One-Pot Asymmetric Synthesis of Spiropyrazolone-Linked Cyclopropanes and Benzofurans through a General Michael Addition/Chlorination/Nucleophilic Substitution Sequence.
Lu, Hong; Zhang, Huan-Xin; Tan, Chang-Yin; Liu, Jin-Yu; Wei, Hao; Xu, Peng-Fei; The Journal of organic chemistry 84 (2019) 10292–10305; doi:10.1021/acs.joc.9b01454

data_4034052
_publ_section_title
;
 One-Pot Asymmetric Synthesis of Spiropyrazolone-Linked Cyclopropanes and
 Benzofurans through a General Michael Addition/Chlorination/Nucleophilic
 Substitution Sequence.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10292
_journal_page_last               10305
_journal_paper_doi               10.1021/acs.joc.9b01454
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C27 H26 N3 O4 S'
_chemical_formula_sum            'C27 H26 N3 O4 S'
_chemical_formula_weight         488.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_cell_length_c                   8.5149(4)
_cell_measurement_reflns_used    3261
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.6130
_cell_measurement_theta_min      4.5340
_cell_volume                     2436.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
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;
  1 omega  -57.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  -30.0000 55

  2 omega  -74.00  -42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   90.0000 32

  3 omega   36.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -150.0000 58

  4 omega   22.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000    8.4586 25

  5 omega   32.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 84

  6 omega   55.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -60.0000 48

  7 omega   63.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 26

  8 omega   34.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 48

  9 omega   85.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -90.0000 93

 10 omega   71.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -120.0000 26

 11 omega   59.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 34

 12 omega   43.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 64

 13 omega  116.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 60

 14 omega   41.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 37

 15 omega   37.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 66

 16 omega   44.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 25

 17 omega  111.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

 18 omega  152.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 25

 19 omega   44.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  150.0000 25

 20 omega   52.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 46
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0436555000
_diffrn_orient_matrix_UB_12      0.0164137000
_diffrn_orient_matrix_UB_13      0.1841530000
_diffrn_orient_matrix_UB_21      -0.0481942000
_diffrn_orient_matrix_UB_22      -0.0458455000
_diffrn_orient_matrix_UB_23      0.0488012000
_diffrn_orient_matrix_UB_31      0.1426304000
_diffrn_orient_matrix_UB_32      -0.0206410000
_diffrn_orient_matrix_UB_33      0.0369983000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9076
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        66.574
_diffrn_reflns_theta_max         66.574
_diffrn_reflns_theta_min         4.750
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.502
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
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_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.180
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_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0672P)^2^+0.8092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1486
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3549
_reflns_number_total             4137
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01454_si_002.cif
_cod_data_source_block           zhanghx_0301
_cod_database_code               4034052
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 96.08
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              97281
_shelx_hkl_checksum              32177
_olex2_date_sample_data_collection 2019-03-01
_olex2_submission_special_instructions 'No special instructions were received'