N′-[4-(Dimethyl­amino)benzyl­idene]acetohydrazide

Li, W.-W.; Yu, T.-M.; Yu, W.-B.; Lv, L.-P.; Hu, X.-C.

doi:10.1107/S1600536809032619

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2197

doi:10.1107/S1600536809032619

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N′-[4-(Dimethylamino)benzylidene]acetohydrazide

Wei-Wei Li,^a Tie-Ming Yu,^a Wen-Bo Yu,^a Lu-Ping Lv ^a and Xian-Chao Hu ^b ^*

^aDepartment of Chemical Engineering, Hangzhou Vocational and Technical College, Hangzhou 310018, People's Republic of China, and ^bResearch Center of Analysis and Measurement, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: zgdhxc@126.com

(Received 20 July 2009; accepted 17 August 2009; online 22 August 2009)

The title compound, C₁₁H₁₅N₃O, crystallizes with two independent molecules per asymmetric unit which differ slightly in their side-chain orientations: the C=N—N—C torsion angle is −176.2 (3)° in one of the molecules and −179.83 (3)° in the other. Each independent molecule adopts a trans configuration with respect to the C=N bond. The two independent molecules are related by a pseudo-inversion center and they exist as a N—H⋯O hydrogen-bonded dimer. The dimers are linked into zigzag chains along [100] by C—H⋯O hydrogen bonds.

Related literature

For general background to this type of compound, see: Cimerman et al. (1997 ); Offe et al. (1952 ); Richardson et al. (1988 ). For related structures, see: Li & Jian (2008 ); Shang et al. (2007 ); Tamboura et al. (2009 ).

Experimental

Crystal data

C₁₁H₁₅N₃O
M_r = 205.26
Orthorhombic, P b c a
a = 8.619 (4) Å
b = 20.063 (3) Å
c = 26.231 (3) Å
V = 4536 (2) Å³
Z = 16
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 223 K
0.25 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.977, T_max = 0.979
25277 measured reflections
3944 independent reflections
2266 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.260
S = 1.05
3944 reflections
278 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.86	2.09	2.930 (4)	166
N6—H6⋯O1ⁱⁱ	0.86	2.04	2.884 (4)	165
C3—H3⋯O1ⁱⁱⁱ	0.93	2.56	3.328 (4)	140
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032619/ci2860sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032619/ci2860Isup2.hkl

checkCIF report

Comment top

Schiff bases have attracted much attention due to the possibility of their analytical applications (Cimerman et al., 1997). They are also important ligands, which have been reported to have mild bacteriostatic activity and as potential oral iron-chelating drugs for genetic disorders such as thalassemia (Offe et al., 1952; Richardson et al., 1988). Metal complexes based on Schiff bases have received considerable attention because they can be utilized as model compounds of active centres in various complexes (Tamboura et al., 2009). We report here the crystal structure of the title compound (Fig. 1).

The title compound contains two independent, but almost identical molecules in the asymmetric unit. Each independent molecule adopts a trans configuration with respect to the C═N bond. The N1/N2/O1/C9/C10/C11 and N5/N6/O2/C10/C21/C22 planes form dihedral angles of 4.68 (6)° and 6.93 (5)°, respectively, with the C3-C8 and C14-C19 planes. The dihedral angle between the two independent benzene rings is 88.26 (9)°. Bond lengths and angles are comparable to those observed for related structures (Li et al., 2008; Shang et al., 2007).

The two independent molecules are related by a pseudo inversion center, and in the crystal they exist as N—H···O hydrogen-bonded dimers. The dimers are linked into a zigzag chain along the 'a' axis by C—H···O hydrogen bonds. (Table 1).

Related literature top

For general background to Schiff bases, see: Cimerman et al. (1997); Offe et al. (1952); Richardson et al. (1988). For related structures, see: Li & Jian (2008); Shang et al. (2007); Tamboura et al. (2009).

Experimental top

4-Dimethylaminobenzaldehyde (1.49 g, 0.01 mol) and acetohydrazide (0.74 g, 0.01 mol) were dissolved in stirred methanol (20 ml) and left for 3.5 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 87% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 490–493 K).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 40% probability level. Dashed lines indicate hydrogen bonds.
	Fig. 2. Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

N'-[4-(Dimethylamino)benzylidene]acetohydrazide top

Crystal data top

C₁₁H₁₅N₃O	F(000) = 1760
M_r = 205.26	D_x = 1.202 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3944 reflections
a = 8.619 (4) Å	θ = 1.5–25.0°
b = 20.063 (3) Å	µ = 0.08 mm⁻¹
c = 26.231 (3) Å	T = 223 K
V = 4536 (2) Å³	Block, colourless
Z = 16	0.25 × 0.21 × 0.19 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3944 independent reflections
Radiation source: fine-focus sealed tube	2266 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
T_min = 0.977, T_max = 0.979	k = −23→23
25277 measured reflections	l = −30→27

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.081	H-atom parameters constrained
wR(F²) = 0.260	w = 1/[σ²(F_o²) + (0.1428P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.009
3944 reflections	Δρ_max = 0.26 e Å⁻³
278 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0088 (18)

Crystal data top

C₁₁H₁₅N₃O	V = 4536 (2) Å³
M_r = 205.26	Z = 16
Orthorhombic, Pbca	Mo Kα radiation
a = 8.619 (4) Å	µ = 0.08 mm⁻¹
b = 20.063 (3) Å	T = 223 K
c = 26.231 (3) Å	0.25 × 0.21 × 0.19 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3944 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2266 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.979	R_int = 0.086
25277 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	0 restraints
wR(F²) = 0.260	H-atom parameters constrained
S = 1.05	Δρ_max = 0.26 e Å⁻³
3944 reflections	Δρ_min = −0.25 e Å⁻³
278 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.0047 (3)	0.29181 (12)	−0.13459 (9)	0.0780 (8)
O2	0.1988 (3)	0.06574 (13)	0.42455 (9)	0.0870 (9)
C1	−0.2222 (5)	0.2853 (2)	0.26167 (14)	0.0876 (12)
H1A	−0.2352	0.2920	0.2977	0.131*
H1B	−0.1581	0.2469	0.2560	0.131*
H1C	−0.3217	0.2784	0.2461	0.131*
C2	−0.0788 (5)	0.3912 (2)	0.27440 (14)	0.0960 (13)
H2A	−0.1206	0.3847	0.3080	0.144*
H2B	−0.1011	0.4357	0.2631	0.144*
H2C	0.0314	0.3845	0.2752	0.144*
C3	−0.1822 (4)	0.30188 (16)	0.15390 (12)	0.0642 (9)
H3	−0.2554	0.2715	0.1657	0.077*
C4	−0.1112 (4)	0.34523 (16)	0.18857 (12)	0.0609 (9)
C5	−0.0040 (4)	0.38962 (16)	0.16863 (13)	0.0705 (10)
H5	0.0450	0.4197	0.1903	0.085*
C6	0.0317 (4)	0.39019 (17)	0.11734 (13)	0.0711 (10)
H6A	0.1039	0.4208	0.1053	0.085*
C7	−0.0365 (4)	0.34675 (16)	0.08350 (12)	0.0602 (9)
C8	−0.1463 (4)	0.30314 (16)	0.10280 (12)	0.0636 (9)
H8	−0.1968	0.2741	0.0807	0.076*
C9	0.0084 (4)	0.34839 (18)	0.03007 (12)	0.0678 (9)
H9	0.0781	0.3809	0.0194	0.081*
C10	−0.0398 (4)	0.27958 (17)	−0.09107 (14)	0.0675 (10)
C11	−0.1489 (5)	0.2237 (2)	−0.08028 (14)	0.0894 (12)
H11A	−0.1751	0.2236	−0.0447	0.134*
H11B	−0.1005	0.1821	−0.0890	0.134*
H11C	−0.2415	0.2292	−0.1002	0.134*
C12	0.0762 (5)	0.1252 (2)	0.01346 (13)	0.0932 (13)
H12A	0.1036	0.1176	−0.0215	0.140*
H12B	0.0797	0.1721	0.0206	0.140*
H12C	−0.0268	0.1087	0.0196	0.140*
C13	0.2661 (6)	0.0345 (2)	0.02456 (15)	0.0972 (14)
H13A	0.2679	0.0387	−0.0119	0.146*
H13B	0.2141	−0.0060	0.0338	0.146*
H13C	0.3705	0.0335	0.0373	0.146*
C14	0.1752 (4)	0.09738 (16)	0.09815 (12)	0.0606 (9)
C15	0.0720 (5)	0.14273 (16)	0.12098 (12)	0.0684 (10)
H15	0.0105	0.1699	0.1005	0.082*
C16	0.0610 (4)	0.14740 (16)	0.17306 (12)	0.0670 (9)
H16	−0.0087	0.1776	0.1871	0.080*
C17	0.1510 (4)	0.10824 (15)	0.20548 (11)	0.0579 (9)
C18	0.2550 (4)	0.06487 (16)	0.18297 (12)	0.0616 (9)
H18	0.3176	0.0384	0.2036	0.074*
C19	0.2681 (4)	0.05990 (15)	0.13102 (12)	0.0647 (9)
H19	0.3408	0.0308	0.1173	0.078*
C20	0.1307 (4)	0.11238 (16)	0.26024 (12)	0.0642 (9)
H20	0.0637	0.1445	0.2732	0.077*
C21	0.2309 (4)	0.05138 (18)	0.37994 (13)	0.0684 (10)
C22	0.3373 (4)	−0.00500 (18)	0.36685 (13)	0.0772 (11)
H22A	0.4084	0.0090	0.3408	0.116*
H22B	0.2775	−0.0421	0.3547	0.116*
H22C	0.3942	−0.0181	0.3967	0.116*
N1	−0.0433 (3)	0.30740 (14)	−0.00272 (10)	0.0689 (8)
N2	0.0109 (3)	0.31648 (14)	−0.05201 (10)	0.0716 (8)
H2	0.0794	0.3468	−0.0576	0.086*
N3	−0.1490 (4)	0.34348 (16)	0.23945 (10)	0.0791 (9)
N4	0.1849 (4)	0.09056 (14)	0.04632 (10)	0.0786 (9)
N5	0.1997 (3)	0.07432 (14)	0.29129 (10)	0.0647 (8)
N6	0.1681 (3)	0.08653 (14)	0.34201 (10)	0.0714 (8)
H6	0.1049	0.1182	0.3495	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0901 (19)	0.0899 (18)	0.0541 (16)	0.0010 (14)	0.0130 (13)	−0.0020 (12)
O2	0.105 (2)	0.107 (2)	0.0488 (15)	0.0166 (16)	0.0105 (14)	0.0072 (12)
C1	0.107 (3)	0.093 (3)	0.063 (2)	0.005 (2)	0.020 (2)	0.0040 (19)
C2	0.098 (3)	0.123 (3)	0.068 (3)	−0.004 (3)	−0.001 (2)	−0.026 (2)
C3	0.066 (2)	0.068 (2)	0.058 (2)	−0.0080 (17)	−0.0004 (17)	0.0067 (16)
C4	0.063 (2)	0.069 (2)	0.050 (2)	0.0069 (17)	−0.0043 (16)	0.0006 (16)
C5	0.079 (3)	0.069 (2)	0.064 (2)	−0.0082 (18)	−0.002 (2)	−0.0084 (17)
C6	0.080 (3)	0.067 (2)	0.067 (2)	−0.0102 (18)	0.003 (2)	0.0036 (17)
C7	0.066 (2)	0.0609 (19)	0.054 (2)	0.0026 (17)	−0.0044 (16)	0.0072 (15)
C8	0.072 (2)	0.068 (2)	0.051 (2)	−0.0029 (18)	−0.0065 (17)	0.0000 (15)
C9	0.078 (3)	0.071 (2)	0.054 (2)	0.0010 (18)	0.0016 (18)	0.0029 (17)
C10	0.069 (2)	0.077 (2)	0.057 (2)	0.0096 (19)	0.0052 (18)	0.0013 (18)
C11	0.098 (3)	0.097 (3)	0.073 (3)	−0.023 (2)	−0.006 (2)	0.006 (2)
C12	0.114 (3)	0.109 (3)	0.057 (2)	0.002 (3)	−0.010 (2)	0.010 (2)
C13	0.135 (4)	0.091 (3)	0.066 (3)	0.011 (3)	0.007 (2)	−0.010 (2)
C14	0.073 (2)	0.0649 (19)	0.0436 (19)	−0.0063 (18)	−0.0001 (17)	−0.0009 (15)
C15	0.088 (3)	0.063 (2)	0.054 (2)	0.0069 (19)	−0.0034 (18)	0.0038 (16)
C16	0.072 (2)	0.068 (2)	0.062 (2)	0.0115 (18)	0.0025 (18)	−0.0035 (16)
C17	0.067 (2)	0.0607 (19)	0.0461 (19)	−0.0017 (16)	0.0002 (16)	0.0010 (14)
C18	0.068 (2)	0.0658 (19)	0.052 (2)	0.0061 (16)	−0.0032 (17)	0.0034 (15)
C19	0.079 (2)	0.0608 (19)	0.054 (2)	0.0037 (17)	0.0038 (18)	−0.0007 (15)
C20	0.067 (2)	0.072 (2)	0.054 (2)	0.0025 (18)	0.0035 (17)	−0.0050 (17)
C21	0.071 (2)	0.087 (2)	0.047 (2)	−0.0010 (19)	0.0036 (18)	0.0094 (18)
C22	0.080 (3)	0.083 (2)	0.068 (2)	0.004 (2)	0.0007 (19)	0.0059 (18)
N1	0.076 (2)	0.0802 (19)	0.0506 (17)	0.0032 (15)	0.0036 (14)	0.0104 (14)
N2	0.082 (2)	0.0794 (18)	0.0530 (18)	−0.0102 (16)	0.0073 (15)	0.0002 (14)
N3	0.095 (2)	0.092 (2)	0.0505 (18)	−0.0090 (18)	0.0027 (16)	−0.0076 (15)
N4	0.105 (3)	0.083 (2)	0.0478 (18)	0.0107 (17)	0.0013 (16)	0.0013 (14)
N5	0.0686 (19)	0.0819 (18)	0.0435 (16)	0.0004 (15)	0.0037 (14)	0.0026 (13)
N6	0.077 (2)	0.091 (2)	0.0465 (17)	0.0135 (16)	0.0070 (15)	0.0007 (14)

Geometric parameters (Å, º) top

O1—C10	1.229 (4)	C12—H12A	0.96
O2—C21	1.236 (4)	C12—H12B	0.96
C1—N3	1.449 (5)	C12—H12C	0.96
C1—H1A	0.96	C13—N4	1.443 (5)
C1—H1B	0.96	C13—H13A	0.96
C1—H1C	0.96	C13—H13B	0.96
C2—N3	1.456 (5)	C13—H13C	0.96
C2—H2A	0.96	C14—N4	1.369 (4)
C2—H2B	0.96	C14—C19	1.396 (5)
C2—H2C	0.96	C14—C15	1.406 (5)
C3—C8	1.376 (4)	C15—C16	1.373 (4)
C3—C4	1.399 (4)	C15—H15	0.93
C3—H3	0.93	C16—C17	1.394 (4)
C4—N3	1.374 (4)	C16—H16	0.93
C4—C5	1.386 (5)	C17—C18	1.381 (4)
C5—C6	1.380 (4)	C17—C20	1.450 (4)
C5—H5	0.93	C18—C19	1.371 (4)
C6—C7	1.376 (5)	C18—H18	0.93
C6—H6A	0.93	C19—H19	0.93
C7—C8	1.384 (5)	C20—N5	1.265 (4)
C7—C9	1.454 (4)	C20—H20	0.93
C8—H8	0.93	C21—N6	1.334 (4)
C9—N1	1.271 (4)	C21—C22	1.496 (5)
C9—H9	0.93	C22—H22A	0.96
C10—N2	1.337 (4)	C22—H22B	0.96
C10—C11	1.491 (5)	C22—H22C	0.96
C11—H11A	0.96	N1—N2	1.387 (3)
C11—H11B	0.96	N2—H2	0.86
C11—H11C	0.96	N5—N6	1.380 (4)
C12—N4	1.450 (5)	N6—H6	0.86

N3—C1—H1A	109.5	N4—C13—H13B	109.5
N3—C1—H1B	109.5	H13A—C13—H13B	109.5
H1A—C1—H1B	109.5	N4—C13—H13C	109.4
N3—C1—H1C	109.5	H13A—C13—H13C	109.5
H1A—C1—H1C	109.5	H13B—C13—H13C	109.5
H1B—C1—H1C	109.5	N4—C14—C19	121.6 (3)
N3—C2—H2A	109.5	N4—C14—C15	121.7 (3)
N3—C2—H2B	109.5	C19—C14—C15	116.6 (3)
H2A—C2—H2B	109.5	C16—C15—C14	120.8 (3)
N3—C2—H2C	109.5	C16—C15—H15	119.6
H2A—C2—H2C	109.5	C14—C15—H15	119.6
H2B—C2—H2C	109.5	C15—C16—C17	122.0 (3)
C8—C3—C4	121.5 (3)	C15—C16—H16	119.0
C8—C3—H3	119.2	C17—C16—H16	119.0
C4—C3—H3	119.2	C18—C17—C16	117.1 (3)
N3—C4—C5	122.8 (3)	C18—C17—C20	122.6 (3)
N3—C4—C3	120.7 (3)	C16—C17—C20	120.3 (3)
C5—C4—C3	116.5 (3)	C19—C18—C17	121.6 (3)
C6—C5—C4	121.4 (3)	C19—C18—H18	119.2
C6—C5—H5	119.3	C17—C18—H18	119.2
C4—C5—H5	119.3	C18—C19—C14	121.8 (3)
C7—C6—C5	121.9 (3)	C18—C19—H19	119.1
C7—C6—H6A	119.0	C14—C19—H19	119.1
C5—C6—H6A	119.1	N5—C20—C17	123.1 (3)
C6—C7—C8	117.2 (3)	N5—C20—H20	118.4
C6—C7—C9	119.6 (3)	C17—C20—H20	118.4
C8—C7—C9	123.3 (3)	O2—C21—N6	119.5 (3)
C3—C8—C7	121.4 (3)	O2—C21—C22	122.0 (3)
C3—C8—H8	119.3	N6—C21—C22	118.5 (3)
C7—C8—H8	119.3	C21—C22—H22A	109.5
N1—C9—C7	123.0 (3)	C21—C22—H22B	109.5
N1—C9—H9	118.5	H22A—C22—H22B	109.5
C7—C9—H9	118.5	C21—C22—H22C	109.5
O1—C10—N2	120.0 (3)	H22A—C22—H22C	109.5
O1—C10—C11	121.5 (3)	H22B—C22—H22C	109.5
N2—C10—C11	118.5 (3)	C9—N1—N2	115.3 (3)
C10—C11—H11A	109.5	C10—N2—N1	122.1 (3)
C10—C11—H11B	109.4	C10—N2—H2	119.0
H11A—C11—H11B	109.5	N1—N2—H2	119.0
C10—C11—H11C	109.5	C4—N3—C2	119.7 (3)
H11A—C11—H11C	109.5	C4—N3—C1	121.0 (3)
H11B—C11—H11C	109.5	C2—N3—C1	117.2 (3)
N4—C12—H12A	109.5	C14—N4—C13	120.0 (3)
N4—C12—H12B	109.5	C14—N4—C12	120.2 (3)
H12A—C12—H12B	109.5	C13—N4—C12	116.9 (3)
N4—C12—H12C	109.5	C20—N5—N6	114.9 (3)
H12A—C12—H12C	109.5	C21—N6—N5	123.0 (3)
H12B—C12—H12C	109.5	C21—N6—H6	118.5
N4—C13—H13A	109.5	N5—N6—H6	118.5

C8—C3—C4—N3	179.7 (3)	N4—C14—C19—C18	−177.7 (3)
C8—C3—C4—C5	0.5 (5)	C15—C14—C19—C18	2.7 (5)
N3—C4—C5—C6	180.0 (3)	C18—C17—C20—N5	−4.0 (5)
C3—C4—C5—C6	−0.8 (5)	C16—C17—C20—N5	174.0 (3)
C4—C5—C6—C7	−0.3 (5)	C7—C9—N1—N2	179.6 (3)
C5—C6—C7—C8	1.6 (5)	O1—C10—N2—N1	175.8 (3)
C5—C6—C7—C9	−178.4 (3)	C11—C10—N2—N1	−4.8 (5)
C4—C3—C8—C7	0.9 (5)	C9—N1—N2—C10	−176.2 (3)
C6—C7—C8—C3	−1.9 (5)	C5—C4—N3—C2	2.0 (5)
C9—C7—C8—C3	178.1 (3)	C3—C4—N3—C2	−177.1 (3)
C6—C7—C9—N1	176.0 (3)	C5—C4—N3—C1	−160.9 (3)
C8—C7—C9—N1	−4.0 (5)	C3—C4—N3—C1	20.0 (5)
N4—C14—C15—C16	178.1 (3)	C19—C14—N4—C13	13.6 (5)
C19—C14—C15—C16	−2.3 (5)	C15—C14—N4—C13	−166.8 (4)
C14—C15—C16—C17	0.4 (5)	C19—C14—N4—C12	173.7 (3)
C15—C16—C17—C18	1.1 (5)	C15—C14—N4—C12	−6.6 (5)
C15—C16—C17—C20	−177.0 (3)	C17—C20—N5—N6	178.8 (3)
C16—C17—C18—C19	−0.7 (5)	O2—C21—N6—N5	179.0 (3)
C20—C17—C18—C19	177.4 (3)	C22—C21—N6—N5	−1.7 (5)
C17—C18—C19—C14	−1.3 (5)	C20—N5—N6—C21	−179.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	2.09	2.930 (4)	166
N6—H6···O1ⁱⁱ	0.86	2.04	2.884 (4)	165
C3—H3···O1ⁱⁱⁱ	0.93	2.56	3.328 (4)	140
C11—H11A···N1	0.96	2.31	2.791 (5)	110

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₅N₃O
M_r	205.26
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	223
a, b, c (Å)	8.619 (4), 20.063 (3), 26.231 (3)
V (Å³)	4536 (2)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.21 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.977, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	25277, 3944, 2266
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.260, 1.05
No. of reflections	3944
No. of parameters	278
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.25

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	2.09	2.930 (4)	166
N6—H6···O1ⁱⁱ	0.86	2.04	2.884 (4)	165
C3—H3···O1ⁱⁱⁱ	0.93	2.56	3.328 (4)	140

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

Acknowledgements

The authors thank the Science and Technology Project of Zhejiang Province (grant No. 2007 F70077) and Hangzhou Vocational and Technical College for financial support.

References

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