3,11-Dibromo-14-(4-chloro­phen­yl)-14H-dibenzo[a,j]xanthene dimethyl­formamide monosolvate

Song, Y.B.; Liu, B.

doi:10.1107/S1600536812016200

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1460

doi:10.1107/S1600536812016200

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3,11-Dibromo-14-(4-chlorophenyl)-14H-dibenzo[a,j]xanthene dimethylformamide monosolvate

Yong Bin Song ^a and Bo Liu ^a ^*

^aKey Laboratory of Green Chemical Technology of College of Heilongjiang Province, School of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin, People's Republic of China
^*Correspondence e-mail: songyongbin1981@sina.com

(Received 25 March 2012; accepted 13 April 2012; online 21 April 2012)

In the title compound, C₂₇H₁₅Br₂ClO·C₃H₇NO, the xanthene moiety has a flattened boat conformation with a folding angle between the naphthalene units of 9.46 (3)°. The mean planes of the xanthene system and its 4-chlorophenyl substituent are nearly perpendicular [dihedral angle = 89.43 (5)°]. The dimethylformamide solvent molecule is disordered over two sets of sites with an occupancy ratio of 0.520 (11):0.480 (11).

Related literature

For related structures and the preparation of the title compound, see: Wu et al. (2009 ); Seethalakshmi et al. (2006 ). For the biological activity of benzoxanthene derivatives, see: Lambert et al. (1997 ); Hideo (1981 ); Poupelin et al. (1978 ). For related structures, see: Cai et al. (2009 ); Lu et al. (2008 ); Rahmani et al. (2009 ); Dalla Via et al. (2008 ); Gaurrand et al. (2006 ); Petit et al. (2007 ).

Experimental

Crystal data

C₂₇H₁₅Br₂ClO·C₃H₇NO
M_r = 623.74
Triclinic, $[P \overline 1]$
a = 10.8558 (12) Å
b = 10.9385 (12) Å
c = 11.8946 (13) Å
α = 74.443 (1)°
β = 80.967 (1)°
γ = 71.448 (1)°
V = 1286.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 3.29 mm⁻¹
T = 293 K
0.28 × 0.26 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.415, T_max = 0.518
8696 measured reflections
4522 independent reflections
2902 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.091
S = 1.03
4522 reflections
375 parameters
55 restraints
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812016200/ld2054sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016200/ld2054Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812016200/ld2054Isup3.cml

checkCIF report

Comment top

Derivatives of benzoxanthenes have received much attention due to their wide range of biological and pharmacological activities, such as antiviral (Lambert et al., 1997), antibacterial (Hideo, 1981), and anti-inflammatory (Poupelin et al., 1978). In the present paper we describe the crystal structure of the title compound.

The molecular structure of the compound is shown in the Figure 1. The chlorophenyl substituent (C12–C17) at C11 forms dihedral angle of 89.43 (5)° with the mean plane of the xanthene ring system. The pyran ring (O1/C9/C10/C11/C18/C19) adopts a boat conformation with the O1 and C11 displaced by 0.112 and 0.253 (4) Å, respectively, from the mean plane of the rest of the atoms.

The packing is characterized by Cl···Br contacts and π···π stacking interactions. The distance between the Cl and Br atoms is 3.5668 (9) Å; The angles C1—Br1···Cl1 and C15—Cl1···Br1 are 161.43 (1)° and 85.97 (1)°, respectively. Some π···π stacking interactions between phenyl rings (containing Br1 and Br2, respectively) were detected with the centroid-to-centroid distance of 3.688 (2) Å. Short C-H···O contacts take place between the title molecule and the solvent.

Related literature top

For related structures and the preparation of the title compound, see: Wu et al. (2009); Seethalakshmi et al. (2006). For the biological activity of benzoxanthene derivatives, see: Lambert et al. (1997); Hideo (1981); Poupelin et al. (1978). For related structures, see: Cai et al. (2009); Lu et al. (2008); Rahmani et al. (2009). For other related literature [on what subject(s)?], see: Dalla Via et al. (2008); Gaurrand et al. (2006); Petit et al. (2007).

Experimental top

A solution of the 6-bromo-2-naphthol (2.2 g, 10 mmol), and 4-chloro-benzaldehyde (0.7 g, 5 mmol), acetic acid (5 ml) was refluxed with 1 ml of hydrochloric acid for two hours (Wu et al., 2009). The system was cooled to room temperature, and the formed precipitate was filtered and washed with water. The product was recrystallized from the mixed solution of ethanol and dimethylformamide (DMF), and yielded raw crystals (2.2 g, yield 81%). The colourless single crystals of the title compound were grown by recystallization from DMF solution.

Computing details top

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. The solvent molecule have been omitted for clarity.
	Fig. 2. The crystal packing of the title compound viewed along the b axis. The solvent molecules have been omitted for clarity. Short Cl···Br contacts are shown by dashed lines (see Comments).

3,11-Dibromo-14-(4-chlorophenyl)-14H-dibenzo[a,j]xanthene dimethylformamide monosolvate top

Crystal data top

C₂₇H₁₅Br₂ClO·C₃H₇NO	Z = 2
M_r = 623.74	F(000) = 624.0
Triclinic, P1	D_x = 1.611 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.8558 (12) Å	Cell parameters from 2346 reflections
b = 10.9385 (12) Å	θ = 2.4–23.0°
c = 11.8946 (13) Å	µ = 3.29 mm⁻¹
α = 74.443 (1)°	T = 293 K
β = 80.967 (1)°	Block, colourless
γ = 71.448 (1)°	0.28 × 0.26 × 0.20 mm
V = 1286.0 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4522 independent reflections
Radiation source: fine-focus sealed tube	2902 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
phi and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = 12→12
T_min = 0.415, T_max = 0.518	k = 13→13
8696 measured reflections	l = 14→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0445P)² + 0.0361P] where P = (F_o² + 2F_c²)/3
4522 reflections	(Δ/σ)_max = 0.001
375 parameters	Δρ_max = 0.41 e Å⁻³
55 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₂₇H₁₅Br₂ClO·C₃H₇NO	γ = 71.448 (1)°
M_r = 623.74	V = 1286.0 (2) Å³
Triclinic, P1	Z = 2
a = 10.8558 (12) Å	Mo Kα radiation
b = 10.9385 (12) Å	µ = 3.29 mm⁻¹
c = 11.8946 (13) Å	T = 293 K
α = 74.443 (1)°	0.28 × 0.26 × 0.20 mm
β = 80.967 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4522 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2902 reflections with I > 2σ(I)
T_min = 0.415, T_max = 0.518	R_int = 0.025
8696 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	55 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.03	Δρ_max = 0.41 e Å⁻³
4522 reflections	Δρ_min = −0.52 e Å⁻³
375 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	Occ. (<1)
Br1	0.52851 (4)	0.29861 (5)	0.12824 (4)	0.08221 (18)
Br2	1.12806 (5)	−0.43299 (4)	1.11655 (4)	0.08279 (18)
Cl1	0.34543 (9)	0.24873 (11)	0.92900 (9)	0.0742 (3)
C1	0.6372 (3)	0.2652 (4)	0.2508 (3)	0.0561 (9)
C2	0.7071 (4)	0.3483 (4)	0.2477 (3)	0.0568 (10)
H2	0.7036	0.4213	0.1850	0.068*
C3	0.6406 (3)	0.1539 (4)	0.3421 (3)	0.0565 (9)
H3	0.5926	0.0973	0.3412	0.068*
C4	0.7150 (3)	0.1283 (3)	0.4333 (3)	0.0508 (9)
H4	0.7166	0.0541	0.4943	0.061*
C5	0.7893 (3)	0.2122 (3)	0.4366 (3)	0.0440 (8)
C6	0.7857 (3)	0.3240 (3)	0.3399 (3)	0.0508 (9)
C7	0.8624 (4)	0.4075 (4)	0.3393 (3)	0.0587 (10)
H7	0.8626	0.4792	0.2761	0.070*
C8	0.9352 (4)	0.3849 (4)	0.4288 (3)	0.0571 (10)
H8	0.9860	0.4400	0.4267	0.068*
C9	0.9339 (3)	0.2778 (4)	0.5253 (3)	0.0507 (9)
C10	0.8637 (3)	0.1914 (3)	0.5327 (3)	0.0443 (8)
C11	0.8579 (3)	0.0831 (3)	0.6435 (3)	0.0438 (8)
H11	0.8662	0.0007	0.6211	0.053*
C12	0.7273 (3)	0.1214 (3)	0.7159 (3)	0.0394 (7)
C13	0.6464 (3)	0.0415 (3)	0.7511 (3)	0.0517 (9)
H13	0.6697	−0.0390	0.7295	0.062*
C14	0.5302 (3)	0.0793 (4)	0.8187 (3)	0.0591 (10)
H14	0.4768	0.0238	0.8432	0.071*
C15	0.4951 (3)	0.1983 (4)	0.8487 (3)	0.0477 (8)
C16	0.5733 (3)	0.2804 (3)	0.8162 (3)	0.0505 (9)
H16	0.5489	0.3611	0.8375	0.061*
C17	0.6901 (3)	0.2400 (3)	0.7506 (3)	0.0480 (8)
H17	0.7448	0.2942	0.7294	0.058*
C18	1.0316 (3)	0.1546 (3)	0.7020 (3)	0.0476 (8)
C19	0.9692 (3)	0.0601 (3)	0.7161 (3)	0.0432 (8)
C20	1.1238 (3)	0.1442 (4)	0.7777 (3)	0.0547 (9)
H20	1.1634	0.2111	0.7652	0.066*
C21	1.1551 (3)	0.0378 (4)	0.8683 (3)	0.0509 (9)
H21	1.2141	0.0331	0.9193	0.061*
C22	1.0987 (3)	−0.0661 (3)	0.8857 (3)	0.0449 (8)
C23	1.0052 (3)	−0.0563 (3)	0.8097 (3)	0.0441 (8)
C24	1.1331 (3)	−0.1794 (4)	0.9783 (3)	0.0517 (9)
H24	1.1934	−0.1859	1.0288	0.062*
C25	1.0783 (3)	−0.2792 (3)	0.9939 (3)	0.0520 (9)
C26	0.9516 (3)	−0.1635 (3)	0.8306 (3)	0.0486 (8)
H26	0.8905	−0.1592	0.7819	0.058*
C27	0.9868 (3)	−0.2727 (3)	0.9200 (3)	0.0529 (9)
H27	0.9504	−0.3419	0.9318	0.063*
O1S	0.2639 (19)	0.1711 (15)	0.4104 (17)	0.146 (7)	0.480 (11)
N1S	0.336 (3)	0.321 (2)	0.464 (3)	0.067 (4)	0.480 (11)
C1S	0.2884 (11)	0.2997 (12)	0.3778 (11)	0.080 (3)	0.480 (11)
H1S	0.2724	0.3592	0.3057	0.096*	0.480 (11)
C2S	0.3677 (10)	0.2212 (13)	0.5620 (9)	0.091 (4)	0.480 (11)
H2SA	0.2894	0.2086	0.6071	0.136*	0.480 (11)
H2SB	0.4180	0.2444	0.6083	0.136*	0.480 (11)
H2SC	0.4179	0.1406	0.5394	0.136*	0.480 (11)
C3S	0.3956 (14)	0.4246 (12)	0.4441 (14)	0.107 (4)	0.480 (11)
H3SA	0.3941	0.4703	0.3630	0.160*	0.480 (11)
H3SB	0.4842	0.3873	0.4646	0.160*	0.480 (11)
H3SC	0.3485	0.4858	0.4915	0.160*	0.480 (11)
O1	1.0076 (2)	0.2689 (2)	0.6136 (2)	0.0576 (6)
O1Q	0.2462 (12)	0.226 (2)	0.3776 (18)	0.174 (9)	0.520 (11)
N1Q	0.349 (3)	0.315 (3)	0.463 (3)	0.070 (4)	0.520 (11)
C1Q	0.3174 (14)	0.2003 (14)	0.4823 (11)	0.128 (5)	0.520 (11)
H1Q	0.3355	0.1260	0.5443	0.153*	0.520 (11)
C2Q	0.3047 (14)	0.4214 (14)	0.3741 (10)	0.147 (8)	0.520 (11)
H2QA	0.2946	0.3914	0.3082	0.221*	0.520 (11)
H2QB	0.3659	0.4722	0.3518	0.221*	0.520 (11)
H2QC	0.2220	0.4758	0.3994	0.221*	0.520 (11)
C3Q	0.4112 (14)	0.336 (2)	0.5499 (17)	0.196 (11)	0.520 (11)
H3QA	0.4956	0.2722	0.5586	0.294*	0.520 (11)
H3QB	0.3592	0.3261	0.6231	0.294*	0.520 (11)
H3QC	0.4208	0.4239	0.5269	0.294*	0.520 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0733 (3)	0.1133 (4)	0.0549 (3)	−0.0121 (3)	−0.0207 (2)	−0.0202 (2)
Br2	0.1060 (4)	0.0687 (3)	0.0758 (3)	−0.0264 (3)	−0.0362 (3)	−0.0026 (2)
Cl1	0.0487 (6)	0.1130 (9)	0.0696 (7)	−0.0302 (6)	0.0088 (5)	−0.0353 (6)
C1	0.057 (2)	0.070 (3)	0.039 (2)	−0.005 (2)	−0.0072 (17)	−0.023 (2)
C2	0.063 (2)	0.060 (2)	0.038 (2)	−0.007 (2)	0.0002 (17)	−0.0135 (18)
C3	0.062 (2)	0.065 (3)	0.049 (2)	−0.0176 (19)	−0.0057 (18)	−0.024 (2)
C4	0.056 (2)	0.056 (2)	0.044 (2)	−0.0175 (18)	−0.0070 (16)	−0.0140 (17)
C5	0.0429 (19)	0.053 (2)	0.0359 (19)	−0.0108 (16)	0.0036 (14)	−0.0176 (16)
C6	0.049 (2)	0.056 (2)	0.044 (2)	−0.0094 (18)	0.0044 (16)	−0.0184 (18)
C7	0.070 (3)	0.057 (2)	0.046 (2)	−0.024 (2)	0.0081 (19)	−0.0097 (18)
C8	0.063 (2)	0.064 (2)	0.051 (2)	−0.030 (2)	0.0061 (19)	−0.017 (2)
C9	0.053 (2)	0.063 (2)	0.043 (2)	−0.0222 (19)	0.0017 (16)	−0.0205 (18)
C10	0.0443 (19)	0.050 (2)	0.041 (2)	−0.0149 (16)	0.0063 (15)	−0.0176 (16)
C11	0.0455 (19)	0.049 (2)	0.045 (2)	−0.0199 (16)	−0.0032 (15)	−0.0172 (16)
C12	0.0409 (18)	0.048 (2)	0.0365 (18)	−0.0180 (16)	−0.0092 (14)	−0.0109 (15)
C13	0.053 (2)	0.053 (2)	0.059 (2)	−0.0250 (18)	−0.0058 (17)	−0.0171 (18)
C14	0.048 (2)	0.078 (3)	0.061 (2)	−0.036 (2)	0.0011 (18)	−0.015 (2)
C15	0.0389 (19)	0.068 (2)	0.040 (2)	−0.0186 (18)	−0.0036 (14)	−0.0161 (18)
C16	0.052 (2)	0.058 (2)	0.047 (2)	−0.0193 (18)	−0.0018 (16)	−0.0182 (17)
C17	0.045 (2)	0.058 (2)	0.047 (2)	−0.0249 (17)	−0.0014 (16)	−0.0119 (17)
C18	0.044 (2)	0.056 (2)	0.051 (2)	−0.0202 (18)	0.0009 (16)	−0.0225 (18)
C19	0.0373 (18)	0.054 (2)	0.044 (2)	−0.0141 (16)	−0.0022 (14)	−0.0193 (17)
C20	0.048 (2)	0.068 (3)	0.062 (3)	−0.0268 (19)	−0.0010 (18)	−0.028 (2)
C21	0.040 (2)	0.067 (2)	0.056 (2)	−0.0183 (18)	−0.0060 (16)	−0.028 (2)
C22	0.0354 (18)	0.059 (2)	0.046 (2)	−0.0136 (17)	0.0002 (15)	−0.0223 (18)
C23	0.0359 (18)	0.054 (2)	0.048 (2)	−0.0112 (16)	0.0036 (15)	−0.0261 (17)
C24	0.041 (2)	0.068 (2)	0.049 (2)	−0.0086 (18)	−0.0058 (15)	−0.0255 (19)
C25	0.055 (2)	0.052 (2)	0.049 (2)	−0.0109 (18)	−0.0051 (17)	−0.0147 (17)
C26	0.045 (2)	0.053 (2)	0.053 (2)	−0.0129 (17)	−0.0094 (16)	−0.0198 (18)
C27	0.050 (2)	0.056 (2)	0.056 (2)	−0.0157 (18)	−0.0043 (17)	−0.0184 (19)
O1S	0.219 (18)	0.105 (8)	0.152 (11)	−0.095 (10)	0.051 (10)	−0.071 (7)
N1S	0.066 (10)	0.033 (6)	0.091 (9)	0.000 (6)	0.001 (7)	−0.017 (5)
C1S	0.066 (6)	0.090 (7)	0.071 (5)	−0.016 (5)	−0.004 (4)	−0.008 (5)
C2S	0.088 (6)	0.121 (8)	0.061 (6)	−0.047 (6)	−0.009 (5)	0.005 (5)
C3S	0.111 (8)	0.089 (7)	0.124 (9)	−0.039 (6)	0.024 (7)	−0.038 (6)
O1	0.0637 (16)	0.0636 (16)	0.0566 (16)	−0.0333 (13)	−0.0057 (12)	−0.0140 (13)
O1Q	0.058 (6)	0.28 (2)	0.247 (18)	−0.025 (9)	0.000 (8)	−0.201 (17)
N1Q	0.063 (7)	0.087 (8)	0.063 (6)	−0.032 (6)	−0.003 (5)	−0.009 (6)
C1Q	0.157 (12)	0.112 (9)	0.119 (11)	−0.055 (8)	0.039 (8)	−0.045 (8)
C2Q	0.137 (11)	0.118 (10)	0.084 (8)	0.045 (9)	0.023 (7)	0.029 (7)
C3Q	0.126 (11)	0.26 (2)	0.236 (19)	0.050 (12)	−0.093 (12)	−0.191 (18)

Geometric parameters (Å, º) top

Br1—C1	1.906 (4)	C19—C23	1.440 (4)
Br2—C25	1.898 (3)	C20—C21	1.350 (4)
Cl1—C15	1.756 (3)	C20—H20	0.9300
C1—C2	1.346 (5)	C21—C22	1.410 (4)
C1—C3	1.392 (5)	C21—H21	0.9300
C2—C6	1.413 (5)	C22—C24	1.411 (4)
C2—H2	0.9300	C22—C23	1.424 (4)
C3—C4	1.370 (5)	C23—C26	1.416 (4)
C3—H3	0.9300	C24—C25	1.360 (5)
C4—C5	1.413 (4)	C24—H24	0.9300
C4—H4	0.9300	C25—C27	1.400 (5)
C5—C10	1.429 (4)	C26—C27	1.363 (4)
C5—C6	1.432 (4)	C26—H26	0.9300
C6—C7	1.416 (5)	C27—H27	0.9300
C7—C8	1.347 (5)	O1S—C1S	1.453 (17)
C7—H7	0.9300	N1S—C1S	1.32 (2)
C8—C9	1.406 (5)	N1S—C2S	1.37 (3)
C8—H8	0.9300	N1S—C3S	1.42 (2)
C9—C10	1.369 (4)	C1S—H1S	0.9300
C9—O1	1.383 (4)	C2S—H2SA	0.9600
C10—C11	1.527 (4)	C2S—H2SB	0.9600
C11—C19	1.512 (4)	C2S—H2SC	0.9600
C11—C12	1.536 (4)	C3S—H3SA	0.9600
C11—H11	0.9800	C3S—H3SB	0.9600
C12—C13	1.374 (4)	C3S—H3SC	0.9600
C12—C17	1.384 (4)	O1Q—C1Q	1.485 (18)
C13—C14	1.392 (5)	N1Q—C2Q	1.36 (3)
C13—H13	0.9300	N1Q—C1Q	1.36 (2)
C14—C15	1.363 (5)	N1Q—C3Q	1.42 (2)
C14—H14	0.9300	C1Q—H1Q	0.9300
C15—C16	1.369 (4)	C2Q—H2QA	0.9600
C16—C17	1.388 (4)	C2Q—H2QB	0.9600
C16—H16	0.9300	C2Q—H2QC	0.9600
C17—H17	0.9300	C3Q—H3QA	0.9600
C18—C19	1.368 (4)	C3Q—H3QB	0.9600
C18—O1	1.381 (4)	C3Q—H3QC	0.9600
C18—C20	1.408 (5)

C2—C1—C3	122.1 (3)	C19—C18—C20	122.6 (3)
C2—C1—Br1	120.1 (3)	O1—C18—C20	114.6 (3)
C3—C1—Br1	117.8 (3)	C18—C19—C23	117.5 (3)
C1—C2—C6	119.7 (3)	C18—C19—C11	121.1 (3)
C1—C2—H2	120.1	C23—C19—C11	121.2 (3)
C6—C2—H2	120.1	C21—C20—C18	120.5 (3)
C4—C3—C1	119.5 (3)	C21—C20—H20	119.8
C4—C3—H3	120.2	C18—C20—H20	119.8
C1—C3—H3	120.2	C20—C21—C22	120.2 (3)
C3—C4—C5	121.4 (3)	C20—C21—H21	119.9
C3—C4—H4	119.3	C22—C21—H21	119.9
C5—C4—H4	119.3	C21—C22—C24	120.7 (3)
C4—C5—C10	122.8 (3)	C21—C22—C23	119.7 (3)
C4—C5—C6	117.4 (3)	C24—C22—C23	119.5 (3)
C10—C5—C6	119.8 (3)	C26—C23—C22	117.6 (3)
C2—C6—C7	121.7 (3)	C26—C23—C19	123.0 (3)
C2—C6—C5	119.7 (3)	C22—C23—C19	119.4 (3)
C7—C6—C5	118.6 (3)	C25—C24—C22	120.2 (3)
C8—C7—C6	121.2 (3)	C25—C24—H24	119.9
C8—C7—H7	119.4	C22—C24—H24	119.9
C6—C7—H7	119.4	C24—C25—C27	121.5 (3)
C7—C8—C9	119.6 (4)	C24—C25—Br2	119.8 (3)
C7—C8—H8	120.2	C27—C25—Br2	118.6 (3)
C9—C8—H8	120.2	C27—C26—C23	122.1 (3)
C10—C9—O1	122.8 (3)	C27—C26—H26	119.0
C10—C9—C8	123.1 (3)	C23—C26—H26	119.0
O1—C9—C8	114.1 (3)	C26—C27—C25	119.1 (3)
C9—C10—C5	117.6 (3)	C26—C27—H27	120.4
C9—C10—C11	120.8 (3)	C25—C27—H27	120.4
C5—C10—C11	121.4 (3)	C1S—N1S—C2S	119.2 (16)
C19—C11—C10	109.9 (3)	C1S—N1S—C3S	121 (3)
C19—C11—C12	109.9 (3)	C2S—N1S—C3S	116.1 (18)
C10—C11—C12	110.6 (3)	N1S—C1S—O1S	111.3 (17)
C19—C11—H11	108.8	N1S—C1S—H1S	124.3
C10—C11—H11	108.8	O1S—C1S—H1S	124.3
C12—C11—H11	108.8	C18—O1—C9	118.2 (3)
C13—C12—C17	117.9 (3)	C2Q—N1Q—C1Q	123.1 (17)
C13—C12—C11	123.0 (3)	C2Q—N1Q—C3Q	116.9 (19)
C17—C12—C11	119.1 (3)	C1Q—N1Q—C3Q	119 (2)
C12—C13—C14	120.9 (3)	N1Q—C1Q—O1Q	100.8 (16)
C12—C13—H13	119.5	N1Q—C1Q—H1Q	129.6
C14—C13—H13	119.5	O1Q—C1Q—H1Q	129.6
C15—C14—C13	119.5 (3)	N1Q—C2Q—H2QA	109.5
C15—C14—H14	120.3	N1Q—C2Q—H2QB	109.5
C13—C14—H14	120.3	H2QA—C2Q—H2QB	109.5
C14—C15—C16	121.4 (3)	N1Q—C2Q—H2QC	109.5
C14—C15—Cl1	119.4 (3)	H2QA—C2Q—H2QC	109.5
C16—C15—Cl1	119.1 (3)	H2QB—C2Q—H2QC	109.5
C15—C16—C17	118.3 (3)	N1Q—C3Q—H3QA	109.5
C15—C16—H16	120.8	N1Q—C3Q—H3QB	109.5
C17—C16—H16	120.8	H3QA—C3Q—H3QB	109.5
C12—C17—C16	121.9 (3)	N1Q—C3Q—H3QC	109.5
C12—C17—H17	119.1	H3QA—C3Q—H3QC	109.5
C16—C17—H17	119.1	H3QB—C3Q—H3QC	109.5
C19—C18—O1	122.8 (3)

Experimental details

Crystal data
Chemical formula	C₂₇H₁₅Br₂ClO·C₃H₇NO
M_r	623.74
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.8558 (12), 10.9385 (12), 11.8946 (13)
α, β, γ (°)	74.443 (1), 80.967 (1), 71.448 (1)
V (Å³)	1286.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.29
Crystal size (mm)	0.28 × 0.26 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.415, 0.518
No. of measured, independent and observed [I > 2σ(I)] reflections	8696, 4522, 2902
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.091, 1.03
No. of reflections	4522
No. of parameters	375
No. of restraints	55
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.52

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank Zhanhua Su for help with the data collection.

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