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#$Date: 2024-07-05 18:57:56 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293006 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/61/7716186.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_7716186
loop_
_publ_author_name
'Ogawa, Naoki'
'Suzuki, Nobuhiro'
'Katsura, Yoshifumi'
'Minoura, Mao'
'Nakanishi, Waro'
'Hayashi, Satoko'
_publ_section_title
;
 Extremely stable system of 1-haloselanyl-anthraquinones: experimental and
 theoretical investigations.
;
_journal_issue                   24
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10099
_journal_page_last               10112
_journal_paper_doi               10.1039/d4dt00760c
_journal_volume                  53
_journal_year                    2024
_chemical_formula_sum            'C14 H7 I O2 Se'
_chemical_formula_weight         413.06
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-05-09 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                107.639(15)
_cell_angle_beta                 92.822(16)
_cell_angle_gamma                111.661(12)
_cell_formula_units_Z            2
_cell_length_a                   7.122(3)
_cell_length_b                   8.016(3)
_cell_length_c                   12.208(5)
_cell_measurement_temperature    100(2)
_cell_volume                     607.0(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            47829
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.437
_diffrn_reflns_theta_min         2.841
_exptl_absorpt_coefficient_mu    5.625
_exptl_crystal_density_diffrn    2.260
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.557
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.300
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.300
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0266
_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)+(0.0222P)²+2.4859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0769
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2575
_reflns_number_total             2710
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt00760c2.cif
_cod_data_source_block           1_1-AnqSeI
_cod_depositor_comments
'Adding full bibliography for 7716186--7716189.cif.'
_cod_database_code               7716186
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.603
_shelx_estimated_absorpt_t_max   0.603
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.82962(5) 0.67225(4) 1.00028(2) 0.02505(10) Uani 1 1 d . . . . .
Se1 Se 0.76566(6) 0.45291(5) 0.78513(3) 0.01708(11) Uani 1 1 d . . . . .
C1 C 0.7871(6) 0.6318(5) 0.7068(3) 0.0147(7) Uani 1 1 d . . . . .
C2 C 0.7631(6) 0.5621(5) 0.5839(3) 0.0141(7) Uani 1 1 d . . . . .
C3 C 0.7246(6) 0.3616(5) 0.5249(3) 0.0149(7) Uani 1 1 d . . . . .
C4 C 0.6996(6) 0.2850(5) 0.3964(3) 0.0145(7) Uani 1 1 d . . . . .
C5 C 0.6616(6) 0.0937(5) 0.3401(3) 0.0174(7) Uani 1 1 d . . . . .
H1 H 0.6480 0.0117 0.3841 0.021 Uiso 1 1 calc R U . . .
C6 C 0.6433(6) 0.0221(6) 0.2186(3) 0.0204(8) Uani 1 1 d . . . . .
H2 H 0.6179 -0.1085 0.1802 0.024 Uiso 1 1 calc R U . . .
C7 C 0.6624(6) 0.1418(6) 0.1538(3) 0.0217(8) Uani 1 1 d . . . . .
H3 H 0.6523 0.0929 0.0715 0.026 Uiso 1 1 calc R U . . .
C8 C 0.6965(6) 0.3341(6) 0.2092(3) 0.0195(8) Uani 1 1 d . . . . .
H4 H 0.7062 0.4144 0.1644 0.023 Uiso 1 1 calc R U . . .
C9 C 0.7163(6) 0.4068(5) 0.3307(3) 0.0159(7) Uani 1 1 d . . . . .
C10 C 0.7543(6) 0.6119(5) 0.3891(3) 0.0162(7) Uani 1 1 d . . . . .
C11 C 0.7781(6) 0.6855(5) 0.5196(3) 0.0149(7) Uani 1 1 d . . . . .
C12 C 0.8168(6) 0.8763(5) 0.5775(3) 0.0175(7) Uani 1 1 d . . . . .
H5 H 0.8295 0.9601 0.5349 0.021 Uiso 1 1 calc R U . . .
C13 C 0.8370(6) 0.9436(5) 0.6992(3) 0.0191(8) Uani 1 1 d . . . . .
H6 H 0.8603 1.0733 0.7387 0.023 Uiso 1 1 calc R U . . .
C14 C 0.8235(6) 0.8246(5) 0.7637(3) 0.0173(7) Uani 1 1 d . . . . .
H7 H 0.8390 0.8737 0.8464 0.021 Uiso 1 1 calc R U . . .
O1 O 0.7141(5) 0.2588(4) 0.5858(2) 0.0206(6) Uani 1 1 d . . . . .
O2 O 0.7668(5) 0.7172(4) 0.3326(3) 0.0231(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'
I I -0.4742 1.8119 '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
C1 Se1 I1 100.34(11) . . ?
C14 C1 C2 118.8(3) . . ?
C14 C1 Se1 124.4(3) . . ?
C2 C1 Se1 116.9(3) . . ?
C1 C2 C11 120.3(3) . . ?
C1 C2 C3 118.7(3) . . ?
C11 C2 C3 121.0(3) . . ?
O1 C3 C2 118.4(3) . . ?
O1 C3 C4 121.7(3) . . ?
C2 C3 C4 119.8(3) . . ?
C5 C4 C9 120.2(3) . . ?
C5 C4 C3 119.9(3) . . ?
C9 C4 C3 120.0(3) . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H1 120.0 . . ?
C6 C5 H1 120.0 . . ?
C7 C6 C5 120.2(4) . . ?
C7 C6 H2 119.9 . . ?
C5 C6 H2 119.9 . . ?
C6 C7 C8 120.5(4) . . ?
C6 C7 H3 119.8 . . ?
C8 C7 H3 119.8 . . ?
C9 C8 C7 119.6(4) . . ?
C9 C8 H4 120.2 . . ?
C7 C8 H4 120.2 . . ?
C8 C9 C4 119.6(3) . . ?
C8 C9 C10 119.2(3) . . ?
C4 C9 C10 121.1(3) . . ?
O2 C10 C9 121.4(3) . . ?
O2 C10 C11 120.9(3) . . ?
C9 C10 C11 117.7(3) . . ?
C12 C11 C2 120.1(3) . . ?
C12 C11 C10 119.6(3) . . ?
C2 C11 C10 120.4(3) . . ?
C11 C12 C13 119.3(3) . . ?
C11 C12 H5 120.4 . . ?
C13 C12 H5 120.4 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H6 119.3 . . ?
C12 C13 H6 119.3 . . ?
C13 C14 C1 120.2(4) . . ?
C13 C14 H7 119.9 . . ?
C1 C14 H7 119.9 . . ?
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
I1 Se1 2.5866(11) . ?
Se1 C1 1.918(4) . ?
C1 C14 1.404(5) . ?
C1 C2 1.411(5) . ?
C2 C11 1.416(5) . ?
C2 C3 1.460(5) . ?
C3 O1 1.253(4) . ?
C3 C4 1.475(5) . ?
C4 C5 1.391(5) . ?
C4 C9 1.417(5) . ?
C5 C6 1.398(6) . ?
C5 H1 0.9500 . ?
C6 C7 1.393(6) . ?
C6 H2 0.9500 . ?
C7 C8 1.403(6) . ?
C7 H3 0.9500 . ?
C8 C9 1.399(5) . ?
C8 H4 0.9500 . ?
C9 C10 1.493(5) . ?
C10 O2 1.224(5) . ?
C10 C11 1.499(5) . ?
C11 C12 1.389(5) . ?
C12 C13 1.398(6) . ?
C12 H5 0.9500 . ?
C13 C14 1.391(5) . ?
C13 H6 0.9500 . ?
C14 H7 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
C14 C1 C2 C11 0.8(6) . . . . ?
Se1 C1 C2 C11 -179.6(3) . . . . ?
C14 C1 C2 C3 -179.8(3) . . . . ?
Se1 C1 C2 C3 -0.2(5) . . . . ?
C1 C2 C3 O1 0.1(6) . . . . ?
C11 C2 C3 O1 179.5(4) . . . . ?
C1 C2 C3 C4 -179.8(3) . . . . ?
C11 C2 C3 C4 -0.3(6) . . . . ?
O1 C3 C4 C5 0.6(6) . . . . ?
C2 C3 C4 C5 -179.6(4) . . . . ?
O1 C3 C4 C9 -178.8(4) . . . . ?
C2 C3 C4 C9 1.0(6) . . . . ?
C9 C4 C5 C6 1.1(6) . . . . ?
C3 C4 C5 C6 -178.3(4) . . . . ?
C4 C5 C6 C7 -0.2(6) . . . . ?
C5 C6 C7 C8 -1.1(6) . . . . ?
C6 C7 C8 C9 1.5(6) . . . . ?
C7 C8 C9 C4 -0.6(6) . . . . ?
C7 C8 C9 C10 179.5(4) . . . . ?
C5 C4 C9 C8 -0.7(6) . . . . ?
C3 C4 C9 C8 178.7(4) . . . . ?
C5 C4 C9 C10 179.2(4) . . . . ?
C3 C4 C9 C10 -1.4(6) . . . . ?
C8 C9 C10 O2 0.6(6) . . . . ?
C4 C9 C10 O2 -179.3(4) . . . . ?
C8 C9 C10 C11 -179.0(4) . . . . ?
C4 C9 C10 C11 1.1(6) . . . . ?
C1 C2 C11 C12 0.1(6) . . . . ?
C3 C2 C11 C12 -179.4(4) . . . . ?
C1 C2 C11 C10 179.5(3) . . . . ?
C3 C2 C11 C10 0.1(6) . . . . ?
O2 C10 C11 C12 -0.6(6) . . . . ?
C9 C10 C11 C12 179.0(4) . . . . ?
O2 C10 C11 C2 179.9(4) . . . . ?
C9 C10 C11 C2 -0.4(5) . . . . ?
C2 C11 C12 C13 -1.2(6) . . . . ?
C10 C11 C12 C13 179.4(4) . . . . ?
C11 C12 C13 C14 1.4(6) . . . . ?
C12 C13 C14 C1 -0.6(6) . . . . ?
C2 C1 C14 C13 -0.5(6) . . . . ?
Se1 C1 C14 C13 179.9(3) . . . . ?
