#------------------------------------------------------------------------------
#$Date: 2015-09-06 01:02:34 +0300 (Sun, 06 Sep 2015) $
#$Revision: 154608 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/36/4343612.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_4343612
loop_
_publ_author_name
'Radwan, Yousf K.'
'Maity, Ayan'
'Teets, Thomas S.'
_publ_section_title
;
 Manipulating the Excited States of Cyclometalated Iridium Complexes with
 β-Ketoiminate and β-Diketiminate Ligands.
;
_journal_issue                   14
_journal_name_full               'Inorganic chemistry'
_journal_page_first              7122
_journal_page_last               7131
_journal_paper_doi               10.1021/acs.inorgchem.5b01401
_journal_volume                  54
_journal_year                    2015
_chemical_formula_sum            'C37 H28 Ir N3 O S2'
_chemical_formula_weight         786.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.194(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.925(4)
_cell_length_b                   9.708(2)
_cell_length_c                   18.743(4)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.37
_cell_measurement_theta_min      2.36
_cell_volume                     3071.4(12)
_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      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.921
_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  0.0151
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19604
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.423
_diffrn_reflns_theta_min         1.206
_exptl_absorpt_coefficient_mu    4.519
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.105
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         7826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0184
_refine_ls_R_factor_gt           0.0166
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0146P)²+2.8702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0372
_refine_ls_wR_factor_ref         0.0397
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7385
_reflns_number_total             7826
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic5b01401_si_001.cif
_cod_data_source_block           Complex5
_cod_depositor_comments
'Adding full bibliography for 4343610--4343613.cif.'
_cod_original_cell_volume        3071.5(12)
_cod_database_code               4343612
_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   0.344
_shelx_estimated_absorpt_t_max   0.465
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.67689(8) -0.04014(14) -0.11813(7) 0.0167(3) Uani 1 1 d . .
Ir1 Ir 0.72937(2) 0.11811(2) -0.05041(2) 0.01059(2) Uani 1 1 d . .
S1 S 0.52276(3) 0.08359(5) 0.08648(3) 0.01594(9) Uani 1 1 d . .
S2 S 0.99268(3) 0.16996(6) -0.05685(3) 0.02670(12) Uani 1 1 d . .
N1 N 0.62025(9) 0.14091(16) -0.00921(8) 0.0126(3) Uani 1 1 d . .
N2 N 0.84552(10) 0.09951(16) -0.07556(9) 0.0140(3) Uani 1 1 d . .
N3 N 0.71679(9) 0.25592(17) -0.14027(8) 0.0143(3) Uani 1 1 d . .
C1 C 0.64657(12) -0.0222(2) -0.18209(11) 0.0184(4) Uani 1 1 d . .
C2 C 0.61129(14) -0.1523(2) -0.21649(12) 0.0258(5) Uani 1 1 d . .
H2A H 0.6497 -0.2276 -0.2104 0.039 Uiso 1 1 calc R U
H2B H 0.5984 -0.1360 -0.2676 0.039 Uiso 1 1 calc R U
H2C H 0.5630 -0.1771 -0.1936 0.039 Uiso 1 1 calc R U
C3 C 0.64575(13) 0.0981(2) -0.22171(11) 0.0222(4) Uani 1 1 d . .
H3 H 0.6168 0.0945 -0.2670 0.027 Uiso 1 1 calc R U
C4 C 0.68252(12) 0.2269(2) -0.20365(10) 0.0191(4) Uani 1 1 d . .
C5 C 0.67955(16) 0.3343(2) -0.26241(12) 0.0300(5) Uani 1 1 d . .
H5A H 0.6759 0.4262 -0.2413 0.045 Uiso 1 1 calc R U
H5B H 0.6331 0.3179 -0.2957 0.045 Uiso 1 1 calc R U
H5C H 0.7277 0.3282 -0.2882 0.045 Uiso 1 1 calc R U
C10 C 0.61113(11) 0.06228(19) 0.04741(10) 0.0130(3) Uani 1 1 d . .
C11 C 0.55463(11) 0.22709(19) -0.02412(10) 0.0141(4) Uani 1 1 d . .
C12 C 0.54306(11) 0.3212(2) -0.08011(11) 0.0169(4) Uani 1 1 d . .
H12 H 0.5815 0.3319 -0.1142 0.020 Uiso 1 1 calc R U
C13 C 0.47397(13) 0.3986(2) -0.08487(11) 0.0203(4) Uani 1 1 d . .
H13 H 0.4662 0.4652 -0.1219 0.024 Uiso 1 1 calc R U
C14 C 0.41568(12) 0.3815(2) -0.03680(12) 0.0216(4) Uani 1 1 d . .
H14 H 0.3689 0.4358 -0.0418 0.026 Uiso 1 1 calc R U
C15 C 0.42516(12) 0.2861(2) 0.01818(11) 0.0199(4) Uani 1 1 d . .
H15 H 0.3853 0.2729 0.0507 0.024 Uiso 1 1 calc R U
C16 C 0.49528(11) 0.2104(2) 0.02401(10) 0.0153(4) Uani 1 1 d . .
C21 C 0.67452(11) -0.03022(19) 0.07152(10) 0.0128(3) Uani 1 1 d . .
C22 C 0.67206(12) -0.12114(19) 0.12926(10) 0.0166(4) Uani 1 1 d . .
H22 H 0.6271 -0.1240 0.1567 0.020 Uiso 1 1 calc R U
C23 C 0.73624(12) -0.2069(2) 0.14576(11) 0.0206(4) Uani 1 1 d . .
H23 H 0.7359 -0.2689 0.1850 0.025 Uiso 1 1 calc R U
C24 C 0.80108(12) -0.2015(2) 0.10449(11) 0.0207(4) Uani 1 1 d . .
H24 H 0.8446 -0.2616 0.1153 0.025 Uiso 1 1 calc R U
C25 C 0.80350(12) -0.10975(19) 0.04753(11) 0.0164(4) Uani 1 1 d . .
H25 H 0.8489 -0.1076 0.0206 0.020 Uiso 1 1 calc R U
C26 C 0.73997(11) -0.02050(19) 0.02927(10) 0.0123(3) Uani 1 1 d . .
C30 C 0.89508(11) 0.1802(2) -0.03647(11) 0.0174(4) Uani 1 1 d . .
C31 C 0.96671(12) 0.0469(2) -0.12214(12) 0.0209(4) Uani 1 1 d . .
C32 C 1.01583(13) -0.0241(2) -0.16597(13) 0.0267(5) Uani 1 1 d . .
H32 H 1.0713 -0.0076 -0.1633 0.032 Uiso 1 1 calc R U
C33 C 0.98131(14) -0.1192(2) -0.21346(12) 0.0257(5) Uani 1 1 d . .
H33 H 1.0136 -0.1696 -0.2436 0.031 Uiso 1 1 calc R U
C34 C 0.89975(13) -0.1422(2) -0.21776(11) 0.0226(4) Uani 1 1 d . .
H34 H 0.8774 -0.2072 -0.2513 0.027 Uiso 1 1 calc R U
C35 C 0.85061(12) -0.0719(2) -0.17409(11) 0.0187(4) Uani 1 1 d . .
H35 H 0.7951 -0.0882 -0.1774 0.022 Uiso 1 1 calc R U
C36 C 0.88452(11) 0.0228(2) -0.12531(10) 0.0149(4) Uani 1 1 d . .
C41 C 0.78115(11) 0.25165(19) 0.02027(10) 0.0138(3) Uani 1 1 d . .
C42 C 0.74725(12) 0.3275(2) 0.07418(11) 0.0172(4) Uani 1 1 d . .
H42 H 0.6917 0.3220 0.0784 0.021 Uiso 1 1 calc R U
C43 C 0.79302(14) 0.4103(2) 0.12140(12) 0.0235(4) Uani 1 1 d . .
H43 H 0.7683 0.4594 0.1576 0.028 Uiso 1 1 calc R U
C44 C 0.87438(14) 0.4226(3) 0.11664(13) 0.0294(5) Uani 1 1 d . .
H44 H 0.9049 0.4802 0.1490 0.035 Uiso 1 1 calc R U
C45 C 0.91044(13) 0.3502(2) 0.06428(13) 0.0271(5) Uani 1 1 d . .
H45 H 0.9658 0.3582 0.0600 0.033 Uiso 1 1 calc R U
C46 C 0.86405(11) 0.2650(2) 0.01775(11) 0.0179(4) Uani 1 1 d . .
C51 C 0.76192(12) 0.38112(19) -0.13111(10) 0.0160(4) Uani 1 1 d . .
C52 C 0.83587(13) 0.3922(2) -0.15874(12) 0.0218(4) Uani 1 1 d . .
H52 H 0.8541 0.3213 -0.1884 0.026 Uiso 1 1 calc R U
C53 C 0.88300(14) 0.5070(2) -0.14286(13) 0.0273(5) Uani 1 1 d . .
H53 H 0.9335 0.5141 -0.1615 0.033 Uiso 1 1 calc R U
C54 C 0.85666(14) 0.6110(2) -0.10001(14) 0.0268(5) Uani 1 1 d . .
H54 H 0.8894 0.6885 -0.0886 0.032 Uiso 1 1 calc R U
C55 C 0.78258(14) 0.6016(2) -0.07387(13) 0.0254(5) Uani 1 1 d . .
H55 H 0.7639 0.6739 -0.0454 0.030 Uiso 1 1 calc R U
C56 C 0.73540(12) 0.4871(2) -0.08912(11) 0.0195(4) Uani 1 1 d . .
H56 H 0.6847 0.4810 -0.0708 0.023 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'
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'
Ir Ir -1.4442 7.9887 '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
C1 O1 Ir1 125.23(13)
C26 Ir1 C41 86.05(7)
C26 Ir1 N2 94.38(7)
C41 Ir1 N2 80.22(7)
C26 Ir1 N1 80.07(7)
C41 Ir1 N1 92.48(7)
N2 Ir1 N1 171.17(6)
C26 Ir1 O1 88.32(6)
C41 Ir1 O1 174.30(6)
N2 Ir1 O1 99.35(6)
N1 Ir1 O1 87.42(6)
C26 Ir1 N3 176.42(7)
C41 Ir1 N3 97.38(7)
N2 Ir1 N3 85.23(6)
N1 Ir1 N3 100.73(6)
O1 Ir1 N3 88.23(6)
C10 S1 C16 89.81(9)
C30 S2 C31 89.92(10)
C10 N1 C11 111.48(16)
C10 N1 Ir1 113.42(12)
C11 N1 Ir1 134.95(13)
C30 N2 C36 111.87(16)
C30 N2 Ir1 113.35(13)
C36 N2 Ir1 134.77(13)
C4 N3 C51 118.97(17)
C4 N3 Ir1 125.94(14)
C51 N3 Ir1 114.26(12)
O1 C1 C3 127.21(19)
O1 C1 C2 113.71(19)
C3 C1 C2 119.04(19)
C1 C3 C4 128.72(19)
N3 C4 C3 123.97(18)
N3 C4 C5 119.92(19)
C3 C4 C5 116.11(18)
N1 C10 C21 118.72(17)
N1 C10 S1 115.23(14)
C21 C10 S1 126.04(15)
C12 C11 N1 127.33(18)
C12 C11 C16 119.36(17)
N1 C11 C16 113.30(17)
C13 C12 C11 118.35(19)
C12 C13 C14 121.78(19)
C15 C14 C13 120.76(19)
C14 C15 C16 117.54(19)
C15 C16 C11 122.18(18)
C15 C16 S1 127.64(16)
C11 C16 S1 110.17(14)
C22 C21 C26 123.03(17)
C22 C21 C10 124.75(17)
C26 C21 C10 112.22(16)
C23 C22 C21 118.98(18)
C22 C23 C24 119.45(19)
C23 C24 C25 121.29(19)
C24 C25 C26 121.10(19)
C25 C26 C21 116.15(17)
C25 C26 Ir1 128.32(14)
C21 C26 Ir1 115.53(13)
N2 C30 C46 118.65(17)
N2 C30 S2 114.85(15)
C46 C30 S2 126.50(15)
C32 C31 C36 121.6(2)
C32 C31 S2 128.47(17)
C36 C31 S2 109.95(15)
C33 C32 C31 117.9(2)
C32 C33 C34 120.9(2)
C35 C34 C33 121.4(2)
C34 C35 C36 118.45(19)
C35 C36 N2 126.81(18)
C35 C36 C31 119.78(18)
N2 C36 C31 113.41(17)
C42 C41 C46 115.73(17)
C42 C41 Ir1 129.11(15)
C46 C41 Ir1 115.07(14)
C43 C42 C41 121.55(19)
C42 C43 C44 121.1(2)
C45 C44 C43 119.4(2)
C44 C45 C46 119.0(2)
C45 C46 C41 123.11(19)
C45 C46 C30 124.18(19)
C41 C46 C30 112.70(17)
C56 C51 C52 119.31(19)
C56 C51 N3 120.16(18)
C52 C51 N3 120.27(18)
C53 C52 C51 120.0(2)
C54 C53 C52 120.3(2)
C55 C54 C53 119.8(2)
C54 C55 C56 120.2(2)
C55 C56 C51 120.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.281(2)
O1 Ir1 2.1437(14)
Ir1 C26 2.0084(18)
Ir1 C41 2.0085(19)
Ir1 N2 2.0627(17)
Ir1 N1 2.0651(16)
Ir1 N3 2.1494(16)
S1 C10 1.7251(19)
S1 C16 1.739(2)
S2 C30 1.725(2)
S2 C31 1.743(2)
N1 C10 1.325(2)
N1 C11 1.402(2)
N2 C30 1.328(3)
N2 C36 1.396(2)
N3 C4 1.314(2)
N3 C51 1.439(2)
C1 C3 1.384(3)
C1 C2 1.520(3)
C3 C4 1.426(3)
C4 C5 1.515(3)
C10 C21 1.446(3)
C11 C12 1.394(3)
C11 C16 1.408(3)
C12 C13 1.388(3)
C13 C14 1.394(3)
C14 C15 1.386(3)
C15 C16 1.394(3)
C21 C22 1.400(3)
C21 C26 1.411(3)
C22 C23 1.386(3)
C23 C24 1.389(3)
C24 C25 1.394(3)
C25 C26 1.404(3)
C30 C46 1.437(3)
C31 C32 1.393(3)
C31 C36 1.408(3)
C32 C33 1.382(3)
C33 C34 1.395(3)
C34 C35 1.388(3)
C35 C36 1.391(3)
C41 C42 1.406(3)
C41 C46 1.413(3)
C42 C43 1.389(3)
C43 C44 1.392(3)
C44 C45 1.385(3)
C45 C46 1.400(3)
C51 C56 1.389(3)
C51 C52 1.393(3)
C52 C53 1.390(3)
C53 C54 1.384(3)
C54 C55 1.382(3)
C55 C56 1.387(3)
