N,N-Dicyclo-hexyl-3,5-dinitro-benzamide.

In the title compound, C(19)H(25)N(3)O(5), the benzene ring is not coplanar with the amide group [dihedral angle = 61.90 (5)°]. The cyclo-hexyl rings are in chair conformations. There is a strong inter-molecular inter-action between the C=O group of the amide group and the nitro group of an adjoining mol-ecule, with a short O⋯N distance of 2.7862 (17) Å. In the crystal, C-H⋯O inter-actions occur along the [100] direction.

Related literature

For background to the biological activity of N-substituted benzamides and their use in synthesis, see: Priya et al. (2005 ▶). For related structures and their use in mol­ecular recognition, see: Toda et al. (1987 ▶); Saeed et al. (2011 ▶, 2012 ▶). For puckering parameters, see Cremer & Pople (1975 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C19H25N3O5

M = 375.42

Triclinic,

a = 6.8187 (7) Å

b = 9.7877 (12) Å

c = 14.7423 (12) Å

α = 92.512 (8)°

β = 98.898 (8)°

γ = 99.704 (9)°

V = 955.67 (17) Å3

Z = 2

Cu Kα radiation

μ = 0.79 mm−1

T = 123 K

0.51 × 0.17 × 0.04 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011 ▶), based on expressions derived from Clark & Reid (1995 ▶)] T min = 0.690, T max = 0.969

6078 measured reflections

3811 independent reflections

3144 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.132

S = 1.03

3811 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038500/nk2179sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038500/nk2179Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038500/nk2179Isup3.cml

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

C19H25N3O5	Z = 2
Mr = 375.42	F(000) = 400
Triclinic, P1	Dx = 1.305 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.8187 (7) Å	Cell parameters from 2277 reflections
b = 9.7877 (12) Å	θ = 3.0–75.2°
c = 14.7423 (12) Å	µ = 0.79 mm−1
α = 92.512 (8)°	T = 123 K
β = 98.898 (8)°	`needle-plate`, colorless
γ = 99.704 (9)°	0.51 × 0.17 × 0.04 mm
V = 955.67 (17) Å3

Agilent Xcalibur Ruby Gemini diffractometer	3811 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3144 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 10.5081 pixels mm-1	θmax = 75.4°, θmin = 3.0°
ω scans	h = −8→7
Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011), based on expressions derived from Clark & Reid (1995)]	k = −10→12
Tmin = 0.690, Tmax = 0.969	l = −18→15
6078 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0695P)2 + 0.0476P] where P = (Fo2 + 2Fc2)/3
3811 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. Absorption correction: CrysAlis RED, (Agilent, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. (Clark & Reid, 1995).

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	0.23442 (17)	0.94242 (13)	0.55223 (8)	0.0308 (3)
O2	0.4677 (2)	0.98065 (14)	0.67312 (8)	0.0362 (3)
O3	1.03595 (18)	0.75165 (13)	0.69435 (7)	0.0325 (3)
O4	1.08761 (16)	0.63134 (13)	0.57626 (8)	0.0303 (3)
O5	0.29440 (16)	0.51429 (12)	0.34083 (7)	0.0274 (3)
N1	0.3957 (2)	0.92478 (14)	0.59620 (9)	0.0259 (3)
N2	0.98833 (19)	0.70201 (14)	0.61477 (8)	0.0252 (3)
N3	0.54384 (18)	0.61099 (13)	0.26430 (8)	0.0220 (3)
C1	0.5115 (2)	0.83290 (15)	0.55400 (10)	0.0234 (3)
C2	0.6958 (2)	0.81731 (16)	0.60284 (9)	0.0234 (3)
H2A	0.7478	0.8646	0.6615	0.028*
C3	0.7997 (2)	0.72959 (16)	0.56194 (10)	0.0226 (3)
C4	0.7312 (2)	0.66292 (16)	0.47469 (9)	0.0228 (3)
H4A	0.8090	0.6051	0.4479	0.027*
C5	0.5460 (2)	0.68296 (16)	0.42755 (9)	0.0227 (3)
C6	0.4320 (2)	0.76562 (16)	0.46813 (10)	0.0233 (3)
H6A	0.3025	0.7759	0.4377	0.028*
C7	0.4509 (2)	0.59667 (16)	0.33856 (9)	0.0222 (3)
C8	0.4805 (2)	0.50539 (16)	0.18488 (9)	0.0230 (3)
H8A	0.5724	0.5316	0.1394	0.028*
C9	0.5117 (2)	0.36144 (17)	0.21379 (10)	0.0291 (3)
H9A	0.4270	0.3328	0.2609	0.035*
H9B	0.6545	0.3654	0.2415	0.035*
C10	0.4561 (3)	0.25421 (18)	0.13107 (11)	0.0329 (4)
H10A	0.5498	0.2776	0.0868	0.040*
H10B	0.4701	0.1610	0.1519	0.040*
C11	0.2403 (3)	0.25131 (18)	0.08358 (11)	0.0338 (4)
H11A	0.2087	0.1835	0.0293	0.041*
H11B	0.1458	0.2211	0.1264	0.041*
C12	0.2126 (3)	0.39444 (18)	0.05318 (10)	0.0325 (4)
H12A	0.0709	0.3907	0.0237	0.039*
H12B	0.3004	0.4216	0.0070	0.039*
C13	0.2648 (2)	0.50401 (17)	0.13510 (10)	0.0270 (3)
H13A	0.2535	0.5969	0.1130	0.032*
H13B	0.1683	0.4825	0.1784	0.032*
C14	0.7089 (2)	0.72822 (15)	0.25786 (9)	0.0216 (3)
H14A	0.7252	0.7921	0.3144	0.026*
C15	0.6558 (2)	0.81222 (16)	0.17448 (9)	0.0236 (3)
H15A	0.6357	0.7516	0.1171	0.028*
H15B	0.5283	0.8461	0.1784	0.028*
C16	0.8253 (2)	0.93638 (17)	0.17186 (10)	0.0275 (3)
H16A	0.7932	0.9849	0.1154	0.033*
H16B	0.8334	1.0027	0.2255	0.033*
C17	1.0291 (2)	0.89085 (18)	0.17335 (11)	0.0294 (3)
H17A	1.1359	0.9739	0.1764	0.035*
H17B	1.0269	0.8340	0.1159	0.035*
C18	1.0770 (2)	0.80630 (17)	0.25612 (10)	0.0276 (3)
H18A	1.0916	0.8660	0.3136	0.033*
H18C	1.2067	0.7745	0.2542	0.033*
C19	0.9104 (2)	0.68002 (16)	0.25653 (10)	0.0251 (3)
H19C	0.9008	0.6170	0.2010	0.030*
H19A	0.9432	0.6283	0.3114	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0303 (6)	0.0312 (6)	0.0329 (6)	0.0102 (5)	0.0063 (4)	0.0034 (5)
O2	0.0422 (7)	0.0403 (7)	0.0264 (5)	0.0109 (5)	0.0059 (5)	−0.0091 (5)
O3	0.0332 (6)	0.0371 (6)	0.0230 (5)	0.0058 (5)	−0.0054 (4)	−0.0046 (5)
O4	0.0261 (5)	0.0339 (6)	0.0309 (5)	0.0080 (5)	0.0028 (4)	−0.0002 (5)
O5	0.0273 (5)	0.0304 (6)	0.0222 (5)	−0.0011 (4)	0.0046 (4)	0.0000 (4)
N1	0.0297 (6)	0.0251 (6)	0.0239 (6)	0.0046 (5)	0.0075 (5)	0.0031 (5)
N2	0.0251 (6)	0.0250 (6)	0.0236 (6)	0.0010 (5)	0.0018 (5)	0.0018 (5)
N3	0.0231 (6)	0.0238 (6)	0.0178 (5)	0.0020 (5)	0.0022 (4)	−0.0009 (4)
C1	0.0281 (7)	0.0222 (7)	0.0208 (6)	0.0032 (6)	0.0077 (5)	0.0030 (5)
C2	0.0281 (7)	0.0239 (7)	0.0171 (6)	0.0007 (5)	0.0048 (5)	0.0006 (5)
C3	0.0223 (6)	0.0241 (7)	0.0204 (6)	0.0009 (5)	0.0031 (5)	0.0031 (5)
C4	0.0248 (7)	0.0243 (7)	0.0195 (6)	0.0030 (5)	0.0065 (5)	0.0006 (5)
C5	0.0266 (7)	0.0248 (7)	0.0158 (6)	0.0009 (5)	0.0045 (5)	0.0024 (5)
C6	0.0241 (6)	0.0264 (7)	0.0192 (6)	0.0030 (5)	0.0033 (5)	0.0051 (5)
C7	0.0242 (6)	0.0230 (7)	0.0194 (6)	0.0055 (5)	0.0020 (5)	0.0017 (5)
C8	0.0272 (7)	0.0239 (7)	0.0167 (6)	0.0021 (5)	0.0035 (5)	−0.0013 (5)
C9	0.0344 (8)	0.0282 (8)	0.0234 (7)	0.0087 (6)	−0.0021 (6)	−0.0001 (6)
C10	0.0441 (9)	0.0260 (8)	0.0292 (8)	0.0103 (7)	0.0044 (7)	−0.0024 (6)
C11	0.0447 (9)	0.0268 (8)	0.0249 (7)	0.0002 (7)	−0.0009 (7)	−0.0044 (6)
C12	0.0403 (9)	0.0312 (8)	0.0213 (7)	0.0040 (7)	−0.0050 (6)	−0.0033 (6)
C13	0.0308 (7)	0.0273 (8)	0.0213 (7)	0.0073 (6)	−0.0017 (6)	−0.0021 (6)
C14	0.0242 (6)	0.0230 (7)	0.0169 (6)	0.0026 (5)	0.0032 (5)	0.0006 (5)
C15	0.0267 (7)	0.0250 (7)	0.0191 (6)	0.0053 (5)	0.0027 (5)	0.0021 (5)
C16	0.0323 (7)	0.0251 (7)	0.0245 (7)	0.0027 (6)	0.0045 (6)	0.0043 (6)
C17	0.0288 (7)	0.0309 (8)	0.0271 (7)	−0.0007 (6)	0.0065 (6)	0.0038 (6)
C18	0.0228 (7)	0.0316 (8)	0.0270 (7)	0.0023 (6)	0.0025 (5)	0.0032 (6)
C19	0.0235 (7)	0.0275 (7)	0.0244 (7)	0.0045 (6)	0.0042 (5)	0.0034 (5)

O1—N1	1.2300 (18)	C10—H10A	0.9900
O2—N1	1.2284 (18)	C10—H10B	0.9900
O3—N2	1.2235 (17)	C11—C12	1.522 (2)
O4—N2	1.2253 (18)	C11—H11A	0.9900
O5—C7	1.2299 (19)	C11—H11B	0.9900
N1—C1	1.470 (2)	C12—C13	1.536 (2)
N2—C3	1.4696 (19)	C12—H12A	0.9900
N3—C7	1.3486 (19)	C12—H12B	0.9900
N3—C14	1.4831 (18)	C13—H13A	0.9900
N3—C8	1.4874 (17)	C13—H13B	0.9900
C1—C2	1.384 (2)	C14—C19	1.528 (2)
C1—C6	1.387 (2)	C14—C15	1.5392 (19)
C2—C3	1.376 (2)	C14—H14A	1.0000
C2—H2A	0.9500	C15—C16	1.536 (2)
C3—C4	1.391 (2)	C15—H15A	0.9900
C4—C5	1.393 (2)	C15—H15B	0.9900
C4—H4A	0.9500	C16—C17	1.526 (2)
C5—C6	1.389 (2)	C16—H16A	0.9900
C5—C7	1.5199 (19)	C16—H16B	0.9900
C6—H6A	0.9500	C17—C18	1.529 (2)
C8—C9	1.529 (2)	C17—H17A	0.9900
C8—C13	1.536 (2)	C17—H17B	0.9900
C8—H8A	1.0000	C18—C19	1.532 (2)
C9—C10	1.531 (2)	C18—H18A	0.9900
C9—H9A	0.9900	C18—H18C	0.9900
C9—H9B	0.9900	C19—H19C	0.9900
C10—C11	1.523 (2)	C19—H19A	0.9900
O2—N1—O1	123.96 (14)	C12—C11—H11B	109.5
O2—N1—C1	117.72 (13)	C10—C11—H11B	109.5
O1—N1—C1	118.31 (13)	H11A—C11—H11B	108.1
O3—N2—O4	124.38 (13)	C11—C12—C13	111.33 (13)
O3—N2—C3	117.65 (13)	C11—C12—H12A	109.4
O4—N2—C3	117.97 (12)	C13—C12—H12A	109.4
C7—N3—C14	122.84 (12)	C11—C12—H12B	109.4
C7—N3—C8	119.34 (12)	C13—C12—H12B	109.4
C14—N3—C8	117.82 (11)	H12A—C12—H12B	108.0
C2—C1—C6	123.08 (15)	C8—C13—C12	110.00 (13)
C2—C1—N1	117.81 (13)	C8—C13—H13A	109.7
C6—C1—N1	119.12 (14)	C12—C13—H13A	109.7
C3—C2—C1	116.45 (13)	C8—C13—H13B	109.7
C3—C2—H2A	121.8	C12—C13—H13B	109.7
C1—C2—H2A	121.8	H13A—C13—H13B	108.2
C2—C3—C4	123.15 (14)	N3—C14—C19	112.10 (12)
C2—C3—N2	117.98 (13)	N3—C14—C15	111.61 (11)
C4—C3—N2	118.84 (14)	C19—C14—C15	111.05 (12)
C3—C4—C5	118.39 (14)	N3—C14—H14A	107.3
C3—C4—H4A	120.8	C19—C14—H14A	107.3
C5—C4—H4A	120.8	C15—C14—H14A	107.3
C6—C5—C4	120.26 (13)	C16—C15—C14	110.47 (12)
C6—C5—C7	118.74 (13)	C16—C15—H15A	109.6
C4—C5—C7	120.25 (14)	C14—C15—H15A	109.6
C1—C6—C5	118.57 (14)	C16—C15—H15B	109.6
C1—C6—H6A	120.7	C14—C15—H15B	109.6
C5—C6—H6A	120.7	H15A—C15—H15B	108.1
O5—C7—N3	124.41 (13)	C17—C16—C15	111.74 (13)
O5—C7—C5	116.40 (12)	C17—C16—H16A	109.3
N3—C7—C5	119.15 (12)	C15—C16—H16A	109.3
N3—C8—C9	110.96 (11)	C17—C16—H16B	109.3
N3—C8—C13	113.26 (12)	C15—C16—H16B	109.3
C9—C8—C13	111.99 (13)	H16A—C16—H16B	107.9
N3—C8—H8A	106.7	C16—C17—C18	110.80 (13)
C9—C8—H8A	106.7	C16—C17—H17A	109.5
C13—C8—H8A	106.7	C18—C17—H17A	109.5
C8—C9—C10	110.91 (12)	C16—C17—H17B	109.5
C8—C9—H9A	109.5	C18—C17—H17B	109.5
C10—C9—H9A	109.5	H17A—C17—H17B	108.1
C8—C9—H9B	109.5	C17—C18—C19	111.27 (12)
C10—C9—H9B	109.5	C17—C18—H18A	109.4
H9A—C9—H9B	108.0	C19—C18—H18A	109.4
C11—C10—C9	110.78 (14)	C17—C18—H18C	109.4
C11—C10—H10A	109.5	C19—C18—H18C	109.4
C9—C10—H10A	109.5	H18A—C18—H18C	108.0
C11—C10—H10B	109.5	C14—C19—C18	109.64 (13)
C9—C10—H10B	109.5	C14—C19—H19C	109.7
H10A—C10—H10B	108.1	C18—C19—H19C	109.7
C12—C11—C10	110.67 (14)	C14—C19—H19A	109.7
C12—C11—H11A	109.5	C18—C19—H19A	109.7
C10—C11—H11A	109.5	H19C—C19—H19A	108.2
O2—N1—C1—C2	−1.2 (2)	C6—C5—C7—N3	124.80 (15)
O1—N1—C1—C2	177.97 (13)	C4—C5—C7—N3	−65.11 (19)
O2—N1—C1—C6	178.46 (14)	C7—N3—C8—C9	−60.72 (17)
O1—N1—C1—C6	−2.4 (2)	C14—N3—C8—C9	119.11 (14)
C6—C1—C2—C3	−0.3 (2)	C7—N3—C8—C13	66.24 (17)
N1—C1—C2—C3	179.38 (12)	C14—N3—C8—C13	−113.94 (14)
C1—C2—C3—C4	2.5 (2)	N3—C8—C9—C10	−177.25 (12)
C1—C2—C3—N2	−175.35 (13)	C13—C8—C9—C10	55.10 (17)
O3—N2—C3—C2	4.5 (2)	C8—C9—C10—C11	−56.00 (18)
O4—N2—C3—C2	−175.30 (13)	C9—C10—C11—C12	57.49 (18)
O3—N2—C3—C4	−173.47 (13)	C10—C11—C12—C13	−57.87 (19)
O4—N2—C3—C4	6.7 (2)	N3—C8—C13—C12	178.94 (12)
C2—C3—C4—C5	−1.8 (2)	C9—C8—C13—C12	−54.65 (17)
N2—C3—C4—C5	176.03 (13)	C11—C12—C13—C8	55.91 (18)
C3—C4—C5—C6	−1.2 (2)	C7—N3—C14—C19	113.34 (15)
C3—C4—C5—C7	−171.14 (13)	C8—N3—C14—C19	−66.48 (16)
C2—C1—C6—C5	−2.6 (2)	C7—N3—C14—C15	−121.37 (14)
N1—C1—C6—C5	177.76 (13)	C8—N3—C14—C15	58.81 (16)
C4—C5—C6—C1	3.3 (2)	N3—C14—C15—C16	177.61 (12)
C7—C5—C6—C1	173.39 (13)	C19—C14—C15—C16	−56.51 (16)
C14—N3—C7—O5	168.10 (14)	C14—C15—C16—C17	54.76 (16)
C8—N3—C7—O5	−12.1 (2)	C15—C16—C17—C18	−54.88 (17)
C14—N3—C7—C5	−14.2 (2)	C16—C17—C18—C19	56.63 (18)
C8—N3—C7—C5	165.61 (13)	N3—C14—C19—C18	−176.37 (11)
C6—C5—C7—O5	−57.32 (19)	C15—C14—C19—C18	58.03 (15)
C4—C5—C7—O5	112.77 (16)	C17—C18—C19—C14	−58.10 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O5	0.99	2.46	3.050 (2)	118
C13—H13B···O5	0.99	2.40	3.0043 (18)	119
C4—H4A···O4i	0.95	2.56	3.418 (2)	151
C16—H16B···O3ii	0.99	2.58	3.468 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O4i	0.95	2.56	3.418 (2)	151
C16—H16B⋯O3ii	0.99	2.58	3.468 (2)	149

Symmetry codes: (i) ; (ii) .