1,8-Dihydr-oxy-2,4,5,7-tetra-nitro-9,10-anthraquinone.

The ring system in the title compound, C(14)H(4)N(4)O(12), is essentially planar (r.m.s. deviation of the carbon atoms = 0.085 Å); the two hydr-oxy groups form intra-molecular hydrogen bonds to the same carbonyl O atom. The nitro groups are twisted with respect to the mean plane of the ring system by 74.3 (1) (1-nitro), 42.3 (3) (3-nitro), 45.7 (3) (6-nitro) and 66.9 (1)° (8-nitro).

Related literature

For the synthesis of the title compound, see: Teich et al. (2004 ▶). For related structures, see: Armaghan et al. (2010 ▶); Brown & Colclough (1983 ▶), Yatsenko et al. (1996 ▶).

Experimental

Crystal data

C14H4N4O12

M = 420.21

Monoclinic,

a = 17.726 (2) Å

b = 9.007 (1) Å

c = 9.731 (1) Å

β = 102.643 (2)°

V = 1515.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 223 K

0.35 × 0.25 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

11323 measured reflections

2672 independent reflections

2034 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.215

S = 1.10

2672 reflections

279 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.36 e Å−3

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/S1600536810014431/bt5249sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014431/bt5249Isup2.hkl

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

C14H4N4O12	F(000) = 848
Mr = 420.21	Dx = 1.841 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2323 reflections
a = 17.726 (2) Å	θ = 2.3–27.5°
b = 9.007 (1) Å	µ = 0.17 mm−1
c = 9.731 (1) Å	T = 223 K
β = 102.643 (2)°	Plate, brown
V = 1515.9 (3) Å3	0.35 × 0.25 × 0.10 mm
Z = 4

Bruker SMART APEX diffractometer	Rint = 0.045
graphite	θmax = 25.0°, θmin = 1.2°
ω scans	h = −19→21
11323 measured reflections	k = −10→10
2672 independent reflections	l = −11→11
2034 reflections with I > 2σ(I)

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.215	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.137P)2 + 0.3859P] where P = (Fo2 + 2Fc2)/3
2672 reflections	(Δ/σ)max = 0.001
279 parameters	Δρmax = 0.35 e Å−3
2 restraints	Δρmin = −0.36 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.34937 (16)	0.2030 (3)	0.4649 (3)	0.0528 (7)
H1	0.323 (2)	0.172 (5)	0.388 (3)	0.082 (16)*
O2	0.24924 (13)	0.2174 (2)	0.2291 (2)	0.0417 (6)
O3	0.15091 (14)	0.2212 (2)	−0.0089 (3)	0.0410 (6)
H3	0.183 (2)	0.186 (6)	0.060 (4)	0.099 (18)*
O4	0.07048 (14)	0.2831 (3)	−0.2661 (3)	0.0503 (7)
O5	−0.02307 (13)	0.4233 (3)	−0.2381 (3)	0.0465 (7)
O6	0.06528 (16)	0.8754 (3)	0.0919 (3)	0.0606 (8)
O7	0.17014 (16)	0.9106 (3)	0.0217 (3)	0.0565 (8)
O8	0.22018 (17)	0.7979 (3)	0.2950 (3)	0.0614 (9)
O9	0.33793 (14)	0.8827 (3)	0.5708 (3)	0.0507 (7)
O10	0.3791 (2)	0.8835 (3)	0.3801 (4)	0.0895 (12)
O11	0.51679 (18)	0.4003 (4)	0.7123 (4)	0.0879 (12)
O12	0.43047 (19)	0.2420 (4)	0.7288 (3)	0.0806 (11)
N1	0.04326 (15)	0.3791 (3)	−0.2055 (3)	0.0333 (6)
N2	0.12252 (16)	0.8324 (3)	0.0558 (3)	0.0348 (6)
N3	0.35601 (16)	0.8218 (3)	0.4727 (3)	0.0413 (7)
N4	0.45331 (17)	0.3494 (3)	0.6774 (3)	0.0438 (7)
C1	0.34783 (18)	0.3492 (4)	0.4612 (3)	0.0348 (7)
C2	0.29723 (16)	0.4320 (3)	0.3556 (3)	0.0293 (7)
C3	0.24621 (16)	0.3536 (3)	0.2380 (3)	0.0305 (7)
C4	0.19253 (16)	0.4400 (3)	0.1305 (3)	0.0279 (7)
C5	0.14731 (17)	0.3649 (3)	0.0136 (3)	0.0292 (7)
C6	0.09371 (17)	0.4510 (3)	−0.0830 (3)	0.0295 (7)
C7	0.08449 (17)	0.5998 (3)	−0.0660 (3)	0.0303 (7)
H7	0.0465	0.6532	−0.1295	0.036*
C8	0.13215 (16)	0.6704 (3)	0.0466 (3)	0.0284 (7)
C9	0.18590 (16)	0.5934 (3)	0.1447 (3)	0.0270 (7)
C10	0.23464 (18)	0.6727 (3)	0.2673 (3)	0.0326 (7)
C11	0.29712 (17)	0.5868 (3)	0.3616 (3)	0.0296 (7)
C12	0.35047 (17)	0.6585 (4)	0.4664 (3)	0.0324 (7)
C13	0.40121 (18)	0.5807 (4)	0.5685 (3)	0.0374 (8)
H13	0.4371	0.6309	0.6386	0.045*
C14	0.39833 (18)	0.4294 (4)	0.5659 (3)	0.0374 (8)

	U11	U22	U33	U12	U13	U23
O1	0.0710 (18)	0.0263 (13)	0.0517 (16)	0.0112 (11)	−0.0070 (13)	0.0058 (11)
O2	0.0511 (14)	0.0192 (12)	0.0471 (14)	0.0043 (9)	−0.0062 (11)	0.0007 (9)
O3	0.0589 (16)	0.0178 (11)	0.0410 (13)	−0.0005 (10)	−0.0008 (11)	−0.0021 (9)
O4	0.0553 (16)	0.0469 (15)	0.0447 (14)	0.0009 (12)	0.0024 (11)	−0.0179 (12)
O5	0.0356 (13)	0.0538 (15)	0.0459 (14)	−0.0033 (11)	−0.0002 (10)	−0.0021 (11)
O6	0.0752 (19)	0.0413 (15)	0.0698 (19)	0.0242 (13)	0.0254 (15)	0.0017 (12)
O7	0.0714 (18)	0.0215 (12)	0.080 (2)	−0.0048 (12)	0.0241 (15)	0.0037 (12)
O8	0.094 (2)	0.0270 (14)	0.0471 (15)	0.0208 (13)	−0.0187 (14)	−0.0113 (11)
O9	0.0628 (16)	0.0403 (14)	0.0484 (15)	0.0035 (11)	0.0108 (12)	−0.0159 (11)
O10	0.174 (4)	0.0379 (16)	0.074 (2)	−0.0259 (18)	0.066 (2)	−0.0057 (14)
O11	0.057 (2)	0.092 (3)	0.097 (3)	0.0004 (17)	−0.0214 (18)	0.020 (2)
O12	0.075 (2)	0.089 (2)	0.067 (2)	0.0012 (17)	−0.0084 (16)	0.0411 (18)
N1	0.0357 (15)	0.0309 (14)	0.0308 (13)	−0.0076 (11)	0.0020 (11)	0.0005 (11)
N2	0.0458 (16)	0.0257 (14)	0.0300 (13)	0.0127 (12)	0.0018 (11)	0.0004 (11)
N3	0.0558 (17)	0.0317 (15)	0.0339 (15)	−0.0049 (13)	0.0047 (13)	−0.0061 (12)
N4	0.0417 (17)	0.0464 (18)	0.0391 (16)	0.0086 (13)	−0.0002 (13)	0.0057 (13)
C1	0.0400 (17)	0.0286 (17)	0.0348 (16)	0.0070 (13)	0.0064 (13)	0.0033 (12)
C2	0.0344 (16)	0.0266 (16)	0.0262 (15)	0.0051 (12)	0.0052 (12)	0.0020 (11)
C3	0.0357 (17)	0.0223 (17)	0.0321 (16)	0.0040 (11)	0.0045 (13)	0.0021 (12)
C4	0.0301 (15)	0.0205 (15)	0.0324 (15)	0.0006 (11)	0.0052 (12)	0.0015 (11)
C5	0.0361 (16)	0.0214 (15)	0.0307 (15)	−0.0014 (12)	0.0085 (12)	0.0007 (11)
C6	0.0315 (15)	0.0259 (16)	0.0297 (15)	−0.0030 (12)	0.0041 (12)	−0.0004 (12)
C7	0.0321 (16)	0.0291 (16)	0.0285 (15)	0.0032 (12)	0.0041 (12)	0.0043 (12)
C8	0.0348 (16)	0.0196 (15)	0.0310 (15)	0.0039 (12)	0.0078 (12)	0.0003 (12)
C9	0.0321 (15)	0.0218 (15)	0.0273 (15)	0.0037 (12)	0.0071 (12)	0.0019 (11)
C10	0.0457 (18)	0.0206 (16)	0.0294 (15)	0.0046 (13)	0.0034 (13)	0.0000 (12)
C11	0.0377 (17)	0.0241 (16)	0.0272 (15)	0.0027 (12)	0.0073 (13)	0.0002 (11)
C12	0.0380 (16)	0.0294 (17)	0.0295 (15)	−0.0012 (13)	0.0064 (12)	−0.0019 (12)
C13	0.0398 (18)	0.0413 (19)	0.0297 (16)	−0.0005 (14)	0.0047 (13)	−0.0039 (13)
C14	0.0355 (17)	0.042 (2)	0.0319 (17)	0.0073 (14)	0.0019 (13)	0.0037 (14)

O1—C1	1.317 (4)	C1—C14	1.401 (4)
O1—H1	0.84 (3)	C1—C2	1.419 (4)
O2—C3	1.232 (4)	C2—C11	1.395 (4)
O3—C5	1.316 (4)	C2—C3	1.474 (4)
O3—H3	0.84 (4)	C3—C4	1.473 (4)
O4—N1	1.206 (3)	C4—C9	1.396 (4)
O5—N1	1.216 (3)	C4—C5	1.412 (4)
O6—N2	1.208 (4)	C5—C6	1.413 (4)
O7—N2	1.201 (4)	C6—C7	1.364 (4)
O8—C10	1.199 (4)	C7—C8	1.383 (4)
O9—N3	1.203 (4)	C7—H7	0.9400
O10—N3	1.205 (4)	C8—C9	1.379 (4)
O11—N4	1.194 (4)	C9—C10	1.493 (4)
O12—N4	1.199 (4)	C10—C11	1.491 (4)
N1—C6	1.475 (4)	C11—C12	1.389 (4)
N2—C8	1.474 (4)	C12—C13	1.377 (4)
N3—C12	1.474 (4)	C13—C14	1.364 (4)
N4—C14	1.478 (4)	C13—H13	0.9400
C1—O1—H1	108 (4)	C4—C5—C6	116.9 (3)
C5—O3—H3	107 (4)	C7—C6—C5	122.7 (3)
O4—N1—O5	125.1 (3)	C7—C6—N1	117.5 (2)
O4—N1—C6	118.3 (2)	C5—C6—N1	119.8 (3)
O5—N1—C6	116.6 (3)	C6—C7—C8	118.6 (3)
O7—N2—O6	125.3 (3)	C6—C7—H7	120.7
O7—N2—C8	117.8 (3)	C8—C7—H7	120.7
O6—N2—C8	116.8 (3)	C9—C8—C7	121.8 (3)
O9—N3—O10	125.2 (3)	C9—C8—N2	121.9 (2)
O9—N3—C12	117.4 (3)	C7—C8—N2	116.4 (2)
O10—N3—C12	117.4 (3)	C8—C9—C4	119.3 (3)
O11—N4—O12	125.1 (3)	C8—C9—C10	120.2 (3)
O11—N4—C14	116.7 (3)	C4—C9—C10	120.4 (2)
O12—N4—C14	118.1 (3)	O8—C10—C11	121.1 (3)
O1—C1—C14	119.3 (3)	O8—C10—C9	121.0 (3)
O1—C1—C2	123.4 (3)	C11—C10—C9	117.7 (3)
C14—C1—C2	117.2 (3)	C12—C11—C2	119.3 (3)
C11—C2—C1	120.1 (3)	C12—C11—C10	120.3 (3)
C11—C2—C3	120.3 (2)	C2—C11—C10	120.0 (2)
C1—C2—C3	119.6 (3)	C13—C12—C11	121.7 (3)
O2—C3—C4	120.5 (3)	C13—C12—N3	116.8 (3)
O2—C3—C2	120.2 (3)	C11—C12—N3	121.6 (3)
C4—C3—C2	119.3 (3)	C14—C13—C12	118.6 (3)
C9—C4—C5	120.6 (3)	C14—C13—H13	120.7
C9—C4—C3	120.5 (3)	C12—C13—H13	120.7
C5—C4—C3	118.9 (3)	C13—C14—C1	123.0 (3)
O3—C5—C4	124.4 (3)	C13—C14—N4	117.3 (3)
O3—C5—C6	118.6 (3)	C1—C14—N4	119.7 (3)
O1—C1—C2—C11	177.7 (3)	C5—C4—C9—C8	2.9 (4)
C14—C1—C2—C11	−2.4 (4)	C3—C4—C9—C8	−176.4 (3)
O1—C1—C2—C3	−3.7 (5)	C5—C4—C9—C10	−179.1 (3)
C14—C1—C2—C3	176.3 (3)	C3—C4—C9—C10	1.6 (4)
C11—C2—C3—O2	176.3 (3)	C8—C9—C10—O8	11.7 (5)
C1—C2—C3—O2	−2.3 (4)	C4—C9—C10—O8	−166.3 (3)
C11—C2—C3—C4	−2.8 (4)	C8—C9—C10—C11	−173.9 (3)
C1—C2—C3—C4	178.6 (3)	C4—C9—C10—C11	8.1 (4)
O2—C3—C4—C9	176.3 (3)	C1—C2—C11—C12	4.3 (4)
C2—C3—C4—C9	−4.5 (4)	C3—C2—C11—C12	−174.3 (3)
O2—C3—C4—C5	−3.0 (4)	C1—C2—C11—C10	−168.6 (3)
C2—C3—C4—C5	176.1 (3)	C3—C2—C11—C10	12.8 (4)
C9—C4—C5—O3	178.9 (3)	O8—C10—C11—C12	−13.8 (5)
C3—C4—C5—O3	−1.8 (4)	C9—C10—C11—C12	171.8 (3)
C9—C4—C5—C6	−2.6 (4)	O8—C10—C11—C2	159.0 (3)
C3—C4—C5—C6	176.7 (3)	C9—C10—C11—C2	−15.4 (4)
O3—C5—C6—C7	178.2 (3)	C2—C11—C12—C13	−3.0 (5)
C4—C5—C6—C7	−0.5 (4)	C10—C11—C12—C13	169.9 (3)
O3—C5—C6—N1	0.2 (4)	C2—C11—C12—N3	176.3 (3)
C4—C5—C6—N1	−178.5 (2)	C10—C11—C12—N3	−10.8 (4)
O4—N1—C6—C7	142.1 (3)	O9—N3—C12—C13	−67.5 (4)
O5—N1—C6—C7	−37.2 (4)	O10—N3—C12—C13	111.6 (4)
O4—N1—C6—C5	−39.8 (4)	O9—N3—C12—C11	113.1 (3)
O5—N1—C6—C5	140.9 (3)	O10—N3—C12—C11	−67.7 (4)
C5—C6—C7—C8	3.2 (4)	C11—C12—C13—C14	−0.2 (5)
N1—C6—C7—C8	−178.8 (3)	N3—C12—C13—C14	−179.6 (3)
C6—C7—C8—C9	−2.9 (4)	C12—C13—C14—C1	2.2 (5)
C6—C7—C8—N2	176.9 (3)	C12—C13—C14—N4	−179.7 (3)
O7—N2—C8—C9	76.1 (4)	O1—C1—C14—C13	179.0 (3)
O6—N2—C8—C9	−106.8 (3)	C2—C1—C14—C13	−1.0 (5)
O7—N2—C8—C7	−103.7 (3)	O1—C1—C14—N4	1.0 (5)
O6—N2—C8—C7	73.4 (3)	C2—C1—C14—N4	−179.0 (3)
C7—C8—C9—C4	−0.1 (4)	O11—N4—C14—C13	−38.1 (5)
N2—C8—C9—C4	−179.9 (3)	O12—N4—C14—C13	139.6 (4)
C7—C8—C9—C10	−178.1 (3)	O11—N4—C14—C1	140.0 (4)
N2—C8—C9—C10	2.1 (4)	O12—N4—C14—C1	−42.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84 (3)	1.84 (3)	2.579 (3)	146 (5)
O3—H3···O2	0.84 (4)	1.82 (3)	2.576 (3)	148 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84 (3)	1.84 (3)	2.579 (3)	146 (5)
O3—H3⋯O2	0.84 (4)	1.82 (3)	2.576 (3)	148 (5)