On the inverse correlation between the hydrogen bond strength and chalcogen bond strength in the cyclic supramolecular heterosynthon [–Se–N]⋯[HOOC–]
Lan, Honghong; Miao, Shaobin; Zhang, Yu; Wang, Weizhou; CrystEngComm 25 (2023) 2159–2164; doi:10.1039/D3CE00100H

data_7246448
_publ_section_title
;
 On the inverse correlation between the hydrogen bond strength and
 chalcogen bond strength in the cyclic supramolecular heterosynthon
 [--Se--N&#xE001;]&#x22EF;[HOOC--]
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              2159
_journal_page_last               2164
_journal_paper_doi               10.1039/D3CE00100H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         '3(C6 H4 N2 Se), C9 H6 O6'
_chemical_formula_sum            'C27 H18 N6 O6 Se3'
_chemical_formula_weight         759.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-02-01 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.977(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.9284(2)
_cell_length_b                   26.3154(12)
_cell_length_c                   13.1324(6)
_cell_measurement_reflns_used    7305
_cell_measurement_temperature    291
_cell_measurement_theta_max      22.5580
_cell_measurement_theta_min      3.8580
_cell_volume                     1356.79(11)
_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)'
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -20.00  25.00   1.00   16.80    --  -13.49 -99.00  30.00   45
  2  \w    -86.00 -35.00   1.00   16.80    --  -13.49-178.00 -30.00   51
  3  \w    -54.00  84.00   1.00   16.80    --   14.89   0.00 150.00  138
  4  \w     -1.00  66.00   1.00   16.80    --   14.89-121.00-112.00   67
  5  \w     -2.00  82.00   1.00   16.80    --   14.89  57.00 -90.00   84
  6  \w     -2.00  82.00   1.00   16.80    --   14.89  57.00   0.00   84
  7  \w     -4.00  84.00   1.00   16.80    --   14.89  38.00-150.00   88
  8  \w     35.00  87.00   1.00   16.80    --   14.89 178.00-120.00   52
  9  \w     -5.00  64.00   1.00   16.80    --   14.89-117.00  34.04   69
 10  \w      1.00  68.00   1.00   16.80    --   14.89-124.00 137.59   67
 11  \w    -86.00 -35.00   1.00   16.80    --  -13.49-178.00 -90.00   51
 12  \w    -20.00  25.00   1.00   16.80    --  -13.49 -99.00-180.00   45
 13  \w    -20.00  25.00   1.00   16.80    --  -13.49 -99.00   0.00   45
 14  \w    -20.00  23.00   1.00   16.80    --   14.89 -99.00-180.00   43
 15  \w    -53.00  42.00   1.00   16.80    --   14.89 -77.00 120.00   95
 16  \w    -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       '\w 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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.859
_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
_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_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_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0660
_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/[\s^2^(Fo^2^)+(0.0265P)^2^+3.3795P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1107
_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_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00100h2.cif
_cod_data_source_block           miao202014-4
_cod_depositor_comments
'Adding full bibliography for 7246446--7246448.cif.'
_cod_database_code               7246448
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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)
;
_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