#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/25/7232541.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_7232541
loop_
_publ_author_name
'Rathore, Vandana'
'Kumar, Sangit'
_publ_section_title
;
 Visible-light-induced metal and reagent-free oxidative coupling of sp2
 C--H bonds with organo-dichalcogenides: synthesis of 3-organochalcogenyl
 indoles
;
_journal_issue                   10
_journal_name_full               'Green Chemistry'
_journal_page_first              2670
_journal_paper_doi               10.1039/C9GC00007K
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C15 H12 Br N Se'
_chemical_formula_sum            'C15 H12 Br N Se'
_chemical_formula_weight         365.13
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-12-30 deposited with the CCDC.    2019-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.553(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.469(4)
_cell_length_b                   6.265(2)
_cell_length_c                   17.738(6)
_cell_measurement_reflns_used    6300
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.31
_cell_volume                     1376.6(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0883
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23179
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.832
_diffrn_reflns_theta_min         2.311
_exptl_absorpt_coefficient_mu    5.611
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .10
_exptl_crystal_size_min          .09
_refine_diff_density_max         1.433
_refine_diff_density_min         -1.278
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0487
_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)+(0.0450P)²+2.5698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1188
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2480
_reflns_number_total             3581
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9gc00007k2.cif
_cod_data_source_block           F2_a
_cod_depositor_comments          'Adding full bibliography for 7232541.cif.'
_cod_database_code               7232541
_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
Se1 Se 0.48060(3) 0.64594(8) 0.59231(2) 0.04270(15) Uani 1 1 d . .
Br1 Br 0.31322(5) 0.26095(9) 0.54261(3) 0.06261(19) Uani 1 1 d . .
N1 N 0.6409(3) 1.1566(6) 0.6874(3) 0.0524(10) Uani 1 1 d . .
H1 H 0.6721 1.2782 0.6842 0.063 Uiso 1 1 calc R U
C10 C 0.5809(3) 0.8515(7) 0.7336(2) 0.0338(8) Uani 1 1 d . .
C6 C 0.3394(3) 0.6528(7) 0.6248(2) 0.0365(9) Uani 1 1 d . .
C7 C 0.5490(3) 0.8620(7) 0.6537(2) 0.0361(9) Uani 1 1 d . .
C11 C 0.5655(3) 0.7058(7) 0.7899(2) 0.0383(9) Uani 1 1 d . .
H11 H 0.5287 0.5790 0.7778 0.046 Uiso 1 1 calc R U
C9 C 0.6379(3) 1.0423(7) 0.7526(3) 0.0417(10) Uani 1 1 d . .
C1 C 0.2680(3) 0.4890(8) 0.6019(2) 0.0453(11) Uani 1 1 d . .
C8 C 0.5872(3) 1.0487(8) 0.6283(3) 0.0471(11) Uani 1 1 d . .
H8 H 0.5779 1.0954 0.5782 0.057 Uiso 1 1 calc R U
C5 C 0.3052(4) 0.8141(8) 0.6687(3) 0.0463(11) Uani 1 1 d . .
H5 H 0.3522 0.9245 0.6848 0.056 Uiso 1 1 calc R U
C14 C 0.6797(4) 1.0866(8) 0.8265(3) 0.0506(12) Uani 1 1 d . .
H14 H 0.7188 1.2106 0.8388 0.061 Uiso 1 1 calc R U
C12 C 0.6049(4) 0.7490(8) 0.8643(3) 0.0491(11) Uani 1 1 d . .
C13 C 0.6611(4) 0.9411(9) 0.8802(3) 0.0555(13) Uani 1 1 d . .
H13 H 0.6871 0.9702 0.9304 0.067 Uiso 1 1 calc R U
C4 C 0.2010(4) 0.8141(10) 0.6894(3) 0.0610(14) Uani 1 1 d . .
H4 H 0.1784 0.9237 0.7192 0.073 Uiso 1 1 calc R U
C2 C 0.1648(4) 0.4884(10) 0.6220(3) 0.0633(15) Uani 1 1 d . .
H2 H 0.1177 0.3779 0.6063 0.076 Uiso 1 1 calc R U
C3 C 0.1317(4) 0.6510(11) 0.6654(3) 0.0678(16) Uani 1 1 d . .
H3 H 0.0617 0.6511 0.6788 0.081 Uiso 1 1 calc R U
C15 C 0.5868(5) 0.5953(11) 0.9272(3) 0.0740(18) Uani 1 1 d . .
H15A H 0.5562 0.6704 0.9668 0.111 Uiso 1 1 calc R U
H15B H 0.6545 0.5332 0.9473 0.111 Uiso 1 1 calc R U
H15C H 0.5383 0.4845 0.9075 0.111 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'
Se Se -0.0929 2.2259 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 Se1 C6 100.45(18)
C8 N1 C9 109.5(4)
C8 N1 H1 125.2
C9 N1 H1 125.2
C11 C10 C9 119.6(4)
C11 C10 C7 134.5(4)
C9 C10 C7 105.9(4)
C5 C6 C1 118.6(4)
C5 C6 Se1 122.9(3)
C1 C6 Se1 118.5(4)
C8 C7 C10 107.5(4)
C8 C7 Se1 125.5(3)
C10 C7 Se1 126.7(3)
C12 C11 C10 119.8(4)
C12 C11 H11 120.1
C10 C11 H11 120.1
N1 C9 C14 130.9(4)
N1 C9 C10 107.7(4)
C14 C9 C10 121.5(4)
C2 C1 C6 121.0(5)
C2 C1 Br1 119.2(4)
C6 C1 Br1 119.8(3)
N1 C8 C7 109.5(4)
N1 C8 H8 125.3
C7 C8 H8 125.3
C6 C5 C4 120.7(5)
C6 C5 H5 119.7
C4 C5 H5 119.7
C13 C14 C9 117.0(4)
C13 C14 H14 121.5
C9 C14 H14 121.5
C11 C12 C13 118.4(5)
C11 C12 C15 120.9(5)
C13 C12 C15 120.7(5)
C14 C13 C12 123.7(5)
C14 C13 H13 118.1
C12 C13 H13 118.1
C3 C4 C5 119.5(5)
C3 C4 H4 120.2
C5 C4 H4 120.2
C3 C2 C1 119.7(5)
C3 C2 H2 120.1
C1 C2 H2 120.1
C2 C3 C4 120.5(5)
C2 C3 H3 119.7
C4 C3 H3 119.7
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 C7 1.880(4)
Se1 C6 1.914(4)
Br1 C1 1.898(5)
N1 C8 1.358(6)
N1 C9 1.365(6)
N1 H1 0.8600
C10 C11 1.383(6)
C10 C9 1.412(6)
C10 C7 1.429(6)
C6 C5 1.374(7)
C6 C1 1.389(6)
C7 C8 1.359(6)
C11 C12 1.380(6)
C11 H11 0.9300
C9 C14 1.382(7)
C1 C2 1.374(7)
C8 H8 0.9300
C5 C4 1.388(7)
C5 H5 0.9300
C14 C13 1.358(8)
C14 H14 0.9300
C12 C13 1.405(8)
C12 C15 1.510(8)
C13 H13 0.9300
C4 C3 1.374(8)
C4 H4 0.9300
C2 C3 1.368(9)
C2 H2 0.9300
C3 H3 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139205547
