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#$Date: 2017-06-20 05:05:04 +0300 (Tue, 20 Jun 2017) $
#$Revision: 197957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/33/7043389.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_7043389
loop_
_publ_author_name
'Orwat, Bartosz'
'Witkowska, Ewelina'
'Kownacki, Ireneusz'
'Oh, Myong-joon'
'Hoffmann, Marcin'
'Kubicki, Maciej'
'Grzelak, Izabela'
'Marciniec, Bogdan'
'Głowacki, Ireneusz'
'Luszczynska, Beata'
'Wiosna-Sałyga, Gabriela'
'Ulanski, Jacek'
'Ledwon, Przemyslaw'
'Lapkowski, Mieczyslaw'
_publ_section_title
;
 Microwave-assisted one-pot synthesis of new ionic cyclometalated iridium
 complexes of [Ir(bzq)2(N^N)]+A- type and their selected
 electroluminescent properties
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT01372H
_journal_year                    2017
_chemical_formula_moiety         'C38 H24 Ir N4, F6 P, C H4 O'
_chemical_formula_sum            'C39 H28 F6 Ir N4 O P'
_chemical_formula_weight         905.82
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-11-22 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.868(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1984(5)
_cell_length_b                   14.8577(5)
_cell_length_c                   18.2375(7)
_cell_measurement_reflns_used    4547
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      28.3510
_cell_measurement_theta_min      3.4050
_cell_volume                     3234.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '/w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11744
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.268
_diffrn_reflns_theta_min         3.407
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.253
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_description       prism
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.369
_refine_diff_density_min         -0.963
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       0.00099(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0214
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0517P)²+3.9975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3141
_reflns_number_total             3565
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt01372h2.cif
_cod_data_source_block           1
_cod_database_code               7043389
_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.
;
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
Ir1 Ir 0.5000 0.99828(2) 0.2500 0.01020(9) Uani 1 2 d S T P
N1A N 0.5944(2) 1.09933(18) 0.31265(15) 0.0160(5) Uani 1 1 d . . .
C2A C 0.6820(2) 1.14416(19) 0.29751(17) 0.0229(6) Uani 1 1 d . . .
H2A H 0.7113 1.1268 0.2552 0.027 Uiso 1 1 calc R U .
C3A C 0.7321(3) 1.2160(2) 0.34185(19) 0.0281(7) Uani 1 1 d . . .
H3A H 0.7950 1.2460 0.3300 0.034 Uiso 1 1 calc R U .
C4A C 0.6900(3) 1.24243(19) 0.40196(18) 0.0268(7) Uani 1 1 d . . .
H4A H 0.7218 1.2926 0.4310 0.032 Uiso 1 1 calc R U .
C5A C 0.6004(2) 1.19639(18) 0.42118(15) 0.0196(6) Uani 1 1 d . . .
C6A C 0.5513(3) 1.2177(2) 0.48407(16) 0.0237(6) Uani 1 1 d . . .
H6A H 0.5783 1.2680 0.5146 0.028 Uiso 1 1 calc R U .
C7A C 0.4672(3) 1.1672(2) 0.50065(16) 0.0225(6) Uani 1 1 d . . .
H7A H 0.4387 1.1812 0.5440 0.027 Uiso 1 1 calc R U .
C8A C 0.4203(2) 1.09360(17) 0.45456(15) 0.0175(6) Uani 1 1 d . . .
C9A C 0.3277(2) 1.04291(19) 0.46551(16) 0.0201(6) Uani 1 1 d . . .
H9A H 0.2969 1.0530 0.5086 0.024 Uiso 1 1 calc R U .
C10A C 0.2819(3) 0.9790(2) 0.4141(2) 0.0232(7) Uani 1 1 d . . .
H10A H 0.2176 0.9465 0.4207 0.028 Uiso 1 1 calc R U .
C11A C 0.3292(2) 0.96115(18) 0.35186(16) 0.0189(6) Uani 1 1 d . . .
H11A H 0.2973 0.9157 0.3174 0.023 Uiso 1 1 calc R U .
C12A C 0.4197(3) 1.00743(15) 0.3397(2) 0.0125(6) Uani 1 1 d . . .
C13A C 0.4639(2) 1.07306(17) 0.39055(15) 0.0147(5) Uani 1 1 d . . .
C14A C 0.5553(2) 1.12376(17) 0.37508(14) 0.0148(5) Uani 1 1 d . . .
N15A N 0.5963(2) 0.89416(19) 0.29922(14) 0.0170(5) Uani 1 1 d . . .
C16A C 0.6982(2) 0.89619(18) 0.34728(15) 0.0174(5) Uani 1 1 d . . .
H16A H 0.7326 0.9525 0.3619 0.021 Uiso 1 1 calc R U .
C17A C 0.7528(2) 0.8166(2) 0.37550(17) 0.0237(7) Uani 1 1 d . . .
H17A H 0.8235 0.8199 0.4090 0.028 Uiso 1 1 calc R U .
C18A C 0.7057(3) 0.7340(2) 0.35551(17) 0.0239(6) Uani 1 1 d . . .
H18A H 0.7423 0.6806 0.3763 0.029 Uiso 1 1 calc R U .
C19A C 0.6028(2) 0.72907(18) 0.30398(16) 0.0197(6) Uani 1 1 d . . .
C20A C 0.5514(2) 0.81028(17) 0.27679(14) 0.0146(5) Uani 1 1 d . . .
C21A C 0.5479(3) 0.6467(2) 0.2753(2) 0.0247(7) Uani 1 1 d . . .
H21A H 0.5809 0.5910 0.2936 0.030 Uiso 1 1 d R U .
P1B P 0.0000 0.0000 0.5000 0.0272(4) Uani 1 2 d S . P
F1B F 0.06333(18) 0.08015(14) 0.46771(13) 0.0418(5) Uani 1 1 d . . .
F2B F -0.00302(19) 0.05841(16) 0.57352(13) 0.0480(6) Uani 1 1 d . . .
F3B F -0.11787(16) 0.04228(16) 0.46063(12) 0.0450(5) Uani 1 1 d . . .
O1C O 0.0000 0.1294(5) 0.7500 0.102(2) Uani 1 2 d S T P
H1C H 0.0426 0.1374 0.7919 0.153 Uiso 0.5 1 d R U P
C1C C -0.0853(5) 0.0763(4) 0.7584(4) 0.0346(16) Uani 0.5 1 d . . P
H1C1 H -0.1094 0.0400 0.7132 0.052 Uiso 0.5 1 d R U P
H1C2 H -0.1479 0.1136 0.7667 0.052 Uiso 0.5 1 d R U P
H1C3 H -0.0610 0.0366 0.8016 0.052 Uiso 0.5 1 d R U P
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'
F F 0.0171 0.0103 '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'
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
N15A Ir1 N15A 81.12(15) 6_656 .
N15A Ir1 C12A 94.24(11) 6_656 .
N15A Ir1 C12A 91.46(10) . .
N15A Ir1 C12A 91.46(10) 6_656 6_656
N15A Ir1 C12A 94.24(11) . 6_656
C12A Ir1 C12A 172.50(12) . 6_656
N15A Ir1 N1A 173.04(8) 6_656 .
N15A Ir1 N1A 95.84(13) . .
C12A Ir1 N1A 79.53(11) . .
C12A Ir1 N1A 95.02(11) 6_656 .
N15A Ir1 N1A 95.84(13) 6_656 6_656
N15A Ir1 N1A 173.04(8) . 6_656
C12A Ir1 N1A 95.02(11) . 6_656
C12A Ir1 N1A 79.53(11) 6_656 6_656
N1A Ir1 N1A 87.85(14) . 6_656
C2A N1A C14A 118.0(3) . .
C2A N1A Ir1 128.4(2) . .
C14A N1A Ir1 113.48(19) . .
N1A C2A C3A 122.2(3) . .
N1A C2A H2A 118.9 . .
C3A C2A H2A 118.9 . .
C4A C3A C2A 119.5(3) . .
C4A C3A H3A 120.2 . .
C2A C3A H3A 120.2 . .
C3A C4A C5A 120.4(3) . .
C3A C4A H4A 119.8 . .
C5A C4A H4A 119.8 . .
C4A C5A C14A 117.1(3) . .
C4A C5A C6A 124.8(3) . .
C14A C5A C6A 118.0(3) . .
C7A C6A C5A 121.1(3) . .
C7A C6A H6A 119.4 . .
C5A C6A H6A 119.4 . .
C6A C7A C8A 121.6(3) . .
C6A C7A H7A 119.2 . .
C8A C7A H7A 119.2 . .
C9A C8A C13A 116.9(3) . .
C9A C8A C7A 124.3(3) . .
C13A C8A C7A 118.7(3) . .
C10A C9A C8A 120.0(3) . .
C10A C9A H9A 120.0 . .
C8A C9A H9A 120.0 . .
C9A C10A C11A 120.5(3) . .
C9A C10A H10A 119.8 . .
C11A C10A H10A 119.8 . .
C12A C11A C10A 121.4(3) . .
C12A C11A H11A 119.3 . .
C10A C11A H11A 119.3 . .
C11A C12A C13A 117.9(3) . .
C11A C12A Ir1 128.8(2) . .
C13A C12A Ir1 113.2(2) . .
C12A C13A C8A 123.2(3) . .
C12A C13A C14A 117.2(3) . .
C8A C13A C14A 119.6(2) . .
N1A C14A C5A 122.6(2) . .
N1A C14A C13A 116.5(2) . .
C5A C14A C13A 120.9(2) . .
C16A N15A C20A 117.4(2) . .
C16A N15A Ir1 129.2(2) . .
C20A N15A Ir1 113.24(19) . .
N15A C16A C17A 121.2(3) . .
N15A C16A H16A 119.4 . .
C17A C16A H16A 119.4 . .
C18A C17A C16A 121.0(3) . .
C18A C17A H17A 119.5 . .
C16A C17A H17A 119.5 . .
C17A C18A C19A 119.4(3) . .
C17A C18A H18A 120.3 . .
C19A C18A H18A 120.3 . .
C20A C19A C18A 117.6(3) . .
C20A C19A C21A 117.5(3) . .
C18A C19A C21A 124.8(3) . .
N15A C20A C19A 123.2(2) . .
N15A C20A C20A 116.19(15) . 6_656
C19A C20A C20A 120.64(16) . 6_656
C21A C21A C19A 121.83(18) 6_656 .
C21A C21A H21A 119.4 6_656 .
C19A C21A H21A 118.7 . .
F1B P1B F1B 180.00(10) 5_556 .
F1B P1B F3B 90.00(11) 5_556 5_556
F1B P1B F3B 90.00(11) . 5_556
F1B P1B F3B 90.00(11) 5_556 .
F1B P1B F3B 90.00(11) . .
F3B P1B F3B 180.0 5_556 .
F1B P1B F2B 89.96(11) 5_556 .
F1B P1B F2B 90.04(11) . .
F3B P1B F2B 90.59(12) 5_556 .
F3B P1B F2B 89.41(12) . .
F1B P1B F2B 90.04(11) 5_556 5_556
F1B P1B F2B 89.96(11) . 5_556
F3B P1B F2B 89.41(12) 5_556 5_556
F3B P1B F2B 90.59(12) . 5_556
F2B P1B F2B 180.00(15) . 5_556
C1C O1C C1C 107.9(8) . 6_557
C1C O1C H1C 109.2 . .
C1C O1C H1C 80.8 6_557 .
O1C C1C H1C1 109.5 . .
O1C C1C H1C2 109.5 . .
H1C1 C1C H1C2 109.5 . .
O1C C1C H1C3 109.5 . .
H1C1 C1C H1C3 109.5 . .
H1C2 C1C H1C3 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 N15A 2.036(3) 6_656
Ir1 N15A 2.036(3) .
Ir1 C12A 2.077(4) .
Ir1 C12A 2.077(4) 6_656
Ir1 N1A 2.084(3) .
Ir1 N1A 2.085(3) 6_656
N1A C2A 1.335(4) .
N1A C14A 1.371(4) .
C2A C3A 1.401(4) .
C2A H2A 0.9500 .
C3A C4A 1.361(5) .
C3A H3A 0.9500 .
C4A C5A 1.393(4) .
C4A H4A 0.9500 .
C5A C14A 1.409(4) .
C5A C6A 1.434(4) .
C6A C7A 1.355(5) .
C6A H6A 0.9500 .
C7A C8A 1.425(4) .
C7A H7A 0.9500 .
C8A C9A 1.406(4) .
C8A C13A 1.412(4) .
C9A C10A 1.371(5) .
C9A H9A 0.9500 .
C10A C11A 1.400(4) .
C10A H10A 0.9500 .
C11A C12A 1.356(4) .
C11A H11A 0.9500 .
C12A C13A 1.377(4) .
C13A C14A 1.421(4) .
N15A C16A 1.365(4) .
N15A C20A 1.389(4) .
C16A C17A 1.402(4) .
C16A H16A 0.9500 .
C17A C18A 1.372(5) .
C17A H17A 0.9500 .
C18A C19A 1.407(4) .
C18A H18A 0.9500 .
C19A C20A 1.402(4) .
C19A C21A 1.441(4) .
C20A C20A 1.422(5) 6_656
C21A C21A 1.332(7) 6_656
C21A H21A 0.9500 .
P1B F1B 1.5964(19) 5_556
P1B F1B 1.5965(19) .
P1B F3B 1.598(2) 5_556
P1B F3B 1.598(2) .
P1B F2B 1.604(2) .
P1B F2B 1.604(2) 5_556
O1C C1C 1.339(7) .
O1C C1C 1.339(7) 6_557
O1C H1C 0.8400 .
C1C H1C1 0.9800 .
C1C H1C2 0.9800 .
C1C H1C3 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_4
C14A N1A C2A C3A -1.8(4) .
Ir1 N1A C2A C3A 174.6(2) .
N1A C2A C3A C4A -0.9(5) .
C2A C3A C4A C5A 2.5(5) .
C3A C4A C5A C14A -1.3(4) .
C3A C4A C5A C6A 178.8(3) .
C4A C5A C6A C7A -177.3(3) .
C14A C5A C6A C7A 2.7(4) .
C5A C6A C7A C8A -2.9(5) .
C6A C7A C8A C9A -175.1(3) .
C6A C7A C8A C13A 0.4(4) .
C13A C8A C9A C10A -1.9(4) .
C7A C8A C9A C10A 173.7(3) .
C8A C9A C10A C11A 2.4(5) .
C9A C10A C11A C12A -1.4(5) .
C10A C11A C12A C13A -0.1(4) .
C10A C11A C12A Ir1 -176.8(2) .
C11A C12A C13A C8A 0.6(4) .
Ir1 C12A C13A C8A 177.7(2) .
C11A C12A C13A C14A -177.1(2) .
Ir1 C12A C13A C14A 0.1(3) .
C9A C8A C13A C12A 0.5(4) .
C7A C8A C13A C12A -175.4(3) .
C9A C8A C13A C14A 178.1(2) .
C7A C8A C13A C14A 2.2(4) .
C2A N1A C14A C5A 3.0(4) .
Ir1 N1A C14A C5A -173.9(2) .
C2A N1A C14A C13A -178.4(3) .
Ir1 N1A C14A C13A 4.7(3) .
C4A C5A C14A N1A -1.5(4) .
C6A C5A C14A N1A 178.4(3) .
C4A C5A C14A C13A 180.0(2) .
C6A C5A C14A C13A -0.1(4) .
C12A C13A C14A N1A -3.2(4) .
C8A C13A C14A N1A 179.1(2) .
C12A C13A C14A C5A 175.4(3) .
C8A C13A C14A C5A -2.3(4) .
C20A N15A C16A C17A -2.8(4) .
Ir1 N15A C16A C17A -179.7(2) .
N15A C16A C17A C18A 0.2(4) .
C16A C17A C18A C19A 2.1(4) .
C17A C18A C19A C20A -1.6(4) .
C17A C18A C19A C21A 176.3(3) .
C16A N15A C20A C19A 3.3(4) .
Ir1 N15A C20A C19A -179.4(2) .
C16A N15A C20A C20A -176.3(3) 6_656
Ir1 N15A C20A C20A 1.1(4) 6_656
C18A C19A C20A N15A -1.1(4) .
C21A C19A C20A N15A -179.2(3) .
C18A C19A C20A C20A 178.4(3) 6_656
C21A C19A C20A C20A 0.3(4) 6_656
C20A C19A C21A C21A 0.3(6) 6_656
C18A C19A C21A C21A -177.7(4) 6_656
