# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_1-AnqSeI
_database_code_depnum_ccdc_archive 'CCDC 2339576'
loop_
_audit_author_name
_audit_author_address
'Mao Minoura'
;Department of Chemistry, College of Science, Rikkyo University,
Japan
;
_audit_update_record             
;
2024-05-09 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H7 I O2 Se'
_chemical_formula_weight         413.06

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.122(3)
_cell_length_b                   8.016(3)
_cell_length_c                   12.208(5)
_cell_angle_alpha                107.639(15)
_cell_angle_beta                 92.822(16)
_cell_angle_gamma                111.661(12)
_cell_volume                     607.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.260
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.625
_shelx_estimated_absorpt_T_min   0.603
_shelx_estimated_absorpt_T_max   0.603
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47829
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.841
_diffrn_reflns_theta_max         27.437
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2710
_reflns_number_gt                2575
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0222P)²+2.4859P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2710
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0769
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.300
_refine_ls_restrained_S_all      1.300
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

_refine_diff_density_max         1.557
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.153

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7_1-AnqBr
_database_code_depnum_ccdc_archive 'CCDC 2339580'
loop_
_audit_author_name
_audit_author_address
'Mao Minoura'
;Department of Chemistry, College of Science, Rikkyo University,
Japan
;
_audit_update_record             
;
2024-05-09 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H7 Br O2'
_chemical_formula_weight         287.11

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.7673(8)
_cell_length_b                   3.9545(4)
_cell_length_c                   16.7397(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.654(4)
_cell_angle_gamma                90
_cell_volume                     512.48(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    3.993
_shelx_estimated_absorpt_T_min   0.691
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9983
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.441
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2336
_reflns_number_gt                2133
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+0.1438P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 831 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.076(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2336
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.6337(6) 0.1617(10) 0.3802(3) 0.0174(11) Uani 1 1 d . . . . .
C2 C 0.4757(5) 0.0433(18) 0.4015(3) 0.0195(11) Uani 1 1 d . . . . .
H2 H 0.4687 -0.0647 0.4518 0.023 Uiso 1 1 calc R U . . .
C3 C 0.3255(5) 0.082(2) 0.3492(2) 0.0222(8) Uani 1 1 d . . . . .
H3 H 0.2165 0.0069 0.3643 0.027 Uiso 1 1 calc R U . . .
C4 C 0.3403(6) 0.2291(13) 0.2764(3) 0.0194(10) Uani 1 1 d . . . . .
H4 H 0.2408 0.2488 0.2398 0.023 Uiso 1 1 calc R U . . .
C5 C 0.4987(6) 0.3521(12) 0.2542(3) 0.0160(9) Uani 1 1 d . . . . .
C6 C 0.4998(6) 0.5109(11) 0.1734(3) 0.0180(12) Uani 1 1 d . . . . .
C7 C 0.6646(6) 0.6569(10) 0.1506(3) 0.0166(11) Uani 1 1 d . . . . .
C8 C 0.6710(6) 0.8145(12) 0.0758(3) 0.0201(10) Uani 1 1 d . . . . .
H8 H 0.5696 0.8271 0.0401 0.024 Uiso 1 1 calc R U . . .
C9 C 0.8241(6) 0.9517(13) 0.0535(3) 0.0219(10) Uani 1 1 d . . . . .
H9 H 0.8277 1.0581 0.0028 0.026 Uiso 1 1 calc R U . . .
C10 C 0.9726(6) 0.9331(13) 0.1058(3) 0.0200(10) Uani 1 1 d . . . . .
H10 H 1.0775 1.0294 0.0910 0.024 Uiso 1 1 calc R U . . .
C11 C 0.9677(6) 0.7747(12) 0.1792(3) 0.0182(10) Uani 1 1 d . . . . .
H11 H 1.0699 0.7612 0.2143 0.022 Uiso 1 1 calc R U . . .
C12 C 0.8150(5) 0.6349(13) 0.2022(3) 0.0156(12) Uani 1 1 d . . . . .
C13 C 0.8163(6) 0.4631(12) 0.2819(3) 0.0169(9) Uani 1 1 d . . . . .
C14 C 0.6491(6) 0.3220(11) 0.3070(3) 0.0157(9) Uani 1 1 d . . . . .
Br1 Br 0.82016(5) 0.08301(18) 0.45896(2) 0.02177(13) Uani 1 1 d . . . . .
O1 O 0.3688(4) 0.5198(11) 0.12824(19) 0.0281(11) Uani 1 1 d . . . . .
O2 O 0.9519(4) 0.4410(10) 0.3241(2) 0.0276(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.387(7) . ?
C1 C14 1.393(6) . ?
C1 Br1 1.904(4) . ?
C2 C3 1.408(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.366(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(7) . ?
C4 H4 0.9500 . ?
C5 C14 1.411(6) . ?
C5 C6 1.492(6) . ?
C6 O1 1.218(5) . ?
C6 C7 1.482(6) . ?
C7 C12 1.399(6) . ?
C7 C8 1.403(6) . ?
C8 C9 1.385(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.495(6) . ?
C13 O2 1.223(5) . ?
C13 C14 1.505(6) . ?

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 C1 C14 121.4(4) . . ?
C2 C1 Br1 113.9(3) . . ?
C14 C1 Br1 124.6(3) . . ?
C1 C2 C3 120.6(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 118.4(4) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 121.6(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C14 120.4(4) . . ?
C4 C5 C6 117.1(4) . . ?
C14 C5 C6 122.5(4) . . ?
O1 C6 C7 121.6(4) . . ?
O1 C6 C5 120.6(4) . . ?
C7 C6 C5 117.8(4) . . ?
C12 C7 C8 119.4(4) . . ?
C12 C7 C6 120.8(4) . . ?
C8 C7 C6 119.8(4) . . ?
C9 C8 C7 120.5(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.8(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C7 119.5(4) . . ?
C11 C12 C13 118.9(4) . . ?
C7 C12 C13 121.6(4) . . ?
O2 C13 C12 119.5(4) . . ?
O2 C13 C14 122.3(4) . . ?
C12 C13 C14 118.3(4) . . ?
C1 C14 C5 117.6(4) . . ?
C1 C14 C13 123.5(4) . . ?
C5 C14 C13 118.9(4) . . ?

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 C3 0.1(9) . . . . ?
Br1 C1 C2 C3 -179.8(6) . . . . ?
C1 C2 C3 C4 1.9(11) . . . . ?
C2 C3 C4 C5 -2.4(10) . . . . ?
C3 C4 C5 C14 0.9(8) . . . . ?
C3 C4 C5 C6 -179.5(6) . . . . ?
C4 C5 C6 O1 -2.6(6) . . . . ?
C14 C5 C6 O1 177.0(5) . . . . ?
C4 C5 C6 C7 177.2(4) . . . . ?
C14 C5 C6 C7 -3.2(6) . . . . ?
O1 C6 C7 C12 -178.0(5) . . . . ?
C5 C6 C7 C12 2.2(6) . . . . ?
O1 C6 C7 C8 1.0(7) . . . . ?
C5 C6 C7 C8 -178.8(4) . . . . ?
C12 C7 C8 C9 -0.9(7) . . . . ?
C6 C7 C8 C9 -179.9(4) . . . . ?
C7 C8 C9 C10 0.0(7) . . . . ?
C8 C9 C10 C11 0.8(7) . . . . ?
C9 C10 C11 C12 -0.6(7) . . . . ?
C10 C11 C12 C7 -0.3(7) . . . . ?
C10 C11 C12 C13 179.4(4) . . . . ?
C8 C7 C12 C11 1.1(7) . . . . ?
C6 C7 C12 C11 -179.9(4) . . . . ?
C8 C7 C12 C13 -178.6(4) . . . . ?
C6 C7 C12 C13 0.3(7) . . . . ?
C11 C12 C13 O2 -1.9(7) . . . . ?
C7 C12 C13 O2 177.9(5) . . . . ?
C11 C12 C13 C14 178.3(4) . . . . ?
C7 C12 C13 C14 -2.0(7) . . . . ?
C2 C1 C14 C5 -1.6(7) . . . . ?
Br1 C1 C14 C5 178.3(3) . . . . ?
C2 C1 C14 C13 178.3(5) . . . . ?
Br1 C1 C14 C13 -1.8(6) . . . . ?
C4 C5 C14 C1 1.1(7) . . . . ?
C6 C5 C14 C1 -178.4(4) . . . . ?
C4 C5 C14 C13 -178.8(4) . . . . ?
C6 C5 C14 C13 1.6(7) . . . . ?
O2 C13 C14 C1 1.2(7) . . . . ?
C12 C13 C14 C1 -178.9(4) . . . . ?
O2 C13 C14 C5 -178.8(4) . . . . ?
C12 C13 C14 C5 1.0(6) . . . . ?

_refine_diff_density_max         0.770
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.087

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2_1-AnqSeBr
_database_code_depnum_ccdc_archive 'CCDC 2339577'
loop_
_audit_author_name
_audit_author_address
'Mao Minoura'
;Department of Chemistry, College of Science, Rikkyo University,
Japan
;
_audit_update_record             
;
2024-05-09 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H7 Br O2 Se'
_chemical_formula_weight         366.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.163(3)
_cell_length_b                   7.945(2)
_cell_length_c                   11.682(4)
_cell_angle_alpha                72.824(19)
_cell_angle_beta                 86.44(2)
_cell_angle_gamma                65.249(14)
_cell_volume                     575.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.113
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    6.723
_shelx_estimated_absorpt_T_min   0.553
_shelx_estimated_absorpt_T_max   0.553
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4207
_diffrn_reflns_av_unetI/netI     0.2505
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.428
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 0.919
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_Laue_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.919
_reflns_number_total             2428
_reflns_number_gt                1586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2428
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   0.534
_refine_ls_restrained_S_all      0.534
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.36411(4) 0.09140(4) 0.86325(2) 0.01666(13) Uani 1 1 d . . . . .
Se1 Se 0.31730(4) 0.15582(3) 0.65096(2) 0.01134(13) Uani 1 1 d . . . . .
O1 O 0.2716(3) 0.2303(3) 0.44738(16) 0.0113(4) Uani 1 1 d . . . . .
O2 O 0.1428(3) 0.9731(3) 0.25944(18) 0.0190(4) Uani 1 1 d . . . . .
C1 C 0.2726(4) 0.4211(4) 0.6029(2) 0.0112(5) Uani 1 1 d . . . . .
C2 C 0.2712(4) 0.5245(4) 0.6814(2) 0.0139(5) Uani 1 1 d . . . . .
H1 H 0.2873 0.4663 0.7640 0.017 Uiso 1 1 calc R U . . .
C3 C 0.2452(4) 0.7176(4) 0.6335(2) 0.0142(5) Uani 1 1 d . . . . .
H2 H 0.2464 0.7862 0.6854 0.017 Uiso 1 1 calc R U . . .
C4 C 0.2180(4) 0.8088(4) 0.5111(2) 0.0129(5) Uani 1 1 d . . . . .
H3 H 0.1998 0.9373 0.4814 0.015 Uiso 1 1 calc R U . . .
C5 C 0.2181(4) 0.7066(4) 0.4327(2) 0.0097(5) Uani 1 1 d . . . . .
C6 C 0.1825(4) 0.8032(4) 0.3009(2) 0.0124(5) Uani 1 1 d . . . . .
C7 C 0.2021(4) 0.6792(4) 0.2217(2) 0.0121(5) Uani 1 1 d . . . . .
C8 C 0.1920(4) 0.7585(4) 0.0982(2) 0.0182(6) Uani 1 1 d . . . . .
H4 H 0.1745 0.8865 0.0656 0.022 Uiso 1 1 calc R U . . .
C9 C 0.2082(4) 0.6458(4) 0.0221(3) 0.0221(6) Uani 1 1 d . . . . .
H5 H 0.2029 0.6988 -0.0607 0.027 Uiso 1 1 calc R U . . .
C10 C 0.2320(5) 0.4578(4) 0.0699(3) 0.0224(6) Uani 1 1 d . . . . .
H6 H 0.2426 0.3832 0.0196 0.027 Uiso 1 1 calc R U . . .
C11 C 0.2403(4) 0.3786(4) 0.1943(2) 0.0121(5) Uani 1 1 d . . . . .
H7 H 0.2550 0.2515 0.2267 0.014 Uiso 1 1 calc R U . . .
C12 C 0.2268(4) 0.4878(4) 0.2692(2) 0.0132(5) Uani 1 1 d . . . . .
C13 C 0.2474(4) 0.4008(4) 0.4003(2) 0.0120(5) Uani 1 1 d . . . . .
C14 C 0.2437(4) 0.5135(4) 0.4793(2) 0.0112(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Br1 Se1 2.3947(9) . ?
Se1 C1 1.902(2) . ?
Se1 O1 2.284(2) . ?
O1 C13 1.242(3) . ?
O2 C6 1.203(3) . ?
C1 C14 1.396(3) . ?
C1 C2 1.398(3) . ?
C2 C3 1.403(3) . ?
C2 H1 0.9300 . ?
C3 C4 1.382(4) . ?
C3 H2 0.9300 . ?
C4 C5 1.392(3) . ?
C4 H3 0.9300 . ?
C5 C14 1.403(4) . ?
C5 C6 1.487(4) . ?
C6 C7 1.501(3) . ?
C7 C8 1.386(3) . ?
C7 C12 1.393(3) . ?
C8 C9 1.406(4) . ?
C8 H4 0.9300 . ?
C9 C10 1.370(4) . ?
C9 H5 0.9300 . ?
C10 C11 1.397(4) . ?
C10 H6 0.9300 . ?
C11 C12 1.376(3) . ?
C11 H7 0.9300 . ?
C12 C13 1.471(4) . ?
C13 C14 1.456(3) . ?

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 O1 79.39(9) . . ?
C1 Se1 Br1 98.16(8) . . ?
O1 Se1 Br1 177.55(4) . . ?
C13 O1 Se1 109.09(16) . . ?
C14 C1 C2 119.3(2) . . ?
C14 C1 Se1 115.86(18) . . ?
C2 C1 Se1 124.82(19) . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 H1 120.5 . . ?
C3 C2 H1 120.5 . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H2 119.1 . . ?
C2 C3 H2 119.1 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H3 120.3 . . ?
C5 C4 H3 120.3 . . ?
C4 C5 C14 119.3(2) . . ?
C4 C5 C6 120.5(2) . . ?
C14 C5 C6 120.1(2) . . ?
O2 C6 C5 121.3(2) . . ?
O2 C6 C7 121.4(2) . . ?
C5 C6 C7 117.3(2) . . ?
C8 C7 C12 119.3(2) . . ?
C8 C7 C6 119.0(2) . . ?
C12 C7 C6 121.6(2) . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H4 119.9 . . ?
C9 C8 H4 119.9 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H5 120.0 . . ?
C8 C9 H5 120.0 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H6 120.1 . . ?
C11 C10 H6 120.1 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H7 119.8 . . ?
C10 C11 H7 119.8 . . ?
C11 C12 C7 120.4(2) . . ?
C11 C12 C13 120.3(2) . . ?
C7 C12 C13 119.3(2) . . ?
O1 C13 C14 117.8(2) . . ?
O1 C13 C12 122.0(2) . . ?
C14 C13 C12 120.2(2) . . ?
C1 C14 C5 121.2(2) . . ?
C1 C14 C13 117.8(2) . . ?
C5 C14 C13 121.1(2) . . ?

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 C3 -1.4(4) . . . . ?
Se1 C1 C2 C3 177.23(19) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C14 0.6(4) . . . . ?
C3 C4 C5 C6 178.08(19) . . . . ?
C4 C5 C6 O2 -3.8(4) . . . . ?
C14 C5 C6 O2 173.6(3) . . . . ?
C4 C5 C6 C7 175.1(2) . . . . ?
C14 C5 C6 C7 -7.4(3) . . . . ?
O2 C6 C7 C8 5.8(4) . . . . ?
C5 C6 C7 C8 -173.2(2) . . . . ?
O2 C6 C7 C12 -173.2(3) . . . . ?
C5 C6 C7 C12 7.8(3) . . . . ?
C12 C7 C8 C9 -0.5(4) . . . . ?
C6 C7 C8 C9 -179.5(2) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C7 0.8(4) . . . . ?
C10 C11 C12 C13 -176.5(2) . . . . ?
C8 C7 C12 C11 -0.3(4) . . . . ?
C6 C7 C12 C11 178.7(2) . . . . ?
C8 C7 C12 C13 177.1(2) . . . . ?
C6 C7 C12 C13 -3.9(4) . . . . ?
Se1 O1 C13 C14 -2.7(3) . . . . ?
Se1 O1 C13 C12 176.23(17) . . . . ?
C11 C12 C13 O1 -2.0(4) . . . . ?
C7 C12 C13 O1 -179.4(2) . . . . ?
C11 C12 C13 C14 176.8(2) . . . . ?
C7 C12 C13 C14 -0.5(3) . . . . ?
C2 C1 C14 C5 1.4(4) . . . . ?
Se1 C1 C14 C5 -177.28(19) . . . . ?
C2 C1 C14 C13 179.6(2) . . . . ?
Se1 C1 C14 C13 0.9(3) . . . . ?
C4 C5 C14 C1 -1.1(4) . . . . ?
C6 C5 C14 C1 -178.5(2) . . . . ?
C4 C5 C14 C13 -179.2(2) . . . . ?
C6 C5 C14 C13 3.4(4) . . . . ?
O1 C13 C14 C1 1.5(3) . . . . ?
C12 C13 C14 C1 -177.39(19) . . . . ?
O1 C13 C14 C5 179.7(2) . . . . ?
C12 C13 C14 C5 0.8(4) . . . . ?

_refine_diff_density_max         0.774
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.113

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6_1-AnqSeMe
_database_code_depnum_ccdc_archive 'CCDC 2339579'
loop_
_audit_author_name
_audit_author_address
'Mao Minoura'
;Department of Chemistry, College of Science, Rikkyo University,
Japan
;
_audit_update_record             
;
2024-05-09 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 O2 Se'
_chemical_formula_weight         301.19

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'
Se Se -0.0929 2.2259 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5235(4)
_cell_length_b                   5.1014(3)
_cell_length_c                   29.9257(19)
_cell_angle_alpha                90
_cell_angle_beta                 95.997(2)
_cell_angle_gamma                90
_cell_volume                     1142.27(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.275
_shelx_estimated_absorpt_T_min   0.735
_shelx_estimated_absorpt_T_max   0.735
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26869
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.722
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2624
_reflns_number_gt                2386
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+1.0470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2624
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.6581(3) 1.0201(4) 0.57250(7) 0.0154(4) Uani 1 1 d . . . . .
C2 C 0.5050(3) 1.1753(4) 0.56366(7) 0.0186(4) Uani 1 1 d . . . . .
H2 H 0.5031 1.3088 0.5415 0.022 Uiso 1 1 calc R U . . .
C3 C 0.3560(3) 1.1383(4) 0.58661(7) 0.0208(4) Uani 1 1 d . . . . .
H3 H 0.2534 1.2455 0.5799 0.025 Uiso 1 1 calc R U . . .
C4 C 0.3558(3) 0.9461(4) 0.61929(7) 0.0194(4) Uani 1 1 d . . . . .
H4 H 0.2528 0.9193 0.6346 0.023 Uiso 1 1 calc R U . . .
C5 C 0.5074(3) 0.7925(4) 0.62959(6) 0.0158(4) Uani 1 1 d . . . . .
C6 C 0.5036(3) 0.5930(4) 0.66605(7) 0.0178(4) Uani 1 1 d . . . . .
C7 C 0.6648(3) 0.4285(4) 0.67705(7) 0.0171(4) Uani 1 1 d . . . . .
C8 C 0.6661(3) 0.2398(4) 0.71086(7) 0.0207(4) Uani 1 1 d . . . . .
H8 H 0.5642 0.2185 0.7268 0.025 Uiso 1 1 calc R U . . .
C9 C 0.8154(3) 0.0833(4) 0.72130(7) 0.0228(5) Uani 1 1 d . . . . .
H9 H 0.8157 -0.0448 0.7444 0.027 Uiso 1 1 calc R U . . .
C10 C 0.9654(3) 0.1139(4) 0.69796(7) 0.0208(4) Uani 1 1 d . . . . .
H10 H 1.0669 0.0046 0.7049 0.025 Uiso 1 1 calc R U . . .
C11 C 0.9668(3) 0.3032(4) 0.66473(7) 0.0176(4) Uani 1 1 d . . . . .
H11 H 1.0698 0.3258 0.6493 0.021 Uiso 1 1 calc R U . . .
C12 C 0.8163(3) 0.4606(4) 0.65399(7) 0.0157(4) Uani 1 1 d . . . . .
C13 C 0.8197(3) 0.6606(4) 0.61775(6) 0.0151(4) Uani 1 1 d . . . . .
C14 C 0.6593(3) 0.8265(4) 0.60635(6) 0.0147(4) Uani 1 1 d . . . . .
Se1 Se 0.85975(3) 1.06932(4) 0.53955(2) 0.01648(8) Uani 1 1 d . . . . .
C15 C 0.7653(3) 1.3423(4) 0.49789(7) 0.0215(4) Uani 1 1 d . . . . .
H15 H 0.6517 1.2838 0.4820 0.032 Uiso 1 1 calc R U . . .
H15A H 0.8510 1.3773 0.4761 0.032 Uiso 1 1 calc R U . . .
H15B H 0.7456 1.5029 0.5147 0.032 Uiso 1 1 calc R U . . .
O1 O 0.3717(2) 0.5682(3) 0.68630(5) 0.0257(4) Uani 1 1 d . . . . .
O2 O 0.95295(18) 0.6872(3) 0.59784(5) 0.0199(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.400(3) . ?
C1 C14 1.414(3) . ?
C1 Se1 1.910(2) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C14 1.409(3) . ?
C5 C6 1.494(3) . ?
C6 O1 1.222(3) . ?
C6 C7 1.484(3) . ?
C7 C8 1.396(3) . ?
C7 C12 1.402(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.491(3) . ?
C13 O2 1.226(2) . ?
C13 C14 1.484(3) . ?
Se1 C15 1.953(2) . ?
C15 H15 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?

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 C1 C14 118.29(19) . . ?
C2 C1 Se1 120.68(16) . . ?
C14 C1 Se1 121.03(15) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 120.42(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C14 120.63(19) . . ?
C4 C5 C6 117.84(18) . . ?
C14 C5 C6 121.53(18) . . ?
O1 C6 C7 121.3(2) . . ?
O1 C6 C5 120.75(19) . . ?
C7 C6 C5 117.99(18) . . ?
C8 C7 C12 119.55(19) . . ?
C8 C7 C6 119.62(19) . . ?
C12 C7 C6 120.83(18) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.89(19) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 120.02(19) . . ?
C11 C12 C13 119.01(18) . . ?
C7 C12 C13 120.97(18) . . ?
O2 C13 C14 120.78(18) . . ?
O2 C13 C12 120.42(18) . . ?
C14 C13 C12 118.80(17) . . ?
C5 C14 C1 119.65(18) . . ?
C5 C14 C13 119.88(18) . . ?
C1 C14 C13 120.47(18) . . ?
C1 Se1 C15 99.64(9) . . ?
Se1 C15 H15 109.5 . . ?
Se1 C15 H15A 109.5 . . ?
H15 C15 H15A 109.5 . . ?
Se1 C15 H15B 109.5 . . ?
H15 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?

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 C3 -1.4(3) . . . . ?
Se1 C1 C2 C3 178.60(16) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C14 -1.5(3) . . . . ?
C3 C4 C5 C6 178.14(19) . . . . ?
C4 C5 C6 O1 -0.6(3) . . . . ?
C14 C5 C6 O1 179.02(19) . . . . ?
C4 C5 C6 C7 179.87(18) . . . . ?
C14 C5 C6 C7 -0.5(3) . . . . ?
O1 C6 C7 C8 0.6(3) . . . . ?
C5 C6 C7 C8 -179.90(18) . . . . ?
O1 C6 C7 C12 -179.2(2) . . . . ?
C5 C6 C7 C12 0.3(3) . . . . ?
C12 C7 C8 C9 -0.6(3) . . . . ?
C6 C7 C8 C9 179.55(19) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C12 -1.2(3) . . . . ?
C10 C11 C12 C7 0.5(3) . . . . ?
C10 C11 C12 C13 -179.23(19) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
C6 C7 C12 C11 -179.79(19) . . . . ?
C8 C7 C12 C13 -179.88(19) . . . . ?
C6 C7 C12 C13 0.0(3) . . . . ?
C11 C12 C13 O2 -0.3(3) . . . . ?
C7 C12 C13 O2 179.93(19) . . . . ?
C11 C12 C13 C14 179.74(18) . . . . ?
C7 C12 C13 C14 0.0(3) . . . . ?
C4 C5 C14 C1 0.5(3) . . . . ?
C6 C5 C14 C1 -179.14(18) . . . . ?
C4 C5 C14 C13 -179.92(18) . . . . ?
C6 C5 C14 C13 0.4(3) . . . . ?
C2 C1 C14 C5 0.9(3) . . . . ?
Se1 C1 C14 C5 -179.07(14) . . . . ?
C2 C1 C14 C13 -178.64(18) . . . . ?
Se1 C1 C14 C13 1.4(3) . . . . ?
O2 C13 C14 C5 179.88(19) . . . . ?
C12 C13 C14 C5 -0.2(3) . . . . ?
O2 C13 C14 C1 -0.6(3) . . . . ?
C12 C13 C14 C1 179.37(18) . . . . ?

_refine_diff_density_max         0.693
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.080

