1,4-Di-n-hept-yloxy-2,5-dinitro-benzene.

The complete molecule of the title compound, C(20)H(32)N(2)O(6), is generated by crystallographic inversion symmetry. The two mutually trans nitro substituents are hence in fully eclipsed conformation and also twisted by 43.2 (2)° with respect to the phenyl ring plane. The benzene-connected portions of the alk-oxy substituents lie almost coplanar with the ring [C-O-C-C torsion angle = 2.0 (2)°]. In the crystal, weak C-H⋯O interactions link the molecules.

Related literature

For general background to the synthesis, see: Baker et al. (2008 ▶); Fisher et al. (1975 ▶); Flader et al. (2000 ▶); Hammershøj et al. (2006 ▶); Kawai et al. (1959 ▶). For a related structure, see: Voss et al. (2003 ▶).

Experimental

Crystal data

C20H32N2O6

M = 396.48

Monoclinic,

a = 13.988 (2) Å

b = 7.9454 (13) Å

c = 9.5344 (15) Å

β = 99.786 (3)°

V = 1044.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.40 × 0.40 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

5776 measured reflections

2110 independent reflections

1733 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.03

2110 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL .

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680905123X/pv2242sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905123X/pv2242Isup2.hkl

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

C20H32N2O6	F(000) = 428
Mr = 396.48	Dx = 1.261 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 776 reflections
a = 13.988 (2) Å	θ = 3.0–26.2°
b = 7.9454 (13) Å	µ = 0.09 mm−1
c = 9.5344 (15) Å	T = 100 K
β = 99.786 (3)°	Block, yellow
V = 1044.3 (3) Å3	0.40 × 0.40 × 0.25 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	1733 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 26.3°, θmin = 3.0°
phi and ω scans	h = −15→17
5776 measured reflections	k = −9→9
2110 independent reflections	l = −8→11

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.0454P] where P = (Fo2 + 2Fc2)/3
2110 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. Characterization data for 1,4-di(n-heptoxy)benzene. Found: C 78.76, H 11.14%. Calculated for C20H34O2: C 78.38, H, 11.18%. 1H NMR (300 MHz, CDCl3): 6.82 (4H, s, C6H4), 3.89 (4H, t, J = 6.6 Hz, 2OCH2), 1.75 (4H, quintet, J = 6.7 Hz, 2CH2), 1.50-1.18 (16H, m, 8CH2), 0.89 (6H, t, J = 6.8 Hz, 2CH3).Characterization data for 1,4-di(n-heptoxy)-2,5-dinitrobenzene (I). Melting point = 387-389 K. Found: C 60.81, H 8.29, N 6.94%. Calculated for C20H32N2O6: C 60.59, H 8.14, N 7.07%. 1H NMR (400 MHz, CDCl3): 7.51 (2H, s, C6H2), 4.08 (4H, t, J = 6.5 Hz, 2OCH2), 1.83 (4H, quintet, J = 6.6 Hz, 2CH2), 1.50-1.25 (16H, m, 8CH2), 0.89 (6H, t, J = 6.7 Hz, 2CH3). +Electrospray MS: m/z = 419.2 [M + Na]+, 815.8 [2M + Na]+. (λmax = 378 nm, ε = 5000 M-1 dm3 in dichloromethane). ν(NO2) = 1531 and 1352 cm-1.Characterization data for 1,4-di(n-heptoxy)-2,3-dinitrobenzene. Melting point = 318-319 K. Found: C 60.66, H 8.56, N 7.09%. Calculated for C20H32N2O6: C 60.59, H 8.14, N 7.07%. 1H NMR (400 MHz, CDCl3): 7.15 (2H, s, C6H2), 4.05 (4H, t, J = 6.5 Hz, 2OCH2), 1.76 (4H, quintet, J = 6.5 Hz, 2CH2), 1.45-1.25 (16H, m, 8CH2), 0.89 (6H, t, J = 6.7 Hz, 2CH3). (λmax = 365 nm, ε = 2300 M-1 dm3 in dichloromethane). ν(NO2) = 1537 and 1358 cm-1.

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.

	x	y	z	Uiso*/Ueq
O1	0.60328 (6)	−0.29610 (10)	0.79050 (10)	0.0209 (2)
O2	0.58901 (6)	−0.06141 (10)	0.67325 (9)	0.0233 (2)
O3	0.63728 (6)	0.17278 (10)	0.87825 (9)	0.0194 (2)
N1	0.58118 (7)	−0.14678 (12)	0.77792 (11)	0.0158 (2)
C1	0.54045 (8)	−0.06789 (14)	0.89396 (12)	0.0146 (3)
C2	0.56913 (8)	0.09431 (15)	0.94007 (12)	0.0153 (3)
C3	0.52640 (8)	0.16163 (14)	1.04846 (13)	0.0156 (3)
H3	0.5431	0.2718	1.0830	0.019*
C4	0.66991 (9)	0.33643 (14)	0.93230 (13)	0.0179 (3)
H4A	0.6913	0.3318	1.0367	0.022*
H4B	0.6168	0.4198	0.9110	0.022*
C5	0.75354 (8)	0.38479 (15)	0.85918 (13)	0.0187 (3)
H5A	0.7716	0.5033	0.8825	0.022*
H5B	0.7324	0.3770	0.7549	0.022*
C6	0.84229 (9)	0.27363 (16)	0.90244 (15)	0.0226 (3)
H6A	0.8267	0.1586	0.8657	0.027*
H6B	0.8565	0.2669	1.0076	0.027*
C7	0.93312 (9)	0.33431 (16)	0.84913 (14)	0.0217 (3)
H7A	0.9219	0.3296	0.7439	0.026*
H7B	0.9457	0.4531	0.8779	0.026*
C8	1.02172 (9)	0.22911 (16)	0.90717 (15)	0.0236 (3)
H8A	1.0301	0.2290	1.0124	0.028*
H8B	1.0095	0.1116	0.8746	0.028*
C9	1.11579 (9)	0.28829 (18)	0.86375 (15)	0.0263 (3)
H9A	1.1257	0.4087	0.8887	0.032*
H9B	1.1104	0.2779	0.7592	0.032*
C10	1.20347 (10)	0.18840 (18)	0.93540 (16)	0.0292 (3)
H10A	1.2101	0.2003	1.0389	0.044*
H10B	1.2620	0.2312	0.9039	0.044*
H10C	1.1947	0.0694	0.9095	0.044*

	U11	U22	U33	U12	U13	U23
O1	0.0233 (5)	0.0140 (5)	0.0262 (5)	0.0037 (3)	0.0066 (4)	0.0002 (4)
O2	0.0337 (5)	0.0197 (5)	0.0184 (5)	−0.0009 (4)	0.0104 (4)	0.0022 (4)
O3	0.0213 (5)	0.0162 (4)	0.0226 (5)	−0.0066 (3)	0.0095 (4)	−0.0030 (4)
N1	0.0154 (5)	0.0146 (5)	0.0175 (5)	−0.0010 (4)	0.0030 (4)	−0.0002 (4)
C1	0.0152 (6)	0.0152 (6)	0.0133 (6)	0.0025 (5)	0.0021 (5)	0.0008 (5)
C2	0.0139 (6)	0.0155 (6)	0.0161 (6)	−0.0002 (5)	0.0016 (5)	0.0030 (5)
C3	0.0165 (6)	0.0125 (6)	0.0167 (6)	−0.0002 (4)	−0.0002 (5)	0.0005 (5)
C4	0.0201 (6)	0.0136 (6)	0.0200 (6)	−0.0031 (5)	0.0032 (5)	−0.0013 (5)
C5	0.0196 (6)	0.0166 (6)	0.0200 (6)	−0.0042 (5)	0.0038 (5)	0.0010 (5)
C6	0.0214 (7)	0.0212 (7)	0.0263 (7)	−0.0012 (5)	0.0069 (6)	0.0033 (5)
C7	0.0209 (7)	0.0252 (7)	0.0191 (7)	−0.0031 (5)	0.0041 (5)	0.0003 (5)
C8	0.0219 (7)	0.0253 (7)	0.0244 (7)	−0.0018 (5)	0.0060 (6)	−0.0024 (6)
C9	0.0214 (7)	0.0366 (8)	0.0215 (7)	−0.0039 (6)	0.0050 (6)	−0.0019 (6)
C10	0.0220 (7)	0.0349 (8)	0.0319 (8)	−0.0012 (6)	0.0079 (6)	−0.0063 (6)

O1—N1	1.2268 (12)	C6—C7	1.5247 (16)
O2—N1	1.2269 (12)	C6—H6A	0.9900
O3—C2	1.3549 (13)	C6—H6B	0.9900
O3—C4	1.4438 (14)	C7—C8	1.5191 (18)
N1—C1	1.4682 (14)	C7—H7A	0.9900
C1—C3i	1.3803 (16)	C7—H7B	0.9900
C1—C2	1.3983 (16)	C8—C9	1.5196 (17)
C2—C3	1.3862 (16)	C8—H8A	0.9900
C3—C1i	1.3804 (16)	C8—H8B	0.9900
C3—H3	0.9500	C9—C10	1.5218 (19)
C4—C5	1.5097 (16)	C9—H9A	0.9900
C4—H4A	0.9900	C9—H9B	0.9900
C4—H4B	0.9900	C10—H10A	0.9800
C5—C6	1.5223 (17)	C10—H10B	0.9800
C5—H5A	0.9900	C10—H10C	0.9800
C5—H5B	0.9900
C2—O3—C4	117.53 (9)	C5—C6—H6B	108.7
O2—N1—O1	123.94 (10)	C7—C6—H6B	108.7
O2—N1—C1	118.47 (9)	H6A—C6—H6B	107.6
O1—N1—C1	117.57 (9)	C8—C7—C6	112.28 (10)
C3i—C1—C2	123.36 (10)	C8—C7—H7A	109.1
C3i—C1—N1	116.43 (10)	C6—C7—H7A	109.1
C2—C1—N1	120.21 (10)	C8—C7—H7B	109.1
O3—C2—C3	124.83 (11)	C6—C7—H7B	109.1
O3—C2—C1	118.22 (10)	H7A—C7—H7B	107.9
C3—C2—C1	116.94 (10)	C9—C8—C7	114.90 (11)
C1i—C3—C2	119.70 (11)	C9—C8—H8A	108.5
C1i—C3—H3	120.1	C7—C8—H8A	108.5
C2—C3—H3	120.1	C9—C8—H8B	108.5
O3—C4—C5	106.69 (9)	C7—C8—H8B	108.5
O3—C4—H4A	110.4	H8A—C8—H8B	107.5
C5—C4—H4A	110.4	C8—C9—C10	112.67 (12)
O3—C4—H4B	110.4	C8—C9—H9A	109.1
C5—C4—H4B	110.4	C10—C9—H9A	109.1
H4A—C4—H4B	108.6	C8—C9—H9B	109.1
C4—C5—C6	112.80 (10)	C10—C9—H9B	109.1
C4—C5—H5A	109.0	H9A—C9—H9B	107.8
C6—C5—H5A	109.0	C9—C10—H10A	109.5
C4—C5—H5B	109.0	C9—C10—H10B	109.5
C6—C5—H5B	109.0	H10A—C10—H10B	109.5
H5A—C5—H5B	107.8	C9—C10—H10C	109.5
C5—C6—C7	114.44 (10)	H10A—C10—H10C	109.5
C5—C6—H6A	108.7	H10B—C10—H10C	109.5
C7—C6—H6A	108.7
O2—N1—C1—C3i	136.39 (11)	N1—C1—C2—C3	178.96 (10)
O1—N1—C1—C3i	−41.95 (14)	O3—C2—C3—C1i	−178.21 (11)
O2—N1—C1—C2	−43.17 (15)	C1—C2—C3—C1i	0.53 (18)
O1—N1—C1—C2	138.49 (11)	C2—O3—C4—C5	172.90 (10)
C4—O3—C2—C3	2.00 (17)	O3—C4—C5—C6	−67.13 (13)
C4—O3—C2—C1	−176.73 (10)	C4—C5—C6—C7	−171.07 (11)
C3i—C1—C2—O3	178.27 (11)	C5—C6—C7—C8	174.35 (11)
N1—C1—C2—O3	−2.21 (16)	C6—C7—C8—C9	−177.18 (11)
C3i—C1—C2—C3	−0.56 (19)	C7—C8—C9—C10	174.81 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ii	0.95	2.50	3.4525 (15)	179
C4—H4B···O1iii	0.99	2.53	3.2852 (15)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.50	3.4525 (15)	179
C4—H4B⋯O1ii	0.99	2.53	3.2852 (15)	133

Symmetry codes: (i) ; (ii) .