4-[2-(3,4-Dimethoxy-phenethyl-amino)prop-oxy]-2-methoxy-benzamide.

The title compound, C(21)H(28)N(2)O(5), has two intra-molecular N-H⋯O hydrogen bonds. Inter-molecular N-H⋯O hydrogen bonds [graph-set motif R(2) (2)(8)] give rise to a dimer. Weak N-H⋯N hydrogen bonds between neighboring dimers further extend the crystal structure, which exhibits an infinite chain motif.

Related literature

For related literature, see: Allen et al. (1987 ▶); Beduschi & Beduachi (1998 ▶); Bernstein et al.(1995 ▶); Boonnak et al. (2005 ▶); Gunderman et al. (1995 ▶); Hieble et al. (1995 ▶); Kasztreiner et al. (1989 ▶); Ng et al. (2005 ▶); Xi et al. (2005 ▶).

Experimental

Crystal data

C21H28N2O5

M = 388.45

Monoclinic,

a = 7.7564 (3) Å

b = 9.3509 (4) Å

c = 29.9987 (12) Å

β = 95.370 (3)°

V = 2166.24 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 (2) K

0.21 × 0.18 × 0.17 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: none

26019 measured reflections

3909 independent reflections

1966 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.183

S = 1.03

3909 reflections

260 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808015134/zl2117sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015134/zl2117Isup2.hkl

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

C21H28N2O5	F000 = 832
Mr = 388.45	Dx = 1.191 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2279 reflections
a = 7.7564 (3) Å	θ = 2.3–28.0º
b = 9.3509 (4) Å	µ = 0.09 mm−1
c = 29.9987 (12) Å	T = 296 (2) K
β = 95.370 (3)º	Block, colorless
V = 2166.24 (15) Å3	0.21 × 0.18 × 0.17 mm
Z = 4

Bruker APEXII area-detector diffractometer	1966 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
Monochromator: graphite	θmax = 25.2º
T = 296(2) K	θmin = 2.3º
φ and ω scans	h = −8→9
Absorption correction: none	k = −11→11
26019 measured reflections	l = −35→35
3909 independent reflections

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)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.183	w = 1/[σ2(Fo2) + (0.0802P)2 + 0.288P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3909 reflections	Δρmax = 0.24 e Å−3
260 parameters	Δρmin = −0.22 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
C1	1.0849 (4)	0.9275 (3)	0.68939 (10)	0.0707 (8)
C2	1.0775 (4)	0.8967 (3)	0.73403 (10)	0.0730 (9)
H2	1.0012	0.8264	0.7419	0.088*
C3	1.1788 (4)	0.9662 (3)	0.76742 (11)	0.0768 (9)
C4	1.2923 (4)	1.0728 (3)	0.75616 (13)	0.0802 (9)
C5	1.3002 (4)	1.1052 (4)	0.71190 (14)	0.0894 (10)
H5	1.3752	1.1762	0.7038	0.107*
C6	1.1968 (5)	1.0324 (4)	0.67897 (12)	0.0854 (10)
H6	1.2040	1.0558	0.6491	0.102*
C7	0.2048 (4)	0.3654 (3)	0.58051 (10)	0.0731 (9)
H7	0.1768	0.2941	0.6002	0.088*
C8	0.2697 (4)	0.4909 (4)	0.59783 (10)	0.0786 (9)
H8	0.2876	0.5034	0.6287	0.094*
C9	0.3086 (4)	0.5986 (3)	0.56951 (10)	0.0652 (8)
C10	0.2844 (3)	0.5786 (3)	0.52359 (9)	0.0637 (8)
H10	0.3093	0.6521	0.5043	0.076*
C11	0.2230 (3)	0.4489 (3)	0.50650 (9)	0.0571 (7)
C12	0.1785 (3)	0.3388 (3)	0.53488 (9)	0.0604 (7)
C13	1.0809 (9)	0.8210 (6)	0.82400 (14)	0.194 (3)
H13A	0.9600	0.8442	0.8191	0.292*
H13B	1.1095	0.7984	0.8550	0.292*
H13C	1.1054	0.7400	0.8059	0.292*
C14	0.4230 (4)	0.8365 (3)	0.56233 (10)	0.0785 (9)
H14A	0.3207	0.8859	0.5491	0.094*
H14B	0.4874	0.8014	0.5384	0.094*
C15	0.5335 (4)	0.9363 (3)	0.59209 (10)	0.0752 (9)
H15	0.4726	0.9616	0.6182	0.090*
C16	0.8086 (4)	0.9358 (3)	0.63960 (10)	0.0766 (9)
H16A	0.7475	0.9578	0.6655	0.092*
H16B	0.8422	1.0254	0.6266	0.092*
C17	0.9687 (4)	0.8500 (4)	0.65416 (10)	0.0833 (10)
H17A	1.0321	0.8313	0.6284	0.100*
H17B	0.9348	0.7588	0.6660	0.100*
C18	1.5228 (7)	1.2293 (6)	0.78212 (16)	0.171 (2)
H18A	1.5999	1.1812	0.7638	0.257*
H18B	1.5858	1.2594	0.8096	0.257*
H18C	1.4738	1.3113	0.7664	0.257*
C19	0.5701 (5)	1.0702 (3)	0.56651 (13)	0.1053 (12)
H19A	0.6320	1.1371	0.5863	0.158*
H19B	0.4628	1.1121	0.5544	0.158*
H19C	0.6388	1.0465	0.5425	0.158*
C20	0.2483 (4)	0.5301 (3)	0.43139 (9)	0.0771 (9)
H20A	0.1776	0.6133	0.4343	0.116*
H20B	0.2303	0.4945	0.4013	0.116*
H20C	0.3679	0.5551	0.4381	0.116*
C21	0.1018 (4)	0.1977 (3)	0.52065 (11)	0.0676 (8)
N1	0.6938 (3)	0.8582 (2)	0.60697 (8)	0.0666 (7)
H1	0.662 (4)	0.780 (2)	0.6217 (8)	0.080*
N2	0.0991 (3)	0.1560 (3)	0.47879 (8)	0.0817 (8)
H2A	0.0548	0.0747	0.4708	0.098*
H2B	0.1417	0.2102	0.4594	0.098*
O1	0.3744 (3)	0.7205 (2)	0.58938 (6)	0.0838 (7)
O2	1.1798 (4)	0.9383 (3)	0.81226 (8)	0.1191 (10)
O3	1.3892 (3)	1.1353 (3)	0.79165 (9)	0.1160 (9)
O4	0.2023 (3)	0.4228 (2)	0.46171 (6)	0.0753 (6)
O5	0.0413 (4)	0.1217 (2)	0.54918 (8)	0.1049 (9)

	U11	U22	U33	U12	U13	U23
C1	0.063 (2)	0.075 (2)	0.073 (2)	0.0073 (17)	0.0014 (16)	0.0039 (17)
C2	0.065 (2)	0.071 (2)	0.082 (2)	−0.0139 (16)	0.0032 (16)	−0.0044 (17)
C3	0.079 (2)	0.076 (2)	0.076 (2)	−0.0129 (19)	0.0067 (18)	−0.0039 (17)
C4	0.072 (2)	0.070 (2)	0.099 (3)	−0.0126 (18)	0.0079 (19)	−0.011 (2)
C5	0.073 (2)	0.077 (2)	0.120 (3)	−0.0097 (19)	0.019 (2)	0.015 (2)
C6	0.081 (2)	0.090 (3)	0.086 (2)	0.011 (2)	0.012 (2)	0.018 (2)
C7	0.082 (2)	0.070 (2)	0.069 (2)	−0.0096 (18)	0.0146 (16)	0.0086 (16)
C8	0.091 (2)	0.083 (2)	0.0625 (18)	−0.0174 (19)	0.0095 (17)	0.0007 (18)
C9	0.0610 (19)	0.0651 (19)	0.069 (2)	−0.0088 (15)	0.0022 (15)	−0.0018 (16)
C10	0.0598 (19)	0.0609 (18)	0.069 (2)	−0.0022 (15)	−0.0005 (14)	0.0091 (15)
C11	0.0533 (17)	0.0567 (17)	0.0608 (18)	0.0012 (14)	0.0018 (13)	0.0001 (14)
C12	0.0518 (17)	0.0616 (18)	0.0688 (19)	−0.0031 (14)	0.0103 (14)	0.0015 (15)
C13	0.327 (8)	0.172 (5)	0.088 (3)	−0.131 (6)	0.039 (4)	−0.003 (3)
C14	0.081 (2)	0.066 (2)	0.085 (2)	−0.0101 (17)	−0.0076 (17)	0.0068 (17)
C15	0.069 (2)	0.0654 (19)	0.088 (2)	−0.0055 (17)	−0.0093 (17)	0.0026 (17)
C16	0.074 (2)	0.075 (2)	0.079 (2)	−0.0001 (17)	−0.0057 (17)	−0.0088 (16)
C17	0.083 (2)	0.087 (2)	0.077 (2)	0.0133 (19)	−0.0053 (18)	−0.0072 (17)
C18	0.145 (4)	0.178 (5)	0.192 (5)	−0.105 (4)	0.023 (4)	−0.035 (4)
C19	0.101 (3)	0.071 (2)	0.137 (3)	−0.008 (2)	−0.022 (2)	0.009 (2)
C20	0.089 (2)	0.073 (2)	0.0697 (19)	0.0018 (18)	0.0097 (17)	0.0126 (16)
C21	0.067 (2)	0.0626 (19)	0.074 (2)	−0.0052 (16)	0.0160 (16)	0.0004 (17)
N1	0.0687 (17)	0.0610 (15)	0.0689 (15)	−0.0033 (13)	0.0005 (13)	−0.0027 (12)
N2	0.101 (2)	0.0681 (16)	0.0786 (18)	−0.0248 (15)	0.0219 (15)	−0.0060 (14)
O1	0.0948 (17)	0.0803 (15)	0.0759 (14)	−0.0244 (13)	0.0059 (12)	−0.0059 (12)
O2	0.157 (2)	0.126 (2)	0.0737 (16)	−0.0677 (19)	0.0075 (15)	−0.0092 (14)
O3	0.1067 (19)	0.113 (2)	0.128 (2)	−0.0478 (17)	0.0056 (16)	−0.0250 (16)
O4	0.0972 (16)	0.0654 (13)	0.0627 (13)	−0.0120 (11)	0.0038 (11)	0.0065 (10)
O5	0.147 (2)	0.0836 (16)	0.0905 (16)	−0.0453 (16)	0.0465 (15)	−0.0088 (13)

C1—C6	1.365 (4)	C14—C15	1.503 (4)
C1—C2	1.376 (4)	C14—H14A	0.9700
C1—C17	1.509 (4)	C14—H14B	0.9700
C2—C3	1.377 (4)	C15—N1	1.475 (4)
C2—H2	0.9300	C15—C19	1.509 (4)
C3—O2	1.369 (4)	C15—H15	0.9800
C3—C4	1.393 (4)	C16—N1	1.454 (3)
C4—C5	1.369 (4)	C16—C17	1.508 (4)
C4—O3	1.375 (4)	C16—H16A	0.9700
C5—C6	1.391 (5)	C16—H16B	0.9700
C5—H5	0.9300	C17—H17A	0.9700
C6—H6	0.9300	C17—H17B	0.9700
C7—C8	1.361 (4)	C18—O3	1.408 (4)
C7—C12	1.387 (4)	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—C9	1.369 (4)	C18—H18C	0.9600
C8—H8	0.9300	C19—H19A	0.9600
C9—O1	1.363 (3)	C19—H19B	0.9600
C9—C10	1.385 (4)	C19—H19C	0.9600
C10—C11	1.383 (4)	C20—O4	1.422 (3)
C10—H10	0.9300	C20—H20A	0.9600
C11—O4	1.360 (3)	C20—H20B	0.9600
C11—C12	1.400 (4)	C20—H20C	0.9600
C12—C21	1.493 (4)	C21—O5	1.238 (3)
C13—O2	1.403 (5)	C21—N2	1.313 (3)
C13—H13A	0.9600	N1—H1	0.903 (17)
C13—H13B	0.9600	N2—H2A	0.8600
C13—H13C	0.9600	N2—H2B	0.8600
C14—O1	1.426 (3)
C6—C1—C2	117.3 (3)	N1—C15—C19	111.8 (3)
C6—C1—C17	122.4 (3)	C14—C15—C19	109.7 (3)
C2—C1—C17	120.3 (3)	N1—C15—H15	109.5
C1—C2—C3	122.4 (3)	C14—C15—H15	109.5
C1—C2—H2	118.8	C19—C15—H15	109.5
C3—C2—H2	118.8	N1—C16—C17	111.4 (2)
O2—C3—C2	125.1 (3)	N1—C16—H16A	109.3
O2—C3—C4	115.4 (3)	C17—C16—H16A	109.3
C2—C3—C4	119.5 (3)	N1—C16—H16B	109.3
C5—C4—O3	125.9 (3)	C17—C16—H16B	109.3
C5—C4—C3	118.7 (3)	H16A—C16—H16B	108.0
O3—C4—C3	115.4 (3)	C16—C17—C1	111.6 (3)
C4—C5—C6	120.4 (3)	C16—C17—H17A	109.3
C4—C5—H5	119.8	C1—C17—H17A	109.3
C6—C5—H5	119.8	C16—C17—H17B	109.3
C1—C6—C5	121.7 (3)	C1—C17—H17B	109.3
C1—C6—H6	119.1	H17A—C17—H17B	108.0
C5—C6—H6	119.1	O3—C18—H18A	109.5
C8—C7—C12	123.2 (3)	O3—C18—H18B	109.5
C8—C7—H7	118.4	H18A—C18—H18B	109.5
C12—C7—H7	118.4	O3—C18—H18C	109.5
C7—C8—C9	119.5 (3)	H18A—C18—H18C	109.5
C7—C8—H8	120.3	H18B—C18—H18C	109.5
C9—C8—H8	120.3	C15—C19—H19A	109.5
O1—C9—C8	116.0 (3)	C15—C19—H19B	109.5
O1—C9—C10	123.9 (3)	H19A—C19—H19B	109.5
C8—C9—C10	120.0 (3)	C15—C19—H19C	109.5
C11—C10—C9	119.8 (3)	H19A—C19—H19C	109.5
C11—C10—H10	120.1	H19B—C19—H19C	109.5
C9—C10—H10	120.1	O4—C20—H20A	109.5
O4—C11—C10	121.9 (2)	O4—C20—H20B	109.5
O4—C11—C12	117.1 (2)	H20A—C20—H20B	109.5
C10—C11—C12	121.0 (3)	O4—C20—H20C	109.5
C7—C12—C11	116.5 (3)	H20A—C20—H20C	109.5
C7—C12—C21	117.3 (3)	H20B—C20—H20C	109.5
C11—C12—C21	126.2 (3)	O5—C21—N2	121.2 (3)
O2—C13—H13A	109.5	O5—C21—C12	118.4 (3)
O2—C13—H13B	109.5	N2—C21—C12	120.4 (3)
H13A—C13—H13B	109.5	C16—N1—C15	113.7 (2)
O2—C13—H13C	109.5	C16—N1—H1	104.8 (18)
H13A—C13—H13C	109.5	C15—N1—H1	106.9 (19)
H13B—C13—H13C	109.5	C21—N2—H2A	120.0
O1—C14—C15	107.5 (2)	C21—N2—H2B	120.0
O1—C14—H14A	110.2	H2A—N2—H2B	120.0
C15—C14—H14A	110.2	C9—O1—C14	119.7 (2)
O1—C14—H14B	110.2	C3—O2—C13	116.3 (3)
C15—C14—H14B	110.2	C4—O3—C18	117.9 (3)
H14A—C14—H14B	108.5	C11—O4—C20	119.4 (2)
N1—C15—C14	106.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5i	0.86	2.05	2.909 (3)	178
N2—H2B···O4	0.86	2.04	2.684 (3)	131
N2—H2B···N1ii	0.86	2.54	3.161 (3)	129
N1—H1···O1	0.903 (17)	2.41 (3)	2.798 (3)	106 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O5i	0.86	2.05	2.909 (3)	178
N2—H2B⋯O4	0.86	2.04	2.684 (3)	131
N2—H2B⋯N1ii	0.86	2.54	3.161 (3)	129
N1—H1⋯O1	0.903 (17)	2.41 (3)	2.798 (3)	106 (2)

Symmetry codes: (i) ; (ii) .