Structures and phase transition of three isomers of 1-phenyl­indolin-2-one derivatives: 6-chloro-1-phenyl­indolin-2-one, 4-chloro-1-phenyl­indolin-2-one and 1-(3-chloro­phen­yl)indolin-2-one

Three 1-phenyl­indolin-2-one derivatives, namely 6-chloro-1-phenyl­indolin-2-one (A), 4-chloro-1-phenyl­indolin-2-one (B) and 1-(3-chloro­phen­yl)indolin-2-one (C), all C₁₄H₁₀ClNO, have been synthesized and the structures of these compounds at room temperature (A_RT, B_RT and C_RT) and low temperature (A_LT, B_LT and C_LT) have been determined. Crystal A at 295 K (A_RT) crystallized in the monoclinic space group P2₁/c and the phenyl ring of the unique mol­ecule exhibits disorder over two positions. At low temperature, the disorder disappeared and crystal A at 90 K (A_LT) crystallized in the triclinic space group P with a doubled unit-cell volume and four mol­ecules in the asymmetric unit. Density functional theory (DFT) calculations revealed a low oscillation barrier (0.24 kcal mol⁻¹) of the phenyl ring of mol­ecule A and the phase transition from the P2₁/c structure to the P structure can be inter­preted in terms of the freezing out of the two conformations at low temperature. Crystal B retains space group P2₁/c in the temperature range from 100 to 297 K. A kind of obtuse-cell to acute-cell change can be recognized; if the unit cell of B_LT at 100 K is set to be a standard obtuse cell [β = 90.341 (2)°] and the cell is kept untransformed in the course of temperature changing, the cell of B_RT at 297 K was found to be acute [β = 89.288 (2)°]. The mol­ecules in structure C are packed in layers, with C—H...O hydrogen bonds between neighbouring layers.

Computing details

Data collection: APEX2 (Bruker, 2005) for A_LT, C_RT; Bruker APEX2 for A_RT, B_LT, B_RT, C_LT. Cell refinement: SAINT (Bruker, 2005) for A_LT, C_RT; Bruker SAINT for A_RT, B_LT, B_RT, C_LT. Data reduction: SAINT (Bruker, 2005) for A_LT, C_RT; Bruker SAINT for A_RT, B_LT, B_RT, C_LT. For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick 2008). Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) for A_LT, C_RT; SHELXL2014/7 (Sheldrick, 2015) for A_RT, B_LT, B_RT, C_LT. Molecular graphics: SHELXTL (Sheldrick 2008) and Mercury (Macrae et al.,2008) for A_LT, C_RT; Bruker SHELXTL and Mercury (Macrae et al.,2008) for A_RT, B_LT, B_RT, C_LT. Software used to prepare material for publication: SHELXTL (Sheldrick 2008) and publCIF (Westrip, 2010) for A_LT, C_RT; Bruker SHELXTL and publCIF (Westrip, 2010) for A_RT, B_LT, B_RT, C_LT.

6-Chloro-1-phenylindolin-2-one (A_LT)

Crystal data

C14H10ClNO	Z = 8
Mr = 243.68	F(000) = 1008
Triclinic, P1	Dx = 1.428 Mg m^−3
a = 9.6212 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.4483 (7) Å	Cell parameters from 9973 reflections
c = 19.7967 (10) Å	θ = 2.3–30.2°
α = 72.681 (1)°	µ = 0.32 mm^−1
β = 89.995 (1)°	T = 90 K
γ = 69.051 (1)°	Block, colorless
V = 2267.4 (2) Å^3	0.38 × 0.32 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer	11212 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm^-1	Rint = 0.028
ω scans	θmax = 30.2°, θmin = 1.1°
Absorption correction: multi-scan (APEX2; Bruker, 2005)	h = −13→13
Tmin = 0.889, Tmax = 0.951	k = −19→18
45213 measured reflections	l = −27→28
12930 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	All H-atom parameters refined
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 0.2422P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
12930 reflections	Δρmax = 0.47 e Å^−3
770 parameters	Δρmin = −0.31 e Å^−3

Special details

Experimental. Scan width 0.5° ω , Crystal to detector distance 5.964 cm, exposure time 18s, 13.8 hours for data collection.In addtion to multi-scan absorption correction,scale procedure has been carried out. The 6 omiga-run take the following theta, initial-omiga, phi values and the following sweep-ranges, respectively. -28, -28, 0, 186 (negatively run) -28, 146, 72, 186 (positively run) -30, -28, 144, 186 (negatively run) -31, 146, 216, 186 (positively run) -33, -28, 288, 200 (negatively run) -33, -28, 90, 180 (negatively run)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2867 (3)	0.21744 (17)	0.16306 (10)	0.0158 (5)
C2	0.3409 (3)	0.11604 (18)	0.22960 (10)	0.0147 (5)
C3	0.4820 (3)	0.03907 (17)	0.21151 (9)	0.0149 (4)
C4	0.5834 (3)	−0.06659 (17)	0.24935 (10)	0.0148 (4)
C5	0.7079 (3)	−0.11853 (17)	0.21809 (10)	0.0161 (5)
C6	0.7249 (3)	−0.06289 (16)	0.14888 (10)	0.0152 (4)
C7	0.6254 (3)	0.04321 (17)	0.10909 (9)	0.0150 (5)
C8	0.5036 (3)	0.09215 (16)	0.14199 (9)	0.0121 (4)
C9	0.3755 (3)	0.27299 (16)	0.04356 (9)	0.0137 (4)
C10	0.2666 (2)	0.28606 (16)	−0.00838 (9)	0.0203 (4)
C11	0.2507 (2)	0.36267 (18)	−0.07553 (10)	0.0248 (5)
C12	0.3409 (3)	0.42542 (19)	−0.09043 (11)	0.0230 (5)
C13	0.4493 (2)	0.40975 (15)	−0.03871 (9)	0.0200 (4)
C14	0.4659 (2)	0.33411 (15)	0.02875 (9)	0.0171 (4)
Cl1	0.87866 (8)	−0.12995 (4)	0.10994 (2)	0.01864 (12)
N1	0.3867 (3)	0.19695 (13)	0.11401 (8)	0.0146 (4)
O1	0.1770 (2)	0.30357 (12)	0.15250 (7)	0.0222 (3)
H4	0.574 (3)	−0.1028 (17)	0.2970 (10)	0.024 (6)*
H5	0.774 (3)	−0.1910 (18)	0.2449 (10)	0.022 (6)*
H7	0.645 (3)	0.0817 (17)	0.0609 (10)	0.024 (5)*
H10	0.203 (3)	0.2456 (18)	0.0018 (11)	0.033 (6)*
H11	0.171 (3)	0.3747 (18)	−0.1104 (11)	0.036 (6)*
H12	0.317 (3)	0.4835 (18)	−0.1359 (11)	0.028 (6)*
H13	0.515 (2)	0.4500 (17)	−0.0481 (10)	0.026 (5)*
H14	0.535 (3)	0.3253 (18)	0.0645 (10)	0.031 (6)*
H2B	0.364 (3)	0.1394 (16)	0.2669 (10)	0.017 (5)*
H2A	0.273 (3)	0.0796 (18)	0.2436 (10)	0.020*
C21	0.8146 (3)	0.20245 (17)	0.16916 (10)	0.0149 (4)
C22	0.8716 (3)	0.09776 (17)	0.23351 (10)	0.0145 (4)
C23	1.0080 (3)	0.02145 (17)	0.21084 (10)	0.0138 (4)
C24	1.1117 (3)	−0.08342 (16)	0.24614 (9)	0.0147 (4)
C25	1.2331 (3)	−0.13302 (17)	0.21223 (10)	0.0150 (4)
C26	1.2444 (3)	−0.07476 (16)	0.14246 (9)	0.0140 (4)
C27	1.1400 (3)	0.03106 (16)	0.10449 (9)	0.0137 (4)
C28	1.0207 (3)	0.07716 (16)	0.14048 (9)	0.0125 (4)
C29	0.8828 (3)	0.26161 (16)	0.04554 (9)	0.0132 (4)
C30	0.8476 (2)	0.23351 (15)	−0.01278 (9)	0.0164 (4)
C31	0.8214 (2)	0.31207 (16)	−0.08046 (9)	0.0193 (4)
C32	0.8290 (3)	0.41622 (19)	−0.08909 (11)	0.0209 (5)
C33	0.8643 (2)	0.44282 (15)	−0.03061 (9)	0.0190 (4)
C34	0.8918 (2)	0.36461 (15)	0.03751 (9)	0.0161 (4)
Cl2	1.39793 (7)	−0.13603 (4)	0.10140 (2)	0.01704 (11)
N2	0.9049 (3)	0.18261 (13)	0.11587 (8)	0.0132 (4)
O2	0.7097 (2)	0.28920 (12)	0.16316 (7)	0.0201 (4)
H24	1.112 (2)	−0.1228 (15)	0.2941 (9)	0.014 (5)*
H25	1.298 (3)	−0.207 (2)	0.2356 (11)	0.029 (6)*
H27	1.152 (4)	0.0735 (18)	0.0542 (11)	0.035*
H30	0.843 (2)	0.1602 (16)	−0.0062 (9)	0.017 (5)*
H31	0.800 (2)	0.2896 (15)	−0.1184 (9)	0.015 (5)*
H32	0.804 (3)	0.4743 (16)	−0.1362 (10)	0.018 (6)*
H33	0.867 (2)	0.5123 (16)	−0.0342 (9)	0.022 (5)*
H34	0.914 (2)	0.3808 (15)	0.0766 (9)	0.013 (5)*
H22A	0.800 (3)	0.0641 (16)	0.2465 (10)	0.016*
H22B	0.900 (2)	0.1158 (14)	0.2719 (9)	0.009 (5)*
C41	0.5162 (3)	0.29434 (17)	0.33062 (9)	0.0148 (4)
C42	0.4681 (3)	0.39964 (18)	0.26548 (10)	0.0146 (4)
C43	0.5276 (3)	0.47495 (16)	0.28759 (9)	0.0121 (4)
C44	0.5278 (3)	0.58049 (17)	0.25115 (9)	0.0161 (4)
C45	0.5986 (3)	0.62997 (18)	0.28463 (10)	0.0165 (4)
C46	0.6675 (3)	0.57407 (16)	0.35372 (9)	0.0133 (4)
C47	0.6679 (3)	0.46825 (16)	0.39238 (10)	0.0132 (4)
C48	0.5989 (3)	0.42123 (16)	0.35759 (9)	0.0126 (4)
C49	0.6411 (3)	0.23703 (16)	0.45317 (9)	0.0132 (4)
C50	0.5795 (2)	0.26423 (15)	0.51157 (9)	0.0162 (4)
C51	0.6324 (2)	0.18647 (17)	0.57956 (9)	0.0192 (4)
C52	0.7445 (3)	0.08334 (18)	0.58807 (10)	0.0182 (5)
C53	0.8074 (2)	0.05670 (15)	0.52943 (9)	0.0195 (4)
C54	0.7571 (2)	0.13392 (15)	0.46154 (9)	0.0166 (4)
Cl3	0.75702 (8)	0.63669 (4)	0.39429 (3)	0.01786 (12)
N3	0.5868 (3)	0.31493 (14)	0.38306 (8)	0.0133 (4)
O3	0.4955 (2)	0.20782 (12)	0.33728 (7)	0.0210 (4)
H44	0.470 (3)	0.6225 (16)	0.2014 (10)	0.020 (6)*
H45	0.610 (3)	0.7006 (19)	0.2555 (10)	0.026 (6)*
H47	0.707 (3)	0.4348 (18)	0.4391 (11)	0.031*
H50	0.500 (2)	0.3326 (16)	0.5045 (9)	0.019 (5)*
H51	0.582 (2)	0.2051 (16)	0.6178 (10)	0.021 (5)*
H52	0.801 (3)	0.0223 (18)	0.6355 (11)	0.029 (6)*
H53	0.882 (2)	−0.0156 (15)	0.5352 (9)	0.015 (5)*
H54	0.796 (2)	0.1186 (15)	0.4214 (9)	0.013 (4)*
H42B	0.496 (3)	0.3845 (18)	0.2199 (11)	0.031 (6)*
H42A	0.356 (3)	0.4227 (19)	0.2617 (11)	0.029 (6)*
C61	0.0068 (3)	0.28499 (17)	0.33803 (9)	0.0160 (5)
C62	−0.0403 (3)	0.38884 (18)	0.27152 (10)	0.0158 (5)
C63	0.0237 (3)	0.46422 (16)	0.29103 (9)	0.0121 (4)
C64	0.0211 (3)	0.57014 (17)	0.25488 (9)	0.0161 (4)
C65	0.0933 (3)	0.62025 (17)	0.28724 (10)	0.0152 (4)
C66	0.1666 (3)	0.56337 (16)	0.35529 (9)	0.0141 (4)
C67	0.1703 (3)	0.45679 (17)	0.39420 (10)	0.0135 (4)
C68	0.0994 (3)	0.40989 (16)	0.36034 (9)	0.0134 (4)
C69	0.1443 (3)	0.22764 (16)	0.45795 (9)	0.0143 (4)
C70	0.0513 (2)	0.21653 (16)	0.50978 (9)	0.0212 (4)
C71	0.1098 (2)	0.13908 (18)	0.57723 (9)	0.0256 (5)
C72	0.2610 (3)	0.07568 (18)	0.59221 (10)	0.0202 (5)
C73	0.3565 (2)	0.08915 (16)	0.54019 (10)	0.0209 (4)
C74	0.2990 (2)	0.16497 (16)	0.47246 (9)	0.0186 (4)
Cl4	0.25518 (8)	0.62717 (4)	0.39532 (3)	0.01752 (11)
N4	0.0858 (3)	0.30472 (14)	0.38786 (8)	0.0144 (4)
O4	−0.0187 (2)	0.19957 (12)	0.34720 (7)	0.0225 (3)
H64	−0.042 (3)	0.6116 (16)	0.2045 (10)	0.022 (6)*
H65	0.103 (3)	0.694 (2)	0.2585 (11)	0.038 (7)*
H67	0.211 (3)	0.4221 (16)	0.4393 (10)	0.016 (5)*
H70	−0.051 (3)	0.2640 (19)	0.4983 (12)	0.044 (7)*
H71	0.048 (2)	0.1317 (17)	0.6134 (10)	0.027 (5)*
H73	0.465 (2)	0.0441 (17)	0.5500 (10)	0.028 (6)*
H74	0.367 (2)	0.1757 (16)	0.4354 (10)	0.024 (5)*
H62A	−0.155 (3)	0.4128 (17)	0.2663 (10)	0.019 (5)*
H62B	−0.006 (3)	0.3664 (18)	0.2271 (10)	0.027 (6)*
H72	0.319 (3)	0.0144 (15)	0.6385 (9)	0.013 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0138 (11)	0.0191 (10)	0.0145 (8)	−0.0057 (8)	0.0026 (7)	−0.0060 (8)
C2	0.0140 (11)	0.0182 (10)	0.0123 (8)	−0.0058 (8)	0.0039 (7)	−0.0058 (7)
C3	0.0159 (11)	0.0174 (10)	0.0147 (8)	−0.0093 (9)	0.0022 (7)	−0.0061 (7)
C4	0.0169 (11)	0.0157 (9)	0.0128 (8)	−0.0092 (8)	0.0004 (7)	−0.0024 (7)
C5	0.0189 (12)	0.0129 (9)	0.0148 (8)	−0.0068 (8)	−0.0013 (8)	−0.0013 (7)
C6	0.0134 (10)	0.0147 (9)	0.0196 (8)	−0.0057 (8)	0.0019 (8)	−0.0079 (7)
C7	0.0171 (12)	0.0150 (9)	0.0128 (8)	−0.0060 (9)	0.0020 (8)	−0.0042 (7)
C8	0.0110 (10)	0.0120 (8)	0.0127 (8)	−0.0036 (8)	0.0000 (7)	−0.0039 (7)
C9	0.0138 (11)	0.0126 (9)	0.0095 (8)	−0.0005 (9)	0.0014 (8)	−0.0017 (7)
C10	0.0197 (10)	0.0232 (10)	0.0205 (9)	−0.0096 (8)	0.0018 (7)	−0.0085 (8)
C11	0.0255 (12)	0.0329 (12)	0.0144 (9)	−0.0091 (10)	−0.0009 (8)	−0.0076 (8)
C12	0.0281 (15)	0.0214 (11)	0.0148 (9)	−0.0054 (10)	0.0092 (9)	−0.0040 (8)
C13	0.0174 (10)	0.0187 (9)	0.0221 (9)	−0.0067 (8)	0.0077 (7)	−0.0040 (7)
C14	0.0124 (9)	0.0181 (9)	0.0181 (8)	−0.0039 (8)	0.0009 (7)	−0.0042 (7)
Cl1	0.0161 (3)	0.0178 (2)	0.0208 (2)	−0.0034 (2)	0.0028 (2)	−0.00805 (19)
N1	0.0155 (10)	0.0126 (8)	0.0119 (7)	−0.0027 (7)	0.0026 (7)	−0.0017 (6)
O1	0.0208 (9)	0.0215 (7)	0.0178 (6)	−0.0014 (7)	0.0052 (6)	−0.0049 (5)
C21	0.0137 (10)	0.0182 (9)	0.0133 (8)	−0.0058 (8)	0.0022 (7)	−0.0060 (7)
C22	0.0166 (10)	0.0163 (9)	0.0121 (8)	−0.0064 (9)	0.0037 (7)	−0.0062 (7)
C23	0.0151 (10)	0.0149 (9)	0.0149 (8)	−0.0080 (8)	0.0033 (7)	−0.0066 (7)
C24	0.0181 (11)	0.0147 (9)	0.0115 (8)	−0.0082 (9)	0.0001 (7)	−0.0018 (7)
C25	0.0170 (11)	0.0100 (9)	0.0153 (8)	−0.0040 (8)	−0.0009 (8)	−0.0015 (7)
C26	0.0132 (11)	0.0139 (9)	0.0171 (8)	−0.0056 (8)	0.0022 (7)	−0.0072 (7)
C27	0.0150 (11)	0.0129 (9)	0.0128 (8)	−0.0053 (8)	0.0022 (8)	−0.0035 (7)
C28	0.0136 (10)	0.0124 (9)	0.0125 (8)	−0.0054 (8)	0.0004 (8)	−0.0047 (7)
C29	0.0093 (10)	0.0137 (9)	0.0100 (8)	0.0008 (8)	0.0005 (8)	−0.0009 (7)
C30	0.0142 (9)	0.0165 (9)	0.0177 (8)	−0.0036 (7)	0.0042 (6)	−0.0070 (7)
C31	0.0152 (10)	0.0244 (10)	0.0140 (8)	−0.0022 (8)	0.0004 (7)	−0.0062 (7)
C32	0.0181 (13)	0.0219 (11)	0.0148 (9)	−0.0014 (10)	0.0051 (8)	−0.0020 (8)
C33	0.0165 (10)	0.0152 (9)	0.0203 (9)	−0.0032 (8)	0.0023 (7)	−0.0017 (7)
C34	0.0142 (9)	0.0151 (9)	0.0166 (8)	−0.0029 (7)	0.0003 (7)	−0.0050 (7)
Cl2	0.0150 (3)	0.0158 (2)	0.0183 (2)	−0.0027 (2)	0.0033 (2)	−0.00628 (18)
N2	0.0147 (9)	0.0123 (7)	0.0102 (7)	−0.0034 (7)	0.0020 (7)	−0.0023 (6)
O2	0.0154 (8)	0.0216 (7)	0.0186 (6)	−0.0006 (6)	0.0046 (6)	−0.0076 (6)
C41	0.0140 (10)	0.0191 (10)	0.0120 (8)	−0.0061 (8)	0.0031 (7)	−0.0060 (7)
C42	0.0167 (10)	0.0155 (9)	0.0099 (7)	−0.0049 (8)	0.0007 (7)	−0.0029 (7)
C43	0.0126 (10)	0.0128 (9)	0.0085 (8)	−0.0029 (8)	0.0021 (7)	−0.0023 (7)
C44	0.0164 (10)	0.0158 (9)	0.0117 (8)	−0.0029 (8)	0.0021 (8)	−0.0020 (7)
C45	0.0171 (11)	0.0123 (9)	0.0172 (9)	−0.0040 (9)	0.0044 (8)	−0.0024 (7)
C46	0.0133 (11)	0.0133 (9)	0.0138 (8)	−0.0055 (8)	0.0026 (7)	−0.0043 (7)
C47	0.0119 (11)	0.0130 (9)	0.0129 (8)	−0.0035 (8)	0.0018 (7)	−0.0031 (7)
C48	0.0132 (11)	0.0114 (9)	0.0108 (8)	−0.0034 (8)	0.0030 (8)	−0.0018 (7)
C49	0.0127 (11)	0.0127 (9)	0.0126 (8)	−0.0049 (8)	−0.0024 (8)	−0.0015 (7)
C50	0.0157 (8)	0.0178 (9)	0.0155 (8)	−0.0070 (7)	0.0015 (6)	−0.0048 (7)
C51	0.0260 (9)	0.0252 (10)	0.0123 (8)	−0.0158 (8)	0.0028 (7)	−0.0065 (7)
C52	0.0256 (12)	0.0191 (10)	0.0129 (8)	−0.0167 (9)	−0.0005 (8)	0.0010 (8)
C53	0.0224 (9)	0.0148 (9)	0.0201 (8)	−0.0082 (7)	−0.0015 (7)	−0.0024 (7)
C54	0.0193 (9)	0.0138 (9)	0.0161 (8)	−0.0064 (7)	0.0023 (7)	−0.0037 (7)
Cl3	0.0214 (3)	0.0159 (2)	0.0187 (2)	−0.0094 (2)	0.0023 (2)	−0.00604 (18)
N3	0.0164 (10)	0.0137 (8)	0.0104 (7)	−0.0077 (7)	0.0007 (7)	−0.0020 (6)
O3	0.0292 (9)	0.0193 (7)	0.0179 (6)	−0.0135 (7)	0.0010 (6)	−0.0051 (5)
C61	0.0184 (11)	0.0188 (10)	0.0128 (8)	−0.0071 (9)	0.0028 (7)	−0.0077 (7)
C62	0.0176 (11)	0.0174 (10)	0.0115 (8)	−0.0059 (8)	0.0004 (8)	−0.0044 (7)
C63	0.0116 (10)	0.0145 (9)	0.0099 (8)	−0.0040 (8)	0.0020 (7)	−0.0046 (7)
C64	0.0167 (11)	0.0177 (9)	0.0107 (7)	−0.0043 (9)	0.0002 (8)	−0.0025 (7)
C65	0.0176 (11)	0.0123 (9)	0.0146 (8)	−0.0057 (8)	0.0029 (8)	−0.0028 (7)
C66	0.0139 (11)	0.0159 (9)	0.0136 (8)	−0.0061 (8)	0.0014 (7)	−0.0059 (7)
C67	0.0121 (11)	0.0138 (9)	0.0122 (8)	−0.0033 (8)	0.0001 (7)	−0.0028 (7)
C68	0.0125 (11)	0.0118 (9)	0.0118 (8)	−0.0013 (8)	0.0009 (8)	−0.0020 (7)
C69	0.0162 (11)	0.0134 (9)	0.0130 (8)	−0.0057 (9)	−0.0011 (8)	−0.0036 (7)
C70	0.0191 (9)	0.0237 (10)	0.0152 (8)	−0.0024 (8)	0.0017 (7)	−0.0049 (7)
C71	0.0309 (11)	0.0312 (12)	0.0140 (8)	−0.0123 (9)	0.0080 (8)	−0.0054 (8)
C72	0.0298 (13)	0.0194 (10)	0.0130 (8)	−0.0141 (10)	−0.0009 (9)	−0.0015 (8)
C73	0.0200 (9)	0.0201 (10)	0.0208 (9)	−0.0088 (8)	−0.0042 (7)	−0.0022 (7)
C74	0.0173 (9)	0.0200 (10)	0.0187 (9)	−0.0093 (7)	0.0031 (7)	−0.0036 (7)
Cl4	0.0210 (3)	0.0170 (2)	0.0179 (2)	−0.0101 (2)	0.00083 (19)	−0.00660 (18)
N4	0.0184 (10)	0.0140 (8)	0.0115 (7)	−0.0081 (8)	−0.0006 (7)	−0.0027 (6)
O4	0.0321 (9)	0.0206 (7)	0.0196 (7)	−0.0156 (7)	0.0004 (6)	−0.0062 (6)

Geometric parameters (Å, º)

C1—O1	1.217 (3)	C41—O3	1.219 (3)
C1—N1	1.384 (3)	C41—N3	1.387 (3)
C1—C2	1.513 (3)	C41—C42	1.525 (3)
C2—C3	1.502 (3)	C42—C43	1.492 (3)
C2—H2B	0.94 (2)	C42—H42B	1.00 (2)
C2—H2A	0.95 (3)	C42—H42A	1.00 (3)
C3—C4	1.381 (3)	C43—C44	1.388 (3)
C3—C8	1.403 (3)	C43—C48	1.401 (2)
C4—C5	1.401 (3)	C44—C45	1.391 (3)
C4—H4	0.947 (19)	C44—H44	1.021 (19)
C5—C6	1.393 (3)	C45—C46	1.381 (3)
C5—H5	0.94 (2)	C45—H45	1.00 (2)
C6—C7	1.388 (3)	C46—C47	1.400 (3)
C6—Cl1	1.748 (2)	C46—Cl3	1.737 (2)
C7—C8	1.391 (3)	C47—C48	1.369 (3)
C7—H7	1.00 (2)	C47—H47	0.91 (2)
C8—N1	1.400 (3)	C48—N3	1.414 (3)
C9—C14	1.373 (3)	C49—C50	1.385 (2)
C9—C10	1.395 (3)	C49—C54	1.397 (3)
C9—N1	1.440 (2)	C49—N3	1.428 (2)
C10—C11	1.387 (3)	C50—C51	1.395 (2)
C10—H10	0.94 (2)	C50—H50	0.935 (19)
C11—C12	1.388 (4)	C51—C52	1.381 (3)
C11—H11	0.96 (2)	C51—H51	0.945 (18)
C12—C13	1.377 (3)	C52—C53	1.391 (3)
C12—H12	0.96 (2)	C52—H52	1.04 (2)
C13—C14	1.385 (2)	C53—C54	1.389 (2)
C13—H13	0.96 (2)	C53—H53	0.954 (18)
C14—H14	0.92 (2)	C54—H54	0.924 (17)
C21—O2	1.212 (3)	C61—O4	1.220 (3)
C21—N2	1.393 (3)	C61—N4	1.386 (3)
C21—C22	1.512 (3)	C61—C62	1.530 (3)
C22—C23	1.512 (3)	C62—C63	1.495 (3)
C22—H22A	0.95 (2)	C62—H62A	1.03 (2)
C22—H22B	0.930 (18)	C62—H62B	1.03 (2)
C23—C24	1.371 (3)	C63—C64	1.382 (3)
C23—C28	1.400 (3)	C63—C68	1.404 (3)
C24—C25	1.404 (3)	C64—C65	1.393 (3)
C24—H24	0.940 (17)	C64—H64	1.05 (2)
C25—C26	1.396 (3)	C65—C66	1.378 (3)
C25—H25	0.93 (2)	C65—H65	1.03 (3)
C26—C27	1.393 (3)	C66—C67	1.398 (3)
C26—Cl2	1.746 (2)	C66—Cl4	1.737 (2)
C27—C28	1.401 (3)	C67—C68	1.368 (3)
C27—H27	1.02 (2)	C67—H67	0.889 (19)
C28—N2	1.396 (3)	C68—N4	1.410 (3)
C29—C34	1.381 (3)	C69—C70	1.371 (3)
C29—C30	1.394 (2)	C69—C74	1.402 (3)
C29—N2	1.439 (2)	C69—N4	1.430 (2)
C30—C31	1.393 (2)	C70—C71	1.392 (2)
C30—H30	0.971 (18)	C70—H70	0.94 (2)
C31—C32	1.388 (3)	C71—C72	1.377 (3)
C31—H31	0.937 (18)	C71—H71	0.94 (2)
C32—C33	1.385 (3)	C72—C73	1.394 (3)
C32—H32	0.985 (18)	C72—H72	1.025 (18)
C33—C34	1.397 (2)	C73—C74	1.388 (2)
C33—H33	0.92 (2)	C73—H73	0.99 (2)
C34—H34	0.909 (18)	C74—H74	0.994 (19)
O1—C1—N1	124.23 (18)	O3—C41—N3	125.11 (18)
O1—C1—C2	128.11 (19)	O3—C41—C42	127.49 (19)
N1—C1—C2	107.66 (18)	N3—C41—C42	107.38 (18)
C3—C2—C1	103.57 (16)	C43—C42—C41	103.28 (16)
C3—C2—H2B	110.0 (14)	C43—C42—H42B	117.4 (15)
C1—C2—H2B	107.8 (12)	C41—C42—H42B	113.9 (13)
C3—C2—H2A	111.0 (13)	C43—C42—H42A	115.5 (13)
C1—C2—H2A	115.4 (13)	C41—C42—H42A	100.8 (13)
H2B—C2—H2A	108.9 (18)	H42B—C42—H42A	105 (2)
C4—C3—C8	119.6 (2)	C44—C43—C48	118.8 (2)
C4—C3—C2	132.32 (19)	C44—C43—C42	131.84 (18)
C8—C3—C2	108.05 (17)	C48—C43—C42	109.34 (17)
C3—C4—C5	119.45 (19)	C43—C44—C45	119.50 (19)
C3—C4—H4	121.2 (13)	C43—C44—H44	119.3 (12)
C5—C4—H4	119.3 (14)	C45—C44—H44	121.1 (12)
C6—C5—C4	119.04 (19)	C46—C45—C44	119.8 (2)
C6—C5—H5	123.5 (13)	C46—C45—H45	121.3 (13)
C4—C5—H5	117.5 (13)	C44—C45—H45	118.3 (12)
C5—C6—C7	123.2 (2)	C45—C46—C47	122.2 (2)
C5—C6—Cl1	118.51 (16)	C45—C46—Cl3	119.14 (16)
C7—C6—Cl1	118.25 (15)	C47—C46—Cl3	118.66 (15)
C8—C7—C6	116.03 (18)	C48—C47—C46	116.50 (18)
C8—C7—H7	123.4 (14)	C48—C47—H47	122.0 (17)
C6—C7—H7	120.6 (15)	C46—C47—H47	121.4 (17)
C7—C8—N1	127.83 (18)	C47—C48—C43	123.16 (19)
C7—C8—C3	122.61 (19)	C47—C48—N3	128.19 (17)
N1—C8—C3	109.56 (18)	C43—C48—N3	108.64 (18)
C14—C9—C10	120.95 (17)	C50—C49—C54	121.00 (17)
C14—C9—N1	120.7 (2)	C50—C49—N3	120.13 (17)
C10—C9—N1	118.3 (2)	C54—C49—N3	118.87 (16)
C11—C10—C9	118.66 (18)	C49—C50—C51	119.34 (16)
C11—C10—H10	120.1 (13)	C49—C50—H50	119.5 (11)
C9—C10—H10	121.3 (13)	C51—C50—H50	121.1 (11)
C12—C11—C10	120.51 (19)	C52—C51—C50	119.98 (16)
C12—C11—H11	121.0 (13)	C52—C51—H51	122.6 (12)
C10—C11—H11	118.3 (13)	C50—C51—H51	117.1 (12)
C13—C12—C11	119.83 (19)	C51—C52—C53	120.58 (18)
C13—C12—H12	123.2 (17)	C51—C52—H52	127.3 (12)
C11—C12—H12	116.7 (18)	C53—C52—H52	111.7 (13)
C12—C13—C14	120.31 (18)	C54—C53—C52	120.03 (18)
C12—C13—H13	121.6 (12)	C54—C53—H53	119.5 (10)
C14—C13—H13	118.1 (12)	C52—C53—H53	120.4 (10)
C9—C14—C13	119.71 (17)	C53—C54—C49	119.05 (16)
C9—C14—H14	119.2 (13)	C53—C54—H54	122.3 (11)
C13—C14—H14	121.1 (13)	C49—C54—H54	118.7 (11)
C1—N1—C8	111.15 (15)	C41—N3—C48	111.23 (15)
C1—N1—C9	125.23 (18)	C41—N3—C49	123.51 (18)
C8—N1—C9	123.61 (18)	C48—N3—C49	125.25 (17)
O2—C21—N2	124.69 (18)	O4—C61—N4	125.00 (18)
O2—C21—C22	127.60 (19)	O4—C61—C62	127.73 (19)
N2—C21—C22	107.71 (18)	N4—C61—C62	107.27 (18)
C21—C22—C23	103.39 (17)	C63—C62—C61	103.53 (17)
C21—C22—H22A	113.3 (12)	C63—C62—H62A	117.7 (12)
C23—C22—H22A	111.8 (12)	C61—C62—H62A	101.5 (11)
C21—C22—H22B	109.1 (11)	C63—C62—H62B	116.5 (15)
C23—C22—H22B	110.2 (12)	C61—C62—H62B	110.5 (12)
H22A—C22—H22B	109.0 (16)	H62A—C62—H62B	105.9 (18)
C24—C23—C28	120.1 (2)	C64—C63—C68	118.5 (2)
C24—C23—C22	132.08 (18)	C64—C63—C62	132.84 (18)
C28—C23—C22	107.84 (17)	C68—C63—C62	108.65 (17)
C23—C24—C25	119.69 (19)	C63—C64—C65	119.93 (19)
C23—C24—H24	123.7 (12)	C63—C64—H64	117.3 (12)
C25—C24—H24	116.4 (12)	C65—C64—H64	122.6 (12)
C26—C25—C24	119.01 (19)	C66—C65—C64	119.41 (19)
C26—C25—H25	122.4 (13)	C66—C65—H65	120.0 (14)
C24—C25—H25	118.3 (14)	C64—C65—H65	120.2 (13)
C25—C26—C27	122.9 (2)	C65—C66—C67	122.6 (2)
C25—C26—Cl2	118.63 (16)	C65—C66—Cl4	118.98 (16)
C27—C26—Cl2	118.43 (15)	C67—C66—Cl4	118.44 (15)
C26—C27—C28	116.03 (17)	C68—C67—C66	116.28 (18)
C26—C27—H27	121.9 (15)	C68—C67—H67	120.8 (15)
C28—C27—H27	122.0 (15)	C66—C67—H67	122.8 (15)
N2—C28—C23	110.10 (18)	C67—C68—C63	123.28 (19)
N2—C28—C27	127.58 (17)	C67—C68—N4	127.37 (18)
C23—C28—C27	122.25 (19)	C63—C68—N4	109.33 (19)
C34—C29—C30	121.55 (17)	C70—C69—C74	121.03 (17)
C34—C29—N2	119.49 (16)	C70—C69—N4	120.6 (2)
C30—C29—N2	118.92 (18)	C74—C69—N4	118.4 (2)
C29—C30—C31	118.51 (17)	C69—C70—C71	119.75 (18)
C29—C30—H30	120.4 (11)	C69—C70—H70	117.8 (14)
C31—C30—H30	121.0 (11)	C71—C70—H70	122.4 (14)
C32—C31—C30	120.41 (17)	C72—C71—C70	120.04 (18)
C32—C31—H31	123.6 (11)	C72—C71—H71	119.2 (13)
C30—C31—H31	116.0 (11)	C70—C71—H71	120.7 (13)
C33—C32—C31	120.39 (19)	C71—C72—C73	120.28 (18)
C33—C32—H32	118.4 (12)	C71—C72—H72	128.6 (13)
C31—C32—H32	121.2 (12)	C73—C72—H72	111.1 (13)
C32—C33—C34	119.82 (18)	C74—C73—C72	120.12 (18)
C32—C33—H33	122.6 (11)	C74—C73—H73	118.6 (11)
C34—C33—H33	117.5 (11)	C72—C73—H73	121.3 (11)
C29—C34—C33	119.32 (16)	C73—C74—C69	118.73 (17)
C29—C34—H34	119.6 (11)	C73—C74—H74	120.4 (11)
C33—C34—H34	121.1 (11)	C69—C74—H74	120.9 (11)
C21—N2—C28	110.85 (15)	C61—N4—C68	111.19 (16)
C21—N2—C29	124.24 (17)	C61—N4—C69	123.69 (18)
C28—N2—C29	124.90 (17)	C68—N4—C69	125.12 (18)
O1—C1—C2—C3	−178.6 (2)	O3—C41—C42—C43	−178.3 (2)
N1—C1—C2—C3	0.6 (2)	N3—C41—C42—C43	2.9 (2)
C1—C2—C3—C4	−179.6 (2)	C41—C42—C43—C44	176.3 (2)
C1—C2—C3—C8	−0.1 (2)	C41—C42—C43—C48	−1.1 (3)
C8—C3—C4—C5	1.0 (3)	C48—C43—C44—C45	0.2 (3)
C2—C3—C4—C5	−179.6 (2)	C42—C43—C44—C45	−177.1 (2)
C3—C4—C5—C6	−1.1 (3)	C43—C44—C45—C46	−0.2 (4)
C4—C5—C6—C7	1.1 (3)	C44—C45—C46—C47	−0.6 (4)
C4—C5—C6—Cl1	−178.72 (17)	C44—C45—C46—Cl3	179.37 (19)
C5—C6—C7—C8	−0.9 (3)	C45—C46—C47—C48	1.4 (3)
Cl1—C6—C7—C8	178.92 (16)	Cl3—C46—C47—C48	−178.58 (16)
C6—C7—C8—N1	−179.3 (2)	C46—C47—C48—C43	−1.4 (3)
C6—C7—C8—C3	0.7 (3)	C46—C47—C48—N3	178.0 (2)
C4—C3—C8—C7	−0.8 (3)	C44—C43—C48—C47	0.6 (3)
C2—C3—C8—C7	179.60 (19)	C42—C43—C48—C47	178.5 (2)
C4—C3—C8—N1	179.2 (2)	C44—C43—C48—N3	−178.9 (2)
C2—C3—C8—N1	−0.3 (3)	C42—C43—C48—N3	−1.0 (3)
C14—C9—C10—C11	−0.3 (3)	C54—C49—C50—C51	−1.2 (3)
N1—C9—C10—C11	177.28 (17)	N3—C49—C50—C51	179.08 (19)
C9—C10—C11—C12	−0.4 (3)	C49—C50—C51—C52	−0.3 (3)
C10—C11—C12—C13	1.5 (3)	C50—C51—C52—C53	1.1 (3)
C11—C12—C13—C14	−1.9 (3)	C51—C52—C53—C54	−0.2 (3)
C10—C9—C14—C13	−0.1 (3)	C52—C53—C54—C49	−1.3 (3)
N1—C9—C14—C13	−177.65 (17)	C50—C49—C54—C53	2.1 (3)
C12—C13—C14—C9	1.3 (3)	N3—C49—C54—C53	−178.25 (19)
O1—C1—N1—C8	178.4 (2)	O3—C41—N3—C48	177.5 (2)
C2—C1—N1—C8	−0.8 (2)	C42—C41—N3—C48	−3.7 (3)
O1—C1—N1—C9	−0.7 (4)	O3—C41—N3—C49	−1.9 (4)
C2—C1—N1—C9	−179.9 (2)	C42—C41—N3—C49	176.9 (2)
C7—C8—N1—C1	−179.2 (2)	C47—C48—N3—C41	−176.4 (2)
C3—C8—N1—C1	0.8 (3)	C43—C48—N3—C41	3.0 (3)
C7—C8—N1—C9	−0.1 (3)	C47—C48—N3—C49	2.9 (4)
C3—C8—N1—C9	179.9 (2)	C43—C48—N3—C49	−177.6 (2)
C14—C9—N1—C1	103.8 (3)	C50—C49—N3—C41	−115.9 (2)
C10—C9—N1—C1	−73.8 (3)	C54—C49—N3—C41	64.4 (3)
C14—C9—N1—C8	−75.2 (3)	C50—C49—N3—C48	64.8 (3)
C10—C9—N1—C8	107.2 (3)	C54—C49—N3—C48	−114.8 (2)
O2—C21—C22—C23	−177.0 (2)	O4—C61—C62—C63	−179.3 (2)
N2—C21—C22—C23	3.1 (2)	N4—C61—C62—C63	0.8 (2)
C21—C22—C23—C24	177.1 (2)	C61—C62—C63—C64	−179.8 (2)
C21—C22—C23—C28	−2.0 (2)	C61—C62—C63—C68	0.4 (2)
C28—C23—C24—C25	2.0 (3)	C68—C63—C64—C65	0.3 (3)
C22—C23—C24—C25	−177.0 (2)	C62—C63—C64—C65	−179.5 (2)
C23—C24—C25—C26	−1.0 (3)	C63—C64—C65—C66	−0.1 (3)
C24—C25—C26—C27	−0.1 (3)	C64—C65—C66—C67	−0.8 (4)
C24—C25—C26—Cl2	178.74 (17)	C64—C65—C66—Cl4	−179.56 (18)
C25—C26—C27—C28	0.1 (3)	C65—C66—C67—C68	1.5 (3)
Cl2—C26—C27—C28	−178.78 (16)	Cl4—C66—C67—C68	−179.82 (17)
C24—C23—C28—N2	−179.1 (2)	C66—C67—C68—C63	−1.2 (3)
C22—C23—C28—N2	0.1 (3)	C66—C67—C68—N4	−179.3 (2)
C24—C23—C28—C27	−2.1 (3)	C64—C63—C68—C67	0.4 (3)
C22—C23—C28—C27	177.09 (19)	C62—C63—C68—C67	−179.8 (2)
C26—C27—C28—N2	177.4 (2)	C64—C63—C68—N4	178.8 (2)
C26—C27—C28—C23	1.0 (3)	C62—C63—C68—N4	−1.4 (3)
C34—C29—C30—C31	0.1 (3)	C74—C69—C70—C71	−2.3 (3)
N2—C29—C30—C31	177.85 (18)	N4—C69—C70—C71	178.44 (19)
C29—C30—C31—C32	−0.6 (3)	C69—C70—C71—C72	1.4 (3)
C30—C31—C32—C33	0.7 (4)	C70—C71—C72—C73	0.4 (3)
C31—C32—C33—C34	−0.3 (4)	C71—C72—C73—C74	−1.4 (3)
C30—C29—C34—C33	0.3 (3)	C72—C73—C74—C69	0.5 (3)
N2—C29—C34—C33	−177.44 (19)	C70—C69—C74—C73	1.4 (3)
C32—C33—C34—C29	−0.2 (3)	N4—C69—C74—C73	−179.37 (18)
O2—C21—N2—C28	176.8 (2)	O4—C61—N4—C68	178.4 (2)
C22—C21—N2—C28	−3.3 (3)	C62—C61—N4—C68	−1.6 (3)
O2—C21—N2—C29	−2.0 (4)	O4—C61—N4—C69	−1.9 (4)
C22—C21—N2—C29	177.9 (2)	C62—C61—N4—C69	178.1 (2)
C23—C28—N2—C21	2.0 (3)	C67—C68—N4—C61	−179.7 (2)
C27—C28—N2—C21	−174.7 (2)	C63—C68—N4—C61	1.9 (3)
C23—C28—N2—C29	−179.2 (2)	C67—C68—N4—C69	0.6 (4)
C27—C28—N2—C29	4.0 (4)	C63—C68—N4—C69	−177.8 (2)
C34—C29—N2—C21	61.5 (3)	C70—C69—N4—C61	−75.9 (3)
C30—C29—N2—C21	−116.3 (2)	C74—C69—N4—C61	104.9 (3)
C34—C29—N2—C28	−117.1 (2)	C70—C69—N4—C68	103.8 (3)
C30—C29—N2—C28	65.1 (3)	C74—C69—N4—C68	−75.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2	0.92 (2)	2.39 (2)	3.314 (2)	175.0 (18)
C2—H2B···O3	0.94 (2)	2.45 (2)	3.340 (3)	159.0 (19)
C22—H22B···O4^i	0.930 (18)	2.397 (19)	3.305 (3)	165.4 (15)
C42—H42B···O2	1.00 (2)	2.47 (2)	3.322 (3)	143 (2)
C74—H74···O3	0.994 (19)	2.319 (19)	3.306 (2)	171.8 (16)
C62—H62B···O1	1.03 (2)	2.38 (2)	3.336 (3)	154 (2)

Symmetry code: (i) x+1, y, z.

6-Chloro-1-phenylindolin-2-one (A_RT)

Crystal data

C14H10ClNO	F(000) = 504
Mr = 243.68	Dx = 1.377 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7217 (8) Å	Cell parameters from 5830 reflections
b = 4.8842 (3) Å	θ = 2.3–25.9°
c = 19.9554 (14) Å	µ = 0.31 mm^−1
β = 108.577 (1)°	T = 295 K
V = 1175.33 (13) Å^3	Block, colorless
Z = 4	0.38 × 0.32 × 0.16 mm

Data collection

Bruker APEX-II CCD diffractometer	2503 reflections with I > 2σ(I)
ω scans	Rint = 0.022
Absorption correction: multi-scan APEX2 Software Suite (Bruker, 2005)	θmax = 30.2°, θmin = 1.7°
Tmin = 0.893, Tmax = 0.953	h = −17→17
18368 measured reflections	k = −6→6
3438 independent reflections	l = −27→26

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0592P)^2 + 0.1874P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3438 reflections	Δρmax = 0.29 e Å^−3
246 parameters	Δρmin = −0.33 e Å^−3

Special details

Experimental. Scan width 0.5° ω , Crystal to detector distance 5.964 cm, exposure time 25s, 14.8 hours for data collection,In addtion to multi-scan absorption correction,scale procedure has been carried out. The 5 omiga-run take the following theta, initial-omiga, phi values and the following sweep-ranges, respectively -28, -28, 0, 186 (negatively run) -28, 146, 72, 186 (positively run) -30, -28, 144, 186 (negatively run) -33, 146, 216, 186 (positively run) -33, -28, 288, 186 (negatively run)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	1.02300 (3)	−0.13142 (9)	0.39339 (2)	0.06708 (15)
O1	0.54649 (11)	0.8081 (3)	0.34224 (7)	0.0801 (4)
N1	0.69396 (9)	0.5144 (2)	0.38432 (5)	0.0492 (3)
C5	0.90732 (13)	0.1921 (3)	0.28554 (8)	0.0566 (4)
C6	0.92024 (11)	0.1067 (3)	0.35376 (7)	0.0498 (3)
C7	0.85347 (11)	0.2032 (3)	0.39196 (7)	0.0470 (3)
C8	0.77239 (10)	0.3888 (3)	0.35832 (6)	0.0434 (3)
C9	0.68828 (11)	0.4769 (3)	0.45445 (6)	0.0469 (3)
C10	0.7745 (5)	0.5750 (11)	0.5097 (2)	0.0568 (10)	0.528 (10)
H10	0.830 (3)	0.665 (7)	0.5036 (17)	0.059 (9)*	0.528 (10)
C11	0.7655 (6)	0.5472 (13)	0.5770 (3)	0.0698 (13)	0.528 (10)
H11	0.821 (3)	0.620 (8)	0.612 (2)	0.077 (11)*	0.528 (10)
C14	0.5989 (4)	0.3505 (14)	0.4624 (2)	0.0581 (12)	0.528 (10)
H14	0.542 (3)	0.299 (8)	0.422 (2)	0.070 (10)*	0.528 (10)
C13	0.5914 (5)	0.3287 (14)	0.5303 (2)	0.0692 (14)	0.528 (10)
H13	0.531 (3)	0.264 (9)	0.530 (2)	0.083*	0.528 (10)
C10'	0.7302 (7)	0.6689 (16)	0.5071 (3)	0.0700 (17)	0.472 (10)
H10'	0.761 (5)	0.816 (11)	0.491 (3)	0.099 (16)*	0.472 (10)
C11'	0.7219 (9)	0.6310 (19)	0.5741 (3)	0.0825 (19)	0.472 (10)
H11'	0.746 (4)	0.761 (10)	0.604 (3)	0.087 (13)*	0.472 (10)
C14'	0.6386 (6)	0.2416 (12)	0.4715 (2)	0.0595 (12)	0.472 (10)
H14'	0.604 (3)	0.123 (8)	0.434 (2)	0.064 (10)*	0.472 (10)
C13'	0.6324 (6)	0.2102 (14)	0.5400 (2)	0.0722 (14)	0.472 (10)
H13'	0.594 (3)	0.046 (9)	0.550 (2)	0.078 (12)*	0.472 (10)
C12	0.67357 (17)	0.4190 (5)	0.58814 (9)	0.0742 (5)
C4	0.82503 (13)	0.3798 (3)	0.25342 (7)	0.0549 (3)
C3	0.75626 (11)	0.4785 (3)	0.28895 (6)	0.0470 (3)
C2	0.66060 (14)	0.6719 (3)	0.26879 (7)	0.0559 (3)
C1	0.62326 (12)	0.6806 (3)	0.33387 (7)	0.0548 (3)
H2A	0.6820 (14)	0.861 (4)	0.2592 (9)	0.067 (5)*
H2B	0.6002 (17)	0.610 (4)	0.2284 (11)	0.081 (6)*
H4	0.8135 (14)	0.445 (4)	0.2049 (9)	0.068 (5)*
H5	0.9551 (14)	0.125 (3)	0.2586 (9)	0.064 (5)*
H7	0.8627 (13)	0.145 (3)	0.4400 (9)	0.054 (4)*
H12	0.6594 (18)	0.383 (4)	0.6330 (12)	0.092 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0615 (2)	0.0706 (3)	0.0708 (3)	0.01147 (18)	0.02344 (19)	−0.00198 (18)
O1	0.0748 (7)	0.0955 (9)	0.0684 (7)	0.0342 (7)	0.0203 (6)	0.0167 (7)
N1	0.0535 (6)	0.0562 (7)	0.0389 (5)	0.0062 (5)	0.0163 (5)	0.0047 (5)
C5	0.0605 (8)	0.0659 (9)	0.0505 (7)	−0.0100 (7)	0.0278 (7)	−0.0094 (7)
C6	0.0494 (7)	0.0516 (7)	0.0499 (7)	−0.0067 (6)	0.0182 (6)	−0.0056 (6)
C7	0.0524 (7)	0.0508 (7)	0.0395 (6)	−0.0025 (6)	0.0168 (5)	0.0008 (5)
C8	0.0484 (6)	0.0468 (7)	0.0362 (6)	−0.0068 (5)	0.0152 (5)	−0.0023 (5)
C9	0.0530 (7)	0.0505 (7)	0.0398 (6)	0.0099 (6)	0.0183 (5)	0.0027 (5)
C10	0.059 (2)	0.063 (2)	0.0473 (15)	0.0070 (18)	0.0162 (15)	0.0031 (15)
C11	0.084 (3)	0.077 (3)	0.0425 (17)	0.024 (2)	0.012 (2)	−0.0003 (17)
C14	0.061 (2)	0.067 (3)	0.0530 (18)	0.002 (2)	0.0277 (17)	−0.0054 (17)
C13	0.071 (2)	0.084 (3)	0.068 (2)	0.014 (2)	0.043 (2)	0.011 (2)
C10'	0.084 (4)	0.072 (3)	0.052 (2)	−0.018 (3)	0.020 (2)	−0.006 (2)
C11'	0.112 (6)	0.090 (5)	0.042 (2)	−0.009 (4)	0.018 (3)	−0.015 (3)
C14'	0.078 (3)	0.051 (2)	0.058 (2)	0.007 (2)	0.032 (2)	−0.0002 (18)
C13'	0.087 (3)	0.070 (3)	0.073 (2)	0.020 (3)	0.045 (2)	0.027 (2)
C12	0.0914 (13)	0.0926 (14)	0.0457 (8)	0.0345 (11)	0.0317 (8)	0.0113 (8)
C4	0.0654 (9)	0.0648 (9)	0.0377 (6)	−0.0142 (7)	0.0208 (6)	−0.0023 (6)
C3	0.0529 (7)	0.0497 (7)	0.0359 (6)	−0.0122 (6)	0.0107 (5)	−0.0010 (5)
C2	0.0605 (8)	0.0607 (9)	0.0399 (7)	−0.0046 (7)	0.0068 (6)	0.0056 (6)
C1	0.0546 (7)	0.0585 (8)	0.0470 (7)	0.0036 (6)	0.0099 (6)	0.0053 (6)

Geometric parameters (Å, º)

Cl1—C6	1.7402 (15)	C14—C13	1.393 (5)
O1—C1	1.2139 (19)	C14—H14	0.92 (4)
N1—C1	1.3801 (17)	C13—C12	1.360 (5)
N1—C8	1.4038 (17)	C13—H13	0.83 (4)
N1—C9	1.4359 (16)	C10'—C11'	1.388 (8)
C5—C6	1.383 (2)	C10'—H10'	0.92 (6)
C5—C4	1.386 (2)	C11'—C12	1.280 (7)
C5—H5	0.988 (18)	C11'—H11'	0.86 (5)
C6—C7	1.3920 (19)	C14'—C13'	1.404 (6)
C7—C8	1.3768 (19)	C14'—H14'	0.93 (4)
C7—H7	0.969 (16)	C13'—C12	1.384 (6)
C8—C3	1.4035 (17)	C13'—H13'	0.98 (5)
C9—C14	1.347 (4)	C12—H12	0.98 (2)
C9—C10	1.370 (5)	C4—C3	1.377 (2)
C9—C10'	1.382 (5)	C4—H4	0.984 (18)
C9—C14'	1.405 (5)	C3—C2	1.491 (2)
C10—C11	1.391 (7)	C2—C1	1.519 (2)
C10—H10	0.88 (4)	C2—H2A	0.998 (18)
C11—C12	1.405 (7)	C2—H2B	0.97 (2)
C11—H11	0.90 (4)
C1—N1—C8	111.23 (11)	C9—C10'—C11'	120.8 (5)
C1—N1—C9	124.24 (11)	C9—C10'—H10'	112 (3)
C8—N1—C9	124.53 (10)	C11'—C10'—H10'	128 (3)
C6—C5—C4	119.37 (13)	C12—C11'—C10'	120.5 (5)
C6—C5—H5	122.4 (10)	C12—C11'—H11'	122 (3)
C4—C5—H5	118.2 (10)	C10'—C11'—H11'	117 (3)
C5—C6—C7	122.36 (14)	C9—C14'—C13'	119.6 (4)
C5—C6—Cl1	119.05 (11)	C9—C14'—H14'	117 (2)
C7—C6—Cl1	118.58 (11)	C13'—C14'—H14'	123 (2)
C8—C7—C6	116.68 (12)	C12—C13'—C14'	118.0 (4)
C8—C7—H7	120.7 (9)	C12—C13'—H13'	125 (2)
C6—C7—H7	122.6 (9)	C14'—C13'—H13'	117 (2)
C7—C8—C3	122.54 (12)	C11'—C12—C13'	123.2 (3)
C7—C8—N1	128.17 (11)	C13—C12—C11	117.6 (3)
C3—C8—N1	109.29 (11)	C11'—C12—H12	125.8 (13)
C14—C9—C10	123.7 (3)	C13—C12—H12	113.5 (13)
C10'—C9—C14'	117.8 (3)	C13'—C12—H12	111.0 (13)
C14—C9—N1	118.7 (2)	C11—C12—H12	128.8 (13)
C10—C9—N1	117.6 (2)	C3—C4—C5	120.25 (13)
C10'—C9—N1	121.8 (2)	C3—C4—H4	118.3 (10)
C14'—C9—N1	120.4 (2)	C5—C4—H4	121.5 (10)
C9—C10—C11	116.8 (4)	C4—C3—C8	118.78 (13)
C9—C10—H10	123 (2)	C4—C3—C2	132.91 (12)
C11—C10—H10	120 (2)	C8—C3—C2	108.31 (12)
C10—C11—C12	121.7 (5)	C3—C2—C1	103.76 (11)
C10—C11—H11	115 (3)	C3—C2—H2A	112.9 (10)
C12—C11—H11	123 (3)	C1—C2—H2A	108.5 (10)
C9—C14—C13	118.2 (3)	C3—C2—H2B	113.0 (12)
C9—C14—H14	119 (2)	C1—C2—H2B	109.8 (12)
C13—C14—H14	123 (2)	H2A—C2—H2B	108.8 (15)
C12—C13—C14	121.8 (3)	O1—C1—N1	124.56 (14)
C12—C13—H13	126 (3)	O1—C1—C2	128.06 (13)
C14—C13—H13	112 (3)	N1—C1—C2	107.38 (12)
C4—C5—C6—C7	−0.2 (2)	N1—C9—C10'—C11'	178.7 (5)
C4—C5—C6—Cl1	179.42 (11)	C9—C10'—C11'—C12	−1.1 (10)
C5—C6—C7—C8	0.4 (2)	C10'—C9—C14'—C13'	0.5 (6)
Cl1—C6—C7—C8	−179.25 (10)	N1—C9—C14'—C13'	−179.1 (3)
C6—C7—C8—C3	0.16 (19)	C9—C14'—C13'—C12	1.7 (7)
C6—C7—C8—N1	179.27 (12)	C10'—C11'—C12—C13'	3.5 (10)
C1—N1—C8—C7	−177.53 (13)	C14—C13—C12—C11	2.7 (6)
C9—N1—C8—C7	2.9 (2)	C14'—C13'—C12—C11'	−3.8 (7)
C1—N1—C8—C3	1.68 (15)	C10—C11—C12—C13	−1.8 (6)
C9—N1—C8—C3	−177.89 (12)	C6—C5—C4—C3	−0.5 (2)
C1—N1—C9—C14	66.2 (4)	C5—C4—C3—C8	1.0 (2)
C8—N1—C9—C14	−114.3 (4)	C5—C4—C3—C2	−178.32 (15)
C1—N1—C9—C10	−113.2 (3)	C7—C8—C3—C4	−0.8 (2)
C8—N1—C9—C10	66.3 (3)	N1—C8—C3—C4	179.90 (12)
C1—N1—C9—C10'	−78.8 (5)	C7—C8—C3—C2	178.64 (12)
C8—N1—C9—C10'	100.8 (5)	N1—C8—C3—C2	−0.62 (15)
C1—N1—C9—C14'	100.8 (4)	C4—C3—C2—C1	178.85 (15)
C8—N1—C9—C14'	−79.7 (4)	C8—C3—C2—C1	−0.53 (15)
C14—C9—C10—C11	−2.0 (5)	C8—N1—C1—O1	178.32 (15)
N1—C9—C10—C11	177.4 (3)	C9—N1—C1—O1	−2.1 (2)
C9—C10—C11—C12	1.4 (6)	C8—N1—C1—C2	−1.99 (16)
C10—C9—C14—C13	2.9 (6)	C9—N1—C1—C2	177.59 (13)
N1—C9—C14—C13	−176.5 (3)	C3—C2—C1—O1	−178.82 (16)
C9—C14—C13—C12	−3.2 (7)	C3—C2—C1—N1	1.51 (16)
C14'—C9—C10'—C11'	−0.9 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14′—H14′···O1^i	0.93 (4)	2.33 (4)	3.253 (5)	171 (3)
C2—H2B···O1^ii	0.97 (2)	2.44 (2)	3.360 (2)	158.0 (16)

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

4-Chloro-1-phenylindolin-2-one (B_LT)

Crystal data

C14H10ClNO	F(000) = 504
Mr = 243.68	Dx = 1.428 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.4274 (9) Å	Cell parameters from 9462 reflections
b = 11.8586 (10) Å	θ = 2.6–30.2°
c = 9.1689 (8) Å	µ = 0.32 mm^−1
β = 90.341 (2)°	T = 100 K
V = 1133.75 (17) Å^3	PLANE, colourless
Z = 4	0.59 × 0.33 × 0.10 mm

Data collection

Bruker APEX-II CCD diffractometer	2937 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm^-1	Rint = 0.034
ω scans	θmax = 30.3°, θmin = 2.0°
Absorption correction: multi-scan APEX2 Software Suite (Bruker, 2005)	h = −14→14
Tmin = 0.834, Tmax = 0.968	k = −16→16
20207 measured reflections	l = −12→12
3317 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	All H-atom parameters refined
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0532P)^2 + 0.3565P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.002
3317 reflections	Δρmax = 0.43 e Å^−3
194 parameters	Δρmin = −0.25 e Å^−3

Special details

Experimental. Scan width 0.5° ω , Crystal to detector distance 5.964 cm, exposure time 10s, 8 hours for data collection.In addtion to multi-scan absorption correction,scale procedure has been carried out. The 6 omiga-run take the following theta, initial-omiga, phi values and the following sweep-ranges, respectively -20.332, -221.333, -80, 223 (positively run) -33, 146, -28.6, 186 (positively run) -28, -28, 22.8, 186 (negatively run) -33, 146, 74.2, 186 (positively run) -33, -28, 125.6, 186 (negatively run) -33, 146, 177, 135 (positively run)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.76721 (10)	0.49310 (9)	0.64644 (12)	0.0186 (2)
C2	0.85830 (11)	0.40374 (9)	0.58832 (12)	0.0194 (2)
C3	0.86181 (10)	0.42828 (9)	0.42814 (11)	0.0174 (2)
C4	0.92785 (10)	0.37865 (9)	0.31494 (12)	0.0191 (2)
C5	0.90912 (11)	0.41479 (10)	0.17124 (12)	0.0217 (2)
C6	0.82162 (11)	0.50041 (10)	0.14285 (12)	0.0215 (2)
C7	0.75357 (10)	0.55343 (9)	0.25525 (12)	0.0192 (2)
C8	0.77632 (10)	0.51624 (9)	0.39652 (11)	0.0166 (2)
C9	0.62732 (10)	0.64194 (9)	0.53875 (11)	0.0168 (2)
C10	0.64796 (11)	0.74572 (9)	0.47135 (12)	0.0195 (2)
C11	0.55612 (12)	0.83056 (10)	0.48458 (13)	0.0229 (2)
C12	0.44611 (12)	0.81288 (10)	0.56664 (13)	0.0244 (2)
C13	0.42704 (11)	0.70949 (10)	0.63459 (13)	0.0232 (2)
C14	0.51636 (10)	0.62325 (10)	0.61973 (12)	0.0198 (2)
Cl1	1.03557 (3)	0.27007 (2)	0.35207 (3)	0.02390 (9)
N1	0.71912 (8)	0.55315 (8)	0.52725 (9)	0.01685 (18)
O1	0.74015 (8)	0.51070 (8)	0.77320 (9)	0.02393 (18)
H5	0.9565 (14)	0.3789 (13)	0.0896 (17)	0.025 (4)*
H6	0.8079 (14)	0.5211 (13)	0.0430 (17)	0.025 (4)*
H7	0.6961 (13)	0.6125 (12)	0.2337 (15)	0.017 (3)*
H10	0.7241 (15)	0.7584 (12)	0.4177 (17)	0.024 (4)*
H11	0.5717 (14)	0.9014 (13)	0.4399 (16)	0.025 (4)*
H12	0.3836 (16)	0.8679 (14)	0.5786 (18)	0.033 (4)*
H13	0.3452 (14)	0.7052 (13)	0.7050 (17)	0.027 (4)*
H14	0.5053 (14)	0.5512 (14)	0.6660 (16)	0.023 (3)*
H2A	0.9405 (15)	0.4094 (14)	0.6355 (17)	0.028 (4)*
H2B	0.8247 (14)	0.3270 (14)	0.6089 (17)	0.030 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0190 (5)	0.0197 (5)	0.0170 (5)	−0.0017 (4)	0.0004 (4)	0.0029 (4)
C2	0.0208 (5)	0.0198 (5)	0.0176 (5)	0.0005 (4)	−0.0001 (4)	0.0025 (4)
C3	0.0172 (4)	0.0181 (5)	0.0168 (5)	−0.0026 (4)	0.0001 (4)	0.0003 (4)
C4	0.0174 (5)	0.0179 (5)	0.0220 (5)	−0.0014 (4)	0.0010 (4)	−0.0016 (4)
C5	0.0237 (5)	0.0222 (5)	0.0193 (5)	−0.0030 (4)	0.0040 (4)	−0.0042 (4)
C6	0.0269 (5)	0.0233 (5)	0.0144 (5)	−0.0038 (4)	0.0010 (4)	−0.0003 (4)
C7	0.0217 (5)	0.0195 (5)	0.0164 (5)	−0.0014 (4)	0.0001 (4)	0.0003 (4)
C8	0.0172 (4)	0.0173 (5)	0.0154 (5)	−0.0028 (4)	0.0011 (4)	−0.0009 (3)
C9	0.0177 (5)	0.0175 (5)	0.0153 (5)	0.0000 (4)	−0.0016 (4)	−0.0020 (3)
C10	0.0218 (5)	0.0200 (5)	0.0168 (5)	−0.0019 (4)	−0.0002 (4)	−0.0004 (4)
C11	0.0298 (6)	0.0178 (5)	0.0211 (5)	0.0005 (4)	−0.0036 (4)	−0.0005 (4)
C12	0.0252 (5)	0.0240 (6)	0.0238 (6)	0.0050 (4)	−0.0037 (4)	−0.0057 (4)
C13	0.0188 (5)	0.0274 (6)	0.0233 (5)	−0.0006 (4)	0.0000 (4)	−0.0045 (4)
C14	0.0197 (5)	0.0212 (5)	0.0185 (5)	−0.0020 (4)	0.0003 (4)	−0.0007 (4)
Cl1	0.02142 (14)	0.02228 (15)	0.02799 (16)	0.00322 (9)	0.00050 (10)	−0.00249 (10)
N1	0.0188 (4)	0.0184 (4)	0.0134 (4)	0.0006 (3)	0.0011 (3)	0.0012 (3)
O1	0.0276 (4)	0.0295 (4)	0.0147 (4)	0.0016 (3)	0.0027 (3)	0.0030 (3)

Geometric parameters (Å, º)

C1—O1	1.2157 (13)	C7—H7	0.942 (14)
C1—N1	1.3951 (14)	C8—N1	1.4116 (13)
C1—C2	1.5216 (15)	C9—C10	1.3944 (15)
C2—C3	1.4978 (15)	C9—C14	1.3962 (14)
C2—H2A	0.960 (16)	C9—N1	1.4274 (13)
C2—H2B	0.994 (16)	C10—C11	1.3948 (16)
C3—C4	1.3808 (15)	C10—H10	0.948 (16)
C3—C8	1.4013 (15)	C11—C12	1.3914 (17)
C4—C5	1.3981 (16)	C11—H11	0.949 (15)
C4—Cl1	1.7409 (11)	C12—C13	1.3901 (18)
C5—C6	1.3886 (17)	C12—H12	0.929 (17)
C5—H5	0.995 (15)	C13—C14	1.3905 (16)
C6—C7	1.4034 (15)	C13—H13	1.074 (15)
C6—H6	0.958 (15)	C14—H14	0.961 (16)
C7—C8	1.3875 (15)
O1—C1—N1	125.23 (10)	C7—C8—C3	122.33 (10)
O1—C1—C2	127.11 (10)	C7—C8—N1	128.57 (10)
N1—C1—C2	107.66 (9)	C3—C8—N1	109.06 (9)
C3—C2—C1	103.12 (9)	C10—C9—C14	120.42 (10)
C3—C2—H2A	113.7 (9)	C10—C9—N1	120.86 (9)
C1—C2—H2A	110.5 (9)	C14—C9—N1	118.72 (9)
C3—C2—H2B	112.0 (9)	C9—C10—C11	119.35 (10)
C1—C2—H2B	110.5 (9)	C9—C10—H10	120.1 (9)
H2A—C2—H2B	107.1 (13)	C11—C10—H10	120.5 (9)
C4—C3—C8	118.77 (10)	C12—C11—C10	120.46 (11)
C4—C3—C2	132.02 (10)	C12—C11—H11	120.7 (9)
C8—C3—C2	109.17 (9)	C10—C11—H11	118.8 (9)
C3—C4—C5	120.68 (10)	C13—C12—C11	119.73 (11)
C3—C4—Cl1	119.49 (9)	C13—C12—H12	117.7 (10)
C5—C4—Cl1	119.83 (8)	C11—C12—H12	122.6 (10)
C6—C5—C4	119.26 (10)	C12—C13—C14	120.47 (11)
C6—C5—H5	120.0 (9)	C12—C13—H13	115.3 (8)
C4—C5—H5	120.7 (9)	C14—C13—H13	124.0 (8)
C5—C6—C7	121.63 (10)	C13—C14—C9	119.54 (11)
C5—C6—H6	117.5 (9)	C13—C14—H14	121.9 (9)
C7—C6—H6	120.9 (9)	C9—C14—H14	118.5 (9)
C8—C7—C6	117.31 (10)	C1—N1—C8	110.80 (9)
C8—C7—H7	122.5 (8)	C1—N1—C9	123.83 (9)
C6—C7—H7	120.2 (8)	C8—N1—C9	125.34 (9)
O1—C1—C2—C3	−175.45 (11)	N1—C9—C10—C11	179.87 (10)
N1—C1—C2—C3	4.34 (11)	C9—C10—C11—C12	1.31 (17)
C1—C2—C3—C4	178.95 (11)	C10—C11—C12—C13	−0.69 (18)
C1—C2—C3—C8	−3.56 (11)	C11—C12—C13—C14	−0.75 (18)
C8—C3—C4—C5	−0.50 (16)	C12—C13—C14—C9	1.54 (17)
C2—C3—C4—C5	176.80 (11)	C10—C9—C14—C13	−0.91 (16)
C8—C3—C4—Cl1	179.44 (8)	N1—C9—C14—C13	178.72 (10)
C2—C3—C4—Cl1	−3.27 (17)	O1—C1—N1—C8	176.10 (11)
C3—C4—C5—C6	−0.95 (16)	C2—C1—N1—C8	−3.69 (12)
Cl1—C4—C5—C6	179.11 (9)	O1—C1—N1—C9	−2.18 (17)
C4—C5—C6—C7	1.49 (17)	C2—C1—N1—C9	178.03 (9)
C5—C6—C7—C8	−0.53 (16)	C7—C8—N1—C1	179.16 (11)
C6—C7—C8—C3	−0.98 (16)	C3—C8—N1—C1	1.41 (12)
C6—C7—C8—N1	−178.46 (10)	C7—C8—N1—C9	−2.60 (17)
C4—C3—C8—C7	1.49 (16)	C3—C8—N1—C9	179.65 (9)
C2—C3—C8—C7	−176.38 (10)	C10—C9—N1—C1	129.80 (11)
C4—C3—C8—N1	179.41 (9)	C14—C9—N1—C1	−49.83 (14)
C2—C3—C8—N1	1.54 (12)	C10—C9—N1—C8	−48.23 (15)
C14—C9—C10—C11	−0.51 (16)	C14—C9—N1—C8	132.15 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1^i	0.958 (15)	2.572 (15)	3.4914 (14)	161.0 (13)
C11—H11···O1^ii	0.949 (15)	2.557 (15)	3.3207 (15)	137.6 (12)
C12—H12···O1^iii	0.929 (17)	2.530 (17)	3.3862 (14)	153.4 (14)

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

4-Chloro-1-phenylindolin-2-one (B_RT)

Crystal data

C14H10ClNO	F(000) = 504
Mr = 243.68	Dx = 1.384 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.5605 (8) Å	Cell parameters from 8615 reflections
b = 12.0485 (9) Å	θ = 2.6–27.8°
c = 9.1939 (7) Å	µ = 0.31 mm^−1
β = 89.288 (2)°	T = 297 K
V = 1169.73 (15) Å^3	Plate, colourless
Z = 4	0.59 × 0.33 × 0.10 mm

Data collection

Bruker APEX-II CCD diffractometer	2575 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm^-1	Rint = 0.022
ω scans	θmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan APEX2 Software Suite (Bruker, 2005)	h = −14→14
Tmin = 0.839, Tmax = 0.969	k = −16→16
23589 measured reflections	l = −12→12
3410 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	All H-atom parameters refined
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0532P)^2 + 0.3065P] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max = 0.001
3410 reflections	Δρmax = 0.29 e Å^−3
194 parameters	Δρmin = −0.30 e Å^−3

Special details

Experimental. Scan width 0.5° ω , Crystal to detector distance 5.964 cm, exposure time 28s, 21 hours for data collection.In addtion to multi-scan absorption correction,scale procedure has been carried out. The 6 omiga-run take the following theta, initial-omiga, phi values and the following sweep-ranges, respectively -20.332, -221.333, -80, 223 (positively run) -33, 146, -28.6, 186 (positively run) -28, -28, 22.8, 186 (negatively run) -33, 146, 74.2, 186 (positively run) -33, -28, 125.6, 186 (negatively run) -33, 146, 177, 186 (positively run) -33, -28, 228.4, 63 (negatively run)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.76562 (13)	0.49276 (12)	0.64486 (14)	0.0495 (3)
C2	0.85585 (14)	0.40585 (12)	0.58575 (15)	0.0511 (3)
C3	0.85988 (12)	0.42980 (11)	0.42606 (14)	0.0453 (3)
C4	0.92506 (12)	0.38062 (12)	0.31262 (15)	0.0504 (3)
C5	0.90718 (15)	0.41639 (13)	0.17034 (16)	0.0583 (4)
C6	0.82218 (16)	0.50083 (14)	0.14390 (15)	0.0588 (4)
C7	0.75498 (14)	0.55303 (12)	0.25600 (14)	0.0504 (3)
C8	0.77665 (11)	0.51631 (10)	0.39620 (13)	0.0427 (3)
C9	0.62896 (12)	0.64046 (11)	0.54016 (13)	0.0442 (3)
C10	0.65075 (15)	0.74267 (12)	0.47462 (15)	0.0517 (3)
C11	0.56094 (17)	0.82574 (14)	0.48807 (18)	0.0621 (4)
C12	0.45172 (17)	0.80830 (15)	0.56878 (19)	0.0662 (4)
C13	0.43101 (15)	0.70694 (15)	0.63495 (18)	0.0632 (4)
C14	0.51839 (13)	0.62236 (13)	0.61987 (16)	0.0530 (3)
Cl1	1.03020 (4)	0.27329 (4)	0.34775 (5)	0.06917 (15)
N1	0.71932 (10)	0.55296 (9)	0.52730 (11)	0.0450 (2)
O1	0.73754 (11)	0.50912 (10)	0.77096 (10)	0.0667 (3)
H5	0.9537 (16)	0.3826 (15)	0.093 (2)	0.068 (5)*
H6	0.8078 (15)	0.5232 (14)	0.0470 (19)	0.066 (5)*
H7	0.6989 (14)	0.6109 (13)	0.2358 (16)	0.048 (4)*
H10	0.7266 (16)	0.7538 (13)	0.4224 (18)	0.058 (4)*
H11	0.5746 (18)	0.8952 (17)	0.445 (2)	0.079 (6)*
H12	0.3920 (18)	0.8602 (17)	0.582 (2)	0.082 (6)*
H13	0.3527 (16)	0.7030 (14)	0.7035 (19)	0.065 (5)*
H14	0.5049 (15)	0.5523 (15)	0.6614 (17)	0.058 (4)*
H2A	0.9360 (16)	0.4121 (14)	0.6312 (19)	0.064 (5)*
H2B	0.8196 (15)	0.3314 (15)	0.6053 (18)	0.063 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0531 (7)	0.0561 (7)	0.0394 (6)	−0.0046 (6)	0.0001 (5)	0.0069 (5)
C2	0.0541 (7)	0.0530 (8)	0.0463 (7)	−0.0007 (6)	−0.0041 (6)	0.0070 (6)
C3	0.0443 (6)	0.0482 (7)	0.0435 (6)	−0.0069 (5)	−0.0011 (5)	0.0009 (5)
C4	0.0463 (6)	0.0490 (7)	0.0559 (7)	−0.0048 (5)	0.0025 (5)	−0.0053 (6)
C5	0.0651 (9)	0.0613 (8)	0.0483 (7)	−0.0070 (7)	0.0114 (6)	−0.0102 (6)
C6	0.0756 (10)	0.0640 (9)	0.0368 (6)	−0.0071 (7)	0.0031 (6)	0.0005 (6)
C7	0.0585 (8)	0.0536 (8)	0.0392 (6)	−0.0023 (6)	−0.0016 (5)	0.0032 (5)
C8	0.0449 (6)	0.0460 (6)	0.0372 (6)	−0.0078 (5)	0.0015 (4)	−0.0004 (5)
C9	0.0470 (6)	0.0484 (7)	0.0374 (6)	−0.0038 (5)	−0.0035 (5)	−0.0030 (5)
C10	0.0585 (8)	0.0504 (7)	0.0461 (7)	−0.0055 (6)	−0.0004 (6)	0.0007 (5)
C11	0.0810 (11)	0.0487 (8)	0.0569 (8)	0.0012 (7)	−0.0114 (7)	−0.0008 (6)
C12	0.0667 (10)	0.0655 (10)	0.0666 (10)	0.0151 (8)	−0.0119 (8)	−0.0151 (8)
C13	0.0505 (8)	0.0757 (10)	0.0632 (9)	0.0004 (7)	0.0011 (7)	−0.0124 (8)
C14	0.0507 (7)	0.0571 (8)	0.0513 (7)	−0.0070 (6)	0.0017 (6)	−0.0016 (6)
Cl1	0.0616 (2)	0.0644 (3)	0.0815 (3)	0.01075 (17)	0.00048 (19)	−0.00778 (19)
N1	0.0501 (6)	0.0494 (6)	0.0356 (5)	−0.0005 (4)	0.0020 (4)	0.0027 (4)
O1	0.0801 (7)	0.0829 (8)	0.0370 (5)	0.0077 (6)	0.0054 (5)	0.0085 (5)

Geometric parameters (Å, º)

C1—O1	1.2093 (16)	C7—H7	0.935 (16)
C1—N1	1.3952 (16)	C8—N1	1.4129 (15)
C1—C2	1.512 (2)	C9—C14	1.3881 (18)
C2—C3	1.4963 (18)	C9—C10	1.3889 (19)
C2—H2A	0.952 (18)	C9—N1	1.4259 (17)
C2—H2B	0.991 (18)	C10—C11	1.383 (2)
C3—C4	1.3765 (18)	C10—H10	0.938 (17)
C3—C8	1.3930 (18)	C11—C12	1.380 (2)
C4—C5	1.392 (2)	C11—H11	0.94 (2)
C4—Cl1	1.7373 (15)	C12—C13	1.381 (3)
C5—C6	1.380 (2)	C12—H12	0.90 (2)
C5—H5	0.948 (18)	C13—C14	1.381 (2)
C6—C7	1.394 (2)	C13—H13	1.034 (17)
C6—H6	0.945 (17)	C14—H14	0.937 (18)
C7—C8	1.3845 (17)
O1—C1—N1	125.01 (13)	C7—C8—C3	122.31 (12)
O1—C1—C2	127.11 (13)	C7—C8—N1	128.34 (13)
N1—C1—C2	107.88 (11)	C3—C8—N1	109.30 (10)
C3—C2—C1	103.25 (11)	C14—C9—C10	120.13 (13)
C3—C2—H2A	113.6 (10)	C14—C9—N1	119.03 (12)
C1—C2—H2A	110.4 (10)	C10—C9—N1	120.83 (12)
C3—C2—H2B	111.1 (10)	C11—C10—C9	119.54 (14)
C1—C2—H2B	108.8 (9)	C11—C10—H10	121.5 (10)
H2A—C2—H2B	109.6 (14)	C9—C10—H10	119.0 (10)
C4—C3—C8	118.92 (12)	C12—C11—C10	120.36 (16)
C4—C3—C2	131.93 (13)	C12—C11—H11	119.2 (12)
C8—C3—C2	109.10 (11)	C10—C11—H11	120.4 (12)
C3—C4—C5	120.41 (14)	C11—C12—C13	119.90 (16)
C3—C4—Cl1	119.62 (11)	C11—C12—H12	123.3 (13)
C5—C4—Cl1	119.97 (11)	C13—C12—H12	116.8 (13)
C6—C5—C4	119.32 (13)	C14—C13—C12	120.44 (15)
C6—C5—H5	121.1 (11)	C14—C13—H13	123.8 (10)
C4—C5—H5	119.6 (11)	C12—C13—H13	115.5 (9)
C5—C6—C7	121.90 (13)	C13—C14—C9	119.60 (15)
C5—C6—H6	119.3 (10)	C13—C14—H14	121.7 (10)
C7—C6—H6	118.8 (10)	C9—C14—H14	118.7 (10)
C8—C7—C6	117.11 (14)	C1—N1—C8	110.35 (11)
C8—C7—H7	122.4 (9)	C1—N1—C9	124.11 (10)
C6—C7—H7	120.5 (9)	C8—N1—C9	125.53 (10)
O1—C1—C2—C3	−176.24 (14)	N1—C9—C10—C11	179.52 (12)
N1—C1—C2—C3	3.45 (14)	C9—C10—C11—C12	1.5 (2)
C1—C2—C3—C4	179.55 (14)	C10—C11—C12—C13	−0.9 (2)
C1—C2—C3—C8	−2.82 (14)	C11—C12—C13—C14	−0.6 (2)
C8—C3—C4—C5	−0.47 (19)	C12—C13—C14—C9	1.4 (2)
C2—C3—C4—C5	176.96 (14)	C10—C9—C14—C13	−0.8 (2)
C8—C3—C4—Cl1	179.52 (9)	N1—C9—C14—C13	179.04 (13)
C2—C3—C4—Cl1	−3.0 (2)	O1—C1—N1—C8	176.77 (14)
C3—C4—C5—C6	−0.8 (2)	C2—C1—N1—C8	−2.93 (14)
Cl1—C4—C5—C6	179.21 (12)	O1—C1—N1—C9	−2.0 (2)
C4—C5—C6—C7	1.2 (2)	C2—C1—N1—C9	178.33 (11)
C5—C6—C7—C8	−0.2 (2)	C7—C8—N1—C1	178.66 (13)
C6—C7—C8—C3	−1.1 (2)	C3—C8—N1—C1	1.11 (14)
C6—C7—C8—N1	−178.38 (13)	C7—C8—N1—C9	−2.6 (2)
C4—C3—C8—C7	1.47 (19)	C3—C8—N1—C9	179.83 (11)
C2—C3—C8—C7	−176.51 (12)	C14—C9—N1—C1	−50.32 (17)
C4—C3—C8—N1	179.19 (11)	C10—C9—N1—C1	129.47 (14)
C2—C3—C8—N1	1.21 (14)	C14—C9—N1—C8	131.12 (13)
C14—C9—C10—C11	−0.7 (2)	C10—C9—N1—C8	−49.09 (18)

1-(3-Chlorophenyl)-indolin-2-one (C_LT)

Crystal data

C14H10ClNO	F(000) = 504
Mr = 243.68	Dx = 1.442 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.1067 (7) Å	Cell parameters from 7732 reflections
b = 13.3924 (8) Å	θ = 2.5–29.8°
c = 8.0288 (5) Å	µ = 0.32 mm^−1
β = 109.920 (2)°	T = 90 K
V = 1122.79 (12) Å^3	Bar, colourless
Z = 4	0.60 × 0.23 × 0.09 mm

Data collection

Bruker APEX-II CCD diffractometer	2765 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm^-1	Rint = 0.027
ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan APEX2 Software Suite (Bruker, 2005)	h = −14→14
Tmin = 0.832, Tmax = 0.972	k = −18→18
17709 measured reflections	l = −11→11
3191 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	All H-atom parameters refined
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0467P)^2 + 0.3999P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3191 reflections	Δρmax = 0.42 e Å^−3
194 parameters	Δρmin = −0.27 e Å^−3

Special details

Experimental. Scan width 0.5° ω , Crystal to detector distance 5.964 cm, exposure time 12s, 8.5 hours for data collection, with scale. The 5 omiga-run take the following theta, initial-omiga, phi values and the following sweep-ranges, respectively -20.332, -221.333, 0, 223 (positively run) -32, 146, 72, 186 (positively run) -28, -28, 144, 186 (negatively run) -33, 146, 216, 186 (positively run) -33, -28, 288, 200 (negatively run)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.83229 (10)	0.37452 (7)	0.24414 (14)	0.0113 (2)
C2	0.97698 (10)	0.37009 (8)	0.33233 (13)	0.0110 (2)
C3	0.99596 (10)	0.37259 (7)	0.52649 (13)	0.0109 (2)
C4	1.10634 (10)	0.37359 (8)	0.67415 (14)	0.0126 (2)
C5	1.09509 (11)	0.38197 (8)	0.84178 (14)	0.0140 (2)
C6	0.97511 (11)	0.38739 (8)	0.86005 (14)	0.0135 (2)
C7	0.86282 (10)	0.38494 (8)	0.71219 (14)	0.0124 (2)
C8	0.87626 (10)	0.37859 (7)	0.54693 (13)	0.0109 (2)
C9	0.64647 (10)	0.39385 (8)	0.34807 (14)	0.0119 (2)
C10	0.58431 (10)	0.32848 (8)	0.42661 (14)	0.0128 (2)
C11	0.45679 (10)	0.34678 (8)	0.40260 (14)	0.0140 (2)
C12	0.38994 (10)	0.42603 (9)	0.30137 (14)	0.0154 (2)
C13	0.45327 (11)	0.48890 (8)	0.22100 (14)	0.0160 (2)
C14	0.58179 (10)	0.47359 (8)	0.24426 (14)	0.0138 (2)
Cl1	0.37737 (3)	0.26618 (2)	0.50010 (4)	0.02190 (9)
N1	0.77963 (8)	0.37973 (7)	0.37787 (11)	0.01154 (18)
O1	0.77119 (8)	0.37345 (6)	0.08629 (10)	0.01483 (17)
H4	1.1910 (14)	0.3693 (10)	0.6601 (18)	0.017 (3)*
H5	1.1752 (14)	0.3848 (11)	0.953 (2)	0.022 (4)*
H6	0.9704 (14)	0.3937 (11)	0.977 (2)	0.019 (4)*
H7	0.7806 (13)	0.3873 (10)	0.7246 (18)	0.013 (3)*
H10	0.6287 (13)	0.2730 (11)	0.4937 (18)	0.015 (3)*
H12	0.3012 (15)	0.4359 (12)	0.288 (2)	0.025 (4)*
H13	0.4077 (15)	0.5432 (11)	0.150 (2)	0.022 (4)*
H14	0.6260 (13)	0.5169 (10)	0.1917 (18)	0.013 (3)*
H2A	1.0093 (14)	0.3108 (11)	0.2957 (18)	0.018 (4)*
H2B	1.0152 (13)	0.4271 (11)	0.2965 (18)	0.017 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0130 (5)	0.0097 (4)	0.0119 (5)	−0.0006 (4)	0.0051 (4)	−0.0003 (3)
C2	0.0112 (5)	0.0118 (5)	0.0107 (5)	0.0003 (4)	0.0046 (4)	−0.0001 (3)
C3	0.0127 (5)	0.0093 (4)	0.0112 (5)	0.0003 (3)	0.0047 (4)	0.0001 (3)
C4	0.0105 (5)	0.0113 (5)	0.0154 (5)	0.0000 (4)	0.0037 (4)	−0.0001 (4)
C5	0.0146 (5)	0.0121 (5)	0.0128 (5)	0.0006 (4)	0.0013 (4)	0.0000 (4)
C6	0.0178 (5)	0.0118 (5)	0.0107 (5)	0.0004 (4)	0.0046 (4)	0.0003 (3)
C7	0.0128 (5)	0.0120 (5)	0.0134 (5)	0.0002 (4)	0.0056 (4)	0.0005 (4)
C8	0.0114 (5)	0.0096 (4)	0.0108 (5)	0.0005 (3)	0.0023 (4)	0.0007 (3)
C9	0.0098 (5)	0.0142 (5)	0.0111 (4)	0.0005 (4)	0.0028 (4)	−0.0009 (4)
C10	0.0120 (5)	0.0137 (5)	0.0118 (5)	0.0002 (4)	0.0029 (4)	0.0008 (4)
C11	0.0125 (5)	0.0173 (5)	0.0127 (5)	−0.0033 (4)	0.0050 (4)	−0.0011 (4)
C12	0.0103 (5)	0.0208 (5)	0.0141 (5)	0.0022 (4)	0.0030 (4)	−0.0025 (4)
C13	0.0159 (5)	0.0164 (5)	0.0139 (5)	0.0044 (4)	0.0027 (4)	0.0008 (4)
C14	0.0152 (5)	0.0137 (5)	0.0122 (5)	0.0000 (4)	0.0043 (4)	0.0011 (4)
Cl1	0.01613 (15)	0.02786 (16)	0.02394 (16)	−0.00485 (10)	0.00973 (11)	0.00480 (11)
N1	0.0091 (4)	0.0155 (4)	0.0096 (4)	0.0004 (3)	0.0027 (3)	0.0009 (3)
O1	0.0152 (4)	0.0177 (4)	0.0107 (4)	−0.0002 (3)	0.0033 (3)	−0.0001 (3)

Geometric parameters (Å, º)

C1—O1	1.2170 (13)	C7—H7	0.953 (14)
C1—N1	1.3884 (13)	C8—N1	1.4148 (13)
C1—C2	1.5205 (15)	C9—C10	1.3919 (15)
C2—C3	1.5006 (14)	C9—C14	1.3940 (14)
C2—H2A	0.958 (15)	C9—N1	1.4281 (13)
C2—H2B	0.964 (15)	C10—C11	1.3845 (15)
C3—C4	1.3850 (14)	C10—H10	0.951 (14)
C3—C8	1.3963 (15)	C11—C12	1.3882 (15)
C4—C5	1.3980 (15)	C11—Cl1	1.7397 (11)
C4—H4	0.986 (15)	C12—C13	1.3890 (16)
C5—C6	1.3913 (16)	C12—H12	0.964 (15)
C5—H5	1.026 (15)	C13—C14	1.3903 (16)
C6—C7	1.3989 (15)	C13—H13	0.957 (15)
C6—H6	0.963 (15)	C14—H14	0.947 (14)
C7—C8	1.3875 (15)
O1—C1—N1	125.00 (10)	C7—C8—C3	122.20 (10)
O1—C1—C2	127.62 (10)	C7—C8—N1	128.55 (10)
N1—C1—C2	107.38 (8)	C3—C8—N1	109.22 (9)
C3—C2—C1	103.59 (8)	C10—C9—C14	121.24 (10)
C3—C2—H2A	113.8 (8)	C10—C9—N1	119.08 (9)
C1—C2—H2A	109.7 (9)	C14—C9—N1	119.67 (9)
C3—C2—H2B	111.8 (8)	C11—C10—C9	117.86 (10)
C1—C2—H2B	109.5 (8)	C11—C10—H10	121.7 (8)
H2A—C2—H2B	108.4 (12)	C9—C10—H10	120.4 (8)
C4—C3—C8	119.96 (9)	C10—C11—C12	122.32 (10)
C4—C3—C2	131.27 (10)	C10—C11—Cl1	118.62 (8)
C8—C3—C2	108.72 (9)	C12—C11—Cl1	119.06 (8)
C3—C4—C5	118.78 (10)	C11—C12—C13	118.75 (10)
C3—C4—H4	120.1 (8)	C11—C12—H12	119.5 (9)
C5—C4—H4	121.1 (8)	C13—C12—H12	121.8 (9)
C6—C5—C4	120.58 (10)	C12—C13—C14	120.49 (10)
C6—C5—H5	118.9 (9)	C12—C13—H13	119.4 (9)
C4—C5—H5	120.5 (9)	C14—C13—H13	120.1 (9)
C5—C6—C7	121.22 (10)	C13—C14—C9	119.32 (10)
C5—C6—H6	118.7 (9)	C13—C14—H14	121.0 (8)
C7—C6—H6	120.1 (9)	C9—C14—H14	119.7 (8)
C8—C7—C6	117.24 (10)	C1—N1—C8	111.08 (9)
C8—C7—H7	121.4 (8)	C1—N1—C9	124.21 (9)
C6—C7—H7	121.3 (8)	C8—N1—C9	124.47 (9)
O1—C1—C2—C3	−179.28 (10)	C10—C11—C12—C13	0.20 (16)
N1—C1—C2—C3	0.47 (10)	Cl1—C11—C12—C13	−178.72 (8)
C1—C2—C3—C4	−177.77 (10)	C11—C12—C13—C14	−1.10 (16)
C1—C2—C3—C8	−0.45 (11)	C12—C13—C14—C9	0.53 (16)
C8—C3—C4—C5	−0.81 (15)	C10—C9—C14—C13	0.97 (16)
C2—C3—C4—C5	176.26 (10)	N1—C9—C14—C13	−177.75 (10)
C3—C4—C5—C6	1.14 (15)	O1—C1—N1—C8	179.42 (10)
C4—C5—C6—C7	−0.19 (16)	C2—C1—N1—C8	−0.33 (11)
C5—C6—C7—C8	−1.05 (15)	O1—C1—N1—C9	−6.05 (16)
C6—C7—C8—C3	1.39 (15)	C2—C1—N1—C9	174.20 (9)
C6—C7—C8—N1	−176.70 (10)	C7—C8—N1—C1	178.34 (10)
C4—C3—C8—C7	−0.47 (15)	C3—C8—N1—C1	0.05 (11)
C2—C3—C8—C7	−178.15 (9)	C7—C8—N1—C9	3.82 (16)
C4—C3—C8—N1	177.95 (9)	C3—C8—N1—C9	−174.47 (9)
C2—C3—C8—N1	0.27 (11)	C10—C9—N1—C1	128.52 (11)
C14—C9—C10—C11	−1.81 (16)	C14—C9—N1—C1	−52.74 (14)
N1—C9—C10—C11	176.90 (9)	C10—C9—N1—C8	−57.67 (14)
C9—C10—C11—C12	1.23 (16)	C14—C9—N1—C8	121.07 (11)
C9—C10—C11—Cl1	−179.84 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1^i	0.951 (14)	2.471 (14)	3.3841 (13)	161.1 (11)
C13—H13···O1^ii	0.957 (15)	2.494 (15)	3.3925 (13)	156.4 (12)

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

1-(3-Chlorophenyl)-indolin-2-one (C_RT)

Crystal data

C14H10ClNO	F(000) = 504
Mr = 243.68	Dx = 1.392 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.1901 (2) Å	Cell parameters from 7649 reflections
b = 13.6596 (3) Å	θ = 2.4–27.6°
c = 8.0965 (2) Å	µ = 0.31 mm^−1
β = 109.996 (1)°	T = 296 K
V = 1162.96 (4) Å^3	Bar, colourless
Z = 4	0.60 × 0.23 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer	2359 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm^-1	Rint = 0.068
ω scans	θmax = 29.4°, θmin = 1.9°
Absorption correction: multi-scan (APEX2; Bruker, 2005)	h = −14→15
Tmin = 0.837, Tmax = 0.973	k = −18→18
21800 measured reflections	l = −11→11
3159 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	All H-atom parameters refined
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0685P)^2 + 0.1297P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3159 reflections	Δρmax = 0.38 e Å^−3
194 parameters	Δρmin = −0.56 e Å^−3

Special details

Experimental. Scan width 0.5° ω , Crystal to detector distance 5.964 cm, exposure time 32s, 21 hours for data collection, without scale. The 6 omiga-run take the following theta, initial-omiga, phi values and the following sweep-ranges, respectively -28, -28, 0, 186 (negatively run) -30, 146, 72, 186 (positively run) -28, -28, 144, 186 (negatively run) -31, 146, 216, 186 (positively run) -32, -28, 288, 186 (negatively run) -29.275, -171.726, 40, 223.0 (positively run)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.83010 (13)	0.37519 (9)	0.24314 (18)	0.0357 (3)
C2	0.97339 (13)	0.36994 (10)	0.33071 (18)	0.0350 (3)
C3	0.99289 (12)	0.37266 (9)	0.52246 (17)	0.0332 (3)
C4	1.10215 (13)	0.37232 (10)	0.6691 (2)	0.0401 (3)
C5	1.09155 (15)	0.38035 (10)	0.8349 (2)	0.0445 (3)
C6	0.97341 (15)	0.38681 (10)	0.85297 (19)	0.0424 (3)
C7	0.86177 (14)	0.38606 (10)	0.70735 (18)	0.0382 (3)
C8	0.87487 (12)	0.37960 (9)	0.54348 (17)	0.0321 (3)
C9	0.64634 (12)	0.39487 (10)	0.34614 (18)	0.0359 (3)
C10	0.58388 (13)	0.32968 (11)	0.42009 (19)	0.0409 (3)
C11	0.45727 (13)	0.34684 (12)	0.39525 (19)	0.0455 (3)
C12	0.39209 (14)	0.42498 (14)	0.2979 (2)	0.0507 (4)
C13	0.45507 (16)	0.48767 (13)	0.2224 (2)	0.0523 (4)
C14	0.58227 (15)	0.47375 (11)	0.2469 (2)	0.0442 (3)
Cl1	0.37809 (5)	0.26605 (5)	0.48804 (8)	0.0793 (2)
N1	0.77845 (10)	0.38116 (8)	0.37545 (14)	0.0362 (3)
O1	0.76945 (10)	0.37418 (8)	0.08714 (13)	0.0490 (3)
H4	1.1840 (16)	0.3671 (12)	0.654 (2)	0.044 (4)*
H5	1.1730 (17)	0.3818 (13)	0.946 (2)	0.057 (5)*
H6	0.9701 (16)	0.3922 (13)	0.970 (3)	0.054 (5)*
H7	0.7811 (16)	0.3894 (11)	0.722 (2)	0.044 (4)*
H10	0.6299 (15)	0.2743 (12)	0.491 (2)	0.044 (4)*
H12	0.3046 (18)	0.4351 (15)	0.281 (3)	0.066 (5)*
H13	0.412 (2)	0.5404 (14)	0.161 (3)	0.065 (5)*
H14	0.6268 (17)	0.5176 (14)	0.195 (2)	0.053 (5)*
H2A	1.0127 (15)	0.4231 (13)	0.298 (2)	0.046 (4)*
H2B	1.0032 (16)	0.3121 (13)	0.296 (2)	0.048 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0367 (7)	0.0345 (6)	0.0357 (7)	−0.0002 (5)	0.0120 (5)	0.0007 (5)
C2	0.0343 (7)	0.0343 (7)	0.0388 (7)	0.0001 (5)	0.0155 (6)	−0.0008 (5)
C3	0.0324 (6)	0.0290 (6)	0.0380 (7)	0.0009 (5)	0.0118 (5)	0.0010 (5)
C4	0.0305 (7)	0.0390 (7)	0.0480 (8)	0.0014 (5)	0.0100 (6)	0.0002 (6)
C5	0.0415 (8)	0.0424 (8)	0.0400 (7)	0.0019 (6)	0.0017 (6)	0.0008 (6)
C6	0.0503 (9)	0.0409 (7)	0.0338 (7)	0.0023 (6)	0.0116 (6)	0.0013 (6)
C7	0.0391 (7)	0.0392 (7)	0.0386 (7)	0.0032 (5)	0.0161 (6)	0.0025 (5)
C8	0.0305 (6)	0.0305 (6)	0.0333 (6)	0.0008 (5)	0.0080 (5)	0.0027 (5)
C9	0.0291 (6)	0.0422 (7)	0.0344 (6)	0.0020 (5)	0.0083 (5)	0.0011 (5)
C10	0.0332 (7)	0.0452 (8)	0.0416 (7)	0.0000 (6)	0.0093 (6)	0.0053 (6)
C11	0.0339 (7)	0.0608 (9)	0.0405 (7)	−0.0071 (6)	0.0112 (6)	−0.0018 (6)
C12	0.0304 (7)	0.0689 (11)	0.0488 (9)	0.0065 (7)	0.0083 (6)	−0.0071 (7)
C13	0.0468 (9)	0.0553 (9)	0.0473 (8)	0.0184 (7)	0.0063 (7)	0.0063 (7)
C14	0.0436 (8)	0.0440 (8)	0.0427 (8)	0.0040 (6)	0.0119 (6)	0.0081 (6)
Cl1	0.0539 (3)	0.1023 (4)	0.0881 (4)	−0.0215 (2)	0.0326 (3)	0.0151 (3)
N1	0.0290 (6)	0.0447 (6)	0.0333 (6)	0.0006 (4)	0.0088 (4)	0.0035 (4)
O1	0.0480 (6)	0.0623 (7)	0.0336 (5)	0.0004 (5)	0.0100 (4)	−0.0002 (5)

Geometric parameters (Å, º)

C1—O1	1.2124 (17)	C7—H7	0.952 (16)
C1—N1	1.3827 (17)	C8—N1	1.4183 (17)
C1—C2	1.5170 (19)	C9—C14	1.388 (2)
C2—C3	1.4925 (19)	C9—C10	1.388 (2)
C2—H2A	0.934 (17)	C9—N1	1.4272 (16)
C2—H2B	0.936 (18)	C10—C11	1.381 (2)
C3—C4	1.383 (2)	C10—H10	0.982 (17)
C3—C8	1.3914 (18)	C11—C12	1.378 (2)
C4—C5	1.392 (2)	C11—Cl1	1.7386 (16)
C4—H4	0.967 (17)	C12—C13	1.378 (2)
C5—C6	1.382 (2)	C12—H12	0.951 (19)
C5—H5	1.037 (18)	C13—C14	1.381 (2)
C6—C7	1.394 (2)	C13—H13	0.91 (2)
C6—H6	0.966 (19)	C14—H14	0.961 (18)
C7—C8	1.3866 (19)
O1—C1—N1	125.06 (13)	C7—C8—C3	122.46 (12)
O1—C1—C2	127.74 (13)	C7—C8—N1	128.48 (12)
N1—C1—C2	107.20 (11)	C3—C8—N1	109.04 (11)
C3—C2—C1	103.90 (11)	C14—C9—C10	120.74 (13)
C3—C2—H2A	111.3 (10)	C14—C9—N1	119.92 (12)
C1—C2—H2A	110.8 (10)	C10—C9—N1	119.33 (12)
C3—C2—H2B	113.0 (10)	C11—C10—C9	118.10 (13)
C1—C2—H2B	109.1 (10)	C11—C10—H10	121.6 (9)
H2A—C2—H2B	108.6 (14)	C9—C10—H10	120.3 (9)
C4—C3—C8	119.52 (12)	C12—C11—C10	122.04 (14)
C4—C3—C2	131.68 (12)	C12—C11—Cl1	119.38 (12)
C8—C3—C2	108.77 (11)	C10—C11—Cl1	118.57 (12)
C3—C4—C5	119.08 (13)	C13—C12—C11	118.96 (14)
C3—C4—H4	119.4 (9)	C13—C12—H12	120.1 (12)
C5—C4—H4	121.6 (10)	C11—C12—H12	120.9 (12)
C6—C5—C4	120.48 (14)	C12—C13—C14	120.58 (15)
C6—C5—H5	119.8 (10)	C12—C13—H13	118.7 (13)
C4—C5—H5	119.7 (10)	C14—C13—H13	120.7 (13)
C5—C6—C7	121.55 (14)	C13—C14—C9	119.55 (15)
C5—C6—H6	118.0 (10)	C13—C14—H14	120.9 (11)
C7—C6—H6	120.5 (10)	C9—C14—H14	119.6 (11)
C8—C7—C6	116.89 (13)	C1—N1—C8	111.09 (11)
C8—C7—H7	122.7 (10)	C1—N1—C9	124.24 (11)
C6—C7—H7	120.4 (10)	C8—N1—C9	124.50 (11)
O1—C1—C2—C3	−179.22 (13)	C10—C11—C12—C13	0.3 (2)
N1—C1—C2—C3	0.56 (13)	Cl1—C11—C12—C13	−178.92 (13)
C1—C2—C3—C4	−178.38 (13)	C11—C12—C13—C14	−1.4 (3)
C1—C2—C3—C8	−0.50 (14)	C12—C13—C14—C9	1.1 (2)
C8—C3—C4—C5	−0.89 (19)	C10—C9—C14—C13	0.3 (2)
C2—C3—C4—C5	176.80 (14)	N1—C9—C14—C13	−178.61 (14)
C3—C4—C5—C6	1.1 (2)	O1—C1—N1—C8	179.35 (13)
C4—C5—C6—C7	−0.3 (2)	C2—C1—N1—C8	−0.44 (14)
C5—C6—C7—C8	−0.7 (2)	O1—C1—N1—C9	−5.2 (2)
C6—C7—C8—C3	0.94 (19)	C2—C1—N1—C9	174.98 (12)
C6—C7—C8—N1	−177.37 (12)	C7—C8—N1—C1	178.61 (13)
C4—C3—C8—C7	−0.16 (19)	C3—C8—N1—C1	0.12 (14)
C2—C3—C8—C7	−178.34 (12)	C7—C8—N1—C9	3.2 (2)
C4—C3—C8—N1	178.44 (11)	C3—C8—N1—C9	−175.28 (11)
C2—C3—C8—N1	0.26 (14)	C14—C9—N1—C1	−54.80 (18)
C14—C9—C10—C11	−1.4 (2)	C10—C9—N1—C1	126.27 (14)
N1—C9—C10—C11	177.55 (13)	C14—C9—N1—C8	120.01 (15)
C9—C10—C11—C12	1.1 (2)	C10—C9—N1—C8	−58.92 (18)
C9—C10—C11—Cl1	−179.71 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1^i	0.982 (17)	2.515 (17)	3.4604 (18)	161.6 (13)
C13—H13···O1^ii	0.91 (2)	2.59 (2)	3.4419 (19)	154.7 (16)

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