#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/61/4026113.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_4026113
loop_
_publ_author_name
'S. Fern Lim'
'Benjamin L. Harris'
'Paul Blanc'
'Jonathan M. White'
_publ_section_title
;
 Orbital Interactions in Selenomethyl-Substituted Pyridinium Ions and
 Carbenium Ions with Higher Electron Demand
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1673
_journal_page_last               1682
_journal_paper_doi               10.1021/jo102307v
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C18 H25 N O3 S Se'
_chemical_formula_weight         414.41
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.464(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5091(16)
_cell_length_b                   33.521(8)
_cell_length_c                   8.747(2)
_cell_measurement_reflns_used    4058
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.41
_cell_volume                     1905.0(8)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11914
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    2.096
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.864
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0407
_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)+(0.0480P)²+1.7742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                3703
_reflns_number_total             4354
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102307v_si_002.cif
_cod_data_source_block           jmwsf13
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4026113
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C9 C 0.6991(5) 0.08616(11) 0.7814(4) 0.0431(8) Uani 1 1 d .
H9C H 0.7331 0.0819 0.6774 0.065 Uiso 1 1 calc R
H9B H 0.7991 0.0731 0.8494 0.065 Uiso 1 1 calc R
H9A H 0.6991 0.1143 0.8027 0.065 Uiso 1 1 calc R
C10 C 0.4782(6) 0.02512(9) 0.7611(4) 0.0415(8) Uani 1 1 d .
H10B H 0.5183 0.0219 0.6580 0.062 Uiso 1 1 calc R
H10C H 0.3401 0.0156 0.7683 0.062 Uiso 1 1 calc R
H10A H 0.5698 0.0102 0.8296 0.062 Uiso 1 1 calc R
C8 C 0.4278(6) 0.07520(10) 0.9669(4) 0.0457(8) Uani 1 1 d .
H81 H 0.2938 0.0640 0.9780 0.068 Uiso 1 1 calc R
H8B H 0.4250 0.1032 0.9894 0.068 Uiso 1 1 calc R
H8C H 0.5261 0.0622 1.0364 0.068 Uiso 1 1 calc R
Se1 Se 0.27786(4) 0.094069(8) 0.66102(3) 0.02559(10) Uani 1 1 d .
S1 S -0.44870(9) 0.188634(19) 0.20801(7) 0.02021(15) Uani 1 1 d .
N1 N -0.2145(3) 0.21662(6) 0.6905(2) 0.0200(4) Uani 1 1 d .
O3 O -0.5650(3) 0.19509(6) 0.3418(2) 0.0334(5) Uani 1 1 d .
C3 C 0.1463(4) 0.17414(7) 0.6912(3) 0.0202(5) Uani 1 1 d .
O2 O -0.3027(3) 0.22028(6) 0.1847(2) 0.0329(5) Uani 1 1 d .
C14 C -0.2641(5) 0.07885(9) 0.3451(3) 0.0313(6) Uani 1 1 d .
H14 H -0.3199 0.0573 0.3949 0.038 Uiso 1 1 calc R
O1 O -0.5771(4) 0.17977(7) 0.0725(2) 0.0419(6) Uani 1 1 d .
C12 C -0.2984(4) 0.14534(8) 0.2473(3) 0.0197(5) Uani 1 1 d .
C5 C -0.1262(4) 0.20971(8) 0.5584(3) 0.0227(5) Uani 1 1 d .
H5 H -0.1879 0.2194 0.4672 0.027 Uiso 1 1 calc R
C6 C 0.3405(4) 0.15095(8) 0.6933(3) 0.0234(5) Uani 1 1 d .
H6A H 0.4170 0.1545 0.7910 0.028 Uiso 1 1 calc R
H6B H 0.4248 0.1605 0.6132 0.028 Uiso 1 1 calc R
C17 C -0.1002(4) 0.14320(9) 0.1997(3) 0.0255(6) Uani 1 1 d .
H17 H -0.0433 0.1650 0.1520 0.031 Uiso 1 1 calc R
C13 C -0.3801(4) 0.11326(8) 0.3226(3) 0.0257(6) Uani 1 1 d .
H13 H -0.5118 0.1148 0.3579 0.031 Uiso 1 1 calc R
C1 C -0.1271(4) 0.20355(8) 0.8234(3) 0.0243(5) Uani 1 1 d .
H1 H -0.1885 0.2089 0.9144 0.029 Uiso 1 1 calc R
C16 C 0.0132(5) 0.10890(10) 0.2229(3) 0.0325(6) Uani 1 1 d .
H16 H 0.1461 0.1077 0.1897 0.039 Uiso 1 1 calc R
C11 C -0.4053(4) 0.24058(8) 0.6897(3) 0.0273(6) Uani 1 1 d .
H11A H -0.4503 0.2424 0.7920 0.041 Uiso 1 1 calc R
H11B H -0.5104 0.2280 0.6246 0.041 Uiso 1 1 calc R
H11C H -0.3790 0.2669 0.6519 0.041 Uiso 1 1 calc R
C4 C 0.0534(4) 0.18856(8) 0.5561(3) 0.0231(5) Uani 1 1 d .
H4 H 0.1129 0.1839 0.4637 0.028 Uiso 1 1 calc R
C7 C 0.4884(4) 0.06916(8) 0.8044(3) 0.0281(6) Uani 1 1 d .
C2 C 0.0519(4) 0.18233(8) 0.8260(3) 0.0245(6) Uani 1 1 d .
H2 H 0.1114 0.1733 0.9189 0.029 Uiso 1 1 calc R
C15 C -0.0670(5) 0.07592(9) 0.2949(3) 0.0318(6) Uani 1 1 d .
C18 C 0.0579(6) 0.03827(10) 0.3170(4) 0.0476(9) Uani 1 1 d .
H18A H 0.1893 0.0418 0.2745 0.071 Uiso 1 1 calc R
H18B H -0.0137 0.0165 0.2661 0.071 Uiso 1 1 calc R
H18C H 0.0776 0.0325 0.4243 0.071 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'
S S 0.1246 0.1234 '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
C6 Se1 C7 100.83(12)
O1 S1 O2 112.88(14)
O1 S1 O3 112.99(14)
O2 S1 O3 112.61(13)
O1 S1 C12 106.06(12)
O2 S1 C12 105.55(12)
O3 S1 C12 105.98(12)
C1 N1 C5 120.7(2)
C1 N1 C11 119.7(2)
C5 N1 C11 119.5(2)
C4 C3 C2 117.6(2)
C4 C3 C6 121.5(2)
C2 C3 C6 120.9(2)
C15 C14 C13 121.4(3)
C17 C12 C13 119.7(2)
C17 C12 S1 119.9(2)
C13 C12 S1 120.3(2)
N1 C5 C4 120.9(2)
C3 C6 Se1 109.70(18)
C16 C17 C12 120.2(3)
C12 C13 C14 119.5(3)
N1 C1 C2 120.3(2)
C17 C16 C15 121.3(3)
C5 C4 C3 119.9(2)
C9 C7 C8 111.5(3)
C9 C7 C10 111.0(3)
C8 C7 C10 110.7(3)
C9 C7 Se1 110.8(2)
C8 C7 Se1 109.2(2)
C10 C7 Se1 103.4(2)
C1 C2 C3 120.7(2)
C14 C15 C16 117.9(3)
C14 C15 C18 121.4(3)
C16 C15 C18 120.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C9 C7 1.510(4)
C10 C7 1.524(4)
C8 C7 1.511(4)
Se1 C6 1.967(3)
Se1 C7 1.985(3)
S1 O1 1.440(2)
S1 O2 1.447(2)
S1 O3 1.4478(19)
S1 C12 1.772(3)
N1 C1 1.337(3)
N1 C5 1.341(3)
N1 C11 1.478(3)
C3 C4 1.382(3)
C3 C2 1.389(3)
C3 C6 1.483(4)
C14 C15 1.385(4)
C14 C13 1.386(4)
C12 C17 1.381(4)
C12 C13 1.384(4)
C5 C4 1.369(4)
C17 C16 1.375(4)
C1 C2 1.364(4)
C16 C15 1.389(5)
C15 C18 1.507(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659348
