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#$Date: 2022-08-06 03:26:35 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277086 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/88/7158811.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_7158811
loop_
_publ_author_name
'Cho, Eun Hee'
'Akhtar, Muhammad Saeed'
'Aslam, Mohammad'
'Thombal, Raju S.'
'Li, Xin'
'Shim, Jae-Jin'
'Lee, Yong Rok'
_publ_section_title
;
 Transition Metal-Catalyzed Regioselective Functionalization of Carbazoles
 and Indolines with Maleimides
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01077A
_journal_year                    2022
_chemical_formula_moiety         'C22 H15 Br N4 O2'
_chemical_formula_sum            'C22 H15 Br N4 O2'
_chemical_formula_weight         447.29
_chemical_melting_point          514
_chemical_name_systematic
3-(5-Bromo-1-(pyrimidin-2-yl)-1H-indol-2-yl)-1-phenylpyrrolidine-2,5-dione
_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
;
2022-06-08 deposited with the CCDC.	2022-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.42(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.315(11)
_cell_length_b                   7.025(5)
_cell_length_c                   17.444(11)
_cell_measurement_reflns_used    9228
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.53
_cell_measurement_theta_min      2.37
_cell_volume                     2093(2)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.999
_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  0.0500
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41083
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.362
_diffrn_reflns_theta_min         2.367
_exptl_absorpt_coefficient_mu    1.988
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             904
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethylacetate'
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0475
_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)+(0.0403P)²+1.8044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1173
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3651
_reflns_number_total             5224
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01077a2.cif
_cod_data_source_block           eh_141a_a_sq
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158811
_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. 
;
_shelx_estimated_absorpt_t_min   0.640
_shelx_estimated_absorpt_t_max   0.768
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 0.31497(3) 0.60483(7) 0.79585(2) 0.08627(17) Uani 1 1 d . . . . .
O1 O 0.31413(10) 0.5491(2) 0.29649(9) 0.0388(4) Uani 1 1 d . . . . .
O2 O 0.38643(12) 1.1259(2) 0.21325(12) 0.0518(5) Uani 1 1 d . . . . .
N1 N 0.40721(10) 0.7677(2) 0.48369(11) 0.0292(4) Uani 1 1 d . . . . .
N2 N 0.54319(11) 0.7558(3) 0.50406(12) 0.0438(5) Uani 1 1 d . . . . .
N3 N 0.47070(11) 0.7822(3) 0.37684(12) 0.0368(4) Uani 1 1 d . . . . .
N4 N 0.34577(11) 0.8226(3) 0.23513(11) 0.0307(4) Uani 1 1 d . . . . .
C1 C 0.34823(17) 0.6622(4) 0.69988(15) 0.0477(6) Uani 1 1 d . . . . .
C2 C 0.42788(17) 0.6672(4) 0.69708(15) 0.0459(6) Uani 1 1 d . . . . .
H2 H 0.464016 0.649098 0.742938 0.055 Uiso 1 1 calc R U . . .
C3 C 0.45469(15) 0.6983(3) 0.62792(14) 0.0365(5) Uani 1 1 d . . . . .
H3 H 0.508591 0.699121 0.625793 0.044 Uiso 1 1 calc R U . . .
C4 C 0.39970(13) 0.7284(3) 0.56130(13) 0.0300(5) Uani 1 1 d . . . . .
C5 C 0.31925(14) 0.7263(3) 0.56496(14) 0.0351(5) Uani 1 1 d . . . . .
C6 C 0.29332(16) 0.6908(4) 0.63505(15) 0.0446(6) Uani 1 1 d . . . . .
H6 H 0.239566 0.686559 0.637748 0.053 Uiso 1 1 calc R U . . .
C7 C 0.27865(14) 0.7685(3) 0.48901(14) 0.0354(5) Uani 1 1 d . . . . .
H7 H 0.223988 0.776634 0.474865 0.042 Uiso 1 1 calc R U . . .
C8 C 0.33091(12) 0.7949(3) 0.44080(13) 0.0298(5) Uani 1 1 d . . . . .
C9 C 0.47727(12) 0.7680(3) 0.45337(13) 0.0299(5) Uani 1 1 d . . . . .
C10 C 0.60866(15) 0.7609(4) 0.47291(17) 0.0488(7) Uani 1 1 d . . . . .
H10 H 0.656882 0.750492 0.506369 0.059 Uiso 1 1 calc R U . . .
C11 C 0.60947(15) 0.7802(4) 0.39560(17) 0.0450(6) Uani 1 1 d . . . . .
H11 H 0.656465 0.786687 0.375319 0.054 Uiso 1 1 calc R U . . .
C12 C 0.53769(15) 0.7896(4) 0.34877(16) 0.0437(6) Uani 1 1 d . . . . .
H12 H 0.535741 0.801835 0.294827 0.052 Uiso 1 1 calc R U . . .
C13 C 0.30940(13) 0.8588(3) 0.35827(13) 0.0314(5) Uani 1 1 d . . . . .
H13 H 0.251909 0.876373 0.350002 0.038 Uiso 1 1 calc R U . . .
C14 C 0.32444(12) 0.7191(3) 0.29664(13) 0.0311(5) Uani 1 1 d . . . . .
C15 C 0.36100(13) 1.0130(3) 0.25465(14) 0.0356(5) Uani 1 1 d . . . . .
C16 C 0.34237(14) 1.0475(3) 0.33429(14) 0.0351(5) Uani 1 1 d . . . . .
H16A H 0.303637 1.149529 0.333366 0.042 Uiso 1 1 calc R U . . .
H16B H 0.389646 1.082835 0.370432 0.042 Uiso 1 1 calc R U . . .
C17 C 0.35672(13) 0.7424(3) 0.16261(13) 0.0314(5) Uani 1 1 d . . . . .
C18 C 0.39999(15) 0.5775(4) 0.16067(15) 0.0407(6) Uani 1 1 d . . . . .
H18 H 0.421237 0.515320 0.207068 0.049 Uiso 1 1 calc R U . . .
C19 C 0.41162(17) 0.5051(4) 0.08995(17) 0.0506(7) Uani 1 1 d . . . . .
H19 H 0.441178 0.393471 0.088152 0.061 Uiso 1 1 calc R U . . .
C20 C 0.37995(18) 0.5962(4) 0.02151(16) 0.0521(7) Uani 1 1 d . . . . .
H20 H 0.388919 0.547670 -0.026477 0.063 Uiso 1 1 calc R U . . .
C21 C 0.33550(17) 0.7572(4) 0.02382(15) 0.0483(7) Uani 1 1 d . . . . .
H21 H 0.313327 0.817419 -0.022723 0.058 Uiso 1 1 calc R U . . .
C22 C 0.32320(14) 0.8311(4) 0.09404(14) 0.0386(5) Uani 1 1 d . . . . .
H22 H 0.292358 0.940766 0.095489 0.046 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'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C4 125.83(18) . . ?
C9 N1 C8 126.10(19) . . ?
C4 N1 C8 107.96(18) . . ?
C9 N2 C10 115.0(2) . . ?
C9 N3 C12 115.9(2) . . ?
C14 N4 C15 112.05(19) . . ?
C14 N4 C17 124.55(19) . . ?
C15 N4 C17 123.25(19) . . ?
C6 C1 C2 121.8(2) . . ?
C6 C1 Br1 119.3(2) . . ?
C2 C1 Br1 118.8(2) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 118.2(2) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 N1 132.3(2) . . ?
C5 C4 N1 107.09(19) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 C7 132.3(2) . . ?
C4 C5 C7 107.3(2) . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C8 C7 C5 109.3(2) . . ?
C8 C7 H7 125.4 . . ?
C5 C7 H7 125.4 . . ?
C7 C8 N1 108.4(2) . . ?
C7 C8 C13 123.8(2) . . ?
N1 C8 C13 127.7(2) . . ?
N3 C9 N2 126.8(2) . . ?
N3 C9 N1 116.34(19) . . ?
N2 C9 N1 116.9(2) . . ?
N2 C10 C11 123.7(2) . . ?
N2 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C10 C11 C12 116.1(2) . . ?
C10 C11 H11 121.9 . . ?
C12 C11 H11 121.9 . . ?
N3 C12 C11 122.5(3) . . ?
N3 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C8 C13 C14 116.46(19) . . ?
C8 C13 C16 118.58(19) . . ?
C14 C13 C16 104.67(19) . . ?
C8 C13 H13 105.3 . . ?
C14 C13 H13 105.3 . . ?
C16 C13 H13 105.3 . . ?
O1 C14 N4 124.9(2) . . ?
O1 C14 C13 127.0(2) . . ?
N4 C14 C13 107.90(19) . . ?
O2 C15 N4 124.0(2) . . ?
O2 C15 C16 127.3(2) . . ?
N4 C15 C16 108.7(2) . . ?
C15 C16 C13 105.11(19) . . ?
C15 C16 H16A 110.7 . . ?
C13 C16 H16A 110.7 . . ?
C15 C16 H16B 110.7 . . ?
C13 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C18 C17 C22 120.4(2) . . ?
C18 C17 N4 120.3(2) . . ?
C22 C17 N4 119.3(2) . . ?
C19 C18 C17 119.3(2) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 119.5(2) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
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 C1 1.901(3) . ?
O1 C14 1.208(3) . ?
O2 C15 1.204(3) . ?
N1 C9 1.400(3) . ?
N1 C4 1.408(3) . ?
N1 C8 1.421(3) . ?
N2 C9 1.327(3) . ?
N2 C10 1.335(3) . ?
N3 C9 1.325(3) . ?
N3 C12 1.332(3) . ?
N4 C14 1.395(3) . ?
N4 C15 1.395(3) . ?
N4 C17 1.425(3) . ?
C1 C6 1.368(4) . ?
C1 C2 1.388(4) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.405(3) . ?
C5 C6 1.392(3) . ?
C5 C7 1.426(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.345(3) . ?
C7 H7 0.9400 . ?
C8 C13 1.496(3) . ?
C10 C11 1.358(4) . ?
C10 H10 0.9400 . ?
C11 C12 1.373(4) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.509(3) . ?
C13 C16 1.528(3) . ?
C13 H13 0.9900 . ?
C15 C16 1.497(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 C18 1.383(3) . ?
C17 C22 1.389(3) . ?
C18 C19 1.379(4) . ?
C18 H18 0.9400 . ?
C19 C20 1.386(4) . ?
C19 H19 0.9400 . ?
C20 C21 1.373(4) . ?
C20 H20 0.9400 . ?
C21 C22 1.379(4) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
