#------------------------------------------------------------------------------
#$Date: 2019-03-05 09:52:05 +0100 (Tue 05 de Mar de 2019) $
#$Revision: 213973 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/04/7150468.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_7150468
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         'C14 H14 O Se'
_chemical_formula_sum            'C14 H14 O Se'
_chemical_formula_weight         277.21
_chemical_name_common            2
_chemical_name_systematic
; 
2,3-dimethyl-4-(phenylseleno)phenol 
;
_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
_cell_angle_alpha                83.594(14)
_cell_angle_beta                 73.236(16)
_cell_angle_gamma                86.000(14)
_cell_formula_units_Z            2
_cell_length_a                   7.2242(15)
_cell_length_b                   7.9556(11)
_cell_length_c                   11.007(2)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    122.0(5)
_cell_measurement_theta_max      42.57
_cell_measurement_theta_min      39.52
_cell_volume                     601.47(19)
_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  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4817
_diffrn_reflns_theta_full        74.85
_diffrn_reflns_theta_max         74.85
_diffrn_reflns_theta_min         4.21
_diffrn_standards_decay_%        2.0
_diffrn_standards_interval_time  167
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    4.014
_exptl_absorpt_correction_T_max  0.199
_exptl_absorpt_correction_T_min  0.030
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(DeTitta, 1985)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.264
_refine_diff_density_min         -1.127
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0247
_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)+(0.0275P)²+0.4290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0678
_reflns_number_gt                2419
_reflns_number_total             2454
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b211130f.txt
_cod_data_source_block           2
_cod_original_cell_volume        601.5(2)
_cod_database_code               7150468
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 0.17393(2) 0.25609(2) 0.121822(16) 0.01567(8) Uani 1 1 d . . .
C1 C 0.2772(3) 0.4657(2) 0.13830(17) 0.0153(3) Uani 1 1 d . . .
C2 C 0.4230(3) 0.4737(2) 0.19842(17) 0.0152(4) Uani 1 1 d . . .
C3 C 0.4998(3) 0.6321(3) 0.19728(17) 0.0159(4) Uani 1 1 d . . .
C4 C 0.4259(3) 0.7762(3) 0.14002(17) 0.0171(4) Uani 1 1 d . . .
C5 C 0.2808(3) 0.7663(3) 0.08090(18) 0.0184(4) Uani 1 1 d . . .
H5 H 0.2325 0.8656 0.0418 0.022 Uiso 1 1 calc R . .
C6 C 0.2080(3) 0.6111(3) 0.07968(17) 0.0181(4) Uani 1 1 d . . .
H6 H 0.1102 0.6032 0.0387 0.022 Uiso 1 1 calc R . .
O4 O 0.5028(2) 0.92766(18) 0.14359(14) 0.0219(3) Uani 1 1 d . . .
H4 H 0.4329 1.0074 0.1219 0.033 Uiso 1 1 calc R . .
C11 C 0.0013(3) 0.2070(3) 0.29029(17) 0.0160(3) Uani 1 1 d . . .
C12 C -0.0869(3) 0.0520(3) 0.31484(19) 0.0211(4) Uani 1 1 d . . .
H12 H -0.0579 -0.0250 0.2512 0.025 Uiso 1 1 calc R . .
C13 C -0.2174(3) 0.0103(3) 0.4330(2) 0.0240(4) Uani 1 1 d . . .
H13 H -0.2782 -0.0953 0.4499 0.029 Uiso 1 1 calc R . .
C14 C -0.2595(3) 0.1217(3) 0.52623(19) 0.0238(4) Uani 1 1 d . . .
H14 H -0.3485 0.0926 0.6070 0.029 Uiso 1 1 calc R . .
C15 C -0.1708(3) 0.2759(3) 0.5010(2) 0.0257(4) Uani 1 1 d . . .
H15 H -0.1996 0.3525 0.5648 0.031 Uiso 1 1 calc R . .
C16 C -0.0398(3) 0.3195(3) 0.38266(19) 0.0207(4) Uani 1 1 d . . .
H16 H 0.0206 0.4253 0.3657 0.025 Uiso 1 1 calc R . .
C7 C 0.4968(3) 0.3197(3) 0.26487(19) 0.0211(4) Uani 1 1 d . . .
H71 H 0.4107 0.2262 0.2743 0.025 Uiso 1 1 calc R . .
H72 H 0.5004 0.3449 0.3493 0.025 Uiso 1 1 calc R . .
H73 H 0.6274 0.2873 0.2144 0.025 Uiso 1 1 calc R . .
C8 C 0.6620(3) 0.6465(3) 0.2564(2) 0.0237(4) Uani 1 1 d . . .
H81 H 0.7684 0.5666 0.2213 0.028 Uiso 1 1 calc R . .
H82 H 0.6143 0.6202 0.3490 0.028 Uiso 1 1 calc R . .
H83 H 0.7083 0.7620 0.2373 0.028 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 101.51(8) . . ?
C6 C1 C2 121.00(17) . . ?
C6 C1 Se1 116.12(14) . . ?
C2 C1 Se1 122.76(14) . . ?
C1 C2 C3 118.55(17) . . ?
C1 C2 C7 122.03(17) . . ?
C3 C2 C7 119.42(17) . . ?
C4 C3 C2 119.42(17) . . ?
C4 C3 C8 119.98(17) . . ?
C2 C3 C8 120.60(17) . . ?
O4 C4 C3 117.18(17) . . ?
O4 C4 C5 121.48(18) . . ?
C3 C4 C5 121.34(18) . . ?
C6 C5 C4 119.40(18) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.27(17) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C4 O4 H4 109.5 . . ?
C16 C11 C12 120.50(18) . . ?
C16 C11 Se1 123.00(15) . . ?
C12 C11 Se1 116.48(15) . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.59(19) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 119.29(19) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C2 C7 H71 109.5 . . ?
C2 C7 H72 109.5 . . ?
H71 C7 H72 109.5 . . ?
C2 C7 H73 109.5 . . ?
H71 C7 H73 109.5 . . ?
H72 C7 H73 109.5 . . ?
C3 C8 H81 109.5 . . ?
C3 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C3 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
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 1.9210(19) . ?
Se1 C11 1.9284(19) . ?
C1 C6 1.394(3) . ?
C1 C2 1.404(3) . ?
C2 C3 1.409(3) . ?
C2 C7 1.502(3) . ?
C3 C4 1.394(3) . ?
C3 C8 1.512(3) . ?
C4 O4 1.371(2) . ?
C4 C5 1.395(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
O4 H4 0.8400 . ?
C11 C16 1.383(3) . ?
C11 C12 1.392(3) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C7 H71 0.9800 . ?
C7 H72 0.9800 . ?
C7 H73 0.9800 . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C8 H83 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9099089
