organic compounds
N,N-Dicyclohexyl-4-nitrobenzamide
aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and dNational Engineering & Scientific Commission, PO Box 2801, Islamabad, Pakistan
*Correspondence e-mail: sohail262001@yahoo.com
The title compound, C19H26N2O3, crystallizes with two independent molecules in the which differ in the twist of the phenyl rings with respect to the plane of the amide group [the C—C—C—O torsion angles are 121.5 (3) and −119.6 (3)° in the two molecules. Both cyclohexane rings adopt chair conformations. In the crystal, weak C—H⋯O interactions occur. The crystal studied was a non-merohedral twin with a minor component of 4.8 (1)%.
Related literature
For background to N-substituted benzamides, see Priya et al. (2005). For see: Cremer & Pople, (1975). For related structures, see: Toda et al. (1987); Saeed et al. (2011).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; 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.
Supporting information
10.1107/S1600536812035660/ng5286sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812035660/ng5286Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812035660/ng5286Isup3.cml
To a 250 ml round flask fitted with a condenser was added dicyclohexyl amine (0.1 mol), dichloromethane (15 ml) and triethylamine (0.5 ml. 4-Nitrobenzoyl chloride (0.1 mol) was added. The reaction mixture was stirred at room temperature for 1 h and then refluxed for 2 h. The product precipitated as a colorless powder, which was washed three times with water and dichloromethane. Recrystallization from ethyl acetate produced the crystals of the title compound.
The
is a non-merohedral twin with the in the reciprocal matrix of -1, 0, 0: 0, -1, 0: 0, -1, 1 and the twin component ratio of 0.048 (1)/0.952 (1)/0.048. In the the HKLF 4 reflection file format in SHELXL was used.All H atoms were placed in calculated positions and then refined using the riding model approximation with atom-H lengths of 0.95 Å (CH) or 0.99 Å (CH2). Isotropic displacement parameters for these atoms were set to 1.2 (CH or CH2) times Ueq of the parent atom.
Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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 (Sheldrick, 2008).Fig. 1. Molecular structure of molecule A in (I) showing the atom labeling scheme and 30% probability displacement ellipsoids. Fig. 2. Molecular structure of molecule B in (I) showing the atom labeling scheme and 30% probability displacement ellipsoids. |
C19H26N2O3 | Z = 4 |
Mr = 330.42 | F(000) = 712 |
Triclinic, P1 | Dx = 1.267 Mg m−3 |
a = 6.1874 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 10.7109 (4) Å | Cell parameters from 6557 reflections |
c = 26.8188 (11) Å | θ = 3.4–75.4° |
α = 79.128 (4)° | µ = 0.69 mm−1 |
β = 89.027 (4)° | T = 123 K |
γ = 82.883 (3)° | Plate, colorless |
V = 1731.97 (13) Å3 | 0.29 × 0.26 × 0.07 mm |
Agilent Xcalibur Ruby Gemini diffractometer | 6952 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 6374 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 75.6°, θmin = 3.4° |
ω scans | h = −5→7 |
Absorption correction: analytical (Clark & Reid, 1995) | k = −13→11 |
Tmin = 0.823, Tmax = 0.950 | l = −33→33 |
12453 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)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.239 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.1113P)2 + 3.0338P] where P = (Fo2 + 2Fc2)/3 |
6952 reflections | (Δ/σ)max < 0.001 |
434 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C19H26N2O3 | γ = 82.883 (3)° |
Mr = 330.42 | V = 1731.97 (13) Å3 |
Triclinic, P1 | Z = 4 |
a = 6.1874 (3) Å | Cu Kα radiation |
b = 10.7109 (4) Å | µ = 0.69 mm−1 |
c = 26.8188 (11) Å | T = 123 K |
α = 79.128 (4)° | 0.29 × 0.26 × 0.07 mm |
β = 89.027 (4)° |
Agilent Xcalibur Ruby Gemini diffractometer | 6952 independent reflections |
Absorption correction: analytical (Clark & Reid, 1995) | 6374 reflections with I > 2σ(I) |
Tmin = 0.823, Tmax = 0.950 | Rint = 0.028 |
12453 measured reflections |
R[F2 > 2σ(F2)] = 0.080 | 0 restraints |
wR(F2) = 0.239 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.41 e Å−3 |
6952 reflections | Δρmin = −0.29 e Å−3 |
434 parameters |
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 | ||
O1A | 1.2037 (5) | 0.5044 (3) | 1.08793 (12) | 0.0488 (7) | |
O2A | 0.9117 (5) | 0.4171 (2) | 1.08150 (10) | 0.0412 (6) | |
O3A | 0.6696 (4) | 1.0644 (2) | 0.95462 (9) | 0.0300 (5) | |
O1B | 0.3898 (5) | −0.0077 (3) | 0.41690 (10) | 0.0426 (6) | |
O2B | 0.6849 (5) | 0.0824 (3) | 0.40932 (11) | 0.0488 (7) | |
O3B | 0.1784 (4) | 0.5172 (2) | 0.54297 (9) | 0.0295 (5) | |
N1A | 1.0181 (5) | 0.5061 (3) | 1.07197 (11) | 0.0324 (6) | |
N2A | 0.5886 (4) | 0.9656 (2) | 0.89045 (10) | 0.0241 (5) | |
N1B | 0.5025 (5) | 0.0694 (3) | 0.42687 (10) | 0.0322 (6) | |
N2B | 0.1038 (4) | 0.3626 (2) | 0.60959 (10) | 0.0235 (5) | |
C1A | 0.9244 (5) | 0.6242 (3) | 1.03726 (11) | 0.0268 (6) | |
C2A | 0.7117 (6) | 0.6306 (3) | 1.01945 (12) | 0.0289 (7) | |
H2AA | 0.6273 | 0.5621 | 1.0300 | 0.035* | |
C3A | 0.6276 (5) | 0.7404 (3) | 0.98588 (12) | 0.0276 (6) | |
H3AA | 0.4837 | 0.7472 | 0.9729 | 0.033* | |
C4A | 0.7519 (5) | 0.8398 (3) | 0.97115 (11) | 0.0241 (6) | |
C5A | 0.9626 (5) | 0.8314 (3) | 0.99050 (12) | 0.0257 (6) | |
H5AA | 1.0470 | 0.9001 | 0.9806 | 0.031* | |
C6A | 1.0485 (5) | 0.7220 (3) | 1.02437 (12) | 0.0283 (7) | |
H6AA | 1.1907 | 0.7157 | 1.0382 | 0.034* | |
C7A | 0.6645 (5) | 0.9660 (3) | 0.93753 (12) | 0.0246 (6) | |
C8A | 0.5043 (5) | 1.0884 (3) | 0.85731 (11) | 0.0246 (6) | |
H8AA | 0.4601 | 1.0661 | 0.8247 | 0.030* | |
C9A | 0.2981 (5) | 1.1545 (3) | 0.87833 (12) | 0.0283 (7) | |
H9AA | 0.3326 | 1.1802 | 0.9106 | 0.034* | |
H9AB | 0.1871 | 1.0945 | 0.8853 | 0.034* | |
C10A | 0.2085 (6) | 1.2733 (3) | 0.83935 (14) | 0.0327 (7) | |
H10A | 0.1599 | 1.2460 | 0.8085 | 0.039* | |
H10B | 0.0804 | 1.3188 | 0.8538 | 0.039* | |
C11A | 0.3790 (7) | 1.3642 (3) | 0.82482 (16) | 0.0416 (9) | |
H11A | 0.4159 | 1.3989 | 0.8549 | 0.050* | |
H11B | 0.3183 | 1.4370 | 0.7984 | 0.050* | |
C12A | 0.5854 (6) | 1.2968 (3) | 0.80490 (15) | 0.0371 (8) | |
H12A | 0.6962 | 1.3569 | 0.7978 | 0.045* | |
H12B | 0.5519 | 1.2704 | 0.7727 | 0.045* | |
C13A | 0.6769 (5) | 1.1789 (3) | 0.84358 (13) | 0.0306 (7) | |
H13A | 0.8054 | 1.1338 | 0.8291 | 0.037* | |
H13B | 0.7243 | 1.2059 | 0.8746 | 0.037* | |
C14A | 0.6076 (5) | 0.8494 (3) | 0.86733 (11) | 0.0222 (6) | |
H14A | 0.6707 | 0.7754 | 0.8936 | 0.027* | |
C15A | 0.7626 (5) | 0.8599 (3) | 0.82207 (11) | 0.0251 (6) | |
H15A | 0.9081 | 0.8736 | 0.8332 | 0.030* | |
H15B | 0.7074 | 0.9344 | 0.7957 | 0.030* | |
C16A | 0.7815 (5) | 0.7375 (3) | 0.79970 (12) | 0.0278 (6) | |
H16A | 0.8781 | 0.7467 | 0.7698 | 0.033* | |
H16B | 0.8473 | 0.6641 | 0.8252 | 0.033* | |
C17A | 0.5575 (6) | 0.7111 (3) | 0.78393 (13) | 0.0307 (7) | |
H17A | 0.4961 | 0.7815 | 0.7566 | 0.037* | |
H17B | 0.5725 | 0.6304 | 0.7706 | 0.037* | |
C18A | 0.4038 (5) | 0.7004 (3) | 0.82904 (12) | 0.0281 (6) | |
H18A | 0.4591 | 0.6252 | 0.8551 | 0.034* | |
H18B | 0.2583 | 0.6867 | 0.8178 | 0.034* | |
C19A | 0.3824 (5) | 0.8210 (3) | 0.85253 (12) | 0.0256 (6) | |
H19A | 0.2894 | 0.8088 | 0.8830 | 0.031* | |
H19B | 0.3118 | 0.8948 | 0.8278 | 0.031* | |
C1B | 0.4191 (6) | 0.1522 (3) | 0.46324 (11) | 0.0277 (7) | |
C2B | 0.2093 (6) | 0.1422 (3) | 0.48212 (12) | 0.0279 (6) | |
H2BA | 0.1217 | 0.0842 | 0.4721 | 0.033* | |
C3B | 0.1331 (5) | 0.2205 (3) | 0.51624 (11) | 0.0266 (6) | |
H3BA | −0.0081 | 0.2151 | 0.5304 | 0.032* | |
C4B | 0.2611 (5) | 0.3060 (3) | 0.52976 (11) | 0.0234 (6) | |
C5B | 0.4682 (5) | 0.3148 (3) | 0.50942 (11) | 0.0261 (6) | |
H5BA | 0.5549 | 0.3742 | 0.5186 | 0.031* | |
C6B | 0.5487 (5) | 0.2367 (3) | 0.47565 (12) | 0.0279 (6) | |
H6BA | 0.6900 | 0.2418 | 0.4616 | 0.033* | |
C7B | 0.1765 (5) | 0.4039 (3) | 0.56197 (11) | 0.0241 (6) | |
C8B | 0.0134 (5) | 0.4579 (3) | 0.64028 (11) | 0.0246 (6) | |
H8BA | −0.0280 | 0.4079 | 0.6737 | 0.030* | |
C9B | 0.1805 (5) | 0.5419 (3) | 0.65189 (13) | 0.0289 (7) | |
H9BA | 0.2298 | 0.5919 | 0.6198 | 0.035* | |
H9BB | 0.3088 | 0.4870 | 0.6690 | 0.035* | |
C10B | 0.0831 (6) | 0.6335 (3) | 0.68602 (13) | 0.0319 (7) | |
H10C | 0.1907 | 0.6911 | 0.6912 | 0.038* | |
H10D | 0.0489 | 0.5838 | 0.7196 | 0.038* | |
C11B | −0.1255 (6) | 0.7136 (3) | 0.66192 (13) | 0.0300 (7) | |
H11C | −0.1895 | 0.7700 | 0.6850 | 0.036* | |
H11D | −0.0891 | 0.7685 | 0.6296 | 0.036* | |
C12B | −0.2904 (5) | 0.6276 (3) | 0.65174 (12) | 0.0288 (7) | |
H12C | −0.4223 | 0.6811 | 0.6358 | 0.035* | |
H12D | −0.3337 | 0.5768 | 0.6843 | 0.035* | |
C13B | −0.1973 (5) | 0.5371 (3) | 0.61686 (12) | 0.0262 (6) | |
H13C | −0.1660 | 0.5872 | 0.5831 | 0.031* | |
H13D | −0.3051 | 0.4791 | 0.6122 | 0.031* | |
C14B | 0.1299 (5) | 0.2268 (3) | 0.63518 (11) | 0.0232 (6) | |
H14B | 0.1956 | 0.1748 | 0.6102 | 0.028* | |
C15B | −0.0898 (5) | 0.1806 (3) | 0.65121 (12) | 0.0262 (6) | |
H15C | −0.1845 | 0.1916 | 0.6209 | 0.031* | |
H15D | −0.1624 | 0.2333 | 0.6747 | 0.031* | |
C16B | −0.0599 (5) | 0.0395 (3) | 0.67733 (13) | 0.0290 (7) | |
H16C | −0.2029 | 0.0133 | 0.6891 | 0.035* | |
H16D | −0.0016 | −0.0140 | 0.6527 | 0.035* | |
C17B | 0.0960 (6) | 0.0174 (3) | 0.72263 (13) | 0.0322 (7) | |
H17C | 0.0320 | 0.0652 | 0.7486 | 0.039* | |
H17D | 0.1173 | −0.0748 | 0.7380 | 0.039* | |
C18B | 0.3159 (5) | 0.0618 (3) | 0.70600 (12) | 0.0291 (7) | |
H18C | 0.3846 | 0.0099 | 0.6818 | 0.035* | |
H18E | 0.4133 | 0.0488 | 0.7359 | 0.035* | |
C19B | 0.2872 (5) | 0.2034 (3) | 0.68080 (12) | 0.0260 (6) | |
H19E | 0.4303 | 0.2298 | 0.6692 | 0.031* | |
H19C | 0.2291 | 0.2560 | 0.7058 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0452 (16) | 0.0435 (15) | 0.0500 (17) | 0.0052 (12) | −0.0178 (13) | 0.0058 (12) |
O2A | 0.0485 (15) | 0.0328 (13) | 0.0373 (14) | −0.0007 (11) | 0.0025 (11) | 0.0032 (10) |
O3A | 0.0343 (12) | 0.0277 (11) | 0.0284 (11) | 0.0000 (9) | −0.0083 (9) | −0.0083 (9) |
O1B | 0.0547 (16) | 0.0393 (14) | 0.0358 (14) | 0.0027 (12) | −0.0033 (12) | −0.0174 (11) |
O2B | 0.0531 (17) | 0.0490 (16) | 0.0445 (16) | 0.0040 (13) | 0.0191 (13) | −0.0179 (13) |
O3B | 0.0346 (12) | 0.0263 (11) | 0.0269 (11) | −0.0022 (9) | 0.0054 (9) | −0.0049 (9) |
N1A | 0.0390 (16) | 0.0302 (15) | 0.0248 (13) | 0.0051 (12) | 0.0004 (11) | −0.0034 (11) |
N2A | 0.0270 (13) | 0.0229 (12) | 0.0219 (12) | −0.0010 (10) | −0.0023 (10) | −0.0042 (10) |
N1B | 0.0428 (16) | 0.0280 (14) | 0.0233 (13) | 0.0077 (12) | −0.0006 (12) | −0.0061 (11) |
N2B | 0.0251 (12) | 0.0230 (12) | 0.0220 (12) | 0.0004 (10) | 0.0014 (10) | −0.0053 (10) |
C1A | 0.0324 (16) | 0.0271 (15) | 0.0190 (14) | 0.0055 (12) | −0.0010 (12) | −0.0050 (11) |
C2A | 0.0326 (17) | 0.0288 (16) | 0.0253 (15) | −0.0046 (13) | 0.0028 (12) | −0.0049 (12) |
C3A | 0.0261 (15) | 0.0323 (16) | 0.0238 (15) | 0.0005 (12) | −0.0016 (12) | −0.0060 (12) |
C4A | 0.0247 (14) | 0.0273 (15) | 0.0200 (14) | 0.0021 (12) | −0.0016 (11) | −0.0073 (11) |
C5A | 0.0255 (15) | 0.0276 (15) | 0.0239 (14) | −0.0005 (12) | −0.0024 (11) | −0.0063 (12) |
C6A | 0.0266 (15) | 0.0331 (17) | 0.0249 (15) | 0.0032 (13) | −0.0037 (12) | −0.0087 (12) |
C7A | 0.0217 (14) | 0.0267 (15) | 0.0249 (15) | −0.0018 (11) | −0.0014 (11) | −0.0043 (12) |
C8A | 0.0258 (15) | 0.0236 (14) | 0.0233 (14) | 0.0006 (12) | −0.0038 (11) | −0.0035 (11) |
C9A | 0.0272 (15) | 0.0273 (15) | 0.0290 (16) | 0.0034 (12) | −0.0037 (12) | −0.0056 (12) |
C10A | 0.0314 (17) | 0.0275 (16) | 0.0373 (18) | 0.0051 (13) | −0.0084 (13) | −0.0060 (13) |
C11A | 0.046 (2) | 0.0243 (16) | 0.051 (2) | 0.0019 (15) | −0.0161 (17) | −0.0024 (15) |
C12A | 0.0381 (19) | 0.0306 (17) | 0.0395 (19) | −0.0083 (14) | −0.0074 (15) | 0.0051 (14) |
C13A | 0.0296 (16) | 0.0267 (16) | 0.0332 (17) | −0.0019 (13) | −0.0057 (13) | −0.0006 (13) |
C14A | 0.0230 (14) | 0.0221 (14) | 0.0210 (14) | 0.0001 (11) | −0.0025 (11) | −0.0050 (11) |
C15A | 0.0225 (14) | 0.0290 (15) | 0.0235 (14) | −0.0016 (12) | −0.0015 (11) | −0.0051 (12) |
C16A | 0.0281 (15) | 0.0303 (16) | 0.0239 (15) | 0.0021 (12) | 0.0012 (12) | −0.0067 (12) |
C17A | 0.0342 (17) | 0.0314 (16) | 0.0275 (16) | −0.0003 (13) | −0.0022 (13) | −0.0097 (13) |
C18A | 0.0283 (15) | 0.0278 (15) | 0.0291 (16) | −0.0044 (12) | −0.0022 (12) | −0.0072 (12) |
C19A | 0.0238 (14) | 0.0275 (15) | 0.0253 (14) | −0.0021 (12) | −0.0002 (11) | −0.0055 (12) |
C1B | 0.0355 (17) | 0.0264 (15) | 0.0182 (14) | 0.0064 (13) | 0.0006 (12) | −0.0032 (11) |
C2B | 0.0342 (16) | 0.0257 (15) | 0.0237 (15) | −0.0023 (12) | −0.0044 (12) | −0.0049 (12) |
C3B | 0.0270 (15) | 0.0298 (15) | 0.0218 (14) | −0.0003 (12) | 0.0012 (11) | −0.0037 (12) |
C4B | 0.0274 (15) | 0.0232 (14) | 0.0175 (13) | 0.0019 (11) | −0.0009 (11) | −0.0015 (11) |
C5B | 0.0274 (15) | 0.0279 (15) | 0.0217 (14) | −0.0010 (12) | −0.0014 (11) | −0.0027 (11) |
C6B | 0.0281 (15) | 0.0298 (16) | 0.0229 (14) | 0.0021 (12) | 0.0031 (12) | −0.0015 (12) |
C7B | 0.0244 (14) | 0.0256 (15) | 0.0224 (14) | −0.0023 (11) | −0.0002 (11) | −0.0055 (11) |
C8B | 0.0279 (15) | 0.0258 (15) | 0.0202 (13) | −0.0003 (12) | 0.0027 (11) | −0.0066 (11) |
C9B | 0.0281 (16) | 0.0300 (16) | 0.0294 (16) | −0.0013 (13) | 0.0001 (12) | −0.0092 (13) |
C10B | 0.0345 (17) | 0.0339 (17) | 0.0299 (16) | −0.0054 (14) | −0.0018 (13) | −0.0118 (13) |
C11B | 0.0356 (17) | 0.0264 (15) | 0.0279 (16) | 0.0004 (13) | 0.0012 (13) | −0.0081 (12) |
C12B | 0.0298 (16) | 0.0279 (15) | 0.0283 (15) | 0.0003 (12) | 0.0037 (12) | −0.0072 (12) |
C13B | 0.0261 (15) | 0.0269 (15) | 0.0254 (15) | 0.0003 (12) | −0.0010 (11) | −0.0072 (12) |
C14B | 0.0262 (14) | 0.0231 (14) | 0.0195 (13) | 0.0001 (11) | 0.0004 (11) | −0.0042 (11) |
C15B | 0.0217 (14) | 0.0268 (15) | 0.0298 (15) | −0.0011 (12) | −0.0028 (12) | −0.0052 (12) |
C16B | 0.0267 (15) | 0.0259 (15) | 0.0346 (17) | −0.0056 (12) | 0.0041 (13) | −0.0056 (13) |
C17B | 0.0338 (17) | 0.0298 (16) | 0.0301 (16) | −0.0013 (13) | 0.0054 (13) | 0.0000 (13) |
C18B | 0.0281 (16) | 0.0316 (16) | 0.0238 (15) | 0.0034 (13) | −0.0025 (12) | 0.0000 (12) |
C19B | 0.0214 (14) | 0.0288 (15) | 0.0264 (15) | 0.0000 (11) | −0.0022 (11) | −0.0034 (12) |
O1A—N1A | 1.229 (4) | C17A—H17A | 0.9900 |
O2A—N1A | 1.211 (4) | C17A—H17B | 0.9900 |
O3A—C7A | 1.230 (4) | C18A—C19A | 1.532 (4) |
O1B—N1B | 1.213 (4) | C18A—H18A | 0.9900 |
O2B—N1B | 1.229 (4) | C18A—H18B | 0.9900 |
O3B—C7B | 1.226 (4) | C19A—H19A | 0.9900 |
N1A—C1A | 1.481 (4) | C19A—H19B | 0.9900 |
N2A—C7A | 1.356 (4) | C1B—C6B | 1.369 (5) |
N2A—C8A | 1.483 (4) | C1B—C2B | 1.395 (5) |
N2A—C14A | 1.483 (4) | C2B—C3B | 1.393 (4) |
N1B—C1B | 1.483 (4) | C2B—H2BA | 0.9500 |
N2B—C7B | 1.359 (4) | C3B—C4B | 1.383 (5) |
N2B—C14B | 1.477 (4) | C3B—H3BA | 0.9500 |
N2B—C8B | 1.480 (4) | C4B—C5B | 1.391 (4) |
C1A—C6A | 1.364 (5) | C4B—C7B | 1.520 (4) |
C1A—C2A | 1.397 (5) | C5B—C6B | 1.391 (4) |
C2A—C3A | 1.389 (5) | C5B—H5BA | 0.9500 |
C2A—H2AA | 0.9500 | C6B—H6BA | 0.9500 |
C3A—C4A | 1.384 (5) | C8B—C9B | 1.524 (4) |
C3A—H3AA | 0.9500 | C8B—C13B | 1.538 (4) |
C4A—C5A | 1.398 (4) | C8B—H8BA | 1.0000 |
C4A—C7A | 1.519 (4) | C9B—C10B | 1.528 (4) |
C5A—C6A | 1.393 (4) | C9B—H9BA | 0.9900 |
C5A—H5AA | 0.9500 | C9B—H9BB | 0.9900 |
C6A—H6AA | 0.9500 | C10B—C11B | 1.538 (5) |
C8A—C13A | 1.524 (5) | C10B—H10C | 0.9900 |
C8A—C9A | 1.533 (4) | C10B—H10D | 0.9900 |
C8A—H8AA | 1.0000 | C11B—C12B | 1.517 (5) |
C9A—C10A | 1.537 (4) | C11B—H11C | 0.9900 |
C9A—H9AA | 0.9900 | C11B—H11D | 0.9900 |
C9A—H9AB | 0.9900 | C12B—C13B | 1.527 (4) |
C10A—C11A | 1.520 (5) | C12B—H12C | 0.9900 |
C10A—H10A | 0.9900 | C12B—H12D | 0.9900 |
C10A—H10B | 0.9900 | C13B—H13C | 0.9900 |
C11A—C12A | 1.527 (6) | C13B—H13D | 0.9900 |
C11A—H11A | 0.9900 | C14B—C15B | 1.530 (4) |
C11A—H11B | 0.9900 | C14B—C19B | 1.540 (4) |
C12A—C13A | 1.530 (4) | C14B—H14B | 1.0000 |
C12A—H12A | 0.9900 | C15B—C16B | 1.531 (4) |
C12A—H12B | 0.9900 | C15B—H15C | 0.9900 |
C13A—H13A | 0.9900 | C15B—H15D | 0.9900 |
C13A—H13B | 0.9900 | C16B—C17B | 1.529 (5) |
C14A—C15A | 1.530 (4) | C16B—H16C | 0.9900 |
C14A—C19A | 1.536 (4) | C16B—H16D | 0.9900 |
C14A—H14A | 1.0000 | C17B—C18B | 1.528 (5) |
C15A—C16A | 1.533 (4) | C17B—H17C | 0.9900 |
C15A—H15A | 0.9900 | C17B—H17D | 0.9900 |
C15A—H15B | 0.9900 | C18B—C19B | 1.530 (4) |
C16A—C17A | 1.530 (5) | C18B—H18C | 0.9900 |
C16A—H16A | 0.9900 | C18B—H18E | 0.9900 |
C16A—H16B | 0.9900 | C19B—H19E | 0.9900 |
C17A—C18A | 1.522 (5) | C19B—H19C | 0.9900 |
O2A—N1A—O1A | 124.4 (3) | C18A—C19A—C14A | 110.5 (2) |
O2A—N1A—C1A | 118.6 (3) | C18A—C19A—H19A | 109.6 |
O1A—N1A—C1A | 116.9 (3) | C14A—C19A—H19A | 109.6 |
C7A—N2A—C8A | 119.5 (2) | C18A—C19A—H19B | 109.6 |
C7A—N2A—C14A | 123.4 (3) | C14A—C19A—H19B | 109.6 |
C8A—N2A—C14A | 116.7 (2) | H19A—C19A—H19B | 108.1 |
O1B—N1B—O2B | 124.1 (3) | C6B—C1B—C2B | 123.2 (3) |
O1B—N1B—C1B | 118.7 (3) | C6B—C1B—N1B | 118.7 (3) |
O2B—N1B—C1B | 117.2 (3) | C2B—C1B—N1B | 118.0 (3) |
C7B—N2B—C14B | 123.6 (2) | C3B—C2B—C1B | 117.4 (3) |
C7B—N2B—C8B | 119.3 (2) | C3B—C2B—H2BA | 121.3 |
C14B—N2B—C8B | 116.8 (2) | C1B—C2B—H2BA | 121.3 |
C6A—C1A—C2A | 122.9 (3) | C4B—C3B—C2B | 120.6 (3) |
C6A—C1A—N1A | 118.7 (3) | C4B—C3B—H3BA | 119.7 |
C2A—C1A—N1A | 118.4 (3) | C2B—C3B—H3BA | 119.7 |
C3A—C2A—C1A | 117.8 (3) | C3B—C4B—C5B | 120.3 (3) |
C3A—C2A—H2AA | 121.1 | C3B—C4B—C7B | 122.6 (3) |
C1A—C2A—H2AA | 121.1 | C5B—C4B—C7B | 116.8 (3) |
C4A—C3A—C2A | 120.5 (3) | C4B—C5B—C6B | 120.2 (3) |
C4A—C3A—H3AA | 119.8 | C4B—C5B—H5BA | 119.9 |
C2A—C3A—H3AA | 119.8 | C6B—C5B—H5BA | 119.9 |
C3A—C4A—C5A | 120.2 (3) | C1B—C6B—C5B | 118.3 (3) |
C3A—C4A—C7A | 123.1 (3) | C1B—C6B—H6BA | 120.9 |
C5A—C4A—C7A | 116.5 (3) | C5B—C6B—H6BA | 120.9 |
C6A—C5A—C4A | 119.9 (3) | O3B—C7B—N2B | 123.6 (3) |
C6A—C5A—H5AA | 120.1 | O3B—C7B—C4B | 117.2 (3) |
C4A—C5A—H5AA | 120.1 | N2B—C7B—C4B | 119.2 (3) |
C1A—C6A—C5A | 118.6 (3) | N2B—C8B—C9B | 112.9 (3) |
C1A—C6A—H6AA | 120.7 | N2B—C8B—C13B | 112.0 (2) |
C5A—C6A—H6AA | 120.7 | C9B—C8B—C13B | 112.3 (3) |
O3A—C7A—N2A | 123.3 (3) | N2B—C8B—H8BA | 106.4 |
O3A—C7A—C4A | 117.5 (3) | C9B—C8B—H8BA | 106.4 |
N2A—C7A—C4A | 119.2 (3) | C13B—C8B—H8BA | 106.4 |
N2A—C8A—C13A | 113.2 (2) | C8B—C9B—C10B | 110.8 (3) |
N2A—C8A—C9A | 112.7 (3) | C8B—C9B—H9BA | 109.5 |
C13A—C8A—C9A | 111.9 (3) | C10B—C9B—H9BA | 109.5 |
N2A—C8A—H8AA | 106.1 | C8B—C9B—H9BB | 109.5 |
C13A—C8A—H8AA | 106.1 | C10B—C9B—H9BB | 109.5 |
C9A—C8A—H8AA | 106.1 | H9BA—C9B—H9BB | 108.1 |
C8A—C9A—C10A | 109.4 (3) | C9B—C10B—C11B | 110.5 (3) |
C8A—C9A—H9AA | 109.8 | C9B—C10B—H10C | 109.6 |
C10A—C9A—H9AA | 109.8 | C11B—C10B—H10C | 109.6 |
C8A—C9A—H9AB | 109.8 | C9B—C10B—H10D | 109.6 |
C10A—C9A—H9AB | 109.8 | C11B—C10B—H10D | 109.6 |
H9AA—C9A—H9AB | 108.2 | H10C—C10B—H10D | 108.1 |
C11A—C10A—C9A | 111.6 (3) | C12B—C11B—C10B | 110.8 (3) |
C11A—C10A—H10A | 109.3 | C12B—C11B—H11C | 109.5 |
C9A—C10A—H10A | 109.3 | C10B—C11B—H11C | 109.5 |
C11A—C10A—H10B | 109.3 | C12B—C11B—H11D | 109.5 |
C9A—C10A—H10B | 109.3 | C10B—C11B—H11D | 109.5 |
H10A—C10A—H10B | 108.0 | H11C—C11B—H11D | 108.1 |
C10A—C11A—C12A | 111.5 (3) | C11B—C12B—C13B | 111.4 (3) |
C10A—C11A—H11A | 109.3 | C11B—C12B—H12C | 109.4 |
C12A—C11A—H11A | 109.3 | C13B—C12B—H12C | 109.4 |
C10A—C11A—H11B | 109.3 | C11B—C12B—H12D | 109.4 |
C12A—C11A—H11B | 109.3 | C13B—C12B—H12D | 109.4 |
H11A—C11A—H11B | 108.0 | H12C—C12B—H12D | 108.0 |
C11A—C12A—C13A | 110.9 (3) | C12B—C13B—C8B | 109.6 (3) |
C11A—C12A—H12A | 109.5 | C12B—C13B—H13C | 109.7 |
C13A—C12A—H12A | 109.5 | C8B—C13B—H13C | 109.7 |
C11A—C12A—H12B | 109.5 | C12B—C13B—H13D | 109.7 |
C13A—C12A—H12B | 109.5 | C8B—C13B—H13D | 109.7 |
H12A—C12A—H12B | 108.0 | H13C—C13B—H13D | 108.2 |
C8A—C13A—C12A | 110.2 (3) | N2B—C14B—C15B | 111.6 (2) |
C8A—C13A—H13A | 109.6 | N2B—C14B—C19B | 111.3 (2) |
C12A—C13A—H13A | 109.6 | C15B—C14B—C19B | 111.0 (2) |
C8A—C13A—H13B | 109.6 | N2B—C14B—H14B | 107.6 |
C12A—C13A—H13B | 109.6 | C15B—C14B—H14B | 107.6 |
H13A—C13A—H13B | 108.1 | C19B—C14B—H14B | 107.6 |
N2A—C14A—C15A | 111.7 (2) | C14B—C15B—C16B | 110.9 (2) |
N2A—C14A—C19A | 110.9 (2) | C14B—C15B—H15C | 109.5 |
C15A—C14A—C19A | 111.5 (2) | C16B—C15B—H15C | 109.5 |
N2A—C14A—H14A | 107.5 | C14B—C15B—H15D | 109.5 |
C15A—C14A—H14A | 107.5 | C16B—C15B—H15D | 109.5 |
C19A—C14A—H14A | 107.5 | H15C—C15B—H15D | 108.0 |
C14A—C15A—C16A | 110.3 (3) | C17B—C16B—C15B | 111.0 (3) |
C14A—C15A—H15A | 109.6 | C17B—C16B—H16C | 109.4 |
C16A—C15A—H15A | 109.6 | C15B—C16B—H16C | 109.4 |
C14A—C15A—H15B | 109.6 | C17B—C16B—H16D | 109.4 |
C16A—C15A—H15B | 109.6 | C15B—C16B—H16D | 109.4 |
H15A—C15A—H15B | 108.1 | H16C—C16B—H16D | 108.0 |
C17A—C16A—C15A | 110.8 (3) | C18B—C17B—C16B | 110.7 (3) |
C17A—C16A—H16A | 109.5 | C18B—C17B—H17C | 109.5 |
C15A—C16A—H16A | 109.5 | C16B—C17B—H17C | 109.5 |
C17A—C16A—H16B | 109.5 | C18B—C17B—H17D | 109.5 |
C15A—C16A—H16B | 109.5 | C16B—C17B—H17D | 109.5 |
H16A—C16A—H16B | 108.1 | H17C—C17B—H17D | 108.1 |
C18A—C17A—C16A | 110.5 (3) | C17B—C18B—C19B | 110.6 (3) |
C18A—C17A—H17A | 109.6 | C17B—C18B—H18C | 109.5 |
C16A—C17A—H17A | 109.6 | C19B—C18B—H18C | 109.5 |
C18A—C17A—H17B | 109.6 | C17B—C18B—H18E | 109.5 |
C16A—C17A—H17B | 109.6 | C19B—C18B—H18E | 109.5 |
H17A—C17A—H17B | 108.1 | H18C—C18B—H18E | 108.1 |
C17A—C18A—C19A | 111.6 (3) | C18B—C19B—C14B | 110.4 (3) |
C17A—C18A—H18A | 109.3 | C18B—C19B—H19E | 109.6 |
C19A—C18A—H18A | 109.3 | C14B—C19B—H19E | 109.6 |
C17A—C18A—H18B | 109.3 | C18B—C19B—H19C | 109.6 |
C19A—C18A—H18B | 109.3 | C14B—C19B—H19C | 109.6 |
H18A—C18A—H18B | 108.0 | H19E—C19B—H19C | 108.1 |
O2A—N1A—C1A—C6A | −176.6 (3) | O1B—N1B—C1B—C6B | 178.1 (3) |
O1A—N1A—C1A—C6A | 1.2 (4) | O2B—N1B—C1B—C6B | −0.7 (4) |
O2A—N1A—C1A—C2A | 3.9 (4) | O1B—N1B—C1B—C2B | −3.5 (4) |
O1A—N1A—C1A—C2A | −178.4 (3) | O2B—N1B—C1B—C2B | 177.7 (3) |
C6A—C1A—C2A—C3A | 2.1 (5) | C6B—C1B—C2B—C3B | −1.7 (5) |
N1A—C1A—C2A—C3A | −178.3 (3) | N1B—C1B—C2B—C3B | 180.0 (3) |
C1A—C2A—C3A—C4A | −0.4 (5) | C1B—C2B—C3B—C4B | 1.2 (5) |
C2A—C3A—C4A—C5A | −0.9 (5) | C2B—C3B—C4B—C5B | −0.1 (5) |
C2A—C3A—C4A—C7A | −175.6 (3) | C2B—C3B—C4B—C7B | 172.8 (3) |
C3A—C4A—C5A—C6A | 0.6 (4) | C3B—C4B—C5B—C6B | −0.6 (4) |
C7A—C4A—C5A—C6A | 175.7 (3) | C7B—C4B—C5B—C6B | −173.9 (3) |
C2A—C1A—C6A—C5A | −2.4 (5) | C2B—C1B—C6B—C5B | 1.1 (5) |
N1A—C1A—C6A—C5A | 178.1 (3) | N1B—C1B—C6B—C5B | 179.4 (3) |
C4A—C5A—C6A—C1A | 1.0 (5) | C4B—C5B—C6B—C1B | 0.1 (5) |
C8A—N2A—C7A—O3A | −0.7 (5) | C14B—N2B—C7B—O3B | −171.0 (3) |
C14A—N2A—C7A—O3A | 172.1 (3) | C8B—N2B—C7B—O3B | 2.4 (5) |
C8A—N2A—C7A—C4A | −179.7 (3) | C14B—N2B—C7B—C4B | 9.0 (4) |
C14A—N2A—C7A—C4A | −6.9 (4) | C8B—N2B—C7B—C4B | −177.7 (3) |
C3A—C4A—C7A—O3A | 121.5 (3) | C3B—C4B—C7B—O3B | −119.6 (3) |
C5A—C4A—C7A—O3A | −53.4 (4) | C5B—C4B—C7B—O3B | 53.5 (4) |
C3A—C4A—C7A—N2A | −59.5 (4) | C3B—C4B—C7B—N2B | 60.4 (4) |
C5A—C4A—C7A—N2A | 125.6 (3) | C5B—C4B—C7B—N2B | −126.5 (3) |
C7A—N2A—C8A—C13A | 63.0 (4) | C7B—N2B—C8B—C9B | −63.0 (4) |
C14A—N2A—C8A—C13A | −110.2 (3) | C14B—N2B—C8B—C9B | 110.8 (3) |
C7A—N2A—C8A—C9A | −65.2 (4) | C7B—N2B—C8B—C13B | 64.9 (4) |
C14A—N2A—C8A—C9A | 121.5 (3) | C14B—N2B—C8B—C13B | −121.2 (3) |
N2A—C8A—C9A—C10A | −174.3 (3) | N2B—C8B—C9B—C10B | −176.9 (3) |
C13A—C8A—C9A—C10A | 56.8 (3) | C13B—C8B—C9B—C10B | 55.3 (3) |
C8A—C9A—C10A—C11A | −55.6 (4) | C8B—C9B—C10B—C11B | −55.3 (4) |
C9A—C10A—C11A—C12A | 55.9 (4) | C9B—C10B—C11B—C12B | 57.1 (4) |
C10A—C11A—C12A—C13A | −55.7 (4) | C10B—C11B—C12B—C13B | −58.2 (4) |
N2A—C8A—C13A—C12A | 173.9 (3) | C11B—C12B—C13B—C8B | 56.5 (3) |
C9A—C8A—C13A—C12A | −57.4 (4) | N2B—C8B—C13B—C12B | 176.5 (3) |
C11A—C12A—C13A—C8A | 56.0 (4) | C9B—C8B—C13B—C12B | −55.3 (3) |
C7A—N2A—C14A—C15A | −112.5 (3) | C7B—N2B—C14B—C15B | −122.7 (3) |
C8A—N2A—C14A—C15A | 60.4 (3) | C8B—N2B—C14B—C15B | 63.7 (3) |
C7A—N2A—C14A—C19A | 122.5 (3) | C7B—N2B—C14B—C19B | 112.6 (3) |
C8A—N2A—C14A—C19A | −64.6 (3) | C8B—N2B—C14B—C19B | −60.9 (3) |
N2A—C14A—C15A—C16A | 179.0 (2) | N2B—C14B—C15B—C16B | 179.6 (2) |
C19A—C14A—C15A—C16A | −56.3 (3) | C19B—C14B—C15B—C16B | −55.6 (3) |
C14A—C15A—C16A—C17A | 57.2 (3) | C14B—C15B—C16B—C17B | 55.9 (3) |
C15A—C16A—C17A—C18A | −57.5 (4) | C15B—C16B—C17B—C18B | −57.0 (4) |
C16A—C17A—C18A—C19A | 56.8 (4) | C16B—C17B—C18B—C19B | 57.8 (4) |
C17A—C18A—C19A—C14A | −55.5 (3) | C17B—C18B—C19B—C14B | −57.2 (3) |
N2A—C14A—C19A—C18A | −179.6 (2) | N2B—C14B—C19B—C18B | −178.7 (2) |
C15A—C14A—C19A—C18A | 55.3 (3) | C15B—C14B—C19B—C18B | 56.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5A—H5AA···O3Ai | 0.95 | 2.60 | 3.155 (4) | 118 |
C5B—H5BA···O3Bii | 0.95 | 2.54 | 3.148 (4) | 122 |
C9A—H9AA···O3A | 0.99 | 2.48 | 3.044 (4) | 115 |
C9B—H9BA···O3B | 0.99 | 2.38 | 2.983 (4) | 118 |
C13A—H13B···O3A | 0.99 | 2.43 | 3.001 (4) | 116 |
C13B—H13C···O3B | 0.99 | 2.47 | 3.043 (4) | 117 |
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C19H26N2O3 |
Mr | 330.42 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 123 |
a, b, c (Å) | 6.1874 (3), 10.7109 (4), 26.8188 (11) |
α, β, γ (°) | 79.128 (4), 89.027 (4), 82.883 (3) |
V (Å3) | 1731.97 (13) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.69 |
Crystal size (mm) | 0.29 × 0.26 × 0.07 |
Data collection | |
Diffractometer | Agilent Xcalibur Ruby Gemini diffractometer |
Absorption correction | Analytical (Clark & Reid, 1995) |
Tmin, Tmax | 0.823, 0.950 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12453, 6952, 6374 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.080, 0.239, 1.11 |
No. of reflections | 6952 |
No. of parameters | 434 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.29 |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C5B—H5BA···O3Bi | 0.95 | 2.54 | 3.148 (4) | 121.8 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
RJB acknowledges the NSF–MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.
References
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In (I), C19H26N2O3, there are two independent molecules (A and B) in the asymmetric unit of the title compound. In molecule A and B the nitro group is almost coplanar with the attached benzene ring in both molecules [C1—C6—N1—O1 = 1.2 (4) ° and C1—C2—N1—O2 = 3.9 (4) ° in molecule A, -3.5 (4) ° and -0.7 (4) ° in molecule B, respectively]. In each molecule, the cyclohexyl rings both adopt a chair conformation as indicated by the puckering parameters Q(2) and ϕ(2) (Cremer & Pople, 1975) which are 0.012 (1) Å and 177.369 (1) ° in C8A—C13A, 0.015 (1) Å and 122.495 (1) ° in C14A—C19A; 0.017 (1) Å, 21.210 (1) ° in C8B—C13B and 0.013 (1) Å, 230.094 (1) ° in C14A—C19A, respectively. In both molecules, the nitrobenzamide moiety (O3, N2, C7, C8 and C14) is planar (maximum deviation for N2, 0.049 (2) and 0.047 (2) Å in molecules A and B respectively). The dihedral angles between these planar nitrobenzamide moieties and the nitrophenyl groups in molecules A and B are 58.61 (11) and 59.95 (12)° respectively. The main difference in the two molecules lies in how the nitrophenyl rings are arranged with respect to the rest of the molecule and is shown in Figures 1 & 2. This is best illustrated by considering the C3 C4 C7 O3 torsion angle which is 121.46 (33)° in molecule A and -119.62 (34)° in molecule B, thus the phenyl groups in each molecule are twisted in different directions with respect to the plane of the amide moiety. Apart from this the bond lengths and angles in the two molecules agree within experimental error. While there are no classic hydrogen bonds found in the crystal, there are weak C—H···O intra- and intermolecular interactions.