#------------------------------------------------------------------------------
#$Date: 2016-03-25 17:01:41 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180000 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/94/7029420.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_7029420
loop_
_publ_author_name
'Frey, Julien'
'Curchod, Basile F. E.'
'Scopelliti, Rosario'
'Tavernelli, Ivano'
'Rothlisberger, Ursula'
'Nazeeruddin, Mohammad K.'
'Baranoff, Etienne'
_publ_section_title
;
 Structure-property relationships based on Hammett constants in
 cyclometalated iridium(iii) complexes: their application to the design of
 a fluorine-free FIrPic-like emitter.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5667
_journal_page_last               5679
_journal_paper_doi               10.1039/c3dt52739e
_journal_volume                  43
_journal_year                    2014
_chemical_formula_moiety         'C29 H29 Ir N4 O4'
_chemical_formula_sum            'C29 H29 Ir N4 O4'
_chemical_formula_weight         689.76
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-07-30 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.716(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1180(13)
_cell_length_b                   22.472(3)
_cell_length_c                   12.1117(14)
_cell_measurement_reflns_used    207
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      3
_cell_volume                     3025.8(6)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs, 1990-2000)'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'phi and 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    0.0242
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34322
_diffrn_reflns_theta_full        30.70
_diffrn_reflns_theta_max         30.70
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    4.450
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008, Bruker AXS, 2008'
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_platon_squeeze_details          ' '
_refine_diff_density_max         1.388
_refine_diff_density_min         -1.079
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         4681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0254
_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)+(0.0140P)²+9.1879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0537
_refine_ls_wR_factor_ref         0.0560
_reflns_number_gt                4263
_reflns_number_total             4681
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt52739e.txt
_cod_data_source_block           eb370
_cod_original_cell_volume        3025.9(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7029420
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ir1 Ir 0.0000 0.252852(6) 0.2500 0.01853(4) Uani 1 2 d S
O1 O 0.32062(18) 0.10068(8) 0.07717(15) 0.0257(4) Uani 1 1 d .
O2 O 0.13384(18) 0.32162(8) 0.23342(15) 0.0270(4) Uani 1 1 d .
N1 N 0.03844(19) 0.24739(8) 0.41498(16) 0.0189(4) Uani 1 1 d .
N2 N 0.2957(2) 0.09715(10) 0.26743(18) 0.0231(4) Uani 1 1 d .
C1 C -0.0100(2) 0.28396(11) 0.49139(19) 0.0225(5) Uani 1 1 d .
H1 H -0.0666 0.3131 0.4679 0.027 Uiso 1 1 calc R
C2 C 0.0199(3) 0.28042(12) 0.6025(2) 0.0244(5) Uani 1 1 d .
H2 H -0.0153 0.3067 0.6543 0.029 Uiso 1 1 calc R
C3 C 0.1025(3) 0.23751(12) 0.6367(2) 0.0264(5) Uani 1 1 d .
H3 H 0.1257 0.2345 0.7123 0.032 Uiso 1 1 calc R
C4 C 0.1505(2) 0.19924(12) 0.55941(19) 0.0239(5) Uani 1 1 d .
H4 H 0.2064 0.1696 0.5825 0.029 Uiso 1 1 calc R
C5 C 0.1177(2) 0.20345(11) 0.44679(19) 0.0194(4) Uani 1 1 d .
C6 C 0.1643(2) 0.16868(11) 0.35352(19) 0.0198(4) Uani 1 1 d .
C7 C 0.2439(2) 0.12042(11) 0.3594(2) 0.0222(5) Uani 1 1 d .
C8 C 0.2652(2) 0.12093(11) 0.1702(2) 0.0224(5) Uani 1 1 d .
C9 C 0.1785(2) 0.16515(11) 0.1541(2) 0.0222(5) Uani 1 1 d .
H9 H 0.1564 0.1780 0.0819 0.027 Uiso 1 1 calc R
C10 C 0.1250(2) 0.19009(10) 0.24741(19) 0.0194(4) Uani 1 1 d .
C11 C 0.2778(3) 0.08733(13) 0.4641(2) 0.0296(6) Uani 1 1 d .
H11A H 0.3079 0.0477 0.4452 0.044 Uiso 1 1 calc R
H11B H 0.2069 0.0835 0.5108 0.044 Uiso 1 1 calc R
H11C H 0.3406 0.1094 0.5041 0.044 Uiso 1 1 calc R
C12 C 0.4073(3) 0.05388(12) 0.0907(2) 0.0282(5) Uani 1 1 d .
H12A H 0.4705 0.0667 0.1426 0.042 Uiso 1 1 calc R
H12B H 0.4431 0.0447 0.0192 0.042 Uiso 1 1 calc R
H12C H 0.3675 0.0183 0.1196 0.042 Uiso 1 1 calc R
C13 C 0.1124(3) 0.37679(12) 0.2327(2) 0.0311(6) Uani 1 1 d .
C14 C 0.0000 0.40447(18) 0.2500 0.0344(9) Uani 1 2 d S
H14 H 0.0000 0.4467 0.2500 0.041 Uiso 1 2 calc SR
C15 C 0.2201(3) 0.41575(14) 0.2095(3) 0.0411(8) Uani 1 1 d .
H15A H 0.2846 0.4068 0.2629 0.062 Uiso 1 1 calc R
H15B H 0.1971 0.4577 0.2162 0.062 Uiso 1 1 calc R
H15C H 0.2484 0.4080 0.1346 0.062 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C10 Ir1 C10 89.17(14) . 2
C10 Ir1 N1 94.59(9) . 2
C10 Ir1 N1 80.47(9) 2 2
C10 Ir1 N1 80.47(9) . .
C10 Ir1 N1 94.59(9) 2 .
N1 Ir1 N1 173.10(11) 2 .
C10 Ir1 O2 175.52(8) . 2
C10 Ir1 O2 91.37(9) 2 2
N1 Ir1 O2 89.88(7) 2 2
N1 Ir1 O2 95.06(8) . 2
C10 Ir1 O2 91.37(9) . .
C10 Ir1 O2 175.52(8) 2 .
N1 Ir1 O2 95.06(8) 2 .
N1 Ir1 O2 89.89(7) . .
O2 Ir1 O2 88.44(11) 2 .
C8 O1 C12 117.3(2) . .
C13 O2 Ir1 125.0(2) . .
C1 N1 C5 120.2(2) . .
C1 N1 Ir1 123.50(16) . .
C5 N1 Ir1 116.29(15) . .
C8 N2 C7 117.6(2) . .
N1 C1 C2 122.4(2) . .
N1 C1 H1 118.8 . .
C2 C1 H1 118.8 . .
C1 C2 C3 118.6(2) . .
C1 C2 H2 120.7 . .
C3 C2 H2 120.7 . .
C4 C3 C2 119.2(2) . .
C4 C3 H3 120.4 . .
C2 C3 H3 120.4 . .
C3 C4 C5 121.1(2) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
N1 C5 C4 118.4(2) . .
N1 C5 C6 113.3(2) . .
C4 C5 C6 128.1(2) . .
C7 C6 C10 119.4(2) . .
C7 C6 C5 126.8(2) . .
C10 C6 C5 113.8(2) . .
N2 C7 C6 121.8(2) . .
N2 C7 C11 113.1(2) . .
C6 C7 C11 125.0(2) . .
N2 C8 O1 118.8(2) . .
N2 C8 C9 125.1(2) . .
O1 C8 C9 116.0(2) . .
C8 C9 C10 118.1(2) . .
C8 C9 H9 120.9 . .
C10 C9 H9 120.9 . .
C9 C10 C6 117.4(2) . .
C9 C10 Ir1 127.07(18) . .
C6 C10 Ir1 115.48(17) . .
C7 C11 H11A 109.5 . .
C7 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C7 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
O1 C12 H12A 109.5 . .
O1 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
O1 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O2 C13 C14 126.7(3) . .
O2 C13 C15 114.8(3) . .
C14 C13 C15 118.4(3) . .
C13 C14 C13 127.8(4) . 2
C13 C14 H14 116.1 . .
C13 C14 H14 116.1 2 .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 C10 1.980(2) .
Ir1 C10 1.981(2) 2
Ir1 N1 2.0418(19) 2
Ir1 N1 2.0419(19) .
Ir1 O2 2.1565(19) 2
Ir1 O2 2.1565(19) .
O1 C8 1.368(3) .
O1 C12 1.434(3) .
O2 C13 1.263(3) .
N1 C1 1.355(3) .
N1 C5 1.375(3) .
N2 C8 1.334(3) .
N2 C7 1.365(3) .
C1 C2 1.385(3) .
C1 H1 0.9500 .
C2 C3 1.392(4) .
C2 H2 0.9500 .
C3 C4 1.383(4) .
C3 H3 0.9500 .
C4 C5 1.411(3) .
C4 H4 0.9500 .
C5 C6 1.473(3) .
C6 C7 1.402(3) .
C6 C10 1.435(3) .
C7 C11 1.513(3) .
C8 C9 1.397(4) .
C9 C10 1.401(3) .
C9 H9 0.9500 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.414(4) .
C13 C15 1.513(4) .
C14 C13 1.414(4) 2
C14 H14 0.9500 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C10 Ir1 O2 C13 -177.8(2) . .
N1 Ir1 O2 C13 87.5(2) 2 .
N1 Ir1 O2 C13 -97.3(2) . .
O2 Ir1 O2 C13 -2.23(16) 2 .
C10 Ir1 N1 C1 175.3(2) . .
C10 Ir1 N1 C1 -96.4(2) 2 .
O2 Ir1 N1 C1 -4.6(2) 2 .
O2 Ir1 N1 C1 83.8(2) . .
C10 Ir1 N1 C5 -5.08(17) . .
C10 Ir1 N1 C5 83.31(18) 2 .
O2 Ir1 N1 C5 175.09(17) 2 .
O2 Ir1 N1 C5 -96.48(18) . .
C5 N1 C1 C2 2.1(4) . .
Ir1 N1 C1 C2 -178.2(2) . .
N1 C1 C2 C3 -0.2(4) . .
C1 C2 C3 C4 -1.1(4) . .
C2 C3 C4 C5 0.6(4) . .
C1 N1 C5 C4 -2.6(3) . .
Ir1 N1 C5 C4 177.74(18) . .
C1 N1 C5 C6 -178.5(2) . .
Ir1 N1 C5 C6 1.8(3) . .
C3 C4 C5 N1 1.3(4) . .
C3 C4 C5 C6 176.6(3) . .
N1 C5 C6 C7 -178.5(2) . .
C4 C5 C6 C7 6.0(4) . .
N1 C5 C6 C10 4.3(3) . .
C4 C5 C6 C10 -171.2(2) . .
C8 N2 C7 C6 -1.8(4) . .
C8 N2 C7 C11 175.8(2) . .
C10 C6 C7 N2 7.2(4) . .
C5 C6 C7 N2 -169.8(2) . .
C5 C6 C7 C11 12.8(4) . .
C7 N2 C8 O1 176.5(2) . .
C7 N2 C8 C9 -4.5(4) . .
C12 O1 C8 N2 1.1(3) . .
C12 O1 C8 C9 -178.0(2) . .
N2 C8 C9 C10 5.1(4) . .
O1 C8 C9 C10 -175.9(2) . .
C8 C9 C10 C6 0.6(4) . .
C8 C9 C10 Ir1 -179.80(19) . .
C7 C6 C10 C9 -6.4(4) . .
C5 C6 C10 C9 171.0(2) . .
C7 C6 C10 Ir1 173.98(19) . .
C5 C6 C10 Ir1 -8.6(3) . .
C10 Ir1 C10 C9 93.0(2) 2 .
N1 Ir1 C10 C9 12.6(2) 2 .
N1 Ir1 C10 C9 -172.2(2) . .
O2 Ir1 C10 C9 -82.6(2) . .
C10 Ir1 C10 C6 -87.41(19) 2 .
N1 Ir1 C10 C6 -167.78(18) 2 .
N1 Ir1 C10 C6 7.38(18) . .
O2 Ir1 C10 C6 97.04(19) . .
Ir1 O2 C13 C14 4.7(3) . .
Ir1 O2 C13 C15 -174.65(17) . .
O2 C13 C14 C13 -2.7(2) . 2
C15 C13 C14 C13 176.6(3) . 2
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.008 276 45 ' '
2 0.500 0.500 0.368 276 45 ' '
