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In the title compound, C9H9Br2NO3, the mol­ecules are linked by inter­molecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028618/wn6374sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028618/wn6374Isup2.hkl
Contains datablock I

CCDC reference: 287744

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](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

Comment top

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).

Experimental top

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).

Refinement top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. C—H···O intermolecular hydrogen-bonding, shown as dashed lines. [Symmetry codes: (a) 1 − x, −1/2 + y, 1/2 − z; (b) 1 − x, 1/2 + y, 1/2 − z; (c) 1/2 + x, −1/2 − y, 1 − z; (d) 1/2 − x, 1 − y, 1/2 + z; (e) 1/2 + x, 1/2 − y, 1 − z.]
(I) top
Crystal data top
C9H9Br2NO3F(000) = 656
Mr = 338.99Dx = 1.989 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2142 reflections
a = 4.7900 (9) Åθ = 2.4–23.8°
b = 13.772 (3) ŵ = 7.15 mm1
c = 17.158 (3) ÅT = 292 K
V = 1131.9 (4) Å3Block, colorless
Z = 40.20 × 0.20 × 0.20 mm
Data collection top
Bruker SMART APEX CCD area detector
diffractometer
2454 independent reflections
Radiation source: fine-focus sealed tube1920 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ϕ and ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
SADABS, (Sheldrick, 1997)
h = 56
Tmin = 0.239, Tmax = 0.243k = 1417
6493 measured reflectionsl = 2021
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-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 reflectionsΔρmax = 0.74 e Å3
137 parametersΔρmin = 0.68 e Å3
0 restraintsAbsolute structure: Flack (1983), 1465 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (3)
Crystal data top
C9H9Br2NO3V = 1131.9 (4) Å3
Mr = 338.99Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.7900 (9) ŵ = 7.15 mm1
b = 13.772 (3) ÅT = 292 K
c = 17.158 (3) Å0.20 × 0.20 × 0.20 mm
Data collection top
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 = 0.243Rint = 0.034
6493 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.133Δρmax = 0.74 e Å3
S = 1.13Δρmin = 0.68 e Å3
2454 reflectionsAbsolute structure: Flack (1983), 1465 Friedel pairs
137 parametersAbsolute structure parameter: 0.04 (3)
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.33783 (11)0.76067 (3)0.37981 (4)0.05730 (14)
Br20.24514 (11)0.50316 (4)0.57797 (3)0.05282 (13)
C10.0810 (9)0.6549 (3)0.4045 (3)0.0395 (12)
H1A0.06770.64910.46070.047*
H1B0.10290.67170.38510.047*
C20.4926 (10)0.5325 (3)0.4876 (3)0.0394 (11)
H2A0.52960.60170.48520.047*
H2B0.66920.49880.49350.047*
C30.1624 (9)0.5585 (3)0.3716 (2)0.0340 (10)
C40.0468 (9)0.5201 (3)0.3046 (3)0.0392 (11)
C50.0927 (12)0.4270 (4)0.2806 (3)0.0483 (13)
H50.00030.40240.23730.058*
C60.2772 (12)0.3701 (3)0.3209 (3)0.0523 (14)
H60.31120.30720.30380.063*
C70.4168 (11)0.4044 (3)0.3877 (3)0.0434 (12)
C80.3485 (9)0.4995 (3)0.4135 (2)0.0335 (9)
C90.6450 (14)0.2542 (4)0.4098 (4)0.0770 (19)
H9A0.50680.21260.43270.115*
H9B0.82690.23540.42780.115*
H9C0.63750.24860.35410.115*
N10.1324 (10)0.5766 (3)0.2535 (2)0.0534 (12)
O10.0828 (11)0.6644 (3)0.2492 (3)0.0763 (13)
O20.3141 (11)0.5353 (4)0.2187 (3)0.0910 (16)
O30.5906 (8)0.3537 (2)0.4321 (2)0.0541 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0627 (3)0.0344 (2)0.0749 (3)0.0016 (2)0.0011 (3)0.0057 (2)
Br20.0697 (3)0.0561 (3)0.0326 (2)0.0035 (3)0.0012 (2)0.0022 (2)
C10.034 (2)0.039 (2)0.045 (3)0.0077 (18)0.0050 (19)0.0002 (18)
C20.041 (2)0.035 (2)0.043 (2)0.0021 (18)0.002 (2)0.0011 (19)
C30.033 (2)0.0327 (19)0.037 (2)0.0043 (17)0.0052 (19)0.0017 (17)
C40.032 (2)0.047 (2)0.038 (2)0.0103 (19)0.0024 (18)0.0070 (19)
C50.056 (3)0.057 (3)0.032 (2)0.018 (2)0.002 (2)0.005 (2)
C60.079 (4)0.033 (2)0.045 (3)0.010 (2)0.000 (3)0.0069 (19)
C70.065 (3)0.029 (2)0.037 (2)0.003 (2)0.007 (2)0.0045 (19)
C80.045 (2)0.0317 (19)0.0237 (17)0.004 (2)0.0049 (16)0.0037 (17)
C90.081 (4)0.044 (3)0.106 (5)0.024 (3)0.003 (3)0.004 (3)
N10.042 (2)0.079 (3)0.040 (2)0.000 (2)0.005 (2)0.014 (2)
O10.086 (3)0.074 (2)0.069 (2)0.011 (2)0.019 (2)0.029 (2)
O20.084 (3)0.125 (4)0.065 (3)0.011 (3)0.037 (2)0.018 (2)
O30.059 (2)0.0409 (16)0.062 (2)0.0164 (16)0.0027 (19)0.0024 (16)
Geometric parameters (Å, º) top
Br1—C11.953 (5)C5—C61.369 (7)
Br2—C21.993 (5)C5—H50.9300
C1—C31.495 (6)C6—C71.408 (7)
C1—H1A0.9700C6—H60.9300
C1—H1B0.9700C7—O31.327 (6)
C2—C81.516 (6)C7—C81.422 (6)
C2—H2A0.9700C9—O31.446 (6)
C2—H2B0.9700C9—H9A0.9600
C3—C41.382 (6)C9—H9B0.9600
C3—C81.404 (6)C9—H9C0.9600
C4—C51.365 (7)N1—O21.199 (6)
C4—N11.452 (6)N1—O11.235 (6)
C3—C1—Br1114.6 (3)C6—C5—H5120.4
C3—C1—H1A108.6C5—C6—C7121.8 (4)
Br1—C1—H1A108.6C5—C6—H6119.1
C3—C1—H1B108.6C7—C6—H6119.1
Br1—C1—H1B108.6O3—C7—C6126.1 (4)
H1A—C1—H1B107.6O3—C7—C8116.8 (4)
C8—C2—Br2108.7 (3)C6—C7—C8117.0 (4)
C8—C2—H2A109.9C3—C8—C7121.3 (4)
Br2—C2—H2A109.9C3—C8—C2123.1 (4)
C8—C2—H2B109.9C7—C8—C2115.6 (4)
Br2—C2—H2B109.9O3—C9—H9A109.5
H2A—C2—H2B108.3O3—C9—H9B109.5
C4—C3—C8117.4 (4)H9A—C9—H9B109.5
C4—C3—C1123.4 (4)O3—C9—H9C109.5
C8—C3—C1119.0 (4)H9A—C9—H9C109.5
C5—C4—C3123.1 (4)H9B—C9—H9C109.5
C5—C4—N1114.7 (4)O2—N1—O1125.0 (5)
C3—C4—N1122.2 (4)O2—N1—C4118.4 (4)
C4—C5—C6119.3 (4)O1—N1—C4116.6 (4)
C4—C5—H5120.4C7—O3—C9117.4 (4)
Br1—C1—C3—C499.7 (4)C1—C3—C8—C25.7 (6)
Br1—C1—C3—C885.7 (4)O3—C7—C8—C3178.8 (4)
C8—C3—C4—C53.9 (7)C6—C7—C8—C33.6 (7)
C1—C3—C4—C5170.7 (4)O3—C7—C8—C22.2 (6)
C8—C3—C4—N1175.5 (4)C6—C7—C8—C2177.3 (4)
C1—C3—C4—N19.9 (7)Br2—C2—C8—C387.3 (4)
C3—C4—C5—C64.9 (8)Br2—C2—C8—C793.6 (4)
N1—C4—C5—C6174.5 (5)C5—C4—N1—O232.2 (7)
C4—C5—C6—C71.4 (8)C3—C4—N1—O2148.4 (5)
C5—C6—C7—O3177.4 (5)C5—C4—N1—O1147.3 (5)
C5—C6—C7—C82.7 (7)C3—C4—N1—O132.1 (7)
C4—C3—C8—C70.5 (6)C6—C7—O3—C90.7 (8)
C1—C3—C8—C7175.4 (4)C8—C7—O3—C9175.3 (4)
C4—C3—C8—C2179.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.433.216 (6)143
Symmetry code: (i) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC9H9Br2NO3
Mr338.99
Crystal system, space groupOrthorhombic, P212121
Temperature (K)292
a, b, c (Å)4.7900 (9), 13.772 (3), 17.158 (3)
V3)1131.9 (4)
Z4
Radiation typeMo Kα
µ (mm1)7.15
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART APEX CCD area detector
diffractometer
Absorption correctionMulti-scan
SADABS, (Sheldrick, 1997)
Tmin, Tmax0.239, 0.243
No. of measured, independent and
observed [I > 2σ(I)] reflections
6493, 2454, 1920
Rint0.034
(sin θ/λ)max1)0.638
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.133, 1.13
No. of reflections2454
No. of parameters137
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.74, 0.68
Absolute structureFlack (1983), 1465 Friedel pairs
Absolute structure parameter0.04 (3)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999)', SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.

Selected geometric parameters (Å, º) top
Br1—C11.953 (5)C9—O31.446 (6)
Br2—C21.993 (5)N1—O21.199 (6)
C4—N11.452 (6)N1—O11.235 (6)
C7—O31.327 (6)
C3—C1—Br1114.6 (3)O2—N1—C4118.4 (4)
C8—C2—Br2108.7 (3)O1—N1—C4116.6 (4)
O2—N1—O1125.0 (5)C7—O3—C9117.4 (4)
C8—C3—C4—N1175.5 (4)C5—C6—C7—O3177.4 (5)
N1—C4—C5—C6174.5 (5)O3—C7—C8—C3178.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.433.216 (6)143
Symmetry code: (i) x, y1/2, z+1/2.
 

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