#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/63/1506371.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_1506371
loop_
_publ_author_name
'Cooper, Thomas M.'
'Hall, Benjamin C.'
'McLean, Daniel G.'
'Rogers, Joy E.'
'Burke, Aaron R.'
'Turnbull, Kenneth'
'Weisner, Andrew'
'Fratini, Albert'
'Liu, Yao'
'Schanze, Kirk S.'
_publ_contact_author
;    Thomas M. Cooper
     Materials and Manufacturing Directorate AFRL/MLPJE    
     Air Force Research Laboratory
     Wright-Patterson Air Force Base, OH 45433
;
_publ_section_title
;
 Structure-optical property relationships in organometallic sydnones.
;
_journal_issue                   6
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              999
_journal_page_last               1007
_journal_paper_doi               10.1021/jp046806t
_journal_volume                  109
_journal_year                    2005
_chemical_formula_sum            'C44 H64 N4 O4 P2 Pt'
_chemical_formula_weight         970.02
_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                110.7380(10)
_cell_angle_beta                 109.7960(10)
_cell_angle_gamma                104.5780(10)
_cell_formula_units_Z            1
_cell_length_a                   10.9367(3)
_cell_length_b                   11.2973(3)
_cell_length_c                   11.4492(3)
_cell_measurement_temperature    150(2)
_cell_volume                     1128.32(6)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0684
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15739
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    3.224
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             496
_exptl_crystal_preparation
'recrystallization from a dichloromethane-methanol mixture'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         2.025
_refine_diff_density_min         -1.478
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         5593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0325P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0593
_reflns_number_gt                5591
_reflns_number_total             5593
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp046806tsi20040719_015304.cif
_cod_data_source_block           0310m
_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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1128.32(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506371
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
Pt Pt 1.0000 0.5000 0.5000 0.01834(5) Uani 1 2 d S
P P 0.95045(5) 0.28499(6) 0.32732(6) 0.01925(10) Uani 1 1 d .
N1 N 0.90132(19) 0.7176(2) 0.14273(19) 0.0220(3) Uani 1 1 d .
O1 O 1.09812(19) 0.8354(2) 0.1612(2) 0.0351(4) Uani 1 1 d .
C11 C 0.9212(2) 0.1456(2) 0.3737(2) 0.0217(4) Uani 1 1 d .
H11A H 0.9048 0.0592 0.2946 0.026 Uiso 1 1 calc R
H11B H 1.0093 0.1709 0.4581 0.026 Uiso 1 1 calc R
C1 C 0.8735(2) 0.5423(2) 0.3639(2) 0.0227(4) Uani 1 1 d .
C8 C 0.7624(2) 0.6912(2) 0.1350(2) 0.0199(4) Uani 1 1 d .
C3 C 0.7181(2) 0.6268(2) 0.2070(2) 0.0203(4) Uani 1 1 d .
N2 N 0.9740(2) 0.8409(2) 0.1616(3) 0.0326(4) Uani 1 1 d .
C2 C 0.8033(2) 0.5787(2) 0.2886(2) 0.0224(4) Uani 1 1 d .
O2 O 1.1978(2) 0.6798(3) 0.1337(3) 0.0489(6) Uani 1 1 d .
C7 C 0.6776(2) 0.7369(3) 0.0561(2) 0.0255(4) Uani 1 1 d .
H7A H 0.7095 0.7776 0.0061 0.031 Uiso 1 1 calc R
C12 C 0.7952(2) 0.1153(3) 0.4048(3) 0.0273(4) Uani 1 1 d .
H12A H 0.8065 0.2032 0.4779 0.033 Uiso 1 1 calc R
H12B H 0.7053 0.0806 0.3177 0.033 Uiso 1 1 calc R
C4 C 0.5841(2) 0.6143(3) 0.2000(2) 0.0260(4) Uani 1 1 d .
H4A H 0.5504 0.5724 0.2483 0.031 Uiso 1 1 calc R
C15 C 1.1029(2) 0.2929(3) 0.2946(3) 0.0300(5) Uani 1 1 d .
H15A H 1.1885 0.3250 0.3845 0.036 Uiso 1 1 calc R
H15B H 1.0836 0.1979 0.2273 0.036 Uiso 1 1 calc R
C6 C 0.5462(3) 0.7220(3) 0.0516(3) 0.0300(5) Uani 1 1 d .
H6A H 0.4877 0.7531 -0.0014 0.036 Uiso 1 1 calc R
C10 C 1.0982(3) 0.7050(3) 0.1408(3) 0.0322(5) Uani 1 1 d .
C5 C 0.4998(2) 0.6619(3) 0.1241(3) 0.0294(5) Uani 1 1 d .
H5A H 0.4103 0.6533 0.1220 0.035 Uiso 1 1 calc R
C9 C 0.9664(3) 0.6320(3) 0.1310(3) 0.0296(5) Uani 1 1 d .
H9A H 0.9312 0.5401 0.1186 0.036 Uiso 1 1 calc R
C17 C 1.2905(3) 0.4594(4) 0.2719(3) 0.0427(6) Uani 1 1 d .
H17A H 1.2977 0.4944 0.2054 0.051 Uiso 1 1 calc R
H17B H 1.3302 0.3888 0.2615 0.051 Uiso 1 1 calc R
C13 C 0.7837(3) 0.0083(3) 0.4561(3) 0.0335(5) Uani 1 1 d .
H13A H 0.8720 0.0448 0.5454 0.040 Uiso 1 1 calc R
H13B H 0.7765 -0.0782 0.3848 0.040 Uiso 1 1 calc R
C16 C 1.1351(3) 0.3916(4) 0.2338(3) 0.0423(7) Uani 1 1 d .
H16A H 1.0775 0.3382 0.1292 0.051 Uiso 1 1 calc R
H16B H 1.1037 0.4659 0.2681 0.051 Uiso 1 1 calc R
C19 C 0.7951(2) 0.2180(2) 0.1558(2) 0.0231(4) Uani 1 1 d .
H19A H 0.7106 0.2146 0.1709 0.028 Uiso 1 1 calc R
H19B H 0.8129 0.2853 0.1202 0.028 Uiso 1 1 calc R
C20 C 0.7578(3) 0.0736(3) 0.0409(2) 0.0263(4) Uani 1 1 d .
C14 C 0.6540(4) -0.0267(4) 0.4816(4) 0.0500(8) Uani 1 1 d .
H14A H 0.6512 -0.0960 0.5145 0.075 Uiso 1 1 calc R
H14B H 0.5661 -0.0648 0.3930 0.075 Uiso 1 1 calc R
H14C H 0.6616 0.0582 0.5536 0.075 Uiso 1 1 calc R
C18 C 1.3788(5) 0.5801(5) 0.4231(4) 0.0695(12) Uani 1 1 d .
H18A H 1.4789 0.6215 0.4440 0.104 Uiso 1 1 calc R
H18B H 1.3734 0.5454 0.4893 0.104 Uiso 1 1 calc R
H18C H 1.3408 0.6509 0.4332 0.104 Uiso 1 1 calc R
C21 C 0.6289(2) 0.0271(3) -0.0991(2) 0.0261(4) Uani 1 1 d .
C22 C 0.5946(3) -0.1141(3) -0.2156(3) 0.0374(6) Uani 1 1 d .
H22A H 0.5114 -0.1391 -0.3029 0.056 Uiso 1 1 calc R
H22B H 0.5729 -0.1851 -0.1864 0.056 Uiso 1 1 calc R
H22C H 0.6773 -0.1089 -0.2326 0.056 Uiso 1 1 calc R
H21A H 0.545(4) 0.024(4) -0.084(3) 0.035(9) Uiso 1 1 d .
H20B H 0.735(4) 0.007(4) 0.078(4) 0.036(9) Uiso 1 1 d .
H21B H 0.650(3) 0.098(4) -0.127(3) 0.028(8) Uiso 1 1 d .
H20A H 0.836(4) 0.070(4) 0.023(4) 0.039(9) 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'
P P 0.1023 0.0942 '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
C1 Pt C1 180.000(1) . 2_766
C1 Pt P 85.89(6) . 2_766
C1 Pt P 94.11(6) 2_766 2_766
C1 Pt P 94.11(6) . .
C1 Pt P 85.89(6) 2_766 .
P Pt P 180.0 2_766 .
C15 P C11 103.49(11) . .
C15 P C19 106.65(11) . .
C11 P C19 105.68(10) . .
C15 P Pt 110.11(9) . .
C11 P Pt 115.02(7) . .
C19 P Pt 114.96(8) . .
N2 N1 C9 115.0(2) . .
N2 N1 C8 116.67(19) . .
C9 N1 C8 128.3(2) . .
N2 O1 C10 111.11(18) . .
C12 C11 P 114.35(15) . .
C12 C11 H11A 108.7 . .
P C11 H11A 108.7 . .
C12 C11 H11B 108.7 . .
P C11 H11B 108.7 . .
H11A C11 H11B 107.6 . .
C2 C1 Pt 174.9(2) . .
C7 C8 C3 122.5(2) . .
C7 C8 N1 116.3(2) . .
C3 C8 N1 121.13(18) . .
C8 C3 C4 116.40(19) . .
C8 C3 C2 123.55(19) . .
C4 C3 C2 120.0(2) . .
N1 N2 O1 103.93(19) . .
C1 C2 C3 176.1(2) . .
C6 C7 C8 119.1(2) . .
C6 C7 H7A 120.4 . .
C8 C7 H7A 120.4 . .
C13 C12 C11 112.4(2) . .
C13 C12 H12A 109.1 . .
C11 C12 H12A 109.1 . .
C13 C12 H12B 109.1 . .
C11 C12 H12B 109.1 . .
H12A C12 H12B 107.9 . .
C5 C4 C3 121.6(2) . .
C5 C4 H4A 119.2 . .
C3 C4 H4A 119.2 . .
C16 C15 P 112.7(2) . .
C16 C15 H15A 109.0 . .
P C15 H15A 109.0 . .
C16 C15 H15B 109.0 . .
P C15 H15B 109.0 . .
H15A C15 H15B 107.8 . .
C5 C6 C7 120.2(2) . .
C5 C6 H6A 119.9 . .
C7 C6 H6A 119.9 . .
O2 C10 O1 120.3(2) . .
O2 C10 C9 136.1(3) . .
O1 C10 C9 103.5(2) . .
C6 C5 C4 120.1(2) . .
C6 C5 H5A 120.0 . .
C4 C5 H5A 120.0 . .
N1 C9 C10 106.4(2) . .
N1 C9 H9A 126.8 . .
C10 C9 H9A 126.8 . .
C16 C17 C18 111.7(3) . .
C16 C17 H17A 109.3 . .
C18 C17 H17A 109.3 . .
C16 C17 H17B 109.3 . .
C18 C17 H17B 109.3 . .
H17A C17 H17B 107.9 . .
C12 C13 C14 112.5(3) . .
C12 C13 H13A 109.1 . .
C14 C13 H13A 109.1 . .
C12 C13 H13B 109.1 . .
C14 C13 H13B 109.1 . .
H13A C13 H13B 107.8 . .
C17 C16 C15 114.7(3) . .
C17 C16 H16A 108.6 . .
C15 C16 H16A 108.6 . .
C17 C16 H16B 108.6 . .
C15 C16 H16B 108.6 . .
H16A C16 H16B 107.6 . .
C20 C19 P 115.78(15) . .
C20 C19 H19A 108.3 . .
P C19 H19A 108.3 . .
C20 C19 H19B 108.3 . .
P C19 H19B 108.3 . .
H19A C19 H19B 107.4 . .
C21 C20 C19 112.28(19) . .
C21 C20 H20B 109(2) . .
C19 C20 H20B 106(2) . .
C21 C20 H20A 108(2) . .
C19 C20 H20A 112(2) . .
H20B C20 H20A 109(3) . .
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 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C22 C21 C20 112.6(2) . .
C22 C21 H21A 110(2) . .
C20 C21 H21A 109.4(19) . .
C22 C21 H21B 110(2) . .
C20 C21 H21B 108.0(19) . .
H21A C21 H21B 106(3) . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pt C1 1.992(2) .
Pt C1 1.992(2) 2_766
Pt P 2.3051(6) 2_766
Pt P 2.3051(5) .
P C15 1.816(2) .
P C11 1.821(2) .
P C19 1.832(2) .
N1 N2 1.316(3) .
N1 C9 1.334(3) .
N1 C8 1.437(3) .
O1 N2 1.377(3) .
O1 C10 1.407(4) .
C11 C12 1.525(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C1 C2 1.210(3) .
C8 C7 1.396(3) .
C8 C3 1.400(3) .
C3 C4 1.409(3) .
C3 C2 1.435(3) .
O2 C10 1.214(3) .
C7 C6 1.385(3) .
C7 H7A 0.9500 .
C12 C13 1.516(4) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C4 C5 1.389(3) .
C4 H4A 0.9500 .
C15 C16 1.540(4) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C6 C5 1.385(4) .
C6 H6A 0.9500 .
C10 C9 1.413(3) .
C5 H5A 0.9500 .
C9 H9A 0.9500 .
C17 C16 1.507(4) .
C17 C18 1.524(5) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C13 C14 1.527(4) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C19 C20 1.530(3) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.528(3) .
C20 H20B 1.00(4) .
C20 H20A 0.96(4) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C21 C22 1.522(4) .
C21 H21A 0.98(4) .
C21 H21B 0.97(4) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 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
_geom_torsion_site_symmetry_1
C1 Pt P C15 106.16(11) .
C1 Pt P C15 -73.84(11) 2_766
C1 Pt P C11 -137.42(10) .
C1 Pt P C11 42.58(10) 2_766
C1 Pt P C19 -14.30(11) .
C1 Pt P C19 165.70(11) 2_766
C15 P C11 C12 -179.15(17) .
C19 P C11 C12 -67.22(18) .
Pt P C11 C12 60.71(17) .
N2 N1 C8 C7 42.1(3) .
C9 N1 C8 C7 -136.8(2) .
N2 N1 C8 C3 -136.1(2) .
C9 N1 C8 C3 45.1(3) .
C7 C8 C3 C4 -2.2(3) .
N1 C8 C3 C4 175.9(2) .
C7 C8 C3 C2 179.9(2) .
N1 C8 C3 C2 -2.1(3) .
C9 N1 N2 O1 0.5(3) .
C8 N1 N2 O1 -178.54(18) .
C10 O1 N2 N1 0.3(3) .
C3 C8 C7 C6 2.0(3) .
N1 C8 C7 C6 -176.2(2) .
P C11 C12 C13 -174.64(17) .
C8 C3 C4 C5 0.8(3) .
C2 C3 C4 C5 178.8(2) .
C11 P C15 C16 172.35(19) .
C19 P C15 C16 61.1(2) .
Pt P C15 C16 -64.2(2) .
C8 C7 C6 C5 -0.3(4) .
N2 O1 C10 O2 178.1(3) .
N2 O1 C10 C9 -0.9(3) .
C7 C6 C5 C4 -1.0(4) .
C3 C4 C5 C6 0.7(4) .
N2 N1 C9 C10 -1.1(3) .
C8 N1 C9 C10 177.8(2) .
O2 C10 C9 N1 -177.6(3) .
O1 C10 C9 N1 1.1(3) .
C11 C12 C13 C14 -177.6(2) .
C18 C17 C16 C15 -77.6(4) .
P C15 C16 C17 150.4(2) .
C15 P C19 C20 59.3(2) .
C11 P C19 C20 -50.4(2) .
Pt P C19 C20 -178.34(15) .
P C19 C20 C21 -178.92(17) .
C19 C20 C21 C22 177.8(2) .
