organic compounds
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—HO non-classical hydrogen bonds and weak C—HCl interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048902/bh2063sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048902/bh2063Isup2.hkl |
CCDC reference: 629432
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
C10H11Cl2NO2 | F(000) = 256 |
Mr = 248.10 | Dx = 1.456 Mg m−3 |
Monoclinic, Pn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yac | Cell parameters from 1425 reflections |
a = 8.350 (4) Å | θ = 2.6–21.0° |
b = 4.5282 (19) Å | µ = 0.55 mm−1 |
c = 15.370 (7) Å | T = 298 K |
β = 103.118 (6)° | Block, colourless |
V = 566.0 (4) Å3 | 0.10 × 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 tube | Rint = 0.043 |
Graphite monochromator | θmax = 27.5°, θmin = 2.6° |
φ and ω scans | h = −10→10 |
4357 measured reflections | k = −5→5 |
2456 independent reflections | l = −19→19 |
Refinement top
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)] = 0.060 | H-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 reflections | Δρmax = 0.32 e Å−3 |
138 parameters | Δρmin = −0.27 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1259 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.11 (11) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 1.0511 (5) | 0.1762 (10) | 0.2076 (2) | 0.0457 (10) | |
C2 | 1.1319 (5) | 0.1238 (9) | 0.2971 (3) | 0.0419 (9) | |
C3 | 1.0638 (5) | 0.2504 (9) | 0.3615 (2) | 0.0404 (9) | |
C4 | 0.9209 (5) | 0.4241 (9) | 0.3464 (2) | 0.0411 (9) | |
C5 | 0.8466 (5) | 0.4776 (9) | 0.2569 (3) | 0.0472 (10) | |
C6 | 0.9128 (5) | 0.3523 (10) | 0.1906 (2) | 0.0502 (11) | |
H6 | 0.8611 | 0.3892 | 0.1314 | 0.060* | |
C7 | 1.1127 (7) | 0.0494 (13) | 0.1315 (3) | 0.0647 (14) | |
H7A | 1.0333 | 0.0834 | 0.0766 | 0.097* | |
H7B | 1.1298 | −0.1591 | 0.1404 | 0.097* | |
H7C | 1.2147 | 0.1424 | 0.1287 | 0.097* | |
C8 | 1.2855 (6) | −0.0627 (11) | 0.3198 (3) | 0.0588 (12) | |
H8A | 1.3762 | 0.0462 | 0.3071 | 0.088* | |
H8B | 1.2692 | −0.2401 | 0.2847 | 0.088* | |
H8C | 1.3090 | −0.1131 | 0.3821 | 0.088* | |
C9 | 0.6960 (6) | 0.6654 (11) | 0.2290 (3) | 0.0612 (12) | |
H9A | 0.7144 | 0.8104 | 0.1858 | 0.073* | |
H9B | 0.6771 | 0.7710 | 0.2806 | 0.073* | |
C10 | 0.8548 (6) | 0.5463 (10) | 0.4212 (3) | 0.0543 (12) | |
H10A | 0.8256 | 0.7521 | 0.4093 | 0.065* | |
H10B | 0.9391 | 0.5366 | 0.4762 | 0.065* | |
Cl1 | 0.67719 (16) | 0.3444 (3) | 0.43469 (10) | 0.0794 (5) | |
Cl2 | 0.51799 (14) | 0.4537 (3) | 0.18103 (9) | 0.0705 (4) | |
N1 | 1.1524 (5) | 0.2105 (9) | 0.4551 (2) | 0.0517 (9) | |
O1 | 1.2738 (5) | 0.3600 (10) | 0.4827 (2) | 0.0870 (13) | |
O2 | 1.1066 (6) | 0.0314 (10) | 0.5005 (2) | 0.0964 (15) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.043 (2) | 0.054 (3) | 0.040 (2) | −0.010 (2) | 0.0113 (17) | −0.0015 (19) |
C2 | 0.037 (2) | 0.042 (2) | 0.046 (2) | −0.0106 (17) | 0.0079 (16) | −0.0006 (18) |
C3 | 0.040 (2) | 0.039 (2) | 0.039 (2) | −0.0090 (17) | 0.0021 (16) | 0.0050 (17) |
C4 | 0.045 (2) | 0.038 (2) | 0.039 (2) | −0.0087 (18) | 0.0077 (17) | 0.0010 (17) |
C5 | 0.038 (2) | 0.042 (2) | 0.056 (2) | −0.0086 (18) | −0.0005 (18) | 0.001 (2) |
C6 | 0.048 (3) | 0.064 (3) | 0.034 (2) | −0.014 (2) | 0.0007 (18) | 0.003 (2) |
C7 | 0.060 (3) | 0.083 (4) | 0.056 (3) | −0.015 (3) | 0.023 (2) | −0.009 (3) |
C8 | 0.046 (3) | 0.063 (3) | 0.067 (3) | 0.003 (2) | 0.010 (2) | 0.001 (2) |
C9 | 0.054 (3) | 0.055 (3) | 0.066 (3) | −0.002 (2) | −0.005 (2) | 0.005 (2) |
C10 | 0.061 (3) | 0.049 (3) | 0.052 (2) | −0.006 (2) | 0.012 (2) | −0.009 (2) |
Cl1 | 0.0701 (9) | 0.0996 (10) | 0.0800 (9) | −0.0218 (9) | 0.0414 (6) | −0.0122 (9) |
Cl2 | 0.0402 (6) | 0.0846 (9) | 0.0809 (8) | 0.0000 (7) | 0.0013 (5) | −0.0030 (8) |
N1 | 0.049 (2) | 0.059 (2) | 0.043 (2) | −0.0028 (19) | 0.0031 (16) | −0.0022 (18) |
O1 | 0.075 (3) | 0.111 (3) | 0.059 (2) | −0.039 (2) | −0.0165 (17) | −0.003 (2) |
O2 | 0.113 (3) | 0.106 (3) | 0.057 (2) | −0.045 (3) | −0.008 (2) | 0.034 (2) |
Geometric parameters (Å, º) top
C1—C6 | 1.378 (6) | C7—H7B | 0.9600 |
C1—C2 | 1.409 (5) | C7—H7C | 0.9600 |
C1—C7 | 1.495 (6) | C8—H8A | 0.9600 |
C2—C3 | 1.374 (6) | C8—H8B | 0.9600 |
C2—C8 | 1.509 (6) | C8—H8C | 0.9600 |
C3—C4 | 1.404 (6) | C9—Cl2 | 1.782 (5) |
C3—N1 | 1.471 (5) | C9—H9A | 0.9700 |
C4—C5 | 1.396 (6) | C9—H9B | 0.9700 |
C4—C10 | 1.491 (6) | C10—Cl1 | 1.793 (5) |
C5—C6 | 1.386 (7) | C10—H10A | 0.9700 |
C5—C9 | 1.498 (7) | C10—H10B | 0.9700 |
C6—H6 | 0.9300 | N1—O2 | 1.189 (5) |
C7—H7A | 0.9600 | N1—O1 | 1.212 (5) |
C6—C1—C2 | 118.5 (4) | H7B—C7—H7C | 109.5 |
C6—C1—C7 | 119.8 (4) | C2—C8—H8A | 109.5 |
C2—C1—C7 | 121.7 (4) | C2—C8—H8B | 109.5 |
C3—C2—C1 | 116.7 (4) | H8A—C8—H8B | 109.5 |
C3—C2—C8 | 122.4 (4) | C2—C8—H8C | 109.5 |
C1—C2—C8 | 120.9 (4) | H8A—C8—H8C | 109.5 |
C2—C3—C4 | 126.1 (3) | H8B—C8—H8C | 109.5 |
C2—C3—N1 | 117.0 (4) | C5—C9—Cl2 | 112.4 (3) |
C4—C3—N1 | 116.8 (4) | C5—C9—H9A | 109.1 |
C5—C4—C3 | 115.6 (4) | Cl2—C9—H9A | 109.1 |
C5—C4—C10 | 122.4 (4) | C5—C9—H9B | 109.1 |
C3—C4—C10 | 122.0 (4) | Cl2—C9—H9B | 109.1 |
C6—C5—C4 | 119.4 (4) | H9A—C9—H9B | 107.9 |
C6—C5—C9 | 118.1 (4) | C4—C10—Cl1 | 111.1 (3) |
C4—C5—C9 | 122.5 (4) | C4—C10—H10A | 109.4 |
C1—C6—C5 | 123.6 (3) | Cl1—C10—H10A | 109.4 |
C1—C6—H6 | 118.2 | C4—C10—H10B | 109.4 |
C5—C6—H6 | 118.2 | Cl1—C10—H10B | 109.4 |
C1—C7—H7A | 109.5 | H10A—C10—H10B | 108.0 |
C1—C7—H7B | 109.5 | O2—N1—O1 | 122.0 (4) |
H7A—C7—H7B | 109.5 | O2—N1—C3 | 120.0 (4) |
C1—C7—H7C | 109.5 | O1—N1—C3 | 118.0 (4) |
H7A—C7—H7C | 109.5 | ||
C6—C1—C2—C3 | 1.1 (5) | C3—C4—C5—C9 | −178.3 (4) |
C7—C1—C2—C3 | −179.7 (4) | C10—C4—C5—C9 | 0.9 (6) |
C6—C1—C2—C8 | −178.9 (4) | C2—C1—C6—C5 | −1.1 (6) |
C7—C1—C2—C8 | 0.3 (6) | C7—C1—C6—C5 | 179.6 (5) |
C1—C2—C3—C4 | 0.6 (6) | C4—C5—C6—C1 | −0.5 (6) |
C8—C2—C3—C4 | −179.4 (4) | C9—C5—C6—C1 | 179.8 (4) |
C1—C2—C3—N1 | −176.7 (4) | C6—C5—C9—Cl2 | 70.8 (5) |
C8—C2—C3—N1 | 3.3 (6) | C4—C5—C9—Cl2 | −108.9 (4) |
C2—C3—C4—C5 | −2.2 (6) | C5—C4—C10—Cl1 | 76.4 (5) |
N1—C3—C4—C5 | 175.1 (4) | C3—C4—C10—Cl1 | −104.5 (4) |
C2—C3—C4—C10 | 178.6 (4) | C2—C3—N1—O2 | −101.4 (6) |
N1—C3—C4—C10 | −4.1 (6) | C4—C3—N1—O2 | 81.0 (6) |
C3—C4—C5—C6 | 2.1 (6) | C2—C3—N1—O1 | 77.0 (5) |
C10—C4—C5—C6 | −178.8 (4) | C4—C3—N1—O1 | −100.6 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.93 | 2.51 | 3.401 (5) | 161 |
C8—H8C···N1 | 0.96 | 2.40 | 2.852 (6) | 108 |
C10—H10B···N1 | 0.97 | 2.39 | 2.859 (7) | 109 |
Symmetry code: (i) x−1/2, −y+1, z−1/2. |