#------------------------------------------------------------------------------
#$Date: 2020-11-04 03:30:52 +0200 (Wed, 04 Nov 2020) $
#$Revision: 258718 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038863.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_4038863
loop_
_publ_author_name
'Debnath, Sudipto'
'Das, Tuluma'
'Pati, Tanmay K.'
'Majumdar, Swapan'
'Maiti, Dilip K.'
_publ_section_title
;
 Metal-Free Indole-Phenacyl Bromide Cyclization: A Regioselective
 Synthesis of 3,5-Diarylcarbazoles.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13272
_journal_page_last               13279
_journal_paper_doi               10.1021/acs.joc.0c01670
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C26 H21 N O2'
_chemical_formula_sum            'C26 H21 N O2'
_chemical_formula_weight         379.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.897(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.676(4)
_cell_length_b                   8.467(3)
_cell_length_c                   11.173(4)
_cell_measurement_reflns_used    1936
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.66
_cell_measurement_theta_min      3.07
_cell_volume                     966.4(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0338
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5350
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        24.526
_diffrn_reflns_theta_max         24.526
_diffrn_reflns_theta_min         1.905
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9694
_exptl_absorpt_correction_T_min  0.9443
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       crystalline
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.71
_exptl_crystal_size_min          0.51
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.846
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.845
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0358
_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)+(0.0709P)²+0.1383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.828
_reflns_Friedel_fraction_max     0.828
_reflns_number_gt                2051
_reflns_number_total             2315
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01670_si_002.cif
_cod_data_source_block           td2_253
_cod_depositor_comments          'Adding full bibliography for 4038863.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038863
_shelx_shelxl_version_number     2014/7
_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, y+1/2, -z'
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
O1 O -0.0874(2) 1.1500(3) -0.2053(3) 0.0649(8) Uani 1 1 d . . . . .
O2 O 0.6723(3) 0.4646(4) 0.6522(3) 0.0833(10) Uani 1 1 d . . . . .
C5 C 0.1710(4) 0.7830(5) -0.0730(3) 0.0471(9) Uani 1 1 d . . . . .
C1 C -0.0392(5) 1.3025(5) -0.2170(5) 0.0773(13) Uani 1 1 d . . . . .
H3 H 0.0119 1.3393 -0.1364 0.116 Uiso 1 1 calc R U . . .
H1 H -0.1113 1.3731 -0.2502 0.116 Uiso 1 1 calc R U . . .
H2 H 0.0146 1.2988 -0.2725 0.116 Uiso 1 1 calc R U . . .
C2 C 0.0023(3) 1.0352(5) -0.1579(3) 0.0497(9) Uani 1 1 d . . . . .
C7 C -0.0466(4) 0.8858(5) -0.1529(4) 0.0573(10) Uani 1 1 d . . . . .
H4 H -0.1366 0.8694 -0.1779 0.069 Uiso 1 1 calc R U . . .
C6 C 0.0362(4) 0.7611(5) -0.1116(4) 0.0594(11) Uani 1 1 d . . . . .
H5 H 0.0019 0.6606 -0.1094 0.071 Uiso 1 1 calc R U . . .
C17 C 0.2618(3) 0.6475(5) -0.0322(3) 0.0480(9) Uani 1 1 d . . . . .
C16 C 0.3303(3) 0.6282(5) 0.0914(3) 0.0509(9) Uani 1 1 d . . . . .
H15 H 0.3209 0.7045 0.1480 0.061 Uiso 1 1 calc R U . . .
C15 C 0.4141(3) 0.4998(5) 0.1376(3) 0.0519(10) Uani 1 1 d . . . . .
C12 C 0.4798(3) 0.4869(5) 0.2724(3) 0.0519(10) Uani 1 1 d . . . . .
C11 C 0.4234(4) 0.5505(6) 0.3587(4) 0.0598(11) Uani 1 1 d . . . . .
H12 H 0.3420 0.5992 0.3301 0.072 Uiso 1 1 calc R U . . .
C10 C 0.4834(4) 0.5441(6) 0.4845(4) 0.0650(11) Uani 1 1 d . . . . .
H11 H 0.4430 0.5879 0.5401 0.078 Uiso 1 1 calc R U . . .
C9 C 0.6029(4) 0.4730(5) 0.5284(4) 0.0618(11) Uani 1 1 d . . . . .
C8 C 0.6303(5) 0.5608(8) 0.7363(4) 0.0912(16) Uani 1 1 d . . . . .
H8 H 0.6258 0.6687 0.7088 0.137 Uiso 1 1 calc R U . . .
H10 H 0.6914 0.5523 0.8182 0.137 Uiso 1 1 calc R U . . .
H9 H 0.5454 0.5270 0.7389 0.137 Uiso 1 1 calc R U . . .
C3 C 0.1342(4) 1.0601(5) -0.1164(4) 0.0574(10) Uani 1 1 d . . . . .
H6 H 0.1681 1.1612 -0.1169 0.069 Uiso 1 1 calc R U . . .
C4 C 0.2170(4) 0.9334(5) -0.0738(3) 0.0556(10) Uani 1 1 d . . . . .
H7 H 0.3067 0.9513 -0.0447 0.067 Uiso 1 1 calc R U . . .
C18 C 0.2804(3) 0.5350(5) -0.1167(3) 0.0511(9) Uani 1 1 d . . . . .
C19 C 0.3670(3) 0.4096(5) -0.0726(3) 0.0529(10) Uani 1 1 d . . . . .
C20 C 0.4319(3) 0.3893(5) 0.0524(4) 0.0541(10) Uani 1 1 d . . . . .
H16 H 0.4867 0.3029 0.0792 0.065 Uiso 1 1 calc R U . . .
C14 C 0.6603(4) 0.4048(6) 0.4459(4) 0.0688(12) Uani 1 1 d . . . . .
H13 H 0.7407 0.3542 0.4755 0.083 Uiso 1 1 calc R U . . .
C13 C 0.5990(4) 0.4114(5) 0.3199(4) 0.0626(11) Uani 1 1 d . . . . .
H14 H 0.6384 0.3641 0.2649 0.075 Uiso 1 1 calc R U . . .
N1 N 0.3690(3) 0.3166(4) -0.1719(3) 0.0613(9) Uani 1 1 d . . . . .
H17 H 0.4154 0.2325 -0.1675 0.074 Uiso 1 1 calc R U . . .
C21 C 0.2855(4) 0.3777(6) -0.2801(4) 0.0612(11) Uani 1 1 d . . . . .
C22 C 0.2548(5) 0.3204(6) -0.4003(4) 0.0771(14) Uani 1 1 d . . . . .
H18 H 0.2941 0.2291 -0.4186 0.093 Uiso 1 1 calc R U . . .
C23 C 0.1658(5) 0.4006(7) -0.4915(4) 0.0821(15) Uani 1 1 d . . . . .
H19 H 0.1433 0.3630 -0.5732 0.099 Uiso 1 1 calc R U . . .
C24 C 0.1075(5) 0.5380(7) -0.4651(4) 0.0792(14) Uani 1 1 d . . . . .
H20 H 0.0465 0.5906 -0.5292 0.095 Uiso 1 1 calc R U . . .
C25 C 0.1389(4) 0.5969(6) -0.3458(4) 0.0653(12) Uani 1 1 d . . . . .
H21 H 0.1007 0.6897 -0.3289 0.078 Uiso 1 1 calc R U . . .
C26 C 0.2289(4) 0.5158(5) -0.2503(3) 0.0545(10) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 117.1(3) . . ?
C9 O2 C8 117.4(4) . . ?
C4 C5 C6 117.7(4) . . ?
C4 C5 C17 121.2(3) . . ?
C6 C5 C17 121.1(4) . . ?
O1 C1 H3 109.5 . . ?
O1 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
O1 C1 H2 109.5 . . ?
H3 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
O1 C2 C3 124.2(4) . . ?
O1 C2 C7 116.1(3) . . ?
C3 C2 C7 119.7(3) . . ?
C6 C7 C2 120.5(3) . . ?
C6 C7 H4 119.7 . . ?
C2 C7 H4 119.7 . . ?
C7 C6 C5 120.7(4) . . ?
C7 C6 H5 119.6 . . ?
C5 C6 H5 119.6 . . ?
C16 C17 C18 117.4(3) . . ?
C16 C17 C5 120.7(3) . . ?
C18 C17 C5 121.8(3) . . ?
C17 C16 C15 123.9(3) . . ?
C17 C16 H15 118.1 . . ?
C15 C16 H15 118.1 . . ?
C20 C15 C16 118.0(3) . . ?
C20 C15 C12 122.3(3) . . ?
C16 C15 C12 119.8(3) . . ?
C13 C12 C11 116.7(3) . . ?
C13 C12 C15 122.6(3) . . ?
C11 C12 C15 120.7(3) . . ?
C10 C11 C12 122.1(4) . . ?
C10 C11 H12 118.9 . . ?
C12 C11 H12 118.9 . . ?
C11 C10 C9 119.8(4) . . ?
C11 C10 H11 120.1 . . ?
C9 C10 H11 120.1 . . ?
O2 C9 C10 124.1(4) . . ?
O2 C9 C14 116.1(4) . . ?
C10 C9 C14 119.8(4) . . ?
O2 C8 H8 109.5 . . ?
O2 C8 H10 109.5 . . ?
H8 C8 H10 109.5 . . ?
O2 C8 H9 109.5 . . ?
H8 C8 H9 109.5 . . ?
H10 C8 H9 109.5 . . ?
C2 C3 C4 119.3(4) . . ?
C2 C3 H6 120.3 . . ?
C4 C3 H6 120.3 . . ?
C5 C4 C3 122.0(3) . . ?
C5 C4 H7 119.0 . . ?
C3 C4 H7 119.0 . . ?
C17 C18 C19 119.2(3) . . ?
C17 C18 C26 133.7(4) . . ?
C19 C18 C26 107.1(3) . . ?
N1 C19 C20 129.0(4) . . ?
N1 C19 C18 108.4(3) . . ?
C20 C19 C18 122.5(4) . . ?
C15 C20 C19 118.9(4) . . ?
C15 C20 H16 120.6 . . ?
C19 C20 H16 120.6 . . ?
C13 C14 C9 119.9(4) . . ?
C13 C14 H13 120.0 . . ?
C9 C14 H13 120.0 . . ?
C14 C13 C12 121.6(4) . . ?
C14 C13 H14 119.2 . . ?
C12 C13 H14 119.2 . . ?
C19 N1 C21 109.7(3) . . ?
C19 N1 H17 125.2 . . ?
C21 N1 H17 125.2 . . ?
N1 C21 C22 129.3(4) . . ?
N1 C21 C26 108.6(4) . . ?
C22 C21 C26 122.0(4) . . ?
C23 C22 C21 118.2(5) . . ?
C23 C22 H18 120.9 . . ?
C21 C22 H18 120.9 . . ?
C22 C23 C24 121.2(4) . . ?
C22 C23 H19 119.4 . . ?
C24 C23 H19 119.4 . . ?
C25 C24 C23 120.8(5) . . ?
C25 C24 H20 119.6 . . ?
C23 C24 H20 119.6 . . ?
C24 C25 C26 119.0(5) . . ?
C24 C25 H21 120.5 . . ?
C26 C25 H21 120.5 . . ?
C25 C26 C21 118.6(4) . . ?
C25 C26 C18 135.1(4) . . ?
C21 C26 C18 106.2(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
O1 C2 1.360(5) . ?
O1 C1 1.411(5) . ?
O2 C9 1.368(5) . ?
O2 C8 1.411(6) . ?
C5 C4 1.366(6) . ?
C5 C6 1.389(5) . ?
C5 C17 1.486(5) . ?
C1 H3 0.9600 . ?
C1 H1 0.9600 . ?
C1 H2 0.9600 . ?
C2 C3 1.365(5) . ?
C2 C7 1.376(6) . ?
C7 C6 1.368(6) . ?
C7 H4 0.9300 . ?
C6 H5 0.9300 . ?
C17 C16 1.371(5) . ?
C17 C18 1.396(5) . ?
C16 C15 1.407(5) . ?
C16 H15 0.9300 . ?
C15 C20 1.387(5) . ?
C15 C12 1.469(5) . ?
C12 C13 1.384(5) . ?
C12 C11 1.386(5) . ?
C11 C10 1.365(6) . ?
C11 H12 0.9300 . ?
C10 C9 1.367(5) . ?
C10 H11 0.9300 . ?
C9 C14 1.373(6) . ?
C8 H8 0.9600 . ?
C8 H10 0.9600 . ?
C8 H9 0.9600 . ?
C3 C4 1.383(6) . ?
C3 H6 0.9300 . ?
C4 H7 0.9300 . ?
C18 C19 1.400(5) . ?
C18 C26 1.441(5) . ?
C19 N1 1.366(5) . ?
C19 C20 1.377(5) . ?
C20 H16 0.9300 . ?
C14 C13 1.371(6) . ?
C14 H13 0.9300 . ?
C13 H14 0.9300 . ?
N1 C21 1.378(5) . ?
N1 H17 0.8600 . ?
C21 C22 1.375(6) . ?
C21 C26 1.400(6) . ?
C22 C23 1.356(7) . ?
C22 H18 0.9300 . ?
C23 C24 1.390(7) . ?
C23 H19 0.9300 . ?
C24 C25 1.371(6) . ?
C24 H20 0.9300 . ?
C25 C26 1.392(6) . ?
C25 H21 0.9300 . ?
