#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/04/7150474.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_7150474
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            8
_chemical_name_systematic
; 
1-methoxy-4-methyl-2-(phenylseleno)benzene 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_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                   14.991(2)
_cell_length_b                   9.9673(18)
_cell_length_c                   15.930(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    122.0(5)
_cell_measurement_theta_max      42.24
_cell_measurement_theta_min      40.04
_cell_volume                     2380.3(6)
_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  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6064
_diffrn_reflns_theta_full        74.91
_diffrn_reflns_theta_max         74.91
_diffrn_reflns_theta_min         5.55
_diffrn_standards_decay_%        7.2
_diffrn_standards_interval_time  167
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    4.057
_exptl_absorpt_correction_T_max  0.242
_exptl_absorpt_correction_T_min  0.121
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(DeTitta, 1985)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.00204(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0267P)²+1.9116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0727
_reflns_number_gt                2384
_reflns_number_total             2447
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b211130f.txt
_cod_data_source_block           8
_cod_database_code               7150474
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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 -0.005245(13) 0.21460(2) 0.500131(10) 0.02166(10) Uani 1 1 d . . .
C1 C 0.10628(12) 0.30767(16) 0.49113(10) 0.0169(3) Uani 1 1 d . . .
C2 C 0.15513(11) 0.28017(15) 0.41824(10) 0.0182(3) Uani 1 1 d . . .
O2 O 0.11432(8) 0.19275(12) 0.36405(7) 0.0223(3) Uani 1 1 d . . .
C7 C 0.15858(13) 0.16256(19) 0.28717(11) 0.0273(4) Uani 1 1 d . . .
H71 H 0.2158 0.1192 0.2992 0.033 Uiso 1 1 calc R . .
H72 H 0.1690 0.2457 0.2558 0.033 Uiso 1 1 calc R . .
H73 H 0.1214 0.1020 0.2537 0.033 Uiso 1 1 calc R . .
C3 C 0.23733(11) 0.34022(17) 0.40556(10) 0.0211(3) Uani 1 1 d . . .
H3 H 0.2712 0.3200 0.3568 0.025 Uiso 1 1 calc R . .
C4 C 0.27010(11) 0.43071(17) 0.46495(11) 0.0214(3) Uani 1 1 d . . .
H4 H 0.3264 0.4721 0.4559 0.026 Uiso 1 1 calc R . .
C5 C 0.22203(11) 0.46146(16) 0.53703(11) 0.0199(3) Uani 1 1 d . . .
C8 C 0.25519(12) 0.56462(18) 0.59901(11) 0.0263(4) Uani 1 1 d . . .
H81 H 0.2371 0.5387 0.6558 0.032 Uiso 1 1 calc R . .
H82 H 0.2296 0.6524 0.5853 0.032 Uiso 1 1 calc R . .
H83 H 0.3204 0.5697 0.5961 0.032 Uiso 1 1 calc R . .
C6 C 0.13991(11) 0.39777(15) 0.54964(10) 0.0180(3) Uani 1 1 d . . .
H6 H 0.1066 0.4165 0.5990 0.022 Uiso 1 1 calc R . .
C11 C -0.03732(10) 0.26125(16) 0.61312(10) 0.0177(3) Uani 1 1 d . . .
C12 C -0.02983(11) 0.16438(17) 0.67575(11) 0.0208(3) Uani 1 1 d . . .
H12 H -0.0061 0.0784 0.6629 0.025 Uiso 1 1 calc R . .
C13 C -0.05718(12) 0.19396(17) 0.75706(11) 0.0232(4) Uani 1 1 d . . .
H13 H -0.0520 0.1280 0.7999 0.028 Uiso 1 1 calc R . .
C14 C -0.09197(11) 0.31940(18) 0.77594(10) 0.0222(3) Uani 1 1 d . . .
H14 H -0.1107 0.3394 0.8315 0.027 Uiso 1 1 calc R . .
C15 C -0.09922(11) 0.41537(17) 0.71337(11) 0.0214(3) Uani 1 1 d . . .
H15 H -0.1225 0.5016 0.7264 0.026 Uiso 1 1 calc R . .
C16 C -0.07282(11) 0.38667(16) 0.63174(10) 0.0201(3) Uani 1 1 d . . .
H16 H -0.0790 0.4523 0.5889 0.024 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 99.87(7) . . ?
C6 C1 C2 119.56(16) . . ?
C6 C1 Se1 125.38(12) . . ?
C2 C1 Se1 115.05(12) . . ?
O2 C2 C3 125.45(15) . . ?
O2 C2 C1 114.42(15) . . ?
C3 C2 C1 120.12(15) . . ?
C2 O2 C7 117.89(13) . . ?
O2 C7 H71 109.5 . . ?
O2 C7 H72 109.5 . . ?
H71 C7 H72 109.5 . . ?
O2 C7 H73 109.5 . . ?
H71 C7 H73 109.5 . . ?
H72 C7 H73 109.5 . . ?
C2 C3 C4 119.57(15) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.32(16) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.33(16) . . ?
C4 C5 C8 121.32(16) . . ?
C6 C5 C8 120.31(15) . . ?
C5 C8 H81 109.5 . . ?
C5 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C5 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
C1 C6 C5 121.08(15) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C16 C11 C12 120.08(15) . . ?
C16 C11 Se1 120.89(12) . . ?
C12 C11 Se1 118.90(12) . . ?
C13 C12 C11 119.78(16) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.25(15) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.70(16) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.59(16) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 119.59(15) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 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 C1 1.9174(18) . ?
Se1 C11 1.9203(16) . ?
C1 C6 1.389(2) . ?
C1 C2 1.400(2) . ?
C2 O2 1.371(2) . ?
C2 C3 1.385(2) . ?
O2 C7 1.425(2) . ?
C7 H71 0.9800 . ?
C7 H72 0.9800 . ?
C7 H73 0.9800 . ?
C3 C4 1.396(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(2) . ?
C5 C8 1.510(2) . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C8 H83 0.9800 . ?
C6 H6 0.9500 . ?
C11 C16 1.391(2) . ?
C11 C12 1.393(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9272970
