23—H232 | 109.5 |
O11—C11—H113 | 109.5 | N21—C23—H233 | 109.5 |
H111—C11—H113 | 109.5 | H231—C23—H233 | 109.5 |
H112—C11—H113 | 109.5 | H232—C23—H233 | 109.5 |
O12—C12—O13 | 125.19 (16) | ||
C9—C1—C2—C3 | 1.59 (19) | C10—C1—C9—C8 | −9.8 (3) |
C10—C1—C2—C3 | −173.26 (17) | C11—O11—C10—O10 | −1.1 (3) |
C9—C1—C2—C12 | 176.65 (16) | C11—O11—C10—C1 | 177.40 (17) |
C10—C1—C2—C12 | 1.8 (3) | C2—C1—C10—O10 | 178.06 (17) |
C1—C2—C3—N4 | 0.04 (19) | C9—C1—C10—O10 | 4.0 (3) |
C12—C2—C3—N4 | −175.08 (15) | C2—C1—C10—O11 | −0.4 (3) |
C1—C2—C3—C14 | 170.81 (17) | C9—C1—C10—O11 | −174.47 (16) |
C12—C2—C3—C14 | −4.3 (3) | C13—O13—C12—O12 | 3.5 (3) |
C5—N4—C3—C2 | −179.87 (16) | C13—O13—C12—C2 | −177.64 (15) |
C9—N4—C3—C2 | −1.73 (18) | C3—C2—C12—O12 | 68.1 (2) |
C5—N4—C3—C14 | 8.5 (3) | C1—C2—C12—O12 | −106.3 (2) |
C9—N4—C3—C14 | −173.36 (15) | C3—C2—C12—O13 | −110.77 (19) |
C9—N4—C5—C6 | −2.9 (2) | C1—C2—C12—O13 | 74.9 (2) |
C3—N4—C5—C6 | 175.11 (17) | C2—C3—C14—O14 | −153.73 (18) |
N4—C5—C6—C7 | −0.3 (3) | N4—C3—C14—O14 | 15.7 (3) |
C23—N21—C7—C8 | 0.5 (3) | C2—C3—C14—C15 | 25.1 (3) |
C22—N21—C7—C8 | 176.70 (17) | N4—C3—C14—C15 | −165.49 (15) |
C23—N21—C7—C6 | 179.80 (17) | O14—C14—C15—C20 | 48.6 (2) |
C22—N21—C7—C6 | −4.0 (3) | C3—C14—C15—C20 | −130.23 (17) |
C5—C6—C7—N21 | −176.09 (17) | O14—C14—C15—C16 | −127.20 (18) |
C5—C6—C7—C8 | 3.2 (3) | C3—C14—C15—C16 | 54.0 (2) |
N21—C7—C8—C9 | 176.23 (16) | C20—C15—C16—C17 | −0.6 (3) |
C6—C7—C8—C9 | −3.1 (2) | C14—C15—C16—C17 | 175.17 (16) |
C5—N4—C9—C8 | 3.0 (2) | C15—C16—C17—C18 | 1.1 (3) |
C3—N4—C9—C8 | −175.38 (15) | C16—C17—C18—C19 | −0.4 (3) |
C5—N4—C9—C1 | −178.96 (14) | C16—C17—C18—Br | −179.82 (13) |
C3—N4—C9—C1 | 2.69 (18) | C17—C18—C19—C20 | −0.8 (3) |
C7—C8—C9—N4 | 0.1 (2) | Br—C18—C19—C20 | 178.68 (13) |
C7—C8—C9—C1 | −177.36 (18) | C18—C19—C20—C15 | 1.2 (3) |
C2—C1—C9—N4 | −2.60 (18) | C16—C15—C20—C19 | −0.6 (3) |
C10—C1—C9—N4 | 172.51 (16) | C14—C15—C20—C19 | −176.50 (16) |
C2—C1—C9—C8 | 175.12 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H133···O12i | 0.98 | 2.45 | 3.419 (3) | 170 |
C17—H17···O10ii | 0.95 | 2.50 | 3.368 (2) | 152 |
C19—H19···O10iii | 0.95 | 2.31 | 3.249 (2) | 172 |
C23—H233···O14iv | 0.98 | 2.44 | 3.167 (2) | 131 |
C13—H131···Brv | 0.98 | 2.84 | 3.480 (2) | 123 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) x+1, y−1, z; (iv) −x+1, −y+2, −z; (v) −x+1, −y, −z+1. |