2-Bromo-5-meth­oxy-N′-[(E)-(2-nitro­phen­yl)methyl­ene]benzohydrazide

Yathirajan, H.S.; Sarojini, B.K.; Narayana, B.; Sunil, K.; Bolte, M.

doi:10.1107/S1600536807020375

2-Bromo-5-methoxy-N′-[(E)-(2-nitrophenyl)methylene]benzohydrazide

H. S. Yathirajan, B. K. Sarojini, B. Narayana, K. Sunil and M. Bolte

Geometric parameters of the title compound, C₁₅H₁₂BrN₃O₄, a Schiff base, are in the usual ranges. There are two molecules in the asymmetric unit, differing in the dihedral angles between the aromatic rings and the central CO—NH—N=C unit. Furthermore, the C_ar—C_ar—O—CH₃ torsion angles differ by almost 180°. The crystal packing is stabilized by N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020375/at2279sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020375/at2279Isup2.hkl Contains datablock I

CCDC reference: 647728

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Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C)= 0.003 Å
R factor = 0.037
wR factor = 0.091
Data-to-parameter ratio = 16.4

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No syntax errors found


No errors found in this datablock

Comment top

Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Moreover, Schiff bases are also known to have biological activities such as antimicrobial, antifungal, antitumor and as herbicides. Schiff bases have also been employed as ligands for complexation of metal ions. On the industrial scale, they have wide range of applications such as dyes and pigments. A new Schiff base, C₁₅H₁₂BrN₃O₄, was synthesized and its crystal structure is reported.

There are two molecules in the asymmetric unit differing in the dihedral angles between the aromatic rings and the central CO—NH—N=C unit [N2—C2—C21—C22 = 159.2 (2)°, N2A—C2A—C21A—C22A = -169.3 (2)°, O1—C1—C11—C12 = 74.2 (3)° and O1A—C1A—C11A—C12A = 104.5 (3)°]. The crystal packing is stabilized by N—H···O hydrogen bonds.

Related literature top

For related structures, see: (E)-N'-(4-benzyloxy-3-methoxybenzylidene)benzohydrazide (He et al., 2005), (E)-N'-(4-butoxy-3-methoxybenzylidene)benzohydrazide (Zhen et al., 2005a), (E)-N'-(3-ethoxy-4-methoxybenzylidene)benzohydrazide (Zhen et al., 2005b), N'-[(E)-4-(2-hydroxyethoxy)-3-methoxybenzylidene]benzohydrazide monohydrate (Diao et al., 2005). For related literature, see: El-Masry et al. (2000); Pandey et al. (1999); Singh et al. (1988); Hodnett et al. (1970); Desai et al. (2001); Aydoğan et al. (2001); Taggi et al. (2002).

Experimental top

A mixture of 2-bromo-5-methoxybenzohydrazide (1.22 g, 0.005 mol) and 2-nitrobenzaldehyde (0.75 g, 0.005 mol) in 25 ml of absolute ethanol containing 2 drops of 4 M sulfuric acid was refluxed for about 3 h. On cooling, the solid separated was filtered and recrystallized from a mixture of (5:5) DMF & acetone (m.p.: 486–488 K). Analysis for C₁₅H₁₂BrN₃O₄: Found (Calculated): C: 47.56 (47.64); H:3.14 (3.20); N:11.04% (11.11%).

Structure description top

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. Perspective view of molecule one in the asymmetric unit of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.
	Fig. 2. Perspective view of molecule two in the asymmetric unit of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.

2-Bromo-5-methoxy-N'-[(E)-(2-nitrophenyl)methylene]benzohydrazide top

Crystal data top

C₁₅H₁₂BrN₃O₄	Z = 4
M_r = 378.19	F(000) = 760
Triclinic, P1	D_x = 1.652 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1611 (6) Å	Cell parameters from 21874 reflections
b = 9.0279 (6) Å	θ = 2.5–26.8°
c = 21.3467 (15) Å	µ = 2.73 mm⁻¹
α = 85.585 (6)°	T = 173 K
β = 89.441 (6)°	Block, colourless
γ = 75.912 (5)°	0.36 × 0.33 × 0.32 mm
V = 1520.88 (18) Å³

Data collection top

Stoe IPDSII two-circle diffractometer	7003 independent reflections
Radiation source: fine-focus sealed tube	5849 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scans	θ_max = 27.6°, θ_min = 2.6°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −10→10
T_min = 0.401, T_max = 0.426	k = −11→11
22860 measured reflections	l = −27→27

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0556P)² + 0.1348P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
7003 reflections	Δρ_max = 0.99 e Å⁻³
426 parameters	Δρ_min = −0.82 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0124 (9)

Crystal data top

C₁₅H₁₂BrN₃O₄	γ = 75.912 (5)°
M_r = 378.19	V = 1520.88 (18) Å³
Triclinic, P1	Z = 4
a = 8.1611 (6) Å	Mo Kα radiation
b = 9.0279 (6) Å	µ = 2.73 mm⁻¹
c = 21.3467 (15) Å	T = 173 K
α = 85.585 (6)°	0.36 × 0.33 × 0.32 mm
β = 89.441 (6)°

Data collection top

Stoe IPDSII two-circle diffractometer	7003 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	5849 reflections with I > 2σ(I)
T_min = 0.401, T_max = 0.426	R_int = 0.061
22860 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.99 e Å⁻³
7003 reflections	Δρ_min = −0.82 e Å⁻³
426 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	0.57284 (3)	0.71784 (3)	0.426996 (11)	0.02848 (8)
C1	0.5711 (3)	0.7471 (3)	0.27886 (10)	0.0187 (4)
O1	0.7255 (2)	0.7090 (2)	0.27580 (9)	0.0286 (4)
N1	0.4720 (2)	0.8821 (2)	0.25625 (9)	0.0196 (4)
H1	0.366 (4)	0.904 (3)	0.2649 (13)	0.019 (7)*
N2	0.5393 (2)	0.9885 (2)	0.22119 (8)	0.0183 (4)
C2	0.4284 (3)	1.1108 (3)	0.20414 (10)	0.0187 (4)
H2	0.3140	1.1220	0.2163	0.022*
C11	0.4685 (3)	0.6411 (2)	0.30862 (10)	0.0179 (4)
C12	0.4638 (3)	0.6110 (3)	0.37360 (10)	0.0202 (4)
C13	0.3702 (3)	0.5126 (3)	0.39970 (11)	0.0234 (5)
H13	0.3714	0.4899	0.4439	0.028*
C14	0.2756 (3)	0.4475 (3)	0.36165 (11)	0.0240 (5)
H14	0.2112	0.3807	0.3797	0.029*
C15	0.2745 (3)	0.4802 (3)	0.29653 (11)	0.0220 (4)
C16	0.3741 (3)	0.5756 (3)	0.27024 (10)	0.0208 (4)
H16	0.3768	0.5953	0.2259	0.025*
O17	0.1820 (2)	0.4259 (2)	0.25485 (9)	0.0311 (4)
C17	0.0475 (3)	0.3619 (3)	0.27988 (14)	0.0342 (6)
H17A	0.0946	0.2731	0.3093	0.051*
H17B	−0.0110	0.3297	0.2454	0.051*
H17C	−0.0326	0.4393	0.3020	0.051*
C21	0.4792 (3)	1.2352 (3)	0.16530 (10)	0.0181 (4)
C22	0.3661 (3)	1.3493 (3)	0.12820 (10)	0.0189 (4)
C23	0.4140 (3)	1.4700 (3)	0.09437 (11)	0.0249 (5)
H23	0.3337	1.5450	0.0696	0.030*
C24	0.5812 (3)	1.4787 (3)	0.09743 (12)	0.0287 (5)
H24	0.6163	1.5600	0.0747	0.034*
C25	0.6968 (3)	1.3684 (3)	0.13376 (12)	0.0273 (5)
H25	0.8108	1.3752	0.1362	0.033*
C26	0.6471 (3)	1.2473 (3)	0.16684 (10)	0.0221 (4)
H26	0.7286	1.1718	0.1909	0.027*
N22	0.1860 (2)	1.3483 (2)	0.12283 (9)	0.0221 (4)
O21	0.0829 (2)	1.4713 (2)	0.11166 (10)	0.0352 (4)
O22	0.1468 (2)	1.2248 (2)	0.12971 (9)	0.0296 (4)
Br1A	0.70200 (3)	1.19678 (3)	0.331535 (11)	0.03073 (9)
C1A	1.0416 (3)	0.9286 (3)	0.32993 (10)	0.0188 (4)
O1A	1.1748 (2)	0.9686 (2)	0.33047 (8)	0.0265 (4)
N1A	0.9787 (2)	0.8805 (2)	0.27891 (9)	0.0211 (4)
H1A	0.889 (4)	0.841 (4)	0.2821 (15)	0.031 (8)*
N2A	1.0619 (2)	0.8881 (2)	0.22218 (9)	0.0201 (4)
C2A	1.0003 (3)	0.8349 (3)	0.17647 (10)	0.0213 (4)
H2A	0.9044	0.7934	0.1822	0.026*
C11A	0.9363 (3)	0.9301 (3)	0.38867 (10)	0.0198 (4)
C12A	0.7888 (3)	1.0420 (3)	0.39665 (11)	0.0221 (4)
C13A	0.7040 (3)	1.0488 (3)	0.45422 (11)	0.0246 (5)
H13A	0.6031	1.1258	0.4592	0.030*
C14A	0.7670 (3)	0.9439 (3)	0.50341 (11)	0.0253 (5)
H14A	0.7100	0.9488	0.5425	0.030*
C15A	0.9152 (3)	0.8296 (3)	0.49627 (11)	0.0231 (5)
C16A	0.9999 (3)	0.8239 (3)	0.43911 (11)	0.0223 (4)
H16A	1.1014	0.7475	0.4344	0.027*
O17A	0.9665 (2)	0.7305 (2)	0.54816 (8)	0.0321 (4)
C17A	1.1194 (4)	0.6155 (3)	0.54411 (12)	0.0323 (6)
H17D	1.1087	0.5494	0.5108	0.048*
H17E	1.1422	0.5538	0.5843	0.048*
H17F	1.2128	0.6640	0.5344	0.048*
C21A	1.0826 (3)	0.8397 (2)	0.11419 (10)	0.0184 (4)
C22A	1.0152 (3)	0.8091 (3)	0.05801 (10)	0.0201 (4)
C23A	1.1006 (3)	0.8080 (3)	0.00099 (11)	0.0242 (5)
H23A	1.0523	0.7838	−0.0360	0.029*
C24A	1.2573 (3)	0.8428 (3)	−0.00072 (11)	0.0246 (5)
H24A	1.3161	0.8443	−0.0393	0.029*
C25A	1.3278 (3)	0.8752 (3)	0.05375 (11)	0.0236 (5)
H25A	1.4345	0.9001	0.0524	0.028*
C26A	1.2426 (3)	0.8714 (3)	0.11056 (11)	0.0220 (4)
H26A	1.2942	0.8907	0.1478	0.026*
N22A	0.8456 (3)	0.7797 (3)	0.05512 (9)	0.0289 (5)
O21A	0.8153 (3)	0.7032 (3)	0.01402 (10)	0.0466 (6)
O22A	0.7404 (2)	0.8375 (3)	0.09338 (10)	0.0445 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03308 (14)	0.03262 (15)	0.02237 (12)	−0.01171 (10)	−0.00104 (9)	−0.00635 (9)
C1	0.0179 (10)	0.0197 (10)	0.0196 (10)	−0.0073 (8)	0.0003 (8)	0.0010 (8)
O1	0.0158 (7)	0.0255 (9)	0.0434 (10)	−0.0054 (7)	0.0025 (7)	0.0055 (8)
N1	0.0148 (9)	0.0210 (9)	0.0232 (9)	−0.0067 (7)	0.0038 (7)	0.0039 (7)
N2	0.0199 (9)	0.0191 (9)	0.0177 (8)	−0.0094 (7)	0.0020 (7)	0.0011 (7)
C2	0.0166 (9)	0.0232 (11)	0.0173 (9)	−0.0079 (8)	0.0016 (7)	0.0011 (8)
C11	0.0153 (9)	0.0174 (10)	0.0209 (10)	−0.0045 (8)	0.0025 (8)	0.0005 (8)
C12	0.0210 (10)	0.0195 (10)	0.0196 (10)	−0.0040 (8)	0.0005 (8)	−0.0009 (8)
C13	0.0265 (11)	0.0223 (11)	0.0199 (10)	−0.0045 (9)	0.0065 (9)	0.0021 (8)
C14	0.0246 (11)	0.0206 (11)	0.0271 (11)	−0.0079 (9)	0.0071 (9)	0.0024 (9)
C15	0.0215 (10)	0.0207 (11)	0.0251 (11)	−0.0075 (9)	0.0040 (9)	−0.0032 (9)
C16	0.0216 (10)	0.0230 (11)	0.0185 (10)	−0.0072 (9)	0.0031 (8)	−0.0004 (8)
O17	0.0316 (9)	0.0406 (11)	0.0294 (9)	−0.0234 (8)	0.0076 (7)	−0.0092 (8)
C17	0.0309 (13)	0.0412 (15)	0.0393 (14)	−0.0245 (12)	0.0080 (11)	−0.0083 (12)
C21	0.0206 (10)	0.0192 (10)	0.0160 (9)	−0.0077 (8)	0.0018 (8)	−0.0016 (8)
C22	0.0182 (10)	0.0206 (10)	0.0196 (10)	−0.0085 (8)	0.0001 (8)	−0.0009 (8)
C23	0.0272 (12)	0.0213 (11)	0.0257 (11)	−0.0071 (9)	−0.0001 (9)	0.0047 (9)
C24	0.0324 (13)	0.0263 (12)	0.0306 (12)	−0.0151 (10)	0.0079 (10)	0.0025 (10)
C25	0.0217 (11)	0.0335 (13)	0.0303 (12)	−0.0138 (10)	0.0039 (9)	−0.0020 (10)
C26	0.0185 (10)	0.0279 (12)	0.0202 (10)	−0.0070 (9)	−0.0010 (8)	0.0009 (9)
N22	0.0209 (9)	0.0231 (10)	0.0227 (9)	−0.0079 (8)	−0.0030 (7)	0.0034 (8)
O21	0.0243 (9)	0.0255 (9)	0.0515 (12)	−0.0013 (7)	−0.0046 (8)	0.0094 (8)
O22	0.0270 (9)	0.0253 (9)	0.0392 (10)	−0.0138 (7)	−0.0099 (7)	0.0068 (7)
Br1A	0.02832 (14)	0.03399 (15)	0.02517 (13)	0.00198 (10)	−0.00220 (9)	−0.00360 (10)
C1A	0.0164 (10)	0.0203 (10)	0.0198 (10)	−0.0041 (8)	0.0041 (8)	−0.0039 (8)
O1A	0.0203 (8)	0.0398 (10)	0.0235 (8)	−0.0133 (7)	0.0064 (6)	−0.0096 (7)
N1A	0.0187 (9)	0.0293 (10)	0.0189 (9)	−0.0119 (8)	0.0058 (7)	−0.0044 (7)
N2A	0.0192 (9)	0.0233 (9)	0.0176 (8)	−0.0055 (7)	0.0051 (7)	−0.0011 (7)
C2A	0.0194 (10)	0.0274 (12)	0.0191 (10)	−0.0096 (9)	0.0018 (8)	−0.0015 (8)
C11A	0.0173 (10)	0.0254 (11)	0.0191 (10)	−0.0092 (9)	0.0037 (8)	−0.0053 (8)
C12A	0.0220 (10)	0.0244 (11)	0.0208 (10)	−0.0060 (9)	0.0022 (8)	−0.0057 (8)
C13A	0.0190 (10)	0.0321 (13)	0.0241 (11)	−0.0064 (9)	0.0045 (9)	−0.0107 (9)
C14A	0.0226 (11)	0.0344 (13)	0.0228 (11)	−0.0128 (10)	0.0089 (9)	−0.0090 (9)
C15A	0.0249 (11)	0.0268 (12)	0.0207 (10)	−0.0119 (10)	0.0046 (9)	−0.0029 (9)
C16A	0.0191 (10)	0.0268 (11)	0.0223 (10)	−0.0072 (9)	0.0052 (8)	−0.0047 (9)
O17A	0.0354 (10)	0.0353 (10)	0.0232 (8)	−0.0057 (8)	0.0089 (7)	0.0029 (7)
C17A	0.0368 (14)	0.0314 (14)	0.0260 (12)	−0.0042 (11)	0.0022 (10)	0.0011 (10)
C21A	0.0198 (10)	0.0178 (10)	0.0173 (9)	−0.0046 (8)	−0.0002 (8)	0.0001 (8)
C22A	0.0199 (10)	0.0213 (11)	0.0200 (10)	−0.0075 (8)	−0.0010 (8)	0.0013 (8)
C23A	0.0288 (12)	0.0280 (12)	0.0168 (10)	−0.0092 (10)	−0.0001 (8)	−0.0009 (9)
C24A	0.0276 (12)	0.0262 (12)	0.0204 (10)	−0.0081 (9)	0.0046 (9)	0.0004 (9)
C25A	0.0214 (11)	0.0260 (12)	0.0253 (11)	−0.0099 (9)	0.0040 (9)	−0.0013 (9)
C26A	0.0223 (11)	0.0259 (12)	0.0202 (10)	−0.0095 (9)	−0.0001 (8)	−0.0033 (9)
N22A	0.0287 (11)	0.0424 (13)	0.0191 (9)	−0.0174 (10)	−0.0052 (8)	0.0057 (9)
O21A	0.0521 (13)	0.0743 (16)	0.0291 (10)	−0.0441 (12)	−0.0038 (9)	−0.0078 (10)
O22A	0.0220 (9)	0.0772 (17)	0.0362 (10)	−0.0146 (10)	0.0027 (8)	−0.0087 (10)

Geometric parameters (Å, º) top

Br1—C12	1.905 (2)	Br1A—C12A	1.904 (2)
C1—O1	1.225 (3)	C1A—O1A	1.226 (3)
C1—N1	1.345 (3)	C1A—N1A	1.353 (3)
C1—C11	1.519 (3)	C1A—C11A	1.513 (3)
N1—N2	1.387 (2)	N1A—N2A	1.388 (2)
N1—H1	0.86 (3)	N1A—H1A	0.89 (3)
N2—C2	1.276 (3)	N2A—C2A	1.279 (3)
C2—C21	1.482 (3)	C2A—C21A	1.486 (3)
C2—H2	0.9500	C2A—H2A	0.9500
C11—C16	1.387 (3)	C11A—C12A	1.389 (3)
C11—C12	1.395 (3)	C11A—C16A	1.399 (3)
C12—C13	1.389 (3)	C12A—C13A	1.403 (3)
C13—C14	1.381 (4)	C13A—C14A	1.373 (4)
C13—H13	0.9500	C13A—H13A	0.9500
C14—C15	1.398 (3)	C14A—C15A	1.401 (4)
C14—H14	0.9500	C14A—H14A	0.9500
C15—O17	1.365 (3)	C15A—O17A	1.370 (3)
C15—C16	1.405 (3)	C15A—C16A	1.395 (3)
C16—H16	0.9500	C16A—H16A	0.9500
O17—C17	1.440 (3)	O17A—C17A	1.423 (3)
C17—H17A	0.9800	C17A—H17D	0.9800
C17—H17B	0.9800	C17A—H17E	0.9800
C17—H17C	0.9800	C17A—H17F	0.9800
C21—C26	1.402 (3)	C21A—C22A	1.398 (3)
C21—C22	1.402 (3)	C21A—C26A	1.403 (3)
C22—C23	1.394 (3)	C22A—C23A	1.396 (3)
C22—N22	1.478 (3)	C22A—N22A	1.474 (3)
C23—C24	1.388 (3)	C23A—C24A	1.389 (3)
C23—H23	0.9500	C23A—H23A	0.9500
C24—C25	1.386 (4)	C24A—C25A	1.384 (3)
C24—H24	0.9500	C24A—H24A	0.9500
C25—C26	1.396 (3)	C25A—C26A	1.395 (3)
C25—H25	0.9500	C25A—H25A	0.9500
C26—H26	0.9500	C26A—H26A	0.9500
N22—O21	1.228 (3)	N22A—O21A	1.220 (3)
N22—O22	1.230 (3)	N22A—O22A	1.229 (3)

O1—C1—N1	125.8 (2)	O1A—C1A—N1A	124.10 (19)
O1—C1—C11	122.3 (2)	O1A—C1A—C11A	120.4 (2)
N1—C1—C11	111.86 (18)	N1A—C1A—C11A	115.47 (19)
C1—N1—N2	120.90 (18)	C1A—N1A—N2A	118.40 (18)
C1—N1—H1	119.3 (18)	C1A—N1A—H1A	121 (2)
N2—N1—H1	119.8 (18)	N2A—N1A—H1A	121 (2)
C2—N2—N1	112.79 (18)	C2A—N2A—N1A	115.31 (19)
N2—C2—C21	119.58 (19)	N2A—C2A—C21A	118.3 (2)
N2—C2—H2	120.2	N2A—C2A—H2A	120.8
C21—C2—H2	120.2	C21A—C2A—H2A	120.8
C16—C11—C12	119.29 (19)	C12A—C11A—C16A	119.0 (2)
C16—C11—C1	119.10 (19)	C12A—C11A—C1A	122.5 (2)
C12—C11—C1	121.6 (2)	C16A—C11A—C1A	118.2 (2)
C13—C12—C11	120.6 (2)	C11A—C12A—C13A	120.8 (2)
C13—C12—Br1	119.77 (17)	C11A—C12A—Br1A	121.18 (16)
C11—C12—Br1	119.51 (16)	C13A—C12A—Br1A	117.95 (18)
C14—C13—C12	120.3 (2)	C14A—C13A—C12A	119.8 (2)
C14—C13—H13	119.8	C14A—C13A—H13A	120.1
C12—C13—H13	119.8	C12A—C13A—H13A	120.1
C13—C14—C15	119.9 (2)	C13A—C14A—C15A	120.3 (2)
C13—C14—H14	120.0	C13A—C14A—H14A	119.8
C15—C14—H14	120.0	C15A—C14A—H14A	119.8
O17—C15—C14	124.8 (2)	O17A—C15A—C16A	124.8 (2)
O17—C15—C16	115.7 (2)	O17A—C15A—C14A	115.5 (2)
C14—C15—C16	119.5 (2)	C16A—C15A—C14A	119.7 (2)
C11—C16—C15	120.4 (2)	C15A—C16A—C11A	120.4 (2)
C11—C16—H16	119.8	C15A—C16A—H16A	119.8
C15—C16—H16	119.8	C11A—C16A—H16A	119.8
C15—O17—C17	117.21 (19)	C15A—O17A—C17A	117.79 (18)
O17—C17—H17A	109.5	O17A—C17A—H17D	109.5
O17—C17—H17B	109.5	O17A—C17A—H17E	109.5
H17A—C17—H17B	109.5	H17D—C17A—H17E	109.5
O17—C17—H17C	109.5	O17A—C17A—H17F	109.5
H17A—C17—H17C	109.5	H17D—C17A—H17F	109.5
H17B—C17—H17C	109.5	H17E—C17A—H17F	109.5
C26—C21—C22	116.39 (19)	C22A—C21A—C26A	116.33 (19)
C26—C21—C2	119.9 (2)	C22A—C21A—C2A	124.8 (2)
C22—C21—C2	123.7 (2)	C26A—C21A—C2A	118.8 (2)
C23—C22—C21	123.1 (2)	C23A—C22A—C21A	122.8 (2)
C23—C22—N22	115.7 (2)	C23A—C22A—N22A	115.6 (2)
C21—C22—N22	121.25 (18)	C21A—C22A—N22A	121.60 (19)
C24—C23—C22	118.8 (2)	C24A—C23A—C22A	118.9 (2)
C24—C23—H23	120.6	C24A—C23A—H23A	120.5
C22—C23—H23	120.6	C22A—C23A—H23A	120.5
C25—C24—C23	119.9 (2)	C25A—C24A—C23A	120.1 (2)
C25—C24—H24	120.1	C25A—C24A—H24A	120.0
C23—C24—H24	120.1	C23A—C24A—H24A	120.0
C24—C25—C26	120.6 (2)	C24A—C25A—C26A	120.1 (2)
C24—C25—H25	119.7	C24A—C25A—H25A	120.0
C26—C25—H25	119.7	C26A—C25A—H25A	120.0
C25—C26—C21	121.2 (2)	C25A—C26A—C21A	121.7 (2)
C25—C26—H26	119.4	C25A—C26A—H26A	119.1
C21—C26—H26	119.4	C21A—C26A—H26A	119.1
O21—N22—O22	123.3 (2)	O21A—N22A—O22A	123.4 (2)
O21—N22—C22	118.03 (19)	O21A—N22A—C22A	118.6 (2)
O22—N22—C22	118.63 (19)	O22A—N22A—C22A	117.9 (2)

O1—C1—N1—N2	5.9 (4)	O1A—C1A—N1A—N2A	−5.4 (3)
C11—C1—N1—N2	−172.86 (19)	C11A—C1A—N1A—N2A	174.89 (19)
C1—N1—N2—C2	−179.1 (2)	C1A—N1A—N2A—C2A	177.2 (2)
N1—N2—C2—C21	−178.92 (19)	N1A—N2A—C2A—C21A	179.8 (2)
O1—C1—C11—C16	−107.3 (3)	O1A—C1A—C11A—C12A	104.5 (3)
N1—C1—C11—C16	71.5 (3)	N1A—C1A—C11A—C12A	−75.8 (3)
O1—C1—C11—C12	74.2 (3)	O1A—C1A—C11A—C16A	−68.7 (3)
N1—C1—C11—C12	−106.9 (2)	N1A—C1A—C11A—C16A	111.0 (2)
C16—C11—C12—C13	2.1 (3)	C16A—C11A—C12A—C13A	−0.2 (3)
C1—C11—C12—C13	−179.4 (2)	C1A—C11A—C12A—C13A	−173.3 (2)
C16—C11—C12—Br1	−173.15 (17)	C16A—C11A—C12A—Br1A	176.51 (17)
C1—C11—C12—Br1	5.3 (3)	C1A—C11A—C12A—Br1A	3.4 (3)
C11—C12—C13—C14	−2.4 (4)	C11A—C12A—C13A—C14A	0.0 (4)
Br1—C12—C13—C14	172.88 (18)	Br1A—C12A—C13A—C14A	−176.78 (19)
C12—C13—C14—C15	0.3 (4)	C12A—C13A—C14A—C15A	−0.3 (4)
C13—C14—C15—O17	−178.0 (2)	C13A—C14A—C15A—O17A	−179.7 (2)
C13—C14—C15—C16	1.9 (4)	C13A—C14A—C15A—C16A	0.8 (4)
C12—C11—C16—C15	0.1 (3)	O17A—C15A—C16A—C11A	179.5 (2)
C1—C11—C16—C15	−178.3 (2)	C14A—C15A—C16A—C11A	−1.0 (4)
O17—C15—C16—C11	177.8 (2)	C12A—C11A—C16A—C15A	0.7 (3)
C14—C15—C16—C11	−2.1 (3)	C1A—C11A—C16A—C15A	174.1 (2)
C14—C15—O17—C17	15.5 (4)	C16A—C15A—O17A—C17A	1.6 (4)
C16—C15—O17—C17	−164.4 (2)	C14A—C15A—O17A—C17A	−177.9 (2)
N2—C2—C21—C26	−24.0 (3)	N2A—C2A—C21A—C22A	−169.3 (2)
N2—C2—C21—C22	159.2 (2)	N2A—C2A—C21A—C26A	13.2 (3)
C26—C21—C22—C23	−0.2 (3)	C26A—C21A—C22A—C23A	0.6 (3)
C2—C21—C22—C23	176.7 (2)	C2A—C21A—C22A—C23A	−176.9 (2)
C26—C21—C22—N22	179.8 (2)	C26A—C21A—C22A—N22A	−177.7 (2)
C2—C21—C22—N22	−3.2 (3)	C2A—C21A—C22A—N22A	4.7 (4)
C21—C22—C23—C24	−0.2 (4)	C21A—C22A—C23A—C24A	−1.8 (4)
N22—C22—C23—C24	179.7 (2)	N22A—C22A—C23A—C24A	176.6 (2)
C22—C23—C24—C25	−0.1 (4)	C22A—C23A—C24A—C25A	1.1 (4)
C23—C24—C25—C26	0.7 (4)	C23A—C24A—C25A—C26A	0.7 (4)
C24—C25—C26—C21	−1.2 (4)	C24A—C25A—C26A—C21A	−1.9 (4)
C22—C21—C26—C25	0.9 (3)	C22A—C21A—C26A—C25A	1.3 (3)
C2—C21—C26—C25	−176.1 (2)	C2A—C21A—C26A—C25A	179.0 (2)
C23—C22—N22—O21	−27.5 (3)	C23A—C22A—N22A—O21A	27.1 (3)
C21—C22—N22—O21	152.4 (2)	C21A—C22A—N22A—O21A	−154.4 (2)
C23—C22—N22—O22	152.5 (2)	C23A—C22A—N22A—O22A	−150.8 (2)
C21—C22—N22—O22	−27.6 (3)	C21A—C22A—N22A—O22A	27.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1Aⁱ	0.86 (3)	2.09 (3)	2.863 (2)	149 (3)
N1A—H1A···O1	0.89 (3)	2.00 (3)	2.872 (3)	165 (3)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂BrN₃O₄
M_r	378.19
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.1611 (6), 9.0279 (6), 21.3467 (15)
α, β, γ (°)	85.585 (6), 89.441 (6), 75.912 (5)
V (Å³)	1520.88 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.73
Crystal size (mm)	0.36 × 0.33 × 0.32

Data collection
Diffractometer	Stoe IPDSII two-circle
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.401, 0.426
No. of measured, independent and observed [I > 2σ(I)] reflections	22860, 7003, 5849
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.091, 1.01
No. of reflections	7003
No. of parameters	426
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.99, −0.82

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97.