2,4-Dibromo-6-{(E)-[(R)-1-phenyl­ethyl]imino­meth­yl}phenol

Xia, D.-G.; Ye, Y.-F.; Lei, K.-W.

doi:10.1107/S1600536809044638

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3168

doi:10.1107/S1600536809044638

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2,4-Dibromo-6-{(E)-[(R)-1-phenylethyl]iminomethyl}phenol

Dong-Guo Xia,^a Ya-Fen Ye ^a and Ke-Wei Lei ^a ^*

^aState Key Laboratory Base of Novel Functional Materials and Preparation Science Institute of solid Materials Chemistry, Faculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, People's Republic of China
^*Correspondence e-mail: leikeweipublic@hotmail.com

(Received 21 July 2009; accepted 27 October 2009; online 21 November 2009)

In the title Schiff base, C₁₅H₁₃Br₂NO, the benzene and phenyl rings form a dihedral angle of 75.18 (13)°. The N=C bond length of 1.263 (6) Å is shorter than of the N—C bond [1.476 (5) Å], indicating a double bond. In the crystal, there is some pseudosymmetry. This occurs because most of the two molecules are centrosymmetrically related. The molecular structure is stabilized by intramolecular O—H⋯N hydrogen bonds.

Related literature

For photochromism and thermochromism in Schiff base compounds, see: Cohen et al. (1964 ).

Experimental

Crystal data

C₁₅H₁₃Br₂NO
M_r = 383.08
Monoclinic, I 2
a = 15.523 (2) Å
b = 9.3533 (12) Å
c = 21.527 (4) Å
β = 109.287 (2)°
V = 2950.1 (7) Å³
Z = 8
Mo Kα radiation
μ = 5.49 mm⁻¹
T = 296 K
0.38 × 0.31 × 0.26 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.158, T_max = 0.236
12876 measured reflections
6480 independent reflections
4357 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.082
S = 0.99
6480 reflections
346 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.50 e Å⁻³
Absolute structure: Flack (1983 ), 3189 Friedel pairs
Flack parameter: 0.022 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.81	1.89	2.603 (4)	147
O2—H2⋯N2	0.87	1.79	2.558 (5)	147

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044638/bv2125sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809044638/bv2125Isup2.hkl

checkCIF report

Comment top

Schiff bases have been used extensively as ligands in the field of coordination chemistry. Some of the reasons are that the N atom plays an important role in the formation of metal complexes, and that Schiff base coppounds show photochromism and thermochromism in the solid state by proton transfer from the hydroxyl O atom to the imine N atom (Cohen et al., 1964). Here we report on a new chiral Schiff base(I).

The chiral molecular structures of (I) which are two molecules in the illustrated in Fig. 1. The bond lengths and bond angles in (I) are within normal ranges. The N1–C7 distance of 1.263 (6) Å is a slightly smaller than the distance of N2–C22(1.270 (6)). The C7, N1, C8 and C2, C1, Br1 atoms form a bond angle of 119.3 (4) and 119.5 (3) °, respectively (Table 1). The molecular conformation is stabiized by an intramolecular O–H···N hydrogen bond (Table 2).

Related literature top

For photochromism and thermochromism in Schiff base coppounds, see: Cohen et al. (1964).

Experimental top

R-1-phenylethanamine (0.02 mol,2.42 g) and 3,5-dibromo-2-hydroxybenzaldehyde (0.02 mol,5.60 g) were dissolved in ethanol and the solution was refluxed for 4 h. After evaporation, a crude product was recrystallized twice from ethanol to give a pure yellow product. Yield: 83.7%. Calcd.for C₁₅H₁₃Br₂NO: C, 47.03; H, 3.42; N, 3.66; Found: C, 46.95; H, 3.49; N, 3.62%.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

2,4-Dibromo-6-{(E)-[(R)-1-phenylethyl]iminomethyl}phenol top

Crystal data top

C₁₅H₁₃Br₂NO	F(000) = 1504
M_r = 383.08	D_x = 1.725 Mg m⁻³
Monoclinic, I2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2y	Cell parameters from 3597 reflections
a = 15.523 (2) Å	θ = 2.4–23.4°
b = 9.3533 (12) Å	µ = 5.49 mm⁻¹
c = 21.527 (4) Å	T = 296 K
β = 109.287 (2)°	Block, yellow
V = 2950.1 (7) Å³	0.38 × 0.31 × 0.26 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD diffractometer	6480 independent reflections
Radiation source: fine-focus sealed tube	4357 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −20→20
T_min = 0.158, T_max = 0.236	k = −12→11
12876 measured reflections	l = −27→26

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0192P)² + 1.2456P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.002
6480 reflections	Δρ_max = 0.62 e Å⁻³
346 parameters	Δρ_min = −0.50 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2872 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.022 (9)

Crystal data top

C₁₅H₁₃Br₂NO	V = 2950.1 (7) Å³
M_r = 383.08	Z = 8
Monoclinic, I2	Mo Kα radiation
a = 15.523 (2) Å	µ = 5.49 mm⁻¹
b = 9.3533 (12) Å	T = 296 K
c = 21.527 (4) Å	0.38 × 0.31 × 0.26 mm
β = 109.287 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	6480 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	4357 reflections with I > 2σ(I)
T_min = 0.158, T_max = 0.236	R_int = 0.026
12876 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	Δρ_max = 0.62 e Å⁻³
S = 0.99	Δρ_min = −0.50 e Å⁻³
6480 reflections	Absolute structure: Flack (1983), 2872 Friedel pairs
346 parameters	Absolute structure parameter: 0.022 (9)
1 restraint

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	0.37953 (5)	−0.48288 (5)	1.03409 (3)	0.0857 (2)
Br2	0.34338 (4)	0.04283 (6)	1.15258 (2)	0.07989 (19)
Br3	0.16026 (3)	0.83627 (6)	0.83602 (2)	0.06812 (15)
Br4	0.11106 (5)	1.32687 (6)	0.97217 (3)	0.0987 (2)
N1	0.3623 (2)	0.1446 (4)	0.90617 (16)	0.0519 (9)
N2	0.1352 (2)	0.6719 (4)	1.07323 (16)	0.0545 (9)
O1	0.3584 (2)	0.1594 (3)	1.02596 (14)	0.0596 (9)
H1	0.3621 (3)	0.1891 (19)	0.992 (2)	0.089*
O2	0.1494 (2)	0.6885 (3)	0.95843 (14)	0.0616 (9)
H2	0.1469 (3)	0.649 (2)	0.994 (2)	0.092*
C1	0.3775 (3)	−0.2791 (5)	1.0328 (2)	0.0527 (11)
C2	0.3679 (3)	−0.2060 (5)	1.0852 (2)	0.0492 (11)
H2B	0.3653	−0.2546	1.1222	0.059*
C3	0.3622 (3)	−0.0595 (5)	1.08201 (19)	0.0512 (11)
C4	0.3661 (3)	0.0165 (5)	1.02755 (18)	0.0434 (9)
C5	0.3760 (3)	−0.0612 (5)	0.97431 (19)	0.0459 (10)
C6	0.3816 (3)	−0.2091 (5)	0.9777 (2)	0.0540 (12)
H6A	0.3881	−0.2610	0.9427	0.065*
C7	0.3746 (3)	0.0115 (5)	0.9143 (2)	0.0515 (10)
H7A	0.3832	−0.0423	0.8805	0.062*
C8	0.3566 (3)	0.2086 (5)	0.84227 (19)	0.0549 (11)
H8A	0.3705	0.1353	0.8144	0.066*
C9	0.2603 (3)	0.2606 (4)	0.80995 (18)	0.0448 (10)
C10	0.2032 (3)	0.1924 (5)	0.7561 (2)	0.0555 (11)
H10A	0.2249	0.1156	0.7382	0.067*
C11	0.1137 (3)	0.2351 (7)	0.7277 (2)	0.0750 (15)
H11A	0.0756	0.1862	0.6914	0.090*
C12	0.0810 (3)	0.3481 (7)	0.7525 (3)	0.0783 (16)
H12A	0.0211	0.3784	0.7326	0.094*
C13	0.1371 (4)	0.4176 (6)	0.8071 (3)	0.0737 (15)
H13A	0.1145	0.4935	0.8250	0.088*
C14	0.2261 (3)	0.3758 (5)	0.8354 (2)	0.0601 (12)
H14A	0.2639	0.4249	0.8717	0.072*
C15	0.4278 (3)	0.3274 (6)	0.8551 (2)	0.0783 (15)
H15A	0.4876	0.2875	0.8750	0.117*
H15B	0.4164	0.3970	0.8843	0.117*
H15C	0.4242	0.3724	0.8143	0.117*
C16	0.1200 (3)	1.1252 (5)	0.9680 (2)	0.0541 (11)
C17	0.1326 (2)	1.0647 (5)	0.91308 (18)	0.0465 (9)
H17A	0.1352	1.1218	0.8784	0.056*
C18	0.1413 (3)	0.9194 (5)	0.91066 (18)	0.0447 (10)
C19	0.1391 (2)	0.8311 (6)	0.96208 (17)	0.0460 (9)
C20	0.1247 (3)	0.8938 (5)	1.01712 (19)	0.0468 (10)
C21	0.1163 (3)	1.0434 (5)	1.01940 (19)	0.0553 (12)
H21A	0.1082	1.0864	1.0560	0.066*
C22	0.1220 (3)	0.8060 (6)	1.0725 (2)	0.0591 (13)
H22A	0.1104	0.8490	1.1079	0.071*
C23	0.1351 (3)	0.5817 (5)	1.12971 (19)	0.0582 (12)
H23A	0.1198	0.4849	1.1121	0.070*
C24	0.2320 (3)	0.5733 (5)	1.17797 (19)	0.0508 (10)
C25	0.2650 (3)	0.6751 (6)	1.2257 (2)	0.0672 (13)
H25A	0.2273	0.7496	1.2294	0.081*
C26	0.3544 (4)	0.6682 (7)	1.2688 (3)	0.0884 (18)
H26A	0.3766	0.7378	1.3010	0.106*
C27	0.4104 (4)	0.5554 (9)	1.2630 (3)	0.094 (2)
H27A	0.4697	0.5475	1.2920	0.113*
C28	0.3767 (4)	0.4568 (8)	1.2141 (3)	0.0921 (19)
H28A	0.4137	0.3824	1.2092	0.111*
C29	0.2892 (3)	0.4672 (6)	1.1726 (2)	0.0691 (14)
H29A	0.2678	0.3995	1.1394	0.083*
C30	0.0640 (3)	0.6210 (7)	1.1599 (2)	0.0813 (16)
H30A	0.0051	0.6225	1.1264	0.122*
H30B	0.0774	0.7139	1.1797	0.122*
H30C	0.0641	0.5519	1.1929	0.122*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1247 (5)	0.0516 (3)	0.0857 (4)	0.0224 (3)	0.0414 (4)	0.0129 (3)
Br2	0.1140 (4)	0.0779 (4)	0.0438 (2)	0.0113 (3)	0.0207 (2)	−0.0087 (3)
Br3	0.0959 (4)	0.0645 (3)	0.0470 (2)	−0.0069 (3)	0.0277 (2)	−0.0083 (3)
Br4	0.1556 (6)	0.0524 (3)	0.1062 (4)	0.0174 (4)	0.0676 (4)	0.0002 (4)
N1	0.055 (2)	0.055 (3)	0.0459 (19)	−0.0056 (18)	0.0166 (16)	0.0031 (18)
N2	0.050 (2)	0.061 (3)	0.049 (2)	−0.0049 (18)	0.0103 (17)	0.0050 (18)
O1	0.083 (2)	0.0407 (18)	0.0500 (18)	0.0035 (15)	0.0152 (16)	−0.0009 (14)
O2	0.080 (2)	0.050 (2)	0.0496 (18)	−0.0038 (16)	0.0148 (16)	0.0040 (15)
C1	0.048 (3)	0.047 (3)	0.059 (3)	0.009 (2)	0.013 (2)	0.008 (2)
C2	0.049 (3)	0.053 (3)	0.044 (2)	0.003 (2)	0.0131 (19)	0.0082 (19)
C3	0.048 (3)	0.059 (3)	0.040 (2)	0.001 (2)	0.006 (2)	−0.009 (2)
C4	0.039 (2)	0.039 (2)	0.044 (2)	−0.0001 (19)	0.0036 (17)	0.0030 (19)
C5	0.040 (2)	0.048 (3)	0.047 (2)	0.005 (2)	0.0122 (19)	0.003 (2)
C6	0.050 (3)	0.062 (3)	0.053 (3)	0.014 (2)	0.021 (2)	0.001 (2)
C7	0.045 (2)	0.059 (3)	0.051 (2)	0.006 (2)	0.0177 (19)	0.000 (2)
C8	0.057 (3)	0.067 (3)	0.047 (2)	−0.001 (2)	0.025 (2)	0.008 (2)
C9	0.050 (3)	0.047 (2)	0.042 (2)	−0.003 (2)	0.022 (2)	0.0084 (19)
C10	0.068 (3)	0.049 (3)	0.056 (3)	0.002 (2)	0.028 (2)	0.004 (2)
C11	0.062 (3)	0.089 (4)	0.065 (3)	−0.019 (3)	0.008 (3)	0.017 (3)
C12	0.060 (3)	0.077 (4)	0.098 (4)	0.019 (3)	0.027 (3)	0.036 (4)
C13	0.081 (4)	0.058 (3)	0.096 (4)	0.009 (3)	0.049 (3)	0.015 (3)
C14	0.062 (3)	0.058 (3)	0.066 (3)	−0.007 (2)	0.029 (2)	−0.003 (2)
C15	0.056 (3)	0.095 (4)	0.083 (3)	−0.011 (3)	0.022 (2)	0.032 (3)
C16	0.062 (3)	0.051 (3)	0.052 (3)	0.006 (2)	0.022 (2)	0.003 (2)
C17	0.048 (2)	0.045 (2)	0.043 (2)	−0.001 (2)	0.0105 (18)	0.008 (2)
C18	0.041 (2)	0.053 (3)	0.039 (2)	−0.0018 (19)	0.0110 (19)	−0.0010 (19)
C19	0.034 (2)	0.052 (3)	0.046 (2)	−0.008 (2)	0.0057 (17)	−0.001 (2)
C20	0.041 (2)	0.060 (3)	0.038 (2)	0.0021 (19)	0.0121 (18)	0.011 (2)
C21	0.055 (3)	0.067 (3)	0.048 (2)	0.002 (2)	0.023 (2)	−0.005 (2)
C22	0.054 (3)	0.078 (4)	0.046 (2)	−0.002 (3)	0.019 (2)	−0.007 (2)
C23	0.060 (3)	0.065 (3)	0.045 (2)	−0.009 (2)	0.011 (2)	0.013 (2)
C24	0.049 (2)	0.061 (3)	0.044 (2)	−0.003 (2)	0.0170 (18)	0.015 (2)
C25	0.057 (3)	0.074 (3)	0.067 (3)	0.005 (3)	0.015 (2)	0.007 (3)
C26	0.088 (5)	0.093 (5)	0.071 (4)	−0.026 (4)	0.008 (3)	−0.003 (3)
C27	0.046 (3)	0.124 (6)	0.099 (4)	−0.005 (4)	0.006 (3)	0.044 (5)
C28	0.066 (4)	0.103 (5)	0.116 (5)	0.030 (4)	0.042 (4)	0.044 (4)
C29	0.070 (3)	0.073 (4)	0.071 (3)	0.013 (3)	0.032 (3)	0.020 (3)
C30	0.051 (3)	0.124 (5)	0.068 (3)	0.000 (3)	0.018 (2)	0.037 (3)

Geometric parameters (Å, º) top

Br1—C1	1.907 (5)	C13—C14	1.370 (7)
Br2—C3	1.898 (4)	C13—H13A	0.9300
Br3—C18	1.894 (4)	C14—H14A	0.9300
Br4—C16	1.896 (5)	C15—H15A	0.9600
N1—C7	1.263 (6)	C15—H15B	0.9600
N1—C8	1.476 (5)	C15—H15C	0.9600
N2—C22	1.270 (6)	C16—C21	1.362 (6)
N2—C23	1.480 (5)	C16—C17	1.381 (6)
O1—C4	1.342 (5)	C17—C18	1.369 (6)
O1—H1	0.8066	C17—H17A	0.9300
O2—C19	1.348 (6)	C18—C19	1.390 (6)
O2—H2	0.8662	C19—C20	1.405 (6)
C1—C2	1.368 (6)	C20—C21	1.408 (7)
C1—C6	1.374 (6)	C20—C22	1.460 (6)
C2—C3	1.373 (6)	C21—H21A	0.9300
C2—H2B	0.9300	C22—H22A	0.9300
C3—C4	1.389 (6)	C23—C30	1.500 (6)
C4—C5	1.408 (6)	C23—C24	1.521 (6)
C5—C6	1.386 (6)	C23—H23A	0.9800
C5—C7	1.453 (6)	C24—C29	1.362 (6)
C6—H6A	0.9300	C24—C25	1.370 (6)
C7—H7A	0.9300	C25—C26	1.392 (7)
C8—C9	1.507 (6)	C25—H25A	0.9300
C8—C15	1.527 (6)	C26—C27	1.399 (9)
C8—H8A	0.9800	C26—H26A	0.9300
C9—C10	1.363 (5)	C27—C28	1.366 (9)
C9—C14	1.390 (6)	C27—H27A	0.9300
C10—C11	1.379 (6)	C28—C29	1.360 (7)
C10—H10A	0.9300	C28—H28A	0.9300
C11—C12	1.355 (8)	C29—H29A	0.9300
C11—H11A	0.9300	C30—H30A	0.9600
C12—C13	1.373 (7)	C30—H30B	0.9600
C12—H12A	0.9300	C30—H30C	0.9600

C7—N1—C8	119.3 (4)	H15A—C15—H15C	109.5
C22—N2—C23	121.9 (4)	H15B—C15—H15C	109.5
C4—O1—H1	109.5	C21—C16—C17	121.4 (4)
C19—O2—H2	109.5	C21—C16—Br4	119.8 (3)
C2—C1—C6	121.5 (4)	C17—C16—Br4	118.8 (3)
C2—C1—Br1	119.5 (3)	C18—C17—C16	118.8 (4)
C6—C1—Br1	118.9 (4)	C18—C17—H17A	120.6
C1—C2—C3	118.7 (4)	C16—C17—H17A	120.6
C1—C2—H2B	120.7	C17—C18—C19	122.1 (4)
C3—C2—H2B	120.7	C17—C18—Br3	119.0 (3)
C2—C3—C4	122.2 (4)	C19—C18—Br3	118.9 (3)
C2—C3—Br2	119.2 (4)	O2—C19—C18	120.4 (4)
C4—C3—Br2	118.6 (3)	O2—C19—C20	121.1 (4)
O1—C4—C3	120.2 (4)	C18—C19—C20	118.4 (5)
O1—C4—C5	121.8 (4)	C19—C20—C21	119.1 (4)
C3—C4—C5	118.0 (4)	C19—C20—C22	120.6 (4)
C6—C5—C4	119.6 (4)	C21—C20—C22	120.2 (4)
C6—C5—C7	119.7 (4)	C16—C21—C20	120.0 (4)
C4—C5—C7	120.6 (4)	C16—C21—H21A	120.0
C1—C6—C5	120.0 (4)	C20—C21—H21A	120.0
C1—C6—H6A	120.0	N2—C22—C20	121.1 (4)
C5—C6—H6A	120.0	N2—C22—H22A	119.4
N1—C7—C5	122.8 (4)	C20—C22—H22A	119.4
N1—C7—H7A	118.6	N2—C23—C30	114.6 (4)
C5—C7—H7A	118.6	N2—C23—C24	108.8 (3)
N1—C8—C9	107.8 (3)	C30—C23—C24	114.8 (4)
N1—C8—C15	108.0 (3)	N2—C23—H23A	106.0
C9—C8—C15	113.4 (4)	C30—C23—H23A	106.0
N1—C8—H8A	109.2	C24—C23—H23A	106.0
C9—C8—H8A	109.2	C29—C24—C25	118.5 (4)
C15—C8—H8A	109.2	C29—C24—C23	120.3 (5)
C10—C9—C14	118.2 (4)	C25—C24—C23	121.1 (4)
C10—C9—C8	120.6 (4)	C24—C25—C26	120.8 (5)
C14—C9—C8	121.2 (4)	C24—C25—H25A	119.6
C9—C10—C11	121.2 (4)	C26—C25—H25A	119.6
C9—C10—H10A	119.4	C25—C26—C27	119.1 (5)
C11—C10—H10A	119.4	C25—C26—H26A	120.4
C12—C11—C10	120.3 (5)	C27—C26—H26A	120.4
C12—C11—H11A	119.8	C28—C27—C26	119.2 (5)
C10—C11—H11A	119.8	C28—C27—H27A	120.4
C11—C12—C13	119.5 (5)	C26—C27—H27A	120.4
C11—C12—H12A	120.3	C29—C28—C27	120.2 (6)
C13—C12—H12A	120.3	C29—C28—H28A	119.9
C14—C13—C12	120.4 (5)	C27—C28—H28A	119.9
C14—C13—H13A	119.8	C28—C29—C24	122.2 (6)
C12—C13—H13A	119.8	C28—C29—H29A	118.9
C13—C14—C9	120.4 (4)	C24—C29—H29A	118.9
C13—C14—H14A	119.8	C23—C30—H30A	109.5
C9—C14—H14A	119.8	C23—C30—H30B	109.5
C8—C15—H15A	109.5	H30A—C30—H30B	109.5
C8—C15—H15B	109.5	C23—C30—H30C	109.5
H15A—C15—H15B	109.5	H30A—C30—H30C	109.5
C8—C15—H15C	109.5	H30B—C30—H30C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.81	1.89	2.603 (4)	147
O2—H2···N2	0.87	1.79	2.558 (5)	147

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃Br₂NO
M_r	383.08
Crystal system, space group	Monoclinic, I2
Temperature (K)	296
a, b, c (Å)	15.523 (2), 9.3533 (12), 21.527 (4)
β (°)	109.287 (2)
V (Å³)	2950.1 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.49
Crystal size (mm)	0.38 × 0.31 × 0.26

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.158, 0.236
No. of measured, independent and observed [I > 2σ(I)] reflections	12876, 6480, 4357
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.082, 0.99
No. of reflections	6480
No. of parameters	346
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.50
Absolute structure	Flack (1983), 2872 Friedel pairs
Absolute structure parameter	0.022 (9)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Br1—C1	1.907 (5)	N1—C7	1.263 (6)
Br2—C3	1.898 (4)	N1—C8	1.476 (5)
Br3—C18	1.894 (4)	N2—C22	1.270 (6)
Br4—C16	1.896 (5)	N2—C23	1.480 (5)

C7—N1—C8	119.3 (4)	C4—C3—Br2	118.6 (3)
C22—N2—C23	121.9 (4)	N1—C8—C9	107.8 (3)
C2—C1—Br1	119.5 (3)	N1—C8—C15	108.0 (3)
C6—C1—Br1	118.9 (4)	N2—C23—C30	114.6 (4)
C2—C3—Br2	119.2 (4)	N2—C23—C24	108.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.81	1.89	2.603 (4)	146.9
O2—H2···N2	0.87	1.79	2.558 (5)	147.4

Acknowledgements

This project was supported by the Talent Fund of Ningbo University (grant No. 2006668) and sponsored by the K.C. Wong Magna Fund of Ningbo University.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cohen, M. D., Schmidt, G. M. J. & Flavian, S. (1964). J. Chem. Soc. pp. 2041–2043. CrossRef Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar