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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 (ART, BRT and CRT) and low temperature (ALT, BLT and CLT) have been determined. Crystal A at 295 K (ART) 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 (ALT) crystallized in the triclinic space group P\overline{1} 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\overline{1} 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 BLT 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 BRT 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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618015796/yo3056sup1.cif
Contains datablocks A_LT, A_RT, B_LT, B_RT, C_LT, C_RT, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015796/yo3056A_LTsup2.hkl
Contains datablock A_LT

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015796/yo3056A_RTsup3.hkl
Contains datablock A_RT

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015796/yo3056B_LTsup4.hkl
Contains datablock B_LT

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015796/yo3056B_RTsup5.hkl
Contains datablock B_RT

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015796/yo3056C_LTsup6.hkl
Contains datablock C_LT

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015796/yo3056C_RTsup7.hkl
Contains datablock C_RT

CCDC references: 1877592; 1877591; 1877590; 1877589; 1877588; 1877587

Computing details top

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) top
Crystal data top
C14H10ClNOZ = 8
Mr = 243.68F(000) = 1008
Triclinic, P1Dx = 1.428 Mg m3
a = 9.6212 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.4483 (7) ÅCell parameters from 9973 reflections
c = 19.7967 (10) Åθ = 2.3–30.2°
α = 72.681 (1)°µ = 0.32 mm1
β = 89.995 (1)°T = 90 K
γ = 69.051 (1)°Block, colorless
V = 2267.4 (2) Å30.38 × 0.32 × 0.16 mm
Data collection top
Bruker APEXII CCD
diffractometer
11212 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm-1Rint = 0.028
ω scansθmax = 30.2°, θmin = 1.1°
Absorption correction: multi-scan
(APEX2; Bruker, 2005)
h = 1313
Tmin = 0.889, Tmax = 0.951k = 1918
45213 measured reflectionsl = 2728
12930 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035All H-atom parameters refined
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.052P)2 + 0.2422P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
12930 reflectionsΔρmax = 0.47 e Å3
770 parametersΔρmin = 0.31 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.2867 (3)0.21744 (17)0.16306 (10)0.0158 (5)
C20.3409 (3)0.11604 (18)0.22960 (10)0.0147 (5)
C30.4820 (3)0.03907 (17)0.21151 (9)0.0149 (4)
C40.5834 (3)0.06659 (17)0.24935 (10)0.0148 (4)
C50.7079 (3)0.11853 (17)0.21809 (10)0.0161 (5)
C60.7249 (3)0.06289 (16)0.14888 (10)0.0152 (4)
C70.6254 (3)0.04321 (17)0.10909 (9)0.0150 (5)
C80.5036 (3)0.09215 (16)0.14199 (9)0.0121 (4)
C90.3755 (3)0.27299 (16)0.04356 (9)0.0137 (4)
C100.2666 (2)0.28606 (16)0.00838 (9)0.0203 (4)
C110.2507 (2)0.36267 (18)0.07553 (10)0.0248 (5)
C120.3409 (3)0.42542 (19)0.09043 (11)0.0230 (5)
C130.4493 (2)0.40975 (15)0.03871 (9)0.0200 (4)
C140.4659 (2)0.33411 (15)0.02875 (9)0.0171 (4)
Cl10.87866 (8)0.12995 (4)0.10994 (2)0.01864 (12)
N10.3867 (3)0.19695 (13)0.11401 (8)0.0146 (4)
O10.1770 (2)0.30357 (12)0.15250 (7)0.0222 (3)
H40.574 (3)0.1028 (17)0.2970 (10)0.024 (6)*
H50.774 (3)0.1910 (18)0.2449 (10)0.022 (6)*
H70.645 (3)0.0817 (17)0.0609 (10)0.024 (5)*
H100.203 (3)0.2456 (18)0.0018 (11)0.033 (6)*
H110.171 (3)0.3747 (18)0.1104 (11)0.036 (6)*
H120.317 (3)0.4835 (18)0.1359 (11)0.028 (6)*
H130.515 (2)0.4500 (17)0.0481 (10)0.026 (5)*
H140.535 (3)0.3253 (18)0.0645 (10)0.031 (6)*
H2B0.364 (3)0.1394 (16)0.2669 (10)0.017 (5)*
H2A0.273 (3)0.0796 (18)0.2436 (10)0.020*
C210.8146 (3)0.20245 (17)0.16916 (10)0.0149 (4)
C220.8716 (3)0.09776 (17)0.23351 (10)0.0145 (4)
C231.0080 (3)0.02145 (17)0.21084 (10)0.0138 (4)
C241.1117 (3)0.08342 (16)0.24614 (9)0.0147 (4)
C251.2331 (3)0.13302 (17)0.21223 (10)0.0150 (4)
C261.2444 (3)0.07476 (16)0.14246 (9)0.0140 (4)
C271.1400 (3)0.03106 (16)0.10449 (9)0.0137 (4)
C281.0207 (3)0.07716 (16)0.14048 (9)0.0125 (4)
C290.8828 (3)0.26161 (16)0.04554 (9)0.0132 (4)
C300.8476 (2)0.23351 (15)0.01278 (9)0.0164 (4)
C310.8214 (2)0.31207 (16)0.08046 (9)0.0193 (4)
C320.8290 (3)0.41622 (19)0.08909 (11)0.0209 (5)
C330.8643 (2)0.44282 (15)0.03061 (9)0.0190 (4)
C340.8918 (2)0.36461 (15)0.03751 (9)0.0161 (4)
Cl21.39793 (7)0.13603 (4)0.10140 (2)0.01704 (11)
N20.9049 (3)0.18261 (13)0.11587 (8)0.0132 (4)
O20.7097 (2)0.28920 (12)0.16316 (7)0.0201 (4)
H241.112 (2)0.1228 (15)0.2941 (9)0.014 (5)*
H251.298 (3)0.207 (2)0.2356 (11)0.029 (6)*
H271.152 (4)0.0735 (18)0.0542 (11)0.035*
H300.843 (2)0.1602 (16)0.0062 (9)0.017 (5)*
H310.800 (2)0.2896 (15)0.1184 (9)0.015 (5)*
H320.804 (3)0.4743 (16)0.1362 (10)0.018 (6)*
H330.867 (2)0.5123 (16)0.0342 (9)0.022 (5)*
H340.914 (2)0.3808 (15)0.0766 (9)0.013 (5)*
H22A0.800 (3)0.0641 (16)0.2465 (10)0.016*
H22B0.900 (2)0.1158 (14)0.2719 (9)0.009 (5)*
C410.5162 (3)0.29434 (17)0.33062 (9)0.0148 (4)
C420.4681 (3)0.39964 (18)0.26548 (10)0.0146 (4)
C430.5276 (3)0.47495 (16)0.28759 (9)0.0121 (4)
C440.5278 (3)0.58049 (17)0.25115 (9)0.0161 (4)
C450.5986 (3)0.62997 (18)0.28463 (10)0.0165 (4)
C460.6675 (3)0.57407 (16)0.35372 (9)0.0133 (4)
C470.6679 (3)0.46825 (16)0.39238 (10)0.0132 (4)
C480.5989 (3)0.42123 (16)0.35759 (9)0.0126 (4)
C490.6411 (3)0.23703 (16)0.45317 (9)0.0132 (4)
C500.5795 (2)0.26423 (15)0.51157 (9)0.0162 (4)
C510.6324 (2)0.18647 (17)0.57956 (9)0.0192 (4)
C520.7445 (3)0.08334 (18)0.58807 (10)0.0182 (5)
C530.8074 (2)0.05670 (15)0.52943 (9)0.0195 (4)
C540.7571 (2)0.13392 (15)0.46154 (9)0.0166 (4)
Cl30.75702 (8)0.63669 (4)0.39429 (3)0.01786 (12)
N30.5868 (3)0.31493 (14)0.38306 (8)0.0133 (4)
O30.4955 (2)0.20782 (12)0.33728 (7)0.0210 (4)
H440.470 (3)0.6225 (16)0.2014 (10)0.020 (6)*
H450.610 (3)0.7006 (19)0.2555 (10)0.026 (6)*
H470.707 (3)0.4348 (18)0.4391 (11)0.031*
H500.500 (2)0.3326 (16)0.5045 (9)0.019 (5)*
H510.582 (2)0.2051 (16)0.6178 (10)0.021 (5)*
H520.801 (3)0.0223 (18)0.6355 (11)0.029 (6)*
H530.882 (2)0.0156 (15)0.5352 (9)0.015 (5)*
H540.796 (2)0.1186 (15)0.4214 (9)0.013 (4)*
H42B0.496 (3)0.3845 (18)0.2199 (11)0.031 (6)*
H42A0.356 (3)0.4227 (19)0.2617 (11)0.029 (6)*
C610.0068 (3)0.28499 (17)0.33803 (9)0.0160 (5)
C620.0403 (3)0.38884 (18)0.27152 (10)0.0158 (5)
C630.0237 (3)0.46422 (16)0.29103 (9)0.0121 (4)
C640.0211 (3)0.57014 (17)0.25488 (9)0.0161 (4)
C650.0933 (3)0.62025 (17)0.28724 (10)0.0152 (4)
C660.1666 (3)0.56337 (16)0.35529 (9)0.0141 (4)
C670.1703 (3)0.45679 (17)0.39420 (10)0.0135 (4)
C680.0994 (3)0.40989 (16)0.36034 (9)0.0134 (4)
C690.1443 (3)0.22764 (16)0.45795 (9)0.0143 (4)
C700.0513 (2)0.21653 (16)0.50978 (9)0.0212 (4)
C710.1098 (2)0.13908 (18)0.57723 (9)0.0256 (5)
C720.2610 (3)0.07568 (18)0.59221 (10)0.0202 (5)
C730.3565 (2)0.08915 (16)0.54019 (10)0.0209 (4)
C740.2990 (2)0.16497 (16)0.47246 (9)0.0186 (4)
Cl40.25518 (8)0.62717 (4)0.39532 (3)0.01752 (11)
N40.0858 (3)0.30472 (14)0.38786 (8)0.0144 (4)
O40.0187 (2)0.19957 (12)0.34720 (7)0.0225 (3)
H640.042 (3)0.6116 (16)0.2045 (10)0.022 (6)*
H650.103 (3)0.694 (2)0.2585 (11)0.038 (7)*
H670.211 (3)0.4221 (16)0.4393 (10)0.016 (5)*
H700.051 (3)0.2640 (19)0.4983 (12)0.044 (7)*
H710.048 (2)0.1317 (17)0.6134 (10)0.027 (5)*
H730.465 (2)0.0441 (17)0.5500 (10)0.028 (6)*
H740.367 (2)0.1757 (16)0.4354 (10)0.024 (5)*
H62A0.155 (3)0.4128 (17)0.2663 (10)0.019 (5)*
H62B0.006 (3)0.3664 (18)0.2271 (10)0.027 (6)*
H720.319 (3)0.0144 (15)0.6385 (9)0.013 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0138 (11)0.0191 (10)0.0145 (8)0.0057 (8)0.0026 (7)0.0060 (8)
C20.0140 (11)0.0182 (10)0.0123 (8)0.0058 (8)0.0039 (7)0.0058 (7)
C30.0159 (11)0.0174 (10)0.0147 (8)0.0093 (9)0.0022 (7)0.0061 (7)
C40.0169 (11)0.0157 (9)0.0128 (8)0.0092 (8)0.0004 (7)0.0024 (7)
C50.0189 (12)0.0129 (9)0.0148 (8)0.0068 (8)0.0013 (8)0.0013 (7)
C60.0134 (10)0.0147 (9)0.0196 (8)0.0057 (8)0.0019 (8)0.0079 (7)
C70.0171 (12)0.0150 (9)0.0128 (8)0.0060 (9)0.0020 (8)0.0042 (7)
C80.0110 (10)0.0120 (8)0.0127 (8)0.0036 (8)0.0000 (7)0.0039 (7)
C90.0138 (11)0.0126 (9)0.0095 (8)0.0005 (9)0.0014 (8)0.0017 (7)
C100.0197 (10)0.0232 (10)0.0205 (9)0.0096 (8)0.0018 (7)0.0085 (8)
C110.0255 (12)0.0329 (12)0.0144 (9)0.0091 (10)0.0009 (8)0.0076 (8)
C120.0281 (15)0.0214 (11)0.0148 (9)0.0054 (10)0.0092 (9)0.0040 (8)
C130.0174 (10)0.0187 (9)0.0221 (9)0.0067 (8)0.0077 (7)0.0040 (7)
C140.0124 (9)0.0181 (9)0.0181 (8)0.0039 (8)0.0009 (7)0.0042 (7)
Cl10.0161 (3)0.0178 (2)0.0208 (2)0.0034 (2)0.0028 (2)0.00805 (19)
N10.0155 (10)0.0126 (8)0.0119 (7)0.0027 (7)0.0026 (7)0.0017 (6)
O10.0208 (9)0.0215 (7)0.0178 (6)0.0014 (7)0.0052 (6)0.0049 (5)
C210.0137 (10)0.0182 (9)0.0133 (8)0.0058 (8)0.0022 (7)0.0060 (7)
C220.0166 (10)0.0163 (9)0.0121 (8)0.0064 (9)0.0037 (7)0.0062 (7)
C230.0151 (10)0.0149 (9)0.0149 (8)0.0080 (8)0.0033 (7)0.0066 (7)
C240.0181 (11)0.0147 (9)0.0115 (8)0.0082 (9)0.0001 (7)0.0018 (7)
C250.0170 (11)0.0100 (9)0.0153 (8)0.0040 (8)0.0009 (8)0.0015 (7)
C260.0132 (11)0.0139 (9)0.0171 (8)0.0056 (8)0.0022 (7)0.0072 (7)
C270.0150 (11)0.0129 (9)0.0128 (8)0.0053 (8)0.0022 (8)0.0035 (7)
C280.0136 (10)0.0124 (9)0.0125 (8)0.0054 (8)0.0004 (8)0.0047 (7)
C290.0093 (10)0.0137 (9)0.0100 (8)0.0008 (8)0.0005 (8)0.0009 (7)
C300.0142 (9)0.0165 (9)0.0177 (8)0.0036 (7)0.0042 (6)0.0070 (7)
C310.0152 (10)0.0244 (10)0.0140 (8)0.0022 (8)0.0004 (7)0.0062 (7)
C320.0181 (13)0.0219 (11)0.0148 (9)0.0014 (10)0.0051 (8)0.0020 (8)
C330.0165 (10)0.0152 (9)0.0203 (9)0.0032 (8)0.0023 (7)0.0017 (7)
C340.0142 (9)0.0151 (9)0.0166 (8)0.0029 (7)0.0003 (7)0.0050 (7)
Cl20.0150 (3)0.0158 (2)0.0183 (2)0.0027 (2)0.0033 (2)0.00628 (18)
N20.0147 (9)0.0123 (7)0.0102 (7)0.0034 (7)0.0020 (7)0.0023 (6)
O20.0154 (8)0.0216 (7)0.0186 (6)0.0006 (6)0.0046 (6)0.0076 (6)
C410.0140 (10)0.0191 (10)0.0120 (8)0.0061 (8)0.0031 (7)0.0060 (7)
C420.0167 (10)0.0155 (9)0.0099 (7)0.0049 (8)0.0007 (7)0.0029 (7)
C430.0126 (10)0.0128 (9)0.0085 (8)0.0029 (8)0.0021 (7)0.0023 (7)
C440.0164 (10)0.0158 (9)0.0117 (8)0.0029 (8)0.0021 (8)0.0020 (7)
C450.0171 (11)0.0123 (9)0.0172 (9)0.0040 (9)0.0044 (8)0.0024 (7)
C460.0133 (11)0.0133 (9)0.0138 (8)0.0055 (8)0.0026 (7)0.0043 (7)
C470.0119 (11)0.0130 (9)0.0129 (8)0.0035 (8)0.0018 (7)0.0031 (7)
C480.0132 (11)0.0114 (9)0.0108 (8)0.0034 (8)0.0030 (8)0.0018 (7)
C490.0127 (11)0.0127 (9)0.0126 (8)0.0049 (8)0.0024 (8)0.0015 (7)
C500.0157 (8)0.0178 (9)0.0155 (8)0.0070 (7)0.0015 (6)0.0048 (7)
C510.0260 (9)0.0252 (10)0.0123 (8)0.0158 (8)0.0028 (7)0.0065 (7)
C520.0256 (12)0.0191 (10)0.0129 (8)0.0167 (9)0.0005 (8)0.0010 (8)
C530.0224 (9)0.0148 (9)0.0201 (8)0.0082 (7)0.0015 (7)0.0024 (7)
C540.0193 (9)0.0138 (9)0.0161 (8)0.0064 (7)0.0023 (7)0.0037 (7)
Cl30.0214 (3)0.0159 (2)0.0187 (2)0.0094 (2)0.0023 (2)0.00604 (18)
N30.0164 (10)0.0137 (8)0.0104 (7)0.0077 (7)0.0007 (7)0.0020 (6)
O30.0292 (9)0.0193 (7)0.0179 (6)0.0135 (7)0.0010 (6)0.0051 (5)
C610.0184 (11)0.0188 (10)0.0128 (8)0.0071 (9)0.0028 (7)0.0077 (7)
C620.0176 (11)0.0174 (10)0.0115 (8)0.0059 (8)0.0004 (8)0.0044 (7)
C630.0116 (10)0.0145 (9)0.0099 (8)0.0040 (8)0.0020 (7)0.0046 (7)
C640.0167 (11)0.0177 (9)0.0107 (7)0.0043 (9)0.0002 (8)0.0025 (7)
C650.0176 (11)0.0123 (9)0.0146 (8)0.0057 (8)0.0029 (8)0.0028 (7)
C660.0139 (11)0.0159 (9)0.0136 (8)0.0061 (8)0.0014 (7)0.0059 (7)
C670.0121 (11)0.0138 (9)0.0122 (8)0.0033 (8)0.0001 (7)0.0028 (7)
C680.0125 (11)0.0118 (9)0.0118 (8)0.0013 (8)0.0009 (8)0.0020 (7)
C690.0162 (11)0.0134 (9)0.0130 (8)0.0057 (9)0.0011 (8)0.0036 (7)
C700.0191 (9)0.0237 (10)0.0152 (8)0.0024 (8)0.0017 (7)0.0049 (7)
C710.0309 (11)0.0312 (12)0.0140 (8)0.0123 (9)0.0080 (8)0.0054 (8)
C720.0298 (13)0.0194 (10)0.0130 (8)0.0141 (10)0.0009 (9)0.0015 (8)
C730.0200 (9)0.0201 (10)0.0208 (9)0.0088 (8)0.0042 (7)0.0022 (7)
C740.0173 (9)0.0200 (10)0.0187 (9)0.0093 (7)0.0031 (7)0.0036 (7)
Cl40.0210 (3)0.0170 (2)0.0179 (2)0.0101 (2)0.00083 (19)0.00660 (18)
N40.0184 (10)0.0140 (8)0.0115 (7)0.0081 (8)0.0006 (7)0.0027 (6)
O40.0321 (9)0.0206 (7)0.0196 (7)0.0156 (7)0.0004 (6)0.0062 (6)
Geometric parameters (Å, º) top
C1—O11.217 (3)C41—O31.219 (3)
C1—N11.384 (3)C41—N31.387 (3)
C1—C21.513 (3)C41—C421.525 (3)
C2—C31.502 (3)C42—C431.492 (3)
C2—H2B0.94 (2)C42—H42B1.00 (2)
C2—H2A0.95 (3)C42—H42A1.00 (3)
C3—C41.381 (3)C43—C441.388 (3)
C3—C81.403 (3)C43—C481.401 (2)
C4—C51.401 (3)C44—C451.391 (3)
C4—H40.947 (19)C44—H441.021 (19)
C5—C61.393 (3)C45—C461.381 (3)
C5—H50.94 (2)C45—H451.00 (2)
C6—C71.388 (3)C46—C471.400 (3)
C6—Cl11.748 (2)C46—Cl31.737 (2)
C7—C81.391 (3)C47—C481.369 (3)
C7—H71.00 (2)C47—H470.91 (2)
C8—N11.400 (3)C48—N31.414 (3)
C9—C141.373 (3)C49—C501.385 (2)
C9—C101.395 (3)C49—C541.397 (3)
C9—N11.440 (2)C49—N31.428 (2)
C10—C111.387 (3)C50—C511.395 (2)
C10—H100.94 (2)C50—H500.935 (19)
C11—C121.388 (4)C51—C521.381 (3)
C11—H110.96 (2)C51—H510.945 (18)
C12—C131.377 (3)C52—C531.391 (3)
C12—H120.96 (2)C52—H521.04 (2)
C13—C141.385 (2)C53—C541.389 (2)
C13—H130.96 (2)C53—H530.954 (18)
C14—H140.92 (2)C54—H540.924 (17)
C21—O21.212 (3)C61—O41.220 (3)
C21—N21.393 (3)C61—N41.386 (3)
C21—C221.512 (3)C61—C621.530 (3)
C22—C231.512 (3)C62—C631.495 (3)
C22—H22A0.95 (2)C62—H62A1.03 (2)
C22—H22B0.930 (18)C62—H62B1.03 (2)
C23—C241.371 (3)C63—C641.382 (3)
C23—C281.400 (3)C63—C681.404 (3)
C24—C251.404 (3)C64—C651.393 (3)
C24—H240.940 (17)C64—H641.05 (2)
C25—C261.396 (3)C65—C661.378 (3)
C25—H250.93 (2)C65—H651.03 (3)
C26—C271.393 (3)C66—C671.398 (3)
C26—Cl21.746 (2)C66—Cl41.737 (2)
C27—C281.401 (3)C67—C681.368 (3)
C27—H271.02 (2)C67—H670.889 (19)
C28—N21.396 (3)C68—N41.410 (3)
C29—C341.381 (3)C69—C701.371 (3)
C29—C301.394 (2)C69—C741.402 (3)
C29—N21.439 (2)C69—N41.430 (2)
C30—C311.393 (2)C70—C711.392 (2)
C30—H300.971 (18)C70—H700.94 (2)
C31—C321.388 (3)C71—C721.377 (3)
C31—H310.937 (18)C71—H710.94 (2)
C32—C331.385 (3)C72—C731.394 (3)
C32—H320.985 (18)C72—H721.025 (18)
C33—C341.397 (2)C73—C741.388 (2)
C33—H330.92 (2)C73—H730.99 (2)
C34—H340.909 (18)C74—H740.994 (19)
O1—C1—N1124.23 (18)O3—C41—N3125.11 (18)
O1—C1—C2128.11 (19)O3—C41—C42127.49 (19)
N1—C1—C2107.66 (18)N3—C41—C42107.38 (18)
C3—C2—C1103.57 (16)C43—C42—C41103.28 (16)
C3—C2—H2B110.0 (14)C43—C42—H42B117.4 (15)
C1—C2—H2B107.8 (12)C41—C42—H42B113.9 (13)
C3—C2—H2A111.0 (13)C43—C42—H42A115.5 (13)
C1—C2—H2A115.4 (13)C41—C42—H42A100.8 (13)
H2B—C2—H2A108.9 (18)H42B—C42—H42A105 (2)
C4—C3—C8119.6 (2)C44—C43—C48118.8 (2)
C4—C3—C2132.32 (19)C44—C43—C42131.84 (18)
C8—C3—C2108.05 (17)C48—C43—C42109.34 (17)
C3—C4—C5119.45 (19)C43—C44—C45119.50 (19)
C3—C4—H4121.2 (13)C43—C44—H44119.3 (12)
C5—C4—H4119.3 (14)C45—C44—H44121.1 (12)
C6—C5—C4119.04 (19)C46—C45—C44119.8 (2)
C6—C5—H5123.5 (13)C46—C45—H45121.3 (13)
C4—C5—H5117.5 (13)C44—C45—H45118.3 (12)
C5—C6—C7123.2 (2)C45—C46—C47122.2 (2)
C5—C6—Cl1118.51 (16)C45—C46—Cl3119.14 (16)
C7—C6—Cl1118.25 (15)C47—C46—Cl3118.66 (15)
C8—C7—C6116.03 (18)C48—C47—C46116.50 (18)
C8—C7—H7123.4 (14)C48—C47—H47122.0 (17)
C6—C7—H7120.6 (15)C46—C47—H47121.4 (17)
C7—C8—N1127.83 (18)C47—C48—C43123.16 (19)
C7—C8—C3122.61 (19)C47—C48—N3128.19 (17)
N1—C8—C3109.56 (18)C43—C48—N3108.64 (18)
C14—C9—C10120.95 (17)C50—C49—C54121.00 (17)
C14—C9—N1120.7 (2)C50—C49—N3120.13 (17)
C10—C9—N1118.3 (2)C54—C49—N3118.87 (16)
C11—C10—C9118.66 (18)C49—C50—C51119.34 (16)
C11—C10—H10120.1 (13)C49—C50—H50119.5 (11)
C9—C10—H10121.3 (13)C51—C50—H50121.1 (11)
C12—C11—C10120.51 (19)C52—C51—C50119.98 (16)
C12—C11—H11121.0 (13)C52—C51—H51122.6 (12)
C10—C11—H11118.3 (13)C50—C51—H51117.1 (12)
C13—C12—C11119.83 (19)C51—C52—C53120.58 (18)
C13—C12—H12123.2 (17)C51—C52—H52127.3 (12)
C11—C12—H12116.7 (18)C53—C52—H52111.7 (13)
C12—C13—C14120.31 (18)C54—C53—C52120.03 (18)
C12—C13—H13121.6 (12)C54—C53—H53119.5 (10)
C14—C13—H13118.1 (12)C52—C53—H53120.4 (10)
C9—C14—C13119.71 (17)C53—C54—C49119.05 (16)
C9—C14—H14119.2 (13)C53—C54—H54122.3 (11)
C13—C14—H14121.1 (13)C49—C54—H54118.7 (11)
C1—N1—C8111.15 (15)C41—N3—C48111.23 (15)
C1—N1—C9125.23 (18)C41—N3—C49123.51 (18)
C8—N1—C9123.61 (18)C48—N3—C49125.25 (17)
O2—C21—N2124.69 (18)O4—C61—N4125.00 (18)
O2—C21—C22127.60 (19)O4—C61—C62127.73 (19)
N2—C21—C22107.71 (18)N4—C61—C62107.27 (18)
C21—C22—C23103.39 (17)C63—C62—C61103.53 (17)
C21—C22—H22A113.3 (12)C63—C62—H62A117.7 (12)
C23—C22—H22A111.8 (12)C61—C62—H62A101.5 (11)
C21—C22—H22B109.1 (11)C63—C62—H62B116.5 (15)
C23—C22—H22B110.2 (12)C61—C62—H62B110.5 (12)
H22A—C22—H22B109.0 (16)H62A—C62—H62B105.9 (18)
C24—C23—C28120.1 (2)C64—C63—C68118.5 (2)
C24—C23—C22132.08 (18)C64—C63—C62132.84 (18)
C28—C23—C22107.84 (17)C68—C63—C62108.65 (17)
C23—C24—C25119.69 (19)C63—C64—C65119.93 (19)
C23—C24—H24123.7 (12)C63—C64—H64117.3 (12)
C25—C24—H24116.4 (12)C65—C64—H64122.6 (12)
C26—C25—C24119.01 (19)C66—C65—C64119.41 (19)
C26—C25—H25122.4 (13)C66—C65—H65120.0 (14)
C24—C25—H25118.3 (14)C64—C65—H65120.2 (13)
C25—C26—C27122.9 (2)C65—C66—C67122.6 (2)
C25—C26—Cl2118.63 (16)C65—C66—Cl4118.98 (16)
C27—C26—Cl2118.43 (15)C67—C66—Cl4118.44 (15)
C26—C27—C28116.03 (17)C68—C67—C66116.28 (18)
C26—C27—H27121.9 (15)C68—C67—H67120.8 (15)
C28—C27—H27122.0 (15)C66—C67—H67122.8 (15)
N2—C28—C23110.10 (18)C67—C68—C63123.28 (19)
N2—C28—C27127.58 (17)C67—C68—N4127.37 (18)
C23—C28—C27122.25 (19)C63—C68—N4109.33 (19)
C34—C29—C30121.55 (17)C70—C69—C74121.03 (17)
C34—C29—N2119.49 (16)C70—C69—N4120.6 (2)
C30—C29—N2118.92 (18)C74—C69—N4118.4 (2)
C29—C30—C31118.51 (17)C69—C70—C71119.75 (18)
C29—C30—H30120.4 (11)C69—C70—H70117.8 (14)
C31—C30—H30121.0 (11)C71—C70—H70122.4 (14)
C32—C31—C30120.41 (17)C72—C71—C70120.04 (18)
C32—C31—H31123.6 (11)C72—C71—H71119.2 (13)
C30—C31—H31116.0 (11)C70—C71—H71120.7 (13)
C33—C32—C31120.39 (19)C71—C72—C73120.28 (18)
C33—C32—H32118.4 (12)C71—C72—H72128.6 (13)
C31—C32—H32121.2 (12)C73—C72—H72111.1 (13)
C32—C33—C34119.82 (18)C74—C73—C72120.12 (18)
C32—C33—H33122.6 (11)C74—C73—H73118.6 (11)
C34—C33—H33117.5 (11)C72—C73—H73121.3 (11)
C29—C34—C33119.32 (16)C73—C74—C69118.73 (17)
C29—C34—H34119.6 (11)C73—C74—H74120.4 (11)
C33—C34—H34121.1 (11)C69—C74—H74120.9 (11)
C21—N2—C28110.85 (15)C61—N4—C68111.19 (16)
C21—N2—C29124.24 (17)C61—N4—C69123.69 (18)
C28—N2—C29124.90 (17)C68—N4—C69125.12 (18)
O1—C1—C2—C3178.6 (2)O3—C41—C42—C43178.3 (2)
N1—C1—C2—C30.6 (2)N3—C41—C42—C432.9 (2)
C1—C2—C3—C4179.6 (2)C41—C42—C43—C44176.3 (2)
C1—C2—C3—C80.1 (2)C41—C42—C43—C481.1 (3)
C8—C3—C4—C51.0 (3)C48—C43—C44—C450.2 (3)
C2—C3—C4—C5179.6 (2)C42—C43—C44—C45177.1 (2)
C3—C4—C5—C61.1 (3)C43—C44—C45—C460.2 (4)
C4—C5—C6—C71.1 (3)C44—C45—C46—C470.6 (4)
C4—C5—C6—Cl1178.72 (17)C44—C45—C46—Cl3179.37 (19)
C5—C6—C7—C80.9 (3)C45—C46—C47—C481.4 (3)
Cl1—C6—C7—C8178.92 (16)Cl3—C46—C47—C48178.58 (16)
C6—C7—C8—N1179.3 (2)C46—C47—C48—C431.4 (3)
C6—C7—C8—C30.7 (3)C46—C47—C48—N3178.0 (2)
C4—C3—C8—C70.8 (3)C44—C43—C48—C470.6 (3)
C2—C3—C8—C7179.60 (19)C42—C43—C48—C47178.5 (2)
C4—C3—C8—N1179.2 (2)C44—C43—C48—N3178.9 (2)
C2—C3—C8—N10.3 (3)C42—C43—C48—N31.0 (3)
C14—C9—C10—C110.3 (3)C54—C49—C50—C511.2 (3)
N1—C9—C10—C11177.28 (17)N3—C49—C50—C51179.08 (19)
C9—C10—C11—C120.4 (3)C49—C50—C51—C520.3 (3)
C10—C11—C12—C131.5 (3)C50—C51—C52—C531.1 (3)
C11—C12—C13—C141.9 (3)C51—C52—C53—C540.2 (3)
C10—C9—C14—C130.1 (3)C52—C53—C54—C491.3 (3)
N1—C9—C14—C13177.65 (17)C50—C49—C54—C532.1 (3)
C12—C13—C14—C91.3 (3)N3—C49—C54—C53178.25 (19)
O1—C1—N1—C8178.4 (2)O3—C41—N3—C48177.5 (2)
C2—C1—N1—C80.8 (2)C42—C41—N3—C483.7 (3)
O1—C1—N1—C90.7 (4)O3—C41—N3—C491.9 (4)
C2—C1—N1—C9179.9 (2)C42—C41—N3—C49176.9 (2)
C7—C8—N1—C1179.2 (2)C47—C48—N3—C41176.4 (2)
C3—C8—N1—C10.8 (3)C43—C48—N3—C413.0 (3)
C7—C8—N1—C90.1 (3)C47—C48—N3—C492.9 (4)
C3—C8—N1—C9179.9 (2)C43—C48—N3—C49177.6 (2)
C14—C9—N1—C1103.8 (3)C50—C49—N3—C41115.9 (2)
C10—C9—N1—C173.8 (3)C54—C49—N3—C4164.4 (3)
C14—C9—N1—C875.2 (3)C50—C49—N3—C4864.8 (3)
C10—C9—N1—C8107.2 (3)C54—C49—N3—C48114.8 (2)
O2—C21—C22—C23177.0 (2)O4—C61—C62—C63179.3 (2)
N2—C21—C22—C233.1 (2)N4—C61—C62—C630.8 (2)
C21—C22—C23—C24177.1 (2)C61—C62—C63—C64179.8 (2)
C21—C22—C23—C282.0 (2)C61—C62—C63—C680.4 (2)
C28—C23—C24—C252.0 (3)C68—C63—C64—C650.3 (3)
C22—C23—C24—C25177.0 (2)C62—C63—C64—C65179.5 (2)
C23—C24—C25—C261.0 (3)C63—C64—C65—C660.1 (3)
C24—C25—C26—C270.1 (3)C64—C65—C66—C670.8 (4)
C24—C25—C26—Cl2178.74 (17)C64—C65—C66—Cl4179.56 (18)
C25—C26—C27—C280.1 (3)C65—C66—C67—C681.5 (3)
Cl2—C26—C27—C28178.78 (16)Cl4—C66—C67—C68179.82 (17)
C24—C23—C28—N2179.1 (2)C66—C67—C68—C631.2 (3)
C22—C23—C28—N20.1 (3)C66—C67—C68—N4179.3 (2)
C24—C23—C28—C272.1 (3)C64—C63—C68—C670.4 (3)
C22—C23—C28—C27177.09 (19)C62—C63—C68—C67179.8 (2)
C26—C27—C28—N2177.4 (2)C64—C63—C68—N4178.8 (2)
C26—C27—C28—C231.0 (3)C62—C63—C68—N41.4 (3)
C34—C29—C30—C310.1 (3)C74—C69—C70—C712.3 (3)
N2—C29—C30—C31177.85 (18)N4—C69—C70—C71178.44 (19)
C29—C30—C31—C320.6 (3)C69—C70—C71—C721.4 (3)
C30—C31—C32—C330.7 (4)C70—C71—C72—C730.4 (3)
C31—C32—C33—C340.3 (4)C71—C72—C73—C741.4 (3)
C30—C29—C34—C330.3 (3)C72—C73—C74—C690.5 (3)
N2—C29—C34—C33177.44 (19)C70—C69—C74—C731.4 (3)
C32—C33—C34—C290.2 (3)N4—C69—C74—C73179.37 (18)
O2—C21—N2—C28176.8 (2)O4—C61—N4—C68178.4 (2)
C22—C21—N2—C283.3 (3)C62—C61—N4—C681.6 (3)
O2—C21—N2—C292.0 (4)O4—C61—N4—C691.9 (4)
C22—C21—N2—C29177.9 (2)C62—C61—N4—C69178.1 (2)
C23—C28—N2—C212.0 (3)C67—C68—N4—C61179.7 (2)
C27—C28—N2—C21174.7 (2)C63—C68—N4—C611.9 (3)
C23—C28—N2—C29179.2 (2)C67—C68—N4—C690.6 (4)
C27—C28—N2—C294.0 (4)C63—C68—N4—C69177.8 (2)
C34—C29—N2—C2161.5 (3)C70—C69—N4—C6175.9 (3)
C30—C29—N2—C21116.3 (2)C74—C69—N4—C61104.9 (3)
C34—C29—N2—C28117.1 (2)C70—C69—N4—C68103.8 (3)
C30—C29—N2—C2865.1 (3)C74—C69—N4—C6875.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O20.92 (2)2.39 (2)3.314 (2)175.0 (18)
C2—H2B···O30.94 (2)2.45 (2)3.340 (3)159.0 (19)
C22—H22B···O4i0.930 (18)2.397 (19)3.305 (3)165.4 (15)
C42—H42B···O21.00 (2)2.47 (2)3.322 (3)143 (2)
C74—H74···O30.994 (19)2.319 (19)3.306 (2)171.8 (16)
C62—H62B···O11.03 (2)2.38 (2)3.336 (3)154 (2)
Symmetry code: (i) x+1, y, z.
6-Chloro-1-phenylindolin-2-one (A_RT) top
Crystal data top
C14H10ClNOF(000) = 504
Mr = 243.68Dx = 1.377 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.7217 (8) ÅCell parameters from 5830 reflections
b = 4.8842 (3) Åθ = 2.3–25.9°
c = 19.9554 (14) ŵ = 0.31 mm1
β = 108.577 (1)°T = 295 K
V = 1175.33 (13) Å3Block, colorless
Z = 40.38 × 0.32 × 0.16 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2503 reflections with I > 2σ(I)
ω scansRint = 0.022
Absorption correction: multi-scan
APEX2 Software Suite (Bruker, 2005)
θmax = 30.2°, θmin = 1.7°
Tmin = 0.893, Tmax = 0.953h = 1717
18368 measured reflectionsk = 66
3438 independent reflectionsl = 2726
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041All H-atom parameters refined
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0592P)2 + 0.1874P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3438 reflectionsΔρmax = 0.29 e Å3
246 parametersΔρmin = 0.33 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl11.02300 (3)0.13142 (9)0.39339 (2)0.06708 (15)
O10.54649 (11)0.8081 (3)0.34224 (7)0.0801 (4)
N10.69396 (9)0.5144 (2)0.38432 (5)0.0492 (3)
C50.90732 (13)0.1921 (3)0.28554 (8)0.0566 (4)
C60.92024 (11)0.1067 (3)0.35376 (7)0.0498 (3)
C70.85347 (11)0.2032 (3)0.39196 (7)0.0470 (3)
C80.77239 (10)0.3888 (3)0.35832 (6)0.0434 (3)
C90.68828 (11)0.4769 (3)0.45445 (6)0.0469 (3)
C100.7745 (5)0.5750 (11)0.5097 (2)0.0568 (10)0.528 (10)
H100.830 (3)0.665 (7)0.5036 (17)0.059 (9)*0.528 (10)
C110.7655 (6)0.5472 (13)0.5770 (3)0.0698 (13)0.528 (10)
H110.821 (3)0.620 (8)0.612 (2)0.077 (11)*0.528 (10)
C140.5989 (4)0.3505 (14)0.4624 (2)0.0581 (12)0.528 (10)
H140.542 (3)0.299 (8)0.422 (2)0.070 (10)*0.528 (10)
C130.5914 (5)0.3287 (14)0.5303 (2)0.0692 (14)0.528 (10)
H130.531 (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)
C120.67357 (17)0.4190 (5)0.58814 (9)0.0742 (5)
C40.82503 (13)0.3798 (3)0.25342 (7)0.0549 (3)
C30.75626 (11)0.4785 (3)0.28895 (6)0.0470 (3)
C20.66060 (14)0.6719 (3)0.26879 (7)0.0559 (3)
C10.62326 (12)0.6806 (3)0.33387 (7)0.0548 (3)
H2A0.6820 (14)0.861 (4)0.2592 (9)0.067 (5)*
H2B0.6002 (17)0.610 (4)0.2284 (11)0.081 (6)*
H40.8135 (14)0.445 (4)0.2049 (9)0.068 (5)*
H50.9551 (14)0.125 (3)0.2586 (9)0.064 (5)*
H70.8627 (13)0.145 (3)0.4400 (9)0.054 (4)*
H120.6594 (18)0.383 (4)0.6330 (12)0.092 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0615 (2)0.0706 (3)0.0708 (3)0.01147 (18)0.02344 (19)0.00198 (18)
O10.0748 (7)0.0955 (9)0.0684 (7)0.0342 (7)0.0203 (6)0.0167 (7)
N10.0535 (6)0.0562 (7)0.0389 (5)0.0062 (5)0.0163 (5)0.0047 (5)
C50.0605 (8)0.0659 (9)0.0505 (7)0.0100 (7)0.0278 (7)0.0094 (7)
C60.0494 (7)0.0516 (7)0.0499 (7)0.0067 (6)0.0182 (6)0.0056 (6)
C70.0524 (7)0.0508 (7)0.0395 (6)0.0025 (6)0.0168 (5)0.0008 (5)
C80.0484 (6)0.0468 (7)0.0362 (6)0.0068 (5)0.0152 (5)0.0023 (5)
C90.0530 (7)0.0505 (7)0.0398 (6)0.0099 (6)0.0183 (5)0.0027 (5)
C100.059 (2)0.063 (2)0.0473 (15)0.0070 (18)0.0162 (15)0.0031 (15)
C110.084 (3)0.077 (3)0.0425 (17)0.024 (2)0.012 (2)0.0003 (17)
C140.061 (2)0.067 (3)0.0530 (18)0.002 (2)0.0277 (17)0.0054 (17)
C130.071 (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)
C120.0914 (13)0.0926 (14)0.0457 (8)0.0345 (11)0.0317 (8)0.0113 (8)
C40.0654 (9)0.0648 (9)0.0377 (6)0.0142 (7)0.0208 (6)0.0023 (6)
C30.0529 (7)0.0497 (7)0.0359 (6)0.0122 (6)0.0107 (5)0.0010 (5)
C20.0605 (8)0.0607 (9)0.0399 (7)0.0046 (7)0.0068 (6)0.0056 (6)
C10.0546 (7)0.0585 (8)0.0470 (7)0.0036 (6)0.0099 (6)0.0053 (6)
Geometric parameters (Å, º) top
Cl1—C61.7402 (15)C14—C131.393 (5)
O1—C11.2139 (19)C14—H140.92 (4)
N1—C11.3801 (17)C13—C121.360 (5)
N1—C81.4038 (17)C13—H130.83 (4)
N1—C91.4359 (16)C10'—C11'1.388 (8)
C5—C61.383 (2)C10'—H10'0.92 (6)
C5—C41.386 (2)C11'—C121.280 (7)
C5—H50.988 (18)C11'—H11'0.86 (5)
C6—C71.3920 (19)C14'—C13'1.404 (6)
C7—C81.3768 (19)C14'—H14'0.93 (4)
C7—H70.969 (16)C13'—C121.384 (6)
C8—C31.4035 (17)C13'—H13'0.98 (5)
C9—C141.347 (4)C12—H120.98 (2)
C9—C101.370 (5)C4—C31.377 (2)
C9—C10'1.382 (5)C4—H40.984 (18)
C9—C14'1.405 (5)C3—C21.491 (2)
C10—C111.391 (7)C2—C11.519 (2)
C10—H100.88 (4)C2—H2A0.998 (18)
C11—C121.405 (7)C2—H2B0.97 (2)
C11—H110.90 (4)
C1—N1—C8111.23 (11)C9—C10'—C11'120.8 (5)
C1—N1—C9124.24 (11)C9—C10'—H10'112 (3)
C8—N1—C9124.53 (10)C11'—C10'—H10'128 (3)
C6—C5—C4119.37 (13)C12—C11'—C10'120.5 (5)
C6—C5—H5122.4 (10)C12—C11'—H11'122 (3)
C4—C5—H5118.2 (10)C10'—C11'—H11'117 (3)
C5—C6—C7122.36 (14)C9—C14'—C13'119.6 (4)
C5—C6—Cl1119.05 (11)C9—C14'—H14'117 (2)
C7—C6—Cl1118.58 (11)C13'—C14'—H14'123 (2)
C8—C7—C6116.68 (12)C12—C13'—C14'118.0 (4)
C8—C7—H7120.7 (9)C12—C13'—H13'125 (2)
C6—C7—H7122.6 (9)C14'—C13'—H13'117 (2)
C7—C8—C3122.54 (12)C11'—C12—C13'123.2 (3)
C7—C8—N1128.17 (11)C13—C12—C11117.6 (3)
C3—C8—N1109.29 (11)C11'—C12—H12125.8 (13)
C14—C9—C10123.7 (3)C13—C12—H12113.5 (13)
C10'—C9—C14'117.8 (3)C13'—C12—H12111.0 (13)
C14—C9—N1118.7 (2)C11—C12—H12128.8 (13)
C10—C9—N1117.6 (2)C3—C4—C5120.25 (13)
C10'—C9—N1121.8 (2)C3—C4—H4118.3 (10)
C14'—C9—N1120.4 (2)C5—C4—H4121.5 (10)
C9—C10—C11116.8 (4)C4—C3—C8118.78 (13)
C9—C10—H10123 (2)C4—C3—C2132.91 (12)
C11—C10—H10120 (2)C8—C3—C2108.31 (12)
C10—C11—C12121.7 (5)C3—C2—C1103.76 (11)
C10—C11—H11115 (3)C3—C2—H2A112.9 (10)
C12—C11—H11123 (3)C1—C2—H2A108.5 (10)
C9—C14—C13118.2 (3)C3—C2—H2B113.0 (12)
C9—C14—H14119 (2)C1—C2—H2B109.8 (12)
C13—C14—H14123 (2)H2A—C2—H2B108.8 (15)
C12—C13—C14121.8 (3)O1—C1—N1124.56 (14)
C12—C13—H13126 (3)O1—C1—C2128.06 (13)
C14—C13—H13112 (3)N1—C1—C2107.38 (12)
C4—C5—C6—C70.2 (2)N1—C9—C10'—C11'178.7 (5)
C4—C5—C6—Cl1179.42 (11)C9—C10'—C11'—C121.1 (10)
C5—C6—C7—C80.4 (2)C10'—C9—C14'—C13'0.5 (6)
Cl1—C6—C7—C8179.25 (10)N1—C9—C14'—C13'179.1 (3)
C6—C7—C8—C30.16 (19)C9—C14'—C13'—C121.7 (7)
C6—C7—C8—N1179.27 (12)C10'—C11'—C12—C13'3.5 (10)
C1—N1—C8—C7177.53 (13)C14—C13—C12—C112.7 (6)
C9—N1—C8—C72.9 (2)C14'—C13'—C12—C11'3.8 (7)
C1—N1—C8—C31.68 (15)C10—C11—C12—C131.8 (6)
C9—N1—C8—C3177.89 (12)C6—C5—C4—C30.5 (2)
C1—N1—C9—C1466.2 (4)C5—C4—C3—C81.0 (2)
C8—N1—C9—C14114.3 (4)C5—C4—C3—C2178.32 (15)
C1—N1—C9—C10113.2 (3)C7—C8—C3—C40.8 (2)
C8—N1—C9—C1066.3 (3)N1—C8—C3—C4179.90 (12)
C1—N1—C9—C10'78.8 (5)C7—C8—C3—C2178.64 (12)
C8—N1—C9—C10'100.8 (5)N1—C8—C3—C20.62 (15)
C1—N1—C9—C14'100.8 (4)C4—C3—C2—C1178.85 (15)
C8—N1—C9—C14'79.7 (4)C8—C3—C2—C10.53 (15)
C14—C9—C10—C112.0 (5)C8—N1—C1—O1178.32 (15)
N1—C9—C10—C11177.4 (3)C9—N1—C1—O12.1 (2)
C9—C10—C11—C121.4 (6)C8—N1—C1—C21.99 (16)
C10—C9—C14—C132.9 (6)C9—N1—C1—C2177.59 (13)
N1—C9—C14—C13176.5 (3)C3—C2—C1—O1178.82 (16)
C9—C14—C13—C123.2 (7)C3—C2—C1—N11.51 (16)
C14'—C9—C10'—C11'0.9 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O1i0.93 (4)2.33 (4)3.253 (5)171 (3)
C2—H2B···O1ii0.97 (2)2.44 (2)3.360 (2)158.0 (16)
Symmetry codes: (i) x, y1, z; (ii) x+1, y1/2, z+1/2.
4-Chloro-1-phenylindolin-2-one (B_LT) top
Crystal data top
C14H10ClNOF(000) = 504
Mr = 243.68Dx = 1.428 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.4274 (9) ÅCell parameters from 9462 reflections
b = 11.8586 (10) Åθ = 2.6–30.2°
c = 9.1689 (8) ŵ = 0.32 mm1
β = 90.341 (2)°T = 100 K
V = 1133.75 (17) Å3PLANE, colourless
Z = 40.59 × 0.33 × 0.10 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2937 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm-1Rint = 0.034
ω scansθmax = 30.3°, θmin = 2.0°
Absorption correction: multi-scan
APEX2 Software Suite (Bruker, 2005)
h = 1414
Tmin = 0.834, Tmax = 0.968k = 1616
20207 measured reflectionsl = 1212
3317 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034All H-atom parameters refined
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0532P)2 + 0.3565P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.002
3317 reflectionsΔρmax = 0.43 e Å3
194 parametersΔρmin = 0.25 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.76721 (10)0.49310 (9)0.64644 (12)0.0186 (2)
C20.85830 (11)0.40374 (9)0.58832 (12)0.0194 (2)
C30.86181 (10)0.42828 (9)0.42814 (11)0.0174 (2)
C40.92785 (10)0.37865 (9)0.31494 (12)0.0191 (2)
C50.90912 (11)0.41479 (10)0.17124 (12)0.0217 (2)
C60.82162 (11)0.50041 (10)0.14285 (12)0.0215 (2)
C70.75357 (10)0.55343 (9)0.25525 (12)0.0192 (2)
C80.77632 (10)0.51624 (9)0.39652 (11)0.0166 (2)
C90.62732 (10)0.64194 (9)0.53875 (11)0.0168 (2)
C100.64796 (11)0.74572 (9)0.47135 (12)0.0195 (2)
C110.55612 (12)0.83056 (10)0.48458 (13)0.0229 (2)
C120.44611 (12)0.81288 (10)0.56664 (13)0.0244 (2)
C130.42704 (11)0.70949 (10)0.63459 (13)0.0232 (2)
C140.51636 (10)0.62325 (10)0.61973 (12)0.0198 (2)
Cl11.03557 (3)0.27007 (2)0.35207 (3)0.02390 (9)
N10.71912 (8)0.55315 (8)0.52725 (9)0.01685 (18)
O10.74015 (8)0.51070 (8)0.77320 (9)0.02393 (18)
H50.9565 (14)0.3789 (13)0.0896 (17)0.025 (4)*
H60.8079 (14)0.5211 (13)0.0430 (17)0.025 (4)*
H70.6961 (13)0.6125 (12)0.2337 (15)0.017 (3)*
H100.7241 (15)0.7584 (12)0.4177 (17)0.024 (4)*
H110.5717 (14)0.9014 (13)0.4399 (16)0.025 (4)*
H120.3836 (16)0.8679 (14)0.5786 (18)0.033 (4)*
H130.3452 (14)0.7052 (13)0.7050 (17)0.027 (4)*
H140.5053 (14)0.5512 (14)0.6660 (16)0.023 (3)*
H2A0.9405 (15)0.4094 (14)0.6355 (17)0.028 (4)*
H2B0.8247 (14)0.3270 (14)0.6089 (17)0.030 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0190 (5)0.0197 (5)0.0170 (5)0.0017 (4)0.0004 (4)0.0029 (4)
C20.0208 (5)0.0198 (5)0.0176 (5)0.0005 (4)0.0001 (4)0.0025 (4)
C30.0172 (4)0.0181 (5)0.0168 (5)0.0026 (4)0.0001 (4)0.0003 (4)
C40.0174 (5)0.0179 (5)0.0220 (5)0.0014 (4)0.0010 (4)0.0016 (4)
C50.0237 (5)0.0222 (5)0.0193 (5)0.0030 (4)0.0040 (4)0.0042 (4)
C60.0269 (5)0.0233 (5)0.0144 (5)0.0038 (4)0.0010 (4)0.0003 (4)
C70.0217 (5)0.0195 (5)0.0164 (5)0.0014 (4)0.0001 (4)0.0003 (4)
C80.0172 (4)0.0173 (5)0.0154 (5)0.0028 (4)0.0011 (4)0.0009 (3)
C90.0177 (5)0.0175 (5)0.0153 (5)0.0000 (4)0.0016 (4)0.0020 (3)
C100.0218 (5)0.0200 (5)0.0168 (5)0.0019 (4)0.0002 (4)0.0004 (4)
C110.0298 (6)0.0178 (5)0.0211 (5)0.0005 (4)0.0036 (4)0.0005 (4)
C120.0252 (5)0.0240 (6)0.0238 (6)0.0050 (4)0.0037 (4)0.0057 (4)
C130.0188 (5)0.0274 (6)0.0233 (5)0.0006 (4)0.0000 (4)0.0045 (4)
C140.0197 (5)0.0212 (5)0.0185 (5)0.0020 (4)0.0003 (4)0.0007 (4)
Cl10.02142 (14)0.02228 (15)0.02799 (16)0.00322 (9)0.00050 (10)0.00249 (10)
N10.0188 (4)0.0184 (4)0.0134 (4)0.0006 (3)0.0011 (3)0.0012 (3)
O10.0276 (4)0.0295 (4)0.0147 (4)0.0016 (3)0.0027 (3)0.0030 (3)
Geometric parameters (Å, º) top
C1—O11.2157 (13)C7—H70.942 (14)
C1—N11.3951 (14)C8—N11.4116 (13)
C1—C21.5216 (15)C9—C101.3944 (15)
C2—C31.4978 (15)C9—C141.3962 (14)
C2—H2A0.960 (16)C9—N11.4274 (13)
C2—H2B0.994 (16)C10—C111.3948 (16)
C3—C41.3808 (15)C10—H100.948 (16)
C3—C81.4013 (15)C11—C121.3914 (17)
C4—C51.3981 (16)C11—H110.949 (15)
C4—Cl11.7409 (11)C12—C131.3901 (18)
C5—C61.3886 (17)C12—H120.929 (17)
C5—H50.995 (15)C13—C141.3905 (16)
C6—C71.4034 (15)C13—H131.074 (15)
C6—H60.958 (15)C14—H140.961 (16)
C7—C81.3875 (15)
O1—C1—N1125.23 (10)C7—C8—C3122.33 (10)
O1—C1—C2127.11 (10)C7—C8—N1128.57 (10)
N1—C1—C2107.66 (9)C3—C8—N1109.06 (9)
C3—C2—C1103.12 (9)C10—C9—C14120.42 (10)
C3—C2—H2A113.7 (9)C10—C9—N1120.86 (9)
C1—C2—H2A110.5 (9)C14—C9—N1118.72 (9)
C3—C2—H2B112.0 (9)C9—C10—C11119.35 (10)
C1—C2—H2B110.5 (9)C9—C10—H10120.1 (9)
H2A—C2—H2B107.1 (13)C11—C10—H10120.5 (9)
C4—C3—C8118.77 (10)C12—C11—C10120.46 (11)
C4—C3—C2132.02 (10)C12—C11—H11120.7 (9)
C8—C3—C2109.17 (9)C10—C11—H11118.8 (9)
C3—C4—C5120.68 (10)C13—C12—C11119.73 (11)
C3—C4—Cl1119.49 (9)C13—C12—H12117.7 (10)
C5—C4—Cl1119.83 (8)C11—C12—H12122.6 (10)
C6—C5—C4119.26 (10)C12—C13—C14120.47 (11)
C6—C5—H5120.0 (9)C12—C13—H13115.3 (8)
C4—C5—H5120.7 (9)C14—C13—H13124.0 (8)
C5—C6—C7121.63 (10)C13—C14—C9119.54 (11)
C5—C6—H6117.5 (9)C13—C14—H14121.9 (9)
C7—C6—H6120.9 (9)C9—C14—H14118.5 (9)
C8—C7—C6117.31 (10)C1—N1—C8110.80 (9)
C8—C7—H7122.5 (8)C1—N1—C9123.83 (9)
C6—C7—H7120.2 (8)C8—N1—C9125.34 (9)
O1—C1—C2—C3175.45 (11)N1—C9—C10—C11179.87 (10)
N1—C1—C2—C34.34 (11)C9—C10—C11—C121.31 (17)
C1—C2—C3—C4178.95 (11)C10—C11—C12—C130.69 (18)
C1—C2—C3—C83.56 (11)C11—C12—C13—C140.75 (18)
C8—C3—C4—C50.50 (16)C12—C13—C14—C91.54 (17)
C2—C3—C4—C5176.80 (11)C10—C9—C14—C130.91 (16)
C8—C3—C4—Cl1179.44 (8)N1—C9—C14—C13178.72 (10)
C2—C3—C4—Cl13.27 (17)O1—C1—N1—C8176.10 (11)
C3—C4—C5—C60.95 (16)C2—C1—N1—C83.69 (12)
Cl1—C4—C5—C6179.11 (9)O1—C1—N1—C92.18 (17)
C4—C5—C6—C71.49 (17)C2—C1—N1—C9178.03 (9)
C5—C6—C7—C80.53 (16)C7—C8—N1—C1179.16 (11)
C6—C7—C8—C30.98 (16)C3—C8—N1—C11.41 (12)
C6—C7—C8—N1178.46 (10)C7—C8—N1—C92.60 (17)
C4—C3—C8—C71.49 (16)C3—C8—N1—C9179.65 (9)
C2—C3—C8—C7176.38 (10)C10—C9—N1—C1129.80 (11)
C4—C3—C8—N1179.41 (9)C14—C9—N1—C149.83 (14)
C2—C3—C8—N11.54 (12)C10—C9—N1—C848.23 (15)
C14—C9—C10—C110.51 (16)C14—C9—N1—C8132.15 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.958 (15)2.572 (15)3.4914 (14)161.0 (13)
C11—H11···O1ii0.949 (15)2.557 (15)3.3207 (15)137.6 (12)
C12—H12···O1iii0.929 (17)2.530 (17)3.3862 (14)153.4 (14)
Symmetry codes: (i) x, y, z1; (ii) x, y+3/2, z1/2; (iii) x+1, y+1/2, z+3/2.
4-Chloro-1-phenylindolin-2-one (B_RT) top
Crystal data top
C14H10ClNOF(000) = 504
Mr = 243.68Dx = 1.384 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.5605 (8) ÅCell parameters from 8615 reflections
b = 12.0485 (9) Åθ = 2.6–27.8°
c = 9.1939 (7) ŵ = 0.31 mm1
β = 89.288 (2)°T = 297 K
V = 1169.73 (15) Å3Plate, colourless
Z = 40.59 × 0.33 × 0.10 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2575 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm-1Rint = 0.022
ω scansθmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan
APEX2 Software Suite (Bruker, 2005)
h = 1414
Tmin = 0.839, Tmax = 0.969k = 1616
23589 measured reflectionsl = 1212
3410 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040All H-atom parameters refined
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0532P)2 + 0.3065P]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.001
3410 reflectionsΔρmax = 0.29 e Å3
194 parametersΔρmin = 0.30 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.76562 (13)0.49276 (12)0.64486 (14)0.0495 (3)
C20.85585 (14)0.40585 (12)0.58575 (15)0.0511 (3)
C30.85988 (12)0.42980 (11)0.42606 (14)0.0453 (3)
C40.92506 (12)0.38062 (12)0.31262 (15)0.0504 (3)
C50.90718 (15)0.41639 (13)0.17034 (16)0.0583 (4)
C60.82218 (16)0.50083 (14)0.14390 (15)0.0588 (4)
C70.75498 (14)0.55303 (12)0.25600 (14)0.0504 (3)
C80.77665 (11)0.51631 (10)0.39620 (13)0.0427 (3)
C90.62896 (12)0.64046 (11)0.54016 (13)0.0442 (3)
C100.65075 (15)0.74267 (12)0.47462 (15)0.0517 (3)
C110.56094 (17)0.82574 (14)0.48807 (18)0.0621 (4)
C120.45172 (17)0.80830 (15)0.56878 (19)0.0662 (4)
C130.43101 (15)0.70694 (15)0.63495 (18)0.0632 (4)
C140.51839 (13)0.62236 (13)0.61987 (16)0.0530 (3)
Cl11.03020 (4)0.27329 (4)0.34775 (5)0.06917 (15)
N10.71932 (10)0.55296 (9)0.52730 (11)0.0450 (2)
O10.73754 (11)0.50912 (10)0.77096 (10)0.0667 (3)
H50.9537 (16)0.3826 (15)0.093 (2)0.068 (5)*
H60.8078 (15)0.5232 (14)0.0470 (19)0.066 (5)*
H70.6989 (14)0.6109 (13)0.2358 (16)0.048 (4)*
H100.7266 (16)0.7538 (13)0.4224 (18)0.058 (4)*
H110.5746 (18)0.8952 (17)0.445 (2)0.079 (6)*
H120.3920 (18)0.8602 (17)0.582 (2)0.082 (6)*
H130.3527 (16)0.7030 (14)0.7035 (19)0.065 (5)*
H140.5049 (15)0.5523 (15)0.6614 (17)0.058 (4)*
H2A0.9360 (16)0.4121 (14)0.6312 (19)0.064 (5)*
H2B0.8196 (15)0.3314 (15)0.6053 (18)0.063 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0531 (7)0.0561 (7)0.0394 (6)0.0046 (6)0.0001 (5)0.0069 (5)
C20.0541 (7)0.0530 (8)0.0463 (7)0.0007 (6)0.0041 (6)0.0070 (6)
C30.0443 (6)0.0482 (7)0.0435 (6)0.0069 (5)0.0011 (5)0.0009 (5)
C40.0463 (6)0.0490 (7)0.0559 (7)0.0048 (5)0.0025 (5)0.0053 (6)
C50.0651 (9)0.0613 (8)0.0483 (7)0.0070 (7)0.0114 (6)0.0102 (6)
C60.0756 (10)0.0640 (9)0.0368 (6)0.0071 (7)0.0031 (6)0.0005 (6)
C70.0585 (8)0.0536 (8)0.0392 (6)0.0023 (6)0.0016 (5)0.0032 (5)
C80.0449 (6)0.0460 (6)0.0372 (6)0.0078 (5)0.0015 (4)0.0004 (5)
C90.0470 (6)0.0484 (7)0.0374 (6)0.0038 (5)0.0035 (5)0.0030 (5)
C100.0585 (8)0.0504 (7)0.0461 (7)0.0055 (6)0.0004 (6)0.0007 (5)
C110.0810 (11)0.0487 (8)0.0569 (8)0.0012 (7)0.0114 (7)0.0008 (6)
C120.0667 (10)0.0655 (10)0.0666 (10)0.0151 (8)0.0119 (8)0.0151 (8)
C130.0505 (8)0.0757 (10)0.0632 (9)0.0004 (7)0.0011 (7)0.0124 (8)
C140.0507 (7)0.0571 (8)0.0513 (7)0.0070 (6)0.0017 (6)0.0016 (6)
Cl10.0616 (2)0.0644 (3)0.0815 (3)0.01075 (17)0.00048 (19)0.00778 (19)
N10.0501 (6)0.0494 (6)0.0356 (5)0.0005 (4)0.0020 (4)0.0027 (4)
O10.0801 (7)0.0829 (8)0.0370 (5)0.0077 (6)0.0054 (5)0.0085 (5)
Geometric parameters (Å, º) top
C1—O11.2093 (16)C7—H70.935 (16)
C1—N11.3952 (16)C8—N11.4129 (15)
C1—C21.512 (2)C9—C141.3881 (18)
C2—C31.4963 (18)C9—C101.3889 (19)
C2—H2A0.952 (18)C9—N11.4259 (17)
C2—H2B0.991 (18)C10—C111.383 (2)
C3—C41.3765 (18)C10—H100.938 (17)
C3—C81.3930 (18)C11—C121.380 (2)
C4—C51.392 (2)C11—H110.94 (2)
C4—Cl11.7373 (15)C12—C131.381 (3)
C5—C61.380 (2)C12—H120.90 (2)
C5—H50.948 (18)C13—C141.381 (2)
C6—C71.394 (2)C13—H131.034 (17)
C6—H60.945 (17)C14—H140.937 (18)
C7—C81.3845 (17)
O1—C1—N1125.01 (13)C7—C8—C3122.31 (12)
O1—C1—C2127.11 (13)C7—C8—N1128.34 (13)
N1—C1—C2107.88 (11)C3—C8—N1109.30 (10)
C3—C2—C1103.25 (11)C14—C9—C10120.13 (13)
C3—C2—H2A113.6 (10)C14—C9—N1119.03 (12)
C1—C2—H2A110.4 (10)C10—C9—N1120.83 (12)
C3—C2—H2B111.1 (10)C11—C10—C9119.54 (14)
C1—C2—H2B108.8 (9)C11—C10—H10121.5 (10)
H2A—C2—H2B109.6 (14)C9—C10—H10119.0 (10)
C4—C3—C8118.92 (12)C12—C11—C10120.36 (16)
C4—C3—C2131.93 (13)C12—C11—H11119.2 (12)
C8—C3—C2109.10 (11)C10—C11—H11120.4 (12)
C3—C4—C5120.41 (14)C11—C12—C13119.90 (16)
C3—C4—Cl1119.62 (11)C11—C12—H12123.3 (13)
C5—C4—Cl1119.97 (11)C13—C12—H12116.8 (13)
C6—C5—C4119.32 (13)C14—C13—C12120.44 (15)
C6—C5—H5121.1 (11)C14—C13—H13123.8 (10)
C4—C5—H5119.6 (11)C12—C13—H13115.5 (9)
C5—C6—C7121.90 (13)C13—C14—C9119.60 (15)
C5—C6—H6119.3 (10)C13—C14—H14121.7 (10)
C7—C6—H6118.8 (10)C9—C14—H14118.7 (10)
C8—C7—C6117.11 (14)C1—N1—C8110.35 (11)
C8—C7—H7122.4 (9)C1—N1—C9124.11 (10)
C6—C7—H7120.5 (9)C8—N1—C9125.53 (10)
O1—C1—C2—C3176.24 (14)N1—C9—C10—C11179.52 (12)
N1—C1—C2—C33.45 (14)C9—C10—C11—C121.5 (2)
C1—C2—C3—C4179.55 (14)C10—C11—C12—C130.9 (2)
C1—C2—C3—C82.82 (14)C11—C12—C13—C140.6 (2)
C8—C3—C4—C50.47 (19)C12—C13—C14—C91.4 (2)
C2—C3—C4—C5176.96 (14)C10—C9—C14—C130.8 (2)
C8—C3—C4—Cl1179.52 (9)N1—C9—C14—C13179.04 (13)
C2—C3—C4—Cl13.0 (2)O1—C1—N1—C8176.77 (14)
C3—C4—C5—C60.8 (2)C2—C1—N1—C82.93 (14)
Cl1—C4—C5—C6179.21 (12)O1—C1—N1—C92.0 (2)
C4—C5—C6—C71.2 (2)C2—C1—N1—C9178.33 (11)
C5—C6—C7—C80.2 (2)C7—C8—N1—C1178.66 (13)
C6—C7—C8—C31.1 (2)C3—C8—N1—C11.11 (14)
C6—C7—C8—N1178.38 (13)C7—C8—N1—C92.6 (2)
C4—C3—C8—C71.47 (19)C3—C8—N1—C9179.83 (11)
C2—C3—C8—C7176.51 (12)C14—C9—N1—C150.32 (17)
C4—C3—C8—N1179.19 (11)C10—C9—N1—C1129.47 (14)
C2—C3—C8—N11.21 (14)C14—C9—N1—C8131.12 (13)
C14—C9—C10—C110.7 (2)C10—C9—N1—C849.09 (18)
1-(3-Chlorophenyl)-indolin-2-one (C_LT) top
Crystal data top
C14H10ClNOF(000) = 504
Mr = 243.68Dx = 1.442 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.1067 (7) ÅCell parameters from 7732 reflections
b = 13.3924 (8) Åθ = 2.5–29.8°
c = 8.0288 (5) ŵ = 0.32 mm1
β = 109.920 (2)°T = 90 K
V = 1122.79 (12) Å3Bar, colourless
Z = 40.60 × 0.23 × 0.09 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2765 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm-1Rint = 0.027
ω scansθmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan
APEX2 Software Suite (Bruker, 2005)
h = 1414
Tmin = 0.832, Tmax = 0.972k = 1818
17709 measured reflectionsl = 1111
3191 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032All H-atom parameters refined
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0467P)2 + 0.3999P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3191 reflectionsΔρmax = 0.42 e Å3
194 parametersΔρmin = 0.27 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.83229 (10)0.37452 (7)0.24414 (14)0.0113 (2)
C20.97698 (10)0.37009 (8)0.33233 (13)0.0110 (2)
C30.99596 (10)0.37259 (7)0.52649 (13)0.0109 (2)
C41.10634 (10)0.37359 (8)0.67415 (14)0.0126 (2)
C51.09509 (11)0.38197 (8)0.84178 (14)0.0140 (2)
C60.97511 (11)0.38739 (8)0.86005 (14)0.0135 (2)
C70.86282 (10)0.38494 (8)0.71219 (14)0.0124 (2)
C80.87626 (10)0.37859 (7)0.54693 (13)0.0109 (2)
C90.64647 (10)0.39385 (8)0.34807 (14)0.0119 (2)
C100.58431 (10)0.32848 (8)0.42661 (14)0.0128 (2)
C110.45679 (10)0.34678 (8)0.40260 (14)0.0140 (2)
C120.38994 (10)0.42603 (9)0.30137 (14)0.0154 (2)
C130.45327 (11)0.48890 (8)0.22100 (14)0.0160 (2)
C140.58179 (10)0.47359 (8)0.24426 (14)0.0138 (2)
Cl10.37737 (3)0.26618 (2)0.50010 (4)0.02190 (9)
N10.77963 (8)0.37973 (7)0.37787 (11)0.01154 (18)
O10.77119 (8)0.37345 (6)0.08629 (10)0.01483 (17)
H41.1910 (14)0.3693 (10)0.6601 (18)0.017 (3)*
H51.1752 (14)0.3848 (11)0.953 (2)0.022 (4)*
H60.9704 (14)0.3937 (11)0.977 (2)0.019 (4)*
H70.7806 (13)0.3873 (10)0.7246 (18)0.013 (3)*
H100.6287 (13)0.2730 (11)0.4937 (18)0.015 (3)*
H120.3012 (15)0.4359 (12)0.288 (2)0.025 (4)*
H130.4077 (15)0.5432 (11)0.150 (2)0.022 (4)*
H140.6260 (13)0.5169 (10)0.1917 (18)0.013 (3)*
H2A1.0093 (14)0.3108 (11)0.2957 (18)0.018 (4)*
H2B1.0152 (13)0.4271 (11)0.2965 (18)0.017 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0130 (5)0.0097 (4)0.0119 (5)0.0006 (4)0.0051 (4)0.0003 (3)
C20.0112 (5)0.0118 (5)0.0107 (5)0.0003 (4)0.0046 (4)0.0001 (3)
C30.0127 (5)0.0093 (4)0.0112 (5)0.0003 (3)0.0047 (4)0.0001 (3)
C40.0105 (5)0.0113 (5)0.0154 (5)0.0000 (4)0.0037 (4)0.0001 (4)
C50.0146 (5)0.0121 (5)0.0128 (5)0.0006 (4)0.0013 (4)0.0000 (4)
C60.0178 (5)0.0118 (5)0.0107 (5)0.0004 (4)0.0046 (4)0.0003 (3)
C70.0128 (5)0.0120 (5)0.0134 (5)0.0002 (4)0.0056 (4)0.0005 (4)
C80.0114 (5)0.0096 (4)0.0108 (5)0.0005 (3)0.0023 (4)0.0007 (3)
C90.0098 (5)0.0142 (5)0.0111 (4)0.0005 (4)0.0028 (4)0.0009 (4)
C100.0120 (5)0.0137 (5)0.0118 (5)0.0002 (4)0.0029 (4)0.0008 (4)
C110.0125 (5)0.0173 (5)0.0127 (5)0.0033 (4)0.0050 (4)0.0011 (4)
C120.0103 (5)0.0208 (5)0.0141 (5)0.0022 (4)0.0030 (4)0.0025 (4)
C130.0159 (5)0.0164 (5)0.0139 (5)0.0044 (4)0.0027 (4)0.0008 (4)
C140.0152 (5)0.0137 (5)0.0122 (5)0.0000 (4)0.0043 (4)0.0011 (4)
Cl10.01613 (15)0.02786 (16)0.02394 (16)0.00485 (10)0.00973 (11)0.00480 (11)
N10.0091 (4)0.0155 (4)0.0096 (4)0.0004 (3)0.0027 (3)0.0009 (3)
O10.0152 (4)0.0177 (4)0.0107 (4)0.0002 (3)0.0033 (3)0.0001 (3)
Geometric parameters (Å, º) top
C1—O11.2170 (13)C7—H70.953 (14)
C1—N11.3884 (13)C8—N11.4148 (13)
C1—C21.5205 (15)C9—C101.3919 (15)
C2—C31.5006 (14)C9—C141.3940 (14)
C2—H2A0.958 (15)C9—N11.4281 (13)
C2—H2B0.964 (15)C10—C111.3845 (15)
C3—C41.3850 (14)C10—H100.951 (14)
C3—C81.3963 (15)C11—C121.3882 (15)
C4—C51.3980 (15)C11—Cl11.7397 (11)
C4—H40.986 (15)C12—C131.3890 (16)
C5—C61.3913 (16)C12—H120.964 (15)
C5—H51.026 (15)C13—C141.3903 (16)
C6—C71.3989 (15)C13—H130.957 (15)
C6—H60.963 (15)C14—H140.947 (14)
C7—C81.3875 (15)
O1—C1—N1125.00 (10)C7—C8—C3122.20 (10)
O1—C1—C2127.62 (10)C7—C8—N1128.55 (10)
N1—C1—C2107.38 (8)C3—C8—N1109.22 (9)
C3—C2—C1103.59 (8)C10—C9—C14121.24 (10)
C3—C2—H2A113.8 (8)C10—C9—N1119.08 (9)
C1—C2—H2A109.7 (9)C14—C9—N1119.67 (9)
C3—C2—H2B111.8 (8)C11—C10—C9117.86 (10)
C1—C2—H2B109.5 (8)C11—C10—H10121.7 (8)
H2A—C2—H2B108.4 (12)C9—C10—H10120.4 (8)
C4—C3—C8119.96 (9)C10—C11—C12122.32 (10)
C4—C3—C2131.27 (10)C10—C11—Cl1118.62 (8)
C8—C3—C2108.72 (9)C12—C11—Cl1119.06 (8)
C3—C4—C5118.78 (10)C11—C12—C13118.75 (10)
C3—C4—H4120.1 (8)C11—C12—H12119.5 (9)
C5—C4—H4121.1 (8)C13—C12—H12121.8 (9)
C6—C5—C4120.58 (10)C12—C13—C14120.49 (10)
C6—C5—H5118.9 (9)C12—C13—H13119.4 (9)
C4—C5—H5120.5 (9)C14—C13—H13120.1 (9)
C5—C6—C7121.22 (10)C13—C14—C9119.32 (10)
C5—C6—H6118.7 (9)C13—C14—H14121.0 (8)
C7—C6—H6120.1 (9)C9—C14—H14119.7 (8)
C8—C7—C6117.24 (10)C1—N1—C8111.08 (9)
C8—C7—H7121.4 (8)C1—N1—C9124.21 (9)
C6—C7—H7121.3 (8)C8—N1—C9124.47 (9)
O1—C1—C2—C3179.28 (10)C10—C11—C12—C130.20 (16)
N1—C1—C2—C30.47 (10)Cl1—C11—C12—C13178.72 (8)
C1—C2—C3—C4177.77 (10)C11—C12—C13—C141.10 (16)
C1—C2—C3—C80.45 (11)C12—C13—C14—C90.53 (16)
C8—C3—C4—C50.81 (15)C10—C9—C14—C130.97 (16)
C2—C3—C4—C5176.26 (10)N1—C9—C14—C13177.75 (10)
C3—C4—C5—C61.14 (15)O1—C1—N1—C8179.42 (10)
C4—C5—C6—C70.19 (16)C2—C1—N1—C80.33 (11)
C5—C6—C7—C81.05 (15)O1—C1—N1—C96.05 (16)
C6—C7—C8—C31.39 (15)C2—C1—N1—C9174.20 (9)
C6—C7—C8—N1176.70 (10)C7—C8—N1—C1178.34 (10)
C4—C3—C8—C70.47 (15)C3—C8—N1—C10.05 (11)
C2—C3—C8—C7178.15 (9)C7—C8—N1—C93.82 (16)
C4—C3—C8—N1177.95 (9)C3—C8—N1—C9174.47 (9)
C2—C3—C8—N10.27 (11)C10—C9—N1—C1128.52 (11)
C14—C9—C10—C111.81 (16)C14—C9—N1—C152.74 (14)
N1—C9—C10—C11176.90 (9)C10—C9—N1—C857.67 (14)
C9—C10—C11—C121.23 (16)C14—C9—N1—C8121.07 (11)
C9—C10—C11—Cl1179.84 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O1i0.951 (14)2.471 (14)3.3841 (13)161.1 (11)
C13—H13···O1ii0.957 (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) top
Crystal data top
C14H10ClNOF(000) = 504
Mr = 243.68Dx = 1.392 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.1901 (2) ÅCell parameters from 7649 reflections
b = 13.6596 (3) Åθ = 2.4–27.6°
c = 8.0965 (2) ŵ = 0.31 mm1
β = 109.996 (1)°T = 296 K
V = 1162.96 (4) Å3Bar, colourless
Z = 40.60 × 0.23 × 0.09 mm
Data collection top
Bruker APEXII CCD
diffractometer
2359 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm-1Rint = 0.068
ω scansθmax = 29.4°, θmin = 1.9°
Absorption correction: multi-scan
(APEX2; Bruker, 2005)
h = 1415
Tmin = 0.837, Tmax = 0.973k = 1818
21800 measured reflectionsl = 1111
3159 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045All H-atom parameters refined
wR(F2) = 0.131 w = 1/[σ2(Fo2) + (0.0685P)2 + 0.1297P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
3159 reflectionsΔρmax = 0.38 e Å3
194 parametersΔρmin = 0.56 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.83010 (13)0.37519 (9)0.24314 (18)0.0357 (3)
C20.97339 (13)0.36994 (10)0.33071 (18)0.0350 (3)
C30.99289 (12)0.37266 (9)0.52246 (17)0.0332 (3)
C41.10215 (13)0.37232 (10)0.6691 (2)0.0401 (3)
C51.09155 (15)0.38035 (10)0.8349 (2)0.0445 (3)
C60.97341 (15)0.38681 (10)0.85297 (19)0.0424 (3)
C70.86177 (14)0.38606 (10)0.70735 (18)0.0382 (3)
C80.87487 (12)0.37960 (9)0.54348 (17)0.0321 (3)
C90.64634 (12)0.39487 (10)0.34614 (18)0.0359 (3)
C100.58388 (13)0.32968 (11)0.42009 (19)0.0409 (3)
C110.45727 (13)0.34684 (12)0.39525 (19)0.0455 (3)
C120.39209 (14)0.42498 (14)0.2979 (2)0.0507 (4)
C130.45507 (16)0.48767 (13)0.2224 (2)0.0523 (4)
C140.58227 (15)0.47375 (11)0.2469 (2)0.0442 (3)
Cl10.37809 (5)0.26605 (5)0.48804 (8)0.0793 (2)
N10.77845 (10)0.38116 (8)0.37545 (14)0.0362 (3)
O10.76945 (10)0.37418 (8)0.08714 (13)0.0490 (3)
H41.1840 (16)0.3671 (12)0.654 (2)0.044 (4)*
H51.1730 (17)0.3818 (13)0.946 (2)0.057 (5)*
H60.9701 (16)0.3922 (13)0.970 (3)0.054 (5)*
H70.7811 (16)0.3894 (11)0.722 (2)0.044 (4)*
H100.6299 (15)0.2743 (12)0.491 (2)0.044 (4)*
H120.3046 (18)0.4351 (15)0.281 (3)0.066 (5)*
H130.412 (2)0.5404 (14)0.161 (3)0.065 (5)*
H140.6268 (17)0.5176 (14)0.195 (2)0.053 (5)*
H2A1.0127 (15)0.4231 (13)0.298 (2)0.046 (4)*
H2B1.0032 (16)0.3121 (13)0.296 (2)0.048 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0367 (7)0.0345 (6)0.0357 (7)0.0002 (5)0.0120 (5)0.0007 (5)
C20.0343 (7)0.0343 (7)0.0388 (7)0.0001 (5)0.0155 (6)0.0008 (5)
C30.0324 (6)0.0290 (6)0.0380 (7)0.0009 (5)0.0118 (5)0.0010 (5)
C40.0305 (7)0.0390 (7)0.0480 (8)0.0014 (5)0.0100 (6)0.0002 (6)
C50.0415 (8)0.0424 (8)0.0400 (7)0.0019 (6)0.0017 (6)0.0008 (6)
C60.0503 (9)0.0409 (7)0.0338 (7)0.0023 (6)0.0116 (6)0.0013 (6)
C70.0391 (7)0.0392 (7)0.0386 (7)0.0032 (5)0.0161 (6)0.0025 (5)
C80.0305 (6)0.0305 (6)0.0333 (6)0.0008 (5)0.0080 (5)0.0027 (5)
C90.0291 (6)0.0422 (7)0.0344 (6)0.0020 (5)0.0083 (5)0.0011 (5)
C100.0332 (7)0.0452 (8)0.0416 (7)0.0000 (6)0.0093 (6)0.0053 (6)
C110.0339 (7)0.0608 (9)0.0405 (7)0.0071 (6)0.0112 (6)0.0018 (6)
C120.0304 (7)0.0689 (11)0.0488 (9)0.0065 (7)0.0083 (6)0.0071 (7)
C130.0468 (9)0.0553 (9)0.0473 (8)0.0184 (7)0.0063 (7)0.0063 (7)
C140.0436 (8)0.0440 (8)0.0427 (8)0.0040 (6)0.0119 (6)0.0081 (6)
Cl10.0539 (3)0.1023 (4)0.0881 (4)0.0215 (2)0.0326 (3)0.0151 (3)
N10.0290 (6)0.0447 (6)0.0333 (6)0.0006 (4)0.0088 (4)0.0035 (4)
O10.0480 (6)0.0623 (7)0.0336 (5)0.0004 (5)0.0100 (4)0.0002 (5)
Geometric parameters (Å, º) top
C1—O11.2124 (17)C7—H70.952 (16)
C1—N11.3827 (17)C8—N11.4183 (17)
C1—C21.5170 (19)C9—C141.388 (2)
C2—C31.4925 (19)C9—C101.388 (2)
C2—H2A0.934 (17)C9—N11.4272 (16)
C2—H2B0.936 (18)C10—C111.381 (2)
C3—C41.383 (2)C10—H100.982 (17)
C3—C81.3914 (18)C11—C121.378 (2)
C4—C51.392 (2)C11—Cl11.7386 (16)
C4—H40.967 (17)C12—C131.378 (2)
C5—C61.382 (2)C12—H120.951 (19)
C5—H51.037 (18)C13—C141.381 (2)
C6—C71.394 (2)C13—H130.91 (2)
C6—H60.966 (19)C14—H140.961 (18)
C7—C81.3866 (19)
O1—C1—N1125.06 (13)C7—C8—C3122.46 (12)
O1—C1—C2127.74 (13)C7—C8—N1128.48 (12)
N1—C1—C2107.20 (11)C3—C8—N1109.04 (11)
C3—C2—C1103.90 (11)C14—C9—C10120.74 (13)
C3—C2—H2A111.3 (10)C14—C9—N1119.92 (12)
C1—C2—H2A110.8 (10)C10—C9—N1119.33 (12)
C3—C2—H2B113.0 (10)C11—C10—C9118.10 (13)
C1—C2—H2B109.1 (10)C11—C10—H10121.6 (9)
H2A—C2—H2B108.6 (14)C9—C10—H10120.3 (9)
C4—C3—C8119.52 (12)C12—C11—C10122.04 (14)
C4—C3—C2131.68 (12)C12—C11—Cl1119.38 (12)
C8—C3—C2108.77 (11)C10—C11—Cl1118.57 (12)
C3—C4—C5119.08 (13)C13—C12—C11118.96 (14)
C3—C4—H4119.4 (9)C13—C12—H12120.1 (12)
C5—C4—H4121.6 (10)C11—C12—H12120.9 (12)
C6—C5—C4120.48 (14)C12—C13—C14120.58 (15)
C6—C5—H5119.8 (10)C12—C13—H13118.7 (13)
C4—C5—H5119.7 (10)C14—C13—H13120.7 (13)
C5—C6—C7121.55 (14)C13—C14—C9119.55 (15)
C5—C6—H6118.0 (10)C13—C14—H14120.9 (11)
C7—C6—H6120.5 (10)C9—C14—H14119.6 (11)
C8—C7—C6116.89 (13)C1—N1—C8111.09 (11)
C8—C7—H7122.7 (10)C1—N1—C9124.24 (11)
C6—C7—H7120.4 (10)C8—N1—C9124.50 (11)
O1—C1—C2—C3179.22 (13)C10—C11—C12—C130.3 (2)
N1—C1—C2—C30.56 (13)Cl1—C11—C12—C13178.92 (13)
C1—C2—C3—C4178.38 (13)C11—C12—C13—C141.4 (3)
C1—C2—C3—C80.50 (14)C12—C13—C14—C91.1 (2)
C8—C3—C4—C50.89 (19)C10—C9—C14—C130.3 (2)
C2—C3—C4—C5176.80 (14)N1—C9—C14—C13178.61 (14)
C3—C4—C5—C61.1 (2)O1—C1—N1—C8179.35 (13)
C4—C5—C6—C70.3 (2)C2—C1—N1—C80.44 (14)
C5—C6—C7—C80.7 (2)O1—C1—N1—C95.2 (2)
C6—C7—C8—C30.94 (19)C2—C1—N1—C9174.98 (12)
C6—C7—C8—N1177.37 (12)C7—C8—N1—C1178.61 (13)
C4—C3—C8—C70.16 (19)C3—C8—N1—C10.12 (14)
C2—C3—C8—C7178.34 (12)C7—C8—N1—C93.2 (2)
C4—C3—C8—N1178.44 (11)C3—C8—N1—C9175.28 (11)
C2—C3—C8—N10.26 (14)C14—C9—N1—C154.80 (18)
C14—C9—C10—C111.4 (2)C10—C9—N1—C1126.27 (14)
N1—C9—C10—C11177.55 (13)C14—C9—N1—C8120.01 (15)
C9—C10—C11—C121.1 (2)C10—C9—N1—C858.92 (18)
C9—C10—C11—Cl1179.71 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O1i0.982 (17)2.515 (17)3.4604 (18)161.6 (13)
C13—H13···O1ii0.91 (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.
Structure parameters of the title structures top
ALT (90 K)ART (295 K)BLT(100 K)BRT(297 K)CLT (90 K)CRT (296 K)
Mean deviation (Å)a0.014 (3)b0.011 (1)0.016 (1)0.014 (1)0.018 (1)0.015 (1)
Dihedral angle (°)74.17 (9) 114.52 (10) 113.78 (10) 75.33 (9)112.91 (17) (major) 78.11 (17) (minor)48.60 (1)49.53 (6)56.51 (4)57.73 (1)
Cell volume (Å3)1175.33 (13)1169.73 (15)1162.96 (4)
C9—N1 length (Å)1.434 (2) b1.4359 (16)1.4274 (13)1.4259 (17)1.4281 (13)1.4272 (16)
C—Cl length (Å)1.742 (2) b1.7402 (15)1.7409 (11)1.7373 (15)1.7397 (11)1.7386 (16)
CO length (Å)1.217 (3) b1.2139 (19)1.2157 (13)1.2093 (16)1.2170 (13)1.2124 (17)
Angle sum (°)c360.0 (2)360.0 (1)360.0 (1)360.0 (1)359.8 (1)359.8 (1)
Note: (a) mean deviation from the mean plane of C1–C8/N1; (b) the average value of the four independent molecules; (c) the sum of the angles surrounding atom N1.
Hydrogen-bond geometry (Å, °) for the title structures top
D—H···AD—HH···AD···AD—H···A
ALTC14—H14···O20.92 (2)2.39 (2)3.314 (2)175.0 (18)
C2—H2B···O30.94 (2)2.45 (2)3.340 (3)159.0 (19)
C22—H22B···O4i0.930 (18)2.397 (19)3.305 (3)165.4 (15)
C42—H42B···O21.00 (2)2.47 (2)3.322 (3)143 (2)
C74—H74···O30.994 (19)2.319 (19)3.306 (2)171.8 (16)
C62—H62B···O11.03 (2)2.38 (2)3.336 (3)154 (2)
ARTC14'—H14'···O1i0.93 (4)2.33 (4)3.253 (5)171 (3)
C2—H2B···O1ii0.97 (2)2.44 (2)3.360 (2)158.0 (16)
BLTC6—H6···O1i0.958 (15)2.572 (15)3.4914 (14)161.0 (13)
C11—H11···O1ii0.949 (15)2.557 (15)3.3207 (15)137.6 (12)
C12—H12···O1iii0.929 (17)2.530 (17)3.3862 (14)153.4 (14)
CLTC10—H10···O1i0.951 (14)2.471 (14)3.3841 (13)161.1 (11)
C13—H13···O1ii0.957 (15)2.494 (15)3.3925 (13)156.4 (12)
CRTC10—H10···O1i0.982 (17)2.515 (17)3.4604 (18)161.6 (13)
C13—H13···O1ii0.91 (2)2.59 (2)3.4419 (19)154.7 (16)
Symmetry code for ALT: (i) x+1, y, z. For ART: (i) x, y-1, z; (ii) -x+1, y-1/2, -z+1/2. For BLT: (i) x, y, z-1; (ii) x, -y+3/2, z-1/2; (iii) -x+1, y+1/2, -z+3/2. For CLT: (i) x, -y+1/2, z+1/2; (ii) -x+1, -y+1, -z. For CRT: (i) x, -y+1/2, z+1/2; (ii) -x+1, -y+1, -z.
 

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