#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:56:35 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179162 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/23/4312350.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_4312350
loop_
_publ_author_name
'Kenneth Kam-Wing Lo'
'Chi-Keung Chung'
'Terence Kwok-Ming Lee'
'Lok-Hei Lui'
'Keith Hing-Kit Tsang'
'Nianyong Zhu'
_publ_section_title
;
 New Luminescent Cyclometalated Iridium(III) Diimine Complexes as
 Biological Labeling Reagents
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6886
_journal_page_last               6897
_journal_paper_doi               10.1021/ic0346984
_journal_volume                  42
_journal_year                    2003
_chemical_formula_moiety         'C31 H30 Cl2 F6 Ir N7 O P'
_chemical_formula_sum            'C31 H30 Cl2 F6 Ir N7 O P'
_chemical_formula_weight         924.69
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           64
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2ac 2'
_symmetry_space_group_name_H-M   'C m c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.772(5)
_cell_length_b                   18.227(4)
_cell_length_c                   17.728(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     7358(3)
_computing_cell_refinement       Scalepack
_computing_data_collection       Marcontrol
_computing_data_reduction        Denzo
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Shelxs-97
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Marresearch imaging plate mar300'
_diffrn_measurement_method       Oscillation
_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  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22424
_diffrn_reflns_theta_full        25.54
_diffrn_reflns_theta_max         25.54
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    3.884
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3624
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.910
_refine_diff_density_min         -1.211
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0930P)²+24.9383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.1682
_reflns_number_gt                2167
_reflns_number_total             3324
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0346984si20030619_025721.cif
_cod_data_source_block           mar348a
_cod_database_code               4312350
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'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x, y, z'
'x, -y-1/2, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y, 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
Ir1 Ir 0.2500 0.49163(2) 0.2500 0.0648(2) Uani 1 2 d S . .
N1 N 0.3631(4) 0.5533(5) 0.2156(6) 0.097(2) Uani 1 1 d . . .
N2 N 0.3253(3) 0.4998(4) 0.1874(4) 0.0756(19) Uani 1 1 d . . .
N3 N 0.2111(3) 0.3999(3) 0.1946(3) 0.0705(17) Uani 1 1 d . . .
N4 N 0.1450(8) 0.2124(9) 0.1068(10) 0.117(6) Uani 0.50 1 d P . .
H4A H 0.1624 0.1764 0.1322 0.176 Uiso 0.33 1 calc PR . .
H4B H 0.1558 0.2105 0.0586 0.176 Uiso 0.33 1 calc PR . .
H4C H 0.1062 0.2073 0.1100 0.176 Uiso 0.33 1 calc PR . .
C1 C 0.2909(4) 0.5714(4) 0.3095(5) 0.082(2) Uani 1 1 d . . .
C2 C 0.2732(5) 0.6060(5) 0.3752(6) 0.103(3) Uani 1 1 d . . .
H2 H 0.2370 0.5943 0.3962 0.124 Uiso 1 1 calc R . .
C3 C 0.3082(7) 0.6575(6) 0.4099(8) 0.142(5) Uani 1 1 d . . .
H3 H 0.2962 0.6785 0.4552 0.170 Uiso 1 1 calc R . .
C4 C 0.3598(8) 0.6779(8) 0.3784(11) 0.166(8) Uani 1 1 d . . .
H4 H 0.3817 0.7156 0.3998 0.199 Uiso 1 1 calc R . .
C5 C 0.3797(6) 0.6432(7) 0.3155(10) 0.149(6) Uani 1 1 d . . .
H5 H 0.4163 0.6551 0.2958 0.179 Uiso 1 1 calc R . .
C6 C 0.3458(5) 0.5904(6) 0.2809(7) 0.095(3) Uani 1 1 d . . .
C7 C 0.4111(5) 0.5568(9) 0.1689(9) 0.139(6) Uani 1 1 d . . .
H7 H 0.4431 0.5881 0.1744 0.167 Uiso 1 1 calc R . .
C8 C 0.4040(6) 0.5094(10) 0.1161(9) 0.147(6) Uani 1 1 d . . .
H8 H 0.4302 0.5015 0.0767 0.177 Uiso 1 1 calc R . .
C9 C 0.3497(4) 0.4700(6) 0.1266(6) 0.097(3) Uani 1 1 d . . .
C10 C 0.3234(5) 0.4117(7) 0.0820(6) 0.123(4) Uani 1 1 d . . .
H10A H 0.2872 0.3965 0.1051 0.185 Uiso 1 1 calc R . .
H10B H 0.3499 0.3707 0.0797 0.185 Uiso 1 1 calc R . .
H10C H 0.3157 0.4293 0.0320 0.185 Uiso 1 1 calc R . .
C11 C 0.2284(4) 0.3321(5) 0.2211(5) 0.070(2) Uani 1 1 d . . .
C12 C 0.2019(5) 0.2691(4) 0.1925(6) 0.096(3) Uani 1 1 d . . .
H12 H 0.2121 0.2234 0.2118 0.116 Uiso 1 1 calc R . .
C13 C 0.1599(5) 0.2740(6) 0.1348(7) 0.106(3) Uani 1 1 d . . .
C14 C 0.1441(5) 0.3401(6) 0.1127(6) 0.103(3) Uani 1 1 d . . .
H14 H 0.1152 0.3442 0.0759 0.124 Uiso 1 1 calc R . .
C15 C 0.1683(4) 0.4036(5) 0.1417(5) 0.084(3) Uani 1 1 d . . .
H15 H 0.1552 0.4490 0.1248 0.101 Uiso 1 1 calc R . .
P1 P 0.0000 0.1905(3) -0.0022(2) 0.0940(13) Uani 1 2 d S . .
F1 F 0.0675(3) 0.1930(9) 0.0011(6) 0.235(6) Uani 1 1 d . . .
F2 F 0.0000 0.1690(7) 0.0860(7) 0.178(5) Uani 1 2 d S . .
F3 F 0.0000 0.2745(10) 0.0139(9) 0.238(11) Uani 1 2 d S . .
F4 F 0.0000 0.2045(12) -0.0866(8) 0.274(9) Uani 1 2 d S . .
F5 F 0.0000 0.1126(8) -0.0178(12) 0.332(12) Uani 1 2 d S . .
Cl1 Cl 0.5000 0.4475(6) 0.2966(5) 0.251(4) Uani 1 2 d S . .
Cl2 Cl 0.5000 0.2893(9) 0.2763(6) 0.274(5) Uani 1 2 d S . .
C16 C 0.5000 0.372(2) 0.2309(12) 0.36(3) Uani 1 2 d S . .
H16A H 0.4655 0.3757 0.1989 0.438 Uiso 0.50 1 calc PR . .
H16B H 0.5345 0.3757 0.1989 0.438 Uiso 0.50 1 calc PR . .
O1 O 0.0634(5) 0.5000 0.0000 0.138(4) Uani 1 2 d S . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Ir Ir -1.4442 7.9887 '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'
C C 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'
H H 0.0000 0.0000 '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
_geom_angle_publ_flag
C1 Ir1 C1 88.1(5) . 8_545 ?
C1 Ir1 N2 81.1(4) . . ?
C1 Ir1 N2 92.9(3) 8_545 . ?
C1 Ir1 N2 92.9(3) . 8_545 ?
C1 Ir1 N2 81.1(4) 8_545 8_545 ?
N2 Ir1 N2 171.7(4) . 8_545 ?
C1 Ir1 N3 174.3(3) . . ?
C1 Ir1 N3 97.6(3) 8_545 . ?
N2 Ir1 N3 98.9(3) . . ?
N2 Ir1 N3 87.6(2) 8_545 . ?
C1 Ir1 N3 97.6(3) . 8_545 ?
C1 Ir1 N3 174.3(3) 8_545 8_545 ?
N2 Ir1 N3 87.6(2) . 8_545 ?
N2 Ir1 N3 98.9(3) 8_545 8_545 ?
N3 Ir1 N3 76.7(4) . 8_545 ?
C7 N1 N2 108.0(10) . . ?
C7 N1 C6 134.5(11) . . ?
N2 N1 C6 117.5(8) . . ?
C9 N2 N1 108.6(8) . . ?
C9 N2 Ir1 139.5(7) . . ?
N1 N2 Ir1 111.9(6) . . ?
C15 N3 C11 119.0(7) . . ?
C15 N3 Ir1 125.4(5) . . ?
C11 N3 Ir1 115.3(5) . . ?
C2 C1 C6 117.0(10) . . ?
C2 C1 Ir1 129.2(8) . . ?
C6 C1 Ir1 113.7(8) . . ?
C3 C2 C1 121.2(12) . . ?
C4 C3 C2 120.4(15) . . ?
C3 C4 C5 119.9(13) . . ?
C4 C5 C6 120.3(15) . . ?
C5 C6 C1 121.0(13) . . ?
C5 C6 N1 123.3(12) . . ?
C1 C6 N1 115.7(9) . . ?
C8 C7 N1 107.9(12) . . ?
C7 C8 C9 110.4(13) . . ?
N2 C9 C8 105.1(12) . . ?
N2 C9 C10 124.6(9) . . ?
C8 C9 C10 130.3(12) . . ?
N3 C11 C12 119.5(8) . . ?
N3 C11 C11 116.3(5) . 8_545 ?
C12 C11 C11 124.2(6) . 8_545 ?
C11 C12 C13 120.5(8) . . ?
N4 C13 C14 128.0(14) . . ?
N4 C13 C12 114.2(13) . . ?
C14 C13 C12 117.6(9) . . ?
C13 C14 C15 123.1(10) . . ?
N3 C15 C14 120.3(9) . . ?
F5 P1 F4 88.6(11) . . ?
F5 P1 F1 92.1(6) . 11 ?
F4 P1 F1 91.9(4) . 11 ?
F5 P1 F1 92.1(6) . . ?
F4 P1 F1 91.9(4) . . ?
F1 P1 F1 174.4(11) 11 . ?
F5 P1 F3 179.5(11) . . ?
F4 P1 F3 90.8(9) . . ?
F1 P1 F3 87.9(6) 11 . ?
F1 P1 F3 87.9(6) . . ?
F5 P1 F2 87.0(9) . . ?
F4 P1 F2 175.6(10) . . ?
F1 P1 F2 88.3(4) 11 . ?
F1 P1 F2 88.3(4) . . ?
F3 P1 F2 93.5(8) . . ?
Cl2 C16 Cl1 111.6(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C1 2.022(8) . ?
Ir1 C1 2.022(8) 8_545 ?
Ir1 N2 2.047(7) . ?
Ir1 N2 2.047(7) 8_545 ?
Ir1 N3 2.131(6) . ?
Ir1 N3 2.131(6) 8_545 ?
N1 C7 1.374(14) . ?
N1 N2 1.394(10) . ?
N1 C6 1.397(14) . ?
N2 C9 1.329(12) . ?
N3 C15 1.353(10) . ?
N3 C11 1.379(10) . ?
N4 C13 1.275(16) . ?
C1 C2 1.385(13) . ?
C1 C6 1.394(13) . ?
C2 C3 1.377(14) . ?
C3 C4 1.35(2) . ?
C4 C5 1.36(2) . ?
C5 C6 1.377(15) . ?
C7 C8 1.285(18) . ?
C8 C9 1.442(17) . ?
C9 C10 1.453(14) . ?
C11 C12 1.393(12) . ?
C11 C11 1.422(17) 8_545 ?
C12 C13 1.403(14) . ?
C13 C14 1.316(14) . ?
C14 C15 1.382(12) . ?
P1 F5 1.447(14) . ?
P1 F4 1.518(14) . ?
P1 F1 1.538(8) 11 ?
P1 F1 1.538(8) . ?
P1 F3 1.557(18) . ?
P1 F2 1.612(11) . ?
Cl1 C16 1.80(3) . ?
Cl2 C16 1.71(3) . ?
