N,N-Di­cyclo­hexyl­nitramine

Mol­ecules of the title compound, C₁₂H₂₂N₂O₂, are composed of an nitramine group substituted by two cyclo­hexane rings. The cyclo­hexane rings have chair conformations, with the exocyclic C—N bonds in axial orientations. In the crystal, C—H...O hydrogen bonds connect the mol­ecules into C(6) [-101] zigzag chains.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.084
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     --  N2      ..        6.0 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     --  N2      ..        5.1 s.u.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.530 Check

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           7 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis CCD (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

N-Cyclohexyl-N-nitrocyclohexanamine

Crystal data

C12H22N2O2	F(000) = 496
Mr = 226.31	Dx = 1.218 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.9136 (1) Å	Cell parameters from 8287 reflections
b = 19.1658 (4) Å	θ = 3.6–26.0°
c = 10.8946 (2) Å	µ = 0.08 mm^−1
β = 91.852 (2)°	T = 100 K
V = 1234.14 (4) Å^3	Plate, colourless
Z = 4	0.04 × 0.04 × 0.03 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer	1892 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm^-1	θmax = 26.0°, θmin = 3.6°
ω–scan	h = −7→7
8287 measured reflections	k = −23→23
2425 independent reflections	l = −13→10

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0401P)^2 + 0.1204P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2425 reflections	Δρmax = 0.18 e Å^−3
145 parameters	Δρmin = −0.15 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.72029 (16)	0.12483 (4)	0.64176 (8)	0.0372 (2)
O2	0.64140 (15)	0.23560 (5)	0.64377 (8)	0.0380 (2)
N1	0.83491 (16)	0.19259 (5)	0.49004 (9)	0.0257 (2)
N2	0.72928 (17)	0.18401 (5)	0.59711 (9)	0.0269 (2)
C1	0.94810 (19)	0.13124 (6)	0.43775 (10)	0.0229 (3)
H1A	0.8895	0.0901	0.4795	0.027*
C2	0.8906 (2)	0.12227 (6)	0.30137 (11)	0.0272 (3)
H2A	0.9519	0.1609	0.2556	0.033*
H2B	0.7277	0.1218	0.2877	0.033*
C3	0.9913 (2)	0.05376 (6)	0.25735 (12)	0.0332 (3)
H3A	0.9191	0.0151	0.2982	0.040*
H3B	0.9610	0.0489	0.1697	0.040*
C4	1.2452 (2)	0.05060 (7)	0.28348 (12)	0.0334 (3)
H4A	1.3010	0.0050	0.2606	0.040*
H4B	1.3194	0.0852	0.2337	0.040*
C5	1.3044 (2)	0.06395 (6)	0.41772 (12)	0.0324 (3)
H5A	1.4677	0.0657	0.4293	0.039*
H5B	1.2488	0.0257	0.4665	0.039*
C6	1.20285 (19)	0.13213 (6)	0.46228 (11)	0.0267 (3)
H6A	1.2356	0.1377	0.5495	0.032*
H6B	1.2693	0.1711	0.4197	0.032*
C7	0.87648 (19)	0.26368 (6)	0.44305 (11)	0.0238 (3)
H7A	0.9683	0.2572	0.3706	0.029*
C8	0.6611 (2)	0.30047 (6)	0.39599 (12)	0.0295 (3)
H8A	0.5820	0.2711	0.3361	0.035*
H8B	0.5617	0.3084	0.4637	0.035*
C9	0.7201 (2)	0.36990 (6)	0.33712 (12)	0.0316 (3)
H9A	0.8051	0.3614	0.2639	0.038*
H9B	0.5817	0.3940	0.3125	0.038*
C10	0.8586 (2)	0.41578 (6)	0.42459 (12)	0.0325 (3)
H10A	0.7687	0.4280	0.4943	0.039*
H10B	0.8988	0.4586	0.3831	0.039*
C11	1.0727 (2)	0.37853 (6)	0.46953 (12)	0.0319 (3)
H11A	1.1548	0.4081	0.5279	0.038*
H11B	1.1691	0.3703	0.4006	0.038*
C12	1.0191 (2)	0.30900 (6)	0.53055 (11)	0.0281 (3)
H12A	1.1588	0.2850	0.5529	0.034*
H12B	0.9374	0.3173	0.6049	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0500 (6)	0.0309 (5)	0.0315 (5)	0.0028 (4)	0.0135 (4)	0.0110 (4)
O2	0.0488 (6)	0.0336 (5)	0.0326 (5)	0.0083 (4)	0.0195 (4)	−0.0017 (4)
N1	0.0321 (6)	0.0234 (5)	0.0221 (5)	0.0019 (4)	0.0107 (4)	0.0028 (4)
N2	0.0291 (5)	0.0294 (6)	0.0224 (5)	0.0017 (4)	0.0055 (4)	0.0030 (4)
C1	0.0263 (6)	0.0199 (6)	0.0227 (6)	0.0002 (5)	0.0038 (5)	0.0010 (5)
C2	0.0249 (6)	0.0288 (7)	0.0277 (6)	−0.0029 (5)	−0.0031 (5)	−0.0019 (5)
C3	0.0415 (8)	0.0301 (7)	0.0283 (7)	−0.0070 (6)	0.0042 (6)	−0.0075 (5)
C4	0.0401 (7)	0.0249 (7)	0.0359 (7)	0.0043 (6)	0.0120 (6)	−0.0001 (5)
C5	0.0280 (7)	0.0325 (7)	0.0370 (7)	0.0061 (5)	0.0040 (5)	0.0077 (6)
C6	0.0277 (7)	0.0289 (6)	0.0232 (6)	0.0001 (5)	−0.0034 (5)	0.0019 (5)
C7	0.0283 (6)	0.0208 (6)	0.0227 (6)	0.0008 (5)	0.0055 (5)	0.0015 (5)
C8	0.0273 (6)	0.0295 (7)	0.0315 (7)	0.0001 (5)	−0.0007 (5)	0.0029 (5)
C9	0.0317 (7)	0.0322 (7)	0.0308 (7)	0.0048 (5)	0.0007 (5)	0.0082 (5)
C10	0.0393 (7)	0.0235 (6)	0.0351 (7)	0.0029 (6)	0.0065 (6)	0.0018 (5)
C11	0.0322 (7)	0.0290 (7)	0.0345 (7)	−0.0045 (5)	−0.0006 (5)	−0.0023 (5)
C12	0.0308 (6)	0.0260 (6)	0.0274 (6)	0.0037 (5)	−0.0016 (5)	−0.0014 (5)

Geometric parameters (Å, º)

O1—N2	1.2360 (12)	C6—H6A	0.9700
O2—N2	1.2342 (12)	C6—H6B	0.9700
N1—N2	1.3509 (13)	C7—C12	1.5238 (16)
N1—C1	1.4764 (14)	C7—C8	1.5297 (16)
N1—C7	1.4789 (14)	C7—H7A	0.9800
C1—C6	1.5216 (16)	C8—C9	1.5225 (16)
C1—C2	1.5231 (16)	C8—H8A	0.9700
C1—H1A	0.9800	C8—H8B	0.9700
C2—C3	1.5255 (17)	C9—C10	1.5172 (18)
C2—H2A	0.9700	C9—H9A	0.9700
C2—H2B	0.9700	C9—H9B	0.9700
C3—C4	1.5202 (18)	C10—C11	1.5206 (18)
C3—H3A	0.9700	C10—H10A	0.9700
C3—H3B	0.9700	C10—H10B	0.9700
C4—C5	1.5145 (18)	C11—C12	1.5271 (17)
C4—H4A	0.9700	C11—H11A	0.9700
C4—H4B	0.9700	C11—H11B	0.9700
C5—C6	1.5240 (16)	C12—H12A	0.9700
C5—H5A	0.9700	C12—H12B	0.9700
C5—H5B	0.9700
N2—N1—C1	117.66 (9)	C1—C6—H6B	109.8
N2—N1—C7	119.84 (9)	C5—C6—H6B	109.8
C1—N1—C7	121.18 (9)	H6A—C6—H6B	108.2
O2—N2—O1	123.29 (9)	N1—C7—C12	113.79 (9)
O2—N2—N1	118.09 (9)	N1—C7—C8	113.25 (9)
O1—N2—N1	118.59 (9)	C12—C7—C8	112.64 (10)
N1—C1—C6	112.45 (9)	N1—C7—H7A	105.4
N1—C1—C2	112.12 (9)	C12—C7—H7A	105.4
C6—C1—C2	111.17 (9)	C8—C7—H7A	105.4
N1—C1—H1A	106.9	C9—C8—C7	110.15 (10)
C6—C1—H1A	106.9	C9—C8—H8A	109.6
C2—C1—H1A	106.9	C7—C8—H8A	109.6
C1—C2—C3	109.07 (10)	C9—C8—H8B	109.6
C1—C2—H2A	109.9	C7—C8—H8B	109.6
C3—C2—H2A	109.9	H8A—C8—H8B	108.1
C1—C2—H2B	109.9	C10—C9—C8	111.61 (10)
C3—C2—H2B	109.9	C10—C9—H9A	109.3
H2A—C2—H2B	108.3	C8—C9—H9A	109.3
C4—C3—C2	111.63 (10)	C10—C9—H9B	109.3
C4—C3—H3A	109.3	C8—C9—H9B	109.3
C2—C3—H3A	109.3	H9A—C9—H9B	108.0
C4—C3—H3B	109.3	C9—C10—C11	110.93 (10)
C2—C3—H3B	109.3	C9—C10—H10A	109.5
H3A—C3—H3B	108.0	C11—C10—H10A	109.5
C5—C4—C3	111.73 (10)	C9—C10—H10B	109.5
C5—C4—H4A	109.3	C11—C10—H10B	109.5
C3—C4—H4A	109.3	H10A—C10—H10B	108.0
C5—C4—H4B	109.3	C10—C11—C12	111.54 (10)
C3—C4—H4B	109.3	C10—C11—H11A	109.3
H4A—C4—H4B	107.9	C12—C11—H11A	109.3
C4—C5—C6	111.79 (10)	C10—C11—H11B	109.3
C4—C5—H5A	109.3	C12—C11—H11B	109.3
C6—C5—H5A	109.3	H11A—C11—H11B	108.0
C4—C5—H5B	109.3	C7—C12—C11	110.10 (10)
C6—C5—H5B	109.3	C7—C12—H12A	109.6
H5A—C5—H5B	107.9	C11—C12—H12A	109.6
C1—C6—C5	109.42 (10)	C7—C12—H12B	109.6
C1—C6—H6A	109.8	C11—C12—H12B	109.6
C5—C6—H6A	109.8	H12A—C12—H12B	108.2
C1—N1—N2—O2	177.38 (10)	C2—C1—C6—C5	−59.24 (12)
C7—N1—N2—O2	10.30 (16)	C4—C5—C6—C1	55.84 (13)
C1—N1—N2—O1	−4.46 (15)	N2—N1—C7—C12	58.93 (14)
C7—N1—N2—O1	−171.54 (10)	C1—N1—C7—C12	−107.69 (12)
N2—N1—C1—C6	−100.93 (12)	N2—N1—C7—C8	−71.41 (13)
C7—N1—C1—C6	65.97 (13)	C1—N1—C7—C8	121.98 (11)
N2—N1—C1—C2	132.93 (11)	N1—C7—C8—C9	−174.08 (9)
C7—N1—C1—C2	−60.17 (13)	C12—C7—C8—C9	55.01 (13)
N1—C1—C2—C3	−173.68 (9)	C7—C8—C9—C10	−55.28 (13)
C6—C1—C2—C3	59.49 (12)	C8—C9—C10—C11	56.61 (14)
C1—C2—C3—C4	−56.37 (13)	C9—C10—C11—C12	−56.53 (14)
C2—C3—C4—C5	54.20 (14)	N1—C7—C12—C11	174.42 (9)
C3—C4—C5—C6	−53.84 (14)	C8—C7—C12—C11	−54.94 (13)
N1—C1—C6—C5	174.10 (9)	C10—C11—C12—C7	55.23 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2^i	0.97	2.60	3.5684 (14)	176

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.