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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

(Received 3 August 2012; accepted 13 August 2012; online 25 August 2012)

The title compound, C19H26N2O3, crystallizes with two independent mol­ecules in the asymmetric unit 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[Priya, B. S., Swamy, B. S. N. & Rangapa, K. S. (2005). Bioorg. Med. Chem. 13, 2623-2628.]). For conformational analysis, see: Cremer & Pople, (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For related structures, see: Toda et al. (1987[Toda, F., Kai, A., Tagami, Y. & Mak, T. C. W. (1987). Chem. Lett. pp. 1393-1396.]); Saeed et al. (2011[Saeed, S., Jasinski, J. P. & Butcher, R. J. (2011). Acta Cryst. E67, o279.]).

[Scheme 1]

Experimental

Crystal data
  • C19H26N2O3

  • Mr = 330.42

  • Triclinic, [P \overline 1]

  • a = 6.1874 (3) Å

  • b = 10.7109 (4) Å

  • c = 26.8188 (11) Å

  • α = 79.128 (4)°

  • β = 89.027 (4)°

  • γ = 82.883 (3)°

  • V = 1731.97 (13) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.69 mm−1

  • T = 123 K

  • 0.29 × 0.26 × 0.07 mm

Data collection
  • Agilent Xcalibur Ruby Gemini diffractometer

  • Absorption correction: analytical (Clark & Reid, 1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.]) Tmin = 0.823, Tmax = 0.950

  • 12453 measured reflections

  • 6952 independent reflections

  • 6374 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.080

  • wR(F2) = 0.239

  • S = 1.11

  • 6952 reflections

  • 434 parameters

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C5B—H5BA⋯O3Bi 0.95 2.54 3.148 (4) 122
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

For background to N-substituted benzamides, see Priya et al. (2005). For conformational analysis, see: Cremer & Pople, (1975). For related structures, see: Toda et al. (1987); Saeed et al. (2011).

Experimental top

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.

Refinement top

The crystal structure is a non-merohedral twin with the twin law 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 refinement 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.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: 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).

Figures top
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.
N,N-Dicyclohexyl-4-nitrobenzamide top
Crystal data top
C19H26N2O3Z = 4
Mr = 330.42F(000) = 712
Triclinic, P1Dx = 1.267 Mg m3
a = 6.1874 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 10.7109 (4) ÅCell parameters from 6557 reflections
c = 26.8188 (11) Åθ = 3.4–75.4°
α = 79.128 (4)°µ = 0.69 mm1
β = 89.027 (4)°T = 123 K
γ = 82.883 (3)°Plate, colorless
V = 1731.97 (13) Å30.29 × 0.26 × 0.07 mm
Data collection top
Agilent Xcalibur Ruby Gemini
diffractometer
6952 independent reflections
Radiation source: Enhance (Cu) X-ray Source6374 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 10.5081 pixels mm-1θmax = 75.6°, θmin = 3.4°
ω scansh = 57
Absorption correction: analytical
(Clark & Reid, 1995)
k = 1311
Tmin = 0.823, Tmax = 0.950l = 3333
12453 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.080Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.239H-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 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C19H26N2O3γ = 82.883 (3)°
Mr = 330.42V = 1731.97 (13) Å3
Triclinic, P1Z = 4
a = 6.1874 (3) ÅCu Kα radiation
b = 10.7109 (4) ŵ = 0.69 mm1
c = 26.8188 (11) ÅT = 123 K
α = 79.128 (4)°0.29 × 0.26 × 0.07 mm
β = 89.027 (4)°
Data collection top
Agilent Xcalibur Ruby Gemini
diffractometer
6952 independent reflections
Absorption correction: analytical
(Clark & Reid, 1995)
6374 reflections with I > 2σ(I)
Tmin = 0.823, Tmax = 0.950Rint = 0.028
12453 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0800 restraints
wR(F2) = 0.239H-atom parameters constrained
S = 1.11Δρmax = 0.41 e Å3
6952 reflectionsΔρmin = 0.29 e Å3
434 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
O1A1.2037 (5)0.5044 (3)1.08793 (12)0.0488 (7)
O2A0.9117 (5)0.4171 (2)1.08150 (10)0.0412 (6)
O3A0.6696 (4)1.0644 (2)0.95462 (9)0.0300 (5)
O1B0.3898 (5)0.0077 (3)0.41690 (10)0.0426 (6)
O2B0.6849 (5)0.0824 (3)0.40932 (11)0.0488 (7)
O3B0.1784 (4)0.5172 (2)0.54297 (9)0.0295 (5)
N1A1.0181 (5)0.5061 (3)1.07197 (11)0.0324 (6)
N2A0.5886 (4)0.9656 (2)0.89045 (10)0.0241 (5)
N1B0.5025 (5)0.0694 (3)0.42687 (10)0.0322 (6)
N2B0.1038 (4)0.3626 (2)0.60959 (10)0.0235 (5)
C1A0.9244 (5)0.6242 (3)1.03726 (11)0.0268 (6)
C2A0.7117 (6)0.6306 (3)1.01945 (12)0.0289 (7)
H2AA0.62730.56211.03000.035*
C3A0.6276 (5)0.7404 (3)0.98588 (12)0.0276 (6)
H3AA0.48370.74720.97290.033*
C4A0.7519 (5)0.8398 (3)0.97115 (11)0.0241 (6)
C5A0.9626 (5)0.8314 (3)0.99050 (12)0.0257 (6)
H5AA1.04700.90010.98060.031*
C6A1.0485 (5)0.7220 (3)1.02437 (12)0.0283 (7)
H6AA1.19070.71571.03820.034*
C7A0.6645 (5)0.9660 (3)0.93753 (12)0.0246 (6)
C8A0.5043 (5)1.0884 (3)0.85731 (11)0.0246 (6)
H8AA0.46011.06610.82470.030*
C9A0.2981 (5)1.1545 (3)0.87833 (12)0.0283 (7)
H9AA0.33261.18020.91060.034*
H9AB0.18711.09450.88530.034*
C10A0.2085 (6)1.2733 (3)0.83935 (14)0.0327 (7)
H10A0.15991.24600.80850.039*
H10B0.08041.31880.85380.039*
C11A0.3790 (7)1.3642 (3)0.82482 (16)0.0416 (9)
H11A0.41591.39890.85490.050*
H11B0.31831.43700.79840.050*
C12A0.5854 (6)1.2968 (3)0.80490 (15)0.0371 (8)
H12A0.69621.35690.79780.045*
H12B0.55191.27040.77270.045*
C13A0.6769 (5)1.1789 (3)0.84358 (13)0.0306 (7)
H13A0.80541.13380.82910.037*
H13B0.72431.20590.87460.037*
C14A0.6076 (5)0.8494 (3)0.86733 (11)0.0222 (6)
H14A0.67070.77540.89360.027*
C15A0.7626 (5)0.8599 (3)0.82207 (11)0.0251 (6)
H15A0.90810.87360.83320.030*
H15B0.70740.93440.79570.030*
C16A0.7815 (5)0.7375 (3)0.79970 (12)0.0278 (6)
H16A0.87810.74670.76980.033*
H16B0.84730.66410.82520.033*
C17A0.5575 (6)0.7111 (3)0.78393 (13)0.0307 (7)
H17A0.49610.78150.75660.037*
H17B0.57250.63040.77060.037*
C18A0.4038 (5)0.7004 (3)0.82904 (12)0.0281 (6)
H18A0.45910.62520.85510.034*
H18B0.25830.68670.81780.034*
C19A0.3824 (5)0.8210 (3)0.85253 (12)0.0256 (6)
H19A0.28940.80880.88300.031*
H19B0.31180.89480.82780.031*
C1B0.4191 (6)0.1522 (3)0.46324 (11)0.0277 (7)
C2B0.2093 (6)0.1422 (3)0.48212 (12)0.0279 (6)
H2BA0.12170.08420.47210.033*
C3B0.1331 (5)0.2205 (3)0.51624 (11)0.0266 (6)
H3BA0.00810.21510.53040.032*
C4B0.2611 (5)0.3060 (3)0.52976 (11)0.0234 (6)
C5B0.4682 (5)0.3148 (3)0.50942 (11)0.0261 (6)
H5BA0.55490.37420.51860.031*
C6B0.5487 (5)0.2367 (3)0.47565 (12)0.0279 (6)
H6BA0.69000.24180.46160.033*
C7B0.1765 (5)0.4039 (3)0.56197 (11)0.0241 (6)
C8B0.0134 (5)0.4579 (3)0.64028 (11)0.0246 (6)
H8BA0.02800.40790.67370.030*
C9B0.1805 (5)0.5419 (3)0.65189 (13)0.0289 (7)
H9BA0.22980.59190.61980.035*
H9BB0.30880.48700.66900.035*
C10B0.0831 (6)0.6335 (3)0.68602 (13)0.0319 (7)
H10C0.19070.69110.69120.038*
H10D0.04890.58380.71960.038*
C11B0.1255 (6)0.7136 (3)0.66192 (13)0.0300 (7)
H11C0.18950.77000.68500.036*
H11D0.08910.76850.62960.036*
C12B0.2904 (5)0.6276 (3)0.65174 (12)0.0288 (7)
H12C0.42230.68110.63580.035*
H12D0.33370.57680.68430.035*
C13B0.1973 (5)0.5371 (3)0.61686 (12)0.0262 (6)
H13C0.16600.58720.58310.031*
H13D0.30510.47910.61220.031*
C14B0.1299 (5)0.2268 (3)0.63518 (11)0.0232 (6)
H14B0.19560.17480.61020.028*
C15B0.0898 (5)0.1806 (3)0.65121 (12)0.0262 (6)
H15C0.18450.19160.62090.031*
H15D0.16240.23330.67470.031*
C16B0.0599 (5)0.0395 (3)0.67733 (13)0.0290 (7)
H16C0.20290.01330.68910.035*
H16D0.00160.01400.65270.035*
C17B0.0960 (6)0.0174 (3)0.72263 (13)0.0322 (7)
H17C0.03200.06520.74860.039*
H17D0.11730.07480.73800.039*
C18B0.3159 (5)0.0618 (3)0.70600 (12)0.0291 (7)
H18C0.38460.00990.68180.035*
H18E0.41330.04880.73590.035*
C19B0.2872 (5)0.2034 (3)0.68080 (12)0.0260 (6)
H19E0.43030.22980.66920.031*
H19C0.22910.25600.70580.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0452 (16)0.0435 (15)0.0500 (17)0.0052 (12)0.0178 (13)0.0058 (12)
O2A0.0485 (15)0.0328 (13)0.0373 (14)0.0007 (11)0.0025 (11)0.0032 (10)
O3A0.0343 (12)0.0277 (11)0.0284 (11)0.0000 (9)0.0083 (9)0.0083 (9)
O1B0.0547 (16)0.0393 (14)0.0358 (14)0.0027 (12)0.0033 (12)0.0174 (11)
O2B0.0531 (17)0.0490 (16)0.0445 (16)0.0040 (13)0.0191 (13)0.0179 (13)
O3B0.0346 (12)0.0263 (11)0.0269 (11)0.0022 (9)0.0054 (9)0.0049 (9)
N1A0.0390 (16)0.0302 (15)0.0248 (13)0.0051 (12)0.0004 (11)0.0034 (11)
N2A0.0270 (13)0.0229 (12)0.0219 (12)0.0010 (10)0.0023 (10)0.0042 (10)
N1B0.0428 (16)0.0280 (14)0.0233 (13)0.0077 (12)0.0006 (12)0.0061 (11)
N2B0.0251 (12)0.0230 (12)0.0220 (12)0.0004 (10)0.0014 (10)0.0053 (10)
C1A0.0324 (16)0.0271 (15)0.0190 (14)0.0055 (12)0.0010 (12)0.0050 (11)
C2A0.0326 (17)0.0288 (16)0.0253 (15)0.0046 (13)0.0028 (12)0.0049 (12)
C3A0.0261 (15)0.0323 (16)0.0238 (15)0.0005 (12)0.0016 (12)0.0060 (12)
C4A0.0247 (14)0.0273 (15)0.0200 (14)0.0021 (12)0.0016 (11)0.0073 (11)
C5A0.0255 (15)0.0276 (15)0.0239 (14)0.0005 (12)0.0024 (11)0.0063 (12)
C6A0.0266 (15)0.0331 (17)0.0249 (15)0.0032 (13)0.0037 (12)0.0087 (12)
C7A0.0217 (14)0.0267 (15)0.0249 (15)0.0018 (11)0.0014 (11)0.0043 (12)
C8A0.0258 (15)0.0236 (14)0.0233 (14)0.0006 (12)0.0038 (11)0.0035 (11)
C9A0.0272 (15)0.0273 (15)0.0290 (16)0.0034 (12)0.0037 (12)0.0056 (12)
C10A0.0314 (17)0.0275 (16)0.0373 (18)0.0051 (13)0.0084 (13)0.0060 (13)
C11A0.046 (2)0.0243 (16)0.051 (2)0.0019 (15)0.0161 (17)0.0024 (15)
C12A0.0381 (19)0.0306 (17)0.0395 (19)0.0083 (14)0.0074 (15)0.0051 (14)
C13A0.0296 (16)0.0267 (16)0.0332 (17)0.0019 (13)0.0057 (13)0.0006 (13)
C14A0.0230 (14)0.0221 (14)0.0210 (14)0.0001 (11)0.0025 (11)0.0050 (11)
C15A0.0225 (14)0.0290 (15)0.0235 (14)0.0016 (12)0.0015 (11)0.0051 (12)
C16A0.0281 (15)0.0303 (16)0.0239 (15)0.0021 (12)0.0012 (12)0.0067 (12)
C17A0.0342 (17)0.0314 (16)0.0275 (16)0.0003 (13)0.0022 (13)0.0097 (13)
C18A0.0283 (15)0.0278 (15)0.0291 (16)0.0044 (12)0.0022 (12)0.0072 (12)
C19A0.0238 (14)0.0275 (15)0.0253 (14)0.0021 (12)0.0002 (11)0.0055 (12)
C1B0.0355 (17)0.0264 (15)0.0182 (14)0.0064 (13)0.0006 (12)0.0032 (11)
C2B0.0342 (16)0.0257 (15)0.0237 (15)0.0023 (12)0.0044 (12)0.0049 (12)
C3B0.0270 (15)0.0298 (15)0.0218 (14)0.0003 (12)0.0012 (11)0.0037 (12)
C4B0.0274 (15)0.0232 (14)0.0175 (13)0.0019 (11)0.0009 (11)0.0015 (11)
C5B0.0274 (15)0.0279 (15)0.0217 (14)0.0010 (12)0.0014 (11)0.0027 (11)
C6B0.0281 (15)0.0298 (16)0.0229 (14)0.0021 (12)0.0031 (12)0.0015 (12)
C7B0.0244 (14)0.0256 (15)0.0224 (14)0.0023 (11)0.0002 (11)0.0055 (11)
C8B0.0279 (15)0.0258 (15)0.0202 (13)0.0003 (12)0.0027 (11)0.0066 (11)
C9B0.0281 (16)0.0300 (16)0.0294 (16)0.0013 (13)0.0001 (12)0.0092 (13)
C10B0.0345 (17)0.0339 (17)0.0299 (16)0.0054 (14)0.0018 (13)0.0118 (13)
C11B0.0356 (17)0.0264 (15)0.0279 (16)0.0004 (13)0.0012 (13)0.0081 (12)
C12B0.0298 (16)0.0279 (15)0.0283 (15)0.0003 (12)0.0037 (12)0.0072 (12)
C13B0.0261 (15)0.0269 (15)0.0254 (15)0.0003 (12)0.0010 (11)0.0072 (12)
C14B0.0262 (14)0.0231 (14)0.0195 (13)0.0001 (11)0.0004 (11)0.0042 (11)
C15B0.0217 (14)0.0268 (15)0.0298 (15)0.0011 (12)0.0028 (12)0.0052 (12)
C16B0.0267 (15)0.0259 (15)0.0346 (17)0.0056 (12)0.0041 (13)0.0056 (13)
C17B0.0338 (17)0.0298 (16)0.0301 (16)0.0013 (13)0.0054 (13)0.0000 (13)
C18B0.0281 (16)0.0316 (16)0.0238 (15)0.0034 (13)0.0025 (12)0.0000 (12)
C19B0.0214 (14)0.0288 (15)0.0264 (15)0.0000 (11)0.0022 (11)0.0034 (12)
Geometric parameters (Å, º) top
O1A—N1A1.229 (4)C17A—H17A0.9900
O2A—N1A1.211 (4)C17A—H17B0.9900
O3A—C7A1.230 (4)C18A—C19A1.532 (4)
O1B—N1B1.213 (4)C18A—H18A0.9900
O2B—N1B1.229 (4)C18A—H18B0.9900
O3B—C7B1.226 (4)C19A—H19A0.9900
N1A—C1A1.481 (4)C19A—H19B0.9900
N2A—C7A1.356 (4)C1B—C6B1.369 (5)
N2A—C8A1.483 (4)C1B—C2B1.395 (5)
N2A—C14A1.483 (4)C2B—C3B1.393 (4)
N1B—C1B1.483 (4)C2B—H2BA0.9500
N2B—C7B1.359 (4)C3B—C4B1.383 (5)
N2B—C14B1.477 (4)C3B—H3BA0.9500
N2B—C8B1.480 (4)C4B—C5B1.391 (4)
C1A—C6A1.364 (5)C4B—C7B1.520 (4)
C1A—C2A1.397 (5)C5B—C6B1.391 (4)
C2A—C3A1.389 (5)C5B—H5BA0.9500
C2A—H2AA0.9500C6B—H6BA0.9500
C3A—C4A1.384 (5)C8B—C9B1.524 (4)
C3A—H3AA0.9500C8B—C13B1.538 (4)
C4A—C5A1.398 (4)C8B—H8BA1.0000
C4A—C7A1.519 (4)C9B—C10B1.528 (4)
C5A—C6A1.393 (4)C9B—H9BA0.9900
C5A—H5AA0.9500C9B—H9BB0.9900
C6A—H6AA0.9500C10B—C11B1.538 (5)
C8A—C13A1.524 (5)C10B—H10C0.9900
C8A—C9A1.533 (4)C10B—H10D0.9900
C8A—H8AA1.0000C11B—C12B1.517 (5)
C9A—C10A1.537 (4)C11B—H11C0.9900
C9A—H9AA0.9900C11B—H11D0.9900
C9A—H9AB0.9900C12B—C13B1.527 (4)
C10A—C11A1.520 (5)C12B—H12C0.9900
C10A—H10A0.9900C12B—H12D0.9900
C10A—H10B0.9900C13B—H13C0.9900
C11A—C12A1.527 (6)C13B—H13D0.9900
C11A—H11A0.9900C14B—C15B1.530 (4)
C11A—H11B0.9900C14B—C19B1.540 (4)
C12A—C13A1.530 (4)C14B—H14B1.0000
C12A—H12A0.9900C15B—C16B1.531 (4)
C12A—H12B0.9900C15B—H15C0.9900
C13A—H13A0.9900C15B—H15D0.9900
C13A—H13B0.9900C16B—C17B1.529 (5)
C14A—C15A1.530 (4)C16B—H16C0.9900
C14A—C19A1.536 (4)C16B—H16D0.9900
C14A—H14A1.0000C17B—C18B1.528 (5)
C15A—C16A1.533 (4)C17B—H17C0.9900
C15A—H15A0.9900C17B—H17D0.9900
C15A—H15B0.9900C18B—C19B1.530 (4)
C16A—C17A1.530 (5)C18B—H18C0.9900
C16A—H16A0.9900C18B—H18E0.9900
C16A—H16B0.9900C19B—H19E0.9900
C17A—C18A1.522 (5)C19B—H19C0.9900
O2A—N1A—O1A124.4 (3)C18A—C19A—C14A110.5 (2)
O2A—N1A—C1A118.6 (3)C18A—C19A—H19A109.6
O1A—N1A—C1A116.9 (3)C14A—C19A—H19A109.6
C7A—N2A—C8A119.5 (2)C18A—C19A—H19B109.6
C7A—N2A—C14A123.4 (3)C14A—C19A—H19B109.6
C8A—N2A—C14A116.7 (2)H19A—C19A—H19B108.1
O1B—N1B—O2B124.1 (3)C6B—C1B—C2B123.2 (3)
O1B—N1B—C1B118.7 (3)C6B—C1B—N1B118.7 (3)
O2B—N1B—C1B117.2 (3)C2B—C1B—N1B118.0 (3)
C7B—N2B—C14B123.6 (2)C3B—C2B—C1B117.4 (3)
C7B—N2B—C8B119.3 (2)C3B—C2B—H2BA121.3
C14B—N2B—C8B116.8 (2)C1B—C2B—H2BA121.3
C6A—C1A—C2A122.9 (3)C4B—C3B—C2B120.6 (3)
C6A—C1A—N1A118.7 (3)C4B—C3B—H3BA119.7
C2A—C1A—N1A118.4 (3)C2B—C3B—H3BA119.7
C3A—C2A—C1A117.8 (3)C3B—C4B—C5B120.3 (3)
C3A—C2A—H2AA121.1C3B—C4B—C7B122.6 (3)
C1A—C2A—H2AA121.1C5B—C4B—C7B116.8 (3)
C4A—C3A—C2A120.5 (3)C4B—C5B—C6B120.2 (3)
C4A—C3A—H3AA119.8C4B—C5B—H5BA119.9
C2A—C3A—H3AA119.8C6B—C5B—H5BA119.9
C3A—C4A—C5A120.2 (3)C1B—C6B—C5B118.3 (3)
C3A—C4A—C7A123.1 (3)C1B—C6B—H6BA120.9
C5A—C4A—C7A116.5 (3)C5B—C6B—H6BA120.9
C6A—C5A—C4A119.9 (3)O3B—C7B—N2B123.6 (3)
C6A—C5A—H5AA120.1O3B—C7B—C4B117.2 (3)
C4A—C5A—H5AA120.1N2B—C7B—C4B119.2 (3)
C1A—C6A—C5A118.6 (3)N2B—C8B—C9B112.9 (3)
C1A—C6A—H6AA120.7N2B—C8B—C13B112.0 (2)
C5A—C6A—H6AA120.7C9B—C8B—C13B112.3 (3)
O3A—C7A—N2A123.3 (3)N2B—C8B—H8BA106.4
O3A—C7A—C4A117.5 (3)C9B—C8B—H8BA106.4
N2A—C7A—C4A119.2 (3)C13B—C8B—H8BA106.4
N2A—C8A—C13A113.2 (2)C8B—C9B—C10B110.8 (3)
N2A—C8A—C9A112.7 (3)C8B—C9B—H9BA109.5
C13A—C8A—C9A111.9 (3)C10B—C9B—H9BA109.5
N2A—C8A—H8AA106.1C8B—C9B—H9BB109.5
C13A—C8A—H8AA106.1C10B—C9B—H9BB109.5
C9A—C8A—H8AA106.1H9BA—C9B—H9BB108.1
C8A—C9A—C10A109.4 (3)C9B—C10B—C11B110.5 (3)
C8A—C9A—H9AA109.8C9B—C10B—H10C109.6
C10A—C9A—H9AA109.8C11B—C10B—H10C109.6
C8A—C9A—H9AB109.8C9B—C10B—H10D109.6
C10A—C9A—H9AB109.8C11B—C10B—H10D109.6
H9AA—C9A—H9AB108.2H10C—C10B—H10D108.1
C11A—C10A—C9A111.6 (3)C12B—C11B—C10B110.8 (3)
C11A—C10A—H10A109.3C12B—C11B—H11C109.5
C9A—C10A—H10A109.3C10B—C11B—H11C109.5
C11A—C10A—H10B109.3C12B—C11B—H11D109.5
C9A—C10A—H10B109.3C10B—C11B—H11D109.5
H10A—C10A—H10B108.0H11C—C11B—H11D108.1
C10A—C11A—C12A111.5 (3)C11B—C12B—C13B111.4 (3)
C10A—C11A—H11A109.3C11B—C12B—H12C109.4
C12A—C11A—H11A109.3C13B—C12B—H12C109.4
C10A—C11A—H11B109.3C11B—C12B—H12D109.4
C12A—C11A—H11B109.3C13B—C12B—H12D109.4
H11A—C11A—H11B108.0H12C—C12B—H12D108.0
C11A—C12A—C13A110.9 (3)C12B—C13B—C8B109.6 (3)
C11A—C12A—H12A109.5C12B—C13B—H13C109.7
C13A—C12A—H12A109.5C8B—C13B—H13C109.7
C11A—C12A—H12B109.5C12B—C13B—H13D109.7
C13A—C12A—H12B109.5C8B—C13B—H13D109.7
H12A—C12A—H12B108.0H13C—C13B—H13D108.2
C8A—C13A—C12A110.2 (3)N2B—C14B—C15B111.6 (2)
C8A—C13A—H13A109.6N2B—C14B—C19B111.3 (2)
C12A—C13A—H13A109.6C15B—C14B—C19B111.0 (2)
C8A—C13A—H13B109.6N2B—C14B—H14B107.6
C12A—C13A—H13B109.6C15B—C14B—H14B107.6
H13A—C13A—H13B108.1C19B—C14B—H14B107.6
N2A—C14A—C15A111.7 (2)C14B—C15B—C16B110.9 (2)
N2A—C14A—C19A110.9 (2)C14B—C15B—H15C109.5
C15A—C14A—C19A111.5 (2)C16B—C15B—H15C109.5
N2A—C14A—H14A107.5C14B—C15B—H15D109.5
C15A—C14A—H14A107.5C16B—C15B—H15D109.5
C19A—C14A—H14A107.5H15C—C15B—H15D108.0
C14A—C15A—C16A110.3 (3)C17B—C16B—C15B111.0 (3)
C14A—C15A—H15A109.6C17B—C16B—H16C109.4
C16A—C15A—H15A109.6C15B—C16B—H16C109.4
C14A—C15A—H15B109.6C17B—C16B—H16D109.4
C16A—C15A—H15B109.6C15B—C16B—H16D109.4
H15A—C15A—H15B108.1H16C—C16B—H16D108.0
C17A—C16A—C15A110.8 (3)C18B—C17B—C16B110.7 (3)
C17A—C16A—H16A109.5C18B—C17B—H17C109.5
C15A—C16A—H16A109.5C16B—C17B—H17C109.5
C17A—C16A—H16B109.5C18B—C17B—H17D109.5
C15A—C16A—H16B109.5C16B—C17B—H17D109.5
H16A—C16A—H16B108.1H17C—C17B—H17D108.1
C18A—C17A—C16A110.5 (3)C17B—C18B—C19B110.6 (3)
C18A—C17A—H17A109.6C17B—C18B—H18C109.5
C16A—C17A—H17A109.6C19B—C18B—H18C109.5
C18A—C17A—H17B109.6C17B—C18B—H18E109.5
C16A—C17A—H17B109.6C19B—C18B—H18E109.5
H17A—C17A—H17B108.1H18C—C18B—H18E108.1
C17A—C18A—C19A111.6 (3)C18B—C19B—C14B110.4 (3)
C17A—C18A—H18A109.3C18B—C19B—H19E109.6
C19A—C18A—H18A109.3C14B—C19B—H19E109.6
C17A—C18A—H18B109.3C18B—C19B—H19C109.6
C19A—C18A—H18B109.3C14B—C19B—H19C109.6
H18A—C18A—H18B108.0H19E—C19B—H19C108.1
O2A—N1A—C1A—C6A176.6 (3)O1B—N1B—C1B—C6B178.1 (3)
O1A—N1A—C1A—C6A1.2 (4)O2B—N1B—C1B—C6B0.7 (4)
O2A—N1A—C1A—C2A3.9 (4)O1B—N1B—C1B—C2B3.5 (4)
O1A—N1A—C1A—C2A178.4 (3)O2B—N1B—C1B—C2B177.7 (3)
C6A—C1A—C2A—C3A2.1 (5)C6B—C1B—C2B—C3B1.7 (5)
N1A—C1A—C2A—C3A178.3 (3)N1B—C1B—C2B—C3B180.0 (3)
C1A—C2A—C3A—C4A0.4 (5)C1B—C2B—C3B—C4B1.2 (5)
C2A—C3A—C4A—C5A0.9 (5)C2B—C3B—C4B—C5B0.1 (5)
C2A—C3A—C4A—C7A175.6 (3)C2B—C3B—C4B—C7B172.8 (3)
C3A—C4A—C5A—C6A0.6 (4)C3B—C4B—C5B—C6B0.6 (4)
C7A—C4A—C5A—C6A175.7 (3)C7B—C4B—C5B—C6B173.9 (3)
C2A—C1A—C6A—C5A2.4 (5)C2B—C1B—C6B—C5B1.1 (5)
N1A—C1A—C6A—C5A178.1 (3)N1B—C1B—C6B—C5B179.4 (3)
C4A—C5A—C6A—C1A1.0 (5)C4B—C5B—C6B—C1B0.1 (5)
C8A—N2A—C7A—O3A0.7 (5)C14B—N2B—C7B—O3B171.0 (3)
C14A—N2A—C7A—O3A172.1 (3)C8B—N2B—C7B—O3B2.4 (5)
C8A—N2A—C7A—C4A179.7 (3)C14B—N2B—C7B—C4B9.0 (4)
C14A—N2A—C7A—C4A6.9 (4)C8B—N2B—C7B—C4B177.7 (3)
C3A—C4A—C7A—O3A121.5 (3)C3B—C4B—C7B—O3B119.6 (3)
C5A—C4A—C7A—O3A53.4 (4)C5B—C4B—C7B—O3B53.5 (4)
C3A—C4A—C7A—N2A59.5 (4)C3B—C4B—C7B—N2B60.4 (4)
C5A—C4A—C7A—N2A125.6 (3)C5B—C4B—C7B—N2B126.5 (3)
C7A—N2A—C8A—C13A63.0 (4)C7B—N2B—C8B—C9B63.0 (4)
C14A—N2A—C8A—C13A110.2 (3)C14B—N2B—C8B—C9B110.8 (3)
C7A—N2A—C8A—C9A65.2 (4)C7B—N2B—C8B—C13B64.9 (4)
C14A—N2A—C8A—C9A121.5 (3)C14B—N2B—C8B—C13B121.2 (3)
N2A—C8A—C9A—C10A174.3 (3)N2B—C8B—C9B—C10B176.9 (3)
C13A—C8A—C9A—C10A56.8 (3)C13B—C8B—C9B—C10B55.3 (3)
C8A—C9A—C10A—C11A55.6 (4)C8B—C9B—C10B—C11B55.3 (4)
C9A—C10A—C11A—C12A55.9 (4)C9B—C10B—C11B—C12B57.1 (4)
C10A—C11A—C12A—C13A55.7 (4)C10B—C11B—C12B—C13B58.2 (4)
N2A—C8A—C13A—C12A173.9 (3)C11B—C12B—C13B—C8B56.5 (3)
C9A—C8A—C13A—C12A57.4 (4)N2B—C8B—C13B—C12B176.5 (3)
C11A—C12A—C13A—C8A56.0 (4)C9B—C8B—C13B—C12B55.3 (3)
C7A—N2A—C14A—C15A112.5 (3)C7B—N2B—C14B—C15B122.7 (3)
C8A—N2A—C14A—C15A60.4 (3)C8B—N2B—C14B—C15B63.7 (3)
C7A—N2A—C14A—C19A122.5 (3)C7B—N2B—C14B—C19B112.6 (3)
C8A—N2A—C14A—C19A64.6 (3)C8B—N2B—C14B—C19B60.9 (3)
N2A—C14A—C15A—C16A179.0 (2)N2B—C14B—C15B—C16B179.6 (2)
C19A—C14A—C15A—C16A56.3 (3)C19B—C14B—C15B—C16B55.6 (3)
C14A—C15A—C16A—C17A57.2 (3)C14B—C15B—C16B—C17B55.9 (3)
C15A—C16A—C17A—C18A57.5 (4)C15B—C16B—C17B—C18B57.0 (4)
C16A—C17A—C18A—C19A56.8 (4)C16B—C17B—C18B—C19B57.8 (4)
C17A—C18A—C19A—C14A55.5 (3)C17B—C18B—C19B—C14B57.2 (3)
N2A—C14A—C19A—C18A179.6 (2)N2B—C14B—C19B—C18B178.7 (2)
C15A—C14A—C19A—C18A55.3 (3)C15B—C14B—C19B—C18B56.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5A—H5AA···O3Ai0.952.603.155 (4)118
C5B—H5BA···O3Bii0.952.543.148 (4)122
C9A—H9AA···O3A0.992.483.044 (4)115
C9B—H9BA···O3B0.992.382.983 (4)118
C13A—H13B···O3A0.992.433.001 (4)116
C13B—H13C···O3B0.992.473.043 (4)117
Symmetry codes: (i) x+2, y+2, z+2; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC19H26N2O3
Mr330.42
Crystal system, space groupTriclinic, 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)
V3)1731.97 (13)
Z4
Radiation typeCu Kα
µ (mm1)0.69
Crystal size (mm)0.29 × 0.26 × 0.07
Data collection
DiffractometerAgilent Xcalibur Ruby Gemini
diffractometer
Absorption correctionAnalytical
(Clark & Reid, 1995)
Tmin, Tmax0.823, 0.950
No. of measured, independent and
observed [I > 2σ(I)] reflections
12453, 6952, 6374
Rint0.028
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.080, 0.239, 1.11
No. of reflections6952
No. of parameters434
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.29

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5B—H5BA···O3Bi0.952.543.148 (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

First citationAgilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
First citationClark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897.  CrossRef CAS Web of Science IUCr Journals
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
First citationPriya, B. S., Swamy, B. S. N. & Rangapa, K. S. (2005). Bioorg. Med. Chem. 13, 2623–2628.  Web of Science CrossRef PubMed CAS
First citationSaeed, S., Jasinski, J. P. & Butcher, R. J. (2011). Acta Cryst. E67, o279.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationToda, F., Kai, A., Tagami, Y. & Mak, T. C. W. (1987). Chem. Lett. pp. 1393–1396.  CrossRef Web of Science

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