#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:39:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178575 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/85/4068580.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_4068580
loop_
_publ_author_name
'Bokach, Nadezhda A.'
'Kuznetsov, Maxim L.'
'Haukka, Matti'
'Ovcharenko, Victor I.'
'Tretyakov, Eugeny V.'
'Kukushkin, Vadim Yu.'
_publ_section_title
;
 Platinum(II)-Complexed Tetrahydroimidazo[1,2-b][1,2,4]oxadiazoles Derived
 from Metal-Mediated 1,3-Dipolar Cycloaddition. Novel Type of
 Heterocycles, Which Do Not Exist without the Metal Center
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1406
_journal_paper_doi               10.1021/om800963d
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C20 H40 Cl2 N8 O2 Pt'
_chemical_formula_sum            'C20 H40 Cl2 N8 O2 Pt'
_chemical_formula_weight         690.59
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.330(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8650(2)
_cell_length_b                   12.4316(4)
_cell_length_c                   20.0399(6)
_cell_measurement_reflns_used    13817
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      1.00
_cell_volume                     2690.27(13)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Diamond v.3.1f (Brandenburg, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            55769
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    5.447
_exptl_absorpt_correction_T_max  0.6887
_exptl_absorpt_correction_T_min  0.4578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v.2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         7.805
_refine_diff_density_min         -3.035
_refine_diff_density_rms         0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         7082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0572
_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)+(0.0000P)²+46.6745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                5939
_reflns_number_total             7082
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800963d_si_002.cif
_cod_data_source_block           trans_4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4068580
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 0.76724(2) 0.07253(3) 0.586937(14) 0.02324(9) Uani 1 1 d .
Cl1 Cl 0.76942(19) 0.1268(2) 0.69714(10) 0.0363(5) Uani 1 1 d .
Cl2 Cl 0.77432(16) 0.01794(15) 0.47738(9) 0.0246(4) Uani 1 1 d .
O1 O 0.8446(5) 0.3993(5) 0.5518(3) 0.0304(13) Uani 1 1 d .
O2 O 0.7018(5) -0.2524(5) 0.6338(3) 0.0287(12) Uani 1 1 d .
N1 N 0.8179(5) 0.2219(5) 0.5604(3) 0.0237(13) Uani 1 1 d .
N2 N 1.0396(5) 0.1824(5) 0.5654(3) 0.0236(13) Uani 1 1 d .
H2N H 1.0630 0.1419 0.5378 0.035 Uiso 1 1 d R
N3 N 0.9631(6) 0.3526(6) 0.5395(3) 0.0268(14) Uani 1 1 d .
N4 N 0.6602(6) 0.3458(6) 0.5840(4) 0.0333(16) Uani 1 1 d .
N5 N 0.7142(5) -0.0779(6) 0.6085(3) 0.0253(13) Uani 1 1 d .
N6 N 0.4955(5) -0.0518(5) 0.6236(3) 0.0215(13) Uani 1 1 d .
H6N H 0.4235 -0.0344 0.6032 0.032 Uiso 1 1 d R
N7 N 0.5764(5) -0.2257(5) 0.6009(3) 0.0230(13) Uani 1 1 d .
N8 N 0.8917(6) -0.1764(6) 0.6560(3) 0.0334(16) Uani 1 1 d .
C1 C 0.9349(6) 0.2372(6) 0.5301(4) 0.0229(15) Uani 1 1 d .
H1 H 0.9247 0.2177 0.4814 0.027 Uiso 1 1 calc R
C2 C 1.1368(6) 0.2628(6) 0.5843(3) 0.0208(14) Uani 1 1 d .
C3 C 1.2146(7) 0.2859(7) 0.5264(4) 0.0277(16) Uani 1 1 d .
H3A H 1.2532 0.2191 0.5132 0.042 Uiso 1 1 calc R
H3B H 1.2791 0.3386 0.5410 0.042 Uiso 1 1 calc R
H3C H 1.1611 0.3148 0.4880 0.042 Uiso 1 1 calc R
C4 C 1.2216(8) 0.2205(8) 0.6444(4) 0.036(2) Uani 1 1 d .
H4A H 1.1713 0.1942 0.6787 0.054 Uiso 1 1 calc R
H4B H 1.2757 0.2786 0.6631 0.054 Uiso 1 1 calc R
H4C H 1.2722 0.1615 0.6298 0.054 Uiso 1 1 calc R
C5 C 1.0571(7) 0.3612(7) 0.6000(4) 0.0260(16) Uani 1 1 d .
C6 C 1.1229(9) 0.4687(7) 0.5987(5) 0.037(2) Uani 1 1 d .
H6A H 1.1532 0.4788 0.5548 0.055 Uiso 1 1 calc R
H6B H 1.1930 0.4701 0.6340 0.055 Uiso 1 1 calc R
H6C H 1.0651 0.5267 0.6065 0.055 Uiso 1 1 calc R
C7 C 1.0020(8) 0.3477(7) 0.6663(4) 0.0327(18) Uani 1 1 d .
H7A H 1.0668 0.3591 0.7037 0.049 Uiso 1 1 calc R
H7B H 0.9684 0.2748 0.6690 0.049 Uiso 1 1 calc R
H7C H 0.9357 0.4004 0.6689 0.049 Uiso 1 1 calc R
C8 C 0.7703(7) 0.3156(7) 0.5671(4) 0.0311(18) Uani 1 1 d .
C9 C 0.6317(10) 0.4578(8) 0.5928(6) 0.050(3) Uani 1 1 d .
H9A H 0.7036 0.4941 0.6166 0.076 Uiso 1 1 calc R
H9B H 0.5610 0.4640 0.6190 0.076 Uiso 1 1 calc R
H9C H 0.6110 0.4915 0.5488 0.076 Uiso 1 1 calc R
C10 C 0.5575(8) 0.2686(9) 0.5820(5) 0.043(2) Uani 1 1 d .
H10A H 0.5860 0.1976 0.5690 0.064 Uiso 1 1 calc R
H10B H 0.4894 0.2926 0.5492 0.064 Uiso 1 1 calc R
H10C H 0.5284 0.2641 0.6265 0.064 Uiso 1 1 calc R
C14 C 0.5836(7) -0.1069(6) 0.5874(4) 0.0221(15) Uani 1 1 d .
H14 H 0.5640 -0.0932 0.5382 0.027 Uiso 1 1 calc R
C15 C 0.4712(6) -0.1216(6) 0.6811(4) 0.0221(15) Uani 1 1 d .
C16 C 0.5674(7) -0.0973(7) 0.7405(4) 0.0276(17) Uani 1 1 d .
H16A H 0.6492 -0.1210 0.7301 0.041 Uiso 1 1 calc R
H16B H 0.5456 -0.1356 0.7803 0.041 Uiso 1 1 calc R
H16C H 0.5692 -0.0197 0.7493 0.041 Uiso 1 1 calc R
C17 C 0.3431(7) -0.0955(7) 0.7016(4) 0.0280(17) Uani 1 1 d .
H17A H 0.3417 -0.0208 0.7171 0.042 Uiso 1 1 calc R
H17B H 0.3248 -0.1438 0.7378 0.042 Uiso 1 1 calc R
H17C H 0.2806 -0.1050 0.6629 0.042 Uiso 1 1 calc R
C18 C 0.4826(7) -0.2376(6) 0.6520(4) 0.0231(15) Uani 1 1 d .
C19 C 0.5208(9) -0.3225(7) 0.7049(4) 0.0338(19) Uani 1 1 d .
H20A H 0.4553 -0.3309 0.7344 0.051 Uiso 1 1 calc R
H20B H 0.5976 -0.3001 0.7315 0.051 Uiso 1 1 calc R
H20C H 0.5342 -0.3912 0.6829 0.051 Uiso 1 1 calc R
C20 C 0.3653(8) -0.2728(7) 0.6087(4) 0.0324(18) Uani 1 1 d .
H19A H 0.3817 -0.3393 0.5849 0.049 Uiso 1 1 calc R
H19B H 0.3395 -0.2163 0.5760 0.049 Uiso 1 1 calc R
H19C H 0.2992 -0.2855 0.6373 0.049 Uiso 1 1 calc R
C21 C 0.7724(6) -0.1645(7) 0.6305(4) 0.0230(15) Uani 1 1 d .
C22 C 0.9402(10) -0.2850(10) 0.6692(5) 0.054(3) Uani 1 1 d .
H22A H 0.8767 -0.3295 0.6869 0.081 Uiso 1 1 calc R
H22B H 1.0137 -0.2817 0.7022 0.081 Uiso 1 1 calc R
H22C H 0.9626 -0.3166 0.6274 0.081 Uiso 1 1 calc R
C23 C 0.9837(7) -0.0917(9) 0.6515(5) 0.043(2) Uani 1 1 d .
H23A H 0.9999 -0.0832 0.6046 0.065 Uiso 1 1 calc R
H23B H 1.0607 -0.1113 0.6790 0.065 Uiso 1 1 calc R
H23C H 0.9523 -0.0238 0.6678 0.065 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'
Cl Cl 0.1484 0.1585 '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_publ_flag
N5 Pt1 N1 177.1(2) yes
N5 Pt1 Cl1 92.23(18) ?
N1 Pt1 Cl1 90.51(19) ?
N5 Pt1 Cl2 88.37(18) ?
N1 Pt1 Cl2 88.93(19) ?
Cl1 Pt1 Cl2 177.51(7) yes
C8 O1 N3 106.7(6) ?
C21 O2 N7 107.3(5) ?
C8 N1 C1 107.4(7) ?
C8 N1 Pt1 132.7(5) ?
C1 N1 Pt1 119.8(5) ?
C1 N2 C2 108.0(6) ?
C1 N2 H2N 104.4 ?
C2 N2 H2N 109.1 ?
O1 N3 C1 103.5(5) ?
O1 N3 C5 111.8(6) ?
C1 N3 C5 106.6(6) ?
C8 N4 C9 120.9(8) ?
C8 N4 C10 120.7(8) ?
C9 N4 C10 117.5(7) ?
C21 N5 C14 108.1(7) ?
C21 N5 Pt1 134.4(5) ?
C14 N5 Pt1 116.9(5) ?
C14 N6 C15 107.3(6) ?
C14 N6 H6N 119.7 ?
C15 N6 H6N 106.4 ?
O2 N7 C14 103.7(5) ?
O2 N7 C18 109.1(5) ?
C14 N7 C18 105.5(5) ?
C21 N8 C23 122.3(7) ?
C21 N8 C22 118.8(8) ?
C23 N8 C22 116.2(7) ?
N2 C1 N3 104.8(6) ?
N2 C1 N1 113.8(6) ?
N3 C1 N1 104.4(6) ?
N2 C1 H1 111.2 ?
N3 C1 H1 111.2 ?
N1 C1 H1 111.2 ?
N2 C2 C4 108.8(6) ?
N2 C2 C3 111.8(6) ?
C4 C2 C3 109.0(6) ?
N2 C2 C5 100.8(5) ?
C4 C2 C5 114.5(6) ?
C3 C2 C5 111.8(6) ?
C2 C3 H3A 109.5 ?
C2 C3 H3B 109.5 ?
H3A C3 H3B 109.5 ?
C2 C3 H3C 109.5 ?
H3A C3 H3C 109.5 ?
H3B C3 H3C 109.5 ?
C2 C4 H4A 109.5 ?
C2 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
C2 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
N3 C5 C6 109.2(7) ?
N3 C5 C7 113.5(6) ?
C6 C5 C7 110.0(7) ?
N3 C5 C2 97.2(6) ?
C6 C5 C2 114.6(6) ?
C7 C5 C2 111.8(7) ?
C5 C6 H6A 109.5 ?
C5 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C5 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
C5 C7 H7A 109.5 ?
C5 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
C5 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
N1 C8 N4 131.5(8) ?
N1 C8 O1 114.2(7) ?
N4 C8 O1 114.2(8) ?
N4 C9 H9A 109.5 ?
N4 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
N4 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
N4 C10 H10A 109.5 ?
N4 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
N4 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
N6 C14 N5 114.2(6) ?
N6 C14 N7 109.0(6) ?
N5 C14 N7 104.8(6) ?
N6 C14 H14 109.6 ?
N5 C14 H14 109.6 ?
N7 C14 H14 109.6 ?
N6 C15 C16 108.9(6) ?
N6 C15 C17 109.2(6) ?
C16 C15 C17 108.3(6) ?
N6 C15 C18 102.8(6) ?
C16 C15 C18 113.4(6) ?
C17 C15 C18 114.1(6) ?
C15 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C15 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C15 C17 H17A 109.5 ?
C15 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C15 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C19 C18 C20 110.1(7) ?
C19 C18 N7 112.5(6) ?
C20 C18 N7 102.9(6) ?
C19 C18 C15 114.0(6) ?
C20 C18 C15 112.4(6) ?
N7 C18 C15 104.2(6) ?
C18 C19 H20A 109.5 ?
C18 C19 H20B 109.5 ?
H20A C19 H20B 109.5 ?
C18 C19 H20C 109.5 ?
H20A C19 H20C 109.5 ?
H20B C19 H20C 109.5 ?
C18 C20 H19A 109.5 ?
C18 C20 H19B 109.5 ?
H19A C20 H19B 109.5 ?
C18 C20 H19C 109.5 ?
H19A C20 H19C 109.5 ?
H19B C20 H19C 109.5 ?
N5 C21 O2 115.6(6) ?
N5 C21 N8 129.0(8) ?
O2 C21 N8 115.1(7) ?
N8 C22 H22A 109.5 ?
N8 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
N8 C22 H22C 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
N8 C23 H23A 109.5 ?
N8 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
N8 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Pt1 N5 2.018(7) yes
Pt1 N1 2.025(7) yes
Pt1 Cl1 2.307(2) yes
Pt1 Cl2 2.3074(18) yes
O1 C8 1.372(10) ?
O1 N3 1.458(8) ?
O2 C21 1.341(10) ?
O2 N7 1.484(8) ?
N1 C8 1.288(11) ?
N1 C1 1.481(9) ?
N2 C1 1.443(9) ?
N2 C2 1.473(9) ?
N2 H2N 0.8090 ?
N3 C1 1.475(10) ?
N3 C5 1.500(10) ?
N4 C8 1.333(10) ?
N4 C9 1.442(12) ?
N4 C10 1.469(12) ?
N5 C21 1.301(10) ?
N5 C14 1.479(9) ?
N6 C14 1.438(9) ?
N6 C15 1.489(9) ?
N6 H6N 0.8688 ?
N7 C14 1.505(10) ?
N7 C18 1.530(9) ?
N8 C21 1.348(9) ?
N8 C23 1.461(12) ?
N8 C22 1.463(12) ?
C1 H1 1.0000 ?
C2 C4 1.526(10) ?
C2 C3 1.537(10) ?
C2 C5 1.551(11) ?
C3 H3A 0.9800 ?
C3 H3B 0.9800 ?
C3 H3C 0.9800 ?
C4 H4A 0.9800 ?
C4 H4B 0.9800 ?
C4 H4C 0.9800 ?
C5 C6 1.518(12) ?
C5 C7 1.526(11) ?
C6 H6A 0.9800 ?
C6 H6B 0.9800 ?
C6 H6C 0.9800 ?
C7 H7A 0.9800 ?
C7 H7B 0.9800 ?
C7 H7C 0.9800 ?
C9 H9A 0.9800 ?
C9 H9B 0.9800 ?
C9 H9C 0.9800 ?
C10 H10A 0.9800 ?
C10 H10B 0.9800 ?
C10 H10C 0.9800 ?
C14 H14 1.0000 ?
C15 C16 1.526(10) ?
C15 C17 1.529(10) ?
C15 C18 1.565(11) ?
C16 H16A 0.9800 ?
C16 H16B 0.9800 ?
C16 H16C 0.9800 ?
C17 H17A 0.9800 ?
C17 H17B 0.9800 ?
C17 H17C 0.9800 ?
C18 C19 1.521(11) ?
C18 C20 1.525(11) ?
C19 H20A 0.9800 ?
C19 H20B 0.9800 ?
C19 H20C 0.9800 ?
C20 H19A 0.9800 ?
C20 H19B 0.9800 ?
C20 H19C 0.9800 ?
C22 H22A 0.9800 ?
C22 H22B 0.9800 ?
C22 H22C 0.9800 ?
C23 H23A 0.9800 ?
C23 H23B 0.9800 ?
C23 H23C 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2N Cl2 0.81 2.70 3.377(6) 142.5 3_756 yes
N6 H6N Cl2 0.87 2.55 3.399(6) 165.9 3_656 yes
