Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028618/wn6374sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028618/wn6374Isup2.hkl |
CCDC reference: 287744
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.007 Å
- R factor = 0.040
- wR factor = 0.133
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. O2 .. 3.22 Ang.
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 26.98 From the CIF: _reflns_number_total 2454 Count of symmetry unique reflns 1470 Completeness (_total/calc) 166.94% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 984 Fraction of Friedel pairs measured 0.669 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
The title compound was synthesized by bromination of 1-methoxy-2,3- dimethyl-4-nitrobenzene with N-bromosuccinimide in CCl4, according to the literature method (Lai & Yap, 1993; Knölker et al., 1993). Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in hexane-MeOH (2:1).
After their location in a difference Fourier map, H atoms were placed in calculated positions and allowed to ride on their parent atoms, with C—H = 0.93–0.97 Å, and Uiso(H) = 1.2 − 1.5 Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999)'; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
C9H9Br2NO3 | F(000) = 656 |
Mr = 338.99 | Dx = 1.989 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2142 reflections |
a = 4.7900 (9) Å | θ = 2.4–23.8° |
b = 13.772 (3) Å | µ = 7.15 mm−1 |
c = 17.158 (3) Å | T = 292 K |
V = 1131.9 (4) Å3 | Block, colorless |
Z = 4 | 0.20 × 0.20 × 0.20 mm |
Bruker SMART APEX CCD area detector diffractometer | 2454 independent reflections |
Radiation source: fine-focus sealed tube | 1920 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ϕ and ω scans | θmax = 27.0°, θmin = 1.9° |
Absorption correction: multi-scan SADABS, (Sheldrick, 1997) | h = −5→6 |
Tmin = 0.239, Tmax = 0.243 | k = −14→17 |
6493 measured reflections | l = −20→21 |
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)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0709P)2 + 0.0631P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max = 0.001 |
2454 reflections | Δρmax = 0.74 e Å−3 |
137 parameters | Δρmin = −0.68 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1465 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (3) |
C9H9Br2NO3 | V = 1131.9 (4) Å3 |
Mr = 338.99 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 4.7900 (9) Å | µ = 7.15 mm−1 |
b = 13.772 (3) Å | T = 292 K |
c = 17.158 (3) Å | 0.20 × 0.20 × 0.20 mm |
Bruker SMART APEX CCD area detector diffractometer | 2454 independent reflections |
Absorption correction: multi-scan SADABS, (Sheldrick, 1997) | 1920 reflections with I > 2σ(I) |
Tmin = 0.239, Tmax = 0.243 | Rint = 0.034 |
6493 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.133 | Δρmax = 0.74 e Å−3 |
S = 1.13 | Δρmin = −0.68 e Å−3 |
2454 reflections | Absolute structure: Flack (1983), 1465 Friedel pairs |
137 parameters | Absolute structure parameter: 0.04 (3) |
0 restraints |
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 | 0.33783 (11) | 0.76067 (3) | 0.37981 (4) | 0.05730 (14) | |
Br2 | 0.24514 (11) | 0.50316 (4) | 0.57797 (3) | 0.05282 (13) | |
C1 | 0.0810 (9) | 0.6549 (3) | 0.4045 (3) | 0.0395 (12) | |
H1A | 0.0677 | 0.6491 | 0.4607 | 0.047* | |
H1B | −0.1029 | 0.6717 | 0.3851 | 0.047* | |
C2 | 0.4926 (10) | 0.5325 (3) | 0.4876 (3) | 0.0394 (11) | |
H2A | 0.5296 | 0.6017 | 0.4852 | 0.047* | |
H2B | 0.6692 | 0.4988 | 0.4935 | 0.047* | |
C3 | 0.1624 (9) | 0.5585 (3) | 0.3716 (2) | 0.0340 (10) | |
C4 | 0.0468 (9) | 0.5201 (3) | 0.3046 (3) | 0.0392 (11) | |
C5 | 0.0927 (12) | 0.4270 (4) | 0.2806 (3) | 0.0483 (13) | |
H5 | −0.0003 | 0.4024 | 0.2373 | 0.058* | |
C6 | 0.2772 (12) | 0.3701 (3) | 0.3209 (3) | 0.0523 (14) | |
H6 | 0.3112 | 0.3072 | 0.3038 | 0.063* | |
C7 | 0.4168 (11) | 0.4044 (3) | 0.3877 (3) | 0.0434 (12) | |
C8 | 0.3485 (9) | 0.4995 (3) | 0.4135 (2) | 0.0335 (9) | |
C9 | 0.6450 (14) | 0.2542 (4) | 0.4098 (4) | 0.0770 (19) | |
H9A | 0.5068 | 0.2126 | 0.4327 | 0.115* | |
H9B | 0.8269 | 0.2354 | 0.4278 | 0.115* | |
H9C | 0.6375 | 0.2486 | 0.3541 | 0.115* | |
N1 | −0.1324 (10) | 0.5766 (3) | 0.2535 (2) | 0.0534 (12) | |
O1 | −0.0828 (11) | 0.6644 (3) | 0.2492 (3) | 0.0763 (13) | |
O2 | −0.3141 (11) | 0.5353 (4) | 0.2187 (3) | 0.0910 (16) | |
O3 | 0.5906 (8) | 0.3537 (2) | 0.4321 (2) | 0.0541 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0627 (3) | 0.0344 (2) | 0.0749 (3) | 0.0016 (2) | 0.0011 (3) | 0.0057 (2) |
Br2 | 0.0697 (3) | 0.0561 (3) | 0.0326 (2) | −0.0035 (3) | −0.0012 (2) | 0.0022 (2) |
C1 | 0.034 (2) | 0.039 (2) | 0.045 (3) | 0.0077 (18) | 0.0050 (19) | −0.0002 (18) |
C2 | 0.041 (2) | 0.035 (2) | 0.043 (2) | −0.0021 (18) | −0.002 (2) | 0.0011 (19) |
C3 | 0.033 (2) | 0.0327 (19) | 0.037 (2) | −0.0043 (17) | 0.0052 (19) | 0.0017 (17) |
C4 | 0.032 (2) | 0.047 (2) | 0.038 (2) | −0.0103 (19) | −0.0024 (18) | 0.0070 (19) |
C5 | 0.056 (3) | 0.057 (3) | 0.032 (2) | −0.018 (2) | −0.002 (2) | −0.005 (2) |
C6 | 0.079 (4) | 0.033 (2) | 0.045 (3) | −0.010 (2) | 0.000 (3) | −0.0069 (19) |
C7 | 0.065 (3) | 0.029 (2) | 0.037 (2) | −0.003 (2) | 0.007 (2) | 0.0045 (19) |
C8 | 0.045 (2) | 0.0317 (19) | 0.0237 (17) | −0.004 (2) | 0.0049 (16) | −0.0037 (17) |
C9 | 0.081 (4) | 0.044 (3) | 0.106 (5) | 0.024 (3) | −0.003 (3) | 0.004 (3) |
N1 | 0.042 (2) | 0.079 (3) | 0.040 (2) | 0.000 (2) | −0.005 (2) | 0.014 (2) |
O1 | 0.086 (3) | 0.074 (2) | 0.069 (2) | 0.011 (2) | −0.019 (2) | 0.029 (2) |
O2 | 0.084 (3) | 0.125 (4) | 0.065 (3) | −0.011 (3) | −0.037 (2) | 0.018 (2) |
O3 | 0.059 (2) | 0.0409 (16) | 0.062 (2) | 0.0164 (16) | −0.0027 (19) | 0.0024 (16) |
Br1—C1 | 1.953 (5) | C5—C6 | 1.369 (7) |
Br2—C2 | 1.993 (5) | C5—H5 | 0.9300 |
C1—C3 | 1.495 (6) | C6—C7 | 1.408 (7) |
C1—H1A | 0.9700 | C6—H6 | 0.9300 |
C1—H1B | 0.9700 | C7—O3 | 1.327 (6) |
C2—C8 | 1.516 (6) | C7—C8 | 1.422 (6) |
C2—H2A | 0.9700 | C9—O3 | 1.446 (6) |
C2—H2B | 0.9700 | C9—H9A | 0.9600 |
C3—C4 | 1.382 (6) | C9—H9B | 0.9600 |
C3—C8 | 1.404 (6) | C9—H9C | 0.9600 |
C4—C5 | 1.365 (7) | N1—O2 | 1.199 (6) |
C4—N1 | 1.452 (6) | N1—O1 | 1.235 (6) |
C3—C1—Br1 | 114.6 (3) | C6—C5—H5 | 120.4 |
C3—C1—H1A | 108.6 | C5—C6—C7 | 121.8 (4) |
Br1—C1—H1A | 108.6 | C5—C6—H6 | 119.1 |
C3—C1—H1B | 108.6 | C7—C6—H6 | 119.1 |
Br1—C1—H1B | 108.6 | O3—C7—C6 | 126.1 (4) |
H1A—C1—H1B | 107.6 | O3—C7—C8 | 116.8 (4) |
C8—C2—Br2 | 108.7 (3) | C6—C7—C8 | 117.0 (4) |
C8—C2—H2A | 109.9 | C3—C8—C7 | 121.3 (4) |
Br2—C2—H2A | 109.9 | C3—C8—C2 | 123.1 (4) |
C8—C2—H2B | 109.9 | C7—C8—C2 | 115.6 (4) |
Br2—C2—H2B | 109.9 | O3—C9—H9A | 109.5 |
H2A—C2—H2B | 108.3 | O3—C9—H9B | 109.5 |
C4—C3—C8 | 117.4 (4) | H9A—C9—H9B | 109.5 |
C4—C3—C1 | 123.4 (4) | O3—C9—H9C | 109.5 |
C8—C3—C1 | 119.0 (4) | H9A—C9—H9C | 109.5 |
C5—C4—C3 | 123.1 (4) | H9B—C9—H9C | 109.5 |
C5—C4—N1 | 114.7 (4) | O2—N1—O1 | 125.0 (5) |
C3—C4—N1 | 122.2 (4) | O2—N1—C4 | 118.4 (4) |
C4—C5—C6 | 119.3 (4) | O1—N1—C4 | 116.6 (4) |
C4—C5—H5 | 120.4 | C7—O3—C9 | 117.4 (4) |
Br1—C1—C3—C4 | −99.7 (4) | C1—C3—C8—C2 | −5.7 (6) |
Br1—C1—C3—C8 | 85.7 (4) | O3—C7—C8—C3 | −178.8 (4) |
C8—C3—C4—C5 | 3.9 (7) | C6—C7—C8—C3 | −3.6 (7) |
C1—C3—C4—C5 | −170.7 (4) | O3—C7—C8—C2 | 2.2 (6) |
C8—C3—C4—N1 | −175.5 (4) | C6—C7—C8—C2 | 177.3 (4) |
C1—C3—C4—N1 | 9.9 (7) | Br2—C2—C8—C3 | 87.3 (4) |
C3—C4—C5—C6 | −4.9 (8) | Br2—C2—C8—C7 | −93.6 (4) |
N1—C4—C5—C6 | 174.5 (5) | C5—C4—N1—O2 | 32.2 (7) |
C4—C5—C6—C7 | 1.4 (8) | C3—C4—N1—O2 | −148.4 (5) |
C5—C6—C7—O3 | 177.4 (5) | C5—C4—N1—O1 | −147.3 (5) |
C5—C6—C7—C8 | 2.7 (7) | C3—C4—N1—O1 | 32.1 (7) |
C4—C3—C8—C7 | 0.5 (6) | C6—C7—O3—C9 | 0.7 (8) |
C1—C3—C8—C7 | 175.4 (4) | C8—C7—O3—C9 | 175.3 (4) |
C4—C3—C8—C2 | 179.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.93 | 2.43 | 3.216 (6) | 143 |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C9H9Br2NO3 |
Mr | 338.99 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 292 |
a, b, c (Å) | 4.7900 (9), 13.772 (3), 17.158 (3) |
V (Å3) | 1131.9 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 7.15 |
Crystal size (mm) | 0.20 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area detector diffractometer |
Absorption correction | Multi-scan SADABS, (Sheldrick, 1997) |
Tmin, Tmax | 0.239, 0.243 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6493, 2454, 1920 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.638 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.133, 1.13 |
No. of reflections | 2454 |
No. of parameters | 137 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.74, −0.68 |
Absolute structure | Flack (1983), 1465 Friedel pairs |
Absolute structure parameter | 0.04 (3) |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999)', SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.
Br1—C1 | 1.953 (5) | C9—O3 | 1.446 (6) |
Br2—C2 | 1.993 (5) | N1—O2 | 1.199 (6) |
C4—N1 | 1.452 (6) | N1—O1 | 1.235 (6) |
C7—O3 | 1.327 (6) | ||
C3—C1—Br1 | 114.6 (3) | O2—N1—C4 | 118.4 (4) |
C8—C2—Br2 | 108.7 (3) | O1—N1—C4 | 116.6 (4) |
O2—N1—O1 | 125.0 (5) | C7—O3—C9 | 117.4 (4) |
C8—C3—C4—N1 | −175.5 (4) | C5—C6—C7—O3 | 177.4 (5) |
N1—C4—C5—C6 | 174.5 (5) | O3—C7—C8—C3 | −178.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.93 | 2.43 | 3.216 (6) | 143 |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
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1,2-Bis(bromomethyl)benzene and its derivatives are important building blocks in supramolecular chemistry (Wu et al., 2002). In this paper, we report the crystal structure of the title compound, (I) (Fig. 1). The bond lengths and angles are within normal ranges (Allen et al., 1987). The crystal structure is stabilized by intermolecular C—H···O interactions (Table 2 and Fig. 2).