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#$Date: 2022-10-22 00:44:13 +0300 (Sat, 22 Oct 2022) $
#$Revision: 278715 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/78/1567824.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_1567824
loop_
_publ_author_name
'Rit, Arnab'
'Illam, Praseetha Mathoor'
'Tiwari, Chandra Shekhar'
_publ_section_title
;
 Towards New Coordination Modes of 1,2,3-Triazolylidene: Controlled by the
 Nature of 1st Metalation in a Heteroditopic Bis-NHC Ligand
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC05024B
_journal_year                    2022
_chemical_formula_moiety         'C15 H16 Br2 N4 Pd'
_chemical_formula_sum            'C15 H16 Br2 N4 Pd'
_chemical_formula_weight         518.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-31 deposited with the CCDC.	2022-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.771(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7060(18)
_cell_length_b                   6.2505(7)
_cell_length_c                   15.8120(14)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.24
_cell_measurement_theta_min      3.01
_cell_volume                     1729.5(3)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            59679
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.516
_diffrn_reflns_theta_min         3.461
_exptl_absorpt_coefficient_mu    5.694
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.991
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.894
_refine_diff_density_min         -1.469
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         5270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0311
_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)+(0.0277P)²+2.4420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0757
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4165
_reflns_number_total             5270
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc05024b2.cif
_cod_data_source_block           shelx_CCDC1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1567824
_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.
;
_shelx_estimated_absorpt_t_min   0.427
_shelx_estimated_absorpt_t_max   0.698
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Pd1 Pd 0.19440(2) 0.36201(3) 0.68694(2) 0.03467(6) Uani 1 1 d . . . . .
C1 C 0.34839(17) 0.6406(5) 0.6532(2) 0.0417(6) Uani 1 1 d . . . . .
H1 H 0.297343 0.651667 0.660280 0.050 Uiso 1 1 calc R U . . .
C2 C 0.39988(19) 0.8015(5) 0.6825(2) 0.0460(7) Uani 1 1 d . . . . .
H2 H 0.383250 0.920173 0.710012 0.055 Uiso 1 1 calc R U . . .
C3 C 0.47521(19) 0.7872(6) 0.6712(2) 0.0485(7) Uani 1 1 d . . . . .
H3 H 0.509236 0.896036 0.690910 0.058 Uiso 1 1 calc R U . . .
C4 C 0.50024(18) 0.6111(6) 0.6307(2) 0.0511(8) Uani 1 1 d . . . . .
H4 H 0.551068 0.602176 0.622531 0.061 Uiso 1 1 calc R U . . .
C5 C 0.44999(17) 0.4478(5) 0.6021(2) 0.0460(7) Uani 1 1 d . . . . .
H5 H 0.466986 0.328214 0.575535 0.055 Uiso 1 1 calc R U . . .
C6 C 0.37402(15) 0.4641(5) 0.61344(17) 0.0347(5) Uani 1 1 d . . . . .
C7 C 0.25264(15) 0.2391(5) 0.60231(18) 0.0368(6) Uani 1 1 d . . . . .
C8 C 0.23216(17) 0.0667(5) 0.5504(2) 0.0417(6) Uani 1 1 d . . . . .
H8 H 0.187560 -0.012944 0.548303 0.050 Uiso 1 1 calc R U . . .
C9 C 0.2907(2) -0.1333(6) 0.4372(2) 0.0514(8) Uani 1 1 d . . . . .
H9A H 0.270661 -0.265921 0.456725 0.062 Uiso 1 1 calc R U . . .
H9B H 0.257918 -0.090604 0.385112 0.062 Uiso 1 1 calc R U . . .
C10 C 0.3684(2) -0.1714(7) 0.4180(3) 0.0640(10) Uani 1 1 d . . . . .
H10A H 0.387318 -0.043349 0.395013 0.096 Uiso 1 1 calc R U . . .
H10B H 0.367186 -0.284898 0.376882 0.096 Uiso 1 1 calc R U . . .
H10C H 0.401461 -0.210868 0.469536 0.096 Uiso 1 1 calc R U . . .
C11 C 0.10004(18) 0.6798(5) 0.7746(2) 0.0470(7) Uani 1 1 d . . . . .
H11 H 0.116030 0.775874 0.736007 0.056 Uiso 1 1 calc R U . . .
C12 C 0.0502(2) 0.7493(6) 0.8277(2) 0.0573(9) Uani 1 1 d . . . . .
H12 H 0.032792 0.889876 0.824727 0.069 Uiso 1 1 calc R U . . .
C13 C 0.0266(2) 0.6085(7) 0.8853(2) 0.0605(10) Uani 1 1 d . . . . .
H13 H -0.007436 0.652112 0.921185 0.073 Uiso 1 1 calc R U . . .
C14 C 0.0540(2) 0.4030(7) 0.8889(2) 0.0578(9) Uani 1 1 d . . . . .
H14 H 0.039100 0.305025 0.927445 0.069 Uiso 1 1 calc R U . . .
C15 C 0.10411(19) 0.3446(6) 0.8344(2) 0.0478(7) Uani 1 1 d . . . . .
H15 H 0.123465 0.206011 0.837967 0.057 Uiso 1 1 calc R U . . .
N1 N 0.32173(13) 0.2963(4) 0.58065(14) 0.0344(5) Uani 1 1 d . . . . .
N2 N 0.34351(14) 0.1721(4) 0.51962(15) 0.0389(5) Uani 1 1 d . . . . .
N3 N 0.28787(14) 0.0332(4) 0.50307(15) 0.0396(5) Uani 1 1 d . . . . .
N4 N 0.12630(13) 0.4777(4) 0.77659(16) 0.0388(5) Uani 1 1 d . . . . .
Br1 Br 0.27182(2) 0.14822(7) 0.79566(2) 0.06590(12) Uani 1 1 d . . . . .
Br2 Br 0.11927(2) 0.55320(6) 0.56819(2) 0.05063(9) 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'
Br Br -0.2901 2.4595 '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'
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
C7 Pd1 N4 176.19(11) . . ?
C7 Pd1 Br1 88.20(8) . . ?
N4 Pd1 Br1 91.80(7) . . ?
C7 Pd1 Br2 87.06(8) . . ?
N4 Pd1 Br2 92.78(7) . . ?
Br1 Pd1 Br2 174.815(16) . . ?
C6 C1 C2 119.1(3) . . ?
C6 C1 H1 120.5 . . ?
C2 C1 H1 120.5 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 120.7(3) . . ?
C1 C6 N1 120.5(2) . . ?
C5 C6 N1 118.8(3) . . ?
N1 C7 C8 102.8(2) . . ?
N1 C7 Pd1 130.6(2) . . ?
C8 C7 Pd1 126.7(2) . . ?
N3 C8 C7 107.9(3) . . ?
N3 C8 H8 126.1 . . ?
C7 C8 H8 126.1 . . ?
C10 C9 N3 113.1(3) . . ?
C10 C9 H9A 109.0 . . ?
N3 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
N3 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C11 C12 122.2(3) . . ?
N4 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 118.7(4) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
N4 C15 C14 123.2(3) . . ?
N4 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
N2 N1 C7 113.3(2) . . ?
N2 N1 C6 116.1(2) . . ?
C7 N1 C6 130.5(2) . . ?
N3 N2 N1 103.7(2) . . ?
N2 N3 C8 112.3(2) . . ?
N2 N3 C9 120.2(3) . . ?
C8 N3 C9 127.5(3) . . ?
C15 N4 C11 117.6(3) . . ?
C15 N4 Pd1 120.0(2) . . ?
C11 N4 Pd1 122.2(2) . . ?
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
Pd1 C7 1.966(3) . ?
Pd1 N4 2.123(2) . ?
Pd1 Br1 2.4294(4) . ?
Pd1 Br2 2.4417(4) . ?
C1 C6 1.381(4) . ?
C1 C2 1.389(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.442(4) . ?
C7 N1 1.367(3) . ?
C7 C8 1.369(4) . ?
C8 N3 1.342(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.474(5) . ?
C9 N3 1.478(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N4 1.345(4) . ?
C11 C12 1.378(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(5) . ?
C14 H14 0.9300 . ?
C15 N4 1.339(4) . ?
C15 H15 0.9300 . ?
N1 N2 1.340(3) . ?
N2 N3 1.310(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H8 Br2 0.93 3.01 3.814(3) 146.4 1_545 yes
C9 H9B Br1 0.97 3.13 3.753(4) 123.3 4_565 yes
C10 H10B Br1 0.96 3.00 3.813(4) 143.4 4 yes
C15 H15 Br1 0.93 2.83 3.355(3) 116.8 . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.8(5) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
C2 C1 C6 N1 -178.7(3) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C4 C5 C6 N1 177.8(3) . . . . ?
N1 C7 C8 N3 0.0(3) . . . . ?
Pd1 C7 C8 N3 -179.2(2) . . . . ?
N4 C11 C12 C13 0.3(6) . . . . ?
C11 C12 C13 C14 0.8(6) . . . . ?
C12 C13 C14 C15 -0.3(6) . . . . ?
C13 C14 C15 N4 -1.4(6) . . . . ?
C8 C7 N1 N2 0.4(3) . . . . ?
Pd1 C7 N1 N2 179.6(2) . . . . ?
C8 C7 N1 C6 -178.7(3) . . . . ?
Pd1 C7 N1 C6 0.5(5) . . . . ?
C1 C6 N1 N2 158.1(3) . . . . ?
C5 C6 N1 N2 -20.0(4) . . . . ?
C1 C6 N1 C7 -22.8(4) . . . . ?
C5 C6 N1 C7 159.1(3) . . . . ?
C7 N1 N2 N3 -0.6(3) . . . . ?
C6 N1 N2 N3 178.6(2) . . . . ?
N1 N2 N3 C8 0.6(3) . . . . ?
N1 N2 N3 C9 179.5(3) . . . . ?
C7 C8 N3 N2 -0.4(4) . . . . ?
C7 C8 N3 C9 -179.2(3) . . . . ?
C10 C9 N3 N2 20.2(5) . . . . ?
C10 C9 N3 C8 -161.1(3) . . . . ?
C14 C15 N4 C11 2.5(5) . . . . ?
C14 C15 N4 Pd1 -173.5(3) . . . . ?
C12 C11 N4 C15 -1.9(5) . . . . ?
C12 C11 N4 Pd1 174.0(3) . . . . ?
