# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_SRS_2349_0m_b
_database_code_depnum_ccdc_archive 'CCDC 1963733'
loop_
_audit_author_name
_audit_author_address
'Hans Reuter'
;Institut of Chemistry of New Materials, University of Osnabrueck
Germany
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 O3 Se'
_chemical_formula_weight         421.33

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   12.2311(4)
_cell_length_b                   5.5378(2)
_cell_length_c                   13.6984(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.773(2)
_cell_angle_gamma                90
_cell_volume                     923.13(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    966
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.17

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.064
_exptl_absorpt_coefficient_mu    2.055
_shelx_estimated_absorpt_T_min   0.435
_shelx_estimated_absorpt_T_max   0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.581
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            87218
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.989
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4465
_reflns_number_gt                4229
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0252P)²+0.2542P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1824 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.008(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4465
_refine_ls_number_parameters     249
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0498
_refine_ls_wR_factor_gt          0.0487
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.31195(2) 1.03816(5) 0.80642(2) 0.02422(7) Uani 1 1 d . . . . .
C1 C 0.25286(19) 0.7977(4) 0.71640(17) 0.0182(5) Uani 1 1 d . . . . .
C2 C 0.1735(2) 0.6561(4) 0.74570(17) 0.0184(5) Uani 1 1 d . . . . .
C3 C 0.1248(2) 0.6582(5) 0.84036(17) 0.0196(5) Uani 1 1 d . . . . .
O1 O 0.14800(15) 0.8007(4) 0.90764(12) 0.0257(4) Uani 1 1 d . . . . .
C4 C 0.0460(2) 0.4598(4) 0.83241(17) 0.0198(5) Uani 1 1 d . . . . .
C5 C -0.0254(2) 0.3668(5) 0.89619(18) 0.0241(5) Uani 1 1 d . . . . .
H5 H -0.0281 0.4320 0.9601 0.026(5) Uiso 1 1 calc R U . . .
C6 C -0.0919(2) 0.1766(5) 0.86298(19) 0.0266(6) Uani 1 1 d . . . . .
H6 H -0.1417 0.1105 0.9048 0.026(5) Uiso 1 1 calc R U . . .
C7 C -0.0878(2) 0.0785(5) 0.76876(18) 0.0249(6) Uani 1 1 d . . . . .
H7 H -0.1344 -0.0532 0.7483 0.026(5) Uiso 1 1 calc R U . . .
C8 C -0.0166(2) 0.1710(5) 0.70505(18) 0.0214(5) Uani 1 1 d . . . . .
O3 O -0.00413(15) 0.0915(3) 0.61269(12) 0.0279(5) Uani 1 1 d . . . . .
C9 C 0.04940(19) 0.3639(5) 0.73933(17) 0.0195(5) Uani 1 1 d . . . . .
O2 O 0.12275(13) 0.4780(3) 0.68434(11) 0.0198(4) Uani 1 1 d . . . . .
C10 C -0.0737(2) -0.1007(5) 0.5752(2) 0.0297(6) Uani 1 1 d . . . . .
H10A H -0.0601 -0.2435 0.6169 0.046(6) Uiso 1 1 calc R U . . .
H10B H -0.0579 -0.1391 0.5082 0.046(6) Uiso 1 1 calc R U . . .
H10C H -0.1507 -0.0515 0.5748 0.046(6) Uiso 1 1 calc R U . . .
C11 C 0.4564(2) 1.0952(4) 0.75766(18) 0.0236(6) Uani 1 1 d . . . . .
H11A H 0.4526 1.0489 0.6876 0.037(3) Uiso 1 1 calc R U . . .
H11B H 0.4742 1.2694 0.7627 0.037(3) Uiso 1 1 calc R U . . .
C12 C 0.5452(2) 0.9541(4) 0.81449(18) 0.0224(5) Uani 1 1 d . . . . .
C13 C 0.58139(19) 1.0208(7) 0.91081(17) 0.0275(5) Uani 1 1 d . . . . .
H13 H 0.5506 1.1586 0.9390 0.037(3) Uiso 1 1 calc R U . . .
C14 C 0.6616(2) 0.8878(6) 0.9656(2) 0.0328(6) Uani 1 1 d . . . . .
H14 H 0.6854 0.9346 1.0310 0.037(3) Uiso 1 1 calc R U . . .
C15 C 0.7072(2) 0.6867(6) 0.9252(2) 0.0363(7) Uani 1 1 d . . . . .
H15 H 0.7614 0.5941 0.9631 0.037(3) Uiso 1 1 calc R U . . .
C16 C 0.6735(3) 0.6212(5) 0.8291(2) 0.0351(7) Uani 1 1 d . . . . .
H16 H 0.7055 0.4852 0.8007 0.037(3) Uiso 1 1 calc R U . . .
C17 C 0.5931(2) 0.7543(5) 0.7745(2) 0.0291(6) Uani 1 1 d . . . . .
H17 H 0.5703 0.7083 0.7087 0.037(3) Uiso 1 1 calc R U . . .
C21 C 0.28847(19) 0.7824(5) 0.61584(17) 0.0176(5) Uani 1 1 d . . . . .
C22 C 0.2583(2) 0.9629(5) 0.54810(19) 0.0264(6) Uani 1 1 d . . . . .
H22 H 0.2173 1.0981 0.5667 0.037(4) Uiso 1 1 calc R U . . .
C23 C 0.2882(2) 0.9459(5) 0.4530(2) 0.0310(6) Uani 1 1 d . . . . .
H23 H 0.2665 1.0689 0.4067 0.037(4) Uiso 1 1 calc R U . . .
C24 C 0.3488(2) 0.7521(5) 0.42526(19) 0.0254(6) Uani 1 1 d . . . . .
H24 H 0.3685 0.7409 0.3601 0.037(4) Uiso 1 1 calc R U . . .
C25 C 0.3807(2) 0.5749(5) 0.49294(18) 0.0266(6) Uani 1 1 d . . . . .
H25 H 0.4241 0.4431 0.4748 0.037(4) Uiso 1 1 calc R U . . .
C26 C 0.3494(2) 0.5885(4) 0.58780(18) 0.0245(6) Uani 1 1 d . . . . .
H26 H 0.3701 0.4637 0.6336 0.037(4) 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 1.907(2) . ?
Se1 C11 1.976(2) . ?
C1 C2 1.340(3) . ?
C1 C21 1.488(3) . ?
C2 O2 1.400(3) . ?
C2 C3 1.481(3) . ?
C3 O1 1.225(3) . ?
C3 C4 1.458(3) . ?
C4 C9 1.386(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.380(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.406(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(4) . ?
C7 H7 0.9500 . ?
C8 O3 1.363(3) . ?
C8 C9 1.392(3) . ?
O3 C10 1.425(3) . ?
C9 O2 1.381(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.492(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.390(4) . ?
C12 C13 1.398(3) . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C21 C26 1.383(3) . ?
C21 C22 1.388(3) . ?
C22 C23 1.391(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.393(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se1 C11 100.76(10) . . ?
C2 C1 C21 122.1(2) . . ?
C2 C1 Se1 116.98(18) . . ?
C21 C1 Se1 120.74(18) . . ?
C1 C2 O2 121.6(2) . . ?
C1 C2 C3 128.7(2) . . ?
O2 C2 C3 109.7(2) . . ?
O1 C3 C4 130.0(2) . . ?
O1 C3 C2 125.5(2) . . ?
C4 C3 C2 104.5(2) . . ?
C9 C4 C5 120.9(2) . . ?
C9 C4 C3 106.1(2) . . ?
C5 C4 C3 133.0(2) . . ?
C6 C5 C4 117.4(2) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C5 C6 C7 121.6(2) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
O3 C8 C7 126.8(2) . . ?
O3 C8 C9 116.5(2) . . ?
C7 C8 C9 116.7(2) . . ?
C8 O3 C10 117.2(2) . . ?
O2 C9 C4 114.0(2) . . ?
O2 C9 C8 123.6(2) . . ?
C4 C9 C8 122.3(2) . . ?
C9 O2 C2 105.56(17) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 Se1 111.65(16) . . ?
C12 C11 H11A 109.3 . . ?
Se1 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
Se1 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C17 C12 C13 118.5(3) . . ?
C17 C12 C11 121.6(2) . . ?
C13 C12 C11 119.9(2) . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C26 C21 C22 119.2(2) . . ?
C26 C21 C1 121.1(2) . . ?
C22 C21 C1 119.7(2) . . ?
C21 C22 C23 120.0(2) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.5(2) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 120.5(2) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?

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
C21 C1 C2 O2 2.8(4) . . . . ?
Se1 C1 C2 O2 178.41(16) . . . . ?
C21 C1 C2 C3 -176.3(2) . . . . ?
Se1 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 O1 2.7(4) . . . . ?
O2 C2 C3 O1 -176.4(2) . . . . ?
C1 C2 C3 C4 -177.8(2) . . . . ?
O2 C2 C3 C4 3.1(3) . . . . ?
O1 C3 C4 C9 177.5(3) . . . . ?
C2 C3 C4 C9 -1.9(3) . . . . ?
O1 C3 C4 C5 -1.0(5) . . . . ?
C2 C3 C4 C5 179.6(3) . . . . ?
C9 C4 C5 C6 0.1(4) . . . . ?
C3 C4 C5 C6 178.4(3) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C6 C7 C8 O3 179.5(2) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C8 O3 C10 2.5(4) . . . . ?
C9 C8 O3 C10 -178.0(2) . . . . ?
C5 C4 C9 O2 178.9(2) . . . . ?
C3 C4 C9 O2 0.2(3) . . . . ?
C5 C4 C9 C8 -0.6(4) . . . . ?
C3 C4 C9 C8 -179.3(2) . . . . ?
O3 C8 C9 O2 1.6(4) . . . . ?
C7 C8 C9 O2 -178.8(2) . . . . ?
O3 C8 C9 C4 -179.0(2) . . . . ?
C7 C8 C9 C4 0.5(4) . . . . ?
C4 C9 O2 C2 1.8(3) . . . . ?
C8 C9 O2 C2 -178.8(2) . . . . ?
C1 C2 O2 C9 177.9(2) . . . . ?
C3 C2 O2 C9 -3.0(2) . . . . ?
Se1 C11 C12 C17 107.6(2) . . . . ?
Se1 C11 C12 C13 -71.8(3) . . . . ?
C17 C12 C13 C14 -1.2(4) . . . . ?
C11 C12 C13 C14 178.2(2) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C16 1.0(5) . . . . ?
C14 C15 C16 C17 -1.1(5) . . . . ?
C15 C16 C17 C12 0.1(5) . . . . ?
C13 C12 C17 C16 1.1(4) . . . . ?
C11 C12 C17 C16 -178.3(3) . . . . ?
C2 C1 C21 C26 -72.3(3) . . . . ?
Se1 C1 C21 C26 112.2(2) . . . . ?
C2 C1 C21 C22 106.3(3) . . . . ?
Se1 C1 C21 C22 -69.2(3) . . . . ?
C26 C21 C22 C23 0.8(4) . . . . ?
C1 C21 C22 C23 -177.9(3) . . . . ?
C21 C22 C23 C24 -0.8(5) . . . . ?
C22 C23 C24 C25 -0.4(5) . . . . ?
C23 C24 C25 C26 1.6(4) . . . . ?
C22 C21 C26 C25 0.3(4) . . . . ?
C1 C21 C26 C25 179.0(2) . . . . ?
C24 C25 C26 C21 -1.6(4) . . . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.043

