6-Bromo-2,4-bis­(3-methoxy­phen­yl)-3,4-dihydro-2H-1,3-naphthoxazine

Sarojini, B.K.; Narayana, B.; Mayekar, A.N.; Yathirajan, H.S.; Bolte, M.

doi:10.1107/S1600536807057832

6-Bromo-2,4-bis(3-methoxyphenyl)-3,4-dihydro-2H-1,3-naphthoxazine

B. K. Sarojini, B. Narayana, A. N. Mayekar, H. S. Yathirajan and M. Bolte

The oxazine ring in the title compound, C₂₆H₂₂BrNO₃, adopts a half-chair conformation. The amino H atom is not involved in a classical hydrogen bond, but there is a weak N—H

π interaction to the centre of an aromatic ring.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057832/pv2044sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057832/pv2044Isup2.hkl Contains datablock I

CCDC reference: 674657

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.032
wR factor = 0.086
Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N8     -   H8     ...          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br21   ..  Br21    ..       3.48 Ang.

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C7     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C9     = ...          R

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Domino (Tietze, 1996; Armstrong et al., 1996) and multicomponent (Domling & Ugi, 2000; Kappe, 2000; Bienayme et al., 2000; Simon et al., 2004) reactions (MCRs) are powerful strategies in current organic synthesis. Consistently, several reported MCRs feature Diels-Alder chemistry with heterodiene (Tailor & Hall, 2000; Tietze & Rachkelmann, 2004;) building blocks for the synthesis of six-membered heterocyclic rings. In 1950's, oxazinic derivatives have drawn the attention because of their antitumoraly antituberculostatic activities and assigned a conformation with an axial N—R group when R= methyl and ethyl whereas a conformation with an equatorial N—R group when R= cyclohexyl and tert-butyl. The same series of compounds with n-propyl and iso-propyl derivatives have been studied by Allingham et al. (1968) using the 1H-NMR. Some related structures viz, (Z)-7-chloro-3-[(3-chlorophenyl)methylidene]-4-p-tosyl-3,4-dihydro-2H-1,4- benzoxazine (Chaudhuri et al., 2001), 2-amino-4,6-diphenyl-4H-1,3-oxazinium trifluoroacetate (Huang & Sun, 2005) and spirocyclohexane oxazines, thiazines and selenazines (Baert et al., 1989) have been reported. A new compound, (I), C₂₆H₂₂BrNO₃ was synthesized and its crystal structure is reported.

Geometric parameters in (I) are in the usual ranges. The amino H atom is not involved in a classical hydrogen bond but there is a weak N—H···π interaction to the centre of the ring composed of C5, C6, C11, C12, C13 and C14 [N—H 0.86 (2) Å, N···cog 2.709 Å, N···cog 3.496 Å, N—H···cog 153.3°; symmetry operator x - 1,y,z].

Related literature top

For related literature, see: Allingham et al. (1968); Armstrong et al. (1996); Baert et al. (1989); Bienayme et al. (2000); Chaudhuri et al. (2001); Domling & Ugi (2000); Huang & Sun (2005); Kappe (2000); Simon et al. (2004); Tailor & Hall (2000); Tietze (1996); Tietze & Rachkelmann (2004).

Experimental top

To 6-bromo-2-naphthol (2.23 g, 0.01 mol) in methanol (10 ml) was added m-anisaldehyde (2.7 g, 0.02 mol) and 10 ml of 30% methanolic ammonia and stirred at room temperature for 48 h. The solid separated was collected by filtration and crystallized in ethyl acetate and good quality crystals were obtained by evaporation of the solution prepared in acetone (m.p:361–363 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.

6-Bromo-2,4-bis(3-methoxyphenyl)-3,4-dihydro-2H-1,3-naphthoxazine top

Crystal data top

C₂₆H₂₂BrNO₃	Z = 2
M_r = 476.36	F(000) = 488
Triclinic, P1	D_x = 1.492 Mg m⁻³
a = 5.9753 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9177 (7) Å	Cell parameters from 29479 reflections
c = 18.1925 (13) Å	θ = 3.5–27.9°
α = 84.632 (6)°	µ = 1.97 mm⁻¹
β = 88.618 (6)°	T = 173 K
γ = 81.088 (5)°	Block, colourless
V = 1060.37 (13) Å³	0.33 × 0.27 × 0.25 mm

Data collection top

Stoe IPDSII two-circle diffractometer	4875 independent reflections
Radiation source: fine-focus sealed tube	4449 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 27.6°, θ_min = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −7→7
T_min = 0.563, T_max = 0.639	k = −12→12
23965 measured reflections	l = −23→23

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0532P)² + 0.321P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4875 reflections	Δρ_max = 0.37 e Å⁻³
287 parameters	Δρ_min = −0.53 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0214 (18)

Crystal data top

C₂₆H₂₂BrNO₃	γ = 81.088 (5)°
M_r = 476.36	V = 1060.37 (13) Å³
Triclinic, P1	Z = 2
a = 5.9753 (4) Å	Mo Kα radiation
b = 9.9177 (7) Å	µ = 1.97 mm⁻¹
c = 18.1925 (13) Å	T = 173 K
α = 84.632 (6)°	0.33 × 0.27 × 0.25 mm
β = 88.618 (6)°

Data collection top

Stoe IPDSII two-circle diffractometer	4875 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	4449 reflections with I > 2σ(I)
T_min = 0.563, T_max = 0.639	R_int = 0.044
23965 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.37 e Å⁻³
4875 reflections	Δρ_min = −0.53 e Å⁻³
287 parameters

Special details top

Experimental. Analysis found: C, H, N %; 65.48, 4.61, 2.90% for C₂₆H₂₂BrNO₃; required: C 65.55, H 4.66, N 2.94%.

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
C1	1.2244 (3)	1.10888 (19)	0.05325 (9)	0.0293 (3)
H1	1.3472	1.0830	0.0208	0.035*
C2	1.1620 (3)	1.24339 (19)	0.06485 (9)	0.0291 (3)
Br21	1.31702 (3)	1.37957 (2)	0.014156 (11)	0.04071 (9)
C3	0.9805 (3)	1.28612 (19)	0.11293 (10)	0.0309 (3)
H3	0.9389	1.3803	0.1202	0.037*
C4	0.8654 (3)	1.18928 (18)	0.14888 (9)	0.0279 (3)
H4	0.7446	1.2177	0.1816	0.034*
C5	0.9223 (3)	1.04756 (17)	0.13832 (8)	0.0228 (3)
C6	0.8016 (3)	0.94569 (16)	0.17455 (8)	0.0225 (3)
C7	0.5995 (3)	0.98412 (16)	0.22469 (8)	0.0212 (3)
H7	0.5004	1.0640	0.1987	0.032*
C71	0.6622 (3)	1.02780 (15)	0.29929 (8)	0.0207 (3)
C72	0.8827 (3)	0.99958 (18)	0.32690 (9)	0.0269 (3)
H72	1.0019	0.9528	0.2991	0.032*
C73	0.9255 (3)	1.0409 (2)	0.39569 (10)	0.0321 (4)
H73	1.0754	1.0223	0.4143	0.038*
C74	0.7538 (3)	1.10898 (18)	0.43773 (9)	0.0295 (3)
H74	0.7860	1.1365	0.4845	0.035*
C75	0.5339 (3)	1.13628 (17)	0.41039 (9)	0.0263 (3)
O751	0.3513 (2)	1.20077 (15)	0.44689 (7)	0.0371 (3)
C752	0.3873 (4)	1.2390 (2)	0.51912 (11)	0.0410 (4)
H75A	0.4524	1.1577	0.5508	0.061*
H75B	0.2424	1.2791	0.5402	0.061*
H75C	0.4918	1.3064	0.5158	0.061*
C76	0.4895 (3)	1.09611 (16)	0.34104 (9)	0.0236 (3)
H76	0.3398	1.1157	0.3223	0.028*
N8	0.4640 (2)	0.87111 (14)	0.23740 (8)	0.0231 (3)
H8	0.383 (4)	0.870 (2)	0.1992 (12)	0.026 (5)*
C9	0.6035 (3)	0.74024 (17)	0.25247 (9)	0.0240 (3)
H9	0.6894	0.7416	0.2988	0.036*
C91	0.4583 (3)	0.62705 (16)	0.26350 (9)	0.0246 (3)
C92	0.2967 (3)	0.63350 (17)	0.32011 (9)	0.0280 (3)
H92	0.2815	0.7069	0.3508	0.034*
C93	0.1567 (3)	0.53274 (18)	0.33211 (10)	0.0297 (3)
O931	0.0050 (3)	0.54830 (14)	0.38976 (9)	0.0454 (4)
C932	−0.1263 (4)	0.4403 (2)	0.40788 (14)	0.0440 (5)
H93A	−0.2307	0.4373	0.3676	0.066*
H93B	−0.2129	0.4571	0.4534	0.066*
H93C	−0.0249	0.3525	0.4151	0.066*
C94	0.1746 (3)	0.42578 (18)	0.28676 (11)	0.0324 (4)
H94	0.0785	0.3577	0.2942	0.039*
C95	0.3360 (3)	0.42067 (19)	0.23030 (11)	0.0351 (4)
H95	0.3492	0.3481	0.1991	0.042*
C96	0.4787 (3)	0.51908 (19)	0.21830 (10)	0.0316 (4)
H96	0.5890	0.5130	0.1798	0.038*
O10	0.7651 (2)	0.70462 (12)	0.19325 (7)	0.0286 (3)
C11	0.8681 (3)	0.80986 (17)	0.16211 (9)	0.0237 (3)
C12	1.0515 (3)	0.76955 (18)	0.11308 (9)	0.0272 (3)
H12	1.0938	0.6757	0.1051	0.033*
C13	1.1661 (3)	0.86601 (19)	0.07776 (9)	0.0283 (3)
H13	1.2871	0.8386	0.0449	0.034*
C14	1.1069 (3)	1.00730 (17)	0.08938 (8)	0.0248 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0260 (8)	0.0370 (9)	0.0253 (8)	−0.0079 (7)	0.0056 (6)	−0.0017 (6)
C2	0.0277 (8)	0.0333 (9)	0.0274 (8)	−0.0110 (7)	0.0030 (6)	0.0013 (6)
Br21	0.04119 (13)	0.03886 (12)	0.04419 (13)	−0.01807 (8)	0.01209 (8)	0.00198 (8)
C3	0.0316 (8)	0.0278 (8)	0.0339 (9)	−0.0083 (7)	0.0051 (7)	−0.0012 (7)
C4	0.0262 (8)	0.0285 (8)	0.0291 (8)	−0.0046 (6)	0.0066 (6)	−0.0033 (6)
C5	0.0221 (7)	0.0266 (8)	0.0197 (7)	−0.0044 (6)	0.0012 (5)	−0.0010 (6)
C6	0.0218 (7)	0.0265 (8)	0.0193 (7)	−0.0043 (6)	0.0020 (5)	−0.0021 (6)
C7	0.0204 (7)	0.0218 (7)	0.0214 (7)	−0.0038 (6)	0.0016 (5)	−0.0019 (5)
C71	0.0220 (7)	0.0197 (7)	0.0208 (7)	−0.0054 (6)	0.0017 (5)	−0.0008 (5)
C72	0.0212 (7)	0.0331 (8)	0.0260 (8)	−0.0041 (6)	0.0014 (6)	−0.0010 (6)
C73	0.0254 (8)	0.0437 (10)	0.0282 (8)	−0.0099 (7)	−0.0043 (6)	−0.0002 (7)
C74	0.0367 (9)	0.0326 (9)	0.0220 (7)	−0.0138 (7)	−0.0020 (6)	−0.0019 (6)
C75	0.0319 (8)	0.0221 (7)	0.0253 (7)	−0.0053 (6)	0.0044 (6)	−0.0029 (6)
O751	0.0401 (7)	0.0416 (7)	0.0288 (6)	0.0012 (6)	0.0067 (5)	−0.0140 (5)
C752	0.0582 (13)	0.0375 (10)	0.0297 (9)	−0.0112 (9)	0.0113 (8)	−0.0131 (8)
C76	0.0225 (7)	0.0250 (7)	0.0236 (7)	−0.0041 (6)	0.0010 (6)	−0.0024 (6)
N8	0.0211 (6)	0.0233 (6)	0.0257 (6)	−0.0052 (5)	−0.0006 (5)	−0.0038 (5)
C9	0.0232 (7)	0.0247 (7)	0.0240 (7)	−0.0039 (6)	0.0020 (6)	−0.0015 (6)
C91	0.0255 (7)	0.0227 (7)	0.0255 (7)	−0.0037 (6)	0.0002 (6)	−0.0009 (6)
C92	0.0317 (8)	0.0236 (8)	0.0297 (8)	−0.0065 (7)	0.0058 (6)	−0.0050 (6)
C93	0.0289 (8)	0.0237 (8)	0.0360 (9)	−0.0038 (6)	0.0071 (7)	−0.0013 (6)
O931	0.0507 (9)	0.0302 (7)	0.0576 (9)	−0.0153 (6)	0.0303 (7)	−0.0090 (6)
C932	0.0391 (10)	0.0299 (9)	0.0623 (13)	−0.0095 (8)	0.0189 (9)	0.0016 (9)
C94	0.0310 (9)	0.0233 (8)	0.0444 (10)	−0.0081 (7)	0.0030 (7)	−0.0045 (7)
C95	0.0407 (10)	0.0269 (8)	0.0403 (10)	−0.0089 (7)	0.0043 (8)	−0.0115 (7)
C96	0.0339 (9)	0.0290 (8)	0.0327 (8)	−0.0060 (7)	0.0067 (7)	−0.0068 (7)
O10	0.0282 (6)	0.0218 (5)	0.0351 (6)	−0.0037 (5)	0.0097 (5)	−0.0027 (5)
C11	0.0224 (7)	0.0265 (8)	0.0223 (7)	−0.0047 (6)	0.0015 (6)	−0.0009 (6)
C12	0.0257 (8)	0.0279 (8)	0.0277 (8)	−0.0010 (6)	0.0023 (6)	−0.0071 (6)
C13	0.0262 (8)	0.0345 (9)	0.0243 (7)	−0.0035 (7)	0.0051 (6)	−0.0059 (6)
C14	0.0235 (7)	0.0306 (8)	0.0206 (7)	−0.0057 (6)	0.0017 (6)	−0.0020 (6)

Geometric parameters (Å, º) top

C1—C2	1.363 (3)	C752—H75C	0.9800
C1—C14	1.419 (2)	C76—H76	0.9500
C1—H1	0.9500	N8—C9	1.437 (2)
C2—C3	1.415 (2)	N8—H8	0.86 (2)
C2—Br21	1.9093 (17)	C9—O10	1.4603 (19)
C3—C4	1.375 (2)	C9—C91	1.518 (2)
C3—H3	0.9500	C9—H9	1.0000
C4—C5	1.424 (2)	C91—C92	1.394 (2)
C4—H4	0.9500	C91—C96	1.399 (2)
C5—C14	1.432 (2)	C92—C93	1.399 (2)
C5—C6	1.433 (2)	C92—H92	0.9500
C6—C11	1.382 (2)	C93—O931	1.373 (2)
C6—C7	1.518 (2)	C93—C94	1.394 (2)
C7—N8	1.4796 (19)	O931—C932	1.433 (2)
C7—C71	1.534 (2)	C932—H93A	0.9800
C7—H7	1.0000	C932—H93B	0.9800
C71—C76	1.394 (2)	C932—H93C	0.9800
C71—C72	1.400 (2)	C94—C95	1.391 (3)
C72—C73	1.394 (2)	C94—H94	0.9500
C72—H72	0.9500	C95—C96	1.392 (3)
C73—C74	1.392 (3)	C95—H95	0.9500
C73—H73	0.9500	C96—H96	0.9500
C74—C75	1.394 (2)	O10—C11	1.3644 (19)
C74—H74	0.9500	C11—C12	1.428 (2)
C75—O751	1.367 (2)	C12—C13	1.365 (2)
C75—C76	1.401 (2)	C12—H12	0.9500
O751—C752	1.431 (2)	C13—C14	1.425 (2)
C752—H75A	0.9800	C13—H13	0.9500
C752—H75B	0.9800

C2—C1—C14	120.37 (16)	C75—C76—H76	119.6
C2—C1—H1	119.8	C9—N8—C7	112.20 (12)
C14—C1—H1	119.8	C9—N8—H8	109.6 (14)
C1—C2—C3	121.56 (16)	C7—N8—H8	109.1 (14)
C1—C2—Br21	119.97 (13)	N8—C9—O10	113.44 (13)
C3—C2—Br21	118.45 (13)	N8—C9—C91	110.47 (13)
C4—C3—C2	119.02 (16)	O10—C9—C91	106.88 (13)
C4—C3—H3	120.5	N8—C9—H9	108.6
C2—C3—H3	120.5	O10—C9—H9	108.6
C3—C4—C5	121.73 (15)	C91—C9—H9	108.6
C3—C4—H4	119.1	C92—C91—C96	119.41 (16)
C5—C4—H4	119.1	C92—C91—C9	118.17 (14)
C4—C5—C14	118.02 (15)	C96—C91—C9	122.40 (15)
C4—C5—C6	122.37 (14)	C91—C92—C93	120.51 (15)
C14—C5—C6	119.62 (15)	C91—C92—H92	119.7
C11—C6—C5	119.06 (14)	C93—C92—H92	119.7
C11—C6—C7	119.46 (14)	O931—C93—C94	123.98 (16)
C5—C6—C7	121.47 (14)	O931—C93—C92	115.70 (15)
N8—C7—C6	111.18 (13)	C94—C93—C92	120.32 (16)
N8—C7—C71	109.34 (12)	C93—O931—C932	117.07 (15)
C6—C7—C71	113.95 (12)	O931—C932—H93A	109.5
N8—C7—H7	107.4	O931—C932—H93B	109.5
C6—C7—H7	107.4	H93A—C932—H93B	109.5
C71—C7—H7	107.4	O931—C932—H93C	109.5
C76—C71—C72	119.53 (14)	H93A—C932—H93C	109.5
C76—C71—C7	117.80 (13)	H93B—C932—H93C	109.5
C72—C71—C7	122.66 (14)	C95—C94—C93	118.64 (16)
C73—C72—C71	119.22 (15)	C95—C94—H94	120.7
C73—C72—H72	120.4	C93—C94—H94	120.7
C71—C72—H72	120.4	C94—C95—C96	121.71 (16)
C74—C73—C72	121.55 (15)	C94—C95—H95	119.1
C74—C73—H73	119.2	C96—C95—H95	119.1
C72—C73—H73	119.2	C95—C96—C91	119.39 (16)
C73—C74—C75	119.18 (15)	C95—C96—H96	120.3
C73—C74—H74	120.4	C91—C96—H96	120.3
C75—C74—H74	120.4	C11—O10—C9	115.03 (12)
O751—C75—C74	124.50 (15)	O10—C11—C6	124.07 (14)
O751—C75—C76	115.79 (15)	O10—C11—C12	114.49 (14)
C74—C75—C76	119.71 (15)	C6—C11—C12	121.42 (15)
C75—O751—C752	117.67 (16)	C13—C12—C11	119.94 (16)
O751—C752—H75A	109.5	C13—C12—H12	120.0
O751—C752—H75B	109.5	C11—C12—H12	120.0
H75A—C752—H75B	109.5	C12—C13—C14	121.01 (15)
O751—C752—H75C	109.5	C12—C13—H13	119.5
H75A—C752—H75C	109.5	C14—C13—H13	119.5
H75B—C752—H75C	109.5	C1—C14—C13	121.75 (15)
C71—C76—C75	120.80 (15)	C1—C14—C5	119.30 (15)
C71—C76—H76	119.6	C13—C14—C5	118.94 (15)

C14—C1—C2—C3	0.2 (3)	N8—C9—C91—C92	−59.34 (19)
C14—C1—C2—Br21	−178.56 (12)	O10—C9—C91—C92	176.81 (14)
C1—C2—C3—C4	0.2 (3)	N8—C9—C91—C96	119.51 (17)
Br21—C2—C3—C4	179.02 (13)	O10—C9—C91—C96	−4.3 (2)
C2—C3—C4—C5	−0.8 (3)	C96—C91—C92—C93	0.4 (3)
C3—C4—C5—C14	0.8 (2)	C9—C91—C92—C93	179.25 (15)
C3—C4—C5—C6	−179.05 (16)	C91—C92—C93—O931	179.39 (16)
C4—C5—C6—C11	−179.36 (15)	C91—C92—C93—C94	−1.1 (3)
C14—C5—C6—C11	0.8 (2)	C94—C93—O931—C932	6.1 (3)
C4—C5—C6—C7	2.1 (2)	C92—C93—O931—C932	−174.35 (18)
C14—C5—C6—C7	−177.75 (14)	O931—C93—C94—C95	−179.65 (19)
C11—C6—C7—N8	−15.49 (19)	C92—C93—C94—C95	0.9 (3)
C5—C6—C7—N8	163.04 (13)	C93—C94—C95—C96	0.1 (3)
C11—C6—C7—C71	108.62 (16)	C94—C95—C96—C91	−0.7 (3)
C5—C6—C7—C71	−72.85 (18)	C92—C91—C96—C95	0.5 (3)
N8—C7—C71—C76	−70.34 (17)	C9—C91—C96—C95	−178.31 (16)
C6—C7—C71—C76	164.57 (14)	N8—C9—O10—C11	41.16 (18)
N8—C7—C71—C72	108.51 (16)	C91—C9—O10—C11	163.16 (13)
C6—C7—C71—C72	−16.6 (2)	C9—O10—C11—C6	−11.2 (2)
C76—C71—C72—C73	−0.2 (2)	C9—O10—C11—C12	170.21 (13)
C7—C71—C72—C73	−179.07 (15)	C5—C6—C11—O10	−179.62 (14)
C71—C72—C73—C74	0.4 (3)	C7—C6—C11—O10	−1.1 (2)
C72—C73—C74—C75	0.0 (3)	C5—C6—C11—C12	−1.1 (2)
C73—C74—C75—O751	179.20 (16)	C7—C6—C11—C12	177.48 (14)
C73—C74—C75—C76	−0.6 (3)	O10—C11—C12—C13	179.12 (14)
C74—C75—O751—C752	−2.0 (3)	C6—C11—C12—C13	0.5 (2)
C76—C75—O751—C752	177.72 (15)	C11—C12—C13—C14	0.5 (2)
C72—C71—C76—C75	−0.3 (2)	C2—C1—C14—C13	179.23 (16)
C7—C71—C76—C75	178.61 (14)	C2—C1—C14—C5	−0.1 (2)
O751—C75—C76—C71	−179.09 (15)	C12—C13—C14—C1	179.86 (16)
C74—C75—C76—C71	0.7 (2)	C12—C13—C14—C5	−0.8 (2)
C6—C7—N8—C9	44.30 (17)	C4—C5—C14—C1	−0.3 (2)
C71—C7—N8—C9	−82.39 (15)	C6—C5—C14—C1	179.50 (14)
C7—N8—C9—O10	−58.80 (17)	C4—C5—C14—C13	−179.74 (15)
C7—N8—C9—C91	−178.77 (12)	C6—C5—C14—C13	0.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···Cg1ⁱ	0.86 (2)	2.709 (s.u.?)	3.496 (s.u.?)	153.3 (s.u.?)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₂BrNO₃
M_r	476.36
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	5.9753 (4), 9.9177 (7), 18.1925 (13)
α, β, γ (°)	84.632 (6), 88.618 (6), 81.088 (5)
V (Å³)	1060.37 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.97
Crystal size (mm)	0.33 × 0.27 × 0.25

Data collection
Diffractometer	Stoe IPDSII two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.563, 0.639
No. of measured, independent and observed [I > 2σ(I)] reflections	23965, 4875, 4449
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.086, 1.04
No. of reflections	4875
No. of parameters	287
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.53

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991).