N-(4-Chloro-phen-yl)-3,4,5-trimethoxy-benzamide.

In the title compound, C(16)H(16)ClNO(4), the dihedral angle between the two aromatic rings is 67.33 (8)°. The crystal packing shows strong inter-molecular N-H⋯O hydrogen bonds that link the mol-ecules to form chains along [01].

Related literature

For related literature, see: Capdeville et al. (2002 ▶); Ho et al. (2002 ▶); Igawa et al. (1999 ▶); Jackson et al. (1994 ▶); Makino et al. (2003 ▶); Zhichkin et al. (2007 ▶).

Experimental

Crystal data

C16H16n class="Chemical">ClNO4

M = 321.75

Monoclinic,

a = 9.487 (2) Å

b = 25.666 (6) Å

c = 6.9781 (15) Å

β = 112.340 (5)°

V = 1571.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 120 (2) K

0.41 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.901, T max = 0.975

6765 measured reflections

3581 independent reflections

3104 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.106

S = 1.02

3581 reflections

202 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), with 1780 Friedel pairs

Flack parameter: 0.06 (6)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAIn class="Chemical">NT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023234/bt2747sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023234/bt2747Isup2.hkl

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

C16H16ClNO4	F000 = 672
Mr = 321.75	Dx = 1.360 Mg m−3
Monoclinic, Cc	Mo Kα radiation λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 879 reflections
a = 9.487 (2) Å	θ = 2.5–26.6º
b = 25.666 (6) Å	µ = 0.26 mm−1
c = 6.9781 (15) Å	T = 120 (2) K
β = 112.340 (5)º	Prism, colourless
V = 1571.5 (6) Å3	0.41 × 0.10 × 0.10 mm
Z = 4

Bruker SMART APEX diffractometer	3581 independent reflections
Radiation source: sealed tube	3104 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
T = 120(2) K	θmax = 27.9º
φ and ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −12→12
Tmin = 0.901, Tmax = 0.975	k = −33→29
6765 measured reflections	l = −9→9

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.1374P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.106	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.33 e Å−3
3581 reflections	Δρmin = −0.24 e Å−3
202 parameters	Extinction correction: none
2 restraints	Absolute structure: Flack (1983), with 1780 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (6)
Secondary atom site location: difference Fourier map

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
Cl1	0.24506 (8)	0.52096 (2)	−0.45259 (9)	0.03098 (17)
O1	0.0700 (2)	0.75731 (7)	−0.2052 (3)	0.0251 (4)
O2	0.3495 (2)	0.83040 (7)	0.6718 (3)	0.0293 (4)
O3	0.2739 (2)	0.92522 (7)	0.5093 (3)	0.0287 (4)
O4	0.1760 (2)	0.94204 (7)	0.1029 (3)	0.0293 (4)
N1	0.2656 (2)	0.71265 (7)	0.0305 (3)	0.0206 (4)
H1	0.3366	0.7136	0.1562	0.025*
C1	0.1742 (3)	0.75494 (10)	−0.0350 (4)	0.0201 (5)
C2	0.2087 (3)	0.79915 (9)	0.1153 (4)	0.0190 (5)
C3	0.2689 (3)	0.79115 (10)	0.3293 (4)	0.0207 (5)
H3A	0.2926	0.7570	0.3846	0.025*
C4	0.2938 (3)	0.83381 (10)	0.4601 (4)	0.0217 (5)
C5	0.2589 (3)	0.88383 (10)	0.3797 (4)	0.0217 (5)
C6	0.2015 (3)	0.89163 (10)	0.1650 (4)	0.0226 (6)
C7	0.1739 (3)	0.84890 (9)	0.0330 (4)	0.0209 (5)
H7A	0.1314	0.8538	−0.1129	0.025*
C8	0.4275 (4)	0.78426 (12)	0.7598 (5)	0.0380 (7)
H8A	0.3560	0.7549	0.7223	0.057*
H8B	0.4727	0.7878	0.9109	0.057*
H8C	0.5083	0.7779	0.7073	0.057*
C9	0.4195 (4)	0.94971 (13)	0.5730 (6)	0.0457 (8)
H9A	0.4986	0.9251	0.6541	0.069*
H9B	0.4213	0.9803	0.6582	0.069*
H9C	0.4387	0.9606	0.4506	0.069*
C10	0.1094 (4)	0.95144 (11)	−0.1151 (5)	0.0375 (7)
H10A	0.1764	0.9377	−0.1807	0.056*
H10B	0.0960	0.9890	−0.1405	0.056*
H10C	0.0100	0.9341	−0.1736	0.056*
C11	0.2554 (3)	0.66682 (9)	−0.0888 (4)	0.0194 (5)
C12	0.1169 (3)	0.64558 (10)	−0.2157 (4)	0.0238 (5)
H12A	0.0244	0.6618	−0.2258	0.029*
C13	0.1133 (3)	0.60093 (10)	−0.3273 (4)	0.0269 (6)
H13A	0.0184	0.5868	−0.4158	0.032*
C14	0.2479 (3)	0.57674 (10)	−0.3103 (4)	0.0218 (5)
C15	0.3862 (3)	0.59685 (10)	−0.1809 (4)	0.0259 (6)
H15A	0.4784	0.5798	−0.1675	0.031*
C16	0.3897 (3)	0.64200 (10)	−0.0706 (4)	0.0250 (6)
H16A	0.4847	0.6561	0.0182	0.030*

	U11	U22	U33	U12	U13	U23
Cl1	0.0333 (3)	0.0268 (3)	0.0286 (3)	0.0033 (3)	0.0071 (3)	−0.0101 (3)
O1	0.0181 (9)	0.0240 (10)	0.0225 (9)	0.0011 (7)	−0.0043 (7)	−0.0031 (7)
O2	0.0373 (11)	0.0277 (10)	0.0193 (9)	0.0051 (8)	0.0066 (8)	0.0008 (8)
O3	0.0346 (11)	0.0236 (9)	0.0262 (10)	−0.0009 (8)	0.0097 (8)	−0.0075 (8)
O4	0.0406 (12)	0.0171 (9)	0.0248 (10)	0.0013 (8)	0.0062 (9)	0.0014 (8)
N1	0.0170 (10)	0.0186 (10)	0.0186 (10)	0.0016 (8)	−0.0019 (8)	−0.0021 (9)
C1	0.0157 (11)	0.0203 (12)	0.0207 (13)	−0.0004 (9)	0.0026 (11)	−0.0003 (10)
C2	0.0154 (12)	0.0179 (12)	0.0214 (13)	−0.0006 (9)	0.0046 (10)	−0.0017 (10)
C3	0.0172 (11)	0.0188 (12)	0.0221 (13)	−0.0002 (9)	0.0027 (10)	0.0033 (10)
C4	0.0218 (13)	0.0241 (14)	0.0184 (13)	−0.0003 (10)	0.0068 (11)	−0.0015 (10)
C5	0.0218 (12)	0.0203 (13)	0.0230 (13)	−0.0009 (10)	0.0085 (11)	−0.0056 (10)
C6	0.0227 (13)	0.0181 (13)	0.0248 (14)	0.0016 (10)	0.0065 (11)	0.0010 (10)
C7	0.0192 (11)	0.0211 (13)	0.0187 (12)	0.0010 (9)	0.0029 (10)	0.0005 (10)
C8	0.052 (2)	0.0397 (17)	0.0211 (14)	0.0166 (15)	0.0126 (14)	0.0076 (13)
C9	0.0401 (18)	0.0386 (18)	0.050 (2)	−0.0104 (14)	0.0079 (16)	−0.0163 (15)
C10	0.058 (2)	0.0190 (14)	0.0282 (15)	0.0046 (13)	0.0084 (14)	0.0044 (12)
C11	0.0225 (12)	0.0159 (12)	0.0161 (11)	−0.0007 (9)	0.0031 (10)	0.0018 (9)
C12	0.0176 (12)	0.0218 (13)	0.0294 (14)	0.0030 (10)	0.0059 (11)	−0.0023 (11)
C13	0.0200 (13)	0.0283 (15)	0.0255 (14)	−0.0029 (10)	0.0011 (11)	−0.0080 (11)
C14	0.0286 (13)	0.0161 (12)	0.0209 (13)	0.0003 (10)	0.0095 (11)	−0.0039 (10)
C15	0.0208 (13)	0.0263 (14)	0.0285 (14)	0.0057 (10)	0.0069 (11)	0.0015 (11)
C16	0.0191 (13)	0.0233 (14)	0.0255 (14)	−0.0013 (10)	0.0005 (11)	−0.0014 (11)

Cl1—C14	1.737 (2)	C8—H8A	0.9800
O1—C1	1.225 (3)	C8—H8B	0.9800
O2—C4	1.369 (3)	C8—H8C	0.9800
O2—C8	1.408 (3)	C9—H9A	0.9800
O3—C5	1.367 (3)	C9—H9B	0.9800
O3—C9	1.426 (4)	C9—H9C	0.9800
O4—C6	1.357 (3)	C10—H10A	0.9800
O4—C10	1.429 (4)	C10—H10B	0.9800
N1—C1	1.356 (3)	C10—H10C	0.9800
N1—C11	1.423 (3)	C11—C16	1.386 (4)
N1—H1	0.8800	C11—C12	1.386 (4)
C1—C2	1.494 (3)	C12—C13	1.378 (4)
C2—C7	1.387 (3)	C12—H12A	0.9500
C2—C3	1.397 (4)	C13—C14	1.384 (4)
C3—C4	1.387 (3)	C13—H13A	0.9500
C3—H3A	0.9500	C14—C15	1.380 (4)
C4—C5	1.390 (4)	C15—C16	1.385 (4)
C5—C6	1.400 (3)	C15—H15A	0.9500
C6—C7	1.392 (4)	C16—H16A	0.9500
C7—H7A	0.9500
C4—O2—C8	116.6 (2)	H8B—C8—H8C	109.5
C5—O3—C9	113.2 (2)	O3—C9—H9A	109.5
C6—O4—C10	117.0 (2)	O3—C9—H9B	109.5
C1—N1—C11	124.9 (2)	H9A—C9—H9B	109.5
C1—N1—H1	117.5	O3—C9—H9C	109.5
C11—N1—H1	117.5	H9A—C9—H9C	109.5
O1—C1—N1	123.0 (2)	H9B—C9—H9C	109.5
O1—C1—C2	121.6 (2)	O4—C10—H10A	109.5
N1—C1—C2	115.5 (2)	O4—C10—H10B	109.5
C7—C2—C3	120.9 (2)	H10A—C10—H10B	109.5
C7—C2—C1	117.0 (2)	O4—C10—H10C	109.5
C3—C2—C1	122.0 (2)	H10A—C10—H10C	109.5
C4—C3—C2	119.1 (2)	H10B—C10—H10C	109.5
C4—C3—H3A	120.5	C16—C11—C12	119.5 (2)
C2—C3—H3A	120.5	C16—C11—N1	118.1 (2)
O2—C4—C3	124.0 (2)	C12—C11—N1	122.4 (2)
O2—C4—C5	115.4 (2)	C13—C12—C11	120.1 (2)
C3—C4—C5	120.6 (2)	C13—C12—H12A	119.9
O3—C5—C4	120.1 (2)	C11—C12—H12A	119.9
O3—C5—C6	119.8 (2)	C12—C13—C14	120.0 (2)
C4—C5—C6	120.0 (2)	C12—C13—H13A	120.0
O4—C6—C7	125.0 (2)	C14—C13—H13A	120.0
O4—C6—C5	115.3 (2)	C15—C14—C13	120.3 (2)
C7—C6—C5	119.6 (2)	C15—C14—Cl1	119.1 (2)
C2—C7—C6	119.7 (2)	C13—C14—Cl1	120.5 (2)
C2—C7—H7A	120.1	C14—C15—C16	119.5 (2)
C6—C7—H7A	120.1	C14—C15—H15A	120.2
O2—C8—H8A	109.5	C16—C15—H15A	120.2
O2—C8—H8B	109.5	C15—C16—C11	120.5 (2)
H8A—C8—H8B	109.5	C15—C16—H16A	119.8
O2—C8—H8C	109.5	C11—C16—H16A	119.8
H8A—C8—H8C	109.5
C11—N1—C1—O1	1.5 (4)	O3—C5—C6—O4	5.1 (3)
C11—N1—C1—C2	−178.5 (2)	C4—C5—C6—O4	−177.9 (2)
O1—C1—C2—C7	−29.2 (3)	O3—C5—C6—C7	−174.4 (2)
N1—C1—C2—C7	150.8 (2)	C4—C5—C6—C7	2.6 (4)
O1—C1—C2—C3	148.9 (2)	C3—C2—C7—C6	1.1 (4)
N1—C1—C2—C3	−31.1 (3)	C1—C2—C7—C6	179.2 (2)
C7—C2—C3—C4	0.0 (4)	O4—C6—C7—C2	178.2 (2)
C1—C2—C3—C4	−178.0 (2)	C5—C6—C7—C2	−2.4 (4)
C8—O2—C4—C3	19.9 (4)	C1—N1—C11—C16	143.0 (3)
C8—O2—C4—C5	−161.6 (3)	C1—N1—C11—C12	−39.2 (4)
C2—C3—C4—O2	178.7 (2)	C16—C11—C12—C13	−1.8 (4)
C2—C3—C4—C5	0.2 (4)	N1—C11—C12—C13	−179.6 (2)
C9—O3—C5—C4	92.2 (3)	C11—C12—C13—C14	1.0 (4)
C9—O3—C5—C6	−90.8 (3)	C12—C13—C14—C15	0.5 (4)
O2—C4—C5—O3	−3.1 (3)	C12—C13—C14—Cl1	−179.1 (2)
C3—C4—C5—O3	175.5 (2)	C13—C14—C15—C16	−1.1 (4)
O2—C4—C5—C6	179.8 (2)	Cl1—C14—C15—C16	178.5 (2)
C3—C4—C5—C6	−1.6 (4)	C14—C15—C16—C11	0.3 (4)
C10—O4—C6—C7	2.9 (4)	C12—C11—C16—C15	1.2 (4)
C10—O4—C6—C5	−176.6 (3)	N1—C11—C16—C15	179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	2.18	2.878 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	2.18	2.878 (3)	136

Symmetry code: (i) .