#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/25/7202587.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_7202587
loop_
_publ_author_name
'Shih, Ping-I'
'Chien, Chen-Han'
'Chuang, Chu-Ying'
'Shu, Ching-Fong'
'Yang, Cheng-Han'
'Chen, Jian-Hong'
'Chi, Yun'
_publ_section_title
;
 Novel host material for highly efficient blue phosphorescent OLEDs
;
_journal_issue                   17
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              1692
_journal_paper_doi               10.1039/b616043c
_journal_volume                  17
_journal_year                    2007
_chemical_formula_sum            'C33.5 H18 Cl F10 Ir N4'
_chemical_formula_weight         894.17
_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                96.0383(7)
_cell_angle_beta                 90.7590(6)
_cell_angle_gamma                107.0188(5)
_cell_formula_units_Z            2
_cell_length_a                   10.0361(1)
_cell_length_b                   11.1106(1)
_cell_length_c                   14.0054(1)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.00
_cell_volume                     1483.43(2)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'NONIUS COLLECT'
_computing_data_reduction        DENZO-SMN
_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      150(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω 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  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28743
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    4.687
_exptl_absorpt_correction_T_max  0.639
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.002
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             862
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.369
_refine_diff_density_min         -1.670
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0275
_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)+(0.0371P)²+1.8610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0696
_reflns_number_gt                6265
_reflns_number_total             6797
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b616043c.txt
_cod_data_source_block           ic11593
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_original_formula_sum        'C33.50 H18 Cl F10 Ir N4'
_cod_database_code               7202587
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
Ir Ir 0.289347(13) 0.202103(11) 0.211679(9) 0.01821(6) Uani 1 1 d . . .
F1 F -0.0513(3) 0.2973(3) -0.05430(17) 0.0412(6) Uani 1 1 d . . .
F2 F -0.0441(3) 0.4903(2) 0.25930(19) 0.0399(6) Uani 1 1 d . . .
F3 F 0.6266(2) 0.6850(2) 0.25046(18) 0.0365(5) Uani 1 1 d . . .
F4 F 0.6620(2) 0.4238(2) -0.02574(16) 0.0347(5) Uani 1 1 d . . .
F5 F 0.2877(3) -0.2213(2) 0.44599(17) 0.0392(6) Uani 1 1 d . . .
F6 F 0.3437(3) -0.2965(2) 0.31009(18) 0.0388(6) Uani 1 1 d . . .
F7 F 0.5009(3) -0.2178(3) 0.42468(19) 0.0441(6) Uani 1 1 d . . .
F8 F 0.6303(3) 0.3418(2) 0.35481(18) 0.0387(6) Uani 1 1 d . . .
F9 F 0.6813(2) 0.2610(2) 0.21915(17) 0.0355(5) Uani 1 1 d . . .
F10 F 0.7749(2) 0.2319(3) 0.35020(19) 0.0412(6) Uani 1 1 d . . .
N1 N 0.2453(3) 0.2955(3) 0.3354(2) 0.0215(6) Uani 1 1 d . . .
N2 N 0.3390(3) 0.1308(3) 0.0802(2) 0.0213(6) Uani 1 1 d . . .
N3 N 0.1370(3) 0.0294(3) 0.2375(2) 0.0225(6) Uani 1 1 d . . .
N4 N 0.4081(3) 0.1012(3) 0.2824(2) 0.0219(6) Uani 1 1 d . . .
C1 C 0.1516(4) 0.2794(3) 0.1577(3) 0.0213(7) Uani 1 1 d . . .
C2 C 0.0985(4) 0.2602(3) 0.0622(3) 0.0243(7) Uani 1 1 d . . .
H2A H 0.1293 0.2079 0.0149 0.029 Uiso 1 1 calc R . .
C3 C 0.0009(4) 0.3186(4) 0.0383(3) 0.0283(8) Uani 1 1 d . . .
C4 C -0.0469(4) 0.3968(4) 0.1024(3) 0.0315(9) Uani 1 1 d . . .
H4A H -0.1123 0.4375 0.0832 0.038 Uiso 1 1 calc R . .
C5 C 0.0046(4) 0.4135(4) 0.1958(3) 0.0292(8) Uani 1 1 d . . .
C6 C 0.1013(4) 0.3562(3) 0.2261(3) 0.0220(7) Uani 1 1 d . . .
C7 C 0.1554(4) 0.3661(4) 0.3255(3) 0.0265(8) Uani 1 1 d . . .
C8 C 0.1292(4) 0.4408(4) 0.4064(3) 0.0346(9) Uani 1 1 d . . .
H8A H 0.0681 0.4909 0.4001 0.042 Uiso 1 1 calc R . .
C9 C 0.1914(5) 0.4416(5) 0.4939(3) 0.0392(10) Uani 1 1 d . . .
H9A H 0.1729 0.4915 0.5486 0.047 Uiso 1 1 calc R . .
C10 C 0.2813(5) 0.3695(5) 0.5026(3) 0.0389(10) Uani 1 1 d . . .
H10A H 0.3256 0.3695 0.5630 0.047 Uiso 1 1 calc R . .
C11 C 0.3056(4) 0.2975(4) 0.4221(3) 0.0279(8) Uani 1 1 d . . .
H11A H 0.3670 0.2477 0.4280 0.034 Uiso 1 1 calc R . .
C12 C 0.4356(4) 0.3558(3) 0.1778(3) 0.0198(7) Uani 1 1 d . . .
C13 C 0.4813(4) 0.4750(3) 0.2315(3) 0.0230(7) Uani 1 1 d . . .
H13A H 0.4419 0.4904 0.2911 0.028 Uiso 1 1 calc R . .
C14 C 0.5840(4) 0.5696(4) 0.1968(3) 0.0266(8) Uani 1 1 d . . .
C15 C 0.6472(4) 0.5555(4) 0.1116(3) 0.0274(8) Uani 1 1 d . . .
H15A H 0.7196 0.6225 0.0908 0.033 Uiso 1 1 calc R . .
C16 C 0.5996(4) 0.4389(4) 0.0580(3) 0.0253(8) Uani 1 1 d . . .
C17 C 0.4947(4) 0.3385(3) 0.0875(3) 0.0215(7) Uani 1 1 d . . .
C18 C 0.4382(4) 0.2129(3) 0.0334(2) 0.0221(7) Uani 1 1 d . . .
C19 C 0.4736(4) 0.1736(4) -0.0584(3) 0.0286(8) Uani 1 1 d . . .
H19A H 0.5419 0.2304 -0.0917 0.034 Uiso 1 1 calc R . .
C20 C 0.4088(4) 0.0512(4) -0.1007(3) 0.0322(9) Uani 1 1 d . . .
H20A H 0.4326 0.0240 -0.1630 0.039 Uiso 1 1 calc R . .
C21 C 0.3095(4) -0.0309(4) -0.0517(3) 0.0310(9) Uani 1 1 d . . .
H21A H 0.2643 -0.1150 -0.0796 0.037 Uiso 1 1 calc R . .
C22 C 0.2775(4) 0.0120(4) 0.0382(3) 0.0267(8) Uani 1 1 d . . .
H22A H 0.2095 -0.0442 0.0721 0.032 Uiso 1 1 calc R . .
C23 C -0.0013(4) 0.0015(4) 0.2141(3) 0.0292(8) Uani 1 1 d . . .
H23A H -0.0342 0.0647 0.1895 0.035 Uiso 1 1 calc R . .
C24 C -0.0956(4) -0.1133(4) 0.2241(3) 0.0335(9) Uani 1 1 d . . .
H24A H -0.1917 -0.1295 0.2073 0.040 Uiso 1 1 calc R . .
C25 C -0.0465(4) -0.2057(4) 0.2597(3) 0.0348(9) Uani 1 1 d . . .
H25A H -0.1088 -0.2870 0.2663 0.042 Uiso 1 1 calc R . .
C26 C 0.0919(4) -0.1786(4) 0.2851(3) 0.0298(8) Uani 1 1 d . . .
H26A H 0.1255 -0.2409 0.3103 0.036 Uiso 1 1 calc R . .
C27 C 0.1845(4) -0.0598(3) 0.2741(3) 0.0237(7) Uani 1 1 d . . .
C28 C 0.3325(4) -0.0182(3) 0.3008(2) 0.0231(7) Uani 1 1 d . . .
C29 C 0.4207(4) -0.0736(4) 0.3480(3) 0.0259(8) Uani 1 1 d . . .
C30 C 0.5522(4) 0.0146(4) 0.3587(3) 0.0263(8) Uani 1 1 d . . .
H30A H 0.6336 0.0049 0.3882 0.032 Uiso 1 1 calc R . .
C31 C 0.5406(4) 0.1193(4) 0.3180(3) 0.0245(8) Uani 1 1 d . . .
C32 C 0.3881(5) -0.2006(4) 0.3816(3) 0.0328(9) Uani 1 1 d . . .
C33 C 0.6541(4) 0.2370(4) 0.3106(3) 0.0277(8) Uani 1 1 d . . .
C34 C 0.8923(13) -0.0470(10) 0.4887(7) 0.061(3) Uani 0.50 1 d P . .
H34A H 0.8475 -0.1042 0.4307 0.074 Uiso 0.50 1 calc PR . .
H34B H 0.8204 -0.0478 0.5365 0.074 Uiso 0.50 1 calc PR . .
Cl1 Cl 0.96342(18) 0.10288(16) 0.45967(12) 0.0727(4) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C12 Ir C1 85.69(13) . . ?
C12 Ir N1 93.08(13) . . ?
C1 Ir N1 80.49(13) . . ?
C12 Ir N2 80.58(13) . . ?
C1 Ir N2 94.88(13) . . ?
N1 Ir N2 172.46(11) . . ?
C12 Ir N3 175.30(12) . . ?
C1 Ir N3 95.26(12) . . ?
N1 Ir N3 91.62(12) . . ?
N2 Ir N3 94.75(12) . . ?
C12 Ir N4 103.32(12) . . ?
C1 Ir N4 170.31(12) . . ?
N1 Ir N4 95.28(11) . . ?
N2 Ir N4 90.18(11) . . ?
N3 Ir N4 76.06(11) . . ?
C11 N1 C7 119.7(3) . . ?
C11 N1 Ir 123.9(3) . . ?
C7 N1 Ir 116.2(2) . . ?
C22 N2 C18 119.8(3) . . ?
C22 N2 Ir 124.2(3) . . ?
C18 N2 Ir 116.0(2) . . ?
C23 N3 C27 118.8(3) . . ?
C23 N3 Ir 123.9(2) . . ?
C27 N3 Ir 117.2(2) . . ?
C31 N4 C28 106.2(3) . . ?
C31 N4 Ir 139.4(3) . . ?
C28 N4 Ir 114.4(2) . . ?
C2 C1 C6 118.7(3) . . ?
C2 C1 Ir 126.8(3) . . ?
C6 C1 Ir 114.5(3) . . ?
C3 C2 C1 118.9(4) . . ?
F1 C3 C4 118.1(3) . . ?
F1 C3 C2 118.2(4) . . ?
C4 C3 C2 123.8(4) . . ?
C3 C4 C5 116.7(4) . . ?
F2 C5 C4 116.5(3) . . ?
F2 C5 C6 120.5(4) . . ?
C4 C5 C6 123.0(4) . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 125.5(4) . . ?
C1 C6 C7 115.6(3) . . ?
N1 C7 C8 119.2(3) . . ?
N1 C7 C6 113.1(3) . . ?
C8 C7 C6 127.7(4) . . ?
C9 C8 C7 120.2(4) . . ?
C8 C9 C10 119.7(4) . . ?
C11 C10 C9 118.8(4) . . ?
N1 C11 C10 122.3(4) . . ?
C13 C12 C17 118.3(3) . . ?
C13 C12 Ir 127.3(3) . . ?
C17 C12 Ir 114.3(3) . . ?
C14 C13 C12 119.2(4) . . ?
F3 C14 C13 118.0(4) . . ?
F3 C14 C15 117.7(3) . . ?
C13 C14 C15 124.3(4) . . ?
C14 C15 C16 116.3(3) . . ?
F4 C16 C15 116.7(3) . . ?
F4 C16 C17 120.3(3) . . ?
C15 C16 C17 123.0(4) . . ?
C16 C17 C12 118.9(3) . . ?
C16 C17 C18 125.6(3) . . ?
C12 C17 C18 115.5(3) . . ?
N2 C18 C19 119.6(3) . . ?
N2 C18 C17 113.6(3) . . ?
C19 C18 C17 126.8(3) . . ?
C20 C19 C18 119.8(4) . . ?
C21 C20 C19 119.7(4) . . ?
C22 C21 C20 118.5(4) . . ?
N2 C22 C21 122.5(4) . . ?
N3 C23 C24 123.1(4) . . ?
C23 C24 C25 118.1(4) . . ?
C26 C25 C24 119.5(4) . . ?
C25 C26 C27 120.5(4) . . ?
N3 C27 C26 120.0(3) . . ?
N3 C27 C28 114.2(3) . . ?
C26 C27 C28 125.8(3) . . ?
N4 C28 C29 109.1(3) . . ?
N4 C28 C27 117.7(3) . . ?
C29 C28 C27 133.2(3) . . ?
C30 C29 C28 107.1(3) . . ?
C30 C29 C32 123.6(3) . . ?
C28 C29 C32 129.3(4) . . ?
C31 C30 C29 106.2(3) . . ?
N4 C31 C30 111.4(3) . . ?
N4 C31 C33 122.4(3) . . ?
C30 C31 C33 126.2(3) . . ?
F5 C32 F7 106.2(3) . . ?
F5 C32 F6 105.5(3) . . ?
F7 C32 F6 106.3(3) . . ?
F5 C32 C29 113.5(3) . . ?
F7 C32 C29 111.4(4) . . ?
F6 C32 C29 113.4(3) . . ?
F8 C33 F10 106.1(3) . . ?
F8 C33 F9 105.6(3) . . ?
F10 C33 F9 105.6(3) . . ?
F8 C33 C31 114.0(3) . . ?
F10 C33 C31 111.3(3) . . ?
F9 C33 C31 113.6(3) . . ?
Cl1 C34 Cl1 108.5(6) . 2_756 ?
C34 Cl1 C34 71.5(6) . 2_756 ?
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
Ir C12 2.004(3) . ?
Ir C1 2.006(4) . ?
Ir N1 2.046(3) . ?
Ir N2 2.053(3) . ?
Ir N3 2.144(3) . ?
Ir N4 2.155(3) . ?
F1 C3 1.363(4) . ?
F2 C5 1.362(5) . ?
F3 C14 1.364(4) . ?
F4 C16 1.355(4) . ?
F5 C32 1.347(5) . ?
F6 C32 1.350(5) . ?
F7 C32 1.348(5) . ?
F8 C33 1.345(5) . ?
F9 C33 1.350(4) . ?
F10 C33 1.346(4) . ?
N1 C11 1.344(5) . ?
N1 C7 1.372(5) . ?
N2 C22 1.349(5) . ?
N2 C18 1.366(5) . ?
N3 C23 1.359(5) . ?
N3 C27 1.359(5) . ?
N4 C31 1.364(5) . ?
N4 C28 1.375(5) . ?
C1 C2 1.405(5) . ?
C1 C6 1.412(5) . ?
C2 C3 1.379(5) . ?
C3 C4 1.372(6) . ?
C4 C5 1.373(6) . ?
C5 C6 1.391(5) . ?
C6 C7 1.469(5) . ?
C7 C8 1.407(6) . ?
C8 C9 1.367(6) . ?
C9 C10 1.383(6) . ?
C10 C11 1.379(6) . ?
C12 C13 1.398(5) . ?
C12 C17 1.422(5) . ?
C13 C14 1.374(5) . ?
C14 C15 1.375(6) . ?
C15 C16 1.375(6) . ?
C16 C17 1.395(5) . ?
C17 C18 1.465(5) . ?
C18 C19 1.398(5) . ?
C19 C20 1.387(6) . ?
C20 C21 1.384(6) . ?
C21 C22 1.374(5) . ?
C23 C24 1.370(5) . ?
C24 C25 1.395(6) . ?
C25 C26 1.365(6) . ?
C26 C27 1.399(5) . ?
C27 C28 1.451(5) . ?
C28 C29 1.410(5) . ?
C29 C30 1.390(6) . ?
C29 C32 1.481(5) . ?
C30 C31 1.382(5) . ?
C31 C33 1.476(5) . ?
C34 Cl1 1.703(10) . ?
C34 Cl1 1.897(14) 2_756 ?
Cl1 C34 1.897(14) 2_756 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139194845
