#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/08/4020865.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_4020865
loop_
_publ_author_name
'Warô Nakanishi'
'Satoko Hayashi'
'Norio Itoh'
_publ_section_title
;
 Extended Hypervalent 5c-6e Interactions:
 Linear Alignment of Five C-Se---O---Se-C Atoms in Anthraquinone
 and 9-Methoxyanthracene Bearing Arylselanyl Groups
 at the 1,8-Positions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1676
_journal_page_last               1684
_journal_paper_doi               10.1021/jo035393+
_journal_volume                  69
_journal_year                    2004
_chemical_formula_moiety         'C27 H20 O Se2 '
_chemical_formula_sum            'C27 H20 O Se2'
_chemical_formula_weight         518.37
_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'
_cell_angle_alpha                96.64(2)
_cell_angle_beta                 102.20(3)
_cell_angle_gamma                106.48(2)
_cell_formula_units_Z            2
_cell_length_a                   10.930(3)
_cell_length_b                   13.673(4)
_cell_length_c                   8.052(2)
_cell_measurement_temperature    298.2
_cell_volume                     1107.9(6)
_diffrn_ambient_temperature      298.2
_exptl_crystal_density_diffrn    1.554
_refine_ls_R_factor_obs          0.0401
_refine_ls_wR_factor_obs         0.0303
_cod_original_formula_sum        'C27 H20 O Se2 '
_cod_database_code               4020865
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_occupancy
_atom_site_refinement_flags
Se(1) 0.18833(6) 0.40279(4) -0.03239(7) 0.0602(2) Uani d . 1.00 .
Se(2) -0.15732(6) 0.02749(4) -0.22365(7) 0.0619(2) Uani d . 1.00 .
O(1) 0.0395(3) 0.2077(2) -0.2085(4) 0.048(1) Uani d . 1.00 .
C(1) 0.1540(5) 0.4132(4) -0.2738(6) 0.044(2) Uani d . 1.00 .
C(2) 0.2154(5) 0.5027(4) -0.3238(6) 0.051(2) Uani d . 1.00 .
C(3) 0.1845(5) 0.5164(4) -0.4958(7) 0.054(2) Uani d . 1.00 .
C(4) 0.0892(5) 0.4410(4) -0.6179(6) 0.052(2) Uani d . 1.00 .
C(5) 0.0219(5) 0.3454(4) -0.5765(6) 0.044(2) Uani d . 1.00 .
C(6) -0.0758(5) 0.2681(4) -0.6995(6) 0.051(2) Uani d . 1.00 .
C(7) -0.1448(5) 0.1750(4) -0.6624(6) 0.045(2) Uani d . 1.00 .
C(8) -0.2496(5) 0.1003(4) -0.7911(6) 0.056(2) Uani d . 1.00 .
C(9) -0.3177(6) 0.0112(4) -0.7524(7) 0.061(2) Uani d . 1.00 .
C(10) -0.2889(5) -0.0088(4) -0.5828(7) 0.055(2) Uani d . 1.00 .
C(11) -0.1885(5) 0.0586(4) -0.4540(6) 0.048(2) Uani d . 1.00 .
C(12) -0.1105(5) 0.1545(3) -0.4893(6) 0.040(1) Uani d . 1.00 .
C(13) -0.0051(5) 0.2305(4) -0.3693(6) 0.041(1) Uani d . 1.00 .
C(14) 0.0580(5) 0.3281(3) -0.4011(6) 0.039(1) Uani d . 1.00 .
C(15) 0.2753(5) 0.5471(4) 0.0683(6) 0.050(2) Uani d . 1.00 .
C(16) 0.4094(7) 0.5851(6) 0.1347(8) 0.084(3) Uani d . 1.00 .
C(17) 0.4665(7) 0.6899(7) 0.221(1) 0.112(3) Uani d . 1.00 .
C(18) 0.3885(9) 0.7515(6) 0.2333(10) 0.104(3) Uani d . 1.00 .
C(19) 0.2584(7) 0.7129(5) 0.1677(8) 0.075(2) Uani d . 1.00 .
C(20) 0.2017(5) 0.6112(4) 0.0873(6) 0.055(2) Uani d . 1.00 .
C(21) -0.2811(6) -0.1117(4) -0.2688(6) 0.054(2) Uani d . 1.00 .
C(22) -0.2407(5) -0.1944(4) -0.3170(7) 0.062(2) Uani d . 1.00 .
C(23) -0.3246(7) -0.2939(4) -0.3396(8) 0.073(2) Uani d . 1.00 .
C(24) -0.4476(7) -0.3107(5) -0.3152(9) 0.082(2) Uani d . 1.00 .
C(25) -0.4875(6) -0.2285(6) -0.2656(9) 0.090(3) Uani d . 1.00 .
C(26) -0.4047(6) -0.1273(5) -0.2427(8) 0.070(2) Uani d . 1.00 .
C(27) 0.1432(5) 0.1623(4) -0.2065(7) 0.068(2) Uani d . 1.00 .
H(1) 0.2769 0.5585 -0.2312 0.0380 Uiso calc . 1.00 .
H(2) 0.2202 0.5786 -0.5440 0.0380 Uiso calc . 1.00 .
H(3) 0.0615 0.4647 -0.7251 0.0380 Uiso calc . 1.00 .
H(4) -0.0979 0.2802 -0.8220 0.0612 Uiso calc . 1.00 .
H(5) -0.2729 0.1109 -0.9090 0.0380 Uiso calc . 1.00 .
H(6) -0.3827 -0.0450 -0.8421 0.0380 Uiso calc . 1.00 .
H(7) -0.3331 -0.0725 -0.5478 0.0380 Uiso calc . 1.00 .
H(8) 0.4616 0.5362 0.1502 0.0380 Uiso calc . 1.00 .
H(9) 0.5596 0.7077 0.2774 0.0380 Uiso calc . 1.00 .
H(10) 0.4296 0.8239 0.2954 0.1248 Uiso calc . 1.00 .
H(11) 0.2131 0.7643 0.1983 0.0380 Uiso calc . 1.00 .
H(12) 0.1044 0.5935 0.0442 0.0380 Uiso calc . 1.00 .
H(13) -0.4416 -0.0708 -0.2208 0.0380 Uiso calc . 1.00 .
H(14) -0.5790 -0.2416 -0.2467 0.1076 Uiso calc . 1.00 .
H(15) -0.5071 -0.3818 -0.3286 0.0984 Uiso calc . 1.00 .
H(16) -0.3011 -0.3559 -0.3765 0.0380 Uiso calc . 1.00 .
H(17) -0.1527 -0.1945 -0.3285 0.0380 Uiso calc . 1.00 .
H(18) 0.1684 0.1565 -0.0850 0.0380 Uiso calc . 1.00 .
H(19) 0.2302 0.2054 -0.2062 0.0380 Uiso calc . 1.00 .
H(20) 0.1064 0.0922 -0.2670 0.0380 Uiso calc . 1.00 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se(1) C(1) 1.930(4) 1_555 1_555 yes
Se(1) C(15) 1.921(5) 1_555 1_555 yes
Se(2) C(11) 1.932(5) 1_555 1_555 yes
Se(2) C(21) 1.938(5) 1_555 1_555 yes
O(1) C(13) 1.387(5) 1_555 1_555 yes
O(1) C(27) 1.436(6) 1_555 1_555 yes
C(1) C(2) 1.368(6) 1_555 1_555 yes
C(1) C(14) 1.444(6) 1_555 1_555 yes
C(2) C(3) 1.402(6) 1_555 1_555 yes
C(3) C(4) 1.356(7) 1_555 1_555 yes
C(4) C(5) 1.421(6) 1_555 1_555 yes
C(5) C(6) 1.382(6) 1_555 1_555 yes
C(5) C(14) 1.449(6) 1_555 1_555 yes
C(6) C(7) 1.385(6) 1_555 1_555 yes
C(7) C(8) 1.420(6) 1_555 1_555 yes
C(7) C(12) 1.447(6) 1_555 1_555 yes
C(8) C(9) 1.344(7) 1_555 1_555 yes
C(9) C(10) 1.412(7) 1_555 1_555 yes
C(10) C(11) 1.362(6) 1_555 1_555 yes
C(11) C(12) 1.442(6) 1_555 1_555 yes
C(12) C(13) 1.400(6) 1_555 1_555 yes
C(13) C(14) 1.397(6) 1_555 1_555 yes
C(15) C(16) 1.370(7) 1_555 1_555 yes
C(15) C(20) 1.365(7) 1_555 1_555 yes
C(16) C(17) 1.415(9) 1_555 1_555 yes
C(17) C(18) 1.368(10) 1_555 1_555 yes
C(18) C(19) 1.331(9) 1_555 1_555 yes
C(19) C(20) 1.367(7) 1_555 1_555 yes
C(21) C(22) 1.370(7) 1_555 1_555 yes
C(21) C(26) 1.372(7) 1_555 1_555 yes
C(22) C(23) 1.375(7) 1_555 1_555 yes
C(23) C(24) 1.359(8) 1_555 1_555 yes
C(24) C(25) 1.364(8) 1_555 1_555 yes
C(25) C(26) 1.389(8) 1_555 1_555 yes
