1-Bromo-3,4-bis­(bromo­meth­yl)-2,5-dimethoxy­benzene

1,4-Dimeth­oxy-2,3-dimethyl­benzene was brominated under radical conditions to give the title compound, C₁₀H₁₁Br₃O₄. The bond lengths and angles are generally within the normal ranges. The crystal packing is stabilized by weak inter­molecular C—H...O and C—H...Br hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 122 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.078
• Data-to-parameter ratio = 39.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) .......          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br2A   ..  Br3B    ..       3.44 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         20
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C10 H11 Br3 O2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C10 H11 Br3 O2

Alert level G
ABSTY01_ALERT_1_G  Extra text has been found in the _exptl_absorpt_correction_type
            field, which should be only a single keyword. A literature
            citation should be included in the _exptl_absorpt_process_details
            field.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

1-Bromo-3,4-bis(bromomethyl)-2,5-dimethoxybenzene

Crystal data

C10H11Br3O2	F(000) = 1536
Mr = 402.91	Dx = 2.199 Mg m^−3
Monoclinic, P21/c	Melting point = 359–361 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.5660 (9) Å	Cell parameters from 47424 reflections
b = 17.1420 (16) Å	θ = 1.2–35.0°
c = 8.6720 (12) Å	µ = 9.92 mm^−1
β = 98.672 (7)°	T = 122 K
V = 2434.5 (4) Å^3	Prism, white
Z = 8	0.36 × 0.26 × 0.16 mm

Data collection

Nonius KappaCCD area-detector diffractometer	10710 independent reflections
Radiation source: fine-focus sealed tube	8305 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
ω and φ scans	θmax = 35.0°, θmin = 1.2°
Absorption correction: gaussian integration (Coppens, 1970)	h = −26→26
Tmin = 0.195, Tmax = 0.419	k = −27→27
106756 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0187P)^2 + 7.2256P] where P = (Fo^2 + 2Fc^2)/3
10710 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 1.33 e Å^−3
0 restraints	Δρmin = −1.14 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1A	0.095015 (17)	0.130891 (16)	−0.25685 (3)	0.01737 (6)
Br2B	0.440108 (18)	−0.147362 (18)	−0.40794 (3)	0.02031 (6)
Br2A	0.083382 (18)	−0.230676 (17)	−0.33247 (4)	0.02017 (6)
Br3A	−0.190834 (18)	−0.178882 (18)	−0.18949 (4)	0.02050 (6)
Br3B	0.257974 (18)	−0.20596 (2)	0.03512 (4)	0.02677 (7)
Br1B	0.671527 (18)	−0.07728 (2)	0.21042 (4)	0.02718 (7)
O1A	0.13175 (11)	−0.03734 (11)	−0.1505 (2)	0.0134 (3)
O1B	0.60942 (12)	−0.18204 (13)	−0.0695 (3)	0.0202 (4)
C2A	0.05328 (15)	−0.02814 (15)	−0.2258 (3)	0.0116 (4)
C4A	−0.07787 (15)	−0.08505 (15)	−0.3319 (3)	0.0117 (4)
C9A	−0.13230 (16)	−0.15409 (16)	−0.3658 (3)	0.0150 (5)
H9AA	−0.0992	−0.1997	−0.3879	0.018*
H9AB	−0.1725	−0.1435	−0.4600	0.018*
C6A	−0.05418 (15)	0.05361 (15)	−0.3611 (3)	0.0126 (4)
H6A	−0.0729	0.1035	−0.3984	0.015*
C10A	0.03235 (16)	−0.16919 (15)	−0.1825 (3)	0.0145 (5)
H10AA	−0.0136	−0.1991	−0.1509	0.017*
H10AB	0.0728	−0.1597	−0.0880	0.017*
C3A	0.00154 (15)	−0.09304 (15)	−0.2501 (3)	0.0113 (4)
O2B	0.35364 (13)	−0.04014 (13)	0.1607 (3)	0.0222 (4)
C9B	0.45156 (17)	−0.21191 (16)	−0.2167 (3)	0.0175 (5)
H9BA	0.4013	−0.2429	−0.2151	0.021*
H9BB	0.4979	−0.2485	−0.2157	0.021*
C3B	0.46608 (15)	−0.16055 (15)	−0.0761 (3)	0.0145 (5)
O2A	−0.18440 (12)	−0.00719 (12)	−0.4546 (2)	0.0172 (4)
C10B	0.31520 (16)	−0.13416 (17)	−0.0895 (3)	0.0179 (5)
H10BA	0.3131	−0.1553	−0.1963	0.021*
H10BB	0.2872	−0.0830	−0.0973	0.021*
C1B	0.56262 (16)	−0.09786 (17)	0.1202 (3)	0.0177 (5)
C6B	0.49979 (17)	−0.05976 (17)	0.1798 (3)	0.0183 (5)
H6B	0.5115	−0.0251	0.2657	0.022*
C1A	0.02454 (15)	0.04410 (14)	−0.2832 (3)	0.0116 (4)
C2B	0.54702 (16)	−0.14796 (17)	−0.0060 (3)	0.0166 (5)
C4B	0.40199 (16)	−0.12355 (16)	−0.0174 (3)	0.0157 (5)
C8A	−0.21614 (18)	0.06814 (18)	−0.5007 (4)	0.0217 (6)
H8AA	−0.2732	0.0632	−0.5499	0.026*
H8AB	−0.1839	0.0911	−0.5751	0.026*
H8AC	−0.2131	0.1018	−0.4087	0.026*
C5B	0.41979 (16)	−0.07338 (17)	0.1114 (3)	0.0170 (5)
C8B	0.3677 (2)	0.01603 (18)	0.2832 (4)	0.0231 (6)
H8BA	0.3152	0.0351	0.3072	0.028*
H8BB	0.3991	0.0598	0.2503	0.028*
H8BC	0.3983	−0.0083	0.3764	0.028*
C5A	−0.10554 (15)	−0.01083 (15)	−0.3838 (3)	0.0125 (4)
C7A	0.13977 (18)	−0.01821 (19)	0.0130 (3)	0.0218 (6)
H7AA	0.1966	−0.0256	0.0615	0.026*
H7AB	0.1042	−0.0523	0.0637	0.026*
H7AC	0.1240	0.0363	0.0248	0.026*
C7B	0.6407 (2)	−0.2523 (2)	0.0084 (4)	0.0289 (7)
H7BA	0.6849	−0.2731	−0.0428	0.035*
H7BB	0.5968	−0.2909	0.0034	0.035*
H7BC	0.6616	−0.2406	0.1177	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.01750 (12)	0.01271 (11)	0.02179 (13)	−0.00352 (9)	0.00257 (9)	−0.00270 (10)
Br2B	0.02227 (13)	0.01913 (13)	0.01896 (13)	0.00046 (10)	0.00129 (10)	0.00101 (10)
Br2A	0.02330 (13)	0.01404 (12)	0.02457 (14)	0.00443 (10)	0.00813 (11)	−0.00341 (10)
Br3A	0.02053 (13)	0.01962 (13)	0.02245 (13)	−0.00613 (10)	0.00680 (10)	−0.00038 (11)
Br3B	0.01238 (11)	0.02525 (15)	0.04156 (19)	−0.00258 (10)	0.00043 (11)	0.01239 (13)
Br1B	0.01394 (12)	0.02795 (16)	0.03661 (17)	−0.00589 (11)	−0.00603 (11)	0.00368 (13)
O1A	0.0093 (7)	0.0175 (9)	0.0130 (8)	0.0027 (6)	0.0002 (6)	−0.0029 (7)
O1B	0.0123 (8)	0.0233 (10)	0.0259 (10)	0.0030 (8)	0.0057 (7)	0.0060 (9)
C2A	0.0103 (10)	0.0129 (10)	0.0115 (10)	0.0020 (8)	0.0020 (8)	−0.0021 (8)
C4A	0.0132 (10)	0.0112 (10)	0.0108 (10)	−0.0014 (8)	0.0023 (8)	−0.0003 (8)
C9A	0.0159 (11)	0.0147 (11)	0.0148 (11)	−0.0026 (9)	0.0036 (9)	−0.0006 (9)
C6A	0.0136 (10)	0.0110 (10)	0.0132 (10)	0.0018 (8)	0.0022 (8)	−0.0003 (8)
C10A	0.0167 (11)	0.0128 (11)	0.0138 (11)	0.0021 (9)	0.0019 (9)	−0.0008 (9)
C3A	0.0128 (10)	0.0097 (10)	0.0116 (10)	0.0009 (8)	0.0024 (8)	−0.0006 (8)
O2B	0.0162 (9)	0.0231 (11)	0.0274 (11)	0.0004 (8)	0.0042 (8)	−0.0054 (9)
C9B	0.0157 (11)	0.0150 (12)	0.0207 (13)	0.0017 (9)	−0.0008 (10)	0.0019 (10)
C3B	0.0112 (10)	0.0132 (11)	0.0186 (12)	−0.0006 (8)	0.0001 (9)	0.0039 (9)
O2A	0.0114 (8)	0.0156 (9)	0.0229 (10)	0.0005 (7)	−0.0025 (7)	0.0020 (8)
C10B	0.0112 (10)	0.0195 (13)	0.0221 (13)	0.0002 (9)	−0.0002 (9)	0.0040 (10)
C1B	0.0110 (10)	0.0180 (12)	0.0227 (13)	−0.0031 (9)	−0.0022 (9)	0.0034 (10)
C6B	0.0171 (12)	0.0184 (12)	0.0181 (12)	−0.0027 (10)	−0.0011 (10)	−0.0004 (10)
C1A	0.0134 (10)	0.0095 (10)	0.0122 (10)	−0.0013 (8)	0.0032 (8)	−0.0007 (8)
C2B	0.0115 (10)	0.0168 (12)	0.0213 (12)	0.0002 (9)	0.0019 (9)	0.0048 (10)
C4B	0.0102 (10)	0.0154 (11)	0.0203 (12)	−0.0008 (9)	−0.0015 (9)	0.0048 (10)
C8A	0.0162 (12)	0.0197 (13)	0.0280 (15)	0.0050 (10)	−0.0003 (11)	0.0060 (11)
C5B	0.0118 (10)	0.0178 (12)	0.0211 (13)	0.0004 (9)	0.0012 (9)	0.0018 (10)
C8B	0.0274 (15)	0.0198 (14)	0.0235 (14)	0.0021 (11)	0.0080 (12)	0.0001 (11)
C5A	0.0110 (10)	0.0146 (11)	0.0114 (10)	0.0007 (8)	0.0001 (8)	0.0000 (9)
C7A	0.0203 (13)	0.0283 (15)	0.0149 (12)	0.0063 (11)	−0.0033 (10)	−0.0070 (11)
C7B	0.0223 (14)	0.0285 (16)	0.0376 (18)	0.0113 (12)	0.0097 (13)	0.0112 (14)

Geometric parameters (Å, º)

Br1A—C1A	1.884 (2)	C9B—H9BA	0.9900
Br2B—C9B	1.979 (3)	C9B—H9BB	0.9900
Br2A—C10A	1.962 (3)	C3B—C2B	1.403 (4)
Br3A—C9A	1.977 (3)	C3B—C4B	1.397 (4)
Br3B—C10B	1.972 (3)	O2A—C5A	1.359 (3)
Br1B—C1B	1.888 (3)	O2A—C8A	1.428 (3)
O1A—C2A	1.373 (3)	C10B—C4B	1.490 (4)
O1A—C7A	1.442 (3)	C10B—H10BA	0.9900
O1B—C2B	1.373 (3)	C10B—H10BB	0.9900
O1B—C7B	1.438 (4)	C1B—C2B	1.384 (4)
C2A—C1A	1.392 (4)	C1B—C6B	1.393 (4)
C2A—C3A	1.401 (4)	C6B—C5B	1.388 (4)
C4A—C5A	1.403 (4)	C6B—H6B	0.9500
C4A—C3A	1.404 (3)	C4B—C5B	1.405 (4)
C4A—C9A	1.490 (4)	C8A—H8AA	0.9800
C9A—H9AA	0.9900	C8A—H8AB	0.9800
C9A—H9AB	0.9900	C8A—H8AC	0.9800
C6A—C1A	1.385 (3)	C8B—H8BA	0.9800
C6A—C5A	1.390 (4)	C8B—H8BB	0.9800
C6A—H6A	0.9500	C8B—H8BC	0.9800
C10A—C3A	1.489 (4)	C7A—H7AA	0.9800
C10A—H10AA	0.9900	C7A—H7AB	0.9800
C10A—H10AB	0.9900	C7A—H7AC	0.9800
O2B—C5B	1.360 (3)	C7B—H7BA	0.9800
O2B—C8B	1.427 (4)	C7B—H7BB	0.9800
C9B—C3B	1.494 (4)	C7B—H7BC	0.9800
C2A—O1A—C7A	112.4 (2)	C2B—C1B—Br1B	119.8 (2)
C2B—O1B—C7B	114.0 (2)	C6B—C1B—Br1B	118.6 (2)
O1A—C2A—C1A	121.4 (2)	C5B—C6B—C1B	118.8 (3)
O1A—C2A—C3A	119.6 (2)	C5B—C6B—H6B	120.6
C1A—C2A—C3A	119.0 (2)	C1B—C6B—H6B	120.6
C5A—C4A—C3A	119.1 (2)	C6A—C1A—C2A	121.7 (2)
C5A—C4A—C9A	119.9 (2)	C6A—C1A—Br1A	119.15 (19)
C3A—C4A—C9A	121.0 (2)	C2A—C1A—Br1A	119.14 (19)
C4A—C9A—Br3A	111.76 (18)	O1B—C2B—C1B	121.3 (2)
C4A—C9A—H9AA	109.3	O1B—C2B—C3B	119.3 (3)
Br3A—C9A—H9AA	109.3	C1B—C2B—C3B	119.3 (3)
C4A—C9A—H9AB	109.3	C3B—C4B—C5B	119.2 (2)
Br3A—C9A—H9AB	109.3	C3B—C4B—C10B	122.0 (3)
H9AA—C9A—H9AB	107.9	C5B—C4B—C10B	118.8 (2)
C1A—C6A—C5A	119.1 (2)	O2A—C8A—H8AA	109.5
C1A—C6A—H6A	120.4	O2A—C8A—H8AB	109.5
C5A—C6A—H6A	120.4	H8AA—C8A—H8AB	109.5
C3A—C10A—Br2A	111.47 (18)	O2A—C8A—H8AC	109.5
C3A—C10A—H10AA	109.3	H8AA—C8A—H8AC	109.5
Br2A—C10A—H10AA	109.3	H8AB—C8A—H8AC	109.5
C3A—C10A—H10AB	109.3	O2B—C5B—C6B	123.9 (3)
Br2A—C10A—H10AB	109.3	O2B—C5B—C4B	115.1 (2)
H10AA—C10A—H10AB	108.0	C6B—C5B—C4B	121.0 (3)
C2A—C3A—C4A	120.3 (2)	O2B—C8B—H8BA	109.5
C2A—C3A—C10A	118.1 (2)	O2B—C8B—H8BB	109.5
C4A—C3A—C10A	121.6 (2)	H8BA—C8B—H8BB	109.5
C5B—O2B—C8B	117.9 (2)	O2B—C8B—H8BC	109.5
C3B—C9B—Br2B	109.76 (19)	H8BA—C8B—H8BC	109.5
C3B—C9B—H9BA	109.7	H8BB—C8B—H8BC	109.5
Br2B—C9B—H9BA	109.7	O2A—C5A—C6A	123.6 (2)
C3B—C9B—H9BB	109.7	O2A—C5A—C4A	115.6 (2)
Br2B—C9B—H9BB	109.7	C6A—C5A—C4A	120.8 (2)
H9BA—C9B—H9BB	108.2	O1A—C7A—H7AA	109.5
C2B—C3B—C4B	120.1 (3)	O1A—C7A—H7AB	109.5
C2B—C3B—C9B	118.0 (2)	H7AA—C7A—H7AB	109.5
C4B—C3B—C9B	121.8 (2)	O1A—C7A—H7AC	109.5
C5A—O2A—C8A	117.1 (2)	H7AA—C7A—H7AC	109.5
C4B—C10B—Br3B	111.07 (19)	H7AB—C7A—H7AC	109.5
C4B—C10B—H10BA	109.4	O1B—C7B—H7BA	109.5
Br3B—C10B—H10BA	109.4	O1B—C7B—H7BB	109.5
C4B—C10B—H10BB	109.4	H7BA—C7B—H7BB	109.5
Br3B—C10B—H10BB	109.4	O1B—C7B—H7BC	109.5
H10BA—C10B—H10BB	108.0	H7BA—C7B—H7BC	109.5
C2B—C1B—C6B	121.6 (2)	H7BB—C7B—H7BC	109.5
C7A—O1A—C2A—C1A	84.7 (3)	C6B—C1B—C2B—C3B	0.2 (4)
C7A—O1A—C2A—C3A	−97.4 (3)	Br1B—C1B—C2B—C3B	−177.6 (2)
C5A—C4A—C9A—Br3A	−96.0 (2)	C4B—C3B—C2B—O1B	−177.1 (2)
C3A—C4A—C9A—Br3A	84.9 (3)	C9B—C3B—C2B—O1B	0.8 (4)
O1A—C2A—C3A—C4A	−177.7 (2)	C4B—C3B—C2B—C1B	−0.8 (4)
C1A—C2A—C3A—C4A	0.3 (4)	C9B—C3B—C2B—C1B	177.1 (3)
O1A—C2A—C3A—C10A	4.3 (4)	C2B—C3B—C4B—C5B	0.4 (4)
C1A—C2A—C3A—C10A	−177.7 (2)	C9B—C3B—C4B—C5B	−177.4 (3)
C5A—C4A—C3A—C2A	−2.3 (4)	C2B—C3B—C4B—C10B	179.0 (3)
C9A—C4A—C3A—C2A	176.9 (2)	C9B—C3B—C4B—C10B	1.2 (4)
C5A—C4A—C3A—C10A	175.6 (2)	Br3B—C10B—C4B—C3B	103.2 (3)
C9A—C4A—C3A—C10A	−5.2 (4)	Br3B—C10B—C4B—C5B	−78.3 (3)
Br2A—C10A—C3A—C2A	−92.7 (2)	C8B—O2B—C5B—C6B	4.3 (4)
Br2A—C10A—C3A—C4A	89.3 (3)	C8B—O2B—C5B—C4B	−175.3 (3)
Br2B—C9B—C3B—C2B	−95.7 (3)	C1B—C6B—C5B—O2B	179.3 (3)
Br2B—C9B—C3B—C4B	82.2 (3)	C1B—C6B—C5B—C4B	−1.1 (4)
C2B—C1B—C6B—C5B	0.7 (4)	C3B—C4B—C5B—O2B	−179.9 (2)
Br1B—C1B—C6B—C5B	178.5 (2)	C10B—C4B—C5B—O2B	1.5 (4)
C5A—C6A—C1A—C2A	−0.7 (4)	C3B—C4B—C5B—C6B	0.5 (4)
C5A—C6A—C1A—Br1A	178.48 (19)	C10B—C4B—C5B—C6B	−178.1 (3)
O1A—C2A—C1A—C6A	179.1 (2)	C8A—O2A—C5A—C6A	−3.1 (4)
C3A—C2A—C1A—C6A	1.2 (4)	C8A—O2A—C5A—C4A	176.4 (2)
O1A—C2A—C1A—Br1A	0.0 (3)	C1A—C6A—C5A—O2A	178.1 (2)
C3A—C2A—C1A—Br1A	−177.93 (19)	C1A—C6A—C5A—C4A	−1.4 (4)
C7B—O1B—C2B—C1B	84.5 (3)	C3A—C4A—C5A—O2A	−176.6 (2)
C7B—O1B—C2B—C3B	−99.2 (3)	C9A—C4A—C5A—O2A	4.2 (4)
C6B—C1B—C2B—O1B	176.4 (3)	C3A—C4A—C5A—C6A	2.9 (4)
Br1B—C1B—C2B—O1B	−1.3 (4)	C9A—C4A—C5A—C6A	−176.3 (2)