# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1906750'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2019-03-30 deposited with the CCDC.	2019-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 O2 Se'
_chemical_formula_weight         327.23

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'

_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                   7.9308(6)
_cell_length_b                   7.9752(6)
_cell_length_c                   12.3077(12)
_cell_angle_alpha                89.175(7)
_cell_angle_beta                 73.899(8)
_cell_angle_gamma                68.845(7)
_cell_volume                     694.32(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1592
_cell_measurement_theta_min      2.7450
_cell_measurement_theta_max      24.7570

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.621
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    2.701
_shelx_estimated_absorpt_T_min   0.285
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69009
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            4785
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.751
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2837
_reflns_number_gt                2130
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    superflip
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0372P)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         2837
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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
Se01 Se 0.06248(5) 0.25495(5) 0.26480(3) 0.04164(16) Uani 1 1 d . . . . .
O2 O 0.4220(3) 0.2080(3) 0.1476(2) 0.0431(7) Uani 1 1 d . . . . .
O1 O 0.7633(4) -0.5043(4) 0.0560(2) 0.0550(8) Uani 1 1 d . . . . .
C6 C 0.1904(4) 0.0021(4) 0.2171(3) 0.0293(8) Uani 1 1 d . . . . .
C4 C 0.4974(5) 0.0433(5) 0.1342(3) 0.0334(8) Uani 1 1 d . . . . .
C5 C 0.3848(4) -0.0724(4) 0.1622(3) 0.0287(8) Uani 1 1 d . . . . .
C10 C 0.4751(5) -0.2587(5) 0.1322(3) 0.0319(8) Uani 1 1 d . . . . .
C11 C -0.1741(5) 0.2512(5) 0.3590(3) 0.0363(9) Uani 1 1 d . . . . .
C9 C 0.3729(5) -0.3702(5) 0.1529(3) 0.0393(9) Uani 1 1 d . . . . .
H9 H 0.433027 -0.493916 0.132646 0.047 Uiso 1 1 calc R U . . .
C1 C 0.6832(5) -0.3422(5) 0.0798(3) 0.0374(9) Uani 1 1 d . . . . .
C15 C -0.3642(5) 0.2186(6) 0.5403(3) 0.0505(11) Uani 1 1 d . . . . .
H15 H -0.374695 0.193665 0.615384 0.061 Uiso 1 1 calc R U . . .
C14 C -0.5195(5) 0.2578(5) 0.5020(3) 0.0418(10) Uani 1 1 d . . . . .
C12 C -0.3295(5) 0.2938(5) 0.3197(3) 0.0437(10) Uani 1 1 d . . . . .
H12 H -0.319457 0.320219 0.244862 0.052 Uiso 1 1 calc R U . . .
C3 C 0.7039(5) -0.0443(5) 0.0859(3) 0.0419(10) Uani 1 1 d . . . . .
H3 H 0.776540 0.027099 0.073586 0.050 Uiso 1 1 calc R U . . .
C8 C 0.1809(5) -0.2954(5) 0.2041(3) 0.0437(10) Uani 1 1 d . . . . .
H8 H 0.110929 -0.369232 0.216440 0.052 Uiso 1 1 calc R U . . .
C13 C -0.5004(5) 0.2977(5) 0.3903(3) 0.0486(10) Uani 1 1 d . . . . .
H13 H -0.604181 0.327437 0.362397 0.058 Uiso 1 1 calc R U . . .
C7 C 0.0908(5) -0.1135(5) 0.2372(3) 0.0371(9) Uani 1 1 d . . . . .
H7 H -0.038507 -0.066749 0.273464 0.045 Uiso 1 1 calc R U . . .
C2 C 0.7901(5) -0.2211(6) 0.0594(3) 0.0435(10) Uani 1 1 d . . . . .
H2 H 0.920578 -0.269969 0.027380 0.052 Uiso 1 1 calc R U . . .
C16 C -0.1934(5) 0.2148(5) 0.4714(3) 0.0464(10) Uani 1 1 d . . . . .
H16 H -0.090731 0.187752 0.500164 0.056 Uiso 1 1 calc R U . . .
C17 C -0.7050(6) 0.2601(6) 0.5789(4) 0.0673(14) Uani 1 1 d . . . . .
H17A H -0.796779 0.290110 0.537624 0.101 Uiso 1 1 calc R U . . .
H17B H -0.688131 0.143127 0.605543 0.101 Uiso 1 1 calc R U . . .
H17C H -0.748148 0.348601 0.642552 0.101 Uiso 1 1 calc R U . . .


_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
Se01 C6 1.915(3) . ?
Se01 C11 1.924(3) . ?
O2 C4 1.223(4) . ?
O1 C1 1.214(4) . ?
C6 C7 1.395(4) . ?
C6 C5 1.400(4) . ?
C4 C3 1.473(5) . ?
C4 C5 1.477(4) . ?
C5 C10 1.400(5) . ?
C10 C9 1.382(4) . ?
C10 C1 1.488(5) . ?
C11 C12 1.376(5) . ?
C11 C16 1.387(5) . ?
C9 C8 1.376(5) . ?
C9 H9 0.9300 . ?
C1 C2 1.476(5) . ?
C15 C14 1.370(5) . ?
C15 C16 1.374(5) . ?
C15 H15 0.9300 . ?
C14 C13 1.386(5) . ?
C14 C17 1.506(5) . ?
C12 C13 1.382(5) . ?
C12 H12 0.9300 . ?
C3 C2 1.325(5) . ?
C3 H3 0.9300 . ?
C8 C7 1.374(5) . ?
C8 H8 0.9300 . ?
C13 H13 0.9300 . ?
C7 H7 0.9300 . ?
C2 H2 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C6 Se01 C11 98.93(14) . . ?
C7 C6 C5 118.1(3) . . ?
C7 C6 Se01 120.3(2) . . ?
C5 C6 Se01 121.6(2) . . ?
O2 C4 C3 120.3(3) . . ?
O2 C4 C5 121.3(3) . . ?
C3 C4 C5 118.4(3) . . ?
C10 C5 C6 120.0(3) . . ?
C10 C5 C4 119.0(3) . . ?
C6 C5 C4 120.9(3) . . ?
C9 C10 C5 120.6(3) . . ?
C9 C10 C1 118.4(3) . . ?
C5 C10 C1 121.0(3) . . ?
C12 C11 C16 118.6(3) . . ?
C12 C11 Se01 121.6(3) . . ?
C16 C11 Se01 119.7(3) . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
O1 C1 C2 121.0(3) . . ?
O1 C1 C10 121.4(3) . . ?
C2 C1 C10 117.6(3) . . ?
C14 C15 C16 122.2(4) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C15 C14 C13 117.6(3) . . ?
C15 C14 C17 121.2(4) . . ?
C13 C14 C17 121.2(4) . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C2 C3 C4 122.5(3) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C12 C13 C14 121.0(4) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C15 C16 C11 119.9(4) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C7 C6 C5 C10 -2.0(5) . . . . ?
Se01 C6 C5 C10 177.6(2) . . . . ?
C7 C6 C5 C4 177.5(3) . . . . ?
Se01 C6 C5 C4 -2.8(4) . . . . ?
O2 C4 C5 C10 172.1(3) . . . . ?
C3 C4 C5 C10 -5.9(5) . . . . ?
O2 C4 C5 C6 -7.4(5) . . . . ?
C3 C4 C5 C6 174.5(3) . . . . ?
C6 C5 C10 C9 2.2(5) . . . . ?
C4 C5 C10 C9 -177.4(3) . . . . ?
C6 C5 C10 C1 -176.5(3) . . . . ?
C4 C5 C10 C1 4.0(5) . . . . ?
C5 C10 C9 C8 -0.3(5) . . . . ?
C1 C10 C9 C8 178.3(3) . . . . ?
C9 C10 C1 O1 -0.4(5) . . . . ?
C5 C10 C1 O1 178.2(3) . . . . ?
C9 C10 C1 C2 -179.4(3) . . . . ?
C5 C10 C1 C2 -0.7(5) . . . . ?
C16 C15 C14 C13 -1.2(6) . . . . ?
C16 C15 C14 C17 179.6(4) . . . . ?
C16 C11 C12 C13 -0.9(6) . . . . ?
Se01 C11 C12 C13 -177.3(3) . . . . ?
O2 C4 C3 C2 -173.2(4) . . . . ?
C5 C4 C3 C2 4.9(5) . . . . ?
C10 C9 C8 C7 -1.7(6) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C15 C14 C13 C12 1.4(6) . . . . ?
C17 C14 C13 C12 -179.4(3) . . . . ?
C9 C8 C7 C6 1.8(6) . . . . ?
C5 C6 C7 C8 0.1(5) . . . . ?
Se01 C6 C7 C8 -179.6(3) . . . . ?
C4 C3 C2 C1 -1.6(6) . . . . ?
O1 C1 C2 C3 -179.5(4) . . . . ?
C10 C1 C2 C3 -0.5(5) . . . . ?
C14 C15 C16 C11 -0.1(6) . . . . ?
C12 C11 C16 C15 1.1(6) . . . . ?
Se01 C11 C16 C15 177.6(3) . . . . ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.084

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1906751'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2019-03-30 deposited with the CCDC.	2019-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H9 F O2 Se'
_chemical_formula_weight         331.19

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'
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'
F F 0.0171 0.0103 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.1532(6)
_cell_length_b                   9.0889(7)
_cell_length_c                   12.7922(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.441(5)
_cell_angle_gamma                90
_cell_volume                     1296.34(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    1612
_cell_measurement_theta_min      2.4440
_cell_measurement_theta_max      25.2280

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.139
_exptl_absorpt_coefficient_mu    2.905
_shelx_estimated_absorpt_T_min   0.341
_shelx_estimated_absorpt_T_max   0.688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78428
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            6016
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.393
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2644
_reflns_number_gt                1813
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    superflip
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0821P)²+0.0993P] 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         2644
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.1695
_refine_ls_wR_factor_gt          0.1437
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
Se01 Se 0.75932(5) 0.37134(7) 0.32784(4) 0.0507(3) Uani 1 1 d . . . . .
F1 F 0.9091(3) 0.3961(5) -0.1206(2) 0.0790(13) Uani 1 1 d . . . . .
O1 O 0.9374(3) 0.8769(5) 0.6567(3) 0.0551(11) Uani 1 1 d . . . . .
O2 O 0.7073(4) 0.3938(5) 0.5329(3) 0.0613(12) Uani 1 1 d . . . . .
C10 C 0.9087(4) 0.7021(6) 0.5208(3) 0.0378(12) Uani 1 1 d . . . . .
C1 C 0.8922(4) 0.7611(7) 0.6286(4) 0.0425(12) Uani 1 1 d . . . . .
C9 C 0.9860(4) 0.7747(6) 0.4568(4) 0.0415(12) Uani 1 1 d . . . . .
H9 H 1.028776 0.857561 0.481019 0.050 Uiso 1 1 calc R U . . .
C11 C 0.8086(5) 0.3780(6) 0.1842(4) 0.0423(13) Uani 1 1 d . . . . .
C8 C 0.9998(4) 0.7231(6) 0.3556(4) 0.0433(13) Uani 1 1 d . . . . .
H8 H 1.054552 0.769602 0.311742 0.052 Uiso 1 1 calc R U . . .
C5 C 0.8432(4) 0.5791(6) 0.4859(4) 0.0368(11) Uani 1 1 d . . . . .
C16 C 0.7590(5) 0.4815(7) 0.1158(4) 0.0512(14) Uani 1 1 d . . . . .
H16 H 0.700544 0.546819 0.140003 0.061 Uiso 1 1 calc R U . . .
C6 C 0.8550(4) 0.5308(6) 0.3820(3) 0.0380(11) Uani 1 1 d . . . . .
C4 C 0.7632(4) 0.5033(7) 0.5586(4) 0.0432(13) Uani 1 1 d . . . . .
C14 C 0.8761(5) 0.3906(7) -0.0194(4) 0.0528(16) Uani 1 1 d . . . . .
C2 C 0.8145(5) 0.6796(7) 0.6993(4) 0.0507(14) Uani 1 1 d . . . . .
H2 H 0.807013 0.711447 0.768712 0.061 Uiso 1 1 calc R U . . .
C12 C 0.8936(4) 0.2799(7) 0.1483(4) 0.0492(14) Uani 1 1 d . . . . .
H12 H 0.928269 0.210242 0.194219 0.059 Uiso 1 1 calc R U . . .
C7 C 0.9348(4) 0.6055(6) 0.3187(4) 0.0407(12) Uani 1 1 d . . . . .
H7 H 0.944046 0.574503 0.249310 0.049 Uiso 1 1 calc R U . . .
C3 C 0.7545(5) 0.5611(8) 0.6662(4) 0.0499(15) Uani 1 1 d . . . . .
H3 H 0.704576 0.512291 0.713045 0.060 Uiso 1 1 calc R U . . .
C13 C 0.9273(4) 0.2845(8) 0.0447(4) 0.0561(16) Uani 1 1 d . . . . .
H13 H 0.983365 0.217336 0.018871 0.067 Uiso 1 1 calc R U . . .
C15 C 0.7935(5) 0.4904(8) 0.0140(4) 0.0549(15) Uani 1 1 d . . . . .
H15 H 0.761497 0.562578 -0.031371 0.066 Uiso 1 1 calc R U . . .


_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
Se01 C6 1.919(5) . ?
Se01 C11 1.932(5) . ?
F1 C14 1.355(6) . ?
O1 C1 1.217(6) . ?
O2 C4 1.216(6) . ?
C10 C9 1.373(7) . ?
C10 C5 1.402(7) . ?
C10 C1 1.496(7) . ?
C1 C2 1.468(7) . ?
C9 C8 1.390(7) . ?
C9 H9 0.9400 . ?
C11 C12 1.388(7) . ?
C11 C16 1.389(8) . ?
C8 C7 1.368(7) . ?
C8 H8 0.9400 . ?
C5 C6 1.410(6) . ?
C5 C4 1.474(7) . ?
C16 C15 1.370(7) . ?
C16 H16 0.9400 . ?
C6 C7 1.394(7) . ?
C4 C3 1.479(7) . ?
C14 C15 1.369(8) . ?
C14 C13 1.380(9) . ?
C2 C3 1.331(8) . ?
C2 H2 0.9400 . ?
C12 C13 1.388(7) . ?
C12 H12 0.9400 . ?
C7 H7 0.9400 . ?
C3 H3 0.9400 . ?
C13 H13 0.9400 . ?
C15 H15 0.9400 . ?

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
C6 Se01 C11 98.7(2) . . ?
C9 C10 C5 121.6(4) . . ?
C9 C10 C1 118.1(5) . . ?
C5 C10 C1 120.3(4) . . ?
O1 C1 C2 120.1(5) . . ?
O1 C1 C10 121.5(5) . . ?
C2 C1 C10 118.3(5) . . ?
C10 C9 C8 118.6(5) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C12 C11 C16 119.4(5) . . ?
C12 C11 Se01 120.5(4) . . ?
C16 C11 Se01 120.1(4) . . ?
C7 C8 C9 121.0(5) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C5 C6 119.2(4) . . ?
C10 C5 C4 119.4(4) . . ?
C6 C5 C4 121.4(5) . . ?
C15 C16 C11 121.5(5) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C7 C6 C5 118.2(5) . . ?
C7 C6 Se01 121.1(4) . . ?
C5 C6 Se01 120.7(4) . . ?
O2 C4 C5 121.8(5) . . ?
O2 C4 C3 119.8(5) . . ?
C5 C4 C3 118.4(5) . . ?
F1 C14 C15 118.4(6) . . ?
F1 C14 C13 118.3(5) . . ?
C15 C14 C13 123.3(5) . . ?
C3 C2 C1 120.8(5) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C13 C12 C11 120.0(5) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C8 C7 C6 121.4(4) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C2 C3 C4 122.6(5) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C14 C13 C12 118.1(5) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C14 C15 C16 117.7(6) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 H15 121.2 . . ?

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
C9 C10 C1 O1 6.2(7) . . . . ?
C5 C10 C1 O1 -171.5(5) . . . . ?
C9 C10 C1 C2 -176.9(5) . . . . ?
C5 C10 C1 C2 5.3(7) . . . . ?
C5 C10 C9 C8 -0.6(7) . . . . ?
C1 C10 C9 C8 -178.4(4) . . . . ?
C10 C9 C8 C7 2.2(8) . . . . ?
C9 C10 C5 C6 -1.4(7) . . . . ?
C1 C10 C5 C6 176.3(4) . . . . ?
C9 C10 C5 C4 178.7(4) . . . . ?
C1 C10 C5 C4 -3.6(7) . . . . ?
C12 C11 C16 C15 -1.0(8) . . . . ?
Se01 C11 C16 C15 179.0(4) . . . . ?
C10 C5 C6 C7 1.8(7) . . . . ?
C4 C5 C6 C7 -178.3(5) . . . . ?
C10 C5 C6 Se01 -175.8(4) . . . . ?
C4 C5 C6 Se01 4.1(6) . . . . ?
C10 C5 C4 O2 -177.8(5) . . . . ?
C6 C5 C4 O2 2.3(8) . . . . ?
C10 C5 C4 C3 0.4(7) . . . . ?
C6 C5 C4 C3 -179.4(5) . . . . ?
O1 C1 C2 C3 172.9(5) . . . . ?
C10 C1 C2 C3 -4.0(8) . . . . ?
C16 C11 C12 C13 -0.7(8) . . . . ?
Se01 C11 C12 C13 179.2(4) . . . . ?
C9 C8 C7 C6 -1.8(8) . . . . ?
C5 C6 C7 C8 -0.3(7) . . . . ?
Se01 C6 C7 C8 177.3(4) . . . . ?
C1 C2 C3 C4 0.9(9) . . . . ?
O2 C4 C3 C2 179.2(6) . . . . ?
C5 C4 C3 C2 0.9(8) . . . . ?
F1 C14 C13 C12 179.7(4) . . . . ?
C15 C14 C13 C12 -0.4(9) . . . . ?
C11 C12 C13 C14 1.4(8) . . . . ?
F1 C14 C15 C16 178.6(5) . . . . ?
C13 C14 C15 C16 -1.3(9) . . . . ?
C11 C16 C15 C14 2.0(8) . . . . ?

_refine_diff_density_max         1.210
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.125

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1921235'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2019-06-05 deposited with the CCDC.	2019-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H11 F O2 Se'
_chemical_formula_weight         381.25

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'
F F 0.0171 0.0103 '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                   7.9915(3)
_cell_length_b                   9.0274(4)
_cell_length_c                   11.5170(4)
_cell_angle_alpha                103.912(4)
_cell_angle_beta                 101.386(4)
_cell_angle_gamma                93.706(4)
_cell_volume                     785.11(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4815
_cell_measurement_theta_min      3.4620
_cell_measurement_theta_max      25.1210

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    2.411
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.461
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_reflns_number            11420
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.589
_diffrn_reflns_theta_max         26.367
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3209
_reflns_number_gt                2710
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0440P)²+0.1127P] 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         3209
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0837
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
Se1 Se 0.88749(3) 0.31429(3) 0.81990(2) 0.05597(12) Uani 1 1 d . . . . .
O1 O 0.9417(2) 0.5100(2) 0.68838(17) 0.0599(5) Uani 1 1 d . . . . .
O2 O 0.3390(2) 0.7329(3) 0.5977(2) 0.0821(7) Uani 1 1 d . . . . .
C4A C 0.5035(3) 0.5743(3) 0.6984(2) 0.0438(5) Uani 1 1 d . . . . .
C1 C 0.6807(3) 0.4107(3) 0.7955(2) 0.0437(5) Uani 1 1 d . . . . .
C9A C 0.6612(3) 0.5136(3) 0.72096(19) 0.0411(5) Uani 1 1 d . . . . .
C8A C 0.7760(3) 0.6663(3) 0.5880(2) 0.0442(5) Uani 1 1 d . . . . .
C9 C 0.8026(3) 0.5588(3) 0.6672(2) 0.0436(5) Uani 1 1 d . . . . .
C4 C 0.3709(3) 0.5353(3) 0.7499(2) 0.0543(6) Uani 1 1 d . . . . .
H4 H 0.266364 0.574181 0.733306 0.065 Uiso 1 1 calc R U . . .
C5 C 0.5963(4) 0.8222(3) 0.4867(2) 0.0581(7) Uani 1 1 d . . . . .
H5 H 0.490905 0.859133 0.468618 0.070 Uiso 1 1 calc R U . . .
C16 C 0.8244(3) 0.1828(3) 0.9170(2) 0.0509(6) Uani 1 1 d . . . . .
C10 C 0.4759(3) 0.6815(3) 0.6177(2) 0.0512(6) Uani 1 1 d . . . . .
C5A C 0.6178(3) 0.7234(3) 0.5630(2) 0.0457(5) Uani 1 1 d . . . . .
C13 C 0.7588(4) -0.0107(4) 1.0563(3) 0.0687(8) Uani 1 1 d . . . . .
C2 C 0.5459(3) 0.3760(3) 0.8482(2) 0.0547(6) Uani 1 1 d . . . . .
H2 H 0.558542 0.309608 0.898988 0.066 Uiso 1 1 calc R U . . .
C8 C 0.9092(3) 0.7098(3) 0.5368(2) 0.0546(6) Uani 1 1 d . . . . .
H8 H 1.014422 0.671889 0.552875 0.066 Uiso 1 1 calc R U . . .
C11 C 0.8775(4) 0.2269(3) 1.0422(3) 0.0641(7) Uani 1 1 d . . . . .
H11 H 0.937408 0.323736 1.080230 0.077 Uiso 1 1 calc R U . . .
C3 C 0.3939(3) 0.4385(3) 0.8260(3) 0.0600(7) Uani 1 1 d . . . . .
H3 H 0.305700 0.415004 0.862966 0.072 Uiso 1 1 calc R U . . .
C7 C 0.8852(4) 0.8087(3) 0.4625(3) 0.0658(7) Uani 1 1 d . . . . .
H7 H 0.974482 0.837405 0.428499 0.079 Uiso 1 1 calc R U . . .
C15 C 0.7353(5) 0.0380(4) 0.8626(3) 0.0789(9) Uani 1 1 d . . . . .
H15 H 0.698198 0.005922 0.777717 0.095 Uiso 1 1 calc R U . . .
C6 C 0.7293(4) 0.8659(3) 0.4379(3) 0.0679(8) Uani 1 1 d . . . . .
H6 H 0.714425 0.933774 0.388377 0.081 Uiso 1 1 calc R U . . .
C14 C 0.7012(5) -0.0589(4) 0.9333(4) 0.0899(11) Uani 1 1 d . . . . .
H14 H 0.639774 -0.155542 0.897017 0.108 Uiso 1 1 calc R U . . .
C12 C 0.8433(4) 0.1296(4) 1.1125(3) 0.0733(8) Uani 1 1 d . . . . .
H12 H 0.878201 0.160621 1.197535 0.088 Uiso 1 1 calc R U . . .
F1 F 0.7290(3) -0.1080(2) 1.1249(2) 0.1090(7) 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
Se1 C1 1.920(2) . ?
Se1 C16 1.922(3) . ?
O1 C9 1.224(3) . ?
O2 C10 1.218(3) . ?
C4A C4 1.378(3) . ?
C4A C9A 1.409(3) . ?
C4A C10 1.492(3) . ?
C1 C2 1.390(3) . ?
C1 C9A 1.405(3) . ?
C9A C9 1.471(3) . ?
C8A C8 1.392(3) . ?
C8A C5A 1.400(3) . ?
C8A C9 1.482(3) . ?
C4 C3 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(4) . ?
C5 C5A 1.390(4) . ?
C5 H5 0.9300 . ?
C16 C11 1.370(4) . ?
C16 C15 1.385(4) . ?
C10 C5A 1.473(3) . ?
C13 C12 1.342(4) . ?
C13 C14 1.353(5) . ?
C13 F1 1.353(3) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C8 C7 1.376(4) . ?
C8 H8 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C3 H3 0.9300 . ?
C7 C6 1.383(4) . ?
C7 H7 0.9300 . ?
C15 C14 1.379(5) . ?
C15 H15 0.9300 . ?
C6 H6 0.9300 . ?
C14 H14 0.9300 . ?
C12 H12 0.9300 . ?

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 C16 99.19(10) . . ?
C4 C4A C9A 120.7(2) . . ?
C4 C4A C10 118.5(2) . . ?
C9A C4A C10 120.8(2) . . ?
C2 C1 C9A 119.0(2) . . ?
C2 C1 Se1 120.48(18) . . ?
C9A C1 Se1 120.51(17) . . ?
C1 C9A C4A 119.0(2) . . ?
C1 C9A C9 121.0(2) . . ?
C4A C9A C9 120.0(2) . . ?
C8 C8A C5A 119.6(2) . . ?
C8 C8A C9 119.7(2) . . ?
C5A C8A C9 120.7(2) . . ?
O1 C9 C9A 120.8(2) . . ?
O1 C9 C8A 119.9(2) . . ?
C9A C9 C8A 119.31(19) . . ?
C3 C4 C4A 119.7(2) . . ?
C3 C4 H4 120.2 . . ?
C4A C4 H4 120.2 . . ?
C6 C5 C5A 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C5A C5 H5 119.6 . . ?
C11 C16 C15 118.4(3) . . ?
C11 C16 Se1 120.2(2) . . ?
C15 C16 Se1 121.2(2) . . ?
O2 C10 C5A 120.8(2) . . ?
O2 C10 C4A 120.7(2) . . ?
C5A C10 C4A 118.5(2) . . ?
C5 C5A C8A 119.2(2) . . ?
C5 C5A C10 120.1(2) . . ?
C8A C5A C10 120.7(2) . . ?
C12 C13 C14 122.5(3) . . ?
C12 C13 F1 119.1(3) . . ?
C14 C13 F1 118.4(3) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C7 C8 C8A 120.1(3) . . ?
C7 C8 H8 120.0 . . ?
C8A C8 H8 120.0 . . ?
C16 C11 C12 120.9(3) . . ?
C16 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C13 C14 C15 118.7(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C13 C12 C11 118.9(3) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?

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
C2 C1 C9A C4A -2.2(3) . . . . ?
Se1 C1 C9A C4A 175.79(16) . . . . ?
C2 C1 C9A C9 177.5(2) . . . . ?
Se1 C1 C9A C9 -4.5(3) . . . . ?
C4 C4A C9A C1 0.9(3) . . . . ?
C10 C4A C9A C1 -178.7(2) . . . . ?
C4 C4A C9A C9 -178.8(2) . . . . ?
C10 C4A C9A C9 1.6(3) . . . . ?
C1 C9A C9 O1 -1.5(3) . . . . ?
C4A C9A C9 O1 178.2(2) . . . . ?
C1 C9A C9 C8A 179.3(2) . . . . ?
C4A C9A C9 C8A -1.0(3) . . . . ?
C8 C8A C9 O1 0.8(3) . . . . ?
C5A C8A C9 O1 -179.9(2) . . . . ?
C8 C8A C9 C9A 180.0(2) . . . . ?
C5A C8A C9 C9A -0.7(3) . . . . ?
C9A C4A C4 C3 1.3(4) . . . . ?
C10 C4A C4 C3 -179.1(2) . . . . ?
C4 C4A C10 O2 -0.2(4) . . . . ?
C9A C4A C10 O2 179.4(2) . . . . ?
C4 C4A C10 C5A 179.9(2) . . . . ?
C9A C4A C10 C5A -0.5(3) . . . . ?
C6 C5 C5A C8A -1.1(4) . . . . ?
C6 C5 C5A C10 178.1(2) . . . . ?
C8 C8A C5A C5 0.3(3) . . . . ?
C9 C8A C5A C5 -179.0(2) . . . . ?
C8 C8A C5A C10 -178.9(2) . . . . ?
C9 C8A C5A C10 1.8(3) . . . . ?
O2 C10 C5A C5 -0.3(4) . . . . ?
C4A C10 C5A C5 179.6(2) . . . . ?
O2 C10 C5A C8A 178.8(2) . . . . ?
C4A C10 C5A C8A -1.2(3) . . . . ?
C9A C1 C2 C3 1.3(4) . . . . ?
Se1 C1 C2 C3 -176.6(2) . . . . ?
C5A C8A C8 C7 0.2(4) . . . . ?
C9 C8A C8 C7 179.6(2) . . . . ?
C15 C16 C11 C12 0.0(4) . . . . ?
Se1 C16 C11 C12 -175.6(2) . . . . ?
C4A C4 C3 C2 -2.2(4) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C8A C8 C7 C6 0.0(4) . . . . ?
C11 C16 C15 C14 0.0(5) . . . . ?
Se1 C16 C15 C14 175.6(3) . . . . ?
C5A C5 C6 C7 1.4(4) . . . . ?
C8 C7 C6 C5 -0.8(5) . . . . ?
C12 C13 C14 C15 2.1(6) . . . . ?
F1 C13 C14 C15 -178.2(3) . . . . ?
C16 C15 C14 C13 -1.1(6) . . . . ?
C14 C13 C12 C11 -2.0(5) . . . . ?
F1 C13 C12 C11 178.3(3) . . . . ?
C16 C11 C12 C13 0.9(5) . . . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1921237'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2019-06-05 deposited with the CCDC.	2019-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H11 I O2 Se'
_chemical_formula_weight         489.15

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'
I I -0.4742 1.8119 '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                   7.8103(3)
_cell_length_b                   7.9730(4)
_cell_length_c                   14.4279(6)
_cell_angle_alpha                95.901(4)
_cell_angle_beta                 95.642(4)
_cell_angle_gamma                104.780(4)
_cell_volume                     856.84(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5126
_cell_measurement_theta_min      3.2380
_cell_measurement_theta_max      28.0120

_exptl_crystal_description       Plate
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.732
_exptl_crystal_size_mid          0.368
_exptl_crystal_size_min          0.034
_exptl_absorpt_coefficient_mu    4.001
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.107
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_reflns_number            10146
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.666
_diffrn_reflns_theta_max         26.368
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3495
_reflns_number_gt                2756
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0509P)²+1.0832P] 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         3495
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
I1 I -0.01102(5) 0.37278(5) 0.37009(3) 0.06360(17) Uani 1 1 d . . . . .
Se02 Se 0.12031(8) -0.00196(7) 0.27153(4) 0.04984(18) Uani 1 1 d . . . . .
O1 O 0.1158(5) -0.1159(4) 0.0839(2) 0.0453(8) Uani 1 1 d . . . . .
O2 O 0.3026(7) 0.4743(5) -0.0645(3) 0.0760(13) Uani 1 1 d . . . . .
C5A C 0.3170(6) 0.1828(7) -0.0694(3) 0.0422(11) Uani 1 1 d . . . . .
C4A C 0.2123(7) 0.3405(6) 0.0669(4) 0.0430(11) Uani 1 1 d . . . . .
C10 C 0.2794(7) 0.3438(7) -0.0256(4) 0.0490(12) Uani 1 1 d . . . . .
C4 C 0.1808(8) 0.4933(7) 0.1102(4) 0.0556(14) Uani 1 1 d . . . . .
H4 H 0.199538 0.593080 0.080275 0.067 Uiso 1 1 calc R U . . .
C8A C 0.2707(6) 0.0293(6) -0.0287(3) 0.0369(10) Uani 1 1 d . . . . .
C8 C 0.2979(7) -0.1240(7) -0.0725(4) 0.0468(12) Uani 1 1 d . . . . .
H8 H 0.264664 -0.227980 -0.046747 0.056 Uiso 1 1 calc R U . . .
C9 C 0.1881(6) 0.0234(6) 0.0592(3) 0.0349(10) Uani 1 1 d . . . . .
C5 C 0.3920(7) 0.1827(8) -0.1529(4) 0.0557(14) Uani 1 1 d . . . . .
H5 H 0.421676 0.284690 -0.180629 0.067 Uiso 1 1 calc R U . . .
C7 C 0.3748(7) -0.1197(8) -0.1544(4) 0.0541(14) Uani 1 1 d . . . . .
H7 H 0.395084 -0.221289 -0.183342 0.065 Uiso 1 1 calc R U . . .
C3 C 0.1228(8) 0.4956(7) 0.1963(4) 0.0573(14) Uani 1 1 d . . . . .
H3 H 0.099770 0.596757 0.224084 0.069 Uiso 1 1 calc R U . . .
C11 C 0.2645(7) 0.1073(7) 0.3868(4) 0.0483(12) Uani 1 1 d . . . . .
C16 C 0.2167(9) 0.0346(9) 0.4670(4) 0.0624(15) Uani 1 1 d . . . . .
H16 H 0.113938 -0.056913 0.463647 0.075 Uiso 1 1 calc R U . . .
C12 C 0.4209(7) 0.2402(8) 0.3931(4) 0.0542(13) Uani 1 1 d . . . . .
H12 H 0.455977 0.287727 0.339492 0.065 Uiso 1 1 calc R U . . .
C9A C 0.1841(6) 0.1922(6) 0.1137(3) 0.0368(10) Uani 1 1 d . . . . .
C6 C 0.4219(8) 0.0326(9) -0.1940(4) 0.0600(15) Uani 1 1 d . . . . .
H6 H 0.474528 0.033286 -0.249094 0.072 Uiso 1 1 calc R U . . .
C1 C 0.1363(6) 0.1978(6) 0.2048(3) 0.0399(10) Uani 1 1 d . . . . .
C14 C 0.4738(11) 0.2321(11) 0.5585(5) 0.083(2) Uani 1 1 d . . . . .
H14 H 0.542315 0.275538 0.616537 0.100 Uiso 1 1 calc R U . . .
C13 C 0.5245(8) 0.3018(9) 0.4787(5) 0.0668(16) Uani 1 1 d . . . . .
H13 H 0.629299 0.391066 0.482678 0.080 Uiso 1 1 calc R U . . .
C2 C 0.0980(7) 0.3514(7) 0.2425(3) 0.0448(12) Uani 1 1 d . . . . .
C15 C 0.3223(11) 0.0991(12) 0.5512(5) 0.085(2) Uani 1 1 d . . . . .
H15 H 0.289379 0.050423 0.604840 0.103 Uiso 1 1 calc R U . . .


_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 C2 2.112(5) . ?
Se02 C11 1.904(6) . ?
Se02 C1 1.928(5) . ?
O1 C9 1.217(5) . ?
O2 C10 1.215(6) . ?
C5A C5 1.390(7) . ?
C5A C8A 1.392(7) . ?
C5A C10 1.481(7) . ?
C4A C9A 1.401(7) . ?
C4A C4 1.400(7) . ?
C4A C10 1.481(7) . ?
C4 C3 1.364(8) . ?
C4 H4 0.9300 . ?
C8A C8 1.392(7) . ?
C8A C9 1.479(6) . ?
C8 C7 1.376(8) . ?
C8 H8 0.9300 . ?
C9 C9A 1.496(6) . ?
C5 C6 1.365(8) . ?
C5 H5 0.9300 . ?
C7 C6 1.376(8) . ?
C7 H7 0.9300 . ?
C3 C2 1.369(8) . ?
C3 H3 0.9300 . ?
C11 C12 1.386(8) . ?
C11 C16 1.389(8) . ?
C16 C15 1.371(9) . ?
C16 H16 0.9300 . ?
C12 C13 1.378(8) . ?
C12 H12 0.9300 . ?
C9A C1 1.401(7) . ?
C6 H6 0.9300 . ?
C1 C2 1.402(7) . ?
C14 C15 1.360(11) . ?
C14 C13 1.379(10) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?

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
C11 Se02 C1 100.3(2) . . ?
C5 C5A C8A 119.8(5) . . ?
C5 C5A C10 120.3(5) . . ?
C8A C5A C10 119.9(4) . . ?
C9A C4A C4 118.9(5) . . ?
C9A C4A C10 122.5(4) . . ?
C4 C4A C10 118.5(5) . . ?
O2 C10 C5A 121.0(5) . . ?
O2 C10 C4A 121.0(5) . . ?
C5A C10 C4A 118.0(4) . . ?
C3 C4 C4A 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C4A C4 H4 120.0 . . ?
C8 C8A C5A 119.8(5) . . ?
C8 C8A C9 118.7(4) . . ?
C5A C8A C9 121.5(4) . . ?
C7 C8 C8A 119.1(5) . . ?
C7 C8 H8 120.4 . . ?
C8A C8 H8 120.4 . . ?
O1 C9 C8A 120.7(4) . . ?
O1 C9 C9A 120.6(4) . . ?
C8A C9 C9A 118.5(4) . . ?
C6 C5 C5A 119.9(5) . . ?
C6 C5 H5 120.1 . . ?
C5A C5 H5 120.1 . . ?
C6 C7 C8 121.0(5) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C12 C11 C16 119.2(5) . . ?
C12 C11 Se02 124.0(4) . . ?
C16 C11 Se02 116.4(4) . . ?
C15 C16 C11 119.4(7) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
C13 C12 C11 120.0(6) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C4A C9A C1 121.2(4) . . ?
C4A C9A C9 117.5(4) . . ?
C1 C9A C9 121.0(4) . . ?
C5 C6 C7 120.4(5) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C1 C9A 117.0(4) . . ?
C2 C1 Se02 122.9(4) . . ?
C9A C1 Se02 120.1(3) . . ?
C15 C14 C13 119.1(7) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C13 C12 120.5(7) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C3 C2 C1 121.5(5) . . ?
C3 C2 I1 115.6(4) . . ?
C1 C2 I1 122.8(4) . . ?
C14 C15 C16 121.8(7) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?

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
C5 C5A C10 O2 4.7(8) . . . . ?
C8A C5A C10 O2 -172.8(5) . . . . ?
C5 C5A C10 C4A -175.5(5) . . . . ?
C8A C5A C10 C4A 7.1(7) . . . . ?
C9A C4A C10 O2 -180.0(5) . . . . ?
C4 C4A C10 O2 -1.9(8) . . . . ?
C9A C4A C10 C5A 0.1(7) . . . . ?
C4 C4A C10 C5A 178.3(5) . . . . ?
C9A C4A C4 C3 -0.4(8) . . . . ?
C10 C4A C4 C3 -178.6(5) . . . . ?
C5 C5A C8A C8 -0.7(7) . . . . ?
C10 C5A C8A C8 176.8(4) . . . . ?
C5 C5A C8A C9 -179.0(4) . . . . ?
C10 C5A C8A C9 -1.6(7) . . . . ?
C5A C8A C8 C7 1.6(7) . . . . ?
C9 C8A C8 C7 -180.0(4) . . . . ?
C8 C8A C9 O1 -13.3(6) . . . . ?
C5A C8A C9 O1 165.0(4) . . . . ?
C8 C8A C9 C9A 170.9(4) . . . . ?
C5A C8A C9 C9A -10.8(6) . . . . ?
C8A C5A C5 C6 -0.8(8) . . . . ?
C10 C5A C5 C6 -178.3(5) . . . . ?
C8A C8 C7 C6 -1.1(8) . . . . ?
C4A C4 C3 C2 1.4(9) . . . . ?
C12 C11 C16 C15 1.9(9) . . . . ?
Se02 C11 C16 C15 175.4(5) . . . . ?
C16 C11 C12 C13 -1.7(8) . . . . ?
Se02 C11 C12 C13 -174.7(4) . . . . ?
C4 C4A C9A C1 -4.0(7) . . . . ?
C10 C4A C9A C1 174.1(5) . . . . ?
C4 C4A C9A C9 169.7(5) . . . . ?
C10 C4A C9A C9 -12.2(7) . . . . ?
O1 C9 C9A C4A -158.4(4) . . . . ?
C8A C9 C9A C4A 17.4(6) . . . . ?
O1 C9 C9A C1 15.3(6) . . . . ?
C8A C9 C9A C1 -168.9(4) . . . . ?
C5A C5 C6 C7 1.4(9) . . . . ?
C8 C7 C6 C5 -0.5(9) . . . . ?
C4A C9A C1 C2 7.2(7) . . . . ?
C9 C9A C1 C2 -166.3(4) . . . . ?
C4A C9A C1 Se02 -174.2(3) . . . . ?
C9 C9A C1 Se02 12.3(6) . . . . ?
C15 C14 C13 C12 1.4(11) . . . . ?
C11 C12 C13 C14 0.1(9) . . . . ?
C4 C3 C2 C1 2.0(9) . . . . ?
C4 C3 C2 I1 -175.5(5) . . . . ?
C9A C1 C2 C3 -6.2(7) . . . . ?
Se02 C1 C2 C3 175.2(4) . . . . ?
C9A C1 C2 I1 171.2(3) . . . . ?
Se02 C1 C2 I1 -7.4(6) . . . . ?
C13 C14 C15 C16 -1.3(12) . . . . ?
C11 C16 C15 C14 -0.4(11) . . . . ?

_refine_diff_density_max         0.834
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.120

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1921236'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2019-06-05 deposited with the CCDC.	2019-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H11 Cl O2 Se'
_chemical_formula_weight         397.70

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'
Cl Cl 0.1484 0.1585 '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                   8.0372(2)
_cell_length_b                   9.3175(3)
_cell_length_c                   11.5027(4)
_cell_angle_alpha                106.318(3)
_cell_angle_beta                 102.141(3)
_cell_angle_gamma                90.953(3)
_cell_volume                     805.57(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6881
_cell_measurement_theta_min      3.3050
_cell_measurement_theta_max      26.9530

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.148
_exptl_absorpt_coefficient_mu    2.505
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.390
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_reflns_number            16242
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.601
_diffrn_reflns_theta_max         26.369
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3286
_reflns_number_gt                2856
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0300P)²+0.2782P] 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         3286
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
Se1 Se 1.39643(3) -0.17407(3) 0.81333(2) 0.04733(10) Uani 1 1 d . . . . .
Cl1 Cl 1.22377(11) -0.61700(10) 1.11718(9) 0.0881(3) Uani 1 1 d . . . . .
O1 O 1.44662(19) 0.01642(19) 0.68785(16) 0.0514(4) Uani 1 1 d . . . . .
O2 O 0.8354(2) 0.2315(2) 0.5889(2) 0.0725(6) Uani 1 1 d . . . . .
C9A C 1.1655(2) 0.0219(2) 0.71612(19) 0.0342(4) Uani 1 1 d . . . . .
C4A C 1.0063(3) 0.0822(2) 0.6924(2) 0.0378(5) Uani 1 1 d . . . . .
C8A C 1.2770(3) 0.1703(2) 0.58911(19) 0.0364(5) Uani 1 1 d . . . . .
C9 C 1.3063(3) 0.0644(2) 0.66535(19) 0.0360(5) Uani 1 1 d . . . . .
C5A C 1.1175(3) 0.2262(2) 0.5626(2) 0.0383(5) Uani 1 1 d . . . . .
C10 C 0.9751(3) 0.1840(3) 0.6126(2) 0.0433(5) Uani 1 1 d . . . . .
C4 C 0.8747(3) 0.0464(3) 0.7428(2) 0.0484(6) Uani 1 1 d . . . . .
H4 H 0.769181 0.084671 0.725663 0.058 Uiso 1 1 calc R U . . .
C1 C 1.1878(3) -0.0778(2) 0.7893(2) 0.0369(5) Uani 1 1 d . . . . .
C5 C 1.0939(3) 0.3238(3) 0.4897(2) 0.0494(6) Uani 1 1 d . . . . .
H5 H 0.987346 0.359654 0.470413 0.059 Uiso 1 1 calc R U . . .
C8 C 1.4097(3) 0.2137(3) 0.5427(2) 0.0471(6) Uani 1 1 d . . . . .
H8 H 1.515632 0.175835 0.559082 0.057 Uiso 1 1 calc R U . . .
C11 C 1.3336(3) -0.3040(2) 0.9039(2) 0.0422(5) Uani 1 1 d . . . . .
C6 C 1.2272(4) 0.3678(3) 0.4459(2) 0.0579(7) Uani 1 1 d . . . . .
H6 H 1.211120 0.434590 0.398510 0.069 Uiso 1 1 calc R U . . .
C16 C 1.2496(4) -0.4424(3) 0.8425(3) 0.0663(8) Uani 1 1 d . . . . .
H16 H 1.216716 -0.472283 0.756198 0.080 Uiso 1 1 calc R U . . .
C12 C 1.3833(3) -0.2625(3) 1.0312(2) 0.0569(7) Uani 1 1 d . . . . .
H12 H 1.440969 -0.168918 1.073627 0.068 Uiso 1 1 calc R U . . .
C7 C 1.3849(3) 0.3125(3) 0.4725(2) 0.0570(6) Uani 1 1 d . . . . .
H7 H 1.474665 0.342181 0.442758 0.068 Uiso 1 1 calc R U . . .
C3 C 0.9011(3) -0.0459(3) 0.8181(2) 0.0526(6) Uani 1 1 d . . . . .
H3 H 0.813844 -0.066959 0.854041 0.063 Uiso 1 1 calc R U . . .
C13 C 1.3485(4) -0.3584(3) 1.0970(2) 0.0609(7) Uani 1 1 d . . . . .
H13 H 1.382133 -0.329690 1.183318 0.073 Uiso 1 1 calc R U . . .
C2 C 1.0546(3) -0.1079(3) 0.8414(2) 0.0475(6) Uani 1 1 d . . . . .
H2 H 1.069355 -0.170516 0.892406 0.057 Uiso 1 1 calc R U . . .
C14 C 1.2651(3) -0.4946(3) 1.0346(3) 0.0521(6) Uani 1 1 d . . . . .
C15 C 1.2133(4) -0.5382(3) 0.9087(3) 0.0734(9) Uani 1 1 d . . . . .
H15 H 1.154047 -0.631264 0.867180 0.088 Uiso 1 1 calc R U . . .


_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
Se1 C1 1.921(2) . ?
Se1 C11 1.928(2) . ?
Cl1 C14 1.744(2) . ?
O1 C9 1.223(2) . ?
O2 C10 1.218(3) . ?
C9A C1 1.409(3) . ?
C9A C4A 1.411(3) . ?
C9A C9 1.474(3) . ?
C4A C4 1.385(3) . ?
C4A C10 1.486(3) . ?
C8A C8 1.390(3) . ?
C8A C5A 1.398(3) . ?
C8A C9 1.485(3) . ?
C5A C5 1.391(3) . ?
C5A C10 1.478(3) . ?
C4 C3 1.371(3) . ?
C4 H4 0.9300 . ?
C1 C2 1.391(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C8 C7 1.376(3) . ?
C8 H8 0.9300 . ?
C11 C16 1.370(3) . ?
C11 C12 1.372(3) . ?
C6 C7 1.383(4) . ?
C6 H6 0.9300 . ?
C16 C15 1.388(4) . ?
C16 H16 0.9300 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C7 H7 0.9300 . ?
C3 C2 1.378(3) . ?
C3 H3 0.9300 . ?
C13 C14 1.354(4) . ?
C13 H13 0.9300 . ?
C2 H2 0.9300 . ?
C14 C15 1.359(4) . ?
C15 H15 0.9300 . ?

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 98.88(9) . . ?
C1 C9A C4A 119.15(18) . . ?
C1 C9A C9 120.88(18) . . ?
C4A C9A C9 119.96(19) . . ?
C4 C4A C9A 120.4(2) . . ?
C4 C4A C10 118.5(2) . . ?
C9A C4A C10 121.10(19) . . ?
C8 C8A C5A 119.5(2) . . ?
C8 C8A C9 119.56(19) . . ?
C5A C8A C9 120.92(19) . . ?
O1 C9 C9A 120.81(19) . . ?
O1 C9 C8A 120.23(19) . . ?
C9A C9 C8A 118.94(18) . . ?
C5 C5A C8A 119.5(2) . . ?
C5 C5A C10 119.9(2) . . ?
C8A C5A C10 120.67(19) . . ?
O2 C10 C5A 120.9(2) . . ?
O2 C10 C4A 120.8(2) . . ?
C5A C10 C4A 118.34(19) . . ?
C3 C4 C4A 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C4A C4 H4 120.2 . . ?
C2 C1 C9A 118.9(2) . . ?
C2 C1 Se1 120.65(17) . . ?
C9A C1 Se1 120.44(15) . . ?
C6 C5 C5A 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C5A C5 H5 119.8 . . ?
C7 C8 C8A 120.3(2) . . ?
C7 C8 H8 119.9 . . ?
C8A C8 H8 119.9 . . ?
C16 C11 C12 119.1(2) . . ?
C16 C11 Se1 120.78(19) . . ?
C12 C11 Se1 119.94(18) . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C11 C16 C15 120.2(3) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C13 C14 C15 121.3(2) . . ?
C13 C14 Cl1 119.5(2) . . ?
C15 C14 Cl1 119.3(2) . . ?
C14 C15 C16 119.4(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?

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
C1 C9A C4A C4 1.4(3) . . . . ?
C9 C9A C4A C4 -178.1(2) . . . . ?
C1 C9A C4A C10 -178.10(19) . . . . ?
C9 C9A C4A C10 2.4(3) . . . . ?
C1 C9A C9 O1 -1.5(3) . . . . ?
C4A C9A C9 O1 178.0(2) . . . . ?
C1 C9A C9 C8A -179.74(19) . . . . ?
C4A C9A C9 C8A -0.3(3) . . . . ?
C8 C8A C9 O1 0.5(3) . . . . ?
C5A C8A C9 O1 -180.0(2) . . . . ?
C8 C8A C9 C9A 178.7(2) . . . . ?
C5A C8A C9 C9A -1.7(3) . . . . ?
C8 C8A C5A C5 0.3(3) . . . . ?
C9 C8A C5A C5 -179.2(2) . . . . ?
C8 C8A C5A C10 -178.9(2) . . . . ?
C9 C8A C5A C10 1.5(3) . . . . ?
C5 C5A C10 O2 1.3(4) . . . . ?
C8A C5A C10 O2 -179.4(2) . . . . ?
C5 C5A C10 C4A -178.6(2) . . . . ?
C8A C5A C10 C4A 0.6(3) . . . . ?
C4 C4A C10 O2 -2.1(3) . . . . ?
C9A C4A C10 O2 177.4(2) . . . . ?
C4 C4A C10 C5A 177.9(2) . . . . ?
C9A C4A C10 C5A -2.6(3) . . . . ?
C9A C4A C4 C3 1.3(4) . . . . ?
C10 C4A C4 C3 -179.2(2) . . . . ?
C4A C9A C1 C2 -3.2(3) . . . . ?
C9 C9A C1 C2 176.3(2) . . . . ?
C4A C9A C1 Se1 175.27(15) . . . . ?
C9 C9A C1 Se1 -5.3(3) . . . . ?
C8A C5A C5 C6 -1.3(4) . . . . ?
C10 C5A C5 C6 177.9(2) . . . . ?
C5A C8A C8 C7 0.8(4) . . . . ?
C9 C8A C8 C7 -179.6(2) . . . . ?
C5A C5 C6 C7 1.2(4) . . . . ?
C12 C11 C16 C15 0.9(4) . . . . ?
Se1 C11 C16 C15 176.5(2) . . . . ?
C16 C11 C12 C13 -0.3(4) . . . . ?
Se1 C11 C12 C13 -175.9(2) . . . . ?
C8A C8 C7 C6 -1.0(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C4A C4 C3 C2 -2.2(4) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C4 C3 C2 C1 0.3(4) . . . . ?
C9A C1 C2 C3 2.4(4) . . . . ?
Se1 C1 C2 C3 -176.07(19) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C12 C13 C14 Cl1 179.1(2) . . . . ?
C13 C14 C15 C16 1.3(5) . . . . ?
Cl1 C14 C15 C16 -178.5(2) . . . . ?
C11 C16 C15 C14 -1.4(5) . . . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1906753'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2019-03-30 deposited with the CCDC.	2019-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 O2 Se'
_chemical_formula_weight         313.20

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'

_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                   8.3211(6)
_cell_length_b                   22.0040(12)
_cell_length_c                   6.9051(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.333(7)
_cell_angle_gamma                90
_cell_volume                     1250.96(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5261
_cell_measurement_theta_min      2.6180
_cell_measurement_theta_max      26.8430

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3664
_exptl_crystal_size_mid          0.1632
_exptl_crystal_size_min          0.0611
_exptl_absorpt_coefficient_mu    2.995
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.569
_exptl_absorpt_correction_T_max  0.880
_exptl_absorpt_process_details   
;
'Mon Apr 23 15:53:57 2018'
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            4577
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.474
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4577
_reflns_number_gt                2884
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    Superflip
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1783P)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         4577
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1391
_refine_ls_R_factor_gt           0.1064
_refine_ls_wR_factor_ref         0.2654
_refine_ls_wR_factor_gt          0.2508
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
Se1 Se 0.52525(13) 0.59474(4) 0.22624(16) 0.0378(4) Uani 1 1 d . . . . .
O1 O 0.7611(9) 0.8779(3) 0.2820(10) 0.0437(18) Uani 1 1 d . . . . .
O2 O 0.3354(8) 0.6948(3) 0.1928(11) 0.0413(17) Uani 1 1 d . . . . .
C7 C 0.9488(12) 0.7003(4) 0.3058(14) 0.036(2) Uani 1 1 d . . . . .
H7 H 1.059906 0.692709 0.325776 0.043 Uiso 1 1 calc R U . . .
C6 C 0.8394(12) 0.6529(4) 0.2826(14) 0.030(2) Uani 1 1 d . . . . .
H6 H 0.878776 0.613277 0.284736 0.037 Uiso 1 1 calc R U . . .
C4A C 0.6131(11) 0.7229(4) 0.2482(12) 0.025(2) Uani 1 1 d . . . . .
C4 C 0.4385(12) 0.7353(4) 0.2149(14) 0.034(2) Uani 1 1 d . . . . .
C2 C 0.4937(13) 0.8451(4) 0.2334(14) 0.043(3) Uani 1 1 d . . . . .
H2 H 0.454804 0.884775 0.232331 0.052 Uiso 1 1 calc R U . . .
C5 C 0.6726(12) 0.6620(4) 0.2564(12) 0.026(2) Uani 1 1 d . . . . .
C8A C 0.7278(12) 0.7711(4) 0.2701(13) 0.029(2) Uani 1 1 d . . . . .
C9 C 0.6809(12) 0.5294(4) 0.2674(14) 0.033(2) Uani 1 1 d . . . . .
C8 C 0.8900(11) 0.7602(4) 0.2987(13) 0.032(2) Uani 1 1 d . . . . .
H8 H 0.962662 0.792603 0.313712 0.039 Uiso 1 1 calc R U . . .
C1 C 0.6665(14) 0.8358(4) 0.2603(13) 0.034(2) Uani 1 1 d . . . . .
C3 C 0.3856(13) 0.7993(4) 0.2097(15) 0.039(2) Uani 1 1 d . . . . .
H3 H 0.275113 0.808173 0.189576 0.047 Uiso 1 1 calc R U . . .
C10 C 0.7170(12) 0.5027(4) 0.4505(15) 0.035(2) Uani 1 1 d . . . . .
H10 H 0.669813 0.517996 0.554503 0.042 Uiso 1 1 calc R U . . .
C12 C 0.8920(12) 0.4312(4) 0.3288(17) 0.041(3) Uani 1 1 d . . . . .
H12 H 0.963070 0.398381 0.348659 0.050 Uiso 1 1 calc R U . . .
C11 C 0.8214(13) 0.4538(4) 0.4814(16) 0.040(2) Uani 1 1 d . . . . .
H11 H 0.843781 0.436298 0.604989 0.048 Uiso 1 1 calc R U . . .
C14 C 0.7509(14) 0.5057(5) 0.1117(17) 0.045(3) Uani 1 1 d . . . . .
H14 H 0.726300 0.522250 -0.012950 0.054 Uiso 1 1 calc R U . . .
C13 C 0.8570(14) 0.4574(5) 0.1448(17) 0.046(3) Uani 1 1 d . . . . .
H13 H 0.905928 0.442185 0.042034 0.055 Uiso 1 1 calc R U . . .


_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
Se1 C5 1.914(9) . ?
Se1 C9 1.928(9) . ?
O1 C1 1.212(12) . ?
O2 C4 1.231(11) . ?
C7 C6 1.379(13) . ?
C7 C8 1.405(13) . ?
C6 C5 1.388(14) . ?
C4A C8A 1.421(12) . ?
C4A C5 1.427(12) . ?
C4A C4 1.463(13) . ?
C4 C3 1.474(13) . ?
C2 C3 1.346(14) . ?
C2 C1 1.437(15) . ?
C8A C8 1.357(13) . ?
C8A C1 1.509(12) . ?
C9 C10 1.388(14) . ?
C9 C14 1.396(15) . ?
C10 C11 1.379(14) . ?
C12 C11 1.373(15) . ?
C12 C13 1.388(16) . ?
C14 C13 1.379(15) . ?

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
C5 Se1 C9 98.9(4) . . ?
C6 C7 C8 119.1(9) . . ?
C7 C6 C5 122.4(8) . . ?
C8A C4A C5 118.3(8) . . ?
C8A C4A C4 120.9(8) . . ?
C5 C4A C4 120.9(8) . . ?
O2 C4 C4A 122.8(9) . . ?
O2 C4 C3 119.2(9) . . ?
C4A C4 C3 118.0(8) . . ?
C3 C2 C1 123.2(9) . . ?
C6 C5 C4A 118.4(8) . . ?
C6 C5 Se1 121.0(6) . . ?
C4A C5 Se1 120.6(7) . . ?
C8 C8A C4A 121.5(8) . . ?
C8 C8A C1 119.7(9) . . ?
C4A C8A C1 118.8(9) . . ?
C10 C9 C14 118.9(10) . . ?
C10 C9 Se1 120.2(8) . . ?
C14 C9 Se1 120.8(8) . . ?
C8A C8 C7 120.3(9) . . ?
O1 C1 C2 121.8(8) . . ?
O1 C1 C8A 120.4(10) . . ?
C2 C1 C8A 117.8(9) . . ?
C2 C3 C4 121.4(9) . . ?
C11 C10 C9 121.3(10) . . ?
C11 C12 C13 119.7(10) . . ?
C12 C11 C10 119.6(10) . . ?
C13 C14 C9 119.3(10) . . ?
C14 C13 C12 121.1(10) . . ?

_refine_diff_density_max         3.279
_refine_diff_density_min         -1.205
_refine_diff_density_rms         0.185

####################################################################### 
# 
# 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_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1906752'
loop_
_audit_author_name
_audit_author_address
'Willian Oliveira'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2019-03-30 deposited with the CCDC.	2019-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H9 Cl O2 Se'
_chemical_formula_weight         347.64

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   7.7944(8)
_cell_length_b                   7.9496(7)
_cell_length_c                   12.1938(11)
_cell_angle_alpha                91.575(7)
_cell_angle_beta                 105.071(8)
_cell_angle_gamma                110.273(9)
_cell_volume                     678.58(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    1808
_cell_measurement_theta_min      2.7350
_cell_measurement_theta_max      27.0830

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.609
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.133
_exptl_absorpt_coefficient_mu    2.960
_shelx_estimated_absorpt_T_min   0.266
_shelx_estimated_absorpt_T_max   0.694
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.264
_exptl_absorpt_correction_T_max  0.739
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            4652
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.755
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2779
_reflns_number_gt                2154
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    superflip
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0206P)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         2779
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0749
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
Se1 Se 1.05807(5) 0.23416(5) 0.73404(3) 0.03226(13) Uani 1 1 d . . . . .
Cl1 Cl 0.27390(14) 0.24339(16) 0.40245(10) 0.0648(4) Uani 1 1 d . . . . .
O2 O 1.4210(3) 0.2830(3) 0.8505(2) 0.0349(6) Uani 1 1 d . . . . .
O1 O 1.7656(3) 0.9979(4) 0.9394(2) 0.0460(7) Uani 1 1 d . . . . .
C4 C 1.4973(4) 0.4472(5) 0.8646(3) 0.0251(8) Uani 1 1 d . . . . .
C6 C 1.1849(4) 0.4878(4) 0.7826(3) 0.0242(8) Uani 1 1 d . . . . .
C5 C 1.3837(4) 0.5627(4) 0.8368(3) 0.0215(7) Uani 1 1 d . . . . .
C16 C 0.8134(5) 0.2832(5) 0.5266(3) 0.0360(9) Uani 1 1 d . . . . .
H16 H 0.921982 0.310613 0.500351 0.043 Uiso 1 1 calc R U . . .
C10 C 1.4736(4) 0.7512(5) 0.8667(3) 0.0247(8) Uani 1 1 d . . . . .
C9 C 1.3706(4) 0.8636(5) 0.8484(3) 0.0308(8) Uani 1 1 d . . . . .
H9 H 1.431829 0.989181 0.869825 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4915(5) 0.1953(5) 0.6015(3) 0.0379(9) Uani 1 1 d . . . . .
H13 H 0.381166 0.163964 0.626253 0.046 Uiso 1 1 calc R U . . .
C12 C 0.6611(4) 0.1955(5) 0.6735(3) 0.0325(9) Uani 1 1 d . . . . .
H12 H 0.666407 0.165076 0.747974 0.039 Uiso 1 1 calc R U . . .
C8 C 1.1757(5) 0.7875(5) 0.7980(3) 0.0338(9) Uani 1 1 d . . . . .
H8 H 1.103970 0.862577 0.786265 0.041 Uiso 1 1 calc R U . . .
C11 C 0.8223(4) 0.2401(5) 0.6369(3) 0.0291(8) Uani 1 1 d . . . . .
C3 C 1.7060(4) 0.5353(5) 0.9135(3) 0.0327(9) Uani 1 1 d . . . . .
H3 H 1.780434 0.462728 0.926556 0.039 Uiso 1 1 calc R U . . .
C7 C 1.0847(4) 0.6049(5) 0.7647(3) 0.0284(8) Uani 1 1 d . . . . .
H7 H 0.952370 0.557553 0.729038 0.034 Uiso 1 1 calc R U . . .
C2 C 1.7922(4) 0.7125(5) 0.9396(3) 0.0344(9) Uani 1 1 d . . . . .
H2 H 1.925130 0.761850 0.972922 0.041 Uiso 1 1 calc R U . . .
C15 C 0.6448(5) 0.2860(5) 0.4555(3) 0.0418(10) Uani 1 1 d . . . . .
H15 H 0.638809 0.318297 0.381366 0.050 Uiso 1 1 calc R U . . .
C14 C 0.4868(5) 0.2411(5) 0.4940(3) 0.0362(9) Uani 1 1 d . . . . .
C1 C 1.6853(5) 0.8348(5) 0.9179(3) 0.0300(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
Se1 C6 1.908(3) . ?
Se1 C11 1.927(3) . ?
Cl1 C14 1.749(3) . ?
O2 C4 1.218(4) . ?
O1 C1 1.214(4) . ?
C4 C5 1.472(4) . ?
C4 C3 1.475(4) . ?
C6 C7 1.397(4) . ?
C6 C5 1.413(4) . ?
C5 C10 1.407(4) . ?
C16 C15 1.381(4) . ?
C16 C11 1.387(4) . ?
C16 H16 0.9400 . ?
C10 C9 1.380(4) . ?
C10 C1 1.495(4) . ?
C9 C8 1.381(4) . ?
C9 H9 0.9400 . ?
C13 C14 1.366(5) . ?
C13 C12 1.383(4) . ?
C13 H13 0.9400 . ?
C12 C11 1.377(4) . ?
C12 H12 0.9400 . ?
C8 C7 1.371(5) . ?
C8 H8 0.9400 . ?
C3 C2 1.321(5) . ?
C3 H3 0.9400 . ?
C7 H7 0.9400 . ?
C2 C1 1.473(5) . ?
C2 H2 0.9400 . ?
C15 C14 1.368(5) . ?
C15 H15 0.9400 . ?

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
C6 Se1 C11 97.88(13) . . ?
O2 C4 C5 121.0(3) . . ?
O2 C4 C3 120.6(3) . . ?
C5 C4 C3 118.3(3) . . ?
C7 C6 C5 118.1(3) . . ?
C7 C6 Se1 121.1(2) . . ?
C5 C6 Se1 120.8(2) . . ?
C10 C5 C6 119.2(3) . . ?
C10 C5 C4 119.5(3) . . ?
C6 C5 C4 121.3(3) . . ?
C15 C16 C11 119.9(3) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C9 C10 C5 121.4(3) . . ?
C9 C10 C1 118.4(3) . . ?
C5 C10 C1 120.2(3) . . ?
C10 C9 C8 118.6(3) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C14 C13 C12 119.0(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C7 C8 C9 121.4(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C12 C11 C16 119.6(3) . . ?
C12 C11 Se1 121.1(2) . . ?
C16 C11 Se1 119.2(2) . . ?
C2 C3 C4 122.4(3) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C14 C15 C16 119.3(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C13 C14 C15 121.7(3) . . ?
C13 C14 Cl1 119.5(3) . . ?
C15 C14 Cl1 118.8(3) . . ?
O1 C1 C2 121.5(3) . . ?
O1 C1 C10 120.8(3) . . ?
C2 C1 C10 117.6(3) . . ?

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
C7 C6 C5 C10 -2.2(4) . . . . ?
Se1 C6 C5 C10 177.1(2) . . . . ?
C7 C6 C5 C4 176.5(3) . . . . ?
Se1 C6 C5 C4 -4.1(4) . . . . ?
O2 C4 C5 C10 172.5(3) . . . . ?
C3 C4 C5 C10 -5.7(4) . . . . ?
O2 C4 C5 C6 -6.2(5) . . . . ?
C3 C4 C5 C6 175.6(3) . . . . ?
C6 C5 C10 C9 2.6(5) . . . . ?
C4 C5 C10 C9 -176.1(3) . . . . ?
C6 C5 C10 C1 -176.4(3) . . . . ?
C4 C5 C10 C1 4.9(4) . . . . ?
C5 C10 C9 C8 -1.0(5) . . . . ?
C1 C10 C9 C8 178.0(3) . . . . ?
C14 C13 C12 C11 -0.5(6) . . . . ?
C10 C9 C8 C7 -1.0(5) . . . . ?
C13 C12 C11 C16 -0.6(6) . . . . ?
C13 C12 C11 Se1 -178.1(3) . . . . ?
C15 C16 C11 C12 1.7(6) . . . . ?
C15 C16 C11 Se1 179.2(3) . . . . ?
O2 C4 C3 C2 -173.8(3) . . . . ?
C5 C4 C3 C2 4.3(5) . . . . ?
C9 C8 C7 C6 1.4(5) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
Se1 C6 C7 C8 -179.1(3) . . . . ?
C4 C3 C2 C1 -2.1(5) . . . . ?
C11 C16 C15 C14 -1.7(6) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C12 C13 C14 Cl1 -179.4(3) . . . . ?
C16 C15 C14 C13 0.6(6) . . . . ?
C16 C15 C14 Cl1 -179.5(3) . . . . ?
C3 C2 C1 O1 -178.2(3) . . . . ?
C3 C2 C1 C10 1.1(5) . . . . ?
C9 C10 C1 O1 -2.3(5) . . . . ?
C5 C10 C1 O1 176.7(3) . . . . ?
C9 C10 C1 C2 178.4(3) . . . . ?
C5 C10 C1 C2 -2.5(5) . . . . ?

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.093

