Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804015491/wk6020sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804015491/wk6020Isup2.hkl |
CCDC reference: 248764
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.027
- wR factor = 0.068
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Br1 .. O1 .. 3.01 Ang.
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G 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 27.04 From the CIF: _reflns_number_total 2621 Count of symmetry unique reflns 1547 Completeness (_total/calc) 169.42% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1074 Fraction of Friedel pairs measured 0.694 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
C9H10Br2N2O3 | Dx = 1.937 Mg m−3 |
Mr = 354.01 | Melting point: 389 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.4237 (18) Å | Cell parameters from 907 reflections |
b = 13.445 (4) Å | θ = 2.9–26.1° |
c = 14.054 (4) Å | µ = 6.67 mm−1 |
V = 1213.8 (6) Å3 | T = 273 K |
Z = 4 | Block, colorless |
F(000) = 688 | 0.50 × 0.30 × 0.17 mm |
Bruker SMART 1000 CCD area-detector diffractometer | 2621 independent reflections |
Radiation source: fine-focus sealed tube | 2257 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 27.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→8 |
Tmin = 0.109, Tmax = 0.322 | k = −8→17 |
7341 measured reflections | l = −17→17 |
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)] = 0.028 | H-atom parameters constrained |
wR(F2) = 0.068 | w = 1/[σ2(Fo2) + (0.0323P)2 + 0.0575P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2621 reflections | Δρmax = 0.27 e Å−3 |
145 parameters | Δρmin = −0.58 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.028 (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 | ||
Br1 | 0.80110 (6) | 0.93562 (3) | 0.86822 (3) | 0.05792 (13) | |
Br2 | 0.34587 (7) | 0.78812 (4) | 0.92941 (2) | 0.06719 (15) | |
C1 | 0.5839 (5) | 0.8972 (3) | 0.7897 (2) | 0.0387 (7) | |
C2 | 0.4104 (5) | 0.8420 (3) | 0.8109 (2) | 0.0395 (7) | |
C3 | 0.2917 (5) | 0.8336 (3) | 0.7281 (2) | 0.0399 (7) | |
H3A | 0.1661 | 0.7998 | 0.7219 | 0.048* | |
C4 | 0.3940 (5) | 0.8845 (2) | 0.6576 (2) | 0.0341 (7) | |
C5 | 0.7331 (6) | 0.9813 (4) | 0.6468 (3) | 0.0624 (10) | |
H5A | 0.8414 | 0.9986 | 0.6909 | 0.094* | |
H5B | 0.6721 | 1.0409 | 0.6215 | 0.094* | |
H5C | 0.7908 | 0.9426 | 0.5959 | 0.094* | |
C6 | 0.3315 (5) | 0.9014 (2) | 0.5578 (2) | 0.0388 (7) | |
C7 | 0.0871 (5) | 0.8657 (3) | 0.4341 (2) | 0.0449 (8) | |
H7A | 0.0590 | 0.9364 | 0.4284 | 0.054* | |
H7B | −0.0442 | 0.8308 | 0.4275 | 0.054* | |
C8 | 0.2300 (5) | 0.8346 (2) | 0.3548 (2) | 0.0373 (7) | |
C9 | 0.2957 (7) | 0.8563 (3) | 0.1911 (2) | 0.0581 (10) | |
H9A | 0.2413 | 0.8925 | 0.1378 | 0.087* | |
H9B | 0.2885 | 0.7863 | 0.1783 | 0.087* | |
H9C | 0.4381 | 0.8751 | 0.2016 | 0.087* | |
N1 | 0.5750 (4) | 0.9239 (2) | 0.69537 (17) | 0.0377 (6) | |
N2 | 0.1711 (4) | 0.8461 (2) | 0.52682 (16) | 0.0411 (6) | |
H2A | 0.1197 | 0.7998 | 0.5619 | 0.049* | |
O1 | 0.4118 (4) | 0.9631 (2) | 0.50695 (17) | 0.0620 (7) | |
O2 | 0.3706 (4) | 0.7764 (2) | 0.36135 (17) | 0.0587 (7) | |
O3 | 0.1756 (4) | 0.87870 (18) | 0.27403 (15) | 0.0513 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.04399 (19) | 0.0715 (3) | 0.0582 (2) | 0.00563 (18) | −0.01661 (16) | −0.02274 (19) |
Br2 | 0.0695 (3) | 0.1003 (3) | 0.03177 (17) | 0.0035 (2) | 0.00218 (17) | 0.0141 (2) |
C1 | 0.0331 (14) | 0.0463 (19) | 0.0366 (16) | 0.0069 (14) | −0.0040 (12) | −0.0141 (13) |
C2 | 0.0417 (17) | 0.050 (2) | 0.0269 (14) | 0.0032 (15) | 0.0012 (12) | −0.0005 (14) |
C3 | 0.0364 (15) | 0.0482 (18) | 0.0350 (15) | −0.0044 (16) | 0.0030 (13) | 0.0009 (14) |
C4 | 0.0327 (14) | 0.0389 (17) | 0.0305 (15) | −0.0010 (13) | −0.0001 (11) | −0.0029 (12) |
C5 | 0.0449 (19) | 0.076 (3) | 0.066 (2) | −0.0219 (19) | 0.0044 (17) | 0.007 (2) |
C6 | 0.0411 (16) | 0.0446 (18) | 0.0308 (14) | −0.0046 (14) | 0.0046 (13) | 0.0024 (13) |
C7 | 0.0420 (16) | 0.056 (2) | 0.0366 (16) | 0.0061 (16) | −0.0033 (14) | −0.0013 (16) |
C8 | 0.0412 (16) | 0.0377 (16) | 0.0331 (15) | −0.0001 (14) | −0.0041 (12) | 0.0010 (13) |
C9 | 0.082 (3) | 0.060 (2) | 0.0333 (17) | −0.012 (2) | 0.0102 (18) | 0.0009 (16) |
N1 | 0.0337 (12) | 0.0423 (16) | 0.0371 (13) | −0.0052 (12) | 0.0026 (10) | −0.0056 (12) |
N2 | 0.0434 (14) | 0.0517 (16) | 0.0281 (12) | −0.0061 (15) | −0.0003 (11) | 0.0023 (12) |
O1 | 0.0747 (18) | 0.0682 (17) | 0.0431 (13) | −0.0267 (15) | 0.0005 (12) | 0.0148 (13) |
O2 | 0.0620 (16) | 0.0673 (17) | 0.0467 (13) | 0.0279 (14) | 0.0008 (12) | 0.0033 (13) |
O3 | 0.0672 (15) | 0.0527 (14) | 0.0341 (11) | 0.0146 (14) | −0.0021 (12) | 0.0074 (10) |
Br1—C1 | 1.853 (3) | C5—N1 | 1.447 (4) |
Br2—C2 | 1.863 (3) | C6—O1 | 1.211 (4) |
C1—C2 | 1.372 (5) | C6—N2 | 1.343 (4) |
C1—N1 | 1.374 (4) | C7—N2 | 1.435 (4) |
C2—C3 | 1.396 (4) | C7—C8 | 1.503 (4) |
C3—C4 | 1.372 (4) | C8—O2 | 1.199 (4) |
C4—N1 | 1.384 (4) | C8—O3 | 1.328 (4) |
C4—C6 | 1.476 (4) | C9—O3 | 1.430 (4) |
C2—C1—N1 | 108.5 (3) | O1—C6—C4 | 123.4 (3) |
C2—C1—Br1 | 129.3 (2) | N2—C6—C4 | 115.6 (3) |
N1—C1—Br1 | 122.2 (2) | N2—C7—C8 | 113.1 (3) |
C1—C2—C3 | 107.8 (3) | O2—C8—O3 | 123.7 (3) |
C1—C2—Br2 | 125.8 (2) | O2—C8—C7 | 125.8 (3) |
C3—C2—Br2 | 126.3 (2) | O3—C8—C7 | 110.4 (3) |
C4—C3—C2 | 107.5 (3) | C1—N1—C4 | 107.8 (3) |
C3—C4—N1 | 108.4 (3) | C1—N1—C5 | 124.4 (3) |
C3—C4—C6 | 129.2 (3) | C4—N1—C5 | 127.8 (3) |
N1—C4—C6 | 122.3 (3) | C6—N2—C7 | 118.7 (3) |
O1—C6—N2 | 121.0 (3) | C8—O3—C9 | 117.5 (3) |
N1—C1—C2—C3 | 0.4 (4) | C2—C1—N1—C4 | −0.2 (4) |
Br1—C1—C2—C3 | 179.5 (3) | Br1—C1—N1—C4 | −179.4 (2) |
N1—C1—C2—Br2 | −179.6 (2) | C2—C1—N1—C5 | −178.9 (3) |
Br1—C1—C2—Br2 | −0.5 (5) | Br1—C1—N1—C5 | 1.9 (5) |
C1—C2—C3—C4 | −0.4 (4) | C3—C4—N1—C1 | 0.0 (4) |
Br2—C2—C3—C4 | 179.6 (3) | C6—C4—N1—C1 | 178.1 (3) |
C2—C3—C4—N1 | 0.3 (4) | C3—C4—N1—C5 | 178.7 (4) |
C2—C3—C4—C6 | −177.8 (3) | C6—C4—N1—C5 | −3.2 (5) |
C3—C4—C6—O1 | 164.9 (4) | O1—C6—N2—C7 | −4.0 (5) |
N1—C4—C6—O1 | −12.9 (5) | C4—C6—N2—C7 | 173.4 (3) |
C3—C4—C6—N2 | −12.5 (5) | C8—C7—N2—C6 | 71.0 (4) |
N1—C4—C6—N2 | 169.8 (3) | O2—C8—O3—C9 | −1.4 (5) |
N2—C7—C8—O2 | 19.6 (5) | C7—C8—O3—C9 | −179.6 (3) |
N2—C7—C8—O3 | −162.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2i | 0.86 | 2.18 | 2.984 (4) | 155 |
Symmetry code: (i) x−1/2, −y+3/2, −z+1. |
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