#------------------------------------------------------------------------------
#$Date: 2021-06-05 21:18:58 +0200 (Sat 05 de Jun de 2021) $
#$Revision: 266126 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/05/7060552.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_7060552
loop_
_publ_author_name
'Devi, Manju'
'Jadhav, Amol P.'
'Singh, Ravi P.'
_publ_section_title
;
 KOH-mediated stereoselective alkylation of 3-bromooxindoles for the
 synthesis of 3,3′-disubstituted oxindoles with two contiguous all
 carbon quaternary centres
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8445
_journal_page_last               8448
_journal_paper_doi               10.1039/D0NJ06283A
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C24 H18 Br N2 0, C H Cl3'
_chemical_formula_sum            'C25 H19 Br Cl3 N2 O'
_chemical_formula_weight         549.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-10-19 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.314(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0457(6)
_cell_length_b                   13.8112(6)
_cell_length_c                   14.5205(6)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.24
_cell_volume                     2413.74(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
_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       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0994
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            69097
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.390
_diffrn_reflns_theta_min         2.036
_exptl_absorpt_coefficient_mu    2.056
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       block
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   0.814
_exptl_transmission_factor_min   0.698
_refine_diff_density_max         1.436
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.460
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         6039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.460
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0898
_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)+(0.1000P)²+0.3517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2211
_refine_ls_wR_factor_ref         0.2348
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4488
_reflns_number_total             6039
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj06283a2.cif
_cod_data_source_block           MANJU01_0m_a
_cod_depositor_comments          'Adding full bibliography for 7060552.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7060552
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.66372(4) 0.43028(3) 0.51583(4) 0.0607(2) Uani 1 1 d . . . . .
Cl2 Cl 0.35135(15) 0.98847(13) 0.50570(9) 0.0886(5) Uani 1 1 d . . . . .
Cl1 Cl 0.38070(19) 0.98871(12) 0.70224(9) 0.1022(7) Uani 1 1 d . . . . .
Cl3 Cl 0.3111(2) 0.81521(14) 0.60972(12) 0.1113(7) Uani 1 1 d . . . . .
O1 O 0.6358(3) 0.85153(18) 0.6608(2) 0.0474(7) Uani 1 1 d . . . . .
N2 N 0.6321(3) 0.5208(2) 0.8379(2) 0.0467(8) Uani 1 1 d . . . . .
N1 N 0.8153(3) 0.8216(2) 0.6271(2) 0.0443(7) Uani 1 1 d . . . . .
C8 C 0.7130(3) 0.7957(2) 0.6515(2) 0.0371(8) Uani 1 1 d . . . . .
C1 C 0.7112(3) 0.6844(2) 0.6689(2) 0.0328(7) Uani 1 1 d . . . . .
C18 C 0.5807(4) 0.6808(3) 0.8093(2) 0.0403(8) Uani 1 1 d . . . . .
C2 C 0.8264(3) 0.6560(2) 0.6401(2) 0.0366(7) Uani 1 1 d . . . . .
C16 C 0.6965(3) 0.6682(2) 0.7759(2) 0.0381(8) Uani 1 1 d . . . . .
C10 C 0.6215(3) 0.6354(3) 0.5097(2) 0.0385(8) Uani 1 1 d . . . . .
C19 C 0.7131(4) 0.5620(3) 0.7997(3) 0.0466(10) Uani 1 1 d . . . . .
H19 H 0.778132 0.529034 0.787166 0.056 Uiso 1 1 calc R U . . .
C9 C 0.6133(3) 0.6359(3) 0.6132(2) 0.0367(7) Uani 1 1 d . . . . .
H9A H 0.607114 0.569405 0.633914 0.044 Uiso 1 1 calc R U . . .
H9B H 0.545225 0.668840 0.628077 0.044 Uiso 1 1 calc R U . . .
C7 C 0.8847(4) 0.7403(3) 0.6185(2) 0.0414(8) Uani 1 1 d . . . . .
C20 C 0.5464(4) 0.5913(3) 0.8441(3) 0.0447(9) Uani 1 1 d . . . . .
C21 C 0.4453(5) 0.5781(3) 0.8825(3) 0.0577(12) Uani 1 1 d . . . . .
H21 H 0.424832 0.518110 0.905329 0.069 Uiso 1 1 calc R U . . .
C24 C 0.5096(4) 0.7592(3) 0.8160(3) 0.0536(11) Uani 1 1 d . . . . .
H24 H 0.530731 0.819818 0.795110 0.064 Uiso 1 1 calc R U . . .
C3 C 0.8783(4) 0.5675(3) 0.6317(3) 0.0451(9) Uani 1 1 d . . . . .
H3 H 0.841091 0.510359 0.644579 0.054 Uiso 1 1 calc R U . . .
C6 C 0.9926(4) 0.7387(4) 0.5912(3) 0.0568(11) Uani 1 1 d . . . . .
H6 H 1.030152 0.795557 0.577963 0.068 Uiso 1 1 calc R U . . .
C15 C 0.6409(4) 0.5524(3) 0.4583(3) 0.0466(9) Uani 1 1 d . . . . .
C4 C 0.9880(4) 0.5653(3) 0.6035(3) 0.0552(11) Uani 1 1 d . . . . .
H4 H 1.023927 0.506153 0.597806 0.066 Uiso 1 1 calc R U . . .
C5 C 1.0433(4) 0.6489(4) 0.5841(3) 0.0612(12) Uani 1 1 d . . . . .
H5 H 1.116267 0.645550 0.565802 0.073 Uiso 1 1 calc R U . . .
C23 C 0.4067(5) 0.7469(4) 0.8541(3) 0.0661(14) Uani 1 1 d . . . . .
H23 H 0.359000 0.799535 0.858050 0.079 Uiso 1 1 calc R U . . .
C17 C 0.7827(4) 0.7290(3) 0.8337(3) 0.0564(12) Uani 1 1 d . . . . .
H17A H 0.772565 0.796439 0.819749 0.085 Uiso 1 1 calc R U . . .
H17B H 0.856461 0.709693 0.819028 0.085 Uiso 1 1 calc R U . . .
H17C H 0.772257 0.718421 0.898156 0.085 Uiso 1 1 calc R U . . .
C22 C 0.3742(5) 0.6576(4) 0.8861(3) 0.0684(14) Uani 1 1 d . . . . .
H22 H 0.304318 0.650429 0.910232 0.082 Uiso 1 1 calc R U . . .
C11 C 0.6001(4) 0.7219(3) 0.4589(3) 0.0540(10) Uani 1 1 d . . . . .
H11 H 0.587431 0.779200 0.490376 0.065 Uiso 1 1 calc R U . . .
C25 C 0.3892(5) 0.9193(3) 0.6039(3) 0.0582(12) Uani 1 1 d . . . . .
H25 H 0.467008 0.900027 0.598746 0.070 Uiso 1 1 calc R U . . .
C12 C 0.5979(5) 0.7224(4) 0.3642(3) 0.0703(15) Uani 1 1 d . . . . .
H12 H 0.584590 0.779780 0.332099 0.084 Uiso 1 1 calc R U . . .
C13 C 0.6154(5) 0.6375(5) 0.3170(3) 0.0797(17) Uani 1 1 d . . . . .
H13 H 0.612468 0.638028 0.252943 0.096 Uiso 1 1 calc R U . . .
C14 C 0.6368(5) 0.5528(4) 0.3625(3) 0.0693(14) Uani 1 1 d . . . . .
H14 H 0.648568 0.496060 0.329865 0.083 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 N2 C20 106.9(3) . . ?
C8 N1 C7 111.4(3) . . ?
O1 C8 N1 124.9(3) . . ?
O1 C8 C1 126.2(3) . . ?
N1 C8 C1 108.9(3) . . ?
C2 C1 C9 115.4(3) . . ?
C2 C1 C8 101.0(3) . . ?
C9 C1 C8 110.9(3) . . ?
C2 C1 C16 111.9(3) . . ?
C9 C1 C16 109.6(3) . . ?
C8 C1 C16 107.5(3) . . ?
C24 C18 C20 118.1(4) . . ?
C24 C18 C16 134.2(4) . . ?
C20 C18 C16 107.7(3) . . ?
C3 C2 C7 118.9(4) . . ?
C3 C2 C1 132.5(3) . . ?
C7 C2 C1 108.6(3) . . ?
C18 C16 C19 98.8(3) . . ?
C18 C16 C17 111.7(3) . . ?
C19 C16 C17 108.7(3) . . ?
C18 C16 C1 116.1(3) . . ?
C19 C16 C1 109.9(3) . . ?
C17 C16 C1 110.8(3) . . ?
C15 C10 C11 116.4(3) . . ?
C15 C10 C9 123.8(3) . . ?
C11 C10 C9 119.7(3) . . ?
N2 C19 C16 115.7(4) . . ?
N2 C19 H19 122.1 . . ?
C16 C19 H19 122.1 . . ?
C10 C9 C1 116.1(3) . . ?
C10 C9 H9A 108.3 . . ?
C1 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
C1 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C6 C7 C2 122.7(4) . . ?
C6 C7 N1 127.6(4) . . ?
C2 C7 N1 109.7(3) . . ?
C21 C20 C18 122.8(4) . . ?
C21 C20 N2 126.3(4) . . ?
C18 C20 N2 110.8(4) . . ?
C20 C21 C22 117.9(4) . . ?
C20 C21 H21 121.1 . . ?
C22 C21 H21 121.1 . . ?
C18 C24 C23 119.8(4) . . ?
C18 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C2 C3 C4 118.7(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C7 C6 C5 117.4(4) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C14 C15 C10 122.2(4) . . ?
C14 C15 Br1 116.3(4) . . ?
C10 C15 Br1 121.4(3) . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C22 C23 C24 120.9(5) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C22 C21 120.5(5) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C12 C11 C10 121.3(4) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
Cl3 C25 Cl1 111.8(3) . . ?
Cl3 C25 Cl2 111.6(3) . . ?
Cl1 C25 Cl2 110.3(3) . . ?
Cl3 C25 H25 107.6 . . ?
Cl1 C25 H25 107.6 . . ?
Cl2 C25 H25 107.6 . . ?
C11 C12 C13 119.7(5) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 121.3(4) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 119.2(5) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C15 1.897(4) . ?
Cl2 C25 1.761(5) . ?
Cl1 C25 1.726(5) . ?
Cl3 C25 1.722(5) . ?
O1 C8 1.220(5) . ?
N2 C19 1.276(6) . ?
N2 C20 1.424(5) . ?
N1 C8 1.344(5) . ?
N1 C7 1.408(5) . ?
C8 C1 1.558(4) . ?
C1 C2 1.516(5) . ?
C1 C9 1.554(5) . ?
C1 C16 1.587(5) . ?
C18 C24 1.386(6) . ?
C18 C20 1.405(5) . ?
C18 C16 1.506(6) . ?
C2 C3 1.382(5) . ?
C2 C7 1.401(5) . ?
C16 C19 1.519(5) . ?
C16 C17 1.555(5) . ?
C10 C15 1.393(5) . ?
C10 C11 1.422(6) . ?
C10 C9 1.510(5) . ?
C19 H19 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 C6 1.374(6) . ?
C20 C21 1.372(7) . ?
C21 C22 1.395(7) . ?
C21 H21 0.9300 . ?
C24 C23 1.387(7) . ?
C24 H24 0.9300 . ?
C3 C4 1.400(7) . ?
C3 H3 0.9300 . ?
C6 C5 1.388(7) . ?
C6 H6 0.9300 . ?
C15 C14 1.390(6) . ?
C4 C5 1.367(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C23 C22 1.380(8) . ?
C23 H23 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C22 H22 0.9300 . ?
C11 C12 1.374(7) . ?
C11 H11 0.9300 . ?
C25 H25 0.9800 . ?
C12 C13 1.378(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.363(9) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
