#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/60/4066096.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_4066096
loop_
_publ_author_name
'Murai, Toshiaki'
'Hori, Rumi'
'Maruyama, Toshifumi'
'Shibahara, Fumitoshi'
_publ_section_title
;
 (Selenocarbamoyl)silanes and -germanes: Their Synthesis Using
 (Selenocarbamoyl)lithium and Characterization
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              2400
_journal_paper_doi               10.1021/om100290h
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C15 H15 N Se'
_chemical_formula_sum            'C15 H15 N Se'
_chemical_formula_weight         288.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.785(7)
_cell_length_b                   9.856(6)
_cell_length_c                   25.027(16)
_cell_measurement_reflns_used    7416
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      3.1
_cell_volume                     2660(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 14.62
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            20092
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    2.800
_exptl_absorpt_correction_T_max  0.531
_exptl_absorpt_correction_T_min  0.378
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Higashi, 1999)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+7.8700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                2939
_reflns_number_total             3024
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100290h_si_002.cif
_cod_data_source_block           rh1117
_cod_original_sg_symbol_H-M      'P bca       '
_cod_database_code               4066096
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
Se1 Se 0.45873(3) 0.08162(3) 0.580492(12) 0.03469(12) Uani 1 1 d .
N1 N 0.6945(2) -0.0281(2) 0.60204(9) 0.0259(5) Uani 1 1 d .
C8 C 0.6625(3) -0.0975(3) 0.69670(11) 0.0271(6) Uani 1 1 d .
C9 C 0.8065(3) -0.1014(3) 0.58481(13) 0.0319(6) Uani 1 1 d .
H3-A H 0.7917 -0.1415 0.5491 0.038 Uiso 1 1 calc R
H3-B H 0.8233 -0.1766 0.6101 0.038 Uiso 1 1 calc R
C13 C 1.1268(3) 0.1562(3) 0.57671(15) 0.0415(8) Uani 1 1 d .
H13 H 1.1979 0.2129 0.5750 0.050 Uiso 1 1 calc R
C4 C 0.5335(3) -0.2829(4) 0.72590(14) 0.0415(8) Uani 1 1 d .
H4 H 0.4650 -0.3416 0.7198 0.050 Uiso 1 1 calc R
C3 C 0.5628(3) -0.1833(3) 0.68838(13) 0.0368(7) Uani 1 1 d .
H3 H 0.5139 -0.1743 0.6569 0.044 Uiso 1 1 calc R
C15 C 0.9216(3) 0.0994(3) 0.54696(13) 0.0325(7) Uani 1 1 d .
H15 H 0.8524 0.1173 0.5245 0.039 Uiso 1 1 calc R
C2 C 0.6921(3) 0.0166(3) 0.65830(11) 0.0279(6) Uani 1 1 d .
H2-A H 0.6292 0.0890 0.6623 0.033 Uiso 1 1 calc R
H2-B H 0.7738 0.0557 0.6677 0.033 Uiso 1 1 calc R
C11 C 1.0198(3) -0.0347(3) 0.61471(14) 0.0349(7) Uani 1 1 d .
H11 H 1.0183 -0.1086 0.6391 0.042 Uiso 1 1 calc R
C10 C 0.9181(3) -0.0098(3) 0.58233(12) 0.0279(6) Uani 1 1 d .
C14 C 1.0256(3) 0.1820(3) 0.54426(14) 0.0371(7) Uani 1 1 d .
H14 H 1.0272 0.2563 0.5201 0.045 Uiso 1 1 calc R
C12 C 1.1240(3) 0.0474(4) 0.61177(16) 0.0435(8) Uani 1 1 d .
H12 H 1.1938 0.0290 0.6339 0.052 Uiso 1 1 calc R
C1 C 0.6043(3) -0.0028(3) 0.56797(12) 0.0280(6) Uani 1 1 d .
C5 C 0.6034(3) -0.2966(3) 0.77173(13) 0.0388(8) Uani 1 1 d .
H5 H 0.5823 -0.3637 0.7974 0.047 Uiso 1 1 calc R
C6 C 0.7033(4) -0.2134(4) 0.78020(14) 0.0437(8) Uani 1 1 d .
H6 H 0.7521 -0.2231 0.8116 0.052 Uiso 1 1 calc R
C7 C 0.7332(3) -0.1146(3) 0.74268(13) 0.0378(7) Uani 1 1 d .
H7 H 0.8030 -0.0578 0.7486 0.045 Uiso 1 1 calc R
H1 H 0.620(3) -0.031(3) 0.5335(13) 0.026(8) 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'
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
C1 N1 C9 120.6(3)
C1 N1 C2 123.1(2)
C9 N1 C2 116.3(2)
C3 C8 C7 118.4(3)
C3 C8 C2 121.5(3)
C7 C8 C2 120.0(3)
N1 C9 C10 111.9(2)
N1 C9 H3-A 109.2
C10 C9 H3-A 109.2
N1 C9 H3-B 109.2
C10 C9 H3-B 109.2
H3-A C9 H3-B 107.9
C14 C13 C12 119.7(3)
C14 C13 H13 120.1
C12 C13 H13 120.1
C5 C4 C3 120.3(3)
C5 C4 H4 119.8
C3 C4 H4 119.8
C8 C3 C4 120.4(3)
C8 C3 H3 119.8
C4 C3 H3 119.8
C14 C15 C10 120.5(3)
C14 C15 H15 119.7
C10 C15 H15 119.7
N1 C2 C8 112.8(2)
N1 C2 H2-A 109.0
C8 C2 H2-A 109.0
N1 C2 H2-B 109.0
C8 C2 H2-B 109.0
H2-A C2 H2-B 107.8
C10 C11 C12 120.4(3)
C10 C11 H11 119.8
C12 C11 H11 119.8
C11 C10 C15 119.1(3)
C11 C10 C9 120.1(3)
C15 C10 C9 120.8(3)
C13 C14 C15 120.0(3)
C13 C14 H14 120.0
C15 C14 H14 120.0
C13 C12 C11 120.2(3)
C13 C12 H12 119.9
C11 C12 H12 119.9
N1 C1 Se1 128.1(2)
N1 C1 H1 114(2)
Se1 C1 H1 118(2)
C6 C5 C4 119.9(3)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C7 119.9(3)
C5 C6 H6 120.1
C7 C6 H6 120.1
C8 C7 C6 121.1(3)
C8 C7 H7 119.4
C6 C7 H7 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 C1 1.805(3)
N1 C1 1.316(4)
N1 C9 1.473(4)
N1 C2 1.476(4)
C8 C3 1.383(4)
C8 C7 1.389(4)
C8 C2 1.514(4)
C9 C10 1.506(4)
C9 H3-A 0.9900
C9 H3-B 0.9900
C13 C14 1.383(5)
C13 C12 1.386(5)
C13 H13 0.9500
C4 C5 1.378(5)
C4 C3 1.395(5)
C4 H4 0.9500
C3 H3 0.9500
C15 C14 1.387(5)
C15 C10 1.394(4)
C15 H15 0.9500
C2 H2-A 0.9900
C2 H2-B 0.9900
C11 C10 1.385(4)
C11 C12 1.387(5)
C11 H11 0.9500
C14 H14 0.9500
C12 H12 0.9500
C1 H1 0.92(3)
C5 C6 1.371(5)
C5 H5 0.9500
C6 C7 1.391(5)
C6 H6 0.9500
C7 H7 0.9500
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
C1 N1 C9 C10 109.0(3)
C2 N1 C9 C10 -69.7(3)
C7 C8 C3 C4 0.9(5)
C2 C8 C3 C4 -176.4(3)
C5 C4 C3 C8 0.2(5)
C1 N1 C2 C8 103.7(3)
C9 N1 C2 C8 -77.7(3)
C3 C8 C2 N1 -49.2(4)
C7 C8 C2 N1 133.5(3)
C12 C11 C10 C15 -0.3(5)
C12 C11 C10 C9 178.5(3)
C14 C15 C10 C11 -0.1(5)
C14 C15 C10 C9 -178.9(3)
N1 C9 C10 C11 118.1(3)
N1 C9 C10 C15 -63.1(4)
C12 C13 C14 C15 0.2(5)
C10 C15 C14 C13 0.1(5)
C14 C13 C12 C11 -0.6(5)
C10 C11 C12 C13 0.7(5)
C9 N1 C1 Se1 178.6(2)
C2 N1 C1 Se1 -2.8(4)
C3 C4 C5 C6 -1.0(5)
C4 C5 C6 C7 0.5(5)
C3 C8 C7 C6 -1.4(5)
C2 C8 C7 C6 176.0(3)
C5 C6 C7 C8 0.6(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659677
