N′-(5-Bromo-2-methoxy­benzyl­idene)-3-hydroxy­benzohydrazide methanol hemisolvate

Zhou, Z.

doi:10.1107/S1600536808018205

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1298

doi:10.1107/S1600536808018205

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N′-(5-Bromo-2-methoxybenzylidene)-3-hydroxybenzohydrazide methanol hemisolvate

Zhi Zhou ^a ^*

^aDepartment of Chemistry, Kaili College, Kaili Guizhou 556000, People's Republic of China
^*Correspondence e-mail: zhou82zhi@126.com

(Received 13 June 2008; accepted 16 June 2008; online 19 June 2008)

The asymmetric unit of the title compound, C₁₅H₁₃BrN₂O₃·0.5CH₃OH, contains two Schiff base molecules and a methanol molecule of crystallization. The dihedral angles between the benzene rings in the two molecules are 23.8 (2) and 18.6 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For related literature, see: Zhou & Tang (2007 ); Zhou & Xiao (2007 ). For related structures, see: Ali et al. (2007 ); Butcher et al. (2007 ); He (2008 ); Jing & Yu (2007 ); Nie (2008 ).

Experimental

Crystal data

C₁₅H₁₃BrN₂O₃·0.5CH₄O
M_r = 365.21
Monoclinic, P 2₁ /n
a = 12.906 (2) Å
b = 11.177 (2) Å
c = 22.607 (3) Å
β = 93.706 (3)°
V = 3254.3 (9) Å³
Z = 8
Mo Kα radiation
μ = 2.54 mm⁻¹
T = 298 (2) K
0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.630, T_max = 0.672
21623 measured reflections
6725 independent reflections
2610 reflections with I > 2σ(I)
R_int = 0.104

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.170
S = 0.98
6725 reflections
409 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O2ⁱ	0.902 (10)	2.045 (18)	2.923 (5)	164 (5)
N2—H2⋯O7ⁱ	0.894 (10)	1.977 (13)	2.866 (5)	173 (5)
O7—H7⋯O3	0.82	1.96	2.737 (5)	157
O6—H6⋯N1ⁱⁱ	0.82	2.48	3.140 (5)	138
O6—H6⋯O2ⁱⁱ	0.82	2.06	2.777 (5)	146
O3—H3⋯N3ⁱⁱⁱ	0.82	2.64	3.110 (6)	118
O3—H3⋯O5ⁱⁱⁱ	0.82	1.92	2.692 (5)	157
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y+1, z; (iii) x+1, y, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018205/at2575sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018205/at2575Isup2.hkl

checkCIF report

Comment top

Recently, we have reported two metal complexes with Schiff base ligands (Zhou & Tang, 2007; Zhou & Xiao, 2007). We report herein the crystal structure of the title Schiff base compound (I), Fig. 1.

The asymmetric unit of (I) consists of two Schiff base molecules and a methanol molecule of crystallization. The dihedral angles are 23.8 (2) ° and 18.6 (2) °, respectively, between the benzene rings (C1-C6) and (C10-C15) for molecule A, and (C16-C21), (C25-C3015) for molecule B. All the bond values are comparable to the similar compounds (Ali et al., 2007; Nie, 2008; He, 2008; Butcher et al., 2007; Jing & Yu, 2007).

In the crystal structure, molecules are linked through intermolecular N–H···O, O–H···O and O—H···N hydrogen bonds (Table 1) to form a three-dimensional network (Fig. 2).

Related literature top

For related literature, see: Zhou & Tang (2007); Zhou & Xiao (2007). For related structures, see: Ali et al. (2007); Butcher et al. (2007); He (2008); Jing & Yu (2007); Nie (2008).

Experimental top

2-Methoxy-5-bromobenzaldehyde (1.0 mmol, 215.0 mg) and 3-hydroxybenzohydrazide (1.0 mmol, 152.1 mg) were dissolved in methanol (30 ml). The mixture was stirred at reflux for 30 min to give a colourless solution. After keeping the solution in air for a few days, colourless block-like crystals were formed.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The molecular packing of (I), viewed along the c axis. Hydrogen bonds are shown as dashed lines.

N'-(5-Bromo-2-methoxybenzylidene)-3-hydroxybenzohydrazide methanol hemisolvate top

Crystal data top

C₁₅H₁₃BrN₂O₃·0.5CH₄O	F(000) = 1480
M_r = 365.21	D_x = 1.491 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1690 reflections
a = 12.906 (2) Å	θ = 2.4–24.1°
b = 11.177 (2) Å	µ = 2.54 mm⁻¹
c = 22.607 (3) Å	T = 298 K
β = 93.706 (3)°	Block, colourless
V = 3254.3 (9) Å³	0.20 × 0.18 × 0.17 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	6725 independent reflections
Radiation source: fine-focus sealed tube	2610 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.104
ω scans	θ_max = 26.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→16
T_min = 0.630, T_max = 0.672	k = −13→14
21623 measured reflections	l = −28→27

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0522P)²] where P = (F_o² + 2F_c²)/3
6725 reflections	(Δ/σ)_max = 0.001
409 parameters	Δρ_max = 0.51 e Å⁻³
2 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₅H₁₃BrN₂O₃·0.5CH₄O	V = 3254.3 (9) Å³
M_r = 365.21	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.906 (2) Å	µ = 2.54 mm⁻¹
b = 11.177 (2) Å	T = 298 K
c = 22.607 (3) Å	0.20 × 0.18 × 0.17 mm
β = 93.706 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6725 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2610 reflections with I > 2σ(I)
T_min = 0.630, T_max = 0.672	R_int = 0.104
21623 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	2 restraints
wR(F²) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.51 e Å⁻³
6725 reflections	Δρ_min = −0.47 e Å⁻³
409 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
Br1	0.89733 (6)	−0.03746 (6)	0.19990 (3)	0.0896 (3)
Br2	−0.27606 (8)	0.47236 (11)	0.74505 (4)	0.1632 (5)
O1	0.4978 (3)	−0.1249 (3)	0.31384 (17)	0.0705 (11)
O2	0.8013 (2)	0.2809 (3)	0.44744 (14)	0.0499 (9)
O3	0.6978 (3)	0.6557 (3)	0.55948 (18)	0.0680 (11)
H3	0.7389	0.6728	0.5346	0.102*
O4	0.1231 (4)	0.3770 (4)	0.6320 (2)	0.0868 (14)
O5	−0.1758 (3)	0.7734 (3)	0.48927 (15)	0.0563 (10)
O6	−0.0715 (3)	1.1472 (3)	0.37821 (15)	0.0551 (10)
H6	−0.1226	1.1603	0.3970	0.083*
O7	0.5718 (3)	0.8519 (4)	0.5649 (3)	0.0984 (16)
H7	0.6018	0.7923	0.5537	0.148*
N1	0.6877 (3)	0.1219 (3)	0.38704 (17)	0.0435 (10)
N2	0.6465 (3)	0.1906 (4)	0.43049 (18)	0.0454 (11)
N3	−0.0639 (3)	0.6176 (4)	0.55665 (18)	0.0489 (11)
N4	−0.0209 (3)	0.6887 (4)	0.51548 (18)	0.0448 (11)
C1	0.6526 (4)	−0.0203 (5)	0.3091 (2)	0.0476 (14)
C2	0.5840 (4)	−0.1083 (5)	0.2848 (2)	0.0494 (14)
C3	0.6097 (5)	−0.1693 (5)	0.2347 (2)	0.0599 (16)
H3A	0.5641	−0.2261	0.2179	0.072*
C4	0.7018 (5)	−0.1475 (5)	0.2094 (2)	0.0623 (16)
H4	0.7181	−0.1892	0.1756	0.075*
C5	0.7690 (4)	−0.0647 (5)	0.2338 (2)	0.0532 (15)
C6	0.7453 (4)	−0.0001 (4)	0.2831 (2)	0.0466 (14)
H6A	0.7916	0.0571	0.2990	0.056*
C7	0.4258 (4)	−0.2131 (5)	0.2916 (3)	0.0795 (19)
H7A	0.4041	−0.1949	0.2512	0.119*
H7B	0.3664	−0.2133	0.3151	0.119*
H7C	0.4582	−0.2904	0.2936	0.119*
C8	0.6233 (4)	0.0517 (5)	0.3595 (2)	0.0485 (14)
H8	0.5560	0.0460	0.3717	0.058*
C9	0.7095 (4)	0.2717 (4)	0.4583 (2)	0.0403 (12)
C10	0.6619 (4)	0.3512 (4)	0.5019 (2)	0.0424 (13)
C11	0.7043 (4)	0.4646 (4)	0.5105 (2)	0.0441 (13)
H11	0.7613	0.4877	0.4901	0.053*
C12	0.6614 (4)	0.5429 (5)	0.5494 (2)	0.0475 (13)
C13	0.5772 (4)	0.5085 (5)	0.5794 (2)	0.0562 (15)
H13	0.5487	0.5610	0.6058	0.067*
C14	0.5352 (4)	0.3978 (5)	0.5707 (2)	0.0610 (16)
H14	0.4775	0.3758	0.5908	0.073*
C15	0.5772 (4)	0.3173 (5)	0.5321 (2)	0.0533 (15)
H15	0.5486	0.2414	0.5267	0.064*
C16	0.0358 (7)	0.3912 (5)	0.6599 (3)	0.075 (2)
C17	−0.0323 (5)	0.4802 (5)	0.6358 (2)	0.0563 (16)
C18	−0.1248 (5)	0.5010 (5)	0.6608 (3)	0.0716 (19)
H18	−0.1693	0.5598	0.6448	0.086*
C19	−0.1527 (7)	0.4368 (8)	0.7089 (3)	0.105 (3)
C20	−0.0841 (10)	0.3495 (9)	0.7327 (4)	0.134 (5)
H20	−0.1013	0.3062	0.7658	0.161*
C21	0.0056 (9)	0.3278 (7)	0.7085 (3)	0.116 (4)
H21	0.0491	0.2684	0.7247	0.140*
C22	0.1976 (6)	0.2885 (6)	0.6549 (3)	0.125 (3)
H22A	0.2229	0.3105	0.6942	0.187*
H22B	0.2546	0.2846	0.6297	0.187*
H22C	0.1645	0.2116	0.6559	0.187*
C23	0.0025 (4)	0.5525 (4)	0.5873 (2)	0.0501 (14)
H23	0.0719	0.5518	0.5784	0.060*
C24	−0.0810 (4)	0.7700 (4)	0.4857 (2)	0.0422 (13)
C25	−0.0264 (4)	0.8531 (4)	0.4470 (2)	0.0411 (13)
C26	−0.0762 (4)	0.9601 (4)	0.43118 (19)	0.0412 (12)
H26	−0.1412	0.9771	0.4445	0.049*
C27	−0.0283 (4)	1.0406 (5)	0.3956 (2)	0.0429 (13)
C28	0.0680 (4)	1.0164 (5)	0.3763 (2)	0.0561 (15)
H28	0.1007	1.0720	0.3532	0.067*
C29	0.1162 (4)	0.9099 (5)	0.3910 (2)	0.0577 (15)
H29	0.1806	0.8927	0.3768	0.069*
C30	0.0696 (4)	0.8282 (4)	0.4267 (2)	0.0455 (13)
H30	0.1030	0.7568	0.4370	0.055*
C31	0.6289 (6)	0.9488 (7)	0.5556 (5)	0.173 (5)
H31A	0.5889	1.0194	0.5622	0.260*
H31B	0.6491	0.9484	0.5154	0.260*
H31C	0.6898	0.9483	0.5823	0.260*
H2	0.5782 (11)	0.183 (5)	0.434 (2)	0.080*
H4A	0.0489 (9)	0.695 (5)	0.520 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1071 (6)	0.0787 (5)	0.0892 (5)	0.0026 (4)	0.0552 (4)	0.0009 (4)
Br2	0.1725 (10)	0.2271 (12)	0.0980 (7)	−0.1320 (9)	0.0695 (6)	−0.0473 (7)
O1	0.057 (3)	0.071 (3)	0.084 (3)	−0.018 (2)	0.008 (2)	−0.022 (2)
O2	0.035 (2)	0.056 (2)	0.059 (2)	0.0003 (18)	0.0038 (17)	−0.0118 (18)
O3	0.067 (3)	0.046 (2)	0.096 (3)	−0.010 (2)	0.042 (2)	−0.018 (2)
O4	0.119 (4)	0.055 (3)	0.082 (3)	0.019 (3)	−0.028 (3)	0.003 (2)
O5	0.040 (2)	0.060 (2)	0.070 (3)	0.0084 (19)	0.0117 (19)	0.0173 (19)
O6	0.061 (3)	0.046 (2)	0.060 (2)	0.0045 (19)	0.0187 (19)	0.0093 (19)
O7	0.047 (3)	0.057 (3)	0.193 (5)	−0.005 (2)	0.028 (3)	−0.036 (3)
N1	0.047 (3)	0.036 (3)	0.048 (3)	0.000 (2)	0.004 (2)	−0.008 (2)
N2	0.039 (3)	0.044 (3)	0.054 (3)	−0.006 (2)	0.012 (2)	−0.017 (2)
N3	0.049 (3)	0.046 (3)	0.052 (3)	−0.010 (2)	0.005 (2)	−0.001 (2)
N4	0.033 (3)	0.048 (3)	0.054 (3)	−0.004 (2)	0.004 (2)	0.011 (2)
C1	0.060 (4)	0.041 (3)	0.042 (3)	0.002 (3)	0.000 (3)	0.001 (3)
C2	0.055 (4)	0.041 (3)	0.051 (4)	0.007 (3)	−0.004 (3)	−0.006 (3)
C3	0.081 (5)	0.045 (4)	0.051 (4)	0.001 (3)	−0.011 (3)	−0.006 (3)
C4	0.094 (5)	0.046 (4)	0.047 (4)	0.002 (4)	0.012 (3)	−0.009 (3)
C5	0.073 (4)	0.043 (4)	0.046 (3)	0.000 (3)	0.019 (3)	0.005 (3)
C6	0.054 (4)	0.036 (3)	0.050 (3)	−0.002 (3)	0.002 (3)	0.002 (3)
C7	0.056 (4)	0.071 (4)	0.110 (5)	−0.014 (4)	−0.009 (4)	0.000 (4)
C8	0.045 (3)	0.049 (4)	0.053 (3)	−0.001 (3)	0.014 (3)	−0.004 (3)
C9	0.041 (3)	0.036 (3)	0.044 (3)	0.002 (3)	0.004 (3)	0.001 (3)
C10	0.038 (3)	0.042 (3)	0.047 (3)	0.002 (3)	0.004 (2)	−0.005 (3)
C11	0.034 (3)	0.045 (3)	0.054 (3)	0.000 (3)	0.011 (2)	−0.004 (3)
C12	0.042 (3)	0.043 (3)	0.059 (3)	−0.002 (3)	0.015 (3)	−0.007 (3)
C13	0.064 (4)	0.050 (4)	0.058 (4)	−0.003 (3)	0.025 (3)	−0.018 (3)
C14	0.064 (4)	0.065 (4)	0.057 (4)	−0.011 (3)	0.028 (3)	−0.013 (3)
C15	0.059 (4)	0.049 (4)	0.053 (4)	−0.020 (3)	0.013 (3)	−0.011 (3)
C16	0.134 (7)	0.033 (4)	0.055 (5)	−0.025 (4)	−0.021 (5)	0.008 (3)
C17	0.075 (4)	0.049 (4)	0.044 (4)	−0.025 (3)	−0.002 (3)	0.003 (3)
C18	0.096 (5)	0.069 (5)	0.048 (4)	−0.043 (4)	−0.002 (4)	−0.001 (3)
C19	0.151 (8)	0.114 (7)	0.050 (5)	−0.074 (6)	0.016 (5)	−0.008 (5)
C20	0.235 (15)	0.115 (9)	0.052 (6)	−0.108 (10)	0.002 (7)	0.018 (5)
C21	0.219 (12)	0.061 (5)	0.063 (6)	−0.039 (7)	−0.034 (6)	0.020 (5)
C22	0.175 (8)	0.067 (5)	0.120 (6)	0.046 (5)	−0.082 (6)	−0.020 (4)
C23	0.054 (4)	0.042 (3)	0.054 (4)	−0.001 (3)	0.002 (3)	0.001 (3)
C24	0.038 (3)	0.041 (3)	0.047 (3)	−0.001 (3)	0.001 (3)	−0.004 (3)
C25	0.040 (3)	0.042 (3)	0.041 (3)	−0.006 (3)	0.002 (2)	−0.001 (3)
C26	0.040 (3)	0.048 (3)	0.035 (3)	0.000 (3)	0.000 (2)	−0.003 (3)
C27	0.050 (3)	0.038 (3)	0.042 (3)	0.002 (3)	0.005 (3)	−0.002 (3)
C28	0.051 (4)	0.057 (4)	0.062 (4)	−0.004 (3)	0.018 (3)	0.010 (3)
C29	0.043 (3)	0.061 (4)	0.071 (4)	0.003 (3)	0.022 (3)	0.005 (3)
C30	0.038 (3)	0.046 (3)	0.052 (3)	0.009 (3)	0.005 (3)	0.000 (3)
C31	0.093 (6)	0.077 (6)	0.357 (15)	−0.022 (5)	0.076 (8)	−0.013 (8)

Geometric parameters (Å, º) top

Br1—C5	1.893 (5)	C10—C11	1.389 (6)
Br2—C19	1.879 (9)	C11—C12	1.382 (6)
O1—C2	1.342 (6)	C11—H11	0.9300
O1—C7	1.423 (6)	C12—C13	1.372 (7)
O2—C9	1.230 (5)	C13—C14	1.360 (7)
O3—C12	1.360 (5)	C13—H13	0.9300
O3—H3	0.8200	C14—C15	1.387 (7)
O4—C16	1.336 (8)	C14—H14	0.9300
O4—C22	1.452 (6)	C15—H15	0.9300
O5—C24	1.233 (5)	C16—C21	1.384 (9)
O6—C27	1.363 (5)	C16—C17	1.413 (8)
O6—H6	0.8200	C17—C18	1.374 (8)
O7—C31	1.335 (7)	C17—C23	1.456 (7)
O7—H7	0.8200	C18—C19	1.370 (9)
N1—C8	1.276 (5)	C18—H18	0.9300
N1—N2	1.379 (5)	C19—C20	1.401 (12)
N2—C9	1.346 (6)	C20—C21	1.335 (12)
N2—H2	0.894 (10)	C20—H20	0.9300
N3—C23	1.290 (6)	C21—H21	0.9300
N3—N4	1.369 (5)	C22—H22A	0.9600
N4—C24	1.347 (6)	C22—H22B	0.9600
N4—H4A	0.902 (10)	C22—H22C	0.9600
C1—C6	1.384 (7)	C23—H23	0.9300
C1—C2	1.411 (7)	C24—C25	1.484 (6)
C1—C8	1.465 (7)	C25—C30	1.377 (6)
C2—C3	1.380 (7)	C25—C26	1.393 (6)
C3—C4	1.374 (7)	C26—C27	1.380 (6)
C3—H3A	0.9300	C26—H26	0.9300
C4—C5	1.361 (7)	C27—C28	1.371 (7)
C4—H4	0.9300	C28—C29	1.374 (7)
C5—C6	1.380 (7)	C28—H28	0.9300
C6—H6A	0.9300	C29—C30	1.382 (6)
C7—H7A	0.9600	C29—H29	0.9300
C7—H7B	0.9600	C30—H30	0.9300
C7—H7C	0.9600	C31—H31A	0.9600
C8—H8	0.9300	C31—H31B	0.9600
C9—C10	1.489 (6)	C31—H31C	0.9600
C10—C15	1.379 (6)

C2—O1—C7	117.8 (4)	C10—C15—C14	119.2 (5)
C12—O3—H3	109.5	C10—C15—H15	120.4
C16—O4—C22	118.1 (6)	C14—C15—H15	120.4
C27—O6—H6	109.5	O4—C16—C21	127.1 (8)
C31—O7—H7	109.5	O4—C16—C17	115.0 (6)
C8—N1—N2	114.9 (4)	C21—C16—C17	117.8 (8)
C9—N2—N1	117.3 (4)	C18—C17—C16	119.7 (6)
C9—N2—H2	126 (3)	C18—C17—C23	122.3 (6)
N1—N2—H2	116 (3)	C16—C17—C23	117.9 (6)
C23—N3—N4	114.1 (4)	C19—C18—C17	121.2 (7)
C24—N4—N3	119.1 (4)	C19—C18—H18	119.4
C24—N4—H4A	123 (3)	C17—C18—H18	119.4
N3—N4—H4A	115 (3)	C18—C19—C20	118.5 (9)
C6—C1—C2	119.1 (5)	C18—C19—Br2	120.6 (8)
C6—C1—C8	120.9 (5)	C20—C19—Br2	120.8 (7)
C2—C1—C8	119.9 (5)	C21—C20—C19	120.8 (9)
O1—C2—C3	125.8 (5)	C21—C20—H20	119.6
O1—C2—C1	115.2 (5)	C19—C20—H20	119.6
C3—C2—C1	119.1 (5)	C20—C21—C16	121.9 (10)
C4—C3—C2	120.9 (5)	C20—C21—H21	119.0
C4—C3—H3A	119.5	C16—C21—H21	119.0
C2—C3—H3A	119.5	O4—C22—H22A	109.5
C5—C4—C3	119.9 (5)	O4—C22—H22B	109.5
C5—C4—H4	120.1	H22A—C22—H22B	109.5
C3—C4—H4	120.1	O4—C22—H22C	109.5
C4—C5—C6	121.0 (5)	H22A—C22—H22C	109.5
C4—C5—Br1	119.8 (4)	H22B—C22—H22C	109.5
C6—C5—Br1	119.2 (4)	N3—C23—C17	119.4 (5)
C5—C6—C1	120.0 (5)	N3—C23—H23	120.3
C5—C6—H6A	120.0	C17—C23—H23	120.3
C1—C6—H6A	120.0	O5—C24—N4	122.0 (5)
O1—C7—H7A	109.5	O5—C24—C25	122.1 (5)
O1—C7—H7B	109.5	N4—C24—C25	116.0 (5)
H7A—C7—H7B	109.5	C30—C25—C26	119.9 (5)
O1—C7—H7C	109.5	C30—C25—C24	122.8 (5)
H7A—C7—H7C	109.5	C26—C25—C24	117.4 (4)
H7B—C7—H7C	109.5	C27—C26—C25	119.6 (5)
N1—C8—C1	121.7 (5)	C27—C26—H26	120.2
N1—C8—H8	119.2	C25—C26—H26	120.2
C1—C8—H8	119.2	O6—C27—C28	116.3 (5)
O2—C9—N2	121.6 (5)	O6—C27—C26	123.3 (5)
O2—C9—C10	121.7 (5)	C28—C27—C26	120.4 (5)
N2—C9—C10	116.7 (4)	C27—C28—C29	120.0 (5)
C15—C10—C11	119.9 (4)	C27—C28—H28	120.0
C15—C10—C9	122.5 (5)	C29—C28—H28	120.0
C11—C10—C9	117.5 (4)	C28—C29—C30	120.4 (5)
C12—C11—C10	119.8 (5)	C28—C29—H29	119.8
C12—C11—H11	120.1	C30—C29—H29	119.8
C10—C11—H11	120.1	C25—C30—C29	119.7 (5)
O3—C12—C13	117.0 (5)	C25—C30—H30	120.1
O3—C12—C11	123.1 (5)	C29—C30—H30	120.1
C13—C12—C11	119.9 (5)	O7—C31—H31A	109.5
C14—C13—C12	120.3 (5)	O7—C31—H31B	109.5
C14—C13—H13	119.8	H31A—C31—H31B	109.5
C12—C13—H13	119.8	O7—C31—H31C	109.5
C13—C14—C15	120.8 (5)	H31A—C31—H31C	109.5
C13—C14—H14	119.6	H31B—C31—H31C	109.5
C15—C14—H14	119.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2ⁱ	0.90 (1)	2.05 (2)	2.923 (5)	164 (5)
N2—H2···O7ⁱ	0.89 (1)	1.98 (1)	2.866 (5)	173 (5)
O7—H7···O3	0.82	1.96	2.737 (5)	157
O6—H6···N1ⁱⁱ	0.82	2.48	3.140 (5)	138
O6—H6···O2ⁱⁱ	0.82	2.06	2.777 (5)	146
O3—H3···N3ⁱⁱⁱ	0.82	2.64	3.110 (6)	118
O3—H3···O5ⁱⁱⁱ	0.82	1.92	2.692 (5)	157

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃BrN₂O₃·0.5CH₄O
M_r	365.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	12.906 (2), 11.177 (2), 22.607 (3)
β (°)	93.706 (3)
V (Å³)	3254.3 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.54
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.630, 0.672
No. of measured, independent and observed [I > 2σ(I)] reflections	21623, 6725, 2610
R_int	0.104
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.170, 0.98
No. of reflections	6725
No. of parameters	409
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.47

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2ⁱ	0.902 (10)	2.045 (18)	2.923 (5)	164 (5)
N2—H2···O7ⁱ	0.894 (10)	1.977 (13)	2.866 (5)	173 (5)
O7—H7···O3	0.82	1.96	2.737 (5)	156.8
O6—H6···N1ⁱⁱ	0.82	2.48	3.140 (5)	138.0
O6—H6···O2ⁱⁱ	0.82	2.06	2.777 (5)	146.4
O3—H3···N3ⁱⁱⁱ	0.82	2.64	3.110 (6)	118.4
O3—H3···O5ⁱⁱⁱ	0.82	1.92	2.692 (5)	157.4

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

Acknowledgements

The author thanks Kaili College for financial support.

References

Ali, H. M., Zuraini, K., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1729–o1730. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Butcher, R. J., Jasinski, J. P., Narayana, B., Sunil, K. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3652. Web of Science CSD CrossRef IUCr Journals Google Scholar
He, L. (2008). Acta Cryst. E64, o82. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jing, Z.-L. & Yu, M. (2007). Acta Cryst. E63, o509–o510. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nie, Y. (2008). Acta Cryst. E64, o471. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Zhou, Z. & Xiao, Z.-H. (2007). Acta Cryst. E63, m2012. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 7| July 2008| Page o1298

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-(5-Bromo-2-meth­oxy­benzyl­­idene)-3-hy­droxy­benzohydrazide methanol hemisolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-(5-Bromo-2-methoxybenzylidene)-3-hydroxybenzohydrazide methanol hemisolvate