#------------------------------------------------------------------------------
#$Date: 2024-09-06 01:48:52 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294400 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572058.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_1572058
loop_
_publ_author_name
'Nayak, Mukesh Kumar'
'Maharana, Rajat Rajiv'
'Mohanty, Anuradha'
'Samanta, Kousik'
'Roy, Sujit'
_publ_section_title
;
 Effect of N-heterocyclic carbene in palladium--tin heterobimetallic
 catalysis: a DFT supported study on the C3--H functionalization of
 unprotected indoles
;
_journal_issue                   16
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              4674
_journal_page_last               4683
_journal_paper_doi               10.1039/D4CY00224E
_journal_volume                  14
_journal_year                    2024
_chemical_formula_sum            'C14 H19 Br Cl6 N2 Pd Sn'
_chemical_formula_weight         733.01
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-08-29 deposited with the CCDC.	2024-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                103.95(11)
_cell_angle_beta                 106.54(8)
_cell_angle_gamma                97.14(12)
_cell_formula_units_Z            2
_cell_length_a                   9.03(2)
_cell_length_b                   10.515(19)
_cell_length_c                   14.250(19)
_cell_measurement_reflns_used    18945
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.726
_cell_measurement_theta_min      2.402
_cell_volume                     1231(4)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18945
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.726
_diffrn_reflns_theta_min         2.402
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.022
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             700
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_refine_diff_density_max         1.476
_refine_diff_density_min         -2.446
_refine_diff_density_rms         0.356
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         5150
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0598
_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)+(0.1031P)²+6.0808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.2002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3621
_reflns_number_total             5150
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cy00224e3.cif
_cod_data_source_block           SRMKN_1191_1_0m_a
_cod_depositor_comments          'Adding full bibliography for 1572058.cif.'
_cod_database_code               1572058
_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.
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.22670(7) 0.45663(6) 0.17377(4) 0.0431(2) Uani 1 1 d . . . . .
Pd1 Pd 0.42731(7) 0.55083(6) 0.10337(4) 0.0345(2) Uani 1 1 d . . . . .
Br1 Br 0.37331(13) 0.33978(11) -0.03806(8) 0.0617(3) Uani 1 1 d . . . . .
Cl2 Cl -0.0404(3) 0.4787(3) 0.1147(2) 0.0705(7) Uani 1 1 d . . . . .
Cl3 Cl 0.1737(4) 0.2236(3) 0.1474(4) 0.0980(12) Uani 1 1 d . . . . .
Cl1 Cl 0.2619(4) 0.5361(5) 0.3505(2) 0.1054(13) Uani 1 1 d . . . . .
Cl5 Cl 0.3552(5) 0.7342(5) 0.8058(3) 0.1115(13) Uani 1 1 d . . . . .
Cl6 Cl 0.2012(8) 0.9505(7) 0.7865(6) 0.182(3) Uani 1 1 d . . . . .
N2 N 0.4022(8) 0.8219(7) 0.2150(5) 0.0425(16) Uani 1 1 d . . . . .
Cl4 Cl 0.0934(7) 0.6903(9) 0.6267(6) 0.217(4) Uani 1 1 d . . . . .
N1 N 0.5961(8) 0.7523(7) 0.3063(5) 0.0453(16) Uani 1 1 d . . . . .
C8 C 0.2630(11) 0.8215(10) 0.1265(7) 0.053(2) Uani 1 1 d . . . . .
H8 H 0.229922 0.729942 0.080345 0.064 Uiso 1 1 calc R U . . .
C7 C 0.4745(9) 0.7187(8) 0.2180(6) 0.0380(17) Uani 1 1 d . . . . .
C12 C 0.7095(12) 0.6637(11) 0.3338(8) 0.061(3) Uani 1 1 d . . . . .
H12 H 0.673299 0.578363 0.279390 0.073 Uiso 1 1 calc R U . . .
C9 C 0.3097(14) 0.9111(11) 0.0662(8) 0.067(3) Uani 1 1 d . . . . .
H9A H 0.347969 1.001679 0.109661 0.100 Uiso 1 1 calc R U . . .
H9B H 0.219424 0.907409 0.009386 0.100 Uiso 1 1 calc R U . . .
H9C H 0.391349 0.881022 0.041257 0.100 Uiso 1 1 calc R U . . .
C2 C 0.4560(13) 1.0611(9) 0.3342(8) 0.059(2) Uani 1 1 d . . . . .
H2 H 0.374865 1.091190 0.294514 0.071 Uiso 1 1 calc R U . . .
C10 C 0.1222(13) 0.8525(12) 0.1616(11) 0.078(3) Uani 1 1 d . . . . .
H10A H 0.124519 0.820209 0.219429 0.116 Uiso 1 1 calc R U . . .
H10B H 0.025439 0.809114 0.106752 0.116 Uiso 1 1 calc R U . . .
H10C H 0.128491 0.947526 0.180544 0.116 Uiso 1 1 calc R U . . .
C13 C 0.8729(13) 0.7247(16) 0.3381(11) 0.089(4) Uani 1 1 d . . . . .
H13A H 0.864425 0.777207 0.290936 0.134 Uiso 1 1 calc R U . . .
H13B H 0.927422 0.654714 0.319915 0.134 Uiso 1 1 calc R U . . .
H13C H 0.930769 0.781063 0.406143 0.134 Uiso 1 1 calc R U . . .
C6 C 0.6038(11) 0.8843(10) 0.3614(7) 0.050(2) Uani 1 1 d . . . . .
C1 C 0.4810(11) 0.9313(9) 0.3038(6) 0.046(2) Uani 1 1 d . . . . .
C11 C 0.7043(16) 0.6346(17) 0.4333(11) 0.095(4) Uani 1 1 d . . . . .
H11A H 0.752389 0.714324 0.489643 0.142 Uiso 1 1 calc R U . . .
H11B H 0.760898 0.565049 0.444141 0.142 Uiso 1 1 calc R U . . .
H11C H 0.596475 0.606226 0.428575 0.142 Uiso 1 1 calc R U . . .
C5 C 0.7087(13) 0.9696(12) 0.4576(7) 0.064(3) Uani 1 1 d . . . . .
H5 H 0.789948 0.940502 0.498125 0.077 Uiso 1 1 calc R U . . .
C3 C 0.5622(15) 1.1439(12) 0.4295(9) 0.075(3) Uani 1 1 d . . . . .
H3 H 0.550324 1.231169 0.453461 0.090 Uiso 1 1 calc R U . . .
C4 C 0.6824(15) 1.0991(13) 0.4876(8) 0.078(4) Uani 1 1 d . . . . .
H4 H 0.749202 1.157566 0.549604 0.093 Uiso 1 1 calc R U . . .
C14 C 0.1795(19) 0.771(2) 0.7558(15) 0.131(7) Uani 1 1 d . . . . .
H14 H 0.109113 0.739033 0.790254 0.157 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'
Cl Cl 0.1484 0.1585 '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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 '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
Cl3 Sn1 Cl1 101.0(2) . . ?
Cl3 Sn1 Cl2 96.85(19) . . ?
Cl1 Sn1 Cl2 96.30(16) . . ?
Cl3 Sn1 Pd1 117.71(14) . . ?
Cl1 Sn1 Pd1 119.76(15) . . ?
Cl2 Sn1 Pd1 120.57(15) . . ?
C7 Pd1 Br1 178.8(2) . . ?
C7 Pd1 Sn1 87.1(3) . . ?
Br1 Pd1 Sn1 93.15(14) . . ?
C7 Pd1 Br1 89.5(3) . 2_665 ?
Br1 Pd1 Br1 90.21(14) . 2_665 ?
Sn1 Pd1 Br1 176.33(3) . 2_665 ?
Pd1 Br1 Pd1 89.79(14) . 2_665 ?
C7 N2 C1 110.1(7) . . ?
C7 N2 C8 123.8(7) . . ?
C1 N2 C8 126.0(7) . . ?
C7 N1 C6 108.7(7) . . ?
C7 N1 C12 124.0(8) . . ?
C6 N1 C12 127.2(8) . . ?
N2 C8 C9 111.3(8) . . ?
N2 C8 C10 111.2(9) . . ?
C9 C8 C10 113.9(9) . . ?
N2 C8 H8 106.6 . . ?
C9 C8 H8 106.6 . . ?
C10 C8 H8 106.6 . . ?
N2 C7 N1 108.9(7) . . ?
N2 C7 Pd1 125.6(6) . . ?
N1 C7 Pd1 125.1(6) . . ?
N1 C12 C13 110.5(10) . . ?
N1 C12 C11 109.5(9) . . ?
C13 C12 C11 113.6(10) . . ?
N1 C12 H12 107.7 . . ?
C13 C12 H12 107.7 . . ?
C11 C12 H12 107.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C2 C3 115.6(11) . . ?
C1 C2 H2 122.2 . . ?
C3 C2 H2 122.2 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C6 N1 107.7(7) . . ?
C1 C6 C5 120.0(9) . . ?
N1 C6 C5 132.4(10) . . ?
C2 C1 C6 123.3(9) . . ?
C2 C1 N2 132.1(9) . . ?
C6 C1 N2 104.6(7) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C5 C6 116.3(11) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
C4 C3 C2 121.9(11) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 122.9(10) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
Cl5 C14 Cl4 112.9(12) . . ?
Cl5 C14 Cl6 109.1(11) . . ?
Cl4 C14 Cl6 113.2(9) . . ?
Cl5 C14 H14 107.1 . . ?
Cl4 C14 H14 107.1 . . ?
Cl6 C14 H14 107.1 . . ?
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
Sn1 Cl3 2.353(5) . ?
Sn1 Cl1 2.368(5) . ?
Sn1 Cl2 2.378(6) . ?
Sn1 Pd1 2.517(4) . ?
Pd1 C7 1.998(9) . ?
Pd1 Br1 2.498(5) . ?
Pd1 Br1 2.526(4) 2_665 ?
Cl5 C14 1.676(17) . ?
Cl6 C14 1.81(2) . ?
N2 C7 1.337(10) . ?
N2 C1 1.418(11) . ?
N2 C8 1.505(11) . ?
Cl4 C14 1.73(2) . ?
N1 C7 1.347(10) . ?
N1 C6 1.403(12) . ?
N1 C12 1.501(12) . ?
C8 C9 1.518(15) . ?
C8 C10 1.536(15) . ?
C8 H8 0.9800 . ?
C12 C13 1.512(17) . ?
C12 C11 1.534(17) . ?
C12 H12 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C2 C1 1.396(13) . ?
C2 C3 1.414(15) . ?
C2 H2 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C6 C1 1.400(13) . ?
C6 C5 1.427(13) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C5 C4 1.396(17) . ?
C5 H5 0.9300 . ?
C3 C4 1.374(18) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C14 H14 0.9800 . ?
