#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/04/7150473.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_7150473
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         'C12 H10 O2 Se'
_chemical_formula_sum            'C12 H10 O2 Se'
_chemical_formula_weight         265.16
_chemical_name_common            7
_chemical_name_systematic
; 
4-(phenylseleno)benzene-1,3-diol 
;
_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                92.369(8)
_cell_angle_beta                 90.070(10)
_cell_angle_gamma                94.027(9)
_cell_formula_units_Z            4
_cell_length_a                   8.7061(11)
_cell_length_b                   10.3054(8)
_cell_length_c                   11.8008(13)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    122.0(5)
_cell_measurement_theta_max      42.48
_cell_measurement_theta_min      37.65
_cell_volume                     1055.2(2)
_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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0097
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11170
_diffrn_reflns_theta_full        74.87
_diffrn_reflns_theta_max         74.87
_diffrn_reflns_theta_min         3.75
_diffrn_standards_decay_%        'no decay'
_diffrn_standards_interval_time  167
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    4.622
_exptl_absorpt_correction_T_max  0.225
_exptl_absorpt_correction_T_min  0.071
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(DeTitta, 1985)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.592
_refine_diff_density_min         -1.234
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.0092(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0292
_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)+(0.0412P)²+1.4749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0783
_reflns_number_gt                4320
_reflns_number_total             4334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b211130f.txt
_cod_data_source_block           7
_cod_original_cell_volume        1055.24(19)
_cod_database_code               7150473
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
Se1A Se 0.26728(3) 0.89611(2) 1.108819(18) 0.01808(10) Uani 1 1 d . . .
C1A C 0.1735(2) 0.9193(2) 0.96564(18) 0.0163(4) Uani 1 1 d . . .
C2A C 0.0670(3) 0.8249(2) 0.91840(18) 0.0163(4) Uani 1 1 d . . .
O2A O 0.0311(2) 0.70824(15) 0.96704(13) 0.0214(3) Uani 1 1 d . . .
H2A H 0.0756 0.7076 1.0302 0.032 Uiso 1 1 calc R . .
C3A C -0.0065(3) 0.8440(2) 0.81666(19) 0.0176(4) Uani 1 1 d . . .
H3A H -0.0800 0.7796 0.7857 0.021 Uiso 1 1 calc R . .
C4A C 0.0281(2) 0.9580(2) 0.76034(18) 0.0162(4) Uani 1 1 d . . .
O4A O -0.04664(19) 0.96929(15) 0.65941(13) 0.0196(3) Uani 1 1 d . . .
H4A H -0.0127 1.0377 0.6290 0.029 Uiso 1 1 calc R . .
C5A C 0.1326(3) 1.0546(2) 0.80668(19) 0.0189(4) Uani 1 1 d . . .
H5A H 0.1549 1.1331 0.7686 0.023 Uiso 1 1 calc R . .
C6A C 0.2033(2) 1.0345(2) 0.90913(19) 0.0181(4) Uani 1 1 d . . .
H6A H 0.2736 1.1005 0.9415 0.022 Uiso 1 1 calc R . .
C11A C 0.4213(2) 0.7778(2) 1.0666(2) 0.0186(4) Uani 1 1 d . . .
C12A C 0.4649(3) 0.7503(2) 0.9558(2) 0.0221(5) Uani 1 1 d . . .
H12A H 0.4162 0.7882 0.8944 0.027 Uiso 1 1 calc R . .
C13A C 0.5816(3) 0.6662(2) 0.9358(2) 0.0293(5) Uani 1 1 d . . .
H13A H 0.6116 0.6457 0.8602 0.035 Uiso 1 1 calc R . .
C14A C 0.6541(3) 0.6120(2) 1.0254(3) 0.0314(6) Uani 1 1 d . . .
H14A H 0.7343 0.5556 1.0112 0.038 Uiso 1 1 calc R . .
C15A C 0.6095(3) 0.6403(3) 1.1350(3) 0.0334(6) Uani 1 1 d . . .
H15A H 0.6589 0.6032 1.1965 0.040 Uiso 1 1 calc R . .
C16A C 0.4927(3) 0.7228(3) 1.1560(2) 0.0280(5) Uani 1 1 d . . .
H16A H 0.4616 0.7416 1.2317 0.034 Uiso 1 1 calc R . .
Se1B Se 0.25156(3) 0.37806(2) 0.397240(19) 0.01905(10) Uani 1 1 d . . .
C1B C 0.1674(2) 0.4051(2) 0.54499(18) 0.0167(4) Uani 1 1 d . . .
C2B C 0.0631(3) 0.3120(2) 0.59121(19) 0.0175(4) Uani 1 1 d . . .
O2B O 0.0277(2) 0.19246(15) 0.54009(14) 0.0225(3) Uani 1 1 d . . .
H2B H 0.0665 0.1898 0.4750 0.034 Uiso 1 1 calc R . .
C3B C -0.0082(3) 0.3378(2) 0.69369(19) 0.0181(4) Uani 1 1 d . . .
H3B H -0.0798 0.2745 0.7238 0.022 Uiso 1 1 calc R . .
C4B C 0.0247(3) 0.4560(2) 0.75258(18) 0.0174(4) Uani 1 1 d . . .
O4B O -0.0493(2) 0.47330(16) 0.85336(14) 0.0221(3) Uani 1 1 d . . .
H4B H -0.0177 0.5450 0.8845 0.033 Uiso 1 1 calc R . .
C5B C 0.1289(3) 0.5499(2) 0.7085(2) 0.0195(4) Uani 1 1 d . . .
H5B H 0.1520 0.6308 0.7487 0.023 Uiso 1 1 calc R . .
C6B C 0.1981(3) 0.5233(2) 0.6052(2) 0.0197(4) Uani 1 1 d . . .
H6B H 0.2683 0.5873 0.5746 0.024 Uiso 1 1 calc R . .
C11B C 0.4083(3) 0.2604(2) 0.42557(19) 0.0188(4) Uani 1 1 d . . .
C12B C 0.4973(3) 0.2692(2) 0.5236(2) 0.0235(5) Uani 1 1 d . . .
H12B H 0.4765 0.3298 0.5834 0.028 Uiso 1 1 calc R . .
C13B C 0.6178(3) 0.1877(3) 0.5331(2) 0.0287(5) Uani 1 1 d . . .
H13B H 0.6781 0.1923 0.6005 0.034 Uiso 1 1 calc R . .
C14B C 0.6503(3) 0.1006(3) 0.4458(2) 0.0302(6) Uani 1 1 d . . .
H14B H 0.7342 0.0473 0.4523 0.036 Uiso 1 1 calc R . .
C15B C 0.5599(3) 0.0914(3) 0.3486(2) 0.0299(5) Uani 1 1 d . . .
H15B H 0.5815 0.0311 0.2887 0.036 Uiso 1 1 calc R . .
C16B C 0.4376(3) 0.1702(2) 0.3387(2) 0.0248(5) Uani 1 1 d . . .
H16B H 0.3743 0.1625 0.2728 0.030 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
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'
H H 0.0000 0.0000 '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
C1A Se1A C11A 101.21(9) . . ?
C6A C1A C2A 118.5(2) . . ?
C6A C1A Se1A 120.54(16) . . ?
C2A C1A Se1A 120.81(16) . . ?
O2A C2A C3A 116.22(19) . . ?
O2A C2A C1A 122.8(2) . . ?
C3A C2A C1A 120.9(2) . . ?
C2A O2A H2A 109.5 . . ?
C2A C3A C4A 119.5(2) . . ?
C2A C3A H3A 120.3 . . ?
C4A C3A H3A 120.3 . . ?
O4A C4A C3A 116.33(19) . . ?
O4A C4A C5A 123.1(2) . . ?
C3A C4A C5A 120.6(2) . . ?
C4A O4A H4A 109.5 . . ?
C6A C5A C4A 119.0(2) . . ?
C6A C5A H5A 120.5 . . ?
C4A C5A H5A 120.5 . . ?
C5A C6A C1A 121.4(2) . . ?
C5A C6A H6A 119.3 . . ?
C1A C6A H6A 119.3 . . ?
C16A C11A C12A 120.5(2) . . ?
C16A C11A Se1A 115.40(18) . . ?
C12A C11A Se1A 124.06(18) . . ?
C11A C12A C13A 118.9(2) . . ?
C11A C12A H12A 120.6 . . ?
C13A C12A H12A 120.6 . . ?
C14A C13A C12A 120.6(2) . . ?
C14A C13A H13A 119.7 . . ?
C12A C13A H13A 119.7 . . ?
C15A C14A C13A 119.8(2) . . ?
C15A C14A H14A 120.1 . . ?
C13A C14A H14A 120.1 . . ?
C14A C15A C16A 120.2(3) . . ?
C14A C15A H15A 119.9 . . ?
C16A C15A H15A 119.9 . . ?
C11A C16A C15A 120.0(2) . . ?
C11A C16A H16A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C1B Se1B C11B 101.97(9) . . ?
C6B C1B C2B 118.3(2) . . ?
C6B C1B Se1B 120.33(16) . . ?
C2B C1B Se1B 121.12(16) . . ?
O2B C2B C3B 116.57(19) . . ?
O2B C2B C1B 122.8(2) . . ?
C3B C2B C1B 120.6(2) . . ?
C2B O2B H2B 109.5 . . ?
C2B C3B C4B 120.1(2) . . ?
C2B C3B H3B 119.9 . . ?
C4B C3B H3B 119.9 . . ?
O4B C4B C3B 116.48(19) . . ?
O4B C4B C5B 123.2(2) . . ?
C3B C4B C5B 120.3(2) . . ?
C4B O4B H4B 109.5 . . ?
C6B C5B C4B 118.9(2) . . ?
C6B C5B H5B 120.5 . . ?
C4B C5B H5B 120.5 . . ?
C5B C6B C1B 121.8(2) . . ?
C5B C6B H6B 119.1 . . ?
C1B C6B H6B 119.1 . . ?
C12B C11B C16B 120.3(2) . . ?
C12B C11B Se1B 122.75(18) . . ?
C16B C11B Se1B 116.75(18) . . ?
C11B C12B C13B 119.2(2) . . ?
C11B C12B H12B 120.4 . . ?
C13B C12B H12B 120.4 . . ?
C14B C13B C12B 120.8(2) . . ?
C14B C13B H13B 119.6 . . ?
C12B C13B H13B 119.6 . . ?
C13B C14B C15B 119.8(2) . . ?
C13B C14B H14B 120.1 . . ?
C15B C14B H14B 120.1 . . ?
C14B C15B C16B 120.2(2) . . ?
C14B C15B H15B 119.9 . . ?
C16B C15B H15B 119.9 . . ?
C11B C16B C15B 119.8(2) . . ?
C11B C16B H16B 120.1 . . ?
C15B C16B H16B 120.1 . . ?
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
Se1A C1A 1.907(2) . ?
Se1A C11A 1.928(2) . ?
C1A C6A 1.394(3) . ?
C1A C2A 1.394(3) . ?
C2A O2A 1.370(3) . ?
C2A C3A 1.387(3) . ?
O2A H2A 0.8400 . ?
C3A C4A 1.389(3) . ?
C3A H3A 0.9500 . ?
C4A O4A 1.370(3) . ?
C4A C5A 1.394(3) . ?
O4A H4A 0.8400 . ?
C5A C6A 1.386(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C11A C16A 1.385(3) . ?
C11A C12A 1.385(3) . ?
C12A C13A 1.395(3) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.387(4) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.377(4) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.387(4) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
Se1B C1B 1.910(2) . ?
Se1B C11B 1.926(2) . ?
C1B C6B 1.394(3) . ?
C1B C2B 1.401(3) . ?
C2B O2B 1.365(3) . ?
C2B C3B 1.384(3) . ?
O2B H2B 0.8400 . ?
C3B C4B 1.390(3) . ?
C3B H3B 0.9500 . ?
C4B O4B 1.364(3) . ?
C4B C5B 1.396(3) . ?
O4B H4B 0.8400 . ?
C5B C6B 1.387(3) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C11B C12B 1.388(3) . ?
C11B C16B 1.391(3) . ?
C12B C13B 1.395(4) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.382(4) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.385(4) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.392(4) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9120562
