# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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. 
# 
#######################################################################

data_b230214b_0m
_database_code_depnum_ccdc_archive 'CCDC 2243152'
loop_
_audit_author_name
_audit_author_address
'Huan Liu'
;Soochow university
China
;
_audit_update_record             
;
2023-02-20 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2023-02-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 Cl N3 O3 Se'
_chemical_formula_sum            'C17 H16 Cl N3 O3 Se'
_chemical_formula_weight         424.74
_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'
N N 0.0061 0.0033 '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                   7.3092(6)
_cell_length_b                   10.4613(9)
_cell_length_c                   12.1430(10)
_cell_angle_alpha                72.439(3)
_cell_angle_beta                 87.404(3)
_cell_angle_gamma                81.976(3)
_cell_volume                     876.56(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.654
_shelx_estimated_absorpt_T_min   0.347
_exptl_absorpt_coefficient_mu    2.316
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1454 before and 0.0865 after correction.
The Ratio of minimum to maximum transmission is 0.6104.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35035
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.759
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3230
_reflns_number_total             4029
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4029
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.030
_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)+(0.0522P)²+0.5310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1061
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C14(H14), C17(H17), C3(H3A), C15(H15), C2(H2), C6(H6), C5(H5)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
Se11 Se 0.19102(4) 0.65000(3) 0.55881(2) 0.05165(13) Uani 1 1 d . . . . .
Cl1 Cl 0.86314(15) 1.03404(11) 0.31257(7) 0.0767(3) Uani 1 1 d . . . . .
O3 O -0.1888(3) 0.5539(3) 0.86299(18) 0.0597(6) Uani 1 1 d . . . . .
H3 H -0.2533 0.5740 0.8052 0.090 Uiso 1 1 calc GR . . . .
N2 N 0.2981(3) 0.4992(2) 0.77507(18) 0.0395(5) Uani 1 1 d . . . . .
N3 N 0.5194(3) 0.6360(2) 0.68916(18) 0.0431(5) Uani 1 1 d . . . . .
N1 N 0.8212(4) -0.0739(3) 0.9600(3) 0.0660(8) Uani 1 1 d . . . . .
O2 O 0.8492(4) -0.1193(3) 0.8791(3) 0.0927(9) Uani 1 1 d . . . . .
C7 C 0.3977(4) 0.4470(3) 0.8845(2) 0.0395(5) Uani 1 1 d . . . . .
H7A H 0.3089 0.4384 0.9473 0.047 Uiso 1 1 calc R . . . .
H7B H 0.4766 0.5122 0.8896 0.047 Uiso 1 1 calc R . . . .
C4 C 0.5142(3) 0.3124(3) 0.9004(2) 0.0362(5) Uani 1 1 d . . . . .
C12 C 0.3645(3) 0.5937(3) 0.6847(2) 0.0376(5) Uani 1 1 d . . . . .
C13 C 0.5892(3) 0.7326(3) 0.5941(2) 0.0394(6) Uani 1 1 d . . . . .
O1 O 0.8678(4) -0.1364(3) 1.0599(3) 0.0923(9) Uani 1 1 d . . . . .
C18 C 0.6127(4) 0.7173(3) 0.4844(2) 0.0484(6) Uani 1 1 d . . . . .
H18 H 0.5728 0.6439 0.4689 0.058 Uiso 1 1 calc R . . . .
C8 C 0.1001(3) 0.4881(3) 0.7760(2) 0.0416(6) Uani 1 1 d . . . . .
H8 H 0.0802 0.3961 0.8212 0.050 Uiso 1 1 calc R . . . .
C14 C 0.6534(4) 0.8416(3) 0.6158(2) 0.0462(6) Uani 1 1 d . . . . .
H14 H 0.6408 0.8517 0.6894 0.055 Uiso 1 1 calc R . . . .
C17 C 0.6956(4) 0.8114(3) 0.3977(2) 0.0504(7) Uani 1 1 d . . . . .
H17 H 0.7102 0.8016 0.3241 0.060 Uiso 1 1 calc R . . . .
C3 C 0.5529(4) 0.2294(3) 1.0117(2) 0.0481(7) Uani 1 1 d . . . . .
H3A H 0.5074 0.2584 1.0741 0.058 Uiso 1 1 calc R . . . .
C9 C -0.0104(4) 0.5887(3) 0.8309(3) 0.0457(6) Uani 1 1 d . . . . .
H9A H 0.0542 0.5897 0.8985 0.055 Uiso 1 1 calc R . . . .
H9B H -0.0202 0.6788 0.7763 0.055 Uiso 1 1 calc R . . . .
C1 C 0.7195(4) 0.0628(3) 0.9385(3) 0.0485(7) Uani 1 1 d . . . . .
C16 C 0.7557(4) 0.9187(3) 0.4210(2) 0.0479(6) Uani 1 1 d . . . . .
C15 C 0.7360(4) 0.9356(3) 0.5291(3) 0.0510(7) Uani 1 1 d . . . . .
H15 H 0.7775 1.0089 0.5439 0.061 Uiso 1 1 calc R . . . .
C10 C 0.0449(4) 0.5120(3) 0.6519(3) 0.0501(7) Uani 1 1 d . . . . .
H10A H -0.0862 0.5436 0.6413 0.060 Uiso 1 1 calc R . . . .
H10B H 0.0723 0.4293 0.6303 0.060 Uiso 1 1 calc R . . . .
C2 C 0.6575(5) 0.1047(3) 1.0313(3) 0.0537(7) Uani 1 1 d . . . . .
H2 H 0.6853 0.0501 1.1062 0.064 Uiso 1 1 calc R . . . .
C6 C 0.6873(4) 0.1424(3) 0.8272(3) 0.0567(7) Uani 1 1 d . . . . .
H6 H 0.7334 0.1125 0.7653 0.068 Uiso 1 1 calc R . . . .
C5 C 0.5850(4) 0.2679(3) 0.8087(2) 0.0520(7) Uani 1 1 d . . . . .
H5 H 0.5632 0.3236 0.7335 0.062 Uiso 1 1 calc R . . . .


_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
Se11 C12 1.927(2) . ?
Se11 C10 1.960(3) . ?
Cl1 C16 1.738(3) . ?
O3 C9 1.409(3) . ?
N2 C7 1.461(3) . ?
N2 C12 1.360(3) . ?
N2 C8 1.467(3) . ?
N3 C12 1.281(3) . ?
N3 C13 1.414(3) . ?
N1 O2 1.212(4) . ?
N1 O1 1.229(4) . ?
N1 C1 1.470(4) . ?
C7 C4 1.504(4) . ?
C4 C3 1.385(4) . ?
C4 C5 1.384(4) . ?
C13 C18 1.389(4) . ?
C13 C14 1.391(4) . ?
C18 C17 1.388(4) . ?
C8 C9 1.530(4) . ?
C8 C10 1.516(4) . ?
C14 C15 1.386(4) . ?
C17 C16 1.368(4) . ?
C3 C2 1.376(4) . ?
C1 C2 1.366(5) . ?
C1 C6 1.368(4) . ?
C16 C15 1.375(4) . ?
C6 C5 1.377(4) . ?

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
C12 Se11 C10 87.26(12) . . ?
C7 N2 C8 118.2(2) . . ?
C12 N2 C7 120.6(2) . . ?
C12 N2 C8 117.6(2) . . ?
C12 N3 C13 121.9(2) . . ?
O2 N1 O1 124.2(3) . . ?
O2 N1 C1 118.1(3) . . ?
O1 N1 C1 117.7(3) . . ?
N2 C7 C4 114.1(2) . . ?
C3 C4 C7 118.5(2) . . ?
C5 C4 C7 123.0(2) . . ?
C5 C4 C3 118.5(3) . . ?
N2 C12 Se11 109.80(18) . . ?
N3 C12 Se11 128.0(2) . . ?
N3 C12 N2 122.2(2) . . ?
C18 C13 N3 123.6(2) . . ?
C18 C13 C14 118.9(2) . . ?
C14 C13 N3 117.2(2) . . ?
C17 C18 C13 120.2(3) . . ?
N2 C8 C9 110.6(2) . . ?
N2 C8 C10 106.9(2) . . ?
C10 C8 C9 112.5(2) . . ?
C15 C14 C13 120.9(3) . . ?
C16 C17 C18 119.8(3) . . ?
C2 C3 C4 121.1(3) . . ?
O3 C9 C8 111.1(2) . . ?
C2 C1 N1 118.3(3) . . ?
C2 C1 C6 122.3(3) . . ?
C6 C1 N1 119.3(3) . . ?
C17 C16 Cl1 119.3(2) . . ?
C17 C16 C15 121.3(3) . . ?
C15 C16 Cl1 119.3(2) . . ?
C16 C15 C14 119.0(3) . . ?
C8 C10 Se11 105.54(18) . . ?
C1 C2 C3 118.5(3) . . ?
C1 C6 C5 118.5(3) . . ?
C6 C5 C4 121.0(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
