(Z)-3-(9-Anthr­yl)-1-(4-bromo­phen­yl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one

Lu, Y.-H.; Wang, G.-Z.; Zhou, C.-H.; Zhang, Y.-Y.

doi:10.1107/S1600536809018352

(Z)-3-(9-Anthryl)-1-(4-bromophenyl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one

Y.-H. Lu, G.-Z. Wang, C.-H. Zhou and Y.-Y. Zhang

In the title molecule, C₂₆H₁₆BrN₃O₃, the anthracene and benzene mean planes make dihedral angles of 63.79 (2) and 14.67 (2)°, respectively, with the plane of the imidazole ring. In the crystal structure, weak intermolecular C—H

O hydrogen bonds link molecules to form centrosymmetric dimers. Weak π–π stacking interactions, with centroid–centroid distances of 3.779 (2) and 3.826 (2) Å, supply additional stabilization. The crystal packing also exhibits short intermolecular contacts between the nitro groups and Br atoms [Br

O = 3.114 (2) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809018352/lh2825sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809018352/lh2825Isup2.hkl Contains datablock I

CCDC reference: 738286

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.005 Å
R factor = 0.044
wR factor = 0.116
Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O1      ..       3.11 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C20     ..       2.97 Ang.

Alert level G
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C1     -C14           1.41 Ang.
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        200 Deg.

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

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

Comment top

Chalcones and their derivatives have been reported responsible for a variety of pharmacological activities, including antibacterial, antifungal, anti-leishmanial, antimalarial, analgesic, anti-inflammatory and chemopreventive ones (Corréa et al., 2001; Jasinski et al., 2009; Simon et al., 1998; Vogel et al., 2008). Due to these varied applications, we have synthesized the title compound and report its crystal structure.

In the molecular structure of the title compound (I) (Fig. 1), the dihedral angle between the anthracene unit and imidazole ring is 63.79 (2) ° and that between the imidazole ring and benzene ring is 14.67 (2) °. In the crystal structure, weak intermolecular C—H···O hydrogen bonds link molecules to form centrosymmetric dimers (Fig. 2). Weak π–π staking interactions, with centroid to centroid distances of 3.779 (2) and 3.826 (2)Å supply additional stabilization.

Related literature top

For the crystal structure of the chloro analog of the title compound, see: Wang et al. (2009). For general background on the pharmacological activities of chalcones, see: Corréa et al. (2001); Jasinski et al. (2009); Simon et al. (1998); Vogel et al. (2008). For the synthetic details, see: Erhardt et al. (1985); Kranz et al. (1980).

Experimental top

Compound (I) was synthesized according to the procedure of Erhardt et al. (1985); Kranz et al. (1980). A crystal suitable for X-ray analysis was grown from a chloroform and acetone solution of (I) by slow evaporation at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of (I). Hydrogen bonds are shown as dashed lines.

(Z)-3-(9-Anthryl)-1-(4-bromophenyl)-2-(4-nitro-1H-imidazol- 1-yl)prop-2-en-1-one top

Crystal data top

C₂₆H₁₆BrN₃O₃	Z = 2
M_r = 498.33	F(000) = 504
Triclinic, P1	D_x = 1.549 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1438 (11) Å	Cell parameters from 2344 reflections
b = 11.0916 (14) Å	θ = 2.3–26.9°
c = 12.7979 (17) Å	µ = 1.96 mm⁻¹
α = 78.146 (2)°	T = 292 K
β = 86.193 (2)°	Block, orange
γ = 70.768 (2)°	0.13 × 0.12 × 0.10 mm
V = 1068.2 (2) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4315 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	3095 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
0.3° wide ω exposures scans	θ_max = 26.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→10
T_min = 0.775, T_max = 0.828	k = −13→13
6422 measured reflections	l = −16→15

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0524P)² + 0.6665P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.008
4315 reflections	Δρ_max = 0.56 e Å⁻³
298 parameters	Δρ_min = −0.67 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0078 (11)

Crystal data top

C₂₆H₁₆BrN₃O₃	γ = 70.768 (2)°
M_r = 498.33	V = 1068.2 (2) Å³
Triclinic, P1	Z = 2
a = 8.1438 (11) Å	Mo Kα radiation
b = 11.0916 (14) Å	µ = 1.96 mm⁻¹
c = 12.7979 (17) Å	T = 292 K
α = 78.146 (2)°	0.13 × 0.12 × 0.10 mm
β = 86.193 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4315 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3095 reflections with I > 2σ(I)
T_min = 0.775, T_max = 0.828	R_int = 0.019
6422 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	Δρ_max = 0.56 e Å⁻³
4315 reflections	Δρ_min = −0.67 e Å⁻³
298 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	0.93749 (6)	0.89457 (4)	0.12755 (3)	0.06983 (18)
C1	0.4551 (4)	0.4031 (3)	0.3854 (2)	0.0356 (6)
C2	0.3193 (4)	0.4914 (3)	0.4320 (2)	0.0406 (7)
C3	0.2357 (4)	0.6217 (3)	0.3799 (3)	0.0496 (8)
H3	0.2699	0.6506	0.3111	0.060*
C4	0.1080 (5)	0.7050 (4)	0.4276 (4)	0.0691 (11)
H4	0.0565	0.7902	0.3917	0.083*
C5	0.0521 (5)	0.6637 (5)	0.5312 (4)	0.0740 (13)
H5	−0.0342	0.7224	0.5639	0.089*
C6	0.1223 (5)	0.5405 (5)	0.5832 (3)	0.0647 (11)
H6	0.0819	0.5144	0.6509	0.078*
C7	0.2583 (4)	0.4483 (4)	0.5363 (2)	0.0510 (9)
C8	0.3318 (5)	0.3209 (4)	0.5877 (3)	0.0570 (10)
H8	0.2893	0.2930	0.6543	0.068*
C9	0.4663 (5)	0.2335 (4)	0.5435 (3)	0.0545 (9)
C10	0.5444 (7)	0.1041 (4)	0.5990 (3)	0.0804 (14)
H10	0.5007	0.0765	0.6653	0.096*
C11	0.6795 (8)	0.0206 (5)	0.5582 (4)	0.0943 (17)
H11	0.7273	−0.0642	0.5957	0.113*
C12	0.7504 (7)	0.0613 (4)	0.4575 (4)	0.0792 (13)
H12	0.8461	0.0034	0.4305	0.095*
C13	0.6790 (5)	0.1839 (3)	0.4007 (3)	0.0538 (9)
H13	0.7270	0.2092	0.3353	0.065*
C14	0.5326 (4)	0.2738 (3)	0.4394 (2)	0.0415 (7)
C15	0.5261 (4)	0.4522 (3)	0.2830 (2)	0.0327 (6)
H15	0.5626	0.5235	0.2820	0.039*
C16	0.5458 (4)	0.4098 (2)	0.1916 (2)	0.0308 (6)
C17	0.3147 (4)	0.3086 (3)	0.1964 (2)	0.0391 (7)
H17	0.2215	0.3730	0.2185	0.047*
C18	0.5712 (5)	0.1936 (3)	0.1475 (3)	0.0456 (7)
H18	0.6886	0.1698	0.1296	0.055*
C19	0.3157 (5)	0.1937 (3)	0.1754 (2)	0.0448 (8)
C20	0.6441 (4)	0.4580 (3)	0.0995 (2)	0.0322 (6)
C21	0.7038 (4)	0.5703 (3)	0.1060 (2)	0.0332 (6)
C22	0.8822 (4)	0.5456 (3)	0.1056 (2)	0.0422 (7)
H22	0.9569	0.4628	0.1014	0.051*
C23	0.9499 (4)	0.6436 (3)	0.1113 (3)	0.0490 (8)
H23	1.0696	0.6267	0.1122	0.059*
C24	0.8383 (4)	0.7651 (3)	0.1157 (2)	0.0438 (7)
C25	0.6602 (4)	0.7937 (3)	0.1138 (2)	0.0426 (7)
H25	0.5861	0.8775	0.1155	0.051*
C26	0.5943 (4)	0.6947 (3)	0.1094 (2)	0.0389 (7)
H26	0.4746	0.7121	0.1087	0.047*
N1	0.4811 (3)	0.3085 (2)	0.17774 (18)	0.0342 (5)
N2	0.4740 (4)	0.1210 (2)	0.1464 (2)	0.0515 (7)
N3	0.1680 (5)	0.1482 (3)	0.1818 (3)	0.0663 (9)
O1	0.1909 (5)	0.0414 (3)	0.1602 (3)	0.1002 (11)
O2	0.0289 (5)	0.2194 (4)	0.2088 (3)	0.0920 (10)
O3	0.6822 (3)	0.4034 (2)	0.02424 (17)	0.0464 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0870 (3)	0.0579 (2)	0.0872 (3)	−0.0537 (2)	0.0032 (2)	−0.01466 (19)
C1	0.0423 (17)	0.0457 (16)	0.0284 (14)	−0.0269 (14)	0.0004 (12)	−0.0071 (12)
C2	0.0426 (18)	0.0551 (19)	0.0351 (16)	−0.0264 (15)	0.0010 (13)	−0.0159 (14)
C3	0.048 (2)	0.056 (2)	0.0514 (19)	−0.0203 (17)	0.0012 (15)	−0.0194 (16)
C4	0.058 (2)	0.073 (3)	0.079 (3)	−0.012 (2)	−0.004 (2)	−0.036 (2)
C5	0.049 (2)	0.108 (4)	0.079 (3)	−0.021 (2)	0.009 (2)	−0.057 (3)
C6	0.047 (2)	0.119 (4)	0.047 (2)	−0.040 (2)	0.0134 (17)	−0.038 (2)
C7	0.0468 (19)	0.089 (3)	0.0349 (17)	−0.0403 (19)	0.0018 (14)	−0.0203 (17)
C8	0.065 (2)	0.090 (3)	0.0297 (17)	−0.049 (2)	0.0024 (16)	−0.0047 (18)
C9	0.074 (3)	0.065 (2)	0.0363 (17)	−0.044 (2)	−0.0098 (17)	0.0023 (16)
C10	0.124 (4)	0.070 (3)	0.050 (2)	−0.049 (3)	−0.018 (2)	0.016 (2)
C11	0.156 (5)	0.054 (3)	0.061 (3)	−0.030 (3)	−0.026 (3)	0.016 (2)
C12	0.101 (3)	0.050 (2)	0.076 (3)	−0.008 (2)	−0.019 (2)	−0.009 (2)
C13	0.069 (2)	0.0462 (19)	0.0451 (19)	−0.0187 (18)	−0.0118 (17)	−0.0038 (15)
C14	0.0523 (19)	0.0446 (17)	0.0352 (16)	−0.0268 (15)	−0.0055 (14)	−0.0043 (13)
C15	0.0364 (16)	0.0331 (14)	0.0342 (15)	−0.0187 (12)	0.0007 (12)	−0.0065 (11)
C16	0.0360 (15)	0.0274 (13)	0.0345 (15)	−0.0171 (12)	−0.0003 (11)	−0.0066 (11)
C17	0.0398 (17)	0.0420 (16)	0.0412 (16)	−0.0219 (14)	−0.0027 (13)	−0.0052 (13)
C18	0.054 (2)	0.0340 (16)	0.0535 (19)	−0.0187 (14)	0.0031 (15)	−0.0123 (13)
C19	0.062 (2)	0.0461 (17)	0.0374 (16)	−0.0354 (17)	−0.0100 (15)	0.0011 (13)
C20	0.0317 (15)	0.0346 (14)	0.0327 (15)	−0.0129 (12)	0.0002 (12)	−0.0087 (12)
C21	0.0422 (17)	0.0358 (15)	0.0265 (14)	−0.0207 (13)	0.0045 (11)	−0.0049 (11)
C22	0.0423 (18)	0.0411 (16)	0.0498 (18)	−0.0197 (14)	0.0098 (14)	−0.0162 (14)
C23	0.0414 (18)	0.058 (2)	0.061 (2)	−0.0303 (16)	0.0103 (15)	−0.0203 (16)
C24	0.061 (2)	0.0409 (17)	0.0423 (17)	−0.0348 (16)	0.0083 (14)	−0.0084 (13)
C25	0.054 (2)	0.0329 (15)	0.0429 (17)	−0.0188 (14)	0.0001 (14)	−0.0040 (13)
C26	0.0395 (17)	0.0380 (16)	0.0430 (17)	−0.0178 (14)	0.0032 (13)	−0.0082 (13)
N1	0.0426 (14)	0.0311 (12)	0.0362 (12)	−0.0203 (11)	−0.0023 (10)	−0.0079 (10)
N2	0.075 (2)	0.0366 (14)	0.0513 (16)	−0.0297 (15)	−0.0045 (14)	−0.0068 (12)
N3	0.088 (3)	0.070 (2)	0.063 (2)	−0.061 (2)	−0.0171 (19)	0.0032 (16)
O1	0.133 (3)	0.089 (2)	0.121 (3)	−0.087 (2)	−0.009 (2)	−0.0254 (19)
O2	0.074 (2)	0.101 (2)	0.121 (3)	−0.063 (2)	−0.002 (2)	−0.007 (2)
O3	0.0553 (14)	0.0526 (13)	0.0437 (12)	−0.0285 (11)	0.0144 (10)	−0.0226 (10)

Geometric parameters (Å, º) top

Br1—C24	1.899 (3)	C15—C16	1.329 (4)
C1—C2	1.405 (4)	C15—H15	0.9300
C1—C14	1.410 (4)	C16—N1	1.434 (3)
C1—C15	1.471 (4)	C16—C20	1.487 (4)
C2—C3	1.419 (5)	C17—C19	1.353 (4)
C2—C7	1.436 (4)	C17—N1	1.359 (4)
C3—C4	1.349 (5)	C17—H17	0.9300
C3—H3	0.9300	C18—N2	1.305 (4)
C4—C5	1.408 (6)	C18—N1	1.365 (4)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.341 (6)	C19—N2	1.351 (4)
C5—H5	0.9300	C19—N3	1.442 (4)
C6—C7	1.432 (5)	C20—O3	1.211 (3)
C6—H6	0.9300	C20—C21	1.497 (4)
C7—C8	1.379 (5)	C21—C26	1.382 (4)
C8—C9	1.379 (5)	C21—C22	1.387 (4)
C8—H8	0.9300	C22—C23	1.387 (4)
C9—C10	1.417 (5)	C22—H22	0.9300
C9—C14	1.444 (5)	C23—C24	1.365 (5)
C10—C11	1.338 (7)	C23—H23	0.9300
C10—H10	0.9300	C24—C25	1.380 (5)
C11—C12	1.426 (7)	C25—C26	1.384 (4)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.358 (5)	C26—H26	0.9300
C12—H12	0.9300	N3—O1	1.222 (4)
C13—C14	1.415 (5)	N3—O2	1.224 (5)
C13—H13	0.9300

C2—C1—C14	121.2 (3)	C16—C15—H15	115.2
C2—C1—C15	118.2 (3)	C1—C15—H15	115.2
C14—C1—C15	120.3 (3)	C15—C16—N1	121.6 (2)
C1—C2—C3	123.1 (3)	C15—C16—C20	122.8 (2)
C1—C2—C7	119.1 (3)	N1—C16—C20	115.5 (2)
C3—C2—C7	117.7 (3)	C19—C17—N1	104.3 (3)
C4—C3—C2	121.8 (4)	C19—C17—H17	127.8
C4—C3—H3	119.1	N1—C17—H17	127.8
C2—C3—H3	119.1	N2—C18—N1	112.3 (3)
C3—C4—C5	120.4 (4)	N2—C18—H18	123.9
C3—C4—H4	119.8	N1—C18—H18	123.9
C5—C4—H4	119.8	N2—C19—C17	112.9 (3)
C6—C5—C4	120.6 (4)	N2—C19—N3	121.2 (3)
C6—C5—H5	119.7	C17—C19—N3	125.9 (4)
C4—C5—H5	119.7	O3—C20—C16	120.7 (2)
C5—C6—C7	121.2 (4)	O3—C20—C21	121.2 (2)
C5—C6—H6	119.4	C16—C20—C21	118.0 (2)
C7—C6—H6	119.4	C26—C21—C22	119.1 (3)
C8—C7—C2	119.4 (3)	C26—C21—C20	124.6 (3)
C8—C7—C6	122.3 (3)	C22—C21—C20	116.3 (3)
C2—C7—C6	118.3 (3)	C23—C22—C21	120.5 (3)
C9—C8—C7	122.1 (3)	C23—C22—H22	119.8
C9—C8—H8	118.9	C21—C22—H22	119.8
C7—C8—H8	118.9	C24—C23—C22	119.0 (3)
C8—C9—C10	121.4 (4)	C24—C23—H23	120.5
C8—C9—C14	120.0 (3)	C22—C23—H23	120.5
C10—C9—C14	118.6 (4)	C23—C24—C25	122.0 (3)
C11—C10—C9	121.5 (4)	C23—C24—Br1	117.4 (2)
C11—C10—H10	119.2	C25—C24—Br1	120.6 (2)
C9—C10—H10	119.2	C26—C25—C24	118.4 (3)
C10—C11—C12	120.2 (4)	C26—C25—H25	120.8
C10—C11—H11	119.9	C24—C25—H25	120.8
C12—C11—H11	119.9	C21—C26—C25	121.0 (3)
C13—C12—C11	120.4 (4)	C21—C26—H26	119.5
C13—C12—H12	119.8	C25—C26—H26	119.5
C11—C12—H12	119.8	C17—N1—C18	106.8 (2)
C12—C13—C14	121.0 (4)	C17—N1—C16	125.3 (2)
C12—C13—H13	119.5	C18—N1—C16	128.0 (2)
C14—C13—H13	119.5	C18—N2—C19	103.7 (3)
C1—C14—C13	123.7 (3)	O1—N3—O2	124.9 (4)
C1—C14—C9	118.1 (3)	O1—N3—C19	117.7 (4)
C13—C14—C9	118.1 (3)	O2—N3—C19	117.4 (3)
C16—C15—C1	129.6 (2)

C14—C1—C2—C3	−179.0 (3)	C1—C15—C16—C20	−170.6 (3)
C15—C1—C2—C3	6.7 (4)	N1—C17—C19—N2	1.0 (3)
C14—C1—C2—C7	−0.3 (4)	N1—C17—C19—N3	−178.9 (3)
C15—C1—C2—C7	−174.6 (2)	C15—C16—C20—O3	168.5 (3)
C1—C2—C3—C4	−178.6 (3)	N1—C16—C20—O3	−8.1 (4)
C7—C2—C3—C4	2.6 (5)	C15—C16—C20—C21	−7.7 (4)
C2—C3—C4—C5	−0.7 (5)	N1—C16—C20—C21	175.6 (2)
C3—C4—C5—C6	−1.4 (6)	O3—C20—C21—C26	118.6 (3)
C4—C5—C6—C7	1.5 (6)	C16—C20—C21—C26	−65.2 (4)
C1—C2—C7—C8	−1.2 (4)	O3—C20—C21—C22	−59.7 (4)
C3—C2—C7—C8	177.6 (3)	C16—C20—C21—C22	116.5 (3)
C1—C2—C7—C6	178.7 (3)	C26—C21—C22—C23	1.7 (4)
C3—C2—C7—C6	−2.5 (4)	C20—C21—C22—C23	−180.0 (3)
C5—C6—C7—C8	−179.5 (3)	C21—C22—C23—C24	−1.0 (5)
C5—C6—C7—C2	0.5 (5)	C22—C23—C24—C25	−0.4 (5)
C2—C7—C8—C9	1.9 (5)	C22—C23—C24—Br1	178.3 (2)
C6—C7—C8—C9	−178.0 (3)	C23—C24—C25—C26	1.2 (5)
C7—C8—C9—C10	177.8 (3)	Br1—C24—C25—C26	−177.4 (2)
C7—C8—C9—C14	−1.1 (5)	C22—C21—C26—C25	−0.9 (4)
C8—C9—C10—C11	−177.3 (4)	C20—C21—C26—C25	−179.1 (3)
C14—C9—C10—C11	1.7 (6)	C24—C25—C26—C21	−0.5 (4)
C9—C10—C11—C12	0.9 (7)	C19—C17—N1—C18	−0.3 (3)
C10—C11—C12—C13	−1.6 (7)	C19—C17—N1—C16	−178.5 (2)
C11—C12—C13—C14	−0.4 (6)	N2—C18—N1—C17	−0.5 (3)
C2—C1—C14—C13	−174.5 (3)	N2—C18—N1—C16	177.6 (3)
C15—C1—C14—C13	−0.3 (4)	C15—C16—N1—C17	53.4 (4)
C2—C1—C14—C9	1.1 (4)	C20—C16—N1—C17	−129.9 (3)
C15—C1—C14—C9	175.3 (3)	C15—C16—N1—C18	−124.4 (3)
C12—C13—C14—C1	178.5 (3)	C20—C16—N1—C18	52.4 (4)
C12—C13—C14—C9	3.0 (5)	N1—C18—N2—C19	1.0 (3)
C8—C9—C14—C1	−0.4 (4)	C17—C19—N2—C18	−1.3 (4)
C10—C9—C14—C1	−179.4 (3)	N3—C19—N2—C18	178.6 (3)
C8—C9—C14—C13	175.4 (3)	N2—C19—N3—O1	0.2 (5)
C10—C9—C14—C13	−3.6 (5)	C17—C19—N3—O1	−180.0 (3)
C2—C1—C15—C16	−126.2 (3)	N2—C19—N3—O2	179.8 (3)
C14—C1—C15—C16	59.4 (4)	C17—C19—N3—O2	−0.3 (5)
C1—C15—C16—N1	5.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O3ⁱ	0.93	2.56	3.303 (4)	137

Symmetry code: (i) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₆BrN₃O₃
M_r	498.33
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	8.1438 (11), 11.0916 (14), 12.7979 (17)
α, β, γ (°)	78.146 (2), 86.193 (2), 70.768 (2)
V (Å³)	1068.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.96
Crystal size (mm)	0.13 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.775, 0.828
No. of measured, independent and observed [I > 2σ(I)] reflections	6422, 4315, 3095
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.116, 1.02
No. of reflections	4315
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.67

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).