N′-(5-Bromo-2-hydroxy­benzyl­idene)-3-hydroxy­benzohydrazide

Nie, Y.

doi:10.1107/S1600536808002250

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o514

doi:10.1107/S1600536808002250

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N′-(5-Bromo-2-hydroxybenzylidene)-3-hydroxybenzohydrazide

Yi Nie ^a ^*

^aDepartment of Chemistry, Qufu Normal University, Qufu 273165, People's Republic of China
^*Correspondence e-mail: nieyi68@126.com

(Received 4 January 2008; accepted 22 January 2008; online 25 January 2008)

The asymmetric unit of the title compound, C₁₄H₁₁BrN₂O₃, contains two crystallographically independent molecules with slightly different conformations with respect to the aromatic rings; the dihedral angles between the two benzene rings in the two molecules are 55.0 (7) and 16.3 (7)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds, forming chains running along the a axis.

Related literature

For related literature, see: Akitsu & Einaga (2006 ); Bahner et al. (1968 ); Butcher et al. (2005 ); Hodnett & Mooney (1970 ); Merchant & Chothia (1970 ); Pradeep (2005 ); Sigman & Jacobsen (1998 ).

Experimental

Crystal data

C₁₄H₁₁BrN₂O₃
M_r = 335.16
Triclinic, $[P \overline 1]$
a = 6.295 (3) Å
b = 14.988 (4) Å
c = 15.423 (3) Å
α = 70.97 (2)°
β = 80.64 (2)°
γ = 78.02 (2)°
V = 1338.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 3.08 mm⁻¹
T = 298 (2) K
0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.549, T_max = 0.577
11037 measured reflections
5652 independent reflections
2286 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.193
S = 0.93
5652 reflections
371 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯O6ⁱ	0.90 (5)	2.60 (8)	3.045 (9)	111 (6)
N2—H2⋯O3ⁱⁱ	0.90 (6)	2.39 (7)	3.021 (9)	127 (7)
O6—H6⋯O5ⁱⁱⁱ	0.82	2.14	2.760 (8)	132
O4—H4⋯N3	0.82	1.95	2.665 (8)	145
O3—H3⋯O2^iv	0.82	1.93	2.737 (8)	167
O1—H1⋯N1	0.82	1.94	2.654 (8)	145
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+1, -y+2, -z+2; (iii) -x+1, -y+1, -z+2; (iv) -x, -y+2, -z+2.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002250/rz2193sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002250/rz2193Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have been widely investigated due to their easy synthesis, versatile structures and widely applications (Sigman & Jacobsen, 1998; Akitsu & Einaga, 2006; Pradeep, 2005; Butcher et al., 2005). The excellent antibacterial and antitumor properties of such compounds have attracted much interest in recent years (Hodnett & Mooney, 1970; Bahner et al., 1968; Merchant & Chothia, 1970). In order to further investigate the structures of such compounds, a new Schiff base compound is reported in this paper.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1) with slightly different conformation with respect to the aromatic ring planes. The dihedral angles between the two benzene rings in the molecules are 55.0 (7) and 16.3 (7)°, respectively. The molecular conformation is stabilized by intramolecular N—H···O hydrogen bonding interactions (Table 1). In the crystal structure, molecules are linked through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1), forming chains running along the a axis (Fig. 2).

Related literature top

For related literature, see: Akitsu & Einaga (2006); Bahner et al. (1968); Butcher et al. (2005); Hodnett & Mooney (1970); Merchant & Chothia (1970); Pradeep (2005); Sigman & Jacobsen (1998).

Experimental top

The title compound was obtained by stirring of 5-bromosalicylaldehyde (0.1 mmol, 20.1 mg) and 3-hydroxybenzoic acid hydrazide (0.1 mmol, 15.2 mg) in a methanol solution (10 ml) at room temperature. Yellow block-shaped single crystals suitable for X-ray diffraction were formed from the solution after three days.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability ellipsoids.
	Fig. 2. Molecular packing of the title compound. Hydrogen atoms not involved in intermolecular hydrogen bonds (dashed lines) are omitted for clarity.

N'-(5-Bromo-2-hydroxybenzylidene)-3-hydroxybenzohydrazide top

Crystal data top

C₁₄H₁₁BrN₂O₃	Z = 4
M_r = 335.16	F(000) = 672
Triclinic, P1	D_x = 1.663 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.295 (3) Å	Cell parameters from 819 reflections
b = 14.988 (4) Å	θ = 2.3–24.3°
c = 15.423 (3) Å	µ = 3.08 mm⁻¹
α = 70.97 (2)°	T = 298 K
β = 80.64 (2)°	Block, yellow
γ = 78.02 (2)°	0.20 × 0.18 × 0.18 mm
V = 1338.6 (8) Å³

Data collection top

Bruker SMART APEX area-detector diffractometer	5652 independent reflections
Radiation source: fine-focus sealed tube	2286 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
ω scans	θ_max = 27.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.549, T_max = 0.577	k = −19→19
11037 measured reflections	l = −19→19

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.193	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ²(F_o²) + (0.0728P)²] where P = (F_o² + 2F_c²)/3
5652 reflections	(Δ/σ)_max < 0.001
371 parameters	Δρ_max = 0.70 e Å⁻³
2 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₄H₁₁BrN₂O₃	γ = 78.02 (2)°
M_r = 335.16	V = 1338.6 (8) Å³
Triclinic, P1	Z = 4
a = 6.295 (3) Å	Mo Kα radiation
b = 14.988 (4) Å	µ = 3.08 mm⁻¹
c = 15.423 (3) Å	T = 298 K
α = 70.97 (2)°	0.20 × 0.18 × 0.18 mm
β = 80.64 (2)°

Data collection top

Bruker SMART APEX area-detector diffractometer	5652 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2286 reflections with I > 2σ(I)
T_min = 0.549, T_max = 0.577	R_int = 0.078
11037 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	2 restraints
wR(F²) = 0.193	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	Δρ_max = 0.70 e Å⁻³
5652 reflections	Δρ_min = −0.50 e Å⁻³
371 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	0.88585 (14)	0.92277 (7)	0.36574 (6)	0.0631 (3)
Br2	1.22791 (15)	0.68828 (8)	0.26774 (6)	0.0759 (4)
O1	0.1995 (9)	0.8047 (5)	0.6860 (4)	0.0657 (17)
H1	0.2224	0.8173	0.7312	0.099*
O2	0.1318 (8)	0.8815 (4)	0.9236 (4)	0.0558 (15)
O3	0.1855 (9)	1.0107 (5)	1.1872 (4)	0.0620 (16)
H3	0.0778	1.0365	1.1593	0.093*
O4	0.5513 (9)	0.5809 (5)	0.5941 (4)	0.0649 (17)
H4	0.5871	0.5866	0.6406	0.097*
O5	0.5448 (9)	0.6020 (4)	0.8512 (3)	0.0600 (16)
O6	0.7038 (9)	0.5109 (5)	1.1850 (3)	0.0656 (17)
H6	0.5797	0.5050	1.1805	0.098*
N1	0.4379 (10)	0.8497 (4)	0.7878 (4)	0.0450 (16)
N2	0.4909 (11)	0.8521 (5)	0.8700 (4)	0.0530 (18)
N3	0.8090 (10)	0.6223 (5)	0.6916 (4)	0.0504 (18)
N4	0.8723 (10)	0.6282 (5)	0.7716 (4)	0.0491 (17)
C1	0.5485 (13)	0.8594 (5)	0.6307 (5)	0.047 (2)
C2	0.3583 (13)	0.8316 (6)	0.6156 (6)	0.050 (2)
C3	0.3325 (14)	0.8293 (6)	0.5294 (6)	0.058 (2)
H3A	0.2083	0.8102	0.5207	0.069*
C4	0.4872 (14)	0.8549 (6)	0.4561 (6)	0.059 (2)
H4A	0.4682	0.8530	0.3982	0.070*
C5	0.6726 (13)	0.8837 (5)	0.4693 (5)	0.049 (2)
C6	0.7046 (12)	0.8877 (5)	0.5549 (5)	0.049 (2)
H6A	0.8276	0.9088	0.5621	0.059*
C7	0.5847 (14)	0.8639 (5)	0.7195 (5)	0.051 (2)
H7	0.7172	0.8774	0.7269	0.061*
C8	0.3276 (13)	0.8706 (5)	0.9354 (5)	0.044 (2)
C9	0.3987 (13)	0.8760 (5)	1.0207 (5)	0.044 (2)
C10	0.2543 (12)	0.9334 (5)	1.0679 (5)	0.045 (2)
H10	0.1160	0.9607	1.0493	0.054*
C11	0.3203 (13)	0.9490 (6)	1.1430 (5)	0.052 (2)
C12	0.5208 (13)	0.9068 (6)	1.1729 (5)	0.053 (2)
H12	0.5649	0.9182	1.2225	0.064*
C13	0.6573 (14)	0.8467 (6)	1.1277 (6)	0.061 (2)
H13	0.7898	0.8149	1.1503	0.073*
C14	0.6038 (13)	0.8326 (6)	1.0512 (6)	0.056 (2)
H14	0.7017	0.7950	1.0201	0.067*
C15	0.9095 (12)	0.6284 (5)	0.5347 (5)	0.044 (2)
C16	0.7120 (13)	0.6035 (5)	0.5224 (5)	0.046 (2)
C17	0.6807 (13)	0.5990 (6)	0.4375 (6)	0.057 (2)
H17	0.5559	0.5784	0.4314	0.069*
C18	0.8289 (13)	0.6240 (6)	0.3624 (6)	0.056 (2)
H18	0.8024	0.6229	0.3051	0.067*
C19	1.0199 (13)	0.6510 (6)	0.3722 (5)	0.052 (2)
C20	1.0584 (12)	0.6519 (6)	0.4565 (5)	0.049 (2)
H20	1.1885	0.6687	0.4621	0.059*
C21	0.9532 (13)	0.6323 (5)	0.6225 (5)	0.048 (2)
H21	1.0901	0.6425	0.6286	0.058*
C22	0.7317 (13)	0.6159 (5)	0.8508 (5)	0.046 (2)
C23	0.8148 (11)	0.6196 (5)	0.9341 (5)	0.0408 (19)
C24	0.7138 (12)	0.5723 (5)	1.0196 (5)	0.048 (2)
H24	0.5921	0.5451	1.0220	0.057*
C25	0.7917 (13)	0.5653 (6)	1.1006 (5)	0.047 (2)
C26	0.9760 (13)	0.6038 (6)	1.0988 (6)	0.052 (2)
H26	1.0320	0.5964	1.1534	0.063*
C27	1.0751 (12)	0.6534 (5)	1.0148 (5)	0.047 (2)
H27	1.1933	0.6824	1.0133	0.056*
C28	0.9992 (12)	0.6601 (5)	0.9322 (6)	0.050 (2)
H28	1.0703	0.6912	0.8761	0.060*
H2	0.615 (7)	0.860 (6)	0.886 (5)	0.080*
H4B	1.004 (6)	0.643 (6)	0.771 (5)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0515 (6)	0.0820 (7)	0.0483 (6)	−0.0067 (5)	0.0040 (4)	−0.0167 (5)
Br2	0.0608 (6)	0.1244 (10)	0.0477 (6)	−0.0376 (6)	0.0053 (5)	−0.0243 (6)
O1	0.055 (4)	0.095 (5)	0.056 (4)	−0.035 (3)	0.002 (3)	−0.025 (4)
O2	0.038 (3)	0.077 (4)	0.058 (4)	−0.011 (3)	−0.001 (3)	−0.029 (3)
O3	0.043 (3)	0.100 (5)	0.056 (4)	−0.015 (3)	0.002 (3)	−0.042 (4)
O4	0.054 (4)	0.095 (5)	0.051 (4)	−0.033 (3)	−0.002 (3)	−0.017 (4)
O5	0.045 (4)	0.090 (5)	0.048 (3)	−0.031 (3)	−0.005 (3)	−0.013 (3)
O6	0.045 (4)	0.112 (5)	0.042 (3)	−0.028 (4)	−0.001 (3)	−0.019 (3)
N1	0.046 (4)	0.049 (4)	0.042 (4)	−0.005 (3)	0.000 (3)	−0.019 (3)
N2	0.043 (4)	0.076 (5)	0.041 (4)	−0.007 (4)	−0.001 (3)	−0.023 (4)
N3	0.039 (4)	0.067 (5)	0.040 (4)	−0.005 (3)	−0.003 (3)	−0.013 (4)
N4	0.035 (4)	0.071 (5)	0.045 (4)	−0.018 (4)	−0.002 (3)	−0.017 (4)
C1	0.053 (5)	0.034 (5)	0.048 (5)	−0.004 (4)	0.003 (4)	−0.011 (4)
C2	0.041 (5)	0.057 (6)	0.055 (6)	−0.011 (4)	−0.008 (4)	−0.016 (4)
C3	0.052 (6)	0.068 (6)	0.057 (6)	−0.017 (5)	−0.009 (5)	−0.019 (5)
C4	0.061 (6)	0.075 (7)	0.049 (5)	−0.020 (5)	−0.001 (5)	−0.028 (5)
C5	0.051 (5)	0.044 (5)	0.039 (5)	0.008 (4)	0.000 (4)	−0.006 (4)
C6	0.042 (5)	0.052 (6)	0.055 (5)	−0.011 (4)	−0.010 (4)	−0.013 (4)
C7	0.054 (5)	0.058 (6)	0.043 (5)	−0.014 (4)	−0.001 (4)	−0.017 (4)
C8	0.048 (5)	0.040 (5)	0.046 (5)	−0.011 (4)	−0.005 (4)	−0.013 (4)
C9	0.049 (5)	0.041 (5)	0.039 (5)	−0.007 (4)	−0.002 (4)	−0.012 (4)
C10	0.038 (5)	0.053 (5)	0.039 (5)	−0.009 (4)	0.003 (4)	−0.010 (4)
C11	0.046 (5)	0.066 (6)	0.043 (5)	−0.018 (5)	0.001 (4)	−0.013 (4)
C12	0.052 (6)	0.069 (6)	0.040 (5)	−0.010 (5)	−0.009 (4)	−0.016 (4)
C13	0.057 (6)	0.054 (6)	0.058 (6)	0.002 (5)	−0.015 (5)	−0.001 (5)
C14	0.049 (5)	0.062 (6)	0.057 (6)	−0.007 (5)	−0.007 (4)	−0.019 (5)
C15	0.039 (5)	0.057 (6)	0.040 (5)	−0.012 (4)	−0.006 (4)	−0.015 (4)
C16	0.049 (5)	0.050 (5)	0.041 (5)	−0.014 (4)	−0.008 (4)	−0.011 (4)
C17	0.046 (5)	0.076 (7)	0.057 (6)	−0.020 (5)	−0.008 (5)	−0.021 (5)
C18	0.049 (5)	0.065 (6)	0.059 (6)	−0.008 (5)	−0.016 (5)	−0.023 (5)
C19	0.047 (5)	0.067 (6)	0.041 (5)	−0.010 (4)	−0.005 (4)	−0.017 (4)
C20	0.037 (5)	0.064 (6)	0.052 (5)	−0.022 (4)	−0.001 (4)	−0.018 (4)
C21	0.041 (5)	0.053 (6)	0.047 (5)	−0.009 (4)	−0.007 (4)	−0.009 (4)
C22	0.036 (5)	0.041 (5)	0.056 (5)	−0.012 (4)	0.000 (4)	−0.009 (4)
C23	0.031 (4)	0.041 (5)	0.056 (5)	−0.005 (4)	−0.012 (4)	−0.019 (4)
C24	0.033 (4)	0.057 (6)	0.059 (5)	−0.023 (4)	0.011 (4)	−0.024 (4)
C25	0.040 (5)	0.058 (6)	0.049 (5)	−0.002 (4)	−0.005 (4)	−0.025 (4)
C26	0.045 (5)	0.061 (6)	0.056 (5)	−0.007 (4)	−0.006 (4)	−0.027 (5)
C27	0.042 (5)	0.040 (5)	0.061 (5)	−0.013 (4)	−0.012 (4)	−0.012 (4)
C28	0.044 (5)	0.049 (5)	0.059 (5)	−0.015 (4)	0.001 (4)	−0.015 (4)

Geometric parameters (Å, º) top

Br1—C5	1.928 (7)	C9—C14	1.400 (10)
Br2—C19	1.912 (8)	C9—C10	1.401 (9)
O1—C2	1.368 (9)	C10—C11	1.395 (10)
O1—H1	0.8200	C10—H10	0.9300
O2—C8	1.245 (9)	C11—C12	1.369 (11)
O3—C11	1.392 (9)	C12—C13	1.388 (10)
O3—H3	0.8200	C12—H12	0.9300
O4—C16	1.377 (8)	C13—C14	1.369 (11)
O4—H4	0.8200	C13—H13	0.9300
O5—C22	1.235 (8)	C14—H14	0.9300
O6—C25	1.388 (9)	C15—C20	1.396 (9)
O6—H6	0.8200	C15—C16	1.427 (10)
N1—C7	1.276 (8)	C15—C21	1.447 (10)
N1—N2	1.375 (8)	C16—C17	1.380 (10)
N2—C8	1.371 (9)	C17—C18	1.365 (10)
N2—H2	0.90 (6)	C17—H17	0.9300
N3—C21	1.273 (8)	C18—C19	1.391 (11)
N3—N4	1.390 (8)	C18—H18	0.9300
N4—C22	1.371 (9)	C19—C20	1.365 (10)
N4—H4B	0.90 (5)	C20—H20	0.9300
C1—C6	1.410 (10)	C21—H21	0.9300
C1—C2	1.422 (10)	C22—C23	1.485 (10)
C1—C7	1.450 (10)	C23—C24	1.397 (10)
C2—C3	1.377 (10)	C23—C28	1.410 (10)
C3—C4	1.374 (10)	C24—C25	1.380 (10)
C3—H3A	0.9300	C24—H24	0.9300
C4—C5	1.391 (11)	C25—C26	1.392 (10)
C4—H4A	0.9300	C26—C27	1.386 (10)
C5—C6	1.388 (10)	C26—H26	0.9300
C6—H6A	0.9300	C27—C28	1.398 (10)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.488 (10)	C28—H28	0.9300

C2—O1—H1	109.5	C14—C13—C12	122.3 (8)
C11—O3—H3	109.5	C14—C13—H13	118.8
C16—O4—H4	109.5	C12—C13—H13	118.8
C25—O6—H6	109.5	C13—C14—C9	118.7 (8)
C7—N1—N2	116.6 (7)	C13—C14—H14	120.7
C8—N2—N1	119.5 (6)	C9—C14—H14	120.7
C8—N2—H2	107 (5)	C20—C15—C16	116.6 (7)
N1—N2—H2	132 (5)	C20—C15—C21	120.9 (7)
C21—N3—N4	115.7 (7)	C16—C15—C21	122.5 (7)
C22—N4—N3	120.6 (6)	O4—C16—C17	118.2 (7)
C22—N4—H4B	119 (5)	O4—C16—C15	121.7 (7)
N3—N4—H4B	120 (5)	C17—C16—C15	120.1 (7)
C6—C1—C2	118.4 (7)	C18—C17—C16	121.5 (8)
C6—C1—C7	118.5 (8)	C18—C17—H17	119.3
C2—C1—C7	123.1 (7)	C16—C17—H17	119.3
O1—C2—C3	118.5 (7)	C17—C18—C19	119.3 (8)
O1—C2—C1	121.2 (7)	C17—C18—H18	120.3
C3—C2—C1	120.4 (8)	C19—C18—H18	120.3
C4—C3—C2	121.1 (8)	C20—C19—C18	120.0 (7)
C4—C3—H3A	119.4	C20—C19—Br2	119.8 (6)
C2—C3—H3A	119.4	C18—C19—Br2	120.2 (6)
C3—C4—C5	119.3 (8)	C19—C20—C15	122.4 (7)
C3—C4—H4A	120.4	C19—C20—H20	118.8
C5—C4—H4A	120.4	C15—C20—H20	118.8
C6—C5—C4	121.6 (7)	N3—C21—C15	121.7 (7)
C6—C5—Br1	119.2 (7)	N3—C21—H21	119.2
C4—C5—Br1	119.2 (6)	C15—C21—H21	119.2
C5—C6—C1	119.3 (8)	O5—C22—N4	120.2 (7)
C5—C6—H6A	120.4	O5—C22—C23	122.6 (7)
C1—C6—H6A	120.4	N4—C22—C23	117.2 (7)
N1—C7—C1	121.1 (8)	C24—C23—C28	118.4 (7)
N1—C7—H7	119.5	C24—C23—C22	117.1 (7)
C1—C7—H7	119.5	C28—C23—C22	124.2 (7)
O2—C8—N2	121.4 (7)	C25—C24—C23	121.1 (7)
O2—C8—C9	122.5 (7)	C25—C24—H24	119.5
N2—C8—C9	116.1 (7)	C23—C24—H24	119.5
C14—C9—C10	119.9 (7)	C24—C25—O6	120.9 (7)
C14—C9—C8	123.5 (7)	C24—C25—C26	120.6 (8)
C10—C9—C8	116.5 (7)	O6—C25—C26	118.2 (7)
C11—C10—C9	119.3 (7)	C27—C26—C25	119.3 (8)
C11—C10—H10	120.4	C27—C26—H26	120.4
C9—C10—H10	120.4	C25—C26—H26	120.4
C12—C11—O3	118.7 (7)	C26—C27—C28	120.6 (7)
C12—C11—C10	120.9 (8)	C26—C27—H27	119.7
O3—C11—C10	120.3 (7)	C28—C27—H27	119.7
C11—C12—C13	118.8 (8)	C27—C28—C23	119.9 (7)
C11—C12—H12	120.6	C27—C28—H28	120.0
C13—C12—H12	120.6	C23—C28—H28	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O6ⁱ	0.90 (5)	2.60 (8)	3.045 (9)	111 (6)
N2—H2···O3ⁱⁱ	0.90 (6)	2.39 (7)	3.021 (9)	127 (7)
O6—H6···O5ⁱⁱⁱ	0.82	2.14	2.760 (8)	132
O4—H4···N3	0.82	1.95	2.665 (8)	145
O3—H3···O2^iv	0.82	1.93	2.737 (8)	167
O1—H1···N1	0.82	1.94	2.654 (8)	145

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁BrN₂O₃
M_r	335.16
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.295 (3), 14.988 (4), 15.423 (3)
α, β, γ (°)	70.97 (2), 80.64 (2), 78.02 (2)
V (Å³)	1338.6 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.08
Crystal size (mm)	0.20 × 0.18 × 0.18

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.549, 0.577
No. of measured, independent and observed [I > 2σ(I)] reflections	11037, 5652, 2286
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.193, 0.93
No. of reflections	5652
No. of parameters	371
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)	0.70, −0.50

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
N4—H4B···O6ⁱ	0.90 (5)	2.60 (8)	3.045 (9)	111 (6)
N2—H2···O3ⁱⁱ	0.90 (6)	2.39 (7)	3.021 (9)	127 (7)
O6—H6···O5ⁱⁱⁱ	0.82	2.14	2.760 (8)	132.3
O4—H4···N3	0.82	1.95	2.665 (8)	145.3
O3—H3···O2^iv	0.82	1.93	2.737 (8)	166.5
O1—H1···N1	0.82	1.94	2.654 (8)	144.8

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

References

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Volume 64| Part 2| February 2008| Page o514

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