# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1PYR
_database_code_depnum_ccdc_archive 'CCDC 2000583'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_1PYR                
;
PROBLEM: Short Inter D...A Contact  Se1      ..N5       .       2.47 Ang.
RESPONSE: Chalcogen bonding interaction
;
# Added during the CSD deposition process: Saturday 02 May 2020 07:31 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            'C24 H17 N5 O4 Se'
_chemical_formula_weight         518.39
_chemical_oxdiff_usercomment     'Tom Fellowes Se intermediate with 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           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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'

_cell_length_a                   4.9726(2)
_cell_length_b                   14.6836(5)
_cell_length_c                   14.4255(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.154(4)
_cell_angle_gamma                90
_cell_volume                     1042.64(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    3423
_cell_measurement_theta_min      3.0190
_cell_measurement_theta_max      75.4450

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    2.829
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.88658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.36a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.759
_oxdiff_exptl_absorpt_empirical_full_max 1.299
_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 (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  '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            6794
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.010
_diffrn_reflns_theta_max         76.785
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.710
_diffrn_reflns_point_group_measured_fraction_full 0.750
_reflns_number_total             3132
_reflns_number_gt                2977
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.451
_reflns_Friedel_fraction_max     0.443
_reflns_Friedel_fraction_full    0.501

_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 1.171.40.36a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.36a (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)+(0.0561P)²+0.3921P] 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 848 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3132
_refine_ls_number_parameters     307
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_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 1.2330(12) 0.5110(4) 0.6729(5) 0.0243(12) Uani 1 1 d . . . . .
C2 C 1.3093(12) 0.5973(4) 0.7088(4) 0.0222(11) Uani 1 1 d . . . . .
C3 C 1.5305(13) 0.6068(4) 0.7777(4) 0.0258(12) Uani 1 1 d . . . . .
H3 H 1.585177 0.665562 0.800853 0.031 Uiso 1 1 calc R U . . .
C4 C 1.6726(13) 0.5298(4) 0.8131(4) 0.0276(12) Uani 1 1 d . . . . .
H4 H 1.826941 0.535827 0.859711 0.033 Uiso 1 1 calc R U . . .
C5 C 1.5884(13) 0.4443(4) 0.7800(4) 0.0267(12) Uani 1 1 d . . . . .
H5 H 1.683687 0.391914 0.805695 0.032 Uiso 1 1 calc R U . . .
C6 C 1.3673(12) 0.4335(4) 0.7101(4) 0.0252(12) Uani 1 1 d . . . . .
H6 H 1.309680 0.374611 0.688401 0.030 Uiso 1 1 calc R U . . .
C7 C 1.1338(12) 0.6740(4) 0.6708(4) 0.0226(11) Uani 1 1 d . . . . .
C8 C 0.7315(11) 0.7019(4) 0.5529(4) 0.0188(10) Uani 1 1 d . . . . .
C9 C 0.7489(12) 0.7959(4) 0.5531(4) 0.0206(11) Uani 1 1 d . . . . .
H9 H 0.898111 0.825070 0.589689 0.025 Uiso 1 1 calc R U . . .
C10 C 0.5510(11) 0.8479(4) 0.5003(4) 0.0208(11) Uani 1 1 d . . . . .
C11 C 0.3249(11) 0.8090(4) 0.4432(4) 0.0202(11) Uani 1 1 d . . . . .
C12 C 0.3142(12) 0.7135(4) 0.4435(4) 0.0216(11) Uani 1 1 d . . . . .
H12 H 0.167971 0.683691 0.405880 0.026 Uiso 1 1 calc R U . . .
C13 C 0.5102(12) 0.6615(4) 0.4967(4) 0.0230(11) Uani 1 1 d . . . . .
H13 H 0.494649 0.596976 0.495271 0.028 Uiso 1 1 calc R U . . .
C14 C -0.0780(13) 0.8320(4) 0.3234(4) 0.0238(12) Uani 1 1 d . . . . .
C15 C -0.2640(12) 0.9071(4) 0.2835(4) 0.0217(11) Uani 1 1 d . . . . .
C16 C -0.4970(13) 0.8841(4) 0.2221(5) 0.0265(12) Uani 1 1 d . . . . .
H16 H -0.537524 0.822443 0.205752 0.032 Uiso 1 1 calc R U . . .
C17 C -0.6674(13) 0.9540(5) 0.1859(4) 0.0287(13) Uani 1 1 d . . . . .
H17 H -0.829039 0.941124 0.144456 0.034 Uiso 1 1 calc R U . . .
C18 C -0.5991(15) 1.0423(5) 0.2107(5) 0.0320(14) Uani 1 1 d . . . . .
H18 H -0.712318 1.091243 0.186143 0.038 Uiso 1 1 calc R U . . .
C19 C -0.3628(14) 1.0594(5) 0.2721(5) 0.0310(13) Uani 1 1 d . . . . .
H19 H -0.318420 1.120705 0.288790 0.037 Uiso 1 1 calc R U . . .
C20 C 1.1517(13) 0.3338(4) 0.4694(5) 0.0305(13) Uani 1 1 d . . . . .
H20 H 1.258002 0.379910 0.446034 0.037 Uiso 1 1 calc R U . . .
C21 C 1.1528(14) 0.2469(4) 0.4313(5) 0.0319(13) Uani 1 1 d . . . . .
H21 H 1.257190 0.234340 0.382528 0.038 Uiso 1 1 calc R U . . .
C22 C 1.0007(13) 0.1792(4) 0.4650(5) 0.0296(13) Uani 1 1 d . . . . .
H22 H 1.000860 0.118973 0.440906 0.035 Uiso 1 1 calc R U . . .
C23 C 0.8476(15) 0.2014(4) 0.5349(5) 0.0327(14) Uani 1 1 d . . . . .
H23 H 0.738970 0.156688 0.559480 0.039 Uiso 1 1 calc R U . . .
C24 C 0.8561(14) 0.2904(4) 0.5684(5) 0.0319(14) Uani 1 1 d . . . . .
H24 H 0.748712 0.305730 0.615640 0.038 Uiso 1 1 calc R U . . .
N1 N 0.9300(10) 0.6454(3) 0.6041(3) 0.0218(10) Uani 1 1 d . . . . .
N2 N 0.5932(10) 0.9462(3) 0.5051(4) 0.0220(9) Uani 1 1 d . . . . .
N3 N 0.1254(10) 0.8612(3) 0.3905(4) 0.0212(10) Uani 1 1 d . . . . .
H3A H 0.130909 0.920130 0.401723 0.025 Uiso 1 1 calc R U . . .
N4 N -0.1937(11) 0.9929(4) 0.3092(4) 0.0271(11) Uani 1 1 d . . . . .
N5 N 1.0086(12) 0.3549(4) 0.5370(4) 0.0278(11) Uani 1 1 d . . . . .
O1 O 1.1730(9) 0.7536(3) 0.6982(3) 0.0301(9) Uani 1 1 d . . . . .
O2 O 0.8152(9) 0.9745(3) 0.5429(3) 0.0282(10) Uani 1 1 d . . . . .
O3 O 0.4095(10) 0.9986(3) 0.4719(4) 0.0269(9) Uani 1 1 d . . . . .
O4 O -0.1123(10) 0.7533(3) 0.2960(4) 0.0318(10) Uani 1 1 d . . . . .
Se1 Se 0.93855(7) 0.51659(3) 0.57303(5) 0.02229(18) 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 1.389(9) . ?
C1 C2 1.400(9) . ?
C1 Se1 1.905(7) . ?
C2 C3 1.382(9) . ?
C2 C7 1.482(8) . ?
C3 C4 1.391(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(9) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.240(7) . ?
C7 N1 1.361(8) . ?
C8 C9 1.382(8) . ?
C8 C13 1.403(8) . ?
C8 N1 1.415(7) . ?
C9 C10 1.385(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.417(8) . ?
C10 N2 1.459(7) . ?
C11 N3 1.392(7) . ?
C11 C12 1.403(8) . ?
C12 C13 1.383(8) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O4 1.224(8) . ?
C14 N3 1.366(8) . ?
C14 C15 1.500(8) . ?
C15 N4 1.346(8) . ?
C15 C16 1.396(9) . ?
C16 C17 1.385(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.375(11) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(10) . ?
C18 H18 0.9500 . ?
C19 N4 1.348(9) . ?
C19 H19 0.9500 . ?
C20 N5 1.323(9) . ?
C20 C21 1.389(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(10) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(9) . ?
C23 H23 0.9500 . ?
C24 N5 1.332(9) . ?
C24 H24 0.9500 . ?
N1 Se1 1.945(5) . ?
N2 O2 1.232(7) . ?
N2 O3 1.237(7) . ?
N3 H3A 0.8800 . ?
N5 Se1 2.466(5) . ?

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 120.6(6) . . ?
C6 C1 Se1 127.1(5) . . ?
C2 C1 Se1 112.3(5) . . ?
C3 C2 C1 120.3(6) . . ?
C3 C2 C7 123.8(5) . . ?
C1 C2 C7 115.9(5) . . ?
C2 C3 C4 119.5(6) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.8(6) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.4(6) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.3(6) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O1 C7 N1 125.8(5) . . ?
O1 C7 C2 122.7(5) . . ?
N1 C7 C2 111.5(5) . . ?
C9 C8 C13 117.8(5) . . ?
C9 C8 N1 123.1(5) . . ?
C13 C8 N1 119.0(5) . . ?
C8 C9 C10 120.7(5) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 122.7(5) . . ?
C9 C10 N2 115.7(5) . . ?
C11 C10 N2 121.6(5) . . ?
N3 C11 C12 121.9(5) . . ?
N3 C11 C10 122.7(5) . . ?
C12 C11 C10 115.4(5) . . ?
C13 C12 C11 122.0(5) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C8 121.4(5) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
O4 C14 N3 125.5(6) . . ?
O4 C14 C15 121.3(6) . . ?
N3 C14 C15 113.3(5) . . ?
N4 C15 C16 124.1(6) . . ?
N4 C15 C14 117.4(5) . . ?
C16 C15 C14 118.5(5) . . ?
C17 C16 C15 117.9(6) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C18 C17 C16 119.0(6) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 119.4(6) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
N4 C19 C18 123.0(6) . . ?
N4 C19 H19 118.5 . . ?
C18 C19 H19 118.5 . . ?
N5 C20 C21 122.6(6) . . ?
N5 C20 H20 118.7 . . ?
C21 C20 H20 118.7 . . ?
C22 C21 C20 119.3(6) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 118.2(6) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
C22 C23 C24 118.8(6) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
N5 C24 C23 122.7(6) . . ?
N5 C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?
C7 N1 C8 125.6(5) . . ?
C7 N1 Se1 115.1(4) . . ?
C8 N1 Se1 119.1(4) . . ?
O2 N2 O3 121.8(5) . . ?
O2 N2 C10 117.9(5) . . ?
O3 N2 C10 120.2(5) . . ?
C14 N3 C11 127.8(5) . . ?
C14 N3 H3A 116.1 . . ?
C11 N3 H3A 116.1 . . ?
C15 N4 C19 116.5(6) . . ?
C20 N5 C24 118.4(6) . . ?
C20 N5 Se1 119.2(4) . . ?
C24 N5 Se1 120.6(4) . . ?
C1 Se1 N1 84.7(2) . . ?
C1 Se1 N5 90.1(2) . . ?
N1 Se1 N5 173.2(2) . . ?

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 4.1(9) . . . . ?
Se1 C1 C2 C3 -176.0(5) . . . . ?
C6 C1 C2 C7 -173.7(5) . . . . ?
Se1 C1 C2 C7 6.2(7) . . . . ?
C1 C2 C3 C4 -1.7(10) . . . . ?
C7 C2 C3 C4 175.9(6) . . . . ?
C2 C3 C4 C5 -1.1(10) . . . . ?
C3 C4 C5 C6 1.6(10) . . . . ?
C2 C1 C6 C5 -3.5(9) . . . . ?
Se1 C1 C6 C5 176.5(5) . . . . ?
C4 C5 C6 C1 0.7(9) . . . . ?
C3 C2 C7 O1 0.1(10) . . . . ?
C1 C2 C7 O1 177.9(6) . . . . ?
C3 C2 C7 N1 -179.6(6) . . . . ?
C1 C2 C7 N1 -1.9(8) . . . . ?
C13 C8 C9 C10 1.0(9) . . . . ?
N1 C8 C9 C10 178.8(5) . . . . ?
C8 C9 C10 C11 -0.8(9) . . . . ?
C8 C9 C10 N2 -179.2(5) . . . . ?
C9 C10 C11 N3 179.8(5) . . . . ?
N2 C10 C11 N3 -2.0(8) . . . . ?
C9 C10 C11 C12 0.0(8) . . . . ?
N2 C10 C11 C12 178.2(5) . . . . ?
N3 C11 C12 C13 -179.1(6) . . . . ?
C10 C11 C12 C13 0.7(8) . . . . ?
C11 C12 C13 C8 -0.5(9) . . . . ?
C9 C8 C13 C12 -0.4(9) . . . . ?
N1 C8 C13 C12 -178.3(5) . . . . ?
O4 C14 C15 N4 -172.3(6) . . . . ?
N3 C14 C15 N4 7.4(8) . . . . ?
O4 C14 C15 C16 7.5(9) . . . . ?
N3 C14 C15 C16 -172.8(5) . . . . ?
N4 C15 C16 C17 -0.4(9) . . . . ?
C14 C15 C16 C17 179.9(6) . . . . ?
C15 C16 C17 C18 0.7(9) . . . . ?
C16 C17 C18 C19 -0.6(10) . . . . ?
C17 C18 C19 N4 0.1(11) . . . . ?
N5 C20 C21 C22 -0.4(11) . . . . ?
C20 C21 C22 C23 1.2(10) . . . . ?
C21 C22 C23 C24 -0.6(10) . . . . ?
C22 C23 C24 N5 -1.0(11) . . . . ?
O1 C7 N1 C8 1.7(10) . . . . ?
C2 C7 N1 C8 -178.6(5) . . . . ?
O1 C7 N1 Se1 176.9(5) . . . . ?
C2 C7 N1 Se1 -3.4(6) . . . . ?
C9 C8 N1 C7 11.7(9) . . . . ?
C13 C8 N1 C7 -170.5(6) . . . . ?
C9 C8 N1 Se1 -163.4(4) . . . . ?
C13 C8 N1 Se1 14.4(7) . . . . ?
C9 C10 N2 O2 10.6(8) . . . . ?
C11 C10 N2 O2 -167.8(6) . . . . ?
C9 C10 N2 O3 -169.3(5) . . . . ?
C11 C10 N2 O3 12.3(8) . . . . ?
O4 C14 N3 C11 -2.7(10) . . . . ?
C15 C14 N3 C11 177.6(5) . . . . ?
C12 C11 N3 C14 -10.5(9) . . . . ?
C10 C11 N3 C14 169.8(6) . . . . ?
C16 C15 N4 C19 -0.1(9) . . . . ?
C14 C15 N4 C19 179.7(6) . . . . ?
C18 C19 N4 C15 0.2(10) . . . . ?
C21 C20 N5 C24 -1.2(10) . . . . ?
C21 C20 N5 Se1 -165.9(5) . . . . ?
C23 C24 N5 C20 1.9(10) . . . . ?
C23 C24 N5 Se1 166.4(5) . . . . ?

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 N5 0.95 2.48 3.080(8) 120.8 .
C9 H9 O1 0.95 2.19 2.822(7) 122.7 .
C12 H12 O4 0.95 2.21 2.843(7) 123.4 .
C13 H13 Se1 0.95 2.61 3.100(6) 112.3 .
C18 H18 O1 0.95 2.36 3.200(8) 147.0 2_374
C21 H21 O1 0.95 2.64 3.378(8) 135.1 2_564
N3 H3A N4 0.88 2.22 2.665(7) 111.2 .
N3 H3A O3 0.88 1.97 2.641(7) 132.2 .

_refine_diff_density_max         0.635
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_1DMF
_database_code_depnum_ccdc_archive 'CCDC 2000585'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2020-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_1DMF                
;
PROBLEM: Short Inter D...A Contact  Se1      ..O1       .       2.66 Ang.
RESPONSE: CHALCOGEN BONDING
;
# Added during the CSD deposition process: Saturday 02 May 2020 08:00 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 H12 N4 O4 Se'
_chemical_formula_weight         439.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0051 0.0024 '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 0.0096 0.0048 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0160 0.0088 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.6943 2.8678 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   12.652(3)
_cell_length_b                   7.5250(15)
_cell_length_c                   34.367(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3272.0(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    3751
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      32.3

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    3.383
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.82656
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_measurement_device_type  'Dectris Eiger 16M'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35758
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.325
_diffrn_reflns_theta_max         32.284
_diffrn_reflns_theta_full        29.731
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3282
_reflns_number_gt                2513
_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       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_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)+(0.1223P)²+1.2109P] 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         3282
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1802
_refine_ls_wR_factor_gt          0.1641
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_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
Se1 Se 0.06817(3) 0.56221(6) 0.73370(2) 0.0445(2) Uani 1 1 d . . . . .
O1 O 0.3823(2) 0.5936(4) 0.73082(8) 0.0433(7) Uani 1 1 d . . . . .
O4 O 0.0810(2) 0.1683(5) 0.54788(10) 0.0594(9) Uani 1 1 d . . . . .
O3 O 0.4564(2) 0.2543(5) 0.57878(9) 0.0580(9) Uani 1 1 d . . . . .
N3 N 0.2530(3) 0.2437(5) 0.56301(10) 0.0445(8) Uani 1 1 d . . . . .
N1 N 0.2086(3) 0.5407(5) 0.71384(10) 0.0427(8) Uani 1 1 d . . . . .
N4 N 0.3248(3) 0.0900(5) 0.49974(11) 0.0487(9) Uani 1 1 d . . . . .
N2 N 0.4396(3) 0.3180(6) 0.61097(11) 0.0504(9) Uani 1 1 d . . . . .
O2 O 0.5109(3) 0.3481(7) 0.63355(11) 0.0872(14) Uani 1 1 d . . . . .
C11 C 0.2431(3) 0.3197(5) 0.59976(12) 0.0414(9) Uani 1 1 d . . . . .
C8 C 0.2233(3) 0.4699(6) 0.67565(11) 0.0411(9) Uani 1 1 d . . . . .
C10 C 0.3314(3) 0.3562(6) 0.62345(12) 0.0430(9) Uani 1 1 d . . . . .
C9 C 0.3221(3) 0.4266(6) 0.66094(13) 0.0451(10) Uani 1 1 d . . . . .
H9 H 0.382157 0.444301 0.676035 0.054 Uiso 1 1 calc R U . . .
C12 C 0.1444(3) 0.3682(6) 0.61518(12) 0.0460(9) Uani 1 1 d . . . . .
H12 H 0.083790 0.349738 0.600394 0.055 Uiso 1 1 calc R U . . .
C13 C 0.1351(3) 0.4426(6) 0.65177(13) 0.0447(10) Uani 1 1 d . . . . .
H13 H 0.068598 0.475476 0.660777 0.054 Uiso 1 1 calc R U . . .
C2 C 0.2427(3) 0.6654(6) 0.77525(12) 0.0430(9) Uani 1 1 d . . . . .
C1 C 0.1339(3) 0.6561(6) 0.77891(11) 0.0427(9) Uani 1 1 d . . . . .
C15 C 0.2183(3) 0.0962(6) 0.50242(12) 0.0461(10) Uani 1 1 d . . . . .
C6 C 0.0830(3) 0.7101(6) 0.81274(14) 0.0475(10) Uani 1 1 d . . . . .
H6 H 0.009874 0.702614 0.815049 0.057 Uiso 1 1 calc R U . . .
C7 C 0.2882(4) 0.5986(6) 0.73824(12) 0.0432(9) Uani 1 1 d . . . . .
C4 C 0.2537(3) 0.7888(6) 0.83943(12) 0.0468(10) Uani 1 1 d . . . . .
H4 H 0.293037 0.836351 0.859780 0.056 Uiso 1 1 calc R U . . .
C3 C 0.3042(3) 0.7319(6) 0.80584(12) 0.0461(10) Uani 1 1 d . . . . .
H3 H 0.377354 0.737837 0.803688 0.055 Uiso 1 1 calc R U . . .
C5 C 0.1441(3) 0.7751(6) 0.84281(12) 0.0476(10) Uani 1 1 d . . . . .
H5 H 0.111564 0.810530 0.865807 0.057 Uiso 1 1 calc R U . . .
C19 C 0.3650(4) 0.0219(7) 0.46694(13) 0.0533(11) Uani 1 1 d . . . . .
H19 H 0.438161 0.016645 0.464439 0.064 Uiso 1 1 calc R U . . .
C14 C 0.1754(3) 0.1720(6) 0.53968(12) 0.0477(10) Uani 1 1 d . . . . .
C18 C 0.3036(4) -0.0414(6) 0.43641(14) 0.0551(12) Uani 1 1 d . . . . .
H18 H 0.334683 -0.089398 0.414251 0.066 Uiso 1 1 calc R U . . .
C16 C 0.1504(4) 0.0372(6) 0.47378(13) 0.0510(10) Uani 1 1 d . . . . .
H16 H 0.077462 0.042768 0.476977 0.061 Uiso 1 1 calc R U . . .
C17 C 0.1950(4) -0.0311(6) 0.43993(13) 0.0536(11) Uani 1 1 d . . . . .
H17 H 0.151879 -0.069648 0.419721 0.064 Uiso 1 1 calc R U . . .
H3A H 0.313(5) 0.227(7) 0.5525(16) 0.071(17) 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
Se1 C1 1.898(4) . ?
Se1 N1 1.910(3) . ?
O1 C7 1.218(5) . ?
O4 C14 1.227(5) . ?
O3 N2 1.225(5) . ?
N3 C14 1.377(6) . ?
N3 C11 1.392(5) . ?
N3 H3A 0.85(6) . ?
N1 C7 1.382(6) . ?
N1 C8 1.428(5) . ?
N4 C19 1.339(6) . ?
N4 C15 1.351(6) . ?
N2 O2 1.210(5) . ?
N2 C10 1.464(5) . ?
C11 C12 1.405(6) . ?
C11 C10 1.409(6) . ?
C8 C9 1.386(6) . ?
C8 C13 1.401(6) . ?
C10 C9 1.398(6) . ?
C9 H9 0.9300 . ?
C12 C13 1.382(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C2 C1 1.385(6) . ?
C2 C3 1.400(6) . ?
C2 C7 1.484(6) . ?
C1 C6 1.390(6) . ?
C15 C16 1.380(6) . ?
C15 C14 1.503(6) . ?
C6 C5 1.381(6) . ?
C6 H6 0.9300 . ?
C4 C3 1.387(6) . ?
C4 C5 1.395(6) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C19 C18 1.390(7) . ?
C19 H19 0.9300 . ?
C18 C17 1.381(7) . ?
C18 H18 0.9300 . ?
C16 C17 1.391(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?

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
C1 Se1 N1 85.24(16) . . ?
C14 N3 C11 128.7(4) . . ?
C14 N3 H3A 109(4) . . ?
C11 N3 H3A 122(4) . . ?
C7 N1 C8 125.4(3) . . ?
C7 N1 Se1 115.8(3) . . ?
C8 N1 Se1 118.8(3) . . ?
C19 N4 C15 116.7(4) . . ?
O2 N2 O3 121.5(3) . . ?
O2 N2 C10 118.2(4) . . ?
O3 N2 C10 120.2(3) . . ?
N3 C11 C12 121.9(4) . . ?
N3 C11 C10 122.2(3) . . ?
C12 C11 C10 115.9(4) . . ?
C9 C8 C13 118.0(4) . . ?
C9 C8 N1 122.7(4) . . ?
C13 C8 N1 119.2(4) . . ?
C9 C10 C11 122.6(4) . . ?
C9 C10 N2 115.0(4) . . ?
C11 C10 N2 122.3(4) . . ?
C8 C9 C10 120.1(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C13 C12 C11 121.6(4) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C8 121.7(4) . . ?
C12 C13 H13 119.2 . . ?
C8 C13 H13 119.2 . . ?
C1 C2 C3 120.1(4) . . ?
C1 C2 C7 116.5(4) . . ?
C3 C2 C7 123.4(4) . . ?
C2 C1 C6 121.5(4) . . ?
C2 C1 Se1 112.3(3) . . ?
C6 C1 Se1 126.2(3) . . ?
N4 C15 C16 124.1(4) . . ?
N4 C15 C14 115.6(4) . . ?
C16 C15 C14 120.3(4) . . ?
C5 C6 C1 118.1(4) . . ?
C5 C6 H6 121.0 . . ?
C1 C6 H6 121.0 . . ?
O1 C7 N1 125.2(4) . . ?
O1 C7 C2 124.7(4) . . ?
N1 C7 C2 110.2(4) . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C6 C5 C4 121.4(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
N4 C19 C18 123.6(4) . . ?
N4 C19 H19 118.2 . . ?
C18 C19 H19 118.2 . . ?
O4 C14 N3 124.6(4) . . ?
O4 C14 C15 122.6(4) . . ?
N3 C14 C15 112.8(4) . . ?
C17 C18 C19 118.1(4) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 H18 121.0 . . ?
C15 C16 C17 117.5(4) . . ?
C15 C16 H16 121.2 . . ?
C17 C16 H16 121.2 . . ?
C18 C17 C16 119.9(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?

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
C14 N3 C11 C12 -14.1(7) . . . . ?
C14 N3 C11 C10 167.3(4) . . . . ?
C7 N1 C8 C9 10.1(6) . . . . ?
Se1 N1 C8 C9 -170.8(3) . . . . ?
C7 N1 C8 C13 -169.9(4) . . . . ?
Se1 N1 C8 C13 9.2(5) . . . . ?
N3 C11 C10 C9 -177.7(4) . . . . ?
C12 C11 C10 C9 3.7(6) . . . . ?
N3 C11 C10 N2 0.4(7) . . . . ?
C12 C11 C10 N2 -178.2(4) . . . . ?
O2 N2 C10 C9 0.6(7) . . . . ?
O3 N2 C10 C9 179.2(4) . . . . ?
O2 N2 C10 C11 -177.6(5) . . . . ?
O3 N2 C10 C11 1.0(7) . . . . ?
C13 C8 C9 C10 -0.6(6) . . . . ?
N1 C8 C9 C10 179.4(4) . . . . ?
C11 C10 C9 C8 -2.6(6) . . . . ?
N2 C10 C9 C8 179.2(4) . . . . ?
N3 C11 C12 C13 179.6(4) . . . . ?
C10 C11 C12 C13 -1.7(6) . . . . ?
C11 C12 C13 C8 -1.4(7) . . . . ?
C9 C8 C13 C12 2.6(6) . . . . ?
N1 C8 C13 C12 -177.4(4) . . . . ?
C3 C2 C1 C6 -0.6(7) . . . . ?
C7 C2 C1 C6 178.1(4) . . . . ?
C3 C2 C1 Se1 179.8(3) . . . . ?
C7 C2 C1 Se1 -1.4(5) . . . . ?
N1 Se1 C1 C2 1.1(3) . . . . ?
N1 Se1 C1 C6 -178.4(4) . . . . ?
C19 N4 C15 C16 0.1(7) . . . . ?
C19 N4 C15 C14 179.5(4) . . . . ?
C2 C1 C6 C5 0.5(7) . . . . ?
Se1 C1 C6 C5 179.9(3) . . . . ?
C8 N1 C7 O1 -1.7(7) . . . . ?
Se1 N1 C7 O1 179.1(4) . . . . ?
C8 N1 C7 C2 179.2(4) . . . . ?
Se1 N1 C7 C2 0.1(5) . . . . ?
C1 C2 C7 O1 -178.2(4) . . . . ?
C3 C2 C7 O1 0.5(7) . . . . ?
C1 C2 C7 N1 0.9(6) . . . . ?
C3 C2 C7 N1 179.6(4) . . . . ?
C5 C4 C3 C2 1.7(7) . . . . ?
C1 C2 C3 C4 -0.5(7) . . . . ?
C7 C2 C3 C4 -179.1(4) . . . . ?
C1 C6 C5 C4 0.8(7) . . . . ?
C3 C4 C5 C6 -1.9(7) . . . . ?
C15 N4 C19 C18 -0.2(7) . . . . ?
C11 N3 C14 O4 2.0(8) . . . . ?
C11 N3 C14 C15 -177.8(4) . . . . ?
N4 C15 C14 O4 -172.0(4) . . . . ?
C16 C15 C14 O4 7.5(7) . . . . ?
N4 C15 C14 N3 7.8(6) . . . . ?
C16 C15 C14 N3 -172.7(4) . . . . ?
N4 C19 C18 C17 1.0(7) . . . . ?
N4 C15 C16 C17 -0.7(7) . . . . ?
C14 C15 C16 C17 179.8(4) . . . . ?
C19 C18 C17 C16 -1.6(7) . . . . ?
C15 C16 C17 C18 1.5(7) . . . . ?

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
C9 H9 O1 0.93 2.19 2.815(5) 123.6 .
C12 H12 O4 0.93 2.26 2.873(5) 122.6 .
C13 H13 Se1 0.93 2.59 3.075(4) 113.0 .
C6 H6 O1 0.93 2.40 3.075(5) 129.3 6_557
N3 H3A O3 0.85(6) 2.04(6) 2.632(5) 126(5) .
N3 H3A N4 0.85(6) 2.09(6) 2.625(5) 120(5) .
C9 H9 O1 0.93 2.19 2.815(5) 123.6 .
C12 H12 O4 0.93 2.26 2.873(5) 122.6 .
C13 H13 Se1 0.93 2.59 3.075(4) 113.0 .
C6 H6 O1 0.93 2.40 3.075(5) 129.3 6_557
N3 H3A O3 0.85(6) 2.04(6) 2.632(5) 126(5) .
N3 H3A N4 0.85(6) 2.09(6) 2.625(5) 120(5) .

_refine_diff_density_max         0.972
_refine_diff_density_min         -1.364
_refine_diff_density_rms         0.113

