1,5-Dichloro-4,8-dinitro-anthraquinone.

The ring skeleton of the title compound, C(14)H(4)Cl(2)N(2)O(6), is close to planar (r.m.s. deviation of the carbon atoms 0.091 Å); the nitro goups are twisted with respect to the mean plane of the ring system by 70.8 (1) and 86.7 (2)°. The crystal studied was found to be a merohedral twin, with a domain ratio of 0.61 (8):0.39 (8).

Related literature

For dehydro­sulfurization by using anthraquinone-based catalysts, see: Nagai et al. (1993 ▶). For a related structure, see: Armaghan et al. (2010 ▶).

Experimental

Crystal data

C14H4Cl2N2O6

M = 367.09

Monoclinic,

a = 5.9596 (6) Å

b = 11.3897 (11) Å

c = 9.8667 (9) Å

β = 93.519 (1)°

V = 668.47 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.53 mm−1

T = 100 K

0.12 × 0.12 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS, Sheldrick, 1996 ▶) T min = 0.940, T max = 0.940

6510 measured reflections

3028 independent reflections

2779 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.095

S = 1.04

3028 reflections

218 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.34 e Å−3

Absolute structure: Flack (Flack, 1983 ▶), 1402 Friedel pairs

Flack parameter: 0.39 (8)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029156/kp2270sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029156/kp2270Isup2.hkl

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

C14H4Cl2N2O6	F(000) = 368
Mr = 367.09	Dx = 1.824 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2429 reflections
a = 5.9596 (6) Å	θ = 2.7–28.3°
b = 11.3897 (11) Å	µ = 0.53 mm−1
c = 9.8667 (9) Å	T = 100 K
β = 93.519 (1)°	Cube, yellow
V = 668.47 (11) Å3	0.12 × 0.12 × 0.12 mm
Z = 2

Bruker SMART APEX diffractometer	3028 independent reflections
Radiation source: fine-focus sealed tube	2779 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS, Sheldrick, 1996)	h = −7→7
Tmin = 0.940, Tmax = 0.940	k = −14→14
6510 measured reflections	l = −12→12

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.339P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3028 reflections	Δρmax = 0.54 e Å−3
218 parameters	Δρmin = −0.34 e Å−3
1 restraint	Absolute structure: Flack (Flack, 1983) parameter from 1402 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.39 (8)

	x	y	z	Uiso*/Ueq
Cl1	0.62144 (12)	0.00005 (6)	0.17540 (8)	0.02356 (19)
Cl2	0.36066 (13)	0.69418 (6)	0.31405 (8)	0.0250 (2)
O1	0.0933 (4)	0.3072 (2)	0.6211 (2)	0.0271 (5)
O2	−0.1258 (4)	0.3417 (2)	0.4440 (2)	0.0277 (5)
O3	0.2920 (4)	0.4726 (2)	0.4346 (2)	0.0339 (6)
O4	1.1628 (4)	0.3759 (2)	0.0667 (2)	0.0280 (5)
O5	0.9158 (4)	0.3677 (3)	−0.1002 (2)	0.0404 (7)
O6	0.8065 (5)	0.2199 (2)	0.1277 (3)	0.0548 (9)
N1	0.0447 (4)	0.3022 (2)	0.4997 (3)	0.0147 (5)
N2	0.9756 (4)	0.3942 (2)	0.0136 (3)	0.0163 (5)
C1	0.4613 (5)	0.0953 (3)	0.2635 (3)	0.0142 (6)
C2	0.2957 (5)	0.0447 (3)	0.3375 (3)	0.0198 (6)
H2	0.2742	−0.0379	0.3350	0.024*
C3	0.1616 (5)	0.1141 (3)	0.4149 (3)	0.0162 (7)
H3	0.0494	0.0799	0.4668	0.019*
C4	0.1953 (5)	0.2341 (3)	0.4148 (3)	0.0136 (6)
C5	0.3553 (5)	0.2890 (3)	0.3409 (3)	0.0126 (6)
C6	0.3801 (5)	0.4179 (3)	0.3468 (3)	0.0181 (6)
C7	0.5285 (4)	0.4765 (3)	0.2507 (3)	0.0150 (6)
C8	0.5362 (5)	0.5992 (3)	0.2339 (3)	0.0153 (6)
C9	0.6860 (5)	0.6510 (3)	0.1494 (3)	0.0170 (6)
H9	0.6890	0.7340	0.1399	0.020*
C10	0.8297 (5)	0.5827 (3)	0.0795 (3)	0.0183 (7)
H10	0.9342	0.6178	0.0229	0.022*
C11	0.8195 (5)	0.4621 (3)	0.0930 (3)	0.0132 (6)
C12	0.6693 (5)	0.4075 (3)	0.1766 (3)	0.0132 (6)
C13	0.6668 (5)	0.2752 (3)	0.1839 (3)	0.0224 (7)
C14	0.4913 (4)	0.2177 (3)	0.2625 (3)	0.0121 (6)

	U11	U22	U33	U12	U13	U23
Cl1	0.0243 (3)	0.0116 (4)	0.0366 (4)	0.0019 (3)	0.0164 (3)	−0.0016 (3)
Cl2	0.0267 (4)	0.0132 (4)	0.0370 (4)	0.0049 (3)	0.0168 (3)	0.0022 (3)
O1	0.0307 (11)	0.0364 (13)	0.0147 (9)	0.0029 (10)	0.0041 (8)	−0.0053 (9)
O2	0.0209 (10)	0.0342 (13)	0.0276 (11)	0.0143 (10)	−0.0015 (9)	−0.0066 (10)
O3	0.0459 (13)	0.0198 (12)	0.0393 (13)	−0.0033 (10)	0.0285 (11)	−0.0054 (10)
O4	0.0191 (11)	0.0362 (14)	0.0284 (11)	0.0091 (9)	−0.0015 (9)	−0.0033 (10)
O5	0.0300 (12)	0.070 (2)	0.0210 (11)	0.0167 (12)	0.0000 (9)	−0.0185 (12)
O6	0.0656 (17)	0.0125 (12)	0.094 (2)	−0.0058 (12)	0.0693 (17)	−0.0087 (12)
N1	0.0140 (11)	0.0161 (13)	0.0147 (11)	−0.0012 (9)	0.0070 (9)	0.0004 (10)
N2	0.0167 (12)	0.0142 (13)	0.0188 (12)	−0.0046 (10)	0.0064 (10)	0.0013 (10)
C1	0.0172 (13)	0.0089 (14)	0.0168 (14)	−0.0012 (11)	0.0039 (11)	0.0026 (11)
C2	0.0225 (15)	0.0122 (15)	0.0252 (15)	−0.0012 (12)	0.0051 (12)	0.0029 (12)
C3	0.0133 (14)	0.0175 (18)	0.0183 (14)	−0.0027 (12)	0.0048 (11)	0.0054 (12)
C4	0.0109 (12)	0.0172 (16)	0.0133 (13)	0.0020 (11)	0.0036 (10)	−0.0002 (11)
C5	0.0140 (13)	0.0131 (15)	0.0106 (12)	−0.0012 (10)	0.0009 (10)	−0.0013 (10)
C6	0.0212 (14)	0.0118 (14)	0.0226 (14)	−0.0022 (11)	0.0104 (12)	−0.0021 (11)
C7	0.0144 (12)	0.0151 (17)	0.0154 (13)	−0.0035 (11)	0.0018 (10)	0.0006 (10)
C8	0.0108 (13)	0.0167 (16)	0.0186 (14)	0.0029 (11)	0.0025 (11)	−0.0036 (12)
C9	0.0208 (13)	0.0108 (14)	0.0198 (13)	−0.0027 (11)	0.0046 (11)	0.0010 (11)
C10	0.0232 (16)	0.0157 (17)	0.0166 (14)	−0.0026 (13)	0.0053 (12)	0.0008 (12)
C11	0.0136 (12)	0.0127 (15)	0.0137 (12)	−0.0025 (11)	0.0045 (10)	−0.0013 (10)
C12	0.0131 (12)	0.0129 (16)	0.0138 (13)	−0.0017 (12)	0.0013 (10)	0.0002 (10)
C13	0.0279 (15)	0.0142 (15)	0.0271 (16)	−0.0009 (12)	0.0170 (13)	−0.0024 (12)
C14	0.0109 (12)	0.0115 (16)	0.0142 (12)	0.0004 (10)	0.0039 (10)	0.0002 (10)

Cl1—C1	1.716 (3)	C3—H3	0.9500
Cl2—C8	1.730 (3)	C4—C5	1.385 (4)
O1—N1	1.216 (3)	C5—C14	1.411 (4)
O2—N1	1.211 (3)	C5—C6	1.476 (5)
O3—C6	1.213 (4)	C6—C7	1.493 (4)
O4—N2	1.221 (3)	C7—C12	1.390 (4)
O5—N2	1.197 (3)	C7—C8	1.408 (5)
O6—C13	1.205 (4)	C8—C9	1.390 (4)
N1—C4	1.483 (4)	C9—C10	1.373 (5)
N2—C11	1.472 (4)	C9—H9	0.9500
C1—C2	1.388 (4)	C10—C11	1.382 (5)
C1—C14	1.405 (5)	C10—H10	0.9500
C2—C3	1.386 (5)	C11—C12	1.399 (4)
C2—H2	0.9500	C12—C13	1.509 (5)
C3—C4	1.382 (4)	C13—C14	1.492 (4)
O2—N1—O1	124.9 (3)	C12—C7—C8	118.3 (3)
O2—N1—C4	117.3 (2)	C12—C7—C6	118.8 (3)
O1—N1—C4	117.7 (2)	C8—C7—C6	122.9 (3)
O5—N2—O4	124.8 (3)	C9—C8—C7	121.2 (3)
O5—N2—C11	118.1 (3)	C9—C8—Cl2	115.9 (3)
O4—N2—C11	116.9 (2)	C7—C8—Cl2	122.8 (3)
C2—C1—C14	120.7 (3)	C10—C9—C8	120.3 (3)
C2—C1—Cl1	116.0 (3)	C10—C9—H9	119.9
C14—C1—Cl1	123.3 (2)	C8—C9—H9	119.9
C3—C2—C1	120.4 (3)	C9—C10—C11	118.8 (3)
C3—C2—H2	119.8	C9—C10—H10	120.6
C1—C2—H2	119.8	C11—C10—H10	120.6
C4—C3—C2	118.3 (3)	C10—C11—C12	122.1 (3)
C4—C3—H3	120.8	C10—C11—N2	116.0 (3)
C2—C3—H3	120.8	C12—C11—N2	121.9 (3)
C3—C4—C5	123.4 (3)	C7—C12—C11	119.2 (3)
C3—C4—N1	115.1 (3)	C7—C12—C13	122.1 (3)
C5—C4—N1	121.5 (3)	C11—C12—C13	118.7 (3)
C4—C5—C14	117.8 (3)	O6—C13—C14	122.4 (3)
C4—C5—C6	119.8 (3)	O6—C13—C12	119.4 (3)
C14—C5—C6	122.3 (3)	C14—C13—C12	118.2 (3)
O3—C6—C5	119.6 (3)	C1—C14—C5	119.3 (3)
O3—C6—C7	121.5 (3)	C1—C14—C13	122.2 (3)
C5—C6—C7	118.7 (3)	C5—C14—C13	118.5 (3)
C14—C1—C2—C3	−2.0 (4)	C9—C10—C11—N2	179.0 (2)
Cl1—C1—C2—C3	178.3 (2)	O5—N2—C11—C10	−87.6 (4)
C1—C2—C3—C4	0.9 (4)	O4—N2—C11—C10	87.7 (4)
C2—C3—C4—C5	0.3 (5)	O5—N2—C11—C12	92.1 (4)
C2—C3—C4—N1	179.8 (2)	O4—N2—C11—C12	−92.5 (3)
O2—N1—C4—C3	−94.0 (3)	C8—C7—C12—C11	2.7 (4)
O1—N1—C4—C3	81.0 (3)	C6—C7—C12—C11	−175.8 (3)
O2—N1—C4—C5	85.4 (3)	C8—C7—C12—C13	−177.7 (3)
O1—N1—C4—C5	−99.5 (3)	C6—C7—C12—C13	3.8 (4)
C3—C4—C5—C14	−0.4 (4)	C10—C11—C12—C7	−1.3 (4)
N1—C4—C5—C14	−179.8 (2)	N2—C11—C12—C7	179.0 (2)
C3—C4—C5—C6	−179.9 (3)	C10—C11—C12—C13	179.1 (3)
N1—C4—C5—C6	0.7 (4)	N2—C11—C12—C13	−0.6 (4)
C4—C5—C6—O3	13.8 (5)	C7—C12—C13—O6	−173.0 (3)
C14—C5—C6—O3	−165.6 (3)	C11—C12—C13—O6	6.6 (5)
C4—C5—C6—C7	−170.8 (2)	C7—C12—C13—C14	6.2 (5)
C14—C5—C6—C7	9.7 (4)	C11—C12—C13—C14	−174.2 (2)
O3—C6—C7—C12	163.6 (3)	C2—C1—C14—C5	1.9 (4)
C5—C6—C7—C12	−11.6 (4)	Cl1—C1—C14—C5	−178.4 (2)
O3—C6—C7—C8	−14.9 (5)	C2—C1—C14—C13	−179.7 (3)
C5—C6—C7—C8	169.9 (3)	Cl1—C1—C14—C13	0.0 (4)
C12—C7—C8—C9	−2.3 (4)	C4—C5—C14—C1	−0.7 (4)
C6—C7—C8—C9	176.2 (3)	C6—C5—C14—C1	178.8 (3)
C12—C7—C8—Cl2	176.9 (2)	C4—C5—C14—C13	−179.1 (3)
C6—C7—C8—Cl2	−4.6 (4)	C6—C5—C14—C13	0.4 (4)
C7—C8—C9—C10	0.3 (4)	O6—C13—C14—C1	−7.4 (5)
Cl2—C8—C9—C10	−178.9 (2)	C12—C13—C14—C1	173.4 (3)
C8—C9—C10—C11	1.2 (4)	O6—C13—C14—C5	171.0 (3)
C9—C10—C11—C12	−0.7 (5)	C12—C13—C14—C5	−8.2 (4)