4-(2-Chloro­anilino)-3-phenyl­furan-2(5H)-one

Xiao, Z.-P.; Huang, Z.-J.; Liu, X.-Y.; Xiang, K.-S.; Yu, S.-R.

doi:10.1107/S1600536811044308

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3091

doi:10.1107/S1600536811044308

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4-(2-Chloroanilino)-3-phenylfuran-2(5H)-one

Zhu-Ping Xiao,^a ^* Ze-Jun Huang,^a Xiao-Yang Liu,^a Kai-Shuang Xiang ^a and She-Rong Yu ^a

^aCollege of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China
^*Correspondence e-mail: xiaozhuping2005@163.com

(Received 23 October 2011; accepted 24 October 2011; online 29 October 2011)

The title compound, C₁₆H₁₂ClNO₂, featuring a furan-2(5H)-one (γ-butyrolactone) core, contains two molecules (A and B) in the asymmetric unit, with different dihedral angles between the central ring and the pendant phenyl and chlorobenzene rings [43.33 (8) and 20.16 (8)°, respectively, for A, and 47.79 (8) and 13.87 (8)°, respectively, for B]. In the crystal, the A molecules are linked into [001] chains by single C—H⋯O interactions. The B molecules also form [001] chains, but their relative orientations in the chains are quite different to those of the A molecules so that adjacent B molecules are linked by two C—H⋯O hydrogen bonds. Finally, C—H⋯O interactions and aromatic π–π stacking contacts [centroid–centroid separations = 3.754 (1) and 3.817 (1) Å] link the chains into a two-dimensional array parallel to (010).

Related literature

For a related structure and background references, see: Xiao et al. (2011 ).

Experimental

Crystal data

C₁₆H₁₂ClNO₂
M_r = 285.72
Monoclinic, P 2₁ /c
a = 7.7305 (5) Å
b = 27.4374 (18) Å
c = 12.6242 (9) Å
β = 92.145 (1)°
V = 2675.8 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.919, T_max = 0.945
32744 measured reflections
6603 independent reflections
5086 reflections with I > 2σ(I)
R_int = 0.096

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.144
S = 1.06
6603 reflections
370 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1ⁱ	0.93	2.47	3.305 (2)	149
C31—H31⋯O4ⁱⁱ	0.93	2.58	3.422 (2)	151
C32—H32⋯O3ⁱⁱ	0.93	2.48	3.305 (2)	148
C19—H19⋯Cg2ⁱⁱⁱ	0.93	2.84	3.553 (2)	134
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811044308/hb6469sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044308/hb6469Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811044308/hb6469Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of compounds with a γ-butyrolactone (furanone) core (Xiao et al., 2011), we now report the structure of the title compound, (I).

The crystal structure of the title compound, 4-(2-chlorophenylamino)-3-phenylfuran-2(5H)-one, contains two crystallographically independent molecules (Fig. 1) in an asymmetric unit with difference of bond length lower than 0.009 Å. In molecule A (from C1 to C16, O1, O2, N1 and Cl1), the central furan-2(5H)-one ring make a dihedral angles of 43.33 (8) and 20.16 (8) ° with the benzene ring and the o-chloroaniline ring, repectively. While in the molecule B (from C17 to C32, O3, O4, N2 and Cl2), they are 47.79 (8) and 13.87 (8) °, respectively. For the convenience of description, molecular structure was discussed based on A. Bond distance C7—C10 (1.3490 (19) Å) is indicative of a double bond, and the title compound was therefore identified as a furan-2(5H)-one.

Interestingly, molecule A and molecule B show different interemolecular hydrogen bonding patterns. For molecule A, an infinite one-dimensional line is formed by C—H···O hydrogen bondings (Fig 2a). While molecules B are linked into a line by R²₂(7) rings, which built from C31—H31···O4 and C32—H32···O3 hydrogen bonds centred at (0, 0, n) and (0, 0.0695, n) respectively, where n represents an integer (Fig. 2 b). Between the resulted lines, three kinds of intermolecular interactions were found and link molecules to further generate an infinite two-dimensional sheet. Of them, C—H···π occurs between C19 (in molecule B) and 3-benzene ring with "H···centroid" length of 2.840 Å, while π–π contacts occur between furanone rings and aniline rings with "centroid···centroid" lengths of 3.754 (1) and 3.817 (1) Å, respectively (Fig. 3a and Fig. 3 b).

Related literature top

For a related structure and background references, see: Xiao et al. (2011).

Experimental top

To a methanol solution (20 ml) of 2-methoxy-1-naphthaldehyde (0.1 mmol, 17.4 mg) and 4-methylbenzohydrazide (0.1 mmol, 15.0 mg), a few drops of acetic acid were added. The mixture was refluxed for 1 h and then cooled to room temperature. The white crystalline solid was collected by filtration, washed with cold methanol and dried in air. Single crystals, suitable for X-ray diffraction, were obtained by slow evaporation of a methanol solution of the product in air.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. a. Molecules (A) form a one-dimensional line through intermolecular C—H···O hydrogen bonds. For the sake of clarity, the H atoms have been omitted except that involving in hydrogen bonds.
	Fig. 3. b. Molecules (B) form a one-dimensional line through intermolecular C—H···O hydrogen bonds. For the sake of clarity, the H atoms have been omitted except that involving in hydrogen bonds.
	Fig. 4. a. A two-dimensional sheet is formed by intermolecular C—H···π interactions and π–π contacts.
	Fig. 5. b. A two-dimensional sheet is formed by intermolecular C—H···π interactions and π–π contacts.

4-(2-Chloroanilino)-3-phenylfuran-2(5H)-one top

Crystal data top

C₁₆H₁₂ClNO₂	Z = 8
M_r = 285.72	F(000) = 1184
Monoclinic, P2₁/c	D_x = 1.418 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.7305 (5) Å	θ = 2.6–27.8°
b = 27.4374 (18) Å	µ = 0.29 mm⁻¹
c = 12.6242 (9) Å	T = 298 K
β = 92.145 (1)°	Block, colorless
V = 2675.8 (3) Å³	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	6603 independent reflections
Radiation source: fine-focus sealed tube	5086 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
ϕ and ω scan	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.919, T_max = 0.945	k = −36→36
32744 measured reflections	l = −16→16

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.144	w = 1/[σ²(F_o²) + (0.080P)² + 0.1033P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
6603 reflections	Δρ_max = 0.36 e Å⁻³
370 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0084 (10)

Crystal data top

C₁₆H₁₂ClNO₂	V = 2675.8 (3) Å³
M_r = 285.72	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7305 (5) Å	µ = 0.29 mm⁻¹
b = 27.4374 (18) Å	T = 298 K
c = 12.6242 (9) Å	0.30 × 0.20 × 0.20 mm
β = 92.145 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	6603 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5086 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.945	R_int = 0.096
32744 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.36 e Å⁻³
6603 reflections	Δρ_min = −0.30 e Å⁻³
370 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
C1	0.27814 (18)	0.35945 (5)	0.29763 (10)	0.0461 (3)
C2	0.3577 (2)	0.34203 (6)	0.20759 (12)	0.0583 (4)
H2	0.3631	0.3086	0.1954	0.070*
C3	0.4284 (2)	0.37386 (8)	0.13655 (13)	0.0682 (5)
H3	0.4800	0.3618	0.0766	0.082*
C4	0.4231 (2)	0.42301 (7)	0.15360 (13)	0.0684 (5)
H4	0.4722	0.4442	0.1058	0.082*
C5	0.3450 (2)	0.44111 (6)	0.24147 (13)	0.0609 (4)
H5	0.3413	0.4746	0.2529	0.073*
C6	0.27233 (19)	0.40972 (5)	0.31272 (11)	0.0504 (3)
H6	0.2188	0.4223	0.3715	0.060*
C7	0.20474 (18)	0.32524 (5)	0.37337 (11)	0.0475 (3)
C8	0.1029 (2)	0.28279 (5)	0.34135 (13)	0.0608 (4)
C9	0.1273 (2)	0.28158 (5)	0.52194 (13)	0.0578 (4)
H9A	0.2096	0.2607	0.5599	0.069*
H9B	0.0365	0.2906	0.5691	0.069*
C10	0.21487 (17)	0.32582 (5)	0.48027 (11)	0.0454 (3)
C11	0.28478 (17)	0.37210 (5)	0.64825 (10)	0.0457 (3)
C12	0.33208 (18)	0.41894 (5)	0.68118 (11)	0.0500 (3)
C13	0.3164 (2)	0.43397 (7)	0.78420 (13)	0.0656 (4)
H13	0.3484	0.4655	0.8038	0.079*
C14	0.2536 (2)	0.40257 (8)	0.85839 (13)	0.0729 (5)
H14	0.2403	0.4129	0.9278	0.088*
C15	0.2108 (2)	0.35592 (7)	0.82878 (13)	0.0681 (5)
H15	0.1711	0.3343	0.8791	0.082*
C16	0.2257 (2)	0.34051 (6)	0.72529 (12)	0.0561 (4)
H16	0.1959	0.3087	0.7069	0.067*
C17	0.22903 (18)	0.63216 (5)	0.06184 (11)	0.0487 (3)
C18	0.1337 (2)	0.64534 (7)	−0.02958 (12)	0.0626 (4)
H18	0.1155	0.6781	−0.0452	0.075*
C19	0.0664 (2)	0.61005 (9)	−0.09697 (13)	0.0758 (6)
H19	0.0023	0.6193	−0.1575	0.091*
C20	0.0925 (2)	0.56142 (9)	−0.07617 (15)	0.0782 (6)
H20	0.0468	0.5379	−0.1223	0.094*
C21	0.1860 (2)	0.54794 (7)	0.01279 (15)	0.0692 (5)
H21	0.2038	0.5150	0.0273	0.083*
C22	0.2544 (2)	0.58261 (5)	0.08146 (12)	0.0554 (4)
H22	0.3183	0.5728	0.1416	0.066*
C23	0.29904 (19)	0.66934 (5)	0.13540 (11)	0.0490 (3)
C24	0.3918 (2)	0.71252 (6)	0.10214 (13)	0.0621 (4)
C25	0.3729 (2)	0.71710 (5)	0.28216 (12)	0.0559 (4)
H25A	0.2888	0.7379	0.3150	0.067*
H25B	0.4661	0.7101	0.3335	0.067*
C26	0.29004 (18)	0.67104 (5)	0.24190 (11)	0.0458 (3)
C27	0.21703 (17)	0.62944 (5)	0.41166 (11)	0.0451 (3)
C28	0.16217 (18)	0.58432 (5)	0.44911 (12)	0.0499 (3)
C29	0.1665 (2)	0.57327 (6)	0.55559 (14)	0.0648 (4)
H29	0.1286	0.5430	0.5783	0.078*
C30	0.2268 (2)	0.60706 (7)	0.62796 (13)	0.0708 (5)
H30	0.2321	0.5996	0.6999	0.085*
C31	0.2794 (2)	0.65192 (7)	0.59359 (13)	0.0640 (4)
H31	0.3190	0.6750	0.6428	0.077*
C32	0.2744 (2)	0.66332 (6)	0.48734 (12)	0.0548 (4)
H32	0.3098	0.6940	0.4658	0.066*
Cl1	0.40795 (6)	0.460028 (15)	0.58859 (4)	0.06829 (15)
Cl2	0.09240 (6)	0.540051 (15)	0.35831 (4)	0.06933 (16)
N1	0.30072 (17)	0.35959 (5)	0.54159 (10)	0.0512 (3)
N2	0.21099 (18)	0.63755 (5)	0.30234 (10)	0.0553 (3)
O1	0.05550 (19)	0.26896 (4)	0.25415 (10)	0.0813 (4)
O2	0.05665 (17)	0.25763 (4)	0.42950 (10)	0.0711 (3)
O3	0.4329 (2)	0.72534 (4)	0.01522 (10)	0.0833 (4)
O4	0.43819 (18)	0.73964 (4)	0.18943 (10)	0.0716 (3)
H1	0.354 (2)	0.3800 (6)	0.5078 (13)	0.054 (4)*
H2A	0.164 (2)	0.6156 (6)	0.2687 (14)	0.061 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0511 (7)	0.0492 (7)	0.0377 (6)	0.0074 (6)	−0.0023 (5)	−0.0037 (5)
C2	0.0671 (9)	0.0633 (9)	0.0442 (8)	0.0156 (7)	0.0002 (7)	−0.0096 (7)
C3	0.0691 (10)	0.0927 (13)	0.0437 (8)	0.0134 (9)	0.0127 (7)	−0.0060 (8)
C4	0.0713 (10)	0.0840 (13)	0.0506 (9)	−0.0060 (9)	0.0108 (8)	0.0071 (8)
C5	0.0717 (10)	0.0574 (9)	0.0538 (8)	−0.0063 (7)	0.0037 (7)	0.0001 (7)
C6	0.0591 (8)	0.0521 (8)	0.0401 (7)	0.0035 (6)	0.0037 (6)	−0.0043 (6)
C7	0.0551 (8)	0.0409 (7)	0.0464 (7)	0.0075 (5)	0.0001 (6)	−0.0039 (5)
C8	0.0805 (11)	0.0430 (8)	0.0585 (9)	0.0052 (7)	−0.0026 (8)	−0.0088 (7)
C9	0.0736 (10)	0.0434 (8)	0.0565 (9)	−0.0004 (7)	0.0014 (7)	0.0026 (6)
C10	0.0498 (7)	0.0411 (7)	0.0455 (7)	0.0071 (5)	0.0028 (6)	−0.0014 (5)
C11	0.0437 (7)	0.0534 (8)	0.0399 (7)	0.0039 (5)	0.0008 (5)	−0.0001 (6)
C12	0.0482 (7)	0.0535 (8)	0.0481 (7)	0.0027 (6)	−0.0014 (6)	−0.0021 (6)
C13	0.0693 (10)	0.0725 (11)	0.0545 (9)	0.0040 (8)	−0.0057 (7)	−0.0160 (8)
C14	0.0790 (11)	0.0965 (14)	0.0434 (8)	0.0055 (10)	0.0022 (8)	−0.0121 (9)
C15	0.0726 (10)	0.0881 (13)	0.0440 (8)	0.0045 (9)	0.0078 (7)	0.0088 (8)
C16	0.0619 (9)	0.0595 (9)	0.0472 (8)	0.0006 (7)	0.0053 (6)	0.0040 (7)
C17	0.0500 (7)	0.0552 (8)	0.0411 (7)	0.0031 (6)	0.0045 (6)	0.0018 (6)
C18	0.0627 (9)	0.0801 (11)	0.0451 (8)	0.0156 (8)	0.0036 (7)	0.0056 (8)
C19	0.0630 (10)	0.1212 (18)	0.0428 (8)	0.0052 (10)	−0.0054 (7)	−0.0056 (10)
C20	0.0736 (11)	0.1020 (16)	0.0588 (10)	−0.0176 (10)	0.0018 (9)	−0.0241 (10)
C21	0.0794 (11)	0.0623 (10)	0.0662 (11)	−0.0134 (8)	0.0068 (9)	−0.0119 (8)
C22	0.0615 (9)	0.0550 (9)	0.0493 (8)	−0.0023 (7)	−0.0016 (7)	−0.0003 (6)
C23	0.0588 (8)	0.0424 (7)	0.0458 (7)	0.0057 (6)	0.0017 (6)	0.0049 (6)
C24	0.0901 (12)	0.0408 (8)	0.0559 (9)	0.0046 (7)	0.0109 (8)	0.0076 (7)
C25	0.0767 (10)	0.0398 (7)	0.0513 (8)	−0.0004 (6)	0.0055 (7)	0.0003 (6)
C26	0.0509 (7)	0.0409 (7)	0.0454 (7)	0.0032 (5)	−0.0005 (6)	0.0032 (5)
C27	0.0447 (7)	0.0465 (7)	0.0442 (7)	0.0031 (5)	0.0024 (5)	0.0026 (5)
C28	0.0472 (7)	0.0479 (8)	0.0550 (8)	0.0042 (6)	0.0071 (6)	0.0025 (6)
C29	0.0677 (10)	0.0620 (10)	0.0655 (10)	0.0057 (8)	0.0139 (8)	0.0197 (8)
C30	0.0814 (11)	0.0846 (12)	0.0469 (9)	0.0096 (10)	0.0076 (8)	0.0123 (8)
C31	0.0689 (10)	0.0760 (11)	0.0469 (8)	0.0049 (8)	−0.0009 (7)	−0.0058 (8)
C32	0.0633 (9)	0.0528 (8)	0.0482 (8)	0.0000 (6)	−0.0008 (6)	0.0000 (6)
Cl1	0.0816 (3)	0.0550 (3)	0.0685 (3)	−0.01316 (18)	0.0057 (2)	0.00081 (18)
Cl2	0.0762 (3)	0.0517 (2)	0.0803 (3)	−0.01332 (18)	0.0058 (2)	−0.00368 (19)
N1	0.0619 (7)	0.0526 (7)	0.0397 (6)	−0.0100 (6)	0.0081 (5)	−0.0016 (5)
N2	0.0683 (8)	0.0554 (7)	0.0419 (6)	−0.0165 (6)	−0.0028 (6)	0.0001 (5)
O1	0.1134 (10)	0.0628 (7)	0.0665 (8)	−0.0094 (7)	−0.0115 (7)	−0.0203 (6)
O2	0.0986 (9)	0.0456 (6)	0.0688 (7)	−0.0136 (6)	−0.0024 (7)	−0.0031 (5)
O3	0.1370 (12)	0.0537 (7)	0.0611 (7)	−0.0046 (7)	0.0279 (8)	0.0119 (6)
O4	0.1118 (10)	0.0415 (6)	0.0624 (7)	−0.0131 (6)	0.0159 (7)	0.0007 (5)

Geometric parameters (Å, º) top

C1—C6	1.393 (2)	C17—C22	1.395 (2)
C1—C2	1.3968 (19)	C17—C23	1.469 (2)
C1—C7	1.469 (2)	C18—C19	1.378 (3)
C2—C3	1.379 (3)	C18—H18	0.9300
C2—H2	0.9300	C19—C20	1.373 (3)
C3—C4	1.367 (3)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.364 (3)
C4—C5	1.375 (2)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.379 (2)
C5—C6	1.380 (2)	C21—H21	0.9300
C5—H5	0.9300	C22—H22	0.9300
C6—H6	0.9300	C23—C26	1.3497 (19)
C7—C10	1.3490 (19)	C23—C24	1.455 (2)
C7—C8	1.455 (2)	C24—O3	1.2063 (19)
C8—O1	1.208 (2)	C24—O4	1.367 (2)
C8—O2	1.368 (2)	C25—O4	1.4323 (19)
C9—O2	1.4296 (19)	C25—C26	1.4972 (19)
C9—C10	1.495 (2)	C25—H25A	0.9700
C9—H9A	0.9700	C25—H25B	0.9700
C9—H9B	0.9700	C26—N2	1.3547 (18)
C10—N1	1.3637 (18)	C27—C32	1.394 (2)
C11—C16	1.393 (2)	C27—C28	1.3966 (19)
C11—C12	1.395 (2)	C27—N2	1.3969 (18)
C11—N1	1.3995 (18)	C28—C29	1.377 (2)
C12—C13	1.374 (2)	C28—Cl2	1.7419 (16)
C12—Cl1	1.7415 (15)	C29—C30	1.371 (3)
C13—C14	1.374 (3)	C29—H29	0.9300
C13—H13	0.9300	C30—C31	1.372 (3)
C14—C15	1.371 (3)	C30—H30	0.9300
C14—H14	0.9300	C31—C32	1.377 (2)
C15—C16	1.382 (2)	C31—H31	0.9300
C15—H15	0.9300	C32—H32	0.9300
C16—H16	0.9300	N1—H1	0.824 (16)
C17—C18	1.393 (2)	N2—H2A	0.815 (17)

C6—C1—C2	117.86 (14)	C19—C18—H18	119.8
C6—C1—C7	121.89 (12)	C17—C18—H18	119.8
C2—C1—C7	120.25 (13)	C20—C19—C18	121.00 (16)
C3—C2—C1	120.65 (16)	C20—C19—H19	119.5
C3—C2—H2	119.7	C18—C19—H19	119.5
C1—C2—H2	119.7	C21—C20—C19	119.37 (17)
C4—C3—C2	120.50 (15)	C21—C20—H20	120.3
C4—C3—H3	119.7	C19—C20—H20	120.3
C2—C3—H3	119.7	C20—C21—C22	120.64 (18)
C3—C4—C5	120.00 (16)	C20—C21—H21	119.7
C3—C4—H4	120.0	C22—C21—H21	119.7
C5—C4—H4	120.0	C21—C22—C17	120.84 (15)
C4—C5—C6	120.14 (16)	C21—C22—H22	119.6
C4—C5—H5	119.9	C17—C22—H22	119.6
C6—C5—H5	119.9	C26—C23—C24	107.68 (13)
C5—C6—C1	120.84 (14)	C26—C23—C17	128.47 (13)
C5—C6—H6	119.6	C24—C23—C17	123.84 (13)
C1—C6—H6	119.6	O3—C24—O4	120.29 (15)
C10—C7—C8	107.34 (13)	O3—C24—C23	130.52 (16)
C10—C7—C1	129.37 (13)	O4—C24—C23	109.15 (13)
C8—C7—C1	123.29 (13)	O4—C25—C26	104.26 (12)
O1—C8—O2	120.20 (15)	O4—C25—H25A	110.9
O1—C8—C7	130.33 (17)	C26—C25—H25A	110.9
O2—C8—C7	109.45 (13)	O4—C25—H25B	110.9
O2—C9—C10	104.48 (12)	C26—C25—H25B	110.9
O2—C9—H9A	110.9	H25A—C25—H25B	108.9
C10—C9—H9A	110.9	C23—C26—N2	125.37 (13)
O2—C9—H9B	110.9	C23—C26—C25	109.27 (12)
C10—C9—H9B	110.9	N2—C26—C25	125.29 (13)
H9A—C9—H9B	108.9	C32—C27—C28	116.88 (13)
C7—C10—N1	125.78 (13)	C32—C27—N2	124.67 (13)
C7—C10—C9	109.41 (12)	C28—C27—N2	118.45 (13)
N1—C10—C9	124.69 (12)	C29—C28—C27	121.94 (15)
C16—C11—C12	117.02 (13)	C29—C28—Cl2	118.97 (12)
C16—C11—N1	124.21 (14)	C27—C28—Cl2	119.06 (11)
C12—C11—N1	118.76 (13)	C30—C29—C28	119.78 (15)
C13—C12—C11	121.81 (15)	C30—C29—H29	120.1
C13—C12—Cl1	119.00 (13)	C28—C29—H29	120.1
C11—C12—Cl1	119.17 (11)	C29—C30—C31	119.56 (16)
C12—C13—C14	120.18 (17)	C29—C30—H30	120.2
C12—C13—H13	119.9	C31—C30—H30	120.2
C14—C13—H13	119.9	C30—C31—C32	120.96 (17)
C15—C14—C13	119.17 (16)	C30—C31—H31	119.5
C15—C14—H14	120.4	C32—C31—H31	119.5
C13—C14—H14	120.4	C31—C32—C27	120.86 (15)
C14—C15—C16	121.04 (17)	C31—C32—H32	119.6
C14—C15—H15	119.5	C27—C32—H32	119.6
C16—C15—H15	119.5	C10—N1—C11	130.87 (13)
C15—C16—C11	120.73 (16)	C10—N1—H1	114.2 (12)
C15—C16—H16	119.6	C11—N1—H1	113.3 (12)
C11—C16—H16	119.6	C26—N2—C27	131.72 (13)
C18—C17—C22	117.82 (14)	C26—N2—H2A	114.2 (13)
C18—C17—C23	120.94 (14)	C27—N2—H2A	113.2 (13)
C22—C17—C23	121.24 (13)	C8—O2—C9	109.19 (12)
C19—C18—C17	120.33 (17)	C24—O4—C25	109.52 (12)

C6—C1—C2—C3	0.2 (2)	C23—C17—C22—C21	179.00 (14)
C7—C1—C2—C3	−179.41 (14)	C18—C17—C23—C26	132.18 (16)
C1—C2—C3—C4	0.6 (2)	C22—C17—C23—C26	−47.3 (2)
C2—C3—C4—C5	−0.8 (3)	C18—C17—C23—C24	−47.0 (2)
C3—C4—C5—C6	0.1 (3)	C22—C17—C23—C24	133.49 (16)
C4—C5—C6—C1	0.7 (2)	C26—C23—C24—O3	178.08 (19)
C2—C1—C6—C5	−0.8 (2)	C17—C23—C24—O3	−2.6 (3)
C7—C1—C6—C5	178.78 (13)	C26—C23—C24—O4	0.26 (18)
C6—C1—C7—C10	−42.7 (2)	C17—C23—C24—O4	179.59 (13)
C2—C1—C7—C10	136.91 (16)	C24—C23—C26—N2	178.94 (14)
C6—C1—C7—C8	137.21 (15)	C17—C23—C26—N2	−0.3 (2)
C2—C1—C7—C8	−43.2 (2)	C24—C23—C26—C25	1.93 (17)
C10—C7—C8—O1	176.81 (18)	C17—C23—C26—C25	−177.36 (14)
C1—C7—C8—O1	−3.1 (3)	O4—C25—C26—C23	−3.30 (17)
C10—C7—C8—O2	−1.51 (17)	O4—C25—C26—N2	179.68 (13)
C1—C7—C8—O2	178.58 (13)	C32—C27—C28—C29	−0.9 (2)
C8—C7—C10—N1	179.36 (13)	N2—C27—C28—C29	179.05 (14)
C1—C7—C10—N1	−0.7 (2)	C32—C27—C28—Cl2	−178.93 (11)
C8—C7—C10—C9	3.25 (16)	N2—C27—C28—Cl2	1.05 (18)
C1—C7—C10—C9	−176.85 (13)	C27—C28—C29—C30	−0.3 (2)
O2—C9—C10—C7	−3.77 (16)	Cl2—C28—C29—C30	177.69 (13)
O2—C9—C10—N1	−179.94 (13)	C28—C29—C30—C31	1.2 (3)
C16—C11—C12—C13	−2.0 (2)	C29—C30—C31—C32	−0.8 (3)
N1—C11—C12—C13	178.63 (14)	C30—C31—C32—C27	−0.5 (3)
C16—C11—C12—Cl1	179.71 (10)	C28—C27—C32—C31	1.3 (2)
N1—C11—C12—Cl1	0.30 (18)	N2—C27—C32—C31	−178.65 (15)
C11—C12—C13—C14	0.4 (2)	C7—C10—N1—C11	160.68 (15)
Cl1—C12—C13—C14	178.70 (13)	C9—C10—N1—C11	−23.8 (2)
C12—C13—C14—C15	1.5 (3)	C16—C11—N1—C10	26.5 (2)
C13—C14—C15—C16	−1.7 (3)	C12—C11—N1—C10	−154.17 (14)
C14—C15—C16—C11	0.0 (3)	C23—C26—N2—C27	166.70 (15)
C12—C11—C16—C15	1.8 (2)	C25—C26—N2—C27	−16.8 (3)
N1—C11—C16—C15	−178.88 (15)	C32—C27—N2—C26	18.0 (3)
C22—C17—C18—C19	0.6 (2)	C28—C27—N2—C26	−161.96 (15)
C23—C17—C18—C19	−178.91 (14)	O1—C8—O2—C9	−179.46 (16)
C17—C18—C19—C20	−0.5 (3)	C7—C8—O2—C9	−0.95 (18)
C18—C19—C20—C21	0.2 (3)	C10—C9—O2—C8	2.77 (17)
C19—C20—C21—C22	−0.1 (3)	O3—C24—O4—C25	179.48 (17)
C20—C21—C22—C17	0.3 (3)	C23—C24—O4—C25	−2.43 (19)
C18—C17—C22—C21	−0.5 (2)	C26—C25—O4—C24	3.44 (17)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1ⁱ	0.93	2.47	3.305 (2)	149
C31—H31···O4ⁱⁱ	0.93	2.58	3.422 (2)	151
C32—H32···O3ⁱⁱ	0.93	2.48	3.305 (2)	148
C19—H19···Cg2ⁱⁱⁱ	0.93	2.84	3.553 (2)	134

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂ClNO₂
M_r	285.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.7305 (5), 27.4374 (18), 12.6242 (9)
β (°)	92.145 (1)
V (Å³)	2675.8 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.919, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	32744, 6603, 5086
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.144, 1.06
No. of reflections	6603
No. of parameters	370
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.30

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1ⁱ	0.93	2.47	3.305 (2)	149
C31—H31···O4ⁱⁱ	0.93	2.58	3.422 (2)	151
C32—H32···O3ⁱⁱ	0.93	2.48	3.305 (2)	148
C19—H19···Cg2ⁱⁱⁱ	0.93	2.84	3.553 (2)	134

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

Acknowledgements

The work was financed by a project supported by the Hunan Provincial Natural Science Foundation of China (grant No. 11 J J3113), by the Key Laboratory of Hunan Forest Products and Chemical Industry Engineering of Hunan Province (grant No. JDZ201102) and by an aid program for the Science and Technology Innovative Research Team (Chemicals of Forestry Resources and Development of Forest Products) in Higher Educational Institutions of Hunan Province.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Xiao, Z.-P., Yi, L.-C., Li, J.-L., Zhang, B. & Liao, M.-L. (2011). Acta Cryst. E57, o3086. CrossRef Google Scholar

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Volume 67| Part 11| November 2011| Page o3091

doi:10.1107/S1600536811044308

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