#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/04/7150469.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_7150469
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         'C18 H14 O2 Se2'
_chemical_formula_sum            'C18 H14 O2 Se2'
_chemical_formula_weight         420.21
_chemical_name_common            3
_chemical_name_systematic
; 
4,6-bis(phenylseleno)benzene-1,3-diol 
;
_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                 101.673(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0339(15)
_cell_length_b                   5.6420(7)
_cell_length_c                   18.9279(13)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    122.0(5)
_cell_measurement_theta_max      42.48
_cell_measurement_theta_min      39.38
_cell_volume                     1572.3(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6277
_diffrn_reflns_theta_full        74.91
_diffrn_reflns_theta_max         74.91
_diffrn_reflns_theta_min         3.44
_diffrn_standards_decay_%        28
_diffrn_standards_interval_time  167
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    5.911
_exptl_absorpt_correction_T_max  0.245
_exptl_absorpt_correction_T_min  0.066
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(DeTitta, 1985)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.431
_refine_diff_density_min         -1.408
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       0.00456(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0301
_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)+(0.0338P)²+2.6447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                3203
_reflns_number_total             3226
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b211130f.txt
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7150469
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.632094(18) 1.16785(5) 0.593932(14) 0.01987(12) Uani 1 1 d . . .
Se2 Se 0.391435(19) 0.37536(5) 0.576191(15) 0.02223(12) Uani 1 1 d . . .
C1 C 0.58645(17) 0.9037(5) 0.63848(13) 0.0190(5) Uani 1 1 d . . .
C2 C 0.61944(18) 0.8542(6) 0.71185(15) 0.0237(6) Uani 1 1 d . . .
C3 C 0.58300(19) 0.6691(6) 0.74507(15) 0.0260(6) Uani 1 1 d . . .
H3 H 0.6047 0.6376 0.7949 0.031 Uiso 1 1 calc R . .
C4 C 0.51459(18) 0.5303(6) 0.70509(15) 0.0249(6) Uani 1 1 d . . .
C5 C 0.47954(17) 0.5803(5) 0.63224(14) 0.0199(5) Uani 1 1 d . . .
C6 C 0.51602(16) 0.7679(5) 0.59972(14) 0.0190(5) Uani 1 1 d . . .
H6 H 0.4925 0.8036 0.5504 0.023 Uiso 1 1 calc R . .
C11 C 0.74639(17) 1.0453(5) 0.57976(13) 0.0175(5) Uani 1 1 d . . .
C21 C 0.28634(17) 0.4454(5) 0.61613(14) 0.0191(5) Uani 1 1 d . . .
O2 O 0.68820(14) 0.9786(4) 0.75269(10) 0.0314(5) Uani 1 1 d . . .
H2 H 0.6970 1.1036 0.7310 0.047 Uiso 1 1 calc R . .
O4 O 0.48368(16) 0.3448(4) 0.73919(12) 0.0350(5) Uani 1 1 d . . .
H4 H 0.4443 0.2702 0.7097 0.052 Uiso 1 1 calc R . .
C12 C 0.78141(18) 0.8269(5) 0.60450(14) 0.0193(5) Uani 1 1 d . . .
H12 H 0.7457 0.7192 0.6256 0.023 Uiso 1 1 calc R . .
C13 C 0.86931(18) 0.7657(5) 0.59826(15) 0.0223(5) Uani 1 1 d . . .
H13 H 0.8938 0.6169 0.6159 0.027 Uiso 1 1 calc R . .
C14 C 0.92128(18) 0.9203(6) 0.56644(16) 0.0257(6) Uani 1 1 d . . .
H14 H 0.9813 0.8780 0.5626 0.031 Uiso 1 1 calc R . .
C15 C 0.8852(2) 1.1368(5) 0.54019(16) 0.0260(6) Uani 1 1 d . . .
H15 H 0.9204 1.2417 0.5177 0.031 Uiso 1 1 calc R . .
C16 C 0.79785(19) 1.2014(5) 0.54656(14) 0.0219(5) Uani 1 1 d . . .
H16 H 0.7733 1.3498 0.5286 0.026 Uiso 1 1 calc R . .
C22 C 0.21593(19) 0.2810(6) 0.60185(16) 0.0273(6) Uani 1 1 d . . .
H22 H 0.2219 0.1416 0.5750 0.033 Uiso 1 1 calc R . .
C23 C 0.1368(2) 0.3227(6) 0.62713(19) 0.0348(7) Uani 1 1 d . . .
H23 H 0.0883 0.2118 0.6173 0.042 Uiso 1 1 calc R . .
C24 C 0.1282(2) 0.5248(6) 0.66662(17) 0.0311(7) Uani 1 1 d . . .
H24 H 0.0740 0.5519 0.6839 0.037 Uiso 1 1 calc R . .
C25 C 0.1980(2) 0.6866(6) 0.68089(17) 0.0290(6) Uani 1 1 d . . .
H25 H 0.1918 0.8249 0.7081 0.035 Uiso 1 1 calc R . .
C26 C 0.2779(2) 0.6485(5) 0.65558(16) 0.0245(6) Uani 1 1 d . . .
H26 H 0.3260 0.7606 0.6653 0.029 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
C1 Se1 C11 101.10(11) . . ?
C5 Se2 C21 100.93(11) . . ?
C6 C1 C2 119.4(3) . . ?
C6 C1 Se1 120.08(19) . . ?
C2 C1 Se1 120.4(2) . . ?
O2 C2 C3 117.2(2) . . ?
O2 C2 C1 122.5(3) . . ?
C3 C2 C1 120.3(3) . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
O4 C4 C3 117.5(2) . . ?
O4 C4 C5 121.7(3) . . ?
C3 C4 C5 120.8(3) . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 Se2 120.39(19) . . ?
C4 C5 Se2 120.3(2) . . ?
C1 C6 C5 120.8(2) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C12 C11 C16 120.3(2) . . ?
C12 C11 Se1 124.3(2) . . ?
C16 C11 Se1 115.3(2) . . ?
C26 C21 C22 120.4(3) . . ?
C26 C21 Se2 123.5(2) . . ?
C22 C21 Se2 116.0(2) . . ?
C2 O2 H2 109.5 . . ?
C4 O4 H4 109.5 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 119.3(3) . . ?
C21 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
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 C1 1.907(3) . ?
Se1 C11 1.921(3) . ?
Se2 C5 1.910(3) . ?
Se2 C21 1.925(3) . ?
C1 C6 1.390(4) . ?
C1 C2 1.405(4) . ?
C2 O2 1.355(3) . ?
C2 C3 1.387(4) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 O4 1.360(4) . ?
C4 C5 1.402(4) . ?
C5 C6 1.391(4) . ?
C6 H6 0.9500 . ?
C11 C12 1.384(4) . ?
C11 C16 1.402(4) . ?
C21 C26 1.387(4) . ?
C21 C22 1.392(4) . ?
O2 H2 0.8400 . ?
O4 H4 0.8400 . ?
C12 C13 1.394(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C22 C23 1.389(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.376(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.397(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9244981
