#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/37/7003721.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_7003721
loop_
_publ_author_name
'Levason, William'
'Manning, Joanna M.'
'Nirwan, Manisha'
'Ratnani, Raju'
'Reid, Gillian'
'Smith, Hayley L.'
'Webster, Michael'
_publ_section_title
;
 Selenoether macrocyclic chemistry---syntheses and properties of new
 potentially tridentate and hexadentate Se/O-donor macrocycles
;
_journal_issue                   26
_journal_name_full               'Dalton Transactions'
_journal_page_first              3486
_journal_page_last               3492
_journal_paper_doi               10.1039/b718950h
_journal_year                    2008
_chemical_formula_moiety         'C12 H16 O Se2'
_chemical_formula_sum            'C12 H16 O Se2'
_chemical_formula_weight         334.17
_chemical_name_systematic
;
9,10-benzo-1,7-diselena-4-oxa-cycloundeca-9-ene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_date             2007-10-10
_audit_creation_method           'SHELXL-97 + hand edit'
_cell_angle_alpha                108.104(10)
_cell_angle_beta                 92.404(10)
_cell_angle_gamma                91.037(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9226(15)
_cell_length_b                   7.9778(15)
_cell_length_c                   10.1088(15)
_cell_measurement_reflns_used    2736
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     606.43(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13054
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.25
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.068
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'G.M. Sheldrick, (2003). SADABS. Version 2.10. Bruker AXS Inc.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.488
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0265P)²+1.1144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0734
_reflns_number_gt                2406
_reflns_number_total             2783
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b718950h.txt
_cod_data_source_block           07sdr015_[C12H16OSe2]
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7003721
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 0.29853(4) 0.20941(4) 0.82231(3) 0.01643(10) Uani 1 1 d . . .
Se2 Se 0.68227(4) -0.27965(4) 0.69455(3) 0.01768(10) Uani 1 1 d . . .
O1 O 0.2987(3) -0.2105(3) 0.7895(2) 0.0178(4) Uani 1 1 d . . .
C1 C 0.5179(4) 0.1463(4) 0.8922(3) 0.0174(6) Uani 1 1 d . . .
H1A H 0.5385 0.2153 0.9917 0.021 Uiso 1 1 calc R . .
H1B H 0.5148 0.0195 0.8846 0.021 Uiso 1 1 calc R . .
C2 C 0.1499(4) 0.0548(4) 0.8875(3) 0.0194(6) Uani 1 1 d . . .
H2A H 0.1930 0.0545 0.9808 0.023 Uiso 1 1 calc R . .
H2B H 0.0354 0.1036 0.8974 0.023 Uiso 1 1 calc R . .
C3 C 0.1370(4) -0.1341(4) 0.7907(3) 0.0180(6) Uani 1 1 d . . .
H3A H 0.0522 -0.2029 0.8235 0.022 Uiso 1 1 calc R . .
H3B H 0.1007 -0.1358 0.6953 0.022 Uiso 1 1 calc R . .
C4 C 0.3137(4) -0.3663(4) 0.6761(3) 0.0192(6) Uani 1 1 d . . .
H4A H 0.2987 -0.3396 0.5871 0.023 Uiso 1 1 calc R . .
H4B H 0.2252 -0.4545 0.6781 0.023 Uiso 1 1 calc R . .
C5 C 0.4866(4) -0.4394(4) 0.6867(3) 0.0192(6) Uani 1 1 d . . .
H5A H 0.4965 -0.5463 0.6055 0.023 Uiso 1 1 calc R . .
H5B H 0.4936 -0.4769 0.7714 0.023 Uiso 1 1 calc R . .
C6 C 0.5885(4) -0.1020(4) 0.6142(3) 0.0162(6) Uani 1 1 d . . .
H6A H 0.5956 -0.1430 0.5116 0.019 Uiso 1 1 calc R . .
H6B H 0.4683 -0.0837 0.6361 0.019 Uiso 1 1 calc R . .
C7 C 0.6895(4) 0.0670(4) 0.6760(3) 0.0140(6) Uani 1 1 d . . .
C8 C 0.8196(4) 0.1108(4) 0.6016(3) 0.0179(6) Uani 1 1 d . . .
H8 H 0.8416 0.0327 0.5122 0.021 Uiso 1 1 calc R . .
C9 C 0.9173(4) 0.2657(4) 0.6556(4) 0.0216(7) Uani 1 1 d . . .
H9 H 1.0036 0.2938 0.6027 0.026 Uiso 1 1 calc R . .
C10 C 0.8876(4) 0.3793(4) 0.7873(4) 0.0221(7) Uani 1 1 d . . .
H10 H 0.9546 0.4847 0.8256 0.027 Uiso 1 1 calc R . .
C11 C 0.7593(4) 0.3375(4) 0.8628(3) 0.0193(6) Uani 1 1 d . . .
H11 H 0.7399 0.4154 0.9529 0.023 Uiso 1 1 calc R . .
C12 C 0.6585(4) 0.1840(4) 0.8092(3) 0.0146(6) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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
C2 Se1 C1 98.42(13) . . ?
C5 Se2 C6 103.47(13) . . ?
C4 O1 C3 113.1(2) . . ?
C12 C1 Se1 110.1(2) . . ?
C12 C1 H1A 109.6 . . ?
Se1 C1 H1A 109.6 . . ?
C12 C1 H1B 109.6 . . ?
Se1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.2 . . ?
C3 C2 Se1 113.4(2) . . ?
C3 C2 H2A 108.9 . . ?
Se1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
Se1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
O1 C3 C2 108.6(2) . . ?
O1 C3 H3A 110.0 . . ?
C2 C3 H3A 110.0 . . ?
O1 C3 H3B 110.0 . . ?
C2 C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
O1 C4 C5 109.0(2) . . ?
O1 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
O1 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C4 C5 Se2 116.6(2) . . ?
C4 C5 H5A 108.1 . . ?
Se2 C5 H5A 108.1 . . ?
C4 C5 H5B 108.1 . . ?
Se2 C5 H5B 108.1 . . ?
H5A C5 H5B 107.3 . . ?
C7 C6 Se2 108.02(19) . . ?
C7 C6 H6A 110.1 . . ?
Se2 C6 H6A 110.1 . . ?
C7 C6 H6B 110.1 . . ?
Se2 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C8 C7 C12 118.7(3) . . ?
C8 C7 C6 119.7(3) . . ?
C12 C7 C6 121.6(3) . . ?
C9 C8 C7 121.6(3) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 121.5(3) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C7 119.1(3) . . ?
C11 C12 C1 119.9(3) . . ?
C7 C12 C1 121.0(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 C2 1.965(3) . ?
Se1 C1 1.981(3) . ?
Se2 C5 1.972(3) . ?
Se2 C6 1.981(3) . ?
O1 C4 1.416(4) . ?
O1 C3 1.427(4) . ?
C1 C12 1.503(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.520(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.511(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.498(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.401(4) . ?
C7 C12 1.414(4) . ?
C8 C9 1.391(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(4) . ?
C11 H11 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 Se1 C1 C12 156.3(2) . . . . ?
C1 Se1 C2 C3 -82.4(2) . . . . ?
C4 O1 C3 C2 -163.7(3) . . . . ?
Se1 C2 C3 O1 65.2(3) . . . . ?
C3 O1 C4 C5 -178.3(2) . . . . ?
O1 C4 C5 Se2 -56.4(3) . . . . ?
C6 Se2 C5 C4 -21.0(3) . . . . ?
C5 Se2 C6 C7 152.1(2) . . . . ?
Se2 C6 C7 C8 98.1(3) . . . . ?
Se2 C6 C7 C12 -81.2(3) . . . . ?
C12 C7 C8 C9 -0.2(4) . . . . ?
C6 C7 C8 C9 -179.5(3) . . . . ?
C7 C8 C9 C10 1.0(5) . . . . ?
C8 C9 C10 C11 -0.8(5) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C10 C11 C12 C7 1.0(4) . . . . ?
C10 C11 C12 C1 -178.2(3) . . . . ?
C8 C7 C12 C11 -0.8(4) . . . . ?
C6 C7 C12 C11 178.5(3) . . . . ?
C8 C7 C12 C1 178.5(3) . . . . ?
C6 C7 C12 C1 -2.3(4) . . . . ?
Se1 C1 C12 C11 100.3(3) . . . . ?
Se1 C1 C12 C7 -78.9(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652651
