# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1976347'
loop_
_audit_author_name
_audit_author_address
'Shun-Yi Wang'
;Soochow University
China
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-02-18 downloaded from the CCDC.
;
_audit_creation_date             2018-06-08
_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         'C21 H16 N2 Se'
_chemical_formula_sum            'C21 H16 N2 Se'
_chemical_formula_weight         375.32
_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'
N N 0.0061 0.0033 '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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.244(2)
_cell_length_b                   9.6663(19)
_cell_length_c                   16.765(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.91(3)
_cell_angle_gamma                90
_cell_volume                     1658.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5461
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.7606
_cell_measurement_theta_min      2.2796
_shelx_estimated_absorpt_T_max   0.343
_shelx_estimated_absorpt_T_min   0.300
_exptl_absorpt_coefficient_mu    2.268
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8464
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.6
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.8464
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8260
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.280
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Saturn 724+'
_diffrn_measurement_method       'ω scan'
_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                3191
_reflns_number_total             3360
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+0.9680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0828
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.6520(2) 0.0916(3) -0.11771(14) 0.0223(5) Uani 1 1 d . . . . .
H1 H 0.7333 0.0692 -0.1393 0.027 Uiso 1 1 calc R . . . .
C2 C 0.5359(3) 0.0601(3) -0.16025(15) 0.0276(5) Uani 1 1 d . . . . .
H2 H 0.5380 0.0163 -0.2109 0.033 Uiso 1 1 calc R . . . .
C3 C 0.4175(2) 0.0924(3) -0.12907(16) 0.0288(5) Uani 1 1 d . . . . .
H3 H 0.3382 0.0703 -0.1581 0.035 Uiso 1 1 calc R . . . .
C4 C 0.4143(2) 0.1570(3) -0.05527(15) 0.0264(5) Uani 1 1 d . . . . .
H4 H 0.3326 0.1797 -0.0342 0.032 Uiso 1 1 calc R . . . .
C5 C 0.5298(2) 0.1888(2) -0.01188(14) 0.0214(5) Uani 1 1 d . . . . .
H5 H 0.5269 0.2325 0.0388 0.026 Uiso 1 1 calc R . . . .
C6 C 0.6497(2) 0.1565(2) -0.04303(12) 0.0176(4) Uani 1 1 d . . . . .
C7 C 0.7749(2) 0.1884(2) 0.00002(12) 0.0156(4) Uani 1 1 d . . . . .
C8 C 0.8211(2) 0.3039(2) 0.04227(12) 0.0150(4) Uani 1 1 d . . . . .
C9 C 0.9561(2) 0.2768(2) 0.06097(11) 0.0147(4) Uani 1 1 d . . . . .
C10 C 0.6635(2) 0.4183(2) 0.16577(12) 0.0173(4) Uani 1 1 d . . . . .
C11 C 0.6130(2) 0.5260(3) 0.21028(15) 0.0229(5) Uani 1 1 d . . . . .
H11 H 0.6082 0.6170 0.1889 0.027 Uiso 1 1 calc R . . . .
C12 C 0.5699(2) 0.4996(3) 0.28581(15) 0.0286(6) Uani 1 1 d . . . . .
H12 H 0.5358 0.5730 0.3162 0.034 Uiso 1 1 calc R . . . .
C13 C 0.5761(2) 0.3672(3) 0.31734(14) 0.0285(6) Uani 1 1 d . . . . .
H13 H 0.5469 0.3498 0.3693 0.034 Uiso 1 1 calc R . . . .
C14 C 0.6250(2) 0.2605(3) 0.27280(14) 0.0246(5) Uani 1 1 d . . . . .
H14 H 0.6283 0.1695 0.2942 0.030 Uiso 1 1 calc R . . . .
C15 C 0.6693(2) 0.2847(2) 0.19715(13) 0.0203(5) Uani 1 1 d . . . . .
H15 H 0.7033 0.2110 0.1670 0.024 Uiso 1 1 calc R . . . .
C16 C 1.0595(2) 0.3599(2) 0.10275(12) 0.0167(4) Uani 1 1 d . . . . .
C17 C 1.0514(2) 0.5035(3) 0.10887(13) 0.0195(4) Uani 1 1 d . . . . .
H17 H 0.9757 0.5501 0.0876 0.023 Uiso 1 1 calc R . . . .
C18 C 1.1531(2) 0.5792(3) 0.14576(14) 0.0236(5) Uani 1 1 d . . . . .
H18 H 1.1459 0.6769 0.1499 0.028 Uiso 1 1 calc R . . . .
C19 C 1.2641(3) 0.5137(3) 0.17637(15) 0.0281(5) Uani 1 1 d . . . . .
H19 H 1.3333 0.5660 0.2013 0.034 Uiso 1 1 calc R . . . .
C20 C 1.2741(2) 0.3707(3) 0.17055(16) 0.0309(6) Uani 1 1 d . . . . .
H20 H 1.3507 0.3250 0.1913 0.037 Uiso 1 1 calc R . . . .
C21 C 1.1726(2) 0.2944(3) 0.13452(14) 0.0249(5) Uani 1 1 d . . . . .
H21 H 1.1799 0.1966 0.1313 0.030 Uiso 1 1 calc R . . . .
N1 N 0.87718(18) 0.1012(2) -0.00336(11) 0.0171(4) Uani 1 1 d . . . . .
H1A H 0.877(3) 0.015(3) -0.0202(16) 0.021 Uiso 1 1 d R . . . .
N2 N 0.98826(17) 0.1524(2) 0.03325(10) 0.0173(4) Uani 1 1 d . . . . .
Se1 Se 0.71972(2) 0.46359(2) 0.06111(2) 0.01792(9) 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
C1 H1 0.9500 . ?
C1 C2 1.389(3) . ?
C1 C6 1.401(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(3) . ?
C6 C7 1.472(3) . ?
C7 C8 1.393(3) . ?
C7 N1 1.348(3) . ?
C8 C9 1.426(3) . ?
C8 Se1 1.896(2) . ?
C9 C16 1.477(3) . ?
C9 N2 1.336(3) . ?
C10 C11 1.395(3) . ?
C10 C15 1.394(3) . ?
C10 Se1 1.925(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(3) . ?
C16 C21 1.402(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.377(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(3) . ?
C21 H21 0.9500 . ?
N1 H1A 0.88(3) . ?
N1 N2 1.359(3) . ?

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
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.2(2) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 118.5(2) . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 C7 122.1(2) . . ?
C8 C7 C6 133.0(2) . . ?
N1 C7 C6 120.6(2) . . ?
N1 C7 C8 106.11(19) . . ?
C7 C8 C9 105.39(18) . . ?
C7 C8 Se1 124.24(16) . . ?
C9 C8 Se1 130.24(16) . . ?
C8 C9 C16 131.9(2) . . ?
N2 C9 C8 110.02(19) . . ?
N2 C9 C16 118.05(19) . . ?
C11 C10 Se1 117.01(18) . . ?
C15 C10 C11 119.9(2) . . ?
C15 C10 Se1 123.04(16) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(2) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 120.3 . . ?
C14 C15 C10 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C9 122.2(2) . . ?
C17 C16 C21 118.2(2) . . ?
C21 C16 C9 119.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.1(2) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C7 N1 H1A 128.0(18) . . ?
C7 N1 N2 112.86(18) . . ?
N2 N1 H1A 118.7(18) . . ?
C9 N2 N1 105.61(17) . . ?
C8 Se1 C10 99.13(9) . . ?

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
N1 H1A N2 0.88(3) 2.15(3) 2.869(3) 139(2) 3_755

_olex2_submission_special_instructions 'No special instructions were received'
