#------------------------------------------------------------------------------
#$Date: 2019-11-24 11:18:36 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237773 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/75/7237562.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_7237562
loop_
_publ_author_name
'Russell, Steven M.'
'Brewer, Anthony M.'
'Stoltzfus, Dani M.'
'Saghaei, Jaber'
'Burn, Paul L.'
_publ_section_title
;
 Organic light-emitting diodes comprising highly luminescent red-emitting
 dendrimers with carbazole-based dendrons
;
_journal_issue                   16
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4681
_journal_paper_doi               10.1039/C8TC05703F
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C57 H33 Br3 Ir1 N3 S3, 0.17(O1)'
_chemical_formula_sum            'C57 H33 Br3 Ir N3 O0.17 S3'
_chemical_formula_weight         1290.65
_chemical_name_common
'Tris[2-(4-(4-bromophenyl)-2-quinolinyl)-3-thienyl-]iridium (III)'
_chemical_name_systematic
'Tris[2-(4-(4-bromophenyl)-2-quinolinyl)-3-thienyl-]iridium (III)'
_space_group_crystal_system      trigonal
_space_group_IT_number           165
_space_group_name_Hall           '-P 3 2"c'
_space_group_name_H-M_alt        'P -3 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2018-11-13 deposited with the CCDC.	2019-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            4
_cell_length_a                   17.712(3)
_cell_length_b                   17.712(3)
_cell_length_c                   17.804(4)
_cell_measurement_reflns_used    67451
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.372
_cell_measurement_theta_min      1.328
_cell_volume                     4837.1(16)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            67451
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.244
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.328
_diffrn_source                   Synchrotron
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_description       prism
_exptl_crystal_F_000             2509
_exptl_crystal_preparation       Cyclometallation
_exptl_crystal_recrystallization_method
'XRD quality crystals were grown from a solution of iridium (III) complex in dimethylsulfoxide and dichloromethane through evaporation. Hexagonal Prism form.'
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.669
_refine_diff_density_min         -1.227
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       0.0015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0468
_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)+(0.0738P)²+18.1691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1371
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2655
_reflns_number_total             3313
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8tc05703f2.cif
_cod_data_source_block           pbar3c1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        4837.1(17)
_cod_database_code               7237562
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: O1(0.05556)
3.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C2(H2), C18(H18), C9(H9), C6(H6), C16(H16), C17(H17), C10(H10),
 C3(H3), C13(H13), C12(H12)
;
_shelx_shelxl_version_number     2016/6
_olex2_exptl_crystal_mounting_method 'In oil on hoop.'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, 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
Ir1 Ir 0.333333 0.666667 0.55856(2) 0.04228(18) Uani 1 3 d S T P
Br1 Br 0.97671(5) 0.76179(6) 0.36003(5) 0.0713(3) Uani 1 1 d . . .
S003 S 0.47063(11) 0.53546(11) 0.65972(11) 0.0547(4) Uani 1 1 d . . .
N1 N 0.4581(3) 0.6921(3) 0.5043(3) 0.0451(12) Uani 1 1 d . . .
C1 C 0.3661(4) 0.5934(4) 0.6203(4) 0.0436(13) Uani 1 1 d . . .
C7 C 0.6208(4) 0.7108(4) 0.4580(4) 0.0474(14) Uani 1 1 d . . .
C19 C 0.5031(4) 0.7444(4) 0.4434(4) 0.0465(14) Uani 1 1 d . . .
C14 C 0.5835(4) 0.7549(4) 0.4182(4) 0.0455(14) Uani 1 1 d . . .
C15 C 0.6220(5) 0.8051(4) 0.3526(4) 0.0539(16) Uani 1 1 d . . .
H15 H 0.674476 0.810110 0.333696 0.065 Uiso 1 1 calc R . .
C2 C 0.3297(5) 0.5408(4) 0.6856(4) 0.0529(16) Uani 1 1 d . . .
H2 H 0.277579 0.531787 0.708844 0.063 Uiso 1 1 calc R . .
C4 C 0.4434(4) 0.5970(4) 0.6010(4) 0.0468(14) Uani 1 1 d . . .
C5 C 0.4936(4) 0.6493(4) 0.5389(4) 0.0441(14) Uani 1 1 d . . .
C18 C 0.4669(4) 0.7876(4) 0.4042(4) 0.0525(16) Uani 1 1 d . . .
H18 H 0.412937 0.781029 0.420581 0.063 Uiso 1 1 calc R . .
C9 C 0.7191(4) 0.6525(4) 0.4244(4) 0.0538(16) Uani 1 1 d . . .
H9 H 0.671537 0.595224 0.431923 0.065 Uiso 1 1 calc R . .
C6 C 0.5749(4) 0.6581(4) 0.5161(4) 0.0499(15) Uani 1 1 d . . .
H6 H 0.597197 0.626590 0.542015 0.060 Uiso 1 1 calc R . .
C16 C 0.5852(4) 0.8464(4) 0.3162(4) 0.0555(17) Uani 1 1 d . . .
H16 H 0.612041 0.880292 0.272620 0.067 Uiso 1 1 calc R . .
C17 C 0.5071(5) 0.8383(5) 0.3435(4) 0.0566(17) Uani 1 1 d . . .
H17 H 0.482204 0.868638 0.319414 0.068 Uiso 1 1 calc R . .
C10 C 0.7999(4) 0.6643(5) 0.4012(4) 0.0571(17) Uani 1 1 d . . .
H10 H 0.807084 0.615536 0.391130 0.069 Uiso 1 1 calc R . .
C8 C 0.7077(4) 0.7233(4) 0.4366(4) 0.0515(16) Uani 1 1 d . . .
C3 C 0.3775(5) 0.5045(5) 0.7118(4) 0.0554(16) Uani 1 1 d . . .
H3 H 0.361047 0.466537 0.753880 0.066 Uiso 1 1 calc R . .
C13 C 0.7795(4) 0.8075(4) 0.4295(5) 0.0572(18) Uani 1 1 d . . .
H13 H 0.773264 0.856967 0.438495 0.069 Uiso 1 1 calc R . .
C11 C 0.8672(4) 0.7462(6) 0.3934(5) 0.0616(19) Uani 1 1 d . . .
C12 C 0.8604(5) 0.8179(5) 0.4090(5) 0.064(2) Uani 1 1 d . . .
H12 H 0.910211 0.874509 0.406054 0.077 Uiso 1 1 calc R . .
O1 O 1.000000 1.000000 0.250000 0.13(3) Uani 0.3334 6 d S T P
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'
Ir Ir -1.4442 7.9887 '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'
S S 0.1246 0.1234 '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
N1 Ir1 N1 102.80(17) 3_565 .
N1 Ir1 N1 102.80(17) 2_665 .
N1 Ir1 N1 102.80(17) 2_665 3_565
C1 Ir1 N1 77.9(2) 3_565 3_565
C1 Ir1 N1 170.3(2) 3_565 .
C1 Ir1 N1 170.3(2) 2_665 3_565
C1 Ir1 N1 86.3(2) . 3_565
C1 Ir1 N1 77.9(2) . .
C1 Ir1 N1 170.3(2) . 2_665
C1 Ir1 N1 86.3(2) 3_565 2_665
C1 Ir1 N1 86.3(2) 2_665 .
C1 Ir1 N1 77.9(2) 2_665 2_665
C1 Ir1 C1 92.6(3) 3_565 .
C1 Ir1 C1 92.6(3) 3_565 2_665
C1 Ir1 C1 92.6(3) 2_665 .
C3 S003 C4 90.1(3) . .
C19 N1 Ir1 130.4(4) . .
C5 N1 Ir1 112.3(4) . .
C5 N1 C19 117.3(5) . .
C2 C1 Ir1 133.7(5) . .
C4 C1 Ir1 115.9(5) . .
C4 C1 C2 110.2(6) . .
C14 C7 C8 121.0(6) . .
C6 C7 C14 118.0(6) . .
C6 C7 C8 121.1(6) . .
N1 C19 C14 122.6(6) . .
N1 C19 C18 119.0(6) . .
C18 C19 C14 118.4(6) . .
C19 C14 C7 118.6(6) . .
C19 C14 C15 118.6(6) . .
C15 C14 C7 122.7(6) . .
C14 C15 H15 119.4 . .
C16 C15 C14 121.3(7) . .
C16 C15 H15 119.4 . .
C1 C2 H2 123.2 . .
C3 C2 C1 113.5(6) . .
C3 C2 H2 123.2 . .
C1 C4 S003 113.5(5) . .
C1 C4 C5 120.1(6) . .
C5 C4 S003 126.3(5) . .
N1 C5 C4 113.8(5) . .
N1 C5 C6 122.4(6) . .
C6 C5 C4 123.8(6) . .
C19 C18 H18 119.1 . .
C17 C18 C19 121.7(6) . .
C17 C18 H18 119.1 . .
C10 C9 H9 119.6 . .
C8 C9 H9 119.6 . .
C8 C9 C10 120.9(6) . .
C7 C6 C5 121.1(6) . .
C7 C6 H6 119.4 . .
C5 C6 H6 119.4 . .
C15 C16 H16 120.3 . .
C15 C16 C17 119.5(7) . .
C17 C16 H16 120.3 . .
C18 C17 C16 120.4(7) . .
C18 C17 H17 119.8 . .
C16 C17 H17 119.8 . .
C9 C10 H10 120.8 . .
C11 C10 C9 118.5(7) . .
C11 C10 H10 120.8 . .
C9 C8 C7 120.9(6) . .
C9 C8 C13 119.0(6) . .
C13 C8 C7 120.1(6) . .
S003 C3 H3 123.7 . .
C2 C3 S003 112.5(6) . .
C2 C3 H3 123.7 . .
C8 C13 H13 120.4 . .
C12 C13 C8 119.3(7) . .
C12 C13 H13 120.4 . .
C10 C11 Br1 118.3(6) . .
C10 C11 C12 122.7(6) . .
C12 C11 Br1 119.0(6) . .
C13 C12 H12 120.2 . .
C11 C12 C13 119.5(7) . .
C11 C12 H12 120.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 N1 2.242(5) 2_665
Ir1 N1 2.242(5) .
Ir1 N1 2.242(5) 3_565
Ir1 C1 1.995(6) 3_565
Ir1 C1 1.995(6) 2_665
Ir1 C1 1.995(6) .
Br1 C11 1.912(6) .
S003 C4 1.743(7) .
S003 C3 1.725(7) .
N1 C19 1.391(8) .
N1 C5 1.350(8) .
C1 C2 1.427(9) .
C1 C4 1.383(9) .
C7 C14 1.437(9) .
C7 C6 1.357(10) .
C7 C8 1.491(9) .
C19 C14 1.414(9) .
C19 C18 1.404(9) .
C14 C15 1.420(10) .
C15 H15 0.9500 .
C15 C16 1.363(10) .
C2 H2 0.9500 .
C2 C3 1.375(10) .
C4 C5 1.430(9) .
C5 C6 1.428(8) .
C18 H18 0.9500 .
C18 C17 1.357(10) .
C9 H9 0.9500 .
C9 C10 1.403(9) .
C9 C8 1.382(9) .
C6 H6 0.9500 .
C16 H16 0.9500 .
C16 C17 1.405(10) .
C17 H17 0.9500 .
C10 H10 0.9500 .
C10 C11 1.348(11) .
C8 C13 1.400(9) .
C3 H3 0.9500 .
C13 H13 0.9500 .
C13 C12 1.399(10) .
C11 C12 1.362(11) .
C12 H12 0.9500 .
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
Ir1 N1 C19 C14 177.8(4)
Ir1 N1 C19 C18 -3.4(9)
Ir1 N1 C5 C4 0.9(7)
Ir1 N1 C5 C6 -177.6(5)
Ir1 C1 C2 C3 -176.9(5)
Ir1 C1 C4 S003 177.2(3)
Ir1 C1 C4 C5 -1.5(8)
Br1 C11 C12 C13 176.5(6)
S003 C4 C5 N1 -178.3(5)
S003 C4 C5 C6 0.1(10)
N1 C19 C14 C7 -1.1(9)
N1 C19 C14 C15 176.0(6)
N1 C19 C18 C17 -178.9(7)
N1 C5 C6 C7 0.3(10)
C1 C2 C3 S003 1.9(8)
C1 C4 C5 N1 0.3(9)
C1 C4 C5 C6 178.8(6)
C7 C14 C15 C16 -179.8(6)
C7 C8 C13 C12 -179.7(7)
C19 N1 C5 C4 179.9(6)
C19 N1 C5 C6 1.5(9)
C19 C14 C15 C16 3.2(10)
C19 C18 C17 C16 2.6(11)
C14 C7 C6 C5 -2.4(10)
C14 C7 C8 C9 -129.3(7)
C14 C7 C8 C13 51.5(10)
C14 C19 C18 C17 0.0(10)
C14 C15 C16 C17 -0.7(10)
C15 C16 C17 C18 -2.2(11)
C2 C1 C4 S003 1.5(7)
C2 C1 C4 C5 -177.3(6)
C4 S003 C3 C2 -0.9(6)
C4 C1 C2 C3 -2.2(9)
C4 C5 C6 C7 -178.0(6)
C5 N1 C19 C14 -1.0(9)
C5 N1 C19 C18 177.8(6)
C18 C19 C14 C7 -179.9(6)
C18 C19 C14 C15 -2.8(9)
C9 C10 C11 Br1 -179.0(6)
C9 C10 C11 C12 1.7(13)
C9 C8 C13 C12 1.1(12)
C6 C7 C14 C19 2.8(9)
C6 C7 C14 C15 -174.2(6)
C6 C7 C8 C9 51.3(10)
C6 C7 C8 C13 -127.9(8)
C10 C9 C8 C7 177.2(7)
C10 C9 C8 C13 -3.5(12)
C10 C11 C12 C13 -4.2(14)
C8 C7 C14 C19 -176.6(6)
C8 C7 C14 C15 6.4(9)
C8 C7 C6 C5 177.0(6)
C8 C9 C10 C11 2.2(12)
C8 C13 C12 C11 2.7(13)
C3 S003 C4 C1 -0.4(6)
C3 S003 C4 C5 178.3(6)
