#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/58/2235863.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2235863
loop_
_publ_author_name
'Ge, Guo-Ping'
'Li, Chun-Yan'
_publ_section_title
;
 (Acetylacetonato-κ²O,O')bis{5-fluoro-2-[3-(4-fluorophenyl)pyrazin-2-yl]phenyl-κ²N¹,C¹}iridium(III)
;
_journal_coeditor_code           HY2570
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1079
_journal_paper_doi               10.1107/S1600536812031546
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Ir (C16 H9 F2 N2)2 (C5 H7 O2)]'
_chemical_formula_moiety         'C37 H25 F4 Ir N4 O2'
_chemical_formula_sum            'C37 H25 F4 Ir N4 O2'
_chemical_formula_weight         825.83
_chemical_name_systematic
;
(Acetylacetonato-κ²O,O')bis{5-fluoro-2-[3-(4-
fluorophenyl)pyrazin-2-yl]phenyl-κ²N¹,C¹}iridium(III)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.58(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.030(4)
_cell_length_b                   10.010(2)
_cell_length_c                   16.118(3)
_cell_measurement_reflns_used    3730
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.26
_cell_volume                     3268.3(12)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotation anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14813
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    4.148
_exptl_absorpt_correction_T_max  0.470
_exptl_absorpt_correction_T_min  0.263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylindric
_exptl_crystal_F_000             1616.0
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         2.147
_refine_diff_density_min         -2.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0320
_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)+(0.0468P)²+2.1663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0787
_reflns_number_gt                3573
_reflns_number_total             3714
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2570.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235863
_cod_database_fobs_code          2235863
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Ir Ir 0.0000 0.399077(13) 0.2500 0.02715(8) Uani d S 1 2
N N1 -0.08587(17) 0.4046(2) 0.1576(2) 0.0322(6) Uani d . 1 1
N N2 -0.20277(17) 0.4187(3) 0.0278(2) 0.0438(8) Uani d . 1 1
F F1 0.15157(10) 0.7392(3) 0.12655(16) 0.0565(6) Uani d . 1 1
F F2 -0.2418(2) 0.9357(4) -0.1927(3) 0.0993(12) Uani d . 1 1
C C1 -0.13642(17) 0.3191(3) 0.1545(2) 0.0403(7) Uani d . 1 1
H H2A -0.1330 0.2571 0.1985 0.048 Uiso calc R 1 1
C C2 -0.19232(18) 0.3227(4) 0.0876(3) 0.0491(9) Uani d . 1 1
H H1A -0.2240 0.2565 0.0836 0.059 Uiso calc R 1 1
C C3 -0.15473(15) 0.5090(3) 0.03242(19) 0.0340(6) Uani d . 1 1
C C4 -0.09249(14) 0.4969(3) 0.09367(18) 0.0294(6) Uani d . 1 1
C C5 -0.03044(15) 0.5686(3) 0.0989(2) 0.0287(6) Uani d . 1 1
C C6 0.02113(15) 0.5378(3) 0.1734(2) 0.0286(6) Uani d . 1 1
C C7 0.0829(2) 0.5995(3) 0.1821(3) 0.0360(8) Uani d . 1 1
H H25A 0.1175 0.5854 0.2311 0.043 Uiso calc R 1 1
C C8 0.09109(16) 0.6806(3) 0.1172(2) 0.0377(7) Uani d . 1 1
C C9 0.04288(16) 0.7039(3) 0.0422(2) 0.0362(6) Uani d . 1 1
H H16A 0.0514 0.7559 -0.0014 0.043 Uiso calc R 1 1
C C10 -0.01820(16) 0.6482(3) 0.0333(2) 0.0326(6) Uani d . 1 1
H H15A -0.0518 0.6634 -0.0167 0.039 Uiso calc R 1 1
C C11 -0.17425(18) 0.6233(4) -0.0285(3) 0.0375(8) Uani d . 1 1
C C12 -0.16476(17) 0.7527(4) 0.0010(2) 0.0439(8) Uani d . 1 1
H H14A -0.1429 0.7691 0.0583 0.053 Uiso calc R 1 1
C C13 -0.1875(2) 0.8589(5) -0.0543(3) 0.0549(10) Uani d . 1 1
H H12A -0.1811 0.9467 -0.0350 0.066 Uiso calc R 1 1
C C14 -0.2196(2) 0.8303(5) -0.1381(3) 0.0632(12) Uani d . 1 1
C C15 -0.2303(2) 0.7040(5) -0.1699(3) 0.0624(12) Uani d . 1 1
H H13A -0.2524 0.6887 -0.2273 0.075 Uiso calc R 1 1
C C16 -0.2074(2) 0.5988(4) -0.1142(3) 0.0492(11) Uani d . 1 1
H H3A -0.2141 0.5114 -0.1341 0.059 Uiso calc R 1 1
C C17 0.0240(2) 0.1210(4) 0.1865(3) 0.0475(10) Uani d . 1 1
C C18 0.0470(3) 0.0333(5) 0.1240(4) 0.0766(15) Uani d . 1 1
H H21A 0.0621 0.0883 0.0844 0.115 Uiso calc R 1 1
H H21B 0.0110 -0.0214 0.0928 0.115 Uiso calc R 1 1
H H21C 0.0825 -0.0227 0.1552 0.115 Uiso calc R 1 1
C C19 0.0000 0.0599(6) 0.2500 0.0603(16) Uani d S 1 2
H H22A 0.0000 -0.0330 0.2500 0.072 Uiso calc SR 1 2
O O1 0.02969(13) 0.2442(3) 0.17557(16) 0.0398(5) Uani d . 1 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C6 Ir C6 2 . 91.30(18)
C6 Ir N1 2 . 97.75(12)
C6 Ir N1 . . 80.01(12)
C6 Ir N1 2 2 80.01(12)
C6 Ir N1 . 2 97.75(12)
N1 Ir N1 . 2 176.82(13)
C6 Ir O1 2 . 175.30(9)
C6 Ir O1 . . 90.58(13)
N1 Ir O1 . . 86.82(11)
N1 Ir O1 2 . 95.48(11)
C6 Ir O1 2 2 90.58(13)
C6 Ir O1 . 2 175.30(9)
N1 Ir O1 . 2 95.48(11)
N1 Ir O1 2 2 86.82(11)
O1 Ir O1 . 2 87.88(15)
C4 N1 C1 . . 118.7(3)
C4 N1 Ir . . 117.9(2)
C1 N1 Ir . . 123.3(2)
C3 N2 C2 . . 117.9(3)
N1 C1 C2 . . 120.8(3)
N1 C1 H2A . . 119.6
C2 C1 H2A . . 119.6
N2 C2 C1 . . 121.9(3)
N2 C2 H1A . . 119.0
C1 C2 H1A . . 119.0
N2 C3 C4 . . 121.5(3)
N2 C3 C11 . . 114.2(3)
C4 C3 C11 . . 124.3(3)
N1 C4 C3 . . 118.2(3)
N1 C4 C5 . . 112.2(3)
C3 C4 C5 . . 129.6(3)
C10 C5 C6 . . 120.5(3)
C10 C5 C4 . . 125.0(3)
C6 C5 C4 . . 114.0(3)
C7 C6 C5 . . 117.6(3)
C7 C6 Ir . . 126.7(2)
C5 C6 Ir . . 115.5(2)
C8 C7 C6 . . 118.9(3)
C8 C7 H25A . . 120.6
C6 C7 H25A . . 120.6
F1 C8 C7 . . 118.2(3)
F1 C8 C9 . . 117.9(3)
C7 C8 C9 . . 123.9(3)
C10 C9 C8 . . 118.2(3)
C10 C9 H16A . . 120.9
C8 C9 H16A . . 120.9
C9 C10 C5 . . 120.5(3)
C9 C10 H15A . . 119.7
C5 C10 H15A . . 119.7
C12 C11 C16 . . 119.7(3)
C12 C11 C3 . . 120.5(3)
C16 C11 C3 . . 119.6(3)
C11 C12 C13 . . 120.5(4)
C11 C12 H14A . . 119.8
C13 C12 H14A . . 119.8
C14 C13 C12 . . 117.9(5)
C14 C13 H12A . . 121.1
C12 C13 H12A . . 121.1
C13 C14 C15 . . 123.6(4)
C13 C14 F2 . . 117.7(5)
C15 C14 F2 . . 118.7(5)
C14 C15 C16 . . 118.0(4)
C14 C15 H13A . . 121.0
C16 C15 H13A . . 121.0
C15 C16 C11 . . 120.3(4)
C15 C16 H3A . . 119.9
C11 C16 H3A . . 119.9
O1 C17 C19 . . 126.8(4)
O1 C17 C18 . . 114.7(4)
C19 C17 C18 . . 118.5(4)
C17 C18 H21A . . 109.5
C17 C18 H21B . . 109.5
H21A C18 H21B . . 109.5
C17 C18 H21C . . 109.5
H21A C18 H21C . . 109.5
H21B C18 H21C . . 109.5
C17 C19 C17 2 . 128.1(6)
C17 C19 H22A 2 . 115.9
C17 C19 H22A . . 115.9
C17 O1 Ir . . 125.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ir C6 . 1.987(3) y
Ir N1 . 2.009(3) y
Ir O1 . 2.153(2) y
N1 C4 . 1.363(4) ?
N1 C1 . 1.356(4) ?
N2 C3 . 1.342(5) ?
N2 C2 . 1.337(5) ?
F1 C8 . 1.372(4) ?
F2 C14 . 1.373(5) ?
C1 C2 . 1.366(5) ?
C1 H2A . 0.9300 ?
C2 H1A . 0.9300 ?
C3 C4 . 1.417(4) ?
C3 C11 . 1.492(5) ?
C4 C5 . 1.472(4) ?
C5 C10 . 1.403(5) ?
C5 C6 . 1.418(4) ?
C6 C7 . 1.411(5) ?
C7 C8 . 1.371(5) ?
C7 H25A . 0.9300 ?
C8 C9 . 1.374(5) ?
C9 C10 . 1.372(5) ?
C9 H16A . 0.9300 ?
C10 H15A . 0.9300 ?
C11 C12 . 1.375(6) ?
C11 C16 . 1.392(6) ?
C12 C13 . 1.387(6) ?
C12 H14A . 0.9300 ?
C13 C14 . 1.369(7) ?
C13 H12A . 0.9300 ?
C14 C15 . 1.360(7) ?
C15 C16 . 1.384(6) ?
C15 H13A . 0.9300 ?
C16 H3A . 0.9300 ?
C17 O1 . 1.256(5) ?
C17 C19 . 1.399(6) ?
C17 C18 . 1.509(6) ?
C18 H21A . 0.9600 ?
C18 H21B . 0.9600 ?
C18 H21C . 0.9600 ?
C19 C17 2 1.399(6) ?
C19 H22A . 0.9300 ?
