4-[4-(3-Methoxy-benzamido)phen-oxy]-N-methyl-picolinamide.

In the title compound, C(21)H(19)N(3)O(4), the central benzene ring makes dihedral angles of 78.54 (6) and 75.30 (6)° with the pyridine and 3-methoxy-phenyl rings, respectively. An intra-molecular N-H⋯N interaction occurs, generating an S(?). The crystal packing shows inter-molecular N-H⋯O hydrogen-bonding inter-actions between the N-H groups and the O atoms of the 3-methoxy-phenyl ring and the carbonyl groups of the amide functions. Inter-molecular C-H⋯O inter-actions are also present.

Related literature

For related compounds and their biological activity, see: Khire et al. (2004 ▶); Dominguez et al. (2007 ▶).

Experimental

Crystal data

C21H19N3O4

M = 377.39

Triclinic,

a = 5.0915 (10) Å

b = 8.3251 (17) Å

c = 11.611 (2) Å

α = 71.29 (3)°

β = 87.74 (3)°

γ = 76.10 (3)°

V = 452.14 (16) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 113 K

0.34 × 0.29 × 0.19 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.968, T max = 0.982

3733 measured reflections

2108 independent reflections

1811 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.085

S = 1.10

2108 reflections

263 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809055688/om2308sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055688/om2308Isup2.hkl

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

C21H19N3O4	Z = 1
Mr = 377.39	F(000) = 198
Triclinic, P1	Dx = 1.386 Mg m−3
a = 5.0915 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3251 (17) Å	Cell parameters from 1652 reflections
c = 11.611 (2) Å	θ = 2.7–27.8°
α = 71.29 (3)°	µ = 0.10 mm−1
β = 87.74 (3)°	T = 113 K
γ = 76.10 (3)°	Block, colourless
V = 452.14 (16) Å3	0.34 × 0.29 × 0.19 mm

Rigaku Saturn CCD area-detector diffractometer	2108 independent reflections
Radiation source: rotating anode	1811 reflections with I > 2σ(I)
confocal	Rint = 0.026
Detector resolution: 7.31 pixels mm-1	θmax = 27.8°, θmin = 2.7°
ω and φ scans	h = −6→4
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→10
Tmin = 0.968, Tmax = 0.982	l = −14→15
3733 measured reflections

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)] = 0.035	Hydrogen site location: mixed
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0481P)2] where P = (Fo2 + 2Fc2)/3
2108 reflections	(Δ/σ)max < 0.001
263 parameters	Δρmax = 0.22 e Å−3
3 restraints	Δρmin = −0.24 e Å−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
O1	−0.3679 (3)	1.5504 (2)	0.23318 (15)	0.0212 (4)
O2	−0.1469 (3)	0.9491 (2)	0.56055 (17)	0.0249 (4)
O3	0.4394 (3)	0.1895 (2)	0.81518 (15)	0.0220 (4)
O4	1.1345 (3)	0.2263 (2)	1.10678 (16)	0.0230 (4)
N1	0.3007 (3)	0.9089 (2)	0.60459 (17)	0.0154 (4)
H1N	0.443 (6)	0.954 (4)	0.579 (3)	0.031 (8)*
N2	1.0377 (4)	−0.1617 (2)	1.06587 (18)	0.0197 (4)
N3	1.3326 (4)	−0.0601 (3)	1.20340 (18)	0.0202 (4)
H3N	1.353 (6)	−0.166 (4)	1.208 (3)	0.025 (7)*
C1	0.0404 (4)	1.1969 (3)	0.48677 (19)	0.0138 (4)
C2	−0.1555 (4)	1.2811 (3)	0.3920 (2)	0.0157 (4)
H2	−0.2683	1.2179	0.3713	0.019*
C3	−0.1849 (4)	1.4569 (3)	0.3282 (2)	0.0166 (5)
C4	−0.0230 (4)	1.5503 (3)	0.3610 (2)	0.0186 (5)
H4	−0.0441	1.6711	0.3181	0.022*
C5	0.1675 (4)	1.4670 (3)	0.4559 (2)	0.0196 (5)
H5	0.2754	1.5316	0.4784	0.024*
C6	0.2036 (4)	1.2891 (3)	0.5190 (2)	0.0167 (5)
H6	0.3377	1.2318	0.5830	0.020*
C7	−0.4855 (5)	1.4516 (3)	0.1769 (2)	0.0240 (5)
H7A	−0.6035	1.3902	0.2340	0.036*
H7B	−0.3410	1.3663	0.1549	0.036*
H7C	−0.5919	1.5310	0.1034	0.036*
C8	0.0553 (4)	1.0091 (3)	0.5533 (2)	0.0163 (4)
C9	0.3486 (4)	0.7259 (3)	0.66625 (19)	0.0145 (4)
C10	0.5761 (4)	0.6131 (3)	0.6406 (2)	0.0162 (4)
H10	0.7046	0.6589	0.5865	0.019*
C11	0.6152 (4)	0.4336 (3)	0.6942 (2)	0.0190 (5)
H11	0.7689	0.3560	0.6763	0.023*
C12	0.4271 (4)	0.3690 (3)	0.7740 (2)	0.0174 (5)
C13	0.2105 (4)	0.4795 (3)	0.8055 (2)	0.0213 (5)
H13	0.0892	0.4336	0.8640	0.026*
C14	0.1710 (4)	0.6586 (3)	0.7512 (2)	0.0204 (5)
H14	0.0215	0.7356	0.7723	0.025*
C15	0.6403 (4)	0.0792 (3)	0.8978 (2)	0.0169 (5)
C16	0.6760 (5)	−0.0977 (3)	0.9182 (2)	0.0194 (5)
H16	0.5661	−0.1394	0.8757	0.023*
C17	0.8763 (5)	−0.2126 (3)	1.0024 (2)	0.0210 (5)
H17	0.9012	−0.3341	1.0161	0.025*
C18	0.9936 (4)	0.0107 (3)	1.0450 (2)	0.0163 (4)
C19	0.8000 (4)	0.1369 (3)	0.9625 (2)	0.0161 (4)
H19	0.7777	0.2578	0.9509	0.019*
C20	1.1623 (4)	0.0692 (3)	1.1206 (2)	0.0172 (5)
C21	1.4960 (5)	−0.0250 (3)	1.2878 (2)	0.0220 (5)
H21A	1.3916	0.0733	1.3122	0.033*
H21B	1.6598	0.0043	1.2484	0.033*
H21C	1.5470	−0.1288	1.3599	0.033*

	U11	U22	U33	U12	U13	U23
O1	0.0201 (8)	0.0162 (9)	0.0232 (9)	−0.0018 (6)	−0.0079 (6)	−0.0016 (7)
O2	0.0138 (7)	0.0175 (8)	0.0376 (10)	−0.0063 (6)	−0.0052 (7)	0.0017 (7)
O3	0.0228 (8)	0.0134 (8)	0.0260 (9)	−0.0053 (6)	−0.0103 (7)	0.0010 (7)
O4	0.0243 (8)	0.0170 (9)	0.0262 (9)	−0.0024 (6)	−0.0048 (7)	−0.0060 (7)
N1	0.0118 (8)	0.0135 (9)	0.0184 (9)	−0.0030 (7)	0.0003 (7)	−0.0017 (8)
N2	0.0229 (10)	0.0139 (10)	0.0209 (10)	−0.0021 (7)	−0.0008 (8)	−0.0053 (8)
N3	0.0245 (10)	0.0165 (11)	0.0183 (10)	−0.0019 (8)	−0.0045 (8)	−0.0054 (8)
C1	0.0115 (9)	0.0125 (10)	0.0163 (11)	−0.0010 (7)	0.0023 (8)	−0.0047 (8)
C2	0.0125 (9)	0.0155 (11)	0.0195 (11)	−0.0034 (8)	0.0000 (8)	−0.0059 (9)
C3	0.0138 (10)	0.0149 (11)	0.0180 (11)	−0.0004 (8)	−0.0001 (8)	−0.0032 (9)
C4	0.0187 (11)	0.0121 (11)	0.0227 (12)	−0.0029 (8)	0.0017 (9)	−0.0032 (9)
C5	0.0179 (11)	0.0174 (12)	0.0260 (13)	−0.0069 (8)	0.0007 (9)	−0.0085 (10)
C6	0.0136 (10)	0.0171 (12)	0.0189 (11)	−0.0029 (8)	−0.0014 (8)	−0.0056 (9)
C7	0.0237 (12)	0.0198 (12)	0.0272 (12)	0.0009 (9)	−0.0095 (10)	−0.0088 (10)
C8	0.0139 (10)	0.0159 (11)	0.0174 (11)	−0.0024 (8)	0.0000 (8)	−0.0038 (9)
C9	0.0134 (9)	0.0137 (11)	0.0142 (10)	−0.0016 (8)	−0.0038 (8)	−0.0021 (8)
C10	0.0129 (10)	0.0169 (11)	0.0179 (11)	−0.0037 (8)	0.0012 (8)	−0.0043 (9)
C11	0.0168 (10)	0.0166 (11)	0.0217 (11)	−0.0005 (8)	−0.0025 (9)	−0.0057 (9)
C12	0.0200 (11)	0.0130 (11)	0.0164 (11)	−0.0055 (8)	−0.0073 (9)	0.0010 (9)
C13	0.0188 (11)	0.0206 (12)	0.0206 (12)	−0.0061 (8)	0.0018 (9)	−0.0006 (9)
C14	0.0177 (11)	0.0209 (12)	0.0185 (11)	−0.0017 (8)	0.0027 (8)	−0.0031 (9)
C15	0.0168 (10)	0.0147 (11)	0.0146 (11)	−0.0018 (8)	−0.0010 (8)	0.0002 (9)
C16	0.0229 (11)	0.0179 (12)	0.0190 (11)	−0.0069 (9)	0.0001 (8)	−0.0064 (9)
C17	0.0276 (12)	0.0116 (10)	0.0220 (12)	−0.0034 (8)	0.0005 (9)	−0.0040 (9)
C18	0.0182 (11)	0.0152 (11)	0.0143 (10)	−0.0053 (8)	0.0034 (8)	−0.0027 (9)
C19	0.0189 (10)	0.0131 (10)	0.0147 (10)	−0.0043 (8)	0.0014 (8)	−0.0021 (9)
C20	0.0155 (10)	0.0195 (12)	0.0162 (11)	−0.0034 (8)	0.0022 (8)	−0.0060 (9)
C21	0.0206 (11)	0.0253 (13)	0.0203 (11)	−0.0024 (9)	−0.0031 (9)	−0.0091 (10)

O1—C3	1.369 (3)	C7—H7A	0.9800
O1—C7	1.440 (3)	C7—H7B	0.9800
O2—C8	1.237 (3)	C7—H7C	0.9800
O3—C15	1.368 (3)	C9—C14	1.387 (3)
O3—C12	1.402 (3)	C9—C10	1.394 (3)
O4—C20	1.239 (3)	C10—C11	1.389 (3)
N1—C8	1.360 (3)	C10—H10	0.9500
N1—C9	1.424 (3)	C11—C12	1.387 (3)
N1—H1N	0.89 (3)	C11—H11	0.9500
N2—C18	1.340 (3)	C12—C13	1.376 (3)
N2—C17	1.346 (3)	C13—C14	1.387 (3)
N3—C20	1.337 (3)	C13—H13	0.9500
N3—C21	1.450 (3)	C14—H14	0.9500
N3—H3N	0.85 (3)	C15—C16	1.382 (3)
C1—C6	1.391 (3)	C15—C19	1.387 (3)
C1—C2	1.397 (3)	C16—C17	1.386 (3)
C1—C8	1.491 (3)	C16—H16	0.9500
C2—C3	1.386 (3)	C17—H17	0.9500
C2—H2	0.9500	C18—C19	1.387 (3)
C3—C4	1.397 (3)	C18—C20	1.510 (3)
C4—C5	1.380 (3)	C19—H19	0.9500
C4—H4	0.9500	C21—H21A	0.9800
C5—C6	1.396 (3)	C21—H21B	0.9800
C5—H5	0.9500	C21—H21C	0.9800
C6—H6	0.9500
C3—O1—C7	116.81 (17)	C11—C10—C9	120.1 (2)
C15—O3—C12	119.17 (17)	C11—C10—H10	120.0
C8—N1—C9	122.98 (18)	C9—C10—H10	120.0
C8—N1—H1N	116 (2)	C12—C11—C10	119.2 (2)
C9—N1—H1N	118 (2)	C12—C11—H11	120.4
C18—N2—C17	116.25 (18)	C10—C11—H11	120.4
C20—N3—C21	121.4 (2)	C13—C12—C11	121.2 (2)
C20—N3—H3N	122 (2)	C13—C12—O3	118.26 (19)
C21—N3—H3N	117 (2)	C11—C12—O3	120.3 (2)
C6—C1—C2	120.42 (19)	C12—C13—C14	119.4 (2)
C6—C1—C8	122.61 (19)	C12—C13—H13	120.3
C2—C1—C8	116.91 (19)	C14—C13—H13	120.3
C3—C2—C1	119.96 (19)	C13—C14—C9	120.4 (2)
C3—C2—H2	120.0	C13—C14—H14	119.8
C1—C2—H2	120.0	C9—C14—H14	119.8
O1—C3—C2	124.4 (2)	O3—C15—C16	116.9 (2)
O1—C3—C4	115.84 (19)	O3—C15—C19	123.2 (2)
C2—C3—C4	119.77 (19)	C16—C15—C19	119.86 (19)
C5—C4—C3	120.0 (2)	C15—C16—C17	118.2 (2)
C5—C4—H4	120.0	C15—C16—H16	120.9
C3—C4—H4	120.0	C17—C16—H16	120.9
C4—C5—C6	120.8 (2)	N2—C17—C16	123.7 (2)
C4—C5—H5	119.6	N2—C17—H17	118.1
C6—C5—H5	119.6	C16—C17—H17	118.1
C1—C6—C5	119.04 (19)	N2—C18—C19	124.8 (2)
C1—C6—H6	120.5	N2—C18—C20	116.87 (18)
C5—C6—H6	120.5	C19—C18—C20	118.32 (19)
O1—C7—H7A	109.5	C18—C19—C15	117.2 (2)
O1—C7—H7B	109.5	C18—C19—H19	121.4
H7A—C7—H7B	109.5	C15—C19—H19	121.4
O1—C7—H7C	109.5	O4—C20—N3	124.1 (2)
H7A—C7—H7C	109.5	O4—C20—C18	120.93 (19)
H7B—C7—H7C	109.5	N3—C20—C18	115.0 (2)
O2—C8—N1	122.4 (2)	N3—C21—H21A	109.5
O2—C8—C1	120.97 (19)	N3—C21—H21B	109.5
N1—C8—C1	116.65 (19)	H21A—C21—H21B	109.5
C14—C9—C10	119.6 (2)	N3—C21—H21C	109.5
C14—C9—N1	120.77 (18)	H21A—C21—H21C	109.5
C10—C9—N1	119.64 (19)	H21B—C21—H21C	109.5
C6—C1—C2—C3	1.0 (3)	C15—O3—C12—C13	−113.2 (2)
C8—C1—C2—C3	178.42 (18)	C15—O3—C12—C11	72.9 (3)
C7—O1—C3—C2	−16.6 (3)	C11—C12—C13—C14	3.7 (3)
C7—O1—C3—C4	164.13 (19)	O3—C12—C13—C14	−170.2 (2)
C1—C2—C3—O1	179.13 (19)	C12—C13—C14—C9	−0.3 (3)
C1—C2—C3—C4	−1.6 (3)	C10—C9—C14—C13	−3.6 (3)
O1—C3—C4—C5	−180.0 (2)	N1—C9—C14—C13	176.2 (2)
C2—C3—C4—C5	0.7 (3)	C12—O3—C15—C16	−168.06 (19)
C3—C4—C5—C6	0.8 (3)	C12—O3—C15—C19	13.8 (3)
C2—C1—C6—C5	0.5 (3)	O3—C15—C16—C17	−179.4 (2)
C8—C1—C6—C5	−176.77 (19)	C19—C15—C16—C17	−1.1 (3)
C4—C5—C6—C1	−1.4 (3)	C18—N2—C17—C16	0.8 (3)
C9—N1—C8—O2	2.7 (3)	C15—C16—C17—N2	0.3 (4)
C9—N1—C8—C1	−177.13 (19)	C17—N2—C18—C19	−1.2 (3)
C6—C1—C8—O2	149.6 (2)	C17—N2—C18—C20	176.7 (2)
C2—C1—C8—O2	−27.7 (3)	N2—C18—C19—C15	0.3 (3)
C6—C1—C8—N1	−30.6 (3)	C20—C18—C19—C15	−177.45 (19)
C2—C1—C8—N1	152.10 (19)	O3—C15—C19—C18	178.95 (19)
C8—N1—C9—C14	−46.8 (3)	C16—C15—C19—C18	0.8 (3)
C8—N1—C9—C10	133.0 (2)	C21—N3—C20—O4	1.9 (3)
C14—C9—C10—C11	4.1 (3)	C21—N3—C20—C18	−176.19 (19)
N1—C9—C10—C11	−175.67 (19)	N2—C18—C20—O4	179.9 (2)
C9—C10—C11—C12	−0.7 (3)	C19—C18—C20—O4	−2.2 (3)
C10—C11—C12—C13	−3.2 (3)	N2—C18—C20—N3	−2.0 (3)
C10—C11—C12—O3	170.56 (18)	C19—C18—C20—N3	175.94 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.89 (3)	2.08 (3)	2.918 (2)	155 (3)
N3—H3N···O1ii	0.85 (3)	2.38 (3)	3.148 (3)	151 (2)
N3—H3N···N2	0.85 (3)	2.33 (3)	2.681 (3)	105 (2)
C7—H7B···O4iii	0.98	2.55	3.475 (3)	158
C14—H14···O2	0.95	2.56	2.887 (3)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.89 (3)	2.08 (3)	2.918 (2)	155 (3)
N3—H3N⋯O1ii	0.85 (3)	2.38 (3)	3.148 (3)	151 (2)
N3—H3N⋯N2	0.85 (3)	2.33 (3)	2.681 (3)	105 (2)
C7—H7B⋯O4iii	0.98	2.55	3.475 (3)	158

Symmetry codes: (i) ; (ii) ; (iii) .