2'-Chloro-4-meth-oxy-3-nitro-benzil.

In the title compound, C(15)H(10)ClNO(5), the dihedral angle between the aromatic rings is 87.99 (5)°. The O-C-C-O torsion angle between the two carbonyl units is -119.03 (16)°. The crystal structure is stabilized by a weak intermolecular C-H⋯O hydrogen bond.

Related literature

For the biological activity of benzil derivatives, see: Mousset et al. (2008 ▶); Mahabusarakam et al. (2004 ▶); Ganapaty et al. (2009 ▶). For bond-length data and related structures, see: Allen et al. (1987 ▶); Fun & Kia (2008a ▶,b ▶).

Experimental

Crystal data

C15H10ClNO5

M = 319.69

Triclinic,

a = 7.8559 (2) Å

b = 8.1003 (2) Å

c = 12.4961 (3) Å

α = 74.893 (1)°

β = 74.809 (2)°

γ = 68.593 (1)°

V = 702.32 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 295 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.917, T max = 0.943

17487 measured reflections

3937 independent reflections

3150 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.128

S = 1.06

3937 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019532/bt5555sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019532/bt5555Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019532/bt5555Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H10ClNO5	Z = 2
Mr = 319.69	F(000) = 328
Triclinic, P1	Dx = 1.512 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8559 (2) Å	Cell parameters from 8570 reflections
b = 8.1003 (2) Å	θ = 2.7–29.0°
c = 12.4961 (3) Å	µ = 0.30 mm−1
α = 74.893 (1)°	T = 295 K
β = 74.809 (2)°	Block, colourless
γ = 68.593 (1)°	0.30 × 0.20 × 0.20 mm
V = 702.32 (3) Å3

Bruker Kappa APEXII diffractometer	3937 independent reflections
Radiation source: fine-focus sealed tube	3150 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω and φ scans	θmax = 29.6°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.917, Tmax = 0.943	k = −11→10
17487 measured reflections	l = −12→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0635P)2 + 0.160P] where P = (Fo2 + 2Fc2)/3
3937 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.15981 (6)	0.62735 (6)	0.72481 (4)	0.06164 (15)
O1	0.66183 (15)	0.31713 (16)	0.83551 (11)	0.0568 (3)
O2	0.39794 (18)	0.70912 (17)	0.88704 (10)	0.0583 (3)
O3	0.82025 (17)	0.96590 (15)	0.40294 (9)	0.0523 (3)
O4	0.5354 (2)	1.23772 (19)	0.64274 (14)	0.0786 (5)
O5	0.7972 (2)	1.19529 (19)	0.52797 (13)	0.0714 (4)
N1	0.6714 (2)	1.14290 (17)	0.58676 (11)	0.0457 (3)
C1	0.17355 (19)	0.45206 (19)	0.83978 (12)	0.0404 (3)
C2	0.0214 (2)	0.3912 (2)	0.88416 (15)	0.0505 (4)
H2	−0.0877	0.4486	0.8552	0.061*
C3	0.0327 (2)	0.2455 (2)	0.97122 (17)	0.0571 (4)
H3	−0.0693	0.2046	1.0012	0.069*
C4	0.1931 (3)	0.1598 (2)	1.01429 (16)	0.0587 (4)
H4	0.1997	0.0611	1.0730	0.070*
C5	0.3451 (2)	0.2209 (2)	0.96994 (14)	0.0480 (3)
H5	0.4537	0.1627	0.9993	0.058*
C6	0.33717 (18)	0.36820 (18)	0.88208 (12)	0.0376 (3)
C7	0.50704 (19)	0.4244 (2)	0.83798 (12)	0.0402 (3)
C8	0.4875 (2)	0.6252 (2)	0.81244 (12)	0.0411 (3)
C9	0.59015 (19)	0.70248 (18)	0.70630 (12)	0.0384 (3)
C10	0.59340 (19)	0.87676 (18)	0.69408 (12)	0.0383 (3)
H10	0.5392	0.9386	0.7540	0.046*
C11	0.67654 (19)	0.95783 (17)	0.59376 (12)	0.0370 (3)
C12	0.7569 (2)	0.87131 (19)	0.50031 (12)	0.0397 (3)
C13	0.7560 (2)	0.6947 (2)	0.51480 (13)	0.0471 (3)
H13	0.8119	0.6315	0.4556	0.057*
C14	0.6734 (2)	0.61296 (19)	0.61536 (13)	0.0453 (3)
H14	0.6732	0.4958	0.6228	0.054*
C15	0.8938 (3)	0.8816 (3)	0.30568 (15)	0.0650 (5)
H15A	1.0008	0.7784	0.3192	0.098*
H15B	0.9292	0.9660	0.2416	0.098*
H15C	0.8008	0.8441	0.2911	0.098*

	U11	U22	U33	U12	U13	U23
Cl1	0.0595 (3)	0.0632 (3)	0.0616 (3)	−0.0207 (2)	−0.0251 (2)	0.0054 (2)
O1	0.0354 (5)	0.0565 (7)	0.0711 (8)	−0.0172 (5)	−0.0089 (5)	0.0038 (6)
O2	0.0625 (7)	0.0654 (7)	0.0542 (7)	−0.0350 (6)	0.0107 (5)	−0.0236 (6)
O3	0.0677 (7)	0.0483 (6)	0.0396 (5)	−0.0255 (5)	0.0027 (5)	−0.0083 (4)
O4	0.0917 (11)	0.0534 (7)	0.0943 (11)	−0.0305 (7)	0.0123 (8)	−0.0384 (8)
O5	0.0858 (10)	0.0603 (8)	0.0791 (9)	−0.0483 (7)	0.0052 (7)	−0.0153 (7)
N1	0.0600 (8)	0.0395 (6)	0.0464 (7)	−0.0238 (6)	−0.0113 (6)	−0.0094 (5)
C1	0.0379 (7)	0.0413 (7)	0.0461 (7)	−0.0148 (6)	−0.0065 (5)	−0.0128 (6)
C2	0.0344 (7)	0.0574 (9)	0.0682 (10)	−0.0180 (6)	−0.0040 (7)	−0.0265 (8)
C3	0.0434 (8)	0.0594 (10)	0.0749 (11)	−0.0309 (7)	0.0117 (8)	−0.0246 (9)
C4	0.0578 (10)	0.0507 (9)	0.0641 (10)	−0.0294 (8)	0.0054 (8)	−0.0036 (8)
C5	0.0434 (7)	0.0443 (8)	0.0538 (9)	−0.0187 (6)	−0.0059 (6)	−0.0013 (6)
C6	0.0344 (6)	0.0384 (6)	0.0425 (7)	−0.0170 (5)	−0.0023 (5)	−0.0088 (5)
C7	0.0368 (7)	0.0461 (7)	0.0403 (7)	−0.0199 (6)	−0.0060 (5)	−0.0035 (6)
C8	0.0387 (7)	0.0463 (7)	0.0448 (7)	−0.0226 (6)	−0.0046 (6)	−0.0090 (6)
C9	0.0385 (6)	0.0377 (7)	0.0431 (7)	−0.0180 (5)	−0.0054 (5)	−0.0080 (5)
C10	0.0406 (7)	0.0397 (7)	0.0398 (7)	−0.0175 (6)	−0.0045 (5)	−0.0122 (5)
C11	0.0419 (7)	0.0333 (6)	0.0414 (7)	−0.0174 (5)	−0.0090 (5)	−0.0070 (5)
C12	0.0412 (7)	0.0403 (7)	0.0388 (7)	−0.0158 (6)	−0.0040 (5)	−0.0084 (5)
C13	0.0570 (9)	0.0404 (7)	0.0447 (8)	−0.0172 (7)	0.0010 (6)	−0.0173 (6)
C14	0.0535 (8)	0.0352 (7)	0.0510 (8)	−0.0191 (6)	−0.0041 (6)	−0.0126 (6)
C15	0.0772 (12)	0.0696 (11)	0.0423 (8)	−0.0258 (10)	0.0097 (8)	−0.0175 (8)

Cl1—C1	1.7315 (16)	C5—H5	0.9300
O1—C7	1.2072 (18)	C6—C7	1.4894 (18)
O2—C8	1.2098 (18)	C7—C8	1.531 (2)
O3—C12	1.3379 (17)	C8—C9	1.4755 (19)
O3—C15	1.4329 (19)	C9—C10	1.3888 (18)
O4—N1	1.2288 (19)	C9—C14	1.392 (2)
O5—N1	1.2081 (18)	C10—C11	1.3727 (19)
N1—C11	1.4649 (17)	C10—H10	0.9300
C1—C2	1.386 (2)	C11—C12	1.4039 (19)
C1—C6	1.387 (2)	C12—C13	1.397 (2)
C2—C3	1.375 (3)	C13—C14	1.375 (2)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.371 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.386 (2)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.390 (2)
C12—O3—C15	118.41 (13)	O2—C8—C7	116.30 (13)
O5—N1—O4	123.29 (13)	C9—C8—C7	120.11 (12)
O5—N1—C11	119.95 (13)	C10—C9—C14	118.62 (13)
O4—N1—C11	116.76 (13)	C10—C9—C8	118.39 (12)
C2—C1—C6	120.96 (14)	C14—C9—C8	122.86 (12)
C2—C1—Cl1	118.46 (12)	C11—C10—C9	120.09 (12)
C6—C1—Cl1	120.49 (11)	C11—C10—H10	120.0
C3—C2—C1	119.54 (15)	C9—C10—H10	120.0
C3—C2—H2	120.2	C10—C11—C12	122.04 (12)
C1—C2—H2	120.2	C10—C11—N1	116.88 (12)
C4—C3—C2	120.65 (14)	C12—C11—N1	121.04 (12)
C4—C3—H3	119.7	O3—C12—C13	124.79 (13)
C2—C3—H3	119.7	O3—C12—C11	118.04 (12)
C3—C4—C5	119.75 (16)	C13—C12—C11	117.09 (13)
C3—C4—H4	120.1	C14—C13—C12	120.92 (13)
C5—C4—H4	120.1	C14—C13—H13	119.5
C4—C5—C6	120.75 (16)	C12—C13—H13	119.5
C4—C5—H5	119.6	C13—C14—C9	121.19 (13)
C6—C5—H5	119.6	C13—C14—H14	119.4
C1—C6—C5	118.35 (12)	C9—C14—H14	119.4
C1—C6—C7	124.05 (13)	O3—C15—H15A	109.5
C5—C6—C7	117.59 (13)	O3—C15—H15B	109.5
O1—C7—C6	122.20 (13)	H15A—C15—H15B	109.5
O1—C7—C8	117.75 (12)	O3—C15—H15C	109.5
C6—C7—C8	119.31 (12)	H15A—C15—H15C	109.5
O2—C8—C9	123.30 (13)	H15B—C15—H15C	109.5
C6—C1—C2—C3	−0.1 (2)	O2—C8—C9—C14	−171.77 (15)
Cl1—C1—C2—C3	176.25 (12)	C7—C8—C9—C14	14.6 (2)
C1—C2—C3—C4	−0.1 (3)	C14—C9—C10—C11	0.4 (2)
C2—C3—C4—C5	0.2 (3)	C8—C9—C10—C11	−175.55 (13)
C3—C4—C5—C6	−0.1 (3)	C9—C10—C11—C12	1.3 (2)
C2—C1—C6—C5	0.3 (2)	C9—C10—C11—N1	178.94 (12)
Cl1—C1—C6—C5	−176.05 (11)	O5—N1—C11—C10	148.61 (15)
C2—C1—C6—C7	179.26 (13)	O4—N1—C11—C10	−31.4 (2)
Cl1—C1—C6—C7	3.0 (2)	O5—N1—C11—C12	−33.7 (2)
C4—C5—C6—C1	−0.2 (2)	O4—N1—C11—C12	146.30 (16)
C4—C5—C6—C7	−179.23 (15)	C15—O3—C12—C13	−0.3 (2)
C1—C6—C7—O1	−145.86 (16)	C15—O3—C12—C11	−176.86 (15)
C5—C6—C7—O1	33.2 (2)	C10—C11—C12—O3	174.20 (14)
C1—C6—C7—C8	44.2 (2)	N1—C11—C12—O3	−3.4 (2)
C5—C6—C7—C8	−136.81 (14)	C10—C11—C12—C13	−2.6 (2)
O1—C7—C8—O2	−119.03 (16)	N1—C11—C12—C13	179.86 (14)
C6—C7—C8—O2	51.37 (19)	O3—C12—C13—C14	−174.26 (15)
O1—C7—C8—C9	55.0 (2)	C11—C12—C13—C14	2.3 (2)
C6—C7—C8—C9	−134.60 (14)	C12—C13—C14—C9	−0.7 (3)
O2—C8—C9—C10	4.0 (2)	C10—C9—C14—C13	−0.6 (2)
C7—C8—C9—C10	−169.64 (13)	C8—C9—C14—C13	175.07 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.53	3.318 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.53	3.318 (2)	143

Symmetry code: (i) .