#------------------------------------------------------------------------------
#$Date: 2018-11-28 21:04:59 +0200 (Wed, 28 Nov 2018) $
#$Revision: 212224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/13/2021387.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_2021387
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
;
1-(3-Chlorophenyl)-indolin-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                 109.9960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1901(2)
_cell_length_b                   13.6596(3)
_cell_length_c                   8.0965(2)
_cell_measurement_reflns_used    7649
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.44
_cell_volume                     1162.96(4)
_computing_cell_refinement
;
SAINT (Bruker, 2005)
;
_computing_data_collection
;
APEX2 (Bruker, 2005)
;
_computing_data_reduction
;
SAINT (Bruker, 2005)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick 2008) and Mercury (Macrae et al.,2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21800
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.430
_diffrn_reflns_theta_min         1.937
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(APEX2; Bruker, 2005)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       bar
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.596
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.564
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0685P)²+0.1297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                2359
_reflns_number_total             3159
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yo3056sup1.cif
_cod_data_source_block           C_RT
_cod_database_code               2021387
_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   0.837
_shelx_estimated_absorpt_t_max   0.973
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 0.83010(13) 0.37519(9) 0.24314(18) 0.0357(3) Uani d 1
C C2 0.97339(13) 0.36994(10) 0.33071(18) 0.0350(3) Uani d 1
C C3 0.99289(12) 0.37266(9) 0.52246(17) 0.0332(3) Uani d 1
C C4 1.10215(13) 0.37232(10) 0.6691(2) 0.0401(3) Uani d 1
C C5 1.09155(15) 0.38035(10) 0.8349(2) 0.0445(3) Uani d 1
C C6 0.97341(15) 0.38681(10) 0.85297(19) 0.0424(3) Uani d 1
C C7 0.86177(14) 0.38606(10) 0.70735(18) 0.0382(3) Uani d 1
C C8 0.87487(12) 0.37960(9) 0.54348(17) 0.0321(3) Uani d 1
C C9 0.64634(12) 0.39487(10) 0.34614(18) 0.0359(3) Uani d 1
C C10 0.58388(13) 0.32968(11) 0.42009(19) 0.0409(3) Uani d 1
C C11 0.45727(13) 0.34684(12) 0.39525(19) 0.0455(3) Uani d 1
C C12 0.39209(14) 0.42498(14) 0.2979(2) 0.0507(4) Uani d 1
C C13 0.45507(16) 0.48767(13) 0.2224(2) 0.0523(4) Uani d 1
C C14 0.58227(15) 0.47375(11) 0.2469(2) 0.0442(3) Uani d 1
Cl Cl1 0.37809(5) 0.26605(5) 0.48804(8) 0.0793(2) Uani d 1
N N1 0.77845(10) 0.38116(8) 0.37545(14) 0.0362(3) Uani d 1
O O1 0.76945(10) 0.37418(8) 0.08714(13) 0.0490(3) Uani d 1
H H4 1.1840(16) 0.3671(12) 0.654(2) 0.044(4) Uiso d 1
H H5 1.1730(17) 0.3818(13) 0.946(2) 0.057(5) Uiso d 1
H H6 0.9701(16) 0.3922(13) 0.970(3) 0.054(5) Uiso d 1
H H7 0.7811(16) 0.3894(11) 0.722(2) 0.044(4) Uiso d 1
H H10 0.6299(15) 0.2743(12) 0.491(2) 0.044(4) Uiso d 1
H H12 0.3046(18) 0.4351(15) 0.281(3) 0.066(5) Uiso d 1
H H13 0.412(2) 0.5404(14) 0.161(3) 0.065(5) Uiso d 1
H H14 0.6268(17) 0.5176(14) 0.195(2) 0.053(5) Uiso d 1
H H2A 1.0127(15) 0.4231(13) 0.298(2) 0.046(4) Uiso d 1
H H2B 1.0032(16) 0.3121(13) 0.296(2) 0.048(4) 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 125.06(13)
O1 C1 C2 127.74(13)
N1 C1 C2 107.20(11)
C3 C2 C1 103.90(11)
C3 C2 H2A 111.3(10)
C1 C2 H2A 110.8(10)
C3 C2 H2B 113.0(10)
C1 C2 H2B 109.1(10)
H2A C2 H2B 108.6(14)
C4 C3 C8 119.52(12)
C4 C3 C2 131.68(12)
C8 C3 C2 108.77(11)
C3 C4 C5 119.08(13)
C3 C4 H4 119.4(9)
C5 C4 H4 121.6(10)
C6 C5 C4 120.48(14)
C6 C5 H5 119.8(10)
C4 C5 H5 119.7(10)
C5 C6 C7 121.55(14)
C5 C6 H6 118.0(10)
C7 C6 H6 120.5(10)
C8 C7 C6 116.89(13)
C8 C7 H7 122.7(10)
C6 C7 H7 120.4(10)
C7 C8 C3 122.46(12)
C7 C8 N1 128.48(12)
C3 C8 N1 109.04(11)
C14 C9 C10 120.74(13)
C14 C9 N1 119.92(12)
C10 C9 N1 119.33(12)
C11 C10 C9 118.10(13)
C11 C10 H10 121.6(9)
C9 C10 H10 120.3(9)
C12 C11 C10 122.04(14)
C12 C11 Cl1 119.38(12)
C10 C11 Cl1 118.57(12)
C13 C12 C11 118.96(14)
C13 C12 H12 120.1(12)
C11 C12 H12 120.9(12)
C12 C13 C14 120.58(15)
C12 C13 H13 118.7(13)
C14 C13 H13 120.7(13)
C13 C14 C9 119.55(15)
C13 C14 H14 120.9(11)
C9 C14 H14 119.6(11)
C1 N1 C8 111.09(11)
C1 N1 C9 124.24(11)
C8 N1 C9 124.50(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2124(17)
C1 N1 1.3827(17)
C1 C2 1.5170(19)
C2 C3 1.4925(19)
C2 H2A 0.934(17)
C2 H2B 0.936(18)
C3 C4 1.383(2)
C3 C8 1.3914(18)
C4 C5 1.392(2)
C4 H4 0.967(17)
C5 C6 1.382(2)
C5 H5 1.037(18)
C6 C7 1.394(2)
C6 H6 0.966(19)
C7 C8 1.3866(19)
C7 H7 0.952(16)
C8 N1 1.4183(17)
C9 C14 1.388(2)
C9 C10 1.388(2)
C9 N1 1.4272(16)
C10 C11 1.381(2)
C10 H10 0.982(17)
C11 C12 1.378(2)
C11 Cl1 1.7386(16)
C12 C13 1.378(2)
C12 H12 0.951(19)
C13 C14 1.381(2)
C13 H13 0.91(2)
C14 H14 0.961(18)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C10 H10 O1 4_566 0.982(17) 2.515(17) 3.4604(18) 161.6(13)
C13 H13 O1 3_665 0.91(2) 2.59(2) 3.4419(19) 154.7(16)
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 -179.22(13)
N1 C1 C2 C3 0.56(13)
C1 C2 C3 C4 -178.38(13)
C1 C2 C3 C8 -0.50(14)
C8 C3 C4 C5 -0.89(19)
C2 C3 C4 C5 176.80(14)
C3 C4 C5 C6 1.1(2)
C4 C5 C6 C7 -0.3(2)
C5 C6 C7 C8 -0.7(2)
C6 C7 C8 C3 0.94(19)
C6 C7 C8 N1 -177.37(12)
C4 C3 C8 C7 -0.16(19)
C2 C3 C8 C7 -178.34(12)
C4 C3 C8 N1 178.44(11)
C2 C3 C8 N1 0.26(14)
C14 C9 C10 C11 -1.4(2)
N1 C9 C10 C11 177.55(13)
C9 C10 C11 C12 1.1(2)
C9 C10 C11 Cl1 -179.71(11)
C10 C11 C12 C13 0.3(2)
Cl1 C11 C12 C13 -178.92(13)
C11 C12 C13 C14 -1.4(3)
C12 C13 C14 C9 1.1(2)
C10 C9 C14 C13 0.3(2)
N1 C9 C14 C13 -178.61(14)
O1 C1 N1 C8 179.35(13)
C2 C1 N1 C8 -0.44(14)
O1 C1 N1 C9 -5.2(2)
C2 C1 N1 C9 174.98(12)
C7 C8 N1 C1 178.61(13)
C3 C8 N1 C1 0.12(14)
C7 C8 N1 C9 3.2(2)
C3 C8 N1 C9 -175.28(11)
C14 C9 N1 C1 -54.80(18)
C10 C9 N1 C1 126.27(14)
C14 C9 N1 C8 120.01(15)
C10 C9 N1 C8 -58.92(18)

_cod_database_fobs_code 2021387
