#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:07:28 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179741 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/37/7003739.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_7003739
loop_
_publ_author_name
'Byun, Younghun'
'Jeon, Woo Sung'
'Lee, Tae-Woo'
'Lyu, Yi-Yeol'
'Chang, Seok'
'Kwon, Ohyun'
'Han, Eunsil'
'Kim, Heekyung'
'Kim, Myeongsuk'
'Lee, Ha-Jin'
'Das, Rupasree Ragini'
_publ_section_title
;
 Study on a set of bis-cyclometalated Ir(iii) complexes with a common
 ancillary ligand
;
_journal_issue                   35
_journal_name_full               'Dalton Transactions'
_journal_page_first              4732
_journal_page_last               4741
_journal_paper_doi               10.1039/b719205c
_journal_year                    2008
_chemical_formula_sum            'C28 H20 F4 Ir N5 O'
_chemical_formula_weight         710.69
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 96.012(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.572(2)
_cell_length_b                   9.523(2)
_cell_length_c                   22.409(5)
_cell_measurement_reflns_used    5004
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.251
_cell_measurement_theta_min      2.326
_cell_volume                     2455.9(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP3
_computing_publication_material  WinGX
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14916
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        <2.0
_exptl_absorpt_coefficient_mu    5.500
_exptl_absorpt_correction_T_max  0.4925
_exptl_absorpt_correction_T_min  0.2290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.561
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0225
_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)+(0.0209P)²+2.2776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0499
_refine_ls_wR_factor_ref         0.0517
_reflns_number_gt                5131
_reflns_number_total             5851
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b719205c.txt
_cod_data_source_block           o4_77mo
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7003739
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.280150(9) 0.762096(10) 0.574649(5) 0.01943(4) Uani 1 1 d . . .
F1 F -0.0033(2) 0.3658(2) 0.65520(10) 0.0534(6) Uani 1 1 d . . .
F2 F 0.00600(18) 0.8044(2) 0.74811(8) 0.0376(5) Uani 1 1 d . . .
F3 F 0.6428(2) 0.7603(2) 0.74753(10) 0.0521(6) Uani 1 1 d . . .
F4 F 0.58256(19) 0.3574(2) 0.62878(9) 0.0446(5) Uani 1 1 d . . .
O1 O 0.39126(19) 1.0002(2) 0.43254(9) 0.0282(5) Uani 1 1 d . . .
N1 N 0.1630(2) 0.8445(2) 0.50278(10) 0.0218(5) Uani 1 1 d . . .
N2 N 0.2203(2) 0.9085(2) 0.45909(10) 0.0213(5) Uani 1 1 d . . .
N3 N 0.3871(2) 0.8737(2) 0.52081(11) 0.0231(5) Uani 1 1 d . . .
H3 H 0.4601 0.8816 0.5322 0.028 Uiso 1 1 calc R . .
N4 N 0.2517(2) 0.9299(2) 0.62836(10) 0.0220(5) Uani 1 1 d . . .
N5 N 0.3062(2) 0.5808(2) 0.52951(11) 0.0234(5) Uani 1 1 d . . .
C1 C 0.1452(3) 0.9399(3) 0.41010(13) 0.0275(6) Uani 1 1 d . . .
C2 C 0.0383(3) 0.8954(3) 0.42268(14) 0.0309(7) Uani 1 1 d . . .
H2 H -0.0308 0.9028 0.3976 0.037 Uiso 1 1 calc R . .
C3 C 0.0515(3) 0.8363(3) 0.48027(13) 0.0249(6) Uani 1 1 d . . .
C4 C 0.3444(3) 0.9310(3) 0.47032(12) 0.0214(6) Uani 1 1 d . . .
C5 C 0.1798(3) 1.0092(4) 0.35466(15) 0.0418(9) Uani 1 1 d . . .
H5A H 0.2418 0.9570 0.3399 0.063 Uiso 1 1 calc R . .
H5B H 0.2054 1.1032 0.3640 0.063 Uiso 1 1 calc R . .
H5C H 0.1143 1.0116 0.3246 0.063 Uiso 1 1 calc R . .
C6 C -0.0381(3) 0.7675(3) 0.51329(17) 0.0343(7) Uani 1 1 d . . .
H6A H -0.0226 0.7872 0.5554 0.052 Uiso 1 1 calc R . .
H6B H -0.0361 0.6678 0.5070 0.052 Uiso 1 1 calc R . .
H6C H -0.1136 0.8029 0.4988 0.052 Uiso 1 1 calc R . .
C7 C 0.3024(3) 1.0568(3) 0.62373(13) 0.0282(7) Uani 1 1 d . . .
H7 H 0.3530 1.0697 0.5946 0.034 Uiso 1 1 calc R . .
C8 C 0.2817(3) 1.1675(3) 0.66056(15) 0.0324(7) Uani 1 1 d . . .
H8 H 0.3160 1.2545 0.6556 0.039 Uiso 1 1 calc R . .
C9 C 0.2085(3) 1.1473(3) 0.70531(14) 0.0327(7) Uani 1 1 d . . .
H9 H 0.1938 1.2204 0.7310 0.039 Uiso 1 1 calc R . .
C10 C 0.1581(3) 1.0175(3) 0.71112(13) 0.0282(7) Uani 1 1 d . . .
H10 H 0.1103 1.0023 0.7414 0.034 Uiso 1 1 calc R . .
C11 C 0.1785(3) 0.9086(3) 0.67171(12) 0.0232(6) Uani 1 1 d . . .
C12 C 0.1278(3) 0.7672(3) 0.66976(13) 0.0223(6) Uani 1 1 d . . .
C13 C 0.1671(3) 0.6746(3) 0.62638(12) 0.0224(6) Uani 1 1 d . . .
C14 C 0.1224(3) 0.5378(3) 0.62329(14) 0.0293(7) Uani 1 1 d . . .
H14 H 0.1480 0.4739 0.5962 0.035 Uiso 1 1 calc R . .
C15 C 0.0409(3) 0.4980(3) 0.66021(15) 0.0339(7) Uani 1 1 d . . .
C16 C -0.0005(3) 0.5851(4) 0.70230(14) 0.0335(7) Uani 1 1 d . . .
H16 H -0.0558 0.5553 0.7268 0.040 Uiso 1 1 calc R . .
C17 C 0.0449(3) 0.7189(3) 0.70599(13) 0.0275(6) Uani 1 1 d . . .
C18 C 0.2465(3) 0.5452(3) 0.47682(13) 0.0267(6) Uani 1 1 d . . .
H18 H 0.1916 0.6076 0.4589 0.032 Uiso 1 1 calc R . .
C19 C 0.2640(3) 0.4192(3) 0.44850(15) 0.0305(7) Uani 1 1 d . . .
H19 H 0.2216 0.3976 0.4121 0.037 Uiso 1 1 calc R . .
C20 C 0.3452(3) 0.3257(3) 0.47483(16) 0.0355(8) Uani 1 1 d . . .
H20 H 0.3581 0.2402 0.4566 0.043 Uiso 1 1 calc R . .
C21 C 0.4069(3) 0.3617(3) 0.52892(15) 0.0323(7) Uani 1 1 d . . .
H21 H 0.4614 0.2995 0.5473 0.039 Uiso 1 1 calc R . .
C22 C 0.3879(3) 0.4909(3) 0.55615(13) 0.0254(6) Uani 1 1 d . . .
C23 C 0.4498(3) 0.5480(3) 0.61085(13) 0.0256(6) Uani 1 1 d . . .
C24 C 0.4143(3) 0.6832(3) 0.62811(13) 0.0240(6) Uani 1 1 d . . .
C25 C 0.4798(3) 0.7525(3) 0.67524(13) 0.0292(7) Uani 1 1 d . . .
H25 H 0.4579 0.8411 0.6874 0.035 Uiso 1 1 calc R . .
C26 C 0.5771(3) 0.6876(4) 0.70330(14) 0.0343(7) Uani 1 1 d . . .
C27 C 0.6117(3) 0.5548(4) 0.68929(15) 0.0374(8) Uani 1 1 d . . .
H27 H 0.6762 0.5123 0.7101 0.045 Uiso 1 1 calc R . .
C28 C 0.5472(3) 0.4883(3) 0.64351(14) 0.0315(7) Uani 1 1 d . . .
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'
O O 0.0106 0.0060 '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'
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
_geom_angle_publ_flag
C24 Ir1 C13 90.56(11) . . ?
C24 Ir1 N5 80.43(11) . . ?
C13 Ir1 N5 94.24(10) . . ?
C24 Ir1 N4 95.91(11) . . ?
C13 Ir1 N4 80.25(11) . . ?
N5 Ir1 N4 173.41(9) . . ?
C24 Ir1 N3 93.84(11) . . ?
C13 Ir1 N3 173.68(10) . . ?
N5 Ir1 N3 90.96(9) . . ?
N4 Ir1 N3 94.78(9) . . ?
C24 Ir1 N1 167.36(10) . . ?
C13 Ir1 N1 100.73(10) . . ?
N5 Ir1 N1 92.99(9) . . ?
N4 Ir1 N1 91.61(9) . . ?
N3 Ir1 N1 75.38(9) . . ?
C3 N1 N2 105.9(2) . . ?
C3 N1 Ir1 140.5(2) . . ?
N2 N1 Ir1 112.45(17) . . ?
C1 N2 N1 110.8(2) . . ?
C1 N2 C4 130.3(2) . . ?
N1 N2 C4 118.9(2) . . ?
C4 N3 Ir1 121.1(2) . . ?
C7 N4 C11 119.5(2) . . ?
C7 N4 Ir1 123.7(2) . . ?
C11 N4 Ir1 116.81(19) . . ?
C18 N5 C22 119.6(3) . . ?
C18 N5 Ir1 124.0(2) . . ?
C22 N5 Ir1 116.5(2) . . ?
N2 C1 C2 106.4(3) . . ?
N2 C1 C5 124.2(3) . . ?
C2 C1 C5 129.4(3) . . ?
C1 C2 C3 107.5(3) . . ?
N1 C3 C2 109.4(3) . . ?
N1 C3 C6 122.2(3) . . ?
C2 C3 C6 128.3(3) . . ?
O1 C4 N3 131.3(3) . . ?
O1 C4 N2 117.2(3) . . ?
N3 C4 N2 111.5(2) . . ?
N4 C7 C8 122.4(3) . . ?
C7 C8 C9 118.9(3) . . ?
C10 C9 C8 119.2(3) . . ?
C9 C10 C11 120.3(3) . . ?
N4 C11 C10 119.8(3) . . ?
N4 C11 C12 112.9(2) . . ?
C10 C11 C12 127.3(3) . . ?
C17 C12 C13 118.8(3) . . ?
C17 C12 C11 125.5(3) . . ?
C13 C12 C11 115.7(3) . . ?
C14 C13 C12 117.9(3) . . ?
C14 C13 Ir1 127.9(2) . . ?
C12 C13 Ir1 114.2(2) . . ?
C15 C14 C13 120.1(3) . . ?
F1 C15 C14 118.8(3) . . ?
F1 C15 C16 117.3(3) . . ?
C14 C15 C16 123.8(3) . . ?
C17 C16 C15 116.1(3) . . ?
F2 C17 C16 116.4(3) . . ?
F2 C17 C12 120.2(3) . . ?
C16 C17 C12 123.4(3) . . ?
N5 C18 C19 122.3(3) . . ?
C20 C19 C18 119.3(3) . . ?
C19 C20 C21 118.7(3) . . ?
C20 C21 C22 120.6(3) . . ?
N5 C22 C21 119.5(3) . . ?
N5 C22 C23 113.0(3) . . ?
C21 C22 C23 127.5(3) . . ?
C28 C23 C24 117.9(3) . . ?
C28 C23 C22 125.9(3) . . ?
C24 C23 C22 115.9(3) . . ?
C25 C24 C23 119.0(3) . . ?
C25 C24 Ir1 126.8(2) . . ?
C23 C24 Ir1 113.9(2) . . ?
C26 C25 C24 119.1(3) . . ?
F3 C26 C27 118.5(3) . . ?
F3 C26 C25 118.0(3) . . ?
C27 C26 C25 123.6(3) . . ?
C28 C27 C26 116.8(3) . . ?
C27 C28 F4 116.9(3) . . ?
C27 C28 C23 123.7(3) . . ?
F4 C28 C23 119.4(3) . . ?
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 C24 2.005(3) . ?
Ir1 C13 2.016(3) . ?
Ir1 N5 2.039(2) . ?
Ir1 N4 2.048(2) . ?
Ir1 N3 2.104(2) . ?
Ir1 N1 2.142(2) . ?
F1 C15 1.359(4) . ?
F2 C17 1.358(3) . ?
F3 C26 1.372(4) . ?
F4 C28 1.364(4) . ?
O1 C4 1.241(3) . ?
N1 C3 1.338(4) . ?
N1 N2 1.380(3) . ?
N2 C1 1.360(4) . ?
N2 C4 1.447(4) . ?
N3 C4 1.306(4) . ?
N4 C7 1.352(4) . ?
N4 C11 1.370(4) . ?
N5 C18 1.347(4) . ?
N5 C22 1.366(4) . ?
C1 C2 1.365(5) . ?
C1 C5 1.498(4) . ?
C2 C3 1.401(4) . ?
C3 C6 1.488(4) . ?
C7 C8 1.376(4) . ?
C8 C9 1.392(5) . ?
C9 C10 1.379(5) . ?
C10 C11 1.398(4) . ?
C11 C12 1.468(4) . ?
C12 C17 1.398(4) . ?
C12 C13 1.422(4) . ?
C13 C14 1.401(4) . ?
C14 C15 1.371(4) . ?
C15 C16 1.379(5) . ?
C16 C17 1.377(4) . ?
C18 C19 1.382(4) . ?
C19 C20 1.381(5) . ?
C20 C21 1.384(5) . ?
C21 C22 1.401(4) . ?
C22 C23 1.459(4) . ?
C23 C28 1.398(4) . ?
C23 C24 1.418(4) . ?
C24 C25 1.399(4) . ?
C25 C26 1.377(5) . ?
C26 C27 1.374(5) . ?
C27 C28 1.360(5) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O1 0.86 2.14 2.925(3) 152.1 3_676
