N-(2,6-Dimethyl­phen­yl)-2,2-diphenyl­acetamide

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

doi:10.1107/S1600536812013451

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1287-o1288

doi:10.1107/S1600536812013451

Open

access

N-(2,6-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 26 March 2012; accepted 28 March 2012; online 4 April 2012)

In the title compound, C₂₂H₂₁NO, the dihedral angle between the phenyl rings is 82.59 (7)°. The dimethylbenzene ring forms dihedral angles of 52.86 (4) and 49.65 (5)° with the two phenyl rings. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming a C(4) chain along the c axis. The crystal also features C—H⋯π interactions.

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 reference bond lengths, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₂H₂₁NO
M_r = 315.40
Monoclinic, P 2₁ /c
a = 12.0606 (10) Å
b = 16.6747 (13) Å
c = 8.9469 (7) Å
β = 108.080 (2)°
V = 1710.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.56 × 0.21 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.959, T_max = 0.991
19127 measured reflections
4994 independent reflections
3661 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.139
S = 1.03
4994 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.88 (2)	1.97 (2)	2.8207 (16)	163.2 (17)
C12—H12A⋯Cg1ⁱⁱ	0.95	2.80	3.6981 (17)	158
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -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/S1600536812013451/is5102sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013451/is5102Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013451/is5102Isup3.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 title compound (Fig. 1) consists of two benzene rings (C1–C6 & C8–C13) and one dimethylbenzene ring (C15–C22) [maximum deviation = 0.0159 (10) at atom C22]. The dihedral angle between the two phenyl rings is 82.59 (7)°. The dimethylbenzene ring forms dihedral angles of 52.86 (4) and 49.65 (5) Å with the C1–C6 and C8–C13 phenyl rings, respectively. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2011a,b).

In the crystal (Fig. 2), molecules are linked by intermolecular N1—H1N1···O1 hydrogen bonds (Table 1), forming an infinite chain along the c axis. The crystal is further stabilized by C—H···π interaction (Table 1), involving Cg1 which is the centroid of C1–C6 ring.

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 reference bond lengths, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Diphenylacetic acid (0.212 g, 1 mmol), 2,6-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 acetone (1:1) mixture by the slow evaporation method (M.P.: 469–471 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.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds.

N-(2,6-Dimethylphenyl)-2,2-diphenylacetamide top

Crystal data top

C₂₂H₂₁NO	F(000) = 672
M_r = 315.40	D_x = 1.225 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4188 reflections
a = 12.0606 (10) Å	θ = 2.4–29.9°
b = 16.6747 (13) Å	µ = 0.07 mm⁻¹
c = 8.9469 (7) Å	T = 100 K
β = 108.080 (2)°	Block, colourless
V = 1710.4 (2) Å³	0.56 × 0.21 × 0.12 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4994 independent reflections
Radiation source: fine-focus sealed tube	3661 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→16
T_min = 0.959, T_max = 0.991	k = −23→23
19127 measured reflections	l = −12→12

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0585P)² + 0.6024P] where P = (F_o² + 2F_c²)/3
4994 reflections	(Δ/σ)_max < 0.001
223 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₂H₂₁NO	V = 1710.4 (2) Å³
M_r = 315.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0606 (10) Å	µ = 0.07 mm⁻¹
b = 16.6747 (13) Å	T = 100 K
c = 8.9469 (7) Å	0.56 × 0.21 × 0.12 mm
β = 108.080 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4994 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3661 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.991	R_int = 0.049
19127 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.37 e Å⁻³
4994 reflections	Δρ_min = −0.27 e Å⁻³
223 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
O1	0.20052 (9)	0.19921 (6)	1.02094 (12)	0.0242 (2)
N1	0.27147 (10)	0.26010 (7)	0.84282 (14)	0.0170 (2)
C1	0.09237 (12)	0.00933 (8)	0.86256 (17)	0.0219 (3)
H1A	0.0137	0.0271	0.8351	0.026*
C2	0.12231 (14)	−0.06573 (9)	0.93123 (19)	0.0266 (3)
H2A	0.0638	−0.0992	0.9488	0.032*
C3	0.23640 (14)	−0.09192 (9)	0.97397 (19)	0.0289 (4)
H3A	0.2566	−0.1431	1.0214	0.035*
C4	0.32122 (14)	−0.04310 (9)	0.9472 (2)	0.0293 (4)
H4A	0.4000	−0.0607	0.9768	0.035*
C5	0.29162 (13)	0.03156 (9)	0.87732 (18)	0.0238 (3)
H5A	0.3503	0.0645	0.8589	0.029*
C6	0.17645 (12)	0.05855 (8)	0.83388 (17)	0.0185 (3)
C7	0.14945 (11)	0.14193 (8)	0.76064 (16)	0.0174 (3)
H7A	0.1869	0.1460	0.6757	0.021*
C8	0.01942 (12)	0.15663 (8)	0.68561 (17)	0.0183 (3)
C9	−0.04747 (13)	0.20118 (8)	0.75703 (18)	0.0228 (3)
H9A	−0.0115	0.2265	0.8553	0.027*
C10	−0.16715 (13)	0.20883 (9)	0.6849 (2)	0.0269 (3)
H10A	−0.2122	0.2397	0.7340	0.032*
C11	−0.22128 (13)	0.17175 (9)	0.54190 (19)	0.0257 (3)
H11A	−0.3031	0.1767	0.4939	0.031*
C12	−0.15501 (13)	0.12737 (9)	0.46949 (19)	0.0254 (3)
H12A	−0.1913	0.1020	0.3714	0.031*
C13	−0.03575 (13)	0.12027 (8)	0.54073 (17)	0.0222 (3)
H13A	0.0093	0.0902	0.4903	0.027*
C14	0.20834 (12)	0.20360 (8)	0.88693 (17)	0.0176 (3)
C15	0.33925 (11)	0.31871 (8)	0.95000 (16)	0.0174 (3)
C16	0.30565 (12)	0.39937 (8)	0.93049 (17)	0.0195 (3)
C17	0.37580 (13)	0.45554 (9)	1.03253 (18)	0.0245 (3)
H17A	0.3545	0.5106	1.0217	0.029*
C18	0.47589 (13)	0.43236 (9)	1.14927 (19)	0.0271 (3)
H18A	0.5230	0.4715	1.2171	0.033*
C19	0.50738 (12)	0.35244 (10)	1.16725 (18)	0.0251 (3)
H19A	0.5758	0.3370	1.2484	0.030*
C20	0.44015 (12)	0.29401 (8)	1.06793 (18)	0.0214 (3)
C21	0.19801 (14)	0.42557 (9)	0.80384 (19)	0.0269 (3)
H21A	0.1777	0.4803	0.8254	0.040*
H21B	0.1335	0.3894	0.8013	0.040*
H21C	0.2125	0.4242	0.7020	0.040*
C22	0.47809 (14)	0.20760 (9)	1.0863 (2)	0.0292 (4)
H22A	0.4740	0.1854	0.9833	0.044*
H22B	0.4265	0.1770	1.1309	0.044*
H22C	0.5584	0.2041	1.1568	0.044*
H1N1	0.2599 (16)	0.2654 (11)	0.742 (2)	0.030 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0360 (6)	0.0259 (5)	0.0127 (5)	−0.0079 (4)	0.0105 (4)	−0.0027 (4)
N1	0.0219 (5)	0.0189 (5)	0.0098 (6)	−0.0018 (4)	0.0041 (5)	−0.0006 (5)
C1	0.0240 (6)	0.0216 (6)	0.0193 (7)	0.0000 (5)	0.0055 (6)	−0.0009 (6)
C2	0.0346 (8)	0.0226 (7)	0.0204 (8)	−0.0028 (6)	0.0055 (6)	0.0023 (6)
C3	0.0405 (8)	0.0198 (6)	0.0192 (8)	0.0055 (6)	−0.0010 (7)	−0.0013 (6)
C4	0.0288 (7)	0.0279 (7)	0.0253 (8)	0.0080 (6)	0.0001 (6)	−0.0082 (7)
C5	0.0247 (6)	0.0254 (7)	0.0212 (8)	0.0006 (5)	0.0071 (6)	−0.0063 (6)
C6	0.0236 (6)	0.0192 (6)	0.0118 (6)	0.0001 (5)	0.0041 (5)	−0.0039 (5)
C7	0.0223 (6)	0.0192 (6)	0.0110 (6)	−0.0020 (5)	0.0058 (5)	−0.0022 (5)
C8	0.0247 (6)	0.0163 (6)	0.0135 (6)	−0.0011 (5)	0.0052 (5)	0.0022 (5)
C9	0.0289 (7)	0.0199 (6)	0.0188 (7)	−0.0003 (5)	0.0060 (6)	−0.0027 (6)
C10	0.0294 (7)	0.0238 (7)	0.0280 (9)	0.0045 (6)	0.0097 (7)	0.0004 (7)
C11	0.0258 (7)	0.0231 (7)	0.0244 (8)	0.0004 (5)	0.0021 (6)	0.0055 (6)
C12	0.0302 (7)	0.0264 (7)	0.0166 (7)	−0.0049 (6)	0.0028 (6)	0.0019 (6)
C13	0.0294 (7)	0.0220 (6)	0.0157 (7)	−0.0016 (5)	0.0077 (6)	−0.0025 (6)
C14	0.0209 (6)	0.0185 (6)	0.0135 (6)	0.0004 (5)	0.0054 (5)	0.0011 (5)
C15	0.0185 (6)	0.0205 (6)	0.0141 (6)	−0.0020 (5)	0.0064 (5)	−0.0001 (5)
C16	0.0235 (6)	0.0207 (6)	0.0168 (7)	0.0000 (5)	0.0097 (6)	0.0003 (6)
C17	0.0330 (7)	0.0199 (6)	0.0231 (8)	−0.0039 (6)	0.0124 (6)	−0.0027 (6)
C18	0.0296 (7)	0.0298 (7)	0.0234 (8)	−0.0110 (6)	0.0102 (6)	−0.0065 (7)
C19	0.0199 (6)	0.0362 (8)	0.0178 (7)	−0.0044 (6)	0.0041 (6)	−0.0032 (7)
C20	0.0200 (6)	0.0258 (7)	0.0187 (7)	−0.0001 (5)	0.0068 (6)	−0.0009 (6)
C21	0.0339 (8)	0.0238 (7)	0.0209 (8)	0.0071 (6)	0.0054 (7)	0.0019 (6)
C22	0.0275 (7)	0.0298 (7)	0.0255 (8)	0.0080 (6)	0.0012 (6)	−0.0006 (7)

Geometric parameters (Å, º) top

O1—C14	1.2337 (17)	C10—H10A	0.9500
N1—C14	1.3452 (18)	C11—C12	1.388 (2)
N1—C15	1.4340 (17)	C11—H11A	0.9500
N1—H1N1	0.88 (2)	C12—C13	1.386 (2)
C1—C6	1.389 (2)	C12—H12A	0.9500
C1—C2	1.392 (2)	C13—H13A	0.9500
C1—H1A	0.9500	C15—C16	1.3998 (19)
C2—C3	1.380 (2)	C15—C20	1.4024 (19)
C2—H2A	0.9500	C16—C17	1.395 (2)
C3—C4	1.385 (2)	C16—C21	1.499 (2)
C3—H3A	0.9500	C17—C18	1.384 (2)
C4—C5	1.389 (2)	C17—H17A	0.9500
C4—H4A	0.9500	C18—C19	1.381 (2)
C5—C6	1.3957 (19)	C18—H18A	0.9500
C5—H5A	0.9500	C19—C20	1.396 (2)
C6—C7	1.5285 (19)	C19—H19A	0.9500
C7—C8	1.5221 (18)	C20—C22	1.505 (2)
C7—C14	1.5298 (18)	C21—H21A	0.9800
C7—H7A	1.0000	C21—H21B	0.9800
C8—C9	1.389 (2)	C21—H21C	0.9800
C8—C13	1.398 (2)	C22—H22A	0.9800
C9—C10	1.392 (2)	C22—H22B	0.9800
C9—H9A	0.9500	C22—H22C	0.9800
C10—C11	1.388 (2)

C14—N1—C15	122.57 (12)	C13—C12—C11	119.78 (14)
C14—N1—H1N1	116.8 (12)	C13—C12—H12A	120.1
C15—N1—H1N1	119.8 (12)	C11—C12—H12A	120.1
C6—C1—C2	120.58 (14)	C12—C13—C8	121.11 (14)
C6—C1—H1A	119.7	C12—C13—H13A	119.4
C2—C1—H1A	119.7	C8—C13—H13A	119.4
C3—C2—C1	120.45 (15)	O1—C14—N1	123.20 (13)
C3—C2—H2A	119.8	O1—C14—C7	121.33 (12)
C1—C2—H2A	119.8	N1—C14—C7	115.43 (12)
C2—C3—C4	119.52 (14)	C16—C15—C20	121.74 (13)
C2—C3—H3A	120.2	C16—C15—N1	119.24 (12)
C4—C3—H3A	120.2	C20—C15—N1	118.97 (12)
C3—C4—C5	120.27 (14)	C17—C16—C15	118.04 (13)
C3—C4—H4A	119.9	C17—C16—C21	120.39 (13)
C5—C4—H4A	119.9	C15—C16—C21	121.57 (13)
C4—C5—C6	120.58 (14)	C18—C17—C16	121.07 (14)
C4—C5—H5A	119.7	C18—C17—H17A	119.5
C6—C5—H5A	119.7	C16—C17—H17A	119.5
C1—C6—C5	118.59 (13)	C19—C18—C17	120.08 (14)
C1—C6—C7	123.10 (12)	C19—C18—H18A	120.0
C5—C6—C7	118.29 (13)	C17—C18—H18A	120.0
C8—C7—C6	112.88 (11)	C18—C19—C20	120.98 (14)
C8—C7—C14	113.34 (11)	C18—C19—H19A	119.5
C6—C7—C14	107.85 (11)	C20—C19—H19A	119.5
C8—C7—H7A	107.5	C19—C20—C15	118.09 (13)
C6—C7—H7A	107.5	C19—C20—C22	120.10 (13)
C14—C7—H7A	107.5	C15—C20—C22	121.79 (13)
C9—C8—C13	118.75 (13)	C16—C21—H21A	109.5
C9—C8—C7	123.30 (13)	C16—C21—H21B	109.5
C13—C8—C7	117.88 (13)	H21A—C21—H21B	109.5
C8—C9—C10	120.14 (14)	C16—C21—H21C	109.5
C8—C9—H9A	119.9	H21A—C21—H21C	109.5
C10—C9—H9A	119.9	H21B—C21—H21C	109.5
C11—C10—C9	120.66 (15)	C20—C22—H22A	109.5
C11—C10—H10A	119.7	C20—C22—H22B	109.5
C9—C10—H10A	119.7	H22A—C22—H22B	109.5
C10—C11—C12	119.55 (14)	C20—C22—H22C	109.5
C10—C11—H11A	120.2	H22A—C22—H22C	109.5
C12—C11—H11A	120.2	H22B—C22—H22C	109.5

C6—C1—C2—C3	0.9 (2)	C7—C8—C13—C12	176.47 (13)
C1—C2—C3—C4	−0.4 (2)	C15—N1—C14—O1	2.5 (2)
C2—C3—C4—C5	−0.3 (2)	C15—N1—C14—C7	−175.23 (11)
C3—C4—C5—C6	0.3 (2)	C8—C7—C14—O1	79.21 (16)
C2—C1—C6—C5	−0.9 (2)	C6—C7—C14—O1	−46.51 (17)
C2—C1—C6—C7	−179.26 (14)	C8—C7—C14—N1	−103.05 (14)
C4—C5—C6—C1	0.2 (2)	C6—C7—C14—N1	131.23 (12)
C4—C5—C6—C7	178.71 (13)	C14—N1—C15—C16	−112.23 (15)
C1—C6—C7—C8	−14.54 (19)	C14—N1—C15—C20	70.24 (18)
C5—C6—C7—C8	167.05 (13)	C20—C15—C16—C17	0.0 (2)
C1—C6—C7—C14	111.45 (15)	N1—C15—C16—C17	−177.47 (13)
C5—C6—C7—C14	−66.97 (16)	C20—C15—C16—C21	179.73 (14)
C6—C7—C8—C9	101.42 (15)	N1—C15—C16—C21	2.3 (2)
C14—C7—C8—C9	−21.56 (19)	C15—C16—C17—C18	0.2 (2)
C6—C7—C8—C13	−75.63 (16)	C21—C16—C17—C18	−179.52 (14)
C14—C7—C8—C13	161.39 (12)	C16—C17—C18—C19	−0.5 (2)
C13—C8—C9—C10	0.2 (2)	C17—C18—C19—C20	0.6 (2)
C7—C8—C9—C10	−176.82 (13)	C18—C19—C20—C15	−0.4 (2)
C8—C9—C10—C11	0.5 (2)	C18—C19—C20—C22	178.07 (15)
C9—C10—C11—C12	−0.7 (2)	C16—C15—C20—C19	0.1 (2)
C10—C11—C12—C13	0.2 (2)	N1—C15—C20—C19	177.57 (13)
C11—C12—C13—C8	0.5 (2)	C16—C15—C20—C22	−178.36 (14)
C9—C8—C13—C12	−0.7 (2)	N1—C15—C20—C22	−0.9 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.88 (2)	1.97 (2)	2.8207 (16)	163.2 (17)
C12—H12A···Cg1ⁱⁱ	0.95	2.80	3.6981 (17)	158

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁NO
M_r	315.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.0606 (10), 16.6747 (13), 8.9469 (7)
β (°)	108.080 (2)
V (Å³)	1710.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.56 × 0.21 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.959, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	19127, 4994, 3661
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.139, 1.03
No. of reflections	4994
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.27

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.88 (2)	1.97 (2)	2.8207 (16)	163.2 (17)
C12—H12A···Cg1ⁱⁱ	0.95	2.80	3.6981 (17)	158

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −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). TSC also thanks the Malaysian Government and USM for the award of a Research Fellowship. BN thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS–Phase 1 programme.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011a). Acta Cryst. E67, o2926–o2927. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011b). Acta Cryst. E67, o2941–o2942. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mijin, D. & Marinkovic, A. (2006). Synth. Commun. 36, 193–198. Web of Science CrossRef CAS Google Scholar
Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945–950. Web of Science CrossRef CAS Google Scholar
Praveen, A. S., Jasinski, J. P., Golen, J. A., Narayana, B. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o1826. Web of Science CSD CrossRef IUCr Journals Google Scholar
Praveen, A. S., Jasinski, J. P., Golen, J. A., Yathirajan, H. S. & Narayana, B. (2011b). Acta Cryst. E67, o2602–o2603. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Praveen, A. S., Jasinski, J. P., Golen, J. A., Narayana, B. & Yathirajan, H. S. (2011c). Acta Cryst. E67, o2604. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207–2215. Web of Science CrossRef CAS Google Scholar
Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1287-o1288

doi:10.1107/S1600536812013451

Open

access