9-(4-Bromo­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6,9,10-hexa­hydro­acridine-1,8(2H,7H)-dione

Xu, J.-N.; Zhang, J.-P.; Wang, Q.; Zhu, X.-T.; Tu, S.-J.

doi:10.1107/S1600536805041127

9-(4-Bromophenyl)-3,3,6,6-tetramethyl-3,4,5,6,9,10-hexahydroacridine-1,8(2H,7H)-dione

J.-N. Xu, J.-P. Zhang, Q. Wang, X.-T. Zhu and S.-J. Tu

The title compound, C₂₃H₂₆BrNO₂, was synthesized by the reaction of 4-bromobenzaldehyde with dimedone and ammonium acetate under microwave irradiation. In the molecule, the dihydropyridine ring adopts a slight boat conformation.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041127/lh6563sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041127/lh6563Isup2.hkl Contains datablock I

CCDC reference: 296611

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.007 Å
R factor = 0.037
wR factor = 0.091
Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O1      ..       3.11 Ang.

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           26.35
           From the CIF: _reflns_number_total               3083
           Count of symmetry unique reflns         2334
           Completeness (_total/calc)            132.09%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       749
           Fraction of Friedel pairs measured     0.321
           Are heavy atom types Z>Si present        yes

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

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Acridine derivatives with their interesting chemical and physical properties, have immense utility in the pharmaceutical and dyeing industries, and are well known therapeutic agents (Wysocka-Skrzela & Ledochowski, 1976; Nasim & Brychey, 1979; Thull & Testa, 1994). The discovery of acridines as antimalarial and antitumor agents has attracted the attention of organic chemists and thus led to intensive interest in the synthesis of several drugs based on acridine (Khurana et al., 1990; Matsumoto et al., 1983), We report here the crystal structure of the title compound, (I).

The dihydropyridine ring in (I) is in a slight boat conformmation, with atoms N1 and C9 deviating from the C7/C8/C10/C11 mean plane by 0.077 (3) and 0.150 (3) Å, respectively (Fig. 1). Both cyclohexene rings adopt sofa conformations: atom C3 deviaties from the C1/C2/C6/C7/C8 by −0.617 (3) Å and atom C13 deviates from the C10/C11/C12/C16/C17 plane by 0.651 (3) Å. The dihedral angle between the C7/C8/C10/C11 and C7/C8/C10/C11 planes is 2.61 (7)° and that between the C7/C8/C10/C11 and C10/C11/C12/C16/C17 planes is 7.55 (7)°. In the crystal structure, molecules are linked via N—H···O hydrogen bonds, forming one-dimensional chains in the a-axis direction (Table 1 and Fig. 2).

Experimental top

The title compound was prepared by the reaction of 4-bromobenzaldehyde (1 mmol) with dimedone (2 mmol) and ammonium acetate (1 mmol) under microwave irradiation (yield 93%; m.p. >574 K). Single crystals suitable for X-ray diffraction were obtained by slow evaportation of (I) from an ethanol solution.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. View (Spek, 2003) of the hydrogen bonded (dashed lines) chain in (I).

9-(4-Bromophenyl)-3,3,6,6-tetramethyl-3,4,5,6,9,10-hexahydroacridine- 1,8(2H,7H)-dione top

Crystal data top

C₂₃H₂₆BrNO₂	D_x = 1.315 Mg m⁻³
M_r = 428.36	Melting point > 574 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2822 reflections
a = 14.1598 (16) Å	θ = 2.8–23.0°
b = 14.0629 (16) Å	µ = 1.92 mm⁻¹
c = 10.8624 (12) Å	T = 294 K
V = 2163.0 (4) Å³	Block, yellow
Z = 4	0.26 × 0.20 × 0.16 mm
F(000) = 888

Data collection top

Bruker SMART CCD area-detector diffractometer	3083 independent reflections
Radiation source: fine-focus sealed tube	2016 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
T_min = 0.610, T_max = 0.736	k = −16→17
11747 measured reflections	l = −13→6

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0196P)² + 1.345P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.091	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.42 e Å⁻³
3083 reflections	Δρ_min = −0.54 e Å⁻³
252 parameters	Absolute structure: Flack (1983), 750 Friedel pairs
2 restraints	Absolute structure parameter: 0.003 (13)

Crystal data top

C₂₃H₂₆BrNO₂	V = 2163.0 (4) Å³
M_r = 428.36	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 14.1598 (16) Å	µ = 1.92 mm⁻¹
b = 14.0629 (16) Å	T = 294 K
c = 10.8624 (12) Å	0.26 × 0.20 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3083 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2016 reflections with I > 2σ(I)
T_min = 0.610, T_max = 0.736	R_int = 0.052
11747 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	Δρ_max = 0.42 e Å⁻³
S = 1.00	Δρ_min = −0.54 e Å⁻³
3083 reflections	Absolute structure: Flack (1983), 750 Friedel pairs
252 parameters	Absolute structure parameter: 0.003 (13)
2 restraints

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	0.80581 (4)	0.86019 (5)	0.05271 (7)	0.1019 (3)
O1	0.6134 (2)	0.4835 (2)	0.3398 (3)	0.0626 (9)
O2	0.76103 (19)	0.7332 (2)	0.6366 (3)	0.0575 (9)
N1	0.4359 (2)	0.7000 (3)	0.5773 (4)	0.0493 (11)
H1	0.3813 (16)	0.715 (3)	0.608 (4)	0.063 (15)*
C1	0.5363 (3)	0.5144 (3)	0.3745 (4)	0.0477 (12)
C2	0.4449 (4)	0.4714 (3)	0.3287 (5)	0.0585 (13)
H2A	0.4565	0.4061	0.3041	0.070*
H2B	0.4241	0.5062	0.2565	0.070*
C3	0.3663 (3)	0.4728 (3)	0.4247 (5)	0.0509 (12)
C4	0.3925 (4)	0.4083 (4)	0.5322 (6)	0.0735 (16)
H4A	0.4518	0.4284	0.5663	0.110*
H4B	0.3979	0.3439	0.5037	0.110*
H4C	0.3444	0.4119	0.5943	0.110*
C5	0.2726 (4)	0.4385 (4)	0.3676 (6)	0.0816 (19)
H5A	0.2776	0.3723	0.3471	0.122*
H5B	0.2595	0.4745	0.2945	0.122*
H5C	0.2223	0.4474	0.4258	0.122*
C6	0.3546 (3)	0.5742 (3)	0.4692 (5)	0.0553 (14)
H6A	0.3221	0.6104	0.4060	0.066*
H6B	0.3148	0.5740	0.5419	0.066*
C7	0.4451 (3)	0.6238 (3)	0.4997 (4)	0.0423 (11)
C8	0.5304 (3)	0.5958 (3)	0.4564 (4)	0.0393 (10)
C9	0.6203 (3)	0.6481 (3)	0.4908 (4)	0.0426 (11)
H9	0.6655	0.6011	0.5217	0.051*
C10	0.6010 (3)	0.7182 (3)	0.5932 (4)	0.0396 (10)
C11	0.5125 (3)	0.7435 (3)	0.6280 (4)	0.0425 (11)
C12	0.4902 (3)	0.8153 (3)	0.7259 (5)	0.0558 (13)
H12A	0.4788	0.7823	0.8029	0.067*
H12B	0.4326	0.8485	0.7037	0.067*
C13	0.5690 (3)	0.8880 (3)	0.7447 (5)	0.0536 (12)
C14	0.5759 (4)	0.9559 (4)	0.6370 (6)	0.0829 (18)
H14A	0.5922	0.9212	0.5639	0.124*
H14B	0.6237	1.0026	0.6534	0.124*
H14C	0.5162	0.9871	0.6252	0.124*
C15	0.5499 (4)	0.9446 (4)	0.8623 (5)	0.086 (2)
H15A	0.4948	0.9833	0.8511	0.130*
H15B	0.6032	0.9844	0.8802	0.130*
H15C	0.5398	0.9014	0.9295	0.130*
C16	0.6613 (3)	0.8308 (4)	0.7572 (5)	0.0588 (14)
H16A	0.7138	0.8751	0.7585	0.071*
H16B	0.6605	0.7981	0.8358	0.071*
C17	0.6787 (3)	0.7601 (3)	0.6597 (4)	0.0474 (11)
C18	0.6649 (3)	0.6979 (3)	0.3818 (4)	0.0445 (11)
C19	0.7558 (3)	0.6763 (4)	0.3432 (5)	0.0600 (14)
H19	0.7896	0.6290	0.3839	0.072*
C20	0.7974 (3)	0.7235 (4)	0.2452 (5)	0.0687 (16)
H20	0.8584	0.7079	0.2209	0.082*
C21	0.7489 (4)	0.7927 (4)	0.1847 (5)	0.0656 (15)
C22	0.6584 (4)	0.8155 (4)	0.2208 (5)	0.0704 (16)
H22	0.6253	0.8632	0.1802	0.084*
C23	0.6172 (3)	0.7673 (3)	0.3177 (5)	0.0551 (13)
H23	0.5556	0.7822	0.3402	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1107 (5)	0.1424 (6)	0.0527 (3)	−0.0667 (4)	0.0017 (5)	0.0173 (5)
O1	0.069 (2)	0.058 (2)	0.060 (2)	0.0170 (18)	0.0135 (19)	−0.0044 (19)
O2	0.0302 (16)	0.073 (2)	0.070 (2)	−0.0073 (15)	−0.0019 (17)	0.0091 (19)
N1	0.0268 (18)	0.049 (2)	0.072 (3)	0.0034 (16)	0.000 (2)	−0.022 (2)
C1	0.059 (3)	0.044 (3)	0.039 (3)	0.008 (2)	0.008 (2)	0.007 (2)
C2	0.073 (4)	0.050 (3)	0.052 (3)	−0.010 (3)	0.004 (3)	−0.010 (3)
C3	0.050 (3)	0.045 (3)	0.057 (3)	−0.007 (2)	−0.006 (3)	−0.014 (3)
C4	0.085 (3)	0.065 (3)	0.071 (4)	−0.017 (2)	0.004 (4)	0.003 (4)
C5	0.079 (4)	0.076 (4)	0.090 (5)	−0.017 (3)	−0.009 (3)	−0.034 (4)
C6	0.038 (2)	0.051 (3)	0.078 (4)	−0.006 (2)	−0.003 (3)	−0.013 (3)
C7	0.035 (2)	0.038 (2)	0.054 (3)	−0.0009 (19)	−0.003 (2)	−0.002 (2)
C8	0.040 (2)	0.037 (2)	0.041 (2)	0.0017 (19)	0.004 (2)	−0.001 (2)
C9	0.031 (2)	0.044 (3)	0.053 (3)	0.0066 (19)	0.002 (2)	0.004 (2)
C10	0.032 (2)	0.044 (3)	0.043 (3)	−0.0009 (18)	0.0020 (19)	0.000 (2)
C11	0.031 (2)	0.047 (3)	0.050 (3)	−0.0006 (19)	−0.003 (2)	−0.006 (2)
C12	0.043 (3)	0.058 (3)	0.067 (3)	−0.001 (2)	0.004 (3)	−0.017 (3)
C13	0.051 (3)	0.054 (3)	0.057 (3)	−0.010 (2)	−0.006 (3)	−0.008 (3)
C14	0.101 (4)	0.061 (4)	0.086 (5)	−0.004 (3)	−0.007 (4)	0.010 (3)
C15	0.087 (4)	0.090 (5)	0.082 (5)	−0.013 (3)	0.001 (4)	−0.043 (4)
C16	0.052 (3)	0.066 (3)	0.059 (3)	−0.018 (2)	−0.013 (3)	−0.002 (3)
C17	0.038 (3)	0.058 (3)	0.046 (3)	−0.005 (2)	−0.003 (2)	0.012 (2)
C18	0.038 (3)	0.049 (3)	0.047 (3)	0.001 (2)	0.009 (2)	−0.002 (2)
C19	0.051 (3)	0.064 (3)	0.065 (3)	0.006 (3)	0.012 (3)	0.005 (3)
C20	0.047 (3)	0.094 (4)	0.065 (4)	−0.008 (3)	0.024 (3)	−0.004 (3)
C21	0.074 (4)	0.081 (4)	0.042 (3)	−0.037 (3)	−0.003 (3)	0.001 (3)
C22	0.074 (4)	0.077 (4)	0.060 (4)	−0.007 (3)	−0.012 (3)	0.020 (3)
C23	0.047 (3)	0.063 (3)	0.055 (3)	0.003 (2)	0.002 (3)	0.013 (3)

Geometric parameters (Å, º) top

Br1—C21	1.899 (5)	C10—C11	1.357 (5)
O1—C1	1.234 (5)	C10—C17	1.442 (6)
O2—C17	1.251 (5)	C11—C12	1.499 (6)
N1—C11	1.361 (5)	C12—C13	1.528 (6)
N1—C7	1.370 (5)	C12—H12A	0.9700
N1—H1	0.87 (3)	C12—H12B	0.9700
C1—C8	1.452 (6)	C13—C14	1.513 (7)
C1—C2	1.512 (6)	C13—C15	1.529 (7)
C2—C3	1.525 (7)	C13—C16	1.541 (6)
C2—H2A	0.9700	C14—H14A	0.9600
C2—H2B	0.9700	C14—H14B	0.9600
C3—C6	1.515 (6)	C14—H14C	0.9600
C3—C4	1.525 (7)	C15—H15A	0.9600
C3—C5	1.542 (7)	C15—H15B	0.9600
C4—H4A	0.9600	C15—H15C	0.9600
C4—H4B	0.9600	C16—C17	1.473 (7)
C4—H4C	0.9600	C16—H16A	0.9700
C5—H5A	0.9600	C16—H16B	0.9700
C5—H5B	0.9600	C18—C23	1.377 (6)
C5—H5C	0.9600	C18—C19	1.388 (6)
C6—C7	1.495 (6)	C19—C20	1.385 (7)
C6—H6A	0.9700	C19—H19	0.9300
C6—H6B	0.9700	C20—C21	1.361 (7)
C7—C8	1.355 (5)	C20—H20	0.9300
C8—C9	1.517 (6)	C21—C22	1.378 (8)
C9—C10	1.511 (6)	C22—C23	1.381 (7)
C9—C18	1.513 (6)	C22—H22	0.9300
C9—H9	0.9800	C23—H23	0.9300

C11—N1—C7	121.7 (3)	N1—C11—C12	115.0 (4)
C11—N1—H1	117 (3)	C11—C12—C13	113.0 (4)
C7—N1—H1	120 (3)	C11—C12—H12A	109.0
O1—C1—C8	121.0 (4)	C13—C12—H12A	109.0
O1—C1—C2	121.1 (4)	C11—C12—H12B	109.0
C8—C1—C2	117.9 (4)	C13—C12—H12B	109.0
C1—C2—C3	113.3 (4)	H12A—C12—H12B	107.8
C1—C2—H2A	108.9	C14—C13—C12	111.5 (5)
C3—C2—H2A	108.9	C14—C13—C15	109.2 (4)
C1—C2—H2B	108.9	C12—C13—C15	109.3 (4)
C3—C2—H2B	108.9	C14—C13—C16	110.1 (4)
H2A—C2—H2B	107.7	C12—C13—C16	106.3 (4)
C6—C3—C4	110.0 (4)	C15—C13—C16	110.4 (4)
C6—C3—C2	108.0 (4)	C13—C14—H14A	109.5
C4—C3—C2	109.8 (4)	C13—C14—H14B	109.5
C6—C3—C5	109.2 (4)	H14A—C14—H14B	109.5
C4—C3—C5	109.4 (4)	C13—C14—H14C	109.5
C2—C3—C5	110.4 (4)	H14A—C14—H14C	109.5
C3—C4—H4A	109.5	H14B—C14—H14C	109.5
C3—C4—H4B	109.5	C13—C15—H15A	109.5
H4A—C4—H4B	109.5	C13—C15—H15B	109.5
C3—C4—H4C	109.5	H15A—C15—H15B	109.5
H4A—C4—H4C	109.5	C13—C15—H15C	109.5
H4B—C4—H4C	109.5	H15A—C15—H15C	109.5
C3—C5—H5A	109.5	H15B—C15—H15C	109.5
C3—C5—H5B	109.5	C17—C16—C13	115.5 (4)
H5A—C5—H5B	109.5	C17—C16—H16A	108.4
C3—C5—H5C	109.5	C13—C16—H16A	108.4
H5A—C5—H5C	109.5	C17—C16—H16B	108.4
H5B—C5—H5C	109.5	C13—C16—H16B	108.4
C7—C6—C3	114.6 (4)	H16A—C16—H16B	107.5
C7—C6—H6A	108.6	O2—C17—C10	119.1 (4)
C3—C6—H6A	108.6	O2—C17—C16	120.3 (4)
C7—C6—H6B	108.6	C10—C17—C16	120.5 (4)
C3—C6—H6B	108.6	C23—C18—C19	117.2 (5)
H6A—C6—H6B	107.6	C23—C18—C9	121.2 (4)
C8—C7—N1	121.7 (4)	C19—C18—C9	121.6 (4)
C8—C7—C6	123.5 (4)	C20—C19—C18	121.4 (5)
N1—C7—C6	114.8 (4)	C20—C19—H19	119.3
C7—C8—C1	119.5 (4)	C18—C19—H19	119.3
C7—C8—C9	121.5 (4)	C21—C20—C19	120.0 (5)
C1—C8—C9	119.0 (4)	C21—C20—H20	120.0
C10—C9—C18	110.5 (3)	C19—C20—H20	120.0
C10—C9—C8	110.3 (3)	C20—C21—C22	119.9 (5)
C18—C9—C8	112.5 (4)	C20—C21—Br1	120.5 (4)
C10—C9—H9	107.8	C22—C21—Br1	119.6 (5)
C18—C9—H9	107.8	C21—C22—C23	119.7 (5)
C8—C9—H9	107.8	C21—C22—H22	120.2
C11—C10—C17	117.3 (4)	C23—C22—H22	120.2
C11—C10—C9	122.9 (4)	C18—C23—C22	121.8 (5)
C17—C10—C9	119.8 (4)	C18—C23—H23	119.1
C10—C11—N1	120.3 (4)	C22—C23—H23	119.1
C10—C11—C12	124.6 (4)

O1—C1—C2—C3	146.4 (5)	C9—C10—C11—C12	−177.7 (4)
C8—C1—C2—C3	−36.2 (6)	C7—N1—C11—C10	6.5 (7)
C1—C2—C3—C6	54.3 (5)	C7—N1—C11—C12	−170.7 (4)
C1—C2—C3—C4	−65.7 (5)	C10—C11—C12—C13	25.2 (7)
C1—C2—C3—C5	173.6 (4)	N1—C11—C12—C13	−157.7 (4)
C4—C3—C6—C7	73.4 (5)	C11—C12—C13—C14	70.9 (5)
C2—C3—C6—C7	−46.4 (6)	C11—C12—C13—C15	−168.3 (4)
C5—C3—C6—C7	−166.5 (5)	C11—C12—C13—C16	−49.1 (6)
C11—N1—C7—C8	−8.9 (7)	C14—C13—C16—C17	−70.1 (5)
C11—N1—C7—C6	170.1 (4)	C12—C13—C16—C17	50.9 (6)
C3—C6—C7—C8	20.4 (7)	C15—C13—C16—C17	169.3 (4)
C3—C6—C7—N1	−158.6 (4)	C11—C10—C17—O2	174.7 (4)
N1—C7—C8—C1	179.8 (4)	C9—C10—C17—O2	−4.4 (6)
C6—C7—C8—C1	0.9 (7)	C11—C10—C17—C16	−2.8 (6)
N1—C7—C8—C9	−0.6 (7)	C9—C10—C17—C16	178.1 (4)
C6—C7—C8—C9	−179.5 (4)	C13—C16—C17—O2	156.2 (4)
O1—C1—C8—C7	−175.4 (4)	C13—C16—C17—C10	−26.3 (7)
C2—C1—C8—C7	7.3 (6)	C10—C9—C18—C23	−63.3 (5)
O1—C1—C8—C9	5.1 (7)	C8—C9—C18—C23	60.4 (6)
C2—C1—C8—C9	−172.3 (4)	C10—C9—C18—C19	116.0 (5)
C7—C8—C9—C10	10.6 (6)	C8—C9—C18—C19	−120.3 (5)
C1—C8—C9—C10	−169.8 (4)	C23—C18—C19—C20	0.9 (7)
C7—C8—C9—C18	−113.2 (5)	C9—C18—C19—C20	−178.4 (5)
C1—C8—C9—C18	66.4 (5)	C18—C19—C20—C21	−0.1 (8)
C18—C9—C10—C11	111.9 (5)	C19—C20—C21—C22	−0.1 (8)
C8—C9—C10—C11	−13.1 (5)	C19—C20—C21—Br1	178.5 (4)
C18—C9—C10—C17	−69.1 (5)	C20—C21—C22—C23	−0.6 (8)
C8—C9—C10—C17	166.0 (4)	Br1—C21—C22—C23	−179.2 (4)
C17—C10—C11—N1	−173.7 (4)	C19—C18—C23—C22	−1.6 (8)
C9—C10—C11—N1	5.4 (7)	C9—C18—C23—C22	177.7 (5)
C17—C10—C11—C12	3.3 (7)	C21—C22—C23—C18	1.5 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.87 (3)	1.88 (2)	2.726 (4)	165 (4)

Symmetry code: (i) x−1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₆BrNO₂
M_r	428.36
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	294
a, b, c (Å)	14.1598 (16), 14.0629 (16), 10.8624 (12)
V (Å³)	2163.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.92
Crystal size (mm)	0.26 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.610, 0.736
No. of measured, independent and observed [I > 2σ(I)] reflections	11747, 3083, 2016
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.091, 1.00
No. of reflections	3083
No. of parameters	252
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.54
Absolute structure	Flack (1983), 750 Friedel pairs
Absolute structure parameter	0.003 (13)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003), SHELXTL.