N-(2,6-Dimethyl-phen-yl)-2,2-diphenyl-acetamide.

In the title compound, C(22)H(21)NO, the dihedral angle between the phenyl rings is 82.59 (7)°. The dimethyl-benzene ring forms dihedral angles of 52.86 (4) and 49.65 (5)° with the two phenyl rings. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming a C(4) chain along the c axis. The crystal also features C-H⋯π inter-actions.

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 = 315.40

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.139

S = 1.03

4994 reflections

223 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.27 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013451/is5102sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812013451/is5102Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H21NO	F(000) = 672
Mr = 315.40	Dx = 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

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

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(Fo2) + (0.0585P)2 + 0.6024P] where P = (Fo2 + 2Fc2)/3
4994 reflections	(Δ/σ)max < 0.001
223 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) ; (ii) .