#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:57:47 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179137 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/99/4309902.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_4309902
loop_
_publ_author_name
'Tissa Sajoto'
'Peter I. Djurovich'
'Arnold Tamayo'
'Muhammed Yousufuddin'
'Robert Bau'
'Mark E. Thompson'
'Russell J. Holmes'
'Stephen R. Forrest'
_publ_section_title
;
Blue and Near-UV Phosphorescence from Iridium Complexes with Cyclometalated
Pyrazolyl or N-Heterocyclic Carbene Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7992
_journal_page_last               8003
_journal_paper_doi               10.1021/ic051296i
_journal_volume                  44
_journal_year                    2005
_chemical_formula_sum            'C42 H33 Ir N6'
_chemical_formula_weight         813.94
_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                 92.0720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0771(8)
_cell_length_b                   19.0169(14)
_cell_length_c                   15.5378(11)
_cell_measurement_reflns_used    8399
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.30
_cell_volume                     3270.9(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      143(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19741
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    4.124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1616
_refine_diff_density_max         2.251
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         7334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.089
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0370P)²+1.1017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                5854
_reflns_number_total             7334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic051296isi20050801_030055.cif
_cod_data_source_block           irmerm
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4309902
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 0.619359(14) 0.243998(7) 0.816088(10) 0.02389(6) Uani 1 1 d . . .
N1 N 0.6191(3) 0.18068(17) 1.0036(2) 0.0299(8) Uani 1 1 d . . .
N2 N 0.7621(3) 0.14710(16) 0.9216(2) 0.0260(8) Uani 1 1 d . . .
N3 N 0.3999(3) 0.33823(16) 0.8789(2) 0.0273(8) Uani 1 1 d . . .
N4 N 0.3549(3) 0.23988(16) 0.8157(2) 0.0274(8) Uani 1 1 d . . .
N5 N 0.6222(3) 0.30185(17) 0.6253(2) 0.0287(8) Uani 1 1 d . . .
N6 N 0.7030(3) 0.36722(16) 0.7254(2) 0.0265(8) Uani 1 1 d . . .
C1 C 0.6582(4) 0.1863(2) 0.9226(3) 0.0255(9) Uani 1 1 d . . .
C2 C 0.7014(4) 0.1419(2) 1.0556(3) 0.0294(10) Uani 1 1 d . . .
C3 C 0.7026(5) 0.1263(2) 1.1428(3) 0.0380(11) Uani 1 1 d . . .
H3 H 0.6378 0.1396 1.1778 0.046 Uiso 1 1 calc R . .
C4 C 0.8020(5) 0.0904(2) 1.1768(3) 0.0431(13) Uani 1 1 d . . .
H4 H 0.8056 0.0783 1.2362 0.052 Uiso 1 1 calc R . .
C5 C 0.8963(5) 0.0719(2) 1.1253(3) 0.0387(12) Uani 1 1 d . . .
H5 H 0.9646 0.0487 1.1509 0.046 Uiso 1 1 calc R . .
C6 C 0.8946(4) 0.0858(2) 1.0386(3) 0.0326(10) Uani 1 1 d . . .
H6 H 0.9590 0.0719 1.0036 0.039 Uiso 1 1 calc R . .
C7 C 0.7938(4) 0.1214(2) 1.0042(3) 0.0274(9) Uani 1 1 d . . .
C8 C 0.8208(4) 0.1422(2) 0.8429(3) 0.0271(9) Uani 1 1 d . . .
C9 C 0.9092(4) 0.0936(2) 0.8274(3) 0.0330(10) Uani 1 1 d . . .
H9 H 0.9367 0.0625 0.8718 0.040 Uiso 1 1 calc R . .
C10 C 0.9583(4) 0.0900(2) 0.7464(3) 0.0338(10) Uani 1 1 d . . .
H10 H 1.0192 0.0565 0.7348 0.041 Uiso 1 1 calc R . .
C11 C 0.9174(4) 0.1359(2) 0.6833(3) 0.0342(10) Uani 1 1 d . . .
H11 H 0.9517 0.1347 0.6282 0.041 Uiso 1 1 calc R . .
C12 C 0.8261(4) 0.1842(2) 0.6994(3) 0.0296(9) Uani 1 1 d . . .
H12 H 0.7997 0.2150 0.6544 0.036 Uiso 1 1 calc R . .
C13 C 0.7715(4) 0.1892(2) 0.7795(3) 0.0255(9) Uani 1 1 d . . .
C14 C 0.5115(4) 0.2128(2) 1.0368(3) 0.0390(11) Uani 1 1 d . . .
H14A H 0.5347 0.2517 1.0753 0.059 Uiso 1 1 calc R . .
H14B H 0.4664 0.1777 1.0688 0.059 Uiso 1 1 calc R . .
H14C H 0.4606 0.2307 0.9888 0.059 Uiso 1 1 calc R . .
C15 C 0.4518(4) 0.2813(2) 0.8427(3) 0.0257(9) Uani 1 1 d . . .
C16 C 0.2741(4) 0.3340(2) 0.8742(3) 0.0296(10) Uani 1 1 d . . .
C17 C 0.1884(4) 0.3810(2) 0.9017(3) 0.0367(11) Uani 1 1 d . . .
H17 H 0.2106 0.4236 0.9301 0.044 Uiso 1 1 calc R . .
C18 C 0.0684(4) 0.3629(3) 0.8857(3) 0.0438(12) Uani 1 1 d . . .
H18 H 0.0064 0.3935 0.9038 0.053 Uiso 1 1 calc R . .
C19 C 0.0378(4) 0.3006(3) 0.8436(3) 0.0447(13) Uani 1 1 d . . .
H19 H -0.0452 0.2900 0.8327 0.054 Uiso 1 1 calc R . .
C20 C 0.1234(4) 0.2539(2) 0.8170(3) 0.0395(12) Uani 1 1 d . . .
H20 H 0.1009 0.2114 0.7887 0.047 Uiso 1 1 calc R . .
C21 C 0.2447(4) 0.2712(2) 0.8331(3) 0.0300(9) Uani 1 1 d . . .
C22 C 0.3825(4) 0.1744(2) 0.7751(3) 0.0284(9) Uani 1 1 d . . .
C23 C 0.2958(4) 0.1259(2) 0.7506(3) 0.0336(10) Uani 1 1 d . . .
H23 H 0.2127 0.1358 0.7577 0.040 Uiso 1 1 calc R . .
C24 C 0.3306(5) 0.0629(2) 0.7159(3) 0.0377(11) Uani 1 1 d . . .
H24 H 0.2715 0.0286 0.7004 0.045 Uiso 1 1 calc R . .
C25 C 0.4508(5) 0.0496(2) 0.7038(3) 0.0379(11) Uani 1 1 d . . .
H25 H 0.4749 0.0064 0.6791 0.045 Uiso 1 1 calc R . .
C26 C 0.5366(4) 0.0998(2) 0.7278(3) 0.0329(10) Uani 1 1 d . . .
H26 H 0.6193 0.0900 0.7186 0.039 Uiso 1 1 calc R . .
C27 C 0.5061(4) 0.1647(2) 0.7652(3) 0.0268(9) Uani 1 1 d . . .
C28 C 0.4633(4) 0.3997(2) 0.9143(3) 0.0375(11) Uani 1 1 d . . .
H28A H 0.5441 0.3858 0.9358 0.056 Uiso 1 1 calc R . .
H28B H 0.4178 0.4192 0.9618 0.056 Uiso 1 1 calc R . .
H28C H 0.4704 0.4353 0.8692 0.056 Uiso 1 1 calc R . .
C29 C 0.6368(4) 0.3072(2) 0.7119(3) 0.0265(9) Uani 1 1 d . . .
C30 C 0.6844(4) 0.3556(2) 0.5834(3) 0.0296(10) Uani 1 1 d . . .
C31 C 0.7014(5) 0.3683(2) 0.4973(3) 0.0408(12) Uani 1 1 d . . .
H31 H 0.6634 0.3403 0.4535 0.049 Uiso 1 1 calc R . .
C32 C 0.7765(5) 0.4238(2) 0.4780(3) 0.0442(13) Uani 1 1 d . . .
H32 H 0.7896 0.4346 0.4194 0.053 Uiso 1 1 calc R . .
C33 C 0.8333(5) 0.4642(2) 0.5419(3) 0.0422(12) Uani 1 1 d . . .
H33 H 0.8860 0.5011 0.5260 0.051 Uiso 1 1 calc R . .
C34 C 0.8147(4) 0.4520(2) 0.6282(3) 0.0376(11) Uani 1 1 d . . .
H34 H 0.8527 0.4800 0.6719 0.045 Uiso 1 1 calc R . .
C35 C 0.7386(4) 0.3973(2) 0.6481(3) 0.0310(10) Uani 1 1 d . . .
C36 C 0.7357(4) 0.3845(2) 0.8122(3) 0.0276(9) Uani 1 1 d . . .
C37 C 0.7710(4) 0.4520(2) 0.8369(3) 0.0337(10) Uani 1 1 d . . .
H37 H 0.7753 0.4888 0.7958 0.040 Uiso 1 1 calc R . .
C38 C 0.7994(4) 0.4641(2) 0.9227(3) 0.0392(12) Uani 1 1 d . . .
H38 H 0.8237 0.5097 0.9413 0.047 Uiso 1 1 calc R . .
C39 C 0.7928(4) 0.4099(3) 0.9815(3) 0.0389(11) Uani 1 1 d . . .
H39 H 0.8172 0.4177 1.0400 0.047 Uiso 1 1 calc R . .
C40 C 0.7501(4) 0.3435(2) 0.9556(3) 0.0336(10) Uani 1 1 d . . .
H40 H 0.7445 0.3074 0.9975 0.040 Uiso 1 1 calc R . .
C41 C 0.7155(4) 0.3287(2) 0.8696(3) 0.0250(9) Uani 1 1 d . . .
C42 C 0.5540(5) 0.2479(2) 0.5792(3) 0.0417(12) Uani 1 1 d . . .
H42A H 0.5040 0.2223 0.6195 0.063 Uiso 1 1 calc R . .
H42B H 0.6098 0.2152 0.5525 0.063 Uiso 1 1 calc R . .
H42C H 0.5019 0.2698 0.5344 0.063 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
C1 Ir1 C29 162.07(17) . . ?
C1 Ir1 C15 101.01(17) . . ?
C29 Ir1 C15 93.96(16) . . ?
C1 Ir1 C13 78.48(16) . . ?
C29 Ir1 C13 88.73(16) . . ?
C15 Ir1 C13 168.80(16) . . ?
C1 Ir1 C41 90.17(16) . . ?
C29 Ir1 C41 78.38(16) . . ?
C15 Ir1 C41 96.09(16) . . ?
C13 Ir1 C41 95.10(15) . . ?
C1 Ir1 C27 91.41(15) . . ?
C29 Ir1 C27 101.40(16) . . ?
C15 Ir1 C27 77.90(16) . . ?
C13 Ir1 C27 90.91(16) . . ?
C41 Ir1 C27 173.98(15) . . ?
C1 N1 C2 110.7(4) . . ?
C1 N1 C14 126.4(4) . . ?
C2 N1 C14 122.8(4) . . ?
C1 N2 C7 111.2(4) . . ?
C1 N2 C8 117.3(3) . . ?
C7 N2 C8 131.5(4) . . ?
C15 N3 C16 111.6(3) . . ?
C15 N3 C28 126.2(4) . . ?
C16 N3 C28 122.1(3) . . ?
C15 N4 C21 111.9(3) . . ?
C15 N4 C22 116.9(3) . . ?
C21 N4 C22 131.2(4) . . ?
C29 N5 C30 111.2(3) . . ?
C29 N5 C42 125.9(4) . . ?
C30 N5 C42 122.9(4) . . ?
C29 N6 C35 112.0(3) . . ?
C29 N6 C36 117.1(3) . . ?
C35 N6 C36 130.5(4) . . ?
N1 C1 N2 105.4(3) . . ?
N1 C1 Ir1 137.8(3) . . ?
N2 C1 Ir1 116.1(3) . . ?
C7 C2 C3 121.7(4) . . ?
C7 C2 N1 107.2(4) . . ?
C3 C2 N1 131.1(4) . . ?
C4 C3 C2 117.3(5) . . ?
C3 C4 C5 120.8(4) . . ?
C6 C5 C4 122.3(4) . . ?
C5 C6 C7 116.9(5) . . ?
C2 C7 C6 121.0(4) . . ?
C2 C7 N2 105.4(4) . . ?
C6 C7 N2 133.5(4) . . ?
C9 C8 N2 123.4(4) . . ?
C9 C8 C13 123.9(4) . . ?
N2 C8 C13 112.5(4) . . ?
C8 C9 C10 119.7(4) . . ?
C11 C10 C9 118.9(4) . . ?
C10 C11 C12 120.8(4) . . ?
C11 C12 C13 122.7(4) . . ?
C12 C13 C8 113.8(4) . . ?
C12 C13 Ir1 130.9(3) . . ?
C8 C13 Ir1 114.8(3) . . ?
N3 C15 N4 104.1(3) . . ?
N3 C15 Ir1 139.6(3) . . ?
N4 C15 Ir1 116.2(3) . . ?
C17 C16 C21 123.1(4) . . ?
C17 C16 N3 129.9(4) . . ?
C21 C16 N3 107.0(4) . . ?
C16 C17 C18 116.6(4) . . ?
C17 C18 C19 120.8(4) . . ?
C20 C19 C18 122.2(5) . . ?
C19 C20 C21 117.6(4) . . ?
C16 C21 N4 105.3(4) . . ?
C16 C21 C20 119.6(4) . . ?
N4 C21 C20 135.1(4) . . ?
C23 C22 C27 123.9(4) . . ?
C23 C22 N4 123.1(4) . . ?
C27 C22 N4 113.0(4) . . ?
C24 C23 C22 119.4(4) . . ?
C23 C24 C25 120.1(4) . . ?
C24 C25 C26 119.6(4) . . ?
C25 C26 C27 122.7(4) . . ?
C22 C27 C26 114.4(4) . . ?
C22 C27 Ir1 116.0(3) . . ?
C26 C27 Ir1 129.4(3) . . ?
N5 C29 N6 105.1(3) . . ?
N5 C29 Ir1 137.4(3) . . ?
N6 C29 Ir1 115.9(3) . . ?
C31 C30 C35 121.9(4) . . ?
C31 C30 N5 131.5(4) . . ?
C35 C30 N5 106.5(4) . . ?
C30 C31 C32 116.6(4) . . ?
C31 C32 C33 121.9(5) . . ?
C34 C33 C32 121.3(5) . . ?
C35 C34 C33 117.3(4) . . ?
C34 C35 C30 121.0(4) . . ?
C34 C35 N6 133.9(4) . . ?
C30 C35 N6 105.0(4) . . ?
C37 C36 C41 124.7(4) . . ?
C37 C36 N6 122.3(4) . . ?
C41 C36 N6 112.6(3) . . ?
C38 C37 C36 118.2(4) . . ?
C37 C38 C39 120.0(4) . . ?
C38 C39 C40 120.4(4) . . ?
C39 C40 C41 122.1(4) . . ?
C40 C41 C36 113.9(4) . . ?
C40 C41 Ir1 130.7(3) . . ?
C36 C41 Ir1 114.8(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 C1 2.019(4) . ?
Ir1 C29 2.032(4) . ?
Ir1 C15 2.043(4) . ?
Ir1 C13 2.078(4) . ?
Ir1 C41 2.086(4) . ?
Ir1 C27 2.099(4) . ?
N1 C1 1.351(5) . ?
N1 C2 1.405(5) . ?
N1 C14 1.450(5) . ?
N2 C1 1.372(5) . ?
N2 C7 1.405(5) . ?
N2 C8 1.408(5) . ?
N3 C15 1.358(5) . ?
N3 C16 1.395(5) . ?
N3 C28 1.461(5) . ?
N4 C15 1.383(5) . ?
N4 C21 1.394(6) . ?
N4 C22 1.434(5) . ?
N5 C29 1.353(5) . ?
N5 C30 1.405(5) . ?
N5 C42 1.448(5) . ?
N6 C29 1.368(5) . ?
N6 C35 1.400(5) . ?
N6 C36 1.422(5) . ?
C2 C7 1.377(6) . ?
C2 C3 1.387(6) . ?
C3 C4 1.384(7) . ?
C4 C5 1.384(7) . ?
C5 C6 1.373(6) . ?
C6 C7 1.395(6) . ?
C8 C9 1.376(6) . ?
C8 C13 1.423(5) . ?
C9 C10 1.391(6) . ?
C10 C11 1.377(6) . ?
C11 C12 1.396(6) . ?
C12 C13 1.406(6) . ?
C16 C17 1.384(6) . ?
C16 C21 1.387(6) . ?
C17 C18 1.386(6) . ?
C18 C19 1.390(7) . ?
C19 C20 1.374(6) . ?
C20 C21 1.397(6) . ?
C22 C23 1.376(6) . ?
C22 C27 1.395(6) . ?
C23 C24 1.373(6) . ?
C24 C25 1.375(7) . ?
C25 C26 1.389(6) . ?
C26 C27 1.410(5) . ?
C30 C31 1.379(6) . ?
C30 C35 1.399(6) . ?
C31 C32 1.384(7) . ?
C32 C33 1.388(7) . ?
C33 C34 1.383(6) . ?
C34 C35 1.381(6) . ?
C36 C37 1.393(6) . ?
C36 C41 1.409(6) . ?
C37 C38 1.377(6) . ?
C38 C39 1.381(7) . ?
C39 C40 1.402(6) . ?
C40 C41 1.406(6) . ?
