2,2-Diphenyl­acetamide

Jasinski, J.P.; Golen, J.A.; Siddegowda, M.S.; Yathirajan, H.S.; Swamy, M.T.

doi:10.1107/S1600536811026717

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages o1992-o1993

doi:10.1107/S1600536811026717

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2,2-Diphenylacetamide

Jerry P. Jasinski,^a ^* James A. Golen,^a M. S. Siddegowda,^b H. S. Yathirajan ^b and M. T. Swamy ^c

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Chemistry, Sambhram Institute of Technology, Bangalore 560 097, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 3 July 2011; accepted 5 July 2011; online 9 July 2011)

In the title compound, C₁₄H₁₃NO, which has two molecules in the asymmetric unit, the dihedral angles between the mean planes of the benzene rings are 84.6 (7) and 85.0 (6)°. N—H⋯O hydrogen bonds [forming R₂²(8) ring motifs] and C—H⋯O hydrogen bonds dominate the crystal packing, forming zigzag chains parallel to the a axis. In addition, weak intermolecular C—H⋯π interactions are observed.

Related literature

For the synthesis and antimycobacterial activity of 2,2-diphenylacetamide derivatives, see: Guzel et al. (2006 ). For related structures, see: Akkurt et al. (2007 ); Dutkiewicz et al. (2010 ); Gerkin (1998 ); Krigbaum et al. (1968 ); Narasegowda et al. (2005 ); Yathirajan et al. (2005 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₃NO
M_r = 211.25
Monoclinic, P 2₁
a = 5.1687 (3) Å
b = 28.5511 (13) Å
c = 7.8006 (4) Å
β = 98.152 (5)°
V = 1139.52 (10) Å³
Z = 4
Cu Kα radiation
μ = 0.61 mm⁻¹
T = 173 K
0.40 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.792, T_max = 0.887
6490 measured reflections
3978 independent reflections
3869 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.107
S = 1.07
3978 reflections
303 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of the C3–C8 and C23–C28 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1ⁱ	0.89 (1)	2.20 (2)	2.9409 (17)	140 (2)
N1—H1A⋯O2ⁱⁱ	0.87 (1)	2.09 (1)	2.9575 (19)	177 (2)
N2—H2B⋯O1ⁱⁱⁱ	0.88 (1)	2.07 (1)	2.9526 (19)	176 (2)
N2—H2A⋯O2^iv	0.89 (1)	2.17 (2)	2.9407 (18)	145 (2)
N1—H1A⋯N2ⁱⁱ	0.87 (1)	3.06 (2)	3.7246 (18)	134 (2)
N2—H2B⋯N1ⁱⁱⁱ	0.88 (1)	3.10 (2)	3.7246 (18)	130 (2)
C10—H10A⋯O1	0.95	2.50	3.093 (2)	120
C18—H18A⋯O2	0.95	2.51	3.099 (2)	120
C2—H2C⋯Cg1ⁱ	1.00	2.96	3.9379 (18)	165
C16—H16A⋯Cg4^iv	1.00	2.95	3.9263 (18)	166
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x, y, z-1; (iv) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811026717/jh2307sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026717/jh2307Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026717/jh2307Isup3.cml

checkCIF report

Comment top

The synthesis and antimycobacterial activity of some new 2,2-diphenylacetamide derivatives is described (Guzel et al., 2006). The title compound is used to synthesize various biologically active and pharmaceutical compounds viz., loperamide, darifenacin, fenpiverine, etc. The crystal structures of N,N-diphenylacetamide (Krigbaum et al., 1968), 4,4'-dimethylbiphenyl-2,2'-dicarboxylic acid (Gerkin, 1998), 4'-methylbiphenyl-2-carboxylic acid (Narasegowda et al., 2005) and 4'-(2-butyl-4-chloro-5-formylimidazol-1-ylmethyl)biphenyl-2-carbonitrile (Yathirajan et al., 2005), 2-hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2,2-diphenylacetamide (Akkurt et al., 2007) and 2-Chloro-N-[4-chloro-2-(2-chlorobenzoyl)phenyl]acetamide (Dutkiewicz et al., 2010) have been reported. In view of the importance of the title compound, (I), C₁₄H₁₃NO, and in order to determine the conformation of this molecule, a crystal structure determination has been carried out.

In the title compound, (I), with two molecules in the asymmetric unit, the dihedral angle between the mean planes of the benzene rings is 84.6 (7)° or 85.0 (6)°, respectively (Fig. 1). Extensive N—H···O (forming an R₂²(8) ring-motif) intermolecular and C—H···O intramolecular hydrogen bonds and weak C—H···Cg π-ring intermolecular interactions (dominate the crystal packing forming a zigzag chain along [010] (Table 1, Fg. 2).

Related literature top

For the synthesis and antimycobacterial activity of 2,2-diphenylacetamide derivatives, see: Guzel et al. (2006). For related structures, see: Akkurt et al. (2007); Dutkiewicz et al. (2010); Gerkin (1998); Krigbaum et al. (1968); Narasegowda et al. (2005); Yathirajan et al. (2005). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore. X-ray quality crystals were obtained by slow evaporation of 1:1 acetone:methanol solution (m.p.: 430-433 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); 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 the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed down the a axis. Dashed lines represent N—H···O hydrogen bonds.

2,2-Diphenylacetamide top

Crystal data top

C₁₄H₁₃NO	F(000) = 448
M_r = 211.25	D_x = 1.231 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 5082 reflections
a = 5.1687 (3) Å	θ = 4.6–70.4°
b = 28.5511 (13) Å	µ = 0.61 mm⁻¹
c = 7.8006 (4) Å	T = 173 K
β = 98.152 (5)°	Block, colorless
V = 1139.52 (10) Å³	0.40 × 0.25 × 0.20 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3978 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3869 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 16.1500 pixels mm^-1	θ_max = 70.5°, θ_min = 5.7°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −34→34
T_min = 0.792, T_max = 0.887	l = −9→8
6490 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0695P)² + 0.1057P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.027
3978 reflections	Δρ_max = 0.21 e Å⁻³
303 parameters	Δρ_min = −0.20 e Å⁻³
9 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0118 (13)

Crystal data top

C₁₄H₁₃NO	V = 1139.52 (10) Å³
M_r = 211.25	Z = 4
Monoclinic, P2₁	Cu Kα radiation
a = 5.1687 (3) Å	µ = 0.61 mm⁻¹
b = 28.5511 (13) Å	T = 173 K
c = 7.8006 (4) Å	0.40 × 0.25 × 0.20 mm
β = 98.152 (5)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3978 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	3869 reflections with I > 2σ(I)
T_min = 0.792, T_max = 0.887	R_int = 0.017
6490 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	9 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.21 e Å⁻³
3978 reflections	Δρ_min = −0.20 e Å⁻³
303 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
N1	0.9797 (3)	0.54261 (6)	0.6365 (2)	0.0459 (3)
H1B	1.121 (3)	0.5307 (8)	0.600 (3)	0.055*
H1A	0.984 (5)	0.5667 (6)	0.706 (3)	0.055*
O2	1.0081 (2)	0.62240 (4)	−0.11977 (17)	0.0465 (3)
O1	0.5496 (2)	0.53784 (5)	0.64407 (16)	0.0459 (3)
N2	0.5779 (3)	0.61736 (6)	−0.1120 (2)	0.0469 (4)
H2B	0.561 (5)	0.5935 (6)	−0.185 (3)	0.056*
H2A	0.431 (3)	0.6281 (9)	−0.080 (3)	0.056*
C1	0.7494 (3)	0.52226 (5)	0.5965 (2)	0.0359 (3)
C2	0.7440 (3)	0.47718 (6)	0.4902 (2)	0.0377 (3)
H2C	0.9097	0.4758	0.4381	0.045*
C3	0.5167 (3)	0.47744 (6)	0.3416 (2)	0.0406 (4)
C4	0.4550 (5)	0.51789 (8)	0.2469 (3)	0.0678 (6)
H4A	0.5534	0.5456	0.2759	0.081*
C5	0.2520 (6)	0.51860 (10)	0.1106 (4)	0.0824 (8)
H5A	0.2130	0.5467	0.0469	0.099*
C6	0.1062 (5)	0.47893 (10)	0.0666 (3)	0.0683 (6)
H6A	−0.0353	0.4796	−0.0254	0.082*
C7	0.1684 (4)	0.43851 (9)	0.1575 (3)	0.0577 (5)
H7A	0.0707	0.4108	0.1272	0.069*
C8	0.3724 (4)	0.43764 (7)	0.2933 (2)	0.0461 (4)
H8A	0.4138	0.4092	0.3543	0.055*
C9	0.7419 (3)	0.43519 (5)	0.6105 (2)	0.0375 (3)
C10	0.5760 (4)	0.43225 (7)	0.7334 (3)	0.0518 (4)
H10A	0.4577	0.4571	0.7451	0.062*
C11	0.5795 (5)	0.39352 (9)	0.8402 (3)	0.0606 (5)
H11A	0.4630	0.3921	0.9239	0.073*
C12	0.7488 (5)	0.35715 (8)	0.8270 (3)	0.0607 (5)
H12A	0.7521	0.3309	0.9020	0.073*
C13	0.9135 (5)	0.35925 (9)	0.7036 (4)	0.0738 (7)
H13A	1.0288	0.3340	0.6910	0.089*
C14	0.9117 (4)	0.39807 (8)	0.5981 (3)	0.0607 (5)
H14A	1.0294	0.3994	0.5151	0.073*
C15	0.8083 (3)	0.63780 (6)	−0.0712 (2)	0.0355 (3)
C16	0.8143 (3)	0.68289 (5)	0.0360 (2)	0.0367 (3)
H16A	0.6495	0.6841	0.0892	0.044*
C17	0.8148 (3)	0.72535 (6)	−0.0840 (2)	0.0373 (3)
C18	0.9825 (4)	0.72830 (7)	−0.2076 (2)	0.0505 (4)
H18A	1.1005	0.7034	−0.2201	0.061*
C19	0.9779 (4)	0.76758 (8)	−0.3129 (3)	0.0594 (5)
H19A	1.0941	0.7694	−0.3967	0.071*
C20	0.8089 (5)	0.80352 (7)	−0.2976 (3)	0.0585 (5)
H20A	0.8061	0.8301	−0.3710	0.070*
C21	0.6427 (5)	0.80100 (8)	−0.1751 (3)	0.0654 (6)
H21A	0.5257	0.8260	−0.1627	0.078*
C22	0.6461 (4)	0.76191 (7)	−0.0699 (3)	0.0533 (5)
H22A	0.5294	0.7603	0.0137	0.064*
C23	1.0422 (3)	0.68233 (6)	0.1827 (2)	0.0404 (3)
C24	1.1076 (5)	0.64165 (8)	0.2764 (3)	0.0702 (6)
H24A	1.0119	0.6137	0.2462	0.084*
C25	1.3098 (6)	0.64110 (11)	0.4128 (3)	0.0848 (8)
H25A	1.3508	0.6129	0.4757	0.102*
C26	1.4513 (5)	0.68078 (11)	0.4580 (3)	0.0696 (6)
H26A	1.5922	0.6801	0.5505	0.084*
C27	1.3884 (4)	0.72136 (9)	0.3690 (3)	0.0608 (5)
H27A	1.4847	0.7491	0.4008	0.073*
C28	1.1853 (4)	0.72226 (7)	0.2329 (2)	0.0468 (4)
H28A	1.1432	0.7508	0.1727	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0328 (6)	0.0411 (8)	0.0651 (9)	−0.0033 (6)	0.0110 (6)	−0.0140 (7)
O2	0.0316 (5)	0.0435 (7)	0.0654 (7)	−0.0009 (5)	0.0106 (5)	−0.0159 (5)
O1	0.0321 (5)	0.0424 (6)	0.0639 (7)	−0.0001 (5)	0.0093 (5)	−0.0150 (6)
N2	0.0325 (6)	0.0435 (8)	0.0652 (9)	−0.0021 (6)	0.0086 (6)	−0.0147 (7)
C1	0.0322 (7)	0.0325 (8)	0.0430 (8)	0.0009 (5)	0.0051 (6)	−0.0007 (6)
C2	0.0361 (7)	0.0352 (8)	0.0436 (8)	−0.0012 (6)	0.0116 (6)	−0.0032 (7)
C3	0.0436 (8)	0.0388 (9)	0.0407 (8)	−0.0019 (6)	0.0107 (6)	−0.0039 (7)
C4	0.0871 (15)	0.0441 (11)	0.0663 (13)	−0.0108 (10)	−0.0092 (11)	0.0077 (9)
C5	0.107 (2)	0.0650 (15)	0.0660 (14)	−0.0016 (14)	−0.0202 (14)	0.0137 (12)
C6	0.0713 (13)	0.0847 (16)	0.0442 (10)	0.0011 (12)	−0.0085 (9)	−0.0065 (10)
C7	0.0624 (11)	0.0665 (13)	0.0438 (9)	−0.0133 (10)	0.0061 (8)	−0.0125 (9)
C8	0.0545 (9)	0.0452 (10)	0.0398 (8)	−0.0061 (8)	0.0109 (7)	−0.0068 (7)
C9	0.0368 (7)	0.0332 (8)	0.0423 (8)	−0.0013 (6)	0.0048 (6)	−0.0052 (6)
C10	0.0547 (10)	0.0487 (11)	0.0557 (10)	0.0113 (8)	0.0204 (8)	0.0036 (8)
C11	0.0734 (13)	0.0576 (11)	0.0565 (11)	0.0015 (10)	0.0284 (10)	0.0067 (10)
C12	0.0769 (13)	0.0434 (11)	0.0636 (12)	0.0004 (10)	0.0164 (10)	0.0106 (9)
C13	0.0837 (15)	0.0440 (11)	0.1012 (18)	0.0193 (11)	0.0389 (14)	0.0163 (11)
C14	0.0657 (12)	0.0439 (10)	0.0795 (14)	0.0133 (9)	0.0346 (10)	0.0054 (10)
C15	0.0327 (7)	0.0324 (7)	0.0418 (7)	−0.0002 (6)	0.0066 (6)	−0.0006 (6)
C16	0.0357 (7)	0.0337 (8)	0.0430 (8)	−0.0020 (6)	0.0129 (6)	−0.0041 (7)
C17	0.0363 (7)	0.0358 (8)	0.0399 (7)	−0.0021 (6)	0.0055 (6)	−0.0057 (6)
C18	0.0531 (10)	0.0481 (10)	0.0534 (10)	0.0080 (8)	0.0186 (8)	0.0042 (8)
C19	0.0686 (12)	0.0591 (12)	0.0550 (11)	0.0016 (10)	0.0245 (9)	0.0069 (10)
C20	0.0752 (13)	0.0429 (11)	0.0583 (11)	−0.0010 (9)	0.0123 (10)	0.0104 (8)
C21	0.0786 (15)	0.0409 (10)	0.0818 (15)	0.0171 (9)	0.0294 (12)	0.0066 (10)
C22	0.0597 (10)	0.0404 (9)	0.0655 (11)	0.0073 (8)	0.0291 (9)	0.0050 (8)
C23	0.0451 (8)	0.0399 (9)	0.0381 (7)	−0.0005 (6)	0.0123 (6)	−0.0036 (7)
C24	0.0878 (16)	0.0478 (12)	0.0684 (13)	−0.0088 (11)	−0.0116 (12)	0.0077 (10)
C25	0.109 (2)	0.0685 (16)	0.0669 (14)	0.0064 (15)	−0.0228 (14)	0.0127 (12)
C26	0.0741 (13)	0.0856 (16)	0.0441 (10)	0.0001 (12)	−0.0091 (9)	−0.0043 (11)
C27	0.0643 (12)	0.0720 (14)	0.0462 (9)	−0.0175 (10)	0.0081 (9)	−0.0141 (10)
C28	0.0553 (10)	0.0452 (10)	0.0411 (8)	−0.0090 (8)	0.0112 (7)	−0.0057 (7)

Geometric parameters (Å, º) top

N1—C1	1.322 (2)	C12—H12A	0.9500
N1—H1B	0.889 (13)	C13—C14	1.380 (3)
N1—H1A	0.873 (13)	C13—H13A	0.9500
O2—C15	1.2306 (19)	C14—H14A	0.9500
O1—C1	1.2292 (19)	C15—C16	1.533 (2)
N2—C15	1.324 (2)	C16—C23	1.521 (2)
N2—H2B	0.883 (13)	C16—C17	1.532 (2)
N2—H2A	0.889 (13)	C16—H16A	1.0000
C1—C2	1.529 (2)	C17—C22	1.375 (2)
C2—C9	1.523 (2)	C17—C18	1.387 (2)
C2—C3	1.529 (2)	C18—C19	1.388 (3)
C2—H2C	1.0000	C18—H18A	0.9500
C3—C8	1.382 (2)	C19—C20	1.364 (3)
C3—C4	1.384 (3)	C19—H19A	0.9500
C4—C5	1.384 (3)	C20—C21	1.374 (4)
C4—H4A	0.9500	C20—H20A	0.9500
C5—C6	1.377 (4)	C21—C22	1.384 (3)
C5—H5A	0.9500	C21—H21A	0.9500
C6—C7	1.369 (4)	C22—H22A	0.9500
C6—H6A	0.9500	C23—C28	1.385 (2)
C7—C8	1.385 (3)	C23—C24	1.389 (3)
C7—H7A	0.9500	C24—C25	1.382 (3)
C8—H8A	0.9500	C24—H24A	0.9500
C9—C10	1.377 (3)	C25—C26	1.367 (4)
C9—C14	1.388 (3)	C25—H25A	0.9500
C10—C11	1.383 (3)	C26—C27	1.366 (4)
C10—H10A	0.9500	C26—H26A	0.9500
C11—C12	1.371 (3)	C27—C28	1.384 (3)
C11—H11A	0.9500	C27—H27A	0.9500
C12—C13	1.373 (4)	C28—H28A	0.9500

C1—N1—H1B	120.8 (16)	C13—C14—C9	121.52 (19)
C1—N1—H1A	115.9 (16)	C13—C14—H14A	119.2
H1B—N1—H1A	123 (2)	C9—C14—H14A	119.2
C15—N2—H2B	119.8 (16)	O2—C15—N2	122.28 (16)
C15—N2—H2A	123.8 (16)	O2—C15—C16	120.98 (13)
H2B—N2—H2A	116 (2)	N2—C15—C16	116.72 (13)
O1—C1—N1	122.46 (15)	C23—C16—C17	113.57 (13)
O1—C1—C2	121.11 (14)	C23—C16—C15	110.82 (13)
N1—C1—C2	116.42 (14)	C17—C16—C15	109.44 (12)
C9—C2—C1	109.27 (13)	C23—C16—H16A	107.6
C9—C2—C3	113.52 (13)	C17—C16—H16A	107.6
C1—C2—C3	111.11 (13)	C15—C16—H16A	107.6
C9—C2—H2C	107.6	C22—C17—C18	118.40 (16)
C1—C2—H2C	107.6	C22—C17—C16	119.72 (14)
C3—C2—H2C	107.6	C18—C17—C16	121.88 (14)
C8—C3—C4	117.79 (17)	C17—C18—C19	120.03 (18)
C8—C3—C2	121.97 (15)	C17—C18—H18A	120.0
C4—C3—C2	120.21 (16)	C19—C18—H18A	120.0
C5—C4—C3	121.0 (2)	C20—C19—C18	120.89 (19)
C5—C4—H4A	119.5	C20—C19—H19A	119.6
C3—C4—H4A	119.5	C18—C19—H19A	119.6
C4—C5—C6	120.5 (2)	C19—C20—C21	119.51 (19)
C4—C5—H5A	119.7	C19—C20—H20A	120.2
C6—C5—H5A	119.7	C21—C20—H20A	120.2
C7—C6—C5	119.0 (2)	C20—C21—C22	119.9 (2)
C7—C6—H6A	120.5	C20—C21—H21A	120.1
C5—C6—H6A	120.5	C22—C21—H21A	120.1
C6—C7—C8	120.59 (19)	C17—C22—C21	121.31 (19)
C6—C7—H7A	119.7	C17—C22—H22A	119.3
C8—C7—H7A	119.7	C21—C22—H22A	119.3
C3—C8—C7	121.11 (18)	C28—C23—C24	117.35 (17)
C3—C8—H8A	119.4	C28—C23—C16	121.97 (15)
C7—C8—H8A	119.4	C24—C23—C16	120.64 (16)
C10—C9—C14	117.65 (17)	C25—C24—C23	121.1 (2)
C10—C9—C2	122.44 (15)	C25—C24—H24A	119.5
C14—C9—C2	119.91 (15)	C23—C24—H24A	119.5
C9—C10—C11	120.79 (18)	C26—C25—C24	120.5 (2)
C9—C10—H10A	119.6	C26—C25—H25A	119.7
C11—C10—H10A	119.6	C24—C25—H25A	119.7
C12—C11—C10	120.97 (19)	C25—C26—C27	119.4 (2)
C12—C11—H11A	119.5	C25—C26—H26A	120.3
C10—C11—H11A	119.5	C27—C26—H26A	120.3
C11—C12—C13	119.0 (2)	C26—C27—C28	120.4 (2)
C11—C12—H12A	120.5	C26—C27—H27A	119.8
C13—C12—H12A	120.5	C28—C27—H27A	119.8
C12—C13—C14	120.0 (2)	C27—C28—C23	121.22 (18)
C12—C13—H13A	120.0	C27—C28—H28A	119.4
C14—C13—H13A	120.0	C23—C28—H28A	119.4

O1—C1—C2—C9	−79.23 (19)	O2—C15—C16—C23	−46.8 (2)
N1—C1—C2—C9	99.42 (17)	N2—C15—C16—C23	135.00 (15)
O1—C1—C2—C3	46.8 (2)	O2—C15—C16—C17	79.24 (18)
N1—C1—C2—C3	−134.55 (16)	N2—C15—C16—C17	−99.00 (16)
C9—C2—C3—C8	−17.6 (2)	C23—C16—C17—C22	−103.20 (18)
C1—C2—C3—C8	−141.21 (16)	C15—C16—C17—C22	132.39 (17)
C9—C2—C3—C4	164.54 (19)	C23—C16—C17—C18	76.54 (19)
C1—C2—C3—C4	40.9 (2)	C15—C16—C17—C18	−47.87 (19)
C8—C3—C4—C5	1.2 (4)	C22—C17—C18—C19	0.2 (3)
C2—C3—C4—C5	179.2 (2)	C16—C17—C18—C19	−179.50 (18)
C3—C4—C5—C6	0.2 (5)	C17—C18—C19—C20	−0.4 (3)
C4—C5—C6—C7	−1.3 (5)	C18—C19—C20—C21	0.6 (4)
C5—C6—C7—C8	0.9 (4)	C19—C20—C21—C22	−0.7 (4)
C4—C3—C8—C7	−1.6 (3)	C18—C17—C22—C21	−0.3 (3)
C2—C3—C8—C7	−179.55 (17)	C16—C17—C22—C21	179.4 (2)
C6—C7—C8—C3	0.6 (3)	C20—C21—C22—C17	0.6 (4)
C1—C2—C9—C10	47.5 (2)	C17—C16—C23—C28	18.5 (2)
C3—C2—C9—C10	−77.1 (2)	C15—C16—C23—C28	142.15 (16)
C1—C2—C9—C14	−132.47 (18)	C17—C16—C23—C24	−164.12 (19)
C3—C2—C9—C14	102.9 (2)	C15—C16—C23—C24	−40.5 (2)
C14—C9—C10—C11	−0.1 (3)	C28—C23—C24—C25	−0.8 (4)
C2—C9—C10—C11	179.91 (18)	C16—C23—C24—C25	−178.3 (2)
C9—C10—C11—C12	0.3 (3)	C23—C24—C25—C26	−0.4 (5)
C10—C11—C12—C13	−1.0 (4)	C24—C25—C26—C27	1.1 (5)
C11—C12—C13—C14	1.6 (4)	C25—C26—C27—C28	−0.8 (4)
C12—C13—C14—C9	−1.4 (4)	C26—C27—C28—C23	−0.4 (3)
C10—C9—C14—C13	0.7 (3)	C24—C23—C28—C27	1.1 (3)
C2—C9—C14—C13	−179.3 (2)	C16—C23—C28—C27	178.60 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg4 are the centroids of the C3–C8 and C23–C28 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1ⁱ	0.89 (1)	2.20 (2)	2.9409 (17)	140 (2)
N1—H1A···O2ⁱⁱ	0.87 (1)	2.09 (1)	2.9575 (19)	177 (2)
N2—H2B···O1ⁱⁱⁱ	0.88 (1)	2.07 (1)	2.9526 (19)	176 (2)
N2—H2A···O2^iv	0.89 (1)	2.17 (2)	2.9407 (18)	145 (2)
N1—H1A···N2ⁱⁱ	0.87 (1)	3.06 (2)	3.7246 (18)	134 (2)
N2—H2B···N1ⁱⁱⁱ	0.88 (1)	3.10 (2)	3.7246 (18)	130 (2)
C10—H10A···O1	0.95	2.50	3.093 (2)	120
C18—H18A···O2	0.95	2.51	3.099 (2)	120
C2—H2C···Cg1ⁱ	1.00	2.96	3.9379 (18)	165
C16—H16A···Cg4^iv	1.00	2.95	3.9263 (18)	166

Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x, y, z−1; (iv) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO
M_r	211.25
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	5.1687 (3), 28.5511 (13), 7.8006 (4)
β (°)	98.152 (5)
V (Å³)	1139.52 (10)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.40 × 0.25 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.792, 0.887
No. of measured, independent and observed [I > 2σ(I)] reflections	6490, 3978, 3869
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.612

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.107, 1.07
No. of reflections	3978
No. of parameters	303
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg4 are the centroids of the C3–C8 and C23–C28 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1ⁱ	0.889 (13)	2.201 (18)	2.9409 (17)	140 (2)
N1—H1A···O2ⁱⁱ	0.873 (13)	2.086 (13)	2.9575 (19)	177 (2)
N2—H2B···O1ⁱⁱⁱ	0.883 (13)	2.071 (13)	2.9526 (19)	176 (2)
N2—H2A···O2^iv	0.889 (13)	2.169 (17)	2.9407 (18)	145 (2)
N1—H1A···N2ⁱⁱ	0.873 (13)	3.06 (2)	3.7246 (18)	134.4 (19)
N2—H2B···N1ⁱⁱⁱ	0.883 (13)	3.10 (2)	3.7246 (18)	129.9 (19)
C10—H10A···O1	0.95	2.50	3.093 (2)	120.
C18—H18A···O2	0.95	2.51	3.099 (2)	120
C2—H2C···Cg1ⁱ	1.00	2.96	3.9379 (18)	165
C16—H16A···Cg4^iv	1.00	2.95	3.9263 (18)	166

Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x, y, z−1; (iv) x−1, y, z.

Acknowledgements

JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer. MSS thanks the University of Mysore for the research facilities and R. L. Fine Chem, Bangalore, India, for the gift sample.

References

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Volume 67| Part 8| August 2011| Pages o1992-o1993

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