#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/14/4301447.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_4301447
loop_
_publ_author_name
'Jacob Schneider'
'Pingwu Du'
'Xiaoyong Wang'
'William W. Brennessel'
'Richard Eisenberg'
_publ_section_title
;
Synthesis, Electrochemistry, Photophysics, and Solvatochromism in New
Cyclometalated 6-Phenyl-4-(p-R-phenyl)-2,2'-bipyridyl (R = Me, COOMe,
P(O)(OEt)2) (CNN) Platinum(II) Thiophenolate Chromophores
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1498
_journal_page_last               1506
_journal_paper_doi               10.1021/ic801767q
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C24 H18 N2 O2'
_chemical_formula_sum            'C24 H18 N2 O2'
_chemical_formula_weight         366.40
_chemical_name_common            eisjs20
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.8215(18)
_cell_length_b                   6.9172(4)
_cell_length_c                   18.2398(11)
_cell_measurement_reflns_used    8300
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      33.06
_cell_measurement_theta_min      2.34
_cell_volume                     3636.4(4)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'APEX2, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, ω scans per φ'
_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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            61248
_diffrn_reflns_theta_full        32.56
_diffrn_reflns_theta_max         32.56
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_correction_T_min  0.9582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         6608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0427
_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)+(0.0624P)²+1.1797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                5651
_reflns_number_total             6608
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801767q_si_002_1.cif
_cod_data_source_block           eisjs20
_cod_database_code               4301447
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
N1 N 0.83644(3) 0.54659(11) 0.45146(4) 0.01839(14) Uani 1 1 d . . .
C1 C 0.81543(3) 0.71143(13) 0.43128(5) 0.01991(17) Uani 1 1 d . . .
H1 H 0.8196(5) 0.750(2) 0.3804(8) 0.024(3) Uiso 1 1 d . . .
C2 C 0.78791(3) 0.82149(13) 0.47813(5) 0.01920(16) Uani 1 1 d . . .
H2 H 0.7729(5) 0.939(2) 0.4607(8) 0.029(3) Uiso 1 1 d . . .
C3 C 0.78291(3) 0.76060(13) 0.55030(5) 0.01836(16) Uani 1 1 d . . .
H3 H 0.7650(5) 0.835(2) 0.5853(7) 0.024(3) Uiso 1 1 d . . .
C4 C 0.80504(3) 0.59244(12) 0.57264(5) 0.01653(15) Uani 1 1 d . . .
H4 H 0.8036(5) 0.548(2) 0.6236(8) 0.029(4) Uiso 1 1 d . . .
C5 C 0.83084(3) 0.48767(12) 0.52132(4) 0.01479(14) Uani 1 1 d . . .
N2 N 0.83957(3) 0.22436(10) 0.60628(4) 0.01576(13) Uani 1 1 d . . .
C6 C 0.85292(3) 0.30109(12) 0.54193(4) 0.01482(14) Uani 1 1 d . . .
C7 C 0.88494(3) 0.21214(12) 0.49562(5) 0.01618(15) Uani 1 1 d . . .
H7 H 0.8924(5) 0.2739(19) 0.4489(7) 0.022(3) Uiso 1 1 d . . .
C8 C 0.90465(3) 0.03535(12) 0.51611(5) 0.01498(14) Uani 1 1 d . . .
C9 C 0.89089(3) -0.04314(12) 0.58316(5) 0.01601(15) Uani 1 1 d . . .
H9 H 0.9034(4) -0.1665(19) 0.6013(7) 0.021(3) Uiso 1 1 d . . .
C10 C 0.85819(3) 0.05418(12) 0.62641(4) 0.01533(15) Uani 1 1 d . . .
C11 C 0.84081(3) -0.02762(12) 0.69668(5) 0.01590(15) Uani 1 1 d . . .
C12 C 0.79742(3) 0.02991(13) 0.72335(5) 0.01835(16) Uani 1 1 d . . .
H12 H 0.7794(5) 0.124(2) 0.6956(7) 0.026(3) Uiso 1 1 d . . .
C13 C 0.77991(3) -0.04734(13) 0.78822(5) 0.02066(17) Uani 1 1 d . . .
H13 H 0.7489(5) -0.011(2) 0.8046(8) 0.028(3) Uiso 1 1 d . . .
C14 C 0.80588(3) -0.18056(13) 0.82787(5) 0.02057(17) Uani 1 1 d . . .
H14 H 0.7940(5) -0.233(2) 0.8751(8) 0.028(3) Uiso 1 1 d . . .
C15 C 0.84903(4) -0.23782(14) 0.80185(5) 0.02179(18) Uani 1 1 d . . .
H15 H 0.8679(5) -0.330(2) 0.8306(8) 0.028(3) Uiso 1 1 d . . .
C16 C 0.86645(3) -0.16330(13) 0.73642(5) 0.02040(17) Uani 1 1 d . . .
H16 H 0.8965(6) -0.203(2) 0.7190(8) 0.035(4) Uiso 1 1 d . . .
C17 C 0.93863(3) -0.06405(12) 0.46779(5) 0.01523(14) Uani 1 1 d . . .
C18 C 0.94712(3) -0.26278(13) 0.47493(5) 0.01773(15) Uani 1 1 d . . .
H18 H 0.9296(5) -0.3399(19) 0.5105(7) 0.022(3) Uiso 1 1 d . . .
C19 C 0.97945(3) -0.35404(13) 0.43028(5) 0.01833(16) Uani 1 1 d . . .
H19 H 0.9859(5) -0.495(2) 0.4362(8) 0.028(3) Uiso 1 1 d . . .
C20 C 1.00392(3) -0.25005(12) 0.37749(5) 0.01685(15) Uani 1 1 d . . .
C21 C 0.99557(3) -0.05234(12) 0.36918(5) 0.01776(15) Uani 1 1 d . . .
H21 H 1.0127(5) 0.022(2) 0.3313(8) 0.027(3) Uiso 1 1 d . . .
C22 C 0.96325(3) 0.03842(12) 0.41421(5) 0.01750(15) Uani 1 1 d . . .
H22 H 0.9584(5) 0.177(2) 0.4084(8) 0.023(3) Uiso 1 1 d . . .
C23 C 1.03835(3) -0.35579(13) 0.33163(5) 0.01974(16) Uani 1 1 d . . .
O1 O 1.04813(3) -0.52500(11) 0.33977(5) 0.03309(19) Uani 1 1 d . . .
O2 O 1.05722(2) -0.24301(10) 0.28013(4) 0.02149(14) Uani 1 1 d . . .
C24 C 1.09081(3) -0.33601(16) 0.23308(5) 0.02448(19) Uani 1 1 d . . .
H24A H 1.0990(6) -0.234(2) 0.1959(9) 0.041(4) Uiso 1 1 d . . .
H24B H 1.0760(5) -0.448(2) 0.2090(8) 0.030(4) Uiso 1 1 d . . .
H24C H 1.1175(5) -0.377(2) 0.2623(7) 0.025(3) Uiso 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'
O O 0.0106 0.0060 '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 N1 C5 117.52(8) . . ?
N1 C1 C2 123.57(8) . . ?
N1 C1 H1 116.0(8) . . ?
C2 C1 H1 120.4(8) . . ?
C3 C2 C1 118.34(8) . . ?
C3 C2 H2 121.1(8) . . ?
C1 C2 H2 120.6(8) . . ?
C4 C3 C2 118.98(8) . . ?
C4 C3 H3 119.9(8) . . ?
C2 C3 H3 121.1(8) . . ?
C3 C4 C5 118.84(8) . . ?
C3 C4 H4 121.3(8) . . ?
C5 C4 H4 119.9(8) . . ?
N1 C5 C4 122.69(8) . . ?
N1 C5 C6 116.76(7) . . ?
C4 C5 C6 120.54(7) . . ?
C6 N2 C10 118.01(7) . . ?
N2 C6 C7 122.97(7) . . ?
N2 C6 C5 116.15(7) . . ?
C7 C6 C5 120.87(7) . . ?
C6 C7 C8 119.52(8) . . ?
C6 C7 H7 118.7(8) . . ?
C8 C7 H7 121.7(8) . . ?
C9 C8 C7 117.29(7) . . ?
C9 C8 C17 121.80(7) . . ?
C7 C8 C17 120.91(7) . . ?
C8 C9 C10 119.84(7) . . ?
C8 C9 H9 121.9(8) . . ?
C10 C9 H9 118.3(8) . . ?
N2 C10 C9 122.36(8) . . ?
N2 C10 C11 115.71(7) . . ?
C9 C10 C11 121.91(7) . . ?
C16 C11 C12 118.90(8) . . ?
C16 C11 C10 121.63(8) . . ?
C12 C11 C10 119.47(7) . . ?
C13 C12 C11 120.66(8) . . ?
C13 C12 H12 120.3(8) . . ?
C11 C12 H12 119.0(8) . . ?
C14 C13 C12 120.08(8) . . ?
C14 C13 H13 120.3(8) . . ?
C12 C13 H13 119.6(8) . . ?
C15 C14 C13 119.56(8) . . ?
C15 C14 H14 120.0(8) . . ?
C13 C14 H14 120.4(8) . . ?
C14 C15 C16 120.66(9) . . ?
C14 C15 H15 119.7(8) . . ?
C16 C15 H15 119.6(8) . . ?
C15 C16 C11 120.14(8) . . ?
C15 C16 H16 120.1(9) . . ?
C11 C16 H16 119.7(9) . . ?
C22 C17 C18 118.20(8) . . ?
C22 C17 C8 120.90(7) . . ?
C18 C17 C8 120.90(8) . . ?
C19 C18 C17 120.54(8) . . ?
C19 C18 H18 119.1(8) . . ?
C17 C18 H18 120.3(8) . . ?
C18 C19 C20 120.66(8) . . ?
C18 C19 H19 120.3(8) . . ?
C20 C19 H19 119.0(8) . . ?
C19 C20 C21 119.54(8) . . ?
C19 C20 C23 118.14(8) . . ?
C21 C20 C23 122.32(8) . . ?
C22 C21 C20 119.54(8) . . ?
C22 C21 H21 120.8(8) . . ?
C20 C21 H21 119.7(8) . . ?
C21 C22 C17 121.51(8) . . ?
C21 C22 H22 118.4(8) . . ?
C17 C22 H22 120.1(8) . . ?
O1 C23 O2 123.68(9) . . ?
O1 C23 C20 124.04(9) . . ?
O2 C23 C20 112.28(8) . . ?
C23 O2 C24 115.48(8) . . ?
O2 C24 H24A 104.2(10) . . ?
O2 C24 H24B 108.9(9) . . ?
H24A C24 H24B 110.7(12) . . ?
O2 C24 H24C 109.4(8) . . ?
H24A C24 H24C 112.6(12) . . ?
H24B C24 H24C 110.7(12) . . ?
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
N1 C1 1.3426(11) . ?
N1 C5 1.3475(11) . ?
C1 C2 1.3925(13) . ?
C1 H1 0.973(14) . ?
C2 C3 1.3896(13) . ?
C2 H2 0.972(14) . ?
C3 C4 1.3878(12) . ?
C3 H3 0.971(14) . ?
C4 C5 1.3980(11) . ?
C4 H4 0.980(14) . ?
C5 C6 1.4873(11) . ?
N2 C6 1.3445(11) . ?
N2 C10 1.3448(11) . ?
C6 C7 1.3941(11) . ?
C7 C8 1.3993(11) . ?
C7 H7 0.977(13) . ?
C8 C9 1.3958(12) . ?
C8 C17 1.4860(12) . ?
C9 C10 1.4014(12) . ?
C9 H9 0.984(13) . ?
C10 C11 1.4879(12) . ?
C11 C16 1.3971(12) . ?
C11 C12 1.3997(12) . ?
C12 C13 1.3929(12) . ?
C12 H12 0.973(14) . ?
C13 C14 1.3902(13) . ?
C13 H13 0.974(15) . ?
C14 C15 1.3887(13) . ?
C14 H14 0.994(14) . ?
C15 C16 1.3936(13) . ?
C15 H15 0.990(14) . ?
C16 H16 0.962(16) . ?
C17 C22 1.4005(12) . ?
C17 C18 1.4023(12) . ?
C18 C19 1.3891(12) . ?
C18 H18 0.980(13) . ?
C19 C20 1.3937(12) . ?
C19 H19 0.998(15) . ?
C20 C21 1.3969(12) . ?
C20 C23 1.4897(12) . ?
C21 C22 1.3914(12) . ?
C21 H21 0.991(14) . ?
C22 H22 0.973(14) . ?
C23 O1 1.2130(12) . ?
C23 O2 1.3368(12) . ?
O2 C24 1.4448(11) . ?
C24 H24A 1.007(17) . ?
C24 H24B 0.988(15) . ?
C24 H24C 0.978(14) . ?
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
C5 N1 C1 C2 -0.99(14) . . . . ?
N1 C1 C2 C3 1.86(14) . . . . ?
C1 C2 C3 C4 -0.61(13) . . . . ?
C2 C3 C4 C5 -1.34(13) . . . . ?
C1 N1 C5 C4 -1.13(13) . . . . ?
C1 N1 C5 C6 177.80(8) . . . . ?
C3 C4 C5 N1 2.30(13) . . . . ?
C3 C4 C5 C6 -176.60(8) . . . . ?
C10 N2 C6 C7 0.08(12) . . . . ?
C10 N2 C6 C5 178.99(7) . . . . ?
N1 C5 C6 N2 -166.95(8) . . . . ?
C4 C5 C6 N2 12.00(12) . . . . ?
N1 C5 C6 C7 11.98(12) . . . . ?
C4 C5 C6 C7 -169.06(8) . . . . ?
N2 C6 C7 C8 -0.29(13) . . . . ?
C5 C6 C7 C8 -179.15(7) . . . . ?
C6 C7 C8 C9 -0.11(12) . . . . ?
C6 C7 C8 C17 179.55(8) . . . . ?
C7 C8 C9 C10 0.68(12) . . . . ?
C17 C8 C9 C10 -178.98(8) . . . . ?
C6 N2 C10 C9 0.53(12) . . . . ?
C6 N2 C10 C11 -177.72(7) . . . . ?
C8 C9 C10 N2 -0.92(13) . . . . ?
C8 C9 C10 C11 177.22(8) . . . . ?
N2 C10 C11 C16 -158.38(8) . . . . ?
C9 C10 C11 C16 23.37(13) . . . . ?
N2 C10 C11 C12 22.65(11) . . . . ?
C9 C10 C11 C12 -155.61(8) . . . . ?
C16 C11 C12 C13 -0.31(13) . . . . ?
C10 C11 C12 C13 178.69(8) . . . . ?
C11 C12 C13 C14 1.08(14) . . . . ?
C12 C13 C14 C15 -0.87(14) . . . . ?
C13 C14 C15 C16 -0.09(15) . . . . ?
C14 C15 C16 C11 0.86(15) . . . . ?
C12 C11 C16 C15 -0.65(14) . . . . ?
C10 C11 C16 C15 -179.64(8) . . . . ?
C9 C8 C17 C22 -159.22(8) . . . . ?
C7 C8 C17 C22 21.14(12) . . . . ?
C9 C8 C17 C18 20.37(12) . . . . ?
C7 C8 C17 C18 -159.28(8) . . . . ?
C22 C17 C18 C19 0.57(13) . . . . ?
C8 C17 C18 C19 -179.03(8) . . . . ?
C17 C18 C19 C20 -0.17(14) . . . . ?
C18 C19 C20 C21 -0.43(13) . . . . ?
C18 C19 C20 C23 179.60(8) . . . . ?
C19 C20 C21 C22 0.63(13) . . . . ?
C23 C20 C21 C22 -179.40(8) . . . . ?
C20 C21 C22 C17 -0.23(14) . . . . ?
C18 C17 C22 C21 -0.37(13) . . . . ?
C8 C17 C22 C21 179.23(8) . . . . ?
C19 C20 C23 O1 -3.83(14) . . . . ?
C21 C20 C23 O1 176.21(10) . . . . ?
C19 C20 C23 O2 175.95(8) . . . . ?
C21 C20 C23 O2 -4.02(12) . . . . ?
O1 C23 O2 C24 0.15(14) . . . . ?
C20 C23 O2 C24 -179.63(8) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660711
