Methyl 9-(4-bromo­phen­yl)-8a,9,9a,10,11,12,13,14a-octa­hydro-8H-benzo[f]chromeno[3,4-b]indolizine-8a-car­box­ylate

Gunasekaran, B.; Kathiravan, S.; Raghunathan, R.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536809037994

Methyl 9-(4-bromophenyl)-8a,9,9a,10,11,12,13,14a-octahydro-8H-benzo[f]chromeno[3,4-b]indolizine-8a-carboxylate

B. Gunasekaran, S. Kathiravan, R. Raghunathan, G. Chakkaravarthi and V. Manivannan

In the title compound, C₂₇H₂₆BrNO₃, the mean plane of the naphthalene ring system makes a dihedral angle of 22.0 (1)° with the bromo-substituted benzene ring. The pyrrolidine and piperidine rings exhibit envelope and chair conformations, respectively. An intermolecular C—H

Br interaction is observed.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809037994/is2463sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809037994/is2463Isup2.hkl Contains datablock I

CCDC reference: 750776

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.042
wR factor = 0.108
Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.57
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.80 Ratio
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      64.00 A   3 

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT793_ALERT_4_G The Model has Chirality at C11     (Verify) ....          R
PLAT793_ALERT_4_G The Model has Chirality at C12     (Verify) ....          R
PLAT793_ALERT_4_G The Model has Chirality at C18     (Verify) ....          S
PLAT793_ALERT_4_G The Model has Chirality at C19     (Verify) ....          R

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

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

Comment top

Indolizine derivatives exhibit antioxidative (Teklu et al., 2005), antiherpes (Foster et al., 1995), anti-inflammatory (Malonne et al., 1998) and antiviral (Medda et al., 2003) activities. In addition, indolizines are used as antimycobacterial agents against mycobacterial tuberculosis (Gundersen et al., 2003).

The geometric parameters of the title compound (Fig. 1) agree well with reported similar structures (Gunasekaran et al., 2009; Kamala et al., 2009). The mean plane of naphthalene ring makes the dihedral angle of 22.0 (1)° with the benzene ring. The pyrrolidine ring exhibits an envelope conformation and the piperidine (N1/C14–C18) ring exhibits a chair conformation [C16—C15—C14—N1 = 56.3 (3)° and C16—C17—C18—N1 = -53.9 (3)°]. The sum of bond angles around N1 [338.3 (2)°] indicates sp³ hybridization.

Related literature top

For the biological activities of indolizine derivatives, see: Gundersen et al. (2003); Teklu et al. (2005); Foster et al. (1995); Malonne et al. (1998); Medda et al. (2003). For related structures, see: Gunasekaran et al. (2009); Kamala et al. (2009).

Experimental top

A mixture of (Z)-methyl 2-((1-formylnaphthalen-2-yloxy)methyl) -3-(4-bromophenyl)acrylate (20 mmol) and piperidine-2-carboxylic acid (30 mmol) were refluxed in benzene for 20 h and the solvent was removed under reduced pressure. The crude product was subjected to column chromatography to get the pure product. Chloroform and methanol (1:1) solvent mixture was used for the crystallization under slow evaporation method.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Methyl 9-(4-bromophenyl)-8a,9,9a,10,11,12,13,14a-octahydro-8H- benzo[f]chromeno[3,4-b]indolizine-8a-carboxylate top

Crystal data top

C₂₇H₂₆BrNO₃	D_x = 1.451 Mg m⁻³
M_r = 492.40	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3	Cell parameters from 4759 reflections
Hall symbol: -P 3	θ = 2.2–25.7°
a = 18.4405 (8) Å	µ = 1.85 mm⁻¹
c = 11.4828 (8) Å	T = 293 K
V = 3381.6 (3) Å³	Block, colourless
Z = 6	0.25 × 0.20 × 0.20 mm
F(000) = 1524

Data collection top

Bruker Kappa APEXII CCD diffractometer	5338 independent reflections
Radiation source: fine-focus sealed tube	2509 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.113
Detector resolution: 0 pixels mm^-1	θ_max = 27.8°, θ_min = 2.2°
ω and ϕ scans	h = −22→24
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −24→24
T_min = 0.654, T_max = 0.708	l = −8→15
23085 measured reflections

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 0.85	w = 1/[σ²(F_o²) + (0.0452P)²] where P = (F_o² + 2F_c²)/3
5338 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.85 e Å⁻³
2 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₇H₂₆BrNO₃	Z = 6
M_r = 492.40	Mo Kα radiation
Trigonal, P3	µ = 1.85 mm⁻¹
a = 18.4405 (8) Å	T = 293 K
c = 11.4828 (8) Å	0.25 × 0.20 × 0.20 mm
V = 3381.6 (3) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	5338 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2509 reflections with I > 2σ(I)
T_min = 0.654, T_max = 0.708	R_int = 0.113
23085 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	2 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 0.85	Δρ_max = 0.85 e Å⁻³
5338 reflections	Δρ_min = −0.33 e Å⁻³
290 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.32587 (18)	0.03952 (17)	−0.2836 (3)	0.0450 (7)
C2	0.2679 (2)	0.0537 (2)	−0.3441 (3)	0.0616 (9)
H2	0.2401	0.0769	−0.3050	0.074*
C3	0.2515 (3)	0.0339 (2)	−0.4604 (3)	0.0850 (13)
H3	0.2123	0.0432	−0.4982	0.102*
C4	0.2927 (3)	0.0004 (2)	−0.5221 (3)	0.0859 (13)
H4	0.2821	−0.0115	−0.6011	0.103*
C5	0.3479 (3)	−0.0149 (2)	−0.4667 (3)	0.0786 (12)
H5	0.3752	−0.0375	−0.5082	0.094*
C6	0.3654 (2)	0.00269 (18)	−0.3465 (3)	0.0564 (9)
C7	0.4228 (2)	−0.01415 (18)	−0.2873 (3)	0.0627 (10)
H7	0.4519	−0.0349	−0.3286	0.075*
C8	0.43567 (19)	−0.00053 (17)	−0.1725 (3)	0.0513 (8)
H8	0.4704	−0.0156	−0.1336	0.062*
C9	0.39688 (17)	0.03636 (16)	−0.1111 (2)	0.0384 (7)
C10	0.34630 (16)	0.06057 (15)	−0.1639 (2)	0.0356 (7)
C11	0.32309 (16)	0.11839 (16)	−0.1002 (2)	0.0341 (6)
H11	0.2669	0.1056	−0.1242	0.041*
C12	0.32533 (15)	0.11112 (16)	0.0348 (2)	0.0333 (6)
C13	0.34153 (18)	0.04079 (17)	0.0692 (2)	0.0431 (7)
H13A	0.3526	0.0438	0.1522	0.052*
H13B	0.2920	−0.0127	0.0531	0.052*
C14	0.41242 (18)	0.23382 (17)	−0.2399 (2)	0.0434 (7)
H14A	0.3650	0.2180	−0.2912	0.052*
H14B	0.4416	0.2053	−0.2663	0.052*
C15	0.47016 (18)	0.32660 (18)	−0.2460 (2)	0.0477 (8)
H15A	0.4395	0.3550	−0.2268	0.057*
H15B	0.4914	0.3422	−0.3247	0.057*
C16	0.54293 (18)	0.35396 (18)	−0.1621 (3)	0.0492 (8)
H16A	0.5765	0.3293	−0.1850	0.059*
H16B	0.5782	0.4144	−0.1644	0.059*
C17	0.50984 (18)	0.32634 (16)	−0.0398 (2)	0.0425 (7)
H17A	0.5562	0.3404	0.0128	0.051*
H17B	0.4815	0.3558	−0.0140	0.051*
C18	0.44950 (16)	0.23290 (15)	−0.0361 (2)	0.0329 (6)
H18	0.4799	0.2029	−0.0508	0.039*
C19	0.39796 (15)	0.19968 (16)	0.0742 (2)	0.0323 (6)
H19	0.3722	0.2342	0.0882	0.039*
C20	0.44263 (16)	0.20142 (16)	0.1853 (2)	0.0326 (6)
C21	0.40965 (17)	0.20588 (17)	0.2912 (2)	0.0395 (7)
H21	0.3612	0.2096	0.2925	0.047*
C22	0.44673 (19)	0.20491 (18)	0.3956 (2)	0.0454 (8)
H22	0.4232	0.2072	0.4662	0.054*
C23	0.51857 (18)	0.20047 (17)	0.3933 (2)	0.0414 (7)
C24	0.55532 (18)	0.19869 (17)	0.2895 (3)	0.0461 (8)
H24	0.6053	0.1979	0.2888	0.055*
C25	0.51612 (17)	0.19814 (17)	0.1866 (2)	0.0426 (7)
H25	0.5397	0.1955	0.1162	0.051*
C26	0.24417 (18)	0.09807 (19)	0.0883 (3)	0.0456 (7)
C27	0.1435 (2)	0.0356 (3)	0.2332 (4)	0.0985 (14)
H27A	0.1533	0.0860	0.2714	0.148*
H27B	0.1240	−0.0091	0.2891	0.148*
H27C	0.1021	0.0211	0.1735	0.148*
N1	0.38286 (13)	0.20806 (12)	−0.12185 (17)	0.0301 (5)
O1	0.41141 (11)	0.04609 (11)	0.00670 (17)	0.0446 (5)
O2	0.20524 (13)	0.12926 (15)	0.0531 (2)	0.0685 (7)
O3	0.22148 (12)	0.04877 (13)	0.18093 (17)	0.0569 (6)
Br1	0.56763 (2)	0.19502 (2)	0.53512 (3)	0.06620 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0421 (18)	0.0299 (16)	0.0472 (19)	0.0063 (14)	0.0072 (13)	−0.0069 (14)
C2	0.056 (2)	0.060 (2)	0.052 (2)	0.0171 (17)	−0.0091 (16)	−0.0117 (17)
C3	0.091 (3)	0.073 (3)	0.059 (3)	0.016 (2)	−0.019 (2)	−0.012 (2)
C4	0.116 (4)	0.060 (3)	0.052 (3)	0.021 (3)	0.002 (3)	−0.016 (2)
C5	0.110 (3)	0.042 (2)	0.061 (3)	0.022 (2)	0.020 (2)	−0.0113 (19)
C6	0.070 (2)	0.0282 (18)	0.053 (2)	0.0107 (17)	0.0124 (18)	−0.0059 (15)
C7	0.074 (3)	0.0336 (19)	0.077 (3)	0.0245 (19)	0.036 (2)	0.0021 (18)
C8	0.056 (2)	0.0335 (18)	0.068 (2)	0.0251 (16)	0.0165 (18)	0.0085 (16)
C9	0.0382 (17)	0.0246 (15)	0.0459 (19)	0.0109 (14)	0.0076 (14)	0.0020 (13)
C10	0.0324 (16)	0.0240 (15)	0.0413 (17)	0.0071 (13)	0.0047 (13)	−0.0016 (12)
C11	0.0281 (15)	0.0342 (16)	0.0382 (16)	0.0142 (13)	−0.0002 (12)	−0.0010 (13)
C12	0.0313 (16)	0.0295 (15)	0.0368 (16)	0.0134 (13)	0.0027 (12)	0.0023 (12)
C13	0.0474 (19)	0.0340 (17)	0.0440 (17)	0.0175 (15)	0.0040 (14)	0.0025 (13)
C14	0.0450 (18)	0.0462 (19)	0.0402 (17)	0.0236 (16)	0.0022 (14)	0.0055 (14)
C15	0.051 (2)	0.046 (2)	0.0464 (18)	0.0243 (16)	0.0104 (15)	0.0115 (15)
C16	0.0425 (18)	0.0320 (17)	0.069 (2)	0.0157 (15)	0.0108 (16)	0.0068 (15)
C17	0.0395 (18)	0.0322 (16)	0.0538 (19)	0.0165 (14)	−0.0031 (14)	−0.0018 (14)
C18	0.0354 (16)	0.0291 (15)	0.0369 (15)	0.0182 (13)	−0.0024 (13)	−0.0020 (12)
C19	0.0321 (16)	0.0315 (15)	0.0383 (16)	0.0197 (13)	−0.0019 (12)	−0.0035 (12)
C20	0.0346 (16)	0.0288 (15)	0.0370 (16)	0.0178 (13)	−0.0026 (12)	−0.0039 (12)
C21	0.0344 (16)	0.0452 (18)	0.0452 (18)	0.0246 (15)	−0.0037 (14)	−0.0045 (14)
C22	0.050 (2)	0.055 (2)	0.0356 (17)	0.0298 (17)	−0.0023 (14)	−0.0059 (14)
C23	0.0450 (19)	0.0389 (18)	0.0412 (18)	0.0217 (15)	−0.0112 (14)	0.0008 (13)
C24	0.0398 (18)	0.0508 (19)	0.056 (2)	0.0286 (16)	−0.0092 (15)	−0.0005 (15)
C25	0.0427 (18)	0.0492 (19)	0.0432 (18)	0.0285 (15)	−0.0001 (14)	−0.0020 (14)
C26	0.0377 (18)	0.0465 (19)	0.0462 (19)	0.0162 (14)	0.0011 (14)	−0.0031 (15)
C27	0.079 (3)	0.108 (3)	0.103 (3)	0.043 (3)	0.044 (2)	0.021 (3)
N1	0.0292 (12)	0.0280 (12)	0.0332 (12)	0.0143 (10)	0.0022 (10)	0.0007 (10)
O1	0.0462 (13)	0.0353 (12)	0.0571 (14)	0.0238 (10)	−0.0026 (10)	−0.0004 (10)
O2	0.0512 (15)	0.0940 (19)	0.0727 (16)	0.0455 (13)	0.0179 (12)	0.0238 (13)
O3	0.0493 (14)	0.0684 (15)	0.0484 (13)	0.0260 (12)	0.0151 (10)	0.0127 (11)
Br1	0.0694 (3)	0.0800 (3)	0.0538 (2)	0.0408 (2)	−0.01750 (18)	0.00658 (18)

Geometric parameters (Å, º) top

C1—C2	1.406 (4)	C15—C16	1.518 (4)
C1—C6	1.417 (4)	C15—H15A	0.9700
C1—C10	1.427 (4)	C15—H15B	0.9700
C2—C3	1.377 (4)	C16—C17	1.515 (4)
C2—H2	0.9300	C16—H16A	0.9700
C3—C4	1.390 (6)	C16—H16B	0.9700
C3—H3	0.9300	C17—C18	1.514 (4)
C4—C5	1.344 (5)	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
C5—C6	1.418 (5)	C18—N1	1.459 (3)
C5—H5	0.9300	C18—C19	1.516 (3)
C6—C7	1.416 (5)	C18—H18	0.9800
C7—C8	1.341 (4)	C19—C20	1.511 (3)
C7—H7	0.9300	C19—H19	0.9800
C8—C9	1.399 (4)	C20—C21	1.380 (3)
C8—H8	0.9300	C20—C25	1.387 (4)
C9—C10	1.361 (4)	C21—C22	1.385 (4)
C9—O1	1.374 (3)	C21—H21	0.9300
C10—C11	1.521 (4)	C22—C23	1.368 (4)
C11—N1	1.479 (3)	C22—H22	0.9300
C11—C12	1.558 (3)	C23—C24	1.379 (4)
C11—H11	0.9800	C23—Br1	1.890 (3)
C12—C26	1.521 (4)	C24—C25	1.383 (4)
C12—C13	1.521 (4)	C24—H24	0.9300
C12—C19	1.574 (3)	C25—H25	0.9300
C13—O1	1.435 (3)	C26—O2	1.193 (3)
C13—H13A	0.9700	C26—O3	1.324 (3)
C13—H13B	0.9700	C27—O3	1.461 (4)
C14—N1	1.450 (3)	C27—H27A	0.9600
C14—C15	1.498 (4)	C27—H27B	0.9600
C14—H14A	0.9700	C27—H27C	0.9600
C14—H14B	0.9700

C2—C1—C6	117.4 (3)	C16—C15—H15B	109.5
C2—C1—C10	123.2 (3)	H15A—C15—H15B	108.1
C6—C1—C10	119.4 (3)	C17—C16—C15	109.6 (2)
C3—C2—C1	121.0 (3)	C17—C16—H16A	109.7
C3—C2—H2	119.5	C15—C16—H16A	109.7
C1—C2—H2	119.5	C17—C16—H16B	109.7
C2—C3—C4	121.1 (4)	C15—C16—H16B	109.7
C2—C3—H3	119.4	H16A—C16—H16B	108.2
C4—C3—H3	119.4	C18—C17—C16	110.6 (2)
C5—C4—C3	119.4 (4)	C18—C17—H17A	109.5
C5—C4—H4	120.3	C16—C17—H17A	109.5
C3—C4—H4	120.3	C18—C17—H17B	109.5
C4—C5—C6	121.5 (4)	C16—C17—H17B	109.5
C4—C5—H5	119.2	H17A—C17—H17B	108.1
C6—C5—H5	119.2	N1—C18—C17	111.3 (2)
C7—C6—C1	118.7 (3)	N1—C18—C19	100.2 (2)
C7—C6—C5	121.8 (3)	C17—C18—C19	116.0 (2)
C1—C6—C5	119.5 (4)	N1—C18—H18	109.6
C8—C7—C6	120.8 (3)	C17—C18—H18	109.6
C8—C7—H7	119.6	C19—C18—H18	109.6
C6—C7—H7	119.6	C20—C19—C18	118.2 (2)
C7—C8—C9	120.0 (3)	C20—C19—C12	115.9 (2)
C7—C8—H8	120.0	C18—C19—C12	102.47 (19)
C9—C8—H8	120.0	C20—C19—H19	106.5
C10—C9—O1	121.1 (2)	C18—C19—H19	106.5
C10—C9—C8	122.4 (3)	C12—C19—H19	106.5
O1—C9—C8	116.5 (3)	C21—C20—C25	117.6 (2)
C9—C10—C1	118.1 (3)	C21—C20—C19	119.6 (2)
C9—C10—C11	119.7 (2)	C25—C20—C19	122.8 (2)
C1—C10—C11	121.7 (3)	C20—C21—C22	121.8 (3)
N1—C11—C10	112.9 (2)	C20—C21—H21	119.1
N1—C11—C12	103.10 (19)	C22—C21—H21	119.1
C10—C11—C12	112.9 (2)	C23—C22—C21	118.9 (3)
N1—C11—H11	109.2	C23—C22—H22	120.6
C10—C11—H11	109.2	C21—C22—H22	120.6
C12—C11—H11	109.2	C22—C23—C24	121.4 (2)
C26—C12—C13	111.0 (2)	C22—C23—Br1	119.3 (2)
C26—C12—C11	110.4 (2)	C24—C23—Br1	119.3 (2)
C13—C12—C11	110.9 (2)	C23—C24—C25	118.5 (3)
C26—C12—C19	107.9 (2)	C23—C24—H24	120.7
C13—C12—C19	112.5 (2)	C25—C24—H24	120.7
C11—C12—C19	103.98 (19)	C24—C25—C20	121.8 (3)
O1—C13—C12	111.4 (2)	C24—C25—H25	119.1
O1—C13—H13A	109.3	C20—C25—H25	119.1
C12—C13—H13A	109.3	O2—C26—O3	122.9 (3)
O1—C13—H13B	109.3	O2—C26—C12	124.7 (3)
C12—C13—H13B	109.3	O3—C26—C12	112.4 (3)
H13A—C13—H13B	108.0	O3—C27—H27A	109.5
N1—C14—C15	110.7 (2)	O3—C27—H27B	109.5
N1—C14—H14A	109.5	H27A—C27—H27B	109.5
C15—C14—H14A	109.5	O3—C27—H27C	109.5
N1—C14—H14B	109.5	H27A—C27—H27C	109.5
C15—C14—H14B	109.5	H27B—C27—H27C	109.5
H14A—C14—H14B	108.1	C14—N1—C18	114.1 (2)
C14—C15—C16	110.8 (2)	C14—N1—C11	118.1 (2)
C14—C15—H15A	109.5	C18—N1—C11	106.10 (18)
C16—C15—H15A	109.5	C9—O1—C13	112.0 (2)
C14—C15—H15B	109.5	C26—O3—C27	113.0 (3)

C6—C1—C2—C3	−1.2 (5)	N1—C18—C19—C12	42.9 (2)
C10—C1—C2—C3	178.6 (3)	C17—C18—C19—C12	162.8 (2)
C1—C2—C3—C4	−0.9 (6)	C26—C12—C19—C20	90.7 (3)
C2—C3—C4—C5	1.6 (6)	C13—C12—C19—C20	−32.0 (3)
C3—C4—C5—C6	−0.1 (6)	C11—C12—C19—C20	−152.0 (2)
C2—C1—C6—C7	−178.6 (3)	C26—C12—C19—C18	−139.1 (2)
C10—C1—C6—C7	1.6 (4)	C13—C12—C19—C18	98.1 (2)
C2—C1—C6—C5	2.5 (4)	C11—C12—C19—C18	−21.9 (2)
C10—C1—C6—C5	−177.3 (3)	C18—C19—C20—C21	153.2 (2)
C4—C5—C6—C7	179.2 (3)	C12—C19—C20—C21	−84.7 (3)
C4—C5—C6—C1	−1.9 (5)	C18—C19—C20—C25	−27.3 (4)
C1—C6—C7—C8	4.1 (5)	C12—C19—C20—C25	94.9 (3)
C5—C6—C7—C8	−177.0 (3)	C25—C20—C21—C22	−1.7 (4)
C6—C7—C8—C9	−4.6 (5)	C19—C20—C21—C22	177.9 (3)
C7—C8—C9—C10	−0.8 (4)	C20—C21—C22—C23	0.8 (4)
C7—C8—C9—O1	178.3 (3)	C21—C22—C23—C24	1.3 (4)
O1—C9—C10—C1	−172.6 (2)	C21—C22—C23—Br1	−177.7 (2)
C8—C9—C10—C1	6.5 (4)	C22—C23—C24—C25	−2.5 (4)
O1—C9—C10—C11	15.6 (4)	Br1—C23—C24—C25	176.5 (2)
C8—C9—C10—C11	−165.3 (2)	C23—C24—C25—C20	1.6 (4)
C2—C1—C10—C9	173.5 (3)	C21—C20—C25—C24	0.4 (4)
C6—C1—C10—C9	−6.7 (4)	C19—C20—C25—C24	−179.1 (2)
C2—C1—C10—C11	−14.9 (4)	C13—C12—C26—O2	−159.1 (3)
C6—C1—C10—C11	164.9 (3)	C11—C12—C26—O2	−35.8 (4)
C9—C10—C11—N1	89.9 (3)	C19—C12—C26—O2	77.2 (3)
C1—C10—C11—N1	−81.6 (3)	C13—C12—C26—O3	22.0 (3)
C9—C10—C11—C12	−26.5 (3)	C11—C12—C26—O3	145.3 (2)
C1—C10—C11—C12	162.0 (2)	C19—C12—C26—O3	−101.6 (3)
N1—C11—C12—C26	108.5 (2)	C15—C14—N1—C18	−55.9 (3)
C10—C11—C12—C26	−129.3 (2)	C15—C14—N1—C11	178.3 (2)
N1—C11—C12—C13	−128.1 (2)	C17—C18—N1—C14	54.8 (3)
C10—C11—C12—C13	−6.0 (3)	C19—C18—N1—C14	178.1 (2)
N1—C11—C12—C19	−7.0 (2)	C17—C18—N1—C11	−173.3 (2)
C10—C11—C12—C19	115.1 (2)	C19—C18—N1—C11	−50.0 (2)
C26—C12—C13—O1	172.0 (2)	C10—C11—N1—C14	42.9 (3)
C11—C12—C13—O1	48.9 (3)	C12—C11—N1—C14	165.0 (2)
C19—C12—C13—O1	−67.0 (3)	C10—C11—N1—C18	−86.7 (2)
N1—C14—C15—C16	56.3 (3)	C12—C11—N1—C18	35.5 (2)
C14—C15—C16—C17	−56.7 (3)	C10—C9—O1—C13	30.1 (3)
C15—C16—C17—C18	55.2 (3)	C8—C9—O1—C13	−149.1 (2)
C16—C17—C18—N1	−53.9 (3)	C12—C13—O1—C9	−63.2 (3)
C16—C17—C18—C19	−167.6 (2)	O2—C26—O3—C27	1.2 (4)
N1—C18—C19—C20	171.6 (2)	C12—C26—O3—C27	−180.0 (3)
C17—C18—C19—C20	−68.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···Br1ⁱ	0.97	2.73	3.588 (3)	147

Symmetry code: (i) −x+y+1, −x+1, z−1.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₆BrNO₃
M_r	492.40
Crystal system, space group	Trigonal, P3
Temperature (K)	293
a, c (Å)	18.4405 (8), 11.4828 (8)
V (Å³)	3381.6 (3)
Z	6
Radiation type	Mo Kα
µ (mm⁻¹)	1.85
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.654, 0.708
No. of measured, independent and observed [I > 2σ(I)] reflections	23085, 5338, 2509
R_int	0.113
(sin θ/λ)_max (Å⁻¹)	0.656

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.108, 0.85
No. of reflections	5338
No. of parameters	290
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.33

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).