#------------------------------------------------------------------------------
#$Date: 2018-11-28 21:04:59 +0200 (Wed, 28 Nov 2018) $
#$Revision: 212224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/13/2021385.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021385
loop_
_publ_author_name
'Wang, Bing'
'Fang, Qi'
_publ_section_title
;
 Structures and phase transition of three isomers of 1-phenylindolin-2-one
 derivatives: 6-chloro-1-phenylindolin-2-one,
 4-chloro-1-phenylindolin-2-one and 1-(3-chlorophenyl)indolin-2-one
;
_journal_coeditor_code           YO3056
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618015796
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C14 H10 Cl N O'
_chemical_formula_moiety         'C14 H10 Cl N O'
_chemical_formula_sum            'C14 H10 Cl N O'
_chemical_formula_weight         243.68
_chemical_name_systematic
;
4-Chloro-1-phenylindolin-2-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 89.288(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5605(8)
_cell_length_b                   12.0485(9)
_cell_length_c                   9.1939(7)
_cell_measurement_reflns_used    8615
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.80
_cell_measurement_theta_min      2.56
_cell_volume                     1169.72(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
Bruker SHELXTL and Mercury (Macrae et al.,2008)
;
_computing_publication_material
;
Bruker SHELXTL and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL-2014/7 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick 2008)
;
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23589
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.036
_diffrn_reflns_theta_min         1.929
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
APEX2 Software Suite (Bruker, 2005)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.593
_exptl_crystal_size_mid          0.329
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.305
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0532P)²+0.3065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1103
_reflns_number_gt                2575
_reflns_number_total             3410
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yo3056sup1.cif
_cod_data_source_block           B_RT
_cod_original_cell_volume        1169.73(15)
_cod_database_code               2021385
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.839
_shelx_estimated_absorpt_t_max   0.969
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.76562(13) 0.49276(12) 0.64486(14) 0.0495(3) Uani d 1
C C2 0.85585(14) 0.40585(12) 0.58575(15) 0.0511(3) Uani d 1
C C3 0.85988(12) 0.42980(11) 0.42606(14) 0.0453(3) Uani d 1
C C4 0.92506(12) 0.38062(12) 0.31262(15) 0.0504(3) Uani d 1
C C5 0.90718(15) 0.41639(13) 0.17034(16) 0.0583(4) Uani d 1
C C6 0.82218(16) 0.50083(14) 0.14390(15) 0.0588(4) Uani d 1
C C7 0.75498(14) 0.55303(12) 0.25600(14) 0.0504(3) Uani d 1
C C8 0.77665(11) 0.51631(10) 0.39620(13) 0.0427(3) Uani d 1
C C9 0.62896(12) 0.64046(11) 0.54016(13) 0.0442(3) Uani d 1
C C10 0.65075(15) 0.74267(12) 0.47462(15) 0.0517(3) Uani d 1
C C11 0.56094(17) 0.82574(14) 0.48807(18) 0.0621(4) Uani d 1
C C12 0.45172(17) 0.80830(15) 0.56878(19) 0.0662(4) Uani d 1
C C13 0.43101(15) 0.70694(15) 0.63495(18) 0.0632(4) Uani d 1
C C14 0.51839(13) 0.62236(13) 0.61987(16) 0.0530(3) Uani d 1
Cl Cl1 1.03020(4) 0.27329(4) 0.34775(5) 0.06917(15) Uani d 1
N N1 0.71932(10) 0.55296(9) 0.52730(11) 0.0450(2) Uani d 1
O O1 0.73754(11) 0.50912(10) 0.77096(10) 0.0667(3) Uani d 1
H H5 0.9537(16) 0.3826(15) 0.093(2) 0.068(5) Uiso d 1
H H6 0.8078(15) 0.5232(14) 0.0470(19) 0.066(5) Uiso d 1
H H7 0.6989(14) 0.6109(13) 0.2358(16) 0.048(4) Uiso d 1
H H10 0.7266(16) 0.7538(13) 0.4224(18) 0.058(4) Uiso d 1
H H11 0.5746(18) 0.8952(17) 0.445(2) 0.079(6) Uiso d 1
H H12 0.3920(18) 0.8602(17) 0.582(2) 0.082(6) Uiso d 1
H H13 0.3527(16) 0.7030(14) 0.7035(19) 0.065(5) Uiso d 1
H H14 0.5049(15) 0.5523(15) 0.6614(17) 0.058(4) Uiso d 1
H H2A 0.9360(16) 0.4121(14) 0.6312(19) 0.064(5) Uiso d 1
H H2B 0.8196(15) 0.3314(15) 0.6053(18) 0.063(5) Uiso d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 N1 125.01(13)
O1 C1 C2 127.11(13)
N1 C1 C2 107.88(11)
C3 C2 C1 103.25(11)
C3 C2 H2A 113.6(10)
C1 C2 H2A 110.4(10)
C3 C2 H2B 111.1(10)
C1 C2 H2B 108.8(9)
H2A C2 H2B 109.6(14)
C4 C3 C8 118.92(12)
C4 C3 C2 131.93(13)
C8 C3 C2 109.10(11)
C3 C4 C5 120.41(14)
C3 C4 Cl1 119.62(11)
C5 C4 Cl1 119.97(11)
C6 C5 C4 119.32(13)
C6 C5 H5 121.1(11)
C4 C5 H5 119.6(11)
C5 C6 C7 121.90(13)
C5 C6 H6 119.3(10)
C7 C6 H6 118.8(10)
C8 C7 C6 117.11(14)
C8 C7 H7 122.4(9)
C6 C7 H7 120.5(9)
C7 C8 C3 122.31(12)
C7 C8 N1 128.34(13)
C3 C8 N1 109.30(10)
C14 C9 C10 120.13(13)
C14 C9 N1 119.03(12)
C10 C9 N1 120.83(12)
C11 C10 C9 119.54(14)
C11 C10 H10 121.5(10)
C9 C10 H10 119.0(10)
C12 C11 C10 120.36(16)
C12 C11 H11 119.2(12)
C10 C11 H11 120.4(12)
C11 C12 C13 119.90(16)
C11 C12 H12 123.3(13)
C13 C12 H12 116.8(13)
C14 C13 C12 120.44(15)
C14 C13 H13 123.8(10)
C12 C13 H13 115.5(9)
C13 C14 C9 119.60(15)
C13 C14 H14 121.7(10)
C9 C14 H14 118.7(10)
C1 N1 C8 110.35(11)
C1 N1 C9 124.11(10)
C8 N1 C9 125.53(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2093(16)
C1 N1 1.3952(16)
C1 C2 1.512(2)
C2 C3 1.4963(18)
C2 H2A 0.952(18)
C2 H2B 0.991(18)
C3 C4 1.3765(18)
C3 C8 1.3930(18)
C4 C5 1.392(2)
C4 Cl1 1.7373(15)
C5 C6 1.380(2)
C5 H5 0.948(18)
C6 C7 1.394(2)
C6 H6 0.945(17)
C7 C8 1.3845(17)
C7 H7 0.935(16)
C8 N1 1.4129(15)
C9 C14 1.3881(18)
C9 C10 1.3889(19)
C9 N1 1.4259(17)
C10 C11 1.383(2)
C10 H10 0.938(17)
C11 C12 1.380(2)
C11 H11 0.94(2)
C12 C13 1.381(3)
C12 H12 0.90(2)
C13 C14 1.381(2)
C13 H13 1.034(17)
C14 H14 0.937(18)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 -176.24(14)
N1 C1 C2 C3 3.45(14)
C1 C2 C3 C4 179.55(14)
C1 C2 C3 C8 -2.82(14)
C8 C3 C4 C5 -0.47(19)
C2 C3 C4 C5 176.96(14)
C8 C3 C4 Cl1 179.52(9)
C2 C3 C4 Cl1 -3.0(2)
C3 C4 C5 C6 -0.8(2)
Cl1 C4 C5 C6 179.21(12)
C4 C5 C6 C7 1.2(2)
C5 C6 C7 C8 -0.2(2)
C6 C7 C8 C3 -1.1(2)
C6 C7 C8 N1 -178.38(13)
C4 C3 C8 C7 1.47(19)
C2 C3 C8 C7 -176.51(12)
C4 C3 C8 N1 179.19(11)
C2 C3 C8 N1 1.21(14)
C14 C9 C10 C11 -0.7(2)
N1 C9 C10 C11 179.52(12)
C9 C10 C11 C12 1.5(2)
C10 C11 C12 C13 -0.9(2)
C11 C12 C13 C14 -0.6(2)
C12 C13 C14 C9 1.4(2)
C10 C9 C14 C13 -0.8(2)
N1 C9 C14 C13 179.04(13)
O1 C1 N1 C8 176.77(14)
C2 C1 N1 C8 -2.93(14)
O1 C1 N1 C9 -2.0(2)
C2 C1 N1 C9 178.33(11)
C7 C8 N1 C1 178.66(13)
C3 C8 N1 C1 1.11(14)
C7 C8 N1 C9 -2.6(2)
C3 C8 N1 C9 179.83(11)
C14 C9 N1 C1 -50.32(17)
C10 C9 N1 C1 129.47(14)
C14 C9 N1 C8 131.12(13)
C10 C9 N1 C8 -49.09(18)

_cod_database_fobs_code 2021385
