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#$Date: 2019-11-26 03:35:14 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242518 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/25/4132558.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_4132558
loop_
_publ_author_name
'Lai, Po-Ni'
'Brysacz, Caroline H.'
'Alam, Md Kamrul'
'Ayoub, Nicholas A.'
'Gray, Thomas G.'
'Bao, Jiming'
'Teets, Thomas S.'
_publ_section_title
;
 Highly Efficient Red-Emitting Bis-Cyclometalated Iridium Complexes.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10198
_journal_page_last               10207
_journal_paper_doi               10.1021/jacs.8b04841
_journal_volume                  140
_journal_year                    2018
_chemical_formula_sum            'C40 H37 Cl2 Ir N4 S2'
_chemical_formula_weight         900.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.2146(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2791(8)
_cell_length_b                   21.2737(13)
_cell_length_c                   13.2932(13)
_cell_measurement_reflns_used    4426
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.19
_cell_volume                     3670.3(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0288
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11375
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.588
_diffrn_reflns_theta_min         1.838
_exptl_absorpt_coefficient_mu    3.932
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_description       Block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.094
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.099
_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     226
_refine_ls_number_reflns         4250
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0259
_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)+(0.0247P)²+7.7179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0550
_refine_ls_wR_factor_ref         0.0609
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3159
_reflns_number_total             4250
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b04841_si_002.cif
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4132558
_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. 
;
_shelx_estimated_absorpt_t_min   0.590
_shelx_estimated_absorpt_t_max   0.925
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_refinement_flags_occupancy
Cl1S Cl -0.0001(2) 0.43959(14) 0.8563(2) 0.1603(11) Uani 1 1 d . U .
S1 S 0.21863(8) 0.38409(5) 1.14546(8) 0.0342(2) Uani 1 1 d . . .
Ir1 Ir 0.0000 0.24914(2) 1.2500 0.01722(6) Uani 1 2 d S T P
N1 N 0.0052(2) 0.24822(13) 1.0973(2) 0.0215(5) Uani 1 1 d . . .
N2 N -0.0839(2) 0.16147(12) 1.2382(2) 0.0200(6) Uani 1 1 d . . .
C1 C 0.0000 0.1264(2) 1.2500 0.0204(10) Uani 1 2 d S T P
C1S C 0.0000 0.4857(3) 0.7500 0.098(4) Uani 1 2 d S TU P
H1S1 H -0.0618 0.5130 0.7369 0.117 Uiso 0.5 1 calc R U P
H1S2 H 0.0618 0.5130 0.7631 0.117 Uiso 0.5 1 calc R U P
C12 C -0.0516(3) 0.21043(16) 1.0256(3) 0.0264(8) Uani 1 1 d . . .
H12 H -0.1042 0.1856 1.0442 0.032 Uiso 1 1 calc R U .
C13 C -0.0363(3) 0.20645(18) 0.9266(3) 0.0357(9) Uani 1 1 d . . .
H13 H -0.0781 0.1796 0.8778 0.043 Uiso 1 1 calc R U .
C14 C 0.0407(4) 0.24208(19) 0.8993(3) 0.0428(11) Uani 1 1 d . . .
H14 H 0.0541 0.2389 0.8321 0.051 Uiso 1 1 calc R U .
C15 C 0.0978(3) 0.28215(19) 0.9705(3) 0.0366(9) Uani 1 1 d . . .
H15 H 0.1497 0.3077 0.9520 0.044 Uiso 1 1 calc R U .
C16 C 0.0796(3) 0.28523(16) 1.0696(3) 0.0255(8) Uani 1 1 d . . .
C17 C 0.1302(3) 0.32413(16) 1.1533(3) 0.0247(8) Uani 1 1 d . . .
C20 C 0.1033(3) 0.31799(15) 1.2466(3) 0.0210(7) Uani 1 1 d . . .
C21 C 0.1556(3) 0.36502(15) 1.3180(3) 0.0226(7) Uani 1 1 d . . .
C22 C 0.1474(3) 0.37752(17) 1.4190(3) 0.0310(8) Uani 1 1 d . . .
H22 H 0.1060 0.3512 1.4515 0.037 Uiso 1 1 calc R U .
C23 C 0.1986(4) 0.42749(18) 1.4720(3) 0.0388(10) Uani 1 1 d . . .
H23 H 0.1922 0.4357 1.5406 0.047 Uiso 1 1 calc R U .
C24 C 0.2602(3) 0.46638(17) 1.4251(3) 0.0357(9) Uani 1 1 d . . .
H24 H 0.2950 0.5009 1.4626 0.043 Uiso 1 1 calc R U .
C25 C 0.2716(3) 0.45572(17) 1.3258(3) 0.0334(9) Uani 1 1 d . . .
H25 H 0.3136 0.4823 1.2945 0.040 Uiso 1 1 calc R U .
C26 C 0.2194(3) 0.40469(16) 1.2727(3) 0.0266(8) Uani 1 1 d . . .
C31 C 0.0000 0.0558(2) 1.2500 0.0218(10) Uani 1 2 d S T P
C32 C -0.0372(3) 0.02295(16) 1.1590(3) 0.0250(7) Uani 1 1 d . . .
H32 H -0.0631 0.0451 1.0969 0.030 Uiso 1 1 calc R U .
C33 C -0.0363(3) -0.04264(16) 1.1596(3) 0.0274(8) Uani 1 1 d . . .
H33 H -0.0607 -0.0651 1.0975 0.033 Uiso 1 1 calc R U .
C34 C 0.0000 -0.0750(2) 1.2500 0.0318(12) Uani 1 2 d S T P
H34 H 0.0000 -0.1196 1.2500 0.038 Uiso 1 2 calc R U P
C41 C -0.1850(3) 0.13829(15) 1.2487(3) 0.0265(8) Uani 1 1 d . . .
H41 H -0.1971 0.0967 1.2131 0.032 Uiso 1 1 calc R U .
C42 C -0.1902(3) 0.12876(18) 1.3620(3) 0.0367(10) Uani 1 1 d . . .
H42A H -0.1357 0.0997 1.3945 0.055 Uiso 1 1 calc R U .
H42B H -0.2575 0.1112 1.3659 0.055 Uiso 1 1 calc R U .
H42C H -0.1806 0.1693 1.3979 0.055 Uiso 1 1 calc R U .
C43 C -0.2681(3) 0.18349(18) 1.1955(4) 0.0400(10) Uani 1 1 d . . .
H43A H -0.2597 0.2240 1.2313 0.060 Uiso 1 1 calc R U .
H43B H -0.3361 0.1661 1.1969 0.060 Uiso 1 1 calc R U .
H43C H -0.2621 0.1895 1.1239 0.060 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C26 S1 C17 89.53(17) . .
C20 Ir1 C20 86.67(18) . 2_557
C20 Ir1 N1 79.55(12) . .
C20 Ir1 N1 101.26(12) 2_557 .
C20 Ir1 N1 101.27(12) . 2_557
C20 Ir1 N1 79.55(12) 2_557 2_557
N1 Ir1 N1 178.90(15) . 2_557
C20 Ir1 N2 165.74(11) . .
C20 Ir1 N2 106.63(12) 2_557 .
N1 Ir1 N2 92.56(11) . .
N1 Ir1 N2 86.48(11) 2_557 .
C20 Ir1 N2 106.63(12) . 2_557
C20 Ir1 N2 165.74(11) 2_557 2_557
N1 Ir1 N2 86.49(10) . 2_557
N1 Ir1 N2 92.56(11) 2_557 2_557
N2 Ir1 N2 60.67(14) . 2_557
C20 Ir1 C1 136.66(9) . .
C20 Ir1 C1 136.66(9) 2_557 .
N1 Ir1 C1 89.45(8) . .
N1 Ir1 C1 89.45(8) 2_557 .
N2 Ir1 C1 30.34(7) . .
N2 Ir1 C1 30.34(7) 2_557 .
C12 N1 C16 118.6(3) . .
C12 N1 Ir1 125.2(2) . .
C16 N1 Ir1 116.0(2) . .
C1 N2 C41 124.4(3) . .
C1 N2 Ir1 94.0(2) . .
C41 N2 Ir1 138.8(2) . .
N2 C1 N2 111.3(4) 2_557 .
N2 C1 C31 124.33(19) 2_557 .
N2 C1 C31 124.33(19) . .
N2 C1 Ir1 55.67(19) 2_557 .
N2 C1 Ir1 55.67(19) . .
C31 C1 Ir1 180.0 . .
Cl1S C1S Cl1S 110.5(4) 2_556 .
N1 C12 C13 122.6(3) . .
C12 C13 C14 119.0(4) . .
C15 C14 C13 119.3(4) . .
C14 C15 C16 120.0(4) . .
N1 C16 C15 120.4(3) . .
N1 C16 C17 111.6(3) . .
C15 C16 C17 128.0(3) . .
C20 C17 C16 118.6(3) . .
C20 C17 S1 115.5(3) . .
C16 C17 S1 125.7(3) . .
C17 C20 C21 110.3(3) . .
C17 C20 Ir1 113.6(3) . .
C21 C20 Ir1 136.1(2) . .
C22 C21 C26 118.1(3) . .
C22 C21 C20 129.5(3) . .
C26 C21 C20 112.3(3) . .
C23 C22 C21 120.6(3) . .
C22 C23 C24 120.2(4) . .
C25 C24 C23 121.4(3) . .
C24 C25 C26 118.0(3) . .
C25 C26 C21 121.7(3) . .
C25 C26 S1 125.9(3) . .
C21 C26 S1 112.4(3) . .
C32 C31 C32 119.9(4) 2_557 .
C32 C31 C1 120.1(2) 2_557 .
C32 C31 C1 120.1(2) . .
C31 C32 C33 119.7(3) . .
C34 C33 C32 120.3(4) . .
C33 C34 C33 120.2(5) 2_557 .
N2 C41 C43 109.4(3) . .
N2 C41 C42 111.7(3) . .
C43 C41 C42 111.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1S C1S 1.721(4) .
S1 C26 1.745(4) .
S1 C17 1.752(3) .
Ir1 C20 2.014(3) .
Ir1 C20 2.014(3) 2_557
Ir1 N1 2.046(3) .
Ir1 N1 2.046(3) 2_557
Ir1 N2 2.161(3) .
Ir1 N2 2.161(3) 2_557
Ir1 C1 2.611(4) .
N1 C12 1.348(4) .
N1 C16 1.373(4) .
N2 C1 1.322(4) .
N2 C41 1.464(4) .
C1 N2 1.322(4) 2_557
C1 C31 1.503(6) .
C1S Cl1S 1.721(4) 2_556
C12 C13 1.376(5) .
C13 C14 1.382(6) .
C14 C15 1.376(6) .
C15 C16 1.390(5) .
C16 C17 1.435(5) .
C17 C20 1.367(5) .
C20 C21 1.451(5) .
C21 C22 1.396(5) .
C21 C26 1.417(5) .
C22 C23 1.373(5) .
C23 C24 1.399(5) .
C24 C25 1.378(5) .
C25 C26 1.396(5) .
C31 C32 1.394(4) 2_557
C31 C32 1.394(4) .
C32 C33 1.396(5) .
C33 C34 1.380(4) .
C34 C33 1.380(5) 2_557
C41 C43 1.521(5) .
C41 C42 1.535(5) .
