Palladium-catalyzed diastereo- and enantioselective formal [3 + 2] cycloaddition of vinyl cyclopropanes with cyclic 1-azadienes
Zhou, Qing; Chen, Bo; Huang, Xiao-Bing; Zeng, Ya-Li; Chu, Wen-Dao; He, Long; Liu, Quan-Zhong; Organic Chemistry Frontiers 6 (2019) 1891–; doi:10.1039/C9QO00325H

data_1554865
_publ_section_title
;
 Palladium-catalyzed diastereo- and enantioselective formal [3 + 2]
 cycloaddition of vinyl cyclopropanes with cyclic 1-azadienes
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1891
_journal_paper_doi               10.1039/C9QO00325H
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration S,R,S
_chemical_formula_moiety         'C24 H22 N2 O9 S'
_chemical_formula_sum            'C24 H22 N2 O9 S'
_chemical_formula_weight         514.49
_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             2018-10-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-13 deposited with the CCDC.	2019-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2161(5)
_cell_length_b                   12.5468(5)
_cell_length_c                   16.7879(7)
_cell_measurement_reflns_used    7678
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      59.799
_cell_measurement_theta_min      4.399
_cell_volume                     2573.13(18)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      273.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1518
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17634
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        61.306
_diffrn_reflns_theta_max         61.306
_diffrn_reflns_theta_min         4.399
_exptl_absorpt_coefficient_mu    1.589
_exptl_absorpt_correction_T_max  0.7520
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1193 before and 0.0675 after correction. The Ratio of minimum to maximum transmission is 0.8499. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1184 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.0065(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3955
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+0.3943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1531
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3282
_reflns_number_total             3955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00325h2.cif
_cod_data_source_block           cu_20180628_0m
_cod_database_code               1554865
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.925
_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 C(H,H,H) groups
2. Rigid bond restraints
 C13, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 S1, O2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C12(H12)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C20(H20), C22(H22), C23(H23),
 C24(H24)
4.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
4.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              15128
_shelx_hkl_checksum              12386
_shelx_fab_checksum              92966
_olex2_submission_special_instructions 'No special instructions were received'