3,11-Dibromo-14-(4-chloro-phen-yl)-14H-dibenzo[a,j]xanthene dimethyl-formamide monosolvate.

In the title compound, C(27)H(15)Br(2)ClO·C(3)H(7)NO, 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-chloro-phenyl substituent are nearly perpendicular [dihedral angle = 89.43 (5)°]. The dimethyl-formamide solvent mol-ecule 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 = 623.74

Triclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.091

S = 1.03

4522 reflections

375 parameters

55 restraints

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016200/ld2054sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812016200/ld2054Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H15Br2ClO·C3H7NO	Z = 2
Mr = 623.74	F(000) = 624.0
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0445P)2 + 0.0361P] where P = (Fo2 + 2Fc2)/3
4522 reflections	(Δ/σ)max = 0.001
375 parameters	Δρmax = 0.41 e Å−3
55 restraints	Δρmin = −0.52 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)