# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_20181207gtn112_d_1
_database_code_depnum_ccdc_archive 'CCDC 1890800'
loop_
_audit_author_name
_audit_author_address
'Tao Guo'
;Henan University of Technology
China
;
_audit_update_record             
;
2019-01-14 deposited with the CCDC.	2019-03-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 N2 Se'
_chemical_formula_iupac          ?
_chemical_formula_weight         355.33

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   13.3462(4)
_cell_length_b                   10.2259(3)
_cell_length_c                   12.0633(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.4660(10)
_cell_angle_gamma                90
_cell_volume                     1635.89(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9542
_cell_measurement_theta_min      3.3327
_cell_measurement_theta_max      72.3034
_cell_measurement_temperature    161.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728

_exptl_absorpt_coefficient_mu    3.073
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.5250
_exptl_absorpt_correction_T_max  0.7536

_exptl_special_details           
;
;

_diffrn_ambient_temperature      161.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'cu k\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            37356
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         72.35
_diffrn_reflns_theta_full        72.35
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             3247
_reflns_number_gt                3072
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0712
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_number_reflns         3247
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)²+0.8222P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.474
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se1 0.80105(2) 0.69344(2) 0.70649(2) 0.02397(9) Uani d . . . 1 . .
N N1 0.60966(11) 0.69409(11) 0.79313(11) 0.0210(3) Uani d . . . 1 . .
C C1 0.56168(13) 0.77884(16) 0.71514(13) 0.0255(3) Uani d . . . 1 . .
H H1 0.595373 0.810918 0.655385 0.031 Uiso calc U . R 1 . .
C C9 0.87552(14) 0.36980(18) 1.11308(14) 0.0322(4) Uani d . . . 1 . .
H H9 0.87642 0.347799 1.189692 0.039 Uiso calc U . R 1 . .
C C2 0.46566(14) 0.81521(15) 0.72570(15) 0.0281(4) Uani d . . . 1 . .
H H2 0.431853 0.874038 0.673177 0.034 Uiso calc U . R 1 . .
C C8 0.79940(13) 0.44897(17) 1.06225(13) 0.0277(3) Uani d . . . 1 . .
H H8 0.748888 0.481479 1.10453 0.033 Uiso calc U . R 1 . .
N N2 0.62487(10) 0.56869(12) 0.94685(10) 0.0218(3) Uani d . . . 1 . .
C C3 0.41498(13) 0.76637(17) 0.81440(14) 0.0282(3) Uani d . . . 1 . .
H H3 0.347293 0.791901 0.819957 0.034 Uiso calc U . R 1 . .
C C4 0.46235(13) 0.68318(15) 0.89176(14) 0.0261(3) Uani d . . . 1 . .
H H4 0.428227 0.65024 0.950875 0.031 Uiso calc U . R 1 . .
C C5 0.56323(12) 0.64700(15) 0.88217(12) 0.0216(3) Uani d . . . 1 . .
C C6 0.71280(12) 0.56420(14) 0.89807(12) 0.0204(3) Uani d . . . 1 . .
C C7 0.79635(12) 0.48125(14) 0.94962(13) 0.0217(3) Uani d . . . 1 . .
C C14 0.77954(12) 0.55801(15) 0.58903(12) 0.0229(3) Uani d . . . 1 . .
H H14 0.797823 0.47081 0.623005 0.028 Uiso calc U . R 1 . .
C C10 0.95024(15) 0.32262(17) 1.05288(16) 0.0317(4) Uani d . . . 1 . .
H H10 1.002877 0.269507 1.088177 0.038 Uiso calc U . R 1 . .
C C15 0.85256(13) 0.59009(17) 0.50429(14) 0.0282(3) Uani d . . . 1 . .
H H15A 0.922516 0.589191 0.541649 0.034 Uiso calc U . R 1 . .
H H15B 0.838213 0.678912 0.473913 0.034 Uiso calc U . R 1 . .
C C12 0.87098(13) 0.43167(16) 0.88928(14) 0.0277(3) Uani d . . . 1 . .
H H12 0.869445 0.451526 0.812178 0.033 Uiso calc U . R 1 . .
C C11 0.94762(14) 0.35345(17) 0.94095(15) 0.0315(4) Uani d . . . 1 . .
H H11 0.998493 0.320964 0.899168 0.038 Uiso calc U . R 1 . .
C C16 0.84261(14) 0.49078(18) 0.40888(14) 0.0325(4) Uani d . . . 1 . .
H H16A 0.886224 0.517834 0.351785 0.039 Uiso calc U . R 1 . .
H H16B 0.866175 0.404234 0.43794 0.039 Uiso calc U . R 1 . .
C C13 0.70663(12) 0.64102(16) 0.80249(12) 0.0223(3) Uani d . . . 1 . .
C C17 0.73424(14) 0.47915(17) 0.35506(14) 0.0303(4) Uani d . . . 1 . .
H H17A 0.729767 0.408073 0.299003 0.036 Uiso calc U . R 1 . .
H H17B 0.714168 0.561754 0.315888 0.036 Uiso calc U . R 1 . .
C C19 0.67141(13) 0.55256(17) 0.53429(13) 0.0277(3) Uani d . . . 1 . .
H H19A 0.65125 0.639443 0.503144 0.033 Uiso calc U . R 1 . .
H H19B 0.625887 0.529629 0.590685 0.033 Uiso calc U . R 1 . .
C C18 0.66176(15) 0.45057(19) 0.44110(15) 0.0344(4) Uani d . . . 1 . .
H H18A 0.676297 0.36275 0.473528 0.041 Uiso calc U . R 1 . .
H H18B 0.591722 0.450283 0.403974 0.041 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Se1 C13 . 1.8830(15) ?
Se1 C14 . 1.9789(15) ?
N1 C1 . 1.382(2) ?
N1 C5 . 1.385(2) ?
N1 C13 . 1.396(2) ?
C1 C2 . 1.354(3) ?
C1 H1 . 0.95 ?
C9 C10 . 1.385(3) ?
C9 C8 . 1.387(2) ?
C9 H9 . 0.95 ?
C2 C3 . 1.419(3) ?
C2 H2 . 0.95 ?
C8 C7 . 1.394(2) ?
C8 H8 . 0.95 ?
N2 C5 . 1.335(2) ?
N2 C6 . 1.371(2) ?
C3 C4 . 1.364(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.414(2) ?
C4 H4 . 0.95 ?
C6 C13 . 1.390(2) ?
C6 C7 . 1.481(2) ?
C7 C12 . 1.394(2) ?
C14 C19 . 1.519(2) ?
C14 C15 . 1.525(2) ?
C14 H14 . 1.0 ?
C10 C11 . 1.383(3) ?
C10 H10 . 0.95 ?
C15 C16 . 1.529(2) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C12 C11 . 1.390(2) ?
C12 H12 . 0.95 ?
C11 H11 . 0.95 ?
C16 C17 . 1.522(3) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 C18 . 1.525(2) ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?
C19 C18 . 1.528(2) ?
C19 H19A . 0.99 ?
C19 H19B . 0.99 ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 Se1 C14 . . 100.83(7) ?
C1 N1 C5 . . 122.16(14) ?
C1 N1 C13 . . 130.76(14) ?
C5 N1 C13 . . 107.07(13) ?
C2 C1 N1 . . 118.62(15) ?
C2 C1 H1 . . 120.7 ?
N1 C1 H1 . . 120.7 ?
C10 C9 C8 . . 120.43(16) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C1 C2 C3 . . 120.70(15) ?
C1 C2 H2 . . 119.6 ?
C3 C2 H2 . . 119.6 ?
C9 C8 C7 . . 120.57(16) ?
C9 C8 H8 . . 119.7 ?
C7 C8 H8 . . 119.7 ?
C5 N2 C6 . . 105.67(13) ?
C4 C3 C2 . . 120.77(16) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C3 C4 C5 . . 118.65(16) ?
C3 C4 H4 . . 120.7 ?
C5 C4 H4 . . 120.7 ?
N2 C5 N1 . . 111.20(14) ?
N2 C5 C4 . . 129.72(15) ?
N1 C5 C4 . . 119.06(14) ?
N2 C6 C13 . . 111.30(13) ?
N2 C6 C7 . . 118.64(13) ?
C13 C6 C7 . . 130.05(14) ?
C12 C7 C8 . . 118.60(15) ?
C12 C7 C6 . . 122.52(14) ?
C8 C7 C6 . . 118.86(14) ?
C19 C14 C15 . . 111.34(13) ?
C19 C14 Se1 . . 113.02(11) ?
C15 C14 Se1 . . 106.09(10) ?
C19 C14 H14 . . 108.8 ?
C15 C14 H14 . . 108.8 ?
Se1 C14 H14 . . 108.8 ?
C11 C10 C9 . . 119.47(16) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
C14 C15 C16 . . 110.71(14) ?
C14 C15 H15A . . 109.5 ?
C16 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
C16 C15 H15B . . 109.5 ?
H15A C15 H15B . . 108.1 ?
C11 C12 C7 . . 120.56(15) ?
C11 C12 H12 . . 119.7 ?
C7 C12 H12 . . 119.7 ?
C10 C11 C12 . . 120.36(16) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C17 C16 C15 . . 111.76(14) ?
C17 C16 H16A . . 109.3 ?
C15 C16 H16A . . 109.3 ?
C17 C16 H16B . . 109.3 ?
C15 C16 H16B . . 109.3 ?
H16A C16 H16B . . 107.9 ?
C6 C13 N1 . . 104.75(13) ?
C6 C13 Se1 . . 133.62(12) ?
N1 C13 Se1 . . 121.20(11) ?
C16 C17 C18 . . 111.71(14) ?
C16 C17 H17A . . 109.3 ?
C18 C17 H17A . . 109.3 ?
C16 C17 H17B . . 109.3 ?
C18 C17 H17B . . 109.3 ?
H17A C17 H17B . . 107.9 ?
C14 C19 C18 . . 110.00(14) ?
C14 C19 H19A . . 109.7 ?
C18 C19 H19A . . 109.7 ?
C14 C19 H19B . . 109.7 ?
C18 C19 H19B . . 109.7 ?
H19A C19 H19B . . 108.2 ?
C17 C18 C19 . . 111.26(14) ?
C17 C18 H18A . . 109.4 ?
C19 C18 H18A . . 109.4 ?
C17 C18 H18B . . 109.4 ?
C19 C18 H18B . . 109.4 ?
H18A C18 H18B . . 108.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . -1.0(2) ?
C13 N1 C1 C2 . . . . 179.86(15) ?
N1 C1 C2 C3 . . . . -0.6(2) ?
C10 C9 C8 C7 . . . . 0.6(3) ?
C1 C2 C3 C4 . . . . 0.9(3) ?
C2 C3 C4 C5 . . . . 0.3(2) ?
C6 N2 C5 N1 . . . . -0.48(16) ?
C6 N2 C5 C4 . . . . 178.21(15) ?
C1 N1 C5 N2 . . . . -179.00(13) ?
C13 N1 C5 N2 . . . . 0.35(16) ?
C1 N1 C5 C4 . . . . 2.2(2) ?
C13 N1 C5 C4 . . . . -178.50(14) ?
C3 C4 C5 N2 . . . . 179.63(16) ?
C3 C4 C5 N1 . . . . -1.8(2) ?
C5 N2 C6 C13 . . . . 0.44(17) ?
C5 N2 C6 C7 . . . . -178.48(13) ?
C9 C8 C7 C12 . . . . 0.4(2) ?
C9 C8 C7 C6 . . . . 178.97(15) ?
N2 C6 C7 C12 . . . . 155.80(15) ?
C13 C6 C7 C12 . . . . -22.9(2) ?
N2 C6 C7 C8 . . . . -22.7(2) ?
C13 C6 C7 C8 . . . . 158.57(16) ?
C8 C9 C10 C11 . . . . -1.0(3) ?
C19 C14 C15 C16 . . . . -56.73(18) ?
Se1 C14 C15 C16 . . . . 179.92(11) ?
C8 C7 C12 C11 . . . . -1.0(2) ?
C6 C7 C12 C11 . . . . -179.55(15) ?
C9 C10 C11 C12 . . . . 0.3(3) ?
C7 C12 C11 C10 . . . . 0.7(3) ?
C14 C15 C16 C17 . . . . 54.04(19) ?
N2 C6 C13 N1 . . . . -0.24(17) ?
C7 C6 C13 N1 . . . . 178.54(14) ?
N2 C6 C13 Se1 . . . . 172.05(12) ?
C7 C6 C13 Se1 . . . . -9.2(3) ?
C1 N1 C13 C6 . . . . 179.21(15) ?
C5 N1 C13 C6 . . . . -0.06(16) ?
C1 N1 C13 Se1 . . . . 5.7(2) ?
C5 N1 C13 Se1 . . . . -173.53(10) ?
C14 Se1 C13 C6 . . . . 94.76(16) ?
C14 Se1 C13 N1 . . . . -93.98(13) ?
C15 C16 C17 C18 . . . . -53.4(2) ?
C15 C14 C19 C18 . . . . 58.03(18) ?
Se1 C14 C19 C18 . . . . 177.33(11) ?
C16 C17 C18 C19 . . . . 54.8(2) ?
C14 C19 C18 C17 . . . . -56.8(2) ?



