(2,4-Di­nitro­phenyl)(1-nitro­hexyl)­diazene

The title compound, C₁₂H₁₃N₅O₆, is a new azo compound. Its crystal structure shows that weak intermolecular interactions play an important role in the crystal packing. A dimer is formed via a weak C—H...O interaction between two mol­ecules. Neighboring dimers are connected by weak C—H...O interactions and a three-dimensional framework is formed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.130
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

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Alert level C
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.

   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

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(2,4-Dinitrophenyl)(1-nitrohexyl)diazene

Crystal data

C12H13N5O6	F(000) = 672
Mr = 323.27	Dx = 1.453 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.282 (2) Å	θ = 1.8–25.5°
b = 13.033 (2) Å	µ = 0.12 mm^−1
c = 10.162 (1) Å	T = 293 K
β = 98.50 (1)°	Block, colorless
V = 1477.8 (4) Å^3	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection

Bruker P4 diffractometer	Rint = 0.011
Radiation source: sealed tube	θmax = 25.5°, θmin = 1.8°
Graphite monochromator	h = −13→13
ω scans	k = 0→15
2748 measured reflections	l = 0→12
2748 independent reflections	3 standard reflections every 97 reflections
1811 reflections with I > 2σ(I)	intensity decay: 0.01%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 0.66P] where P = (Fo^2 + 2Fc^2)/3
2748 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.59 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.87669 (17)	0.54489 (16)	0.68623 (19)	0.0586 (5)
O2	0.99002 (17)	0.43034 (16)	0.61948 (18)	0.0546 (5)
O3	0.8410 (3)	0.2309 (3)	0.2173 (4)	0.0559 (9)	0.57
O4	0.6653 (12)	0.2008 (12)	0.2082 (15)	0.073 (3)	0.57
O5	0.44840 (17)	0.38398 (16)	−0.11070 (19)	0.0586 (5)
O6	0.42954 (17)	0.23316 (16)	−0.03275 (19)	0.0577 (5)
N1	0.8956 (2)	0.47701 (18)	0.6106 (2)	0.0461 (5)
N2	0.7499 (3)	0.2595 (2)	0.2345 (3)	0.0591 (7)
N3	0.53801 (19)	0.37311 (16)	0.18282 (19)	0.0422 (5)
N4	0.43320 (19)	0.39521 (16)	0.1931 (2)	0.0435 (5)
N5	0.4121 (2)	0.3253 (2)	−0.0332 (2)	0.0511 (6)
C1	0.7287 (2)	0.3460 (2)	0.3192 (2)	0.0468 (7)
C2	0.8196 (2)	0.3708 (2)	0.4202 (2)	0.0473 (6)
H2	0.8914	0.3346	0.4327	0.057 (8)*
C3	0.7997 (2)	0.45060 (19)	0.5016 (2)	0.0387 (6)
C4	0.6952 (2)	0.5062 (2)	0.4842 (2)	0.0429 (6)
H4	0.6841	0.5596	0.5418	0.047 (7)*
C5	0.6069 (2)	0.48164 (19)	0.3802 (2)	0.0423 (6)
H5	0.5369	0.5202	0.3657	0.047 (7)*
C6	0.6217 (2)	0.39975 (18)	0.2974 (2)	0.0388 (6)
C7	0.3451 (2)	0.37087 (19)	0.0750 (2)	0.0399 (6)
C8	0.2587 (2)	0.2917 (2)	0.1167 (3)	0.0507 (7)
H8A	0.2293	0.3152	0.1965	0.051 (7)*
H8B	0.3012	0.2277	0.1375	0.064 (9)*
C9	0.1530 (3)	0.2728 (2)	0.0077 (3)	0.0566 (8)
H9A	0.1810	0.2401	−0.0678	0.079 (10)*
H9B	0.0967	0.2266	0.0408	0.088 (11)*
C10	0.0898 (3)	0.3727 (2)	−0.0369 (3)	0.0581 (8)
H10A	0.0249	0.3589	−0.1085	0.081 (10)*
H10B	0.0556	0.4023	0.0366	0.085 (11)*
C11	0.1763 (3)	0.4485 (2)	−0.0842 (3)	0.0552 (7)
H11A	0.1347	0.5123	−0.1094	0.082 (11)*
H11B	0.2058	0.4212	−0.1620	0.070 (9)*
C12	0.2819 (2)	0.4694 (2)	0.0255 (3)	0.0505 (7)
H12A	0.3386	0.5146	−0.0086	0.059 (8)*
H12B	0.2531	0.5038	0.0992	0.060 (8)*
O3'	0.8133 (4)	0.2856 (4)	0.1471 (5)	0.0581 (12)	0.43
O4'	0.7004 (15)	0.1817 (16)	0.2363 (19)	0.062 (3)	0.43

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0580 (12)	0.0674 (14)	0.0478 (11)	−0.0060 (10)	−0.0010 (9)	−0.0153 (10)
O2	0.0495 (11)	0.0661 (13)	0.0459 (11)	−0.0052 (10)	−0.0003 (9)	−0.0070 (9)
O3	0.051 (2)	0.068 (3)	0.047 (2)	−0.0044 (19)	−0.0003 (18)	−0.009 (2)
O4	0.096 (9)	0.054 (5)	0.068 (7)	−0.006 (5)	0.015 (5)	−0.014 (4)
O5	0.0598 (12)	0.0709 (14)	0.0455 (11)	−0.0130 (11)	0.0091 (9)	−0.0041 (10)
O6	0.0594 (12)	0.0608 (14)	0.0532 (12)	−0.0099 (10)	0.0096 (9)	−0.0140 (10)
N1	0.0474 (13)	0.0526 (14)	0.0366 (12)	−0.0018 (11)	0.0003 (10)	0.0007 (11)
N2	0.0592 (18)	0.0646 (19)	0.0507 (16)	−0.0023 (16)	−0.0013 (13)	−0.0152 (14)
N3	0.0447 (12)	0.0431 (12)	0.0380 (12)	−0.0026 (10)	0.0031 (9)	−0.0019 (10)
N4	0.0444 (13)	0.0466 (13)	0.0376 (12)	−0.0009 (10)	0.0001 (9)	−0.0011 (10)
N5	0.0505 (14)	0.0602 (16)	0.0417 (13)	−0.0116 (12)	0.0038 (10)	−0.0084 (12)
C1	0.0532 (16)	0.0463 (15)	0.0395 (14)	0.0128 (13)	0.0020 (12)	−0.0077 (12)
C2	0.0466 (15)	0.0524 (16)	0.0410 (14)	0.0146 (13)	0.0000 (12)	−0.0036 (13)
C3	0.0398 (13)	0.0437 (14)	0.0319 (12)	−0.0010 (11)	0.0030 (11)	0.0024 (11)
C4	0.0444 (14)	0.0421 (15)	0.0423 (14)	0.0017 (12)	0.0064 (12)	−0.0064 (12)
C5	0.0381 (14)	0.0421 (14)	0.0466 (15)	0.0047 (12)	0.0060 (12)	−0.0026 (12)
C6	0.0416 (13)	0.0410 (14)	0.0333 (13)	−0.0023 (11)	0.0035 (10)	0.0005 (11)
C7	0.0419 (14)	0.0447 (14)	0.0326 (12)	−0.0055 (11)	0.0042 (10)	−0.0031 (11)
C8	0.0550 (16)	0.0511 (16)	0.0469 (16)	−0.0107 (14)	0.0104 (13)	0.0031 (13)
C9	0.0535 (17)	0.065 (2)	0.0504 (17)	−0.0165 (15)	0.0038 (14)	−0.0076 (15)
C10	0.0503 (16)	0.073 (2)	0.0491 (17)	−0.0128 (15)	0.0001 (14)	−0.0060 (15)
C11	0.0517 (16)	0.065 (2)	0.0471 (16)	−0.0089 (15)	0.0000 (13)	−0.0024 (14)
C12	0.0510 (16)	0.0478 (16)	0.0505 (16)	−0.0025 (13)	0.0003 (13)	0.0049 (13)
O3'	0.050 (3)	0.073 (3)	0.049 (3)	−0.013 (3)	0.000 (2)	−0.006 (3)
O4'	0.064 (7)	0.068 (9)	0.054 (6)	−0.014 (5)	0.008 (5)	−0.007 (5)

Geometric parameters (Å, º)

O1—N1	1.211 (3)	C4—H4	0.9297
O2—N1	1.218 (3)	C5—C6	1.385 (3)
O3—N2	1.131 (4)	C5—H5	0.9294
O4—N2	1.222 (17)	C7—C12	1.518 (4)
O5—N5	1.211 (3)	C7—C8	1.521 (3)
O6—N5	1.217 (3)	C8—C9	1.523 (4)
N1—C3	1.471 (3)	C8—H8A	0.9699
N2—O4'	1.16 (2)	C8—H8B	0.9701
N2—O3'	1.267 (6)	C9—C10	1.522 (4)
N2—C1	1.460 (3)	C9—H9A	0.9699
N3—N4	1.236 (3)	C9—H9B	0.9700
N3—C6	1.429 (3)	C10—C11	1.515 (4)
N4—C7	1.474 (3)	C10—H10A	0.9697
N5—C7	1.543 (3)	C10—H10B	0.9699
C1—C2	1.378 (3)	C11—C12	1.531 (4)
C1—C6	1.385 (3)	C11—H11A	0.9704
C2—C3	1.368 (3)	C11—H11B	0.9696
C2—H2	0.9297	C12—H12A	0.9698
C3—C4	1.373 (3)	C12—H12B	0.9701
C4—C5	1.378 (3)
O1—N1—O2	123.5 (2)	N4—C7—C8	107.57 (19)
O1—N1—C3	118.0 (2)	C12—C7—C8	112.1 (2)
O2—N1—C3	118.5 (2)	N4—C7—N5	108.69 (19)
O3—N2—O4'	99.6 (9)	C12—C7—N5	110.2 (2)
O3—N2—O4	117.4 (7)	C8—C7—N5	109.8 (2)
O3—N2—O3'	50.2 (3)	C7—C8—C9	111.9 (2)
O4'—N2—O3'	124.7 (11)	C7—C8—H8A	109.3
O4—N2—O3'	121.3 (8)	C9—C8—H8A	109.3
O3—N2—C1	125.2 (3)	C7—C8—H8B	109.1
O4'—N2—C1	123.0 (11)	C9—C8—H8B	109.1
O4—N2—C1	114.9 (8)	H8A—C8—H8B	108.0
O3'—N2—C1	111.4 (3)	C10—C9—C8	111.1 (2)
N4—N3—C6	113.6 (2)	C10—C9—H9A	109.4
N3—N4—C7	114.8 (2)	C8—C9—H9A	109.5
O5—N5—O6	123.8 (2)	C10—C9—H9B	109.4
O5—N5—C7	118.0 (2)	C8—C9—H9B	109.3
O6—N5—C7	118.2 (2)	H9A—C9—H9B	108.0
C2—C1—C6	122.4 (2)	C11—C10—C9	110.9 (2)
C2—C1—N2	116.9 (2)	C11—C10—H10A	109.5
C6—C1—N2	120.7 (2)	C9—C10—H10A	109.5
C3—C2—C1	117.3 (2)	C11—C10—H10B	109.4
C3—C2—H2	121.4	C9—C10—H10B	109.4
C1—C2—H2	121.3	H10A—C10—H10B	108.0
C2—C3—C4	122.6 (2)	C10—C11—C12	110.7 (2)
C2—C3—N1	117.7 (2)	C10—C11—H11A	109.5
C4—C3—N1	119.7 (2)	C12—C11—H11A	109.5
C3—C4—C5	119.1 (2)	C10—C11—H11B	109.5
C3—C4—H4	120.5	C12—C11—H11B	109.5
C5—C4—H4	120.5	H11A—C11—H11B	108.1
C4—C5—C6	120.4 (2)	C7—C12—C11	111.6 (2)
C4—C5—H5	119.8	C7—C12—H12A	109.3
C6—C5—H5	119.8	C11—C12—H12A	109.3
C5—C6—C1	118.2 (2)	C7—C12—H12B	109.3
C5—C6—N3	123.9 (2)	C11—C12—H12B	109.3
C1—C6—N3	117.6 (2)	H12A—C12—H12B	108.0
N4—C7—C12	108.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1^i	0.97	2.57	3.433 (4)	148
C9—H9B···O2^ii	0.97	2.56	3.506 (4)	165
C4—H4···O6^iii	0.93	2.60	3.344 (3)	138

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, −y+1/2, z−1/2; (iii) −x+1, y+1/2, −z+1/2.