#------------------------------------------------------------------------------
#$Date: 2019-11-24 13:37:25 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238030 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/92/4089200.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_4089200
loop_
_publ_author_name
'Congrave, Daniel G.'
'Hsu, Yu-ting'
'Batsanov, Andrei S.'
'Beeby, Andrew'
'Bryce, Martin R.'
_publ_section_title
;
 Synthesis, Diastereomer Separation, and Optoelectronic and Structural
 Properties of Dinuclear Cyclometalated Iridium(III) Complexes with
 Bridging Diarylhydrazide Ligands
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              981
_journal_paper_doi               10.1021/acs.organomet.6b00887
_journal_volume                  36
_journal_year                    2017
_chemical_formula_moiety         'C62 H38 F12 Ir2 N6 O2'
_chemical_formula_sum            'C62 H38 F12 Ir2 N6 O2'
_chemical_formula_weight         1511.38
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-07-01
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.0515(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1462(5)
_cell_length_b                   22.4652(11)
_cell_length_c                   23.7388(12)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    120
_cell_measurement_theta_max      35.31
_cell_measurement_theta_min      2.30
_cell_volume                     5380.8(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
'ShelXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            72160
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        32.500
_diffrn_reflns_theta_max         35.574
_diffrn_reflns_theta_min         2.213
_diffrn_source                   'I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.035
_exptl_absorpt_correction_T_max  0.8126
_exptl_absorpt_correction_T_min  0.3216
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1421 before and 0.0463 after correction.
The Ratio of minimum to maximum transmission is 0.3958.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_description       lathe
_exptl_crystal_F_000             2920
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.086
_refine_diff_density_max         2.010
_refine_diff_density_min         -1.627
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         11671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0229
_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)+(0.0110P)²+16.0910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0436
_refine_ls_wR_factor_ref         0.0453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10339
_reflns_number_total             11671
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00887_si_002.cif
_cod_data_source_block           16b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/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_database_code               4089200
_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_max   0.671
_shelx_estimated_absorpt_t_min   0.314
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28),
  C29(H29), C30(H30), C31(H31)
;
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
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
Ir Ir -0.01030(2) 0.12732(2) 0.14232(2) 0.01052(2) Uani 1 1 d .
F1 F 0.47972(14) 0.27039(6) 0.36609(7) 0.0338(3) Uani 1 1 d .
F2 F 0.65689(17) 0.22086(7) 0.39032(8) 0.0516(5) Uani 1 1 d .
F3 F 0.61605(17) 0.25250(7) 0.30595(7) 0.0442(4) Uani 1 1 d .
F4 F 0.5767(2) 0.00230(9) 0.40028(8) 0.0581(5) Uani 1 1 d .
F5 F 0.6351(3) -0.00640(10) 0.31973(10) 0.0804(8) Uani 1 1 d .
F6 F 0.4458(2) -0.03679(8) 0.33707(17) 0.1296(16) Uani 1 1 d .
O O 0.17685(12) 0.13230(6) 0.19328(5) 0.0144(2) Uani 1 1 d .
N1 N -0.05756(13) 0.12368(6) 0.22948(6) 0.0112(2) Uani 1 1 d .
N2 N -0.04486(15) 0.21644(7) 0.14137(6) 0.0137(3) Uani 1 1 d .
N3 N 0.01952(15) 0.03779(7) 0.13520(7) 0.0153(3) Uani 1 1 d .
C1 C 0.16812(15) 0.12729(7) 0.24650(7) 0.0111(2) Uani 1 1 d .
C2 C 0.29608(15) 0.12467(8) 0.28353(7) 0.0118(3) Uani 1 1 d .
C3 C 0.36437(17) 0.17596(8) 0.30083(8) 0.0150(3) Uani 1 1 d .
H3 H 0.3274 0.2138 0.2908 0.018 Uiso 1 1 calc R
C4 C 0.48679(17) 0.17212(8) 0.33277(8) 0.0149(3) Uani 1 1 d .
C5 C 0.54498(17) 0.11750(9) 0.34824(8) 0.0184(3) Uani 1 1 d .
H5 H 0.6291 0.1151 0.3698 0.022 Uiso 1 1 calc R
C6 C 0.47342(18) 0.06622(8) 0.33043(8) 0.0183(3) Uani 1 1 d .
C7 C 0.35163(18) 0.06933(8) 0.29796(8) 0.0172(3) Uani 1 1 d .
H7 H 0.3063 0.0339 0.2856 0.021 Uiso 1 1 calc R
C8 C 0.56017(19) 0.22831(9) 0.34923(9) 0.0218(4) Uani 1 1 d .
C9 C 0.5309(2) 0.00641(10) 0.34656(12) 0.0333(5) Uani 1 1 d .
C10 C -0.18193(16) 0.12929(8) 0.09248(7) 0.0130(3) Uani 1 1 d .
C11 C -0.25605(19) 0.08153(9) 0.06746(8) 0.0185(3) Uani 1 1 d .
H11 H -0.2277 0.0419 0.0759 0.022 Uiso 1 1 calc R
C12 C -0.3697(2) 0.09091(10) 0.03066(8) 0.0226(4) Uani 1 1 d .
H12 H -0.4180 0.0577 0.0146 0.027 Uiso 1 1 calc R
C13 C -0.41398(19) 0.14811(11) 0.01695(8) 0.0234(4) Uani 1 1 d .
H13 H -0.4916 0.1540 -0.0085 0.028 Uiso 1 1 calc R
C14 C -0.34385(19) 0.19646(9) 0.04072(8) 0.0201(3) Uani 1 1 d .
H14 H -0.3732 0.2358 0.0316 0.024 Uiso 1 1 calc R
C15 C -0.22968(17) 0.18715(8) 0.07817(7) 0.0148(3) Uani 1 1 d .
C16 C -0.15356(17) 0.23523(8) 0.10719(7) 0.0142(3) Uani 1 1 d .
C17 C -0.1839(2) 0.29563(9) 0.10341(9) 0.0213(4) Uani 1 1 d .
H17 H -0.2592 0.3087 0.0794 0.026 Uiso 1 1 calc R
C18 C -0.1049(2) 0.33663(9) 0.13444(10) 0.0278(4) Uani 1 1 d .
H18 H -0.1257 0.3778 0.1322 0.033 Uiso 1 1 calc R
C19 C 0.0057(2) 0.31669(9) 0.16909(10) 0.0275(4) Uani 1 1 d .
H19 H 0.0616 0.3440 0.1908 0.033 Uiso 1 1 calc R
C20 C 0.0324(2) 0.25645(8) 0.17127(9) 0.0201(3) Uani 1 1 d .
H20 H 0.1080 0.2428 0.1947 0.024 Uiso 1 1 calc R
C21 C 0.07534(17) 0.12619(8) 0.06994(7) 0.0152(3) Uani 1 1 d .
C22 C 0.10378(19) 0.17407(10) 0.03549(8) 0.0205(4) Uani 1 1 d .
H22 H 0.0725 0.2127 0.0435 0.025 Uiso 1 1 calc R
C23 C 0.1772(2) 0.16618(12) -0.01049(9) 0.0274(4) Uani 1 1 d .
H23 H 0.1959 0.1994 -0.0331 0.033 Uiso 1 1 calc R
C24 C 0.2231(2) 0.11005(12) -0.02352(9) 0.0304(5) Uani 1 1 d .
H24 H 0.2741 0.1050 -0.0545 0.036 Uiso 1 1 calc R
C25 C 0.1942(2) 0.06157(11) 0.00885(9) 0.0266(4) Uani 1 1 d .
H25 H 0.2246 0.0230 0.0000 0.032 Uiso 1 1 calc R
C26 C 0.11975(18) 0.06940(9) 0.05477(8) 0.0184(3) Uani 1 1 d .
C27 C 0.08225(18) 0.02031(8) 0.09006(8) 0.0174(3) Uani 1 1 d .
C28 C 0.1021(2) -0.04036(9) 0.08016(10) 0.0259(4) Uani 1 1 d .
H28 H 0.1456 -0.0526 0.0486 0.031 Uiso 1 1 calc R
C29 C 0.0587(2) -0.08207(9) 0.11616(12) 0.0308(5) Uani 1 1 d .
H29 H 0.0715 -0.1233 0.1095 0.037 Uiso 1 1 calc R
C30 C -0.0038(2) -0.06372(9) 0.16230(11) 0.0288(5) Uani 1 1 d .
H30 H -0.0338 -0.0920 0.1878 0.035 Uiso 1 1 calc R
C31 C -0.0217(2) -0.00350(8) 0.17053(9) 0.0207(4) Uani 1 1 d .
H31 H -0.0646 0.0092 0.2021 0.025 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'
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'
F F 0.0171 0.0103 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0430
0.00 0.00 1.00 0.0070
0.00 -1.00 0.00 0.0440
-1.00 2.00 -2.00 0.1150
2.00 1.00 1.00 0.1290
1.00 1.00 0.00 0.1290
-1.00 -1.00 0.00 0.1320
-2.00 2.00 -1.00 0.1330
2.00 -2.00 1.00 0.1200
0.00 1.00 0.00 0.0380
0.00 1.00 2.00 0.0060
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
O Ir N1 74.70(5) . .
N2 Ir O 95.53(5) . .
N2 Ir N1 89.57(6) . .
N2 Ir N3 174.59(6) . .
N3 Ir O 88.17(5) . .
N3 Ir N1 95.23(6) . .
C10 Ir O 175.35(6) . .
C10 Ir N1 107.35(6) . .
C10 Ir N2 80.40(7) . .
C10 Ir N3 95.75(7) . .
C10 Ir C21 85.54(7) . .
C21 Ir O 92.65(6) . .
C21 Ir N1 166.84(6) . .
C21 Ir N2 95.32(7) . .
C21 Ir N3 80.53(7) . .
C1 O Ir 113.75(10) . .
N1 N1 Ir 113.54(13) 2 .
C1 N1 Ir 134.03(11) 2 .
C1 N1 N1 112.04(16) 2 2
C16 N2 Ir 116.02(12) . .
C20 N2 Ir 124.21(13) . .
C20 N2 C16 119.77(16) . .
C27 N3 Ir 115.78(13) . .
C31 N3 Ir 124.62(13) . .
C31 N3 C27 119.57(16) . .
O C1 N1 125.79(14) . 2
O C1 C2 116.02(14) . .
N1 C1 C2 118.18(14) 2 .
C3 C2 C1 121.31(15) . .
C3 C2 C7 119.54(15) . .
C7 C2 C1 119.03(15) . .
C2 C3 C4 120.09(16) . .
C3 C4 C5 121.90(16) . .
C3 C4 C8 118.83(16) . .
C5 C4 C8 119.24(16) . .
C4 C5 C6 116.87(16) . .
C5 C6 C9 118.95(17) . .
C7 C6 C5 121.90(17) . .
C7 C6 C9 119.15(18) . .
C6 C7 C2 119.69(17) . .
F1 C8 F3 105.29(18) . .
F1 C8 C4 111.83(16) . .
F2 C8 F1 107.36(18) . .
F2 C8 F3 106.05(19) . .
F2 C8 C4 113.38(18) . .
F3 C8 C4 112.39(17) . .
F4 C9 F5 103.5(2) . .
F4 C9 C6 113.5(2) . .
F5 C9 C6 112.4(2) . .
F6 C9 F4 106.0(3) . .
F6 C9 F5 107.7(3) . .
F6 C9 C6 112.99(19) . .
C11 C10 Ir 128.81(14) . .
C11 C10 C15 116.43(16) . .
C15 C10 Ir 114.63(12) . .
C12 C11 C10 121.48(18) . .
C11 C12 C13 121.00(18) . .
C14 C13 C12 119.37(17) . .
C13 C14 C15 119.78(19) . .
C10 C15 C16 114.58(15) . .
C14 C15 C10 121.93(17) . .
C14 C15 C16 123.45(17) . .
N2 C16 C15 113.97(15) . .
N2 C16 C17 119.92(17) . .
C17 C16 C15 126.10(17) . .
C18 C17 C16 120.23(18) . .
C17 C18 C19 119.09(19) . .
C20 C19 C18 118.7(2) . .
N2 C20 C19 122.28(19) . .
C22 C21 Ir 128.72(14) . .
C22 C21 C26 117.02(17) . .
C26 C21 Ir 114.11(13) . .
C23 C22 C21 121.3(2) . .
C24 C23 C22 120.5(2) . .
C25 C24 C23 119.68(19) . .
C24 C25 C26 119.8(2) . .
C21 C26 C27 115.27(16) . .
C25 C26 C21 121.6(2) . .
C25 C26 C27 123.10(19) . .
N3 C27 C26 113.94(16) . .
N3 C27 C28 120.03(19) . .
C28 C27 C26 126.00(18) . .
C29 C28 C27 119.9(2) . .
C28 C29 C30 119.56(19) . .
C31 C30 C29 118.8(2) . .
N3 C31 C30 122.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir O 2.1442(12) .
Ir N1 2.1742(14) .
Ir N2 2.0324(15) .
Ir N3 2.0435(15) .
Ir C10 1.9999(16) .
Ir C21 2.0057(17) .
F1 C8 1.338(2) .
F2 C8 1.319(2) .
F3 C8 1.340(3) .
F4 C9 1.314(3) .
F5 C9 1.322(3) .
F6 C9 1.303(3) .
O C1 1.2806(19) .
N1 N1 1.440(3) 2
N1 C1 1.313(2) 2
N2 C16 1.365(2) .
N2 C20 1.345(2) .
N3 C27 1.361(2) .
N3 C31 1.347(3) .
C1 N1 1.313(2) 2
C1 C2 1.490(2) .
C2 C3 1.384(2) .
C2 C7 1.393(2) .
C3 C4 1.388(2) .
C4 C5 1.394(3) .
C4 C8 1.496(3) .
C5 C6 1.403(3) .
C6 C7 1.387(3) .
C6 C9 1.499(3) .
C10 C11 1.405(2) .
C10 C15 1.416(2) .
C11 C12 1.388(3) .
C12 C13 1.388(3) .
C13 C14 1.386(3) .
C14 C15 1.400(2) .
C15 C16 1.458(3) .
C16 C17 1.392(3) .
C17 C18 1.381(3) .
C18 C19 1.393(3) .
C19 C20 1.380(3) .
C21 C22 1.400(3) .
C21 C26 1.412(3) .
C22 C23 1.396(3) .
C23 C24 1.390(4) .
C24 C25 1.382(4) .
C25 C26 1.401(3) .
C26 C27 1.459(3) .
C27 C28 1.401(3) .
C28 C29 1.372(4) .
C29 C30 1.385(4) .
C30 C31 1.382(3) .
