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_7129937
_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      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             2021-03-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-02-23 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 88.206(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2297(3)
_cell_length_b                   9.0042(3)
_cell_length_c                   22.3918(8)
_cell_measurement_reflns_used    9766
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.185
_cell_measurement_theta_min      3.95
_cell_volume                     1658.46(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            43786
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.397
_diffrn_reflns_theta_min         1.974
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1480 before and 0.0857 after correction.
The Ratio of minimum to maximum transmission is 0.5475.
The \l/2 correction factor is Not present.
;
_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    1.323
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 2560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6055
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0342P)^2^+0.3828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5758
_reflns_number_total             6055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01103d2.cif
_cod_data_source_block           4a
_cod_database_code               7129937
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.729
_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:
 C12(H12), C16(H16), C17(H17), C35(H35), C36(H36), C40(H40)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C28(H28A,H28B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C10(H10), C11(H11), C14(H14), C15(H15), C18(H18),
 C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C31(H31), C32(H32),
  C33(H33), C34(H34), C38(H38), C39(H39), C42(H42), C43(H43)
;
_shelx_res_checksum              38898
_olex2_submission_special_instructions 'No special instructions were received'