4-[4-(3-Methoxy­benzamido)phen­oxy]-N-methyl­picolinamide

Meng, N.-N.; Huang, T.-T.; Li, D.-K.; Zhang, W.-X.; Yu, L.-T.

doi:10.1107/S1600536809055688

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o476

https://doi.org/10.1107/S1600536809055688

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4-[4-(3-Methoxybenzamido)phenoxy]-N-methylpicolinamide

Na-Na Meng,^a Ting-Ting Huang,^a De-Kuan Li,^b Wen-Xin Zhang ^c and Luo-Ting Yu ^a ^*

^aState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China, ^bKey Laboratory of Bio-resources and Eco-environment of the Ministry of Education, College of Life Science, Sichuan University, Chengdu 610041, People's Republic of China, and ^cDepartment of Pharmaceutical and Bioengineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, People's Republic of China
^*Correspondence e-mail: luodyu@163.com

(Received 10 December 2009; accepted 29 December 2009; online 30 January 2010)

In the title compound, C₂₁H₁₉N₃O₄, the central benzene ring makes dihedral angles of 78.54 (6) and 75.30 (6)° with the pyridine and 3-methoxyphenyl rings, respectively. An intramolecular N—H⋯N interaction occurs, generating an S(?). The crystal packing shows intermolecular N—H⋯O hydrogen-bonding interactions between the N—H groups and the O atoms of the 3-methoxyphenyl ring and the carbonyl groups of the amide functions. Intermolecular C—H⋯O interactions 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_r = 377.39
Triclinic, P 1
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.085
S = 1.10
2108 reflections
263 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) x+1, y, z; (ii) x+2, y-2, z+1; (iii) x-1, y+1, z-1.

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055688/om2308Isup2.hkl

checkCIF report

Comment top

Sorafenib is of great importance owing to its antitumor properties (Khire et al., 2004; Dominguez et al., 2007). The title compound, as one of its derivatives, possessed even better in vitro anticancer activity against both two tumor cell lines (HCT116 and HEPG2). As a potent antitumor drug, we report here its crystal structure.

In the title molecule, C₂₁H₁₉N₃O₄, (Fig.1), the phenyl ring makes dihedral angles of 78.54 (6)° and 75.30 (6)° with the pyridine ring and the 3-methoxyphenyl ring, respectively. In the crystal structure, intermolecular N—H···O hydrogen-bonding interactions between the N—H and O atoms of 3-methoxyphenyl ring and carbonyl groups of the amide functionalities form an infinite three-dimensional structure (Table 1 and Fig. 2).

Related literature top

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

Experimental top

To the suspension of anhydrous potassium carbonate (1.635 g,12.5 mmol) and 4-(4-aminophenoxy)-N-methylpicolinamide (1.22 g, 5 mmol) in 11.4 ml THF was added dropwise 3-methoxybenzoyl chloride(1.28 g,7.5 mmol). After being stirred at room temperature for 2 h, the mixture was extracted with 90 ml EA and 30 ml water for three times and the combined organic layers were dried over anhydrous Na₂SO₄. Then the solution was concentrated under vacuum, and the residue was recrystallized from ethanol to give the title compound. Crystals suitable for X-ray analysis were obtained by slow evaporation from a solution of ethanol.

Structure description top

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

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The cell packing of the title compound.

4-[4-(3-Methoxybenzamido)phenoxy]-N-methylpicolinamide top

Crystal data top

C₂₁H₁₉N₃O₄	Z = 1
M_r = 377.39	F(000) = 198
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0481P)²] where P = (F_o² + 2F_c²)/3
2108 reflections	(Δ/σ)_max < 0.001
263 parameters	Δρ_max = 0.22 e Å⁻³
3 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₁₉N₃O₄	γ = 76.10 (3)°
M_r = 377.39	V = 452.14 (16) Å³
Triclinic, P1	Z = 1
a = 5.0915 (10) Å	Mo Kα radiation
b = 8.3251 (17) Å	µ = 0.10 mm⁻¹
c = 11.611 (2) Å	T = 113 K
α = 71.29 (3)°	0.34 × 0.29 × 0.19 mm
β = 87.74 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2108 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1811 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.982	R_int = 0.026
3733 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	3 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.22 e Å⁻³
2108 reflections	Δρ_min = −0.24 e Å⁻³
263 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x+1, y, z; (ii) x+2, y−2, z+1; (iii) x−1, y+1, z−1.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉N₃O₄
M_r	377.39
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	5.0915 (10), 8.3251 (17), 11.611 (2)
α, β, γ (°)	71.29 (3), 87.74 (3), 76.10 (3)
V (Å³)	452.14 (16)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.34 × 0.29 × 0.19

Data collection
Diffractometer	Rigaku Saturn CCD area-detector
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.968, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	3733, 2108, 1811
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.085, 1.10
No. of reflections	2108
No. of parameters	263
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.24

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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)	158.0
C14—H14···O2	0.95	2.56	2.887 (3)	100.2

Symmetry codes: (i) x+1, y, z; (ii) x+2, y−2, z+1; (iii) x−1, y+1, z−1.

Acknowledgements

The project was sponsored by the Scientific Research Foundation for Returned Overseas Chinese Scholars (No. 20071108–18–14), State Education Ministry. We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

References

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Dominguez, C., Smith, L., Huang, Q., Yuan, C. & Ouyang, X. H. (2007). Bioorg. Med. Chem. Lett. 17, 6003–6008. Web of Science CrossRef PubMed CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Khire, U. R., Bankston, D., Barbosa, J., Brittelli, D. R. & Caringal, Y. (2004). Bioorg. Med. Chem. Lett. 14, 783–786. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar