N-(2,4-Dimethyl­phen­yl)-2,2-diphenyl­acetamide

Fun, H.-K.; Chia, T.S.; Nayak, P.S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812014079

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1316-o1317

doi:10.1107/S1600536812014079

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N-(2,4-Dimethylphenyl)-2,2-diphenylacetamide

Hoong-Kun Fun,^a ^*‡ Tze Shyang Chia,^a Prakash S. Nayak,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Montepadavu, PO, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 14 March 2012; accepted 31 March 2012; online 6 April 2012)

The asymmetric unit of the title compound, C₂₂H₂₁NO, consists of two crystallographically independent molecules (A and B). Each molecule contains two benzene rings and one dimethylbenzene ring. The dihedral angle between the two benzene rings is 87.75 (16)° in molecule A and 89.25 (16)° in molecule B. In molecule A, the dimethylbenzene ring forms dihedral angles of 89.65 (8) and 42.98 (11)° with the two benzene rings, whereas the corresponding angles are equal to 63.15 (7) and 58.67 (10)° in molecule B. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif in each molecule. In the crystal, molecules are linked by bifurcated (N,C)—H⋯O hydrogen bonds, generating R₂¹(6) ring motifs and forming infinite chains along the a axis. The crystal is further stabilized by C—H⋯π and π–π interactions with centroid–centroid distances of 3.8543 (18) and 3.930 (2) Å.

Related literature

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006 ); Mijin et al. (2008 ). For the coordination abilities of amides, see: Wu et al. (2008 , 2010 ). For related structures, see: Praveen et al. (2011a ,b ,c ); Fun et al. (2011a ,b ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For reference bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₂H₂₁NO
M_r = 315.40
Triclinic, $[P \overline 1]$
a = 9.5520 (9) Å
b = 10.2011 (10) Å
c = 17.9656 (17) Å
α = 91.030 (2)°
β = 98.957 (2)°
γ = 90.377 (2)°
V = 1728.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.41 × 0.19 × 0.17 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.970, T_max = 0.987
30869 measured reflections
7858 independent reflections
6570 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.085
wR(F²) = 0.261
S = 1.14
7858 reflections
445 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg4 and Cg5 are the centroids of the C1A–C6A, C1B–C6B and C8B–C13B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O1Bⁱ	0.88 (4)	2.13 (4)	2.980 (3)	163 (3)
N1B—H1NB⋯O1A	0.86 (5)	2.18 (5)	3.012 (3)	162 (3)
C7A—H7AA⋯O1Bⁱ	1.00	2.32	3.258 (4)	155
C9A—H9AA⋯O1A	0.95	2.48	3.110 (4)	123
C7B—H7BA⋯O1A	1.00	2.27	3.225 (4)	160
C13B—H13B⋯O1B	0.95	2.46	3.087 (4)	124
C3A—H3AA⋯Cg5ⁱⁱ	0.95	2.89	3.754 (4)	151
C4A—H4AA⋯Cg4	0.95	2.84	3.539 (4)	131
C13A—H13A⋯Cg4ⁱ	0.95	2.68	3.561 (3)	154
C9B—H9BA⋯Cg1	0.95	2.62	3.546 (3)	167
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812014079/ez2289sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014079/ez2289Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812014079/ez2289Isup3.cml

checkCIF report

Comment top

N-Substituted 2-arylacetamides are very interesting compounds because of their structural similarity to the lateral chain of natural benzylpenicillin (Mijin & Marinkovic, 2006; Mijin et al., 2008). Amides are also used as ligands due to their excellent coordination abilities (Wu et al., 2008, 2010). Crystal structures of some acetamide derivatives viz., N-(4-chloro-1,3-benzothiazol-2-yl)-2-(3-methylphenyl)acetamide monohydrate, N-(3-chloro-4-fluorophenyl)-2,2-diphenylacetamide and N-(3-chloro-4-fluorophenyl)-2-(naphthalen-1-yl)acetamide (Praveen et al., 2011a,b,c) have been reported. In continuation of our work on synthesis of amides (Fun et al., 2011a,b), we report herein the crystal structure of the title compound (I).

The asymmetric unit of the title compound consists of two crystallographically independent molecules (A and B) as shown in Fig. 1. Each molecule contains two benzene rings (C1–C6 & C8–C13) and one dimethylbenzene ring (C15–C22) [maximum deviation = 0.0185 (27) Å at atom C19A in molecule A and 0.0155 (21) Å at atom C21B in molecule B]. The dihedral angle between the two benzene rings is 87.75 (16)° in molecule A and 89.25 (16)° in molecule B. In molecule A, the dimethylbenzene ring forms dihedral angles of 89.65 (8) and 42.98 (11)° with the two benzene rings (C1–C6 and C8–C13 respectively), whereas the corresponding angles are equal to 63.15 (7) and 58.67 (10)° in molecule B. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2011a,b). Intramolecular C9A—H9AA···O1A hydrogen bond (Table 1) generates an S(6) ring motif (Fig. 1; Bernstein et al., 1995) in molecule A, whereas the same ring motif is generated by C13B—H13B···O1B hydrogen bonds in molecule B.

In the crystal, molecules are linked by intermolecular bifurcated N1A—H1NA···O1B, N1B—H1NB···O1A, C7A—H7AA···O1B and C7B—H7BA···O1A hydrogen bonds (Table 1), generating R₂¹(6) ring motifs and forming infinite chains along the a axis. The crystal is further stabilized by C—H···π interactions, involving Cg1, Cg4 and Cg5 which are the centroids of C1A–C6A, C1B–C6B and C8B–C13B rings, respectively. π—π interactions are also observed with Cg3···Cg3 and Cg6···Cg6 distances of 3.8543 (18) Å[symmetry code: –X,-Y,-Z] and 3.930 (2) Å[symmetry code: 1-X,1-Y,-Z], where Cg3 and Cg6 are the centroids of C15A–C20A and C15B–C20B, respectively.

Related literature top

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006); Mijin et al. (2008). For the coordination abilities of amides, see: Wu et al. (2008, 2010). For related structures, see: Praveen et al. (2011a,b,c); Fun et al. (2011a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995). For reference bond lengths, see: Allen et al. (1987).

Experimental top

Diphenylacetic acid (0.212 g, 1 mmol), 2,4-dimethylaniline (0.1 ml, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) were dissolved in dichloromethane (20 ml). The mixture was stirred in the presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring which was then extracted thrice with dichloromethane. Organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound (I). Single crystals were grown from methylene chloride and ethanol (1:1) mixture by the slow evaporation method (M.P.: 430–432 K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels with 50% probability displacement ellipsoids. Intramolecular hydrogen bonds are shown by dashed lines.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds.

N-(2,4-Dimethylphenyl)-2,2-diphenylacetamide top

Crystal data top

C₂₂H₂₁NO	Z = 4
M_r = 315.40	F(000) = 672
Triclinic, P1	D_x = 1.212 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5520 (9) Å	Cell parameters from 9946 reflections
b = 10.2011 (10) Å	θ = 2.3–32.3°
c = 17.9656 (17) Å	µ = 0.07 mm⁻¹
α = 91.030 (2)°	T = 100 K
β = 98.957 (2)°	Block, colourless
γ = 90.377 (2)°	0.41 × 0.19 × 0.17 mm
V = 1728.9 (3) Å³

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	7858 independent reflections
Radiation source: fine-focus sealed tube	6570 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.970, T_max = 0.987	k = −13→13
30869 measured reflections	l = −23→23

Refinement top

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)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.261	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.097P)² + 5.029P] where P = (F_o² + 2F_c²)/3
7858 reflections	(Δ/σ)_max < 0.001
445 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₂₂H₂₁NO	γ = 90.377 (2)°
M_r = 315.40	V = 1728.9 (3) Å³
Triclinic, P1	Z = 4
a = 9.5520 (9) Å	Mo Kα radiation
b = 10.2011 (10) Å	µ = 0.07 mm⁻¹
c = 17.9656 (17) Å	T = 100 K
α = 91.030 (2)°	0.41 × 0.19 × 0.17 mm
β = 98.957 (2)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	7858 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6570 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.987	R_int = 0.040
30869 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.085	0 restraints
wR(F²) = 0.261	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.61 e Å⁻³
7858 reflections	Δρ_min = −0.42 e Å⁻³
445 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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

	x	y	z	U_iso*/U_eq
O1A	0.2422 (2)	0.2899 (2)	0.22082 (12)	0.0202 (5)
N1A	0.0206 (3)	0.2282 (3)	0.16612 (14)	0.0173 (5)
C1A	0.0812 (3)	0.1366 (3)	0.3930 (2)	0.0233 (6)
H1AA	−0.0062	0.0995	0.3692	0.028*
C2A	0.1554 (4)	0.0785 (3)	0.4571 (2)	0.0281 (7)
H2AA	0.1171	0.0032	0.4772	0.034*
C3A	0.2845 (4)	0.1301 (3)	0.49134 (18)	0.0255 (7)
H3AA	0.3344	0.0902	0.5349	0.031*
C4A	0.3407 (4)	0.2397 (3)	0.46204 (18)	0.0226 (6)
H4AA	0.4301	0.2743	0.4848	0.027*
C5A	0.2655 (3)	0.2991 (3)	0.39907 (17)	0.0190 (6)
H5AA	0.3033	0.3753	0.3796	0.023*
C6A	0.1347 (3)	0.2479 (3)	0.36411 (16)	0.0163 (6)
C7A	0.0518 (3)	0.3118 (3)	0.29485 (16)	0.0159 (6)
H7AA	−0.0467	0.2749	0.2878	0.019*
C8A	0.0405 (3)	0.4598 (3)	0.30493 (16)	0.0166 (6)
C9A	0.1067 (4)	0.5504 (3)	0.26542 (19)	0.0271 (7)
H9AA	0.1658	0.5209	0.2307	0.033*
C10A	0.0877 (4)	0.6843 (4)	0.2758 (2)	0.0321 (8)
H10A	0.1340	0.7454	0.2484	0.039*
C11A	0.0020 (4)	0.7286 (3)	0.3260 (2)	0.0273 (7)
H11A	−0.0126	0.8199	0.3323	0.033*
C12A	−0.0624 (4)	0.6392 (3)	0.3667 (2)	0.0289 (7)
H12A	−0.1192	0.6694	0.4024	0.035*
C13A	−0.0448 (3)	0.5061 (3)	0.35622 (19)	0.0238 (7)
H13A	−0.0911	0.4455	0.3840	0.029*
C14A	0.1152 (3)	0.2754 (3)	0.22425 (16)	0.0153 (5)
C15A	0.0619 (3)	0.1939 (3)	0.09481 (16)	0.0173 (6)
C16A	0.0185 (3)	0.2723 (3)	0.03354 (17)	0.0218 (6)
H16A	−0.0384	0.3469	0.0389	0.026*
C17A	0.0588 (3)	0.2413 (3)	−0.03656 (18)	0.0247 (7)
H17A	0.0294	0.2954	−0.0785	0.030*
C18A	0.1409 (3)	0.1327 (3)	−0.04488 (17)	0.0224 (6)
C19A	0.1815 (3)	0.0544 (3)	0.01743 (18)	0.0215 (6)
H19A	0.2365	−0.0213	0.0115	0.026*
C20A	0.1447 (3)	0.0825 (3)	0.08783 (17)	0.0188 (6)
C21A	0.1879 (4)	0.0999 (4)	−0.11911 (19)	0.0303 (8)
H21A	0.1206	0.1363	−0.1602	0.045*
H21B	0.1912	0.0044	−0.1257	0.045*
H21C	0.2823	0.1375	−0.1198	0.045*
C22A	0.1939 (4)	−0.0053 (3)	0.15325 (19)	0.0258 (7)
H22A	0.2083	−0.0941	0.1343	0.039*
H22B	0.1220	−0.0078	0.1866	0.039*
H22C	0.2832	0.0288	0.1813	0.039*
O1B	0.7412 (2)	0.1999 (2)	0.21860 (12)	0.0192 (5)
N1B	0.5215 (3)	0.2611 (3)	0.16445 (14)	0.0171 (5)
C1B	0.5909 (3)	0.3858 (3)	0.36734 (19)	0.0216 (6)
H1BA	0.5300	0.4273	0.3280	0.026*
C2B	0.6464 (4)	0.4580 (3)	0.4319 (2)	0.0250 (7)
H2BA	0.6213	0.5472	0.4370	0.030*
C3B	0.7388 (4)	0.3989 (3)	0.48871 (18)	0.0259 (7)
H3BA	0.7778	0.4475	0.5327	0.031*
C4B	0.7732 (4)	0.2688 (3)	0.48044 (18)	0.0255 (7)
H4BA	0.8368	0.2284	0.5190	0.031*
C5B	0.7163 (3)	0.1959 (3)	0.41661 (18)	0.0215 (6)
H5BA	0.7411	0.1065	0.4120	0.026*
C6B	0.6232 (3)	0.2537 (3)	0.35958 (15)	0.0155 (5)
C7B	0.5484 (3)	0.1774 (3)	0.29080 (16)	0.0149 (5)
H7BA	0.4486	0.2093	0.2816	0.018*
C8B	0.5398 (3)	0.0301 (3)	0.30118 (15)	0.0155 (5)
C9B	0.4277 (3)	−0.0183 (3)	0.33470 (18)	0.0209 (6)
H9BA	0.3620	0.0409	0.3511	0.025*
C10B	0.4114 (4)	−0.1520 (3)	0.3442 (2)	0.0267 (7)
H10B	0.3354	−0.1835	0.3675	0.032*
C11B	0.5055 (4)	−0.2397 (3)	0.3198 (2)	0.0277 (7)
H11B	0.4936	−0.3313	0.3257	0.033*
C12B	0.6170 (4)	−0.1927 (3)	0.28682 (19)	0.0275 (7)
H12B	0.6817	−0.2526	0.2700	0.033*
C13B	0.6355 (3)	−0.0590 (3)	0.27790 (18)	0.0220 (6)
H13B	0.7134	−0.0281	0.2559	0.026*
C14B	0.6141 (3)	0.2129 (3)	0.22130 (16)	0.0150 (5)
C15B	0.5644 (3)	0.3007 (3)	0.09483 (16)	0.0175 (6)
C16B	0.5224 (3)	0.2252 (3)	0.03030 (17)	0.0221 (6)
H16B	0.4661	0.1488	0.0326	0.027*
C17B	0.5623 (4)	0.2607 (4)	−0.03800 (18)	0.0267 (7)
H17B	0.5340	0.2078	−0.0819	0.032*
C18B	0.6432 (3)	0.3733 (4)	−0.04225 (18)	0.0249 (7)
C19B	0.6823 (3)	0.4486 (3)	0.02270 (19)	0.0229 (6)
H19B	0.7368	0.5261	0.0198	0.028*
C20B	0.6451 (3)	0.4153 (3)	0.09239 (17)	0.0198 (6)
C21B	0.6900 (4)	0.4120 (4)	−0.1154 (2)	0.0352 (9)
H21D	0.6675	0.5043	−0.1251	0.053*
H21E	0.6405	0.3572	−0.1567	0.053*
H21F	0.7925	0.3996	−0.1118	0.053*
C22B	0.6906 (4)	0.5003 (3)	0.16090 (19)	0.0266 (7)
H22D	0.7101	0.5894	0.1454	0.040*
H22E	0.7766	0.4645	0.1901	0.040*
H22F	0.6149	0.5028	0.1920	0.040*
H1NA	−0.069 (4)	0.224 (3)	0.172 (2)	0.015 (8)*
H1NB	0.434 (5)	0.262 (4)	0.171 (2)	0.030 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0105 (9)	0.0352 (12)	0.0149 (10)	−0.0014 (8)	0.0022 (8)	−0.0017 (8)
N1A	0.0088 (11)	0.0310 (14)	0.0120 (12)	−0.0012 (9)	0.0017 (9)	−0.0047 (10)
C1A	0.0153 (14)	0.0243 (15)	0.0304 (17)	−0.0004 (11)	0.0034 (12)	0.0034 (13)
C2A	0.0234 (16)	0.0298 (17)	0.0338 (19)	0.0040 (13)	0.0117 (14)	0.0122 (14)
C3A	0.0277 (16)	0.0323 (17)	0.0171 (15)	0.0087 (13)	0.0046 (12)	0.0042 (12)
C4A	0.0251 (15)	0.0241 (15)	0.0176 (15)	0.0040 (12)	0.0006 (12)	−0.0024 (11)
C5A	0.0214 (14)	0.0184 (14)	0.0167 (14)	0.0007 (11)	0.0014 (11)	−0.0012 (11)
C6A	0.0148 (13)	0.0218 (14)	0.0131 (13)	0.0024 (10)	0.0044 (10)	−0.0005 (10)
C7A	0.0084 (12)	0.0256 (15)	0.0141 (13)	−0.0003 (10)	0.0030 (10)	−0.0006 (11)
C8A	0.0093 (12)	0.0274 (15)	0.0121 (13)	0.0011 (10)	−0.0013 (10)	0.0014 (11)
C9A	0.0295 (17)	0.0312 (17)	0.0234 (16)	−0.0005 (13)	0.0125 (13)	0.0030 (13)
C10A	0.037 (2)	0.0266 (17)	0.0335 (19)	−0.0049 (14)	0.0076 (15)	0.0053 (14)
C11A	0.0243 (16)	0.0240 (16)	0.0308 (18)	0.0018 (12)	−0.0049 (13)	−0.0005 (13)
C12A	0.0221 (16)	0.0320 (18)	0.0328 (19)	0.0059 (13)	0.0052 (14)	−0.0023 (14)
C13A	0.0194 (15)	0.0280 (16)	0.0262 (16)	0.0025 (12)	0.0099 (12)	0.0001 (13)
C14A	0.0114 (12)	0.0238 (14)	0.0109 (13)	0.0005 (10)	0.0024 (10)	−0.0002 (10)
C15A	0.0117 (12)	0.0286 (15)	0.0114 (13)	−0.0021 (11)	0.0014 (10)	−0.0041 (11)
C16A	0.0192 (14)	0.0293 (16)	0.0163 (14)	0.0028 (12)	0.0016 (11)	−0.0028 (12)
C17A	0.0241 (16)	0.0349 (18)	0.0139 (14)	−0.0017 (13)	−0.0004 (12)	−0.0003 (12)
C18A	0.0176 (14)	0.0345 (17)	0.0153 (14)	−0.0078 (12)	0.0043 (11)	−0.0069 (12)
C19A	0.0156 (14)	0.0268 (16)	0.0221 (15)	−0.0006 (11)	0.0040 (11)	−0.0063 (12)
C20A	0.0120 (13)	0.0260 (15)	0.0178 (14)	−0.0023 (11)	0.0013 (10)	−0.0022 (11)
C21A	0.0262 (17)	0.046 (2)	0.0197 (16)	−0.0060 (15)	0.0089 (13)	−0.0096 (14)
C22A	0.0242 (16)	0.0276 (16)	0.0244 (16)	0.0021 (12)	0.0004 (13)	0.0010 (13)
O1B	0.0102 (9)	0.0326 (12)	0.0149 (10)	−0.0001 (8)	0.0023 (7)	0.0016 (8)
N1B	0.0094 (11)	0.0297 (14)	0.0125 (12)	0.0004 (9)	0.0027 (9)	0.0034 (9)
C1B	0.0173 (14)	0.0231 (15)	0.0239 (16)	0.0006 (11)	0.0021 (11)	0.0009 (12)
C2B	0.0233 (16)	0.0210 (15)	0.0322 (18)	−0.0007 (12)	0.0101 (13)	−0.0050 (13)
C3B	0.0305 (17)	0.0308 (17)	0.0159 (15)	−0.0051 (13)	0.0035 (12)	−0.0064 (12)
C4B	0.0273 (16)	0.0314 (17)	0.0167 (15)	−0.0003 (13)	0.0001 (12)	0.0023 (12)
C5B	0.0246 (15)	0.0203 (14)	0.0192 (15)	0.0018 (12)	0.0018 (12)	0.0007 (11)
C6B	0.0135 (12)	0.0234 (14)	0.0105 (12)	−0.0017 (10)	0.0052 (10)	−0.0014 (10)
C7B	0.0110 (12)	0.0216 (14)	0.0123 (13)	0.0011 (10)	0.0023 (10)	−0.0002 (10)
C8B	0.0115 (12)	0.0228 (14)	0.0111 (12)	−0.0001 (10)	−0.0013 (10)	−0.0003 (10)
C9B	0.0186 (14)	0.0240 (15)	0.0211 (15)	0.0008 (11)	0.0061 (11)	0.0002 (11)
C10B	0.0252 (16)	0.0282 (17)	0.0272 (17)	−0.0048 (13)	0.0052 (13)	0.0055 (13)
C11B	0.0344 (18)	0.0190 (15)	0.0271 (17)	−0.0022 (13)	−0.0029 (14)	0.0004 (12)
C12B	0.0305 (17)	0.0274 (17)	0.0241 (16)	0.0080 (13)	0.0029 (13)	−0.0039 (13)
C13B	0.0201 (15)	0.0276 (16)	0.0191 (15)	0.0040 (12)	0.0058 (11)	0.0001 (12)
C14B	0.0122 (12)	0.0200 (14)	0.0125 (13)	−0.0011 (10)	0.0010 (10)	−0.0003 (10)
C15B	0.0101 (12)	0.0298 (16)	0.0128 (13)	0.0018 (11)	0.0016 (10)	0.0045 (11)
C16B	0.0160 (14)	0.0330 (17)	0.0165 (14)	−0.0026 (12)	−0.0001 (11)	0.0015 (12)
C17B	0.0236 (16)	0.0416 (19)	0.0141 (14)	0.0036 (13)	0.0005 (12)	0.0005 (13)
C18B	0.0183 (14)	0.0414 (19)	0.0167 (14)	0.0093 (13)	0.0068 (11)	0.0108 (13)
C19B	0.0136 (13)	0.0318 (17)	0.0242 (16)	0.0019 (11)	0.0042 (11)	0.0096 (13)
C20B	0.0140 (13)	0.0276 (16)	0.0176 (14)	0.0014 (11)	0.0015 (11)	0.0043 (11)
C21B	0.0275 (18)	0.059 (2)	0.0227 (17)	0.0099 (16)	0.0135 (14)	0.0159 (16)
C22B	0.0272 (17)	0.0266 (16)	0.0249 (17)	−0.0036 (13)	0.0009 (13)	0.0005 (13)

Geometric parameters (Å, º) top

O1A—C14A	1.233 (3)	O1B—C14B	1.231 (3)
N1A—C14A	1.350 (4)	N1B—C14B	1.345 (4)
N1A—C15A	1.436 (4)	N1B—C15B	1.440 (4)
N1A—H1NA	0.88 (4)	N1B—H1NB	0.86 (5)
C1A—C6A	1.384 (4)	C1B—C2B	1.393 (5)
C1A—C2A	1.398 (5)	C1B—C6B	1.394 (4)
C1A—H1AA	0.9500	C1B—H1BA	0.9500
C2A—C3A	1.385 (5)	C2B—C3B	1.390 (5)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.385 (5)	C3B—C4B	1.380 (5)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.393 (4)	C4B—C5B	1.390 (4)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.401 (4)	C5B—C6B	1.391 (4)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C6A—C7A	1.526 (4)	C6B—C7B	1.525 (4)
C7A—C8A	1.523 (4)	C7B—C8B	1.521 (4)
C7A—C14A	1.529 (4)	C7B—C14B	1.530 (4)
C7A—H7AA	1.0000	C7B—H7BA	1.0000
C8A—C9A	1.383 (4)	C8B—C13B	1.397 (4)
C8A—C13A	1.400 (4)	C8B—C9B	1.399 (4)
C9A—C10A	1.392 (5)	C9B—C10B	1.388 (5)
C9A—H9AA	0.9500	C9B—H9BA	0.9500
C10A—C11A	1.381 (5)	C10B—C11B	1.385 (5)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.380 (5)	C11B—C12B	1.385 (5)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.383 (5)	C12B—C13B	1.389 (5)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500
C15A—C16A	1.385 (4)	C15B—C16B	1.385 (4)
C15A—C20A	1.404 (4)	C15B—C20B	1.401 (4)
C16A—C17A	1.404 (4)	C16B—C17B	1.393 (4)
C16A—H16A	0.9500	C16B—H16B	0.9500
C17A—C18A	1.381 (5)	C17B—C18B	1.390 (5)
C17A—H17A	0.9500	C17B—H17B	0.9500
C18A—C19A	1.394 (5)	C18B—C19B	1.385 (5)
C18A—C21A	1.505 (4)	C18B—C21B	1.511 (4)
C19A—C20A	1.390 (4)	C19B—C20B	1.401 (4)
C19A—H19A	0.9500	C19B—H19B	0.9500
C20A—C22A	1.508 (4)	C20B—C22B	1.499 (4)
C21A—H21A	0.9800	C21B—H21D	0.9800
C21A—H21B	0.9800	C21B—H21E	0.9800
C21A—H21C	0.9800	C21B—H21F	0.9800
C22A—H22A	0.9800	C22B—H22D	0.9800
C22A—H22B	0.9800	C22B—H22E	0.9800
C22A—H22C	0.9800	C22B—H22F	0.9800

C14A—N1A—C15A	121.6 (2)	C14B—N1B—C15B	122.0 (2)
C14A—N1A—H1NA	118 (2)	C14B—N1B—H1NB	116 (3)
C15A—N1A—H1NA	120 (2)	C15B—N1B—H1NB	122 (3)
C6A—C1A—C2A	120.2 (3)	C2B—C1B—C6B	121.0 (3)
C6A—C1A—H1AA	119.9	C2B—C1B—H1BA	119.5
C2A—C1A—H1AA	119.9	C6B—C1B—H1BA	119.5
C3A—C2A—C1A	120.4 (3)	C3B—C2B—C1B	119.8 (3)
C3A—C2A—H2AA	119.8	C3B—C2B—H2BA	120.1
C1A—C2A—H2AA	119.8	C1B—C2B—H2BA	120.1
C4A—C3A—C2A	119.9 (3)	C4B—C3B—C2B	119.3 (3)
C4A—C3A—H3AA	120.0	C4B—C3B—H3BA	120.4
C2A—C3A—H3AA	120.0	C2B—C3B—H3BA	120.4
C3A—C4A—C5A	119.6 (3)	C3B—C4B—C5B	121.2 (3)
C3A—C4A—H4AA	120.2	C3B—C4B—H4BA	119.4
C5A—C4A—H4AA	120.2	C5B—C4B—H4BA	119.4
C4A—C5A—C6A	120.9 (3)	C4B—C5B—C6B	120.1 (3)
C4A—C5A—H5AA	119.6	C4B—C5B—H5BA	119.9
C6A—C5A—H5AA	119.6	C6B—C5B—H5BA	119.9
C1A—C6A—C5A	118.9 (3)	C5B—C6B—C1B	118.6 (3)
C1A—C6A—C7A	119.8 (3)	C5B—C6B—C7B	123.0 (3)
C5A—C6A—C7A	121.3 (3)	C1B—C6B—C7B	118.3 (3)
C8A—C7A—C6A	112.4 (2)	C8B—C7B—C6B	114.6 (2)
C8A—C7A—C14A	111.8 (2)	C8B—C7B—C14B	112.5 (2)
C6A—C7A—C14A	110.6 (2)	C6B—C7B—C14B	109.8 (2)
C8A—C7A—H7AA	107.3	C8B—C7B—H7BA	106.4
C6A—C7A—H7AA	107.3	C6B—C7B—H7BA	106.4
C14A—C7A—H7AA	107.3	C14B—C7B—H7BA	106.4
C9A—C8A—C13A	118.4 (3)	C13B—C8B—C9B	118.5 (3)
C9A—C8A—C7A	124.0 (3)	C13B—C8B—C7B	123.7 (3)
C13A—C8A—C7A	117.6 (3)	C9B—C8B—C7B	117.7 (3)
C8A—C9A—C10A	120.8 (3)	C10B—C9B—C8B	120.7 (3)
C8A—C9A—H9AA	119.6	C10B—C9B—H9BA	119.6
C10A—C9A—H9AA	119.6	C8B—C9B—H9BA	119.6
C11A—C10A—C9A	120.3 (3)	C11B—C10B—C9B	120.3 (3)
C11A—C10A—H10A	119.9	C11B—C10B—H10B	119.8
C9A—C10A—H10A	119.9	C9B—C10B—H10B	119.8
C12A—C11A—C10A	119.4 (3)	C12B—C11B—C10B	119.4 (3)
C12A—C11A—H11A	120.3	C12B—C11B—H11B	120.3
C10A—C11A—H11A	120.3	C10B—C11B—H11B	120.3
C11A—C12A—C13A	120.6 (3)	C11B—C12B—C13B	120.8 (3)
C11A—C12A—H12A	119.7	C11B—C12B—H12B	119.6
C13A—C12A—H12A	119.7	C13B—C12B—H12B	119.6
C12A—C13A—C8A	120.5 (3)	C12B—C13B—C8B	120.2 (3)
C12A—C13A—H13A	119.7	C12B—C13B—H13B	119.9
C8A—C13A—H13A	119.7	C8B—C13B—H13B	119.9
O1A—C14A—N1A	123.1 (3)	O1B—C14B—N1B	123.4 (3)
O1A—C14A—C7A	122.3 (3)	O1B—C14B—C7B	122.4 (2)
N1A—C14A—C7A	114.6 (2)	N1B—C14B—C7B	114.2 (2)
C16A—C15A—C20A	121.0 (3)	C16B—C15B—C20B	120.7 (3)
C16A—C15A—N1A	118.8 (3)	C16B—C15B—N1B	118.9 (3)
C20A—C15A—N1A	120.2 (3)	C20B—C15B—N1B	120.3 (3)
C15A—C16A—C17A	119.8 (3)	C15B—C16B—C17B	120.4 (3)
C15A—C16A—H16A	120.1	C15B—C16B—H16B	119.8
C17A—C16A—H16A	120.1	C17B—C16B—H16B	119.8
C18A—C17A—C16A	120.4 (3)	C18B—C17B—C16B	120.3 (3)
C18A—C17A—H17A	119.8	C18B—C17B—H17B	119.8
C16A—C17A—H17A	119.8	C16B—C17B—H17B	119.8
C17A—C18A—C19A	118.6 (3)	C19B—C18B—C17B	118.4 (3)
C17A—C18A—C21A	121.1 (3)	C19B—C18B—C21B	120.5 (3)
C19A—C18A—C21A	120.3 (3)	C17B—C18B—C21B	121.1 (3)
C20A—C19A—C18A	122.7 (3)	C18B—C19B—C20B	122.8 (3)
C20A—C19A—H19A	118.7	C18B—C19B—H19B	118.6
C18A—C19A—H19A	118.7	C20B—C19B—H19B	118.6
C19A—C20A—C15A	117.5 (3)	C19B—C20B—C15B	117.3 (3)
C19A—C20A—C22A	120.0 (3)	C19B—C20B—C22B	120.5 (3)
C15A—C20A—C22A	122.5 (3)	C15B—C20B—C22B	122.2 (3)
C18A—C21A—H21A	109.5	C18B—C21B—H21D	109.5
C18A—C21A—H21B	109.5	C18B—C21B—H21E	109.5
H21A—C21A—H21B	109.5	H21D—C21B—H21E	109.5
C18A—C21A—H21C	109.5	C18B—C21B—H21F	109.5
H21A—C21A—H21C	109.5	H21D—C21B—H21F	109.5
H21B—C21A—H21C	109.5	H21E—C21B—H21F	109.5
C20A—C22A—H22A	109.5	C20B—C22B—H22D	109.5
C20A—C22A—H22B	109.5	C20B—C22B—H22E	109.5
H22A—C22A—H22B	109.5	H22D—C22B—H22E	109.5
C20A—C22A—H22C	109.5	C20B—C22B—H22F	109.5
H22A—C22A—H22C	109.5	H22D—C22B—H22F	109.5
H22B—C22A—H22C	109.5	H22E—C22B—H22F	109.5

C6A—C1A—C2A—C3A	−1.4 (5)	C6B—C1B—C2B—C3B	1.8 (5)
C1A—C2A—C3A—C4A	−0.1 (5)	C1B—C2B—C3B—C4B	−0.5 (5)
C2A—C3A—C4A—C5A	1.3 (5)	C2B—C3B—C4B—C5B	−0.5 (5)
C3A—C4A—C5A—C6A	−1.2 (5)	C3B—C4B—C5B—C6B	0.1 (5)
C2A—C1A—C6A—C5A	1.5 (5)	C4B—C5B—C6B—C1B	1.2 (5)
C2A—C1A—C6A—C7A	−179.1 (3)	C4B—C5B—C6B—C7B	−175.4 (3)
C4A—C5A—C6A—C1A	−0.3 (4)	C2B—C1B—C6B—C5B	−2.2 (5)
C4A—C5A—C6A—C7A	−179.7 (3)	C2B—C1B—C6B—C7B	174.6 (3)
C1A—C6A—C7A—C8A	132.8 (3)	C5B—C6B—C7B—C8B	20.8 (4)
C5A—C6A—C7A—C8A	−47.8 (4)	C1B—C6B—C7B—C8B	−155.8 (3)
C1A—C6A—C7A—C14A	−101.5 (3)	C5B—C6B—C7B—C14B	−107.0 (3)
C5A—C6A—C7A—C14A	77.9 (3)	C1B—C6B—C7B—C14B	76.5 (3)
C6A—C7A—C8A—C9A	111.8 (3)	C6B—C7B—C8B—C13B	−96.5 (3)
C14A—C7A—C8A—C9A	−13.2 (4)	C14B—C7B—C8B—C13B	29.9 (4)
C6A—C7A—C8A—C13A	−69.7 (3)	C6B—C7B—C8B—C9B	84.7 (3)
C14A—C7A—C8A—C13A	165.3 (3)	C14B—C7B—C8B—C9B	−148.9 (3)
C13A—C8A—C9A—C10A	−0.6 (5)	C13B—C8B—C9B—C10B	−0.4 (5)
C7A—C8A—C9A—C10A	177.9 (3)	C7B—C8B—C9B—C10B	178.4 (3)
C8A—C9A—C10A—C11A	−0.1 (6)	C8B—C9B—C10B—C11B	−0.6 (5)
C9A—C10A—C11A—C12A	1.3 (6)	C9B—C10B—C11B—C12B	0.8 (5)
C10A—C11A—C12A—C13A	−1.8 (5)	C10B—C11B—C12B—C13B	0.0 (5)
C11A—C12A—C13A—C8A	1.1 (5)	C11B—C12B—C13B—C8B	−1.1 (5)
C9A—C8A—C13A—C12A	0.1 (5)	C9B—C8B—C13B—C12B	1.2 (4)
C7A—C8A—C13A—C12A	−178.5 (3)	C7B—C8B—C13B—C12B	−177.5 (3)
C15A—N1A—C14A—O1A	−1.3 (5)	C15B—N1B—C14B—O1B	0.5 (5)
C15A—N1A—C14A—C7A	177.7 (3)	C15B—N1B—C14B—C7B	179.5 (3)
C8A—C7A—C14A—O1A	73.9 (3)	C8B—C7B—C14B—O1B	−72.0 (3)
C6A—C7A—C14A—O1A	−52.1 (4)	C6B—C7B—C14B—O1B	56.9 (4)
C8A—C7A—C14A—N1A	−105.2 (3)	C8B—C7B—C14B—N1B	108.9 (3)
C6A—C7A—C14A—N1A	128.8 (3)	C6B—C7B—C14B—N1B	−122.1 (3)
C14A—N1A—C15A—C16A	−109.0 (3)	C14B—N1B—C15B—C16B	109.1 (3)
C14A—N1A—C15A—C20A	71.1 (4)	C14B—N1B—C15B—C20B	−72.1 (4)
C20A—C15A—C16A—C17A	−0.7 (5)	C20B—C15B—C16B—C17B	1.3 (5)
N1A—C15A—C16A—C17A	179.4 (3)	N1B—C15B—C16B—C17B	−179.9 (3)
C15A—C16A—C17A—C18A	0.3 (5)	C15B—C16B—C17B—C18B	−0.8 (5)
C16A—C17A—C18A—C19A	0.6 (5)	C16B—C17B—C18B—C19B	−0.2 (5)
C16A—C17A—C18A—C21A	−178.6 (3)	C16B—C17B—C18B—C21B	178.7 (3)
C17A—C18A—C19A—C20A	−1.2 (5)	C17B—C18B—C19B—C20B	0.7 (5)
C21A—C18A—C19A—C20A	178.0 (3)	C21B—C18B—C19B—C20B	−178.2 (3)
C18A—C19A—C20A—C15A	0.8 (5)	C18B—C19B—C20B—C15B	−0.2 (5)
C18A—C19A—C20A—C22A	−179.1 (3)	C18B—C19B—C20B—C22B	179.9 (3)
C16A—C15A—C20A—C19A	0.2 (4)	C16B—C15B—C20B—C19B	−0.8 (4)
N1A—C15A—C20A—C19A	−179.9 (3)	N1B—C15B—C20B—C19B	−179.6 (3)
C16A—C15A—C20A—C22A	−179.9 (3)	C16B—C15B—C20B—C22B	179.1 (3)
N1A—C15A—C20A—C22A	−0.1 (4)	N1B—C15B—C20B—C22B	0.4 (4)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg4 and Cg5 are the centroids of the C1A–C6A, C1B–C6B and C8B–C13B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1Bⁱ	0.88 (4)	2.13 (4)	2.980 (3)	163 (3)
N1B—H1NB···O1A	0.86 (5)	2.18 (5)	3.012 (3)	162 (3)
C7A—H7AA···O1Bⁱ	1.00	2.32	3.258 (4)	155
C9A—H9AA···O1A	0.95	2.48	3.110 (4)	123
C7B—H7BA···O1A	1.00	2.27	3.225 (4)	160
C13B—H13B···O1B	0.95	2.46	3.087 (4)	124
C3A—H3AA···Cg5ⁱⁱ	0.95	2.89	3.754 (4)	151
C4A—H4AA···Cg4	0.95	2.84	3.539 (4)	131
C13A—H13A···Cg4ⁱ	0.95	2.68	3.561 (3)	154
C9B—H9BA···Cg1	0.95	2.62	3.546 (3)	167

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁NO
M_r	315.40
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.5520 (9), 10.2011 (10), 17.9656 (17)
α, β, γ (°)	91.030 (2), 98.957 (2), 90.377 (2)
V (Å³)	1728.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.41 × 0.19 × 0.17

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.970, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	30869, 7858, 6570
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.085, 0.261, 1.14
No. of reflections	7858
No. of parameters	445
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.42

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg4 and Cg5 are the centroids of the C1A–C6A, C1B–C6B and C8B–C13B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1Bⁱ	0.88 (4)	2.13 (4)	2.980 (3)	163 (3)
N1B—H1NB···O1A	0.86 (5)	2.18 (5)	3.012 (3)	162 (3)
C7A—H7AA···O1Bⁱ	1.0000	2.3200	3.258 (4)	155.00
C9A—H9AA···O1A	0.9500	2.4800	3.110 (4)	123.00
C7B—H7BA···O1A	1.0000	2.2700	3.225 (4)	160.00
C13B—H13B···O1B	0.9500	2.4600	3.087 (4)	124.00
C3A—H3AA···Cg5ⁱⁱ	0.95	2.89	3.754 (4)	151
C4A—H4AA···Cg4	0.95	2.84	3.539 (4)	131
C13A—H13A···Cg4ⁱ	0.95	2.68	3.561 (3)	154
C9B—H9BA···Cg1	0.95	2.62	3.546 (3)	167

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). BN thanks UGC, New Delhi and Government of India for the purchase of chemicals through the SAP-DRS-Phase 1 programme.

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Volume 68| Part 5| May 2012| Pages o1316-o1317

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