(E)-1-{4-[Bis(4-bromo-phen-yl)meth-yl]piperazin-1-yl}-3-(4-eth-oxy-3-meth-oxy-phen-yl)prop-2-en-1-one.

In the title mol-ecule, C(29)H(30)Br(2)N(2)O(3), the piperazine ring has a chair conformation and the C=C double bond has an E conformation. The dihedral angle between the bromo-benzene rings is 79.1 (3)°. In the crystal, mol-ecules are linked through C-H⋯O and C-H⋯Br hydrogen bonds.

Related literature

For a related structure and background to cinnamic acid derivatives, see: Teng et al. (2011 ▶); Zhong et al. (2011 ▶). For further synthetic details, see: Wu et al. (2008 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C29H30Br2N2O3

M = 614.37

Triclinic,

a = 8.5520 (17) Å

b = 10.355 (2) Å

c = 16.361 (3) Å

α = 92.85 (3)°

β = 100.52 (3)°

γ = 95.25 (3)°

V = 1415.3 (5) Å3

Z = 2

Mo Kα radiation

μ = 2.90 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.595, T max = 0.761

5569 measured reflections

5190 independent reflections

2233 reflections with I > 2σ(I)

R int = 0.098

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.145

S = 1.01

5190 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811052123/su2344sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052123/su2344Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052123/su2344Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C29H30Br2N2O3	Z = 2
Mr = 614.37	F(000) = 624
Triclinic, P1	Dx = 1.442 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5520 (17) Å	Cell parameters from 25 reflections
b = 10.355 (2) Å	θ = 9–13°
c = 16.361 (3) Å	µ = 2.90 mm−1
α = 92.85 (3)°	T = 293 K
β = 100.52 (3)°	Block, colourless
γ = 95.25 (3)°	0.20 × 0.10 × 0.10 mm
V = 1415.3 (5) Å3

Enraf–Nonius CAD-4 diffractometer	2233 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.098
graphite	θmax = 25.4°, θmin = 1.3°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.595, Tmax = 0.761	l = −19→19
5569 measured reflections	3 standard reflections every 200 reflections
5190 independent reflections	intensity decay: 1%

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.045P)2] where P = (Fo2 + 2Fc2)/3
5190 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	0.65376 (13)	0.34766 (12)	0.57637 (6)	0.1418 (5)
N1	0.9260 (5)	0.3258 (4)	0.2058 (3)	0.0541 (12)
O1	1.3079 (5)	0.4867 (4)	0.0380 (3)	0.0802 (14)
C1	0.7349 (9)	0.3675 (6)	0.3323 (4)	0.083 (2)
H1A	0.7259	0.4241	0.2897	0.099*
Br2	0.20032 (9)	−0.00602 (9)	0.02290 (5)	0.0987 (4)
N2	1.1790 (6)	0.4652 (5)	0.1444 (3)	0.0610 (14)
O2	1.9023 (5)	0.8508 (5)	0.3993 (3)	0.0900 (16)
C2	0.6782 (10)	0.3959 (8)	0.4101 (5)	0.107 (3)
H2A	0.6223	0.4676	0.4162	0.128*
O3	2.1174 (5)	0.9315 (4)	0.3219 (2)	0.0730 (13)
C3	0.7089 (10)	0.3160 (9)	0.4728 (4)	0.092 (3)
C4	0.7929 (9)	0.2026 (9)	0.4636 (4)	0.102 (3)
H4A	0.8159	0.1495	0.5076	0.123*
C5	0.8378 (7)	0.1751 (7)	0.3896 (4)	0.075 (2)
H5A	0.8928	0.1034	0.3820	0.091*
C6	0.7996 (6)	0.2565 (5)	0.3260 (4)	0.0529 (15)
C7	0.8396 (8)	0.2183 (7)	0.2417 (4)	0.080 (2)
H7A	0.9100	0.1486	0.2499	0.096*
C8	0.6895 (7)	0.1635 (6)	0.1820 (4)	0.0630 (17)
C9	0.6436 (7)	0.0372 (6)	0.1727 (4)	0.0648 (17)
H9A	0.7130	−0.0176	0.2001	0.078*
C10	0.5035 (7)	−0.0188 (5)	0.1265 (4)	0.0641 (18)
H10A	0.4772	−0.1083	0.1227	0.077*
C11	0.4077 (6)	0.0579 (6)	0.0878 (3)	0.0526 (14)
C12	0.4392 (8)	0.2000 (6)	0.0887 (4)	0.083 (2)
H12A	0.3687	0.2529	0.0601	0.100*
C13	0.5895 (8)	0.2469 (6)	0.1383 (4)	0.079 (2)
H13A	0.6225	0.3354	0.1419	0.095*
C14	0.9581 (8)	0.2932 (7)	0.1231 (4)	0.083 (2)
H14A	1.0273	0.2237	0.1263	0.100*
H14B	0.8585	0.2622	0.0859	0.100*
C15	1.0330 (8)	0.4036 (6)	0.0898 (4)	0.083 (2)
H15A	0.9571	0.4677	0.0793	0.099*
H15B	1.0592	0.3760	0.0368	0.099*
C16	1.1500 (8)	0.4937 (6)	0.2289 (4)	0.085 (2)
H16A	1.0802	0.5625	0.2282	0.103*
H16B	1.2504	0.5235	0.2658	0.103*
C17	1.0756 (7)	0.3766 (6)	0.2603 (4)	0.0732 (19)
H17A	1.1491	0.3102	0.2647	0.088*
H17B	1.0553	0.3979	0.3156	0.088*
C18	1.3040 (7)	0.5159 (7)	0.1128 (4)	0.0684 (18)
C19	1.4415 (8)	0.5873 (6)	0.1696 (4)	0.074 (2)
H19A	1.4322	0.6116	0.2238	0.089*
C20	1.5779 (7)	0.6173 (6)	0.1446 (4)	0.074 (2)
H20A	1.5825	0.5853	0.0911	0.089*
C21	1.7193 (6)	0.6923 (5)	0.1888 (3)	0.0443 (13)
C22	1.8438 (7)	0.7364 (6)	0.1511 (4)	0.0641 (17)
H22A	1.8393	0.7109	0.0953	0.077*
C23	1.9733 (7)	0.8157 (7)	0.1922 (4)	0.079 (2)
H23A	2.0502	0.8475	0.1627	0.094*
C24	1.9934 (6)	0.8501 (6)	0.2765 (4)	0.0588 (16)
C25	1.8700 (6)	0.8058 (6)	0.3175 (4)	0.0539 (15)
C26	1.7401 (6)	0.7287 (5)	0.2764 (3)	0.0533 (15)
H26A	1.6621	0.6984	0.3056	0.064*
C27	1.7825 (8)	0.8123 (7)	0.4451 (4)	0.096 (2)
H27A	1.8132	0.8494	0.5014	0.144*
H27B	1.7701	0.7192	0.4453	0.144*
H27C	1.6831	0.8420	0.4198	0.144*
C28	2.2484 (7)	0.9702 (7)	0.2786 (4)	0.078 (2)
H28A	2.2110	1.0169	0.2301	0.094*
H28B	2.2975	0.8951	0.2614	0.094*
C29	2.3669 (8)	1.0595 (7)	0.3454 (4)	0.104 (3)
H29A	2.4591	1.0890	0.3230	0.156*
H29B	2.3993	1.0119	0.3935	0.156*
H29C	2.3156	1.1331	0.3612	0.156*

	U11	U22	U33	U12	U13	U23
Br1	0.1442 (9)	0.2104 (13)	0.0742 (6)	−0.0019 (8)	0.0470 (6)	−0.0167 (7)
N1	0.058 (3)	0.061 (3)	0.040 (2)	−0.009 (2)	0.007 (2)	−0.001 (2)
O1	0.090 (3)	0.084 (3)	0.061 (3)	−0.029 (3)	0.017 (3)	0.014 (3)
C1	0.135 (7)	0.050 (4)	0.071 (5)	0.003 (4)	0.038 (5)	0.020 (4)
Br2	0.0657 (5)	0.1419 (8)	0.0789 (5)	−0.0321 (5)	0.0134 (4)	−0.0091 (5)
N2	0.059 (3)	0.071 (3)	0.049 (3)	−0.019 (3)	0.016 (3)	0.000 (3)
O2	0.068 (3)	0.134 (4)	0.069 (3)	−0.025 (3)	0.026 (3)	0.028 (3)
C2	0.120 (7)	0.109 (7)	0.090 (6)	0.003 (6)	0.022 (6)	−0.006 (6)
O3	0.059 (3)	0.107 (4)	0.051 (2)	−0.017 (2)	0.013 (2)	0.026 (2)
C3	0.106 (6)	0.113 (7)	0.046 (4)	−0.034 (5)	0.018 (4)	−0.017 (5)
C4	0.106 (7)	0.148 (9)	0.046 (4)	−0.003 (6)	0.000 (4)	0.005 (5)
C5	0.065 (4)	0.094 (5)	0.064 (4)	0.004 (4)	−0.001 (4)	0.033 (4)
C6	0.057 (3)	0.035 (3)	0.065 (4)	−0.018 (3)	0.015 (3)	0.016 (3)
C7	0.074 (5)	0.097 (6)	0.066 (4)	−0.017 (4)	0.012 (4)	0.020 (4)
C8	0.067 (4)	0.065 (4)	0.058 (4)	0.009 (3)	0.014 (3)	0.001 (3)
C9	0.067 (4)	0.074 (4)	0.058 (4)	0.015 (3)	0.012 (3)	0.030 (4)
C10	0.075 (4)	0.044 (4)	0.081 (5)	0.014 (3)	0.024 (4)	0.031 (3)
C11	0.048 (3)	0.058 (3)	0.056 (4)	0.007 (3)	0.022 (3)	−0.004 (3)
C12	0.090 (5)	0.080 (5)	0.080 (5)	0.027 (4)	0.001 (4)	0.034 (4)
C13	0.094 (5)	0.063 (4)	0.075 (5)	−0.020 (4)	0.009 (4)	0.028 (4)
C14	0.085 (5)	0.091 (6)	0.071 (5)	−0.011 (4)	0.019 (4)	−0.004 (4)
C15	0.083 (5)	0.098 (5)	0.057 (4)	−0.034 (4)	0.002 (4)	0.032 (4)
C16	0.106 (6)	0.073 (5)	0.069 (5)	−0.031 (4)	0.015 (4)	0.003 (4)
C17	0.066 (4)	0.088 (5)	0.058 (4)	−0.012 (4)	0.005 (3)	−0.008 (4)
C18	0.050 (4)	0.100 (5)	0.060 (4)	0.015 (3)	0.013 (3)	0.022 (4)
C19	0.083 (5)	0.073 (4)	0.064 (4)	−0.018 (4)	0.012 (4)	0.026 (4)
C20	0.065 (4)	0.096 (5)	0.061 (4)	−0.019 (4)	0.020 (4)	0.017 (4)
C21	0.044 (3)	0.057 (3)	0.039 (3)	0.029 (3)	0.007 (3)	0.029 (3)
C22	0.074 (4)	0.067 (4)	0.062 (4)	0.016 (3)	0.029 (3)	0.028 (3)
C23	0.046 (4)	0.103 (6)	0.081 (5)	−0.022 (4)	0.013 (4)	0.008 (4)
C24	0.039 (3)	0.056 (4)	0.074 (4)	−0.004 (3)	−0.011 (3)	0.029 (3)
C25	0.039 (3)	0.070 (4)	0.056 (4)	0.003 (3)	0.018 (3)	0.019 (3)
C26	0.040 (3)	0.059 (3)	0.065 (4)	0.002 (2)	0.010 (3)	0.037 (3)
C27	0.099 (6)	0.108 (6)	0.086 (5)	0.005 (5)	0.034 (5)	0.009 (5)
C28	0.046 (3)	0.103 (5)	0.086 (5)	0.000 (4)	0.015 (4)	0.024 (4)
C29	0.088 (5)	0.114 (6)	0.101 (6)	−0.045 (5)	0.028 (5)	−0.012 (5)

Br1—C3	1.862 (7)	C13—H13A	0.9300
N1—C17	1.458 (6)	C14—C15	1.438 (7)
N1—C14	1.458 (7)	C14—H14A	0.9700
N1—C7	1.484 (7)	C14—H14B	0.9700
O1—C18	1.254 (7)	C15—H15A	0.9700
C1—C6	1.328 (8)	C15—H15B	0.9700
C1—C2	1.469 (9)	C16—C17	1.475 (7)
C1—H1A	0.9300	C16—H16A	0.9700
Br2—C11	1.934 (5)	C16—H16B	0.9700
N2—C18	1.346 (7)	C17—H17A	0.9700
N2—C15	1.468 (7)	C17—H17B	0.9700
N2—C16	1.469 (7)	C18—C19	1.471 (8)
O2—C25	1.365 (6)	C19—C20	1.321 (7)
O2—C27	1.416 (7)	C19—H19A	0.9300
C2—C3	1.354 (10)	C20—C21	1.429 (7)
C2—H2A	0.9300	C20—H20A	0.9300
O3—C24	1.369 (6)	C21—C22	1.379 (7)
O3—C28	1.467 (6)	C21—C26	1.438 (7)
C3—C4	1.447 (11)	C22—C23	1.364 (8)
C4—C5	1.360 (9)	C22—H22A	0.9300
C4—H4A	0.9300	C23—C24	1.383 (8)
C5—C6	1.384 (7)	C23—H23A	0.9300
C5—H5A	0.9300	C24—C25	1.406 (7)
C6—C7	1.524 (8)	C25—C26	1.355 (7)
C7—C8	1.509 (8)	C26—H26A	0.9300
C7—H7A	0.9800	C27—H27A	0.9600
C8—C9	1.324 (7)	C27—H27B	0.9600
C8—C13	1.400 (8)	C27—H27C	0.9600
C9—C10	1.358 (8)	C28—C29	1.550 (8)
C9—H9A	0.9300	C28—H28A	0.9700
C10—C11	1.297 (7)	C28—H28B	0.9700
C10—H10A	0.9300	C29—H29A	0.9600
C11—C12	1.470 (8)	C29—H29B	0.9600
C12—C13	1.419 (8)	C29—H29C	0.9600
C12—H12A	0.9300
C17—N1—C14	108.8 (5)	N2—C15—H15B	108.8
C17—N1—C7	112.4 (5)	H15A—C15—H15B	107.6
C14—N1—C7	114.4 (5)	N2—C16—C17	110.5 (5)
C6—C1—C2	116.4 (7)	N2—C16—H16A	109.5
C6—C1—H1A	121.8	C17—C16—H16A	109.5
C2—C1—H1A	121.8	N2—C16—H16B	109.5
C18—N2—C15	121.1 (5)	C17—C16—H16B	109.5
C18—N2—C16	126.0 (5)	H16A—C16—H16B	108.1
C15—N2—C16	110.8 (5)	N1—C17—C16	111.7 (5)
C25—O2—C27	114.8 (5)	N1—C17—H17A	109.3
C3—C2—C1	118.8 (8)	C16—C17—H17A	109.3
C3—C2—H2A	120.6	N1—C17—H17B	109.3
C1—C2—H2A	120.6	C16—C17—H17B	109.3
C24—O3—C28	115.8 (5)	H17A—C17—H17B	107.9
C2—C3—C4	121.2 (7)	O1—C18—N2	118.5 (6)
C2—C3—Br1	122.7 (8)	O1—C18—C19	121.9 (6)
C4—C3—Br1	116.1 (6)	N2—C18—C19	119.0 (6)
C5—C4—C3	118.8 (7)	C20—C19—C18	121.0 (6)
C5—C4—H4A	120.6	C20—C19—H19A	119.5
C3—C4—H4A	120.6	C18—C19—H19A	119.5
C4—C5—C6	118.3 (7)	C19—C20—C21	128.7 (6)
C4—C5—H5A	120.8	C19—C20—H20A	115.6
C6—C5—H5A	120.8	C21—C20—H20A	115.6
C1—C6—C5	125.9 (7)	C22—C21—C20	123.0 (5)
C1—C6—C7	116.6 (6)	C22—C21—C26	115.3 (5)
C5—C6—C7	117.5 (6)	C20—C21—C26	121.7 (5)
N1—C7—C8	111.1 (5)	C23—C22—C21	122.8 (6)
N1—C7—C6	113.5 (5)	C23—C22—H22A	118.6
C8—C7—C6	109.9 (5)	C21—C22—H22A	118.6
N1—C7—H7A	107.4	C22—C23—C24	121.7 (6)
C8—C7—H7A	107.4	C22—C23—H23A	119.1
C6—C7—H7A	107.4	C24—C23—H23A	119.1
C9—C8—C13	118.1 (6)	O3—C24—C23	125.5 (5)
C9—C8—C7	121.6 (6)	O3—C24—C25	117.2 (6)
C13—C8—C7	120.3 (6)	C23—C24—C25	117.2 (5)
C8—C9—C10	125.3 (6)	C26—C25—O2	128.0 (5)
C8—C9—H9A	117.4	C26—C25—C24	121.0 (6)
C10—C9—H9A	117.4	O2—C25—C24	111.0 (5)
C11—C10—C9	117.1 (6)	C25—C26—C21	121.9 (5)
C11—C10—H10A	121.4	C25—C26—H26A	119.0
C9—C10—H10A	121.4	C21—C26—H26A	119.0
C10—C11—C12	125.6 (6)	O2—C27—H27A	109.5
C10—C11—Br2	122.2 (5)	O2—C27—H27B	109.5
C12—C11—Br2	112.2 (4)	H27A—C27—H27B	109.5
C13—C12—C11	112.1 (5)	O2—C27—H27C	109.5
C13—C12—H12A	124.0	H27A—C27—H27C	109.5
C11—C12—H12A	124.0	H27B—C27—H27C	109.5
C8—C13—C12	121.8 (6)	O3—C28—C29	103.1 (5)
C8—C13—H13A	119.1	O3—C28—H28A	111.1
C12—C13—H13A	119.1	C29—C28—H28A	111.1
C15—C14—N1	111.6 (6)	O3—C28—H28B	111.1
C15—C14—H14A	109.3	C29—C28—H28B	111.1
N1—C14—H14A	109.3	H28A—C28—H28B	109.1
C15—C14—H14B	109.3	C28—C29—H29A	109.5
N1—C14—H14B	109.3	C28—C29—H29B	109.5
H14A—C14—H14B	108.0	H29A—C29—H29B	109.5
C14—C15—N2	114.0 (5)	C28—C29—H29C	109.5
C14—C15—H15A	108.8	H29A—C29—H29C	109.5
N2—C15—H15A	108.8	H29B—C29—H29C	109.5
C14—C15—H15B	108.8
C6—C1—C2—C3	6.4 (11)	C18—N2—C15—C14	144.2 (6)
C1—C2—C3—C4	−1.2 (12)	C16—N2—C15—C14	−51.3 (8)
C1—C2—C3—Br1	176.3 (5)	C18—N2—C16—C17	−144.8 (6)
C2—C3—C4—C5	−1.7 (12)	C15—N2—C16—C17	51.7 (8)
Br1—C3—C4—C5	−179.4 (5)	C14—N1—C17—C16	59.4 (7)
C3—C4—C5—C6	−0.5 (10)	C7—N1—C17—C16	−172.9 (6)
C2—C1—C6—C5	−9.3 (10)	N2—C16—C17—N1	−57.7 (8)
C2—C1—C6—C7	172.6 (6)	C15—N2—C18—O1	−14.6 (10)
C4—C5—C6—C1	6.5 (10)	C16—N2—C18—O1	−176.5 (6)
C4—C5—C6—C7	−175.5 (6)	C15—N2—C18—C19	174.4 (6)
C17—N1—C7—C8	−177.2 (5)	C16—N2—C18—C19	12.4 (10)
C14—N1—C7—C8	−52.5 (8)	O1—C18—C19—C20	−3.6 (10)
C17—N1—C7—C6	58.3 (7)	N2—C18—C19—C20	167.1 (6)
C14—N1—C7—C6	−177.0 (5)	C18—C19—C20—C21	175.7 (6)
C1—C6—C7—N1	47.2 (8)	C19—C20—C21—C22	−168.1 (7)
C5—C6—C7—N1	−130.9 (6)	C19—C20—C21—C26	11.0 (10)
C1—C6—C7—C8	−77.8 (7)	C20—C21—C22—C23	175.1 (6)
C5—C6—C7—C8	104.0 (7)	C26—C21—C22—C23	−4.0 (8)
N1—C7—C8—C9	140.8 (6)	C21—C22—C23—C24	4.5 (10)
C6—C7—C8—C9	−92.7 (8)	C28—O3—C24—C23	−8.4 (9)
N1—C7—C8—C13	−43.0 (9)	C28—O3—C24—C25	176.7 (5)
C6—C7—C8—C13	83.4 (7)	C22—C23—C24—O3	−178.3 (5)
C13—C8—C9—C10	−2.7 (10)	C22—C23—C24—C25	−3.4 (10)
C7—C8—C9—C10	173.6 (6)	C27—O2—C25—C26	−0.9 (9)
C8—C9—C10—C11	0.6 (10)	C27—O2—C25—C24	179.1 (5)
C9—C10—C11—C12	1.0 (9)	O3—C24—C25—C26	177.7 (5)
C9—C10—C11—Br2	−177.6 (4)	C23—C24—C25—C26	2.3 (9)
C10—C11—C12—C13	−0.4 (9)	O3—C24—C25—O2	−2.3 (8)
Br2—C11—C12—C13	178.3 (5)	C23—C24—C25—O2	−177.6 (6)
C9—C8—C13—C12	3.2 (10)	O2—C25—C26—C21	177.8 (5)
C7—C8—C13—C12	−173.1 (6)	C24—C25—C26—C21	−2.2 (8)
C11—C12—C13—C8	−1.7 (9)	C22—C21—C26—C25	2.9 (7)
C17—N1—C14—C15	−57.0 (7)	C20—C21—C26—C25	−176.3 (5)
C7—N1—C14—C15	176.4 (5)	C24—O3—C28—C29	−179.9 (5)
N1—C14—C15—N2	54.4 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1i	0.93	2.55	3.358 (8)	145
C20—H20A···O1ii	0.93	2.57	3.461 (8)	161
C16—H16B···Br1iii	0.97	2.79	3.562 (7)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1i	0.93	2.55	3.358 (8)	145
C20—H20A⋯O1ii	0.93	2.57	3.461 (8)	161
C16—H16B⋯Br1iii	0.97	2.79	3.562 (7)	137

Symmetry codes: (i) ; (ii) ; (iii) .