#------------------------------------------------------------------------------
#$Date: 2017-05-31 04:20:59 +0300 (Wed, 31 May 2017) $
#$Revision: 197056 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/61/1546138.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_1546138
loop_
_publ_author_name
'Yan, Hong'
'Li, Xiang'
'Yin, Yongheng'
'Lu, Changsheng'
'Tong, Xiao'
'Zhao, Qiang'
_publ_section_title
;
 Using highly emissive and environmentally sensitive
 o-carborane-functionalized metallophosphors to monitor mitochondrial
 polarity
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC00160F
_journal_year                    2017
_chemical_formula_moiety
'C32 H20 F4 Ir N4, F6 P, 0.5(C4 H10 O), C H2 Cl2'
_chemical_formula_sum            'C35 H27 Cl2 F10 Ir N4 O0.5 P'
_chemical_formula_weight         995.68
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-07-28 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6791(14)
_cell_length_b                   12.7772(18)
_cell_length_c                   28.988(4)
_cell_measurement_reflns_used    9590
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.53
_cell_volume                     3585.0(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  Duo
_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  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            32482
_diffrn_reflns_theta_full        27.63
_diffrn_reflns_theta_max         27.63
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    4.005
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_correction_T_min  0.5326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1940
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.146
_refine_diff_density_min         -1.343
_refine_diff_density_rms         0.115
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.236(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         8309
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0240
_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)+(0.0408P)²+4.9119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0706
_reflns_number_gt                8158
_reflns_number_total             8309
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7sc00160f2.cif
_cod_data_source_block           model
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_original_formula_sum        'C35 H27 Cl2 F10 Ir N4 O0.50 P'
_cod_database_code               1546138
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
C1 C 0.8217(4) 0.8375(3) 0.41359(14) 0.0163(8) Uani 1 1 d . . .
C2 C 0.8447(5) 0.8666(3) 0.46027(14) 0.0188(9) Uani 1 1 d . . .
C3 C 0.7381(5) 0.8569(4) 0.49125(15) 0.0235(9) Uani 1 1 d . . .
C4 C 0.6052(5) 0.8233(4) 0.47923(15) 0.0230(9) Uani 1 1 d . . .
H4 H 0.5322 0.8195 0.5011 0.028 Uiso 1 1 calc R . .
C5 C 0.5875(5) 0.7965(4) 0.43419(17) 0.0240(10) Uani 1 1 d . . .
C6 C 0.6902(5) 0.8031(3) 0.40115(15) 0.0217(9) Uani 1 1 d . . .
H6 H 0.6712 0.7843 0.3701 0.026 Uiso 1 1 calc R . .
C7 C 0.9865(5) 0.8999(3) 0.47133(13) 0.0200(8) Uani 1 1 d . . .
C8 C 1.0334(5) 0.9412(4) 0.51362(15) 0.0258(10) Uani 1 1 d . . .
H8 H 0.9714 0.9480 0.5388 0.031 Uiso 1 1 calc R . .
C9 C 1.1681(6) 0.9714(4) 0.51830(16) 0.0302(11) Uani 1 1 d . . .
H9 H 1.1993 1.0018 0.5463 0.036 Uiso 1 1 calc R . .
C10 C 1.2603(5) 0.9572(4) 0.48134(17) 0.0299(11) Uani 1 1 d . . .
H10 H 1.3551 0.9752 0.4844 0.036 Uiso 1 1 calc R . .
C11 C 1.2101(5) 0.9166(4) 0.44052(15) 0.0208(9) Uani 1 1 d . . .
H11 H 1.2715 0.9078 0.4152 0.025 Uiso 1 1 calc R . .
C12 C 0.9463(4) 0.9966(3) 0.35705(15) 0.0182(8) Uani 1 1 d . . .
C13 C 0.8841(5) 1.0095(4) 0.31305(15) 0.0239(9) Uani 1 1 d . . .
C14 C 0.8597(6) 1.1103(4) 0.29763(18) 0.0329(12) Uani 1 1 d . . .
C15 C 0.8915(6) 1.1997(4) 0.3227(2) 0.0368(13) Uani 1 1 d . . .
H15 H 0.8748 1.2680 0.3110 0.044 Uiso 1 1 calc R . .
C16 C 0.9476(5) 1.1832(4) 0.3646(2) 0.0330(12) Uani 1 1 d . . .
C17 C 0.9767(5) 1.0861(3) 0.38361(17) 0.0263(9) Uani 1 1 d . . .
H17 H 1.0160 1.0800 0.4135 0.032 Uiso 1 1 calc R . .
C18 C 0.8514(5) 0.9111(4) 0.28863(15) 0.0231(9) Uani 1 1 d . . .
C19 C 0.7874(6) 0.9035(5) 0.24576(16) 0.0338(12) Uani 1 1 d . . .
H19 H 0.7611 0.9650 0.2296 0.041 Uiso 1 1 calc R . .
C20 C 0.7625(6) 0.8062(5) 0.22687(18) 0.0374(13) Uani 1 1 d . . .
H20 H 0.7211 0.8007 0.1972 0.045 Uiso 1 1 calc R . .
C21 C 0.7976(6) 0.7165(5) 0.25101(17) 0.0340(12) Uani 1 1 d . . .
H21 H 0.7794 0.6490 0.2386 0.041 Uiso 1 1 calc R . .
C22 C 0.8605(5) 0.7281(4) 0.29396(16) 0.0237(9) Uani 1 1 d . . .
H22 H 0.8842 0.6672 0.3110 0.028 Uiso 1 1 calc R . .
C23 C 1.1746(4) 0.6620(3) 0.36160(13) 0.0175(8) Uani 1 1 d . . .
C24 C 1.2240(5) 0.5604(4) 0.36265(15) 0.0241(10) Uani 1 1 d . . .
H24 H 1.3107 0.5438 0.3491 0.029 Uiso 1 1 calc R . .
C25 C 1.1452(5) 0.4828(4) 0.38373(17) 0.0278(10) Uani 1 1 d . . .
H25 H 1.1784 0.4130 0.3855 0.033 Uiso 1 1 calc R . .
C26 C 1.0201(5) 0.5086(3) 0.40181(17) 0.0275(10) Uani 1 1 d . . .
H26 H 0.9628 0.4561 0.4150 0.033 Uiso 1 1 calc R . .
C27 C 0.9767(5) 0.6119(3) 0.40090(14) 0.0211(9) Uani 1 1 d . . .
H27 H 0.8909 0.6297 0.4147 0.025 Uiso 1 1 calc R . .
C28 C 1.2498(5) 0.7482(3) 0.33823(14) 0.0184(8) Uani 1 1 d . . .
C29 C 1.3758(5) 0.7372(4) 0.31801(16) 0.0251(10) Uani 1 1 d . . .
H29 H 1.4214 0.6714 0.3187 0.030 Uiso 1 1 calc R . .
C30 C 1.4381(6) 0.8222(4) 0.29628(17) 0.0326(11) Uani 1 1 d . . .
H30 H 1.5266 0.8154 0.2824 0.039 Uiso 1 1 calc R . .
C31 C 1.3682(6) 0.9172(4) 0.29523(18) 0.0323(11) Uani 1 1 d . . .
H31 H 1.4073 0.9763 0.2802 0.039 Uiso 1 1 calc R . .
C32 C 1.2426(6) 0.9237(4) 0.31620(17) 0.0294(11) Uani 1 1 d . . .
H32 H 1.1961 0.9892 0.3160 0.035 Uiso 1 1 calc R . .
F1 F 0.7164(3) 0.3926(3) 0.37787(11) 0.0421(7) Uani 1 1 d . . .
F2 F 0.7563(4) 0.4785(3) 0.31057(12) 0.0498(9) Uani 1 1 d . . .
F3 F 0.6347(5) 0.5579(3) 0.36809(12) 0.0589(11) Uani 1 1 d . . .
F4 F 0.5270(4) 0.5070(3) 0.30269(10) 0.0413(8) Uani 1 1 d . . .
F5 F 0.4891(3) 0.4204(3) 0.36957(11) 0.0508(9) Uani 1 1 d . . .
F6 F 0.6103(3) 0.3434(2) 0.31236(11) 0.0383(7) Uani 1 1 d . . .
F7 F 0.4617(3) 0.7616(3) 0.42130(11) 0.0342(7) Uani 1 1 d . . .
F8 F 0.7584(3) 0.8820(3) 0.53640(9) 0.0335(7) Uani 1 1 d . . .
F9 F 0.9819(4) 1.2677(2) 0.38998(14) 0.0529(9) Uani 1 1 d . . .
F10 F 0.8000(5) 1.1247(3) 0.25523(12) 0.0573(11) Uani 1 1 d . . .
Ir1 Ir 0.990181(14) 0.846919(12) 0.373244(4) 0.01412(5) Uani 1 1 d . . .
N1 N 1.0759(4) 0.8890(3) 0.43547(12) 0.0163(7) Uani 1 1 d . . .
N2 N 0.8886(4) 0.8231(3) 0.31211(12) 0.0190(7) Uani 1 1 d . . .
N3 N 1.0518(3) 0.6870(3) 0.38117(12) 0.0144(6) Uani 1 1 d . . .
N4 N 1.1808(4) 0.8421(3) 0.33726(12) 0.0185(7) Uani 1 1 d . . .
P1 P 0.62395(14) 0.45019(10) 0.34020(4) 0.0261(3) Uani 1 1 d . . .
C33 C 0.4970(13) 0.1801(13) 0.3883(8) 0.045(4) Uani 0.56(5) 1 d PDU A 1
H33A H 0.5183 0.2255 0.4150 0.054 Uiso 0.56(5) 1 calc PR A 1
H33B H 0.5351 0.2138 0.3603 0.054 Uiso 0.56(5) 1 calc PR A 1
Cl1 Cl 0.3202(9) 0.1678(9) 0.3828(5) 0.086(5) Uani 0.56(5) 1 d PDU A 1
Cl2 Cl 0.5761(12) 0.0564(15) 0.3961(8) 0.111(5) Uani 0.56(5) 1 d PDU A 1
C33' C 0.4945(14) 0.1583(19) 0.3742(14) 0.053(6) Uani 0.44(5) 1 d PDU A 2
H33C H 0.5366 0.2140 0.3933 0.063 Uiso 0.44(5) 1 calc PR A 2
H33D H 0.5177 0.1736 0.3416 0.063 Uiso 0.44(5) 1 calc PR A 2
Cl1' Cl 0.3191(5) 0.1651(5) 0.3803(4) 0.037(3) Uani 0.44(5) 1 d PDU A 2
Cl2' Cl 0.5709(7) 0.0390(9) 0.3892(4) 0.045(4) Uani 0.44(5) 1 d PDU A 2
C34 C 0.232(2) 0.3649(14) 0.5020(7) 0.045(4) Uiso 0.342(6) 1 d PDU . 3
H34A H 0.3272 0.3467 0.4964 0.067 Uiso 0.342(6) 1 d PR . 3
H34B H 0.2049 0.4189 0.4808 0.067 Uiso 0.342(6) 1 d PR . 3
H34C H 0.2225 0.3898 0.5330 0.067 Uiso 0.342(6) 1 d PR . 3
C35 C 0.1439(17) 0.2734(14) 0.4955(7) 0.043(4) Uiso 0.342(6) 1 d PDU . 3
H35A H 0.1743 0.2194 0.5162 0.051 Uiso 0.342(6) 1 d PR . 3
H35B H 0.1568 0.2481 0.4646 0.051 Uiso 0.342(6) 1 d PR . 3
O1 O 0.0012(14) 0.2901(11) 0.5024(5) 0.062(3) Uiso 0.342(6) 1 d PDU . 3
C36 C -0.0937(15) 0.2247(15) 0.4967(7) 0.040(3) Uiso 0.342(6) 1 d PDU . 3
H36A H -0.0922 0.1819 0.5239 0.048 Uiso 0.342(6) 1 d PR . 3
H36D H -0.0655 0.1807 0.4716 0.048 Uiso 0.342(6) 1 d PR . 3
C37 C -0.2441(17) 0.249(2) 0.4902(8) 0.060(5) Uiso 0.342(6) 1 d PDU . 3
H37A H -0.2975 0.1855 0.4875 0.090 Uiso 0.342(6) 1 d PR . 3
H37B H -0.2784 0.2895 0.5155 0.090 Uiso 0.342(6) 1 d PR . 3
H37C H -0.2513 0.2882 0.4622 0.090 Uiso 0.342(6) 1 d PR . 3
C34' C 0.318(3) 0.347(3) 0.4951(15) 0.051(6) Uiso 0.158(6) 1 d PDU . 4
H34D H 0.3581 0.4158 0.4947 0.077 Uiso 0.158(6) 1 d PR . 4
H34E H 0.3528 0.3091 0.5213 0.077 Uiso 0.158(6) 1 d PR . 4
H34F H 0.3427 0.3106 0.4674 0.077 Uiso 0.158(6) 1 d PR . 4
C35' C 0.163(3) 0.356(2) 0.4951(14) 0.041(5) Uiso 0.158(6) 1 d PDU . 4
H35C H 0.1308 0.3964 0.4693 0.049 Uiso 0.158(6) 1 d PR . 4
H35D H 0.1408 0.3950 0.5225 0.049 Uiso 0.158(6) 1 d PR . 4
O1' O 0.091(2) 0.2659(17) 0.4994(9) 0.035(4) Uiso 0.158(6) 1 d PDU . 4
C36' C -0.062(2) 0.272(2) 0.4932(9) 0.018(4) Uiso 0.158(6) 1 d PDU . 4
H36B H -0.0868 0.2831 0.4615 0.021 Uiso 0.158(6) 1 d PR . 4
H36C H -0.0998 0.3282 0.5113 0.021 Uiso 0.158(6) 1 d PR . 4
C37' C -0.118(3) 0.166(2) 0.5088(12) 0.034(5) Uiso 0.158(6) 1 d PDU . 4
H37D H -0.2169 0.1658 0.5060 0.051 Uiso 0.158(6) 1 d PR . 4
H37E H -0.0797 0.1111 0.4904 0.051 Uiso 0.158(6) 1 d PR . 4
H37F H -0.0927 0.1565 0.5405 0.051 Uiso 0.158(6) 1 d PR . 4
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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 118.2(4) . .
C6 C1 Ir1 127.5(3) . .
C2 C1 Ir1 114.3(3) . .
C3 C2 C1 118.8(4) . .
C3 C2 C7 125.7(4) . .
C1 C2 C7 115.4(4) . .
F8 C3 C2 120.0(4) . .
F8 C3 C4 116.3(4) . .
C2 C3 C4 123.7(4) . .
C5 C4 C3 115.6(4) . .
C5 C4 H4 122.2 . .
C3 C4 H4 122.2 . .
F7 C5 C4 117.5(4) . .
F7 C5 C6 118.5(4) . .
C4 C5 C6 124.0(5) . .
C5 C6 C1 119.7(4) . .
C5 C6 H6 120.1 . .
C1 C6 H6 120.1 . .
N1 C7 C8 119.9(4) . .
N1 C7 C2 113.4(3) . .
C8 C7 C2 126.7(4) . .
C9 C8 C7 119.9(4) . .
C9 C8 H8 120.0 . .
C7 C8 H8 120.0 . .
C8 C9 C10 119.6(4) . .
C8 C9 H9 120.2 . .
C10 C9 H9 120.2 . .
C11 C10 C9 118.6(5) . .
C11 C10 H10 120.7 . .
C9 C10 H10 120.7 . .
N1 C11 C10 121.9(4) . .
N1 C11 H11 119.1 . .
C10 C11 H11 119.1 . .
C17 C12 C13 119.1(4) . .
C17 C12 Ir1 126.8(3) . .
C13 C12 Ir1 114.1(3) . .
C14 C13 C12 118.0(5) . .
C14 C13 C18 127.0(4) . .
C12 C13 C18 115.0(4) . .
F10 C14 C13 119.1(5) . .
F10 C14 C15 116.9(5) . .
C13 C14 C15 124.0(5) . .
C16 C15 C14 115.7(5) . .
C16 C15 H15 122.2 . .
C14 C15 H15 122.2 . .
F9 C16 C15 117.8(5) . .
F9 C16 C17 116.8(5) . .
C15 C16 C17 125.4(5) . .
C16 C17 C12 117.8(4) . .
C16 C17 H17 121.1 . .
C12 C17 H17 121.1 . .
N2 C18 C19 120.4(5) . .
N2 C18 C13 114.0(4) . .
C19 C18 C13 125.6(5) . .
C20 C19 C18 119.7(5) . .
C20 C19 H19 120.2 . .
C18 C19 H19 120.2 . .
C19 C20 C21 120.1(5) . .
C19 C20 H20 119.9 . .
C21 C20 H20 119.9 . .
C20 C21 C22 118.1(5) . .
C20 C21 H21 121.0 . .
C22 C21 H21 121.0 . .
N2 C22 C21 122.1(5) . .
N2 C22 H22 118.9 . .
C21 C22 H22 118.9 . .
N3 C23 C24 121.0(4) . .
N3 C23 C28 116.5(4) . .
C24 C23 C28 122.5(4) . .
C23 C24 C25 119.2(4) . .
C23 C24 H24 120.4 . .
C25 C24 H24 120.4 . .
C26 C25 C24 119.0(4) . .
C26 C25 H25 120.5 . .
C24 C25 H25 120.5 . .
C25 C26 C27 119.5(4) . .
C25 C26 H26 120.2 . .
C27 C26 H26 120.2 . .
N3 C27 C26 121.9(4) . .
N3 C27 H27 119.0 . .
C26 C27 H27 119.0 . .
C29 C28 N4 121.1(4) . .
C29 C28 C23 124.1(4) . .
N4 C28 C23 114.8(4) . .
C28 C29 C30 120.2(5) . .
C28 C29 H29 119.9 . .
C30 C29 H29 119.9 . .
C31 C30 C29 118.7(5) . .
C31 C30 H30 120.7 . .
C29 C30 H30 120.7 . .
C32 C31 C30 118.6(5) . .
C32 C31 H31 120.7 . .
C30 C31 H31 120.7 . .
N4 C32 C31 123.4(5) . .
N4 C32 H32 118.3 . .
C31 C32 H32 118.3 . .
C1 Ir1 C12 91.20(17) . .
C1 Ir1 N2 96.03(16) . .
C12 Ir1 N2 80.71(16) . .
C1 Ir1 N1 80.38(15) . .
C12 Ir1 N1 92.36(16) . .
N2 Ir1 N1 172.16(15) . .
C1 Ir1 N4 172.02(15) . .
C12 Ir1 N4 95.53(16) . .
N2 Ir1 N4 89.30(14) . .
N1 Ir1 N4 95.03(14) . .
C1 Ir1 N3 96.12(15) . .
C12 Ir1 N3 171.81(14) . .
N2 Ir1 N3 94.84(14) . .
N1 Ir1 N3 92.47(13) . .
N4 Ir1 N3 77.46(14) . .
C11 N1 C7 120.1(4) . .
C11 N1 Ir1 123.4(3) . .
C7 N1 Ir1 116.1(3) . .
C22 N2 C18 119.6(4) . .
C22 N2 Ir1 124.6(3) . .
C18 N2 Ir1 115.8(3) . .
C27 N3 C23 119.2(4) . .
C27 N3 Ir1 125.6(3) . .
C23 N3 Ir1 115.1(3) . .
C32 N4 C28 118.0(4) . .
C32 N4 Ir1 125.9(3) . .
C28 N4 Ir1 116.0(3) . .
F2 P1 F6 89.3(2) . .
F2 P1 F1 91.3(2) . .
F6 P1 F1 89.91(18) . .
F2 P1 F3 91.4(2) . .
F6 P1 F3 179.0(2) . .
F1 P1 F3 90.8(2) . .
F2 P1 F5 179.1(2) . .
F6 P1 F5 89.9(2) . .
F1 P1 F5 89.07(18) . .
F3 P1 F5 89.4(2) . .
F2 P1 F4 90.1(2) . .
F6 P1 F4 89.75(17) . .
F1 P1 F4 178.5(2) . .
F3 P1 F4 89.50(19) . .
F5 P1 F4 89.49(18) . .
Cl1 C33 Cl2 111.1(8) . .
Cl1 C33 H33A 109.4 . .
Cl2 C33 H33A 109.4 . .
Cl1 C33 H33B 109.4 . .
Cl2 C33 H33B 109.4 . .
H33A C33 H33B 108.0 . .
Cl1' C33' Cl2' 116.0(11) . .
Cl1' C33' H33C 108.3 . .
Cl2' C33' H33C 108.3 . .
Cl1' C33' H33D 108.3 . .
Cl2' C33' H33D 108.3 . .
H33C C33' H33D 107.4 . .
C35 C34 C37 47.8(10) . 4_556
C35 C34 C36 92.1(11) . 4_556
C37 C34 C36 47.2(9) 4_556 4_556
C35 C34 H34A 110.1 . .
C37 C34 H34A 69.0 4_556 .
C36 C34 H34A 22.6 4_556 .
C35 C34 H34B 109.3 . .
C37 C34 H34B 147.2 4_556 .
C36 C34 H34B 130.2 4_556 .
H34A C34 H34B 109.5 . .
C35 C34 H34C 109.0 . .
C37 C34 H34C 101.3 4_556 .
C36 C34 H34C 104.6 4_556 .
H34A C34 H34C 109.5 . .
H34B C34 H34C 109.5 . .
C35 C34 H34D 149.8 . .
C37 C34 H34D 110.1 4_556 .
C36 C34 H34D 62.9 4_556 .
H34A C34 H34D 41.8 . .
H34B C34 H34D 79.1 . .
H34C C34 H34D 94.3 . .
C35 C34 H34E 97.1 . .
C37 C34 H34E 49.4 4_556 .
C36 C34 H34E 21.4 4_556 .
H34A C34 H34E 36.1 . .
H34B C34 H34E 144.0 . .
H34C C34 H34E 83.3 . .
H34D C34 H34E 66.1 . .
C35 C34 H35C 74.7 . .
C37 C34 H35C 118.9 4_556 .
C36 C34 H35C 137.9 4_556 .
H34A C34 H35C 128.1 . .
H34B C34 H35C 34.9 . .
H34C C34 H35C 117.5 . .
H34D C34 H35C 111.7 . .
H34E C34 H35C 159.1 . .
C35 C34 H35D 83.1 . .
C37 C34 H35D 111.7 4_556 .
C36 C34 H35D 145.7 4_556 .
H34A C34 H35D 156.4 . .
H34B C34 H35D 82.8 . .
H34C C34 H35D 47.0 . .
H34D C34 H35D 127.1 . .
H34E C34 H35D 125.5 . .
H35C C34 H35D 73.4 . .
C37 C35 O1 151(2) 4_556 .
C37 C35 C34 67.1(16) 4_556 .
O1 C35 C34 115.7(14) . .
C37 C35 H35A 48.5 4_556 .
O1 C35 H35A 108.7 . .
C34 C35 H35A 108.4 . .
C37 C35 H35B 97.2 4_556 .
O1 C35 H35B 108.0 . .
C34 C35 H35B 108.2 . .
H35A C35 H35B 107.6 . .
C36 O1 C35 126.7(15) . .
C36 O1 H36B 54.9 . .
C35 O1 H36B 116.5 . .
C36 O1 H36C 71.4 . .
C35 O1 H36C 161.9 . .
H36B O1 H36C 72.8 . .
O1 C36 C37 126.4(17) . .
O1 C36 C34 168.3(16) . 4_456
C37 C36 C34 46.7(11) . 4_456
O1 C36 H36A 105.1 . .
C37 C36 H36A 103.5 . .
C34 C36 H36A 71.1 4_456 .
O1 C36 H36D 106.4 . .
C37 C36 H36D 107.5 . .
C34 C36 H36D 85.4 4_456 .
H36A C36 H36D 106.5 . .
O1 C36 H36B 71.0 . .
C37 C36 H36B 80.2 . .
C34 C36 H36B 112.9 4_456 .
H36A C36 H36B 175.9 . .
H36D C36 H36B 73.6 . .
O1 C36 H36C 49.9 . .
C37 C36 H36C 78.7 . .
C34 C36 H36C 119.7 4_456 .
H36A C36 H36C 107.1 . .
H36D C36 H36C 143.2 . .
H36B C36 H36C 71.8 . .
O1 C36 H37D 159.1 . .
C37 C36 H37D 47.4 . .
C34 C36 H37D 10.0 4_456 .
H36A C36 H37D 63.9 . .
H36D C36 H37D 94.1 . .
H36B C36 H37D 120.2 . .
H36C C36 H37D 114.0 . .
O1 C36 H37E 127.4 . .
C37 C36 H37E 105.9 . .
C34 C36 H37E 61.5 4_456 .
H36A C36 H37E 62.4 . .
H36D C36 H37E 45.6 . .
H36B C36 H37E 118.5 . .
H36C C36 H37E 169.1 . .
H37D C36 H37E 65.3 . .
O1 C36 H37F 105.4 . .
C37 C36 H37F 103.0 . .
C34 C36 H37F 70.8 4_456 .
H36A C36 H37F 0.6 . .
H36D C36 H37F 106.9 . .
H36B C36 H37F 176.3 . .
H36C C36 H37F 106.8 . .
H37D C36 H37F 63.5 . .
H37E C36 H37F 62.7 . .
C35 C37 C34 65.1(15) 4_456 4_456
C35 C37 C36 142(2) 4_456 .
C34 C37 C36 86.1(15) 4_456 .
C35 C37 H37A 48.9 4_456 .
C34 C37 H37A 27.3 4_456 .
C36 C37 H37A 111.3 . .
C35 C37 H37B 63.2 4_456 .
C34 C37 H37B 111.3 4_456 .
C36 C37 H37B 110.6 . .
H37A C37 H37B 109.5 . .
C35 C37 H37C 110.5 4_456 .
C34 C37 H37C 129.3 4_456 .
C36 C37 H37C 106.5 . .
H37A C37 H37C 109.5 . .
H37B C37 H37C 109.5 . .
C35 C37 H37D 81.9 4_456 .
C34 C37 H37D 26.1 4_456 .
C36 C37 H37D 63.5 . .
H37A C37 H37D 53.3 . .
H37B C37 H37D 105.6 . .
H37C C37 H37D 144.7 . .
C37' C34' C35' 165(7) 4_556 .
C37' C34' C36' 42(4) 4_556 4_556
C35' C34' C36' 131(2) . 4_556
C37' C34' H34A 35.8 4_556 .
C35' C34' H34A 156.6 . .
C36' C34' H34A 49.5 4_556 .
C37' C34' H34B 144.4 4_556 .
C35' C34' H34B 38.4 . .
C36' C34' H34B 166.1 4_556 .
H34A C34' H34B 144.3 . .
C37' C34' H34C 142.3 4_556 .
C35' C34' H34C 51.1 . .
C36' C34' H34C 120.9 4_556 .
H34A C34' H34C 106.5 . .
H34B C34' H34C 62.3 . .
C37' C34' H34D 81.9 4_556 .
C35' C34' H34D 109.1 . .
C36' C34' H34D 118.7 4_556 .
H34A C34' H34D 71.2 . .
H34B C34' H34D 74.2 . .
H34C C34' H34D 85.8 . .
C37' C34' H34E 71.1 4_556 .
C35' C34' H34E 112.8 . .
C36' C34' H34E 42.2 4_556 .
H34A C34' H34E 49.1 . .
H34B C34' H34E 141.9 . .
H34C C34' H34E 79.9 . .
H34D C34' H34E 109.5 . .
C37' C34' H34F 59.4 4_556 .
C35' C34' H34F 106.5 . .
C36' C34' H34F 67.7 4_556 .
H34A C34' H34F 95.0 . .
H34B C34' H34F 104.3 . .
H34C C34' H34F 157.0 . .
H34D C34' H34F 109.5 . .
H34E C34' H34F 109.5 . .
O1' C35' C34' 116(2) . .
O1' C35' H34B 160.0 . .
C34' C35' H34B 69.9 . .
O1' C35' H34C 115.3 . .
C34' C35' H34C 65.7 . .
H34B C35' H34C 84.7 . .
O1' C35' H35C 111.0 . .
C34' C35' H35C 111.5 . .
H34B C35' H35C 51.2 . .
H34C C35' H35C 128.5 . .
O1' C35' H35D 104.3 . .
C34' C35' H35D 105.3 . .
H34B C35' H35D 91.3 . .
H34C C35' H35D 40.3 . .
H35C C35' H35D 107.4 . .
C35' O1' C36' 117(2) . .
C35' O1' H35A 96.9 . .
C36' O1' H35A 143.0 . .
C35' O1' H35B 79.2 . .
C36' O1' H35B 115.5 . .
H35A O1' H35B 83.3 . .
O1' C36' C37' 105.7(15) . .
O1' C36' C34' 121.9(16) . 4_456
C37' C36' C34' 16.6(16) . 4_456
O1' C36' H36A 94.6 . .
C37' C36' H36A 20.7 . .
C34' C36' H36A 34.0 4_456 .
O1' C36' H36D 92.0 . .
C37' C36' H36D 49.5 . .
C34' C36' H36D 51.5 4_456 .
H36A C36' H36D 66.1 . .
O1' C36' H36B 111.6 . .
C37' C36' H36B 109.1 . .
C34' C36' H36B 97.7 4_456 .
H36A C36' H36B 129.8 . .
H36D C36' H36B 70.8 . .
O1' C36' H36C 110.4 . .
C37' C36' H36C 111.5 . .
C34' C36' H36C 105.4 4_456 .
H36A C36' H36C 100.3 . .
H36D C36' H36C 155.2 . .
H36B C36' H36C 108.6 . .
C34' C37' C36' 121(6) 4_456 .
C34' C37' H36A 132.5 4_456 .
C36' C37' H36A 75.8 . .
C34' C37' H36D 106.5 4_456 .
C36' C37' H36D 56.7 . .
H36A C37' H36D 118.3 . .
C34' C37' H37D 15.9 4_456 .
C36' C37' H37D 109.7 . .
H36A C37' H37D 122.1 . .
H36D C37' H37D 110.3 . .
C34' C37' H37E 94.3 4_456 .
C36' C37' H37E 110.6 . .
H36A C37' H37E 122.5 . .
H36D C37' H37E 56.8 . .
H37D C37' H37E 109.5 . .
C34' C37' H37F 112.0 4_456 .
C36' C37' H37F 108.2 . .
H36A C37' H37F 32.4 . .
H36D C37' H37F 140.2 . .
H37D C37' H37F 109.5 . .
H37E C37' H37F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.394(6) .
C1 C2 1.421(6) .
C1 Ir1 2.010(4) .
C2 C3 1.373(6) .
C2 C7 1.472(6) .
C3 F8 1.362(5) .
C3 C4 1.400(7) .
C4 C5 1.361(7) .
C4 H4 0.9500 .
C5 F7 1.350(6) .
C5 C6 1.382(7) .
C6 H6 0.9500 .
C7 N1 1.360(5) .
C7 C8 1.410(6) .
C8 C9 1.367(7) .
C8 H8 0.9500 .
C9 C10 1.406(8) .
C9 H9 0.9500 .
C10 C11 1.380(6) .
C10 H10 0.9500 .
C11 N1 1.354(6) .
C11 H11 0.9500 .
C12 C17 1.409(6) .
C12 C13 1.420(6) .
C12 Ir1 2.015(4) .
C13 C14 1.384(7) .
C13 C18 1.477(7) .
C14 F10 1.370(6) .
C14 C15 1.388(8) .
C15 C16 1.348(8) .
C15 H15 0.9500 .
C16 F9 1.348(6) .
C16 C17 1.387(6) .
C17 H17 0.9500 .
C18 N2 1.363(6) .
C18 C19 1.392(7) .
C19 C20 1.380(8) .
C19 H19 0.9500 .
C20 C21 1.385(8) .
C20 H20 0.9500 .
C21 C22 1.394(7) .
C21 H21 0.9500 .
C22 N2 1.351(6) .
C22 H22 0.9500 .
C23 N3 1.355(5) .
C23 C24 1.384(6) .
C23 C28 1.484(6) .
C24 C25 1.392(7) .
C24 H24 0.9500 .
C25 C26 1.360(7) .
C25 H25 0.9500 .
C26 C27 1.385(6) .
C26 H26 0.9500 .
C27 N3 1.333(6) .
C27 H27 0.9500 .
C28 C29 1.360(6) .
C28 N4 1.373(6) .
C29 C30 1.393(7) .
C29 H29 0.9500 .
C30 C31 1.389(8) .
C30 H30 0.9500 .
C31 C32 1.362(7) .
C31 H31 0.9500 .
C32 N4 1.347(6) .
C32 H32 0.9500 .
F1 P1 1.592(3) .
F2 P1 1.584(4) .
F3 P1 1.600(3) .
F4 P1 1.609(3) .
F5 P1 1.604(3) .
F6 P1 1.591(3) .
Ir1 N2 2.049(4) .
Ir1 N1 2.057(3) .
Ir1 N4 2.121(3) .
Ir1 N3 2.141(3) .
C33 Cl1 1.726(11) .
C33 Cl2 1.771(11) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C33' Cl1' 1.710(12) .
C33' Cl2' 1.749(13) .
C33' H33C 0.9900 .
C33' H33D 0.9900 .
C34 C35 1.462(16) .
C34 C37 1.48(3) 4_556
C34 C36 2.04(2) 4_556
C34 H34A 0.9600 .
C34 H34B 0.9600 .
C34 H34C 0.9599 .
C34 H35D 1.1355 .
C35 C37 1.19(2) 4_556
C35 O1 1.412(15) .
C35 H35A 0.9599 .
C35 H35B 0.9599 .
O1 C36 1.252(15) .
C36 C37 1.499(16) .
C36 C34 2.04(2) 4_456
C36 H36A 0.9599 .
C36 H36D 0.9600 .
C36 H36B 1.2663 .
C37 C35 1.19(2) 4_456
C37 C34 1.48(3) 4_456
C37 H37A 0.9600 .
C37 H37B 0.9602 .
C37 H37C 0.9598 .
C37 H37D 1.1809 .
C34' C37' 0.65(4) 4_556
C34' C35' 1.507(19) .
C34' C36' 1.94(5) 4_556
C34' H34A 0.0943 .
C34' H34D 0.9601 .
C34' H34E 0.9602 .
C34' H34F 0.9598 .
C35' O1' 1.357(18) .
C35' H34B 0.9863 .
C35' H35C 0.9601 .
C35' H35D 0.9599 .
O1' C36' 1.495(18) .
C36' C37' 1.521(18) .
C36' C34' 1.94(5) 4_456
C36' H36B 0.9600 .
C36' H36C 0.9600 .
C37' C34' 0.65(4) 4_456
C37' H36A 0.5425 .
C37' H36D 1.2056 .
C37' H37D 0.9600 .
C37' H37E 0.9600 .
C37' H37F 0.9600 .
