1-Benzyl-4-chloro­indoline-2,3-dione

Wang, D.C.; Leng, B.R.; Wang, G.B.; Wei, P.; Ou-yang, P.K.

doi:10.1107/S1600536811051816

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o37

doi:10.1107/S1600536811051816

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1-Benzyl-4-chloroindoline-2,3-dione

De Cai Wang,^a ^* Bo Rong Leng,^a Gui Bin Wang,^b Ping Wei ^a and Ping Kai Ou-yang ^a

^aSate Key Laboratory of Materials-Oriented Chemcial Engineering, College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bPRC DAYAOWAN Administration for Entry & Exit Inspection and Quarantine, Haiqingdao Foreign Area Development Zone, Dalian 116610, Liaoning Province, People's Republic of China
^*Correspondence e-mail: dc_wang@hotmail.com

(Received 27 November 2011; accepted 1 December 2011; online 7 December 2011)

There are two independent molecules in the asymmetric unit of the title compound, C₁₅H₁₀ClNO₂, which differ in the dihedral angles between the mean planes of the phenyl ring and the 4-chloroindoline-2,3-dione ring system [59.48 (9) and 79.0 (1)°]. In the crystal, molecules are linked through C—H⋯O hydrogen bonds, forming polymeric chains in [100].

Related literature

For the preparation, see: Bouhfid et al. (2005 ). For a related structure and background to isatin derivatives, see: Liu et al. (2011 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₀ClNO₂
M_r = 271.69
Orthorhombic, P b c a
a = 22.864 (5) Å
b = 16.600 (3) Å
c = 13.335 (3) Å
V = 5061.2 (18) Å³
Z = 16
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.916, T_max = 0.971
4623 measured reflections
4623 independent reflections
1929 reflections with I > 2σ(I)
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.117
S = 1.00
4623 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1ⁱ	0.93	2.58	3.228 (4)	127
C4—H4A⋯O2ⁱ	0.93	2.56	3.473 (4)	167
C18—H18A⋯O3ⁱⁱ	0.93	2.40	3.329 (4)	173
C19—H19A⋯O4ⁱⁱ	0.93	2.60	3.382 (6)	142
C26—H26A⋯O2ⁱⁱⁱ	0.93	2.59	3.350 (4)	140
C29—H29A⋯O1^iv	0.93	2.59	3.505 (5)	169
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo,1995 ); 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: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811051816/hb6540sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051816/hb6540Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811051816/hb6540Isup3.cml

checkCIF report

Comment top

As a part of our studies into the synthesis and structures of isatin derivatives (Liu et al., 2011), the title compound (I) was synthesized (Bouhfid et al.2005) and its structure is now reported.

The title compound crystallized with two independent molecules (A & B) in the asymmetric unit (Fig. 1). They differ significantly in conformation, as may be seen from the dihedral angle in the mean planes of the benzene and 4-chloroindoline-2,3-dione. For molecule A,the dihedral angle between the mean planes of the benzene and 4-chloroindoline-2,3-dione is 59.481 (88)°,while the corresponding dihedral angle is 79.028 (114)° in molecule B. The bond lengths (Allen et al., 1987) and bond angles are otherwise within normal ranges.

In the crystal structure, intermolecular and intramolecular C—H···O hydrogen bonding interactions (Table 1) link the molecules into a polymeric chain extended along the a axis (Fig. 2).

Related literature top

For the preparation, see: Bouhfid et al. (2005). For a related structure and background to isatin derivatives, see: Liu et al. (2011). For reference bond-length data, see: Allen et al. (1987).

Experimental top

4-chloroisatin (1.81 g, 0.01 mol) was reacted with benzyl bromide (0.02 mol) in the presence of K₂CO₃ (2.76 g, 0.02 mol) and tetrabutylammonium bromide (0.32 g, 0.001 mol) in DMF (60 ml). After 12 h stirring at rt, the precipitate was removed by filtration and purified by recrystallization from ethanol (m.p. 165.8–166.5 °C; yield 70%). Yellow blocks of the title compound were obtained by slow evaporation of an ethanol solution at room temperature.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo,1995); 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: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 30% probability level.
	Fig. 2. A packing diagram of (I). The intermolecular hydrogen bonds are shown as dashed lines.

1-Benzyl-4-chloroindoline-2,3-dione top

Crystal data top

C₁₅H₁₀ClNO₂	F(000) = 2240
M_r = 271.69	D_x = 1.426 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 22.864 (5) Å	θ = 9–13°
b = 16.600 (3) Å	µ = 0.30 mm⁻¹
c = 13.335 (3) Å	T = 293 K
V = 5061.2 (18) Å³	Block, yellow
Z = 16	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1929 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.4°, θ_min = 1.8°
ω/2θ scans	h = 0→27
Absorption correction: ψ scan (North et al., 1968)	k = 0→20
T_min = 0.916, T_max = 0.971	l = 0→16
4623 measured reflections	3 standard reflections every 200 reflections
4623 independent reflections	intensity decay: 1%

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.032P)²] where P = (F_o² + 2F_c²)/3
4623 reflections	(Δ/σ)_max = 0.001
343 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₁₀ClNO₂	V = 5061.2 (18) Å³
M_r = 271.69	Z = 16
Orthorhombic, Pbca	Mo Kα radiation
a = 22.864 (5) Å	µ = 0.30 mm⁻¹
b = 16.600 (3) Å	T = 293 K
c = 13.335 (3) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1929 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.916, T_max = 0.971	3 standard reflections every 200 reflections
4623 measured reflections	intensity decay: 1%
4623 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.00	Δρ_max = 0.18 e Å⁻³
4623 reflections	Δρ_min = −0.20 e Å⁻³
343 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	0.61720 (4)	0.52555 (7)	0.54905 (10)	0.0902 (4)
C1	0.73389 (14)	0.5069 (2)	0.5352 (3)	0.0438 (9)
N1	0.83104 (11)	0.47219 (17)	0.5229 (2)	0.0506 (8)
O1	0.82562 (10)	0.33371 (14)	0.5350 (2)	0.0681 (8)
O2	0.70097 (10)	0.36781 (14)	0.5538 (2)	0.0628 (8)
C2	0.68738 (15)	0.5601 (2)	0.5384 (3)	0.0522 (10)
C3	0.69793 (18)	0.6420 (2)	0.5343 (3)	0.0644 (12)
H3A	0.6671	0.6785	0.5358	0.077*
C4	0.7549 (2)	0.6687 (2)	0.5278 (3)	0.0649 (12)
H4A	0.7617	0.7239	0.5269	0.078*
C5	0.80188 (17)	0.6178 (2)	0.5228 (3)	0.0540 (11)
H5A	0.8398	0.6375	0.5173	0.065*
C6	0.79077 (15)	0.5362 (2)	0.5261 (3)	0.0452 (9)
C7	0.80405 (15)	0.3997 (2)	0.5335 (3)	0.0490 (10)
C8	0.73753 (16)	0.4189 (2)	0.5423 (3)	0.0489 (10)
C9	0.89331 (15)	0.4816 (2)	0.5095 (3)	0.0576 (11)
H9A	0.9002	0.5207	0.4567	0.069*
H9B	0.9096	0.4306	0.4876	0.069*
C10	0.92469 (15)	0.5083 (2)	0.6021 (3)	0.0525 (10)
C11	0.96343 (16)	0.5718 (2)	0.5974 (3)	0.0721 (13)
H11A	0.9693	0.5990	0.5373	0.086*
C12	0.9933 (2)	0.5946 (3)	0.6822 (5)	0.0975 (17)
H12A	1.0196	0.6373	0.6790	0.117*
C13	0.9849 (2)	0.5558 (4)	0.7704 (5)	0.1020 (19)
H13A	1.0054	0.5717	0.8273	0.122*
C14	0.9457 (2)	0.4926 (3)	0.7757 (4)	0.0911 (15)
H14A	0.9398	0.4657	0.8360	0.109*
C15	0.91552 (17)	0.4698 (2)	0.6912 (3)	0.0674 (12)
H15A	0.8886	0.4279	0.6947	0.081*
O3	0.78599 (12)	0.39116 (16)	0.7763 (2)	0.0807 (9)
O4	0.66106 (12)	0.42670 (16)	0.7850 (2)	0.0824 (9)
N2	0.65413 (13)	0.28816 (19)	0.7866 (2)	0.0596 (9)
Cl2	0.86828 (5)	0.23348 (8)	0.78394 (10)	0.1009 (5)
C16	0.69392 (17)	0.2242 (2)	0.7838 (3)	0.0512 (10)
C17	0.6827 (2)	0.1434 (2)	0.7823 (3)	0.0699 (12)
H17A	0.6444	0.1245	0.7811	0.084*
C18	0.7288 (2)	0.0906 (2)	0.7827 (3)	0.0789 (14)
H18A	0.7214	0.0355	0.7817	0.095*
C19	0.7861 (2)	0.1170 (3)	0.7845 (3)	0.0767 (14)
H19A	0.8167	0.0802	0.7859	0.092*
C20	0.79739 (17)	0.1997 (3)	0.7842 (3)	0.0633 (11)
C21	0.75154 (15)	0.2526 (2)	0.7840 (3)	0.0506 (10)
C22	0.74875 (18)	0.3404 (2)	0.7816 (3)	0.0551 (11)
C23	0.68310 (19)	0.3602 (3)	0.7847 (3)	0.0618 (11)
C24	0.59128 (16)	0.2818 (3)	0.7776 (3)	0.0758 (13)
H24A	0.5827	0.2432	0.7252	0.091*
H24B	0.5764	0.3336	0.7556	0.091*
C25	0.55801 (16)	0.2574 (2)	0.8702 (3)	0.0587 (11)
C26	0.58256 (16)	0.2129 (2)	0.9452 (3)	0.0647 (12)
H26A	0.6223	0.2009	0.9437	0.078*
C27	0.5485 (2)	0.1861 (3)	1.0228 (3)	0.0774 (13)
H27A	0.5653	0.1545	1.0727	0.093*
C28	0.4906 (2)	0.2049 (3)	1.0284 (4)	0.0900 (16)
H28A	0.4677	0.1864	1.0813	0.108*
C29	0.46671 (18)	0.2517 (3)	0.9539 (5)	0.0910 (16)
H29A	0.4275	0.2662	0.9573	0.109*
C30	0.49984 (18)	0.2771 (2)	0.8754 (3)	0.0736 (13)
H30A	0.4830	0.3079	0.8249	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0555 (7)	0.0927 (9)	0.1224 (10)	0.0131 (6)	0.0004 (7)	0.0070 (8)
C1	0.046 (2)	0.043 (2)	0.042 (2)	0.0025 (19)	0.001 (2)	−0.0029 (19)
N1	0.0396 (17)	0.0442 (18)	0.068 (2)	−0.0015 (15)	0.0006 (17)	−0.0029 (18)
O1	0.0652 (17)	0.0403 (16)	0.099 (2)	0.0090 (14)	−0.0063 (16)	−0.0039 (16)
O2	0.0551 (16)	0.0472 (16)	0.086 (2)	−0.0117 (14)	−0.0087 (16)	−0.0008 (15)
C2	0.059 (2)	0.048 (2)	0.050 (3)	0.007 (2)	0.001 (2)	−0.002 (2)
C3	0.077 (3)	0.052 (3)	0.064 (3)	0.018 (2)	0.000 (3)	0.001 (2)
C4	0.096 (3)	0.048 (3)	0.051 (3)	0.002 (3)	0.001 (3)	−0.002 (2)
C5	0.066 (3)	0.040 (2)	0.056 (3)	−0.008 (2)	0.007 (2)	0.002 (2)
C6	0.050 (2)	0.043 (2)	0.043 (2)	0.0059 (19)	−0.0061 (19)	−0.001 (2)
C7	0.049 (2)	0.043 (2)	0.056 (3)	−0.001 (2)	−0.009 (2)	−0.002 (2)
C8	0.050 (2)	0.046 (3)	0.050 (3)	−0.007 (2)	−0.010 (2)	−0.005 (2)
C9	0.055 (2)	0.054 (3)	0.063 (3)	−0.002 (2)	0.010 (2)	0.000 (2)
C10	0.045 (2)	0.055 (3)	0.058 (3)	0.0001 (19)	0.007 (2)	0.001 (2)
C11	0.056 (3)	0.071 (3)	0.089 (4)	−0.019 (2)	0.008 (3)	−0.004 (3)
C12	0.066 (3)	0.097 (4)	0.129 (5)	−0.017 (3)	−0.007 (4)	−0.031 (4)
C13	0.081 (4)	0.126 (5)	0.099 (5)	0.016 (4)	−0.041 (4)	−0.041 (4)
C14	0.100 (4)	0.100 (4)	0.073 (4)	0.022 (3)	−0.012 (3)	0.006 (3)
C15	0.070 (3)	0.056 (3)	0.076 (3)	0.004 (2)	−0.006 (3)	0.002 (3)
O3	0.090 (2)	0.0580 (18)	0.095 (2)	−0.0212 (17)	0.0114 (19)	0.0033 (18)
O4	0.107 (2)	0.0579 (18)	0.082 (2)	0.0191 (17)	0.0051 (19)	0.0061 (18)
N2	0.057 (2)	0.059 (2)	0.063 (2)	−0.0011 (18)	0.003 (2)	0.003 (2)
Cl2	0.0643 (7)	0.1260 (11)	0.1124 (11)	0.0158 (8)	0.0084 (8)	0.0130 (9)
C16	0.068 (3)	0.042 (2)	0.044 (2)	−0.002 (2)	0.000 (2)	−0.001 (2)
C17	0.097 (3)	0.053 (3)	0.060 (3)	−0.018 (3)	0.010 (3)	−0.008 (3)
C18	0.137 (5)	0.039 (3)	0.060 (3)	0.003 (3)	0.008 (3)	0.000 (2)
C19	0.105 (4)	0.070 (3)	0.055 (3)	0.031 (3)	0.007 (3)	−0.002 (3)
C20	0.072 (3)	0.066 (3)	0.052 (3)	0.011 (2)	0.009 (2)	0.001 (2)
C21	0.061 (2)	0.044 (2)	0.047 (2)	−0.004 (2)	0.003 (2)	−0.0032 (19)
C22	0.073 (3)	0.048 (3)	0.044 (2)	−0.007 (2)	0.006 (2)	0.000 (2)
C23	0.084 (3)	0.052 (3)	0.049 (3)	0.008 (3)	0.007 (2)	0.000 (3)
C24	0.064 (3)	0.099 (3)	0.065 (3)	−0.002 (2)	−0.018 (3)	0.006 (3)
C25	0.047 (2)	0.069 (3)	0.060 (3)	0.002 (2)	−0.010 (2)	−0.005 (2)
C26	0.055 (3)	0.088 (3)	0.051 (3)	0.007 (2)	−0.002 (2)	−0.003 (3)
C27	0.087 (3)	0.082 (3)	0.063 (3)	0.012 (3)	0.012 (3)	−0.001 (3)
C28	0.090 (4)	0.092 (4)	0.088 (4)	−0.016 (3)	0.035 (3)	−0.023 (3)
C29	0.055 (3)	0.091 (4)	0.128 (5)	−0.001 (3)	0.011 (4)	−0.024 (4)
C30	0.057 (3)	0.074 (3)	0.090 (4)	0.002 (2)	−0.021 (3)	0.002 (3)

Geometric parameters (Å, º) top

Cl1—C2	1.710 (4)	O3—C22	1.200 (4)
C1—C2	1.383 (4)	O4—C23	1.213 (4)
C1—C6	1.394 (4)	N2—C23	1.368 (4)
C1—C8	1.465 (4)	N2—C16	1.399 (4)
N1—C7	1.359 (4)	N2—C24	1.446 (4)
N1—C6	1.407 (4)	Cl2—C20	1.715 (4)
N1—C9	1.444 (4)	C16—C17	1.366 (4)
O1—C7	1.202 (4)	C16—C21	1.399 (4)
O2—C8	1.201 (4)	C17—C18	1.372 (5)
C2—C3	1.382 (4)	C17—H17A	0.9300
C3—C4	1.378 (5)	C18—C19	1.381 (5)
C3—H3A	0.9300	C18—H18A	0.9300
C4—C5	1.369 (5)	C19—C20	1.397 (5)
C4—H4A	0.9300	C19—H19A	0.9300
C5—C6	1.379 (4)	C20—C21	1.368 (5)
C5—H5A	0.9300	C21—C22	1.459 (5)
C7—C8	1.558 (4)	C22—C23	1.537 (5)
C9—C10	1.496 (5)	C24—C25	1.506 (5)
C9—H9A	0.9700	C24—H24A	0.9700
C9—H9B	0.9700	C24—H24B	0.9700
C10—C15	1.365 (5)	C25—C26	1.364 (5)
C10—C11	1.378 (4)	C25—C30	1.371 (5)
C11—C12	1.374 (6)	C26—C27	1.369 (5)
C11—H11A	0.9300	C26—H26A	0.9300
C12—C13	1.354 (6)	C27—C28	1.363 (5)
C12—H12A	0.9300	C27—H27A	0.9300
C13—C14	1.381 (6)	C28—C29	1.374 (6)
C13—H13A	0.9300	C28—H28A	0.9300
C14—C15	1.375 (5)	C29—C30	1.359 (5)
C14—H14A	0.9300	C29—H29A	0.9300
C15—H15A	0.9300	C30—H30A	0.9300

C2—C1—C6	119.8 (3)	C23—N2—C16	110.4 (3)
C2—C1—C8	132.7 (3)	C23—N2—C24	122.9 (4)
C6—C1—C8	107.5 (3)	C16—N2—C24	126.1 (3)
C7—N1—C6	111.6 (3)	C17—C16—N2	128.6 (4)
C7—N1—C9	123.8 (3)	C17—C16—C21	120.6 (4)
C6—N1—C9	124.6 (3)	N2—C16—C21	110.9 (3)
C3—C2—C1	119.5 (3)	C16—C17—C18	118.8 (4)
C3—C2—Cl1	119.8 (3)	C16—C17—H17A	120.6
C1—C2—Cl1	120.7 (3)	C18—C17—H17A	120.6
C4—C3—C2	118.9 (4)	C17—C18—C19	121.8 (4)
C4—C3—H3A	120.5	C17—C18—H18A	119.1
C2—C3—H3A	120.5	C19—C18—H18A	119.1
C5—C4—C3	123.1 (4)	C18—C19—C20	119.2 (4)
C5—C4—H4A	118.4	C18—C19—H19A	120.4
C3—C4—H4A	118.4	C20—C19—H19A	120.4
C4—C5—C6	117.4 (4)	C21—C20—C19	119.3 (4)
C4—C5—H5A	121.3	C21—C20—Cl2	121.0 (3)
C6—C5—H5A	121.3	C19—C20—Cl2	119.7 (4)
C5—C6—C1	121.2 (3)	C20—C21—C16	120.3 (4)
C5—C6—N1	128.4 (3)	C20—C21—C22	132.4 (4)
C1—C6—N1	110.4 (3)	C16—C21—C22	107.2 (3)
O1—C7—N1	128.5 (3)	O3—C22—C21	132.2 (4)
O1—C7—C8	125.9 (3)	O3—C22—C23	123.0 (4)
N1—C7—C8	105.6 (3)	C21—C22—C23	104.8 (3)
O2—C8—C1	132.3 (4)	O4—C23—N2	126.5 (4)
O2—C8—C7	123.0 (3)	O4—C23—C22	126.9 (4)
C1—C8—C7	104.8 (3)	N2—C23—C22	106.6 (3)
N1—C9—C10	113.7 (3)	N2—C24—C25	117.0 (3)
N1—C9—H9A	108.8	N2—C24—H24A	108.1
C10—C9—H9A	108.8	C25—C24—H24A	108.1
N1—C9—H9B	108.8	N2—C24—H24B	108.1
C10—C9—H9B	108.8	C25—C24—H24B	108.1
H9A—C9—H9B	107.7	H24A—C24—H24B	107.3
C15—C10—C11	119.7 (4)	C26—C25—C30	119.4 (4)
C15—C10—C9	120.4 (4)	C26—C25—C24	122.7 (4)
C11—C10—C9	119.8 (4)	C30—C25—C24	117.9 (4)
C12—C11—C10	119.5 (4)	C25—C26—C27	119.8 (4)
C12—C11—H11A	120.2	C25—C26—H26A	120.1
C10—C11—H11A	120.2	C27—C26—H26A	120.1
C13—C12—C11	120.8 (5)	C28—C27—C26	121.3 (5)
C13—C12—H12A	119.6	C28—C27—H27A	119.4
C11—C12—H12A	119.6	C26—C27—H27A	119.4
C12—C13—C14	119.8 (5)	C27—C28—C29	118.4 (5)
C12—C13—H13A	120.1	C27—C28—H28A	120.8
C14—C13—H13A	120.1	C29—C28—H28A	120.8
C15—C14—C13	119.5 (5)	C30—C29—C28	120.7 (4)
C15—C14—H14A	120.2	C30—C29—H29A	119.6
C13—C14—H14A	120.2	C28—C29—H29A	119.6
C10—C15—C14	120.5 (4)	C29—C30—C25	120.4 (4)
C10—C15—H15A	119.8	C29—C30—H30A	119.8
C14—C15—H15A	119.8	C25—C30—H30A	119.8

C6—C1—C2—C3	−1.2 (6)	C23—N2—C16—C17	−178.5 (4)
C8—C1—C2—C3	177.0 (4)	C24—N2—C16—C17	−7.2 (6)
C6—C1—C2—Cl1	179.7 (3)	C23—N2—C16—C21	2.4 (5)
C8—C1—C2—Cl1	−2.1 (6)	C24—N2—C16—C21	173.7 (4)
C1—C2—C3—C4	−0.5 (6)	N2—C16—C17—C18	−178.0 (4)
Cl1—C2—C3—C4	178.6 (3)	C21—C16—C17—C18	1.1 (6)
C2—C3—C4—C5	1.7 (6)	C16—C17—C18—C19	0.0 (7)
C3—C4—C5—C6	−1.1 (6)	C17—C18—C19—C20	−1.1 (7)
C4—C5—C6—C1	−0.7 (6)	C18—C19—C20—C21	1.2 (7)
C4—C5—C6—N1	−179.5 (3)	C18—C19—C20—Cl2	−178.7 (4)
C2—C1—C6—C5	1.8 (6)	C19—C20—C21—C16	−0.1 (6)
C8—C1—C6—C5	−176.8 (3)	Cl2—C20—C21—C16	179.7 (3)
C2—C1—C6—N1	−179.2 (3)	C19—C20—C21—C22	−178.6 (4)
C8—C1—C6—N1	2.2 (4)	Cl2—C20—C21—C22	1.3 (7)
C7—N1—C6—C5	176.6 (4)	C17—C16—C21—C20	−1.0 (6)
C9—N1—C6—C5	−3.8 (6)	N2—C16—C21—C20	178.2 (4)
C7—N1—C6—C1	−2.4 (4)	C17—C16—C21—C22	177.8 (3)
C9—N1—C6—C1	177.2 (3)	N2—C16—C21—C22	−3.0 (5)
C6—N1—C7—O1	−179.3 (4)	C20—C21—C22—O3	2.6 (8)
C9—N1—C7—O1	1.1 (6)	C16—C21—C22—O3	−176.0 (4)
C6—N1—C7—C8	1.4 (4)	C20—C21—C22—C23	−179.0 (4)
C9—N1—C7—C8	−178.2 (3)	C16—C21—C22—C23	2.4 (4)
C2—C1—C8—O2	−0.8 (8)	C16—N2—C23—O4	179.0 (4)
C6—C1—C8—O2	177.5 (4)	C24—N2—C23—O4	7.4 (7)
C2—C1—C8—C7	−179.6 (4)	C16—N2—C23—C22	−0.8 (4)
C6—C1—C8—C7	−1.3 (4)	C24—N2—C23—C22	−172.4 (3)
O1—C7—C8—O2	1.7 (6)	O3—C22—C23—O4	−2.2 (7)
N1—C7—C8—O2	−179.0 (3)	C21—C22—C23—O4	179.2 (4)
O1—C7—C8—C1	−179.3 (4)	O3—C22—C23—N2	177.6 (4)
N1—C7—C8—C1	−0.1 (4)	C21—C22—C23—N2	−1.0 (4)
C7—N1—C9—C10	−102.9 (4)	C23—N2—C24—C25	−109.5 (4)
C6—N1—C9—C10	77.5 (4)	C16—N2—C24—C25	80.3 (5)
N1—C9—C10—C15	49.4 (5)	N2—C24—C25—C26	−25.9 (6)
N1—C9—C10—C11	−131.1 (3)	N2—C24—C25—C30	158.0 (4)
C15—C10—C11—C12	1.2 (6)	C30—C25—C26—C27	2.3 (6)
C9—C10—C11—C12	−178.3 (4)	C24—C25—C26—C27	−173.8 (4)
C10—C11—C12—C13	−0.3 (7)	C25—C26—C27—C28	−1.9 (6)
C11—C12—C13—C14	−0.2 (8)	C26—C27—C28—C29	0.0 (7)
C12—C13—C14—C15	−0.1 (7)	C27—C28—C29—C30	1.5 (7)
C11—C10—C15—C14	−1.6 (6)	C28—C29—C30—C25	−1.1 (7)
C9—C10—C15—C14	177.9 (4)	C26—C25—C30—C29	−0.8 (6)
C13—C14—C15—C10	1.1 (7)	C24—C25—C30—C29	175.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1ⁱ	0.93	2.58	3.228 (4)	127
C4—H4A···O2ⁱ	0.93	2.56	3.473 (4)	167
C18—H18A···O3ⁱⁱ	0.93	2.40	3.329 (4)	173
C19—H19A···O4ⁱⁱ	0.93	2.60	3.382 (6)	142
C26—H26A···O2ⁱⁱⁱ	0.93	2.59	3.350 (4)	140
C29—H29A···O1^iv	0.93	2.59	3.505 (5)	169

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀ClNO₂
M_r	271.69
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	22.864 (5), 16.600 (3), 13.335 (3)
V (Å³)	5061.2 (18)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.916, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	4623, 4623, 1929
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.117, 1.00
No. of reflections	4623
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1ⁱ	0.93	2.58	3.228 (4)	127
C4—H4A···O2ⁱ	0.93	2.56	3.473 (4)	167
C18—H18A···O3ⁱⁱ	0.93	2.40	3.329 (4)	173
C19—H19A···O4ⁱⁱ	0.93	2.60	3.382 (6)	142
C26—H26A···O2ⁱⁱⁱ	0.93	2.59	3.350 (4)	140
C29—H29A···O1^iv	0.93	2.59	3.505 (5)	169

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

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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