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

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

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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809055688/om2308sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809055688/om2308Isup2.hkl Contains datablock I

CCDC reference: 765341

checkCIF report

Key indicators

Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.003 Å
R factor = 0.035
wR factor = 0.085
Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =      18.24
            Cell volume su given      =      16.00
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         17
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          7
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C The Supplied and Calc. Volume s.u. Differ by ...          2 Units
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         30

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.84
           From the CIF: _reflns_number_total               2108
           Count of symmetry unique reflns         2155
           Completeness (_total/calc)             97.82%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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).