N-Cyclo-hexyl-3,4,5-trimethoxy-benzamide.

The 3,5-meth-oxy groups in the title compound, C(16)H(23)NO(4), are almost coplanar with the aromatic ring, whereas the 4-meth-oxy group is bent out of this plane. The three CH(3)-O-C-C torsion angles are -1.51 (18), 0.73 (19) and 75.33 (15)°. The cyclo-hexane ring adopts a chair conformation. In the crystal, mol-ecules are connected by inter-molecular N-H⋯O hydrogen bonds into chains running along the b axis.

Related literature

For the biological activity of benzanilides, see: Olsson et al. (2002 ▶); Lindgren et al. (2001 ▶); Calderone et al. (2006 ▶). For the use of benzamides in organic synthesis, see: Zhichkin et al. (2007 ▶); Beccalli et al. (2005 ▶). For related structures, see: Bowes et al. (2003 ▶); Chopra & Guru Row (2008 ▶); Kashino et al. (1979 ▶); Saeed et al. (2008 ▶).

Experimental

Crystal data

C16H23NO4

M = 293.35

Monoclinic,

a = 23.4539 (19) Å

b = 5.2145 (6) Å

c = 12.4559 (10) Å

β = 92.886 (6)°

V = 1521.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.37 × 0.37 × 0.33 mm

Data collection

Stoe IPDSII two-circle diffractometer

Absorption correction: none

6868 measured reflections

2823 independent reflections

2360 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.109

S = 1.05

2823 reflections

198 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050284/fj2261sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050284/fj2261Isup2.hkl

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

C16H23NO4	F(000) = 632
Mr = 293.35	Dx = 1.281 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6103 reflections
a = 23.4539 (19) Å	θ = 3.4–26.0°
b = 5.2145 (6) Å	µ = 0.09 mm−1
c = 12.4559 (10) Å	T = 173 K
β = 92.886 (6)°	Block, colourless
V = 1521.4 (2) Å3	0.37 × 0.37 × 0.33 mm
Z = 4

Stoe IPDSII two-circle diffractometer	2360 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
graphite	θmax = 25.6°, θmin = 3.4°
ω scans	h = −28→23
6868 measured reflections	k = −5→6
2823 independent reflections	l = −15→15

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.0617P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2823 reflections	Δρmax = 0.27 e Å−3
198 parameters	Δρmin = −0.22 e Å−3
0 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: 0.023 (3)

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
N1	0.19554 (5)	0.4159 (2)	0.53398 (9)	0.0237 (3)
H1	0.2089 (8)	0.579 (4)	0.5241 (13)	0.034 (4)*
O1	0.21507 (4)	−0.01048 (18)	0.53804 (8)	0.0289 (3)
O2	0.42937 (4)	0.00520 (19)	0.45580 (7)	0.0279 (3)
O3	0.43346 (4)	0.36344 (18)	0.30218 (7)	0.0242 (2)
O4	0.34531 (4)	0.66623 (18)	0.25120 (7)	0.0255 (2)
C1	0.22841 (6)	0.2119 (2)	0.51372 (10)	0.0211 (3)
C11	0.28301 (5)	0.2637 (2)	0.45950 (9)	0.0198 (3)
C12	0.32948 (6)	0.1047 (2)	0.48557 (9)	0.0213 (3)
H12	0.3265	−0.0265	0.5379	0.026*
C13	0.38033 (6)	0.1395 (3)	0.43442 (9)	0.0211 (3)
C14	0.38357 (5)	0.3267 (2)	0.35373 (9)	0.0202 (3)
C15	0.33712 (6)	0.4871 (2)	0.32918 (9)	0.0198 (3)
C16	0.28646 (6)	0.4586 (2)	0.38262 (9)	0.0201 (3)
H16	0.2550	0.5693	0.3671	0.024*
C17	0.42929 (6)	−0.1910 (3)	0.53660 (10)	0.0268 (3)
H17A	0.4199	−0.1149	0.6055	0.040*
H17B	0.4671	−0.2707	0.5438	0.040*
H17C	0.4008	−0.3214	0.5157	0.040*
C18	0.44384 (6)	0.1648 (3)	0.22488 (11)	0.0294 (3)
H18A	0.4411	−0.0034	0.2593	0.044*
H18B	0.4821	0.1863	0.1981	0.044*
H18C	0.4154	0.1767	0.1647	0.044*
C19	0.29830 (6)	0.8303 (3)	0.22110 (10)	0.0258 (3)
H19A	0.2659	0.7263	0.1939	0.039*
H19B	0.3095	0.9489	0.1649	0.039*
H19C	0.2873	0.9282	0.2839	0.039*
C21	0.14322 (6)	0.3901 (3)	0.59287 (11)	0.0247 (3)
H21	0.1261	0.2185	0.5755	0.030*
C22	0.15657 (7)	0.4025 (4)	0.71420 (11)	0.0376 (4)
H22A	0.1758	0.5670	0.7323	0.045*
H22B	0.1831	0.2617	0.7357	0.045*
C23	0.10231 (7)	0.3799 (4)	0.77699 (12)	0.0404 (4)
H23A	0.0851	0.2082	0.7649	0.048*
H23B	0.1122	0.3984	0.8548	0.048*
C24	0.05945 (7)	0.5845 (3)	0.74171 (12)	0.0372 (4)
H24A	0.0750	0.7557	0.7612	0.045*
H24B	0.0239	0.5599	0.7800	0.045*
C25	0.04589 (7)	0.5735 (4)	0.62060 (12)	0.0376 (4)
H25A	0.0196	0.7153	0.5994	0.045*
H25B	0.0264	0.4097	0.6023	0.045*
C26	0.10009 (6)	0.5950 (3)	0.55750 (11)	0.0310 (3)
H26A	0.0901	0.5757	0.4797	0.037*
H26B	0.1173	0.7668	0.5692	0.037*

	U11	U22	U33	U12	U13	U23
N1	0.0193 (6)	0.0209 (6)	0.0316 (6)	−0.0013 (5)	0.0099 (4)	0.0005 (4)
O1	0.0248 (5)	0.0215 (5)	0.0413 (6)	−0.0004 (4)	0.0099 (4)	0.0034 (4)
O2	0.0198 (5)	0.0365 (6)	0.0277 (5)	0.0075 (4)	0.0047 (4)	0.0091 (4)
O3	0.0189 (5)	0.0278 (5)	0.0266 (5)	−0.0017 (4)	0.0083 (4)	−0.0024 (4)
O4	0.0250 (5)	0.0272 (5)	0.0248 (4)	0.0026 (4)	0.0065 (4)	0.0070 (4)
C1	0.0188 (6)	0.0230 (6)	0.0215 (6)	−0.0005 (5)	0.0011 (5)	−0.0006 (5)
C11	0.0184 (6)	0.0221 (6)	0.0192 (5)	−0.0026 (5)	0.0036 (5)	−0.0048 (5)
C12	0.0218 (7)	0.0225 (6)	0.0197 (6)	−0.0007 (5)	0.0030 (5)	0.0009 (5)
C13	0.0175 (6)	0.0248 (6)	0.0210 (6)	0.0015 (5)	0.0007 (5)	−0.0025 (5)
C14	0.0172 (6)	0.0240 (6)	0.0197 (6)	−0.0025 (5)	0.0039 (5)	−0.0035 (5)
C15	0.0214 (7)	0.0205 (6)	0.0178 (6)	−0.0012 (5)	0.0024 (5)	−0.0011 (4)
C16	0.0176 (6)	0.0212 (6)	0.0215 (6)	0.0018 (5)	0.0009 (5)	−0.0017 (5)
C17	0.0278 (7)	0.0269 (7)	0.0254 (6)	0.0054 (6)	−0.0003 (5)	0.0037 (5)
C18	0.0293 (8)	0.0299 (7)	0.0301 (7)	0.0031 (6)	0.0125 (6)	−0.0023 (6)
C19	0.0287 (7)	0.0255 (7)	0.0233 (6)	0.0040 (6)	0.0007 (5)	0.0033 (5)
C21	0.0190 (7)	0.0246 (7)	0.0312 (7)	−0.0017 (6)	0.0086 (5)	−0.0003 (5)
C22	0.0250 (8)	0.0572 (10)	0.0312 (8)	0.0053 (7)	0.0064 (6)	0.0073 (7)
C23	0.0338 (9)	0.0543 (10)	0.0342 (8)	0.0028 (8)	0.0124 (7)	0.0066 (7)
C24	0.0318 (8)	0.0385 (9)	0.0431 (8)	−0.0008 (7)	0.0184 (7)	−0.0058 (7)
C25	0.0218 (8)	0.0462 (9)	0.0456 (9)	0.0068 (7)	0.0085 (6)	0.0034 (7)
C26	0.0238 (8)	0.0352 (8)	0.0346 (7)	0.0050 (6)	0.0073 (6)	0.0057 (6)

N1—C1	1.3451 (17)	C18—H18B	0.9800
N1—C21	1.4670 (16)	C18—H18C	0.9800
N1—H1	0.916 (19)	C19—H19A	0.9800
O1—C1	1.2424 (16)	C19—H19B	0.9800
O2—C13	1.3615 (16)	C19—H19C	0.9800
O2—C17	1.4353 (16)	C21—C26	1.521 (2)
O3—C14	1.3761 (15)	C21—C22	1.529 (2)
O3—C18	1.4432 (16)	C21—H21	1.0000
O4—C15	1.3681 (15)	C22—C23	1.532 (2)
O4—C19	1.4307 (17)	C22—H22A	0.9900
C1—C11	1.5020 (17)	C22—H22B	0.9900
C11—C12	1.3945 (19)	C23—C24	1.516 (2)
C11—C16	1.4015 (18)	C23—H23A	0.9900
C12—C13	1.3920 (18)	C23—H23B	0.9900
C12—H12	0.9500	C24—C25	1.527 (2)
C13—C14	1.4058 (18)	C24—H24A	0.9900
C14—C15	1.3951 (19)	C24—H24B	0.9900
C15—C16	1.3988 (18)	C25—C26	1.5320 (19)
C16—H16	0.9500	C25—H25A	0.9900
C17—H17A	0.9800	C25—H25B	0.9900
C17—H17B	0.9800	C26—H26A	0.9900
C17—H17C	0.9800	C26—H26B	0.9900
C18—H18A	0.9800
C1—N1—C21	121.53 (11)	H19A—C19—H19B	109.5
C1—N1—H1	120.3 (11)	O4—C19—H19C	109.5
C21—N1—H1	117.0 (11)	H19A—C19—H19C	109.5
C13—O2—C17	118.23 (10)	H19B—C19—H19C	109.5
C14—O3—C18	112.80 (10)	N1—C21—C26	110.57 (11)
C15—O4—C19	117.42 (10)	N1—C21—C22	110.82 (11)
O1—C1—N1	122.58 (12)	C26—C21—C22	110.89 (12)
O1—C1—C11	120.55 (12)	N1—C21—H21	108.1
N1—C1—C11	116.87 (11)	C26—C21—H21	108.1
C12—C11—C16	121.26 (11)	C22—C21—H21	108.2
C12—C11—C1	117.54 (11)	C21—C22—C23	111.55 (13)
C16—C11—C1	121.16 (11)	C21—C22—H22A	109.3
C13—C12—C11	119.56 (11)	C23—C22—H22A	109.3
C13—C12—H12	120.2	C21—C22—H22B	109.3
C11—C12—H12	120.2	C23—C22—H22B	109.3
O2—C13—C12	125.32 (11)	H22A—C22—H22B	108.0
O2—C13—C14	114.92 (11)	C24—C23—C22	110.72 (13)
C12—C13—C14	119.75 (12)	C24—C23—H23A	109.5
O3—C14—C15	119.15 (11)	C22—C23—H23A	109.5
O3—C14—C13	120.54 (12)	C24—C23—H23B	109.5
C15—C14—C13	120.22 (11)	C22—C23—H23B	109.5
O4—C15—C14	115.40 (11)	H23A—C23—H23B	108.1
O4—C15—C16	124.30 (12)	C23—C24—C25	111.23 (13)
C14—C15—C16	120.29 (11)	C23—C24—H24A	109.4
C15—C16—C11	118.82 (12)	C25—C24—H24A	109.4
C15—C16—H16	120.6	C23—C24—H24B	109.4
C11—C16—H16	120.6	C25—C24—H24B	109.4
O2—C17—H17A	109.5	H24A—C24—H24B	108.0
O2—C17—H17B	109.5	C24—C25—C26	111.54 (13)
H17A—C17—H17B	109.5	C24—C25—H25A	109.3
O2—C17—H17C	109.5	C26—C25—H25A	109.3
H17A—C17—H17C	109.5	C24—C25—H25B	109.3
H17B—C17—H17C	109.5	C26—C25—H25B	109.3
O3—C18—H18A	109.5	H25A—C25—H25B	108.0
O3—C18—H18B	109.5	C21—C26—C25	110.91 (12)
H18A—C18—H18B	109.5	C21—C26—H26A	109.5
O3—C18—H18C	109.5	C25—C26—H26A	109.5
H18A—C18—H18C	109.5	C21—C26—H26B	109.5
H18B—C18—H18C	109.5	C25—C26—H26B	109.5
O4—C19—H19A	109.5	H26A—C26—H26B	108.0
O4—C19—H19B	109.5
C21—N1—C1—O1	4.06 (19)	C19—O4—C15—C16	−1.51 (18)
C21—N1—C1—C11	−175.93 (11)	O3—C14—C15—O4	2.05 (17)
O1—C1—C11—C12	−32.62 (17)	C13—C14—C15—O4	178.53 (11)
N1—C1—C11—C12	147.36 (12)	O3—C14—C15—C16	−178.18 (11)
O1—C1—C11—C16	145.07 (13)	C13—C14—C15—C16	−1.70 (18)
N1—C1—C11—C16	−34.94 (17)	O4—C15—C16—C11	178.64 (11)
C16—C11—C12—C13	−0.02 (18)	C14—C15—C16—C11	−1.11 (18)
C1—C11—C12—C13	177.67 (11)	C12—C11—C16—C15	1.99 (18)
C17—O2—C13—C12	0.73 (19)	C1—C11—C16—C15	−175.62 (11)
C17—O2—C13—C14	−179.46 (11)	C1—N1—C21—C26	−150.78 (12)
C11—C12—C13—O2	177.00 (12)	C1—N1—C21—C22	85.85 (16)
C11—C12—C13—C14	−2.81 (19)	N1—C21—C22—C23	179.14 (13)
C18—O3—C14—C15	−108.20 (13)	C26—C21—C22—C23	55.95 (18)
C18—O3—C14—C13	75.33 (15)	C21—C22—C23—C24	−56.00 (19)
O2—C13—C14—O3	0.29 (17)	C22—C23—C24—C25	55.59 (19)
C12—C13—C14—O3	−179.89 (11)	C23—C24—C25—C26	−55.74 (19)
O2—C13—C14—C15	−176.15 (11)	N1—C21—C26—C25	−178.60 (12)
C12—C13—C14—C15	3.68 (19)	C22—C21—C26—C25	−55.27 (17)
C19—O4—C15—C14	178.25 (11)	C24—C25—C26—C21	55.42 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.916 (19)	2.153 (19)	3.0262 (15)	159.0 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.916 (19)	2.153 (19)	3.0262 (15)	159.0 (15)

Symmetry code: (i) .