2-Anilino-3-benzoyl-4-(2,5-dichloro­phen­yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetra­hydro-4H-benzo[b]pyran

Wen, L.-R.; Sun, J.-H.; Ji, C.; Xie, H.-Y.

doi:10.1107/S1600536807068377

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o407

doi:10.1107/S1600536807068377

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2-Anilino-3-benzoyl-4-(2,5-dichlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyran

Li-Rong Wen,^a ^* Ji-Hui Sun,^a Chen Ji ^a and Huai-Yuan Xie ^a

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: wenlirong@qust.edu.cn

(Received 21 November 2007; accepted 25 December 2007; online 9 January 2008)

The title compound, C₃₀H₂₅Cl₂NO₃, was prepared by the reaction of 3-oxo-N,3-diphenylpropanethioamide, 2,5-dichlorobenzaldehyde and 5,5-dimethyl-1,3-cyclohexanedione (1:1:1) in ethanol. The cyclohexene ring adopts a half-chair conformation. The crystal structure exhibits intramolecular N—H⋯O and C—H⋯O, and intermolecular C—H⋯O interactions.

Related literature

For various biological activities, see: Hassanien et al. (1999 ); Jiang et al. (2001 ); Hamann et al. (1998 ). For other aspects of our research, see: Li et al. (2006 ).

Experimental

Crystal data

C₃₀H₂₅Cl₂NO₃
M_r = 518.41
Monoclinic, P 2₁ /n
a = 12.844 (3) Å
b = 9.256 (2) Å
c = 22.557 (5) Å
β = 103.365 (4)°
V = 2609.1 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 294 (2) K
0.20 × 0.14 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.946, T_max = 0.967
14359 measured reflections
5336 independent reflections
2754 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.123
S = 1.02
5336 reflections
331 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.95 (3)	1.74 (3)	2.565 (3)	144 (3)
C4—H4B⋯O1ⁱ	0.97	2.36	3.308 (3)	164
C13—H13⋯O2	0.93	2.50	2.915 (3)	108
C28—H28⋯O3ⁱⁱ	0.93	2.49	3.329 (4)	150
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068377/ob2103sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068377/ob2103Isup2.hkl

checkCIF report

Comment top

Many 4H-benzo[b]pyran derivatives have been reported to show various biological activities (Hassanien et al.,1999), such as the cure of lower blood sugar (Jiang et al., 2001), mammary cancer and ovarian cancer (Hamann et al.,1998). In the course of our systematic studies aimed at the synthesis of new bioactive compounds (Li et al., 2006), the title compound, (I), was synthesized and its structure is reported here.

In (I), (Fig. 1), the six-membered ring C1—C5/C9 adopts a half-chair conformation with the largest derivation of C3 by 0.369 (3) Å. The phenyl ring C25—C30 is approximately perpendicular to the pyran ring O2/C5—C9, their dihedral angle being 88.51 (8)°. The dihedral angle between the phenyl ring C19—C24 and pyran ring is 67.70 (8) °. In the crystal structure, there are intramolecular N1—H1···O3 and C13—H13···O2 interactions (Table 1). Molecules are linked into chains along the b axis by intermolecular C28—H28···O3ⁱⁱ interactions (Fig. 2). Then the other intermolecular interactions C4—H4B···O1 ⁱconnect the chains to a two-dimensional network.

Related literature top

For various biological activities, see: Hassanien et al. (1999); Jiang et al. (2001); Hamann et al. (1998). For other aspects of our research, see: Li et al. (2006).

Experimental top

The title compound (I) was obtained as follows: 3-oxo-N,3- diphenylpropanethioamide (1 mmol, 0.255 g), 2,5-dichlorobenzaldehyde (1 mmol, 0.161 g), and 5,5-dimethyl-1,3-cyclohexanedione (1 mmol, 0.140 g) were dissolved in ethanol (10 ml), and the solution was refluxed for 10 h in the presence of triethylamine (1 mmol, 0.101 g). Upon cooling, the product was collected by filtration and recrystallized from ethanol and tetrahydrofuran (4:1) (; yield 33%, m.p. 467 K).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 35% probability level.
	Fig. 2. A packing diagram of (I), viewed down the a axis. The C—H···O interactions are shown as dashed lines.

2-Anilino-3-benzoyl-4-(2,5-dichlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-τetrahydro-4H-benzo[b]pyran top

Crystal data top

C₃₀H₂₅Cl₂NO₃	F(000) = 1080
M_r = 518.41	D_x = 1.320 Mg m⁻³ D_m = 1.320 Mg m⁻³ D_m measured by not measured
Monoclinic, P2₁/n	Melting point: 467 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.844 (3) Å	Cell parameters from 2650 reflections
b = 9.256 (2) Å	θ = 2.4–23.6°
c = 22.557 (5) Å	µ = 0.28 mm⁻¹
β = 103.365 (4)°	T = 294 K
V = 2609.1 (10) Å³	Block, colorless
Z = 4	0.20 × 0.14 × 0.12 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	5336 independent reflections
Radiation source: fine-focus sealed tube	2754 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→15
T_min = 0.946, T_max = 0.967	k = −10→11
14359 measured reflections	l = −28→22

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0411P)² + 0.4267P] where P = (F_o² + 2F_c²)/3
5336 reflections	(Δ/σ)_max = 0.004
331 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₃₀H₂₅Cl₂NO₃	V = 2609.1 (10) Å³
M_r = 518.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.844 (3) Å	µ = 0.28 mm⁻¹
b = 9.256 (2) Å	T = 294 K
c = 22.557 (5) Å	0.20 × 0.14 × 0.12 mm
β = 103.365 (4)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	5336 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2754 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.967	R_int = 0.051
14359 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.20 e Å⁻³
5336 reflections	Δρ_min = −0.23 e Å⁻³
331 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
Cl1	1.02394 (6)	0.53547 (9)	0.14792 (4)	0.0680 (3)
Cl2	0.63077 (9)	0.80839 (10)	−0.03029 (4)	0.1032 (4)
N1	1.01125 (19)	0.1076 (3)	0.12728 (11)	0.0550 (7)
O1	0.65405 (15)	0.5247 (2)	0.17605 (9)	0.0658 (6)
O2	0.96352 (13)	0.23945 (17)	0.20044 (7)	0.0447 (5)
O3	0.91053 (15)	0.1391 (2)	0.01577 (8)	0.0587 (5)
C1	0.7347 (2)	0.4727 (3)	0.20864 (12)	0.0452 (7)
C2	0.7538 (2)	0.4781 (3)	0.27707 (12)	0.0560 (8)
H2A	0.7192	0.3954	0.2907	0.067*
H2B	0.7202	0.5644	0.2884	0.067*
C3	0.8716 (2)	0.4783 (3)	0.31028 (12)	0.0502 (7)
C4	0.9243 (2)	0.3467 (3)	0.28778 (11)	0.0463 (7)
H4A	1.0015	0.3561	0.3008	0.056*
H4B	0.9036	0.2601	0.3063	0.056*
C5	0.89396 (19)	0.3311 (2)	0.22046 (11)	0.0383 (6)
C6	0.9429 (2)	0.2043 (3)	0.13997 (12)	0.0416 (6)
C7	0.86258 (19)	0.2673 (3)	0.09639 (11)	0.0398 (6)
C8	0.79466 (19)	0.3875 (3)	0.11449 (11)	0.0392 (6)
H8	0.7195	0.3616	0.0982	0.047*
C9	0.81208 (19)	0.3949 (2)	0.18249 (11)	0.0369 (6)
C10	0.9257 (2)	0.6182 (3)	0.29677 (15)	0.0734 (10)
H10A	0.8928	0.6992	0.3118	0.110*
H10B	0.9177	0.6278	0.2536	0.110*
H10C	1.0003	0.6152	0.3165	0.110*
C11	0.8814 (3)	0.4667 (4)	0.37879 (13)	0.0771 (10)
H11A	0.8455	0.3810	0.3875	0.116*
H11B	0.8493	0.5499	0.3927	0.116*
H11C	0.9556	0.4619	0.3994	0.116*
C12	1.0879 (2)	0.0194 (3)	0.16614 (13)	0.0485 (7)
C13	1.0736 (2)	−0.0379 (3)	0.21985 (14)	0.0609 (8)
H13	1.0137	−0.0131	0.2342	0.073*
C14	1.1488 (3)	−0.1329 (3)	0.25254 (15)	0.0770 (11)
H14	1.1393	−0.1719	0.2889	0.092*
C15	1.2367 (3)	−0.1695 (4)	0.2314 (2)	0.0991 (15)
H15	1.2879	−0.2316	0.2538	0.119*
C16	1.2491 (3)	−0.1147 (5)	0.1776 (2)	0.1075 (15)
H16	1.3078	−0.1423	0.1627	0.129*
C17	1.1760 (2)	−0.0190 (4)	0.14480 (16)	0.0781 (10)
H17	1.1861	0.0194	0.1085	0.094*
C18	0.8497 (2)	0.2257 (3)	0.03393 (12)	0.0457 (7)
C19	0.7627 (2)	0.2933 (3)	−0.01376 (12)	0.0455 (7)
C20	0.6553 (2)	0.2647 (3)	−0.01880 (14)	0.0599 (8)
H20	0.6343	0.2005	0.0079	0.072*
C21	0.5790 (2)	0.3324 (4)	−0.06390 (15)	0.0722 (10)
H21	0.5068	0.3133	−0.0672	0.087*
C22	0.6089 (3)	0.4266 (4)	−0.10348 (15)	0.0785 (11)
H22	0.5572	0.4719	−0.1334	0.094*
C23	0.7149 (3)	0.4542 (4)	−0.09893 (14)	0.0781 (10)
H23	0.7354	0.5180	−0.1260	0.094*
C24	0.7915 (2)	0.3877 (3)	−0.05430 (13)	0.0639 (9)
H24	0.8636	0.4068	−0.0516	0.077*
C25	0.8126 (2)	0.5352 (3)	0.08756 (11)	0.0428 (6)
C26	0.9106 (2)	0.6062 (3)	0.09834 (13)	0.0530 (7)
C27	0.9232 (3)	0.7360 (3)	0.07054 (15)	0.0687 (9)
H27	0.9896	0.7812	0.0788	0.082*
C28	0.8378 (3)	0.7983 (3)	0.03080 (16)	0.0782 (10)
H28	0.8461	0.8849	0.0115	0.094*
C29	0.7397 (3)	0.7304 (3)	0.01996 (14)	0.0666 (9)
C30	0.7271 (2)	0.6016 (3)	0.04800 (12)	0.0542 (8)
H30	0.6600	0.5582	0.0403	0.065*
H1	0.998 (2)	0.096 (3)	0.0845 (13)	0.073 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0498 (4)	0.0769 (6)	0.0765 (6)	−0.0138 (4)	0.0127 (4)	0.0079 (4)
Cl2	0.1407 (9)	0.0856 (7)	0.0772 (6)	0.0470 (6)	0.0125 (6)	0.0360 (5)
N1	0.0586 (15)	0.0595 (16)	0.0444 (15)	0.0226 (13)	0.0066 (13)	−0.0016 (13)
O1	0.0536 (12)	0.0750 (14)	0.0651 (14)	0.0274 (11)	0.0058 (11)	−0.0011 (11)
O2	0.0443 (11)	0.0443 (11)	0.0423 (11)	0.0114 (9)	0.0037 (9)	−0.0008 (9)
O3	0.0700 (13)	0.0590 (13)	0.0473 (12)	0.0196 (11)	0.0141 (10)	−0.0010 (10)
C1	0.0425 (16)	0.0382 (15)	0.0537 (18)	0.0032 (13)	0.0086 (14)	0.0007 (13)
C2	0.0557 (18)	0.0582 (19)	0.0551 (19)	0.0103 (15)	0.0147 (15)	−0.0021 (15)
C3	0.0611 (18)	0.0421 (16)	0.0461 (17)	0.0019 (14)	0.0100 (14)	−0.0056 (13)
C4	0.0510 (17)	0.0405 (16)	0.0440 (16)	0.0019 (13)	0.0042 (13)	0.0015 (13)
C5	0.0401 (15)	0.0287 (14)	0.0458 (16)	−0.0009 (12)	0.0094 (13)	−0.0019 (12)
C6	0.0412 (15)	0.0384 (15)	0.0443 (16)	0.0036 (13)	0.0080 (13)	−0.0006 (13)
C7	0.0403 (15)	0.0366 (14)	0.0406 (15)	0.0029 (12)	0.0055 (12)	0.0016 (12)
C8	0.0368 (14)	0.0372 (14)	0.0414 (15)	0.0022 (12)	0.0042 (12)	0.0033 (12)
C9	0.0350 (14)	0.0319 (14)	0.0423 (15)	0.0018 (11)	0.0057 (12)	0.0014 (12)
C10	0.089 (2)	0.0463 (18)	0.080 (2)	−0.0088 (17)	0.0093 (19)	−0.0055 (17)
C11	0.099 (3)	0.081 (2)	0.0485 (19)	0.012 (2)	0.0121 (18)	−0.0085 (17)
C12	0.0424 (16)	0.0452 (16)	0.0513 (18)	0.0116 (13)	−0.0026 (14)	−0.0085 (14)
C13	0.063 (2)	0.0516 (18)	0.062 (2)	0.0130 (16)	0.0028 (17)	0.0004 (16)
C14	0.098 (3)	0.053 (2)	0.064 (2)	0.017 (2)	−0.013 (2)	−0.0009 (17)
C15	0.091 (3)	0.093 (3)	0.090 (3)	0.049 (2)	−0.026 (3)	−0.016 (2)
C16	0.064 (2)	0.142 (4)	0.108 (4)	0.052 (3)	0.003 (3)	−0.019 (3)
C17	0.059 (2)	0.101 (3)	0.072 (2)	0.031 (2)	0.0102 (18)	−0.003 (2)
C18	0.0461 (16)	0.0393 (16)	0.0509 (17)	0.0018 (13)	0.0092 (14)	0.0022 (14)
C19	0.0503 (17)	0.0451 (16)	0.0396 (16)	0.0039 (13)	0.0071 (14)	−0.0016 (13)
C20	0.0542 (19)	0.063 (2)	0.059 (2)	−0.0079 (16)	0.0060 (16)	−0.0017 (16)
C21	0.0470 (19)	0.093 (3)	0.068 (2)	−0.0026 (18)	−0.0047 (18)	−0.015 (2)
C22	0.070 (2)	0.104 (3)	0.052 (2)	0.024 (2)	−0.0052 (19)	0.003 (2)
C23	0.073 (2)	0.104 (3)	0.057 (2)	0.023 (2)	0.0143 (18)	0.0295 (19)
C24	0.0537 (19)	0.082 (2)	0.0557 (19)	0.0118 (17)	0.0119 (16)	0.0130 (17)
C25	0.0522 (17)	0.0346 (14)	0.0424 (16)	0.0066 (13)	0.0129 (13)	0.0047 (12)
C26	0.0608 (19)	0.0441 (17)	0.0558 (18)	−0.0024 (15)	0.0170 (15)	0.0015 (14)
C27	0.086 (2)	0.050 (2)	0.077 (2)	−0.0123 (18)	0.032 (2)	0.0047 (18)
C28	0.129 (3)	0.0416 (19)	0.073 (2)	0.005 (2)	0.041 (2)	0.0112 (17)
C29	0.099 (3)	0.0466 (19)	0.0545 (19)	0.0207 (19)	0.0191 (19)	0.0126 (16)
C30	0.0639 (19)	0.0459 (17)	0.0520 (18)	0.0113 (15)	0.0119 (15)	0.0059 (14)

Geometric parameters (Å, º) top

Cl1—C26	1.745 (3)	C12—C13	1.373 (4)
Cl2—C29	1.741 (3)	C12—C17	1.374 (4)
N1—C6	1.330 (3)	C13—C14	1.386 (4)
N1—C12	1.417 (3)	C13—H13	0.9300
N1—H1	0.95 (3)	C14—C15	1.366 (5)
O1—C1	1.222 (3)	C14—H14	0.9300
O2—C6	1.367 (3)	C15—C16	1.359 (5)
O2—C5	1.381 (3)	C15—H15	0.9300
O3—C18	1.252 (3)	C16—C17	1.376 (5)
C1—C9	1.458 (3)	C16—H16	0.9300
C1—C2	1.507 (4)	C17—H17	0.9300
C2—C3	1.525 (4)	C18—C19	1.498 (3)
C2—H2A	0.9700	C19—C24	1.376 (4)
C2—H2B	0.9700	C19—C20	1.383 (4)
C3—C11	1.525 (4)	C20—C21	1.388 (4)
C3—C10	1.533 (4)	C20—H20	0.9300
C3—C4	1.536 (4)	C21—C22	1.366 (4)
C4—C5	1.485 (3)	C21—H21	0.9300
C4—H4A	0.9700	C22—C23	1.365 (4)
C4—H4B	0.9700	C22—H22	0.9300
C5—C9	1.331 (3)	C23—C24	1.380 (4)
C6—C7	1.379 (3)	C23—H23	0.9300
C7—C18	1.433 (4)	C24—H24	0.9300
C7—C8	1.527 (3)	C25—C30	1.388 (3)
C8—C9	1.499 (3)	C25—C26	1.391 (3)
C8—C25	1.535 (3)	C26—C27	1.382 (4)
C8—H8	0.9800	C27—C28	1.373 (4)
C10—H10A	0.9600	C27—H27	0.9300
C10—H10B	0.9600	C28—C29	1.379 (4)
C10—H10C	0.9600	C28—H28	0.9300
C11—H11A	0.9600	C29—C30	1.377 (4)
C11—H11B	0.9600	C30—H30	0.9300
C11—H11C	0.9600

C6—N1—C12	130.8 (3)	C13—C12—N1	123.5 (3)
C6—N1—H1	108.8 (17)	C17—C12—N1	116.3 (3)
C12—N1—H1	120.2 (17)	C12—C13—C14	119.7 (3)
C6—O2—C5	118.79 (18)	C12—C13—H13	120.2
O1—C1—C9	120.9 (2)	C14—C13—H13	120.2
O1—C1—C2	121.2 (2)	C15—C14—C13	120.2 (4)
C9—C1—C2	117.8 (2)	C15—C14—H14	119.9
C1—C2—C3	114.3 (2)	C13—C14—H14	119.9
C1—C2—H2A	108.7	C16—C15—C14	119.7 (4)
C3—C2—H2A	108.7	C16—C15—H15	120.1
C1—C2—H2B	108.7	C14—C15—H15	120.1
C3—C2—H2B	108.7	C15—C16—C17	121.0 (4)
H2A—C2—H2B	107.6	C15—C16—H16	119.5
C11—C3—C2	109.7 (2)	C17—C16—H16	119.5
C11—C3—C10	109.0 (2)	C12—C17—C16	119.5 (4)
C2—C3—C10	110.3 (2)	C12—C17—H17	120.2
C11—C3—C4	109.9 (2)	C16—C17—H17	120.2
C2—C3—C4	107.5 (2)	O3—C18—C7	123.7 (2)
C10—C3—C4	110.5 (2)	O3—C18—C19	116.8 (2)
C5—C4—C3	112.6 (2)	C7—C18—C19	119.4 (2)
C5—C4—H4A	109.1	C24—C19—C20	118.9 (3)
C3—C4—H4A	109.1	C24—C19—C18	118.1 (3)
C5—C4—H4B	109.1	C20—C19—C18	123.0 (3)
C3—C4—H4B	109.1	C19—C20—C21	119.7 (3)
H4A—C4—H4B	107.8	C19—C20—H20	120.1
C9—C5—O2	122.5 (2)	C21—C20—H20	120.1
C9—C5—C4	126.6 (2)	C22—C21—C20	120.6 (3)
O2—C5—C4	110.9 (2)	C22—C21—H21	119.7
N1—C6—O2	112.9 (2)	C20—C21—H21	119.7
N1—C6—C7	123.6 (3)	C23—C22—C21	119.8 (3)
O2—C6—C7	123.4 (2)	C23—C22—H22	120.1
C6—C7—C18	119.0 (2)	C21—C22—H22	120.1
C6—C7—C8	119.8 (2)	C22—C23—C24	120.2 (3)
C18—C7—C8	121.1 (2)	C22—C23—H23	119.9
C9—C8—C7	110.32 (19)	C24—C23—H23	119.9
C9—C8—C25	111.3 (2)	C19—C24—C23	120.8 (3)
C7—C8—C25	113.3 (2)	C19—C24—H24	119.6
C9—C8—H8	107.2	C23—C24—H24	119.6
C7—C8—H8	107.2	C30—C25—C26	116.9 (2)
C25—C8—H8	107.2	C30—C25—C8	118.7 (2)
C5—C9—C1	118.0 (2)	C26—C25—C8	124.3 (2)
C5—C9—C8	123.1 (2)	C27—C26—C25	121.8 (3)
C1—C9—C8	118.8 (2)	C27—C26—Cl1	116.7 (2)
C3—C10—H10A	109.5	C25—C26—Cl1	121.5 (2)
C3—C10—H10B	109.5	C28—C27—C26	120.2 (3)
H10A—C10—H10B	109.5	C28—C27—H27	119.9
C3—C10—H10C	109.5	C26—C27—H27	119.9
H10A—C10—H10C	109.5	C27—C28—C29	118.9 (3)
H10B—C10—H10C	109.5	C27—C28—H28	120.5
C3—C11—H11A	109.5	C29—C28—H28	120.5
C3—C11—H11B	109.5	C30—C29—C28	120.9 (3)
H11A—C11—H11B	109.5	C30—C29—Cl2	119.7 (3)
C3—C11—H11C	109.5	C28—C29—Cl2	119.4 (3)
H11A—C11—H11C	109.5	C29—C30—C25	121.3 (3)
H11B—C11—H11C	109.5	C29—C30—H30	119.4
C13—C12—C17	119.9 (3)	C25—C30—H30	119.4

O1—C1—C2—C3	−152.1 (3)	C12—C13—C14—C15	0.0 (5)
C9—C1—C2—C3	32.0 (3)	C13—C14—C15—C16	−1.4 (6)
C1—C2—C3—C11	−173.7 (2)	C14—C15—C16—C17	2.1 (6)
C1—C2—C3—C10	66.2 (3)	C13—C12—C17—C16	0.0 (5)
C1—C2—C3—C4	−54.2 (3)	N1—C12—C17—C16	−174.3 (3)
C11—C3—C4—C5	165.2 (2)	C15—C16—C17—C12	−1.4 (6)
C2—C3—C4—C5	45.8 (3)	C6—C7—C18—O3	−3.2 (4)
C10—C3—C4—C5	−74.5 (3)	C8—C7—C18—O3	172.1 (2)
C6—O2—C5—C9	−5.1 (3)	C6—C7—C18—C19	179.9 (2)
C6—O2—C5—C4	175.3 (2)	C8—C7—C18—C19	−4.8 (4)
C3—C4—C5—C9	−16.4 (4)	O3—C18—C19—C24	−67.0 (3)
C3—C4—C5—O2	163.2 (2)	C7—C18—C19—C24	110.1 (3)
C12—N1—C6—O2	12.1 (4)	O3—C18—C19—C20	112.9 (3)
C12—N1—C6—C7	−170.6 (3)	C7—C18—C19—C20	−70.0 (4)
C5—O2—C6—N1	−175.5 (2)	C24—C19—C20—C21	−0.7 (4)
C5—O2—C6—C7	7.2 (3)	C18—C19—C20—C21	179.5 (3)
N1—C6—C7—C18	1.1 (4)	C19—C20—C21—C22	0.1 (5)
O2—C6—C7—C18	178.2 (2)	C20—C21—C22—C23	0.3 (5)
N1—C6—C7—C8	−174.3 (2)	C21—C22—C23—C24	−0.3 (5)
O2—C6—C7—C8	2.8 (4)	C20—C19—C24—C23	0.7 (5)
C6—C7—C8—C9	−13.0 (3)	C18—C19—C24—C23	−179.5 (3)
C18—C7—C8—C9	171.7 (2)	C22—C23—C24—C19	−0.2 (5)
C6—C7—C8—C25	112.6 (3)	C9—C8—C25—C30	−117.1 (3)
C18—C7—C8—C25	−62.7 (3)	C7—C8—C25—C30	117.9 (3)
O2—C5—C9—C1	171.3 (2)	C9—C8—C25—C26	65.4 (3)
C4—C5—C9—C1	−9.1 (4)	C7—C8—C25—C26	−59.7 (3)
O2—C5—C9—C8	−7.2 (4)	C30—C25—C26—C27	−0.7 (4)
C4—C5—C9—C8	172.3 (2)	C8—C25—C26—C27	176.9 (3)
O1—C1—C9—C5	−174.8 (2)	C30—C25—C26—Cl1	179.1 (2)
C2—C1—C9—C5	1.2 (3)	C8—C25—C26—Cl1	−3.3 (4)
O1—C1—C9—C8	3.8 (4)	C25—C26—C27—C28	−0.3 (5)
C2—C1—C9—C8	179.8 (2)	Cl1—C26—C27—C28	179.8 (2)
C7—C8—C9—C5	15.5 (3)	C26—C27—C28—C29	1.0 (5)
C25—C8—C9—C5	−111.2 (3)	C27—C28—C29—C30	−0.5 (5)
C7—C8—C9—C1	−163.1 (2)	C27—C28—C29—Cl2	179.9 (3)
C25—C8—C9—C1	70.2 (3)	C28—C29—C30—C25	−0.6 (5)
C6—N1—C12—C13	34.3 (5)	Cl2—C29—C30—C25	179.0 (2)
C6—N1—C12—C17	−151.7 (3)	C26—C25—C30—C29	1.2 (4)
C17—C12—C13—C14	0.7 (4)	C8—C25—C30—C29	−176.6 (3)
N1—C12—C13—C14	174.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.95 (3)	1.74 (3)	2.565 (3)	144 (3)
C4—H4B···O1ⁱ	0.97	2.36	3.308 (3)	164
C13—H13···O2	0.93	2.50	2.915 (3)	108
C28—H28···O3ⁱⁱ	0.93	2.49	3.329 (4)	150

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₃₀H₂₅Cl₂NO₃
M_r	518.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	12.844 (3), 9.256 (2), 22.557 (5)
β (°)	103.365 (4)
V (Å³)	2609.1 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.20 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.946, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	14359, 5336, 2754
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.123, 1.02
No. of reflections	5336
No. of parameters	331
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.23

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.95 (3)	1.74 (3)	2.565 (3)	144 (3)
C4—H4B···O1ⁱ	0.97	2.36	3.308 (3)	164
C13—H13···O2	0.93	2.50	2.915 (3)	108
C28—H28···O3ⁱⁱ	0.93	2.49	3.329 (4)	150

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x, y+1, z.

Acknowledgements

This project was supported by the National Science Foundation of China (No. 20572057), the Natural Science Foundation of Shandong Province (Y2006B11) and the Doctoral Foundation of Qingdao University of Science and Technology.

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hamann, L. G., Higuchi, R. I., Zhi, L. & Edwards, J. P. (1998). J. Med. Chem. 41, 623–639. Web of Science CrossRef CAS PubMed Google Scholar
Hassanien, A. A., Zahran, M. A., El-Gaby, M. S. A. & Ghorab, M. M. (1999). J. Ind. Chem. Soc. 76, 350–354. CAS Google Scholar
Jiang, H., Wang, L. J. & Zhao, Z. X. (2001). J. Beihua Univ. 12, 489–490. Google Scholar
Li, M., Sun, E.-T. & Wen, L.-R. (2006). Acta Cryst. E62, o5607–o5608. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Anilino-3-benzoyl-4-(2,5-di­chloro­phen­yl)-7,7-di­methyl-5-oxo-5,6,7,8-tetra­hydro-4H-benzo[b]pyran

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Anilino-3-benzoyl-4-(2,5-dichlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyran