#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:00:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180164 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/60/7106085.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_7106085
loop_
_publ_author_name
'Tai Peng'
'Yu Yang'
'Yu Liu'
'Dongge Ma'
'Zhaomin Hou'
'Yue Wang'
_publ_section_title
;
 A phosphorescent material with high and balanced carrier mobility for
 efficient OLEDs
;
_journal_name_full               Chem.Commun.
_journal_page_first              3150
_journal_paper_doi               10.1039/c0cc04684a
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C35 H32 F4 Ir N4'
_chemical_formula_weight         776.85
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.85(3)
_cell_angle_beta                 102.09(3)
_cell_angle_gamma                103.01(3)
_cell_formula_units_Z            2
_cell_length_a                   10.465(2)
_cell_length_b                   10.914(2)
_cell_length_c                   14.783(3)
_cell_measurement_reflns_used    13734
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.09
_cell_volume                     1578.4(6)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15585
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    4.283
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
Higashi, T. (1995) Progrom for Absorption Correcttion.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             766
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.539
_refine_diff_density_min         -1.421
_refine_diff_density_rms         0.149
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         7178
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0358
_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)+(0.0490P)²+1.2143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                6233
_reflns_number_total             7178
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC04684A.TXT
_cod_data_source_block           pt2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1578.6(6)
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               7106085
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C7 C 0.9744(7) 0.1857(7) -0.0302(5) 0.0603(17) Uani 1 1 d . . .
Ir1 Ir 0.822140(18) 0.214101(18) 0.212141(13) 0.03463(8) Uani 1 1 d . . .
N3 N 0.6887(5) 0.0501(5) 0.2199(3) 0.0416(10) Uani 1 1 d . . .
N4 N 0.9622(4) 0.3673(4) 0.1973(3) 0.0405(10) Uani 1 1 d . . .
C22 C 0.9507(5) 0.1198(5) 0.2660(4) 0.0361(10) Uani 1 1 d . . .
C11 C 0.8475(5) 0.1459(5) 0.0857(4) 0.0395(11) Uani 1 1 d . . .
N2 N 0.7778(4) 0.3129(4) 0.3336(3) 0.0405(10) Uani 1 1 d . . .
N1 N 0.6744(4) 0.3236(4) 0.1914(3) 0.0392(9) Uani 1 1 d . . .
C29 C 0.6868(5) 0.3622(5) 0.2828(4) 0.0402(11) Uani 1 1 d . . .
F1 F 0.7469(5) -0.1229(5) -0.1111(3) 0.0885(14) Uani 1 1 d . . .
F3 F 1.3047(4) 0.1275(4) 0.3601(3) 0.0790(13) Uani 1 1 d . . .
F2 F 1.0737(5) 0.2646(5) -0.0593(3) 0.0908(15) Uani 1 1 d . . .
C33 C 0.6052(6) 0.3846(6) 0.1172(4) 0.0469(13) Uani 1 1 d . . .
H33 H 0.5312 0.4126 0.1374 0.056 Uiso 1 1 calc R . .
C17 C 0.8903(6) -0.0033(6) 0.2803(4) 0.0463(13) Uani 1 1 d . . .
C28 C 0.6109(5) 0.4439(5) 0.3246(4) 0.0415(12) Uani 1 1 d . . .
C5 C 1.0091(5) 0.3544(5) 0.1185(4) 0.0420(12) Uani 1 1 d . . .
F4 F 0.9161(5) -0.1938(4) 0.3354(4) 0.0993(17) Uani 1 1 d . . .
C6 C 0.9463(5) 0.2283(6) 0.0548(4) 0.0439(12) Uani 1 1 d . . .
C18 C 0.9743(7) -0.0765(6) 0.3208(5) 0.0595(17) Uani 1 1 d . . .
C1 C 1.0091(6) 0.4775(6) 0.2588(5) 0.0504(14) Uani 1 1 d . . .
H1 H 0.9796 0.4846 0.3139 0.060 Uiso 1 1 calc R . .
C20 C 1.1670(6) 0.0836(7) 0.3338(4) 0.0531(14) Uani 1 1 d . . .
C9 C 0.8130(7) -0.0048(7) -0.0551(5) 0.0578(16) Uani 1 1 d . . .
C30 C 0.7900(6) 0.3062(6) 0.4324(4) 0.0494(13) Uani 1 1 d . . .
H30 H 0.7690 0.3820 0.4632 0.059 Uiso 1 1 calc R . .
C3 C 1.1462(8) 0.5710(7) 0.1649(6) 0.074(2) Uani 1 1 d . . .
H3 H 1.2071 0.6401 0.1536 0.089 Uiso 1 1 calc R . .
C10 C 0.7785(6) 0.0274(6) 0.0275(4) 0.0491(13) Uani 1 1 d . . .
H10 H 0.7104 -0.0284 0.0445 0.059 Uiso 1 1 calc R . .
C32 C 0.6903(8) 0.1875(7) 0.4442(5) 0.069(2) Uani 1 1 d . . .
H32A H 0.6004 0.1851 0.4106 0.104 Uiso 1 1 calc R . .
H32B H 0.6936 0.1906 0.5099 0.104 Uiso 1 1 calc R . .
H32C H 0.7141 0.1121 0.4194 0.104 Uiso 1 1 calc R . .
C8 C 0.9112(8) 0.0721(7) -0.0866(5) 0.0637(18) Uani 1 1 d . . .
H8 H 0.9321 0.0468 -0.1431 0.076 Uiso 1 1 calc R . .
C12 C 0.5536(6) 0.0306(6) 0.1948(5) 0.0535(15) Uani 1 1 d . . .
H12 H 0.5172 0.0948 0.1735 0.064 Uiso 1 1 calc R . .
C16 C 0.7422(6) -0.0409(5) 0.2535(4) 0.0478(13) Uani 1 1 d . . .
C4 C 1.1022(7) 0.4571(7) 0.1019(5) 0.0652(18) Uani 1 1 d . . .
H4 H 1.1342 0.4481 0.0479 0.078 Uiso 1 1 calc R . .
C15 C 0.6567(7) -0.1558(7) 0.2600(6) 0.078(2) Uani 1 1 d . . .
H15 H 0.6928 -0.2204 0.2809 0.094 Uiso 1 1 calc R . .
C19 C 1.1119(7) -0.0325(7) 0.3492(5) 0.0643(18) Uani 1 1 d . . .
H19 H 1.1650 -0.0809 0.3781 0.077 Uiso 1 1 calc R . .
C21 C 1.0929(5) 0.1629(5) 0.2936(4) 0.0462(13) Uani 1 1 d . . .
H21 H 1.1370 0.2431 0.2852 0.055 Uiso 1 1 calc R . .
C2 C 1.0997(7) 0.5821(7) 0.2446(6) 0.0692(19) Uani 1 1 d . . .
H2 H 1.1284 0.6586 0.2885 0.083 Uiso 1 1 calc R . .
C14 C 0.5167(8) -0.1731(8) 0.2348(7) 0.084(3) Uani 1 1 d . . .
H14 H 0.4589 -0.2471 0.2425 0.101 Uiso 1 1 calc R . .
C31 C 0.9357(7) 0.3105(8) 0.4782(5) 0.0700(19) Uani 1 1 d . . .
H31A H 0.9552 0.2324 0.4541 0.105 Uiso 1 1 calc R . .
H31B H 0.9482 0.3200 0.5453 0.105 Uiso 1 1 calc R . .
H31C H 0.9957 0.3818 0.4642 0.105 Uiso 1 1 calc R . .
C13 C 0.4674(7) -0.0839(7) 0.2001(6) 0.077(2) Uani 1 1 d . . .
H13 H 0.3742 -0.0975 0.1790 0.092 Uiso 1 1 calc R . .
C23 C 0.6814(7) 0.5618(6) 0.3828(4) 0.0552(15) Uani 1 1 d . . .
H23 H 0.7750 0.5894 0.3938 0.066 Uiso 1 1 calc R . .
C27 C 0.4715(7) 0.4056(7) 0.3082(5) 0.0615(17) Uani 1 1 d . . .
H27 H 0.4225 0.3277 0.2691 0.074 Uiso 1 1 calc R . .
C24 C 0.6113(11) 0.6380(7) 0.4244(6) 0.080(2) Uani 1 1 d . . .
H24 H 0.6578 0.7164 0.4637 0.096 Uiso 1 1 calc R . .
C25 C 0.4729(10) 0.5967(9) 0.4070(6) 0.084(3) Uani 1 1 d . . .
H25 H 0.4259 0.6476 0.4349 0.101 Uiso 1 1 calc R . .
C26 C 0.4053(9) 0.4854(9) 0.3513(7) 0.084(3) Uani 1 1 d . . .
H26 H 0.3116 0.4598 0.3406 0.100 Uiso 1 1 calc R . .
C35 C 0.7050(10) 0.4984(9) 0.1035(8) 0.109(4) Uani 1 1 d . . .
H35A H 0.7715 0.5362 0.1619 0.163 Uiso 1 1 calc R . .
H35B H 0.6585 0.5602 0.0836 0.163 Uiso 1 1 calc R . .
H35C H 0.7489 0.4716 0.0564 0.163 Uiso 1 1 calc R . .
C34 C 0.5482(14) 0.2844(11) 0.0293(6) 0.146(6) Uani 1 1 d . . .
H34A H 0.6204 0.2692 0.0024 0.220 Uiso 1 1 calc R . .
H34B H 0.4861 0.3132 -0.0151 0.220 Uiso 1 1 calc R . .
H34C H 0.5014 0.2064 0.0442 0.220 Uiso 1 1 calc R . .
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'
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
C8 C7 F2 116.9(6) . . ?
C8 C7 C6 124.4(6) . . ?
F2 C7 C6 118.6(7) . . ?
C22 Ir1 C11 86.8(2) . . ?
C22 Ir1 N4 96.94(19) . . ?
C11 Ir1 N4 80.3(2) . . ?
C22 Ir1 N3 80.2(2) . . ?
C11 Ir1 N3 95.3(2) . . ?
N4 Ir1 N3 174.88(17) . . ?
C22 Ir1 N2 104.02(19) . . ?
C11 Ir1 N2 168.79(18) . . ?
N4 Ir1 N2 95.28(18) . . ?
N3 Ir1 N2 89.56(18) . . ?
C22 Ir1 N1 164.53(18) . . ?
C11 Ir1 N1 108.44(18) . . ?
N4 Ir1 N1 88.49(16) . . ?
N3 Ir1 N1 95.33(17) . . ?
N2 Ir1 N1 60.93(16) . . ?
C12 N3 C16 119.8(5) . . ?
C12 N3 Ir1 123.5(4) . . ?
C16 N3 Ir1 116.7(4) . . ?
C1 N4 C5 118.8(5) . . ?
C1 N4 Ir1 124.4(4) . . ?
C5 N4 Ir1 116.8(4) . . ?
C21 C22 C17 117.5(5) . . ?
C21 C22 Ir1 127.4(4) . . ?
C17 C22 Ir1 115.1(4) . . ?
C10 C11 C6 118.2(5) . . ?
C10 C11 Ir1 126.9(4) . . ?
C6 C11 Ir1 114.9(4) . . ?
C29 N2 C30 124.1(5) . . ?
C29 N2 Ir1 94.4(3) . . ?
C30 N2 Ir1 138.4(4) . . ?
C29 N1 C33 122.5(5) . . ?
C29 N1 Ir1 94.8(3) . . ?
C33 N1 Ir1 140.1(3) . . ?
N1 C29 N2 109.8(5) . . ?
N1 C29 C28 126.4(5) . . ?
N2 C29 C28 123.8(5) . . ?
C34 C33 C35 112.2(8) . . ?
C34 C33 N1 107.1(6) . . ?
C35 C33 N1 109.5(5) . . ?
C18 C17 C22 119.0(5) . . ?
C18 C17 C16 125.9(5) . . ?
C22 C17 C16 115.0(5) . . ?
C27 C28 C23 119.1(6) . . ?
C27 C28 C29 121.5(6) . . ?
C23 C28 C29 119.4(5) . . ?
N4 C5 C4 120.1(6) . . ?
N4 C5 C6 113.4(4) . . ?
C4 C5 C6 126.4(5) . . ?
C7 C6 C11 118.5(6) . . ?
C7 C6 C5 127.0(5) . . ?
C11 C6 C5 114.5(5) . . ?
F4 C18 C19 118.1(5) . . ?
F4 C18 C17 118.9(6) . . ?
C19 C18 C17 122.9(6) . . ?
N4 C1 C2 123.0(6) . . ?
C19 C20 F3 117.6(6) . . ?
C19 C20 C21 124.4(5) . . ?
F3 C20 C21 118.0(6) . . ?
C10 C9 F1 118.5(6) . . ?
C10 C9 C8 124.7(6) . . ?
F1 C9 C8 116.8(6) . . ?
N2 C30 C31 108.9(5) . . ?
N2 C30 C32 111.4(5) . . ?
C31 C30 C32 112.0(5) . . ?
C2 C3 C4 119.2(6) . . ?
C9 C10 C11 118.7(6) . . ?
C7 C8 C9 115.5(6) . . ?
N3 C12 C13 121.0(6) . . ?
N3 C16 C15 119.7(6) . . ?
N3 C16 C17 113.0(5) . . ?
C15 C16 C17 127.3(6) . . ?
C3 C4 C5 120.1(7) . . ?
C16 C15 C14 119.5(7) . . ?
C20 C19 C18 117.0(5) . . ?
C20 C21 C22 119.1(5) . . ?
C3 C2 C1 118.7(7) . . ?
C13 C14 C15 119.4(7) . . ?
C14 C13 C12 120.4(7) . . ?
C24 C23 C28 119.8(7) . . ?
C28 C27 C26 119.0(7) . . ?
C25 C24 C23 119.5(8) . . ?
C26 C25 C24 121.0(7) . . ?
C25 C26 C27 121.5(8) . . ?
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
C7 C8 1.336(10) . ?
C7 F2 1.376(8) . ?
C7 C6 1.393(9) . ?
Ir1 C22 1.975(5) . ?
Ir1 C11 2.009(5) . ?
Ir1 N4 2.031(5) . ?
Ir1 N3 2.041(5) . ?
Ir1 N2 2.156(4) . ?
Ir1 N1 2.156(4) . ?
N3 C12 1.343(7) . ?
N3 C16 1.348(7) . ?
N4 C1 1.328(8) . ?
N4 C5 1.357(7) . ?
C22 C21 1.408(7) . ?
C22 C17 1.415(8) . ?
C11 C10 1.396(8) . ?
C11 C6 1.406(8) . ?
N2 C29 1.342(7) . ?
N2 C30 1.453(7) . ?
N1 C29 1.329(7) . ?
N1 C33 1.502(6) . ?
C29 C28 1.477(7) . ?
F1 C9 1.375(7) . ?
F3 C20 1.364(7) . ?
C33 C34 1.494(11) . ?
C33 C35 1.499(10) . ?
C17 C18 1.412(8) . ?
C17 C16 1.463(8) . ?
C28 C27 1.383(8) . ?
C28 C23 1.395(9) . ?
C5 C4 1.396(8) . ?
C5 C6 1.481(8) . ?
F4 C18 1.356(7) . ?
C18 C19 1.363(9) . ?
C1 C2 1.380(9) . ?
C20 C19 1.340(9) . ?
C20 C21 1.398(8) . ?
C9 C10 1.367(9) . ?
C9 C8 1.377(10) . ?
C30 C31 1.521(9) . ?
C30 C32 1.525(9) . ?
C3 C2 1.367(11) . ?
C3 C4 1.368(11) . ?
C12 C13 1.390(9) . ?
C16 C15 1.395(8) . ?
C15 C14 1.396(11) . ?
C14 C13 1.316(10) . ?
C23 C24 1.390(10) . ?
C27 C26 1.397(10) . ?
C24 C25 1.374(13) . ?
C25 C26 1.322(12) . ?
