# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_1a-DMAP
_database_code_depnum_ccdc_archive 'CCDC 1867205'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_1a-DMAP             
;
PROBLEM: Short Inter D...A Contact  Se1      ..N2       .       2.37 Ang.
RESPONSE: CHALCOGEN BONDING
;
# Added during the CSD deposition process: Wednesday 12 September 2018 03:20 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N3 O Se'
_chemical_formula_weight         396.34
_chemical_oxdiff_usercomment     'Tom Fellowes Ph-Ebselon DMAP from DCM/pentane'

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'
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'

_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                   8.3674(3)
_cell_length_b                   9.8399(5)
_cell_length_c                   10.6622(5)
_cell_angle_alpha                93.296(4)
_cell_angle_beta                 93.021(4)
_cell_angle_gamma                101.210(4)
_cell_volume                     857.86(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    4171
_cell_measurement_theta_min      3.8890
_cell_measurement_theta_max      36.6090

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.524
_exptl_crystal_size_mid          0.343
_exptl_crystal_size_min          0.233
_exptl_absorpt_coefficient_mu    2.202
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.512
_exptl_absorpt_correction_T_max  0.704
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.701
_oxdiff_exptl_absorpt_empirical_full_max 1.309
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (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  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            11339
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.493
_diffrn_reflns_theta_max         36.664
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7889
_reflns_number_gt                6882
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0306P)²+0.2644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7889
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.001
_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
C1 C 0.63281(14) 0.24961(12) 0.48695(11) 0.01677(19) Uani 1 1 d . . . . .
C2 C 0.71605(14) 0.21013(12) 0.59019(11) 0.01653(19) Uani 1 1 d . . . . .
C3 C 0.88639(15) 0.23957(13) 0.60273(12) 0.0204(2) Uani 1 1 d . . . . .
H3 H 0.942439 0.213176 0.674323 0.024 Uiso 1 1 calc R U . . .
C4 C 0.97261(16) 0.30743(14) 0.51007(13) 0.0234(2) Uani 1 1 d . . . . .
H4 H 1.088577 0.328275 0.517516 0.028 Uiso 1 1 calc R U . . .
C5 C 0.88858(16) 0.34510(14) 0.40570(13) 0.0244(2) Uani 1 1 d . . . . .
H5 H 0.948581 0.390833 0.341787 0.029 Uiso 1 1 calc R U . . .
C6 C 0.71958(16) 0.31753(14) 0.39276(12) 0.0215(2) Uani 1 1 d . . . . .
H6 H 0.663845 0.344318 0.321202 0.026 Uiso 1 1 calc R U . . .
C7 C 0.61786(14) 0.13837(12) 0.68653(11) 0.01702(19) Uani 1 1 d . . . . .
C8 C 0.32790(14) 0.05479(12) 0.72211(11) 0.01642(19) Uani 1 1 d . . . . .
C9 C 0.16964(15) 0.02119(13) 0.66465(12) 0.0206(2) Uani 1 1 d . . . . .
H9 H 0.151110 0.040525 0.579418 0.025 Uiso 1 1 calc R U . . .
C10 C 0.03950(16) -0.04018(14) 0.73115(13) 0.0242(2) Uani 1 1 d . . . . .
H10 H -0.067442 -0.061826 0.691236 0.029 Uiso 1 1 calc R U . . .
C11 C 0.06424(17) -0.07005(14) 0.85500(13) 0.0241(2) Uani 1 1 d . . . . .
H11 H -0.025064 -0.112021 0.900231 0.029 Uiso 1 1 calc R U . . .
C12 C 0.22084(17) -0.03808(14) 0.91249(12) 0.0222(2) Uani 1 1 d . . . . .
H12 H 0.238495 -0.058846 0.997426 0.027 Uiso 1 1 calc R U . . .
C13 C 0.35232(16) 0.02400(13) 0.84730(11) 0.0193(2) Uani 1 1 d . . . . .
H13 H 0.458893 0.045522 0.887858 0.023 Uiso 1 1 calc R U . . .
C14 C 0.32734(17) 0.43816(13) 0.30625(12) 0.0221(2) Uani 1 1 d . . . . .
H14 H 0.326876 0.488298 0.385036 0.027 Uiso 1 1 calc R U . . .
C15 C 0.28708(17) 0.49885(13) 0.19911(12) 0.0218(2) Uani 1 1 d . . . . .
H15 H 0.259248 0.588005 0.205050 0.026 Uiso 1 1 calc R U . . .
C16 C 0.28736(15) 0.42792(12) 0.08031(11) 0.0185(2) Uani 1 1 d . . . . .
C17 C 0.33198(16) 0.29707(13) 0.08161(12) 0.0210(2) Uani 1 1 d . . . . .
H17 H 0.337152 0.244978 0.004615 0.025 Uiso 1 1 calc R U . . .
C18 C 0.36793(17) 0.24490(13) 0.19378(12) 0.0221(2) Uani 1 1 d . . . . .
H18 H 0.394984 0.155438 0.191671 0.027 Uiso 1 1 calc R U . . .
C19 C 0.2098(2) 0.61898(15) -0.02901(15) 0.0305(3) Uani 1 1 d . . . . .
H19A H 0.107979 0.620813 0.011830 0.046 Uiso 1 1 calc R U . . .
H19B H 0.198112 0.644053 -0.116173 0.046 Uiso 1 1 calc R U . . .
H19C H 0.299243 0.685585 0.016641 0.046 Uiso 1 1 calc R U . . .
C20 C 0.2394(2) 0.40022(17) -0.14743(13) 0.0318(3) Uani 1 1 d . . . . .
H20A H 0.350214 0.391607 -0.167200 0.048 Uiso 1 1 calc R U . . .
H20B H 0.191383 0.447350 -0.213996 0.048 Uiso 1 1 calc R U . . .
H20C H 0.172419 0.307573 -0.141697 0.048 Uiso 1 1 calc R U . . .
N1 N 0.45621(12) 0.12028(11) 0.65194(9) 0.01674(17) Uani 1 1 d . . . . .
N2 N 0.36713(14) 0.31283(11) 0.30642(10) 0.02062(19) Uani 1 1 d . . . . .
N3 N 0.24562(16) 0.48046(12) -0.02799(11) 0.0255(2) Uani 1 1 d . . . . .
O1 O 0.67984(12) 0.10207(11) 0.78351(9) 0.02428(19) Uani 1 1 d . . . . .
Se1 Se 0.40302(2) 0.20233(2) 0.49486(2) 0.01677(3) 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 C2 1.3861(17) . ?
C1 C6 1.3956(16) . ?
C1 Se1 1.8959(12) . ?
C2 C3 1.3957(17) . ?
C2 C7 1.4750(16) . ?
C3 C4 1.3807(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3850(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.2345(14) . ?
C7 N1 1.3577(15) . ?
C8 C13 1.3989(16) . ?
C8 C9 1.3997(17) . ?
C8 N1 1.4138(15) . ?
C9 C10 1.3886(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3829(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3910(17) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 N2 1.3385(17) . ?
C14 C15 1.3752(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.4110(18) . ?
C15 H15 0.9500 . ?
C16 N3 1.3487(16) . ?
C16 C17 1.4092(17) . ?
C17 C18 1.3701(18) . ?
C17 H17 0.9500 . ?
C18 N2 1.3413(17) . ?
C18 H18 0.9500 . ?
C19 N3 1.4518(18) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N3 1.4523(19) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1 Se1 1.9676(10) . ?

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 C6 119.93(11) . . ?
C2 C1 Se1 112.56(8) . . ?
C6 C1 Se1 127.51(9) . . ?
C1 C2 C3 120.88(11) . . ?
C1 C2 C7 117.49(10) . . ?
C3 C2 C7 121.62(11) . . ?
C4 C3 C2 119.35(12) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.58(12) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 121.59(12) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 118.67(12) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
O1 C7 N1 126.99(11) . . ?
O1 C7 C2 122.65(11) . . ?
N1 C7 C2 110.37(10) . . ?
C13 C8 C9 118.64(11) . . ?
C13 C8 N1 122.64(11) . . ?
C9 C8 N1 118.70(10) . . ?
C10 C9 C8 120.56(12) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.56(12) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.31(12) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 120.80(12) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 120.12(12) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
N2 C14 C15 124.07(12) . . ?
N2 C14 H14 118.0 . . ?
C15 C14 H14 118.0 . . ?
C14 C15 C16 119.61(12) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
N3 C16 C17 121.74(11) . . ?
N3 C16 C15 122.47(12) . . ?
C17 C16 C15 115.78(11) . . ?
C18 C17 C16 120.08(12) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
N2 C18 C17 123.80(12) . . ?
N2 C18 H18 118.1 . . ?
C17 C18 H18 118.1 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 N1 C8 125.36(10) . . ?
C7 N1 Se1 115.37(8) . . ?
C8 N1 Se1 119.19(8) . . ?
C14 N2 C18 116.65(11) . . ?
C16 N3 C19 121.28(12) . . ?
C16 N3 C20 120.39(12) . . ?
C19 N3 C20 118.31(12) . . ?
C1 Se1 N1 84.09(5) . . ?

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
C6 C1 C2 C3 1.16(18) . . . . ?
Se1 C1 C2 C3 -178.26(9) . . . . ?
C6 C1 C2 C7 -179.84(11) . . . . ?
Se1 C1 C2 C7 0.74(14) . . . . ?
C1 C2 C3 C4 -0.80(19) . . . . ?
C7 C2 C3 C4 -179.76(12) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C2 C1 C6 C5 -0.58(19) . . . . ?
Se1 C1 C6 C5 178.75(10) . . . . ?
C1 C2 C7 O1 -178.10(12) . . . . ?
C3 C2 C7 O1 0.89(19) . . . . ?
C1 C2 C7 N1 1.84(15) . . . . ?
C3 C2 C7 N1 -179.17(11) . . . . ?
C13 C8 C9 C10 0.64(19) . . . . ?
N1 C8 C9 C10 -178.46(12) . . . . ?
C8 C9 C10 C11 -0.5(2) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C8 -0.14(19) . . . . ?
C9 C8 C13 C12 -0.34(18) . . . . ?
N1 C8 C13 C12 178.72(11) . . . . ?
N2 C14 C15 C16 -0.4(2) . . . . ?
C14 C15 C16 N3 178.52(13) . . . . ?
C14 C15 C16 C17 -0.63(19) . . . . ?
N3 C16 C17 C18 -177.64(13) . . . . ?
C15 C16 C17 C18 1.52(18) . . . . ?
C16 C17 C18 N2 -1.5(2) . . . . ?
O1 C7 N1 C8 -0.3(2) . . . . ?
C2 C7 N1 C8 179.75(10) . . . . ?
O1 C7 N1 Se1 176.43(11) . . . . ?
C2 C7 N1 Se1 -3.51(13) . . . . ?
C13 C8 N1 C7 12.42(19) . . . . ?
C9 C8 N1 C7 -168.52(12) . . . . ?
C13 C8 N1 Se1 -164.20(9) . . . . ?
C9 C8 N1 Se1 14.86(15) . . . . ?
C15 C14 N2 C18 0.5(2) . . . . ?
C17 C18 N2 C14 0.5(2) . . . . ?
C17 C16 N3 C19 -176.07(13) . . . . ?
C15 C16 N3 C19 4.8(2) . . . . ?
C17 C16 N3 C20 2.4(2) . . . . ?
C15 C16 N3 C20 -176.70(14) . . . . ?
C2 C1 Se1 N1 -2.07(9) . . . . ?
C6 C1 Se1 N1 178.56(12) . . . . ?

_refine_diff_density_max         0.522
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_1b-DABCO
_database_code_depnum_ccdc_archive 'CCDC 1867206'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_1b-DABCO            
;
PROBLEM: Short Inter D...A Contact  Se1      ..N2       .       2.62 Ang.
RESPONSE: CHALCOGEN BONDING
;
# Added during the CSD deposition process: Wednesday 12 September 2018 03:20 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H23 N3 O Se'
_chemical_formula_weight         400.37
_chemical_oxdiff_usercomment     'benzyl ebeselen and dabco'

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1249(2)
_cell_length_b                   15.9246(3)
_cell_length_c                   11.4660(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.572(2)
_cell_angle_gamma                90
_cell_volume                     1771.93(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    5731
_cell_measurement_theta_min      4.5380
_cell_measurement_theta_max      77.0710

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    2.965
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.763
_oxdiff_exptl_absorpt_empirical_full_max 1.273
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            13121
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.556
_diffrn_reflns_theta_max         77.119
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3711
_reflns_number_gt                3333
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0307P)²+0.9873P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3711
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_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
C1 C 0.35101(17) 0.42908(11) 0.63387(15) 0.0168(3) Uani 1 1 d . . . . .
C2 C 0.26199(18) 0.49711(12) 0.59711(17) 0.0201(3) Uani 1 1 d . . . . .
H2 H 0.224111 0.509887 0.513256 0.024 Uiso 1 1 calc R U . . .
C3 C 0.23008(19) 0.54567(12) 0.68587(18) 0.0235(4) Uani 1 1 d . . . . .
H3 H 0.170322 0.592495 0.662026 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2839(2) 0.52723(12) 0.80963(17) 0.0233(4) Uani 1 1 d . . . . .
H4 H 0.260042 0.561054 0.868824 0.028 Uiso 1 1 calc R U . . .
C5 C 0.37183(19) 0.45972(12) 0.84565(16) 0.0211(4) Uani 1 1 d . . . . .
H5 H 0.408183 0.446522 0.929518 0.025 Uiso 1 1 calc R U . . .
C6 C 0.40662(17) 0.41120(11) 0.75766(16) 0.0169(3) Uani 1 1 d . . . . .
C7 C 0.50841(18) 0.34219(11) 0.78794(16) 0.0183(3) Uani 1 1 d . . . . .
C8 C 0.62775(18) 0.24361(11) 0.68573(16) 0.0189(3) Uani 1 1 d . . . . .
H8A H 0.594607 0.208910 0.611459 0.023 Uiso 1 1 calc R U . . .
H8B H 0.635947 0.206800 0.757028 0.023 Uiso 1 1 calc R U . . .
C9 C 0.76844(18) 0.27931(11) 0.69141(15) 0.0170(3) Uani 1 1 d . . . . .
C10 C 0.80608(19) 0.29159(12) 0.58475(16) 0.0216(4) Uani 1 1 d . . . . .
H10 H 0.744041 0.276693 0.508471 0.026 Uiso 1 1 calc R U . . .
C11 C 0.9341(2) 0.32556(13) 0.58962(17) 0.0243(4) Uani 1 1 d . . . . .
H11 H 0.959343 0.333056 0.516614 0.029 Uiso 1 1 calc R U . . .
C12 C 1.02521(19) 0.34859(12) 0.70012(18) 0.0227(4) Uani 1 1 d . . . . .
H12 H 1.112490 0.371799 0.702925 0.027 Uiso 1 1 calc R U . . .
C13 C 0.9878(2) 0.33743(12) 0.80683(17) 0.0236(4) Uani 1 1 d . . . . .
H13 H 1.049215 0.353541 0.882820 0.028 Uiso 1 1 calc R U . . .
C14 C 0.86034(19) 0.30264(12) 0.80202(16) 0.0211(4) Uani 1 1 d . . . . .
H14 H 0.835642 0.294678 0.875208 0.025 Uiso 1 1 calc R U . . .
C15 C 0.3073(2) 0.33390(14) 0.25990(18) 0.0303(5) Uani 1 1 d . . . . .
H15A H 0.278620 0.280311 0.289114 0.036 Uiso 1 1 calc R U . . .
H15B H 0.409058 0.334028 0.279721 0.036 Uiso 1 1 calc R U . . .
C16 C 0.2440(2) 0.34061(13) 0.12056(17) 0.0264(4) Uani 1 1 d . . . . .
H16A H 0.318631 0.340897 0.080448 0.032 Uiso 1 1 calc R U . . .
H16B H 0.184728 0.291185 0.090661 0.032 Uiso 1 1 calc R U . . .
C17 C 0.2509(2) 0.48972(13) 0.13801(17) 0.0260(4) Uani 1 1 d . . . . .
H17A H 0.198086 0.542444 0.115188 0.031 Uiso 1 1 calc R U . . .
H17B H 0.329225 0.490939 0.102381 0.031 Uiso 1 1 calc R U . . .
C18 C 0.3067(2) 0.48388(13) 0.27899(17) 0.0280(4) Uani 1 1 d . . . . .
H18A H 0.408634 0.486381 0.303757 0.034 Uiso 1 1 calc R U . . .
H18B H 0.272318 0.532109 0.316376 0.034 Uiso 1 1 calc R U . . .
C19 C 0.10992(19) 0.40393(14) 0.28747(18) 0.0276(4) Uani 1 1 d . . . . .
H19A H 0.076316 0.449703 0.330045 0.033 Uiso 1 1 calc R U . . .
H19B H 0.077734 0.349880 0.312211 0.033 Uiso 1 1 calc R U . . .
C20 C 0.0506(2) 0.41541(14) 0.14768(18) 0.0285(4) Uani 1 1 d . . . . .
H20A H -0.012663 0.368406 0.113678 0.034 Uiso 1 1 calc R U . . .
H20B H -0.002775 0.468323 0.130529 0.034 Uiso 1 1 calc R U . . .
N1 N 0.52716(15) 0.30996(10) 0.68443(13) 0.0181(3) Uani 1 1 d . . . . .
N2 N 0.26178(15) 0.40505(9) 0.32233(13) 0.0179(3) Uani 1 1 d . . . . .
N3 N 0.16188(17) 0.41778(10) 0.08895(14) 0.0238(3) Uani 1 1 d . . . . .
O1 O 0.56914(14) 0.31832(9) 0.89196(12) 0.0239(3) Uani 1 1 d . . . . .
Se1 Se 0.41751(2) 0.35478(2) 0.53423(2) 0.01649(7) 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 C2 1.395(2) . ?
C1 C6 1.399(2) . ?
C1 Se1 1.8967(17) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.479(2) . ?
C7 O1 1.236(2) . ?
C7 N1 1.355(2) . ?
C8 N1 1.465(2) . ?
C8 C9 1.518(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.392(2) . ?
C9 C10 1.395(2) . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N2 1.482(2) . ?
C15 C16 1.546(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N3 1.470(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N3 1.467(2) . ?
C17 C18 1.556(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N2 1.469(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N2 1.474(2) . ?
C19 C20 1.554(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 N3 1.469(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
N1 Se1 1.9019(14) . ?

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 C6 120.20(16) . . ?
C2 C1 Se1 127.74(13) . . ?
C6 C1 Se1 112.02(13) . . ?
C3 C2 C1 118.46(17) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.49(18) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 119.86(17) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.30(17) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 120.67(17) . . ?
C5 C6 C7 123.05(16) . . ?
C1 C6 C7 116.19(16) . . ?
O1 C7 N1 124.99(17) . . ?
O1 C7 C6 125.23(17) . . ?
N1 C7 C6 109.77(15) . . ?
N1 C8 C9 111.81(14) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C14 C9 C10 118.85(17) . . ?
C14 C9 C8 120.94(16) . . ?
C10 C9 C8 120.18(15) . . ?
C11 C10 C9 120.26(17) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.59(17) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.51(18) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 119.87(17) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 120.91(17) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
N2 C15 C16 110.62(16) . . ?
N2 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N3 C16 C15 110.54(15) . . ?
N3 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
N3 C17 C18 110.67(15) . . ?
N3 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
N2 C18 C17 110.30(15) . . ?
N2 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
N2 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
N2 C19 C20 110.16(16) . . ?
N2 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
N2 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
N3 C20 C19 110.77(15) . . ?
N3 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C7 N1 C8 122.34(15) . . ?
C7 N1 Se1 117.36(12) . . ?
C8 N1 Se1 120.30(11) . . ?
C18 N2 C19 108.55(16) . . ?
C18 N2 C15 108.72(16) . . ?
C19 N2 C15 107.67(16) . . ?
C17 N3 C20 108.20(15) . . ?
C17 N3 C16 108.39(15) . . ?
C20 N3 C16 108.63(16) . . ?
C1 Se1 N1 84.52(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
C6 C1 C2 C3 -0.3(3) . . . . ?
Se1 C1 C2 C3 -177.60(14) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C4 C5 C6 C7 174.91(17) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
Se1 C1 C6 C5 179.06(14) . . . . ?
C2 C1 C6 C7 -175.25(16) . . . . ?
Se1 C1 C6 C7 2.4(2) . . . . ?
C5 C6 C7 O1 2.6(3) . . . . ?
C1 C6 C7 O1 179.16(17) . . . . ?
C5 C6 C7 N1 -176.24(16) . . . . ?
C1 C6 C7 N1 0.3(2) . . . . ?
N1 C8 C9 C14 83.4(2) . . . . ?
N1 C8 C9 C10 -94.7(2) . . . . ?
C14 C9 C10 C11 0.8(3) . . . . ?
C8 C9 C10 C11 178.97(17) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C9 -0.6(3) . . . . ?
C10 C9 C14 C13 -0.2(3) . . . . ?
C8 C9 C14 C13 -178.28(17) . . . . ?
N2 C15 C16 N3 2.7(3) . . . . ?
N3 C17 C18 N2 3.8(2) . . . . ?
N2 C19 C20 N3 4.2(2) . . . . ?
O1 C7 N1 C8 -2.2(3) . . . . ?
C6 C7 N1 C8 176.63(15) . . . . ?
O1 C7 N1 Se1 178.13(14) . . . . ?
C6 C7 N1 Se1 -3.00(19) . . . . ?
C9 C8 N1 C7 -89.0(2) . . . . ?
C9 C8 N1 Se1 90.65(16) . . . . ?
C17 C18 N2 C19 -60.9(2) . . . . ?
C17 C18 N2 C15 56.0(2) . . . . ?
C20 C19 N2 C18 56.3(2) . . . . ?
C20 C19 N2 C15 -61.2(2) . . . . ?
C16 C15 N2 C18 -59.9(2) . . . . ?
C16 C15 N2 C19 57.5(2) . . . . ?
C18 C17 N3 C20 56.6(2) . . . . ?
C18 C17 N3 C16 -61.1(2) . . . . ?
C19 C20 N3 C17 -61.1(2) . . . . ?
C19 C20 N3 C16 56.3(2) . . . . ?
C15 C16 N3 C17 57.2(2) . . . . ?
C15 C16 N3 C20 -60.1(2) . . . . ?
C2 C1 Se1 N1 174.31(17) . . . . ?
C6 C1 Se1 N1 -3.16(13) . . . . ?

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
C8 H8A O1 0.99 2.49 3.396(2) 151.3 4_565

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_1b-QUIN
_database_code_depnum_ccdc_archive 'CCDC 1867207'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_1b-QUIN             
;
PROBLEM: Short Inter D...A Contact  Se1      ..N2       .       2.59 Ang.
RESPONSE: CHALCOGEN BONDING
;
# Added during the CSD deposition process: Wednesday 12 September 2018 03:20 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 N2 O Se'
_chemical_formula_weight         399.38
_chemical_oxdiff_usercomment     'benzylebselen + quinuclidine'

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1610(2)
_cell_length_b                   16.0506(3)
_cell_length_c                   11.4300(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.622(2)
_cell_angle_gamma                90
_cell_volume                     1803.75(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    5880
_cell_measurement_theta_min      4.8470
_cell_measurement_theta_max      76.4770

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    2.895
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.62320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.646
_oxdiff_exptl_absorpt_empirical_full_max 1.329
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            12588
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.497
_diffrn_reflns_theta_max         77.192
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3771
_reflns_number_gt                3397
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+1.1865P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3771
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_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
C1 C 0.3562(2) 0.57626(12) 0.64002(17) 0.0198(4) Uani 1 1 d . . . . .
C2 C 0.4126(2) 0.59563(13) 0.76151(18) 0.0198(4) Uani 1 1 d . . . . .
C3 C 0.3807(2) 0.54818(13) 0.85273(18) 0.0231(4) Uani 1 1 d . . . . .
H3 H 0.418006 0.562148 0.935216 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2942(2) 0.48059(14) 0.82238(19) 0.0254(4) Uani 1 1 d . . . . .
H4 H 0.272496 0.447588 0.883940 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2389(2) 0.46116(13) 0.7007(2) 0.0244(4) Uani 1 1 d . . . . .
H5 H 0.179613 0.414684 0.680447 0.029 Uiso 1 1 calc R U . . .
C6 C 0.2688(2) 0.50842(13) 0.60832(18) 0.0219(4) Uani 1 1 d . . . . .
H6 H 0.230510 0.494745 0.525869 0.026 Uiso 1 1 calc R U . . .
C7 C 0.5121(2) 0.66478(13) 0.78585(18) 0.0200(4) Uani 1 1 d . . . . .
C8 C 0.6275(2) 0.76064(13) 0.67571(18) 0.0219(4) Uani 1 1 d . . . . .
H8A H 0.631474 0.800452 0.742678 0.026 Uiso 1 1 calc R U . . .
H8B H 0.597657 0.791570 0.598603 0.026 Uiso 1 1 calc R U . . .
C9 C 0.7675(2) 0.72486(12) 0.68606(18) 0.0204(4) Uani 1 1 d . . . . .
C10 C 0.8035(2) 0.69430(14) 0.58384(19) 0.0253(4) Uani 1 1 d . . . . .
H10 H 0.739847 0.696789 0.507130 0.030 Uiso 1 1 calc R U . . .
C11 C 0.9312(2) 0.66044(15) 0.5935(2) 0.0293(5) Uani 1 1 d . . . . .
H11 H 0.954015 0.639556 0.523335 0.035 Uiso 1 1 calc R U . . .
C12 C 1.0261(2) 0.65672(14) 0.7045(2) 0.0282(5) Uani 1 1 d . . . . .
H12 H 1.113606 0.633584 0.710687 0.034 Uiso 1 1 calc R U . . .
C13 C 0.9913(2) 0.68726(14) 0.8064(2) 0.0284(4) Uani 1 1 d . . . . .
H13 H 1.055678 0.685375 0.882766 0.034 Uiso 1 1 calc R U . . .
C14 C 0.8632(2) 0.72047(14) 0.79714(18) 0.0250(4) Uani 1 1 d . . . . .
H14 H 0.840294 0.740546 0.867660 0.030 Uiso 1 1 calc R U . . .
C15 C 0.1175(2) 0.59073(16) 0.3084(2) 0.0284(5) Uani 1 1 d . . . . .
H15A H 0.084990 0.642362 0.339356 0.034 Uiso 1 1 calc R U . . .
H15B H 0.090762 0.542976 0.352148 0.034 Uiso 1 1 calc R U . . .
C16 C 0.0496(2) 0.58215(17) 0.1721(2) 0.0333(5) Uani 1 1 d . . . . .
H16A H -0.009393 0.532195 0.157425 0.040 Uiso 1 1 calc R U . . .
H16B H -0.007499 0.631630 0.143168 0.040 Uiso 1 1 calc R U . . .
C17 C 0.1604(2) 0.57437(14) 0.10355(18) 0.0261(4) Uani 1 1 d . . . . .
H17 H 0.118723 0.566788 0.015102 0.031 Uiso 1 1 calc R U . . .
C18 C 0.2464(3) 0.65387(14) 0.1260(2) 0.0316(5) Uani 1 1 d . . . . .
H18A H 0.189706 0.702663 0.092590 0.038 Uiso 1 1 calc R U . . .
H18B H 0.321729 0.649803 0.085727 0.038 Uiso 1 1 calc R U . . .
C19 C 0.3040(3) 0.66416(15) 0.2637(2) 0.0290(5) Uani 1 1 d . . . . .
H19A H 0.404278 0.668778 0.281994 0.035 Uiso 1 1 calc R U . . .
H19B H 0.268475 0.716414 0.290149 0.035 Uiso 1 1 calc R U . . .
C20 C 0.3164(3) 0.51554(15) 0.2900(2) 0.0306(5) Uani 1 1 d . . . . .
H20A H 0.294647 0.468273 0.337557 0.037 Uiso 1 1 calc R U . . .
H20B H 0.416484 0.518198 0.303843 0.037 Uiso 1 1 calc R U . . .
C21 C 0.2511(3) 0.50017(14) 0.1542(2) 0.0295(5) Uani 1 1 d . . . . .
H21A H 0.322917 0.493713 0.110264 0.035 Uiso 1 1 calc R U . . .
H21B H 0.196306 0.448427 0.143650 0.035 Uiso 1 1 calc R U . . .
N1 N 0.52839(17) 0.69540(11) 0.68001(15) 0.0205(3) Uani 1 1 d . . . . .
N2 N 0.26738(17) 0.59343(11) 0.33225(15) 0.0203(3) Uani 1 1 d . . . . .
O1 O 0.57282(16) 0.69035(10) 0.88697(13) 0.0262(3) Uani 1 1 d . . . . .
Se1 Se 0.41910(2) 0.64853(2) 0.53429(2) 0.01893(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 C6 1.394(3) . ?
C1 C2 1.397(3) . ?
C1 Se1 1.898(2) . ?
C2 C3 1.394(3) . ?
C2 C7 1.479(3) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.235(3) . ?
C7 N1 1.354(3) . ?
C8 N1 1.462(3) . ?
C8 C9 1.512(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.392(3) . ?
C9 C10 1.398(3) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N2 1.478(3) . ?
C15 C16 1.543(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.530(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C21 1.527(3) . ?
C17 C18 1.531(3) . ?
C17 H17 1.0000 . ?
C18 C19 1.543(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N2 1.479(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 N2 1.471(3) . ?
C20 C21 1.547(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
N1 Se1 1.9077(17) . ?

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
C6 C1 C2 120.44(19) . . ?
C6 C1 Se1 127.34(15) . . ?
C2 C1 Se1 112.17(15) . . ?
C3 C2 C1 120.48(19) . . ?
C3 C2 C7 123.11(18) . . ?
C1 C2 C7 116.31(18) . . ?
C4 C3 C2 119.59(19) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.65(19) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 118.32(19) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O1 C7 N1 124.8(2) . . ?
O1 C7 C2 125.58(19) . . ?
N1 C7 C2 109.64(17) . . ?
N1 C8 C9 111.59(17) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C14 C9 C10 118.3(2) . . ?
C14 C9 C8 121.16(19) . . ?
C10 C9 C8 120.50(18) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 119.1(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 121.0(2) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
N2 C15 C16 111.45(18) . . ?
N2 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
N2 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 108.98(18) . . ?
C17 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C21 C17 C16 108.74(19) . . ?
C21 C17 C18 108.79(19) . . ?
C16 C17 C18 108.0(2) . . ?
C21 C17 H17 110.4 . . ?
C16 C17 H17 110.4 . . ?
C18 C17 H17 110.4 . . ?
C17 C18 C19 108.28(18) . . ?
C17 C18 H18A 110.0 . . ?
C19 C18 H18A 110.0 . . ?
C17 C18 H18B 110.0 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
N2 C19 C18 112.13(18) . . ?
N2 C19 H19A 109.2 . . ?
C18 C19 H19A 109.2 . . ?
N2 C19 H19B 109.2 . . ?
C18 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
N2 C20 C21 111.71(18) . . ?
N2 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
N2 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
C17 C21 C20 108.71(17) . . ?
C17 C21 H21A 109.9 . . ?
C20 C21 H21A 109.9 . . ?
C17 C21 H21B 109.9 . . ?
C20 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
C7 N1 C8 122.05(17) . . ?
C7 N1 Se1 117.47(14) . . ?
C8 N1 Se1 120.47(13) . . ?
C20 N2 C19 109.09(18) . . ?
C20 N2 C15 109.44(18) . . ?
C19 N2 C15 108.05(17) . . ?
C1 Se1 N1 84.28(8) . . ?

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
C6 C1 C2 C3 -1.0(3) . . . . ?
Se1 C1 C2 C3 -178.65(15) . . . . ?
C6 C1 C2 C7 175.56(18) . . . . ?
Se1 C1 C2 C7 -2.1(2) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C7 C2 C3 C4 -175.21(19) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
Se1 C1 C6 C5 177.65(15) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C3 C2 C7 O1 -3.1(3) . . . . ?
C1 C2 C7 O1 -179.54(19) . . . . ?
C3 C2 C7 N1 175.98(19) . . . . ?
C1 C2 C7 N1 -0.5(3) . . . . ?
N1 C8 C9 C14 -95.1(2) . . . . ?
N1 C8 C9 C10 84.1(2) . . . . ?
C14 C9 C10 C11 0.1(3) . . . . ?
C8 C9 C10 C11 -179.1(2) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C9 -0.8(3) . . . . ?
C10 C9 C14 C13 0.5(3) . . . . ?
C8 C9 C14 C13 179.7(2) . . . . ?
N2 C15 C16 C17 3.0(3) . . . . ?
C15 C16 C17 C21 56.8(3) . . . . ?
C15 C16 C17 C18 -61.1(2) . . . . ?
C21 C17 C18 C19 -60.6(3) . . . . ?
C16 C17 C18 C19 57.2(3) . . . . ?
C17 C18 C19 N2 3.4(3) . . . . ?
C16 C17 C21 C20 -60.2(2) . . . . ?
C18 C17 C21 C20 57.1(2) . . . . ?
N2 C20 C21 C17 3.2(3) . . . . ?
O1 C7 N1 C8 3.3(3) . . . . ?
C2 C7 N1 C8 -175.81(17) . . . . ?
O1 C7 N1 Se1 -177.99(16) . . . . ?
C2 C7 N1 Se1 2.9(2) . . . . ?
C9 C8 N1 C7 84.3(2) . . . . ?
C9 C8 N1 Se1 -94.36(18) . . . . ?
C21 C20 N2 C19 -60.8(2) . . . . ?
C21 C20 N2 C15 57.3(2) . . . . ?
C18 C19 N2 C20 57.1(3) . . . . ?
C18 C19 N2 C15 -61.8(3) . . . . ?
C16 C15 N2 C20 -60.9(2) . . . . ?
C16 C15 N2 C19 57.8(2) . . . . ?
C6 C1 Se1 N1 -174.61(19) . . . . ?
C2 C1 Se1 N1 2.87(14) . . . . ?

_refine_diff_density_max         0.465
_refine_diff_density_min         -0.886
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1867208'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_3                   
;
PROBLEM: Short Inter D...A Contact  Se1      ..N2       .       2.81 Ang.
RESPONSE: CHALCOGEN BONDING
;
# Added during the CSD deposition process: Wednesday 12 September 2018 03:20 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H8 N2 O Se'
_chemical_formula_weight         299.18

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   17.371(4)
_cell_length_b                   5.3080(11)
_cell_length_c                   11.633(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1072.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    1779
_cell_measurement_theta_min      4.3
_cell_measurement_theta_max      31.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    3.486
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.710920
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'MX1 Beamline Australian Synchrotron'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16031
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.380
_diffrn_reflns_theta_max         31.564
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             2967
_reflns_number_gt                2895
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_max     0.817
_reflns_Friedel_fraction_full    0.962

_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       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.4292P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1327 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.045(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2967
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_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
C1 C 0.79112(14) 0.0869(5) 0.3891(2) 0.0136(4) Uani 1 1 d . . . . .
C2 C 0.75360(12) 0.0662(6) 0.4948(3) 0.0152(6) Uani 1 1 d . . . . .
C3 C 0.77554(15) -0.1195(5) 0.5736(2) 0.0152(4) Uani 1 1 d . . . . .
H3 H 0.749843 -0.135661 0.643378 0.018 Uiso 1 1 calc R U . . .
C4 C 0.83609(14) -0.2792(5) 0.5465(2) 0.0167(4) Uani 1 1 d . . . . .
H4 H 0.851430 -0.402743 0.598346 0.020 Uiso 1 1 calc R U . . .
C5 C 0.87426(14) -0.2540(5) 0.4405(2) 0.0168(5) Uani 1 1 d . . . . .
H5 H 0.915215 -0.360449 0.423404 0.020 Uiso 1 1 calc R U . . .
C6 C 0.85202(14) -0.0732(5) 0.3607(2) 0.0164(5) Uani 1 1 d . . . . .
H6 H 0.877034 -0.059191 0.290335 0.020 Uiso 1 1 calc R U . . .
C7 C 0.69211(14) 0.2484(5) 0.5134(2) 0.0142(4) Uani 1 1 d . . . . .
C8 C 0.63333(14) 0.6066(5) 0.4142(2) 0.0151(4) Uani 1 1 d . . . . .
C9 C 0.58424(14) 0.6241(5) 0.5155(2) 0.0154(4) Uani 1 1 d . . . . .
C10 C 0.59403(14) 0.4510(5) 0.6070(2) 0.0146(4) Uani 1 1 d . . . . .
C11 C 0.54423(15) 0.4690(5) 0.7025(2) 0.0169(4) Uani 1 1 d . . . . .
H11 H 0.548589 0.354324 0.762550 0.020 Uiso 1 1 calc R U . . .
C12 C 0.48911(17) 0.6560(5) 0.7072(3) 0.0186(5) Uani 1 1 d . . . . .
H12 H 0.457082 0.666872 0.771095 0.022 Uiso 1 1 calc R U . . .
C13 C 0.48055(16) 0.8304(5) 0.6170(3) 0.0200(5) Uani 1 1 d . . . . .
H13 H 0.443438 0.956298 0.621607 0.024 Uiso 1 1 calc R U . . .
C14 C 0.52748(15) 0.8135(5) 0.5219(2) 0.0181(5) Uani 1 1 d . . . . .
H14 H 0.521720 0.927343 0.461711 0.022 Uiso 1 1 calc R U . . .
N1 N 0.68315(12) 0.4012(4) 0.41873(17) 0.0138(4) Uani 1 1 d . . . . .
N2 N 0.65081(13) 0.2666(4) 0.60679(19) 0.0149(4) Uani 1 1 d . . . . .
O1 O 0.63230(11) 0.7444(4) 0.32937(17) 0.0186(4) Uani 1 1 d . . . . .
Se1 Se 0.74924(2) 0.34228(4) 0.29331(9) 0.01508(10) 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 C6 1.396(4) . ?
C1 C2 1.397(4) . ?
C1 Se1 1.899(3) . ?
C2 C3 1.399(4) . ?
C2 C7 1.457(4) . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.407(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.305(3) . ?
C7 N1 1.377(3) . ?
C8 O1 1.228(3) . ?
C8 N1 1.393(3) . ?
C8 C9 1.458(3) . ?
C9 C14 1.410(3) . ?
C9 C10 1.416(3) . ?
C10 N2 1.390(3) . ?
C10 C11 1.411(3) . ?
C11 C12 1.380(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.407(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
N1 Se1 1.883(2) . ?

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
C6 C1 C2 120.9(2) . . ?
C6 C1 Se1 125.88(18) . . ?
C2 C1 Se1 113.19(19) . . ?
C1 C2 C3 120.4(2) . . ?
C1 C2 C7 114.9(3) . . ?
C3 C2 C7 124.7(3) . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 H6 120.9 . . ?
C1 C6 H6 120.9 . . ?
N2 C7 N1 124.1(2) . . ?
N2 C7 C2 125.2(2) . . ?
N1 C7 C2 110.8(2) . . ?
O1 C8 N1 120.4(2) . . ?
O1 C8 C9 127.1(2) . . ?
N1 C8 C9 112.5(2) . . ?
C14 C9 C10 120.5(2) . . ?
C14 C9 C8 119.8(2) . . ?
C10 C9 C8 119.7(2) . . ?
N2 C10 C11 118.9(2) . . ?
N2 C10 C9 122.8(2) . . ?
C11 C10 C9 118.3(2) . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C9 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C7 N1 C8 124.2(2) . . ?
C7 N1 Se1 116.96(17) . . ?
C8 N1 Se1 118.64(16) . . ?
C7 N2 C10 116.3(2) . . ?
N1 Se1 C1 84.12(10) . . ?

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
C6 C1 C2 C3 -1.3(4) . . . . ?
Se1 C1 C2 C3 177.6(2) . . . . ?
C6 C1 C2 C7 178.9(2) . . . . ?
Se1 C1 C2 C7 -2.2(3) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C7 C2 C3 C4 -178.8(2) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
Se1 C1 C6 C5 -178.58(19) . . . . ?
C1 C2 C7 N2 -178.4(2) . . . . ?
C3 C2 C7 N2 1.8(4) . . . . ?
C1 C2 C7 N1 1.5(3) . . . . ?
C3 C2 C7 N1 -178.3(2) . . . . ?
O1 C8 C9 C14 0.9(4) . . . . ?
N1 C8 C9 C14 -176.5(2) . . . . ?
O1 C8 C9 C10 -179.0(2) . . . . ?
N1 C8 C9 C10 3.6(3) . . . . ?
C14 C9 C10 N2 -177.7(2) . . . . ?
C8 C9 C10 N2 2.2(4) . . . . ?
C14 C9 C10 C11 1.8(4) . . . . ?
C8 C9 C10 C11 -178.4(2) . . . . ?
N2 C10 C11 C12 177.6(2) . . . . ?
C9 C10 C11 C12 -1.9(4) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C12 C13 C14 C9 -0.6(4) . . . . ?
C10 C9 C14 C13 -0.5(4) . . . . ?
C8 C9 C14 C13 179.6(2) . . . . ?
N2 C7 N1 C8 5.4(4) . . . . ?
C2 C7 N1 C8 -174.5(2) . . . . ?
N2 C7 N1 Se1 179.85(19) . . . . ?
C2 C7 N1 Se1 0.0(3) . . . . ?
O1 C8 N1 C7 175.0(2) . . . . ?
C9 C8 N1 C7 -7.3(3) . . . . ?
O1 C8 N1 Se1 0.7(3) . . . . ?
C9 C8 N1 Se1 178.32(16) . . . . ?
N1 C7 N2 C10 1.0(3) . . . . ?
C2 C7 N2 C10 -179.1(2) . . . . ?
C11 C10 N2 C7 175.9(2) . . . . ?
C9 C10 N2 C7 -4.6(3) . . . . ?
C7 N1 Se1 C1 -0.93(18) . . . . ?
C8 N1 Se1 C1 173.81(19) . . . . ?
C6 C1 Se1 N1 -179.5(2) . . . . ?
C2 C1 Se1 N1 1.72(19) . . . . ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -1.411
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1867210'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O Se'
_chemical_formula_weight         288.20
_chemical_oxdiff_usercomment     'benzyl ebselen '

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   11.7848(3)
_cell_length_b                   4.58690(10)
_cell_length_c                   21.3572(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1154.48(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    17511
_cell_measurement_theta_min      2.8110
_cell_measurement_theta_max      45.1230

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.684
_exptl_crystal_size_mid          0.545
_exptl_crystal_size_min          0.441
_exptl_absorpt_coefficient_mu    3.233
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.127
_exptl_absorpt_correction_T_max  0.768
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.776
_oxdiff_exptl_absorpt_empirical_full_max 1.260
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_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, Dualflex, HyPix'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44918
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         3.458
_diffrn_reflns_theta_max         45.375
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9588
_reflns_number_gt                7848
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.997

_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0068(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 3392 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9588
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_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
C1 C 0.20272(14) 0.6373(4) 0.59915(7) 0.0128(2) Uani 1 1 d . . . . .
C2 C 0.31743(14) 0.5656(3) 0.60426(7) 0.0133(2) Uani 1 1 d . . . . .
C3 C 0.38519(15) 0.6944(4) 0.65043(8) 0.0164(3) Uani 1 1 d . . . . .
H3 H 0.461570 0.646034 0.653934 0.020 Uiso 1 1 calc R U . . .
C4 C 0.33654(19) 0.8952(4) 0.69085(8) 0.0187(3) Uani 1 1 d . . . . .
H4 H 0.380701 0.983808 0.721503 0.022 Uiso 1 1 calc R U . . .
C5 C 0.22153(17) 0.9650(4) 0.68577(8) 0.0185(3) Uani 1 1 d . . . . .
H5 H 0.190088 1.099510 0.713357 0.022 Uiso 1 1 calc R U . . .
C6 C 0.15291(15) 0.8375(4) 0.64022(8) 0.0153(2) Uani 1 1 d . . . . .
H6 H 0.076294 0.884042 0.637219 0.018 Uiso 1 1 calc R U . . .
C7 C 0.35928(13) 0.3510(4) 0.55866(7) 0.0131(2) Uani 1 1 d . . . . .
C8 C 0.29554(16) 0.0497(4) 0.47084(8) 0.0161(3) Uani 1 1 d . . . . .
H8A H 0.223948 -0.037120 0.458423 0.019 Uiso 1 1 calc R U . . .
H8B H 0.343646 -0.104604 0.486941 0.019 Uiso 1 1 calc R U . . .
C9 C 0.35125(15) 0.1826(4) 0.41414(8) 0.0164(3) Uani 1 1 d . . . . .
C10 C 0.46340(19) 0.1187(6) 0.39997(10) 0.0279(4) Uani 1 1 d . . . . .
H10 H 0.504729 -0.004673 0.425926 0.033 Uiso 1 1 calc R U . . .
C11 C 0.5145(2) 0.2386(7) 0.34706(11) 0.0397(7) Uani 1 1 d . . . . .
H11 H 0.589461 0.193536 0.337590 0.048 Uiso 1 1 calc R U . . .
C12 C 0.4536(4) 0.4250(6) 0.30848(12) 0.0444(9) Uani 1 1 d . . . . .
H12 H 0.487681 0.506288 0.273300 0.053 Uiso 1 1 calc R U . . .
C13 C 0.3417(4) 0.4892(8) 0.32271(13) 0.0458(8) Uani 1 1 d . . . . .
H13 H 0.300866 0.615460 0.297148 0.055 Uiso 1 1 calc R U . . .
C14 C 0.2900(3) 0.3664(5) 0.37494(10) 0.0307(5) Uani 1 1 d . . . . .
H14 H 0.214308 0.407255 0.383661 0.037 Uiso 1 1 calc R U . . .
N1 N 0.27466(12) 0.2617(3) 0.52065(6) 0.0136(2) Uani 1 1 d . . . . .
O1 O 0.45815(11) 0.2582(3) 0.55437(7) 0.0177(2) Uani 1 1 d . . . . .
Se1 Se 0.13164(2) 0.43398(3) 0.53313(2) 0.01271(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
C1 C2 1.396(2) . ?
C1 C6 1.399(2) . ?
C1 Se1 1.8867(16) . ?
C2 C3 1.400(2) . ?
C2 C7 1.470(2) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.244(2) . ?
C7 N1 1.350(2) . ?
C8 N1 1.462(2) . ?
C8 C9 1.506(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.387(3) . ?
C9 C14 1.391(3) . ?
C10 C11 1.393(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
N1 Se1 1.8805(14) . ?

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 C6 120.80(15) . . ?
C2 C1 Se1 111.84(12) . . ?
C6 C1 Se1 127.35(13) . . ?
C1 C2 C3 120.56(15) . . ?
C1 C2 C7 115.53(14) . . ?
C3 C2 C7 123.91(15) . . ?
C4 C3 C2 118.88(17) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 120.35(17) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 121.38(17) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 118.02(16) . . ?
C5 C6 H6 121.0 . . ?
C1 C6 H6 121.0 . . ?
O1 C7 N1 122.95(16) . . ?
O1 C7 C2 126.32(15) . . ?
N1 C7 C2 110.72(14) . . ?
N1 C8 C9 112.92(14) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C14 119.44(19) . . ?
C10 C9 C8 120.35(18) . . ?
C14 C9 C8 120.20(18) . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 120.1(3) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C7 N1 C8 121.01(14) . . ?
C7 N1 Se1 116.71(11) . . ?
C8 N1 Se1 122.24(11) . . ?
N1 Se1 C1 85.16(6) . . ?

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
C6 C1 C2 C3 -0.4(2) . . . . ?
Se1 C1 C2 C3 179.83(12) . . . . ?
C6 C1 C2 C7 179.54(14) . . . . ?
Se1 C1 C2 C7 -0.22(17) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C7 C2 C3 C4 179.80(16) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
Se1 C1 C6 C5 -179.57(13) . . . . ?
C1 C2 C7 O1 179.32(16) . . . . ?
C3 C2 C7 O1 -0.7(3) . . . . ?
C1 C2 C7 N1 -1.0(2) . . . . ?
C3 C2 C7 N1 178.99(15) . . . . ?
N1 C8 C9 C10 109.3(2) . . . . ?
N1 C8 C9 C14 -71.8(2) . . . . ?
C14 C9 C10 C11 0.3(3) . . . . ?
C8 C9 C10 C11 179.1(2) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C12 C13 C14 C9 1.4(5) . . . . ?
C10 C9 C14 C13 -1.3(4) . . . . ?
C8 C9 C14 C13 179.9(3) . . . . ?
O1 C7 N1 C8 -0.9(2) . . . . ?
C2 C7 N1 C8 179.39(14) . . . . ?
O1 C7 N1 Se1 -178.54(13) . . . . ?
C2 C7 N1 Se1 1.73(17) . . . . ?
C9 C8 N1 C7 -78.2(2) . . . . ?
C9 C8 N1 Se1 99.37(16) . . . . ?
C7 N1 Se1 C1 -1.55(12) . . . . ?
C8 N1 Se1 C1 -179.18(13) . . . . ?
C2 C1 Se1 N1 0.91(11) . . . . ?
C6 C1 Se1 N1 -178.83(15) . . . . ?

_refine_diff_density_max         1.010
_refine_diff_density_min         -1.479
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_3-pyridine
_database_code_depnum_ccdc_archive 'CCDC 1867211'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_3-pyridine          
;
PROBLEM: Short Inter D...A Contact  Se1      ..N3       .       2.46 Ang.
RESPONSE: CHALCOGEN BONDING
;
# Added during the CSD deposition process: Wednesday 12 September 2018 03:20 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 N3 O Se'
_chemical_formula_weight         378.28
_chemical_oxdiff_usercomment     'Toms Se compound (TF57) from pyridine'

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.7476(9)
_cell_length_b                   4.9407(2)
_cell_length_c                   17.6687(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.376(4)
_cell_angle_gamma                90
_cell_volume                     1728.52(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.01(10)
_cell_measurement_reflns_used    2450
_cell_measurement_theta_min      5.0370
_cell_measurement_theta_max      75.2980

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.564
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.018
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.670
_oxdiff_exptl_absorpt_empirical_full_max 1.534
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            5766
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.466
_diffrn_reflns_theta_max         75.764
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3419
_reflns_number_gt                2889
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.5473P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3419
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_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
C1 C 0.80998(14) 0.1037(5) 0.73159(16) 0.0244(5) Uani 1 1 d . . . . .
C2 C 0.86557(14) 0.2437(5) 0.72223(15) 0.0230(5) Uani 1 1 d . . . . .
C3 C 0.93052(14) 0.1840(5) 0.76965(16) 0.0243(5) Uani 1 1 d . . . . .
H3 H 0.967315 0.279123 0.763531 0.029 Uiso 1 1 calc R U . . .
C4 C 0.93997(14) -0.0187(6) 0.82614(16) 0.0271(5) Uani 1 1 d . . . . .
H4 H 0.983207 -0.058649 0.858542 0.033 Uiso 1 1 calc R U . . .
C5 C 0.88461(15) -0.1627(5) 0.83441(16) 0.0279(6) Uani 1 1 d . . . . .
H5 H 0.891468 -0.299854 0.872043 0.033 Uiso 1 1 calc R U . . .
C6 C 0.81952(15) -0.1048(5) 0.78743(17) 0.0276(6) Uani 1 1 d . . . . .
H6 H 0.782915 -0.202795 0.792963 0.033 Uiso 1 1 calc R U . . .
C7 C 0.84984(14) 0.4475(5) 0.65942(15) 0.0228(5) Uani 1 1 d . . . . .
C8 C 0.75304(14) 0.6168(6) 0.55661(16) 0.0262(5) Uani 1 1 d . . . . .
C9 C 0.80125(14) 0.7934(5) 0.53586(16) 0.0260(5) Uani 1 1 d . . . . .
C10 C 0.86987(14) 0.7793(5) 0.57982(15) 0.0235(5) Uani 1 1 d . . . . .
C11 C 0.91587(15) 0.9551(5) 0.55972(16) 0.0276(5) Uani 1 1 d . . . . .
H11 H 0.961542 0.946865 0.587792 0.033 Uiso 1 1 calc R U . . .
C12 C 0.89353(16) 1.1388(6) 0.49878(17) 0.0307(6) Uani 1 1 d . . . . .
H12 H 0.924164 1.255345 0.486530 0.037 Uiso 1 1 calc R U . . .
C13 C 0.82455(16) 1.1514(6) 0.45483(17) 0.0326(6) Uani 1 1 d . . . . .
H13 H 0.809867 1.275460 0.413675 0.039 Uiso 1 1 calc R U . . .
C14 C 0.77920(16) 0.9804(6) 0.47292(17) 0.0311(6) Uani 1 1 d . . . . .
H14 H 0.733801 0.987619 0.443662 0.037 Uiso 1 1 calc R U . . .
C15 C 0.61966(16) -0.2447(7) 0.6826(2) 0.0365(7) Uani 1 1 d . . . . .
H15 H 0.622412 -0.277621 0.631869 0.044 Uiso 1 1 calc R U . . .
C16 C 0.57223(18) -0.3857(8) 0.7081(2) 0.0459(8) Uani 1 1 d . . . . .
H16 H 0.543734 -0.510649 0.675073 0.055 Uiso 1 1 calc R U . . .
C17 C 0.56819(18) -0.3371(7) 0.7832(2) 0.0424(7) Uani 1 1 d . . . . .
H17 H 0.537153 -0.430494 0.801917 0.051 Uiso 1 1 calc R U . . .
C18 C 0.61082(17) -0.1475(8) 0.8305(2) 0.0415(7) Uani 1 1 d . . . . .
H18 H 0.608990 -0.109551 0.881418 0.050 Uiso 1 1 calc R U . . .
C19 C 0.65634(16) -0.0164(7) 0.7995(2) 0.0399(7) Uani 1 1 d . . . . .
H19 H 0.684883 0.112179 0.830785 0.048 Uiso 1 1 calc R U . . .
N1 N 0.78193(12) 0.4529(5) 0.62047(13) 0.0254(5) Uani 1 1 d . . . . .
N2 N 0.89461(12) 0.6009(4) 0.64182(13) 0.0241(4) Uani 1 1 d . . . . .
N3 N 0.66147(12) -0.0639(5) 0.72784(15) 0.0332(5) Uani 1 1 d . . . . .
O1 O 0.69143(10) 0.6069(5) 0.52330(12) 0.0355(5) Uani 1 1 d . . . . .
Se1 Se 0.72557(2) 0.22153(6) 0.66162(2) 0.02704(11) 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 C2 1.396(4) . ?
C1 C6 1.399(4) . ?
C1 Se1 1.908(3) . ?
C2 C3 1.389(4) . ?
C2 C7 1.462(4) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.306(3) . ?
C7 N1 1.371(4) . ?
C8 O1 1.238(3) . ?
C8 N1 1.373(4) . ?
C8 C9 1.454(4) . ?
C9 C10 1.405(4) . ?
C9 C14 1.413(4) . ?
C10 N2 1.380(3) . ?
C10 C11 1.412(4) . ?
C11 C12 1.378(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.411(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 N3 1.332(4) . ?
C15 C16 1.386(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(5) . ?
C18 H18 0.9300 . ?
C19 N3 1.322(4) . ?
C19 H19 0.9300 . ?
N1 Se1 1.926(2) . ?

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 C6 120.0(3) . . ?
C2 C1 Se1 113.8(2) . . ?
C6 C1 Se1 126.2(2) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 C7 124.1(2) . . ?
C1 C2 C7 115.2(2) . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N2 C7 N1 124.5(2) . . ?
N2 C7 C2 124.5(2) . . ?
N1 C7 C2 110.9(2) . . ?
O1 C8 N1 120.2(3) . . ?
O1 C8 C9 126.4(3) . . ?
N1 C8 C9 113.4(2) . . ?
C10 C9 C14 120.3(3) . . ?
C10 C9 C8 119.4(2) . . ?
C14 C9 C8 120.4(3) . . ?
N2 C10 C9 123.1(2) . . ?
N2 C10 C11 118.3(2) . . ?
C9 C10 C11 118.7(2) . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
N3 C15 C16 122.7(3) . . ?
N3 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C17 C16 C15 118.6(3) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 119.3(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C19 117.6(3) . . ?
C17 C18 H18 121.2 . . ?
C19 C18 H18 121.2 . . ?
N3 C19 C18 123.7(3) . . ?
N3 C19 H19 118.1 . . ?
C18 C19 H19 118.1 . . ?
C7 N1 C8 123.7(2) . . ?
C7 N1 Se1 116.60(18) . . ?
C8 N1 Se1 119.67(19) . . ?
C7 N2 C10 115.9(2) . . ?
C19 N3 C15 117.9(3) . . ?
C1 Se1 N1 83.25(11) . . ?

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
C6 C1 C2 C3 -2.0(4) . . . . ?
Se1 C1 C2 C3 179.08(19) . . . . ?
C6 C1 C2 C7 177.0(2) . . . . ?
Se1 C1 C2 C7 -1.9(3) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C7 C2 C3 C4 -178.2(2) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
Se1 C1 C6 C5 -179.3(2) . . . . ?
C3 C2 C7 N2 -1.6(4) . . . . ?
C1 C2 C7 N2 179.4(2) . . . . ?
C3 C2 C7 N1 177.3(2) . . . . ?
C1 C2 C7 N1 -1.7(3) . . . . ?
O1 C8 C9 C10 -179.9(3) . . . . ?
N1 C8 C9 C10 0.9(4) . . . . ?
O1 C8 C9 C14 1.1(4) . . . . ?
N1 C8 C9 C14 -178.1(2) . . . . ?
C14 C9 C10 N2 -179.9(2) . . . . ?
C8 C9 C10 N2 1.1(4) . . . . ?
C14 C9 C10 C11 0.0(4) . . . . ?
C8 C9 C10 C11 -179.0(2) . . . . ?
N2 C10 C11 C12 -179.3(2) . . . . ?
C9 C10 C11 C12 0.8(4) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 C9 0.6(4) . . . . ?
C10 C9 C14 C13 -0.7(4) . . . . ?
C8 C9 C14 C13 178.3(3) . . . . ?
N3 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 C18 0.7(6) . . . . ?
C16 C17 C18 C19 -0.5(5) . . . . ?
C17 C18 C19 N3 -0.5(5) . . . . ?
N2 C7 N1 C8 1.7(4) . . . . ?
C2 C7 N1 C8 -177.2(2) . . . . ?
N2 C7 N1 Se1 -176.5(2) . . . . ?
C2 C7 N1 Se1 4.6(3) . . . . ?
O1 C8 N1 C7 178.5(2) . . . . ?
C9 C8 N1 C7 -2.3(4) . . . . ?
O1 C8 N1 Se1 -3.4(3) . . . . ?
C9 C8 N1 Se1 175.86(18) . . . . ?
N1 C7 N2 C10 0.5(4) . . . . ?
C2 C7 N2 C10 179.3(2) . . . . ?
C9 C10 N2 C7 -1.8(4) . . . . ?
C11 C10 N2 C7 178.3(2) . . . . ?
C18 C19 N3 C15 1.2(5) . . . . ?
C16 C15 N3 C19 -0.9(5) . . . . ?

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.077




####################################################################### 
# 
# 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_1b-DMAP
_database_code_depnum_ccdc_archive 'CCDC 1867209'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N3 O Se'
_chemical_formula_weight         410.37
_chemical_oxdiff_usercomment     'Benzyl-Ebselen with DMAP from Ether Toluene'

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'
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'

_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                   9.6002(4)
_cell_length_b                   10.2109(4)
_cell_length_c                   19.8380(7)
_cell_angle_alpha                78.710(3)
_cell_angle_beta                 84.901(3)
_cell_angle_gamma                77.458(4)
_cell_volume                     1859.33(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.00(10)
_cell_measurement_reflns_used    6449
_cell_measurement_theta_min      3.7420
_cell_measurement_theta_max      37.6540

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.658
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.272
_exptl_absorpt_coefficient_mu    2.034
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_T_max  0.689
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.698
_oxdiff_exptl_absorpt_empirical_full_max 1.446
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (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  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            36541
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.441
_diffrn_reflns_theta_max         40.953
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             23437
_reflns_number_gt                15177
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+0.6794P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         23437
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_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
Se1A Se 0.21998(2) -0.04524(2) 0.51890(2) 0.01947(3) Uani 1 1 d . . . . .
Se1 Se 0.31812(2) 0.74282(2) 0.03474(2) 0.02065(4) Uani 1 1 d . . . . .
O1A O 0.01705(13) 0.31024(12) 0.57086(6) 0.0257(2) Uani 1 1 d . . . . .
N2A N 0.37448(15) -0.19098(13) 0.44743(7) 0.0222(2) Uani 1 1 d . . . . .
N1A N 0.10518(15) 0.08176(13) 0.57137(6) 0.0207(2) Uani 1 1 d . . . . .
O1 O 0.35862(16) 0.52513(14) 0.22630(7) 0.0375(3) Uani 1 1 d . . . . .
C19A C 0.51604(18) -0.22338(16) 0.45684(8) 0.0241(3) Uani 1 1 d . . . . .
H19A H 0.556339 -0.162666 0.476067 0.029 Uiso 1 1 calc R U . . .
N3A N 0.63417(14) -0.54597(13) 0.39433(7) 0.0223(2) Uani 1 1 d . . . . .
N2 N 0.26302(16) 0.95273(15) -0.04883(7) 0.0249(3) Uani 1 1 d . . . . .
N1 N 0.36102(17) 0.58799(13) 0.10839(8) 0.0271(3) Uani 1 1 d . . . . .
N3 N 0.19060(16) 1.29743(16) -0.20552(8) 0.0291(3) Uani 1 1 d . . . . .
C18A C 0.60606(17) -0.33851(15) 0.44047(8) 0.0215(3) Uani 1 1 d . . . . .
H18A H 0.705042 -0.355341 0.448408 0.026 Uiso 1 1 calc R U . . .
C16 C 0.10783(17) 1.10749(16) -0.13131(8) 0.0225(3) Uani 1 1 d . . . . .
H16 H 0.017144 1.131786 -0.151105 0.027 Uiso 1 1 calc R U . . .
C1 C 0.28499(15) 0.84463(14) 0.10713(7) 0.0176(2) Uani 1 1 d . . . . .
C6 C 0.24606(17) 0.98597(15) 0.10155(8) 0.0214(3) Uani 1 1 d . . . . .
H6 H 0.234337 1.043291 0.057664 0.026 Uiso 1 1 calc R U . . .
C2A C 0.14251(15) 0.23086(14) 0.47072(7) 0.0176(2) Uani 1 1 d . . . . .
C2 C 0.30333(16) 0.76121(16) 0.17182(7) 0.0208(3) Uani 1 1 d . . . . .
C9A C 0.17167(17) -0.02550(15) 0.69020(7) 0.0215(3) Uani 1 1 d . . . . .
C7A C 0.08094(16) 0.21507(15) 0.54230(8) 0.0192(2) Uani 1 1 d . . . . .
C8A C 0.05334(18) 0.03257(17) 0.64062(8) 0.0235(3) Uani 1 1 d . . . . .
H8A1 H -0.000949 -0.038845 0.639182 0.028 Uiso 1 1 calc R U . . .
H8A2 H -0.013151 0.108746 0.657920 0.028 Uiso 1 1 calc R U . . .
C19 C 0.36432(19) 1.02485(19) -0.07242(8) 0.0264(3) Uani 1 1 d . . . . .
H19 H 0.454890 0.995058 -0.052582 0.032 Uiso 1 1 calc R U . . .
C15 C 0.13750(18) 0.99663(17) -0.07921(8) 0.0243(3) Uani 1 1 d . . . . .
H15 H 0.063934 0.947391 -0.063498 0.029 Uiso 1 1 calc R U . . .
C18 C 0.34584(18) 1.13875(19) -0.12328(8) 0.0260(3) Uani 1 1 d . . . . .
H18 H 0.421523 1.186184 -0.136945 0.031 Uiso 1 1 calc R U . . .
C6A C 0.28161(18) 0.11635(16) 0.38323(8) 0.0220(3) Uani 1 1 d . . . . .
H6A H 0.334409 0.035678 0.368799 0.026 Uiso 1 1 calc R U . . .
C17A C 0.55077(16) -0.43128(14) 0.41188(7) 0.0177(2) Uani 1 1 d . . . . .
C15A C 0.32130(16) -0.28015(15) 0.42073(8) 0.0202(2) Uani 1 1 d . . . . .
H15A H 0.221548 -0.260606 0.414214 0.024 Uiso 1 1 calc R U . . .
C3A C 0.13034(16) 0.35681(15) 0.42624(8) 0.0214(3) Uani 1 1 d . . . . .
H3A H 0.080919 0.438177 0.441130 0.026 Uiso 1 1 calc R U . . .
C17 C 0.21357(17) 1.18525(16) -0.15527(7) 0.0217(3) Uani 1 1 d . . . . .
C5A C 0.26705(19) 0.24154(17) 0.33907(8) 0.0248(3) Uani 1 1 d . . . . .
H5A H 0.309215 0.246024 0.293719 0.030 Uiso 1 1 calc R U . . .
C8 C 0.3836(2) 0.44931(17) 0.09524(12) 0.0367(4) Uani 1 1 d . . . . .
H8A H 0.429675 0.385027 0.134946 0.044 Uiso 1 1 calc R U . . .
H8B H 0.449277 0.440867 0.054198 0.044 Uiso 1 1 calc R U . . .
C16A C 0.40179(16) -0.39787(15) 0.40222(8) 0.0196(2) Uani 1 1 d . . . . .
H16A H 0.357841 -0.456231 0.383134 0.024 Uiso 1 1 calc R U . . .
C7 C 0.34383(18) 0.61304(16) 0.17318(9) 0.0255(3) Uani 1 1 d . . . . .
C5 C 0.2247(2) 1.04157(18) 0.16086(9) 0.0279(3) Uani 1 1 d . . . . .
H5 H 0.198502 1.137790 0.157371 0.033 Uiso 1 1 calc R U . . .
C4A C 0.19147(18) 0.36107(17) 0.36014(9) 0.0251(3) Uani 1 1 d . . . . .
H4A H 0.181975 0.445619 0.328986 0.030 Uiso 1 1 calc R U . . .
C10A C 0.1644(2) -0.13920(18) 0.74107(9) 0.0300(3) Uani 1 1 d . . . . .
H10A H 0.085079 -0.182226 0.744514 0.036 Uiso 1 1 calc R U . . .
C9 C 0.2453(2) 0.41049(16) 0.08350(10) 0.0324(4) Uani 1 1 d . . . . .
C21A C 0.78609(17) -0.58014(17) 0.40701(9) 0.0261(3) Uani 1 1 d . . . . .
H21A H 0.829620 -0.502037 0.386883 0.039 Uiso 1 1 calc R U . . .
H21B H 0.832077 -0.658889 0.385955 0.039 Uiso 1 1 calc R U . . .
H21C H 0.798793 -0.602480 0.456711 0.039 Uiso 1 1 calc R U . . .
C14A C 0.28839(19) 0.03602(18) 0.68650(8) 0.0259(3) Uani 1 1 d . . . . .
H14A H 0.294339 0.114068 0.652176 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2412(2) 0.9585(2) 0.22572(9) 0.0307(4) Uani 1 1 d . . . . .
H4 H 0.225334 0.998099 0.265987 0.037 Uiso 1 1 calc R U . . .
C20A C 0.57163(19) -0.63968(16) 0.36595(9) 0.0258(3) Uani 1 1 d . . . . .
H20A H 0.503732 -0.677327 0.400118 0.039 Uiso 1 1 calc R U . . .
H20B H 0.647338 -0.714068 0.354085 0.039 Uiso 1 1 calc R U . . .
H20C H 0.521660 -0.590815 0.324509 0.039 Uiso 1 1 calc R U . . .
C3 C 0.28049(19) 0.8187(2) 0.23110(8) 0.0275(3) Uani 1 1 d . . . . .
H3 H 0.291972 0.761803 0.275096 0.033 Uiso 1 1 calc R U . . .
C1A C 0.21710(16) 0.11156(14) 0.44920(7) 0.0180(2) Uani 1 1 d . . . . .
C12A C 0.3889(2) -0.1288(2) 0.78277(10) 0.0365(4) Uani 1 1 d . . . . .
H12A H 0.462985 -0.164039 0.814152 0.044 Uiso 1 1 calc R U . . .
C10 C 0.2303(3) 0.35438(18) 0.02671(10) 0.0416(5) Uani 1 1 d . . . . .
H10 H 0.308514 0.338944 -0.005638 0.050 Uiso 1 1 calc R U . . .
C14 C 0.1290(2) 0.43155(19) 0.13022(11) 0.0345(4) Uani 1 1 d . . . . .
H14 H 0.137765 0.468904 0.169523 0.041 Uiso 1 1 calc R U . . .
C13A C 0.3965(2) -0.0153(2) 0.73246(10) 0.0325(4) Uani 1 1 d . . . . .
H13A H 0.475848 0.027535 0.729342 0.039 Uiso 1 1 calc R U . . .
C20 C 0.0644(2) 1.3321(2) -0.24608(10) 0.0342(4) Uani 1 1 d . . . . .
H20D H 0.077848 1.275085 -0.281491 0.051 Uiso 1 1 calc R U . . .
H20E H 0.049484 1.428419 -0.268093 0.051 Uiso 1 1 calc R U . . .
H20F H -0.019180 1.316130 -0.215975 0.051 Uiso 1 1 calc R U . . .
C11A C 0.2735(3) -0.1902(2) 0.78705(10) 0.0381(5) Uani 1 1 d . . . . .
H11A H 0.267991 -0.267975 0.821612 0.046 Uiso 1 1 calc R U . . .
C21 C 0.3052(2) 1.3703(2) -0.22985(11) 0.0403(5) Uani 1 1 d . . . . .
H21D H 0.345764 1.390942 -0.190477 0.060 Uiso 1 1 calc R U . . .
H21E H 0.267181 1.455526 -0.260800 0.060 Uiso 1 1 calc R U . . .
H21F H 0.379809 1.313466 -0.254643 0.060 Uiso 1 1 calc R U . . .
C13 C 0.0009(3) 0.3988(2) 0.12014(13) 0.0409(5) Uani 1 1 d . . . . .
H13 H -0.077635 0.414214 0.152287 0.049 Uiso 1 1 calc R U . . .
C11 C 0.1021(3) 0.3208(2) 0.01704(12) 0.0483(6) Uani 1 1 d . . . . .
H11 H 0.093271 0.281896 -0.021717 0.058 Uiso 1 1 calc R U . . .
C12 C -0.0131(3) 0.3436(2) 0.06329(13) 0.0455(5) Uani 1 1 d . . . . .
H12 H -0.101160 0.321491 0.056126 0.055 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
Se1A C1A 1.8966(14) . ?
Se1A N1A 1.9192(13) . ?
Se1 C1 1.8984(15) . ?
Se1 N1 1.9297(13) . ?
O1A C7A 1.2395(18) . ?
N2A C15A 1.345(2) . ?
N2A C19A 1.348(2) . ?
N1A C7A 1.3486(19) . ?
N1A C8A 1.4506(19) . ?
O1 C7 1.2398(19) . ?
C19A C18A 1.376(2) . ?
C19A H19A 0.9500 . ?
N3A C17A 1.3552(19) . ?
N3A C20A 1.454(2) . ?
N3A C21A 1.457(2) . ?
N2 C19 1.342(2) . ?
N2 C15 1.343(2) . ?
N1 C7 1.348(2) . ?
N1 C8 1.457(2) . ?
N3 C17 1.355(2) . ?
N3 C20 1.455(2) . ?
N3 C21 1.455(2) . ?
C18A C17A 1.408(2) . ?
C18A H18A 0.9500 . ?
C16 C15 1.373(2) . ?
C16 C17 1.415(2) . ?
C16 H16 0.9500 . ?
C1 C6 1.395(2) . ?
C1 C2 1.397(2) . ?
C6 C5 1.384(2) . ?
C6 H6 0.9500 . ?
C2A C1A 1.396(2) . ?
C2A C3A 1.398(2) . ?
C2A C7A 1.481(2) . ?
C2 C3 1.394(2) . ?
C2 C7 1.474(2) . ?
C9A C14A 1.389(2) . ?
C9A C10A 1.391(2) . ?
C9A C8A 1.512(2) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C19 C18 1.373(2) . ?
C19 H19 0.9500 . ?
C15 H15 0.9500 . ?
C18 C17 1.416(2) . ?
C18 H18 0.9500 . ?
C6A C5A 1.388(2) . ?
C6A C1A 1.394(2) . ?
C6A H6A 0.9500 . ?
C17A C16A 1.418(2) . ?
C15A C16A 1.377(2) . ?
C15A H15A 0.9500 . ?
C3A C4A 1.385(2) . ?
C3A H3A 0.9500 . ?
C5A C4A 1.397(2) . ?
C5A H5A 0.9500 . ?
C8 C9 1.515(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C16A H16A 0.9500 . ?
C5 C4 1.397(3) . ?
C5 H5 0.9500 . ?
C4A H4A 0.9500 . ?
C10A C11A 1.395(3) . ?
C10A H10A 0.9500 . ?
C9 C10 1.391(3) . ?
C9 C14 1.394(3) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
C14A C13A 1.388(3) . ?
C14A H14A 0.9500 . ?
C4 C3 1.380(3) . ?
C4 H4 0.9500 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C3 H3 0.9500 . ?
C12A C11A 1.376(3) . ?
C12A C13A 1.383(3) . ?
C12A H12A 0.9500 . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C14 C13 1.383(3) . ?
C14 H14 0.9500 . ?
C13A H13A 0.9500 . ?
C20 H20D 0.9800 . ?
C20 H20E 0.9800 . ?
C20 H20F 0.9800 . ?
C11A H11A 0.9500 . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
C13 C12 1.384(3) . ?
C13 H13 0.9500 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9500 . ?
C12 H12 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
C1A Se1A N1A 83.94(6) . . ?
C1 Se1 N1 83.89(6) . . ?
C15A N2A C19A 116.01(13) . . ?
C7A N1A C8A 122.88(13) . . ?
C7A N1A Se1A 117.52(10) . . ?
C8A N1A Se1A 119.55(10) . . ?
N2A C19A C18A 124.37(15) . . ?
N2A C19A H19A 117.8 . . ?
C18A C19A H19A 117.8 . . ?
C17A N3A C20A 120.33(13) . . ?
C17A N3A C21A 120.30(14) . . ?
C20A N3A C21A 119.29(13) . . ?
C19 N2 C15 115.90(14) . . ?
C7 N1 C8 121.00(14) . . ?
C7 N1 Se1 117.13(11) . . ?
C8 N1 Se1 120.82(13) . . ?
C17 N3 C20 121.49(15) . . ?
C17 N3 C21 120.04(16) . . ?
C20 N3 C21 117.27(15) . . ?
C19A C18A C17A 119.69(15) . . ?
C19A C18A H18A 120.2 . . ?
C17A C18A H18A 120.2 . . ?
C15 C16 C17 119.41(15) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C6 C1 C2 120.07(14) . . ?
C6 C1 Se1 127.58(11) . . ?
C2 C1 Se1 112.35(11) . . ?
C5 C6 C1 119.08(14) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C1A C2A C3A 120.52(14) . . ?
C1A C2A C7A 116.23(12) . . ?
C3A C2A C7A 123.24(13) . . ?
C3 C2 C1 120.15(15) . . ?
C3 C2 C7 123.21(14) . . ?
C1 C2 C7 116.62(14) . . ?
C14A C9A C10A 118.82(16) . . ?
C14A C9A C8A 120.28(14) . . ?
C10A C9A C8A 120.89(16) . . ?
O1A C7A N1A 125.44(14) . . ?
O1A C7A C2A 124.96(13) . . ?
N1A C7A C2A 109.60(12) . . ?
N1A C8A C9A 113.16(13) . . ?
N1A C8A H8A1 108.9 . . ?
C9A C8A H8A1 108.9 . . ?
N1A C8A H8A2 108.9 . . ?
C9A C8A H8A2 108.9 . . ?
H8A1 C8A H8A2 107.8 . . ?
N2 C19 C18 124.40(16) . . ?
N2 C19 H19 117.8 . . ?
C18 C19 H19 117.8 . . ?
N2 C15 C16 124.75(15) . . ?
N2 C15 H15 117.6 . . ?
C16 C15 H15 117.6 . . ?
C19 C18 C17 119.75(15) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C5A C6A C1A 118.56(15) . . ?
C5A C6A H6A 120.7 . . ?
C1A C6A H6A 120.7 . . ?
N3A C17A C18A 122.41(14) . . ?
N3A C17A C16A 121.49(14) . . ?
C18A C17A C16A 116.10(13) . . ?
N2A C15A C16A 124.36(15) . . ?
N2A C15A H15A 117.8 . . ?
C16A C15A H15A 117.8 . . ?
C4A C3A C2A 118.94(14) . . ?
C4A C3A H3A 120.5 . . ?
C2A C3A H3A 120.5 . . ?
N3 C17 C16 122.54(15) . . ?
N3 C17 C18 121.69(15) . . ?
C16 C17 C18 115.76(14) . . ?
C6A C5A C4A 121.17(15) . . ?
C6A C5A H5A 119.4 . . ?
C4A C5A H5A 119.4 . . ?
N1 C8 C9 112.22(15) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C15A C16A C17A 119.47(14) . . ?
C15A C16A H16A 120.3 . . ?
C17A C16A H16A 120.3 . . ?
O1 C7 N1 125.43(17) . . ?
O1 C7 C2 124.67(17) . . ?
N1 C7 C2 109.89(13) . . ?
C6 C5 C4 121.08(16) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C3A C4A C5A 120.28(14) . . ?
C3A C4A H4A 119.9 . . ?
C5A C4A H4A 119.9 . . ?
C9A C10A C11A 120.14(19) . . ?
C9A C10A H10A 119.9 . . ?
C11A C10A H10A 119.9 . . ?
C10 C9 C14 118.5(2) . . ?
C10 C9 C8 121.70(19) . . ?
C14 C9 C8 119.77(18) . . ?
N3A C21A H21A 109.5 . . ?
N3A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
N3A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C13A C14A C9A 120.69(16) . . ?
C13A C14A H14A 119.7 . . ?
C9A C14A H14A 119.7 . . ?
C3 C4 C5 119.74(16) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N3A C20A H20A 109.5 . . ?
N3A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
N3A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C4 C3 C2 119.87(15) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C6A C1A C2A 120.50(13) . . ?
C6A C1A Se1A 126.96(11) . . ?
C2A C1A Se1A 112.53(10) . . ?
C11A C12A C13A 119.56(18) . . ?
C11A C12A H12A 120.2 . . ?
C13A C12A H12A 120.2 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C13 C14 C9 120.9(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C12A C13A C14A 120.22(19) . . ?
C12A C13A H13A 119.9 . . ?
C14A C13A H13A 119.9 . . ?
N3 C20 H20D 109.5 . . ?
N3 C20 H20E 109.5 . . ?
H20D C20 H20E 109.5 . . ?
N3 C20 H20F 109.5 . . ?
H20D C20 H20F 109.5 . . ?
H20E C20 H20F 109.5 . . ?
C12A C11A C10A 120.58(18) . . ?
C12A C11A H11A 119.7 . . ?
C10A C11A H11A 119.7 . . ?
N3 C21 H21D 109.5 . . ?
N3 C21 H21E 109.5 . . ?
H21D C21 H21E 109.5 . . ?
N3 C21 H21F 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?

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
C15A N2A C19A C18A 0.6(2) . . . . ?
N2A C19A C18A C17A 0.0(2) . . . . ?
N1 Se1 C1 C6 178.64(15) . . . . ?
N1 Se1 C1 C2 -1.59(11) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
Se1 C1 C6 C5 179.13(13) . . . . ?
C6 C1 C2 C3 1.1(2) . . . . ?
Se1 C1 C2 C3 -178.72(12) . . . . ?
C6 C1 C2 C7 179.73(14) . . . . ?
Se1 C1 C2 C7 -0.06(18) . . . . ?
C8A N1A C7A O1A 2.3(3) . . . . ?
Se1A N1A C7A O1A -175.16(13) . . . . ?
C8A N1A C7A C2A -177.71(14) . . . . ?
Se1A N1A C7A C2A 4.80(17) . . . . ?
C1A C2A C7A O1A 176.71(15) . . . . ?
C3A C2A C7A O1A -2.4(2) . . . . ?
C1A C2A C7A N1A -3.26(19) . . . . ?
C3A C2A C7A N1A 177.65(14) . . . . ?
C7A N1A C8A C9A -111.89(17) . . . . ?
Se1A N1A C8A C9A 65.55(17) . . . . ?
C14A C9A C8A N1A 38.8(2) . . . . ?
C10A C9A C8A N1A -142.62(15) . . . . ?
C15 N2 C19 C18 1.3(3) . . . . ?
C19 N2 C15 C16 0.0(3) . . . . ?
C17 C16 C15 N2 -1.3(3) . . . . ?
N2 C19 C18 C17 -1.3(3) . . . . ?
C20A N3A C17A C18A 179.05(14) . . . . ?
C21A N3A C17A C18A 2.2(2) . . . . ?
C20A N3A C17A C16A -1.1(2) . . . . ?
C21A N3A C17A C16A -177.89(13) . . . . ?
C19A C18A C17A N3A 179.61(14) . . . . ?
C19A C18A C17A C16A -0.3(2) . . . . ?
C19A N2A C15A C16A -1.0(2) . . . . ?
C1A C2A C3A C4A 1.0(2) . . . . ?
C7A C2A C3A C4A -179.91(15) . . . . ?
C20 N3 C17 C16 -10.5(3) . . . . ?
C21 N3 C17 C16 -177.67(18) . . . . ?
C20 N3 C17 C18 169.66(17) . . . . ?
C21 N3 C17 C18 2.5(3) . . . . ?
C15 C16 C17 N3 -178.62(16) . . . . ?
C15 C16 C17 C18 1.2(2) . . . . ?
C19 C18 C17 N3 179.79(17) . . . . ?
C19 C18 C17 C16 -0.1(2) . . . . ?
C1A C6A C5A C4A 1.0(3) . . . . ?
C7 N1 C8 C9 93.6(2) . . . . ?
Se1 N1 C8 C9 -74.30(19) . . . . ?
N2A C15A C16A C17A 0.7(2) . . . . ?
N3A C17A C16A C15A -179.91(14) . . . . ?
C18A C17A C16A C15A 0.0(2) . . . . ?
C8 N1 C7 O1 7.3(3) . . . . ?
Se1 N1 C7 O1 175.63(15) . . . . ?
C8 N1 C7 C2 -172.24(16) . . . . ?
Se1 N1 C7 C2 -3.86(19) . . . . ?
C3 C2 C7 O1 1.6(3) . . . . ?
C1 C2 C7 O1 -176.99(16) . . . . ?
C3 C2 C7 N1 -178.88(16) . . . . ?
C1 C2 C7 N1 2.5(2) . . . . ?
C1 C6 C5 C4 -0.2(3) . . . . ?
C2A C3A C4A C5A -1.6(2) . . . . ?
C6A C5A C4A C3A 0.6(3) . . . . ?
C14A C9A C10A C11A -0.4(3) . . . . ?
C8A C9A C10A C11A -179.01(16) . . . . ?
N1 C8 C9 C10 129.34(18) . . . . ?
N1 C8 C9 C14 -50.4(2) . . . . ?
C10A C9A C14A C13A 0.4(2) . . . . ?
C8A C9A C14A C13A 179.02(16) . . . . ?
C6 C5 C4 C3 0.6(3) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C7 C2 C3 C4 -179.27(16) . . . . ?
C5A C6A C1A C2A -1.5(2) . . . . ?
C5A C6A C1A Se1A 179.74(12) . . . . ?
C3A C2A C1A C6A 0.5(2) . . . . ?
C7A C2A C1A C6A -178.58(14) . . . . ?
C3A C2A C1A Se1A 179.44(11) . . . . ?
C7A C2A C1A Se1A 0.32(17) . . . . ?
N1A Se1A C1A C6A -179.41(15) . . . . ?
N1A Se1A C1A C2A 1.79(11) . . . . ?
C14 C9 C10 C11 0.2(3) . . . . ?
C8 C9 C10 C11 -179.49(17) . . . . ?
C10 C9 C14 C13 -0.7(3) . . . . ?
C8 C9 C14 C13 179.06(18) . . . . ?
C11A C12A C13A C14A -0.1(3) . . . . ?
C9A C14A C13A C12A -0.1(3) . . . . ?
C13A C12A C11A C10A 0.1(3) . . . . ?
C9A C10A C11A C12A 0.1(3) . . . . ?
C9 C14 C13 C12 0.4(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C14 C13 C12 C11 0.4(3) . . . . ?

_refine_diff_density_max         0.926
_refine_diff_density_min         -1.500
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_3-DMAP
_database_code_depnum_ccdc_archive 'CCDC 1867212'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_3-DMAP              
;
PROBLEM: Short Inter D...A Contact  Se1      ..N3       .       2.30 Ang.
RESPONSE: CHALCOGEN BONDING
;
# Added during the CSD deposition process: Wednesday 12 September 2018 03:20 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 N4 O Se'
_chemical_formula_weight         421.35
_chemical_oxdiff_usercomment     'Se Dimer with DMAP repeat of jmwtf78'

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'
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'

_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                   8.8093(2)
_cell_length_b                   10.7445(2)
_cell_length_c                   10.9812(2)
_cell_angle_alpha                111.687(2)
_cell_angle_beta                 109.283(2)
_cell_angle_gamma                96.631(2)
_cell_volume                     877.57(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    20172
_cell_measurement_theta_min      2.5420
_cell_measurement_theta_max      40.8900

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    2.159
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.91296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.786
_oxdiff_exptl_absorpt_empirical_full_max 1.451
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_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, Dualflex, HyPix'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56053
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.182
_diffrn_reflns_theta_max         41.067
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11273
_reflns_number_gt                8667
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11273
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_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
C1 C 0.62509(13) 0.36564(11) 0.66274(11) 0.01335(16) Uani 1 1 d . . . . .
C2 C 0.49312(13) 0.42843(11) 0.64743(11) 0.01283(16) Uani 1 1 d . . . . .
C3 C 0.49107(14) 0.53725(12) 0.76590(12) 0.01679(19) Uani 1 1 d . . . . .
H3 H 0.404717 0.579971 0.754825 0.020 Uiso 1 1 calc R U . . .
C4 C 0.61791(15) 0.58093(13) 0.89938(12) 0.0198(2) Uani 1 1 d . . . . .
H4 H 0.616774 0.652674 0.978737 0.024 Uiso 1 1 calc R U . . .
C5 C 0.74818(15) 0.51699(12) 0.91495(12) 0.0188(2) Uani 1 1 d . . . . .
H5 H 0.832615 0.546271 1.005334 0.023 Uiso 1 1 calc R U . . .
C6 C 0.75373(14) 0.41056(12) 0.79792(12) 0.01619(18) Uani 1 1 d . . . . .
H6 H 0.841820 0.369768 0.809349 0.019 Uiso 1 1 calc R U . . .
C7 C 0.36199(13) 0.37321(11) 0.50314(11) 0.01242(16) Uani 1 1 d . . . . .
C8 C 0.29914(13) 0.20200(11) 0.26458(11) 0.01377(17) Uani 1 1 d . . . . .
C9 C 0.15018(13) 0.24992(11) 0.22286(11) 0.01261(16) Uani 1 1 d . . . . .
C10 C 0.11855(13) 0.35289(11) 0.32934(11) 0.01300(16) Uani 1 1 d . . . . .
C11 C -0.02982(14) 0.39314(12) 0.28699(12) 0.01542(18) Uani 1 1 d . . . . .
H11 H -0.055503 0.457943 0.355593 0.019 Uiso 1 1 calc R U . . .
C12 C -0.13701(14) 0.33685(12) 0.14431(13) 0.01724(19) Uani 1 1 d . . . . .
H12 H -0.233374 0.365547 0.117446 0.021 Uiso 1 1 calc R U . . .
C13 C -0.10253(14) 0.23673(12) 0.03902(12) 0.01676(19) Uani 1 1 d . . . . .
H13 H -0.175010 0.200269 -0.056978 0.020 Uiso 1 1 calc R U . . .
C14 C 0.03879(14) 0.19293(11) 0.07854(12) 0.01525(17) Uani 1 1 d . . . . .
H14 H 0.060631 0.125207 0.009273 0.018 Uiso 1 1 calc R U . . .
C15 C 0.85255(14) 0.08228(12) 0.65647(12) 0.01556(18) Uani 1 1 d . . . . .
H15 H 0.753539 0.040827 0.656013 0.019 Uiso 1 1 calc R U . . .
C16 C 0.99293(13) 0.04310(11) 0.71103(12) 0.01451(17) Uani 1 1 d . . . . .
H16 H 0.987422 -0.023105 0.746199 0.017 Uiso 1 1 calc R U . . .
C17 C 1.14667(13) 0.10386(11) 0.71367(11) 0.01262(16) Uani 1 1 d . . . . .
C18 C 1.14181(14) 0.20343(12) 0.65751(12) 0.01602(18) Uani 1 1 d . . . . .
H18 H 1.238362 0.247674 0.656639 0.019 Uiso 1 1 calc R U . . .
C19 C 0.99403(15) 0.23446(12) 0.60432(13) 0.01780(19) Uani 1 1 d . . . . .
H19 H 0.993954 0.298983 0.566568 0.021 Uiso 1 1 calc R U . . .
C20 C 1.28897(15) -0.03418(13) 0.82307(14) 0.0199(2) Uani 1 1 d . . . . .
H20A H 1.276137 0.004118 0.911952 0.030 Uiso 1 1 calc R U . . .
H20B H 1.393138 -0.058254 0.839188 0.030 Uiso 1 1 calc R U . . .
H20C H 1.198625 -0.115984 0.755889 0.030 Uiso 1 1 calc R U . . .
C21 C 1.44224(14) 0.13284(13) 0.76521(14) 0.0194(2) Uani 1 1 d . . . . .
H21A H 1.425916 0.115580 0.668917 0.029 Uiso 1 1 calc R U . . .
H21B H 1.529039 0.093975 0.802733 0.029 Uiso 1 1 calc R U . . .
H21C H 1.473699 0.231324 0.823721 0.029 Uiso 1 1 calc R U . . .
N1 N 0.40018(11) 0.27141(9) 0.40838(10) 0.01297(14) Uani 1 1 d . . . . .
N2 N 0.22665(11) 0.41490(9) 0.47262(10) 0.01328(15) Uani 1 1 d . . . . .
N3 N 0.84971(12) 0.17717(10) 0.60360(11) 0.01620(16) Uani 1 1 d . . . . .
N4 N 1.28748(12) 0.06851(11) 0.76558(11) 0.01625(16) Uani 1 1 d . . . . .
O1 O 0.33555(11) 0.10727(9) 0.18313(9) 0.01900(16) Uani 1 1 d . . . . .
Se1 Se 0.60635(2) 0.22057(2) 0.48728(2) 0.01390(3) 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 C6 1.3978(15) . ?
C1 C2 1.4039(15) . ?
C1 Se1 1.9184(11) . ?
C2 C3 1.3986(15) . ?
C2 C7 1.4612(15) . ?
C3 C4 1.3806(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.3990(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.3893(17) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.3057(14) . ?
C7 N1 1.3665(13) . ?
C8 O1 1.2373(13) . ?
C8 N1 1.3748(14) . ?
C8 C9 1.4595(14) . ?
C9 C14 1.4022(15) . ?
C9 C10 1.4139(15) . ?
C10 N2 1.3840(14) . ?
C10 C11 1.4104(15) . ?
C11 C12 1.3795(16) . ?
C11 H11 0.9300 . ?
C12 C13 1.4051(17) . ?
C12 H12 0.9300 . ?
C13 C14 1.3745(15) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 N3 1.3457(14) . ?
C15 C16 1.3722(15) . ?
C15 H15 0.9300 . ?
C16 C17 1.4202(14) . ?
C16 H16 0.9300 . ?
C17 N4 1.3453(14) . ?
C17 C18 1.4168(15) . ?
C18 C19 1.3744(16) . ?
C18 H18 0.9300 . ?
C19 N3 1.3432(15) . ?
C19 H19 0.9300 . ?
C20 N4 1.4590(15) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N4 1.4576(14) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 Se1 1.9716(9) . ?
N3 Se1 2.3039(10) . ?

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
C6 C1 C2 119.70(10) . . ?
C6 C1 Se1 126.25(8) . . ?
C2 C1 Se1 114.05(8) . . ?
C3 C2 C1 120.49(10) . . ?
C3 C2 C7 123.33(10) . . ?
C1 C2 C7 116.18(9) . . ?
C4 C3 C2 119.65(11) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.84(11) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121.23(11) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.08(11) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N2 C7 N1 125.89(10) . . ?
N2 C7 C2 123.67(10) . . ?
N1 C7 C2 110.42(9) . . ?
O1 C8 N1 120.88(10) . . ?
O1 C8 C9 125.54(10) . . ?
N1 C8 C9 113.58(9) . . ?
C14 C9 C10 120.49(10) . . ?
C14 C9 C8 120.11(9) . . ?
C10 C9 C8 119.40(9) . . ?
N2 C10 C11 119.01(9) . . ?
N2 C10 C9 122.70(9) . . ?
C11 C10 C9 118.28(10) . . ?
C12 C11 C10 120.33(10) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.87(10) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.71(10) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 120.27(10) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
N3 C15 C16 123.86(10) . . ?
N3 C15 H15 118.1 . . ?
C16 C15 H15 118.1 . . ?
C15 C16 C17 119.86(10) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
N4 C17 C18 122.26(9) . . ?
N4 C17 C16 122.06(9) . . ?
C18 C17 C16 115.68(9) . . ?
C19 C18 C17 119.83(10) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
N3 C19 C18 123.93(10) . . ?
N3 C19 H19 118.0 . . ?
C18 C19 H19 118.0 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C7 N1 C8 122.90(9) . . ?
C7 N1 Se1 117.06(7) . . ?
C8 N1 Se1 120.00(7) . . ?
C7 N2 C10 115.39(9) . . ?
C19 N3 C15 116.84(10) . . ?
C19 N3 Se1 119.71(7) . . ?
C15 N3 Se1 122.90(7) . . ?
C17 N4 C20 121.10(9) . . ?
C17 N4 C21 120.18(9) . . ?
C20 N4 C21 118.72(9) . . ?
C1 Se1 N1 82.23(4) . . ?
C1 Se1 N3 91.64(4) . . ?
N1 Se1 N3 173.81(4) . . ?

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
C6 C1 C2 C3 1.20(16) . . . . ?
Se1 C1 C2 C3 -179.08(8) . . . . ?
C6 C1 C2 C7 -178.68(9) . . . . ?
Se1 C1 C2 C7 1.04(12) . . . . ?
C1 C2 C3 C4 -1.50(16) . . . . ?
C7 C2 C3 C4 178.37(10) . . . . ?
C2 C3 C4 C5 0.58(18) . . . . ?
C3 C4 C5 C6 0.66(18) . . . . ?
C4 C5 C6 C1 -0.96(17) . . . . ?
C2 C1 C6 C5 0.03(16) . . . . ?
Se1 C1 C6 C5 -179.65(8) . . . . ?
C3 C2 C7 N2 -3.81(16) . . . . ?
C1 C2 C7 N2 176.06(9) . . . . ?
C3 C2 C7 N1 177.67(10) . . . . ?
C1 C2 C7 N1 -2.46(13) . . . . ?
O1 C8 C9 C14 -3.71(17) . . . . ?
N1 C8 C9 C14 177.29(9) . . . . ?
O1 C8 C9 C10 175.56(11) . . . . ?
N1 C8 C9 C10 -3.43(14) . . . . ?
C14 C9 C10 N2 -178.30(10) . . . . ?
C8 C9 C10 N2 2.42(15) . . . . ?
C14 C9 C10 C11 1.93(15) . . . . ?
C8 C9 C10 C11 -177.35(9) . . . . ?
N2 C10 C11 C12 177.65(10) . . . . ?
C9 C10 C11 C12 -2.57(16) . . . . ?
C10 C11 C12 C13 1.27(17) . . . . ?
C11 C12 C13 C14 0.75(17) . . . . ?
C12 C13 C14 C9 -1.39(17) . . . . ?
C10 C9 C14 C13 0.04(16) . . . . ?
C8 C9 C14 C13 179.31(10) . . . . ?
N3 C15 C16 C17 -0.02(17) . . . . ?
C15 C16 C17 N4 -179.76(11) . . . . ?
C15 C16 C17 C18 -0.06(16) . . . . ?
N4 C17 C18 C19 179.25(11) . . . . ?
C16 C17 C18 C19 -0.45(16) . . . . ?
C17 C18 C19 N3 1.11(18) . . . . ?
N2 C7 N1 C8 2.04(17) . . . . ?
C2 C7 N1 C8 -179.48(9) . . . . ?
N2 C7 N1 Se1 -175.69(8) . . . . ?
C2 C7 N1 Se1 2.79(11) . . . . ?
O1 C8 N1 C7 -177.59(10) . . . . ?
C9 C8 N1 C7 1.46(14) . . . . ?
O1 C8 N1 Se1 0.08(14) . . . . ?
C9 C8 N1 Se1 179.12(7) . . . . ?
N1 C7 N2 C10 -3.21(15) . . . . ?
C2 C7 N2 C10 178.51(9) . . . . ?
C11 C10 N2 C7 -179.33(9) . . . . ?
C9 C10 N2 C7 0.90(15) . . . . ?
C18 C19 N3 C15 -1.16(18) . . . . ?
C18 C19 N3 Se1 -172.93(9) . . . . ?
C16 C15 N3 C19 0.61(17) . . . . ?
C16 C15 N3 Se1 172.08(9) . . . . ?
C18 C17 N4 C20 179.87(11) . . . . ?
C16 C17 N4 C20 -0.45(17) . . . . ?
C18 C17 N4 C21 -0.14(16) . . . . ?
C16 C17 N4 C21 179.55(10) . . . . ?

_refine_diff_density_max         0.763
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_1b-DMAP-H2O
_database_code_depnum_ccdc_archive 'CCDC 1867213'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_1b-DMAP-H2O         
;
PROBLEM: Short Inter D...A Contact  Se1      ..N2       .       2.40 Ang.
RESPONSE: CHALCOGEN BONDING
;
# Added during the CSD deposition process: Wednesday 12 September 2018 03:20 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N3 O2 Se'
_chemical_formula_weight         428.38

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'
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'

_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                   9.6254(2)
_cell_length_b                   10.2486(2)
_cell_length_c                   10.6505(2)
_cell_angle_alpha                83.660(2)
_cell_angle_beta                 76.398(2)
_cell_angle_gamma                78.423(2)
_cell_volume                     998.19(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200.00(10)
_cell_measurement_reflns_used    13259
_cell_measurement_theta_min      2.6110
_cell_measurement_theta_max      32.8880

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.237
_exptl_absorpt_coefficient_mu    1.901
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.84273
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.861
_oxdiff_exptl_absorpt_empirical_full_max 1.204
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      200.00(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, Dualflex, HyPix'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30047
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.623
_diffrn_reflns_theta_max         41.058
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             12528
_reflns_number_gt                6303
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.2209P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         12528
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
C1 C 0.81086(15) 0.81136(16) 1.08994(15) 0.0406(3) Uani 1 1 d . . . . .
C2 C 0.81394(15) 0.73785(15) 1.20668(16) 0.0411(3) Uani 1 1 d . . . . .
C3 C 0.69226(18) 0.75149(18) 1.30893(18) 0.0508(4) Uani 1 1 d . . . . .
H3 H 0.694608 0.701494 1.387025 0.061 Uiso 1 1 calc R U . . .
C4 C 0.56832(18) 0.8401(2) 1.2928(2) 0.0574(5) Uani 1 1 d . . . . .
H4 H 0.485744 0.848648 1.359528 0.069 Uiso 1 1 calc R U . . .
C5 C 0.56697(19) 0.9156(3) 1.1781(2) 0.0674(6) Uani 1 1 d . . . . .
H5 H 0.483362 0.976124 1.168923 0.081 Uiso 1 1 calc R U . . .
C6 C 0.68679(19) 0.9040(2) 1.07604(19) 0.0596(5) Uani 1 1 d . . . . .
H6 H 0.684766 0.956989 0.999504 0.072 Uiso 1 1 calc R U . . .
C7 C 0.94930(17) 0.64344(16) 1.21318(17) 0.0479(4) Uani 1 1 d . . . . .
C8 C 1.1861(2) 0.5544(2) 1.0849(2) 0.0767(8) Uani 1 1 d . . . . .
H8A H 1.169696 0.468348 1.067725 0.092 Uiso 1 1 calc R U . . .
H8B H 1.219826 0.543131 1.164994 0.092 Uiso 1 1 calc R U . . .
C9 C 1.30241(15) 0.59666(14) 0.97768(15) 0.0399(3) Uani 1 1 d . . . . .
C10 C 1.3388(2) 0.5418(3) 0.8604(2) 0.0728(6) Uani 1 1 d . . . . .
H10 H 1.286152 0.481050 0.844403 0.087 Uiso 1 1 calc R U . . .
C11 C 1.4541(3) 0.5762(3) 0.7646(2) 0.0827(8) Uani 1 1 d . . . . .
H11 H 1.478621 0.537041 0.685758 0.099 Uiso 1 1 calc R U . . .
C12 C 1.5287(2) 0.6638(2) 0.7846(3) 0.0730(7) Uani 1 1 d . . . . .
H12 H 1.604455 0.687409 0.719681 0.088 Uiso 1 1 calc R U . . .
C13 C 1.4949(3) 0.7184(3) 0.8989(4) 0.0917(9) Uani 1 1 d . . . . .
H13 H 1.548047 0.779785 0.912802 0.110 Uiso 1 1 calc R U . . .
C14 C 1.3825(2) 0.6854(2) 0.9965(2) 0.0645(5) Uani 1 1 d . . . . .
H14 H 1.361364 0.723893 1.075434 0.077 Uiso 1 1 calc R U . . .
C15 C 0.8936(2) 1.0482(2) 0.78568(18) 0.0547(4) Uani 1 1 d . . . . .
H15 H 0.921131 1.086931 0.848827 0.066 Uiso 1 1 calc R U . . .
C16 C 0.86496(18) 1.12709(19) 0.67955(18) 0.0497(4) Uani 1 1 d . . . . .
H16 H 0.873473 1.216564 0.672070 0.060 Uiso 1 1 calc R U . . .
C17 C 0.82248(15) 1.07319(17) 0.58105(16) 0.0424(3) Uani 1 1 d . . . . .
C18 C 0.81240(17) 0.93655(17) 0.60231(16) 0.0451(3) Uani 1 1 d . . . . .
H18 H 0.784052 0.894438 0.541960 0.054 Uiso 1 1 calc R U . . .
C19 C 0.84449(18) 0.86643(19) 0.71194(17) 0.0489(4) Uani 1 1 d . . . . .
H19 H 0.838045 0.776385 0.722634 0.059 Uiso 1 1 calc R U . . .
C20 C 0.7431(2) 1.0913(2) 0.37731(18) 0.0585(4) Uani 1 1 d . . . . .
H20A H 0.646635 1.074308 0.412961 0.088 Uiso 1 1 calc R U . . .
H20B H 0.806881 1.009307 0.351857 0.088 Uiso 1 1 calc R U . . .
H20C H 0.742113 1.153603 0.303125 0.088 Uiso 1 1 calc R U . . .
C21 C 0.8062(3) 1.2869(2) 0.4565(2) 0.0658(5) Uani 1 1 d . . . . .
H21D H 0.897950 1.296990 0.471405 0.099 Uiso 1 1 calc R U . . .
H21E H 0.728777 1.336773 0.516567 0.099 Uiso 1 1 calc R U . . .
H21F H 0.799898 1.319590 0.369620 0.099 Uiso 1 1 calc R U . . .
N1 N 1.04711(14) 0.64903(14) 1.10228(14) 0.0457(3) Uani 1 1 d . . . . .
N2 N 0.88440(16) 0.91829(17) 0.80459(14) 0.0526(3) Uani 1 1 d . . . . .
N3 N 0.79428(16) 1.14702(16) 0.47435(15) 0.0491(3) Uani 1 1 d . . . . .
O1 O 0.96966(16) 0.56828(15) 1.30957(15) 0.0746(5) Uani 1 1 d . . . . .
O2 O 1.17480(19) 0.40356(18) 1.43231(19) 0.0726(5) Uani 1 1 d . . . . .
Se1 Se 0.98684(2) 0.76886(2) 0.96334(2) 0.04419(6) Uani 1 1 d . . . . .
H2A H 1.120(4) 0.409(3) 1.509(4) 0.119(12) Uiso 1 1 d . . . . .
H2B H 1.132(3) 0.461(3) 1.395(3) 0.065(7) Uiso 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 C2 1.384(2) . ?
C1 C6 1.395(2) . ?
C1 Se1 1.9070(14) . ?
C2 C3 1.395(2) . ?
C2 C7 1.470(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.243(2) . ?
C7 N1 1.330(2) . ?
C8 N1 1.472(2) . ?
C8 C9 1.493(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.362(3) . ?
C9 C10 1.367(3) . ?
C10 C11 1.393(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.319(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.339(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 N2 1.342(3) . ?
C15 C16 1.365(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.412(2) . ?
C16 H16 0.9300 . ?
C17 N3 1.346(2) . ?
C17 C18 1.413(2) . ?
C18 C19 1.368(2) . ?
C18 H18 0.9300 . ?
C19 N2 1.334(2) . ?
C19 H19 0.9300 . ?
C20 N3 1.456(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N3 1.449(3) . ?
C21 H21D 0.9600 . ?
C21 H21E 0.9600 . ?
C21 H21F 0.9600 . ?
N1 Se1 1.9367(14) . ?
O2 H2A 0.86(4) . ?
O2 H2B 0.77(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 C6 119.68(14) . . ?
C2 C1 Se1 112.70(11) . . ?
C6 C1 Se1 127.62(13) . . ?
C1 C2 C3 120.70(15) . . ?
C1 C2 C7 116.06(13) . . ?
C3 C2 C7 123.20(15) . . ?
C4 C3 C2 119.17(17) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 119.98(16) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.63(18) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.76(19) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
O1 C7 N1 124.48(15) . . ?
O1 C7 C2 124.49(14) . . ?
N1 C7 C2 111.04(14) . . ?
N1 C8 C9 113.99(14) . . ?
N1 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C14 C9 C10 117.56(17) . . ?
C14 C9 C8 120.78(19) . . ?
C10 C9 C8 121.53(19) . . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 121.2(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C9 C14 C13 120.3(2) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
N2 C15 C16 124.05(17) . . ?
N2 C15 H15 118.0 . . ?
C16 C15 H15 118.0 . . ?
C15 C16 C17 120.17(17) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
N3 C17 C16 122.16(16) . . ?
N3 C17 C18 122.55(15) . . ?
C16 C17 C18 115.29(15) . . ?
C19 C18 C17 119.77(16) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
N2 C19 C18 124.51(17) . . ?
N2 C19 H19 117.7 . . ?
C18 C19 H19 117.7 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 H21D 109.5 . . ?
N3 C21 H21E 109.5 . . ?
H21D C21 H21E 109.5 . . ?
N3 C21 H21F 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
C7 N1 C8 119.63(14) . . ?
C7 N1 Se1 116.80(11) . . ?
C8 N1 Se1 123.10(12) . . ?
C19 N2 C15 116.20(16) . . ?
C17 N3 C21 120.67(16) . . ?
C17 N3 C20 121.23(16) . . ?
C21 N3 C20 118.01(16) . . ?
H2A O2 H2B 101(3) . . ?
C1 Se1 N1 83.33(6) . . ?

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
C6 C1 C2 C3 2.6(3) . . . . ?
Se1 C1 C2 C3 -177.24(13) . . . . ?
C6 C1 C2 C7 -179.48(17) . . . . ?
Se1 C1 C2 C7 0.68(19) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C7 C2 C3 C4 -178.16(18) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
C2 C1 C6 C5 -2.9(3) . . . . ?
Se1 C1 C6 C5 176.88(16) . . . . ?
C1 C2 C7 O1 -178.77(19) . . . . ?
C3 C2 C7 O1 -0.9(3) . . . . ?
C1 C2 C7 N1 1.2(2) . . . . ?
C3 C2 C7 N1 179.07(17) . . . . ?
N1 C8 C9 C14 81.9(3) . . . . ?
N1 C8 C9 C10 -102.4(2) . . . . ?
C14 C9 C10 C11 0.1(3) . . . . ?
C8 C9 C10 C11 -175.7(2) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C10 C11 C12 C13 1.1(4) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
C8 C9 C14 C13 176.6(2) . . . . ?
C12 C13 C14 C9 -0.6(4) . . . . ?
N2 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 N3 -179.50(16) . . . . ?
C15 C16 C17 C18 0.2(2) . . . . ?
N3 C17 C18 C19 179.07(15) . . . . ?
C16 C17 C18 C19 -0.7(2) . . . . ?
C17 C18 C19 N2 0.8(2) . . . . ?
O1 C7 N1 C8 5.0(3) . . . . ?
C2 C7 N1 C8 -174.98(19) . . . . ?
O1 C7 N1 Se1 177.41(17) . . . . ?
C2 C7 N1 Se1 -2.6(2) . . . . ?
C9 C8 N1 C7 -161.54(19) . . . . ?
C9 C8 N1 Se1 26.6(3) . . . . ?
C18 C19 N2 C15 -0.4(2) . . . . ?
C16 C15 N2 C19 0.0(3) . . . . ?
C16 C17 N3 C21 -0.2(2) . . . . ?
C18 C17 N3 C21 -179.90(16) . . . . ?
C16 C17 N3 C20 -176.67(16) . . . . ?
C18 C17 N3 C20 3.6(2) . . . . ?

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 N2 0.93 2.48 3.071(2) 121.4 .
C15 H15 Se1 0.93 3.00 3.9248(18) 175.3 2_777
C19 H19 O2 0.93 2.65 3.366(3) 134.8 2_767
O2 H2A O1 0.86(4) 1.94(4) 2.791(2) 169(3) 2_768
O2 H2B O1 0.77(3) 2.06(3) 2.801(2) 160(3) .

_refine_diff_density_max         0.585
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.057

