#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/82/7128293.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_7128293
loop_
_publ_author_name
'Kundu, Samrat'
'Banerjee, Ankush'
'Pal, Shyam Chand'
'Ghosh, Meghna'
'Maji, Modhu Sudan'
_publ_section_title
;
 Cascade annulative π-extension for the rapid construction of carbazole
 based polyaromatic hydrocarbons.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5762
_journal_page_last               5765
_journal_paper_doi               10.1039/d1cc00668a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C33 H19 N'
_chemical_formula_weight         429.49
_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   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc27msj6
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-04-30 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.07(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.09(3)
_cell_length_b                   5.262(13)
_cell_length_c                   23.54(5)
_cell_measurement_reflns_used    2729
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      2.53
_cell_volume                     1982(7)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_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  0.0946
_diffrn_reflns_av_unetI/netI     0.0803
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18085
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.656
_diffrn_reflns_theta_min         2.546
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.3973
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.0624
_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)+(0.0807P)²+0.0538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2028
_reflns_number_total             4124
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc00668a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7128291--7128294.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7128293
_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+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
N1 N 0.63332(13) 0.2488(4) 0.65941(10) 0.0531(6) Uani 1 1 d . . . . .
C1 C 0.61678(17) 0.3831(5) 0.60921(12) 0.0515(7) Uani 1 1 d . . . . .
C2 C 0.65414(18) 0.3569(6) 0.55898(12) 0.0621(8) Uani 1 1 d . . . . .
H2 H 0.6909 0.2243 0.5541 0.075 Uiso 1 1 calc R U . . .
C3 C 0.6349(2) 0.5334(7) 0.51690(13) 0.0676(9) Uani 1 1 d . . . . .
H3 H 0.6581 0.5191 0.4825 0.081 Uiso 1 1 calc R U . . .
C4 C 0.5811(2) 0.7335(6) 0.52488(13) 0.0679(9) Uani 1 1 d . . . . .
H4 H 0.5709 0.8555 0.4964 0.081 Uiso 1 1 calc R U . . .
C5 C 0.54300(18) 0.7540(6) 0.57376(13) 0.0597(8) Uani 1 1 d . . . . .
H5 H 0.5068 0.8886 0.5782 0.072 Uiso 1 1 calc R U . . .
C6 C 0.55811(17) 0.5740(5) 0.61717(12) 0.0518(7) Uani 1 1 d . . . . .
C7 C 0.53733(16) 0.5496(5) 0.67503(12) 0.0479(7) Uani 1 1 d . . . . .
C8 C 0.58874(16) 0.3570(5) 0.70028(11) 0.0471(7) Uani 1 1 d . . . . .
C9 C 0.59635(16) 0.3119(5) 0.75969(12) 0.0472(7) Uani 1 1 d . . . . .
C10 C 0.64612(17) 0.1144(5) 0.78751(12) 0.0545(7) Uani 1 1 d . . . . .
H10 H 0.6691 -0.0087 0.7655 0.065 Uiso 1 1 calc R U . . .
C11 C 0.66034(18) 0.1028(6) 0.84441(13) 0.0589(8) Uani 1 1 d . . . . .
H11 H 0.6935 -0.0276 0.8610 0.071 Uiso 1 1 calc R U . . .
C12 C 0.62655(17) 0.2827(6) 0.88010(12) 0.0549(8) Uani 1 1 d . . . . .
C13 C 0.6456(2) 0.2779(7) 0.93889(14) 0.0710(9) Uani 1 1 d . . . . .
H13 H 0.6812 0.1534 0.9556 0.085 Uiso 1 1 calc R U . . .
C14 C 0.6127(2) 0.4537(8) 0.97205(15) 0.0801(10) Uani 1 1 d . . . . .
H14 H 0.6277 0.4531 1.0113 0.096 Uiso 1 1 calc R U . . .
C15 C 0.5572(2) 0.6340(7) 0.94813(14) 0.0752(10) Uani 1 1 d . . . . .
H15 H 0.5348 0.7514 0.9718 0.090 Uiso 1 1 calc R U . . .
C16 C 0.53423(18) 0.6439(6) 0.88973(13) 0.0569(8) Uani 1 1 d . . . . .
C17 C 0.57102(17) 0.4690(6) 0.85425(12) 0.0520(7) Uani 1 1 d . . . . .
C18 C 0.55483(16) 0.4822(5) 0.79356(11) 0.0463(7) Uani 1 1 d . . . . .
C19 C 0.49824(16) 0.6664(5) 0.76828(12) 0.0479(7) Uani 1 1 d . . . . .
C20 C 0.48375(16) 0.6859(5) 0.70840(12) 0.0483(7) Uani 1 1 d . . . . .
C21 C 0.41516(17) 0.8437(5) 0.68418(13) 0.0539(7) Uani 1 1 d . . . . .
C22 C 0.38089(18) 0.8127(6) 0.62757(14) 0.0639(9) Uani 1 1 d . . . . .
H22 H 0.4007 0.6824 0.6059 0.077 Uiso 1 1 calc R U . . .
C23 C 0.3190(2) 0.9683(7) 0.60294(16) 0.0761(10) Uani 1 1 d . . . . .
H23 H 0.2978 0.9458 0.5650 0.091 Uiso 1 1 calc R U . . .
C24 C 0.2886(2) 1.1588(7) 0.63529(19) 0.0825(11) Uani 1 1 d . . . . .
H24 H 0.2493 1.2726 0.6184 0.099 Uiso 1 1 calc R U . . .
C25 C 0.3160(2) 1.1809(6) 0.69167(18) 0.0759(10) Uani 1 1 d . . . . .
H25 H 0.2935 1.3069 0.7131 0.091 Uiso 1 1 calc R U . . .
C26 C 0.37718(17) 1.0192(5) 0.71830(15) 0.0597(8) Uani 1 1 d . . . . .
C27 C 0.39942(18) 1.0194(5) 0.77924(15) 0.0601(8) Uani 1 1 d . . . . .
C28 C 0.36229(19) 1.1895(6) 0.81492(18) 0.0738(10) Uani 1 1 d . . . . .
H28 H 0.3251 1.3117 0.7989 0.089 Uiso 1 1 calc R U . . .
C29 C 0.3802(2) 1.1775(7) 0.87288(18) 0.0819(11) Uani 1 1 d . . . . .
H29 H 0.3551 1.2912 0.8961 0.098 Uiso 1 1 calc R U . . .
C30 C 0.4348(2) 0.9994(7) 0.89698(15) 0.0729(10) Uani 1 1 d . . . . .
H30 H 0.4457 0.9928 0.9365 0.087 Uiso 1 1 calc R U . . .
C31 C 0.47427(18) 0.8278(6) 0.86398(13) 0.0575(8) Uani 1 1 d . . . . .
C32 C 0.45611(16) 0.8369(5) 0.80397(12) 0.0508(7) Uani 1 1 d . . . . .
C33 C 0.6951(2) 0.0480(7) 0.66618(17) 0.0612(9) Uani 1 1 d . . . . .
33BB H 0.746(2) 0.101(6) 0.6933(12) 0.082(10) Uiso 1 1 d . . . . .
33AA H 0.675(2) -0.116(7) 0.6802(13) 0.089(11) Uiso 1 1 d . . . . .
33CC H 0.714(2) 0.014(7) 0.6279(14) 0.103(12) Uiso 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'
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
C1 N1 C8 108.5(3) . . ?
C1 N1 C33 122.5(3) . . ?
C8 N1 C33 128.7(3) . . ?
N1 C1 C2 128.1(3) . . ?
N1 C1 C6 108.9(3) . . ?
C2 C1 C6 122.8(3) . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 117.1(3) . . ?
C5 C6 C7 135.4(3) . . ?
C1 C6 C7 106.8(3) . . ?
C8 C7 C20 119.8(3) . . ?
C8 C7 C6 106.2(2) . . ?
C20 C7 C6 133.8(3) . . ?
N1 C8 C7 109.3(3) . . ?
N1 C8 C9 128.6(3) . . ?
C7 C8 C9 121.8(3) . . ?
C8 C9 C18 117.1(3) . . ?
C8 C9 C10 124.2(3) . . ?
C18 C9 C10 118.6(3) . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 122.0(3) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 121.6(3) . . ?
C13 C12 C17 120.2(3) . . ?
C11 C12 C17 118.2(3) . . ?
C14 C13 C12 120.3(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 121.6(3) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 118.4(3) . . ?
C15 C16 C31 122.3(3) . . ?
C17 C16 C31 119.2(3) . . ?
C16 C17 C12 118.7(3) . . ?
C16 C17 C18 121.1(3) . . ?
C12 C17 C18 120.2(3) . . ?
C9 C18 C19 121.2(3) . . ?
C9 C18 C17 119.1(3) . . ?
C19 C18 C17 119.7(3) . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 C32 119.9(3) . . ?
C18 C19 C32 120.0(3) . . ?
C19 C20 C7 118.1(3) . . ?
C19 C20 C21 118.3(3) . . ?
C7 C20 C21 123.6(3) . . ?
C22 C21 C26 118.0(3) . . ?
C22 C21 C20 121.1(3) . . ?
C26 C21 C20 120.7(3) . . ?
C23 C22 C21 122.0(3) . . ?
C23 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
C22 C23 C24 119.0(4) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 121.8(3) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 H25 119.1 . . ?
C25 C26 C21 118.1(3) . . ?
C25 C26 C27 122.3(3) . . ?
C21 C26 C27 119.5(3) . . ?
C28 C27 C32 119.1(4) . . ?
C28 C27 C26 121.3(3) . . ?
C32 C27 C26 119.6(3) . . ?
C29 C28 C27 120.7(4) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 120.3(3) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C31 121.8(4) . . ?
C29 C30 H30 119.1 . . ?
C31 C30 H30 119.1 . . ?
C30 C31 C32 118.6(3) . . ?
C30 C31 C16 121.5(3) . . ?
C32 C31 C16 119.8(3) . . ?
C27 C32 C31 119.6(3) . . ?
C27 C32 C19 120.4(3) . . ?
C31 C32 C19 120.0(3) . . ?
N1 C33 33BB 111.3(18) . . ?
N1 C33 33AA 115.3(19) . . ?
33BB C33 33AA 107(3) . . ?
N1 C33 33CC 108(2) . . ?
33BB C33 33CC 108(3) . . ?
33AA C33 33CC 107(3) . . ?
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
N1 C1 1.378(4) . ?
N1 C8 1.382(4) . ?
N1 C33 1.448(4) . ?
C1 C2 1.389(5) . ?
C1 C6 1.405(4) . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.442(5) . ?
C7 C8 1.400(4) . ?
C7 C20 1.420(4) . ?
C8 C9 1.411(5) . ?
C9 C18 1.413(4) . ?
C9 C10 1.428(4) . ?
C10 C11 1.336(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.412(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(5) . ?
C12 C17 1.420(4) . ?
C13 C14 1.353(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.414(4) . ?
C16 C31 1.453(5) . ?
C17 C18 1.426(5) . ?
C18 C19 1.417(4) . ?
C19 C20 1.408(5) . ?
C19 C32 1.446(4) . ?
C20 C21 1.449(4) . ?
C21 C22 1.397(5) . ?
C21 C26 1.406(4) . ?
C22 C23 1.369(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.379(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.358(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.398(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.441(5) . ?
C27 C28 1.404(4) . ?
C27 C32 1.407(4) . ?
C28 C29 1.365(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.366(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.388(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.413(5) . ?
C33 33BB 1.02(3) . ?
C33 33AA 0.99(3) . ?
C33 33CC 1.00(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352753
