#------------------------------------------------------------------------------
#$Date: 2019-11-26 14:04:45 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243467 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/61/1556103.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_1556103
loop_
_publ_author_name
'Pietschnig, Rudolf'
'Schäfer, Sven'
'Merz, Klaus'
_publ_section_title
;
 Self-addition of a sterically hindered alkynylselenolate.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              1867
_journal_page_last               1869
_journal_paper_doi               10.1021/ol034476+
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C68 H92 Se10'
_chemical_formula_weight         1699.02
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                101.621(5)
_cell_angle_beta                 96.648(5)
_cell_angle_gamma                94.940(5)
_cell_formula_units_Z            1
_cell_length_a                   10.459(3)
_cell_length_b                   12.983(3)
_cell_length_c                   13.711(4)
_cell_measurement_reflns_used    54
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      19.25
_cell_measurement_theta_min      3.20
_cell_volume                     1799.9(8)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    'BRUKER axs SHELXTL-PLUS'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker axs CCD 1000'
_diffrn_measurement_method       omega-scan
_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  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0894
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9388
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    5.108
_exptl_absorpt_correction_T_max  0.360
_exptl_absorpt_correction_T_min  0.305
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.888
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         6265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0597P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                3919
_reflns_number_total             6265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol034476%2Bsi20030319_090357.cif
_cod_data_source_block           md6761
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. A new data item '_refine_ls_weighting_details' was
created with the value set to
'w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1556103
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_calc_flag
_atom_site_refinement_flags
Se1 Se 0.16821(7) 0.29571(5) 0.60287(5) 0.0363(2) Uani 1 d .
Se2 Se -0.05164(7) 0.30615(5) 0.56769(5) 0.03316(19) Uani 1 d .
Se3 Se 0.18945(8) 0.52321(5) 0.54129(5) 0.0357(2) Uani 1 d .
Se4 Se 0.22822(8) 0.69944(6) 0.75681(5) 0.0413(2) Uani 1 d .
Se5 Se 0.41487(7) 0.61387(6) 0.75114(6) 0.0389(2) Uani 1 d .
C17 C 0.2406(6) 0.4434(5) 0.6391(5) 0.0267(15) Uani 1 d .
C18 C 0.3299(7) 0.4717(5) 0.7183(5) 0.0290(15) Uani 1 d .
C2 C -0.0562(7) 0.1749(5) 0.3634(5) 0.0322(16) Uani 1 d .
C34 C 0.1599(7) 0.6584(5) 0.6181(5) 0.0320(16) Uani 1 d .
C1 C -0.0874(6) 0.2757(5) 0.4242(5) 0.0296(16) Uani 1 d .
C7 C -0.1361(7) 0.0789(5) 0.3585(5) 0.0353(17) Uani 1 d .
C20 C 0.3224(7) 0.3926(5) 0.8710(5) 0.0324(16) Uani 1 d .
C6 C -0.1090(7) -0.0127(5) 0.2975(5) 0.0363(17) Uani 1 d .
H6A H -0.1626 -0.0759 0.2931 0.044 Uiso 1 calc R
C19 C 0.3741(6) 0.3972(5) 0.7819(5) 0.0284(15) Uani 1 d .
C5 C -0.0057(7) -0.0149(5) 0.2424(5) 0.0387(18) Uani 1 d .
C21 C 0.3575(8) 0.3141(6) 0.9229(5) 0.044(2) Uani 1 d .
H21A H 0.3238 0.3109 0.9830 0.053 Uiso 1 calc R
C23 C 0.4924(7) 0.2499(6) 0.8016(6) 0.0428(19) Uani 1 d .
H23A H 0.5515 0.2027 0.7794 0.051 Uiso 1 calc R
C8 C 0.1406(8) 0.2727(6) 0.3131(6) 0.049(2) Uani 1 d .
H8A H 0.1164 0.3306 0.3641 0.058 Uiso 1 calc R
C31 C 0.5301(7) 0.3368(6) 0.6588(5) 0.0421(19) Uani 1 d .
H31A H 0.4757 0.3753 0.6177 0.050 Uiso 1 calc R
C3 C 0.0479(7) 0.1744(6) 0.3085(5) 0.0362(17) Uani 1 d .
C4 C 0.0696(7) 0.0785(6) 0.2494(6) 0.0447(19) Uani 1 d .
H4A H 0.1397 0.0780 0.2122 0.054 Uiso 1 calc R
C14 C -0.2509(8) 0.0746(5) 0.4166(6) 0.0427(19) Uani 1 d .
H14A H -0.2544 0.1470 0.4556 0.051 Uiso 1 calc R
C11 C 0.0210(9) -0.1187(6) 0.1774(6) 0.051(2) Uani 1 d .
H11A H -0.0513 -0.1725 0.1792 0.062 Uiso 1 calc R
C24 C 0.4610(7) 0.3254(5) 0.7460(5) 0.0340(17) Uani 1 d .
C22 C 0.4395(8) 0.2419(6) 0.8886(6) 0.046(2) Uani 1 d .
C25 C 0.2320(7) 0.4725(6) 0.9113(5) 0.0413(19) Uani 1 d .
H25A H 0.2401 0.5314 0.8757 0.050 Uiso 1 calc R
C28 C 0.4780(9) 0.1560(8) 0.9445(7) 0.067(3) Uani 1 d .
H28A H 0.4768 0.0916 0.8913 0.080 Uiso 1 calc R
C32 C 0.5491(9) 0.2341(7) 0.5897(7) 0.067(3) Uani 1 d .
H32A H 0.4662 0.1911 0.5679 0.101 Uiso 1 calc R
H32B H 0.6077 0.1959 0.6254 0.101 Uiso 1 calc R
H32C H 0.5855 0.2494 0.5316 0.101 Uiso 1 calc R
C26 C 0.2665(9) 0.5190(7) 1.0225(6) 0.065(3) Uani 1 d .
H26A H 0.2066 0.5693 1.0438 0.097 Uiso 1 calc R
H26B H 0.3540 0.5547 1.0355 0.097 Uiso 1 calc R
H26C H 0.2610 0.4628 1.0594 0.097 Uiso 1 calc R
C13 C 0.1430(10) -0.1564(7) 0.2200(6) 0.065(3) Uani 1 d .
H13A H 0.1573 -0.2223 0.1771 0.098 Uiso 1 calc R
H13B H 0.1347 -0.1675 0.2869 0.098 Uiso 1 calc R
H13C H 0.2158 -0.1035 0.2234 0.098 Uiso 1 calc R
C33 C 0.6591(8) 0.4073(7) 0.6952(7) 0.060(2) Uani 1 d .
H33A H 0.6441 0.4724 0.7392 0.091 Uiso 1 calc R
H33B H 0.6963 0.4237 0.6378 0.091 Uiso 1 calc R
H33C H 0.7184 0.3703 0.7317 0.091 Uiso 1 calc R
C16 C -0.3799(8) 0.0417(7) 0.3461(7) 0.067(3) Uani 1 d .
H16A H -0.4507 0.0399 0.3858 0.101 Uiso 1 calc R
H16B H -0.3782 -0.0280 0.3045 0.101 Uiso 1 calc R
H16C H -0.3920 0.0924 0.3036 0.101 Uiso 1 calc R
C15 C -0.2317(9) 0.0042(7) 0.4911(7) 0.065(3) Uani 1 d .
H15A H -0.1499 0.0278 0.5342 0.097 Uiso 1 calc R
H15B H -0.2311 -0.0682 0.4552 0.097 Uiso 1 calc R
H15C H -0.3019 0.0077 0.5317 0.097 Uiso 1 calc R
C27 C 0.0921(9) 0.4226(8) 0.8877(7) 0.071(3) Uani 1 d .
H27A H 0.0359 0.4742 0.9135 0.107 Uiso 1 calc R
H27B H 0.0821 0.3623 0.9191 0.107 Uiso 1 calc R
H27C H 0.0691 0.3994 0.8155 0.107 Uiso 1 calc R
C9 C 0.1276(9) 0.3078(7) 0.2107(6) 0.068(3) Uani 1 d .
H9A H 0.1876 0.3705 0.2156 0.102 Uiso 1 calc R
H9B H 0.0397 0.3235 0.1940 0.102 Uiso 1 calc R
H9C H 0.1474 0.2513 0.1586 0.102 Uiso 1 calc R
C12 C 0.0234(10) -0.1143(7) 0.0682(6) 0.074(3) Uani 1 d .
H12A H 0.0407 -0.1823 0.0310 0.110 Uiso 1 calc R
H12B H 0.0909 -0.0601 0.0633 0.110 Uiso 1 calc R
H12C H -0.0598 -0.0974 0.0402 0.110 Uiso 1 calc R
C10 C 0.2798(8) 0.2581(8) 0.3444(7) 0.070(3) Uani 1 d .
H10A H 0.2874 0.2361 0.4081 0.105 Uiso 1 calc R
H10B H 0.3338 0.3245 0.3514 0.105 Uiso 1 calc R
H10C H 0.3077 0.2045 0.2937 0.105 Uiso 1 calc R
C29 C 0.6166(10) 0.1814(8) 0.9927(7) 0.079(3) Uani 1 d .
H29A H 0.6399 0.1268 1.0282 0.118 Uiso 1 calc R
H29B H 0.6270 0.2492 1.0397 0.118 Uiso 1 calc R
H29C H 0.6723 0.1846 0.9413 0.118 Uiso 1 calc R
C30 C 0.3850(12) 0.1277(11) 1.0084(12) 0.142(7) Uani 1 d .
H30A H 0.4158 0.0735 1.0416 0.213 Uiso 1 calc R
H30B H 0.3021 0.1010 0.9677 0.213 Uiso 1 calc R
H30C H 0.3749 0.1897 1.0586 0.213 Uiso 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'
Se Se -0.0929 2.2259 '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
C17 Se1 Se2 102.87(19) .
C1 Se2 Se1 105.1(2) .
C17 Se3 C34 105.0(3) .
C34 Se4 Se5 98.4(2) .
C18 Se5 Se4 96.9(2) .
C18 C17 Se3 128.3(5) .
C18 C17 Se1 117.2(5) .
Se3 C17 Se1 113.9(3) .
C17 C18 C19 123.4(6) .
C17 C18 Se5 118.9(5) .
C19 C18 Se5 117.7(5) .
C3 C2 C7 119.9(6) .
C3 C2 C1 120.4(6) .
C7 C2 C1 119.7(6) .
C1 C34 Se4 119.1(5) 2_566
C1 C34 Se3 121.2(5) 2_566
Se4 C34 Se3 119.7(3) .
C34 C1 C2 121.3(6) 2_566
C34 C1 Se2 117.1(5) 2_566
C2 C1 Se2 120.9(4) .
C6 C7 C2 118.6(7) .
C6 C7 C14 119.2(6) .
C2 C7 C14 122.3(6) .
C19 C20 C21 118.4(7) .
C19 C20 C25 120.5(6) .
C21 C20 C25 121.1(6) .
C7 C6 C5 122.4(7) .
C20 C19 C24 120.7(6) .
C20 C19 C18 120.7(6) .
C24 C19 C18 118.4(6) .
C4 C5 C6 117.4(7) .
C4 C5 C11 122.3(7) .
C6 C5 C11 120.2(7) .
C22 C21 C20 122.2(7) .
C22 C23 C24 122.5(7) .
C10 C8 C3 112.8(7) .
C10 C8 C9 109.8(7) .
C3 C8 C9 111.1(7) .
C24 C31 C32 115.5(7) .
C24 C31 C33 110.2(6) .
C32 C31 C33 111.2(7) .
C2 C3 C4 118.1(7) .
C2 C3 C8 122.9(7) .
C4 C3 C8 119.0(7) .
C5 C4 C3 123.6(7) .
C15 C14 C7 110.8(7) .
C15 C14 C16 112.1(7) .
C7 C14 C16 111.9(7) .
C13 C11 C12 110.9(7) .
C13 C11 C5 111.4(7) .
C12 C11 C5 113.5(7) .
C23 C24 C19 117.9(6) .
C23 C24 C31 119.9(7) .
C19 C24 C31 121.8(6) .
C21 C22 C23 118.3(7) .
C21 C22 C28 122.5(7) .
C23 C22 C28 119.1(7) .
C26 C25 C27 110.6(7) .
C26 C25 C20 113.0(6) .
C27 C25 C20 110.3(6) .
C30 C28 C29 116.1(9) .
C30 C28 C22 114.1(8) .
C29 C28 C22 110.0(8) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 C17 1.943(6) .
Se1 Se2 2.3155(12) .
Se2 C1 1.912(7) .
Se3 C17 1.910(6) .
Se3 C34 1.927(6) .
Se4 C34 1.903(7) .
Se4 Se5 2.3292(12) .
Se5 C18 1.921(7) .
C17 C18 1.317(9) .
C18 C19 1.494(9) .
C2 C3 1.393(10) .
C2 C7 1.424(10) .
C2 C1 1.488(9) .
C34 C1 1.361(9) 2_566
C1 C34 1.361(9) 2_566
C7 C6 1.381(9) .
C7 C14 1.518(10) .
C20 C19 1.402(9) .
C20 C21 1.405(9) .
C20 C25 1.528(10) .
C6 C5 1.388(10) .
C19 C24 1.415(9) .
C5 C4 1.368(10) .
C5 C11 1.526(9) .
C21 C22 1.375(10) .
C23 C22 1.390(11) .
C23 C24 1.397(9) .
C8 C10 1.508(11) .
C8 C3 1.520(10) .
C8 C9 1.557(11) .
C31 C24 1.492(10) .
C31 C32 1.515(11) .
C31 C33 1.534(11) .
C3 C4 1.394(10) .
C14 C15 1.510(11) .
C14 C16 1.539(11) .
C11 C13 1.503(11) .
C11 C12 1.513(11) .
C22 C28 1.530(10) .
C25 C26 1.510(10) .
C25 C27 1.519(11) .
C28 C30 1.455(14) .
C28 C29 1.501(13) .
