#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/85/4078567.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_4078567
loop_
_publ_author_name
'Lin, Cheng-Huei'
'Chiu, Yuan-Chieh'
'Chi, Yun'
'Tao, Yu-Tai'
'Liao, Liang-Sheng'
'Tseng, Meu-Rurng'
'Lee, Gene-Hsiang'
_publ_section_title
;
 Mechanistic Investigation of Improved Syntheses of Iridium(III)-Based
 OLED Phosphors
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              4349
_journal_paper_doi               10.1021/om300325y
_journal_volume                  31
_journal_year                    2012
_chemical_formula_sum            'C27.5 H34.5 Cl3 Ir O1.5 P S2'
_chemical_formula_weight         782.69
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.0332(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1972(7)
_cell_length_b                   10.2905(5)
_cell_length_c                   21.7022(11)
_cell_measurement_reflns_used    6966
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.33
_cell_volume                     2935.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20309
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    5.040
_exptl_absorpt_correction_T_max  0.7867
_exptl_absorpt_correction_T_min  0.2504
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1546
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.475
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         6741
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0272P)²+1.2064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0742
_reflns_number_gt                5593
_reflns_number_total             6741
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300325y_si_001.cif
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_original_formula_sum        'C27.50 H34.50 Cl3 Ir O1.50 P S2'
_cod_database_code               4078567
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir Ir 0.759994(9) -0.004468(11) -0.226026(6) 0.01516(5) Uani 1 1 d . . .
Cl1 Cl 0.94076(6) -0.01063(8) -0.21882(4) 0.02151(18) Uani 1 1 d . . .
Cl2 Cl 0.58078(7) -0.00633(7) -0.23965(4) 0.02172(18) Uani 1 1 d . . .
Cl3 Cl 0.76247(6) -0.09747(8) -0.32817(4) 0.02307(18) Uani 1 1 d . . .
S1 S 0.75408(6) 0.20457(8) -0.27050(4) 0.02076(19) Uani 1 1 d . . .
S2 S 0.75451(7) -0.21582(8) -0.18474(4) 0.02348(19) Uani 1 1 d . . .
P1 P 0.76111(6) 0.08652(8) -0.12944(4) 0.01610(18) Uani 1 1 d . . .
C1 C 0.8563(3) 0.2217(4) -0.32179(17) 0.0285(8) Uani 1 1 d . . .
H1A H 0.8942 0.3035 -0.3128 0.034 Uiso 1 1 calc R . .
H1B H 0.9044 0.1480 -0.3160 0.034 Uiso 1 1 calc R . .
C2 C 0.8059(3) 0.2232(5) -0.38790(19) 0.0440(11) Uani 1 1 d . . .
H2A H 0.8461 0.2768 -0.4148 0.053 Uiso 1 1 calc R . .
H2B H 0.8011 0.1339 -0.4049 0.053 Uiso 1 1 calc R . .
C3 C 0.7017(3) 0.2799(5) -0.3850(2) 0.0484(12) Uani 1 1 d . . .
H3A H 0.6605 0.2672 -0.4250 0.058 Uiso 1 1 calc R . .
H3B H 0.7064 0.3742 -0.3763 0.058 Uiso 1 1 calc R . .
C4 C 0.6533(3) 0.2103(4) -0.33376(18) 0.0315(9) Uani 1 1 d . . .
H4A H 0.6316 0.1216 -0.3468 0.038 Uiso 1 1 calc R . .
H4B H 0.5936 0.2589 -0.3214 0.038 Uiso 1 1 calc R . .
C5 C 0.6487(3) -0.3063(3) -0.2229(2) 0.0342(10) Uani 1 1 d . . .
H5A H 0.5912 -0.3110 -0.1966 0.041 Uiso 1 1 calc R . .
H5B H 0.6248 -0.2660 -0.2630 0.041 Uiso 1 1 calc R . .
C6 C 0.6936(3) -0.4410(4) -0.2324(3) 0.0456(12) Uani 1 1 d . . .
H6A H 0.7015 -0.4890 -0.1927 0.055 Uiso 1 1 calc R . .
H6B H 0.6485 -0.4917 -0.2623 0.055 Uiso 1 1 calc R . .
C7 C 0.7938(3) -0.4205(4) -0.2564(2) 0.0421(11) Uani 1 1 d . . .
H7A H 0.7847 -0.3916 -0.3001 0.051 Uiso 1 1 calc R . .
H7B H 0.8330 -0.5027 -0.2545 0.051 Uiso 1 1 calc R . .
C8 C 0.8507(3) -0.3171(3) -0.2168(2) 0.0336(10) Uani 1 1 d . . .
H8A H 0.8936 -0.2640 -0.2423 0.040 Uiso 1 1 calc R . .
H8B H 0.8950 -0.3583 -0.1831 0.040 Uiso 1 1 calc R . .
C9 C 0.8141(3) -0.0113(3) -0.06335(17) 0.0197(7) Uani 1 1 d . . .
C10 C 0.7784(3) 0.0033(3) -0.00531(19) 0.0269(9) Uani 1 1 d . . .
H10 H 0.7239 0.0614 0.0001 0.032 Uiso 1 1 calc R . .
C11 C 0.8218(3) -0.0664(4) 0.04438(18) 0.0355(10) Uani 1 1 d . . .
H11 H 0.7964 -0.0568 0.0837 0.043 Uiso 1 1 calc R . .
C12 C 0.9014(3) -0.1496(4) 0.0377(2) 0.0388(10) Uani 1 1 d . . .
H12 H 0.9299 -0.1984 0.0721 0.047 Uiso 1 1 calc R . .
C13 C 0.9396(3) -0.1623(4) -0.01894(19) 0.0332(9) Uani 1 1 d . . .
H13 H 0.9958 -0.2183 -0.0233 0.040 Uiso 1 1 calc R . .
C14 C 0.8965(3) -0.0935(3) -0.06974(17) 0.0258(8) Uani 1 1 d . . .
H14 H 0.9232 -0.1024 -0.1088 0.031 Uiso 1 1 calc R . .
C15 C 0.8308(2) 0.2397(3) -0.11467(16) 0.0187(7) Uani 1 1 d . . .
C16 C 0.9075(2) 0.2806(3) -0.15070(16) 0.0210(7) Uani 1 1 d . . .
H16 H 0.9222 0.2314 -0.1859 0.025 Uiso 1 1 calc R . .
C17 C 0.9625(3) 0.3929(3) -0.13517(18) 0.0285(8) Uani 1 1 d . . .
H17 H 1.0140 0.4209 -0.1601 0.034 Uiso 1 1 calc R . .
C18 C 0.9427(3) 0.4640(4) -0.0837(2) 0.0346(10) Uani 1 1 d . . .
H18 H 0.9811 0.5400 -0.0730 0.041 Uiso 1 1 calc R . .
C19 C 0.8673(3) 0.4250(4) -0.04807(19) 0.0361(10) Uani 1 1 d . . .
H19 H 0.8529 0.4751 -0.0131 0.043 Uiso 1 1 calc R . .
C20 C 0.8120(3) 0.3126(3) -0.06277(17) 0.0267(8) Uani 1 1 d . . .
H20 H 0.7610 0.2853 -0.0373 0.032 Uiso 1 1 calc R . .
C21 C 0.6333(2) 0.1278(3) -0.11176(15) 0.0190(7) Uani 1 1 d . . .
C22 C 0.5706(3) 0.0369(4) -0.08710(18) 0.0258(8) Uani 1 1 d . . .
H22 H 0.5966 -0.0464 -0.0755 0.031 Uiso 1 1 calc R . .
C23 C 0.4706(3) 0.0668(5) -0.07936(18) 0.0351(10) Uani 1 1 d . . .
H23 H 0.4289 0.0051 -0.0611 0.042 Uiso 1 1 calc R . .
C24 C 0.4306(3) 0.1868(4) -0.09822(19) 0.0371(10) Uani 1 1 d . . .
H24 H 0.3618 0.2071 -0.0928 0.045 Uiso 1 1 calc R . .
C25 C 0.4909(3) 0.2757(4) -0.12466(18) 0.0341(9) Uani 1 1 d . . .
H25 H 0.4631 0.3567 -0.1387 0.041 Uiso 1 1 calc R . .
C26 C 0.5918(3) 0.2480(4) -0.13103(17) 0.0251(8) Uani 1 1 d . . .
H26 H 0.6334 0.3109 -0.1486 0.030 Uiso 1 1 calc R . .
O1 O 0.5015(7) 0.6795(9) -0.0517(5) 0.096(3) Uiso 0.50 1 d P A 1
O2 O 0.5276(6) 0.5059(8) 0.0086(4) 0.057(2) Uiso 0.50 1 d PD . 1
C27 C 0.5571(10) 0.6059(12) -0.0234(6) 0.065(3) Uiso 0.50 1 d PD . 1
C28 C 0.6704(8) 0.6257(12) -0.0204(6) 0.067(3) Uiso 0.50 1 d P B 1
H28A H 0.7001 0.5630 -0.0476 0.101 Uiso 0.50 1 calc PR B 1
H28B H 0.6999 0.6128 0.0222 0.101 Uiso 0.50 1 calc PR B 1
H28C H 0.6850 0.7142 -0.0338 0.101 Uiso 0.50 1 calc PR B 1
O3 O 0.5797(11) 0.5130(12) -0.0074(7) 0.120(5) Uiso 0.50 1 d PD C 2
H3 H 0.6313 0.4648 -0.0036 0.180 Uiso 0.50 1 calc PR C 2
C29 C 0.5977(11) 0.6225(13) -0.0505(6) 0.081(4) Uiso 0.50 1 d PD C 2
H29A H 0.5664 0.7020 -0.0361 0.121 Uiso 0.50 1 calc PR C 2
H29B H 0.5675 0.6012 -0.0922 0.121 Uiso 0.50 1 calc PR C 2
H29C H 0.6710 0.6361 -0.0516 0.121 Uiso 0.50 1 calc PR C 2
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'
P P 0.1023 0.0942 '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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
P1 Ir S2 91.56(3) . .
P1 Ir S1 89.94(3) . .
S2 Ir S1 176.07(3) . .
P1 Ir Cl2 92.51(3) . .
S2 Ir Cl2 88.64(3) . .
S1 Ir Cl2 87.66(3) . .
P1 Ir Cl1 91.42(3) . .
S2 Ir Cl1 90.83(3) . .
S1 Ir Cl1 92.77(3) . .
Cl2 Ir Cl1 176.04(3) . .
P1 Ir Cl3 178.63(3) . .
S2 Ir Cl3 89.23(3) . .
S1 Ir Cl3 89.34(3) . .
Cl2 Ir Cl3 88.62(3) . .
Cl1 Ir Cl3 87.45(3) . .
C4 S1 C1 93.82(18) . .
C4 S1 Ir 109.46(13) . .
C1 S1 Ir 109.69(12) . .
C5 S2 C8 93.78(18) . .
C5 S2 Ir 110.34(14) . .
C8 S2 Ir 109.67(13) . .
C21 P1 C15 102.87(15) . .
C21 P1 C9 105.10(16) . .
C15 P1 C9 100.54(15) . .
C21 P1 Ir 110.95(11) . .
C15 P1 Ir 118.17(12) . .
C9 P1 Ir 117.42(12) . .
C2 C1 S1 106.8(3) . .
C3 C2 C1 106.9(3) . .
C2 C3 C4 107.1(3) . .
C3 C4 S1 104.0(3) . .
C6 C5 S2 103.5(3) . .
C7 C6 C5 106.7(3) . .
C6 C7 C8 108.2(4) . .
C7 C8 S2 106.8(3) . .
C10 C9 C14 119.0(3) . .
C10 C9 P1 120.7(3) . .
C14 C9 P1 120.1(3) . .
C11 C10 C9 120.1(4) . .
C12 C11 C10 120.8(4) . .
C11 C12 C13 119.9(4) . .
C12 C13 C14 120.2(4) . .
C13 C14 C9 119.9(4) . .
C20 C15 C16 118.7(3) . .
C20 C15 P1 118.7(3) . .
C16 C15 P1 122.4(3) . .
C17 C16 C15 120.2(3) . .
C18 C17 C16 120.3(4) . .
C19 C18 C17 120.0(4) . .
C18 C19 C20 120.4(4) . .
C19 C20 C15 120.4(4) . .
C22 C21 C26 118.6(3) . .
C22 C21 P1 121.4(3) . .
C26 C21 P1 119.4(3) . .
C23 C22 C21 120.4(4) . .
C22 C23 C24 120.3(4) . .
C25 C24 C23 119.8(4) . .
C24 C25 C26 120.3(4) . .
C25 C26 C21 120.5(4) . .
O2 O2 C27 99.8(15) 3_665 .
O2 O2 C27 51.8(11) 3_665 3_665
C27 O2 C27 151.6(6) . 3_665
O1 C27 O2 125.0(12) . .
O1 C27 C28 120.1(12) . .
O2 C27 C28 114.9(11) . .
O1 C27 O2 98.5(10) . 3_665
O2 C27 O2 28.4(6) . 3_665
C28 C27 O2 140.5(10) . 3_665
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir P1 2.2946(9) .
Ir S2 2.3557(9) .
Ir S1 2.3562(9) .
Ir Cl2 2.3577(9) .
Ir Cl1 2.3779(9) .
Ir Cl3 2.4174(8) .
S1 C4 1.827(4) .
S1 C1 1.831(4) .
S2 C5 1.817(4) .
S2 C8 1.827(4) .
P1 C21 1.812(3) .
P1 C15 1.839(3) .
P1 C9 1.840(3) .
C1 C2 1.528(5) .
C2 C3 1.501(6) .
C3 C4 1.511(6) .
C5 C6 1.528(5) .
C6 C7 1.479(6) .
C7 C8 1.523(5) .
C9 C10 1.391(6) .
C9 C14 1.394(5) .
C10 C11 1.377(5) .
C11 C12 1.372(6) .
C12 C13 1.375(6) .
C13 C14 1.390(5) .
C15 C20 1.394(5) .
C15 C16 1.397(5) .
C16 C17 1.391(5) .
C17 C18 1.379(6) .
C18 C19 1.373(6) .
C19 C20 1.390(5) .
C21 C22 1.387(5) .
C21 C26 1.402(5) .
C22 C23 1.379(5) .
C23 C24 1.391(6) .
C24 C25 1.370(6) .
C25 C26 1.381(5) .
O1 C27 1.188(14) .
O2 O2 0.798(14) 3_665
O2 C27 1.319(13) .
O2 C27 1.654(16) 3_665
C27 C28 1.506(16) .
C27 O2 1.654(16) 3_665
O3 C29 1.497(14) .
