Adaptive Covalent Networks Enabled by Dual Reactivity: The Evolution of Reversible Covalent Bonds, Their Molecular Assemblies, and Guest Recognition.
Mao, Jialin; Hai, Yu; Ye, Hebo; You, Lei; The Journal of organic chemistry 85 (2020) 5351–5361; doi:10.1021/acs.joc.0c00051

data_4038227
_publ_section_title
;
 Adaptive Covalent Networks Enabled by Dual Reactivity: The Evolution of
 Reversible Covalent Bonds, Their Molecular Assemblies, and Guest
 Recognition.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5351
_journal_page_last               5361
_journal_paper_doi               10.1021/acs.joc.0c00051
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C11 H10 N O3 S'
_chemical_formula_sum            'C11 H10 N O3 S'
_chemical_formula_weight         236.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.982(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7122(3)
_cell_length_b                   6.9375(2)
_cell_length_c                   20.1264(8)
_cell_measurement_reflns_used    4264
_cell_measurement_temperature    190(4)
_cell_measurement_theta_max      59.6970
_cell_measurement_theta_min      3.8160
_cell_volume                     1072.76(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      190(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_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     15.00  66.00   0.50    0.05    --   -1.41  38.00  60.00  102
  2  \w     27.00  64.00   0.50    0.05    --   -1.41  19.00 -30.00   74
  3  \w    120.00 145.00   0.50    0.07    --   72.34 106.00  97.00   50
  4  \w     17.00  42.00   0.50    0.07    --   72.34 -38.00   0.00   50
  5  \w      6.00  66.00   0.50    0.07    --   72.34 -57.00 -60.00  120
  6  \w     59.00  90.00   0.50    0.07    --   72.34-106.00  -0.00   62
  7  \w      0.00  25.00   0.50    0.07    --   72.34 -38.00 -90.00   50
  8  \w     -3.00  26.00   0.50    0.07    --   72.34 -19.00 -30.00   58
  9  \w     -3.00  23.00   0.50    0.07    --   72.34 -19.00   0.00   52
 10  \w     -3.00  22.00   0.50    0.07    --   72.34 -19.00  60.00   50
 11  \w     -3.00  25.00   0.50    0.07    --   72.34 -19.00  30.00   56
 12  \w   -106.00 -38.00   0.50    0.07    --  -75.15 106.00  97.00  136
 13  \w    -66.00 -33.00   0.50    0.07    --  -75.15  57.00  60.00   66
 14  \w    -37.00  -6.00   0.50    0.07    --  -75.15  38.00  90.00   62
 15  \w    -85.00 -59.00   0.50    0.07    --  -75.15 -57.00  60.00   52
 16  \w    -26.00  -1.00   0.50    0.07    --  -75.15  19.00 -60.00   50
 17  \w    -40.00 -14.00   0.50    0.07    --  -75.15  38.00-180.00   52
 18  \w   -136.00 -95.00   0.50    0.07    --  -75.15-106.00  -0.00   82
 19  \w   -147.00-118.00   0.50    0.07    --  -75.15 -57.00  60.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0091215000
_diffrn_orient_matrix_UB_12      0.1245157000
_diffrn_orient_matrix_UB_13      -0.0504556000
_diffrn_orient_matrix_UB_21      0.0489700000
_diffrn_orient_matrix_UB_22      0.1396281000
_diffrn_orient_matrix_UB_23      0.0435964000
_diffrn_orient_matrix_UB_31      0.1669706000
_diffrn_orient_matrix_UB_32      -0.0477696000
_diffrn_orient_matrix_UB_33      -0.0039721000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34050
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7084
_diffrn_reflns_theta_full        60.63
_diffrn_reflns_theta_max         60.63
_diffrn_reflns_theta_min         3.83
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    1.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             492
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.4780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                1990
_reflns_number_total             2378
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00051_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4038227--4038237.cif.'
_cod_database_code               4038227
_chemical_oxdiff_formula         CHONS
_diffrn_oxdiff_digest_frames
;
017cfcf4d12ea8d88a840d43ab5913f2ee01282f83e
;
_diffrn_oxdiff_digest_hkl
;
0172c70df244a0a1d938339b4abfdb3ecf8dbe
;
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C4(H4), C7(H7), C5(H5), C6(H6)
2.d Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_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 3.214
_oxdiff_exptl_absorpt_empirical_full_min 0.437