#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/04/7150470.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_7150470
loop_
_publ_author_name
'Oddershede, Jette'
'Henriksen, Lars'
'Larsen, Sine'
_publ_section_title
;
 Relations between 77Se NMR chemical shifts of (phenylseleno)benzenes
 and their molecular structures derived from nine X-ray crystal
 structures
;
_journal_issue                   6
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1053
_journal_paper_doi               10.1039/b211130f
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C22 H22 O2 Se2'
_chemical_formula_sum            'C22 H22 O2 Se2'
_chemical_formula_weight         476.32
_chemical_name_common            4
_chemical_name_systematic
; 
1,2-diethoxy-4,5-bis(phenylseleno)benzene 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_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                116.25(2)
_cell_angle_beta                 100.280(17)
_cell_angle_gamma                104.48(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5958(17)
_cell_length_b                   11.370(3)
_cell_length_c                   12.388(3)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    122.0(5)
_cell_measurement_theta_max      41.50
_cell_measurement_theta_min      39.27
_cell_volume                     991.4(5)
_computing_cell_refinement       'CAD4 Express (1994)'
_computing_data_collection       'CAD4 Express (1994)'
_computing_data_reduction        'DREADD (Blessing 1987)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      122.0(5)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6745
_diffrn_reflns_theta_full        74.91
_diffrn_reflns_theta_max         74.91
_diffrn_reflns_theta_min         4.22
_diffrn_standards_decay_%        4.6
_diffrn_standards_interval_time  167
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    4.761
_exptl_absorpt_correction_T_max  0.177
_exptl_absorpt_correction_T_min  0.046
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(DeTitta, 1985)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.960
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0349
_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)+(0.0256P)²+2.6667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0867
_reflns_number_gt                3868
_reflns_number_total             3936
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b211130f.txt
_cod_data_source_block           4
_cod_database_code               7150470
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.28117(4) 0.04554(3) 0.37247(3) 0.02053(10) Uani 1 1 d . . .
Se2 Se 0.57254(4) 0.08358(4) 0.21713(3) 0.02390(10) Uani 1 1 d . . .
C1 C 0.5205(4) 0.1570(3) 0.4614(3) 0.0190(6) Uani 1 1 d . . .
C2 C 0.6364(4) 0.1751(3) 0.3998(3) 0.0201(6) Uani 1 1 d . . .
C3 C 0.8090(4) 0.2590(3) 0.4717(3) 0.0200(6) Uani 1 1 d . . .
H3 H 0.8871 0.2763 0.4300 0.024 Uiso 1 1 calc R . .
C4 C 0.8663(4) 0.3167(3) 0.6024(3) 0.0178(5) Uani 1 1 d . . .
C5 C 0.7494(4) 0.2932(3) 0.6645(3) 0.0167(5) Uani 1 1 d . . .
C6 C 0.5776(4) 0.2178(3) 0.5936(3) 0.0188(6) Uani 1 1 d . . .
H6 H 0.4976 0.2075 0.6358 0.023 Uiso 1 1 calc R . .
C11 C 0.2203(3) 0.1610(3) 0.3107(3) 0.0167(5) Uani 1 1 d . . .
C21 C 0.6685(4) -0.0596(3) 0.1868(3) 0.0201(6) Uani 1 1 d . . .
O4 O 1.0307(3) 0.3981(2) 0.68057(19) 0.0203(4) Uani 1 1 d . . .
O5 O 0.8169(2) 0.3484(2) 0.79215(19) 0.0195(4) Uani 1 1 d . . .
C7 C 1.1541(4) 0.4243(4) 0.6205(3) 0.0270(7) Uani 1 1 d . . .
H71 H 1.1214 0.4706 0.5736 0.032 Uiso 1 1 calc R . .
H72 H 1.1603 0.3343 0.5595 0.032 Uiso 1 1 calc R . .
C8 C 1.3232(4) 0.5192(4) 0.7249(3) 0.0357(8) Uani 1 1 d . . .
H81 H 1.3531 0.4729 0.7716 0.043 Uiso 1 1 calc R . .
H82 H 1.3160 0.6085 0.7837 0.043 Uiso 1 1 calc R . .
H83 H 1.4109 0.5379 0.6875 0.043 Uiso 1 1 calc R . .
C9 C 0.7061(4) 0.3070(3) 0.8545(3) 0.0206(6) Uani 1 1 d . . .
H91 H 0.6302 0.2062 0.7985 0.025 Uiso 1 1 calc R . .
H92 H 0.6345 0.3646 0.8737 0.025 Uiso 1 1 calc R . .
C10 C 0.8174(4) 0.3301(4) 0.9761(3) 0.0259(6) Uani 1 1 d . . .
H101 H 0.8905 0.2752 0.9562 0.031 Uiso 1 1 calc R . .
H102 H 0.7457 0.2994 1.0192 0.031 Uiso 1 1 calc R . .
H103 H 0.8885 0.4307 1.0321 0.031 Uiso 1 1 calc R . .
C12 C 0.0769(4) 0.0963(3) 0.2035(3) 0.0219(6) Uani 1 1 d . . .
H12 H 0.0191 -0.0034 0.1584 0.026 Uiso 1 1 calc R . .
C13 C 0.0177(4) 0.1774(4) 0.1620(3) 0.0273(7) Uani 1 1 d . . .
H13 H -0.0816 0.1330 0.0893 0.033 Uiso 1 1 calc R . .
C14 C 0.1031(4) 0.3230(3) 0.2264(3) 0.0239(6) Uani 1 1 d . . .
H14 H 0.0625 0.3783 0.1980 0.029 Uiso 1 1 calc R . .
C15 C 0.2482(4) 0.3869(3) 0.3324(3) 0.0223(6) Uani 1 1 d . . .
H15 H 0.3075 0.4863 0.3760 0.027 Uiso 1 1 calc R . .
C16 C 0.3074(4) 0.3073(3) 0.3754(3) 0.0197(6) Uani 1 1 d . . .
H16 H 0.4066 0.3519 0.4482 0.024 Uiso 1 1 calc R . .
C22 C 0.6452(4) -0.1526(3) 0.0598(3) 0.0256(6) Uani 1 1 d . . .
H22 H 0.5865 -0.1426 -0.0063 0.031 Uiso 1 1 calc R . .
C23 C 0.7087(4) -0.2603(4) 0.0307(3) 0.0326(7) Uani 1 1 d . . .
H23 H 0.6933 -0.3239 -0.0556 0.039 Uiso 1 1 calc R . .
C24 C 0.7943(4) -0.2750(4) 0.1272(4) 0.0310(7) Uani 1 1 d . . .
H24 H 0.8378 -0.3483 0.1071 0.037 Uiso 1 1 calc R . .
C25 C 0.8160(4) -0.1826(3) 0.2524(3) 0.0275(7) Uani 1 1 d . . .
H25 H 0.8745 -0.1929 0.3185 0.033 Uiso 1 1 calc R . .
C26 C 0.7533(4) -0.0750(3) 0.2832(3) 0.0225(6) Uani 1 1 d . . .
H26 H 0.7684 -0.0123 0.3697 0.027 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 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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
_geom_angle_publ_flag
C11 Se1 C1 99.22(12) . . ?
C2 Se2 C21 98.95(12) . . ?
C2 C1 C6 119.6(3) . . ?
C2 C1 Se1 123.1(2) . . ?
C6 C1 Se1 117.2(2) . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 Se2 122.6(2) . . ?
C3 C2 Se2 117.7(2) . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O4 C4 C3 125.3(3) . . ?
O4 C4 C5 115.1(2) . . ?
C3 C4 C5 119.6(3) . . ?
O5 C5 C6 124.9(3) . . ?
O5 C5 C4 115.9(2) . . ?
C6 C5 C4 119.2(3) . . ?
C5 C6 C1 121.1(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C12 C11 C16 120.0(3) . . ?
C12 C11 Se1 117.7(2) . . ?
C16 C11 Se1 122.2(2) . . ?
C26 C21 C22 120.1(3) . . ?
C26 C21 Se2 123.5(2) . . ?
C22 C21 Se2 116.4(2) . . ?
C4 O4 C7 116.7(2) . . ?
C5 O5 C9 117.1(2) . . ?
O4 C7 C8 107.1(3) . . ?
O4 C7 H71 110.3 . . ?
C8 C7 H71 110.3 . . ?
O4 C7 H72 110.3 . . ?
C8 C7 H72 110.3 . . ?
H71 C7 H72 108.5 . . ?
C7 C8 H81 109.5 . . ?
C7 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C7 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
O5 C9 C10 107.5(2) . . ?
O5 C9 H91 110.2 . . ?
C10 C9 H91 110.2 . . ?
O5 C9 H92 110.2 . . ?
C10 C9 H92 110.2 . . ?
H91 C9 H92 108.5 . . ?
C9 C10 H101 109.5 . . ?
C9 C10 H102 109.5 . . ?
H101 C10 H102 109.5 . . ?
C9 C10 H103 109.5 . . ?
H101 C10 H103 109.5 . . ?
H102 C10 H103 109.5 . . ?
C11 C12 C13 119.9(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 119.5(3) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.6(3) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.8(3) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C21 119.6(3) . . ?
C25 C26 H26 120.2 . . ?
C21 C26 H26 120.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C11 1.917(3) . ?
Se1 C1 1.924(3) . ?
Se2 C2 1.921(3) . ?
Se2 C21 1.927(3) . ?
C1 C2 1.387(4) . ?
C1 C6 1.394(4) . ?
C2 C3 1.405(4) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9500 . ?
C4 O4 1.362(3) . ?
C4 C5 1.413(4) . ?
C5 O5 1.358(3) . ?
C5 C6 1.388(4) . ?
C6 H6 0.9500 . ?
C11 C12 1.387(4) . ?
C11 C16 1.397(4) . ?
C21 C26 1.388(4) . ?
C21 C22 1.394(4) . ?
O4 C7 1.444(3) . ?
O5 C9 1.445(3) . ?
C7 C8 1.503(5) . ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C8 H83 0.9800 . ?
C9 C10 1.504(4) . ?
C9 H91 0.9900 . ?
C9 H92 0.9900 . ?
C10 H101 0.9800 . ?
C10 H102 0.9800 . ?
C10 H103 0.9800 . ?
C12 C13 1.390(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C22 C23 1.393(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9060526
