#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:59:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178798 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/52/4105222.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_4105222
loop_
_publ_author_name
'Caleb D. Martin'
'Christine M. Le'
'Paul J. Ragogna'
_publ_contact_author_address
;Department of Chemistry 
The University of Western Ontario
London, ON
N6A 5B7, CANADA
;
_publ_contact_author_email       pragogna@uwo.ca
_publ_contact_author_fax         1-519-661-3022
_publ_contact_author_name        'Paul J. Ragogna'
_publ_contact_author_phone       1-519-661-2111
_publ_section_title
;
 Remarkably Stable Chalcogen(II) Dications
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15126
_journal_page_last               15127
_journal_paper_doi               10.1021/ja9073968
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C37 H49 F6 N3 O7 S2 Se'
_chemical_formula_weight         904.87
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.00
_cell_angle_beta                 91.768(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.3723(11)
_cell_length_b                   15.4754(9)
_cell_length_c                   14.5351(7)
_cell_measurement_temperature    150(2)
_cell_volume                     4355.5(4)
_computing_cell_refinement       SAINT
_computing_data_collection       APEX2
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full .996
_diffrn_measured_fraction_theta_max .996
_diffrn_measurement_device_type  'KAPPA APEX 11 CCD'
_diffrn_measurement_method       'φ scans, and ω 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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16959
_diffrn_reflns_theta_full        26.73
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    1.031
_exptl_absorpt_correction_T_max  0.8863
_exptl_absorpt_correction_T_min  0.8204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SAINT
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.078
_refine_diff_density_min         -1.195
_refine_diff_density_rms         .074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0549P)²+11.6592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                3924
_reflns_number_total             4616
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9073968_si_002_2.cif
_cod_data_source_block           b09027
_cod_database_code               4105222
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Se1 Se 0.0000 0.22721(2) 0.7500 0.02079(12) Uani 1 2 d S
S1 S 0.13164(3) 0.04643(5) 0.57940(5) 0.02608(17) Uani 1 1 d .
F1 F 0.20068(16) 0.0940(3) 0.43829(18) 0.1105(13) Uani 1 1 d .
F2 F 0.18635(13) 0.19406(18) 0.5380(3) 0.0964(11) Uani 1 1 d .
F3 F 0.26021(10) 0.09477(17) 0.56454(19) 0.0665(7) Uani 1 1 d .
O1 O 0.0000 0.5417(2) 0.7500 0.0433(8) Uani 1 2 d S
O2 O 0.06916(10) 0.07607(15) 0.53273(15) 0.0373(5) Uani 1 1 d .
O3 O 0.13764(12) 0.06809(17) 0.67490(15) 0.0448(6) Uani 1 1 d .
O4 O 0.15060(12) -0.04055(15) 0.55719(18) 0.0462(6) Uani 1 1 d .
N1 N 0.06091(11) 0.20177(14) 0.86245(14) 0.0215(4) Uani 1 1 d .
N2 N 0.0000 0.10625(19) 0.7500 0.0191(6) Uani 1 2 d S
C1 C 0.06846(13) 0.12227(17) 0.88354(17) 0.0223(5) Uani 1 1 d .
H1 H 0.0941 0.1031 0.9364 0.027 Uiso 1 1 calc R
C2 C 0.03409(13) 0.06423(17) 0.81900(16) 0.0213(5) Uani 1 1 d .
C3 C 0.03378(15) -0.02514(18) 0.82101(18) 0.0285(6) Uani 1 1 d .
H3 H 0.0563 -0.0555 0.8702 0.034 Uiso 1 1 calc R
C4 C 0.0000 -0.0699(3) 0.7500 0.0318(9) Uani 1 2 d S
H4 H 0.0000 -0.1312 0.7500 0.038 Uiso 1 2 calc SR
C5 C 0.09081(14) 0.27592(16) 0.90964(17) 0.0225(5) Uani 1 1 d .
C6 C 0.15568(14) 0.30468(19) 0.88166(19) 0.0271(6) Uani 1 1 d .
C7 C 0.19635(16) 0.2568(2) 0.8101(2) 0.0364(7) Uani 1 1 d .
H7A H 0.1624 0.2214 0.7733 0.044 Uiso 1 1 calc R
C8 C 0.2457(2) 0.1943(3) 0.8569(3) 0.0568(5) Uani 1 1 d .
H8A H 0.2203 0.1573 0.8989 0.085 Uiso 1 1 calc R
H8B H 0.2813 0.2265 0.8918 0.085 Uiso 1 1 calc R
H8C H 0.2675 0.1584 0.8105 0.085 Uiso 1 1 calc R
C9 C 0.2308(2) 0.3164(3) 0.7434(3) 0.0568(5) Uani 1 1 d .
H9A H 0.1961 0.3544 0.7143 0.085 Uiso 1 1 calc R
H9B H 0.2531 0.2820 0.6961 0.085 Uiso 1 1 calc R
H9C H 0.2657 0.3514 0.7766 0.085 Uiso 1 1 calc R
C10 C 0.18197(15) 0.37814(19) 0.9253(2) 0.0318(6) Uani 1 1 d .
H10 H 0.2262 0.3992 0.9097 0.038 Uiso 1 1 calc R
C11 C 0.14492(16) 0.42118(19) 0.9911(2) 0.0325(6) Uani 1 1 d .
H11 H 0.1640 0.4712 1.0200 0.039 Uiso 1 1 calc R
C12 C 0.08047(15) 0.39219(18) 1.01520(19) 0.0295(6) Uani 1 1 d .
H12 H 0.0555 0.4229 1.0600 0.035 Uiso 1 1 calc R
C13 C 0.05150(14) 0.31832(17) 0.97442(18) 0.0241(5) Uani 1 1 d .
C14 C -0.01876(15) 0.28617(17) 1.0032(2) 0.0279(6) Uani 1 1 d .
H14A H -0.0325 0.2370 0.9619 0.034 Uiso 1 1 calc R
C15 C -0.0143(2) 0.2526(3) 1.1015(3) 0.0568(5) Uani 1 1 d .
H15A H 0.0212 0.2076 1.1067 0.085 Uiso 1 1 calc R
H15B H -0.0590 0.2283 1.1178 0.085 Uiso 1 1 calc R
H15C H -0.0023 0.3002 1.1435 0.085 Uiso 1 1 calc R
C16 C -0.0739(2) 0.3564(3) 0.9927(3) 0.0568(5) Uani 1 1 d .
H16A H -0.0759 0.3770 0.9290 0.085 Uiso 1 1 calc R
H16B H -0.0622 0.4046 1.0341 0.085 Uiso 1 1 calc R
H16C H -0.1189 0.3325 1.0085 0.085 Uiso 1 1 calc R
C17 C -0.12224(19) 0.5494(3) 0.7363(3) 0.0501(9) Uani 1 1 d .
H17A H -0.1642 0.5142 0.7291 0.075 Uiso 1 1 calc R
H17B H -0.1193 0.5891 0.6842 0.075 Uiso 1 1 calc R
H17C H -0.1239 0.5825 0.7937 0.075 Uiso 1 1 calc R
C18 C -0.06074(18) 0.4920(2) 0.7395(2) 0.0427(8) Uani 1 1 d .
H18A H -0.0639 0.4513 0.7917 0.051 Uiso 1 1 calc R
H18B H -0.0593 0.4579 0.6820 0.051 Uiso 1 1 calc R
C19 C 0.19811(17) 0.1110(3) 0.5276(3) 0.0493(9) Uani 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -.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
_geom_angle_site_symmetry_3
N2 Se1 N1 78.79(6) . .
N2 Se1 N1 78.79(6) . 2_556
N1 Se1 N1 157.58(13) . 2_556
O3 S1 O4 115.14(15) . .
O3 S1 O2 115.07(14) . .
O4 S1 O2 114.15(14) . .
O3 S1 C19 103.70(17) . .
O4 S1 C19 103.50(17) . .
O2 S1 C19 103.04(15) . .
C18 O1 C18 113.9(4) 2_556 .
C1 N1 C5 127.5(2) . .
C1 N1 Se1 116.18(18) . .
C5 N1 Se1 116.28(16) . .
C2 N2 C2 122.4(3) . 2_556
C2 N2 Se1 118.78(15) . .
C2 N2 Se1 118.78(15) 2_556 .
N1 C1 C2 113.3(2) . .
N1 C1 H1 123.3 . .
C2 C1 H1 123.3 . .
N2 C2 C3 119.7(2) . .
N2 C2 C1 112.8(2) . .
C3 C2 C1 127.5(2) . .
C2 C3 C4 119.0(3) . .
C2 C3 H3 120.5 . .
C4 C3 H3 120.5 . .
C3 C4 C3 120.3(4) . 2_556
C3 C4 H4 119.9 . .
C3 C4 H4 119.9 2_556 .
C13 C5 C6 124.0(2) . .
C13 C5 N1 118.3(2) . .
C6 C5 N1 117.5(2) . .
C10 C6 C5 116.4(3) . .
C10 C6 C7 121.4(3) . .
C5 C6 C7 122.1(3) . .
C8 C7 C9 113.3(3) . .
C8 C7 C6 109.9(3) . .
C9 C7 C6 113.1(3) . .
C8 C7 H7A 106.7 . .
C9 C7 H7A 106.7 . .
C6 C7 H7A 106.7 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C11 C10 C6 121.2(3) . .
C11 C10 H10 119.4 . .
C6 C10 H10 119.4 . .
C12 C11 C10 120.7(3) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C11 C12 C13 120.8(3) . .
C11 C12 H12 119.6 . .
C13 C12 H12 119.6 . .
C5 C13 C12 116.8(3) . .
C5 C13 C14 123.0(2) . .
C12 C13 C14 120.2(2) . .
C13 C14 C15 110.2(3) . .
C13 C14 C16 111.7(2) . .
C15 C14 C16 110.8(3) . .
C13 C14 H14A 108.0 . .
C15 C14 H14A 108.0 . .
C16 C14 H14A 108.0 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C14 C16 H16A 109.5 . .
C14 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C14 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C18 C17 H17A 109.5 . .
C18 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C18 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
O1 C18 C17 110.1(3) . .
O1 C18 H18A 109.6 . .
C17 C18 H18A 109.6 . .
O1 C18 H18B 109.6 . .
C17 C18 H18B 109.6 . .
H18A C18 H18B 108.2 . .
F2 C19 F3 107.2(3) . .
F2 C19 F1 108.6(4) . .
F3 C19 F1 107.3(3) . .
F2 C19 S1 111.3(3) . .
F3 C19 S1 112.0(3) . .
F1 C19 S1 110.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 N2 1.872(3) .
Se1 N1 2.025(2) .
Se1 N1 2.025(2) 2_556
S1 O3 1.429(2) .
S1 O4 1.435(2) .
S1 O2 1.444(2) .
S1 C19 1.812(4) .
F1 C19 1.327(5) .
F2 C19 1.315(5) .
F3 C19 1.326(4) .
O1 C18 1.410(4) 2_556
O1 C18 1.410(4) .
N1 C1 1.275(3) .
N1 C5 1.448(3) .
N2 C2 1.350(3) .
N2 C2 1.351(3) 2_556
C1 C2 1.446(4) .
C1 H1 0.9500 .
C2 C3 1.383(4) .
C3 C4 1.390(3) .
C3 H3 0.9500 .
C4 C3 1.390(3) 2_556
C4 H4 0.9500 .
C5 C13 1.393(4) .
C5 C6 1.405(4) .
C6 C10 1.391(4) .
C6 C7 1.517(4) .
C7 C8 1.507(5) .
C7 C9 1.508(5) .
C7 H7A 1.0000 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C11 1.384(4) .
C10 H10 0.9500 .
C11 C12 1.382(4) .
C11 H11 0.9500 .
C12 C13 1.397(4) .
C12 H12 0.9500 .
C13 C14 1.520(4) .
C14 C15 1.521(5) .
C14 C16 1.527(5) .
C14 H14A 1.0000 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 C18 1.485(5) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
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_4
N2 Se1 N1 C1 -3.09(18) . .
N1 Se1 N1 C1 -3.09(18) 2_556 .
N2 Se1 N1 C5 176.95(18) . .
N1 Se1 N1 C5 176.95(18) 2_556 .
N1 Se1 N2 C2 2.53(14) . .
N1 Se1 N2 C2 -177.47(14) 2_556 .
N1 Se1 N2 C2 -177.47(14) . 2_556
N1 Se1 N2 C2 2.54(14) 2_556 2_556
C5 N1 C1 C2 -177.1(2) . .
Se1 N1 C1 C2 3.0(3) . .
C2 N2 C2 C3 -1.02(19) 2_556 .
Se1 N2 C2 C3 178.98(19) . .
C2 N2 C2 C1 178.3(2) 2_556 .
Se1 N2 C2 C1 -1.7(2) . .
N1 C1 C2 N2 -0.9(3) . .
N1 C1 C2 C3 178.3(3) . .
N2 C2 C3 C4 2.0(4) . .
C1 C2 C3 C4 -177.2(2) . .
C2 C3 C4 C3 -1.00(18) . 2_556
C1 N1 C5 C13 -95.3(3) . .
Se1 N1 C5 C13 84.7(2) . .
C1 N1 C5 C6 89.7(3) . .
Se1 N1 C5 C6 -90.3(2) . .
C13 C5 C6 C10 2.7(4) . .
N1 C5 C6 C10 177.4(2) . .
C13 C5 C6 C7 -179.4(3) . .
N1 C5 C6 C7 -4.7(4) . .
C10 C6 C7 C8 84.5(4) . .
C5 C6 C7 C8 -93.3(3) . .
C10 C6 C7 C9 -43.1(4) . .
C5 C6 C7 C9 139.1(3) . .
C5 C6 C10 C11 -1.5(4) . .
C7 C6 C10 C11 -179.4(3) . .
C6 C10 C11 C12 -0.1(4) . .
C10 C11 C12 C13 0.7(4) . .
C6 C5 C13 C12 -2.1(4) . .
N1 C5 C13 C12 -176.8(2) . .
C6 C5 C13 C14 179.6(2) . .
N1 C5 C13 C14 5.0(4) . .
C11 C12 C13 C5 0.4(4) . .
C11 C12 C13 C14 178.7(3) . .
C5 C13 C14 C15 110.1(3) . .
C12 C13 C14 C15 -68.1(3) . .
C5 C13 C14 C16 -126.3(3) . .
C12 C13 C14 C16 55.5(4) . .
C18 O1 C18 C17 175.6(3) 2_556 .
O3 S1 C19 F2 -62.5(3) . .
O4 S1 C19 F2 176.9(3) . .
O2 S1 C19 F2 57.8(3) . .
O3 S1 C19 F3 57.6(3) . .
O4 S1 C19 F3 -63.0(3) . .
O2 S1 C19 F3 177.8(3) . .
O3 S1 C19 F1 177.0(3) . .
O4 S1 C19 F1 56.4(3) . .
O2 S1 C19 F1 -62.8(3) . .
