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The title compound, C10H11Cl2NO2, consists of a benzene core functionalized by one nitro group, two methyl groups, and two chloro­methyl groups. The crystal structure is stabilized by inter­molecular C—H...O non-classical hydrogen bonds and weak C—H...Cl inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048902/bh2063sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048902/bh2063Isup2.hkl
Contains datablock I

CCDC reference: 629432

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.060
  • wR factor = 0.150
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT128_ALERT_4_C Non-standard setting of Space group Pc .... Pn PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 27.49 From the CIF: _reflns_number_total 2456 Count of symmetry unique reflns 1296 Completeness (_total/calc) 189.51% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1160 Fraction of Friedel pairs measured 0.895 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

1,2-Bis(chloromethyl)-4,5-dimethyl-3-nitrobenzene top
Crystal data top
C10H11Cl2NO2F(000) = 256
Mr = 248.10Dx = 1.456 Mg m3
Monoclinic, PnMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yacCell parameters from 1425 reflections
a = 8.350 (4) Åθ = 2.6–21.0°
b = 4.5282 (19) ŵ = 0.55 mm1
c = 15.370 (7) ÅT = 298 K
β = 103.118 (6)°Block, colourless
V = 566.0 (4) Å30.10 × 0.06 × 0.02 mm
Z = 2
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
1709 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.043
Graphite monochromatorθmax = 27.5°, θmin = 2.6°
φ and ω scansh = 1010
4357 measured reflectionsk = 55
2456 independent reflectionsl = 1919
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)] = 0.060H-atom parameters constrained
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.0769P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2456 reflectionsΔρmax = 0.32 e Å3
138 parametersΔρmin = 0.27 e Å3
2 restraintsAbsolute structure: Flack (1983), 1259 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.11 (11)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.0511 (5)0.1762 (10)0.2076 (2)0.0457 (10)
C21.1319 (5)0.1238 (9)0.2971 (3)0.0419 (9)
C31.0638 (5)0.2504 (9)0.3615 (2)0.0404 (9)
C40.9209 (5)0.4241 (9)0.3464 (2)0.0411 (9)
C50.8466 (5)0.4776 (9)0.2569 (3)0.0472 (10)
C60.9128 (5)0.3523 (10)0.1906 (2)0.0502 (11)
H60.86110.38920.13140.060*
C71.1127 (7)0.0494 (13)0.1315 (3)0.0647 (14)
H7A1.03330.08340.07660.097*
H7B1.12980.15910.14040.097*
H7C1.21470.14240.12870.097*
C81.2855 (6)0.0627 (11)0.3198 (3)0.0588 (12)
H8A1.37620.04620.30710.088*
H8B1.26920.24010.28470.088*
H8C1.30900.11310.38210.088*
C90.6960 (6)0.6654 (11)0.2290 (3)0.0612 (12)
H9A0.71440.81040.18580.073*
H9B0.67710.77100.28060.073*
C100.8548 (6)0.5463 (10)0.4212 (3)0.0543 (12)
H10A0.82560.75210.40930.065*
H10B0.93910.53660.47620.065*
Cl10.67719 (16)0.3444 (3)0.43469 (10)0.0794 (5)
Cl20.51799 (14)0.4537 (3)0.18103 (9)0.0705 (4)
N11.1524 (5)0.2105 (9)0.4551 (2)0.0517 (9)
O11.2738 (5)0.3600 (10)0.4827 (2)0.0870 (13)
O21.1066 (6)0.0314 (10)0.5005 (2)0.0964 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.043 (2)0.054 (3)0.040 (2)0.010 (2)0.0113 (17)0.0015 (19)
C20.037 (2)0.042 (2)0.046 (2)0.0106 (17)0.0079 (16)0.0006 (18)
C30.040 (2)0.039 (2)0.039 (2)0.0090 (17)0.0021 (16)0.0050 (17)
C40.045 (2)0.038 (2)0.039 (2)0.0087 (18)0.0077 (17)0.0010 (17)
C50.038 (2)0.042 (2)0.056 (2)0.0086 (18)0.0005 (18)0.001 (2)
C60.048 (3)0.064 (3)0.034 (2)0.014 (2)0.0007 (18)0.003 (2)
C70.060 (3)0.083 (4)0.056 (3)0.015 (3)0.023 (2)0.009 (3)
C80.046 (3)0.063 (3)0.067 (3)0.003 (2)0.010 (2)0.001 (2)
C90.054 (3)0.055 (3)0.066 (3)0.002 (2)0.005 (2)0.005 (2)
C100.061 (3)0.049 (3)0.052 (2)0.006 (2)0.012 (2)0.009 (2)
Cl10.0701 (9)0.0996 (10)0.0800 (9)0.0218 (9)0.0414 (6)0.0122 (9)
Cl20.0402 (6)0.0846 (9)0.0809 (8)0.0000 (7)0.0013 (5)0.0030 (8)
N10.049 (2)0.059 (2)0.043 (2)0.0028 (19)0.0031 (16)0.0022 (18)
O10.075 (3)0.111 (3)0.059 (2)0.039 (2)0.0165 (17)0.003 (2)
O20.113 (3)0.106 (3)0.057 (2)0.045 (3)0.008 (2)0.034 (2)
Geometric parameters (Å, º) top
C1—C61.378 (6)C7—H7B0.9600
C1—C21.409 (5)C7—H7C0.9600
C1—C71.495 (6)C8—H8A0.9600
C2—C31.374 (6)C8—H8B0.9600
C2—C81.509 (6)C8—H8C0.9600
C3—C41.404 (6)C9—Cl21.782 (5)
C3—N11.471 (5)C9—H9A0.9700
C4—C51.396 (6)C9—H9B0.9700
C4—C101.491 (6)C10—Cl11.793 (5)
C5—C61.386 (7)C10—H10A0.9700
C5—C91.498 (7)C10—H10B0.9700
C6—H60.9300N1—O21.189 (5)
C7—H7A0.9600N1—O11.212 (5)
C6—C1—C2118.5 (4)H7B—C7—H7C109.5
C6—C1—C7119.8 (4)C2—C8—H8A109.5
C2—C1—C7121.7 (4)C2—C8—H8B109.5
C3—C2—C1116.7 (4)H8A—C8—H8B109.5
C3—C2—C8122.4 (4)C2—C8—H8C109.5
C1—C2—C8120.9 (4)H8A—C8—H8C109.5
C2—C3—C4126.1 (3)H8B—C8—H8C109.5
C2—C3—N1117.0 (4)C5—C9—Cl2112.4 (3)
C4—C3—N1116.8 (4)C5—C9—H9A109.1
C5—C4—C3115.6 (4)Cl2—C9—H9A109.1
C5—C4—C10122.4 (4)C5—C9—H9B109.1
C3—C4—C10122.0 (4)Cl2—C9—H9B109.1
C6—C5—C4119.4 (4)H9A—C9—H9B107.9
C6—C5—C9118.1 (4)C4—C10—Cl1111.1 (3)
C4—C5—C9122.5 (4)C4—C10—H10A109.4
C1—C6—C5123.6 (3)Cl1—C10—H10A109.4
C1—C6—H6118.2C4—C10—H10B109.4
C5—C6—H6118.2Cl1—C10—H10B109.4
C1—C7—H7A109.5H10A—C10—H10B108.0
C1—C7—H7B109.5O2—N1—O1122.0 (4)
H7A—C7—H7B109.5O2—N1—C3120.0 (4)
C1—C7—H7C109.5O1—N1—C3118.0 (4)
H7A—C7—H7C109.5
C6—C1—C2—C31.1 (5)C3—C4—C5—C9178.3 (4)
C7—C1—C2—C3179.7 (4)C10—C4—C5—C90.9 (6)
C6—C1—C2—C8178.9 (4)C2—C1—C6—C51.1 (6)
C7—C1—C2—C80.3 (6)C7—C1—C6—C5179.6 (5)
C1—C2—C3—C40.6 (6)C4—C5—C6—C10.5 (6)
C8—C2—C3—C4179.4 (4)C9—C5—C6—C1179.8 (4)
C1—C2—C3—N1176.7 (4)C6—C5—C9—Cl270.8 (5)
C8—C2—C3—N13.3 (6)C4—C5—C9—Cl2108.9 (4)
C2—C3—C4—C52.2 (6)C5—C4—C10—Cl176.4 (5)
N1—C3—C4—C5175.1 (4)C3—C4—C10—Cl1104.5 (4)
C2—C3—C4—C10178.6 (4)C2—C3—N1—O2101.4 (6)
N1—C3—C4—C104.1 (6)C4—C3—N1—O281.0 (6)
C3—C4—C5—C62.1 (6)C2—C3—N1—O177.0 (5)
C10—C4—C5—C6178.8 (4)C4—C3—N1—O1100.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.513.401 (5)161
C8—H8C···N10.962.402.852 (6)108
C10—H10B···N10.972.392.859 (7)109
Symmetry code: (i) x1/2, y+1, z1/2.
 

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