#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:00:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180164 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/60/7106084.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_7106084
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            'C39 H35 Ir N4'
_chemical_formula_weight         751.91
_chemical_name_systematic
;
?
;
_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                 93.84(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.245(3)
_cell_length_b                   16.006(3)
_cell_length_c                   29.949(6)
_cell_measurement_reflns_used    23840
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.69
_cell_measurement_theta_min      3.09
_cell_volume                     6335(2)
_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_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Omega scan'
_diffrn_measurement_method       10.0
_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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            26545
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.08
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    4.249
_exptl_absorpt_correction_T_max  0.5496
_exptl_absorpt_correction_T_min  0.4837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Higash,T(1995) Progrom for Absorption Correcttion.
Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_colour            block
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       red
_exptl_crystal_F_000             2992
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.114
_refine_diff_density_min         -1.185
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         7190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0182P)²+21.9813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0661
_reflns_number_gt                5860
_reflns_number_total             7190
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC04684A.TXT
_cod_data_source_block           (bzq)2Ir(diba)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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_sg_symbol_H-M      'C2/c '
_cod_database_code               7106084
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
C1 C 0.5597(3) 0.4851(3) 0.82428(15) 0.0447(11) Uani 1 1 d . . .
H1 H 0.6064 0.4762 0.8029 0.054 Uiso 1 1 calc R . .
Ir1 Ir 0.732161(11) 0.562849(9) 0.881564(5) 0.02876(5) Uani 1 1 d . . .
N1 N 0.5902(2) 0.5220(2) 0.86251(11) 0.0343(7) Uani 1 1 d . . .
C2 C 0.4596(4) 0.4590(3) 0.81494(17) 0.0548(13) Uani 1 1 d . . .
H2 H 0.4408 0.4330 0.7879 0.066 Uiso 1 1 calc R . .
N2 N 0.8758(2) 0.5961(2) 0.90440(10) 0.0327(7) Uani 1 1 d . . .
C3 C 0.3898(4) 0.4719(3) 0.84578(18) 0.0545(13) Uani 1 1 d . . .
H3 H 0.3232 0.4549 0.8397 0.065 Uiso 1 1 calc R . .
N3 N 0.7165(3) 0.6683(2) 0.83641(11) 0.0387(8) Uani 1 1 d . . .
C4 C 0.4183(3) 0.5105(3) 0.88644(16) 0.0431(10) Uani 1 1 d . . .
N4 N 0.7872(3) 0.5530(2) 0.81466(11) 0.0365(8) Uani 1 1 d . . .
C5 C 0.3523(3) 0.5288(3) 0.92128(18) 0.0525(12) Uani 1 1 d . . .
H5 H 0.2845 0.5137 0.9175 0.063 Uiso 1 1 calc R . .
C6 C 0.3865(3) 0.5674(3) 0.95936(17) 0.0525(12) Uani 1 1 d . . .
H6 H 0.3415 0.5780 0.9812 0.063 Uiso 1 1 calc R . .
C7 C 0.4901(3) 0.5926(3) 0.96715(14) 0.0412(10) Uani 1 1 d . . .
C8 C 0.5298(4) 0.6339(3) 1.00536(15) 0.0506(12) Uani 1 1 d . . .
H8 H 0.4884 0.6465 1.0283 0.061 Uiso 1 1 calc R . .
C9 C 0.6304(4) 0.6560(3) 1.00893(14) 0.0489(12) Uani 1 1 d . . .
H9 H 0.6559 0.6837 1.0346 0.059 Uiso 1 1 calc R . .
C10 C 0.6959(3) 0.6381(3) 0.97527(14) 0.0409(10) Uani 1 1 d . . .
H10 H 0.7634 0.6544 0.9790 0.049 Uiso 1 1 calc R . .
C11 C 0.6615(3) 0.5964(2) 0.93636(13) 0.0323(8) Uani 1 1 d . . .
C12 C 0.5576(3) 0.5749(2) 0.93369(13) 0.0333(9) Uani 1 1 d . . .
C13 C 0.5203(3) 0.5346(2) 0.89389(13) 0.0346(9) Uani 1 1 d . . .
C14 C 0.9216(3) 0.6691(3) 0.89974(14) 0.0408(10) Uani 1 1 d . . .
H14 H 0.8849 0.7132 0.8865 0.049 Uiso 1 1 calc R . .
C15 C 1.0227(3) 0.6819(3) 0.91393(16) 0.0496(11) Uani 1 1 d . . .
H15 H 1.0522 0.7341 0.9105 0.059 Uiso 1 1 calc R . .
C16 C 1.0783(3) 0.6179(3) 0.93283(16) 0.0470(11) Uani 1 1 d . . .
H16 H 1.1461 0.6261 0.9420 0.056 Uiso 1 1 calc R . .
C17 C 1.0336(3) 0.5399(3) 0.93839(14) 0.0380(10) Uani 1 1 d . . .
C18 C 1.0828(3) 0.4676(3) 0.95809(15) 0.0446(11) Uani 1 1 d . . .
H18 H 1.1507 0.4710 0.9681 0.053 Uiso 1 1 calc R . .
C19 C 1.0328(3) 0.3949(3) 0.96246(15) 0.0458(11) Uani 1 1 d . . .
H19 H 1.0674 0.3490 0.9749 0.055 Uiso 1 1 calc R . .
C20 C 0.9277(3) 0.3867(3) 0.94842(13) 0.0384(9) Uani 1 1 d . . .
C21 C 0.8706(4) 0.3143(3) 0.95418(15) 0.0469(11) Uani 1 1 d . . .
H21 H 0.9014 0.2670 0.9670 0.056 Uiso 1 1 calc R . .
C22 C 0.7701(4) 0.3130(3) 0.94109(15) 0.0496(11) Uani 1 1 d . . .
H22 H 0.7326 0.2651 0.9460 0.060 Uiso 1 1 calc R . .
C23 C 0.7214(3) 0.3825(3) 0.92027(13) 0.0380(9) Uani 1 1 d . . .
H23 H 0.6529 0.3791 0.9115 0.046 Uiso 1 1 calc R . .
C24 C 0.7735(3) 0.4557(2) 0.91260(12) 0.0291(8) Uani 1 1 d . . .
C25 C 0.8767(3) 0.4561(2) 0.92865(12) 0.0305(8) Uani 1 1 d . . .
C26 C 0.9311(3) 0.5318(2) 0.92407(12) 0.0310(8) Uani 1 1 d . . .
C27 C 0.7590(3) 0.6300(3) 0.80345(13) 0.0348(9) Uani 1 1 d . . .
C28 C 0.7768(3) 0.6687(3) 0.75912(13) 0.0394(10) Uani 1 1 d . . .
C29 C 0.7155(4) 0.6496(4) 0.72191(17) 0.0657(15) Uani 1 1 d . . .
H29 H 0.6614 0.6131 0.7243 0.079 Uiso 1 1 calc R . .
C30 C 0.7332(6) 0.6841(4) 0.68086(18) 0.0836(19) Uani 1 1 d . . .
H30 H 0.6913 0.6707 0.6557 0.100 Uiso 1 1 calc R . .
C31 C 0.8119(6) 0.7378(4) 0.6772(2) 0.083(2) Uani 1 1 d . . .
H31 H 0.8240 0.7608 0.6495 0.100 Uiso 1 1 calc R . .
C32 C 0.8721(5) 0.7575(4) 0.7137(2) 0.085(2) Uani 1 1 d . . .
H32 H 0.9257 0.7943 0.7111 0.101 Uiso 1 1 calc R . .
C33 C 0.8554(4) 0.7237(4) 0.75494(19) 0.0637(15) Uani 1 1 d . . .
H33 H 0.8972 0.7381 0.7799 0.076 Uiso 1 1 calc R . .
C34 C 0.6579(4) 0.7455(3) 0.83075(16) 0.0485(11) Uani 1 1 d . . .
H34 H 0.6779 0.7740 0.8037 0.058 Uiso 1 1 calc R . .
C35 C 0.6804(6) 0.8023(4) 0.8704(2) 0.089(2) Uani 1 1 d . . .
H35A H 0.6675 0.7731 0.8974 0.133 Uiso 1 1 calc R . .
H35B H 0.6378 0.8509 0.8675 0.133 Uiso 1 1 calc R . .
H35C H 0.7501 0.8192 0.8715 0.133 Uiso 1 1 calc R . .
C36 C 0.5464(5) 0.7269(4) 0.8253(3) 0.108(3) Uani 1 1 d . . .
H36A H 0.5341 0.6855 0.8023 0.162 Uiso 1 1 calc R . .
H36B H 0.5101 0.7770 0.8170 0.162 Uiso 1 1 calc R . .
H36C H 0.5239 0.7062 0.8530 0.162 Uiso 1 1 calc R . .
C37 C 0.8577(3) 0.5038(3) 0.78931(14) 0.0421(10) Uani 1 1 d . . .
H37 H 0.8611 0.5292 0.7597 0.051 Uiso 1 1 calc R . .
C38 C 0.8188(5) 0.4158(4) 0.7832(3) 0.105(3) Uani 1 1 d . . .
H38A H 0.8048 0.3929 0.8118 0.158 Uiso 1 1 calc R . .
H38B H 0.8689 0.3822 0.7700 0.158 Uiso 1 1 calc R . .
H38C H 0.7578 0.4162 0.7640 0.158 Uiso 1 1 calc R . .
C39 C 0.9623(4) 0.5034(5) 0.81200(19) 0.081(2) Uani 1 1 d . . .
H39A H 0.9844 0.5598 0.8174 0.122 Uiso 1 1 calc R . .
H39B H 1.0078 0.4759 0.7932 0.122 Uiso 1 1 calc R . .
H39C H 0.9615 0.4741 0.8400 0.122 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'
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
N1 C1 C2 122.3(4) . . ?
C24 Ir1 C11 88.71(15) . . ?
C24 Ir1 N1 94.20(14) . . ?
C11 Ir1 N1 80.96(15) . . ?
C24 Ir1 N2 81.33(14) . . ?
C11 Ir1 N2 97.51(15) . . ?
N1 Ir1 N2 175.33(13) . . ?
C24 Ir1 N3 165.17(14) . . ?
C11 Ir1 N3 105.70(14) . . ?
N1 Ir1 N3 91.57(13) . . ?
N2 Ir1 N3 93.09(13) . . ?
C24 Ir1 N4 105.41(13) . . ?
C11 Ir1 N4 165.51(14) . . ?
N1 Ir1 N4 94.52(13) . . ?
N2 Ir1 N4 88.01(13) . . ?
N3 Ir1 N4 60.45(12) . . ?
C24 Ir1 C27 135.59(13) . . ?
C11 Ir1 C27 135.70(14) . . ?
N1 Ir1 C27 93.42(13) . . ?
N2 Ir1 C27 90.74(13) . . ?
N3 Ir1 C27 30.15(12) . . ?
N4 Ir1 C27 30.31(12) . . ?
C1 N1 C13 118.4(4) . . ?
C1 N1 Ir1 127.3(3) . . ?
C13 N1 Ir1 114.3(3) . . ?
C3 C2 C1 119.7(4) . . ?
C14 N2 C26 118.1(4) . . ?
C14 N2 Ir1 127.9(3) . . ?
C26 N2 Ir1 113.9(3) . . ?
C2 C3 C4 120.1(4) . . ?
C27 N3 C34 123.7(3) . . ?
C27 N3 Ir1 94.4(2) . . ?
C34 N3 Ir1 139.4(3) . . ?
C3 C4 C13 117.4(4) . . ?
C3 C4 C5 125.7(4) . . ?
C13 C4 C5 116.9(4) . . ?
C27 N4 C37 123.0(3) . . ?
C27 N4 Ir1 93.4(2) . . ?
C37 N4 Ir1 140.8(3) . . ?
C6 C5 C4 121.5(4) . . ?
C5 C6 C7 121.9(4) . . ?
C8 C7 C12 117.1(4) . . ?
C8 C7 C6 124.8(4) . . ?
C12 C7 C6 118.1(4) . . ?
C9 C8 C7 119.7(4) . . ?
C8 C9 C10 122.3(4) . . ?
C11 C10 C9 121.0(4) . . ?
C10 C11 C12 115.3(4) . . ?
C10 C11 Ir1 131.6(3) . . ?
C12 C11 Ir1 113.1(3) . . ?
C13 C12 C7 119.1(4) . . ?
C13 C12 C11 116.2(3) . . ?
C7 C12 C11 124.6(4) . . ?
N1 C13 C4 122.2(4) . . ?
N1 C13 C12 115.4(4) . . ?
C4 C13 C12 122.4(4) . . ?
N2 C14 C15 122.3(4) . . ?
C16 C15 C14 119.9(4) . . ?
C15 C16 C17 120.0(4) . . ?
C16 C17 C26 117.1(4) . . ?
C16 C17 C18 125.8(4) . . ?
C26 C17 C18 117.0(4) . . ?
C19 C18 C17 121.5(4) . . ?
C18 C19 C20 121.6(4) . . ?
C21 C20 C25 117.2(4) . . ?
C21 C20 C19 124.2(4) . . ?
C25 C20 C19 118.6(4) . . ?
C22 C21 C20 120.1(4) . . ?
C21 C22 C23 121.6(4) . . ?
C24 C23 C22 121.5(4) . . ?
C23 C24 C25 115.2(4) . . ?
C23 C24 Ir1 132.5(3) . . ?
C25 C24 Ir1 112.3(3) . . ?
C20 C25 C24 124.3(4) . . ?
C20 C25 C26 118.8(4) . . ?
C24 C25 C26 117.0(3) . . ?
N2 C26 C17 122.6(4) . . ?
N2 C26 C25 114.9(3) . . ?
C17 C26 C25 122.4(4) . . ?
N3 C27 N4 111.7(3) . . ?
N3 C27 C28 124.8(4) . . ?
N4 C27 C28 123.4(4) . . ?
N3 C27 Ir1 55.4(2) . . ?
N4 C27 Ir1 56.3(2) . . ?
C28 C27 Ir1 178.7(3) . . ?
C29 C28 C33 118.7(4) . . ?
C29 C28 C27 120.6(4) . . ?
C33 C28 C27 120.7(4) . . ?
C28 C29 C30 120.5(6) . . ?
C31 C30 C29 120.1(6) . . ?
C32 C31 C30 119.9(5) . . ?
C31 C32 C33 120.8(6) . . ?
C28 C33 C32 120.0(6) . . ?
N3 C34 C36 110.7(4) . . ?
N3 C34 C35 110.0(4) . . ?
C36 C34 C35 110.2(5) . . ?
N4 C37 C39 111.6(4) . . ?
N4 C37 C38 109.8(4) . . ?
C39 C37 C38 110.3(5) . . ?
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
C1 N1 1.327(5) . ?
C1 C2 1.400(6) . ?
Ir1 C24 2.008(4) . ?
Ir1 C11 2.016(4) . ?
Ir1 N1 2.037(3) . ?
Ir1 N2 2.049(3) . ?
Ir1 N3 2.165(3) . ?
Ir1 N4 2.183(3) . ?
Ir1 C27 2.620(4) . ?
N1 C13 1.377(5) . ?
C2 C3 1.366(7) . ?
N2 C14 1.328(5) . ?
N2 C26 1.373(5) . ?
C3 C4 1.395(7) . ?
N3 C27 1.320(5) . ?
N3 C34 1.463(5) . ?
C4 C13 1.409(6) . ?
C4 C5 1.435(6) . ?
N4 C27 1.325(5) . ?
N4 C37 1.470(5) . ?
C5 C6 1.348(7) . ?
C6 C7 1.435(7) . ?
C7 C8 1.393(6) . ?
C7 C12 1.415(5) . ?
C8 C9 1.376(7) . ?
C9 C10 1.403(6) . ?
C10 C11 1.393(6) . ?
C11 C12 1.415(6) . ?
C12 C13 1.414(6) . ?
C14 C15 1.392(6) . ?
C15 C16 1.363(7) . ?
C16 C17 1.396(6) . ?
C17 C26 1.402(6) . ?
C17 C18 1.435(6) . ?
C18 C19 1.350(6) . ?
C19 C20 1.433(6) . ?
C20 C21 1.400(6) . ?
C20 C25 1.409(5) . ?
C21 C22 1.363(6) . ?
C22 C23 1.410(6) . ?
C23 C24 1.387(5) . ?
C24 C25 1.419(5) . ?
C25 C26 1.421(5) . ?
C27 C28 1.497(5) . ?
C28 C29 1.369(6) . ?
C28 C33 1.376(6) . ?
C29 C30 1.383(7) . ?
C30 C31 1.360(9) . ?
C31 C32 1.347(9) . ?
C32 C33 1.380(7) . ?
C34 C36 1.506(8) . ?
C34 C35 1.510(7) . ?
C37 C39 1.501(7) . ?
C37 C38 1.508(7) . ?
