#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/29/2232959.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_2232959
loop_
_publ_author_name
'Pevec, Andrej'
'Kafka, Stanislav'
'Košmrlj, Janez'
_publ_section_title
;
 2-Hydroxy-2-methyl-1-phenylindolin-3-one
;
_journal_coeditor_code           TK5007
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3228
_journal_page_last               o3229
_journal_paper_doi               10.1107/S1600536811045302
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H13 N O2'
_chemical_formula_moiety         'C15 H13 N O2'
_chemical_formula_sum            'C15 H13 N O2'
_chemical_formula_weight         239.26
_chemical_melting_point_gt       397
_chemical_melting_point_lt       399
_chemical_name_systematic
;
2-Hydroxy-2-methyl-1-phenylindolin-3-one
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.0146(4)
_cell_length_b                   9.2193(2)
_cell_length_c                   15.3843(4)
_cell_measurement_reflns_used    3116
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2413.22(10)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5144
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9741
_exptl_absorpt_correction_T_min  0.9532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0545P)²+0.3729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                1890
_reflns_number_total             2745
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5007.cif
_cod_data_source_block           I
_cod_database_code               2232959
_cod_database_fobs_code          2232959
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.58436(6) 0.68168(12) 0.29672(6) 0.0524(3) Uani d . 1 1
O O2 0.54290(7) 0.87398(11) 0.15350(7) 0.0562(3) Uani d . 1 1
H H2 0.5002 0.8334 0.1584 0.084 Uiso calc R 1 1
N N1 0.59892(7) 0.68372(12) 0.06732(7) 0.0406(3) Uani d . 1 1
C C1 0.59694(8) 0.51234(15) 0.17738(9) 0.0416(3) Uani d . 1 1
C C2 0.60064(8) 0.53713(15) 0.08779(9) 0.0404(3) Uani d . 1 1
C C3 0.60139(9) 0.42005(16) 0.03007(11) 0.0524(4) Uani d . 1 1
H H3 0.6043 0.4339 -0.0297 0.063 Uiso calc R 1 1
C C4 0.59754(10) 0.28280(17) 0.06584(12) 0.0614(5) Uani d . 1 1
H H4 0.5981 0.2033 0.0286 0.074 Uiso calc R 1 1
C C5 0.59282(10) 0.25788(18) 0.15492(13) 0.0620(5) Uani d . 1 1
H H5 0.5900 0.1635 0.1760 0.074 Uiso calc R 1 1
C C6 0.59237(9) 0.37246(16) 0.21147(11) 0.0526(4) Uani d . 1 1
H H6 0.5891 0.3574 0.2711 0.063 Uiso calc R 1 1
C C7 0.59389(8) 0.65226(15) 0.22002(9) 0.0405(3) Uani d . 1 1
C C8 0.60272(8) 0.76939(15) 0.14873(9) 0.0407(3) Uani d . 1 1
C C9 0.68031(10) 0.84809(18) 0.15897(11) 0.0580(4) Uani d . 1 1
H H9A 0.6833 0.8899 0.2160 0.087 Uiso calc R 1 1
H H9B 0.6840 0.9235 0.1161 0.087 Uiso calc R 1 1
H H9C 0.7228 0.7808 0.1512 0.087 Uiso calc R 1 1
C C10 0.63405(8) 0.74129(14) -0.00952(8) 0.0392(3) Uani d . 1 1
C C11 0.59874(9) 0.85663(15) -0.05174(10) 0.0472(4) Uani d . 1 1
H H11 0.5505 0.8915 -0.0326 0.057 Uiso calc R 1 1
C C12 0.63529(10) 0.92009(17) -0.12243(11) 0.0561(4) Uani d . 1 1
H H12 0.6115 0.9979 -0.1505 0.067 Uiso calc R 1 1
C C13 0.70639(10) 0.86900(16) -0.15140(10) 0.0534(4) Uani d . 1 1
H H13 0.7310 0.9128 -0.1986 0.064 Uiso calc R 1 1
C C14 0.74101(9) 0.75336(16) -0.11069(10) 0.0519(4) Uani d . 1 1
H H14 0.7889 0.7181 -0.1307 0.062 Uiso calc R 1 1
C C15 0.70513(9) 0.68883(16) -0.03994(9) 0.0473(4) Uani d . 1 1
H H15 0.7288 0.6100 -0.0127 0.057 Uiso calc R 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 O2 H2 109.5
C2 N1 C10 122.77(11)
C2 N1 C8 109.04(11)
C10 N1 C8 118.92(10)
C6 C1 C2 121.62(13)
C6 C1 C7 130.66(14)
C2 C1 C7 107.61(12)
N1 C2 C3 127.44(14)
N1 C2 C1 112.44(12)
C3 C2 C1 120.02(13)
C4 C3 C2 116.99(15)
C4 C3 H3 121.5
C2 C3 H3 121.5
C3 C4 C5 123.10(16)
C3 C4 H4 118.4
C5 C4 H4 118.4
C6 C5 C4 119.92(15)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C1 118.33(15)
C5 C6 H6 120.8
C1 C6 H6 120.8
O1 C7 C1 129.80(13)
O1 C7 C8 122.88(13)
C1 C7 C8 107.30(11)
O2 C8 N1 112.24(11)
O2 C8 C9 107.31(12)
N1 C8 C9 112.40(11)
O2 C8 C7 111.84(11)
N1 C8 C7 102.88(10)
C9 C8 C7 110.21(12)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C15 119.30(13)
C11 C10 N1 119.54(12)
C15 C10 N1 121.07(12)
C12 C11 C10 119.95(14)
C12 C11 H11 120.0
C10 C11 H11 120.0
C13 C12 C11 120.44(14)
C13 C12 H12 119.8
C11 C12 H12 119.8
C14 C13 C12 119.84(14)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 120.34(14)
C13 C14 H14 119.8
C15 C14 H14 119.8
C14 C15 C10 120.11(14)
C14 C15 H15 119.9
C10 C15 H15 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2216(16)
O2 C8 1.4040(16)
O2 H2 0.8200
N1 C2 1.3880(17)
N1 C10 1.4271(17)
N1 C8 1.4821(17)
C1 C6 1.3943(19)
C1 C2 1.398(2)
C1 C7 1.4481(19)
C2 C3 1.398(2)
C3 C4 1.381(2)
C3 H3 0.9300
C4 C5 1.392(3)
C4 H4 0.9300
C5 C6 1.368(2)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.5464(19)
C8 C9 1.515(2)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.3833(19)
C10 C15 1.3840(19)
C11 C12 1.383(2)
C11 H11 0.9300
C12 C13 1.373(2)
C12 H12 0.9300
C13 C14 1.370(2)
C13 H13 0.9300
C14 C15 1.383(2)
C14 H14 0.9300
C15 H15 0.9300
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
O2 H2 O1 4_655 0.82 2.12 2.9014(15) 159
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
C10 N1 C2 C3 -31.0(2)
C8 N1 C2 C3 -177.20(14)
C10 N1 C2 C1 152.51(12)
C8 N1 C2 C1 6.35(15)
C6 C1 C2 N1 175.46(12)
C7 C1 C2 N1 -1.03(15)
C6 C1 C2 C3 -1.3(2)
C7 C1 C2 C3 -177.77(13)
N1 C2 C3 C4 -175.56(13)
C1 C2 C3 C4 0.6(2)
C2 C3 C4 C5 0.2(2)
C3 C4 C5 C6 -0.4(3)
C4 C5 C6 C1 -0.2(2)
C2 C1 C6 C5 1.0(2)
C7 C1 C6 C5 176.62(14)
C6 C1 C7 O1 -2.2(3)
C2 C1 C7 O1 173.84(14)
C6 C1 C7 C8 179.50(14)
C2 C1 C7 C8 -4.44(14)
C2 N1 C8 O2 -128.83(11)
C10 N1 C8 O2 83.51(14)
C2 N1 C8 C9 110.09(13)
C10 N1 C8 C9 -37.57(17)
C2 N1 C8 C7 -8.44(13)
C10 N1 C8 C7 -156.10(11)
O1 C7 C8 O2 -50.00(18)
C1 C7 C8 O2 128.43(12)
O1 C7 C8 N1 -170.66(12)
C1 C7 C8 N1 7.77(13)
O1 C7 C8 C9 69.29(16)
C1 C7 C8 C9 -112.29(12)
C2 N1 C10 C11 144.73(13)
C8 N1 C10 C11 -72.24(17)
C2 N1 C10 C15 -38.80(19)
C8 N1 C10 C15 104.23(15)
C15 C10 C11 C12 -1.3(2)
N1 C10 C11 C12 175.20(13)
C10 C11 C12 C13 0.3(2)
C11 C12 C13 C14 0.7(3)
C12 C13 C14 C15 -0.7(2)
C13 C14 C15 C10 -0.3(2)
C11 C10 C15 C14 1.3(2)
N1 C10 C15 C14 -175.13(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9282573
