1,2-Bis(chloro­meth­yl)-4,5-dimethyl-3-nitro­benzene

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.

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

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Computing details

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

Crystal data

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) Å^3	0.10 × 0.06 × 0.02 mm
Z = 2

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.151	w = 1/[σ^2(Fo^2) + (0.0769P)^2] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1^i	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.