#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:54:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178706 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/17/4081758.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_4081758
loop_
_publ_author_name
'Tenne, Mario'
'Metz, Stefan'
'Münster, Ingo'
'Wagenblast, Gerhard'
'Strassner, Thomas'
_publ_section_title
;
 Phosphorescent Platinum(II) Complexes Based on C∧C*
 Cyclometalating Aryltriazol-5-ylidenes
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              6257
_journal_paper_doi               10.1021/om4004576
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C14 H15 N3 O2 Pt'
_chemical_formula_sum            'C14 H15 N3 O2 Pt'
_chemical_formula_weight         452.38
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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
_cell_angle_beta                 110.504(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0950(5)
_cell_length_b                   12.94500(10)
_cell_length_c                   11.7250(6)
_cell_measurement_reflns_used    506
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      22.001
_cell_measurement_theta_min      4.036
_cell_volume                     1435.15(12)
_computing_cell_refinement       'Dirax/lsq (Duisenberg, 1992)'
_computing_data_collection       'Collect (Nonius BV, 1999)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      198(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       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  0.0869
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25700
_diffrn_reflns_theta_full        23.24
_diffrn_reflns_theta_max         23.24
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    9.781
_exptl_absorpt_correction_T_max  0.3106
_exptl_absorpt_correction_T_min  0.0788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.094
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0251
_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)+(0.0130P)²+1.7950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0357
_refine_ls_wR_factor_ref         0.0400
_reflns_number_gt                1534
_reflns_number_total             2053
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4004576_si_001.cif
_cod_data_source_block           compound_9
_cod_original_cell_volume        1435.15(10)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4081758
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Pt1 Pt 0.97052(3) 0.08189(2) 0.38106(2) 0.02325(9) Uani 1 1 d .
O2 O 0.8401(4) 0.0093(3) 0.2297(4) 0.0342(11) Uani 1 1 d .
C2 C 1.0862(8) 0.2637(5) 0.6780(6) 0.0331(17) Uani 1 1 d .
H2 H 1.0566 0.3075 0.7295 0.040 Uiso 1 1 calc R
C13 C 0.8829(8) -0.0431(5) 0.1558(6) 0.044(2) Uani 1 1 d .
N2 N 1.2050(5) 0.1735(4) 0.6001(5) 0.0265(12) Uani 1 1 d .
O1 O 1.1454(4) 0.0186(3) 0.3542(4) 0.0315(11) Uani 1 1 d .
C11 C 1.1437(8) -0.0340(5) 0.2636(7) 0.0361(18) Uani 1 1 d .
C8 C 0.6124(7) 0.2656(5) 0.4765(6) 0.0391(17) Uani 1 1 d .
H8 H 0.5444 0.3037 0.4983 0.047 Uiso 1 1 calc R
N1 N 0.9964(5) 0.2177(3) 0.5750(4) 0.0236(13) Uani 1 1 d .
C6 C 0.6674(7) 0.1490(5) 0.3422(6) 0.0339(17) Uani 1 1 d .
H6 H 0.6361 0.1077 0.2708 0.041 Uiso 1 1 calc R
C12 C 1.0226(8) -0.0637(5) 0.1684(6) 0.0412(19) Uani 1 1 d .
H12 H 1.0369 -0.1024 0.1048 0.049 Uiso 1 1 calc R
C4 C 0.8482(6) 0.2170(4) 0.5118(5) 0.0226(15) Uani 1 1 d .
N3 N 1.2159(6) 0.2403(4) 0.6964(5) 0.0341(14) Uani 1 1 d .
C5 C 0.8100(6) 0.1528(4) 0.4103(5) 0.0215(14) Uani 1 1 d .
C7 C 0.5691(7) 0.2037(5) 0.3755(6) 0.0414(18) Uani 1 1 d .
H7 H 0.4713 0.1984 0.3283 0.050 Uiso 1 1 calc R
C9 C 0.7529(7) 0.2735(5) 0.5467(6) 0.0318(17) Uani 1 1 d .
H9 H 0.7835 0.3163 0.6169 0.038 Uiso 1 1 calc R
C1 C 1.0730(6) 0.1592(4) 0.5256(5) 0.0211(14) Uani 1 1 d .
C3 C 1.3337(6) 0.1293(5) 0.5961(6) 0.0387(17) Uani 1 1 d .
H3A H 1.3119 0.0820 0.5267 0.058 Uiso 1 1 calc R
H3B H 1.3812 0.0912 0.6717 0.058 Uiso 1 1 calc R
H3C H 1.3960 0.1844 0.5874 0.058 Uiso 1 1 calc R
C14 C 0.7636(7) -0.0851(6) 0.0473(6) 0.057(2) Uani 1 1 d .
H14A H 0.7296 -0.1502 0.0699 0.086 Uiso 1 1 calc R
H14B H 0.7979 -0.0975 -0.0200 0.086 Uiso 1 1 calc R
H14C H 0.6860 -0.0349 0.0219 0.086 Uiso 1 1 calc R
C10 C 1.2855(7) -0.0652(5) 0.2607(6) 0.052(2) Uani 1 1 d .
H10A H 1.3374 -0.0035 0.2517 0.077 Uiso 1 1 calc R
H10B H 1.2727 -0.1117 0.1917 0.077 Uiso 1 1 calc R
H10C H 1.3392 -0.1006 0.3367 0.077 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'
O O 0.0106 0.0060 '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
C1 Pt1 C5 80.1(2)
C1 Pt1 O2 172.7(2)
C5 Pt1 O2 92.6(2)
C1 Pt1 O1 96.6(2)
C5 Pt1 O1 175.7(2)
O2 Pt1 O1 90.59(16)
C13 O2 Pt1 124.3(4)
N3 C2 N1 111.5(5)
N3 C2 H2 124.2
N1 C2 H2 124.2
O2 C13 C12 126.6(6)
O2 C13 C14 113.5(7)
C12 C13 C14 119.9(7)
C1 N2 N3 113.3(5)
C1 N2 C3 129.4(5)
N3 N2 C3 117.2(5)
C11 O1 Pt1 125.7(4)
O1 C11 C12 125.2(6)
O1 C11 C10 115.8(7)
C12 C11 C10 119.0(6)
C7 C8 C9 120.8(6)
C7 C8 H8 119.6
C9 C8 H8 119.6
C1 N1 C2 108.7(5)
C1 N1 C4 115.5(5)
C2 N1 C4 135.8(5)
C5 C6 C7 121.6(6)
C5 C6 H6 119.2
C7 C6 H6 119.2
C11 C12 C13 127.3(7)
C11 C12 H12 116.4
C13 C12 H12 116.4
C9 C4 C5 123.8(6)
C9 C4 N1 124.1(6)
C5 C4 N1 112.1(5)
C2 N3 N2 102.9(5)
C6 C5 C4 115.9(5)
C6 C5 Pt1 129.0(5)
C4 C5 Pt1 115.1(4)
C8 C7 C6 120.1(6)
C8 C7 H7 120.0
C6 C7 H7 120.0
C8 C9 C4 117.7(6)
C8 C9 H9 121.1
C4 C9 H9 121.1
N2 C1 N1 103.5(5)
N2 C1 Pt1 139.3(5)
N1 C1 Pt1 117.2(4)
N2 C3 H3A 109.5
N2 C3 H3B 109.5
H3A C3 H3B 109.5
N2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C11 C10 H10A 109.5
C11 C10 H10B 109.5
H10A C10 H10B 109.5
C11 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pt1 C1 1.928(6)
Pt1 C5 1.994(5)
Pt1 O2 2.032(4)
Pt1 O1 2.068(4)
O2 C13 1.289(7)
C2 N3 1.286(7)
C2 N1 1.367(7)
C2 H2 0.9500
C13 C12 1.391(9)
C13 C14 1.513(9)
N2 C1 1.325(7)
N2 N3 1.396(6)
N2 C3 1.436(7)
O1 C11 1.256(7)
C11 C12 1.391(9)
C11 C10 1.500(8)
C8 C7 1.368(9)
C8 C9 1.371(8)
C8 H8 0.9500
N1 C1 1.349(6)
N1 C4 1.418(7)
C6 C5 1.381(8)
C6 C7 1.383(8)
C6 H6 0.9500
C12 H12 0.9500
C4 C9 1.379(7)
C4 C5 1.391(8)
C7 H7 0.9500
C9 H9 0.9500
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
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
C5 Pt1 O2 C13 171.6(5)
O1 Pt1 O2 C13 -5.6(4)
Pt1 O2 C13 C12 3.3(9)
Pt1 O2 C13 C14 -177.4(4)
C1 Pt1 O1 C11 -173.4(5)
O2 Pt1 O1 C11 5.9(5)
Pt1 O1 C11 C12 -3.7(9)
Pt1 O1 C11 C10 175.8(4)
N3 C2 N1 C1 1.4(7)
N3 C2 N1 C4 -179.1(6)
O1 C11 C12 C13 -1.2(11)
C10 C11 C12 C13 179.3(6)
O2 C13 C12 C11 1.4(11)
C14 C13 C12 C11 -177.8(6)
C1 N1 C4 C9 -178.6(5)
C2 N1 C4 C9 1.9(10)
C1 N1 C4 C5 1.3(7)
C2 N1 C4 C5 -178.2(6)
N1 C2 N3 N2 -1.4(7)
C1 N2 N3 C2 1.0(7)
C3 N2 N3 C2 -177.8(5)
C7 C6 C5 C4 -1.6(8)
C7 C6 C5 Pt1 -179.8(4)
C9 C4 C5 C6 1.0(8)
N1 C4 C5 C6 -179.0(5)
C9 C4 C5 Pt1 179.4(4)
N1 C4 C5 Pt1 -0.5(6)
C1 Pt1 C5 C6 178.0(6)
O2 Pt1 C5 C6 -1.6(5)
C1 Pt1 C5 C4 -0.2(4)
O2 Pt1 C5 C4 -179.8(4)
C9 C8 C7 C6 -0.8(9)
C5 C6 C7 C8 1.6(9)
C7 C8 C9 C4 0.1(9)
C5 C4 C9 C8 -0.2(9)
N1 C4 C9 C8 179.7(5)
N3 N2 C1 N1 -0.2(6)
C3 N2 C1 N1 178.4(5)
N3 N2 C1 Pt1 -178.5(5)
C3 N2 C1 Pt1 0.1(10)
C2 N1 C1 N2 -0.7(6)
C4 N1 C1 N2 179.7(4)
C2 N1 C1 Pt1 178.1(4)
C4 N1 C1 Pt1 -1.5(6)
C5 Pt1 C1 N2 179.1(7)
O1 Pt1 C1 N2 -3.7(6)
C5 Pt1 C1 N1 0.9(4)
O1 Pt1 C1 N1 178.1(4)
