#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:26:45 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179246 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/66/4316603.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_4316603
loop_
_publ_author_name
'Deepak Ravindranathan'
'Dileep A. K. Vezzu'
'Libero Bartolotti'
'Paul D. Boyle'
'Shouquan Huo'
_publ_contact_author_address
;
Department of Chemistry
East Carolina University
Greenville, NC 27858
;
_publ_contact_author_email       huos@ecu.edu
_publ_contact_author_fax         252-3286210
_publ_contact_author_name        'Shouquan Huo'
_publ_contact_author_phone       252-328-9784
_publ_section_title
;
 Improvement in Phosphorescence Efficiency through Tuning of Coordination
 Geometry of Tridentate Cyclometalated Platinum(II) Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8922
_journal_page_last               8928
_journal_paper_doi               10.1021/ic101109h
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C23 H18 Cl3 N3 Pt'
_chemical_formula_weight         637.84
_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                62.5123(13)
_cell_angle_beta                 69.6114(14)
_cell_angle_gamma                77.6935(16)
_cell_formula_units_Z            2
_cell_length_a                   10.3427(3)
_cell_length_b                   10.7099(3)
_cell_length_c                   11.3617(3)
_cell_measurement_reflns_used    9098
_cell_measurement_temperature    110
_cell_measurement_theta_max      34.60
_cell_measurement_theta_min      2.29
_cell_volume                     1044.43(5)
_computing_cell_refinement       SAINT
_computing_data_collection       Apex2
_computing_data_reduction        SAINT
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py
_computing_structure_refinement  XL
_computing_structure_solution    XS
_diffrn_ambient_temperature      110
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_device_type  'Bruker-Nonius Kappa Axis X8 Apex2'
_diffrn_measurement_method       'omega and phi 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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            59475
_diffrn_reflns_theta_full        34.28
_diffrn_reflns_theta_max         39.39
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    7.117
_exptl_absorpt_correction_T_max  0.3955
_exptl_absorpt_correction_T_min  0.2985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.028
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.652
_refine_diff_density_min         -1.226
_refine_diff_density_rms         0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         10654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0234P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0444
_refine_ls_wR_factor_ref         0.0462
_reflns_number_gt                9278
_reflns_number_total             10654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic101109h_si_002_2.cif
_cod_data_source_block           CN_NPtCl(1)
_cod_database_code               4316603
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
Pt1 Pt 0.119780(6) 0.200740(6) 0.332969(6) 0.01235(2) Uani 1 1 d . . .
Cl1 Cl 0.01141(5) 0.42201(4) 0.24988(4) 0.02164(8) Uani 1 1 d . . .
N1 N 0.22128(14) 0.01091(14) 0.38534(14) 0.0138(2) Uani 1 1 d . . .
N2 N 0.19782(15) -0.03281(15) 0.61927(15) 0.0161(3) Uani 1 1 d . . .
N3 N 0.05401(15) 0.17939(15) 0.53964(15) 0.0152(3) Uani 1 1 d . . .
C1 C 0.18696(17) 0.20238(18) 0.14589(17) 0.0151(3) Uani 1 1 d . . .
C2 C 0.17184(18) 0.30806(19) 0.01849(18) 0.0180(3) Uani 1 1 d . . .
H2 H 0.1252 0.3960 0.0143 0.022 Uiso 1 1 calc R . .
C3 C 0.22367(19) 0.2866(2) -0.10152(19) 0.0211(3) Uani 1 1 d . . .
H3 H 0.2122 0.3601 -0.1864 0.025 Uiso 1 1 calc R . .
C4 C 0.29213(19) 0.1593(2) -0.09922(19) 0.0218(3) Uani 1 1 d . . .
H4 H 0.3267 0.1454 -0.1817 0.026 Uiso 1 1 calc R . .
C5 C 0.30947(19) 0.0530(2) 0.02460(19) 0.0200(3) Uani 1 1 d . . .
H5 H 0.3564 -0.0344 0.0274 0.024 Uiso 1 1 calc R . .
C6 C 0.25786(17) 0.07446(18) 0.14530(17) 0.0154(3) Uani 1 1 d . . .
C7 C 0.27690(17) -0.03091(18) 0.27859(17) 0.0158(3) Uani 1 1 d . . .
C8 C 0.35022(19) -0.15927(18) 0.29768(18) 0.0189(3) Uani 1 1 d . . .
H8 H 0.3919 -0.1845 0.2221 0.023 Uiso 1 1 calc R . .
C9 C 0.36202(19) -0.25071(18) 0.42867(19) 0.0199(3) Uani 1 1 d . . .
H9 H 0.4088 -0.3411 0.4447 0.024 Uiso 1 1 calc R . .
C10 C 0.30561(19) -0.20969(19) 0.53514(18) 0.0193(3) Uani 1 1 d . . .
H10 H 0.3121 -0.2728 0.6255 0.023 Uiso 1 1 calc R . .
C11 C 0.23834(17) -0.07509(17) 0.51168(17) 0.0147(3) Uani 1 1 d . . .
C12 C 0.10396(17) 0.07665(18) 0.64128(17) 0.0149(3) Uani 1 1 d . . .
C13 C 0.0684(2) 0.0785(2) 0.77212(18) 0.0213(3) Uani 1 1 d . . .
H13 H 0.1056 0.0064 0.8426 0.026 Uiso 1 1 calc R . .
C14 C -0.0200(2) 0.1846(2) 0.79785(19) 0.0226(4) Uani 1 1 d . . .
H14 H -0.0430 0.1873 0.8852 0.027 Uiso 1 1 calc R . .
C15 C -0.07490(19) 0.2873(2) 0.6947(2) 0.0223(4) Uani 1 1 d . . .
H15 H -0.1379 0.3606 0.7103 0.027 Uiso 1 1 calc R . .
C16 C -0.03615(18) 0.28043(19) 0.56972(19) 0.0196(3) Uani 1 1 d . . .
H16 H -0.0747 0.3508 0.4995 0.023 Uiso 1 1 calc R . .
C17 C 0.25881(17) -0.12233(17) 0.73194(17) 0.0157(3) Uani 1 1 d . . .
C18 C 0.19109(18) -0.23721(18) 0.84351(18) 0.0190(3) Uani 1 1 d . . .
H18 H 0.1042 -0.2579 0.8480 0.023 Uiso 1 1 calc R . .
C19 C 0.2525(2) -0.32217(19) 0.94927(18) 0.0220(3) Uani 1 1 d . . .
H19 H 0.2070 -0.4009 1.0268 0.026 Uiso 1 1 calc R . .
C20 C 0.3792(2) -0.2915(2) 0.94074(19) 0.0238(4) Uani 1 1 d . . .
H20 H 0.4208 -0.3496 1.0128 0.029 Uiso 1 1 calc R . .
C21 C 0.4469(2) -0.1769(2) 0.8284(2) 0.0233(4) Uani 1 1 d . . .
H21 H 0.5347 -0.1575 0.8231 0.028 Uiso 1 1 calc R . .
C22 C 0.38571(18) -0.09048(18) 0.72354(18) 0.0179(3) Uani 1 1 d . . .
H22 H 0.4303 -0.0106 0.6471 0.021 Uiso 1 1 calc R . .
C1S C -0.3723(2) 0.6240(2) 0.6331(2) 0.0306(4) Uani 1 1 d . . .
H1S1 H -0.4180 0.7196 0.6146 0.037 Uiso 1 1 calc R . .
H1S2 H -0.3065 0.6085 0.6851 0.037 Uiso 1 1 calc R . .
Cl1S Cl -0.28091(6) 0.61404(6) 0.47479(5) 0.03205(11) Uani 1 1 d . . .
Cl2S Cl -0.49834(5) 0.49737(5) 0.73517(5) 0.02426(9) 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'
Cl Cl 0.1484 0.1585 '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'
Pt Pt -1.7033 8.3905 '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 Pt1 N1 82.80(6) . . ?
C1 Pt1 N3 174.82(6) . . ?
N1 Pt1 N3 92.12(5) . . ?
C1 Pt1 Cl1 91.44(5) . . ?
N1 Pt1 Cl1 174.22(4) . . ?
N3 Pt1 Cl1 93.65(4) . . ?
C11 N1 C7 119.69(14) . . ?
C11 N1 Pt1 126.06(11) . . ?
C7 N1 Pt1 114.24(11) . . ?
C11 N2 C12 131.58(14) . . ?
C11 N2 C17 113.79(13) . . ?
C12 N2 C17 114.55(13) . . ?
C12 N3 C16 117.70(15) . . ?
C12 N3 Pt1 123.68(11) . . ?
C16 N3 Pt1 118.44(11) . . ?
C2 C1 C6 116.72(15) . . ?
C2 C1 Pt1 130.18(13) . . ?
C6 C1 Pt1 113.09(12) . . ?
C3 C2 C1 121.30(16) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.90(17) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.33(17) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 119.86(17) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 121.89(15) . . ?
C5 C6 C7 122.90(15) . . ?
C1 C6 C7 115.18(14) . . ?
C8 C7 N1 121.47(15) . . ?
C8 C7 C6 124.01(15) . . ?
N1 C7 C6 114.44(14) . . ?
C7 C8 C9 119.00(16) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 119.47(16) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.61(16) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
N1 C11 N2 122.33(15) . . ?
N1 C11 C10 119.56(15) . . ?
N2 C11 C10 118.02(15) . . ?
N3 C12 C13 120.68(15) . . ?
N3 C12 N2 121.50(15) . . ?
C13 C12 N2 117.76(15) . . ?
C14 C13 C12 120.08(17) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.06(17) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 118.24(17) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
N3 C16 C15 124.16(17) . . ?
N3 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
C18 C17 C22 121.32(15) . . ?
C18 C17 N2 120.19(15) . . ?
C22 C17 N2 118.49(15) . . ?
C17 C18 C19 119.05(16) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C20 C19 C18 119.81(17) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.88(17) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C22 119.73(17) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C17 C22 C21 119.20(16) . . ?
C17 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
Cl1S C1S Cl2S 111.68(11) . . ?
Cl1S C1S H1S1 109.3 . . ?
Cl2S C1S H1S1 109.3 . . ?
Cl1S C1S H1S2 109.3 . . ?
Cl2S C1S H1S2 109.3 . . ?
H1S1 C1S H1S2 107.9 . . ?
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
Pt1 C1 1.9856(16) . ?
Pt1 N1 1.9995(14) . ?
Pt1 N3 2.1181(14) . ?
Pt1 Cl1 2.3029(4) . ?
N1 C11 1.352(2) . ?
N1 C7 1.381(2) . ?
N2 C11 1.396(2) . ?
N2 C12 1.413(2) . ?
N2 C17 1.459(2) . ?
N3 C12 1.346(2) . ?
N3 C16 1.359(2) . ?
C1 C2 1.404(2) . ?
C1 C6 1.411(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.463(2) . ?
C7 C8 1.381(2) . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.407(2) . ?
C10 H10 0.9500 . ?
C12 C13 1.410(2) . ?
C13 C14 1.375(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.367(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.386(2) . ?
C17 C22 1.386(2) . ?
C18 C19 1.397(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C1S Cl1S 1.757(2) . ?
C1S Cl2S 1.770(2) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 Pt1 N1 C11 175.81(14) . . . . ?
N3 Pt1 N1 C11 -5.19(14) . . . . ?
Cl1 Pt1 N1 C11 171.4(3) . . . . ?
C1 Pt1 N1 C7 -4.23(11) . . . . ?
N3 Pt1 N1 C7 174.77(11) . . . . ?
Cl1 Pt1 N1 C7 -8.6(5) . . . . ?
C1 Pt1 N3 C12 22.4(7) . . . . ?
N1 Pt1 N3 C12 11.23(14) . . . . ?
Cl1 Pt1 N3 C12 -168.43(13) . . . . ?
C1 Pt1 N3 C16 -162.6(6) . . . . ?
N1 Pt1 N3 C16 -173.74(13) . . . . ?
Cl1 Pt1 N3 C16 6.61(13) . . . . ?
N1 Pt1 C1 C2 -177.21(16) . . . . ?
N3 Pt1 C1 C2 171.6(5) . . . . ?
Cl1 Pt1 C1 C2 2.35(16) . . . . ?
N1 Pt1 C1 C6 4.39(12) . . . . ?
N3 Pt1 C1 C6 -6.8(7) . . . . ?
Cl1 Pt1 C1 C6 -176.05(12) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
Pt1 C1 C2 C3 -177.98(14) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -177.58(17) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
Pt1 C1 C6 C5 178.03(13) . . . . ?
C2 C1 C6 C7 177.45(15) . . . . ?
Pt1 C1 C6 C7 -3.91(19) . . . . ?
C11 N1 C7 C8 -0.1(2) . . . . ?
Pt1 N1 C7 C8 179.96(13) . . . . ?
C11 N1 C7 C6 -176.83(14) . . . . ?
Pt1 N1 C7 C6 3.21(18) . . . . ?
C5 C6 C7 C8 1.8(3) . . . . ?
C1 C6 C7 C8 -176.18(16) . . . . ?
C5 C6 C7 N1 178.50(15) . . . . ?
C1 C6 C7 N1 0.5(2) . . . . ?
N1 C7 C8 C9 3.3(3) . . . . ?
C6 C7 C8 C9 179.71(16) . . . . ?
C7 C8 C9 C10 -2.6(3) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C7 N1 C11 N2 172.91(15) . . . . ?
Pt1 N1 C11 N2 -7.1(2) . . . . ?
C7 N1 C11 C10 -3.7(2) . . . . ?
Pt1 N1 C11 C10 176.27(12) . . . . ?
C12 N2 C11 N1 19.9(3) . . . . ?
C17 N2 C11 N1 -163.49(15) . . . . ?
C12 N2 C11 C10 -163.48(17) . . . . ?
C17 N2 C11 C10 13.2(2) . . . . ?
C9 C10 C11 N1 4.3(3) . . . . ?
C9 C10 C11 N2 -172.41(16) . . . . ?
C16 N3 C12 C13 -2.9(2) . . . . ?
Pt1 N3 C12 C13 172.12(13) . . . . ?
C16 N3 C12 N2 179.81(15) . . . . ?
Pt1 N3 C12 N2 -5.1(2) . . . . ?
C11 N2 C12 N3 -12.7(3) . . . . ?
C17 N2 C12 N3 170.65(15) . . . . ?
C11 N2 C12 C13 169.96(17) . . . . ?
C17 N2 C12 C13 -6.7(2) . . . . ?
N3 C12 C13 C14 1.1(3) . . . . ?
N2 C12 C13 C14 178.48(17) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C13 C14 C15 C16 -1.4(3) . . . . ?
C12 N3 C16 C15 2.7(3) . . . . ?
Pt1 N3 C16 C15 -172.64(15) . . . . ?
C14 C15 C16 N3 -0.5(3) . . . . ?
C11 N2 C17 C18 -90.87(19) . . . . ?
C12 N2 C17 C18 86.37(19) . . . . ?
C11 N2 C17 C22 88.42(19) . . . . ?
C12 N2 C17 C22 -94.34(19) . . . . ?
C22 C17 C18 C19 0.0(3) . . . . ?
N2 C17 C18 C19 179.28(16) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
C18 C17 C22 C21 0.9(3) . . . . ?
N2 C17 C22 C21 -178.39(16) . . . . ?
C20 C21 C22 C17 -1.3(3) . . . . ?
