#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/20/4032012.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4032012
loop_
_publ_author_name
'Zhao, Li-Ming'
'Zhang, Ai-Li'
'Zhang, Jie-Huan'
'Gao, Hua-Shuai'
'Zhou, Wei'
_publ_section_title
;
 Zinc-Mediated C-3 α-Prenylation of Isatins with Prenyl Bromide: Access
 to 3-Prenyl-3-hydroxy-2-oxindoles and Its Application.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5487
_journal_page_last               5494
_journal_paper_doi               10.1021/acs.joc.6b00836
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 96.5690(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1491(10)
_cell_length_b                   11.4621(11)
_cell_length_c                   10.7009(10)
_cell_measurement_reflns_used    2580
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      2.61
_cell_volume                     1236.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6740
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_correction_T_min  0.9961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0729P)²+0.1369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                1970
_reflns_number_total             2527
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00836_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4032012
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.02042(11) 0.38771(8) 0.16433(9) 0.0512(3) Uani 1 1 d .
H1 H 0.0084 0.3888 0.0872 0.077 Uiso 1 1 calc R
O2 O 0.01143(12) 0.63637(8) 0.08801(10) 0.0608(3) Uani 1 1 d .
N1 N 0.07434(12) 0.65035(10) 0.29901(10) 0.0478(3) Uani 1 1 d .
H1A H 0.0533 0.7221 0.3092 0.057 Uiso 1 1 calc R
C1 C 0.19895(15) 0.37774(13) 0.42635(15) 0.0562(4) Uani 1 1 d .
H1B H 0.2141 0.3041 0.3943 0.067 Uiso 1 1 calc R
C2 C 0.22396(19) 0.39959(16) 0.55379(16) 0.0673(5) Uani 1 1 d .
H2 H 0.2567 0.3403 0.6080 0.081 Uiso 1 1 calc R
C3 C 0.20081(19) 0.50851(16) 0.60125(16) 0.0682(5) Uani 1 1 d .
H3 H 0.2190 0.5217 0.6873 0.082 Uiso 1 1 calc R
C4 C 0.15104(16) 0.59895(14) 0.52363(14) 0.0579(4) Uani 1 1 d .
H4 H 0.1348 0.6722 0.5559 0.069 Uiso 1 1 calc R
C5 C 0.12679(13) 0.57598(11) 0.39747(12) 0.0440(3) Uani 1 1 d .
C6 C 0.15118(13) 0.46689(11) 0.34744(13) 0.0428(3) Uani 1 1 d .
C7 C 0.11883(13) 0.47125(11) 0.20732(13) 0.0425(3) Uani 1 1 d .
C8 C 0.06145(13) 0.59570(11) 0.18807(12) 0.0434(3) Uani 1 1 d .
C9 C 0.24102(16) 0.45828(14) 0.13575(15) 0.0578(4) Uani 1 1 d .
H9A H 0.2798 0.3819 0.1536 0.069 Uiso 1 1 calc R
H9B H 0.2125 0.4620 0.0462 0.069 Uiso 1 1 calc R
C10 C 0.34468(16) 0.54843(17) 0.16782(17) 0.0662(5) Uani 1 1 d .
H10 H 0.3800 0.5528 0.2518 0.079 Uiso 1 1 calc R
C11 C 0.39218(17) 0.62310(18) 0.09001(19) 0.0736(5) Uani 1 1 d .
C12 C 0.3497(2) 0.6297(2) -0.0483(2) 0.0928(7) Uani 1 1 d .
H12A H 0.4197 0.6014 -0.0934 0.139 Uiso 1 1 calc R
H12B H 0.3301 0.7092 -0.0717 0.139 Uiso 1 1 calc R
H12C H 0.2719 0.5827 -0.0687 0.139 Uiso 1 1 calc R
C13 C 0.4992(3) 0.7092(3) 0.1369(3) 0.1317(11) Uani 1 1 d .
H13A H 0.5197 0.7011 0.2263 0.198 Uiso 1 1 calc R
H13B H 0.4686 0.7871 0.1175 0.198 Uiso 1 1 calc R
H13C H 0.5773 0.6941 0.0967 0.198 Uiso 1 1 calc R
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
C7 O1 H1 109.5
C8 N1 C5 111.75(11)
C8 N1 H1A 124.1
C5 N1 H1A 124.1
C6 C1 C2 118.85(14)
C6 C1 H1B 120.6
C2 C1 H1B 120.6
C3 C2 C1 120.56(15)
C3 C2 H2 119.7
C1 C2 H2 119.7
C2 C3 C4 121.47(15)
C2 C3 H3 119.3
C4 C3 H3 119.3
C5 C4 C3 117.30(14)
C5 C4 H4 121.3
C3 C4 H4 121.3
C4 C5 C6 122.09(13)
C4 C5 N1 129.02(13)
C6 C5 N1 108.88(12)
C1 C6 C5 119.71(13)
C1 C6 C7 131.25(12)
C5 C6 C7 109.04(11)
O1 C7 C6 111.51(11)
O1 C7 C9 110.52(11)
C6 C7 C9 113.47(12)
O1 C7 C8 109.78(10)
C6 C7 C8 101.55(10)
C9 C7 C8 109.63(12)
O2 C8 N1 126.00(13)
O2 C8 C7 125.49(12)
N1 C8 C7 108.50(11)
C10 C9 C7 114.06(12)
C10 C9 H9A 108.7
C7 C9 H9A 108.7
C10 C9 H9B 108.7
C7 C9 H9B 108.7
H9A C9 H9B 107.6
C11 C10 C9 127.13(17)
C11 C10 H10 116.4
C9 C10 H10 116.4
C10 C11 C12 124.81(18)
C10 C11 C13 120.9(2)
C12 C11 C13 114.3(2)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.4216(15)
O1 H1 0.8200
O2 C8 1.2236(15)
N1 C8 1.3354(17)
N1 C5 1.4113(17)
N1 H1A 0.8600
C1 C6 1.3779(19)
C1 C2 1.381(2)
C1 H1B 0.9300
C2 C3 1.378(3)
C2 H2 0.9300
C3 C4 1.387(2)
C3 H3 0.9300
C4 C5 1.3698(19)
C4 H4 0.9300
C5 C6 1.3935(18)
C6 C7 1.4987(19)
C7 C9 1.537(2)
C7 C8 1.5455(18)
C9 C10 1.487(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.323(3)
C10 H10 0.9300
C11 C12 1.496(3)
C11 C13 1.510(3)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139094723
