Experimental evidence of chalcogen bonding at oxygen.
Fellowes, Thomas; Harris, Benjamin L.; White, Jonathan M.; Chemical communications (Cambridge, England) 56 (2020) 3313–3316; doi:10.1039/c9cc09896h

data_7126007
_publ_section_title
;
 Experimental evidence of chalcogen bonding at oxygen.
;
_journal_issue                   22
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3313
_journal_page_last               3316
_journal_paper_doi               10.1039/c9cc09896h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C12 H13 N3 O5'
_chemical_formula_sum            'C12 H13 N3 O5'
_chemical_formula_weight         279.25
_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             2020-01-24
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-01-30 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.0310(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.66740(10)
_cell_length_b                   16.3925(3)
_cell_length_c                   11.6108(2)
_cell_measurement_reflns_used    25403
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      51.0610
_cell_measurement_theta_min      3.5020
_cell_volume                     1245.56(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_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    -16.00  19.00   0.50   45.00    --   55.36 -57.00  30.00   70
  2  \w     47.00  73.00   0.50   45.00    --   55.36-110.00 -35.00   52
  3  \w    -14.00  12.00   0.50   45.00    --   55.36 -37.00 -30.00   52
  4  \w    -15.00  12.00   0.50   45.00    --   55.36 -37.00  30.00   54
  5  \w    -18.00   7.00   0.50   45.00    --   55.36 -37.00   0.00   50
  6  \w    -13.00  20.00   0.50   45.00    --   55.36 -57.00  60.00   66
  7  \w    -16.00  39.00   0.50   45.00    --   55.36 -57.00 -90.00  110
  8  \w     -3.00  23.00   0.50   15.00    --    0.47  77.00-150.00   52
  9  \w    101.00 126.00   0.50   45.00    --   55.36  77.00   0.00   50
 10  \w    101.00 126.00   0.50   45.00    --   55.36  77.00  90.00   50
 11  \w    101.00 126.00   0.50   45.00    --   55.36  77.00-180.00   50
 12  \w    -93.00 -24.00   0.50   45.00    --  -54.43 110.00  59.00  138
 13  \w   -114.00 -89.00   0.50   45.00    --  -54.43 -57.00 -60.00   50
 14  \w   -115.00 -88.00   0.50   45.00    --  -54.43 -57.00   0.00   54
 15  \w   -126.00 -82.00   0.50   45.00    --  -54.43 -57.00  60.00   88
 16  \w   -118.00 -82.00   0.50   45.00    --  -54.43 -57.00 120.00   72
 17  \w    -89.00 -43.00   0.50   45.00    --  -54.43 125.00 -30.00   92
 18  \w   -102.00 -34.00   0.50   45.00    --  -54.43 125.00-150.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0027403000
_diffrn_orient_matrix_UB_12      -0.0413163000
_diffrn_orient_matrix_UB_13      -0.0183991000
_diffrn_orient_matrix_UB_21      -0.0694297000
_diffrn_orient_matrix_UB_22      -0.0091768000
_diffrn_orient_matrix_UB_23      0.0374652000
_diffrn_orient_matrix_UB_31      -0.0831661000
_diffrn_orient_matrix_UB_32      0.0090485000
_diffrn_orient_matrix_UB_33      -0.0461535000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            51580
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         51.319
_diffrn_reflns_theta_min         3.508
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.504
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.489
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.445
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 8110 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.32(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         25111
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0409
_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/[\s^2^(Fo^2^)+(0.0732P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1153
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.828
_reflns_number_gt                20837
_reflns_number_total             25111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09896h2.cif
_cod_data_source_block           cmpd2
_cod_depositor_comments
'Adding full bibliography for 7126005--7126007.cif.'
_cod_database_code               7126007
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H13 N3 O5 '
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     47.63
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C12A(H12A,H12B), C11A(H11A,H11B), C8(H8A,H8B), C8A(H8AA,H8AB),
  C12(H12C,H12D), C10A(H10A,H10B), C9(H9A,H9B), C10(H10C,H10D), C11(H11C,H11D)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C5A(H5A), C3A(H3A), C5(H5), C6A(H6A)
;
_shelx_res_checksum              91830
_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 1.369
_oxdiff_exptl_absorpt_empirical_full_min 0.759