2-Hy­droxy-N′-methyl-5-nitro­benzohydrazide

Yang, M.; Jin, C.; Zhou, X.; Jin, L.

doi:10.1107/S1600536813019776

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1305

doi:10.1107/S1600536813019776

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2-Hydroxy-N′-methyl-5-nitrobenzohydrazide

Ming Yang,^a Chengzhi Jin,^a Xiaodong Zhou ^a and Longfei Jin ^a ^*

^aCollege of Chemistry and Material Science, South-Central University for Nationalities, Wuhan 430074, People's Republic of China
^*Correspondence e-mail: longfei.jin@yahoo.com

(Received 7 July 2013; accepted 17 July 2013; online 24 July 2013)

In the title compound, C₈H₉N₃O₄, there are two molecules in the asymmetric unit, one of which is in the zwitterionic form. The zwitterion contains an intramolecular N—H⋯O hydrogen bond and the other molecule contains both an intramolecular N—H⋯O and an intramolecular O—H⋯O hydrogen bond. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds link the molecules, formimg a two-dimensional network parallel to (10-1).

Related literature

For the biological activities of salicylhydrazide derivatives, see: Bagchi et al. (2004 ); Thompson et al. (2004 ); Al-Mawsawi et al. (2007 ). For metal complexes involving derivatives of the title compound, see: Jin et al. (2006a ,b ). For related crystal structures, see: Liu et al. (2006 ); Luo et al. (2007 ); Xu & Liu (2006 ); Zhang (2012 ).

Experimental

Crystal data

C₈H₉N₃O₄
M_r = 211.18
Monoclinic, P 2₁ /n
a = 7.3818 (15) Å
b = 13.106 (3) Å
c = 18.719 (4) Å
β = 95.25 (3)°
V = 1803.4 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 K
0.26 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.968, T_max = 0.987
11293 measured reflections
3536 independent reflections
2356 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.142
S = 1.06
3536 reflections
291 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O2	0.90 (2)	1.92 (2)	2.756 (3)	154 (3)
N1—H1⋯O1	0.90 (2)	1.78 (2)	2.550 (3)	141 (3)
N2—H2B⋯N5	1.02 (3)	1.84 (3)	2.858 (3)	174 (3)
O5—H5⋯O6	0.85 (2)	1.74 (2)	2.549 (3)	158 (4)
N5—H5A⋯O6	0.83 (2)	2.44 (3)	2.719 (3)	101 (2)
N5—H5A⋯O4ⁱ	0.83 (2)	2.46 (2)	3.162 (3)	143 (3)
N2—H2A⋯O1ⁱⁱ	0.94 (2)	2.08 (3)	2.762 (3)	128 (2)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813019776/lh5633sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019776/lh5633Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813019776/lh5633Isup3.cml

checkCIF report

Comment top

Derivatives of salicylhydrazide exhibit prominent biological activites such as antimicrobial activity, inhibitor of receptor and enzyme inhibitor (Bagchi et al., 2004; Thompson et al., 2004; Al-Mawsawi et al., 2007). Several coordination sites exist in these compounds to lead to potential supramolecular structures. In our previous work, some anologs and their metal complexes were successfully sythesized and some latent functional studies were made (Jin et al., 2006a,b). As part of our ongoing studies, the preparation and X-ray structure determination of the title compound (I) was undertaken.

The asymmetric unit of (I) is shown in Fig. 1. There are two molecules in the asymmetric unit. One of the molecules is in the zwitterionic form. In the zwitterion N2 is protonated and O1 deprotonated. The bond lengths and angles in each molecule are unexceptional and agree with those reported for similar structures (Liu et al., 2006; Luo et al., 2007; Xu & Liu, 2006; Zhang, 2012). In each molecule the non-H atoms, with the exception of the methyl and nitro groups, lie in an approximate plane with r.m.s deviations of 0.073 and 0.104 Å. The zwitterion contains an intramolecular N—H···O hydrogen bond and the other molecule contains intramolecular O—H···O and N—H···O hydrogen bonds. In the crystal, N—H···O and N—H···N hydrogen bonds link the molecules formimg a two-dimensional network (see Fig. 2) parallel to (101).

Related literature top

For the biological activities of salicylhydrazide derivatives, see: Bagchi et al. (2004); Thompson et al. (2004); Al-Mawsawi et al. (2007). For metal complexes involving derivatives of the title compound, see: Jin et al. (2006a,b). For related crystal structures, see: Liu et al. (2006); Luo et al. (2007); Xu & Liu (2006); Zhang (2012).

Experimental top

The title compound was systhesized by refluxing a mixture of ethyl 5-nitro-salicylate (0.1 mol) and methylhydrazine (0.2 mol) for 14 h. To the resulting solution acetic acid was added and it was cooled to room temperature. The mixture was evaporated and washed with diethyl ether. Single crystals suitable for X-ray diffraction analysis were grown by slow evaporation from a solution of (I) in methanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of (I) showing 30% probability displacement ellipsoids. Dashed lines indicate hydrogen bonds.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines

2-Hydroxy-N'-methyl-5-nitrobenzohydrazide top

Crystal data top

C₈H₉N₃O₄	F(000) = 880
M_r = 211.18	D_x = 1.556 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1664 reflections
a = 7.3818 (15) Å	θ = 2.9–21.8°
b = 13.106 (3) Å	µ = 0.13 mm⁻¹
c = 18.719 (4) Å	T = 293 K
β = 95.25 (3)°	Block, yellow
V = 1803.4 (6) Å³	0.26 × 0.20 × 0.10 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	3536 independent reflections
Radiation source: fine-focus sealed tube	2356 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.968, T_max = 0.987	k = −15→16
11293 measured reflections	l = −23→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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0565P)² + 0.5317P] where P = (F_o² + 2F_c²)/3
3536 reflections	(Δ/σ)_max = 0.026
291 parameters	Δρ_max = 0.22 e Å⁻³
5 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₈H₉N₃O₄	V = 1803.4 (6) Å³
M_r = 211.18	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.3818 (15) Å	µ = 0.13 mm⁻¹
b = 13.106 (3) Å	T = 293 K
c = 18.719 (4) Å	0.26 × 0.20 × 0.10 mm
β = 95.25 (3)°

Data collection top

Bruker SMART CCD diffractometer	3536 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2356 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.987	R_int = 0.044
11293 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	5 restraints
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.22 e Å⁻³
3536 reflections	Δρ_min = −0.18 e Å⁻³
291 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
C1	0.5851 (3)	0.42908 (18)	0.18014 (13)	0.0339 (6)
C2	0.5537 (4)	0.53339 (19)	0.15979 (15)	0.0422 (7)
C3	0.5864 (4)	0.6078 (2)	0.21338 (15)	0.0472 (7)
H3	0.5608	0.6757	0.2021	0.057*
C4	0.6544 (4)	0.5839 (2)	0.28124 (15)	0.0445 (7)
H4	0.6754	0.6347	0.3157	0.053*
C5	0.6921 (3)	0.4822 (2)	0.29859 (14)	0.0377 (6)
C6	0.6547 (3)	0.40610 (19)	0.24911 (13)	0.0358 (6)
H6	0.6766	0.3385	0.2622	0.043*
C7	0.5512 (3)	0.34258 (18)	0.12929 (13)	0.0336 (6)
C8	0.6571 (4)	0.2470 (2)	−0.00925 (16)	0.0549 (8)
H8A	0.7340	0.3000	−0.0249	0.082*
H8B	0.6334	0.1979	−0.0471	0.082*
H8C	0.7167	0.2139	0.0322	0.082*
C9	0.3376 (3)	−0.01241 (18)	0.22768 (14)	0.0341 (6)
C10	0.3287 (4)	−0.1136 (2)	0.25337 (15)	0.0427 (7)
C11	0.3917 (4)	−0.1365 (2)	0.32380 (17)	0.0559 (8)
H11	0.3873	−0.2034	0.3400	0.067*
C12	0.4595 (4)	−0.0621 (2)	0.36920 (17)	0.0557 (8)
H12	0.5013	−0.0778	0.4163	0.067*
C13	0.4657 (4)	0.0376 (2)	0.34444 (14)	0.0421 (7)
C14	0.4053 (3)	0.06248 (19)	0.27498 (14)	0.0382 (6)
H14	0.4099	0.1299	0.2597	0.046*
C15	0.2762 (3)	0.00751 (19)	0.15166 (14)	0.0363 (6)
C16	0.0855 (4)	0.1430 (2)	0.03122 (17)	0.0601 (9)
H16A	0.0122	0.0904	0.0497	0.090*
H16B	0.0630	0.1455	−0.0201	0.090*
H16C	0.0550	0.2076	0.0511	0.090*
N1	0.5069 (3)	0.37013 (16)	0.06155 (12)	0.0432 (6)
H1	0.489 (4)	0.4367 (15)	0.0517 (16)	0.072*
N2	0.4833 (3)	0.29164 (17)	0.00913 (12)	0.0400 (5)
H2A	0.420 (4)	0.321 (2)	−0.0313 (12)	0.072*
H2B	0.409 (4)	0.233 (2)	0.0275 (16)	0.072*
N3	0.7769 (3)	0.45572 (19)	0.36861 (12)	0.0463 (6)
N4	0.3109 (3)	0.09987 (16)	0.12471 (12)	0.0422 (6)
H4A	0.393 (3)	0.143 (2)	0.1470 (15)	0.072*
N5	0.2755 (3)	0.12117 (16)	0.05067 (12)	0.0421 (6)
H5A	0.306 (4)	0.0673 (17)	0.0315 (16)	0.072*
N6	0.5389 (3)	0.1169 (2)	0.39330 (13)	0.0570 (7)
O1	0.4975 (3)	0.55896 (14)	0.09395 (10)	0.0593 (6)
O2	0.5657 (3)	0.25254 (12)	0.14945 (10)	0.0452 (5)
O3	0.8350 (3)	0.36913 (18)	0.37959 (11)	0.0684 (7)
O4	0.7919 (3)	0.52224 (16)	0.41560 (11)	0.0664 (6)
O5	0.2604 (3)	−0.19058 (14)	0.21215 (12)	0.0598 (6)
H5	0.223 (5)	−0.159 (3)	0.1736 (14)	0.090*
O6	0.1955 (3)	−0.05861 (14)	0.11305 (10)	0.0507 (5)
O7	0.5987 (4)	0.0933 (2)	0.45398 (13)	0.0933 (9)
O8	0.5409 (4)	0.20419 (19)	0.37205 (13)	0.0902 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0403 (14)	0.0276 (13)	0.0339 (15)	0.0005 (10)	0.0036 (11)	0.0025 (11)
C2	0.0498 (16)	0.0315 (15)	0.0446 (17)	0.0026 (12)	0.0010 (13)	0.0023 (13)
C3	0.0621 (19)	0.0282 (15)	0.0507 (19)	0.0000 (12)	0.0016 (15)	−0.0019 (13)
C4	0.0556 (17)	0.0333 (15)	0.0443 (17)	−0.0073 (12)	0.0033 (14)	−0.0107 (13)
C5	0.0383 (14)	0.0418 (15)	0.0327 (15)	−0.0069 (11)	0.0009 (11)	−0.0009 (12)
C6	0.0388 (14)	0.0310 (14)	0.0373 (15)	−0.0015 (11)	0.0013 (12)	0.0036 (12)
C7	0.0423 (15)	0.0271 (14)	0.0309 (15)	0.0015 (10)	0.0013 (11)	0.0042 (11)
C8	0.067 (2)	0.0474 (17)	0.0516 (19)	0.0106 (15)	0.0131 (16)	0.0002 (15)
C9	0.0372 (14)	0.0276 (13)	0.0379 (15)	0.0025 (10)	0.0056 (11)	0.0001 (12)
C10	0.0430 (15)	0.0366 (15)	0.0483 (18)	−0.0012 (12)	0.0033 (13)	0.0046 (13)
C11	0.064 (2)	0.0409 (17)	0.062 (2)	−0.0032 (14)	0.0016 (16)	0.0222 (16)
C12	0.0602 (19)	0.060 (2)	0.0470 (19)	0.0040 (15)	0.0020 (15)	0.0199 (16)
C13	0.0446 (16)	0.0467 (17)	0.0349 (16)	0.0002 (12)	0.0030 (12)	0.0007 (13)
C14	0.0461 (15)	0.0346 (14)	0.0341 (15)	0.0024 (11)	0.0046 (12)	0.0029 (12)
C15	0.0430 (15)	0.0285 (14)	0.0374 (16)	0.0007 (11)	0.0030 (12)	−0.0033 (12)
C16	0.067 (2)	0.057 (2)	0.054 (2)	−0.0022 (16)	−0.0081 (16)	−0.0028 (16)
N1	0.0739 (16)	0.0235 (11)	0.0315 (13)	0.0052 (11)	0.0010 (11)	0.0010 (10)
N2	0.0568 (15)	0.0314 (12)	0.0304 (13)	0.0039 (10)	−0.0032 (11)	0.0032 (10)
N3	0.0541 (15)	0.0462 (15)	0.0379 (15)	−0.0087 (12)	0.0004 (11)	−0.0008 (12)
N4	0.0580 (15)	0.0364 (13)	0.0305 (13)	−0.0075 (10)	−0.0048 (11)	0.0004 (10)
N5	0.0590 (15)	0.0362 (13)	0.0297 (13)	−0.0020 (11)	−0.0023 (11)	−0.0008 (10)
N6	0.0685 (17)	0.0639 (19)	0.0370 (16)	−0.0011 (14)	−0.0036 (13)	−0.0037 (14)
O1	0.1027 (17)	0.0323 (10)	0.0399 (12)	0.0062 (10)	−0.0102 (11)	0.0077 (9)
O2	0.0681 (13)	0.0256 (10)	0.0391 (11)	−0.0029 (8)	−0.0099 (9)	0.0051 (8)
O3	0.0945 (17)	0.0608 (15)	0.0451 (13)	0.0100 (13)	−0.0185 (12)	0.0041 (11)
O4	0.0981 (17)	0.0579 (14)	0.0412 (13)	−0.0164 (12)	−0.0037 (12)	−0.0104 (11)
O5	0.0765 (15)	0.0308 (11)	0.0702 (16)	−0.0083 (10)	−0.0033 (12)	0.0015 (11)
O6	0.0681 (13)	0.0373 (11)	0.0454 (12)	−0.0088 (9)	−0.0029 (10)	−0.0066 (9)
O7	0.131 (2)	0.102 (2)	0.0402 (14)	−0.0151 (17)	−0.0271 (14)	0.0047 (14)
O8	0.155 (3)	0.0508 (15)	0.0583 (16)	−0.0083 (15)	−0.0239 (16)	−0.0097 (13)

Geometric parameters (Å, º) top

C1—C6	1.379 (3)	C11—H11	0.9300
C1—C2	1.432 (3)	C12—C13	1.389 (4)
C1—C7	1.487 (3)	C12—H12	0.9300
C2—O1	1.308 (3)	C13—C14	1.375 (4)
C2—C3	1.404 (4)	C13—N6	1.455 (4)
C3—C4	1.359 (4)	C14—H14	0.9300
C3—H3	0.9300	C15—O6	1.245 (3)
C4—C5	1.394 (4)	C15—N4	1.345 (3)
C4—H4	0.9300	C16—N5	1.445 (4)
C5—C6	1.372 (3)	C16—H16A	0.9600
C5—N3	1.443 (3)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C7—O2	1.240 (3)	N1—N2	1.421 (3)
C7—N1	1.330 (3)	N1—H1	0.899 (17)
C8—N2	1.479 (3)	N2—H2A	0.937 (17)
C8—H8A	0.9600	N2—H2B	1.02 (3)
C8—H8B	0.9600	N3—O3	1.224 (3)
C8—H8C	0.9600	N3—O4	1.236 (3)
C9—C14	1.384 (3)	N4—N5	1.415 (3)
C9—C10	1.414 (3)	N4—H4A	0.903 (18)
C9—C15	1.477 (3)	N5—H5A	0.832 (17)
C10—O5	1.340 (3)	N6—O8	1.212 (3)
C10—C11	1.390 (4)	N6—O7	1.220 (3)
C11—C12	1.359 (4)	O5—H5	0.854 (18)

C6—C1—C2	119.7 (2)	C13—C12—H12	120.4
C6—C1—C7	117.3 (2)	C14—C13—C12	121.4 (3)
C2—C1—C7	123.0 (2)	C14—C13—N6	119.7 (2)
O1—C2—C3	121.0 (2)	C12—C13—N6	118.9 (3)
O1—C2—C1	121.7 (2)	C13—C14—C9	120.3 (2)
C3—C2—C1	117.4 (2)	C13—C14—H14	119.9
C4—C3—C2	122.2 (3)	C9—C14—H14	119.9
C4—C3—H3	118.9	O6—C15—N4	120.4 (2)
C2—C3—H3	118.9	O6—C15—C9	121.7 (2)
C3—C4—C5	119.2 (2)	N4—C15—C9	117.9 (2)
C3—C4—H4	120.4	N5—C16—H16A	109.5
C5—C4—H4	120.4	N5—C16—H16B	109.5
C6—C5—C4	121.0 (2)	H16A—C16—H16B	109.5
C6—C5—N3	118.8 (2)	N5—C16—H16C	109.5
C4—C5—N3	120.2 (2)	H16A—C16—H16C	109.5
C5—C6—C1	120.5 (2)	H16B—C16—H16C	109.5
C5—C6—H6	119.7	C7—N1—N2	117.7 (2)
C1—C6—H6	119.7	C7—N1—H1	119 (2)
O2—C7—N1	123.7 (2)	N2—N1—H1	124 (2)
O2—C7—C1	121.7 (2)	N1—N2—C8	113.2 (2)
N1—C7—C1	114.6 (2)	N1—N2—H2A	106.1 (19)
N2—C8—H8A	109.5	C8—N2—H2A	110.8 (19)
N2—C8—H8B	109.5	N1—N2—H2B	110.2 (17)
H8A—C8—H8B	109.5	C8—N2—H2B	106.7 (17)
N2—C8—H8C	109.5	H2A—N2—H2B	110 (3)
H8A—C8—H8C	109.5	O3—N3—O4	121.8 (2)
H8B—C8—H8C	109.5	O3—N3—C5	119.5 (2)
C14—C9—C10	118.2 (2)	O4—N3—C5	118.7 (2)
C14—C9—C15	123.5 (2)	C15—N4—N5	121.4 (2)
C10—C9—C15	118.3 (2)	C15—N4—H4A	122 (2)
O5—C10—C11	117.3 (2)	N5—N4—H4A	113 (2)
O5—C10—C9	122.5 (2)	N4—N5—C16	111.9 (2)
C11—C10—C9	120.2 (3)	N4—N5—H5A	103 (2)
C12—C11—C10	120.7 (3)	C16—N5—H5A	111 (2)
C12—C11—H11	119.6	O8—N6—O7	122.1 (3)
C10—C11—H11	119.6	O8—N6—C13	118.9 (2)
C11—C12—C13	119.2 (3)	O7—N6—C13	119.1 (3)
C11—C12—H12	120.4	C10—O5—H5	102 (3)

C6—C1—C2—O1	176.1 (2)	C11—C12—C13—C14	−0.2 (4)
C7—C1—C2—O1	−1.9 (4)	C11—C12—C13—N6	−179.9 (3)
C6—C1—C2—C3	−3.7 (4)	C12—C13—C14—C9	−0.5 (4)
C7—C1—C2—C3	178.3 (2)	N6—C13—C14—C9	179.1 (2)
O1—C2—C3—C4	−176.3 (3)	C10—C9—C14—C13	1.5 (4)
C1—C2—C3—C4	3.5 (4)	C15—C9—C14—C13	−177.8 (2)
C2—C3—C4—C5	−0.4 (4)	C14—C9—C15—O6	−170.9 (2)
C3—C4—C5—C6	−2.7 (4)	C10—C9—C15—O6	9.8 (4)
C3—C4—C5—N3	175.3 (2)	C14—C9—C15—N4	9.4 (4)
C4—C5—C6—C1	2.4 (4)	C10—C9—C15—N4	−169.9 (2)
N3—C5—C6—C1	−175.6 (2)	O2—C7—N1—N2	−3.0 (4)
C2—C1—C6—C5	0.8 (4)	C1—C7—N1—N2	176.3 (2)
C7—C1—C6—C5	179.0 (2)	C7—N1—N2—C8	−75.0 (3)
C6—C1—C7—O2	7.7 (4)	C6—C5—N3—O3	9.4 (4)
C2—C1—C7—O2	−174.2 (2)	C4—C5—N3—O3	−168.7 (3)
C6—C1—C7—N1	−171.6 (2)	C6—C5—N3—O4	−172.0 (2)
C2—C1—C7—N1	6.5 (3)	C4—C5—N3—O4	10.0 (4)
C14—C9—C10—O5	178.0 (2)	O6—C15—N4—N5	−7.0 (4)
C15—C9—C10—O5	−2.7 (4)	C9—C15—N4—N5	172.7 (2)
C14—C9—C10—C11	−1.8 (4)	C15—N4—N5—C16	80.1 (3)
C15—C9—C10—C11	177.5 (2)	C14—C13—N6—O8	1.8 (4)
O5—C10—C11—C12	−178.7 (3)	C12—C13—N6—O8	−178.5 (3)
C9—C10—C11—C12	1.1 (4)	C14—C13—N6—O7	−177.2 (3)
C10—C11—C12—C13	−0.1 (4)	C12—C13—N6—O7	2.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2	0.90 (2)	1.92 (2)	2.756 (3)	154 (3)
N1—H1···O1	0.90 (2)	1.78 (2)	2.550 (3)	141 (3)
N2—H2B···N5	1.02 (3)	1.84 (3)	2.858 (3)	174 (3)
O5—H5···O6	0.85 (2)	1.74 (2)	2.549 (3)	158 (4)
N5—H5A···O6	0.83 (2)	2.44 (3)	2.719 (3)	101 (2)
N5—H5A···O4ⁱ	0.83 (2)	2.46 (2)	3.162 (3)	143 (3)
N2—H2A···O7ⁱ	0.94 (2)	2.61 (3)	3.296 (3)	130 (2)
N2—H2A···O1ⁱⁱ	0.94 (2)	2.08 (3)	2.762 (3)	128 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2	0.903 (18)	1.92 (2)	2.756 (3)	154 (3)
N1—H1···O1	0.899 (17)	1.78 (2)	2.550 (3)	141 (3)
N2—H2B···N5	1.02 (3)	1.84 (3)	2.858 (3)	174 (3)
O5—H5···O6	0.854 (18)	1.74 (2)	2.549 (3)	158 (4)
N5—H5A···O6	0.832 (17)	2.44 (3)	2.719 (3)	101 (2)
N5—H5A···O4ⁱ	0.832 (17)	2.46 (2)	3.162 (3)	143 (3)
N2—H2A···O1ⁱⁱ	0.937 (17)	2.08 (3)	2.762 (3)	128 (2)

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

Acknowledgements

This work was supported by the Key Project of the Natural Science Foundation of Hubei Province, China (grant No. 2008CDA067), and the Graduate Student Research Funds of South-Central University for Nationalities.

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