N-[3-(Dimethyl­amino)­prop­yl]-N′-(2-hy­droxy-5-methyl­phen­yl)oxamide

Zheng, Y.-J.; Zheng, K.; Wu, Z.-Y.; Li, Y.

doi:10.1107/S1600536812007957

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o895

doi:10.1107/S1600536812007957

Open

access

N-[3-(Dimethylamino)propyl]-N′-(2-hydroxy-5-methylphenyl)oxamide

Yong-Jun Zheng,^a Kang Zheng,^a Zhi-Yong Wu ^b and Yantuan Li ^a ^*

^aMarine Drug and Food Institute, Ocean University of China, Qingdao, Shandong 266003, People's Republic of China, and ^bKey Laboratory of Marine Drugs, Chinese Ministry of Education, Ocean University of China, Qingdao, People's Republic of China
^*Correspondence e-mail: yantuanli@ouc.edu.cn

(Received 19 February 2012; accepted 22 February 2012; online 29 February 2012)

In the title compound, C₁₄H₂₁N₃O₃, the oxamide group has a transoid conformation. In the crystal, the molecules are connected by N—H⋯O and O—H⋯N hydrogen bonds into a double chain running along the b axis.

Related literature

For the use of N,N′-bis(substituted)oxamides in the synthesis of nuclear complexes, see: Ojima & Nonoyama (1988 ); Ruiz et al. (1999 ). For related compounds, see: Han et al. (2007 ); Martinez et al. (1998 ); Yue et al. (2012 ).

Experimental

Crystal data

C₁₄H₂₁N₃O₃
M_r = 279.34
Monoclinic, P 2₁ /c
a = 11.542 (2) Å
b = 10.304 (2) Å
c = 13.860 (3) Å
β = 109.16 (3)°
V = 1557.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.27 × 0.24 × 0.17 mm

Data collection

Bruker APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.977, T_max = 0.986
7686 measured reflections
3099 independent reflections
2093 reflections with I > 2σ(I)
R_int = 0.022
Standard reflections: 0

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.151
S = 1.02
3099 reflections
196 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.92 (3)	2.13 (3)	2.945 (2)	147 (2)
O1—H1A⋯N3ⁱⁱ	0.90 (2)	1.76 (2)	2.654 (2)	168 (3)
Symmetry codes: (i) -x+1, -y, -z; (ii) x, y+1, z.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812007957/bt5821sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007957/bt5821Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007957/bt5821Isup3.cml

checkCIF report

Comment top

N,N'-bis(substituented)oxamides as multiatom bridging ligands has played an important role in designing and synthesizing polymetallic systems (Ojima & Nonoyama, 1988; Ruiz et al., 1999). Due to the difficulties of synthesis only few dissymmetrical bis-substituented-oxamide ligand has been reported. In order to provide more examples of such ligand, quite recently, we reported the structure of (3-{[N-(5-Chloro-2-hydroxyphenyl)oxamoyl]amino}propyl)dimethylazanium perchlorate (Yue et al.,2012). In continuation of our earlier work, the title compound was synthesized and its structure is reported here.

As shown in Fig. 1, the title compound has a trans-conformation of the oxamide group. The whole compound likes the alphabet `L'. The benzene ring is almost coplanar to the oxamide group [11.44 (9)°], just like that in the compound of N,N'-bis(2-Hydroxyphenyl)oxamide (Martinez et al., 1998). However, the plane through the other substituent group, aminopropyl, is perpendicular to the oxamide plane [83.49 (12)°]. The torsion angle of C9—N2—C10—C11 is 106.7 (2)° (Table 1). And the conformation for the C10—C11 bond is gauche. While in the compound 2-(N'-[3-(Dimethylammonio)propyl)oxamido]benzoate (Han et al., 2007), the corresponding angle is 151.3 (3)° and the conformation is anti.

A centrosymmetric dimer of a pair of the compounds is formed via the hydrogen bonds of the oxamide groups (Fig. 2, Table 2). These dimers are further assembled to a chain parallel to the b-axis through the hydrogen bonds between the phenolic hydroxyl groups and the tertiary amino groups.

Related literature top

For the use of N,N'-bis(substituted)oxamides in designing and synthesizing polymetallic systems, see: Ojima & Nonoyama (1988); Ruiz et al. (1999). For related compounds, see: Han et al. (2007); Martinez et al. (1998); Yue et al. (2012). [Please check amended text]

Experimental top

All reagents were of AR grade and obtained commercially without further purification. The title compound was prepared according to the method proposed by Han et al. (2007). A tetrahydrofuran (THF) solution (8 ml) of ethyl oxalyl chloride (1.11 ml, 10 mmol) was added dropwise into a THF solution (50 ml) of 2-amino-4-methylphenol (1.23 g, 10 mmol) with continuous stirring. The mixture was stirred quickly for 1 h and became clear. Then 20 ml ethanol was further added and the mixture was added dropwise into the solution (10 ml) of 3-dimethylamino-propylamine (1.02 g, 10 mmol) with stirring and kept the temperature at 273 K for 9 h. The title compound was precipitated as a white powder and washed with ethanol for several times and dried under vacuum. Yield: 1.83 g (66%). Colourless crystals of compound with the suitable size for X-ray analysis were obtained from an ethanol/water (1:1) mixture by slow evaporation for one week at room temperature.

Anal. Calcd. for C₁₄H₂₁N₃O₃ (%): C, 60.20; H, 7.58; N, 15.04. Found: C, 60.33; H, 7.65; N, 15.00.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound. The displacement ellipsoids are drawn at the 30% probability levels and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A view of a hydrogen bonding chain extending along the b-axis. [Symmetry codes: i = -x + 1, -y, -z; ii = x, y + 1, z.]

N-[3-(Dimethylamino)propyl]-N'-(2-hydroxy-5- methylphenyl)ethanediamide top

Crystal data top

C₁₄H₂₁N₃O₃	F(000) = 600
M_r = 279.34	D_x = 1.191 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2107 reflections
a = 11.542 (2) Å	θ = 2.5–23.3°
b = 10.304 (2) Å	µ = 0.09 mm⁻¹
c = 13.860 (3) Å	T = 296 K
β = 109.16 (3)°	Block, colourless
V = 1557.2 (5) Å³	0.27 × 0.24 × 0.17 mm
Z = 4

Data collection top

Bruker APEX diffractometer	3099 independent reflections
Radiation source: fine-focus sealed tube	2093 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 26.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −6→14
T_min = 0.977, T_max = 0.986	k = −12→12
7686 measured reflections	l = −17→12

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.068P)² + 0.3954P] where P = (F_o² + 2F_c²)/3
3099 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₄H₂₁N₃O₃	V = 1557.2 (5) Å³
M_r = 279.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.542 (2) Å	µ = 0.09 mm⁻¹
b = 10.304 (2) Å	T = 296 K
c = 13.860 (3) Å	0.27 × 0.24 × 0.17 mm
β = 109.16 (3)°

Data collection top

Bruker APEX diffractometer	3099 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2093 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.986	R_int = 0.022
7686 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	1 restraint
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.30 e Å⁻³
3099 reflections	Δρ_min = −0.26 e Å⁻³
196 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	0.78563 (15)	0.54467 (14)	0.12601 (15)	0.0756 (5)
O2	0.52711 (14)	0.16017 (13)	0.05547 (12)	0.0675 (4)
O3	0.81264 (15)	0.18892 (16)	0.01920 (14)	0.0812 (5)
N1	0.66500 (17)	0.32727 (16)	0.08912 (13)	0.0551 (4)
N2	0.67544 (19)	0.02499 (17)	−0.02835 (13)	0.0606 (5)
N3	0.92876 (16)	−0.24706 (17)	0.16828 (17)	0.0720 (6)
C1	0.67333 (18)	0.54785 (18)	0.13783 (15)	0.0535 (5)
C2	0.60784 (17)	0.43098 (17)	0.12124 (14)	0.0491 (5)
C3	0.49425 (19)	0.4244 (2)	0.13394 (15)	0.0574 (5)
H3A	0.4521	0.3459	0.1235	0.069*
C4	0.4419 (2)	0.5333 (2)	0.16214 (16)	0.0623 (5)
C5	0.5060 (2)	0.6490 (2)	0.17547 (15)	0.0617 (6)
H5	0.4715	0.7234	0.1927	0.074*
C6	0.62038 (19)	0.65640 (19)	0.16368 (15)	0.0587 (5)
H6	0.6618	0.7353	0.1733	0.070*
C7	0.3173 (2)	0.5254 (3)	0.1756 (3)	0.0982 (9)
H7A	0.3224	0.4715	0.2333	0.147*
H7B	0.2593	0.4890	0.1152	0.147*
H7C	0.2912	0.6109	0.1867	0.147*
C8	0.62327 (18)	0.20947 (18)	0.05512 (14)	0.0522 (5)
C9	0.7136 (2)	0.1393 (2)	0.01338 (15)	0.0568 (5)
C10	0.7491 (3)	−0.0559 (2)	−0.07135 (18)	0.0756 (7)
H10A	0.8154	−0.0044	−0.0798	0.091*
H10B	0.6987	−0.0857	−0.1384	0.091*
C11	0.8022 (2)	−0.1719 (2)	−0.00525 (19)	0.0739 (7)
H11A	0.8523	−0.2210	−0.0365	0.089*
H11B	0.7358	−0.2277	−0.0022	0.089*
C12	0.8800 (2)	−0.1347 (2)	0.10290 (19)	0.0692 (6)
H12A	0.9478	−0.0812	0.0999	0.083*
H12B	0.8306	−0.0833	0.1333	0.083*
C13	1.0343 (3)	−0.3023 (3)	0.1486 (4)	0.1352 (16)
H13A	1.0639	−0.3754	0.1927	0.203*
H13B	1.0979	−0.2381	0.1613	0.203*
H13C	1.0112	−0.3299	0.0787	0.203*
C14	0.9619 (3)	−0.2082 (3)	0.2779 (2)	0.1081 (10)
H14A	1.0234	−0.1416	0.2926	0.162*
H14B	0.9933	−0.2822	0.3206	0.162*
H14C	0.8904	−0.1759	0.2908	0.162*
H1	0.732 (2)	0.343 (2)	0.0811 (16)	0.062 (7)*
H2	0.599 (2)	−0.003 (2)	−0.0308 (18)	0.078 (8)*
H1A	0.824 (2)	0.622 (2)	0.139 (2)	0.109 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0618 (10)	0.0484 (9)	0.1234 (14)	−0.0114 (7)	0.0397 (10)	−0.0126 (9)
O2	0.0639 (9)	0.0513 (8)	0.0878 (11)	−0.0137 (7)	0.0256 (8)	−0.0038 (7)
O3	0.0699 (11)	0.0702 (10)	0.1088 (13)	−0.0180 (9)	0.0365 (10)	−0.0231 (9)
N1	0.0503 (10)	0.0458 (9)	0.0663 (11)	−0.0055 (8)	0.0153 (9)	−0.0007 (8)
N2	0.0644 (12)	0.0522 (10)	0.0612 (11)	−0.0056 (9)	0.0152 (9)	−0.0059 (8)
N3	0.0500 (10)	0.0522 (10)	0.1121 (16)	0.0014 (8)	0.0245 (10)	0.0097 (10)
C1	0.0525 (11)	0.0476 (11)	0.0571 (11)	−0.0021 (9)	0.0134 (9)	0.0028 (9)
C2	0.0503 (11)	0.0444 (10)	0.0477 (10)	−0.0003 (8)	0.0094 (8)	0.0034 (8)
C3	0.0544 (12)	0.0572 (12)	0.0576 (12)	−0.0071 (9)	0.0142 (10)	0.0030 (9)
C4	0.0556 (12)	0.0699 (14)	0.0602 (12)	0.0021 (11)	0.0176 (10)	0.0001 (10)
C5	0.0642 (13)	0.0608 (13)	0.0562 (12)	0.0106 (11)	0.0144 (10)	−0.0013 (10)
C6	0.0639 (13)	0.0459 (11)	0.0620 (12)	−0.0015 (9)	0.0147 (10)	−0.0016 (9)
C7	0.0717 (17)	0.106 (2)	0.128 (2)	−0.0018 (16)	0.0483 (17)	−0.0125 (19)
C8	0.0538 (12)	0.0433 (10)	0.0524 (11)	−0.0039 (9)	0.0078 (9)	0.0045 (8)
C9	0.0580 (12)	0.0503 (11)	0.0562 (11)	−0.0054 (10)	0.0109 (10)	0.0010 (9)
C10	0.1010 (19)	0.0682 (14)	0.0629 (14)	−0.0081 (13)	0.0340 (13)	−0.0143 (11)
C11	0.0895 (17)	0.0542 (13)	0.0863 (16)	−0.0011 (12)	0.0402 (14)	−0.0182 (12)
C12	0.0598 (13)	0.0476 (11)	0.0948 (17)	−0.0030 (10)	0.0182 (12)	−0.0023 (11)
C13	0.0772 (19)	0.096 (2)	0.253 (5)	0.0301 (17)	0.083 (3)	0.056 (3)
C14	0.097 (2)	0.096 (2)	0.100 (2)	0.0002 (17)	−0.0096 (17)	0.0116 (17)

Geometric parameters (Å, º) top

O1—C1	1.359 (3)	C5—H5	0.9300
O2—C8	1.222 (2)	C6—H6	0.9300
O3—C9	1.231 (2)	C7—H7A	0.9600
N1—C2	1.403 (3)	C7—H7B	0.9600
N1—C8	1.334 (2)	C7—H7C	0.9600
N2—C9	1.322 (3)	C8—C9	1.530 (3)
O1—H1A	0.904 (17)	C10—C11	1.509 (3)
N1—H1	0.83 (2)	C10—H10A	0.9700
N2—C10	1.451 (3)	C10—H10B	0.9700
N2—H2	0.92 (3)	C11—C12	1.522 (3)
N3—C13	1.450 (3)	C11—H11A	0.9700
N3—C12	1.464 (3)	C11—H11B	0.9700
N3—C14	1.494 (4)	C12—H12A	0.9700
C1—C6	1.377 (3)	C12—H12B	0.9700
C1—C2	1.400 (3)	C13—H13A	0.9600
C2—C3	1.381 (3)	C13—H13B	0.9600
C3—C4	1.390 (3)	C13—H13C	0.9600
C3—H3A	0.9300	C14—H14A	0.9600
C4—C5	1.383 (3)	C14—H14B	0.9600
C4—C7	1.511 (3)	C14—H14C	0.9600
C5—C6	1.385 (3)

C1—O1—H1A	112.6 (18)	O2—C8—C9	122.52 (18)
C8—N1—C2	130.73 (19)	N1—C8—C9	110.60 (18)
C8—N1—H1	112.0 (15)	O3—C9—N2	124.6 (2)
C2—N1—H1	116.6 (15)	O3—C9—C8	120.83 (19)
C9—N2—C10	122.4 (2)	N2—C9—C8	114.58 (19)
C9—N2—H2	118.2 (16)	N2—C10—C11	112.48 (19)
C10—N2—H2	119.4 (16)	N2—C10—H10A	109.1
C13—N3—C12	111.7 (2)	C11—C10—H10A	109.1
C13—N3—C14	110.2 (3)	N2—C10—H10B	109.1
C12—N3—C14	109.6 (2)	C11—C10—H10B	109.1
O1—C1—C6	124.96 (18)	H10A—C10—H10B	107.8
O1—C1—C2	116.38 (17)	C10—C11—C12	112.92 (18)
C6—C1—C2	118.66 (19)	C10—C11—H11A	109.0
C3—C2—C1	120.35 (18)	C12—C11—H11A	109.0
C3—C2—N1	124.63 (17)	C10—C11—H11B	109.0
C1—C2—N1	114.99 (18)	C12—C11—H11B	109.0
C2—C3—C4	120.99 (19)	H11A—C11—H11B	107.8
C2—C3—H3A	119.5	N3—C12—C11	113.16 (18)
C4—C3—H3A	119.5	N3—C12—H12A	108.9
C5—C4—C3	118.1 (2)	C11—C12—H12A	108.9
C5—C4—C7	121.2 (2)	N3—C12—H12B	108.9
C3—C4—C7	120.7 (2)	C11—C12—H12B	108.9
C4—C5—C6	121.34 (19)	H12A—C12—H12B	107.8
C4—C5—H5	119.3	N3—C13—H13A	109.5
C6—C5—H5	119.3	N3—C13—H13B	109.5
C1—C6—C5	120.51 (19)	H13A—C13—H13B	109.5
C1—C6—H6	119.7	N3—C13—H13C	109.5
C5—C6—H6	119.7	H13A—C13—H13C	109.5
C4—C7—H7A	109.5	H13B—C13—H13C	109.5
C4—C7—H7B	109.5	N3—C14—H14A	109.5
H7A—C7—H7B	109.5	N3—C14—H14B	109.5
C4—C7—H7C	109.5	H14A—C14—H14B	109.5
H7A—C7—H7C	109.5	N3—C14—H14C	109.5
H7B—C7—H7C	109.5	H14A—C14—H14C	109.5
O2—C8—N1	126.9 (2)	H14B—C14—H14C	109.5

C8—N1—C2—C3	7.4 (3)	O1—C1—C6—C5	−178.97 (19)
C8—N1—C2—C1	−170.86 (19)	C2—C1—C6—C5	1.6 (3)
C9—N2—C10—C11	106.7 (2)	C4—C5—C6—C1	0.2 (3)
N2—C10—C11—C12	−57.1 (3)	C2—N1—C8—O2	−9.1 (3)
O1—C1—C2—C3	178.43 (18)	C2—N1—C8—C9	170.82 (19)
C6—C1—C2—C3	−2.1 (3)	C10—N2—C9—O3	0.8 (3)
O1—C1—C2—N1	−3.2 (3)	C10—N2—C9—C8	−179.59 (18)
C6—C1—C2—N1	176.24 (17)	O2—C8—C9—O3	−176.04 (19)
C1—C2—C3—C4	0.8 (3)	N1—C8—C9—O3	4.0 (3)
N1—C2—C3—C4	−177.40 (19)	O2—C8—C9—N2	4.3 (3)
C2—C3—C4—C5	1.1 (3)	N1—C8—C9—N2	−175.62 (17)
C2—C3—C4—C7	179.8 (2)	C13—N3—C12—C11	78.6 (3)
C3—C4—C5—C6	−1.6 (3)	C14—N3—C12—C11	−158.9 (2)
C7—C4—C5—C6	179.7 (2)	C10—C11—C12—N3	178.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.92 (3)	2.13 (3)	2.945 (2)	147 (2)
O1—H1A···N3ⁱⁱ	0.90 (2)	1.76 (2)	2.654 (2)	168 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₂₁N₃O₃
M_r	279.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.542 (2), 10.304 (2), 13.860 (3)
β (°)	109.16 (3)
V (Å³)	1557.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.27 × 0.24 × 0.17

Data collection
Diffractometer	Bruker APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.977, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	7686, 3099, 2093
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.620

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.151, 1.02
No. of reflections	3099
No. of parameters	196
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.26

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Siemens, 1994), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

O1—C1	1.359 (3)	N1—C2	1.403 (3)
O2—C8	1.222 (2)	N1—C8	1.334 (2)
O3—C9	1.231 (2)	N2—C9	1.322 (3)

C8—N1—C2—C3	7.4 (3)	C9—N2—C10—C11	106.7 (2)
C8—N1—C2—C1	−170.86 (19)	N2—C10—C11—C12	−57.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.92 (3)	2.13 (3)	2.945 (2)	147 (2)
O1—H1A···N3ⁱⁱ	0.904 (17)	1.764 (18)	2.654 (2)	168 (3)

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

Acknowledgements

This project was supported by the Natural Science Foundation of China (grant No. 21071133) and the Natural Science Foundation of Qingdao City.

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Han, Y.-T., Li, Y.-T., Wu, Z.-Y., Sun, W. & Zhu, C.-Y. (2007). Acta Cryst. E63, o3945. Web of Science CSD CrossRef IUCr Journals Google Scholar
Martinez, F. J. M., Martinez, I. I. P., Brito, M. A., Geniz, E. D., Rojas, R. C., Saavedra, J. B. R., Höpfl, H., Tlahuextl, M. & Contreras, R. (1998). J. Chem. Soc. Perkin Trans. 2, pp. 401–406. Google Scholar
Ojima, H. & Nonoyama, K. (1988). Coord. Chem. Rev. 92, 85–111. CrossRef CAS Web of Science Google Scholar
Ruiz, R., Faus, J., Lloret, F., Julve, M. & Journaux, Y. (1999). Coord. Chem. Rev. 193–195, 1069–1117. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1994). XP. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Yue, X.-T., Li, X.-W. & Wu, Z.-Y. (2012). Acta Cryst. E68, o8. Web of Science CSD CrossRef IUCr Journals Google Scholar