Organocatalytic asymmetric formal [3 + 2] cycloaddition reaction of isocyanoacetates with saccharin-derived 1-azadienes.
Chang, Li; Zhu, Guang-Yu; Yang, Ting; Zhao, Xiao-Li; Shi, Min; Zhao, Mei-Xin; Organic & biomolecular chemistry 19 (2021) 3687–3697; doi:10.1039/d1ob00115a

data_7157989
_publ_section_title
;
 Organocatalytic asymmetric formal [3 + 2] cycloaddition reaction of
 isocyanoacetates with saccharin-derived 1-azadienes.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3687
_journal_page_last               3697
_journal_paper_doi               10.1039/d1ob00115a
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H19 Br N2 O4 S'
_chemical_formula_sum            'C25 H19 Br N2 O4 S'
_chemical_formula_weight         523.39
_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             2018-05-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2020-06-18 deposited with the CCDC.	2021-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.73540(10)
_cell_length_b                   18.2897(2)
_cell_length_c                   19.0257(2)
_cell_measurement_reflns_used    15522
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.0150
_cell_measurement_theta_min      4.6420
_cell_volume                     2343.75(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -88.00 -58.00   1.00    1.00    --    0.00 -38.00  90.00   30
  2  \w    -15.00  29.00   1.00    1.00    --    0.00  38.00  60.00   44
  3  \w    -55.00  18.00   1.00    1.00    --    0.00 -38.00  90.00   73
  4  \w     64.00  89.00   1.00    1.00    --    0.00  77.00-150.00   25
  5  \w    -57.00  19.00   1.00    1.00    --    0.00 -38.00   0.00   76
  6  \w    -80.00  18.00   1.00    1.00    --    0.00 -38.00-120.00   98
  7  \w      6.00  52.00   1.00    2.00    --   95.80 -45.00-120.00   46
  8  \w     78.00 185.00   1.00    2.00    --   95.80  30.00  60.00  107
  9  \w      7.00  33.00   1.00    2.00    --   95.80 -45.00  90.00   26
 10  \w     76.00 102.00   1.00    2.00    --   95.80 -82.00-150.00   26
 11  \w     96.00 124.00   1.00    2.00    --   95.80 -82.00 150.00   28
 12  \w      7.00 120.00   1.00    2.00    --   95.80 -61.00  60.00  113
 13  \w     77.00 173.00   1.00    2.00    --   95.80  15.00  30.00   96
 14  \w     18.00 128.00   1.00    2.00    --   95.80 -82.00 -60.00  110
 15  \w      7.00 114.00   1.00    2.00    --   95.80 -61.00 -60.00  107
 16  \w     16.00 119.00   1.00    2.00    --   95.80 -15.00  90.00  103
 17  \w     46.00 105.00   1.00    2.00    --   95.80 -61.00 150.00   59
 18  \w     42.00 128.00   1.00    2.00    --   95.80 -82.00  60.00   86
 19  \w    100.00 128.00   1.00    2.00    --   95.80 -82.00  90.00   28
 20  \w     61.00  86.00   1.00    2.00    --   95.80 -45.00  90.00   25
 21  \w     73.00  98.00   1.00    2.00    --   95.80 -82.00  30.00   25
 22  \w     96.00 122.00   1.00    2.00    --   95.80 -82.00 120.00   26
 23  \w     77.00 102.00   1.00    2.00    --   95.80 -82.00 133.99   25
 24  \w     15.00  41.00   1.00    2.00    --   95.80 -82.00 133.99   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0663078000
_diffrn_orient_matrix_UB_12      -0.0799646000
_diffrn_orient_matrix_UB_13      -0.0095926000
_diffrn_orient_matrix_UB_21      0.0023208000
_diffrn_orient_matrix_UB_22      0.0106646000
_diffrn_orient_matrix_UB_23      -0.0803072000
_diffrn_orient_matrix_UB_31      0.2189920000
_diffrn_orient_matrix_UB_32      0.0241309000
_diffrn_orient_matrix_UB_33      0.0037330000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23450
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.648
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.514
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.35
_refine_diff_density_max         1.077
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1632 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(8)
_refine_ls_extinction_coef       0.0026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0640P)^2^+2.4123P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1286
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4040
_reflns_number_total             4171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00115a2.cif
_cod_data_source_block           exp_334
_cod_depositor_comments          'Adding full bibliography for 7157989.cif.'
_cod_database_code               7157989
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.373
_shelx_estimated_absorpt_t_min   0.313
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              238
_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 2.305
_oxdiff_exptl_absorpt_empirical_full_min 0.538