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#$Date: 2019-07-15 12:14:59 +0300 (Mon, 15 Jul 2019) $
#$Revision: 217035 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/31/7233125.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_7233125
loop_
_publ_author_name
'Virendra Kumar Rai'
'Masayoshi Nishiura'
'Masanori Takimoto'
'Zhaomin Hou'
_publ_section_title
;
 Guanidinate ligated iridium(III) complexes with various cyclometalated
 ligands: synthesis, structure, and highly efficient electrophosphorescent
 properties with a wide range of emission colours
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              677
_journal_page_last               689
_journal_paper_doi               10.1039/C2TC00242F
_journal_volume                  1
_journal_year                    2013
_chemical_formula_moiety         'C49 H44 Ir N5, C7 H8'
_chemical_formula_sum            'C56 H52 Ir N5'
_chemical_formula_weight         987.23
_chemical_name_common            '[(Piq)2Ir{iPrN)2C(NPh2)}]'
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 106.707(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.992(7)
_cell_length_b                   29.691(14)
_cell_length_c                   10.583(5)
_cell_measurement_reflns_used    215
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     4512(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0949
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11814
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    3.003
_exptl_absorpt_correction_T_max  0.4661
_exptl_absorpt_correction_T_min  0.3796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.112
_refine_diff_density_min         -0.818
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.859
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0346
_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)+(0.0184P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0631
_reflns_number_gt                3048
_reflns_number_total             3972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Chem-Mat-C-2013-1-677-6.cif
_cod_data_source_block           8
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7233125
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.0000 0.176586(10) 0.2500 0.02867(10) Uani 1 2 d S . .
N1 N -0.1087(3) 0.17837(13) 0.3295(3) 0.0307(9) Uani 1 1 d . . .
N2 N -0.0426(3) 0.11272(12) 0.1466(3) 0.0302(10) Uani 1 1 d . . .
N3 N 0.0000 0.03997(17) 0.2500 0.0345(15) Uani 1 2 d S . .
C1 C 0.0419(4) 0.22582(15) 0.3829(4) 0.0302(13) Uani 1 1 d . . .
C2 C 0.1187(4) 0.25335(16) 0.4008(5) 0.0398(14) Uani 1 1 d . . .
H2 H 0.1610 0.2476 0.3513 0.058 Uiso 1 1 d R . .
C3 C 0.1361(4) 0.28920(17) 0.4890(5) 0.0482(15) Uani 1 1 d . . .
H3 H 0.1909 0.3067 0.5012 0.056 Uiso 1 1 d R . .
C4 C 0.0741(4) 0.29917(17) 0.5579(5) 0.0466(15) Uani 1 1 d . . .
C5 C -0.0026(4) 0.27254(16) 0.5449(5) 0.0400(14) Uani 1 1 d . . .
H4 H 0.0845 0.3246 0.6146 0.048 Uiso 1 1 d R . .
C6 C -0.0190(3) 0.23468(15) 0.4612(4) 0.0288(12) Uani 1 1 d . . .
H5 H -0.0455 0.2797 0.5931 0.035 Uiso 1 1 d R . .
C7 C -0.1831(4) 0.15118(16) 0.2866(5) 0.0348(13) Uani 1 1 d . . .
H7 H -0.1892 0.1342 0.2084 0.042 Uiso 1 1 d R . .
C8 C -0.2499(4) 0.14678(16) 0.3493(5) 0.0383(13) Uani 1 1 d . . .
H8 H -0.3035 0.1289 0.3116 0.046 Uiso 1 1 d R . .
C9 C -0.2395(4) 0.16922(16) 0.4722(4) 0.0351(13) Uani 1 1 d . . .
C10 C -0.1618(4) 0.19740(16) 0.5175(5) 0.0339(13) Uani 1 1 d . . .
C11 C -0.0983(3) 0.20456(15) 0.4385(4) 0.0297(12) Uani 1 1 d . . .
C12 C -0.1455(4) 0.21578(16) 0.6485(5) 0.0427(14) Uani 1 1 d . . .
H12 H -0.0924 0.2341 0.6850 0.051 Uiso 1 1 d R . .
C13 C -0.2060(4) 0.20704(19) 0.7202(5) 0.0520(16) Uani 1 1 d . . .
H13 H -0.1938 0.2193 0.8064 0.062 Uiso 1 1 d R . .
C14 C -0.2845(4) 0.1808(2) 0.6706(5) 0.0502(15) Uani 1 1 d . . .
H14 H -0.3270 0.1762 0.7209 0.060 Uiso 1 1 d R . .
C15 C -0.3007(4) 0.16153(16) 0.5483(5) 0.0456(15) Uani 1 1 d . . .
H15 H -0.3538 0.1429 0.5149 0.055 Uiso 1 1 d R . .
C16 C 0.0000 0.0880(2) 0.2500 0.0319(18) Uani 1 2 d S . .
C17 C -0.0805(4) 0.09514(16) 0.0121(4) 0.0367(13) Uani 1 1 d . . .
H17 H -0.0674 0.0621 0.0134 0.044 Uiso 1 1 d R . .
C18 C -0.1847(4) 0.10188(19) -0.0351(5) 0.0578(17) Uani 1 1 d . . .
H18A H -0.2141 0.0847 0.0213 0.087 Uiso 1 1 d R . .
H18B H -0.2086 0.0914 -0.1264 0.087 Uiso 1 1 d R . .
H18C H -0.1991 0.1339 -0.0307 0.087 Uiso 1 1 d R . .
C19 C -0.0337(4) 0.11781(15) -0.0817(4) 0.0448(15) Uani 1 1 d . . .
H19A H -0.0484 0.1500 -0.0875 0.067 Uiso 1 1 d R . .
H19B H -0.0565 0.1042 -0.1694 0.067 Uiso 1 1 d R . .
H19C H 0.0339 0.1138 -0.0484 0.067 Uiso 1 1 d R . .
C20 C -0.0856(4) 0.01717(16) 0.2251(4) 0.0332(13) Uani 1 1 d . . .
C21 C -0.1538(4) 0.03187(17) 0.2785(5) 0.0460(15) Uani 1 1 d . . .
H21 H -0.1418 0.0574 0.3349 0.055 Uiso 1 1 d R . .
C22 C -0.2389(4) 0.0108(2) 0.2533(6) 0.0605(17) Uani 1 1 d . . .
H22 H -0.2848 0.0219 0.2914 0.073 Uiso 1 1 d R . .
C23 C -0.2571(4) -0.0265(2) 0.1721(6) 0.0610(18) Uani 1 1 d . . .
H23 H -0.3158 -0.0412 0.1525 0.073 Uiso 1 1 d R . .
C24 C -0.1887(5) -0.04217(19) 0.1198(5) 0.0542(16) Uani 1 1 d . . .
H24 H -0.2004 -0.0682 0.0653 0.065 Uiso 1 1 d R . .
C25 C -0.1038(4) -0.02089(16) 0.1449(5) 0.0441(15) Uani 1 1 d . . .
H25 H -0.0578 -0.0321 0.1075 0.053 Uiso 1 1 d R . .
C26 C 0.5000 -0.0380(5) 0.7500 0.190(6) Uiso 1 2 d S . .
H26A H 0.4380 -0.0490 0.7014 0.285 Uiso 0.50 1 d PR . .
H26B H 0.5161 -0.0490 0.8411 0.285 Uiso 0.50 1 d PR . .
H26C H 0.5459 -0.0490 0.7076 0.285 Uiso 0.50 1 d PR . .
C27 C 0.5000 0.0119(4) 0.7500 0.123(4) Uiso 1 2 d S . .
C28 C 0.5469(6) 0.0350(3) 0.8585(8) 0.118(3) Uiso 1 1 d . . .
H28 H 0.5796 0.0193 0.9362 0.142 Uiso 1 1 d R . .
C29 C 0.5474(7) 0.0808(3) 0.8572(10) 0.145(4) Uiso 1 1 d . . .
H29 H 0.5822 0.0965 0.9338 0.174 Uiso 1 1 d R . .
C30 C 0.5000 0.1047(5) 0.7500 0.170(6) Uiso 1 2 d S . .
H30 H 0.5000 0.1367 0.7500 0.204 Uiso 1 2 d SR . .
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'
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
C1 Ir1 C1 86.1(2) . 2
C1 Ir1 N1 98.32(18) . 2
C1 Ir1 N1 79.47(19) 2 2
C1 Ir1 N1 79.47(19) . .
C1 Ir1 N1 98.32(18) 2 .
N1 Ir1 N1 177.0(2) 2 .
C1 Ir1 N2 166.21(15) . .
C1 Ir1 N2 107.08(16) 2 .
N1 Ir1 N2 88.26(15) 2 .
N1 Ir1 N2 94.33(15) . .
C1 Ir1 N2 107.08(16) . 2
C1 Ir1 N2 166.21(15) 2 2
N1 Ir1 N2 94.33(15) 2 2
N1 Ir1 N2 88.26(15) . 2
N2 Ir1 N2 60.10(19) . 2
C7 N1 C11 120.7(4) . .
C7 N1 Ir1 121.9(3) . .
C11 N1 Ir1 117.0(3) . .
C16 N2 C17 124.5(4) . .
C16 N2 Ir1 93.7(3) . .
C17 N2 Ir1 140.1(3) . .
C20 N3 C20 122.5(6) . 2
C20 N3 C16 118.8(3) . .
C20 N3 C16 118.8(3) 2 .
C2 C1 C6 117.4(4) . .
C2 C1 Ir1 127.6(4) . .
C6 C1 Ir1 114.9(4) . .
C1 C2 C3 122.2(5) . .
C1 C2 H2 118.9 . .
C3 C2 H2 118.9 . .
C4 C3 C2 119.9(5) . .
C4 C3 H3 120.1 . .
C2 C3 H3 119.9 . .
C3 C4 C5 120.0(5) . .
C3 C4 H4 119.7 . .
C5 C4 H4 120.3 . .
C4 C5 C6 120.9(5) . .
C4 C5 H5 119.5 . .
C6 C5 H5 119.5 . .
C5 C6 C1 119.3(5) . .
C5 C6 C11 125.6(5) . .
C1 C6 C11 114.9(4) . .
N1 C7 C8 123.3(4) . .
N1 C7 H7 118.4 . .
C8 C7 H7 118.3 . .
C7 C8 C9 119.8(5) . .
C7 C8 H8 120.1 . .
C9 C8 H8 120.1 . .
C10 C9 C15 121.1(5) . .
C10 C9 C8 116.9(5) . .
C15 C9 C8 121.9(5) . .
C9 C10 C12 116.6(5) . .
C9 C10 C11 120.5(4) . .
C12 C10 C11 122.7(5) . .
N1 C11 C10 118.0(4) . .
N1 C11 C6 112.4(4) . .
C10 C11 C6 129.5(4) . .
C13 C12 C10 120.4(5) . .
C13 C12 H12 119.8 . .
C10 C12 H12 119.8 . .
C12 C13 C14 121.7(5) . .
C12 C13 H13 119.1 . .
C14 C13 H13 119.2 . .
C15 C14 C13 119.6(5) . .
C15 C14 H14 120.2 . .
C13 C14 H14 120.2 . .
C14 C15 C9 120.4(5) . .
C14 C15 H15 119.8 . .
C9 C15 H15 119.8 . .
N2 C16 N2 112.5(6) 2 .
N2 C16 N3 123.8(3) 2 .
N2 C16 N3 123.8(3) . .
N2 C17 C18 110.4(4) . .
N2 C17 C19 110.6(4) . .
C18 C17 C19 110.6(4) . .
N2 C17 H17 108.4 . .
C18 C17 H17 108.4 . .
C19 C17 H17 108.4 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C21 C20 C25 118.0(5) . .
C21 C20 N3 121.1(4) . .
C25 C20 N3 120.9(5) . .
C20 C21 C22 122.2(5) . .
C20 C21 H21 118.9 . .
C22 C21 H21 118.9 . .
C21 C22 C23 119.5(6) . .
C21 C22 H22 120.3 . .
C23 C22 H22 120.3 . .
C24 C23 C22 119.0(6) . .
C24 C23 H23 120.5 . .
C22 C23 H23 120.5 . .
C25 C24 C23 121.4(6) . .
C25 C24 H24 119.3 . .
C23 C24 H24 119.3 . .
C24 C25 C20 119.9(6) . .
C24 C25 H25 120.0 . .
C20 C25 H25 120.0 . .
C27 C26 H26A 109.5 . .
C27 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C27 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C28 C27 C28 118.8(13) . 2_656
C28 C27 C26 120.6(6) . .
C28 C27 C26 120.6(6) 2_656 .
C27 C28 C29 120.3(11) . .
C27 C28 H28 119.9 . .
C29 C28 H28 119.9 . .
C30 C29 C28 122.0(12) . .
C30 C29 H29 119.0 . .
C28 C29 H29 119.0 . .
C29 C30 C29 116.8(15) . 2_656
C29 C30 H30 121.6 . .
C29 C30 H30 121.6 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 Ir1 2.000(5) .
Ir1 C1 2.000(5) 2
Ir1 N1 2.038(4) 2
Ir1 N1 2.038(4) .
Ir1 N2 2.191(4) .
Ir1 N2 2.191(4) 2
N1 C7 1.346(5) .
N1 C11 1.363(5) .
N2 C16 1.320(5) .
N2 C17 1.469(5) .
N3 C20 1.408(5) .
N3 C20 1.408(5) 2
N3 C16 1.427(8) .
C2 C1 1.381(6) .
C2 H2 0.9468 .
C3 C2 1.390(6) .
C3 H3 0.9498 .
C4 C3 1.369(7) .
C4 H4 0.9479 .
C5 C4 1.369(7) .
C5 H5 0.9536 .
C6 C5 1.408(6) .
C6 C1 1.422(6) .
C6 C11 1.452(6) .
C7 C8 1.357(6) .
C7 H7 0.9500 .
C8 C9 1.430(6) .
C8 H8 0.9500 .
C9 C10 1.402(6) .
C9 C15 1.403(6) .
C10 C12 1.444(6) .
C10 C11 1.452(6) .
C12 C13 1.363(7) .
C12 H12 0.9500 .
C13 C14 1.384(7) .
C13 H13 0.9500 .
C14 C15 1.371(6) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 N2 1.320(5) 2
C17 C18 1.510(7) .
C17 C19 1.527(6) .
C17 H17 1.0000 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 C21 1.374(7) .
C20 C25 1.392(6) .
C21 C22 1.376(7) .
C21 H21 0.9500 .
C22 C23 1.381(7) .
C22 H22 0.9500 .
C23 C24 1.378(8) .
C23 H23 0.9500 .
C24 C25 1.376(7) .
C24 H24 0.9500 .
C25 H25 0.9500 .
C26 C27 1.482(15) .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 C28 1.350(9) .
C27 C28 1.350(9) 2_656
C28 C29 1.358(9) .
C28 H28 0.9500 .
C29 C30 1.354(10) .
C29 H29 0.9500 .
C30 C29 1.354(10) 2_656
C30 H30 0.9500 .
