Lewis-Base-Catalyzed [1 + 2 + 2] Annulation Reaction of Morita-Baylis-Hillman Carbonates with Unsaturated Pyrazolones: Construction of All-Stereogenic Carbon Cyclopentane-Fused Dispiropyrazolones.
Liang, Jin-Yan; Shen, Shou-Jie; Chai, Xiao-Qian; Lv, Ting; The Journal of organic chemistry 83 (2018) 12744–12752; doi:10.1021/acs.joc.8b02188

data_4035427
_publ_section_title
;
 Lewis-Base-Catalyzed [1 + 2 + 2] Annulation Reaction of
 Morita-Baylis-Hillman Carbonates with Unsaturated Pyrazolones:
 Construction of All-Stereogenic Carbon Cyclopentane-Fused
 Dispiropyrazolones.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12744
_journal_page_last               12752
_journal_paper_doi               10.1021/acs.joc.8b02188
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C39 H30 Cl2 N4 O4'
_chemical_formula_sum            'C39 H30 Cl2 N4 O4'
_chemical_formula_weight         689.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-07-19
_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            8
_cell_length_a                   17.2491(10)
_cell_length_b                   20.1577(12)
_cell_length_c                   21.1430(11)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.148
_cell_measurement_theta_min      2.260
_cell_volume                     7351.5(7)
_computing_cell_refinement       '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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            105458
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.36
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2864
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.013
_refine_diff_density_max         1.215
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         9195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.1558
_refine_ls_R_factor_gt           0.0990
_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^)+(0.1823P)^2^+2.7956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2808
_refine_ls_wR_factor_ref         0.3263
_reflns_number_gt                5535
_reflns_number_total             9195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02188_si_002.cif
_cod_data_source_block           aa
_cod_database_code               4035427
_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:
 C1(H1), C2(H2), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C17(H17), C18(H18), C19(H19), C22(H22), C24(H24), C26(H26),
 C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36),
  C38(H38), C39(H39)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C20(H20A,H20B,H20C), C37(H37A,H37B,H37C)
;
_olex2_submission_special_instructions 'No special instructions were received'