# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2288302'
loop_
_audit_author_name
_audit_author_address
'Andreas Kourtellaris'
;University of Cyprus
Cyprus
;
_audit_update_record             
;
2023-08-12 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_shelx               
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: no response from crystallographer
;
_vrf_PLAT431_shelx               
;
PROBLEM: Short Inter HL..A Contact  Cl1      ..N4       .       2.98 Ang.
RESPONSE: no response from crystallographer
;
_vrf_PLAT971_shelx               
;
PROBLEM: Check Calcd Resid. Dens.  0.95Ang From N1              2.52 eA-3
RESPONSE: no response from crystallographer
;
_vrf_PLAT431_shelx_2             
;
PROBLEM: Short Inter HL..A Contact  Cl2      ..N4       .       3.15 Ang.
RESPONSE: no response from crystallographer
;
_vrf_PLAT911_shelx               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report
RESPONSE: no response from crystallographer
;
_vrf_PLAT971_shelx_2             
;
PROBLEM: Check Calcd Resid. Dens.  1.02Ang From Se1             2.26 eA-3
RESPONSE: no response from crystallographer
;
_vrf_PLAT972_shelx               
;
PROBLEM: Check Calcd Resid. Dens.  0.75Ang From Se1            -1.57 eA-3
RESPONSE: no response from crystallographer
;
_vrf_PLAT975_shelx               
;
PROBLEM: Check Calcd Resid. Dens.  0.69Ang From N3      .       0.69 eA-3
RESPONSE: no response from crystallographer
;
# Added during the CSD deposition process: Saturday 12 August 2023 10:28 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
4,6-Dichloropyrrolo[2,3-c][1,2,6]selenadiazine-5-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 Cl2 N4 Se [+ solvent]'
_chemical_formula_sum            'C6 Cl2 N4 Se [+ solvent]'
_chemical_formula_weight         277.96

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.7340(13)
_cell_length_b                   5.6415(3)
_cell_length_c                   13.8208(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.775(9)
_cell_angle_gamma                90
_cell_volume                     835.11(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1509
_cell_measurement_theta_min      5.0370
_cell_measurement_theta_max      71.2410

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.211
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    11.597
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.31654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.543
_oxdiff_exptl_absorpt_empirical_full_max 2.325
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.4223
_diffrn_reflns_number            2662
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.059
_diffrn_reflns_theta_max         71.778
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1589
_reflns_number_gt                1493
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1496P)²+0.4017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1589
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1858
_refine_ls_wR_factor_gt          0.1810
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.7105(4) 0.7838(7) 0.3310(3) 0.0130(8) Uani 1 1 d . . . . .
C2 C 0.6714(3) 0.5719(6) 0.3829(2) 0.0128(7) Uani 1 1 d . . . . .
C3 C 0.7553(3) 0.4491(7) 0.4487(2) 0.0145(7) Uani 1 1 d . . . . .
C4 C 0.5482(3) 0.5406(7) 0.3509(2) 0.0139(7) Uani 1 1 d . . . . .
C5 C 0.5221(4) 0.7294(7) 0.2816(3) 0.0168(9) Uani 1 1 d . . . . .
C6 C 0.4613(3) 0.3620(7) 0.3746(2) 0.0155(8) Uani 1 1 d . . . . .
Cl1 Cl 0.69905(9) 0.20953(18) 0.51106(7) 0.0150(3) Uani 1 1 d . . . . .
Cl2 Cl 0.38138(11) 0.75283(15) 0.21673(9) 0.0202(4) Uani 1 1 d . . . . .
N1 N 0.8211(3) 0.8841(6) 0.3374(2) 0.0151(7) Uani 1 1 d . . . . .
N2 N 0.8712(3) 0.5003(6) 0.4686(2) 0.0150(7) Uani 1 1 d . . . . .
N3 N 0.6139(3) 0.8735(6) 0.2702(2) 0.0152(7) Uani 1 1 d . . . . .
N4 N 0.3860(4) 0.2268(6) 0.3918(3) 0.0225(9) Uani 1 1 d . . . . .
Se1 Se 0.94141(4) 0.74947(6) 0.41187(3) 0.0142(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 N1 1.313(6) . ?
C1 N3 1.387(5) . ?
C1 C2 1.469(5) . ?
C2 C4 1.378(5) . ?
C2 C3 1.417(5) . ?
C3 N2 1.290(5) . ?
C3 Cl1 1.733(4) . ?
C4 C6 1.425(5) . ?
C4 C5 1.448(6) . ?
C5 N3 1.295(6) . ?
C5 Cl2 1.710(5) . ?
C6 N4 1.148(6) . ?
N1 Se1 1.769(3) . ?
N2 Se1 1.799(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
N1 C1 N3 121.4(4) . . ?
N1 C1 C2 127.1(4) . . ?
N3 C1 C2 111.5(3) . . ?
C4 C2 C3 134.3(3) . . ?
C4 C2 C1 104.3(3) . . ?
C3 C2 C1 121.4(3) . . ?
N2 C3 C2 126.2(4) . . ?
N2 C3 Cl1 115.6(3) . . ?
C2 C3 Cl1 118.2(3) . . ?
C2 C4 C6 130.3(3) . . ?
C2 C4 C5 104.9(3) . . ?
C6 C4 C5 124.8(3) . . ?
N3 C5 C4 115.3(4) . . ?
N3 C5 Cl2 122.7(3) . . ?
C4 C5 Cl2 122.0(3) . . ?
N4 C6 C4 176.1(4) . . ?
C1 N1 Se1 118.4(3) . . ?
C3 N2 Se1 120.5(3) . . ?
C5 N3 C1 104.0(3) . . ?
N1 Se1 N2 106.18(14) . . ?

_refine_diff_density_max         2.437
_refine_diff_density_min         -1.409
_refine_diff_density_rms         0.284



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCE/c-hexane'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2288304'
loop_
_audit_author_name
_audit_author_address
'Andreas Kourtellaris'
;University of Cyprus
Cyprus
;
_audit_update_record             
;
2023-08-12 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT369_shelx               
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C3       - C4       .       1.55 Ang.
RESPONSE: no response from crystallographer
;
_vrf_PLAT767_shelx               
;
PROBLEM: INS Embedded LIST 6 Instruction Should be LIST 4     Please Check
RESPONSE: no response from crystallographer
;
_vrf_PLAT911_shelx               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         13 Report
RESPONSE: no response from crystallographer
;
# Added during the CSD deposition process: Saturday 12 August 2023 10:28 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
3,5-dimorpholino-2-oxo-2H-pyrrole-4-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 N4 O3'
_chemical_formula_sum            'C13 H16 N4 O3'
_chemical_formula_weight         276.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.2254(4)
_cell_length_b                   6.7299(2)
_cell_length_c                   17.5435(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.539(2)
_cell_angle_gamma                90
_cell_volume                     2623.95(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    177(2)
_cell_measurement_reflns_used    5139
_cell_measurement_theta_min      3.9660
_cell_measurement_theta_max      75.8000

_exptl_crystal_description       Rhombohedron
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    0.849
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.739
_oxdiff_exptl_absorpt_empirical_full_max 2.128
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      177(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            8413
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.978
_diffrn_reflns_theta_max         77.675
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2629
_reflns_number_gt                2300
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0509P)²+1.1503P] 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         2629
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0980
_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
C1 C 0.30816(5) 0.53252(17) 0.56331(7) 0.0218(3) Uani 1 1 d . . . . .
C2 C 0.27061(5) 0.48619(17) 0.49938(7) 0.0218(3) Uani 1 1 d . . . . .
C3 C 0.21074(5) 0.52884(17) 0.52149(7) 0.0219(3) Uani 1 1 d . . . . .
C4 C 0.21950(5) 0.59954(17) 0.60484(6) 0.0218(3) Uani 1 1 d . . . . .
C5 C 0.28587(5) 0.42177(18) 0.42559(7) 0.0237(3) Uani 1 1 d . . . . .
C6 C 0.40139(6) 0.6216(2) 0.62845(8) 0.0346(3) Uani 1 1 d . . . . .
H6A H 0.374009 0.657991 0.670392 0.042 Uiso 1 1 calc R U . . .
H6B H 0.417864 0.745817 0.606735 0.042 Uiso 1 1 calc R U . . .
C7 C 0.45209(6) 0.4967(3) 0.65948(8) 0.0414(4) Uani 1 1 d . . . . .
H7A H 0.477101 0.578208 0.694458 0.050 Uiso 1 1 calc R U . . .
H7B H 0.435230 0.385048 0.689185 0.050 Uiso 1 1 calc R U . . .
C8 C 0.45364(6) 0.3009(2) 0.55029(9) 0.0388(3) Uani 1 1 d . . . . .
H8A H 0.434996 0.191349 0.579421 0.047 Uiso 1 1 calc R U . . .
H8B H 0.479986 0.241177 0.511275 0.047 Uiso 1 1 calc R U . . .
C9 C 0.40491(6) 0.4209(2) 0.51129(7) 0.0296(3) Uani 1 1 d . . . . .
H9A H 0.423213 0.524038 0.478638 0.035 Uiso 1 1 calc R U . . .
H9B H 0.379902 0.333210 0.478576 0.035 Uiso 1 1 calc R U . . .
C10 C 0.11155(6) 0.6378(2) 0.63465(8) 0.0326(3) Uani 1 1 d . . . . .
H10A H 0.105201 0.593078 0.581424 0.039 Uiso 1 1 calc R U . . .
H10B H 0.093197 0.771000 0.640268 0.039 Uiso 1 1 calc R U . . .
C11 C 0.08231(6) 0.4929(3) 0.68908(9) 0.0383(3) Uani 1 1 d . . . . .
H11A H 0.038340 0.491098 0.679546 0.046 Uiso 1 1 calc R U . . .
H11B H 0.097978 0.357629 0.679382 0.046 Uiso 1 1 calc R U . . .
C12 C 0.15708(6) 0.5503(2) 0.78210(8) 0.0359(3) Uani 1 1 d . . . . .
H12A H 0.174361 0.416555 0.773688 0.043 Uiso 1 1 calc R U . . .
H12B H 0.163920 0.586089 0.836224 0.043 Uiso 1 1 calc R U . . .
C13 C 0.18880(6) 0.6986(2) 0.73188(7) 0.0299(3) Uani 1 1 d . . . . .
H13A H 0.174285 0.834598 0.742952 0.036 Uiso 1 1 calc R U . . .
H13B H 0.232695 0.694302 0.741868 0.036 Uiso 1 1 calc R U . . .
N1 N 0.27717(4) 0.60314(16) 0.62486(6) 0.0236(2) Uani 1 1 d . . . . .
N2 N 0.29784(5) 0.36900(18) 0.36499(6) 0.0328(3) Uani 1 1 d . . . . .
N3 N 0.36753(5) 0.51431(16) 0.56930(6) 0.0257(2) Uani 1 1 d . . . . .
N4 N 0.17616(5) 0.64811(16) 0.65196(6) 0.0248(2) Uani 1 1 d . . . . .
O1 O 0.16293(4) 0.51586(14) 0.48585(5) 0.0288(2) Uani 1 1 d . . . . .
O2 O 0.48894(4) 0.41956(19) 0.60049(6) 0.0424(3) Uani 1 1 d . . . . .
O3 O 0.09365(4) 0.54469(17) 0.76660(6) 0.0381(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 N3 1.3284(15) . ?
C1 N1 1.3714(15) . ?
C1 C2 1.4263(16) . ?
C2 C5 1.4097(17) . ?
C2 C3 1.4189(17) . ?
C3 O1 1.2309(15) . ?
C3 C4 1.5482(16) . ?
C4 N4 1.3165(16) . ?
C4 N1 1.3260(15) . ?
C5 N2 1.1543(17) . ?
C6 N3 1.4663(17) . ?
C6 C7 1.504(2) . ?
C7 O2 1.4239(19) . ?
C8 O2 1.420(2) . ?
C8 C9 1.5099(19) . ?
C9 N3 1.4619(16) . ?
C10 N4 1.4664(16) . ?
C10 C11 1.516(2) . ?
C11 O3 1.4241(19) . ?
C12 O3 1.4338(17) . ?
C12 C13 1.5106(19) . ?
C13 N4 1.4674(16) . ?

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
N3 C1 N1 118.40(11) . . ?
N3 C1 C2 127.99(11) . . ?
N1 C1 C2 113.60(10) . . ?
C5 C2 C3 123.21(11) . . ?
C5 C2 C1 130.19(11) . . ?
C3 C2 C1 106.51(10) . . ?
O1 C3 C2 130.84(11) . . ?
O1 C3 C4 127.00(11) . . ?
C2 C3 C4 102.15(10) . . ?
N4 C4 N1 122.70(11) . . ?
N4 C4 C3 125.67(11) . . ?
N1 C4 C3 111.62(10) . . ?
N2 C5 C2 179.40(14) . . ?
N3 C6 C7 111.01(12) . . ?
O2 C7 C6 112.01(12) . . ?
O2 C8 C9 111.71(12) . . ?
N3 C9 C8 108.93(11) . . ?
N4 C10 C11 108.95(11) . . ?
O3 C11 C10 111.78(12) . . ?
O3 C12 C13 111.72(11) . . ?
N4 C13 C12 108.53(11) . . ?
C4 N1 C1 106.05(10) . . ?
C1 N3 C9 123.72(11) . . ?
C1 N3 C6 120.88(11) . . ?
C9 N3 C6 114.42(10) . . ?
C4 N4 C10 125.39(10) . . ?
C4 N4 C13 121.52(10) . . ?
C10 N4 C13 112.77(10) . . ?
C8 O2 C7 109.74(11) . . ?
C11 O3 C12 110.63(10) . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCE/c-hexane'
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2288305'
loop_
_audit_author_name
_audit_author_address
'Andreas Kourtellaris'
;University of Cyprus
Cyprus
;
_audit_update_record             
;
2023-08-12 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT411_shelx               
;
PROBLEM: Short Inter H...H Contact  H7A      ..H8A      .       2.14 Ang.
RESPONSE: no response from crystallographer
;
_vrf_PLAT767_shelx               
;
PROBLEM: INS Embedded LIST 6 Instruction Should be LIST 4     Please Check
RESPONSE: no response from crystallographer
;
_vrf_PLAT911_shelx               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report
RESPONSE: no response from crystallographer
;
# Added during the CSD deposition process: Saturday 12 August 2023 10:28 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
4,6-dimorpholinopyrrolo[2,3-c][1,2,6]selenadiazine-5-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 N6 O2 Se'
_chemical_formula_weight         379.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 '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      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                   5.21970(10)
_cell_length_b                   11.2505(2)
_cell_length_c                   13.0616(2)
_cell_angle_alpha                105.672(2)
_cell_angle_beta                 95.717(2)
_cell_angle_gamma                94.437(2)
_cell_volume                     730.48(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5357
_cell_measurement_theta_min      4.0960
_cell_measurement_theta_max      75.9840

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    3.673
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.764
_oxdiff_exptl_absorpt_empirical_full_max 1.348
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8143
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.543
_diffrn_reflns_theta_max         76.535
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2950
_reflns_number_gt                2731
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0445P)²+0.1903P] 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         2950
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.6471(4) 0.43375(18) 0.13032(16) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.5117(4) 0.50665(18) 0.21564(16) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.5605(4) 0.63855(18) 0.25702(16) 0.0230(4) Uani 1 1 d . . . . .
C4 C 0.3930(4) 0.29880(18) 0.17324(16) 0.0233(4) Uani 1 1 d . . . . .
C5 C 0.3421(4) 0.42083(18) 0.24004(16) 0.0221(4) Uani 1 1 d . . . . .
C6 C 0.1482(4) 0.44828(18) 0.30901(17) 0.0246(4) Uani 1 1 d . . . . .
C7 C 0.3270(5) 0.0782(2) 0.0901(2) 0.0378(5) Uani 1 1 d . . . . .
H7A H 0.501224 0.091084 0.068507 0.045 Uiso 1 1 calc R U . . .
H7B H 0.197364 0.068017 0.026756 0.045 Uiso 1 1 calc R U . . .
C8 C 0.3057(6) -0.0382(2) 0.1274(2) 0.0419(6) Uani 1 1 d . . . . .
H8A H 0.316975 -0.111367 0.066220 0.050 Uiso 1 1 calc R U . . .
H8B H 0.452595 -0.033327 0.183000 0.050 Uiso 1 1 calc R U . . .
C9 C 0.0590(5) 0.0481(2) 0.26031(19) 0.0313(5) Uani 1 1 d . . . . .
H9A H 0.210211 0.053447 0.314139 0.038 Uiso 1 1 calc R U . . .
H9B H -0.099699 0.034604 0.293189 0.038 Uiso 1 1 calc R U . . .
C10 C 0.0595(4) 0.1694(2) 0.2304(2) 0.0331(5) Uani 1 1 d . . . . .
H10A H -0.101502 0.168225 0.182969 0.040 Uiso 1 1 calc R U . . .
H10B H 0.064891 0.239344 0.295928 0.040 Uiso 1 1 calc R U . . .
C11 C 0.5331(4) 0.67433(19) 0.44752(16) 0.0256(4) Uani 1 1 d . . . . .
H11A H 0.710281 0.717102 0.472730 0.031 Uiso 1 1 calc R U . . .
H11B H 0.540343 0.584262 0.437343 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3546(4) 0.7227(2) 0.52984(18) 0.0294(4) Uani 1 1 d . . . . .
H12A H 0.180138 0.676387 0.506130 0.035 Uiso 1 1 calc R U . . .
H12B H 0.420772 0.708943 0.598972 0.035 Uiso 1 1 calc R U . . .
C13 C 0.2415(5) 0.8730(2) 0.44523(18) 0.0305(4) Uani 1 1 d . . . . .
H13A H 0.227711 0.962735 0.456187 0.037 Uiso 1 1 calc R U . . .
H13B H 0.065847 0.828231 0.420526 0.037 Uiso 1 1 calc R U . . .
C14 C 0.4162(4) 0.82919(19) 0.35982(17) 0.0274(4) Uani 1 1 d . . . . .
H14A H 0.343260 0.843026 0.291585 0.033 Uiso 1 1 calc R U . . .
H14B H 0.589984 0.876525 0.382020 0.033 Uiso 1 1 calc R U . . .
N1 N 0.8104(4) 0.47621(16) 0.07543(14) 0.0265(4) Uani 1 1 d . . . . .
N2 N 0.7099(4) 0.70786(16) 0.21585(15) 0.0275(4) Uani 1 1 d . . . . .
N3 N 0.5725(4) 0.30929(16) 0.10959(14) 0.0254(4) Uani 1 1 d . . . . .
N4 N 0.2837(4) 0.18720(16) 0.17564(15) 0.0263(4) Uani 1 1 d . . . . .
N5 N -0.0125(4) 0.46932(17) 0.36337(16) 0.0317(4) Uani 1 1 d . . . . .
N6 N 0.4364(3) 0.69662(15) 0.34511(14) 0.0235(3) Uani 1 1 d . . . . .
O1 O 0.0687(3) -0.05405(14) 0.16991(14) 0.0354(4) Uani 1 1 d . . . . .
O2 O 0.3369(3) 0.85256(14) 0.54441(13) 0.0325(3) Uani 1 1 d . . . . .
Se1 Se 0.88141(4) 0.64201(2) 0.10576(2) 0.02722(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 N1 1.309(3) . ?
C1 N3 1.370(3) . ?
C1 C2 1.472(3) . ?
C2 C5 1.381(3) . ?
C2 C3 1.428(3) . ?
C3 N2 1.312(3) . ?
C3 N6 1.406(3) . ?
C4 N3 1.332(3) . ?
C4 N4 1.348(3) . ?
C4 C5 1.474(3) . ?
C5 C6 1.418(3) . ?
C6 N5 1.150(3) . ?
C7 N4 1.468(3) . ?
C7 C8 1.516(3) . ?
C8 O1 1.423(3) . ?
C9 O1 1.416(3) . ?
C9 C10 1.518(3) . ?
C10 N4 1.459(3) . ?
C11 N6 1.474(3) . ?
C11 C12 1.511(3) . ?
C12 O2 1.433(3) . ?
C13 O2 1.424(3) . ?
C13 C14 1.515(3) . ?
C14 N6 1.465(3) . ?
N1 Se1 1.7995(18) . ?
N2 Se1 1.7894(18) . ?

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
N1 C1 N3 121.69(18) . . ?
N1 C1 C2 127.31(18) . . ?
N3 C1 C2 110.94(17) . . ?
C5 C2 C3 131.70(19) . . ?
C5 C2 C1 105.20(17) . . ?
C3 C2 C1 123.09(18) . . ?
N2 C3 N6 118.71(18) . . ?
N2 C3 C2 123.47(18) . . ?
N6 C3 C2 117.81(18) . . ?
N3 C4 N4 121.80(18) . . ?
N3 C4 C5 111.90(18) . . ?
N4 C4 C5 126.27(18) . . ?
C2 C5 C6 125.97(18) . . ?
C2 C5 C4 105.49(17) . . ?
C6 C5 C4 128.37(18) . . ?
N5 C6 C5 178.7(2) . . ?
N4 C7 C8 110.82(19) . . ?
O1 C8 C7 111.8(2) . . ?
O1 C9 C10 111.73(19) . . ?
N4 C10 C9 110.13(18) . . ?
N6 C11 C12 109.37(16) . . ?
O2 C12 C11 110.85(18) . . ?
O2 C13 C14 111.81(17) . . ?
N6 C14 C13 108.64(17) . . ?
C1 N1 Se1 117.55(14) . . ?
C3 N2 Se1 121.87(14) . . ?
C4 N3 C1 106.35(17) . . ?
C4 N4 C10 124.27(17) . . ?
C4 N4 C7 117.37(18) . . ?
C10 N4 C7 114.72(18) . . ?
C3 N6 C14 115.01(16) . . ?
C3 N6 C11 115.14(16) . . ?
C14 N6 C11 110.37(16) . . ?
C9 O1 C8 109.01(18) . . ?
C13 O2 C12 109.77(16) . . ?
N2 Se1 N1 106.35(8) . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.074


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCE/c-hexane'
####################################################################### 
# 
# 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_cory_5b_auto
_database_code_depnum_ccdc_archive 'CCDC 2288303'
loop_
_audit_author_name
_audit_author_address
'Andreas Kourtellaris'
;University of Cyprus
Cyprus
;
_audit_update_record             
;
2023-08-12 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_cory_5b_auto        
;
PROBLEM: Short Inter D...A Contact  N2       ..N2       .       2.86 Ang.
RESPONSE: no response from crystallographer
;
# Added during the CSD deposition process: Saturday 12 August 2023 10:28 AM
# end Validation Reply Form

_audit_creation_date             2023-08-04
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
4-Chloro-6-phenoxypyrrolo[2,3-c][1,2,6]selenadiazine-5-carbonitrile
_chemical_formula_moiety         'C12 H5 Cl N4 O Se'
_chemical_formula_sum            'C12 H5 Cl N4 O Se'
_chemical_formula_weight         335.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Se Cl N C O H'
_chemical_oxdiff_usercomment     triam-Zn
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'
Cl Cl 0.3639 0.7018 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.01700(8)
_cell_length_b                   8.67188(13)
_cell_length_c                   27.5955(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.8291(15)
_cell_angle_gamma                90
_cell_volume                     1200.47(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8326
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      75.8610
_cell_measurement_theta_min      3.2140
_shelx_estimated_absorpt_T_max   0.367
_shelx_estimated_absorpt_T_min   0.097
_exptl_absorpt_coefficient_mu    6.270
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            13273
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.748
_diffrn_reflns_theta_min         3.203
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     65.00  90.00   0.50    0.10    --   47.44 144.00-155.00   50
  2  ω     76.00 115.00   0.50    0.10    --   47.44 127.00  34.00   78
  3  ω    -93.00 -33.00   0.50    0.32    -- -106.00  77.00-180.00  120
  4  ω    -71.00 -35.00   0.50    0.32    -- -106.00  61.00   0.00   72
  5  ω    -69.00 -33.00   0.50    0.32    -- -106.00  61.00  90.00   72
  6  ω     78.00 117.00   0.50    0.10    --   47.44 126.00 -60.00   78
  7  ω     83.00 117.00   0.50    0.10    --   47.44 126.00 -30.00   68
  8  ω     94.00 122.00   0.50    0.32    --  106.24  45.00 -30.00   56
  9  ω    107.00 167.00   0.50    0.32    --  106.24  45.00-180.00  120
 10  ω    103.00 176.00   0.50    0.32    --  106.24  61.00 120.00  146
 11  ω     40.00  92.00   0.50    0.10    --   47.44-127.00 -40.00  104
 12  ω     79.00 111.00   0.50    0.32    --  106.24-127.00 -40.00   64
 13  ω     58.00 105.00   0.50    0.10    --   47.44-144.00 150.00   94
 14  ω     66.00 125.00   0.50    0.32    --  106.24-144.00 150.00  118
 15  ω     36.00  61.00   0.50    0.32    --  106.24-144.00 150.00   50
 16  ω     36.00  74.00   0.50    0.32    --  106.24-126.00 150.00   76
 17  ω    -27.00  29.00   0.50    0.10    --   47.44 -19.00  30.00  112
 18  ω     34.00  61.00   0.50    0.32    --  106.24 -61.00 -90.00   54
 19  ω     44.00  93.00   0.50    0.32    --  106.24 -77.00 -30.00   98
 20  ω     38.00  66.00   0.50    0.32    --  106.24 -61.00   0.00   56
 21  ω     79.00 107.00   0.50    0.32    --  106.24 144.00-155.00   56
 22  ω    102.00 158.00   0.50    0.32    --  106.24 127.00  34.00  112
 23  ω    -26.00  30.00   0.50    0.10    --   47.44 -19.00 120.00  112
 24  ω    -96.00 -71.00   0.50    0.10    --  -47.44-144.00 150.00   50
 25  ω   -137.00 -75.00   0.50    0.32    -- -106.00-144.00 150.00  124
 26  ω   -175.00 -83.00   0.50    0.32    -- -106.00 -95.00  90.00  184
 27  ω   -118.00 -82.00   0.50    0.10    --  -47.44-127.00 -40.00   72
 28  ω   -117.00 -74.00   0.50    0.10    --  -47.44-126.00-120.00   86
 29  ω   -149.00-124.00   0.50    0.32    -- -106.00-127.00 -40.00   50
 30  ω   -118.00 -93.00   0.50    0.32    -- -106.00 -30.00-150.00   50
 31  ω   -171.00-145.00   0.50    0.32    -- -106.00 -30.00-150.00   52
 32  ω   -173.00-108.00   0.50    0.32    -- -106.00 -30.00 150.00  130
 33  ω    -79.00 -54.00   0.50    0.10    --  -47.44 127.00  34.00   50
 34  ω    -97.00 -71.00   0.50    0.32    -- -106.00 127.00  34.00   52
 35  ω   -111.00 -36.00   0.50    0.32    -- -106.00 126.00 150.00  150
 36  ω    -64.00 -38.00   0.50    0.32    -- -106.00 126.00 -30.00   52
 37  ω   -109.00 -83.00   0.50    0.32    -- -106.00 126.00 -30.00   52
 38  ω    -66.00 -40.00   0.50    0.10    --  -47.44 144.00-155.00   52
 39  ω   -121.00 -96.00   0.50    0.32    -- -106.00 144.00-155.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0100075000
_diffrn_orient_matrix_UB_12      -0.0133096000
_diffrn_orient_matrix_UB_13      -0.0556634000
_diffrn_orient_matrix_UB_21      0.1919903000
_diffrn_orient_matrix_UB_22      -0.1385227000
_diffrn_orient_matrix_UB_23      0.0026168000
_diffrn_orient_matrix_UB_31      -0.2395155000
_diffrn_orient_matrix_UB_32      -0.1104077000
_diffrn_orient_matrix_UB_33      0.0034305000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2330
_reflns_number_total             2470
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
'olex2.solve 1.5-ac5-024 (Bourhis et al., 2015)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.00041(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2470
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0214
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0221P)²+0.5087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0528
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.75712(4) 0.02362(2) 0.44410(2) 0.02486(8) Uani 1 1 d . . . . .
Cl1 Cl 0.19681(8) 0.36919(5) 0.48729(2) 0.02667(11) Uani 1 1 d . . . . .
O1 O 0.7584(3) 0.62655(14) 0.33160(5) 0.0274(3) Uani 1 1 d . . . . .
N3 N 0.8836(3) 0.37648(17) 0.35488(5) 0.0238(3) Uani 1 1 d . . . . .
N2 N 0.4989(3) 0.13682(17) 0.47124(5) 0.0241(3) Uani 1 1 d . . . . .
N1 N 0.8910(3) 0.14247(17) 0.39748(5) 0.0239(3) Uani 1 1 d . . . . .
N4 N 0.2321(4) 0.7236(2) 0.41608(7) 0.0379(4) Uani 1 1 d . . . . .
C3 C 0.7910(3) 0.27902(19) 0.39057(6) 0.0208(3) Uani 1 1 d . . . . .
C2 C 0.5741(3) 0.35403(19) 0.41791(6) 0.0191(3) Uani 1 1 d . . . . .
C5 C 0.5450(3) 0.49697(19) 0.39758(6) 0.0214(3) Uani 1 1 d . . . . .
C7 C 0.8939(3) 0.6131(2) 0.28713(6) 0.0242(4) Uani 1 1 d . . . . .
C1 C 0.4486(3) 0.27422(19) 0.45630(6) 0.0205(3) Uani 1 1 d . . . . .
C4 C 0.7396(3) 0.5011(2) 0.35902(6) 0.0224(3) Uani 1 1 d . . . . .
C6 C 0.3682(4) 0.6208(2) 0.40862(6) 0.0251(4) Uani 1 1 d . . . . .
C8 C 1.1107(4) 0.7071(2) 0.27992(7) 0.0299(4) Uani 1 1 d . . . . .
H8 H 1.179263 0.770813 0.305178 0.036 Uiso 1 1 calc R U . . .
C12 C 0.7894(4) 0.5188(2) 0.25151(7) 0.0293(4) Uani 1 1 d . . . . .
H12 H 0.638832 0.455726 0.257628 0.035 Uiso 1 1 calc R U . . .
C9 C 1.2265(4) 0.7056(2) 0.23431(8) 0.0350(4) Uani 1 1 d . . . . .
H9 H 1.376080 0.769440 0.228200 0.042 Uiso 1 1 calc R U . . .
C10 C 1.1257(4) 0.6121(2) 0.19795(7) 0.0349(4) Uani 1 1 d . . . . .
H10 H 1.205606 0.612478 0.166944 0.042 Uiso 1 1 calc R U . . .
C11 C 0.9089(4) 0.5180(2) 0.20647(7) 0.0345(4) Uani 1 1 d . . . . .
H11 H 0.841666 0.452757 0.181490 0.041 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
Se1 N2 1.7973(14) . ?
Se1 N1 1.7871(15) . ?
Cl1 C1 1.7428(17) . ?
O1 C7 1.416(2) . ?
O1 C4 1.329(2) . ?
N3 C3 1.383(2) . ?
N3 C4 1.306(2) . ?
N2 C1 1.285(2) . ?
N1 C3 1.299(2) . ?
N4 C6 1.144(3) . ?
C3 C2 1.483(2) . ?
C2 C5 1.368(2) . ?
C2 C1 1.420(2) . ?
C5 C4 1.455(2) . ?
C5 C6 1.428(2) . ?
C7 C8 1.376(3) . ?
C7 C12 1.376(3) . ?
C8 C9 1.394(3) . ?
C12 C11 1.388(3) . ?
C9 C10 1.380(3) . ?
C10 C11 1.383(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
N1 Se1 N2 105.40(7) . . ?
C4 O1 C7 117.69(13) . . ?
C4 N3 C3 104.57(14) . . ?
C1 N2 Se1 120.81(12) . . ?
C3 N1 Se1 118.89(12) . . ?
N3 C3 C2 110.52(14) . . ?
N1 C3 N3 121.91(15) . . ?
N1 C3 C2 127.56(16) . . ?
C5 C2 C3 105.28(14) . . ?
C5 C2 C1 134.58(16) . . ?
C1 C2 C3 120.14(15) . . ?
C2 C5 C4 104.69(14) . . ?
C2 C5 C6 131.05(16) . . ?
C6 C5 C4 124.26(15) . . ?
C8 C7 O1 117.84(16) . . ?
C8 C7 C12 122.83(17) . . ?
C12 C7 O1 119.02(16) . . ?
N2 C1 Cl1 114.91(13) . . ?
N2 C1 C2 127.18(16) . . ?
C2 C1 Cl1 117.91(13) . . ?
O1 C4 C5 119.36(15) . . ?
N3 C4 O1 125.71(16) . . ?
N3 C4 C5 114.93(15) . . ?
N4 C6 C5 177.1(2) . . ?
C7 C8 C9 117.74(19) . . ?
C7 C12 C11 118.55(18) . . ?
C10 C9 C8 120.62(18) . . ?
C9 C10 C11 120.23(19) . . ?
C10 C11 C12 120.0(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.212
_oxdiff_exptl_absorpt_empirical_full_min 0.843
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCE/c-hexane'
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2288306'
loop_
_audit_author_name
_audit_author_address
'Andreas Kourtellaris'
;University of Cyprus
Cyprus
;
_audit_update_record             
;
2023-08-12 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT097_shelx               
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.93 eA-3
RESPONSE: The twinning has had an adverse effect of the data which require significant displacement parameter restraints. Even tighter restraints would be required, so it was decided to leave it as it is.
;
_vrf_PLAT340_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01675 Ang.
RESPONSE: The twinning has had an adverse effect of the data.
;
_vrf_DIFMX02_shelx               
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: no response from crystallographer
;
_vrf_STRVA01_shelx               
;
PROBLEM: Chirality of atom sites is inverted?
RESPONSE: no response from crystallographer
;
_vrf_PLAT082_shelx               
;
PROBLEM: High R1 Value ..................................       0.13 Report
RESPONSE: no response from crystallographer
;
_vrf_PLAT084_shelx               
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.35 Report
RESPONSE: no response from crystallographer
;
_vrf_PLAT089_shelx               
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.95 Note
RESPONSE: no response from crystallographer
;
_vrf_PLAT094_shelx               
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.27 Report
RESPONSE: no response from crystallographer
;
_vrf_PLAT213_shelx               
;
PROBLEM: Atom C8              has ADP max/min Ratio .....        3.4 prolat
RESPONSE: no response from crystallographer
;
_vrf_PLAT234_shelx               
;
PROBLEM: Large Hirshfeld Difference N1       --C1       .       0.19 Ang.
RESPONSE: no response from crystallographer
;
_vrf_PLAT241_shelx               
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         C8 Check
RESPONSE: no response from crystallographer
;
_vrf_PLAT309_shelx               
;
PROBLEM: Single Bonded Oxygen (C-O > 1.3 Ang) ...........         O1 Check
RESPONSE: no response from crystallographer
;
_vrf_PLAT906_shelx               
;
PROBLEM: Large K Value in the Analysis of Variance ......      3.177 Check
RESPONSE: no response from crystallographer
;
_vrf_PLAT907_shelx               
;
PROBLEM: Flack x > 0.5, Structure Needs to be Inverted? .       1.30 Check
RESPONSE: no response from crystallographer
;
_vrf_PLAT911_shelx               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         19 Report
RESPONSE: no response from crystallographer
;
_vrf_PLAT975_shelx               
;
PROBLEM: Check Calcd Resid. Dens.  0.89Ang From N1      .       0.49 eA-3
RESPONSE: no response from crystallographer
;
# Added during the CSD deposition process: Saturday 12 August 2023 10:28 AM
# end Validation Reply Form

_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
2,5-dimorpholino-2-oxo-2H-pyrrole-4-carbonitrile
_chemical_formula_moiety         'C13 H16 N4 O3 [+ solvent]'
_chemical_formula_sum            'C13 H16 N4 O3 [+ solvent]'
_chemical_formula_weight         275.30
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.2528(4)
_cell_length_b                   9.1018(5)
_cell_length_c                   18.9222(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1249.12(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1599
_cell_measurement_temperature    114(2)
_cell_measurement_theta_max      74.3370
_cell_measurement_theta_min      4.6380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.025
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.022
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.0845
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4143
_diffrn_reflns_point_group_measured_fraction_full 0.826
_diffrn_reflns_point_group_measured_fraction_max 0.766
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.435
_diffrn_reflns_theta_min         4.674
_diffrn_ambient_temperature      114(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.587
_reflns_Friedel_fraction_full    0.659
_reflns_Friedel_fraction_max     0.585
_reflns_number_gt                1784
_reflns_number_total             2007
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    ?
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.3(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2007
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.1325
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3368
_refine_ls_wR_factor_ref         0.3477
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: -0.32296
 1.32296
2. Rigid body (RIGU) restrains
 C1, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C12(H12A,H12B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5430(13) 0.5553(15) 0.4634(6) 0.046(2) Uani 1 1 d . . . . .
C2 C 0.4788(14) 0.6255(12) 0.5303(6) 0.042(2) Uani 1 1 d . . . . .
C3 C 0.4888(12) 0.7707(10) 0.5120(5) 0.0325(19) Uani 1 1 d . . . . .
C4 C 0.5634(13) 0.7746(10) 0.4407(5) 0.033(2) Uani 1 1 d . . . . .
C5 C 0.6677(19) 0.8742(13) 0.3317(7) 0.055(3) Uani 1 1 d . . . . .
H5A H 0.795054 0.912488 0.327860 0.066 Uiso 1 1 calc R U . . .
H5B H 0.670209 0.767374 0.321879 0.066 Uiso 1 1 calc R U . . .
C6 C 0.5487(16) 0.9482(12) 0.2810(7) 0.048(3) Uani 1 1 d . . . . .
H6A H 0.422845 0.906581 0.284068 0.057 Uiso 1 1 calc R U . . .
H6B H 0.595563 0.930538 0.232613 0.057 Uiso 1 1 calc R U . . .
C7 C 0.4596(19) 1.1302(12) 0.3611(6) 0.051(3) Uani 1 1 d . . . . .
H7A H 0.331811 1.091926 0.361598 0.062 Uiso 1 1 calc R U . . .
H7B H 0.454601 1.237401 0.369721 0.062 Uiso 1 1 calc R U . . .
C8 C 0.571(2) 1.057(2) 0.4190(6) 0.071(4) Uani 1 1 d . . . . .
H8A H 0.693418 1.104025 0.422575 0.085 Uiso 1 1 calc R U . . .
H8B H 0.507132 1.068946 0.464869 0.085 Uiso 1 1 calc R U . . .
C9 C 0.3890(19) 0.4127(13) 0.5951(7) 0.058(3) Uani 1 1 d . . . . .
H9A H 0.430307 0.368372 0.550053 0.069 Uiso 1 1 calc R U . . .
H9B H 0.257771 0.386775 0.602399 0.069 Uiso 1 1 calc R U . . .
C10 C 0.5057(18) 0.3529(12) 0.6565(6) 0.049(3) Uani 1 1 d . . . . .
H10A H 0.499806 0.244189 0.656962 0.059 Uiso 1 1 calc R U . . .
H10B H 0.636096 0.382133 0.650000 0.059 Uiso 1 1 calc R U . . .
C11 C 0.4581(17) 0.5632(15) 0.7208(7) 0.054(3) Uani 1 1 d . . . . .
H11A H 0.589763 0.590614 0.716435 0.065 Uiso 1 1 calc R U . . .
H11B H 0.411195 0.602991 0.766036 0.065 Uiso 1 1 calc R U . . .
C12 C 0.3483(17) 0.6299(10) 0.6589(10) 0.070(5) Uani 1 1 d . . . . .
H12A H 0.215251 0.610207 0.665609 0.084 Uiso 1 1 calc R U . . .
H12B H 0.366403 0.737687 0.657974 0.084 Uiso 1 1 calc R U . . .
C13 C 0.4446(15) 0.9079(16) 0.5557(7) 0.055(3) Uani 1 1 d . . . . .
N1 N 0.5973(12) 0.6387(10) 0.4169(7) 0.052(3) Uani 1 1 d . . . . .
N2 N 0.5945(14) 0.9012(12) 0.4044(6) 0.059(3) Uani 1 1 d . . . . .
N3 N 0.4086(14) 0.5672(13) 0.5921(6) 0.061(3) Uani 1 1 d . . . . .
N4 N 0.4110(17) 0.9965(11) 0.5887(6) 0.058(3) Uani 1 1 d . . . . .
O1 O 0.5587(14) 0.4096(10) 0.4578(5) 0.066(3) Uani 1 1 d . . . . .
O2 O 0.5409(11) 1.1028(8) 0.2938(4) 0.0445(19) Uani 1 1 d . . . . .
O3 O 0.4407(10) 0.4076(9) 0.7205(4) 0.050(2) 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 1.492(16) . ?
C1 N1 1.227(17) . ?
C1 O1 1.336(16) . ?
C2 C3 1.368(14) . ?
C2 N3 1.381(15) . ?
C3 C4 1.455(12) . ?
C3 C13 1.531(15) . ?
C4 N1 1.339(12) . ?
C4 N2 1.361(13) . ?
C5 C6 1.456(16) . ?
C5 N2 1.495(18) . ?
C6 O2 1.429(13) . ?
C7 C8 1.518(19) . ?
C7 O2 1.424(13) . ?
C8 N2 1.45(2) . ?
C9 C10 1.538(19) . ?
C9 N3 1.415(17) . ?
C10 O3 1.392(14) . ?
C11 C12 1.54(2) . ?
C11 O3 1.422(16) . ?
C12 N3 1.45(2) . ?
C13 N4 1.048(15) . ?

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
N1 C1 C2 116.4(11) . . ?
N1 C1 O1 122.0(11) . . ?
O1 C1 C2 121.3(10) . . ?
C3 C2 C1 100.5(10) . . ?
C3 C2 N3 127.2(10) . . ?
N3 C2 C1 132.0(11) . . ?
C2 C3 C4 106.1(8) . . ?
C2 C3 C13 129.8(10) . . ?
C4 C3 C13 124.0(9) . . ?
N1 C4 C3 111.0(9) . . ?
N2 C4 C3 123.4(9) . . ?
N2 C4 N1 125.6(10) . . ?
C6 C5 N2 108.6(10) . . ?
C5 C6 O2 111.6(9) . . ?
O2 C7 C8 110.3(9) . . ?
N2 C8 C7 110.8(10) . . ?
N3 C9 C10 109.1(11) . . ?
O3 C10 C9 110.1(9) . . ?
O3 C11 C12 110.1(9) . . ?
N3 C12 C11 110.5(9) . . ?
N4 C13 C3 175.7(17) . . ?
C1 N1 C4 105.7(11) . . ?
C4 N2 C5 112.5(11) . . ?
C4 N2 C8 135.2(11) . . ?
C8 N2 C5 112.2(8) . . ?
C2 N3 C9 117.0(12) . . ?
C2 N3 C12 134.1(11) . . ?
C9 N3 C12 108.9(9) . . ?
C7 O2 C6 109.9(8) . . ?
C10 O3 C11 109.2(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.164
_oxdiff_exptl_absorpt_empirical_full_min 0.483
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -0.32296
2 1.32296
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCE/c-hexane'
####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2288308'
loop_
_audit_author_name
_audit_author_address
'Andreas Kourtellaris'
;University of Cyprus
Cyprus
;
_audit_update_record             
;
2023-08-12 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_shelx               
;
PROBLEM: Short Inter D...A Contact  Se1      ..N8       .       2.86 Ang.
RESPONSE: 'Intermolecular Se...N contacts of ~2.84-3.29 \~A? are not uncommon in selenazoles';doi.org/10.1021/acs.inorgchem.6b01771; and references therein'
;
_vrf_PLAT196_shelx               
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: no response from crystallographer
;
_vrf_PLAT341_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0075 Ang.
RESPONSE: no response from crystallographer
;
_vrf_PLAT767_shelx               
;
PROBLEM: INS Embedded LIST 6 Instruction Should be LIST 4     Please Check
RESPONSE: no response from crystallographer
;
_vrf_PLAT790_shelx               
;
PROBLEM: Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
RESPONSE: no response from crystallographer
;
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          5 Note
RESPONSE: no response from crystallographer
;
_vrf_PLAT975_shelx               
;
PROBLEM: Check Calcd Resid. Dens.  0.97Ang From N6      .       0.63 eA-3
RESPONSE: no response from crystallographer
;
# Added during the CSD deposition process: Saturday 12 August 2023 10:28 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'4 Chloro-6-oxo-6,7-dihydropyrrolo[2,3-c][1,2,6]selenadiazine-5-carbonitrile'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H Cl N4 O Se'
_chemical_formula_sum            "C6 H Cl N4 O Se'"
_chemical_formula_weight         259.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.8205(6)
_cell_length_b                   11.1537(12)
_cell_length_c                   13.4660(13)
_cell_angle_alpha                66.940(10)
_cell_angle_beta                 88.468(8)
_cell_angle_gamma                82.098(9)
_cell_volume                     796.37(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1503
_cell_measurement_theta_min      3.6310
_cell_measurement_theta_max      29.2690

_exptl_crystal_description       polyhedra
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.165
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    5.007
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70454
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.711
_oxdiff_exptl_absorpt_empirical_full_max 1.408
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.4223
_diffrn_reflns_number            6459
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.290
_diffrn_reflns_theta_max         29.646
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3745
_reflns_number_gt                2713
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0357P)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         3745
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.062
_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 -0.1923(9) 0.2187(5) 0.7801(3) 0.0139(10) Uani 1 1 d . . . . .
C2 C -0.0690(8) 0.3337(5) 0.7485(4) 0.0156(10) Uani 1 1 d . . . . .
C3 C -0.1441(9) 0.4458(5) 0.6522(4) 0.0134(10) Uani 1 1 d . . . . .
C4 C 0.1042(8) 0.3054(5) 0.8236(4) 0.0150(10) Uani 1 1 d . . . . .
C5 C 0.0942(9) 0.1724(5) 0.9067(4) 0.0163(11) Uani 1 1 d . . . . .
C6 C 0.2751(9) 0.3803(5) 0.8328(4) 0.0186(11) Uani 1 1 d . . . . .
C7 C 0.7234(8) 0.7929(5) 0.7184(4) 0.0134(10) Uani 1 1 d . . . . .
C8 C 0.9205(8) 0.8379(5) 0.7538(4) 0.0131(10) Uani 1 1 d . . . . .
C9 C 1.0355(8) 0.7570(5) 0.8548(4) 0.0150(10) Uani 1 1 d . . . . .
C10 C 0.9480(8) 0.9572(5) 0.6750(4) 0.0159(11) Uani 1 1 d . . . . .
C11 C 0.7710(8) 0.9904(5) 0.5892(4) 0.0150(11) Uani 1 1 d . . . . .
C12 C 1.1126(9) 1.0447(5) 0.6639(4) 0.0187(11) Uani 1 1 d . . . . .
Cl1 Cl 0.0078(2) 0.57970(12) 0.61580(9) 0.0170(3) Uani 1 1 d . . . . .
Cl2 Cl 1.2597(2) 0.81723(12) 0.89564(9) 0.0160(3) Uani 1 1 d . . . . .
N1 N -0.3618(7) 0.1971(4) 0.7342(3) 0.0163(9) Uani 1 1 d . . . . .
N2 N -0.3142(7) 0.4566(4) 0.5876(3) 0.0139(9) Uani 1 1 d . . . . .
N3 N -0.0895(7) 0.1273(4) 0.8754(3) 0.0158(9) Uani 1 1 d . . . . .
H3 H -0.133704 0.051885 0.910889 0.019 Uiso 1 1 calc R U . . .
N4 N 0.4219(8) 0.4306(4) 0.8460(3) 0.0215(10) Uani 1 1 d . . . . .
N5 N 0.6329(7) 0.6867(4) 0.7642(3) 0.0142(9) Uani 1 1 d . . . . .
N6 N 0.9903(7) 0.6421(4) 0.9188(3) 0.0161(9) Uani 1 1 d . . . . .
N7 N 0.6446(7) 0.8884(4) 0.6204(3) 0.0163(9) Uani 1 1 d . . . . .
H7 H 0.529992 0.884253 0.583379 0.020 Uiso 1 1 calc R U . . .
N8 N 1.2330(8) 1.1229(4) 0.6469(3) 0.0222(10) Uani 1 1 d . . . . .
O1 O 0.2184(6) 0.1129(3) 0.9881(3) 0.0199(8) Uani 1 1 d . . . . .
O2 O 0.7439(6) 1.0901(3) 0.5054(2) 0.0188(8) Uani 1 1 d . . . . .
Se1 Se -0.48280(9) 0.32516(5) 0.60980(4) 0.01549(14) Uani 1 1 d . . . . .
Se2 Se 0.75930(8) 0.56682(5) 0.89008(3) 0.01484(14) 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 N1 1.277(6) . ?
C1 N3 1.376(6) . ?
C1 C2 1.467(6) . ?
C2 C4 1.362(6) . ?
C2 C3 1.431(7) . ?
C3 N2 1.297(6) . ?
C3 Cl1 1.738(4) . ?
C4 C6 1.420(6) . ?
C4 C5 1.475(7) . ?
C5 O1 1.227(6) . ?
C5 N3 1.383(6) . ?
C6 N4 1.139(6) . ?
C7 N5 1.282(6) . ?
C7 N7 1.372(6) . ?
C7 C8 1.473(6) . ?
C8 C10 1.365(6) . ?
C8 C9 1.426(6) . ?
C9 N6 1.292(6) . ?
C9 Cl2 1.739(4) . ?
C10 C12 1.424(6) . ?
C10 C11 1.468(6) . ?
C11 O2 1.231(6) . ?
C11 N7 1.361(6) . ?
C12 N8 1.144(6) . ?
N1 Se1 1.804(4) . ?
N2 Se1 1.799(4) . ?
N5 Se2 1.795(4) . ?
N6 Se2 1.804(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N3 122.3(4) . . ?
N1 C1 C2 130.8(4) . . ?
N3 C1 C2 106.9(4) . . ?
C4 C2 C3 133.7(4) . . ?
C4 C2 C1 107.6(4) . . ?
C3 C2 C1 118.7(4) . . ?
N2 C3 C2 126.0(4) . . ?
N2 C3 Cl1 116.3(4) . . ?
C2 C3 Cl1 117.7(3) . . ?
C2 C4 C6 131.5(5) . . ?
C2 C4 C5 108.6(4) . . ?
C6 C4 C5 119.9(4) . . ?
O1 C5 N3 126.0(4) . . ?
O1 C5 C4 128.2(4) . . ?
N3 C5 C4 105.7(4) . . ?
N4 C6 C4 174.3(6) . . ?
N5 C7 N7 122.9(4) . . ?
N5 C7 C8 130.1(4) . . ?
N7 C7 C8 107.0(4) . . ?
C10 C8 C9 134.5(4) . . ?
C10 C8 C7 106.6(4) . . ?
C9 C8 C7 118.9(4) . . ?
N6 C9 C8 126.1(4) . . ?
N6 C9 Cl2 116.6(4) . . ?
C8 C9 Cl2 117.3(4) . . ?
C8 C10 C12 131.8(4) . . ?
C8 C10 C11 108.7(4) . . ?
C12 C10 C11 119.5(4) . . ?
O2 C11 N7 126.8(4) . . ?
O2 C11 C10 126.8(4) . . ?
N7 C11 C10 106.3(4) . . ?
N8 C12 C10 173.8(5) . . ?
C1 N1 Se1 118.1(3) . . ?
C3 N2 Se1 122.3(3) . . ?
C1 N3 C5 111.2(4) . . ?
C7 N5 Se2 118.5(3) . . ?
C9 N6 Se2 122.3(3) . . ?
C11 N7 C7 111.3(4) . . ?
N2 Se1 N1 104.04(18) . . ?
N5 Se2 N6 104.01(18) . . ?

_refine_diff_density_max         1.235
_refine_diff_density_min         -0.966
_refine_diff_density_rms         0.171


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCE'
####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2288307'
loop_
_audit_author_name
_audit_author_address
'Andreas Kourtellaris'
;University of Cyprus
Cyprus
;
_audit_update_record             
;
2023-08-12 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT196_shelx               
;
PROBLEM: No TEMP record and _measurement_temperature .NE.        293 Degree
RESPONSE: no response from crystallographer
;
_vrf_PLAT052_shelx               
;
PROBLEM: Info on Absorption Correction Method   Not Given     Please Do !
RESPONSE: no response from crystallographer
;
_vrf_PLAT057_shelx               
;
PROBLEM: Correction for Absorption Required   RT(exp) ...       1.15 Do !
RESPONSE: no response from crystallographer
;
_vrf_PLAT220_shelx               
;
PROBLEM: NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.8 Ratio
RESPONSE: no response from crystallographer
;
_vrf_PLAT234_shelx               
;
PROBLEM: Large Hirshfeld Difference C9       --C10      .       0.17 Ang.
RESPONSE: no response from crystallographer
;
_vrf_PLAT241_shelx               
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         C8 Check
RESPONSE: no response from crystallographer
;
_vrf_PLAT242_shelx               
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         O1 Check
RESPONSE: no response from crystallographer
;
_vrf_PLAT250_shelx               
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.1 Note
RESPONSE: no response from crystallographer
;
_vrf_PLAT341_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01229 Ang.
RESPONSE: no response from crystallographer
;
_vrf_PLAT906_shelx               
;
PROBLEM: Large K Value in the Analysis of Variance ......      7.934 Check
RESPONSE: no response from crystallographer
;
_vrf_PLAT971_shelx               
;
PROBLEM: Check Calcd Resid. Dens.  1.03Ang From C8              2.31 eA-3
RESPONSE: no response from crystallographer
;
_vrf_PLAT977_shelx               
;
PROBLEM: Check Negative Difference Density on H7A       .      -0.47 eA-3
RESPONSE: no response from crystallographer
;
# Added during the CSD deposition process: Saturday 12 August 2023 10:28 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
4-Chloro-6-morpholinopyrrolo[2,3-c][1,2,6]selenadiazine-5-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 Cl N5 O Se'
_chemical_formula_sum            'C10 H8 Cl N5 O Se'
_chemical_formula_weight         328.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.3639 0.7018 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.9615(4)
_cell_length_b                   5.9698(3)
_cell_length_c                   18.9005(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.102(4)
_cell_angle_gamma                90
_cell_volume                     1123.22(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1677
_cell_measurement_theta_min      4.4240
_cell_measurement_theta_max      71.2790

_exptl_crystal_description       plates
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.943
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    6.700
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ' multi-scan'
_exptl_absorpt_correction_T_min  0.82083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.709
_oxdiff_exptl_absorpt_empirical_full_max 1.351
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.4223
_diffrn_reflns_number            3867
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.682
_diffrn_reflns_theta_max         71.663
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2138
_reflns_number_gt                1988
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0628P)²+12.8831P] 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         2138
_refine_ls_number_parameters     163
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.1909
_refine_ls_wR_factor_gt          0.1883
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_restrained_S_all      1.241
_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
Cl1 Cl 0.6924(2) 0.3456(4) 0.28873(14) 0.0499(7) Uani 1 1 d . . . . .
N1 N 0.6979(7) 0.6874(12) 0.3717(4) 0.0322(15) Uani 1 1 d . . . . .
N2 N 0.4718(7) 0.7988(11) 0.4538(3) 0.0279(14) Uani 1 1 d . . . . .
N3 N 0.2956(7) 0.5493(11) 0.4334(4) 0.0318(15) Uani 1 1 d . . . . .
N4 N 0.4185(9) -0.0114(13) 0.2663(4) 0.045(2) Uani 1 1 d . . . . .
N5 N 0.1599(8) 0.2563(13) 0.3920(5) 0.0448(19) Uani 1 1 d D . . . .
O1 O -0.0889(6) 0.0388(11) 0.4031(3) 0.0411(14) Uani 1 1 d D U . . .
Se1 Se 0.64057(8) 0.88662(14) 0.43540(4) 0.0287(3) Uani 1 1 d . . . . .
C1 C 0.6234(8) 0.5223(14) 0.3502(4) 0.0311(17) Uani 1 1 d . . . . .
C2 C 0.4899(8) 0.4777(13) 0.3711(4) 0.0258(15) Uani 1 1 d . . . . .
C3 C 0.4224(8) 0.6251(13) 0.4231(4) 0.0277(16) Uani 1 1 d . . . . .
C4 C 0.3976(7) 0.3136(12) 0.3528(4) 0.0264(15) Uani 1 1 d . . . . .
C5 C 0.2771(8) 0.3681(13) 0.3935(5) 0.0332(17) Uani 1 1 d . . . . .
C6 C 0.4130(8) 0.1342(15) 0.3047(5) 0.0344(18) Uani 1 1 d . . . . .
C7 C 0.1443(10) 0.0369(18) 0.3627(8) 0.073(4) Uani 1 1 d D U . . .
H7A H 0.184605 -0.072001 0.395155 0.087 Uiso 1 1 calc R U . . .
H7B H 0.190658 0.028280 0.318546 0.087 Uiso 1 1 calc R U . . .
C8 C -0.0008(10) -0.018(2) 0.3496(8) 0.078(3) Uani 1 1 d D U . . .
H8A H -0.031350 0.057025 0.306404 0.093 Uiso 1 1 calc R U . . .
H8B H -0.008222 -0.177902 0.341170 0.093 Uiso 1 1 calc R U . . .
C9 C -0.0717(10) 0.267(2) 0.4229(8) 0.076(3) Uani 1 1 d D U . . .
H9A H -0.128584 0.298009 0.462336 0.091 Uiso 1 1 calc R U . . .
H9B H -0.102600 0.360350 0.383604 0.091 Uiso 1 1 calc R U . . .
C10 C 0.0688(10) 0.333(3) 0.4436(9) 0.097(5) Uani 1 1 d D U . . .
H10A H 0.074510 0.494410 0.447687 0.117 Uiso 1 1 calc R U . . .
H10B H 0.093536 0.268339 0.489347 0.117 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
Cl1 C1 1.730(8) . ?
N1 C1 1.290(11) . ?
N1 Se1 1.801(7) . ?
N2 C3 1.278(11) . ?
N2 Se1 1.807(6) . ?
N3 C5 1.328(11) . ?
N3 C3 1.362(10) . ?
N4 C6 1.136(11) . ?
N5 C5 1.344(11) . ?
N5 C7 1.428(11) . ?
N5 C10 1.431(12) . ?
O1 C8 1.405(11) . ?
O1 C9 1.421(11) . ?
C1 C2 1.426(10) . ?
C2 C4 1.379(11) . ?
C2 C3 1.497(10) . ?
C4 C6 1.417(11) . ?
C4 C5 1.484(10) . ?
C7 C8 1.495(9) . ?
C9 C10 1.492(9) . ?

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 N1 Se1 121.5(5) . . ?
C3 N2 Se1 119.6(5) . . ?
C5 N3 C3 107.4(6) . . ?
C5 N5 C7 123.1(7) . . ?
C5 N5 C10 113.6(8) . . ?
C7 N5 C10 119.6(9) . . ?
C8 O1 C9 110.4(8) . . ?
N1 Se1 N2 104.9(3) . . ?
N1 C1 C2 125.9(8) . . ?
N1 C1 Cl1 116.0(6) . . ?
C2 C1 Cl1 118.1(6) . . ?
C4 C2 C1 133.0(7) . . ?
C4 C2 C3 105.7(6) . . ?
C1 C2 C3 121.2(7) . . ?
N2 C3 N3 123.3(7) . . ?
N2 C3 C2 126.9(7) . . ?
N3 C3 C2 109.8(7) . . ?
C2 C4 C6 127.7(7) . . ?
C2 C4 C5 105.0(7) . . ?
C6 C4 C5 127.3(7) . . ?
N3 C5 N5 121.2(7) . . ?
N3 C5 C4 112.0(7) . . ?
N5 C5 C4 126.8(8) . . ?
N4 C6 C4 176.6(9) . . ?
N5 C7 C8 110.9(9) . . ?
O1 C8 C7 117.0(10) . . ?
O1 C9 C10 115.1(10) . . ?
N5 C10 C9 110.5(10) . . ?

_refine_diff_density_max         2.126
_refine_diff_density_min         -1.124
_refine_diff_density_rms         0.161


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCE/c-hexane'
