1-(2-Bromo-1,1-di­methoxy­ethyl)-4-nitro­benzene

Methyl 4-nitro­phenyl ketone was brominated by copper(II) bromide in methanol; the ketone reacts with the solvent in situ to yield the title compound, C₁₀H₁₂BrNO₄, which exists as a monomeric mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.088
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

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: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

2-Bromo-1,1-dimethoxyethyl-4-nitrobenzene

Crystal data

C10H12BrNO4	Z = 2
Mr = 290.12	F(000) = 292
Triclinic, P1	Dx = 1.603 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.091 (1) Å	Cell parameters from 967 reflections
b = 9.906 (1) Å	θ = 2.4–27.0°
c = 10.262 (1) Å	µ = 3.42 mm^−1
α = 117.552 (2)°	T = 295 K
β = 102.567 (2)°	Prism, colorless
γ = 97.488 (2)°	0.50 × 0.36 × 0.27 mm
V = 601.1 (1) Å^3

Data collection

Bruker SMART area-detector diffractometer	2599 independent reflections
Radiation source: medium-focus sealed tube	2238 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scan	θmax = 27.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.200, Tmax = 0.397	k = −12→12
5175 measured reflections	l = −13→13

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)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0389P)^2 + 0.3289P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
2599 reflections	Δρmax = 0.46 e Å^−3
148 parameters	Δρmin = −0.70 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.46 (1)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.64781 (5)	0.43738 (3)	0.76792 (3)	0.0649 (2)
O1	1.0712 (2)	0.3484 (2)	0.5501 (2)	0.0471 (4)
O2	0.9218 (3)	0.2052 (2)	0.6460 (2)	0.0456 (4)
O3	0.1835 (3)	0.0191 (3)	−0.0553 (2)	0.0699 (6)
O4	0.1497 (3)	−0.1820 (3)	−0.0251 (3)	0.0743 (6)
N1	0.2307 (3)	−0.0468 (3)	0.0175 (2)	0.0512 (5)
C1	0.7171 (3)	0.2082 (2)	0.4344 (2)	0.0339 (4)
C2	0.6107 (4)	0.0571 (3)	0.3865 (3)	0.0414 (5)
C3	0.4503 (4)	−0.0269 (3)	0.2508 (3)	0.0450 (5)
C4	0.3982 (3)	0.0434 (3)	0.1643 (3)	0.0391 (5)
C5	0.4997 (4)	0.1935 (3)	0.2093 (3)	0.0415 (5)
C6	0.6599 (4)	0.2761 (3)	0.3445 (3)	0.0401 (5)
C7	0.8970 (3)	0.3024 (2)	0.5819 (3)	0.0384 (5)
C8	0.8719 (4)	0.4617 (3)	0.6938 (3)	0.0492 (6)
C9	1.1305 (4)	0.2203 (4)	0.4421 (3)	0.0562 (6)
C10	1.0841 (5)	0.2698 (4)	0.7865 (3)	0.0669 (8)
H2	0.6473	0.0115	0.4462	0.050*
H3	0.3792	−0.1286	0.2185	0.054*
H5	0.4612	0.2389	0.1497	0.050*
H6	0.7302	0.3777	0.3760	0.048*
H8a	0.8510	0.5218	0.6420	0.059*
H8b	0.9939	0.5206	0.7814	0.059*
H9a	1.1244	0.1385	0.4678	0.084*
H9b	1.2651	0.2577	0.4469	0.084*
H9c	1.0417	0.1789	0.3392	0.084*
H10a	1.2045	0.3120	0.7743	0.100*
H10b	1.1027	0.1883	0.8100	0.100*
H10c	1.0541	0.3525	0.8696	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0679 (2)	0.0564 (2)	0.0636 (2)	0.02080 (15)	0.02796 (16)	0.02108 (15)
O1	0.0394 (8)	0.0425 (9)	0.0475 (9)	−0.0028 (7)	0.0072 (7)	0.0198 (8)
O2	0.0488 (9)	0.0439 (9)	0.0407 (8)	0.0050 (7)	0.0023 (7)	0.0256 (7)
O3	0.061 (1)	0.093 (2)	0.048 (1)	0.019 (1)	0.004 (1)	0.037 (1)
O4	0.065 (1)	0.058 (1)	0.056 (1)	−0.012 (1)	−0.001 (1)	0.011 (1)
N1	0.040 (1)	0.058 (1)	0.040 (1)	0.009 (1)	0.012 (1)	0.015 (1)
C1	0.034 (1)	0.029 (1)	0.035 (1)	0.004 (1)	0.009 (1)	0.015 (1)
C2	0.045 (1)	0.034 (1)	0.044 (1)	0.002 (1)	0.007 (1)	0.024 (1)
C3	0.045 (1)	0.032 (1)	0.046 (1)	−0.002 (1)	0.008 (1)	0.017 (1)
C4	0.032 (1)	0.042 (1)	0.035 (1)	0.007 (1)	0.009 (1)	0.014 (1)
C5	0.045 (1)	0.045 (1)	0.041 (1)	0.015 (1)	0.013 (1)	0.026 (1)
C6	0.046 (1)	0.031 (1)	0.044 (1)	0.005 (1)	0.012 (1)	0.021 (1)
C7	0.040 (1)	0.032 (1)	0.037 (1)	0.001 (1)	0.006 (1)	0.017 (1)
C8	0.053 (1)	0.034 (1)	0.046 (1)	0.002 (1)	0.009 (1)	0.015 (1)
C9	0.045 (1)	0.065 (2)	0.054 (2)	0.013 (1)	0.016 (1)	0.027 (1)
C10	0.061 (2)	0.080 (2)	0.051 (2)	0.007 (2)	−0.004 (1)	0.038 (2)

Geometric parameters (Å, º)

Br1—C8	1.938 (3)	C5—C6	1.381 (3)
O1—C7	1.417 (3)	C7—C8	1.525 (3)
O1—C9	1.434 (3)	C2—H2	0.93
O2—C7	1.404 (3)	C3—H3	0.93
O2—C10	1.430 (3)	C5—H5	0.93
O3—N1	1.222 (3)	C6—H6	0.93
O4—N1	1.209 (3)	C8—H8a	0.97
N1—C4	1.476 (3)	C8—H8b	0.97
C1—C2	1.383 (3)	C9—H9a	0.96
C1—C6	1.396 (3)	C9—H9b	0.96
C1—C7	1.527 (3)	C9—H9c	0.96
C2—C3	1.385 (3)	C10—H10a	0.96
C3—C4	1.380 (3)	C10—H10b	0.96
C4—C5	1.372 (3)	C10—H10c	0.96
C7—O1—C9	114.8 (2)	C2—C3—H3	120.7
C7—O2—C10	116.4 (2)	C4—C3—H3	120.7
O3—N1—O4	123.7 (2)	C4—C5—H5	120.5
O3—N1—C4	117.9 (2)	C6—C5—H5	120.5
O4—N1—C4	118.4 (2)	C5—C6—H6	119.7
C2—C1—C6	119.1 (2)	C1—C6—H6	119.7
C2—C1—C7	121.9 (2)	C7—C8—H8a	109.3
C6—C1—C7	119.0 (2)	Br1—C8—H8a	109.3
C1—C2—C3	120.8 (2)	C7—C8—H8b	109.3
C2—C3—C4	118.6 (2)	Br1—C8—H8b	109.3
C3—C4—C5	122.0 (2)	H8a—C8—H8b	107.9
C3—C4—N1	118.9 (2)	O1—C9—H9a	109.5
C5—C4—N1	119.1 (2)	O1—C9—H9b	109.5
C4—C5—C6	119.0 (2)	H9a—C9—H9b	109.5
C1—C6—C5	120.5 (2)	O1—C9—H9c	109.5
O2—C7—O1	111.8 (2)	H9a—C9—H9c	109.5
O1—C7—C8	101.9 (2)	H9b—C9—H9c	109.5
O2—C7—C8	113.1 (2)	O2—C10—H10a	109.5
O1—C7—C1	111.3 (2)	O2—C10—H10b	109.5
O2—C7—C1	106.5 (2)	H10a—C10—H10b	109.5
C1—C7—C8	112.3 (2)	O2—C10—H10c	109.5
C7—C8—Br1	111.8 (2)	H10a—C10—H10c	109.5
C1—C2—H2	119.6	H10b—C10—H10c	109.5
C3—C2—H2	119.6
C6—C1—C2—C3	0.5 (4)	C10—O2—C7—C8	−56.3 (3)
C7—C1—C2—C3	−178.8 (2)	C10—O2—C7—C1	179.8 (2)
C1—C2—C3—C4	−0.2 (4)	C9—O1—C7—O2	60.4 (2)
C2—C3—C4—C5	−0.3 (4)	C9—O1—C7—C8	−178.5 (2)
C2—C3—C4—N1	178.5 (2)	C9—O1—C7—C1	−58.6 (2)
O4—N1—C4—C5	176.0 (2)	C2—C1—C7—O2	0.4 (3)
O3—N1—C4—C5	−3.1 (3)	C6—C1—C7—O2	−178.9 (2)
O4—N1—C4—C3	−2.8 (3)	C2—C1—C7—O1	122.6 (2)
O3—N1—C4—C3	178.1 (2)	C6—C1—C7—O1	−56.7 (3)
C3—C4—C5—C6	0.6 (4)	C2—C1—C7—C8	−123.9 (2)
N1—C4—C5—C6	−178.2 (2)	C6—C1—C7—C8	56.7 (3)
C4—C5—C6—C1	−0.3 (4)	O2—C7—C8—Br1	−57.0 (2)
C2—C1—C6—C5	−0.2 (3)	O1—C7—C8—Br1	−177.2 (2)
C7—C1—C6—C5	179.1 (2)	C1—C7—C8—Br1	63.6 (2)
C10—O2—C7—O1	58.0 (3)