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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 C
14H
10ClNO, 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
P2
1/
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 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
P2
1/
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
P2
1/
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
CCDC references: 1877592; 1877591; 1877590; 1877589; 1877588; 1877587
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
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) Å3 | 0.38 × 0.32 × 0.16 mm |
Data collection top
Bruker APEXII CCD diffractometer | 11212 reflections with I > 2σ(I) |
Detector resolution: 8.3 pixels mm-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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | All 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 reflections | Δρmax = 0.47 e Å−3 |
770 parameters | Δρmin = −0.31 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O4i | 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)
top
Crystal data top
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) Å3 | Block, colorless |
Z = 4 | 0.38 × 0.32 × 0.16 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | All 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 reflections | Δρmax = 0.29 e Å−3 |
246 parameters | Δρmin = −0.33 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C14′—H14′···O1i | 0.93 (4) | 2.33 (4) | 3.253 (5) | 171 (3) |
C2—H2B···O1ii | 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)
top
Crystal data top
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) Å3 | PLANE, colourless |
Z = 4 | 0.59 × 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-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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | All 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 reflections | Δρmax = 0.43 e Å−3 |
194 parameters | Δρmin = −0.25 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.958 (15) | 2.572 (15) | 3.4914 (14) | 161.0 (13) |
C11—H11···O1ii | 0.949 (15) | 2.557 (15) | 3.3207 (15) | 137.6 (12) |
C12—H12···O1iii | 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)
top
Crystal data top
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) Å3 | Plate, colourless |
Z = 4 | 0.59 × 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-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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | All 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 reflections | Δρmax = 0.29 e Å−3 |
194 parameters | Δρmin = −0.30 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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)
top
Crystal data top
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) Å3 | Bar, colourless |
Z = 4 | 0.60 × 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-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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | All 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 reflections | Δρmax = 0.42 e Å−3 |
194 parameters | Δρmin = −0.27 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O1i | 0.951 (14) | 2.471 (14) | 3.3841 (13) | 161.1 (11) |
C13—H13···O1ii | 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)
top
Crystal data top
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) Å3 | Bar, colourless |
Z = 4 | 0.60 × 0.23 × 0.09 mm |
Data collection top
Bruker APEXII CCD diffractometer | 2359 reflections with I > 2σ(I) |
Detector resolution: 8.3 pixels mm-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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | All 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 reflections | Δρmax = 0.38 e Å−3 |
194 parameters | Δρmin = −0.56 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O1i | 0.982 (17) | 2.515 (17) | 3.4604 (18) | 161.6 (13) |
C13—H13···O1ii | 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. |
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)a | 0.014 (3)b | 0.011 (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) b | 1.4359 (16) | 1.4274 (13) | 1.4259 (17) | 1.4281 (13) | 1.4272 (16) |
C—Cl length (Å) | 1.742 (2) b | 1.7402 (15) | 1.7409 (11) | 1.7373 (15) | 1.7397 (11) | 1.7386 (16) |
C═O length (Å) | 1.217 (3) b | 1.2139 (19) | 1.2157 (13) | 1.2093 (16) | 1.2170 (13) | 1.2124 (17) |
Angle sum (°)c | 360.0 (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···A | D—H | H···A | D···A | D—H···A |
ALT | 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···O4i | 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) |
| | | | | |
ART | C14'—H14'···O1i | 0.93 (4) | 2.33 (4) | 3.253 (5) | 171 (3) |
| C2—H2B···O1ii | 0.97 (2) | 2.44 (2) | 3.360 (2) | 158.0 (16) |
| | | | | |
BLT | C6—H6···O1i | 0.958 (15) | 2.572 (15) | 3.4914 (14) | 161.0 (13) |
| C11—H11···O1ii | 0.949 (15) | 2.557 (15) | 3.3207 (15) | 137.6 (12) |
| C12—H12···O1iii | 0.929 (17) | 2.530 (17) | 3.3862 (14) | 153.4 (14) |
| | | | | |
CLT | C10—H10···O1i | 0.951 (14) | 2.471 (14) | 3.3841 (13) | 161.1 (11) |
| C13—H13···O1ii | 0.957 (15) | 2.494 (15) | 3.3925 (13) | 156.4 (12) |
| | | | | |
CRT | C10—H10···O1i | 0.982 (17) | 2.515 (17) | 3.4604 (18) | 161.6 (13) |
| C13—H13···O1ii | 0.91 (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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