#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/36/4033627.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_4033627
loop_
_publ_author_name
'Dey, Amrita'
'Hajra, Alakananda'
_publ_section_title
;
 Iodine-Catalyzed Selenylation of 2H-Indazole.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02199
_journal_year                    2019
_chemical_formula_moiety         'C19 H13 Cl N2 Se'
_chemical_formula_sum            'C19 H13 Cl N2 Se'
_chemical_formula_weight         383.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                117.878(2)
_cell_angle_beta                 91.349(2)
_cell_angle_gamma                98.247(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3670(4)
_cell_length_b                   9.7630(5)
_cell_length_c                   10.3133(5)
_cell_measurement_reflns_used    13295
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.299
_cell_measurement_theta_min      2.380
_cell_volume                     820.63(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13295
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_min         2.380
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.450
_exptl_absorpt_correction_T_max  0.610
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tetragonal
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.856
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.856
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0309
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3470
_reflns_number_total             4075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b02199_si_002.cif
_cod_data_source_block           1350RKM_A_0m_a
_cod_original_cell_volume        820.64(7)
_cod_database_code               4033627
_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, -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
Se1 Se 0.87563(2) 0.48018(2) 0.22893(2) 0.04211(11) Uani 1 1 d . .
Cl1 Cl 0.95728(9) -0.17835(8) 0.10969(9) 0.0706(2) Uani 1 1 d . .
N1 N 0.77178(19) 0.4627(2) 0.48510(18) 0.0383(4) Uani 1 1 d . .
N2 N 0.7638(2) 0.3778(2) 0.5582(2) 0.0454(4) Uani 1 1 d . .
C1 C 0.7131(2) 0.3869(2) 0.0802(2) 0.0357(4) Uani 1 1 d . .
C14 C 0.7263(2) 0.6128(3) 0.5549(2) 0.0390(4) Uani 1 1 d . .
C7 C 0.8214(2) 0.3879(2) 0.3493(2) 0.0367(4) Uani 1 1 d . .
C8 C 0.8425(2) 0.2415(3) 0.3321(2) 0.0366(4) Uani 1 1 d . .
C2 C 0.7265(3) 0.4142(3) -0.0405(2) 0.0455(5) Uani 1 1 d . .
H2 H 0.8125 0.4692 -0.0484 0.055 Uiso 1 1 calc R U
C13 C 0.8067(2) 0.2434(3) 0.4655(2) 0.0409(5) Uani 1 1 d . .
C15 C 0.7701(3) 0.7114(3) 0.7031(3) 0.0496(5) Uani 1 1 d . .
H15 H 0.8286 0.6811 0.7556 0.060 Uiso 1 1 calc R U
C6 C 0.5867(3) 0.2997(3) 0.0884(3) 0.0481(5) Uani 1 1 d . .
H6 H 0.5783 0.2779 0.1669 0.058 Uiso 1 1 calc R U
C9 C 0.8897(2) 0.1109(3) 0.2191(2) 0.0432(5) Uani 1 1 d . .
H9 H 0.9143 0.1091 0.1315 0.052 Uiso 1 1 calc R U
C10 C 0.8974(3) -0.0130(3) 0.2448(3) 0.0461(5) Uani 1 1 d . .
C11 C 0.8609(3) -0.0150(3) 0.3762(3) 0.0533(6) Uani 1 1 d . .
H11 H 0.8673 -0.1033 0.3870 0.064 Uiso 1 1 calc R U
C3 C 0.6112(3) 0.3589(3) -0.1484(3) 0.0522(6) Uani 1 1 d . .
H3 H 0.6194 0.3787 -0.2280 0.063 Uiso 1 1 calc R U
C18 C 0.5921(3) 0.7994(3) 0.5468(3) 0.0609(7) Uani 1 1 d . .
H18 H 0.5318 0.8291 0.4950 0.073 Uiso 1 1 calc R U
C12 C 0.8162(3) 0.1113(3) 0.4871(3) 0.0511(6) Uani 1 1 d . .
H12 H 0.7928 0.1111 0.5741 0.061 Uiso 1 1 calc R U
C4 C 0.4852(3) 0.2755(3) -0.1389(3) 0.0560(6) Uani 1 1 d . .
H4 H 0.4079 0.2391 -0.2117 0.067 Uiso 1 1 calc R U
C19 C 0.6365(3) 0.6548(3) 0.4765(3) 0.0504(5) Uani 1 1 d . .
H19 H 0.6061 0.5866 0.3774 0.060 Uiso 1 1 calc R U
C5 C 0.4728(3) 0.2453(4) -0.0214(3) 0.0586(7) Uani 1 1 d . .
H5 H 0.3872 0.1877 -0.0158 0.070 Uiso 1 1 calc R U
C17 C 0.6379(3) 0.9000(3) 0.6949(4) 0.0641(7) Uani 1 1 d . .
H17 H 0.6093 0.9977 0.7422 0.077 Uiso 1 1 calc R U
C16 C 0.7258(3) 0.8550(3) 0.7717(3) 0.0621(7) Uani 1 1 d . .
H16 H 0.7555 0.9225 0.8711 0.075 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'
Se Se -0.0929 2.2259 '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
C7 Se1 C1 100.58(9)
N2 N1 C7 113.29(18)
N2 N1 C14 117.78(17)
C7 N1 C14 128.91(17)
C13 N2 N1 104.53(17)
C6 C1 C2 119.9(2)
C6 C1 Se1 124.15(15)
C2 C1 Se1 115.94(16)
C15 C14 C19 121.0(2)
C15 C14 N1 118.53(19)
C19 C14 N1 120.42(19)
N1 C7 C8 105.50(17)
N1 C7 Se1 125.62(16)
C8 C7 Se1 128.26(16)
C7 C8 C9 134.0(2)
C7 C8 C13 104.79(19)
C9 C8 C13 121.2(2)
C3 C2 C1 119.6(2)
C3 C2 H2 120.2
C1 C2 H2 120.2
N2 C13 C8 111.85(19)
N2 C13 C12 127.8(2)
C8 C13 C12 120.3(2)
C14 C15 C16 119.1(2)
C14 C15 H15 120.5
C16 C15 H15 120.5
C1 C6 C5 119.3(2)
C1 C6 H6 120.4
C5 C6 H6 120.4
C10 C9 C8 116.4(2)
C10 C9 H9 121.8
C8 C9 H9 121.8
C9 C10 C11 123.6(2)
C9 C10 Cl1 118.77(19)
C11 C10 Cl1 117.65(18)
C12 C11 C10 120.6(2)
C12 C11 H11 119.7
C10 C11 H11 119.7
C4 C3 C2 120.5(2)
C4 C3 H3 119.7
C2 C3 H3 119.7
C17 C18 C19 119.7(3)
C17 C18 H18 120.1
C19 C18 H18 120.1
C11 C12 C13 117.9(2)
C11 C12 H12 121.1
C13 C12 H12 121.1
C3 C4 C5 120.0(2)
C3 C4 H4 120.0
C5 C4 H4 120.0
C14 C19 C18 119.4(2)
C14 C19 H19 120.3
C18 C19 H19 120.3
C4 C5 C6 120.7(2)
C4 C5 H5 119.7
C6 C5 H5 119.7
C18 C17 C16 120.0(3)
C18 C17 H17 120.0
C16 C17 H17 120.0
C15 C16 C17 120.7(2)
C15 C16 H16 119.6
C17 C16 H16 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 C7 1.886(2)
Se1 C1 1.920(2)
Cl1 C10 1.748(2)
N1 N2 1.353(2)
N1 C7 1.372(3)
N1 C14 1.433(3)
N2 C13 1.339(3)
C1 C6 1.385(3)
C1 C2 1.394(3)
C14 C15 1.383(3)
C14 C19 1.381(3)
C7 C8 1.400(3)
C8 C9 1.405(3)
C8 C13 1.417(3)
C2 C3 1.382(4)
C2 H2 0.9300
C13 C12 1.421(3)
C15 C16 1.375(4)
C15 H15 0.9300
C6 C5 1.386(3)
C6 H6 0.9300
C9 C10 1.366(3)
C9 H9 0.9300
C10 C11 1.413(4)
C11 C12 1.362(4)
C11 H11 0.9300
C3 C4 1.368(4)
C3 H3 0.9300
C18 C17 1.388(4)
C18 C19 1.385(4)
C18 H18 0.9300
C12 H12 0.9300
C4 C5 1.378(4)
C4 H4 0.9300
C19 H19 0.9300
C5 H5 0.9300
C17 C16 1.377(5)
C17 H17 0.9300
C16 H16 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168327683
