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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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, Z. & Tang, R.-R. (2007). Acta Cryst. E63, m2960.]); Zhou & Xiao (2007[Zhou, Z. & Xiao, Z.-H. (2007). Acta Cryst. E63, m2012.]). For related structures, see: Ali et al. (2007[Ali, H. M., Zuraini, K., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1729-o1730.]); Butcher et al. (2007[Butcher, R. J., Jasinski, J. P., Narayana, B., Sunil, K. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3652.]); He (2008[He, L. (2008). Acta Cryst. E64, o82.]); Jing & Yu (2007[Jing, Z.-L. & Yu, M. (2007). Acta Cryst. E63, o509-o510.]); Nie (2008[Nie, Y. (2008). Acta Cryst. E64, o471.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13BrN2O3·0.5CH4O

  • Mr = 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[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.630, Tmax = 0.672

  • 21623 measured reflections

  • 6725 independent reflections

  • 2610 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.51 e Å−3

  • Δρmin = −0.47 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

H2 and H4A were located in a difference Fourier map and refined isotropically, with Uiso fixed at 0.08 Å2. Other H atoms were positioned geometrically and refined using a riding model with d(O–H) = 0.82 Å, Uiso = 1.5Ueq(O), and d(C–H) = 0.93 - 0.96 Å, Uiso = 1.2 or 1.5Ueq(C).

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
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] 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
C15H13BrN2O3·0.5CH4OF(000) = 1480
Mr = 365.21Dx = 1.491 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1690 reflections
a = 12.906 (2) Åθ = 2.4–24.1°
b = 11.177 (2) ŵ = 2.54 mm1
c = 22.607 (3) ÅT = 298 K
β = 93.706 (3)°Block, colourless
V = 3254.3 (9) Å30.20 × 0.18 × 0.17 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
6725 independent reflections
Radiation source: fine-focus sealed tube2610 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.104
ω scansθmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1616
Tmin = 0.630, Tmax = 0.672k = 1314
21623 measured reflectionsl = 2827
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.0522P)2]
where P = (Fo2 + 2Fc2)/3
6725 reflections(Δ/σ)max = 0.001
409 parametersΔρmax = 0.51 e Å3
2 restraintsΔρmin = 0.47 e Å3
Crystal data top
C15H13BrN2O3·0.5CH4OV = 3254.3 (9) Å3
Mr = 365.21Z = 8
Monoclinic, P21/nMo Kα radiation
a = 12.906 (2) ŵ = 2.54 mm1
b = 11.177 (2) ÅT = 298 K
c = 22.607 (3) Å0.20 × 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)
Tmin = 0.630, Tmax = 0.672Rint = 0.104
21623 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0612 restraints
wR(F2) = 0.170H atoms treated by a mixture of independent and constrained refinement
S = 0.98Δρmax = 0.51 e Å3
6725 reflectionsΔρmin = 0.47 e Å3
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
xyzUiso*/Ueq
Br10.89733 (6)0.03746 (6)0.19990 (3)0.0896 (3)
Br20.27606 (8)0.47236 (11)0.74505 (4)0.1632 (5)
O10.4978 (3)0.1249 (3)0.31384 (17)0.0705 (11)
O20.8013 (2)0.2809 (3)0.44744 (14)0.0499 (9)
O30.6978 (3)0.6557 (3)0.55948 (18)0.0680 (11)
H30.73890.67280.53460.102*
O40.1231 (4)0.3770 (4)0.6320 (2)0.0868 (14)
O50.1758 (3)0.7734 (3)0.48927 (15)0.0563 (10)
O60.0715 (3)1.1472 (3)0.37821 (15)0.0551 (10)
H60.12261.16030.39700.083*
O70.5718 (3)0.8519 (4)0.5649 (3)0.0984 (16)
H70.60180.79230.55370.148*
N10.6877 (3)0.1219 (3)0.38704 (17)0.0435 (10)
N20.6465 (3)0.1906 (4)0.43049 (18)0.0454 (11)
N30.0639 (3)0.6176 (4)0.55665 (18)0.0489 (11)
N40.0209 (3)0.6887 (4)0.51548 (18)0.0448 (11)
C10.6526 (4)0.0203 (5)0.3091 (2)0.0476 (14)
C20.5840 (4)0.1083 (5)0.2848 (2)0.0494 (14)
C30.6097 (5)0.1693 (5)0.2347 (2)0.0599 (16)
H3A0.56410.22610.21790.072*
C40.7018 (5)0.1475 (5)0.2094 (2)0.0623 (16)
H40.71810.18920.17560.075*
C50.7690 (4)0.0647 (5)0.2338 (2)0.0532 (15)
C60.7453 (4)0.0001 (4)0.2831 (2)0.0466 (14)
H6A0.79160.05710.29900.056*
C70.4258 (4)0.2131 (5)0.2916 (3)0.0795 (19)
H7A0.40410.19490.25120.119*
H7B0.36640.21330.31510.119*
H7C0.45820.29040.29360.119*
C80.6233 (4)0.0517 (5)0.3595 (2)0.0485 (14)
H80.55600.04600.37170.058*
C90.7095 (4)0.2717 (4)0.4583 (2)0.0403 (12)
C100.6619 (4)0.3512 (4)0.5019 (2)0.0424 (13)
C110.7043 (4)0.4646 (4)0.5105 (2)0.0441 (13)
H110.76130.48770.49010.053*
C120.6614 (4)0.5429 (5)0.5494 (2)0.0475 (13)
C130.5772 (4)0.5085 (5)0.5794 (2)0.0562 (15)
H130.54870.56100.60580.067*
C140.5352 (4)0.3978 (5)0.5707 (2)0.0610 (16)
H140.47750.37580.59080.073*
C150.5772 (4)0.3173 (5)0.5321 (2)0.0533 (15)
H150.54860.24140.52670.064*
C160.0358 (7)0.3912 (5)0.6599 (3)0.075 (2)
C170.0323 (5)0.4802 (5)0.6358 (2)0.0563 (16)
C180.1248 (5)0.5010 (5)0.6608 (3)0.0716 (19)
H180.16930.55980.64480.086*
C190.1527 (7)0.4368 (8)0.7089 (3)0.105 (3)
C200.0841 (10)0.3495 (9)0.7327 (4)0.134 (5)
H200.10130.30620.76580.161*
C210.0056 (9)0.3278 (7)0.7085 (3)0.116 (4)
H210.04910.26840.72470.140*
C220.1976 (6)0.2885 (6)0.6549 (3)0.125 (3)
H22A0.22290.31050.69420.187*
H22B0.25460.28460.62970.187*
H22C0.16450.21160.65590.187*
C230.0025 (4)0.5525 (4)0.5873 (2)0.0501 (14)
H230.07190.55180.57840.060*
C240.0810 (4)0.7700 (4)0.4857 (2)0.0422 (13)
C250.0264 (4)0.8531 (4)0.4470 (2)0.0411 (13)
C260.0762 (4)0.9601 (4)0.43118 (19)0.0412 (12)
H260.14120.97710.44450.049*
C270.0283 (4)1.0406 (5)0.3956 (2)0.0429 (13)
C280.0680 (4)1.0164 (5)0.3763 (2)0.0561 (15)
H280.10071.07200.35320.067*
C290.1162 (4)0.9099 (5)0.3910 (2)0.0577 (15)
H290.18060.89270.37680.069*
C300.0696 (4)0.8282 (4)0.4267 (2)0.0455 (13)
H300.10300.75680.43700.055*
C310.6289 (6)0.9488 (7)0.5556 (5)0.173 (5)
H31A0.58891.01940.56220.260*
H31B0.64910.94840.51540.260*
H31C0.68980.94830.58230.260*
H20.5782 (11)0.183 (5)0.434 (2)0.080*
H4A0.0489 (9)0.695 (5)0.520 (2)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1071 (6)0.0787 (5)0.0892 (5)0.0026 (4)0.0552 (4)0.0009 (4)
Br20.1725 (10)0.2271 (12)0.0980 (7)0.1320 (9)0.0695 (6)0.0473 (7)
O10.057 (3)0.071 (3)0.084 (3)0.018 (2)0.008 (2)0.022 (2)
O20.035 (2)0.056 (2)0.059 (2)0.0003 (18)0.0038 (17)0.0118 (18)
O30.067 (3)0.046 (2)0.096 (3)0.010 (2)0.042 (2)0.018 (2)
O40.119 (4)0.055 (3)0.082 (3)0.019 (3)0.028 (3)0.003 (2)
O50.040 (2)0.060 (2)0.070 (3)0.0084 (19)0.0117 (19)0.0173 (19)
O60.061 (3)0.046 (2)0.060 (2)0.0045 (19)0.0187 (19)0.0093 (19)
O70.047 (3)0.057 (3)0.193 (5)0.005 (2)0.028 (3)0.036 (3)
N10.047 (3)0.036 (3)0.048 (3)0.000 (2)0.004 (2)0.008 (2)
N20.039 (3)0.044 (3)0.054 (3)0.006 (2)0.012 (2)0.017 (2)
N30.049 (3)0.046 (3)0.052 (3)0.010 (2)0.005 (2)0.001 (2)
N40.033 (3)0.048 (3)0.054 (3)0.004 (2)0.004 (2)0.011 (2)
C10.060 (4)0.041 (3)0.042 (3)0.002 (3)0.000 (3)0.001 (3)
C20.055 (4)0.041 (3)0.051 (4)0.007 (3)0.004 (3)0.006 (3)
C30.081 (5)0.045 (4)0.051 (4)0.001 (3)0.011 (3)0.006 (3)
C40.094 (5)0.046 (4)0.047 (4)0.002 (4)0.012 (3)0.009 (3)
C50.073 (4)0.043 (4)0.046 (3)0.000 (3)0.019 (3)0.005 (3)
C60.054 (4)0.036 (3)0.050 (3)0.002 (3)0.002 (3)0.002 (3)
C70.056 (4)0.071 (4)0.110 (5)0.014 (4)0.009 (4)0.000 (4)
C80.045 (3)0.049 (4)0.053 (3)0.001 (3)0.014 (3)0.004 (3)
C90.041 (3)0.036 (3)0.044 (3)0.002 (3)0.004 (3)0.001 (3)
C100.038 (3)0.042 (3)0.047 (3)0.002 (3)0.004 (2)0.005 (3)
C110.034 (3)0.045 (3)0.054 (3)0.000 (3)0.011 (2)0.004 (3)
C120.042 (3)0.043 (3)0.059 (3)0.002 (3)0.015 (3)0.007 (3)
C130.064 (4)0.050 (4)0.058 (4)0.003 (3)0.025 (3)0.018 (3)
C140.064 (4)0.065 (4)0.057 (4)0.011 (3)0.028 (3)0.013 (3)
C150.059 (4)0.049 (4)0.053 (4)0.020 (3)0.013 (3)0.011 (3)
C160.134 (7)0.033 (4)0.055 (5)0.025 (4)0.021 (5)0.008 (3)
C170.075 (4)0.049 (4)0.044 (4)0.025 (3)0.002 (3)0.003 (3)
C180.096 (5)0.069 (5)0.048 (4)0.043 (4)0.002 (4)0.001 (3)
C190.151 (8)0.114 (7)0.050 (5)0.074 (6)0.016 (5)0.008 (5)
C200.235 (15)0.115 (9)0.052 (6)0.108 (10)0.002 (7)0.018 (5)
C210.219 (12)0.061 (5)0.063 (6)0.039 (7)0.034 (6)0.020 (5)
C220.175 (8)0.067 (5)0.120 (6)0.046 (5)0.082 (6)0.020 (4)
C230.054 (4)0.042 (3)0.054 (4)0.001 (3)0.002 (3)0.001 (3)
C240.038 (3)0.041 (3)0.047 (3)0.001 (3)0.001 (3)0.004 (3)
C250.040 (3)0.042 (3)0.041 (3)0.006 (3)0.002 (2)0.001 (3)
C260.040 (3)0.048 (3)0.035 (3)0.000 (3)0.000 (2)0.003 (3)
C270.050 (3)0.038 (3)0.042 (3)0.002 (3)0.005 (3)0.002 (3)
C280.051 (4)0.057 (4)0.062 (4)0.004 (3)0.018 (3)0.010 (3)
C290.043 (3)0.061 (4)0.071 (4)0.003 (3)0.022 (3)0.005 (3)
C300.038 (3)0.046 (3)0.052 (3)0.009 (3)0.005 (3)0.000 (3)
C310.093 (6)0.077 (6)0.357 (15)0.022 (5)0.076 (8)0.013 (8)
Geometric parameters (Å, º) top
Br1—C51.893 (5)C10—C111.389 (6)
Br2—C191.879 (9)C11—C121.382 (6)
O1—C21.342 (6)C11—H110.9300
O1—C71.423 (6)C12—C131.372 (7)
O2—C91.230 (5)C13—C141.360 (7)
O3—C121.360 (5)C13—H130.9300
O3—H30.8200C14—C151.387 (7)
O4—C161.336 (8)C14—H140.9300
O4—C221.452 (6)C15—H150.9300
O5—C241.233 (5)C16—C211.384 (9)
O6—C271.363 (5)C16—C171.413 (8)
O6—H60.8200C17—C181.374 (8)
O7—C311.335 (7)C17—C231.456 (7)
O7—H70.8200C18—C191.370 (9)
N1—C81.276 (5)C18—H180.9300
N1—N21.379 (5)C19—C201.401 (12)
N2—C91.346 (6)C20—C211.335 (12)
N2—H20.894 (10)C20—H200.9300
N3—C231.290 (6)C21—H210.9300
N3—N41.369 (5)C22—H22A0.9600
N4—C241.347 (6)C22—H22B0.9600
N4—H4A0.902 (10)C22—H22C0.9600
C1—C61.384 (7)C23—H230.9300
C1—C21.411 (7)C24—C251.484 (6)
C1—C81.465 (7)C25—C301.377 (6)
C2—C31.380 (7)C25—C261.393 (6)
C3—C41.374 (7)C26—C271.380 (6)
C3—H3A0.9300C26—H260.9300
C4—C51.361 (7)C27—C281.371 (7)
C4—H40.9300C28—C291.374 (7)
C5—C61.380 (7)C28—H280.9300
C6—H6A0.9300C29—C301.382 (6)
C7—H7A0.9600C29—H290.9300
C7—H7B0.9600C30—H300.9300
C7—H7C0.9600C31—H31A0.9600
C8—H80.9300C31—H31B0.9600
C9—C101.489 (6)C31—H31C0.9600
C10—C151.379 (6)
C2—O1—C7117.8 (4)C10—C15—C14119.2 (5)
C12—O3—H3109.5C10—C15—H15120.4
C16—O4—C22118.1 (6)C14—C15—H15120.4
C27—O6—H6109.5O4—C16—C21127.1 (8)
C31—O7—H7109.5O4—C16—C17115.0 (6)
C8—N1—N2114.9 (4)C21—C16—C17117.8 (8)
C9—N2—N1117.3 (4)C18—C17—C16119.7 (6)
C9—N2—H2126 (3)C18—C17—C23122.3 (6)
N1—N2—H2116 (3)C16—C17—C23117.9 (6)
C23—N3—N4114.1 (4)C19—C18—C17121.2 (7)
C24—N4—N3119.1 (4)C19—C18—H18119.4
C24—N4—H4A123 (3)C17—C18—H18119.4
N3—N4—H4A115 (3)C18—C19—C20118.5 (9)
C6—C1—C2119.1 (5)C18—C19—Br2120.6 (8)
C6—C1—C8120.9 (5)C20—C19—Br2120.8 (7)
C2—C1—C8119.9 (5)C21—C20—C19120.8 (9)
O1—C2—C3125.8 (5)C21—C20—H20119.6
O1—C2—C1115.2 (5)C19—C20—H20119.6
C3—C2—C1119.1 (5)C20—C21—C16121.9 (10)
C4—C3—C2120.9 (5)C20—C21—H21119.0
C4—C3—H3A119.5C16—C21—H21119.0
C2—C3—H3A119.5O4—C22—H22A109.5
C5—C4—C3119.9 (5)O4—C22—H22B109.5
C5—C4—H4120.1H22A—C22—H22B109.5
C3—C4—H4120.1O4—C22—H22C109.5
C4—C5—C6121.0 (5)H22A—C22—H22C109.5
C4—C5—Br1119.8 (4)H22B—C22—H22C109.5
C6—C5—Br1119.2 (4)N3—C23—C17119.4 (5)
C5—C6—C1120.0 (5)N3—C23—H23120.3
C5—C6—H6A120.0C17—C23—H23120.3
C1—C6—H6A120.0O5—C24—N4122.0 (5)
O1—C7—H7A109.5O5—C24—C25122.1 (5)
O1—C7—H7B109.5N4—C24—C25116.0 (5)
H7A—C7—H7B109.5C30—C25—C26119.9 (5)
O1—C7—H7C109.5C30—C25—C24122.8 (5)
H7A—C7—H7C109.5C26—C25—C24117.4 (4)
H7B—C7—H7C109.5C27—C26—C25119.6 (5)
N1—C8—C1121.7 (5)C27—C26—H26120.2
N1—C8—H8119.2C25—C26—H26120.2
C1—C8—H8119.2O6—C27—C28116.3 (5)
O2—C9—N2121.6 (5)O6—C27—C26123.3 (5)
O2—C9—C10121.7 (5)C28—C27—C26120.4 (5)
N2—C9—C10116.7 (4)C27—C28—C29120.0 (5)
C15—C10—C11119.9 (4)C27—C28—H28120.0
C15—C10—C9122.5 (5)C29—C28—H28120.0
C11—C10—C9117.5 (4)C28—C29—C30120.4 (5)
C12—C11—C10119.8 (5)C28—C29—H29119.8
C12—C11—H11120.1C30—C29—H29119.8
C10—C11—H11120.1C25—C30—C29119.7 (5)
O3—C12—C13117.0 (5)C25—C30—H30120.1
O3—C12—C11123.1 (5)C29—C30—H30120.1
C13—C12—C11119.9 (5)O7—C31—H31A109.5
C14—C13—C12120.3 (5)O7—C31—H31B109.5
C14—C13—H13119.8H31A—C31—H31B109.5
C12—C13—H13119.8O7—C31—H31C109.5
C13—C14—C15120.8 (5)H31A—C31—H31C109.5
C13—C14—H14119.6H31B—C31—H31C109.5
C15—C14—H14119.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O2i0.90 (1)2.05 (2)2.923 (5)164 (5)
N2—H2···O7i0.89 (1)1.98 (1)2.866 (5)173 (5)
O7—H7···O30.821.962.737 (5)157
O6—H6···N1ii0.822.483.140 (5)138
O6—H6···O2ii0.822.062.777 (5)146
O3—H3···N3iii0.822.643.110 (6)118
O3—H3···O5iii0.821.922.692 (5)157
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y+1, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC15H13BrN2O3·0.5CH4O
Mr365.21
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)12.906 (2), 11.177 (2), 22.607 (3)
β (°) 93.706 (3)
V3)3254.3 (9)
Z8
Radiation typeMo Kα
µ (mm1)2.54
Crystal size (mm)0.20 × 0.18 × 0.17
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.630, 0.672
No. of measured, independent and
observed [I > 2σ(I)] reflections
21623, 6725, 2610
Rint0.104
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.170, 0.98
No. of reflections6725
No. of parameters409
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.51, 0.47

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O2i0.902 (10)2.045 (18)2.923 (5)164 (5)
N2—H2···O7i0.894 (10)1.977 (13)2.866 (5)173 (5)
O7—H7···O30.821.962.737 (5)156.8
O6—H6···N1ii0.822.483.140 (5)138.0
O6—H6···O2ii0.822.062.777 (5)146.4
O3—H3···N3iii0.822.643.110 (6)118.4
O3—H3···O5iii0.821.922.692 (5)157.4
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y+1, z; (iii) x+1, y, z.
 

Acknowledgements

The author thanks Kaili College for financial support.

References

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