(E)-Ethyl N′-(2-hydroxy­benzyl­idene)­hydrazinecarboxyl­ate

Gao, B.

doi:10.1107/S1600536808022307

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1547

doi:10.1107/S1600536808022307

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(E)-Ethyl N′-(2-hydroxybenzylidene)hydrazinecarboxylate

Bo Gao ^a ^*

^aMarine College, Zhejiang Institute of Communications, Hangzhou 311112, People's Republic of China
^*Correspondence e-mail: bgao_zjvtit@126.com

(Received 14 July 2008; accepted 16 July 2008; online 19 July 2008)

There are two molecules in the asymmetric unit of the title compound, C₁₀H₁₂N₂O₃, with identical conformations. Each independent molecule is approximately planar and adopts a trans configuration with respect to the C=N double bond. Intramolecular O—H⋯N hydrogen bonds are observed in both molecules. The molecules are linked into a ribbon-like structure running along the b axis by intermolecular N—H⋯O and C—H⋯O hydrogen bonds. The ribbons are arranged into layers parallel to ( $[\overline{3}]$ 02).

Related literature

For the properties of benzaldehyde hydrazone derivatives, see: Parashar et al. (1988 ); Hadjoudis et al. (1987 ); Borg et al. (1999 ). For a related structure, see: Shang et al. (2007 ).

Experimental

Crystal data

C₁₀H₁₂N₂O₃
M_r = 208.12
Monoclinic, P 2₁ /c
a = 11.535 (11) Å
b = 22.05 (2) Å
c = 9.005 (9) Å
β = 111.669 (14)°
V = 2129 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 (2) K
0.27 × 0.24 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.973, T_max = 0.978
14192 measured reflections
3713 independent reflections
1445 reflections with I > 2σ(I)
R_int = 0.146

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.150
S = 0.78
3713 reflections
274 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.573 (3)	147
N2—H2A⋯O4ⁱ	0.86	2.13	2.979 (4)	170
O4—H4A⋯N3	0.82	1.86	2.586 (3)	146
N4—H6⋯O2ⁱⁱ	0.86	2.08	2.931 (4)	170
C5—H5⋯O5ⁱ	0.95	2.27	3.184 (4)	161
C15—H15⋯O1ⁱⁱ	0.95	2.46	3.371 (5)	161
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+1.

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/S1600536808022307/ci2635sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022307/ci2635Isup2.hkl

checkCIF report

Comment top

Benzaldehydehydrazone derivatives have received considerable attention for a long time due to their pharmacological activity (Parashar et al., 1988) and photochromic properties (Hadjoudis et al., 1987). They are important intermediates for 1,3,4-oxadiazoles, which have been reported to be versatile compounds with many properties (Borg et al., 1999). We report here the crystal structure of the title compound.

The asymmetric unit of the title compound contains two independent but essentially identical molecules (Fig. 1). The corresponding bond lengths and angles of the two independent molecules agree with each other and are comparable to those observed for N'-(4-methoxybenzylidene)methoxyformohydrazide (Shang et al., 2007). Each independent molecule is approximately planar and adopts a trans configuration with respect to the C═N bond. The dihedral angle between C1-C6 and O2/O3/N1/N2/C7-C10 planes is 7.6 (1)° and that between C11-C16 and O5/O6/N3/N4/C17-C20 planes is 5.5 (1)°. In both independent molecules intramolecular O—H···N hydrogen bonds are observed.

The molecules are linked into a ribbon-like structure running along the b axis by intermolecular N—H···O and C—H···O hydrogen bonds. (Fig.2). The ribbons are arranged into layers parallel to the (3 0 2) plane.

Related literature top

For the properties of benzaldehyde hydrazone derivatives, see: Parashar et al. (1988); Hadjoudis et al. (1987); Borg et al. (1999). For a related structure, see: Shang et al. (2007).

Experimental top

2-Hydroxybenzaldehyde (1.22 g, 0.01 mol) and ethyl hydrazinecarboxylate (1.04 g, 0.01 mol) were dissolved in methanol (25 ml) and left for 3 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 85% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution at room temperature (m.p. 455–457 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 30% probability level. O—H···N hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of the title compound, viewed approximately down the a axis. Dashed lines indicate hydrogen bonds.

(E)-Ethyl N'-(2-hydroxybenzylidene)hydrazinecarboxylate top

Crystal data top

C₁₀H₁₂N₂O₃	F(000) = 880
M_r = 208.12	D_x = 1.299 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3713 reflections
a = 11.535 (11) Å	θ = 1.9–25.0°
b = 22.05 (2) Å	µ = 0.10 mm⁻¹
c = 9.005 (9) Å	T = 273 K
β = 111.669 (14)°	Block, colourless
V = 2129 (4) Å³	0.27 × 0.24 × 0.23 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3713 independent reflections
Radiation source: fine-focus sealed tube	1445 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.146
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −13→12
T_min = 0.973, T_max = 0.978	k = −26→25
14192 measured reflections	l = −10→10

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)] = 0.058	H-atom parameters constrained
wR(F²) = 0.150	w = 1/[σ²(F_o²) + (0.0618P)²] where P = (F_o² + 2F_c²)/3
S = 0.78	(Δ/σ)_max = 0.001
3713 reflections	Δρ_max = 0.30 e Å⁻³
274 parameters	Δρ_min = −0.16 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: 0.0017 (5)

Crystal data top

C₁₀H₁₂N₂O₃	V = 2129 (4) Å³
M_r = 208.12	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.535 (11) Å	µ = 0.10 mm⁻¹
b = 22.05 (2) Å	T = 273 K
c = 9.005 (9) Å	0.27 × 0.24 × 0.23 mm
β = 111.669 (14)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3713 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1445 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.978	R_int = 0.146
14192 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 0.78	Δρ_max = 0.30 e Å⁻³
3713 reflections	Δρ_min = −0.16 e Å⁻³
274 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	0.6761 (2)	−0.00597 (8)	0.5564 (3)	0.1012 (8)
H1	0.6249	0.0071	0.4725	0.121*
O2	0.43571 (18)	−0.01273 (8)	0.1327 (2)	0.0799 (7)
O3	0.32487 (19)	0.06261 (8)	−0.0314 (2)	0.0781 (7)
N1	0.5648 (2)	0.07322 (10)	0.3410 (3)	0.0661 (7)
N2	0.4749 (2)	0.08742 (10)	0.1969 (3)	0.0740 (8)
H2A	0.4578	0.1246	0.1679	0.089*
C1	0.7458 (3)	0.04071 (13)	0.6420 (4)	0.0744 (10)
C2	0.8384 (3)	0.02856 (15)	0.7861 (4)	0.0988 (12)
H2	0.8519	−0.0121	0.8237	0.119*
C3	0.9126 (3)	0.07430 (16)	0.8778 (4)	0.1005 (12)
H3	0.9765	0.0650	0.9775	0.121*
C4	0.8937 (3)	0.13398 (15)	0.8240 (4)	0.0933 (11)
H4	0.9443	0.1658	0.8859	0.112*
C5	0.8007 (3)	0.14600 (14)	0.6797 (4)	0.0804 (10)
H5	0.7871	0.1868	0.6438	0.096*
C6	0.7250 (3)	0.10084 (12)	0.5834 (3)	0.0635 (8)
C7	0.6293 (3)	0.11571 (12)	0.4328 (3)	0.0669 (9)
H7A	0.6135	0.1569	0.4007	0.080*
C8	0.4133 (3)	0.04080 (14)	0.1007 (4)	0.0676 (9)
C9	0.2552 (3)	0.01839 (14)	−0.1492 (4)	0.0839 (11)
H9A	0.2072	−0.0083	−0.1044	0.101*
H9B	0.3129	−0.0071	−0.1809	0.101*
C10	0.1687 (3)	0.05187 (14)	−0.2907 (4)	0.0954 (11)
H10A	0.1209	0.0228	−0.3728	0.143*
H10B	0.2171	0.0783	−0.3338	0.143*
H10C	0.1113	0.0765	−0.2584	0.143*
O4	0.44788 (19)	0.28071 (8)	0.6198 (2)	0.0858 (7)
H4A	0.4920	0.2570	0.6873	0.103*
O5	0.7029 (2)	0.23103 (9)	0.9891 (3)	0.0972 (8)
O6	0.75313 (19)	0.14080 (8)	1.1180 (2)	0.0784 (7)
N3	0.5222 (2)	0.17646 (9)	0.7524 (3)	0.0661 (7)
N4	0.5985 (2)	0.14460 (10)	0.8822 (3)	0.0722 (8)
H6	0.5909	0.1061	0.8907	0.087*
C11	0.3641 (3)	0.24868 (13)	0.4965 (4)	0.0665 (9)
C12	0.2807 (3)	0.28054 (13)	0.3700 (4)	0.0814 (10)
H12	0.2822	0.3236	0.3710	0.098*
C13	0.1953 (3)	0.25032 (15)	0.2422 (4)	0.0898 (11)
H13	0.1383	0.2728	0.1561	0.108*
C14	0.1915 (3)	0.18688 (15)	0.2380 (4)	0.0929 (11)
H14	0.1337	0.1660	0.1492	0.111*
C15	0.2741 (3)	0.15531 (14)	0.3664 (4)	0.0786 (10)
H15	0.2715	0.1122	0.3647	0.094*
C16	0.3610 (3)	0.18441 (12)	0.4981 (3)	0.0623 (8)
C17	0.4436 (3)	0.14927 (13)	0.6327 (3)	0.0638 (8)
H17	0.4389	0.1063	0.6311	0.077*
C18	0.6864 (3)	0.17732 (15)	0.9965 (4)	0.0728 (9)
C19	0.8531 (3)	0.17077 (14)	1.2461 (4)	0.0906 (11)
H19A	0.8180	0.1976	1.3072	0.109*
H19B	0.9037	0.1958	1.2014	0.109*
C20	0.9322 (3)	0.12260 (14)	1.3527 (4)	0.1046 (12)
H20A	0.9974	0.1416	1.4441	0.157*
H20B	0.9710	0.0981	1.2928	0.157*
H20C	0.8802	0.0966	1.3909	0.157*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.141 (2)	0.0421 (13)	0.0963 (17)	0.0008 (13)	0.0154 (15)	0.0104 (12)
O2	0.0980 (16)	0.0357 (11)	0.0895 (16)	0.0003 (11)	0.0154 (13)	0.0015 (10)
O3	0.0861 (15)	0.0492 (12)	0.0760 (15)	0.0038 (11)	0.0029 (13)	−0.0049 (11)
N1	0.0828 (18)	0.0437 (14)	0.0631 (17)	0.0054 (13)	0.0167 (15)	−0.0015 (12)
N2	0.0922 (19)	0.0389 (14)	0.0692 (18)	0.0031 (13)	0.0045 (16)	−0.0030 (13)
C1	0.097 (3)	0.049 (2)	0.070 (2)	0.0103 (18)	0.022 (2)	0.0070 (17)
C2	0.121 (3)	0.062 (2)	0.092 (3)	0.023 (2)	0.014 (3)	0.023 (2)
C3	0.103 (3)	0.093 (3)	0.078 (3)	0.023 (2)	0.001 (2)	0.012 (2)
C4	0.100 (3)	0.071 (2)	0.085 (3)	0.004 (2)	0.007 (2)	0.000 (2)
C5	0.092 (2)	0.0501 (19)	0.077 (2)	0.0031 (18)	0.005 (2)	0.0025 (17)
C6	0.073 (2)	0.0487 (18)	0.063 (2)	0.0105 (16)	0.0182 (18)	0.0068 (16)
C7	0.084 (2)	0.0419 (17)	0.065 (2)	0.0046 (16)	0.0151 (18)	−0.0006 (15)
C8	0.078 (2)	0.051 (2)	0.068 (2)	0.0029 (18)	0.0194 (19)	−0.0028 (17)
C9	0.090 (2)	0.062 (2)	0.081 (3)	−0.0088 (18)	0.009 (2)	−0.0169 (18)
C10	0.102 (3)	0.084 (2)	0.076 (2)	0.000 (2)	0.005 (2)	0.0031 (19)
O4	0.1091 (17)	0.0377 (11)	0.0897 (16)	−0.0034 (11)	0.0121 (14)	0.0022 (11)
O5	0.128 (2)	0.0383 (13)	0.0981 (17)	−0.0128 (12)	0.0095 (15)	−0.0045 (11)
O6	0.0879 (16)	0.0554 (13)	0.0721 (15)	−0.0046 (11)	0.0062 (13)	0.0023 (11)
N3	0.0805 (18)	0.0402 (14)	0.0678 (17)	0.0020 (13)	0.0159 (15)	0.0016 (13)
N4	0.0864 (19)	0.0336 (13)	0.0771 (18)	−0.0030 (13)	0.0075 (16)	0.0018 (13)
C11	0.081 (2)	0.0425 (18)	0.072 (2)	−0.0037 (16)	0.0228 (19)	−0.0017 (16)
C12	0.095 (3)	0.0512 (19)	0.089 (3)	0.0076 (19)	0.023 (2)	0.0140 (19)
C13	0.101 (3)	0.068 (2)	0.083 (3)	0.004 (2)	0.014 (2)	0.018 (2)
C14	0.099 (3)	0.070 (2)	0.088 (3)	−0.006 (2)	0.009 (2)	0.008 (2)
C15	0.091 (2)	0.0497 (18)	0.079 (2)	−0.0087 (18)	0.012 (2)	−0.0058 (18)
C16	0.070 (2)	0.0446 (17)	0.070 (2)	0.0015 (15)	0.0234 (18)	0.0022 (15)
C17	0.073 (2)	0.0402 (16)	0.072 (2)	0.0004 (16)	0.0197 (18)	0.0004 (16)
C18	0.082 (2)	0.055 (2)	0.069 (2)	0.0013 (19)	0.015 (2)	−0.0019 (18)
C19	0.097 (3)	0.075 (2)	0.079 (2)	−0.008 (2)	0.008 (2)	0.0001 (19)
C20	0.103 (3)	0.096 (3)	0.092 (3)	0.000 (2)	0.010 (2)	0.010 (2)

Geometric parameters (Å, º) top

O1—C1	1.358 (3)	O4—C11	1.369 (3)
O1—H1	0.82	O4—H4A	0.82
O2—C8	1.220 (3)	O5—C18	1.205 (3)
O3—C8	1.338 (3)	O6—C18	1.348 (3)
O3—C9	1.447 (3)	O6—C19	1.454 (3)
N1—C7	1.289 (3)	N3—C17	1.274 (3)
N1—N2	1.365 (3)	N3—N4	1.369 (3)
N2—C8	1.363 (3)	N4—C18	1.355 (3)
N2—H2A	0.86	N4—H6	0.86
C1—C2	1.368 (4)	C11—C12	1.381 (4)
C1—C6	1.414 (4)	C11—C16	1.418 (4)
C2—C3	1.382 (4)	C12—C13	1.379 (4)
C2—H2	0.95	C12—H12	0.95
C3—C4	1.391 (4)	C13—C14	1.400 (4)
C3—H3	0.95	C13—H13	0.95
C4—C5	1.371 (4)	C14—C15	1.384 (4)
C4—H4	0.95	C14—H14	0.95
C5—C6	1.395 (4)	C15—C16	1.395 (4)
C5—H5	0.95	C15—H15	0.95
C6—C7	1.436 (4)	C16—C17	1.458 (4)
C7—H7A	0.95	C17—H17	0.95
C9—C10	1.491 (4)	C19—C20	1.495 (4)
C9—H9A	0.99	C19—H19A	0.99
C9—H9B	0.99	C19—H19B	0.99
C10—H10A	0.98	C20—H20A	0.98
C10—H10B	0.98	C20—H20B	0.98
C10—H10C	0.98	C20—H20C	0.98

C1—O1—H1	109.4	C11—O4—H4A	109.4
C8—O3—C9	116.4 (2)	C18—O6—C19	114.9 (2)
C7—N1—N2	119.9 (2)	C17—N3—N4	120.9 (2)
C8—N2—N1	117.8 (2)	C18—N4—N3	116.1 (2)
C8—N2—H2A	121.2	C18—N4—H6	122.0
N1—N2—H2A	121.0	N3—N4—H6	121.9
O1—C1—C2	118.8 (3)	O4—C11—C12	118.4 (3)
O1—C1—C6	121.0 (3)	O4—C11—C16	121.4 (3)
C2—C1—C6	120.2 (3)	C12—C11—C16	120.3 (3)
C1—C2—C3	121.2 (3)	C13—C12—C11	120.5 (3)
C1—C2—H2	119.4	C13—C12—H12	119.7
C3—C2—H2	119.4	C11—C12—H12	119.7
C2—C3—C4	120.0 (3)	C12—C13—C14	120.7 (3)
C2—C3—H3	120.0	C12—C13—H13	119.6
C4—C3—H3	120.0	C14—C13—H13	119.6
C5—C4—C3	118.7 (3)	C15—C14—C13	118.4 (3)
C5—C4—H4	120.7	C15—C14—H14	120.8
C3—C4—H4	120.7	C13—C14—H14	120.8
C4—C5—C6	122.8 (3)	C14—C15—C16	122.4 (3)
C4—C5—H5	118.6	C14—C15—H15	118.8
C6—C5—H5	118.6	C16—C15—H15	118.8
C5—C6—C1	117.1 (3)	C15—C16—C11	117.6 (3)
C5—C6—C7	120.7 (3)	C15—C16—C17	120.4 (3)
C1—C6—C7	122.1 (3)	C11—C16—C17	121.9 (3)
N1—C7—C6	120.0 (3)	N3—C17—C16	119.8 (3)
N1—C7—H7A	120.0	N3—C17—H17	120.1
C6—C7—H7A	120.0	C16—C17—H17	120.1
O2—C8—O3	125.7 (3)	O5—C18—O6	125.3 (3)
O2—C8—N2	124.3 (3)	O5—C18—N4	124.8 (3)
O3—C8—N2	110.0 (3)	O6—C18—N4	110.0 (3)
O3—C9—C10	107.9 (3)	O6—C19—C20	107.7 (3)
O3—C9—H9A	110.1	O6—C19—H19A	110.2
C10—C9—H9A	110.1	C20—C19—H19A	110.2
O3—C9—H9B	110.1	O6—C19—H19B	110.2
C10—C9—H9B	110.1	C20—C19—H19B	110.2
H9A—C9—H9B	108.4	H19A—C19—H19B	108.5
C9—C10—H10A	109.5	C19—C20—H20A	109.5
C9—C10—H10B	109.5	C19—C20—H20B	109.5
H10A—C10—H10B	109.5	H20A—C20—H20B	109.5
C9—C10—H10C	109.5	C19—C20—H20C	109.5
H10A—C10—H10C	109.5	H20A—C20—H20C	109.5
H10B—C10—H10C	109.5	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.573 (3)	147
N2—H2A···O4ⁱ	0.86	2.13	2.979 (4)	170
O4—H4A···N3	0.82	1.86	2.586 (3)	146
N4—H6···O2ⁱⁱ	0.86	2.08	2.931 (4)	170
C5—H5···O5ⁱ	0.95	2.27	3.184 (4)	161
C15—H15···O1ⁱⁱ	0.95	2.46	3.371 (5)	161

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂N₂O₃
M_r	208.12
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	11.535 (11), 22.05 (2), 9.005 (9)
β (°)	111.669 (14)
V (Å³)	2129 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.27 × 0.24 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.973, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	14192, 3713, 1445
R_int	0.146
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.150, 0.78
No. of reflections	3713
No. of parameters	274
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.16

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
O1—H1···N1	0.82	1.85	2.573 (3)	147
N2—H2A···O4ⁱ	0.86	2.13	2.979 (4)	170
O4—H4A···N3	0.82	1.86	2.586 (3)	146
N4—H6···O2ⁱⁱ	0.86	2.08	2.931 (4)	170
C5—H5···O5ⁱ	0.95	2.27	3.184 (4)	161
C15—H15···O1ⁱⁱ	0.95	2.46	3.371 (5)	161

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

Acknowledgements

The author acknowledges financial support from Zhejiang Institute of Communications, China.

References

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