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_7126006
_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         'C9 H9 N3 O5'
_chemical_formula_sum            'C9 H9 N3 O5'
_chemical_formula_weight         239.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.49110(10)
_cell_length_b                   10.5173(2)
_cell_length_c                   18.2619(3)
_cell_measurement_reflns_used    13003
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      51.0780
_cell_measurement_theta_min      3.6980
_cell_volume                     1054.65(3)
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_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    -36.00 -11.00   0.50   10.00    --    0.47 -19.00 -60.00   50
  2  \w      1.00  33.00   0.50   10.00    --    0.47 -99.00-120.00   64
  3  \w     -6.00  36.00   0.50   15.00    --   55.35 -57.00  60.00   84
  4  \w      4.00  30.00   0.50   15.00    --   55.35 -57.00  90.00   52
  5  \w    -17.00  10.00   0.50   15.00    --   55.35 -37.00 150.00   54
  6  \w    101.00 128.00   0.50   15.00    --   55.35  77.00 -30.00   54
  7  \w    -13.00  13.00   0.50   15.00    --  -54.42  57.00 150.00   52
  8  \w    -62.00 -28.00   0.50   15.00    --  -54.42  57.00 150.00   68
  9  \w    -94.00 -36.00   0.50   15.00    --  -54.42 114.00 134.00  116
 10  \w   -121.00 -42.00   0.50   15.00    --  -54.42 -14.00-163.00  158
;
_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      0.0021631000
_diffrn_orient_matrix_UB_12      -0.0025519000
_diffrn_orient_matrix_UB_13      0.0388035000
_diffrn_orient_matrix_UB_21      0.1270549000
_diffrn_orient_matrix_UB_22      0.0120872000
_diffrn_orient_matrix_UB_23      -0.0003821000
_diffrn_orient_matrix_UB_31      -0.0231269000
_diffrn_orient_matrix_UB_32      0.0663137000
_diffrn_orient_matrix_UB_33      0.0015620000
_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  0.0224
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            24292
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         51.205
_diffrn_reflns_theta_min         2.954
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (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    1.506
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.383
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 3240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(19)
_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     156
_refine_ls_number_reflns         10696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0581P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.837
_reflns_number_gt                9009
_reflns_number_total             10696
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09896h2.cif
_cod_data_source_block           cmpd3
_cod_depositor_comments
'Adding full bibliography for 7126005--7126007.cif.'
_cod_database_code               7126006
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     49.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C3(H3)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              2020
_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 1.318
_oxdiff_exptl_absorpt_empirical_full_min 0.692