# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_miao20201126-1
_database_code_depnum_ccdc_archive 'CCDC 2239190'
loop_
_audit_author_name
_audit_author_address
a
;luoyang normal university
China
;
_audit_update_record             
;
2023-02-01 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;
_audit_creation_date             2020-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N2 Se, C7 H5 N O4'
_chemical_formula_sum            'C13 H9 N3 O4 Se'
_chemical_formula_weight         350.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6846(2)
_cell_length_b                   7.0498(2)
_cell_length_c                   15.0256(4)
_cell_angle_alpha                97.105(2)
_cell_angle_beta                 94.771(2)
_cell_angle_gamma                109.331(3)
_cell_volume                     657.18(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7206
_cell_measurement_temperature    290
_cell_measurement_theta_max      27.3050
_cell_measurement_theta_min      3.9060
_shelx_estimated_absorpt_T_max   0.545
_shelx_estimated_absorpt_T_min   0.500
_exptl_absorpt_coefficient_mu    2.877
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15586
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.469
_diffrn_reflns_theta_min         3.258
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  54.00   1.00    8.59    --  -13.57  57.00 -60.00   84
  2  ω    -20.00  25.00   1.00    8.59    --  -13.57 -99.00-150.00   45
  3  ω    -20.00  54.00   1.00    8.59    --   14.89 -99.00 -90.00   74
  4  ω    -53.00  42.00   1.00    8.59    --   14.89 -77.00  90.00   95
  5  ω     -2.00  82.00   1.00    8.59    --   14.89  57.00   0.00   84
  6  ω     -4.00  84.00   1.00    8.59    --   14.89  38.00-150.00   88
  7  ω     -2.00  82.00   1.00    8.59    --   14.89  57.00  90.00   84
  8  ω    -12.00  82.00   1.00    8.59    --   14.89  77.00-150.00   94
  9  ω    -20.00  54.00   1.00    8.59    --   14.89 -99.00   0.00   74
 10  ω    -53.00  42.00   1.00    8.59    --   14.89 -77.00-180.00   95
 11  ω    -81.00  -6.00   1.00    8.59    --  -13.57 -77.00-150.00   75
 12  ω    -86.00 -35.00   1.00    8.59    --  -13.57-178.00  90.00   51
 13  ω    -20.00  54.00   1.00    8.59    --   14.89 -99.00-180.00   74
 14  ω     -5.00  64.00   1.00    8.59    --   14.89-117.00  91.04   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1054650000
_diffrn_orient_matrix_UB_12      -0.0125453000
_diffrn_orient_matrix_UB_13      0.0093921000
_diffrn_orient_matrix_UB_21      -0.0211915000
_diffrn_orient_matrix_UB_22      0.0352087000
_diffrn_orient_matrix_UB_23      -0.0407542000
_diffrn_orient_matrix_UB_31      -0.0360433000
_diffrn_orient_matrix_UB_32      -0.1013576000
_diffrn_orient_matrix_UB_33      -0.0235456000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2720
_reflns_number_total             3008
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3008
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0267P)²+0.3477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0684
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.05453(4) 0.68079(4) 0.40825(2) 0.03898(9) Uani 1 1 d . . . . .
N1 N 0.3094(3) 0.7224(3) 0.36959(12) 0.0341(4) Uani 1 1 d . . . . .
N2 N -0.0814(3) 0.6521(3) 0.29796(14) 0.0404(5) Uani 1 1 d . . . . .
C1 C 0.2793(3) 0.7119(3) 0.28013(14) 0.0293(4) Uani 1 1 d . . . . .
C2 C 0.0627(3) 0.6745(3) 0.24088(15) 0.0321(5) Uani 1 1 d . . . . .
C3 C 0.0189(4) 0.6647(4) 0.14551(16) 0.0423(6) Uani 1 1 d . . . . .
H3 H -0.1196 0.6395 0.1185 0.051 Uiso 1 1 calc R . . . .
C4 C 0.1793(5) 0.6921(4) 0.09536(16) 0.0468(6) Uani 1 1 d . . . . .
H4 H 0.1508 0.6883 0.0334 0.056 Uiso 1 1 calc R . . . .
C5 C 0.3929(4) 0.7269(4) 0.13427(16) 0.0438(6) Uani 1 1 d . . . . .
H5 H 0.4998 0.7439 0.0970 0.053 Uiso 1 1 calc R . . . .
C6 C 0.4440(4) 0.7359(4) 0.22421(16) 0.0381(5) Uani 1 1 d . . . . .
H6 H 0.5836 0.7574 0.2487 0.046 Uiso 1 1 calc R . . . .
O1 O 0.6307(3) 0.7618(3) 0.50099(11) 0.0478(4) Uani 1 1 d . . . . .
H1 H 0.5436 0.7521 0.4574 0.072 Uiso 1 1 calc GR . . . .
O2 O 0.3525(3) 0.7416(3) 0.57642(11) 0.0506(5) Uani 1 1 d . . . . .
O3 O 0.4525(3) 0.7504(4) 0.90226(13) 0.0716(6) Uani 1 1 d . . . . .
O4 O 0.7618(4) 0.7951(4) 0.97243(13) 0.0765(7) Uani 1 1 d . . . . .
N3 N 0.6429(4) 0.7773(3) 0.90387(14) 0.0470(5) Uani 1 1 d . . . . .
C7 C 0.6847(3) 0.7793(3) 0.65896(14) 0.0301(4) Uani 1 1 d . . . . .
C8 C 0.5994(3) 0.7634(3) 0.74000(15) 0.0330(5) Uani 1 1 d . . . . .
H8 H 0.4536 0.7351 0.7413 0.040 Uiso 1 1 calc R . . . .
C9 C 0.7342(4) 0.7901(3) 0.81822(15) 0.0342(5) Uani 1 1 d . . . . .
C10 C 0.9509(4) 0.8288(4) 0.81969(16) 0.0387(5) Uani 1 1 d . . . . .
H10 H 1.0386 0.8460 0.8736 0.046 Uiso 1 1 calc R . . . .
C11 C 1.0330(4) 0.8411(4) 0.73863(17) 0.0404(5) Uani 1 1 d . . . . .
H11 H 1.1782 0.8653 0.7377 0.049 Uiso 1 1 calc R . . . .
C12 C 0.9028(4) 0.8180(3) 0.65861(16) 0.0354(5) Uani 1 1 d . . . . .
H12 H 0.9610 0.8283 0.6045 0.042 Uiso 1 1 calc R . . . .
C13 C 0.5380(4) 0.7588(3) 0.57558(15) 0.0354(5) 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
Se1 N1 1.7891(18) . ?
Se1 N2 1.777(2) . ?
N1 C1 1.331(3) . ?
N2 C2 1.326(3) . ?
C1 C2 1.443(3) . ?
C1 C6 1.418(3) . ?
C2 C3 1.427(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.337(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.426(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.354(3) . ?
C6 H6 0.9300 . ?
O1 H1 0.8200 . ?
O1 C13 1.324(3) . ?
O2 C13 1.206(3) . ?
O3 N3 1.221(3) . ?
O4 N3 1.214(3) . ?
N3 C9 1.470(3) . ?
C7 C8 1.388(3) . ?
C7 C12 1.392(3) . ?
C7 C13 1.486(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(3) . ?
C9 C10 1.380(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Se1 N1 93.71(8) . . ?
C1 N1 Se1 107.15(14) . . ?
C2 N2 Se1 107.42(15) . . ?
N1 C1 C2 115.58(19) . . ?
N1 C1 C6 124.27(19) . . ?
C6 C1 C2 120.15(19) . . ?
N2 C2 C1 116.1(2) . . ?
N2 C2 C3 125.1(2) . . ?
C3 C2 C1 118.7(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.8(2) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 H6 120.8 . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 H6 120.8 . . ?
C13 O1 H1 109.5 . . ?
O3 N3 C9 118.3(2) . . ?
O4 N3 O3 123.7(2) . . ?
O4 N3 C9 118.0(2) . . ?
C8 C7 C12 119.5(2) . . ?
C8 C7 C13 118.03(19) . . ?
C12 C7 C13 122.46(19) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 N3 118.3(2) . . ?
C8 C9 C10 122.8(2) . . ?
C10 C9 N3 118.9(2) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 C9 117.8(2) . . ?
C11 C10 H10 121.1 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.1(2) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
O1 C13 C7 113.53(19) . . ?
O2 C13 O1 123.6(2) . . ?
O2 C13 C7 122.8(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 1.376
_oxdiff_exptl_absorpt_empirical_full_min 0.762
####################################################################### 
# 
# 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_miao20201204-2
_database_code_depnum_ccdc_archive 'CCDC 2239191'
loop_
_audit_author_name
_audit_author_address
b
;luoyang normal university
China
;
_audit_update_record             
;
2023-02-01 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;
_audit_creation_date             2020-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N2 Se, C7 H5 N O4'
_chemical_formula_sum            'C13 H9 N3 O4 Se'
_chemical_formula_weight         350.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7936(2)
_cell_length_b                   7.3480(3)
_cell_length_c                   14.7847(5)
_cell_angle_alpha                76.886(3)
_cell_angle_beta                 76.865(3)
_cell_angle_gamma                69.400(4)
_cell_volume                     663.98(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5977
_cell_measurement_temperature    290
_cell_measurement_theta_max      24.9730
_cell_measurement_theta_min      3.8190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.848
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15689
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.350
_diffrn_reflns_theta_min         3.330
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00   12.57    --  -13.49 -99.00 -60.00   45
  2  ω    -81.00   3.00   1.00   12.57    --  -13.49 -57.00  30.00   84
  3  ω     -4.00  84.00   1.00   12.57    --   14.89  38.00-180.00   88
  4  ω    -20.00  54.00   1.00   12.57    --   14.89 -99.00   0.00   74
  5  ω     -2.00  82.00   1.00   12.57    --   14.89  57.00 -30.00   84
  6  ω     -4.00  84.00   1.00   12.57    --   14.89  38.00 -90.00   88
  7  ω     -9.00  61.00   1.00   12.57    --   14.89-112.00 104.52   70
  8  ω    -53.00  42.00   1.00   12.57    --   14.89 -77.00-180.00   95
  9  ω      8.00  74.00   1.00   12.57    --   14.89-134.00 -82.84   66
 10  ω    -20.00  25.00   1.00   12.57    --  -13.49 -99.00   0.00   45
 11  ω    -43.00  58.00   1.00   12.57    --  -13.49  19.00 -90.00  101
 12  ω    -10.00  61.00   1.00   12.57    --   14.89-111.00 145.67   71
 13  ω    -20.00  54.00   1.00   12.57    --   14.89 -99.00-180.00   74
 14  ω    -20.00  26.00   1.00   12.57    --   14.89 -99.00  30.00   46
 15  ω     35.00  87.00   1.00   12.57    --   14.89 178.00-150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0893490000
_diffrn_orient_matrix_UB_12      -0.0815778000
_diffrn_orient_matrix_UB_13      0.0118507000
_diffrn_orient_matrix_UB_21      0.0296034000
_diffrn_orient_matrix_UB_22      0.0584651000
_diffrn_orient_matrix_UB_23      0.0232993000
_diffrn_orient_matrix_UB_31      -0.0625735000
_diffrn_orient_matrix_UB_32      -0.0290694000
_diffrn_orient_matrix_UB_33      0.0425252000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2581
_reflns_number_total             3024
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.038
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3024
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.2429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0980
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Se01 Se -0.20445(5) 0.63957(5) 0.14548(2) 0.04080(13) Uani 1 1 d . . . . .
N1 N -0.3028(4) 0.7515(4) 0.03786(18) 0.0420(6) Uani 1 1 d . . . . .
N2 N 0.0578(4) 0.6542(4) 0.09922(16) 0.0350(5) Uani 1 1 d . . . . .
C1 C -0.1428(5) 0.7937(4) -0.0241(2) 0.0343(6) Uani 1 1 d . . . . .
C2 C 0.0568(4) 0.7400(4) 0.00931(18) 0.0302(6) Uani 1 1 d . . . . .
C3 C 0.2371(5) 0.7791(4) -0.0522(2) 0.0371(7) Uani 1 1 d . . . . .
H3 H 0.3667 0.7455 -0.0316 0.045 Uiso 1 1 calc R . . . .
C4 C 0.2131(5) 0.8674(4) -0.1424(2) 0.0431(7) Uani 1 1 d . . . . .
H4 H 0.3290 0.8937 -0.1836 0.052 Uiso 1 1 calc R . . . .
C5 C 0.0159(6) 0.9205(5) -0.1752(2) 0.0464(8) Uani 1 1 d . . . . .
H5 H 0.0064 0.9813 -0.2372 0.056 Uiso 1 1 calc R . . . .
C6 C -0.1567(5) 0.8854(5) -0.1194(2) 0.0442(8) Uani 1 1 d . . . . .
H6 H -0.2836 0.9204 -0.1426 0.053 Uiso 1 1 calc R . . . .
O1 O 0.0340(4) 0.4643(4) 0.31199(16) 0.0576(7) Uani 1 1 d . . . . .
O2 O 0.3312(3) 0.5113(4) 0.22405(15) 0.0558(7) Uani 1 1 d . . . . .
H2 H 0.2575 0.5518 0.1823 0.084 Uiso 1 1 calc GR . . . .
O3 O 0.8637(4) 0.1266(5) 0.60002(18) 0.0704(8) Uani 1 1 d . . . . .
O4 O 0.5843(4) 0.0763(5) 0.68788(16) 0.0696(8) Uani 1 1 d . . . . .
N3 N 0.6787(4) 0.1325(4) 0.61198(17) 0.0425(6) Uani 1 1 d . . . . .
C7 C 0.3449(4) 0.3650(4) 0.38227(19) 0.0331(6) Uani 1 1 d . . . . .
C8 C 0.5620(5) 0.3383(5) 0.3697(2) 0.0389(7) Uani 1 1 d . . . . .
H8 H 0.6334 0.3728 0.3102 0.047 Uiso 1 1 calc R . . . .
C9 C 0.6721(4) 0.2616(5) 0.4442(2) 0.0379(7) Uani 1 1 d . . . . .
H9 H 0.8173 0.2431 0.4359 0.046 Uiso 1 1 calc R . . . .
C10 C 0.5613(4) 0.2123(4) 0.53215(18) 0.0322(6) Uani 1 1 d . . . . .
C11 C 0.3484(5) 0.2345(5) 0.5470(2) 0.0390(7) Uani 1 1 d . . . . .
H11 H 0.2785 0.1988 0.6067 0.047 Uiso 1 1 calc R . . . .
C12 C 0.2392(5) 0.3109(5) 0.4715(2) 0.0379(7) Uani 1 1 d . . . . .
H12 H 0.0946 0.3265 0.4803 0.046 Uiso 1 1 calc R . . . .
C13 C 0.2189(5) 0.4508(5) 0.3034(2) 0.0393(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se01 N1 1.777(3) . ?
Se01 N2 1.789(2) . ?
N1 C1 1.331(4) . ?
N2 C2 1.336(3) . ?
C1 C2 1.442(4) . ?
C1 C6 1.427(4) . ?
C2 C3 1.426(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.423(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.340(5) . ?
C6 H6 0.9300 . ?
O1 C13 1.204(4) . ?
O2 H2 0.8200 . ?
O2 C13 1.323(4) . ?
O3 N3 1.215(3) . ?
O4 N3 1.221(3) . ?
N3 C10 1.469(4) . ?
C7 C8 1.392(4) . ?
C7 C12 1.395(4) . ?
C7 C13 1.493(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(4) . ?
C10 C11 1.369(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(4) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Se01 N2 94.14(11) . . ?
C1 N1 Se01 106.99(19) . . ?
C2 N2 Se01 106.85(19) . . ?
N1 C1 C2 116.4(3) . . ?
N1 C1 C6 124.6(3) . . ?
C6 C1 C2 119.0(3) . . ?
N2 C2 C1 115.6(3) . . ?
N2 C2 C3 124.1(3) . . ?
C3 C2 C1 120.3(3) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 C2 117.8(3) . . ?
C4 C3 H3 121.1 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.9(3) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 H6 120.5 . . ?
C13 O2 H2 109.5 . . ?
O3 N3 O4 123.0(3) . . ?
O3 N3 C10 119.0(2) . . ?
O4 N3 C10 118.0(3) . . ?
C8 C7 C12 119.4(3) . . ?
C8 C7 C13 122.4(2) . . ?
C12 C7 C13 118.3(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.8 . . ?
C8 C9 C10 118.3(3) . . ?
C10 C9 H9 120.8 . . ?
C9 C10 N3 118.3(2) . . ?
C11 C10 N3 119.2(2) . . ?
C11 C10 C9 122.6(3) . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.7(3) . . ?
C12 C11 H11 120.7 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
O1 C13 O2 123.9(3) . . ?
O1 C13 C7 123.1(3) . . ?
O2 C13 C7 113.0(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 1.458
_oxdiff_exptl_absorpt_empirical_full_min 0.670
####################################################################### 
# 
# 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_miao202014-4
_database_code_depnum_ccdc_archive 'CCDC 2239194'
loop_
_audit_author_name
_audit_author_address
c
;luoyang normal university
China
;
_audit_update_record             
;
2023-02-01 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;
_audit_creation_date             2020-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C6 H4 N2 Se), C9 H6 O6'
_chemical_formula_sum            'C27 H18 N6 O6 Se3'
_chemical_formula_weight         759.35
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.9284(2)
_cell_length_b                   26.3154(12)
_cell_length_c                   13.1324(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.977(4)
_cell_angle_gamma                90
_cell_volume                     1356.79(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7305
_cell_measurement_temperature    291
_cell_measurement_theta_max      22.5580
_cell_measurement_theta_min      3.8580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_unetI/netI     0.0947
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32014
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.531
_diffrn_reflns_theta_min         3.464
_diffrn_ambient_temperature      291
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00   16.80    --  -13.49 -99.00  30.00   45
  2  ω    -86.00 -35.00   1.00   16.80    --  -13.49-178.00 -30.00   51
  3  ω    -54.00  84.00   1.00   16.80    --   14.89   0.00 150.00  138
  4  ω     -1.00  66.00   1.00   16.80    --   14.89-121.00-112.00   67
  5  ω     -2.00  82.00   1.00   16.80    --   14.89  57.00 -90.00   84
  6  ω     -2.00  82.00   1.00   16.80    --   14.89  57.00   0.00   84
  7  ω     -4.00  84.00   1.00   16.80    --   14.89  38.00-150.00   88
  8  ω     35.00  87.00   1.00   16.80    --   14.89 178.00-120.00   52
  9  ω     -5.00  64.00   1.00   16.80    --   14.89-117.00  34.04   69
 10  ω      1.00  68.00   1.00   16.80    --   14.89-124.00 137.59   67
 11  ω    -86.00 -35.00   1.00   16.80    --  -13.49-178.00 -90.00   51
 12  ω    -20.00  25.00   1.00   16.80    --  -13.49 -99.00-180.00   45
 13  ω    -20.00  25.00   1.00   16.80    --  -13.49 -99.00   0.00   45
 14  ω    -20.00  23.00   1.00   16.80    --   14.89 -99.00-180.00   43
 15  ω    -53.00  42.00   1.00   16.80    --   14.89 -77.00 120.00   95
 16  ω    -20.00  54.00   1.00   16.80    --   14.89 -99.00 -60.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1454289000
_diffrn_orient_matrix_UB_12      -0.0088776000
_diffrn_orient_matrix_UB_13      0.0281540000
_diffrn_orient_matrix_UB_21      0.0587745000
_diffrn_orient_matrix_UB_22      0.0253563000
_diffrn_orient_matrix_UB_23      0.0058390000
_diffrn_orient_matrix_UB_31      -0.0895218000
_diffrn_orient_matrix_UB_32      0.0022307000
_diffrn_orient_matrix_UB_33      0.0457766000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.850
_reflns_number_gt                4825
_reflns_number_total             6146
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 
;
 Flack x determined using 1661 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.452(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         6146
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²+3.3795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1107
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C24(H24), C25(H25), C26(H26),
 C27(H27), C18(H18), C19(H19), C20(H20), C21(H21), C2(H2), C4(H4A), C6(H6A)
2.b Tetrahedral OH refined with riding coordinates:
 O6(H6)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 -0.1249(3) 0.30924(4) 0.92622(8) 0.0336(3) Uani 1 1 d . . . . .
N1 N -0.202(3) 0.2427(4) 0.9235(7) 0.039(3) Uani 1 1 d . . . . .
N2 N -0.310(3) 0.3188(3) 0.8012(6) 0.035(2) Uani 1 1 d . . . . .
C10 C -0.420(3) 0.2741(4) 0.7658(8) 0.031(3) Uani 1 1 d . . . . .
C11 C -0.356(3) 0.2318(4) 0.8341(8) 0.034(3) Uani 1 1 d . . . . .
C12 C -0.461(4) 0.1823(4) 0.8036(10) 0.048(3) Uani 1 1 d . . . . .
H12 H -0.4293 0.1548 0.8475 0.058 Uiso 1 1 calc R . . . .
C13 C -0.608(4) 0.1755(5) 0.7098(10) 0.049(4) Uani 1 1 d . . . . .
H13 H -0.6671 0.1429 0.6881 0.059 Uiso 1 1 calc R . . . .
C14 C -0.673(3) 0.2177(5) 0.6438(9) 0.048(4) Uani 1 1 d . . . . .
H14 H -0.7822 0.2121 0.5808 0.057 Uiso 1 1 calc R . . . .
C15 C -0.582(3) 0.2656(5) 0.6701(9) 0.042(3) Uani 1 1 d . . . . .
H15 H -0.6256 0.2925 0.6256 0.051 Uiso 1 1 calc R . . . .
Se2 Se -0.1057(3) 0.69992(4) 0.89201(8) 0.0334(3) Uani 1 1 d . . . . .
N3 N -0.168(2) 0.7673(3) 0.8783(7) 0.032(2) Uani 1 1 d . . . . .
N4 N -0.307(3) 0.6860(3) 0.7693(7) 0.036(2) Uani 1 1 d . . . . .
C22 C -0.329(3) 0.7743(4) 0.7877(8) 0.031(3) Uani 1 1 d . . . . .
C23 C -0.405(3) 0.7291(4) 0.7278(8) 0.025(2) Uani 1 1 d . . . . .
C24 C -0.578(3) 0.7343(4) 0.6313(9) 0.040(3) Uani 1 1 d . . . . .
H24 H -0.6285 0.7059 0.5915 0.048 Uiso 1 1 calc R . . . .
C25 C -0.667(3) 0.7810(5) 0.5990(10) 0.045(3) Uani 1 1 d . . . . .
H25 H -0.7850 0.7846 0.5367 0.054 Uiso 1 1 calc R . . . .
C26 C -0.587(3) 0.8254(4) 0.6576(9) 0.039(3) Uani 1 1 d . . . . .
H26 H -0.6515 0.8570 0.6319 0.047 Uiso 1 1 calc R . . . .
C27 C -0.422(3) 0.8228(4) 0.7488(8) 0.035(3) Uani 1 1 d . . . . .
H27 H -0.3692 0.8522 0.7854 0.042 Uiso 1 1 calc R . . . .
Se3 Se 0.7851(3) 0.42712(4) 0.09038(8) 0.0353(3) Uani 1 1 d . . . . .
N5 N 0.980(2) 0.4257(4) -0.0306(7) 0.038(2) Uani 1 1 d . . . . .
N6 N 0.837(2) 0.4952(4) 0.1035(7) 0.035(2) Uani 1 1 d . . . . .
C16 C 0.990(3) 0.5102(4) 0.0212(8) 0.029(2) Uani 1 1 d . . . . .
C17 C 1.072(3) 0.4725(4) -0.0501(8) 0.029(2) Uani 1 1 d . . . . .
C18 C 1.245(3) 0.4870(5) -0.1413(8) 0.038(3) Uani 1 1 d . . . . .
H18 H 1.3008 0.4627 -0.1893 0.045 Uiso 1 1 calc R . . . .
C19 C 1.323(3) 0.5351(5) -0.1552(9) 0.048(3) Uani 1 1 d . . . . .
H19 H 1.4309 0.5446 -0.2142 0.057 Uiso 1 1 calc R . . . .
C20 C 1.245(3) 0.5732(5) -0.0811(10) 0.043(3) Uani 1 1 d . . . . .
H20 H 1.3089 0.6067 -0.0929 0.052 Uiso 1 1 calc R . . . .
C21 C 1.085(3) 0.5623(5) 0.0042(10) 0.043(3) Uani 1 1 d . . . . .
H21 H 1.0358 0.5875 0.0510 0.052 Uiso 1 1 calc R . . . .
O1 O -0.243(2) 0.4107(3) 0.6957(6) 0.041(2) Uani 1 1 d . . . . .
H1 H -0.2556 0.3834 0.7252 0.061 Uiso 1 1 calc GR . . . .
O2 O -0.040(3) 0.3631(3) 0.5720(6) 0.051(3) Uani 1 1 d . . . . .
O3 O 0.474(2) 0.4461(3) 0.2765(6) 0.045(2) Uani 1 1 d . . . . .
O4 O 0.488(2) 0.5306(3) 0.2693(5) 0.039(2) Uani 1 1 d . . . . .
H4 H 0.5867 0.5250 0.2165 0.059 Uiso 1 1 calc GR . . . .
O5 O -0.024(3) 0.6337(3) 0.5370(6) 0.053(3) Uani 1 1 d . . . . .
O6 O -0.215(2) 0.5948(3) 0.6731(6) 0.044(2) Uani 1 1 d . . . . .
H6 H -0.2537 0.6239 0.6916 0.067 Uiso 1 1 calc R . . . .
C1 C -0.016(3) 0.4524(4) 0.5554(7) 0.025(2) Uani 1 1 d . . . . .
C2 C 0.142(3) 0.4497(4) 0.4610(7) 0.025(2) Uani 1 1 d . . . . .
H2 H 0.1896 0.4181 0.4332 0.031 Uiso 1 1 calc R . . . .
C3 C 0.229(3) 0.4934(4) 0.4087(7) 0.023(2) Uani 1 1 d . . . . .
C4 C 0.152(3) 0.5402(4) 0.4496(7) 0.028(2) Uani 1 1 d . . . . .
H4A H 0.2062 0.5695 0.4142 0.033 Uiso 1 1 calc R . . . .
C5 C -0.003(3) 0.5444(4) 0.5421(7) 0.023(2) Uani 1 1 d . . . . .
C6 C -0.083(3) 0.5001(4) 0.5953(8) 0.027(2) Uani 1 1 d . . . . .
H6A H -0.1825 0.5026 0.6584 0.033 Uiso 1 1 calc R . . . .
C7 C -0.096(3) 0.4042(4) 0.6082(8) 0.030(3) Uani 1 1 d . . . . .
C8 C 0.407(3) 0.4872(5) 0.3121(8) 0.034(3) Uani 1 1 d . . . . .
C9 C -0.081(3) 0.5958(4) 0.5834(8) 0.028(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
Se1 N1 1.778(10) . ?
Se1 N2 1.790(9) . ?
N1 C11 1.334(14) . ?
N2 C10 1.331(14) . ?
C10 C11 1.446(15) . ?
C10 C15 1.408(16) . ?
C11 C12 1.420(16) . ?
C12 H12 0.9300 . ?
C12 C13 1.354(17) . ?
C13 H13 0.9300 . ?
C13 C14 1.428(18) . ?
C14 H14 0.9300 . ?
C14 C15 1.351(17) . ?
C15 H15 0.9300 . ?
Se2 N3 1.798(9) . ?
Se2 N4 1.807(9) . ?
N3 C22 1.342(14) . ?
N4 C23 1.310(13) . ?
C22 C23 1.452(14) . ?
C22 C27 1.418(15) . ?
C23 C24 1.425(16) . ?
C24 H24 0.9300 . ?
C24 C25 1.343(16) . ?
C25 H25 0.9300 . ?
C25 C26 1.426(16) . ?
C26 H26 0.9300 . ?
C26 C27 1.344(16) . ?
C27 H27 0.9300 . ?
Se3 N5 1.787(9) . ?
Se3 N6 1.811(9) . ?
N5 C17 1.311(14) . ?
N6 C16 1.316(13) . ?
C16 C17 1.410(15) . ?
C16 C21 1.438(16) . ?
C17 C18 1.449(14) . ?
C18 H18 0.9300 . ?
C18 C19 1.317(16) . ?
C19 H19 0.9300 . ?
C19 C20 1.438(18) . ?
C20 H20 0.9300 . ?
C20 C21 1.335(17) . ?
C21 H21 0.9300 . ?
O1 H1 0.8200 . ?
O1 C7 1.314(13) . ?
O2 C7 1.205(13) . ?
O3 C8 1.209(13) . ?
O4 H4 0.8200 . ?
O4 C8 1.317(13) . ?
O5 C9 1.193(12) . ?
O6 H6 0.8200 . ?
O6 C9 1.306(12) . ?
C1 C2 1.407(13) . ?
C1 C6 1.389(15) . ?
C1 C7 1.486(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(13) . ?
C3 C4 1.382(14) . ?
C3 C8 1.479(15) . ?
C4 H4A 0.9300 . ?
C4 C5 1.382(14) . ?
C5 C6 1.401(14) . ?
C5 C9 1.493(14) . ?
C6 H6A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Se1 N2 93.3(4) . . ?
C11 N1 Se1 107.5(8) . . ?
C10 N2 Se1 108.2(7) . . ?
N2 C10 C11 114.6(10) . . ?
N2 C10 C15 125.7(11) . . ?
C15 C10 C11 119.7(11) . . ?
N1 C11 C10 116.4(10) . . ?
N1 C11 C12 124.4(11) . . ?
C12 C11 C10 119.2(10) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.2(11) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(12) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 122.0(11) . . ?
C15 C14 H14 119.0 . . ?
C10 C15 H15 120.5 . . ?
C14 C15 C10 118.9(12) . . ?
C14 C15 H15 120.5 . . ?
N3 Se2 N4 93.3(4) . . ?
C22 N3 Se2 106.4(7) . . ?
C23 N4 Se2 107.9(7) . . ?
N3 C22 C23 116.6(9) . . ?
N3 C22 C27 123.5(10) . . ?
C27 C22 C23 119.9(10) . . ?
N4 C23 C22 115.7(9) . . ?
N4 C23 C24 125.3(10) . . ?
C24 C23 C22 119.0(10) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 C23 118.8(11) . . ?
C25 C24 H24 120.6 . . ?
C24 C25 H25 119.1 . . ?
C24 C25 C26 121.9(11) . . ?
C26 C25 H25 119.1 . . ?
C25 C26 H26 119.0 . . ?
C27 C26 C25 122.1(11) . . ?
C27 C26 H26 119.0 . . ?
C22 C27 H27 120.8 . . ?
C26 C27 C22 118.4(10) . . ?
C26 C27 H27 120.8 . . ?
N5 Se3 N6 93.2(4) . . ?
C17 N5 Se3 106.5(8) . . ?
C16 N6 Se3 105.8(7) . . ?
N6 C16 C17 117.0(10) . . ?
N6 C16 C21 122.8(10) . . ?
C17 C16 C21 120.1(10) . . ?
N5 C17 C16 117.5(10) . . ?
N5 C17 C18 123.4(11) . . ?
C16 C17 C18 119.1(10) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.1(11) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(11) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 118.8 . . ?
C21 C20 C19 122.4(12) . . ?
C21 C20 H20 118.8 . . ?
C16 C21 H21 121.1 . . ?
C20 C21 C16 117.9(12) . . ?
C20 C21 H21 121.1 . . ?
C7 O1 H1 109.5 . . ?
C8 O4 H4 109.5 . . ?
C9 O6 H6 109.5 . . ?
C2 C1 C7 118.4(9) . . ?
C6 C1 C2 118.3(9) . . ?
C6 C1 C7 123.3(9) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(9) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C8 117.7(9) . . ?
C4 C3 C2 119.0(10) . . ?
C4 C3 C8 123.3(10) . . ?
C3 C4 H4A 119.2 . . ?
C3 C4 C5 121.5(10) . . ?
C5 C4 H4A 119.2 . . ?
C4 C5 C6 119.0(9) . . ?
C4 C5 C9 119.6(9) . . ?
C6 C5 C9 121.4(9) . . ?
C1 C6 C5 121.0(9) . . ?
C1 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
O1 C7 C1 113.8(9) . . ?
O2 C7 O1 123.7(10) . . ?
O2 C7 C1 122.5(10) . . ?
O3 C8 O4 123.5(11) . . ?
O3 C8 C3 123.0(10) . . ?
O4 C8 C3 113.5(9) . . ?
O5 C9 O6 124.5(10) . . ?
O5 C9 C5 121.8(10) . . ?
O6 C9 C5 113.7(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N2 0.82 1.99 2.805(11) 176.6 .
O4 H4 N6 0.82 1.97 2.773(11) 166.3 .
O6 H6 N4 0.82 1.94 2.742(11) 165.2 .


_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 1.529
_oxdiff_exptl_absorpt_empirical_full_min 0.566

# start Validation Reply Form
_vrf_PLAT430_miao202014-4        
;
PROBLEM: Short Inter D...A Contact Se2 ..N1 . 2.90 Ang.
RESPONSE: Our crystallographic data are correct. The Checkcif software has a bug and cannot identify the strong chalcogen bond.
;
