7-Diethyl­amino-2-oxo-2H-chromene-3-carbohydrazide

Zhang, L.-J.; Yin, B.-Z.

doi:10.1107/S1600536811010944

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1107

doi:10.1107/S1600536811010944

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7-Diethylamino-2-oxo-2H-chromene-3-carbohydrazide

Li-Jun Zhang ^a and Bing-Zhu Yin ^a ^*

^aKey Laboratory of Natural Resources of Changbai Mountain, & Functional Molecules (Yanbian University), Ministry of Eduction, Yanji 133002, People's Republic of China
^*Correspondence e-mail: zqcong@ybu.edu.cn

(Received 16 March 2011; accepted 24 March 2011; online 13 April 2011)

The asymmetric unit of the title compound, C₁₄H₁₇N₃O₃, contains two independent molecules with different conformations of the ethyl groups. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into ribbons extending along the a axis.

Related literature

For the bioactivity and chemiluminescence of coumarin derivatives, see: Munasinghe et al. (2007 ). For a related structure, see: Yu et al. (2009 ). For details of the synthesis, see: Ma et al. (2010 ).

Experimental

Crystal data

C₁₄H₁₇N₃O₃
M_r = 275.31
Triclinic, $[P \overline 1]$
a = 9.3438 (19) Å
b = 12.771 (3) Å
c = 12.978 (3) Å
α = 95.17 (3)°
β = 110.13 (3)°
γ = 106.18 (3)°
V = 1366.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 290 K
0.14 × 0.12 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.987, T_max = 0.990
13506 measured reflections
6186 independent reflections
3402 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.117
S = 1.01
6186 reflections
383 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.86 (3)	2.01 (2)	2.7098 (18)	137 (2)
N5—H5⋯O5	0.87 (3)	2.03 (2)	2.733 (2)	138 (2)
N6—H6B⋯O3	0.86 (3)	2.30 (1)	3.131 (2)	164 (2)
N3—H3A⋯O3ⁱ	0.87 (3)	2.20 (1)	3.002 (2)	155 (2)
N3—H3B⋯O6ⁱⁱ	0.87 (3)	2.23 (1)	3.039 (2)	154 (2)
Symmetry codes: (i) -x, -y+1, -z+3; (ii) -x+1, -y+1, -z+3.

Data collection: RAPID-AUTO (Rigaku Corporation, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010944/cv5061sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010944/cv5061Isup2.hkl

checkCIF report

Comment top

Coumarin derivatives have received considerable attention since their diverse bioactivities and chemiluminescence (Munasinghe et al. 2007). Herein, we report the crystal structure of the title compound, an important organic intermediate and a fluorescent tagging agent for chemosensors.

In the title compound, all bond lengths and angles are normal and comparable to those observed in the related struture (Yu et al., 2009). There are two independent molecules in the asymmetric unit with different conformation of the ethyl groups (Fig. 1). Except for four terminal carbon atoms, the other non-hydrogen atoms are nearly coplanar for two components [mean deviations from the mean planes are 0.065 (1) and 0.07 (1), respectively] and form an angle of 19.39 (4) °. Intermolecuar N—H···O hydrogen bonds (Table 1) link the molecules into ribbons extended along axis a.

Related literature top

For the bioactivity and chemiluminescence of coumarin derivatives, see: Munasinghe et al. (2007). For a related structure, see: Yu et al. (2009). For details of the synthesis, see: Ma et al. (2010).

Experimental top

The title compound was prepared according to the literature (Ma et al., 2010). Single crystals suitable for X-ray diffraction were prepared by slow evaporation a mixture of dichloromethane and petroleum (60–90 °C) at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO (Rigaku Corporation, 1998); data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Two independent molecules of the title compound, with the atom numbering. Displacement ellipsoids of non-H atoms are drawn at the 30% probalility level.

7-Diethylamino-2-oxo-2H-chromene-3-carbohydrazide top

Crystal data top

C₁₄H₁₇N₃O₃	Z = 4
M_r = 275.31	F(000) = 584
Triclinic, P1	D_x = 1.338 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3438 (19) Å	Cell parameters from 8202 reflections
b = 12.771 (3) Å	θ = 3.2–27.5°
c = 12.978 (3) Å	µ = 0.10 mm⁻¹
α = 95.17 (3)°	T = 290 K
β = 110.13 (3)°	Block, yellow
γ = 106.18 (3)°	0.14 × 0.12 × 0.11 mm
V = 1366.4 (5) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	6186 independent reflections
Radiation source: fine-focus sealed tube	3402 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→10
T_min = 0.987, T_max = 0.990	k = −16→16
13506 measured reflections	l = −16→16

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0543P)²] where P = (F_o² + 2F_c²)/3
6186 reflections	(Δ/σ)_max = 0.005
383 parameters	Δρ_max = 0.18 e Å⁻³
6 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₄H₁₇N₃O₃	γ = 106.18 (3)°
M_r = 275.31	V = 1366.4 (5) Å³
Triclinic, P1	Z = 4
a = 9.3438 (19) Å	Mo Kα radiation
b = 12.771 (3) Å	µ = 0.10 mm⁻¹
c = 12.978 (3) Å	T = 290 K
α = 95.17 (3)°	0.14 × 0.12 × 0.11 mm
β = 110.13 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	6186 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3402 reflections with I > 2σ(I)
T_min = 0.987, T_max = 0.990	R_int = 0.030
13506 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	6 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.18 e Å⁻³
6186 reflections	Δρ_min = −0.19 e Å⁻³
383 parameters

Special details top

Experimental. (See detailed section in the paper)

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
C1	0.21139 (18)	0.57501 (13)	1.19989 (14)	0.0463 (4)
C2	0.13466 (18)	0.48762 (12)	1.24574 (13)	0.0436 (4)
C3	0.13127 (19)	0.50961 (13)	1.35921 (14)	0.0492 (4)
C4	0.06725 (18)	0.38172 (12)	1.18533 (13)	0.0463 (4)
H4	0.0150	0.3265	1.2146	0.056*
C5	0.07300 (18)	0.35191 (12)	1.08046 (13)	0.0443 (4)
C6	0.15295 (17)	0.43610 (12)	1.03866 (13)	0.0426 (4)
C7	0.17389 (18)	0.41745 (13)	0.93993 (14)	0.0494 (4)
H7	0.2289	0.4764	0.9159	0.059*
C8	0.11153 (18)	0.30841 (13)	0.87521 (13)	0.0484 (4)
C9	0.02840 (19)	0.22172 (13)	0.91645 (14)	0.0524 (4)
H9	−0.0144	0.1489	0.8754	0.063*
C10	0.01086 (19)	0.24390 (13)	1.01450 (14)	0.0516 (4)
H10	−0.0443	0.1855	1.0391	0.062*
C11	0.0769 (2)	0.17291 (15)	0.71424 (16)	0.0645 (5)
H11A	0.0960	0.1239	0.7666	0.077*
H11B	0.1411	0.1699	0.6698	0.077*
C12	−0.0988 (2)	0.13259 (17)	0.63824 (16)	0.0768 (6)
H12A	−0.1625	0.1375	0.6817	0.115*
H12B	−0.1295	0.0565	0.6013	0.115*
H12C	−0.1168	0.1780	0.5832	0.115*
C13	0.2090 (2)	0.37670 (15)	0.72996 (15)	0.0640 (5)
H13A	0.1828	0.4430	0.7462	0.077*
H13B	0.1687	0.3532	0.6491	0.077*
C14	0.3890 (2)	0.40375 (17)	0.77862 (19)	0.0777 (6)
H14A	0.4301	0.4333	0.8577	0.116*
H14B	0.4371	0.4580	0.7430	0.116*
H14C	0.4149	0.3373	0.7662	0.116*
C15	0.2466 (2)	0.11381 (14)	1.16812 (14)	0.0526 (4)
C16	0.36577 (19)	0.22392 (14)	1.21170 (14)	0.0506 (4)
C17	0.3901 (2)	0.29587 (15)	1.31736 (15)	0.0556 (4)
C18	0.4607 (2)	0.26342 (14)	1.15444 (14)	0.0544 (4)
H18	0.5359	0.3349	1.1819	0.065*
C19	0.44932 (19)	0.20030 (13)	1.05563 (14)	0.0493 (4)
C20	0.33527 (18)	0.09381 (13)	1.01525 (13)	0.0466 (4)
C21	0.31367 (19)	0.02453 (13)	0.92049 (14)	0.0512 (4)
H21	0.2345	−0.0454	0.8962	0.061*
C22	0.41151 (19)	0.05924 (13)	0.85967 (14)	0.0494 (4)
C23	0.5282 (2)	0.16798 (14)	0.90010 (14)	0.0547 (4)
H23	0.5936	0.1939	0.8614	0.066*
C24	0.5454 (2)	0.23412 (14)	0.99384 (15)	0.0571 (4)
H24	0.6236	0.3045	1.0184	0.069*
C25	0.4975 (2)	0.02687 (16)	0.70252 (16)	0.0687 (5)
H25A	0.5055	−0.0386	0.6639	0.082*
H25B	0.6054	0.0717	0.7547	0.082*
C26	0.4354 (3)	0.09271 (17)	0.61840 (16)	0.0806 (6)
H26A	0.3285	0.0490	0.5663	0.121*
H26B	0.5055	0.1117	0.5786	0.121*
H26C	0.4322	0.1596	0.6563	0.121*
C27	0.2699 (2)	−0.11834 (14)	0.72177 (16)	0.0646 (5)
H27A	0.2679	−0.1551	0.7837	0.078*
H27B	0.2989	−0.1627	0.6727	0.078*
C28	0.1023 (2)	−0.11651 (16)	0.65768 (16)	0.0717 (5)
H28A	0.0664	−0.0811	0.7077	0.108*
H28B	0.0299	−0.1915	0.6253	0.108*
H28C	0.1040	−0.0758	0.5992	0.108*
N1	0.12851 (17)	0.28688 (11)	0.77682 (12)	0.0596 (4)
N2	0.19388 (19)	0.61432 (12)	1.41508 (12)	0.0581 (4)
H2	0.231 (2)	0.6657 (13)	1.3829 (16)	0.087*
N3	0.1989 (2)	0.64809 (13)	1.52280 (14)	0.0672 (4)
H3B	0.268 (2)	0.6211 (18)	1.5658 (15)	0.101*
H3A	0.1032 (15)	0.6189 (17)	1.5226 (19)	0.101*
N4	0.39535 (17)	−0.00890 (12)	0.76634 (12)	0.0579 (4)
N5	0.3063 (2)	0.25209 (14)	1.37695 (14)	0.0663 (4)
H5	0.241 (2)	0.1841 (10)	1.3507 (18)	0.099*
N6	0.3254 (2)	0.30988 (17)	1.48147 (15)	0.0782 (5)
H6B	0.270 (3)	0.3544 (18)	1.470 (2)	0.117*
H6A	0.4263 (14)	0.3504 (18)	1.5136 (19)	0.117*
O1	0.21779 (13)	0.54484 (8)	1.09751 (9)	0.0493 (3)
O2	0.27280 (15)	0.67378 (9)	1.24139 (10)	0.0638 (3)
O3	0.07200 (17)	0.43205 (10)	1.39865 (11)	0.0697 (4)
O4	0.23680 (13)	0.05352 (9)	1.07136 (9)	0.0542 (3)
O5	0.15179 (15)	0.06693 (10)	1.20795 (11)	0.0694 (4)
O6	0.48723 (17)	0.39132 (11)	1.34921 (11)	0.0751 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0444 (9)	0.0409 (9)	0.0559 (10)	0.0098 (7)	0.0261 (8)	0.0083 (8)
C2	0.0416 (8)	0.0405 (8)	0.0540 (10)	0.0136 (7)	0.0244 (8)	0.0110 (7)
C3	0.0499 (9)	0.0471 (9)	0.0602 (11)	0.0185 (8)	0.0302 (8)	0.0131 (8)
C4	0.0442 (9)	0.0412 (9)	0.0556 (10)	0.0098 (7)	0.0238 (8)	0.0152 (8)
C5	0.0424 (8)	0.0398 (8)	0.0497 (9)	0.0092 (7)	0.0195 (7)	0.0114 (7)
C6	0.0362 (8)	0.0362 (8)	0.0508 (10)	0.0065 (7)	0.0163 (7)	0.0063 (7)
C7	0.0488 (9)	0.0415 (9)	0.0561 (10)	0.0046 (7)	0.0268 (8)	0.0080 (8)
C8	0.0442 (9)	0.0478 (9)	0.0495 (10)	0.0091 (8)	0.0199 (8)	0.0051 (8)
C9	0.0530 (10)	0.0374 (8)	0.0553 (11)	0.0043 (8)	0.0177 (8)	0.0028 (8)
C10	0.0530 (10)	0.0392 (8)	0.0568 (11)	0.0031 (8)	0.0236 (8)	0.0107 (8)
C11	0.0749 (13)	0.0558 (11)	0.0622 (12)	0.0167 (10)	0.0326 (10)	0.0004 (9)
C12	0.0884 (15)	0.0648 (12)	0.0565 (12)	0.0097 (11)	0.0179 (11)	0.0050 (10)
C13	0.0696 (12)	0.0645 (12)	0.0595 (12)	0.0189 (10)	0.0313 (10)	0.0050 (9)
C14	0.0777 (14)	0.0684 (13)	0.1055 (17)	0.0265 (11)	0.0537 (13)	0.0260 (12)
C15	0.0563 (10)	0.0527 (10)	0.0567 (11)	0.0170 (9)	0.0300 (9)	0.0196 (9)
C16	0.0521 (10)	0.0534 (10)	0.0534 (10)	0.0198 (8)	0.0252 (8)	0.0191 (8)
C17	0.0559 (10)	0.0583 (11)	0.0579 (11)	0.0219 (10)	0.0240 (9)	0.0202 (9)
C18	0.0549 (10)	0.0469 (9)	0.0607 (11)	0.0109 (8)	0.0250 (9)	0.0161 (9)
C19	0.0505 (9)	0.0470 (9)	0.0515 (10)	0.0100 (8)	0.0245 (8)	0.0168 (8)
C20	0.0456 (9)	0.0469 (9)	0.0530 (10)	0.0114 (8)	0.0265 (8)	0.0208 (8)
C21	0.0521 (10)	0.0441 (9)	0.0586 (11)	0.0078 (8)	0.0276 (9)	0.0168 (8)
C22	0.0505 (9)	0.0503 (9)	0.0535 (10)	0.0155 (8)	0.0261 (8)	0.0192 (8)
C23	0.0531 (10)	0.0576 (10)	0.0560 (11)	0.0089 (8)	0.0296 (9)	0.0208 (9)
C24	0.0576 (10)	0.0482 (10)	0.0611 (11)	0.0010 (8)	0.0297 (9)	0.0161 (9)
C25	0.0768 (13)	0.0694 (12)	0.0750 (13)	0.0238 (11)	0.0470 (11)	0.0165 (11)
C26	0.0798 (14)	0.0811 (14)	0.0630 (13)	0.0053 (12)	0.0223 (11)	0.0185 (11)
C27	0.0742 (13)	0.0515 (10)	0.0740 (13)	0.0163 (10)	0.0409 (11)	0.0064 (9)
C28	0.0660 (12)	0.0690 (12)	0.0765 (14)	0.0100 (10)	0.0366 (11)	0.0004 (10)
N1	0.0636 (9)	0.0501 (8)	0.0602 (9)	0.0039 (7)	0.0324 (8)	0.0005 (7)
N2	0.0738 (10)	0.0494 (9)	0.0568 (10)	0.0158 (8)	0.0362 (8)	0.0081 (7)
N3	0.0833 (12)	0.0614 (10)	0.0638 (11)	0.0183 (9)	0.0431 (10)	0.0042 (8)
N4	0.0605 (9)	0.0560 (9)	0.0631 (10)	0.0128 (7)	0.0359 (8)	0.0124 (8)
N5	0.0763 (11)	0.0713 (10)	0.0619 (10)	0.0225 (9)	0.0404 (9)	0.0155 (9)
N6	0.0926 (13)	0.0951 (14)	0.0573 (11)	0.0356 (11)	0.0380 (10)	0.0145 (10)
O1	0.0545 (6)	0.0380 (6)	0.0568 (7)	0.0050 (5)	0.0322 (6)	0.0062 (5)
O2	0.0802 (8)	0.0391 (6)	0.0750 (8)	0.0036 (6)	0.0481 (7)	0.0033 (6)
O3	0.0996 (10)	0.0517 (7)	0.0758 (9)	0.0195 (7)	0.0587 (8)	0.0168 (7)
O4	0.0581 (7)	0.0490 (6)	0.0606 (7)	0.0078 (5)	0.0360 (6)	0.0146 (6)
O5	0.0763 (9)	0.0634 (8)	0.0779 (9)	0.0078 (7)	0.0526 (8)	0.0166 (7)
O6	0.0871 (10)	0.0642 (9)	0.0697 (9)	0.0104 (8)	0.0380 (8)	0.0079 (7)

Geometric parameters (Å, º) top

C1—O2	1.2131 (19)	C16—C17	1.489 (2)
C1—O1	1.3757 (18)	C17—O6	1.231 (2)
C1—C2	1.443 (2)	C17—N5	1.332 (2)
C2—C4	1.354 (2)	C18—C19	1.406 (2)
C2—C3	1.487 (2)	C18—H18	0.9300
C3—O3	1.2372 (19)	C19—C20	1.393 (2)
C3—N2	1.324 (2)	C19—C24	1.406 (2)
C4—C5	1.403 (2)	C20—C21	1.367 (2)
C4—H4	0.9300	C20—O4	1.3808 (17)
C5—C6	1.395 (2)	C21—C22	1.410 (2)
C5—C10	1.404 (2)	C21—H21	0.9300
C6—C7	1.371 (2)	C22—N4	1.363 (2)
C6—O1	1.3785 (18)	C22—C23	1.422 (2)
C7—C8	1.409 (2)	C23—C24	1.350 (2)
C7—H7	0.9300	C23—H23	0.9300
C8—N1	1.3534 (19)	C24—H24	0.9300
C8—C9	1.425 (2)	C25—N4	1.475 (2)
C9—C10	1.353 (2)	C25—C26	1.496 (3)
C9—H9	0.9300	C25—H25A	0.9700
C10—H10	0.9300	C25—H25B	0.9700
C11—N1	1.462 (2)	C26—H26A	0.9600
C11—C12	1.502 (3)	C26—H26B	0.9600
C11—H11A	0.9700	C26—H26C	0.9600
C11—H11B	0.9700	C27—N4	1.462 (2)
C12—H12A	0.9600	C27—C28	1.507 (3)
C12—H12B	0.9600	C27—H27A	0.9700
C12—H12C	0.9600	C27—H27B	0.9700
C13—N1	1.487 (2)	C28—H28A	0.9600
C13—C14	1.501 (3)	C28—H28B	0.9600
C13—H13A	0.9700	C28—H28C	0.9600
C13—H13B	0.9700	N2—N3	1.406 (2)
C14—H14A	0.9600	N2—H2	0.86 (3)
C14—H14B	0.9600	N3—H3B	0.87 (3)
C14—H14C	0.9600	N3—H3A	0.87 (3)
C15—O5	1.2187 (18)	N5—N6	1.413 (2)
C15—O4	1.3732 (19)	N5—H5	0.87 (3)
C15—C16	1.445 (3)	N6—H6B	0.86 (3)
C16—C18	1.366 (2)	N6—H6A	0.87 (3)

O2—C1—O1	115.01 (14)	C16—C18—H18	118.7
O2—C1—C2	127.53 (15)	C19—C18—H18	118.7
O1—C1—C2	117.45 (14)	C20—C19—C18	117.92 (15)
C4—C2—C1	119.34 (14)	C20—C19—C24	116.24 (16)
C4—C2—C3	118.69 (14)	C18—C19—C24	125.83 (16)
C1—C2—C3	121.94 (14)	C21—C20—O4	116.70 (14)
O3—C3—N2	122.13 (15)	C21—C20—C19	123.23 (14)
O3—C3—C2	120.46 (15)	O4—C20—C19	120.07 (14)
N2—C3—C2	117.41 (14)	C20—C21—C22	119.95 (16)
C2—C4—C5	122.75 (14)	C20—C21—H21	120.0
C2—C4—H4	118.6	C22—C21—H21	120.0
C5—C4—H4	118.6	N4—C22—C21	121.31 (16)
C6—C5—C4	117.57 (14)	N4—C22—C23	121.43 (15)
C6—C5—C10	116.19 (14)	C21—C22—C23	117.25 (16)
C4—C5—C10	126.19 (14)	C24—C23—C22	121.02 (15)
C7—C6—O1	116.17 (13)	C24—C23—H23	119.5
C7—C6—C5	123.47 (14)	C22—C23—H23	119.5
O1—C6—C5	120.35 (13)	C23—C24—C19	122.30 (16)
C6—C7—C8	119.52 (15)	C23—C24—H24	118.9
C6—C7—H7	120.2	C19—C24—H24	118.9
C8—C7—H7	120.2	N4—C25—C26	113.65 (15)
N1—C8—C7	121.23 (15)	N4—C25—H25A	108.8
N1—C8—C9	121.16 (15)	C26—C25—H25A	108.8
C7—C8—C9	117.60 (14)	N4—C25—H25B	108.8
C10—C9—C8	120.88 (15)	C26—C25—H25B	108.8
C10—C9—H9	119.6	H25A—C25—H25B	107.7
C8—C9—H9	119.6	C25—C26—H26A	109.5
C9—C10—C5	122.33 (15)	C25—C26—H26B	109.5
C9—C10—H10	118.8	H26A—C26—H26B	109.5
C5—C10—H10	118.8	C25—C26—H26C	109.5
N1—C11—C12	111.83 (15)	H26A—C26—H26C	109.5
N1—C11—H11A	109.3	H26B—C26—H26C	109.5
C12—C11—H11A	109.3	N4—C27—C28	114.99 (15)
N1—C11—H11B	109.3	N4—C27—H27A	108.5
C12—C11—H11B	109.3	C28—C27—H27A	108.5
H11A—C11—H11B	107.9	N4—C27—H27B	108.5
C11—C12—H12A	109.5	C28—C27—H27B	108.5
C11—C12—H12B	109.5	H27A—C27—H27B	107.5
H12A—C12—H12B	109.5	C27—C28—H28A	109.5
C11—C12—H12C	109.5	C27—C28—H28B	109.5
H12A—C12—H12C	109.5	H28A—C28—H28B	109.5
H12B—C12—H12C	109.5	C27—C28—H28C	109.5
N1—C13—C14	111.26 (15)	H28A—C28—H28C	109.5
N1—C13—H13A	109.4	H28B—C28—H28C	109.5
C14—C13—H13A	109.4	C8—N1—C11	121.48 (14)
N1—C13—H13B	109.4	C8—N1—C13	122.05 (14)
C14—C13—H13B	109.4	C11—N1—C13	116.37 (13)
H13A—C13—H13B	108.0	C3—N2—N3	123.96 (15)
C13—C14—H14A	109.5	C3—N2—H2	118.5 (14)
C13—C14—H14B	109.5	N3—N2—H2	117.5 (14)
H14A—C14—H14B	109.5	N2—N3—H3B	103.8 (14)
C13—C14—H14C	109.5	N2—N3—H3A	108.3 (16)
H14A—C14—H14C	109.5	H3B—N3—H3A	112 (2)
H14B—C14—H14C	109.5	C22—N4—C27	121.26 (14)
O5—C15—O4	115.15 (15)	C22—N4—C25	121.55 (15)
O5—C15—C16	127.16 (16)	C27—N4—C25	117.10 (15)
O4—C15—C16	117.69 (14)	C17—N5—N6	122.83 (18)
C18—C16—C15	118.90 (16)	C17—N5—H5	117.4 (15)
C18—C16—C17	118.62 (16)	N6—N5—H5	119.7 (15)
C15—C16—C17	122.48 (15)	N5—N6—H6B	108.7 (17)
O6—C17—N5	121.62 (18)	N5—N6—H6A	106.1 (17)
O6—C17—C16	120.77 (16)	H6B—N6—H6A	107 (2)
N5—C17—C16	117.59 (17)	C1—O1—C6	122.45 (12)
C16—C18—C19	122.60 (17)	C15—O4—C20	122.81 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86 (3)	2.01 (2)	2.7098 (18)	137 (2)
N5—H5···O5	0.87 (3)	2.03 (2)	2.733 (2)	138 (2)
N6—H6B···O3	0.86 (3)	2.30 (1)	3.131 (2)	164 (2)
N3—H3A···O3ⁱ	0.87 (3)	2.20 (1)	3.002 (2)	155 (2)
N3—H3B···O6ⁱⁱ	0.87 (3)	2.23 (1)	3.039 (2)	154 (2)

Symmetry codes: (i) −x, −y+1, −z+3; (ii) −x+1, −y+1, −z+3.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₇N₃O₃
M_r	275.31
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	9.3438 (19), 12.771 (3), 12.978 (3)
α, β, γ (°)	95.17 (3), 110.13 (3), 106.18 (3)
V (Å³)	1366.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.14 × 0.12 × 0.11

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.987, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	13506, 6186, 3402
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.117, 1.01
No. of reflections	6186
No. of parameters	383
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

Computer programs: RAPID-AUTO (Rigaku Corporation, 1998), CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86 (3)	2.012 (15)	2.7098 (18)	137.2 (18)
N5—H5···O5	0.87 (3)	2.027 (16)	2.733 (2)	138 (2)
N6—H6B···O3	0.86 (3)	2.296 (12)	3.131 (2)	164 (2)
N3—H3A···O3ⁱ	0.87 (3)	2.197 (13)	3.002 (2)	155 (2)
N3—H3B···O6ⁱⁱ	0.87 (3)	2.230 (13)	3.039 (2)	154 (2)

Symmetry codes: (i) −x, −y+1, −z+3; (ii) −x+1, −y+1, −z+3.

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 21062022) and the Open Project of the State Key Laboratory of Supramolecular Structure and Materials, Jilin University.

References

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