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_4034051
_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_absolute_configuration ad
_chemical_formula_moiety         'C36 H35 Cl N2 O3'
_chemical_formula_sum            'C36 H35 Cl N2 O3'
_chemical_formula_weight         579.11
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2715(8)
_cell_length_b                   16.4258(14)
_cell_length_c                   18.109(2)
_cell_measurement_reflns_used    1723
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.6180
_cell_measurement_theta_min      3.9640
_cell_volume                     3055.3(5)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
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)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -94.00  -55.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000  120.0000 39

  2 omega  -35.00   85.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  -60.0000 120
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0163813000
_diffrn_orient_matrix_UB_12      -0.0101322000
_diffrn_orient_matrix_UB_13      0.0369394000
_diffrn_orient_matrix_UB_21      -0.0355524000
_diffrn_orient_matrix_UB_22      -0.0341947000
_diffrn_orient_matrix_UB_23      -0.0128150000
_diffrn_orient_matrix_UB_31      0.0568890000
_diffrn_orient_matrix_UB_32      -0.0243062000
_diffrn_orient_matrix_UB_33      0.0026422000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8143
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.89
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91179
_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.
;
_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    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1126
_reflns_number_gt                4018
_reflns_number_total             5502
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b01454_si_003.cif
_cod_data_source_block           zhanghx_0910
_cod_database_code               4034051
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C22(H22), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_olex2_date_sample_data_collection 2018-09-10
_olex2_submission_special_instructions 'No special instructions were received'