Asymmetric inverse-electron-demand 1,3-dipolar cycloadditions of cyclopentadienones and thiophene-1,1-dioxide with C,N-cyclic azomethine imines
Chen, Chen; Yang, Xing-Xing; Zhao, Zhi; Han, Bo; Du, Wei; Chen, Ying-Chun; Chemical Communications  (2022) –; doi:10.1039/D2CC01103D

data_7129934
_publ_section_title
;
 Asymmetric inverse-electron-demand 1,3-dipolar cycloadditions of
 cyclopentadienones and thiophene-1,1-dioxide with C,N-cyclic azomethine
 imines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01103D
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H18 N2 O2'
_chemical_formula_sum            'C21 H18 N2 O2'
_chemical_formula_weight         330.37
_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     direct
_audit_creation_date             2020-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2022-02-23 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.21864(13)
_cell_length_b                   10.5120(2)
_cell_length_c                   22.0152(4)
_cell_measurement_reflns_used    3740
_cell_measurement_temperature    293.2(3)
_cell_measurement_theta_max      71.1350
_cell_measurement_theta_min      5.7980
_cell_volume                     1670.56(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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_environment      air
_diffrn_ambient_temperature      293.2(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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    -73.00  37.00   1.00    1.00    --  -34.98  19.00-180.00  110
  2  \w      6.00 104.00   1.00    1.00    --   34.98  77.00-150.00   98
  3  \w      6.00 104.00   1.00    1.00    --   34.98  77.00   0.00   98
  4  \w     23.00  90.00   1.00    1.00    --   34.98-125.00 -60.00   67
  5  \w     23.00  90.00   1.00    1.00    --   34.98-125.00-180.00   67
  6  \w     78.00 176.00   1.00    3.01    --  106.90  77.00 -30.00   98
  7  \w     81.00 178.00   1.00    3.01    --  106.90  30.00  30.00   97
  8  \w     87.00 175.00   1.00    3.01    --  106.90  61.00  60.00   88
  9  \w     38.00 126.00   1.00    3.01    --  106.90 -54.00 -92.00   88
 10  \w     39.00 127.00   1.00    3.01    --  106.90 -61.00 120.00   88
 11  \w     37.00 110.00   1.00    3.01    --  106.90 -94.00  90.00   73
 12  \w     37.00 110.00   1.00    3.01    --  106.90 -94.00 120.00   73
 13  \w     36.00 113.00   1.00    3.01    --  106.90-111.00 -90.00   77
 14  \w    -33.00  20.00   1.00    1.00    --   34.98 -57.00 -30.00   53
 15  \w     16.00 103.00   1.00    1.00    --   34.98  57.00 120.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1300875000
_diffrn_orient_matrix_UB_12      0.0230760000
_diffrn_orient_matrix_UB_13      0.0543922000
_diffrn_orient_matrix_UB_21      0.0490323000
_diffrn_orient_matrix_UB_22      -0.1323338000
_diffrn_orient_matrix_UB_23      0.0254005000
_diffrn_orient_matrix_UB_31      0.1619579000
_diffrn_orient_matrix_UB_32      0.0585871000
_diffrn_orient_matrix_UB_33      0.0359442000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9144
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.315
_diffrn_reflns_theta_min         4.661
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Flack x determined using 1109 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0654
_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^)+(0.1141P)^2^+0.0447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1634
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                2947
_reflns_number_total             3192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01103d2.cif
_cod_data_source_block           3a
_cod_original_cell_volume        1670.57(6)
_cod_database_code               7129934
_reflns_odcompleteness_completeness 99.89
_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 C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00C(H00C), C00I(H00J)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00B,H00E), C00H(H00H,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00D(H00D), C00F(H00F), C00G(H00G), C00J(H00K),
 C00K(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P)
;
_shelx_res_checksum              62469
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-10-10
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.900
_oxdiff_exptl_absorpt_empirical_full_min 0.696