#------------------------------------------------------------------------------
#$Date: 2017-04-21 03:19:07 +0300 (Fri, 21 Apr 2017) $
#$Revision: 195637 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/72/4087258.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_4087258
loop_
_publ_author_name
'Benjamin, Helen'
'Liang, Jie'
'Liu, Yu'
'Geng, Yun'
'Liu, Xingman'
'Zhu, Dongxia'
'Batsanov, Andrei S.'
'Bryce, Martin R.'
_publ_section_title
;
 Color Tuning of Efficient Electroluminescence in the Blue and Green
 Regions Using Heteroleptic Iridium Complexes with 2-Phenoxyoxazole
 Ancillary Ligands
;
_journal_name_full               Organometallics
_journal_paper_doi               10.1021/acs.organomet.7b00161
_journal_year                    2017
_chemical_formula_moiety         'C31 H20 F4 Ir N3 O2, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C31.5 H21 Cl F4 Ir N3 O2'
_chemical_formula_weight         777.16
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.302(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.3108(14)
_cell_length_b                   15.9429(14)
_cell_length_c                   14.7716(10)
_cell_measurement_reflns_used    7110
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.075
_cell_measurement_theta_min      2.554
_cell_volume                     5495.1(7)
_computing_cell_refinement       'SAINT V8.18C (Bruker, 2013)'
_computing_data_collection       APEX2
_computing_data_reduction        'SAINT V8.18C (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 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2002 (Burla et al., 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15352
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.082
_diffrn_reflns_theta_max         25.082
_diffrn_reflns_theta_min         1.547
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    5.020
_exptl_absorpt_correction_T_max  0.4286
_exptl_absorpt_correction_T_min  0.1517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; SADABS-2009/1 (Bruker) was used for absorption correction.
wR2(int) was 0.1259 before and 0.0364 after correction, on
8684 reflections employed for parameter determination.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3016
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         4876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0340P)²+1.9230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0655
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3983
_reflns_number_total             4876
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om7b00161_si_002.cif
_cod_data_source_block           2
_cod_original_formula_sum        'C31.50 H21 Cl F4 Ir N3 O2'
_cod_database_code               4087258
_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   0.465
_shelx_estimated_absorpt_t_min   0.391
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C14(H14), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C25(H25), C29(H29), C30(H30), C31(H31), C32(H32)
;
_shelx_shelxl_version_number     2014/7
_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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Ir Ir 0.34531(2) 0.87219(2) 0.82061(2) 0.03215(7) Uani 1 1 d . . .
F4 F 0.19530(16) 0.9203(2) 0.4790(2) 0.0915(11) Uani 1 1 d . . .
F5 F 0.12152(12) 0.8950(2) 0.7367(2) 0.0713(9) Uani 1 1 d . . .
F6 F 0.31933(14) 1.18009(17) 0.9580(2) 0.0721(9) Uani 1 1 d . . .
F7 F 0.41402(17) 1.1627(2) 0.7246(2) 0.0871(11) Uani 1 1 d . . .
O1 O 0.42172(13) 0.84750(18) 0.9307(2) 0.0433(7) Uani 1 1 d . . .
O2 O 0.36107(15) 0.60470(19) 0.8210(2) 0.0533(9) Uani 1 1 d . . .
N1 N 0.34116(15) 0.7409(2) 0.7970(2) 0.0395(9) Uani 1 1 d . . .
N2 N 0.29299(15) 0.86209(19) 0.9057(2) 0.0347(8) Uani 1 1 d . . .
N3 N 0.39423(15) 0.8968(2) 0.7319(3) 0.0426(9) Uani 1 1 d . . .
C2 C 0.3730(2) 0.6848(3) 0.8498(3) 0.0393(10) Uani 1 1 d . . .
C3 C 0.41810(18) 0.6963(3) 0.9362(3) 0.0397(10) Uani 1 1 d . . .
C4 C 0.43886(17) 0.7764(3) 0.9708(3) 0.0375(10) Uani 1 1 d . . .
C5 C 0.48207(19) 0.7782(3) 1.0577(3) 0.0500(12) Uani 1 1 d . . .
H5 H 0.4971 0.8297 1.0820 0.060 Uiso 1 1 calc R . .
C6 C 0.5027(2) 0.7071(3) 1.1074(4) 0.0657(15) Uani 1 1 d . . .
H6 H 0.5312 0.7104 1.1644 0.079 Uiso 1 1 calc R . .
C7 C 0.4801(3) 0.6289(3) 1.0710(5) 0.0781(19) Uani 1 1 d . . .
H7 H 0.4928 0.5804 1.1055 0.094 Uiso 1 1 calc R . .
C8 C 0.4406(2) 0.6235(3) 0.9878(4) 0.0607(14) Uani 1 1 d . . .
H8 H 0.4277 0.5710 0.9633 0.073 Uiso 1 1 calc R . .
C9 C 0.3122(3) 0.6066(3) 0.7397(4) 0.0648(16) Uani 1 1 d . . .
H9A H 0.2795 0.5797 0.7529 0.078 Uiso 1 1 calc R . .
H9B H 0.3204 0.5784 0.6868 0.078 Uiso 1 1 calc R . .
C10 C 0.3004(2) 0.6994(3) 0.7184(3) 0.0566(14) Uani 1 1 d . . .
H10A H 0.3072 0.7146 0.6589 0.068 Uiso 1 1 calc R . .
H10B H 0.2613 0.7137 0.7164 0.068 Uiso 1 1 calc R . .
C11 C 0.27046(18) 0.8916(2) 0.7266(3) 0.0351(9) Uani 1 1 d . . .
C12 C 0.2595(2) 0.9034(3) 0.6290(3) 0.0487(11) Uani 1 1 d . . .
H12 H 0.2897 0.9062 0.6020 0.058 Uiso 1 1 calc R . .
C13 C 0.2042(3) 0.9109(3) 0.5738(3) 0.0582(14) Uani 1 1 d . . .
C14 C 0.1574(2) 0.9079(3) 0.6058(4) 0.0585(14) Uani 1 1 d . . .
H14 H 0.1206 0.9133 0.5653 0.070 Uiso 1 1 calc R . .
C15 C 0.1668(2) 0.8968(3) 0.7007(4) 0.0458(11) Uani 1 1 d . . .
C16 C 0.22283(18) 0.8877(2) 0.7637(3) 0.0360(9) Uani 1 1 d . . .
C17 C 0.23598(18) 0.8755(2) 0.8653(3) 0.0362(9) Uani 1 1 d . . .
C18 C 0.1989(2) 0.8777(3) 0.9210(4) 0.0539(12) Uani 1 1 d . . .
H18 H 0.1599 0.8858 0.8935 0.065 Uiso 1 1 calc R . .
C19 C 0.2194(3) 0.8680(3) 1.0164(4) 0.0684(16) Uani 1 1 d . . .
H19 H 0.1944 0.8700 1.0538 0.082 Uiso 1 1 calc R . .
C20 C 0.2764(3) 0.8554(3) 1.0569(4) 0.0587(14) Uani 1 1 d . . .
H20 H 0.2907 0.8492 1.1219 0.070 Uiso 1 1 calc R . .
C21 C 0.3121(2) 0.8520(3) 1.0000(3) 0.0457(11) Uani 1 1 d . . .
H21 H 0.3510 0.8424 1.0273 0.055 Uiso 1 1 calc R . .
C22 C 0.35366(17) 0.9965(3) 0.8385(3) 0.0381(10) Uani 1 1 d . . .
C23 C 0.33245(19) 1.0470(3) 0.8977(3) 0.0423(10) Uani 1 1 d . . .
H23 H 0.3128 1.0230 0.9369 0.051 Uiso 1 1 calc R . .
C24 C 0.3404(2) 1.1321(3) 0.8983(4) 0.0526(13) Uani 1 1 d . . .
C25 C 0.3668(2) 1.1716(3) 0.8407(4) 0.0583(14) Uani 1 1 d . . .
H25 H 0.3702 1.2297 0.8403 0.070 Uiso 1 1 calc R . .
C26 C 0.3880(2) 1.1217(3) 0.7832(4) 0.0565(14) Uani 1 1 d . . .
C27 C 0.38274(18) 1.0357(3) 0.7787(3) 0.0421(11) Uani 1 1 d . . .
C28 C 0.40510(19) 0.9797(3) 0.7196(3) 0.0451(11) Uani 1 1 d . . .
C29 C 0.4366(2) 1.0004(4) 0.6575(4) 0.0648(15) Uani 1 1 d . . .
H29 H 0.4436 1.0566 0.6477 0.078 Uiso 1 1 calc R . .
C30 C 0.4575(3) 0.9400(5) 0.6107(4) 0.0776(18) Uani 1 1 d . . .
H30 H 0.4784 0.9547 0.5691 0.093 Uiso 1 1 calc R . .
C31 C 0.4474(3) 0.8570(4) 0.6257(4) 0.0701(17) Uani 1 1 d . . .
H31 H 0.4619 0.8147 0.5956 0.084 Uiso 1 1 calc R . .
C32 C 0.4156(2) 0.8382(3) 0.6854(4) 0.0550(12) Uani 1 1 d . . .
H32 H 0.4083 0.7820 0.6947 0.066 Uiso 1 1 calc R . .
Cl Cl 0.0449(2) 0.8911(3) 0.3376(3) 0.2186(19) Uani 1 1 d . . .
C1 C 0.0000 0.9420(8) 0.2500 0.300(16) Uani 1 2 d S T P
H1 H 0.0230 0.9771 0.2212 0.360 Uiso 1 1 d R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.3040 7.9810 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0120 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
N1 Ir O1 86.23(12) .
N2 Ir O1 94.36(13) .
N2 Ir N1 90.81(13) .
N2 Ir N3 173.05(14) .
N3 Ir O1 89.16(13) .
N3 Ir N1 95.41(15) .
C11 Ir O1 174.71(14) .
C11 Ir N1 92.69(15) .
C11 Ir N2 80.47(16) .
C11 Ir N3 96.10(16) .
C11 Ir C22 88.69(16) .
C22 Ir O1 92.73(14) .
C22 Ir N1 175.99(16) .
C22 Ir N2 93.14(15) .
C22 Ir N3 80.69(17) .
C4 O1 Ir 127.6(3) .
C2 O2 C9 107.3(3) .
C2 N1 Ir 126.3(3) .
C2 N1 C10 108.9(4) .
C10 N1 Ir 124.8(3) .
C17 N2 Ir 116.9(3) .
C21 N2 Ir 123.7(3) .
C21 N2 C17 119.0(4) .
C28 N3 Ir 116.1(3) .
C32 N3 Ir 124.9(3) .
C32 N3 C28 119.0(4) .
O2 C2 C3 116.2(4) .
N1 C2 O2 115.2(4) .
N1 C2 C3 128.6(4) .
C4 C3 C2 122.8(4) .
C8 C3 C2 117.1(4) .
C8 C3 C4 120.1(4) .
O1 C4 C3 126.1(4) .
O1 C4 C5 117.5(4) .
C5 C4 C3 116.5(4) .
C6 C5 C4 122.6(5) .
C5 C6 C7 119.0(5) .
C8 C7 C6 120.8(5) .
C7 C8 C3 120.9(5) .
O2 C9 C10 104.9(4) .
N1 C10 C9 103.3(4) .
C12 C11 Ir 127.9(3) .
C12 C11 C16 117.6(4) .
C16 C11 Ir 114.4(3) .
C13 C12 C11 119.8(5) .
F4 C13 C12 117.9(5) .
C14 C13 F4 117.2(5) .
C14 C13 C12 124.9(5) .
C13 C14 C15 116.7(5) .
F5 C15 C14 119.1(5) .
F5 C15 C16 118.4(4) .
C14 C15 C16 122.5(5) .
C11 C16 C15 118.6(4) .
C11 C16 C17 116.0(4) .
C15 C16 C17 125.4(4) .
N2 C17 C16 112.0(4) .
N2 C17 C18 119.8(4) .
C18 C17 C16 128.2(4) .
C19 C18 C17 120.1(5) .
C20 C19 C18 120.2(5) .
C19 C20 C21 118.6(5) .
N2 C21 C20 122.4(5) .
C23 C22 Ir 127.9(3) .
C23 C22 C27 118.2(4) .
C27 C22 Ir 113.8(3) .
C24 C23 C22 120.1(5) .
C23 C24 F6 118.6(5) .
C25 C24 F6 118.1(4) .
C25 C24 C23 123.2(5) .
C24 C25 C26 116.5(5) .
F7 C26 C27 119.8(5) .
C25 C26 F7 115.9(4) .
C25 C26 C27 124.3(5) .
C22 C27 C28 115.9(4) .
C26 C27 C22 117.6(5) .
C26 C27 C28 126.5(5) .
N3 C28 C27 113.2(4) .
N3 C28 C29 118.7(5) .
C29 C28 C27 128.1(5) .
C30 C29 C28 121.2(5) .
C29 C30 C31 119.2(5) .
C32 C31 C30 118.5(5) .
N3 C32 C31 123.3(5) .
Cl C1 Cl 121.2(9) 2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir O1 2.134(3) .
Ir N1 2.119(3) .
Ir N2 2.030(3) .
Ir N3 2.040(4) .
Ir C11 1.979(4) .
Ir C22 2.001(4) .
F4 C13 1.364(5) .
F5 C15 1.351(6) .
F6 C24 1.371(6) .
F7 C26 1.371(6) .
O1 C4 1.293(5) .
O2 C2 1.351(5) .
O2 C9 1.434(6) .
N1 C2 1.292(6) .
N1 C10 1.457(5) .
N2 C17 1.363(5) .
N2 C21 1.348(5) .
N3 C28 1.369(6) .
N3 C32 1.349(6) .
C2 C3 1.442(6) .
C3 C4 1.415(6) .
C3 C8 1.412(6) .
C4 C5 1.412(6) .
C5 C6 1.366(7) .
C6 C7 1.407(8) .
C7 C8 1.334(8) .
C9 C10 1.522(6) .
C11 C12 1.403(6) .
C11 C16 1.414(6) .
C12 C13 1.368(7) .
C13 C14 1.348(8) .
C14 C15 1.367(7) .
C15 C16 1.425(6) .
C16 C17 1.457(6) .
C17 C18 1.382(6) .
C18 C19 1.366(8) .
C19 C20 1.360(8) .
C20 C21 1.370(7) .
C22 C23 1.390(6) .
C22 C27 1.422(6) .
C23 C24 1.370(6) .
C24 C25 1.356(7) .
C25 C26 1.366(8) .
C26 C27 1.377(6) .
C27 C28 1.457(6) .
C28 C29 1.390(6) .
C29 C30 1.365(8) .
C30 C31 1.375(8) .
C31 C32 1.358(7) .
Cl C1 1.653(7) .
C1 Cl 1.653(7) 2
