Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004137/nc6020sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004137/nc6020Isup2.hkl |
CCDC reference: 269820
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.032
- wR factor = 0.078
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Br12 .. O1 .. 3.06 Ang.
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3' PLAT301_ALERT_3_C Main Residue Disorder ......................... 24.00 Perc. PLAT431_ALERT_2_C Short Inter HL..A Contact Br12 .. O1' .. 3.07 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C3 .. 2.98 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 15.00 Deg. C1' -N1 -C1 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 23.40 Deg. C3 -N1 -C3' 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 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 7 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
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C12H12BrNO4S | F(000) = 696 |
Mr = 346.20 | Dx = 1.722 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6677 (10) Å | Cell parameters from 7895 reflections |
b = 18.5082 (18) Å | θ = 4.2–25.6° |
c = 8.9746 (10) Å | µ = 3.24 mm−1 |
β = 111.950 (9)° | T = 173 K |
V = 1335.4 (3) Å3 | Block, colourless |
Z = 4 | 0.36 × 0.32 × 0.29 mm |
Stoe IPDS-II two-circle diffractometer | 2486 independent reflections |
Radiation source: fine-focus sealed tube | 2242 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 25.7°, θmin = 4.1° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −9→10 |
Tmin = 0.334, Tmax = 0.390 | k = −19→22 |
6240 measured reflections | l = −10→10 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0441P)2 + 0.5152P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max = 0.002 |
2486 reflections | Δρmax = 0.46 e Å−3 |
203 parameters | Δρmin = −0.79 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0107 (12) |
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 | Occ. (<1) | |
Br12 | 1.19325 (3) | 0.303132 (15) | 0.54646 (3) | 0.03067 (13) | |
N1 | 0.7355 (3) | 0.20765 (11) | 0.5607 (2) | 0.0246 (5) | |
S1 | 0.43745 (16) | 0.14830 (6) | 0.49017 (12) | 0.0330 (4) | 0.740 (5) |
C1 | 0.5834 (6) | 0.2152 (3) | 0.5919 (6) | 0.0185 (10) | 0.740 (5) |
O1 | 0.5615 (4) | 0.2613 (2) | 0.6783 (4) | 0.0268 (8) | 0.740 (5) |
C2 | 0.5764 (9) | 0.1064 (4) | 0.4080 (9) | 0.0324 (15) | 0.740 (5) |
H2A | 0.5970 | 0.0565 | 0.4430 | 0.039* | 0.740 (5) |
H2B | 0.5279 | 0.1072 | 0.2915 | 0.039* | 0.740 (5) |
C3 | 0.7378 (7) | 0.14906 (19) | 0.4682 (4) | 0.0218 (8) | 0.740 (5) |
O2 | 0.8605 (6) | 0.13352 (17) | 0.4383 (4) | 0.0355 (9) | 0.740 (5) |
S1' | 0.6378 (10) | 0.0908 (3) | 0.3956 (7) | 0.062 (2) | 0.260 (5) |
C1' | 0.598 (2) | 0.2004 (9) | 0.563 (2) | 0.022 (4)* | 0.260 (5) |
O1' | 0.5488 (18) | 0.2454 (9) | 0.6348 (16) | 0.030 (3)* | 0.260 (5) |
C2' | 0.509 (3) | 0.1371 (8) | 0.4654 (18) | 0.043 (3)* | 0.260 (5) |
H2C | 0.4126 | 0.1538 | 0.3756 | 0.051* | 0.260 (5) |
H2D | 0.4713 | 0.1054 | 0.5307 | 0.051* | 0.260 (5) |
C3' | 0.816 (2) | 0.1494 (9) | 0.4786 (19) | 0.031 (4)* | 0.260 (5) |
O2' | 0.9434 (18) | 0.1456 (7) | 0.4835 (16) | 0.058 (4)* | 0.260 (5) |
O41 | 0.7846 (2) | 0.51026 (10) | 0.2317 (2) | 0.0271 (4) | |
O51 | 0.5405 (2) | 0.46597 (11) | 0.3110 (2) | 0.0306 (4) | |
C4 | 0.8696 (3) | 0.26039 (14) | 0.6299 (3) | 0.0246 (5) | |
H4A | 0.9756 | 0.2369 | 0.6503 | 0.029* | |
H4B | 0.8687 | 0.2770 | 0.7321 | 0.029* | |
C11 | 0.8541 (3) | 0.32519 (13) | 0.5213 (3) | 0.0200 (5) | |
C12 | 0.9815 (3) | 0.34997 (14) | 0.4763 (3) | 0.0209 (5) | |
C13 | 0.9635 (3) | 0.41147 (13) | 0.3805 (3) | 0.0220 (5) | |
H13 | 1.0517 | 0.4267 | 0.3531 | 0.026* | |
C14 | 0.8154 (3) | 0.44994 (13) | 0.3259 (3) | 0.0206 (5) | |
C15 | 0.6829 (3) | 0.42572 (13) | 0.3701 (3) | 0.0210 (5) | |
C16 | 0.7054 (3) | 0.36535 (14) | 0.4664 (3) | 0.0226 (5) | |
H16 | 0.6185 | 0.3506 | 0.4963 | 0.027* | |
C42 | 0.9181 (4) | 0.53475 (16) | 0.1850 (3) | 0.0314 (6) | |
H42A | 1.0140 | 0.5456 | 0.2793 | 0.047* | |
H42B | 0.8836 | 0.5774 | 0.1200 | 0.047* | |
H42C | 0.9456 | 0.4975 | 0.1246 | 0.047* | |
C52 | 0.3979 (4) | 0.43841 (18) | 0.3373 (4) | 0.0382 (7) | |
H52A | 0.3714 | 0.3911 | 0.2907 | 0.057* | |
H52B | 0.3050 | 0.4701 | 0.2882 | 0.057* | |
H52C | 0.4221 | 0.4356 | 0.4506 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br12 | 0.01665 (17) | 0.03972 (19) | 0.03410 (18) | 0.00527 (11) | 0.00770 (11) | 0.00516 (11) |
N1 | 0.0353 (13) | 0.0208 (11) | 0.0171 (9) | 0.0012 (9) | 0.0090 (9) | 0.0013 (7) |
S1 | 0.0307 (7) | 0.0365 (6) | 0.0297 (5) | −0.0097 (4) | 0.0088 (4) | −0.0036 (4) |
C1 | 0.028 (2) | 0.015 (2) | 0.0118 (19) | 0.0012 (17) | 0.0062 (17) | −0.0038 (17) |
O1 | 0.0257 (16) | 0.034 (2) | 0.0233 (16) | 0.0021 (13) | 0.0118 (13) | −0.0065 (15) |
C2 | 0.043 (3) | 0.022 (3) | 0.028 (3) | −0.005 (2) | 0.009 (2) | −0.001 (2) |
C3 | 0.034 (3) | 0.0177 (18) | 0.0182 (16) | 0.0077 (16) | 0.0150 (16) | 0.0067 (12) |
O2 | 0.049 (3) | 0.0315 (16) | 0.0351 (16) | 0.0164 (17) | 0.0260 (18) | 0.0023 (13) |
S1' | 0.111 (6) | 0.025 (3) | 0.0298 (19) | −0.012 (3) | 0.001 (3) | 0.0006 (16) |
O41 | 0.0250 (10) | 0.0261 (9) | 0.0335 (9) | 0.0000 (8) | 0.0148 (8) | 0.0075 (7) |
O51 | 0.0228 (10) | 0.0324 (10) | 0.0416 (10) | 0.0084 (8) | 0.0179 (8) | 0.0138 (8) |
C4 | 0.0194 (12) | 0.0315 (14) | 0.0218 (11) | 0.0044 (10) | 0.0064 (9) | 0.0057 (10) |
C11 | 0.0198 (12) | 0.0225 (12) | 0.0180 (10) | 0.0004 (9) | 0.0075 (9) | −0.0020 (9) |
C12 | 0.0153 (11) | 0.0278 (13) | 0.0185 (10) | 0.0013 (9) | 0.0050 (9) | −0.0063 (9) |
C13 | 0.0190 (12) | 0.0268 (13) | 0.0223 (11) | −0.0045 (10) | 0.0103 (9) | −0.0033 (9) |
C14 | 0.0224 (13) | 0.0199 (12) | 0.0197 (11) | −0.0029 (9) | 0.0079 (9) | −0.0021 (9) |
C15 | 0.0191 (12) | 0.0232 (12) | 0.0213 (11) | 0.0027 (10) | 0.0083 (9) | −0.0010 (9) |
C16 | 0.0203 (12) | 0.0262 (13) | 0.0242 (11) | −0.0004 (10) | 0.0116 (9) | 0.0012 (9) |
C42 | 0.0314 (15) | 0.0311 (14) | 0.0359 (14) | −0.0038 (12) | 0.0174 (12) | 0.0062 (11) |
C52 | 0.0246 (15) | 0.0452 (17) | 0.0521 (17) | 0.0104 (13) | 0.0229 (13) | 0.0151 (14) |
Br12—C12 | 1.911 (2) | O41—C42 | 1.443 (3) |
N1—C1' | 1.206 (18) | O51—C15 | 1.368 (3) |
N1—C3 | 1.371 (4) | O51—C52 | 1.435 (3) |
N1—C1 | 1.453 (6) | C4—C11 | 1.519 (3) |
N1—C4 | 1.466 (3) | C4—H4A | 0.9700 |
N1—C3' | 1.60 (2) | C4—H4B | 0.9700 |
S1—C1 | 1.762 (5) | C11—C12 | 1.388 (3) |
S1—C2 | 1.806 (6) | C11—C16 | 1.408 (3) |
C1—O1 | 1.215 (8) | C12—C13 | 1.400 (4) |
C2—C3 | 1.519 (9) | C13—C14 | 1.387 (3) |
C2—H2A | 0.9700 | C13—H13 | 0.9300 |
C2—H2B | 0.9700 | C14—C15 | 1.420 (3) |
C3—O2 | 1.224 (6) | C15—C16 | 1.381 (3) |
S1'—C2' | 1.70 (2) | C16—H16 | 0.9300 |
S1'—C3' | 1.802 (18) | C42—H42A | 0.9600 |
C1'—O1' | 1.221 (19) | C42—H42B | 0.9600 |
C1'—C2' | 1.50 (2) | C42—H42C | 0.9600 |
C2'—H2C | 0.9700 | C52—H52A | 0.9600 |
C2'—H2D | 0.9700 | C52—H52B | 0.9600 |
C3'—O2' | 1.09 (2) | C52—H52C | 0.9600 |
O41—C14 | 1.365 (3) | ||
C1'—N1—C3 | 99.4 (9) | C15—O51—C52 | 116.8 (2) |
C1'—N1—C1 | 15.0 (8) | N1—C4—C11 | 112.82 (19) |
C3—N1—C1 | 114.4 (4) | N1—C4—H4A | 109.0 |
C1'—N1—C4 | 134.2 (8) | C11—C4—H4A | 109.0 |
C3—N1—C4 | 126.5 (3) | N1—C4—H4B | 109.0 |
C1—N1—C4 | 119.2 (3) | C11—C4—H4B | 109.0 |
C1'—N1—C3' | 122.3 (10) | H4A—C4—H4B | 107.8 |
C3—N1—C3' | 23.4 (5) | C12—C11—C16 | 116.6 (2) |
C1—N1—C3' | 137.1 (7) | C12—C11—C4 | 123.9 (2) |
C4—N1—C3' | 103.4 (6) | C16—C11—C4 | 119.4 (2) |
C1—S1—C2 | 93.1 (3) | C11—C12—C13 | 122.0 (2) |
O1—C1—N1 | 124.0 (4) | C11—C12—Br12 | 121.66 (19) |
O1—C1—S1 | 124.8 (5) | C13—C12—Br12 | 116.37 (18) |
N1—C1—S1 | 111.1 (4) | C14—C13—C12 | 120.7 (2) |
C3—C2—S1 | 107.3 (4) | C14—C13—H13 | 119.7 |
C3—C2—H2A | 110.3 | C12—C13—H13 | 119.7 |
S1—C2—H2A | 110.3 | O41—C14—C13 | 125.4 (2) |
C3—C2—H2B | 110.3 | O41—C14—C15 | 116.1 (2) |
S1—C2—H2B | 110.3 | C13—C14—C15 | 118.5 (2) |
H2A—C2—H2B | 108.5 | O51—C15—C16 | 125.4 (2) |
O2—C3—N1 | 122.0 (5) | O51—C15—C14 | 115.3 (2) |
O2—C3—C2 | 124.0 (4) | C16—C15—C14 | 119.4 (2) |
N1—C3—C2 | 114.0 (4) | C15—C16—C11 | 122.9 (2) |
C2'—S1'—C3' | 97.0 (9) | C15—C16—H16 | 118.6 |
N1—C1'—O1' | 118.5 (17) | C11—C16—H16 | 118.6 |
N1—C1'—C2' | 111.8 (14) | O41—C42—H42A | 109.5 |
O1'—C1'—C2' | 129.6 (18) | O41—C42—H42B | 109.5 |
C1'—C2'—S1' | 110.3 (14) | H42A—C42—H42B | 109.5 |
C1'—C2'—H2C | 109.6 | O41—C42—H42C | 109.5 |
S1'—C2'—H2C | 109.6 | H42A—C42—H42C | 109.5 |
C1'—C2'—H2D | 109.6 | H42B—C42—H42C | 109.5 |
S1'—C2'—H2D | 109.6 | O51—C52—H52A | 109.5 |
H2C—C2'—H2D | 108.1 | O51—C52—H52B | 109.5 |
O2'—C3'—N1 | 129.0 (14) | H52A—C52—H52B | 109.5 |
O2'—C3'—S1' | 132.5 (17) | O51—C52—H52C | 109.5 |
N1—C3'—S1' | 98.3 (11) | H52A—C52—H52C | 109.5 |
C14—O41—C42 | 116.4 (2) | H52B—C52—H52C | 109.5 |
C1'—N1—C1—O1 | 180 (4) | C1—N1—C3'—O2' | −166.8 (13) |
C3—N1—C1—O1 | 175.9 (4) | C4—N1—C3'—O2' | 6.3 (17) |
C4—N1—C1—O1 | −3.2 (5) | C1'—N1—C3'—S1' | 5.2 (13) |
C3'—N1—C1—O1 | 169.1 (8) | C3—N1—C3'—S1' | −7.2 (8) |
C1'—N1—C1—S1 | 1 (3) | C1—N1—C3'—S1' | 8.5 (11) |
C3—N1—C1—S1 | −3.4 (3) | C4—N1—C3'—S1' | −178.4 (5) |
C4—N1—C1—S1 | 177.52 (19) | C2'—S1'—C3'—O2' | 173.9 (17) |
C3'—N1—C1—S1 | −10.2 (9) | C2'—S1'—C3'—N1 | −1.1 (8) |
C2—S1—C1—O1 | −177.6 (4) | C1'—N1—C4—C11 | −88.1 (11) |
C2—S1—C1—N1 | 1.7 (3) | C3—N1—C4—C11 | 91.8 (3) |
C1—S1—C2—C3 | 0.2 (4) | C1—N1—C4—C11 | −89.2 (3) |
C1'—N1—C3—O2 | −177.4 (8) | C3'—N1—C4—C11 | 96.2 (6) |
C1—N1—C3—O2 | −176.4 (3) | N1—C4—C11—C12 | −128.1 (2) |
C4—N1—C3—O2 | 2.6 (5) | N1—C4—C11—C16 | 54.6 (3) |
C3'—N1—C3—O2 | −8.1 (13) | C16—C11—C12—C13 | −0.4 (3) |
C1'—N1—C3—C2 | 2.6 (9) | C4—C11—C12—C13 | −177.7 (2) |
C1—N1—C3—C2 | 3.6 (4) | C16—C11—C12—Br12 | 178.09 (17) |
C4—N1—C3—C2 | −177.4 (4) | C4—C11—C12—Br12 | 0.7 (3) |
C3'—N1—C3—C2 | 172.0 (15) | C11—C12—C13—C14 | −0.3 (3) |
S1—C2—C3—O2 | 177.8 (3) | Br12—C12—C13—C14 | −178.87 (17) |
S1—C2—C3—N1 | −2.2 (5) | C42—O41—C14—C13 | 0.6 (3) |
C3—N1—C1'—O1' | −178.4 (15) | C42—O41—C14—C15 | −179.4 (2) |
C1—N1—C1'—O1' | 5 (2) | C12—C13—C14—O41 | −179.7 (2) |
C4—N1—C1'—O1' | 2 (2) | C12—C13—C14—C15 | 0.3 (3) |
C3'—N1—C1'—O1' | 176.6 (14) | C52—O51—C15—C16 | −7.1 (4) |
C3—N1—C1'—C2' | −2.0 (13) | C52—O51—C15—C14 | 172.9 (2) |
C1—N1—C1'—C2' | −178 (4) | O41—C14—C15—O51 | 0.5 (3) |
C4—N1—C1'—C2' | 177.9 (6) | C13—C14—C15—O51 | −179.5 (2) |
C3'—N1—C1'—C2' | −7.0 (17) | O41—C14—C15—C16 | −179.5 (2) |
N1—C1'—C2'—S1' | 5.3 (16) | C13—C14—C15—C16 | 0.5 (3) |
O1'—C1'—C2'—S1' | −178.8 (17) | O51—C15—C16—C11 | 178.8 (2) |
C3'—S1'—C2'—C1' | −1.9 (12) | C14—C15—C16—C11 | −1.3 (4) |
C1'—N1—C3'—O2' | −170.1 (17) | C12—C11—C16—C15 | 1.2 (3) |
C3—N1—C3'—O2' | 177 (3) | C4—C11—C16—C15 | 178.7 (2) |