#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/37/4303705.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_4303705
loop_
_publ_author_name
'Arup Sinha'
'S. M. Wahidur Rahaman'
'Mithun Sarkar'
'Biswajit Saha'
'Prosenjit Daw'
'Jitendra K. Bera'
_publ_contact_author_address
'Department of Chemistry, IIT Kanpur, Kanpur 208016, INDIA.'
_publ_contact_author_email       jbera@iitk.ac.in
_publ_contact_author_fax         '+ 91-512-2597436'
_publ_contact_author_name        'Jitendra K. Bera'
_publ_contact_author_phone       '+ 91-512-2597336'
_publ_section_title
;
Multifaceted Coordination of Naphthyridine-Functionalized N-Heterocyclic
Carbene: A Novel "IrIII(CN)(CC)" Compound and Its Evaluation as
Transfer Hydrogenation Catalyst
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11114
_journal_page_last               11122
_journal_paper_doi               10.1021/ic901502n
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C20 H19 N4, Br'
_chemical_formula_sum            'C20 H19 Br N4'
_chemical_formula_weight         395.30
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.327(3)
_cell_angle_beta                 75.561(3)
_cell_angle_gamma                72.375(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4940(13)
_cell_length_b                   11.2896(19)
_cell_length_c                   11.612(2)
_cell_measurement_reflns_used    2341
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.76
_cell_volume                     902.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'omega scans'
_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  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5969
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    2.288
_exptl_absorpt_correction_T_max  0.6576
_exptl_absorpt_correction_T_min  0.6576
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0645P)²+1.5247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1542
_reflns_number_gt                3292
_reflns_number_total             4260
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic901502n_si_002_1.cif
_cod_data_source_block           binhbr
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4303705
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.33454(6) 0.95794(4) 0.85587(4) 0.05124(17) Uani 1 1 d . . .
N2 N 0.1799(4) 0.5908(3) -0.0832(3) 0.0344(6) Uani 1 1 d . . .
N3 N 0.1711(4) 0.7235(3) 0.0507(3) 0.0347(6) Uani 1 1 d . . .
N1 N 0.2105(5) 0.4551(3) -0.2181(3) 0.0405(7) Uani 1 1 d . . .
C10 C 0.0786(5) 0.6876(3) -0.0265(3) 0.0342(7) Uani 1 1 d . . .
N4 N 0.2346(4) 0.8323(3) 0.1631(3) 0.0371(7) Uani 1 1 d . . .
C13 C 0.1073(5) 0.8271(4) 0.1062(3) 0.0361(8) Uani 1 1 d . . .
H13 H -0.0096 0.8864 0.1047 0.043 Uiso 1 1 calc R . .
C6 C -0.0889(5) 0.6197(3) -0.1769(3) 0.0359(8) Uani 1 1 d . . .
C9 C -0.1089(5) 0.7586(4) -0.0362(3) 0.0393(8) Uani 1 1 d . . .
H9 H -0.1735 0.8267 0.0073 0.047 Uiso 1 1 calc R . .
C7 C 0.0984(5) 0.5550(3) -0.1600(3) 0.0354(8) Uani 1 1 d . . .
C11 C 0.3526(6) 0.6621(4) 0.0718(4) 0.0472(10) Uani 1 1 d . . .
H11 H 0.4323 0.5877 0.0429 0.057 Uiso 1 1 calc R . .
C3 C -0.0437(6) 0.4785(4) -0.3180(4) 0.0431(9) Uani 1 1 d . . .
H3 H -0.0858 0.4501 -0.3743 0.052 Uiso 1 1 calc R . .
C8 C -0.1906(5) 0.7231(4) -0.1115(4) 0.0406(8) Uani 1 1 d . . .
H8 H -0.3141 0.7671 -0.1202 0.049 Uiso 1 1 calc R . .
C4 C -0.1619(6) 0.5776(4) -0.2589(4) 0.0399(8) Uani 1 1 d . . .
C2 C 0.1411(6) 0.4179(4) -0.2957(4) 0.0428(9) Uani 1 1 d . . .
C12 C 0.3912(6) 0.7303(4) 0.1417(4) 0.0485(10) Uani 1 1 d . . .
H12 H 0.5029 0.7121 0.1704 0.058 Uiso 1 1 calc R . .
C5 C -0.3601(6) 0.6402(5) -0.2809(5) 0.0553(11) Uani 1 1 d . . .
H5A H -0.3672 0.7244 -0.3159 0.083 Uiso 1 1 calc R . .
H5B H -0.4517 0.6411 -0.2065 0.083 Uiso 1 1 calc R . .
H5C H -0.3877 0.5951 -0.3343 0.083 Uiso 1 1 calc R . .
C1 C 0.2667(7) 0.3071(5) -0.3605(5) 0.0621(13) Uani 1 1 d . . .
H1A H 0.3931 0.3175 -0.3906 0.093 Uiso 1 1 calc R . .
H1B H 0.2140 0.3009 -0.4259 0.093 Uiso 1 1 calc R . .
H1C H 0.2731 0.2324 -0.3064 0.093 Uiso 1 1 calc R . .
C15 C 0.2220(5) 0.8945(4) 0.3608(3) 0.0368(8) Uani 1 1 d . . .
C16 C 0.2812(7) 0.9635(4) 0.4235(4) 0.0512(10) Uani 1 1 d . . .
H16 H 0.3217 1.0329 0.3847 0.061 Uiso 1 1 calc R . .
C20 C 0.1680(8) 0.7919(5) 0.4198(4) 0.0566(12) Uani 1 1 d . . .
H20 H 0.1289 0.7434 0.3789 0.068 Uiso 1 1 calc R . .
C18 C 0.2271(7) 0.8293(5) 0.6011(4) 0.0583(12) Uani 1 1 d . . .
H18 H 0.2286 0.8077 0.6818 0.070 Uiso 1 1 calc R . .
C17 C 0.2807(7) 0.9306(5) 0.5434(4) 0.0591(12) Uani 1 1 d . . .
H17 H 0.3182 0.9793 0.5850 0.071 Uiso 1 1 calc R . .
C19 C 0.1704(9) 0.7583(5) 0.5404(4) 0.0663(14) Uani 1 1 d . . .
H19 H 0.1336 0.6878 0.5796 0.080 Uiso 1 1 calc R . .
C14 C 0.2172(6) 0.9353(4) 0.2308(4) 0.0436(9) Uani 1 1 d . . .
H14A H 0.0977 0.9985 0.2254 0.052 Uiso 1 1 calc R . .
H14B H 0.3210 0.9731 0.1947 0.052 Uiso 1 1 calc R . .
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'
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
C10 N2 C7 117.2(3) . . ?
C13 N3 C11 107.6(3) . . ?
C13 N3 C10 126.4(3) . . ?
C11 N3 C10 125.7(3) . . ?
C2 N1 C7 117.7(3) . . ?
N2 C10 C9 125.8(3) . . ?
N2 C10 N3 115.3(3) . . ?
C9 C10 N3 118.8(3) . . ?
C13 N4 C12 108.7(3) . . ?
C13 N4 C14 125.0(3) . . ?
C12 N4 C14 126.2(3) . . ?
N4 C13 N3 109.4(3) . . ?
C8 C6 C4 124.0(3) . . ?
C8 C6 C7 117.8(3) . . ?
C4 C6 C7 118.2(3) . . ?
C8 C9 C10 117.2(3) . . ?
N1 C7 N2 114.9(3) . . ?
N1 C7 C6 123.4(3) . . ?
N2 C7 C6 121.7(3) . . ?
C12 C11 N3 107.0(4) . . ?
C4 C3 C2 121.7(4) . . ?
C9 C8 C6 120.2(3) . . ?
C3 C4 C6 117.0(4) . . ?
C3 C4 C5 121.6(4) . . ?
C6 C4 C5 121.4(4) . . ?
N1 C2 C3 122.1(4) . . ?
N1 C2 C1 117.5(4) . . ?
C3 C2 C1 120.4(4) . . ?
C11 C12 N4 107.2(3) . . ?
C20 C15 C16 118.1(4) . . ?
C20 C15 C14 122.5(4) . . ?
C16 C15 C14 119.3(4) . . ?
C15 C16 C17 120.5(4) . . ?
C15 C20 C19 121.1(4) . . ?
C17 C18 C19 119.6(4) . . ?
C18 C17 C16 121.1(4) . . ?
C18 C19 C20 119.7(5) . . ?
N4 C14 C15 113.1(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
N2 C10 1.302(5) . ?
N2 C7 1.368(5) . ?
N3 C13 1.331(5) . ?
N3 C11 1.389(5) . ?
N3 C10 1.431(5) . ?
N1 C2 1.323(5) . ?
N1 C7 1.354(5) . ?
C10 C9 1.413(5) . ?
N4 C13 1.309(5) . ?
N4 C12 1.378(5) . ?
N4 C14 1.466(5) . ?
C6 C8 1.411(5) . ?
C6 C4 1.415(5) . ?
C6 C7 1.418(5) . ?
C9 C8 1.354(6) . ?
C11 C12 1.341(6) . ?
C3 C4 1.364(6) . ?
C3 C2 1.414(6) . ?
C4 C5 1.504(6) . ?
C2 C1 1.505(6) . ?
C15 C20 1.362(6) . ?
C15 C16 1.377(6) . ?
C15 C14 1.508(5) . ?
C16 C17 1.379(6) . ?
C20 C19 1.391(7) . ?
C18 C17 1.343(7) . ?
C18 C19 1.366(7) . ?
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
C9 C10 N3 C13 -8.1(5) . . . . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.004 -0.004 0.000 829 344 ' '
2 0.085 0.085 0.500 829 345 ' '
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660760
2 PubChem 168336824
