#------------------------------------------------------------------------------
#$Date: 2019-11-24 13:37:25 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238030 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/91/4089192.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_4089192
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         'C58 H46 F8 Ir2 N10 O2'
_chemical_formula_sum            'C58 H46 F8 Ir2 N10 O2'
_chemical_formula_weight         1451.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-27
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.11.25 svn.r3098 for OlexSys, GUI svn.r4951)
;
_cell_angle_alpha                89.1907(18)
_cell_angle_beta                 79.7249(18)
_cell_angle_gamma                72.8004(18)
_cell_formula_units_Z            1
_cell_length_a                   9.6743(6)
_cell_length_b                   11.9790(8)
_cell_length_c                   12.1095(8)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    120
_cell_measurement_theta_max      34.96
_cell_measurement_theta_min      2.24
_cell_volume                     1317.98(15)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω-scan
_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  0.0560
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18770
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.241
_diffrn_source                   'I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.127
_exptl_absorpt_correction_T_max  0.7374
_exptl_absorpt_correction_T_min  0.5457
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.1262 before and 0.0910 after correction.
The Ratio of minimum to maximum transmission is 0.5673.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       trapetsoid
_exptl_crystal_F_000             706
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.104
_refine_diff_density_max         4.989
_refine_diff_density_min         -1.873
_refine_diff_density_rms         0.397
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         7578
_refine_ls_number_restraints     375
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0542
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6985
_reflns_number_total             7578
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00887_si_002.cif
_cod_data_source_block           14a
_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               4089192
_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   0.618
_shelx_estimated_absorpt_t_min   0.438
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C15(H15), C17(H17), C18(H18), C19(H19),
 C20(H20), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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'
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
Ir Ir 0.67897(2) 0.52900(2) 0.33483(2) 0.01463(9) Uani 1 1 d . U
F1 F 0.7379(5) 0.9477(3) 0.2971(4) 0.0455(10) Uani 1 1 d . U
F2 F 0.4751(4) 0.8599(3) 0.0391(3) 0.0337(8) Uani 1 1 d . U
F3 F 0.9657(5) 0.2733(3) -0.0271(3) 0.0364(8) Uani 1 1 d . U
F4 F 1.2346(4) 0.4885(4) 0.1146(3) 0.0406(9) Uani 1 1 d . U
O O 0.7407(4) 0.3791(4) 0.4286(3) 0.0195(8) Uani 1 1 d . U
N1 N 0.4889(4) 0.5471(4) 0.4617(3) 0.0145(7) Uani 1 1 d . U
N2 N 0.7631(5) 0.6204(4) 0.4285(4) 0.0199(8) Uani 1 1 d . U
N3 N 0.7686(5) 0.7265(4) 0.3912(4) 0.0222(8) Uani 1 1 d . U
N4 N 0.6144(5) 0.4308(4) 0.2326(4) 0.0208(9) Uani 1 1 d . U
N5 N 0.7212(5) 0.3720(4) 0.1460(4) 0.0220(8) Uani 1 1 d . U
C1 C 0.6403(5) 0.3747(4) 0.5136(4) 0.0150(8) Uani 1 1 d . U
C2 C 0.6850(5) 0.2744(4) 0.5872(4) 0.0177(8) Uani 1 1 d . U
C3 C 0.7589(6) 0.2839(4) 0.6728(4) 0.0223(10) Uani 1 1 d . U
H3 H 0.7691 0.3575 0.6913 0.027 Uiso 1 1 calc R .
C4 C 0.8184(6) 0.1864(5) 0.7320(5) 0.0225(10) Uani 1 1 d . U
H4 H 0.8690 0.1946 0.7903 0.027 Uiso 1 1 calc R .
C5 C 0.8056(6) 0.0779(4) 0.7080(4) 0.0201(9) Uani 1 1 d . U
C6 C 0.7285(6) 0.0708(4) 0.6224(5) 0.0234(10) Uani 1 1 d . U
H6 H 0.7167 -0.0025 0.6048 0.028 Uiso 1 1 calc R .
C7 C 0.6685(6) 0.1669(4) 0.5623(5) 0.0220(10) Uani 1 1 d . U
H7 H 0.6167 0.1592 0.5045 0.026 Uiso 1 1 calc R .
C8 C 0.8792(6) -0.0328(5) 0.7656(5) 0.0259(10) Uani 1 1 d . U
C9 C 0.9259(9) -0.0056(6) 0.8731(6) 0.0383(15) Uani 1 1 d . U
H9A H 1.0102 0.0251 0.8543 0.057 Uiso 1 1 calc GR .
H9B H 0.9537 -0.0772 0.9146 0.057 Uiso 1 1 calc GR .
H9C H 0.8439 0.0529 0.9196 0.057 Uiso 1 1 calc GR .
C10 C 0.7745(7) -0.1089(5) 0.7952(6) 0.0325(12) Uani 1 1 d . U
H10A H 0.6853 -0.0640 0.8463 0.049 Uiso 1 1 calc GR .
H10B H 0.8240 -0.1792 0.8319 0.049 Uiso 1 1 calc GR .
H10C H 0.7480 -0.1318 0.7264 0.049 Uiso 1 1 calc GR .
C11 C 1.0174(6) -0.1025(5) 0.6840(5) 0.0290(11) Uani 1 1 d . U
H11A H 0.9901 -0.1186 0.6131 0.043 Uiso 1 1 calc GR .
H11B H 1.0630 -0.1764 0.7169 0.043 Uiso 1 1 calc GR .
H11C H 1.0873 -0.0568 0.6698 0.043 Uiso 1 1 calc GR .
C12 C 0.6359(6) 0.6825(5) 0.2564(4) 0.0184(9) Uani 1 1 d . U
C13 C 0.6962(6) 0.7628(5) 0.2979(5) 0.0224(9) Uani 1 1 d . U
C14 C 0.6822(7) 0.8715(5) 0.2528(6) 0.0309(12) Uani 1 1 d . U
C15 C 0.6088(7) 0.9064(5) 0.1642(5) 0.0283(11) Uani 1 1 d . U
H15 H 0.5997 0.9805 0.1322 0.034 Uiso 1 1 calc R .
C16 C 0.5498(6) 0.8265(5) 0.1256(4) 0.0246(10) Uani 1 1 d . U
C17 C 0.5627(6) 0.7174(5) 0.1666(4) 0.0206(9) Uani 1 1 d . U
H17 H 0.5219 0.6656 0.1340 0.025 Uiso 1 1 calc R .
C18 C 0.8492(7) 0.7700(6) 0.4494(6) 0.0319(12) Uani 1 1 d . U
H18 H 0.8710 0.8421 0.4379 0.038 Uiso 1 1 calc R .
C19 C 0.8940(7) 0.6898(6) 0.5290(6) 0.0337(13) Uani 1 1 d . U
H19 H 0.9514 0.6957 0.5834 0.040 Uiso 1 1 calc R .
C20 C 0.8368(6) 0.5980(5) 0.5122(5) 0.0239(10) Uani 1 1 d . U
H20 H 0.8492 0.5296 0.5547 0.029 Uiso 1 1 calc R .
C21 C 0.8644(6) 0.4750(5) 0.2191(4) 0.0208(9) Uani 1 1 d . U
C22 C 0.8573(6) 0.3973(4) 0.1365(4) 0.0203(9) Uani 1 1 d . U
C23 C 0.9775(6) 0.3494(5) 0.0517(4) 0.0244(10) Uani 1 1 d . U
C24 C 1.1065(7) 0.3766(5) 0.0425(5) 0.0303(11) Uani 1 1 d . U
H24 H 1.1880 0.3437 -0.0159 0.036 Uiso 1 1 calc R .
C25 C 1.1113(6) 0.4544(6) 0.1232(5) 0.0275(11) Uani 1 1 d . U
C26 C 0.9956(6) 0.5038(5) 0.2104(4) 0.0236(10) Uani 1 1 d . U
H26 H 1.0054 0.5569 0.2638 0.028 Uiso 1 1 calc R .
C27 C 0.6701(7) 0.2988(5) 0.0927(5) 0.0336(13) Uani 1 1 d . U
H27 H 0.7232 0.2480 0.0298 0.040 Uiso 1 1 calc R .
C28 C 0.5294(8) 0.3101(6) 0.1443(7) 0.0398(15) Uani 1 1 d . U
H28 H 0.4649 0.2706 0.1243 0.048 Uiso 1 1 calc R .
C29 C 0.4997(6) 0.3924(5) 0.2336(5) 0.0278(11) Uani 1 1 d . U
H29 H 0.4105 0.4167 0.2866 0.033 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'
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'
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.0530
0.00 -1.00 0.00 0.0210
0.00 0.00 1.00 0.0850
0.00 1.00 -2.00 0.0230
0.00 -1.00 1.00 0.0580
0.00 0.00 -1.00 0.0210
-1.00 -1.00 1.00 0.0670
2.00 1.00 1.00 0.0600
2.00 0.00 1.00 0.0580
-1.00 -2.00 0.00 0.0470
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 76.75(15) . .
N2 Ir O 92.10(18) . .
N2 Ir N1 92.43(18) . .
N2 Ir N4 174.49(16) . .
N2 Ir C12 80.1(2) . .
N2 Ir C21 94.0(2) . .
N4 Ir O 87.15(18) . .
N4 Ir N1 92.71(18) . .
N4 Ir C12 100.5(2) . .
C12 Ir O 172.14(18) . .
C12 Ir N1 104.57(18) . .
C21 Ir O 92.51(18) . .
C21 Ir N1 167.66(19) . .
C21 Ir N4 80.5(2) . .
C21 Ir C12 86.9(2) . .
C1 O Ir 113.3(3) . .
N1 N1 Ir 111.9(4) 2_666 .
C1 N1 Ir 134.4(3) 2_666 .
C1 N1 N1 113.7(5) 2_666 2_666
N3 N2 Ir 116.3(4) . .
C20 N2 Ir 135.9(4) . .
C20 N2 N3 107.0(5) . .
N2 N3 C13 114.1(4) . .
C18 N3 N2 110.5(5) . .
C18 N3 C13 135.3(5) . .
N5 N4 Ir 115.1(4) . .
C29 N4 Ir 137.0(4) . .
C29 N4 N5 107.0(5) . .
N4 N5 C22 114.9(4) . .
C27 N5 N4 109.4(5) . .
C27 N5 C22 135.7(5) . .
O C1 N1 124.3(4) . 2_666
O C1 C2 114.7(4) . .
N1 C1 C2 121.0(4) 2_666 .
C3 C2 C1 120.0(4) . .
C3 C2 C7 119.3(5) . .
C7 C2 C1 120.2(4) . .
C2 C3 C4 120.4(5) . .
C5 C4 C3 121.6(5) . .
C4 C5 C6 117.0(5) . .
C4 C5 C8 122.9(5) . .
C6 C5 C8 120.1(5) . .
C7 C6 C5 122.4(5) . .
C2 C7 C6 119.3(5) . .
C5 C8 C10 111.0(4) . .
C5 C8 C11 107.8(5) . .
C9 C8 C5 112.4(5) . .
C9 C8 C10 108.1(5) . .
C9 C8 C11 108.1(5) . .
C11 C8 C10 109.3(5) . .
C13 C12 Ir 113.0(4) . .
C17 C12 Ir 130.3(4) . .
C17 C12 C13 116.6(5) . .
C12 C13 N3 115.9(5) . .
C14 C13 N3 122.5(5) . .
C14 C13 C12 121.6(5) . .
F1 C14 C13 119.9(5) . .
F1 C14 C15 118.2(5) . .
C13 C14 C15 121.9(5) . .
C16 C15 C14 115.4(5) . .
F2 C16 C15 116.3(5) . .
F2 C16 C17 118.9(5) . .
C17 C16 C15 124.7(5) . .
C16 C17 C12 119.8(5) . .
N3 C18 C19 107.0(6) . .
C18 C19 C20 105.3(5) . .
N2 C20 C19 110.1(5) . .
C22 C21 Ir 113.5(4) . .
C26 C21 Ir 129.5(4) . .
C26 C21 C22 117.0(5) . .
C21 C22 N5 115.6(4) . .
C23 C22 N5 123.5(5) . .
C23 C22 C21 120.9(5) . .
F3 C23 C22 118.8(5) . .
C24 C23 F3 118.5(5) . .
C24 C23 C22 122.6(6) . .
C23 C24 C25 115.9(5) . .
F4 C25 C24 118.1(5) . .
F4 C25 C26 117.9(6) . .
C24 C25 C26 124.0(6) . .
C25 C26 C21 119.6(6) . .
N5 C27 C28 108.3(5) . .
C27 C28 C29 105.4(6) . .
N4 C29 C28 109.8(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir O 2.102(4) .
Ir N1 2.134(4) .
Ir N2 2.009(5) .
Ir N4 2.014(5) .
Ir C12 2.023(5) .
Ir C21 2.011(5) .
F1 C14 1.349(7) .
F2 C16 1.366(6) .
F3 C23 1.371(7) .
F4 C25 1.357(7) .
O C1 1.295(6) .
N1 N1 1.441(8) 2_666
N1 C1 1.308(6) 2_666
N2 N3 1.356(7) .
N2 C20 1.321(7) .
N3 C13 1.430(7) .
N3 C18 1.350(7) .
N4 N5 1.367(6) .
N4 C29 1.319(7) .
N5 C22 1.420(7) .
N5 C27 1.348(8) .
C1 N1 1.308(6) 2_666
C1 C2 1.492(7) .
C2 C3 1.384(7) .
C2 C7 1.387(7) .
C3 C4 1.391(7) .
C4 C5 1.381(7) .
C5 C6 1.397(7) .
C5 C8 1.532(7) .
C6 C7 1.387(7) .
C8 C9 1.521(9) .
C8 C10 1.547(8) .
C8 C11 1.534(8) .
C12 C13 1.403(8) .
C12 C17 1.395(7) .
C13 C14 1.383(8) .
C14 C15 1.384(9) .
C15 C16 1.376(9) .
C16 C17 1.370(7) .
C18 C19 1.385(9) .
C19 C20 1.402(9) .
C21 C22 1.401(8) .
C21 C26 1.397(8) .
C22 C23 1.390(7) .
C23 C24 1.366(9) .
C24 C25 1.376(10) .
C25 C26 1.386(8) .
C27 C28 1.361(10) .
C28 C29 1.405(8) .
