(E)-4-Bromo-N′-[(5-methyl­furan-2-yl)­methyl­ene]benzohydrazide

Bai, Z.-C.; Jing, Z.-L.

doi:10.1107/S1600536807040081

(E)-4-Bromo-N′-[(5-methylfuran-2-yl)methylene]benzohydrazide

The asymmetric unit of the title compound, C₁₃H₁₁BrN₂O₂, contains two independent molecules. In one molecule, the dihedral angle between the two ring planes is 28.10 (3)°; in the other, it is 28.90 (3)°. Intermolecular N—H

O hydrogen bonds link the molecules to form a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040081/at2374sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040081/at2374Isup2.hkl Contains datablock I

CCDC reference: 660295

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Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R factor = 0.041
wR factor = 0.104
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        300 Deg.
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.00 Ratio
PLAT245_ALERT_2_C U(iso) H4A     Smaller than U(eq) N4      by ...       0.02 AngSq

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al.,2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).

In the structure of the title molecule (I) (Fig. 1), the geometric parameters are normal. In the one molecule of the unit, the furan ring (C2—C5/O1) is approximately planar, with a maximum deviation from the mean plane of 0.0023 (2) Å for atom O1, as are the benzene group (C8—C13) is approximately planar, with a maximum deviation from the mean plane of 0.0060 (5) Å. The dihedral angle between these two planes is 28.10 (3)°. In the other molecule of the unit, the furan ring (C15—C18/O3) is approximately planar, with a maximum deviation from the mean plane of 0.0019 (2) Å for atom O3, as are the benzene group (C21—C26) is approximately planar, with a maximum deviation from the mean plane of 0.0069 (4) Å. The dihedral angle between these two planes is 28.90 (3)°. Intermolecular N—H···O hydrogen bonds link the molecules to form a three-dimensional network, as illustraed in Fig.2 and Table 1.

Related literature top

For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).

Experimental top

An anhydrous ethanol solution (50 ml) of 4-bromobenzohydrazide (2.14 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of 5-methylfuran-2-carbaldehyde (1.10 g, 10 mmol), and the mixture was stirred at 350 K for 6 h under N₂, whereupon a red precipitate appeared. The product was isolated, recrystallized from anhydrous ethanol and then dried in vacuo to give pure compound (I) in 91% yield. Red single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an anhydrous ethanol solution.

Structure description top

For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

	Fig. 1. The structure of the title molecule (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of (I). Hydrogen bonds are indicated by dashed lines.

(E)-4-Bromo-N'-[(5-methylfuran-2-yl)methylene]benzohydrazide top

Crystal data top

C₁₃H₁₁BrN₂O₂	Z = 4
M_r = 307.15	F(000) = 616
Triclinic, P1	D_x = 1.594 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0276 (13) Å	Cell parameters from 2664 reflections
b = 10.0734 (16) Å	θ = 3.3–26.4°
c = 16.458 (3) Å	µ = 3.21 mm⁻¹
α = 105.166 (3)°	T = 294 K
β = 94.668 (3)°	Block, red
γ = 90.576 (3)°	0.20 × 0.18 × 0.16 mm
V = 1279.6 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4482 independent reflections
Radiation source: fine-focus sealed tube	3125 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.566, T_max = 0.628	k = −11→11
6684 measured reflections	l = −18→19

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0417P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4482 reflections	Δρ_max = 0.50 e Å⁻³
336 parameters	Δρ_min = −0.64 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0259 (15)

Crystal data top

C₁₃H₁₁BrN₂O₂	γ = 90.576 (3)°
M_r = 307.15	V = 1279.6 (4) Å³
Triclinic, P1	Z = 4
a = 8.0276 (13) Å	Mo Kα radiation
b = 10.0734 (16) Å	µ = 3.21 mm⁻¹
c = 16.458 (3) Å	T = 294 K
α = 105.166 (3)°	0.20 × 0.18 × 0.16 mm
β = 94.668 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4482 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3125 reflections with I > 2σ(I)
T_min = 0.566, T_max = 0.628	R_int = 0.036
6684 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	2 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.50 e Å⁻³
4482 reflections	Δρ_min = −0.64 e Å⁻³
336 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	0.44683 (6)	0.33727 (4)	0.10793 (2)	0.06531 (18)
Br2	0.82935 (6)	0.82934 (4)	0.09703 (2)	0.06943 (19)
O1	0.9618 (3)	0.5777 (2)	0.77720 (14)	0.0454 (6)
O2	0.6940 (4)	0.2664 (2)	0.49922 (14)	0.0668 (8)
O3	0.6924 (3)	1.0721 (2)	0.78316 (13)	0.0468 (6)
O4	0.8046 (4)	0.7674 (2)	0.49693 (14)	0.0661 (8)
N1	0.8312 (4)	0.5044 (3)	0.60515 (17)	0.0454 (7)
N2	0.7656 (4)	0.4902 (3)	0.52273 (17)	0.0455 (7)
N3	0.7319 (4)	1.0057 (3)	0.60812 (16)	0.0450 (7)
N4	0.7522 (4)	0.9927 (3)	0.52433 (17)	0.0456 (7)
C1	1.0508 (6)	0.5719 (4)	0.9199 (2)	0.0724 (12)
H1A	1.0758	0.6347	0.9746	0.109*
H1B	1.1425	0.5118	0.9066	0.109*
H1C	0.9513	0.5183	0.9201	0.109*
C2	1.0243 (5)	0.6503 (4)	0.8557 (2)	0.0492 (9)
C3	1.0466 (5)	0.7819 (4)	0.8572 (3)	0.0625 (11)
H3	1.0876	0.8524	0.9036	0.075*
C4	0.9965 (5)	0.7946 (4)	0.7760 (3)	0.0588 (10)
H4	0.9976	0.8749	0.7582	0.071*
C5	0.9472 (4)	0.6694 (3)	0.7295 (2)	0.0447 (8)
C6	0.8793 (4)	0.6266 (3)	0.6434 (2)	0.0457 (9)
H6	0.8697	0.6930	0.6134	0.055*
C7	0.7004 (4)	0.3704 (3)	0.4743 (2)	0.0431 (8)
C8	0.6356 (4)	0.3699 (3)	0.3872 (2)	0.0381 (8)
C9	0.5169 (4)	0.2708 (3)	0.3442 (2)	0.0464 (9)
H9	0.4754	0.2092	0.3715	0.056*
C10	0.4596 (4)	0.2615 (3)	0.2627 (2)	0.0464 (9)
H10	0.3791	0.1945	0.2346	0.056*
C11	0.5224 (4)	0.3526 (3)	0.2223 (2)	0.0423 (8)
C12	0.6365 (4)	0.4532 (3)	0.2634 (2)	0.0462 (9)
H12	0.6751	0.5158	0.2359	0.055*
C13	0.6945 (4)	0.4622 (3)	0.3451 (2)	0.0468 (9)
H13	0.7738	0.5304	0.3729	0.056*
C14	0.6697 (6)	1.0567 (4)	0.9257 (2)	0.0773 (13)
H14A	0.6649	1.1158	0.9815	0.116*
H14B	0.7712	1.0067	0.9232	0.116*
H14C	0.5754	0.9930	0.9122	0.116*
C15	0.6659 (5)	1.1406 (4)	0.8640 (2)	0.0516 (9)
C16	0.6427 (5)	1.2732 (4)	0.8694 (2)	0.0571 (10)
H16	0.6233	1.3411	0.9178	0.068*
C17	0.6530 (5)	1.2912 (3)	0.7882 (2)	0.0537 (10)
H17	0.6410	1.3731	0.7726	0.064*
C18	0.6834 (4)	1.1680 (3)	0.7377 (2)	0.0427 (8)
C19	0.7053 (4)	1.1292 (3)	0.6498 (2)	0.0450 (8)
H19	0.7001	1.1972	0.6209	0.054*
C20	0.7872 (4)	0.8710 (3)	0.4727 (2)	0.0430 (8)
C21	0.8010 (4)	0.8691 (3)	0.3830 (2)	0.0372 (8)
C22	0.8982 (4)	0.7703 (3)	0.3355 (2)	0.0437 (8)
H22	0.9568	0.7107	0.3611	0.052*
C23	0.9093 (4)	0.7592 (3)	0.2514 (2)	0.0454 (9)
H23	0.9757	0.6932	0.2199	0.054*
C24	0.8203 (4)	0.8474 (3)	0.2142 (2)	0.0424 (8)
C25	0.7257 (4)	0.9477 (3)	0.2597 (2)	0.0487 (9)
H25	0.6682	1.0076	0.2339	0.058*
C26	0.7172 (4)	0.9581 (3)	0.3436 (2)	0.0452 (9)
H26	0.6539	1.0265	0.3751	0.054*
H4A	0.755 (3)	1.0683 (18)	0.5062 (16)	0.029 (8)*
H2A	0.767 (4)	0.566 (2)	0.5041 (19)	0.050 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0881 (3)	0.0599 (3)	0.0407 (3)	0.0095 (2)	−0.0034 (2)	0.00281 (18)
Br2	0.1012 (4)	0.0675 (3)	0.0386 (3)	0.0067 (2)	0.0212 (2)	0.00751 (19)
O1	0.0665 (16)	0.0364 (13)	0.0347 (13)	0.0082 (11)	0.0074 (12)	0.0106 (11)
O2	0.122 (3)	0.0350 (14)	0.0487 (17)	0.0049 (14)	0.0062 (15)	0.0197 (12)
O3	0.0699 (16)	0.0367 (13)	0.0333 (13)	0.0042 (11)	0.0134 (11)	0.0058 (10)
O4	0.120 (2)	0.0339 (14)	0.0502 (17)	0.0105 (14)	0.0149 (15)	0.0183 (12)
N1	0.063 (2)	0.0404 (17)	0.0360 (17)	0.0135 (14)	0.0060 (14)	0.0143 (13)
N2	0.071 (2)	0.0333 (16)	0.0354 (17)	0.0097 (14)	0.0035 (15)	0.0154 (13)
N3	0.065 (2)	0.0402 (17)	0.0318 (16)	−0.0005 (14)	0.0102 (14)	0.0123 (13)
N4	0.078 (2)	0.0289 (15)	0.0347 (17)	0.0030 (14)	0.0160 (15)	0.0135 (13)
C1	0.117 (4)	0.067 (3)	0.034 (2)	0.008 (2)	0.002 (2)	0.016 (2)
C2	0.064 (2)	0.046 (2)	0.035 (2)	0.0087 (17)	0.0072 (18)	0.0044 (16)
C3	0.077 (3)	0.046 (2)	0.055 (3)	0.0001 (19)	−0.009 (2)	0.0002 (19)
C4	0.073 (3)	0.039 (2)	0.064 (3)	−0.0021 (18)	−0.003 (2)	0.0158 (19)
C5	0.051 (2)	0.039 (2)	0.047 (2)	0.0103 (16)	0.0066 (17)	0.0159 (17)
C6	0.055 (2)	0.039 (2)	0.047 (2)	0.0092 (16)	0.0057 (18)	0.0181 (17)
C7	0.061 (2)	0.0298 (18)	0.041 (2)	0.0099 (16)	0.0175 (17)	0.0102 (16)
C8	0.050 (2)	0.0268 (17)	0.0392 (19)	0.0098 (15)	0.0139 (16)	0.0088 (15)
C9	0.058 (2)	0.0315 (18)	0.054 (2)	0.0066 (16)	0.0196 (19)	0.0145 (17)
C10	0.052 (2)	0.0310 (18)	0.052 (2)	0.0043 (15)	0.0082 (18)	0.0035 (17)
C11	0.050 (2)	0.0394 (19)	0.0337 (19)	0.0127 (16)	0.0098 (16)	0.0014 (15)
C12	0.062 (2)	0.042 (2)	0.038 (2)	−0.0022 (17)	0.0073 (18)	0.0149 (16)
C13	0.054 (2)	0.044 (2)	0.041 (2)	−0.0036 (16)	0.0040 (17)	0.0090 (17)
C14	0.131 (4)	0.065 (3)	0.037 (2)	0.010 (3)	0.017 (2)	0.011 (2)
C15	0.074 (3)	0.046 (2)	0.032 (2)	0.0007 (18)	0.0108 (18)	0.0027 (16)
C16	0.075 (3)	0.045 (2)	0.045 (2)	0.0040 (19)	0.015 (2)	−0.0027 (18)
C17	0.072 (3)	0.037 (2)	0.054 (2)	0.0098 (17)	0.015 (2)	0.0099 (17)
C18	0.054 (2)	0.0362 (19)	0.041 (2)	0.0020 (15)	0.0132 (17)	0.0140 (16)
C19	0.062 (2)	0.037 (2)	0.040 (2)	0.0011 (16)	0.0106 (17)	0.0139 (16)
C20	0.057 (2)	0.0327 (19)	0.042 (2)	0.0011 (15)	0.0071 (17)	0.0142 (16)
C21	0.048 (2)	0.0266 (16)	0.0378 (19)	0.0003 (14)	0.0104 (16)	0.0084 (14)
C22	0.053 (2)	0.0297 (17)	0.050 (2)	0.0050 (15)	0.0070 (17)	0.0119 (15)
C23	0.052 (2)	0.0341 (18)	0.047 (2)	0.0051 (15)	0.0142 (17)	0.0022 (16)
C24	0.053 (2)	0.0409 (19)	0.0308 (18)	−0.0043 (16)	0.0123 (16)	0.0019 (15)
C25	0.063 (2)	0.044 (2)	0.041 (2)	0.0154 (17)	0.0097 (18)	0.0128 (16)
C26	0.058 (2)	0.0387 (19)	0.039 (2)	0.0147 (16)	0.0120 (17)	0.0088 (16)

Geometric parameters (Å, º) top

Br1—C11	1.897 (3)	C9—C10	1.361 (5)
Br2—C24	1.896 (3)	C9—H9	0.9300
O1—C2	1.359 (4)	C10—C11	1.380 (5)
O1—C5	1.360 (4)	C10—H10	0.9300
O2—C7	1.222 (3)	C11—C12	1.358 (5)
O3—C15	1.363 (4)	C12—C13	1.367 (5)
O3—C18	1.367 (4)	C12—H12	0.9300
O4—C20	1.217 (3)	C13—H13	0.9300
N1—C6	1.268 (4)	C14—C15	1.480 (5)
N1—N2	1.385 (4)	C14—H14A	0.9600
N2—C7	1.335 (4)	C14—H14B	0.9600
N2—H2A	0.890 (10)	C14—H14C	0.9600
N3—C19	1.283 (4)	C15—C16	1.331 (5)
N3—N4	1.374 (3)	C16—C17	1.403 (5)
N4—C20	1.343 (4)	C16—H16	0.9300
N4—H4A	0.889 (10)	C17—C18	1.339 (4)
C1—C2	1.479 (5)	C17—H17	0.9300
C1—H1A	0.9600	C18—C19	1.423 (4)
C1—H1B	0.9600	C19—H19	0.9300
C1—H1C	0.9600	C20—C21	1.483 (4)
C2—C3	1.329 (5)	C21—C22	1.385 (4)
C3—C4	1.403 (5)	C21—C26	1.386 (4)
C3—H3	0.9300	C22—C23	1.370 (5)
C4—C5	1.330 (5)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.379 (5)
C5—C6	1.429 (5)	C23—H23	0.9300
C6—H6	0.9300	C24—C25	1.368 (5)
C7—C8	1.484 (5)	C25—C26	1.366 (4)
C8—C9	1.381 (5)	C25—H25	0.9300
C8—C13	1.396 (4)	C26—H26	0.9300

C2—O1—C5	106.3 (3)	C11—C12—H12	120.1
C15—O3—C18	106.1 (2)	C13—C12—H12	120.1
C6—N1—N2	113.3 (3)	C12—C13—C8	120.5 (3)
C7—N2—N1	121.7 (3)	C12—C13—H13	119.8
C7—N2—H2A	122 (2)	C8—C13—H13	119.8
N1—N2—H2A	116 (2)	C15—C14—H14A	109.5
C19—N3—N4	113.6 (3)	C15—C14—H14B	109.5
C20—N4—N3	121.1 (3)	H14A—C14—H14B	109.5
C20—N4—H4A	119.8 (18)	C15—C14—H14C	109.5
N3—N4—H4A	118.7 (18)	H14A—C14—H14C	109.5
C2—C1—H1A	109.5	H14B—C14—H14C	109.5
C2—C1—H1B	109.5	C16—C15—O3	110.1 (3)
H1A—C1—H1B	109.5	C16—C15—C14	133.9 (3)
C2—C1—H1C	109.5	O3—C15—C14	115.9 (3)
H1A—C1—H1C	109.5	C15—C16—C17	107.1 (3)
H1B—C1—H1C	109.5	C15—C16—H16	126.4
C3—C2—O1	109.8 (3)	C17—C16—H16	126.4
C3—C2—C1	133.7 (4)	C18—C17—C16	106.8 (3)
O1—C2—C1	116.5 (3)	C18—C17—H17	126.6
C2—C3—C4	107.2 (3)	C16—C17—H17	126.6
C2—C3—H3	126.4	C17—C18—O3	109.8 (3)
C4—C3—H3	126.4	C17—C18—C19	129.9 (3)
C5—C4—C3	106.5 (3)	O3—C18—C19	120.3 (3)
C5—C4—H4	126.7	N3—C19—C18	123.7 (3)
C3—C4—H4	126.7	N3—C19—H19	118.2
C4—C5—O1	110.2 (3)	C18—C19—H19	118.2
C4—C5—C6	129.2 (3)	O4—C20—N4	122.6 (3)
O1—C5—C6	120.6 (3)	O4—C20—C21	121.4 (3)
N1—C6—C5	124.4 (3)	N4—C20—C21	116.0 (3)
N1—C6—H6	117.8	C22—C21—C26	118.3 (3)
C5—C6—H6	117.8	C22—C21—C20	118.3 (3)
O2—C7—N2	122.8 (3)	C26—C21—C20	123.4 (3)
O2—C7—C8	121.3 (3)	C23—C22—C21	121.0 (3)
N2—C7—C8	115.9 (3)	C23—C22—H22	119.5
C9—C8—C13	118.2 (3)	C21—C22—H22	119.5
C9—C8—C7	119.0 (3)	C22—C23—C24	118.8 (3)
C13—C8—C7	122.8 (3)	C22—C23—H23	120.6
C10—C9—C8	121.3 (3)	C24—C23—H23	120.6
C10—C9—H9	119.3	C25—C24—C23	121.7 (3)
C8—C9—H9	119.3	C25—C24—Br2	119.1 (3)
C9—C10—C11	119.1 (3)	C23—C24—Br2	119.2 (2)
C9—C10—H10	120.4	C26—C25—C24	118.7 (3)
C11—C10—H10	120.4	C26—C25—H25	120.6
C12—C11—C10	121.0 (3)	C24—C25—H25	120.6
C12—C11—Br1	119.7 (3)	C25—C26—C21	121.5 (3)
C10—C11—Br1	119.3 (3)	C25—C26—H26	119.2
C11—C12—C13	119.8 (3)	C21—C26—H26	119.2

C6—N1—N2—C7	−176.3 (3)	C7—C8—C13—C12	176.8 (3)
C19—N3—N4—C20	177.5 (3)	C18—O3—C15—C16	−0.4 (4)
C5—O1—C2—C3	0.5 (4)	C18—O3—C15—C14	179.9 (3)
C5—O1—C2—C1	179.7 (3)	O3—C15—C16—C17	0.6 (4)
O1—C2—C3—C4	−0.2 (5)	C14—C15—C16—C17	−179.9 (5)
C1—C2—C3—C4	−179.2 (4)	C15—C16—C17—C18	−0.5 (5)
C2—C3—C4—C5	−0.3 (5)	C16—C17—C18—O3	0.2 (4)
C3—C4—C5—O1	0.6 (4)	C16—C17—C18—C19	−179.8 (4)
C3—C4—C5—C6	177.6 (4)	C15—O3—C18—C17	0.1 (4)
C2—O1—C5—C4	−0.7 (4)	C15—O3—C18—C19	−179.8 (3)
C2—O1—C5—C6	−178.0 (3)	N4—N3—C19—C18	−178.9 (3)
N2—N1—C6—C5	178.2 (3)	C17—C18—C19—N3	−179.0 (4)
C4—C5—C6—N1	−177.9 (4)	O3—C18—C19—N3	0.9 (5)
O1—C5—C6—N1	−1.2 (5)	N3—N4—C20—O4	−0.9 (5)
N1—N2—C7—O2	0.2 (5)	N3—N4—C20—C21	178.2 (3)
N1—N2—C7—C8	−179.6 (3)	O4—C20—C21—C22	−26.4 (5)
O2—C7—C8—C9	23.0 (5)	N4—C20—C21—C22	154.5 (3)
N2—C7—C8—C9	−157.2 (3)	O4—C20—C21—C26	151.4 (3)
O2—C7—C8—C13	−154.3 (3)	N4—C20—C21—C26	−27.7 (5)
N2—C7—C8—C13	25.5 (5)	C26—C21—C22—C23	−1.1 (5)
C13—C8—C9—C10	0.8 (5)	C20—C21—C22—C23	176.8 (3)
C7—C8—C9—C10	−176.7 (3)	C21—C22—C23—C24	−0.6 (5)
C8—C9—C10—C11	0.4 (5)	C22—C23—C24—C25	1.9 (5)
C9—C10—C11—C12	−1.8 (5)	C22—C23—C24—Br2	−178.1 (2)
C9—C10—C11—Br1	178.5 (2)	C23—C24—C25—C26	−1.3 (5)
C10—C11—C12—C13	2.0 (5)	Br2—C24—C25—C26	178.7 (3)
Br1—C11—C12—C13	−178.2 (3)	C24—C25—C26—C21	−0.5 (5)
C11—C12—C13—C8	−0.9 (5)	C22—C21—C26—C25	1.7 (5)
C9—C8—C13—C12	−0.5 (5)	C20—C21—C26—C25	−176.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2ⁱ	0.89 (1)	2.09 (1)	2.929 (3)	157 (2)
N2—H2A···O4	0.89 (1)	2.09 (1)	2.950 (3)	163 (3)

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁BrN₂O₂
M_r	307.15
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.0276 (13), 10.0734 (16), 16.458 (3)
α, β, γ (°)	105.166 (3), 94.668 (3), 90.576 (3)
V (Å³)	1279.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.21
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.566, 0.628
No. of measured, independent and observed [I > 2σ(I)] reflections	6684, 4482, 3125
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.104, 1.02
No. of reflections	4482
No. of parameters	336
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)	0.50, −0.64

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).