# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
# 
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data_1
_audit_block_doi                 10.5517/ccdc.csd.cc2clwc7
_database_code_depnum_ccdc_archive 'CCDC 2192889'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/anie.202211408 2023
loop_
_audit_author_name
_audit_author_address
'E Tang'
;Yunnan Uinversity
China
;
_audit_update_record             
;
2022-07-27 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;
_audit_creation_date             2022-05-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 Se, Cl4 H2 Mo O2, C D Cl3'
_chemical_formula_sum            'C19 H15  D Cl7 Mo O2 Se'
_chemical_formula_weight         700.37
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mo Mo -1.6832 0.6857 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2075(12)
_cell_length_b                   12.1341(16)
_cell_length_c                   13.2766(19)
_cell_angle_alpha                103.403(5)
_cell_angle_beta                 90.813(6)
_cell_angle_gamma                98.443(5)
_cell_volume                     1270.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8656
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.51
_shelx_estimated_absorpt_T_max   0.774
_shelx_estimated_absorpt_T_min   0.642
_exptl_absorpt_coefficient_mu    2.699
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71098    8.210   12.137   13.289  103.359   90.760   98.467
;
_exptl_crystal_colour            'light green'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'needle-like crystals'
_exptl_crystal_F_000             682
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15684
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.059
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3446
_reflns_number_total             4475
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.715
_refine_diff_density_min         -1.560
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4475
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0740P)²+7.0327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1569
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 C19-Cl7 = C19-Cl6 = C19-Cl8
 1.78 with sigma of 0.02
 C19-Cl7 \\sim C19-Cl6 \\sim C19-Cl8
 with sigma of 0.02
 Cl7-Cl6 \\sim Cl6-Cl8 \\sim Cl8-Cl7
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Cl6 \\sim Cl7 \\sim Cl8 \\sim C19: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
Uanis(Cl6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.005
4. Rigid body (RIGU) restrains
 Cl6, Cl7, Cl8, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Rotating group:
 O2(H2A,H2B)
5.b Ternary CH refined with riding coordinates:
 C19(D19)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Mo1 Mo 0.83120(8) 1.15898(5) 0.15283(5) 0.0375(2) Uani 1 1 d . . . . .
Cl1 Cl 0.7599(3) 1.0891(2) 0.29454(16) 0.0603(6) Uani 1 1 d . . . . .
O2 O 0.7856(6) 0.9633(4) 0.0672(4) 0.0353(10) Uani 1 1 d . . . . .
H2A H 0.878456 0.941729 0.040751 0.053 Uiso 1 1 d R U . . .
H2B H 0.717400 0.950933 0.011377 0.053 Uiso 1 1 d R U . . .
Cl3 Cl 0.5483(2) 1.13871(17) 0.10299(16) 0.0486(5) Uani 1 1 d . . . . .
Cl4 Cl 0.8957(2) 1.17675(15) -0.01975(15) 0.0453(4) Uani 1 1 d . . . . .
Cl5 Cl 1.1013(2) 1.11798(15) 0.17371(14) 0.0423(4) Uani 1 1 d . . . . .
O1 O 0.8657(7) 1.2974(4) 0.2087(5) 0.0580(15) Uani 1 1 d . . . . .
Se1 Se 0.50988(8) 0.77303(5) 0.14541(5) 0.0318(2) Uani 1 1 d . . . . .
C1 C 0.4197(8) 0.8414(5) 0.2738(5) 0.0303(14) Uani 1 1 d . . . . .
C2 C 0.4165(8) 0.7914(6) 0.3569(6) 0.0398(16) Uani 1 1 d . . . . .
H2 H 0.460977 0.722608 0.352895 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3469(10) 0.8437(7) 0.4467(6) 0.051(2) Uani 1 1 d . . . . .
H3 H 0.340365 0.810062 0.504650 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2863(11) 0.9465(7) 0.4508(6) 0.055(2) Uani 1 1 d . . . . .
H4 H 0.241687 0.983973 0.512784 0.066 Uiso 1 1 calc R U . . .
C5 C 0.2906(11) 0.9932(7) 0.3676(7) 0.056(2) Uani 1 1 d . . . . .
H5 H 0.247076 1.062445 0.371894 0.067 Uiso 1 1 calc R U . . .
C6 C 0.3573(9) 0.9423(6) 0.2761(6) 0.0447(18) Uani 1 1 d . . . . .
H6 H 0.360019 0.975049 0.217565 0.054 Uiso 1 1 calc R U . . .
C7 C 0.4021(8) 0.6165(5) 0.1223(5) 0.0337(15) Uani 1 1 d . . . . .
C8 C 0.2444(9) 0.5769(6) 0.0840(6) 0.0419(17) Uani 1 1 d . . . . .
H8 H 0.174632 0.626928 0.067797 0.050 Uiso 1 1 calc R U . . .
C9 C 0.1892(11) 0.4592(7) 0.0696(7) 0.054(2) Uani 1 1 d . . . . .
H9 H 0.079312 0.428210 0.044005 0.065 Uiso 1 1 calc R U . . .
C10 C 0.2936(11) 0.3885(7) 0.0924(6) 0.052(2) Uani 1 1 d . . . . .
H10 H 0.254735 0.308681 0.080890 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4516(11) 0.4298(6) 0.1311(6) 0.0457(18) Uani 1 1 d . . . . .
H11 H 0.521292 0.379271 0.146534 0.055 Uiso 1 1 calc R U . . .
C12 C 0.5094(9) 0.5465(5) 0.1477(5) 0.0339(15) Uani 1 1 d . . . . .
C13 C 0.6729(9) 0.6065(6) 0.1896(5) 0.0355(15) Uani 1 1 d . . . . .
C14 C 0.8016(10) 0.5580(7) 0.2239(6) 0.051(2) Uani 1 1 d . . . . .
H14 H 0.789709 0.478026 0.219781 0.061 Uiso 1 1 calc R U . . .
C15 C 0.9462(10) 0.6292(9) 0.2640(7) 0.062(2) Uani 1 1 d . . . . .
H15 H 1.032908 0.596673 0.288293 0.074 Uiso 1 1 calc R U . . .
C16 C 0.9703(9) 0.7458(8) 0.2702(7) 0.056(2) Uani 1 1 d . . . . .
H16 H 1.071563 0.792059 0.298393 0.067 Uiso 1 1 calc R U . . .
C17 C 0.8437(9) 0.7947(7) 0.2346(6) 0.0454(18) Uani 1 1 d . . . . .
H17 H 0.857649 0.874110 0.235719 0.055 Uiso 1 1 calc R U . . .
C18 C 0.6976(8) 0.7237(6) 0.1976(5) 0.0345(15) Uani 1 1 d . . . . .
Cl6 Cl 0.8102(7) 0.6955(4) 0.5106(3) 0.1417(15) Uani 1 1 d D U . . .
Cl7 Cl 0.5389(6) 0.6834(4) 0.6342(3) 0.1263(14) Uani 1 1 d D U . . .
Cl8 Cl 0.7274(6) 0.5011(3) 0.6027(3) 0.1374(16) Uani 1 1 d D U . . .
C19 C 0.7343(13) 0.6460(7) 0.6161(7) 0.096(4) Uani 1 1 d D U . . .
D19 D 0.806477 0.687101 0.678787 0.116 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
Mo1 Cl1 2.286(2) . ?
Mo1 O2 2.355(4) . ?
Mo1 Cl3 2.3673(19) . ?
Mo1 Cl4 2.4097(19) . ?
Mo1 Cl5 2.3680(18) . ?
Mo1 O1 1.651(5) . ?
O2 H2A 0.8926 . ?
O2 H2B 0.8928 . ?
Se1 C1 1.924(7) . ?
Se1 C7 1.927(6) . ?
Se1 C18 1.909(6) . ?
C1 C2 1.376(9) . ?
C1 C6 1.390(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.352(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.360(10) . ?
C7 C12 1.399(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.400(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(12) . ?
C10 H10 0.9500 . ?
C10 C11 1.367(12) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(10) . ?
C12 C13 1.464(10) . ?
C13 C14 1.401(10) . ?
C13 C18 1.385(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(13) . ?
C16 H16 0.9500 . ?
C16 C17 1.398(11) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(10) . ?
Cl6 C19 1.736(8) . ?
Cl7 C19 1.735(9) . ?
Cl8 C19 1.719(8) . ?
C19 D19 1.0000 . ?

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
Cl1 Mo1 O2 82.99(12) . . ?
Cl1 Mo1 Cl3 89.52(8) . . ?
Cl1 Mo1 Cl4 164.04(8) . . ?
Cl1 Mo1 Cl5 89.00(8) . . ?
O2 Mo1 Cl3 80.58(13) . . ?
O2 Mo1 Cl4 81.06(12) . . ?
O2 Mo1 Cl5 81.34(12) . . ?
Cl3 Mo1 Cl4 88.41(7) . . ?
Cl3 Mo1 Cl5 161.90(7) . . ?
Cl5 Mo1 Cl4 88.07(7) . . ?
O1 Mo1 Cl1 99.2(2) . . ?
O1 Mo1 O2 177.8(3) . . ?
O1 Mo1 Cl3 99.6(2) . . ?
O1 Mo1 Cl4 96.8(2) . . ?
O1 Mo1 Cl5 98.4(2) . . ?
Mo1 O2 H2A 110.4 . . ?
Mo1 O2 H2B 110.7 . . ?
H2A O2 H2B 103.3 . . ?
C1 Se1 C7 101.1(3) . . ?
C18 Se1 C1 100.0(3) . . ?
C18 Se1 C7 87.0(3) . . ?
C2 C1 Se1 121.3(5) . . ?
C2 C1 C6 122.9(7) . . ?
C6 C1 Se1 115.9(5) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.5(6) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(7) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(8) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(7) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 121.5 . . ?
C5 C6 C1 117.1(7) . . ?
C5 C6 H6 121.5 . . ?
C8 C7 Se1 125.5(5) . . ?
C8 C7 C12 123.6(6) . . ?
C12 C7 Se1 110.9(5) . . ?
C7 C8 H8 121.4 . . ?
C7 C8 C9 117.2(7) . . ?
C9 C8 H8 121.4 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(8) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.9(7) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.4(7) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C13 114.9(6) . . ?
C11 C12 C7 117.8(7) . . ?
C11 C12 C13 127.3(6) . . ?
C14 C13 C12 126.8(7) . . ?
C18 C13 C12 115.1(6) . . ?
C18 C13 C14 118.1(7) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.5(8) . . ?
C15 C14 H14 120.8 . . ?
C14 C15 H15 118.5 . . ?
C14 C15 C16 122.9(7) . . ?
C16 C15 H15 118.5 . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.1(8) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 121.1 . . ?
C18 C17 C16 117.7(7) . . ?
C18 C17 H17 121.1 . . ?
C13 C18 Se1 111.9(5) . . ?
C17 C18 Se1 124.4(5) . . ?
C17 C18 C13 123.6(6) . . ?
Cl6 C19 D19 108.3 . . ?
Cl7 C19 Cl6 107.1(5) . . ?
Cl7 C19 D19 108.3 . . ?
Cl8 C19 Cl6 114.2(5) . . ?
Cl8 C19 Cl7 110.6(6) . . ?
Cl8 C19 D19 108.3 . . ?

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
Se1 C1 C2 C3 -178.7(6) . . . . ?
Se1 C1 C6 C5 179.7(6) . . . . ?
Se1 C7 C8 C9 178.1(6) . . . . ?
Se1 C7 C12 C11 -177.4(5) . . . . ?
Se1 C7 C12 C13 2.6(7) . . . . ?
C1 C2 C3 C4 -1.6(12) . . . . ?
C2 C1 C6 C5 0.5(11) . . . . ?
C2 C3 C4 C5 2.0(14) . . . . ?
C3 C4 C5 C6 -1.1(14) . . . . ?
C4 C5 C6 C1 -0.2(13) . . . . ?
C6 C1 C2 C3 0.4(11) . . . . ?
C7 C8 C9 C10 -0.9(12) . . . . ?
C7 C12 C13 C14 178.0(7) . . . . ?
C7 C12 C13 C18 -0.1(9) . . . . ?
C8 C7 C12 C11 1.1(10) . . . . ?
C8 C7 C12 C13 -178.9(6) . . . . ?
C8 C9 C10 C11 1.2(13) . . . . ?
C9 C10 C11 C12 -0.3(12) . . . . ?
C10 C11 C12 C7 -0.9(10) . . . . ?
C10 C11 C12 C13 179.2(7) . . . . ?
C11 C12 C13 C14 -2.1(12) . . . . ?
C11 C12 C13 C18 179.8(7) . . . . ?
C12 C7 C8 C9 -0.2(11) . . . . ?
C12 C13 C14 C15 -178.1(7) . . . . ?
C12 C13 C18 Se1 -2.4(7) . . . . ?
C12 C13 C18 C17 -179.6(6) . . . . ?
C13 C14 C15 C16 -1.0(13) . . . . ?
C14 C13 C18 Se1 179.3(5) . . . . ?
C14 C13 C18 C17 2.1(11) . . . . ?
C14 C15 C16 C17 -0.1(14) . . . . ?
C15 C16 C17 C18 2.1(12) . . . . ?
C16 C17 C18 Se1 -180.0(6) . . . . ?
C16 C17 C18 C13 -3.1(11) . . . . ?
C18 C13 C14 C15 0.0(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2192880'
loop_
_audit_author_name
_audit_author_address
'E Tang'
;Yunnan Uinversity
China
;
_audit_update_record             
;
2022-07-27 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;
_audit_creation_date             2022-07-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
3-bromo-11H-benzo[4,5]selenopheno[3,2-b]chromen-11-one
_chemical_formula_moiety         'C15 H7 Br O2 Se'
_chemical_formula_sum            'C15 H7 Br O2 Se'
_chemical_formula_weight         378.08
_chemical_melting_point          '95.5-98 \%C'
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.133(2)
_cell_length_b                   7.2784(13)
_cell_length_c                   14.645(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.078(6)
_cell_angle_gamma                90
_cell_volume                     1236.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   0.367
_shelx_estimated_absorpt_T_min   0.304
_exptl_absorpt_coefficient_mu    6.261
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1297 before and 0.0793 after correction.
The Ratio of minimum to maximum transmission is 0.6228.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.031
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_min         2.910
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2777
_reflns_number_total             3075
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0035(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3075
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.0174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0510
_refine_ls_wR_factor_ref         0.0524
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.95752(2) 0.41201(3) 0.88627(2) 0.02247(8) Uani 1 1 d . . . . .
Se1 Se 0.54838(2) 0.73159(3) 0.31459(2) 0.01810(7) Uani 1 1 d . . . . .
O1 O 0.63159(11) 0.64876(19) 0.59855(9) 0.0143(3) Uani 1 1 d . . . . .
O2 O 0.80504(13) 0.5569(2) 0.39823(11) 0.0256(3) Uani 1 1 d . . . . .
C1 C 0.89515(17) 0.4628(3) 0.75414(14) 0.0164(4) Uani 1 1 d . . . . .
C2 C 0.95954(17) 0.4209(3) 0.69190(15) 0.0187(4) Uani 1 1 d . . . . .
H2 H 1.0339 0.3671 0.7150 0.022 Uiso 1 1 calc R U . . .
C3 C 0.91270(17) 0.4595(3) 0.59644(15) 0.0175(4) Uani 1 1 d . . . . .
H3 H 0.9558 0.4317 0.5535 0.021 Uiso 1 1 calc R U . . .
C4 C 0.80300(17) 0.5389(3) 0.56071(14) 0.0151(4) Uani 1 1 d . . . . .
C5 C 0.74101(16) 0.5752(3) 0.62559(14) 0.0143(4) Uani 1 1 d . . . . .
C6 C 0.78684(17) 0.5398(3) 0.72313(14) 0.0156(4) Uani 1 1 d . . . . .
H6 H 0.7447 0.5680 0.7667 0.019 Uiso 1 1 calc R U . . .
C7 C 0.75350(17) 0.5810(3) 0.45807(14) 0.0172(4) Uani 1 1 d . . . . .
C8 C 0.63850(17) 0.6553(3) 0.43663(14) 0.0155(4) Uani 1 1 d . . . . .
C9 C 0.58449(16) 0.6873(3) 0.50454(14) 0.0141(4) Uani 1 1 d . . . . .
C10 C 0.47183(16) 0.7696(3) 0.47303(14) 0.0144(4) Uani 1 1 d . . . . .
C11 C 0.43638(17) 0.8046(3) 0.37441(14) 0.0164(4) Uani 1 1 d . . . . .
C12 C 0.32984(18) 0.8862(3) 0.32950(15) 0.0191(4) Uani 1 1 d . . . . .
H12 H 0.3064 0.9097 0.2628 0.023 Uiso 1 1 calc R U . . .
C13 C 0.25993(17) 0.9315(3) 0.38544(16) 0.0200(4) Uani 1 1 d . . . . .
H13 H 0.1871 0.9867 0.3565 0.024 Uiso 1 1 calc R U . . .
C14 C 0.29407(17) 0.8977(3) 0.48430(15) 0.0184(4) Uani 1 1 d . . . . .
H14 H 0.2445 0.9307 0.5212 0.022 Uiso 1 1 calc R U . . .
C15 C 0.39931(16) 0.8168(3) 0.52818(14) 0.0156(4) Uani 1 1 d . . . . .
H15 H 0.4222 0.7934 0.5949 0.019 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
Br1 C1 1.896(2) . ?
Se1 C8 1.884(2) . ?
Se1 C11 1.896(2) . ?
O1 C5 1.377(2) . ?
O1 C9 1.356(2) . ?
O2 C7 1.230(2) . ?
C1 C2 1.397(3) . ?
C1 C6 1.377(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(3) . ?
C4 C5 1.399(3) . ?
C4 C7 1.478(3) . ?
C5 C6 1.396(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.442(3) . ?
C8 C9 1.362(3) . ?
C9 C10 1.438(3) . ?
C10 C11 1.404(3) . ?
C10 C15 1.401(3) . ?
C11 C12 1.399(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.406(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(3) . ?
C15 H15 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
C8 Se1 C11 86.52(9) . . ?
C9 O1 C5 117.10(15) . . ?
C2 C1 Br1 119.43(15) . . ?
C6 C1 Br1 118.17(15) . . ?
C6 C1 C2 122.40(18) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.39(18) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.80(18) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C7 121.49(18) . . ?
C5 C4 C3 117.67(18) . . ?
C5 C4 C7 120.84(17) . . ?
O1 C5 C4 122.89(17) . . ?
O1 C5 C6 115.23(17) . . ?
C6 C5 C4 121.88(18) . . ?
C1 C6 C5 117.84(18) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
O2 C7 C4 123.73(18) . . ?
O2 C7 C8 124.09(19) . . ?
C8 C7 C4 112.18(17) . . ?
C7 C8 Se1 124.87(14) . . ?
C9 C8 Se1 111.88(15) . . ?
C9 C8 C7 123.17(18) . . ?
O1 C9 C8 123.80(17) . . ?
O1 C9 C10 119.30(17) . . ?
C8 C9 C10 116.90(18) . . ?
C11 C10 C9 112.39(17) . . ?
C15 C10 C9 128.00(18) . . ?
C15 C10 C11 119.61(18) . . ?
C10 C11 Se1 112.32(15) . . ?
C12 C11 Se1 126.18(16) . . ?
C12 C11 C10 121.49(19) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 C11 117.78(19) . . ?
C13 C12 H12 121.1 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.51(19) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.42(19) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 120.4 . . ?
C14 C15 C10 119.19(18) . . ?
C14 C15 H15 120.4 . . ?

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
C6 H6 Se1 0.95 3.05 3.900(2) 150.4 4_576
C12 H12 O2 0.95 2.58 3.484(3) 158.9 2_655

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
Br1 C1 C2 C3 -179.80(15) . . . . ?
Br1 C1 C6 C5 -179.38(14) . . . . ?
Se1 C8 C9 O1 -178.59(14) . . . . ?
Se1 C8 C9 C10 0.4(2) . . . . ?
Se1 C11 C12 C13 -179.41(15) . . . . ?
O1 C5 C6 C1 178.76(17) . . . . ?
O1 C9 C10 C11 178.67(16) . . . . ?
O1 C9 C10 C15 -0.6(3) . . . . ?
O2 C7 C8 Se1 -1.1(3) . . . . ?
O2 C7 C8 C9 -177.5(2) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C2 C3 C4 C7 179.62(18) . . . . ?
C3 C4 C5 O1 -178.45(17) . . . . ?
C3 C4 C5 C6 2.0(3) . . . . ?
C3 C4 C7 O2 -2.8(3) . . . . ?
C3 C4 C7 C8 177.79(18) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C7 C8 Se1 178.35(14) . . . . ?
C4 C7 C8 C9 1.9(3) . . . . ?
C5 O1 C9 C8 0.9(3) . . . . ?
C5 O1 C9 C10 -178.12(16) . . . . ?
C5 C4 C7 O2 178.0(2) . . . . ?
C5 C4 C7 C8 -1.5(3) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C7 C4 C5 O1 0.8(3) . . . . ?
C7 C4 C5 C6 -178.75(18) . . . . ?
C7 C8 C9 O1 -1.7(3) . . . . ?
C7 C8 C9 C10 177.26(18) . . . . ?
C8 Se1 C11 C10 0.05(15) . . . . ?
C8 Se1 C11 C12 179.44(19) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C8 C9 C10 C15 -179.67(19) . . . . ?
C9 O1 C5 C4 -0.4(3) . . . . ?
C9 O1 C5 C6 179.17(16) . . . . ?
C9 C10 C11 Se1 0.2(2) . . . . ?
C9 C10 C11 C12 -179.27(18) . . . . ?
C9 C10 C15 C14 179.05(19) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 Se1 C8 C7 -177.04(18) . . . . ?
C11 Se1 C8 C9 -0.25(15) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C10 0.3(3) . . . . ?
C15 C10 C11 Se1 179.51(14) . . . . ?
C15 C10 C11 C12 0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
