# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_2jasecl
_database_code_depnum_ccdc_archive 'CCDC 2210773'
loop_
_audit_author_name
_audit_author_address
'Peter G. Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2022-10-03 deposited with the CCDC.	2022-11-07 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            'C15 H15 Cl O4 Se'
_chemical_formula_weight         373.68

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                   7.85998(10)
_cell_length_b                   9.94396(14)
_cell_length_c                   11.27503(17)
_cell_angle_alpha                114.4747(13)
_cell_angle_beta                 96.3936(12)
_cell_angle_gamma                101.6968(12)
_cell_volume                     766.31(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    53905
_cell_measurement_theta_min      2.2940
_cell_measurement_theta_max      38.1390

_exptl_crystal_description       'irregular block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.636
_shelx_estimated_absorpt_T_min   0.743
_shelx_estimated_absorpt_T_max   0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89451
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.65a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            91637
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.034
_diffrn_reflns_theta_max         38.304
_diffrn_reflns_theta_full        37.500
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             8149
_reflns_number_gt                7657
_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 1.171.42.65a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.65a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.65a (Rigaku OD, 2022)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;
 The hydrogen atoms at C5 were refined freely, but with C-H distances restrained
 to be approximately equal (command "SADI").
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0288P)²+0.1962P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8149
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0574
_refine_ls_wR_factor_gt          0.0564
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.002
_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 0.40440(2) 0.80310(2) 0.50589(2) 0.01211(2) Uani 1 1 d . . . . .
C1 C 0.26170(10) 0.71813(9) 0.32974(8) 0.01166(12) Uani 1 1 d . . . . .
C2 C 0.37784(10) 0.68410(9) 0.22655(8) 0.01189(12) Uani 1 1 d . . . . .
C3 C 0.54826(11) 0.66137(10) 0.28855(8) 0.01405(13) Uani 1 1 d . . . . .
H3A H 0.520931 0.561192 0.291327 0.017 Uiso 1 1 calc R U . . .
H3B H 0.638481 0.662427 0.234040 0.017 Uiso 1 1 calc R U . . .
C4 C 0.62008(10) 0.79251(9) 0.43038(8) 0.01229(12) Uani 1 1 d . . . . .
H4 H 0.667568 0.890497 0.424911 0.015 Uiso 1 1 calc R U . . .
C5 C 0.08471(11) 0.68679(10) 0.30271(9) 0.01506(13) Uani 1 1 d D . . . .
H051 H 0.019(2) 0.7045(18) 0.3700(15) 0.025(4) Uiso 1 1 d D . . . .
H052 H 0.020(2) 0.6411(17) 0.2143(14) 0.021(4) Uiso 1 1 d D . . . .
C6 C 0.27467(11) 0.53909(9) 0.09877(8) 0.01323(12) Uani 1 1 d . . . . .
C7 C 0.12799(13) 0.27564(10) 0.01079(10) 0.01911(15) Uani 1 1 d . . . . .
H7A H 0.184482 0.249262 -0.066004 0.029 Uiso 1 1 calc R U . . .
H7B H 0.011941 0.290422 -0.013437 0.029 Uiso 1 1 calc R U . . .
H7C H 0.111538 0.192184 0.036967 0.029 Uiso 1 1 calc R U . . .
O1 O 0.22873(11) 0.53825(8) -0.00736(7) 0.02200(13) Uani 1 1 d . . . . .
O2 O 0.24048(10) 0.41631(7) 0.12158(7) 0.01775(11) Uani 1 1 d . . . . .
C8 C 0.42775(11) 0.81403(9) 0.18495(8) 0.01321(12) Uani 1 1 d . . . . .
C9 C 0.33645(13) 1.00424(11) 0.14309(10) 0.01912(15) Uani 1 1 d . . . . .
H9A H 0.334989 0.956589 0.047385 0.029 Uiso 1 1 calc R U . . .
H9B H 0.453377 1.076946 0.192454 0.029 Uiso 1 1 calc R U . . .
H9C H 0.244321 1.058956 0.159041 0.029 Uiso 1 1 calc R U . . .
O3 O 0.56601(9) 0.84495(9) 0.15209(8) 0.02040(13) Uani 1 1 d . . . . .
O4 O 0.30192(9) 0.88625(8) 0.18803(7) 0.01588(11) Uani 1 1 d . . . . .
C11 C 0.76129(10) 0.77167(9) 0.51789(8) 0.01170(12) Uani 1 1 d . . . . .
C12 C 0.74899(11) 0.63044(9) 0.52016(9) 0.01453(13) Uani 1 1 d . . . . .
H12 H 0.648405 0.545704 0.466374 0.017 Uiso 1 1 calc R U . . .
C13 C 0.88166(11) 0.61225(10) 0.59987(9) 0.01566(13) Uani 1 1 d . . . . .
H13 H 0.871978 0.516069 0.601097 0.019 Uiso 1 1 calc R U . . .
C14 C 1.02910(11) 0.73694(10) 0.67798(8) 0.01394(13) Uani 1 1 d . . . . .
C15 C 1.04455(11) 0.87906(9) 0.67915(8) 0.01457(13) Uani 1 1 d . . . . .
H15 H 1.145139 0.963549 0.733458 0.017 Uiso 1 1 calc R U . . .
C16 C 0.90941(11) 0.89554(9) 0.59895(8) 0.01365(12) Uani 1 1 d . . . . .
H16 H 0.918261 0.992505 0.599489 0.016 Uiso 1 1 calc R U . . .
Cl1 Cl 1.19446(3) 0.71086(3) 0.77590(2) 0.01953(4) 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 1.9093(8) . ?
Se1 C4 1.9822(8) . ?
C1 C5 1.3328(11) . ?
C1 C2 1.5287(11) . ?
C2 C6 1.5352(11) . ?
C2 C3 1.5424(11) . ?
C2 C8 1.5430(11) . ?
C3 C4 1.5326(12) . ?
C4 C11 1.5057(11) . ?
C6 O1 1.2069(11) . ?
C6 O2 1.3310(10) . ?
C7 O2 1.4503(11) . ?
C8 O3 1.2089(10) . ?
C8 O4 1.3305(10) . ?
C9 O4 1.4495(11) . ?
C11 C16 1.3988(11) . ?
C11 C12 1.3991(11) . ?
C12 C13 1.3894(12) . ?
C13 C14 1.3933(12) . ?
C14 C15 1.3881(12) . ?
C14 Cl1 1.7406(9) . ?
C15 C16 1.3972(12) . ?

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 C4 89.56(3) . . ?
C5 C1 C2 125.73(7) . . ?
C5 C1 Se1 123.67(6) . . ?
C2 C1 Se1 110.52(5) . . ?
C1 C2 C6 109.40(6) . . ?
C1 C2 C3 107.56(6) . . ?
C6 C2 C3 111.10(6) . . ?
C1 C2 C8 112.69(6) . . ?
C6 C2 C8 106.35(6) . . ?
C3 C2 C8 109.79(6) . . ?
C4 C3 C2 108.26(6) . . ?
C11 C4 C3 115.93(7) . . ?
C11 C4 Se1 110.54(5) . . ?
C3 C4 Se1 103.26(5) . . ?
O1 C6 O2 124.95(8) . . ?
O1 C6 C2 124.00(8) . . ?
O2 C6 C2 111.04(7) . . ?
C6 O2 C7 115.61(7) . . ?
O3 C8 O4 124.13(8) . . ?
O3 C8 C2 123.13(8) . . ?
O4 C8 C2 112.74(7) . . ?
C8 O4 C9 115.48(7) . . ?
C16 C11 C12 118.64(7) . . ?
C16 C11 C4 119.73(7) . . ?
C12 C11 C4 121.62(7) . . ?
C13 C12 C11 121.00(7) . . ?
C12 C13 C14 119.13(8) . . ?
C15 C14 C13 121.34(8) . . ?
C15 C14 Cl1 120.38(6) . . ?
C13 C14 Cl1 118.27(7) . . ?
C14 C15 C16 118.76(7) . . ?
C15 C16 C11 121.12(7) . . ?

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 C1 C2 C6 -31.44(11) . . . . ?
Se1 C1 C2 C6 145.39(5) . . . . ?
C5 C1 C2 C3 -152.22(8) . . . . ?
Se1 C1 C2 C3 24.62(7) . . . . ?
C5 C1 C2 C8 86.64(10) . . . . ?
Se1 C1 C2 C8 -96.53(7) . . . . ?
C1 C2 C3 C4 -46.99(8) . . . . ?
C6 C2 C3 C4 -166.69(7) . . . . ?
C8 C2 C3 C4 75.96(8) . . . . ?
C2 C3 C4 C11 166.79(7) . . . . ?
C2 C3 C4 Se1 45.78(7) . . . . ?
C1 C2 C6 O1 114.69(9) . . . . ?
C3 C2 C6 O1 -126.72(9) . . . . ?
C8 C2 C6 O1 -7.29(11) . . . . ?
C1 C2 C6 O2 -64.19(9) . . . . ?
C3 C2 C6 O2 54.41(9) . . . . ?
C8 C2 C6 O2 173.84(7) . . . . ?
O1 C6 O2 C7 -4.81(13) . . . . ?
C2 C6 O2 C7 174.05(7) . . . . ?
C1 C2 C8 O3 148.84(8) . . . . ?
C6 C2 C8 O3 -91.31(10) . . . . ?
C3 C2 C8 O3 28.97(11) . . . . ?
C1 C2 C8 O4 -31.80(9) . . . . ?
C6 C2 C8 O4 88.05(8) . . . . ?
C3 C2 C8 O4 -151.67(7) . . . . ?
O3 C8 O4 C9 2.54(13) . . . . ?
C2 C8 O4 C9 -176.81(7) . . . . ?
C3 C4 C11 C16 137.62(8) . . . . ?
Se1 C4 C11 C16 -105.35(7) . . . . ?
C3 C4 C11 C12 -42.11(11) . . . . ?
Se1 C4 C11 C12 74.92(9) . . . . ?
C16 C11 C12 C13 -0.73(13) . . . . ?
C4 C11 C12 C13 179.00(8) . . . . ?
C11 C12 C13 C14 -0.28(14) . . . . ?
C12 C13 C14 C15 0.97(14) . . . . ?
C12 C13 C14 Cl1 -179.45(7) . . . . ?
C13 C14 C15 C16 -0.61(13) . . . . ?
Cl1 C14 C15 C16 179.82(6) . . . . ?
C14 C15 C16 C11 -0.44(13) . . . . ?
C12 C11 C16 C15 1.10(12) . . . . ?
C4 C11 C16 C15 -178.63(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H052 O1 0.937(13) 2.562(14) 3.4539(11) 159.1(13) 2_565 yes
C7 H7A O3 0.98 2.47 3.3051(12) 143.4 2_665 yes
C9 H9A Cl1 0.98 2.92 3.8131(10) 152.3 1_454 yes
C15 H15 O3 0.95 2.45 3.3900(11) 170.0 2_776 yes

_refine_diff_density_max         0.809
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.079



