Asymmetric Organocatalytic [4 + 1] Annulations Involving Polarity Reversal Process: A Tandem Catalytic Approach to Highly Functionalized Spiropyrazolone Derivatives.
Tan, Chang-Yin; Lu, Hong; Zhang, Jia-Lu; Liu, Jin-Yu; Xu, Peng-Fei; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02684

data_4037642
_publ_section_title
;
 Asymmetric Organocatalytic [4 + 1] Annulations Involving Polarity
 Reversal Process: A Tandem Catalytic Approach to Highly Functionalized
 Spiropyrazolone Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02684
_journal_year                    2019
_chemical_formula_moiety         'C34 H27 Cl N3 O4'
_chemical_formula_sum            'C34 H27 Cl N3 O4'
_chemical_formula_weight         577.03
_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     direct
_audit_creation_date             2019-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.655(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6986(6)
_cell_length_b                   19.3964(11)
_cell_length_c                   15.0120(8)
_cell_measurement_reflns_used    9102
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.711
_cell_measurement_theta_min      3.869
_cell_volume                     2933.7(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      149.99
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0419
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37020
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         3.126
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.507
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0889 before and 0.0687 after correction. The Ratio of minimum to maximum transmission is 0.8872. 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    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             1204
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 4659 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     759
_refine_ls_number_reflns         10324
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0296
_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^)+(0.0358P)^2^+0.3683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0740
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                10042
_reflns_number_total             10324
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02684_si_002.cif
_cod_data_source_block           20181221_tanchy_choncl_0m_a
_cod_depositor_comments
;

2020-07-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C68 H54 Cl2 N6 O8'
_cod_original_formula_weight         1154.07
_cod_original_formula_moiety         '2(C34 H27 Cl N3 O4)'
_cod_original_formula_units_Z            2
_cod_database_code               4037642
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.840
_shelx_estimated_absorpt_t_min   0.773
_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.a Ternary CH refined with riding coordinates:
 C22(H22), C2'(H2')
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C23'(H23C,H23D), C26'(H26A,H26B), C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C9'(H9'), C8(H8), C8'(H8'), C7(H7), C7'(H7'), C6(H6), C6'(H6'),
 C5(H5), C5'(H5'), C12(H12), C12'(H12'), C11(H11), C11'(H11'), C13'(H13'),
 C13(H13), C14'(H14'), C14(H14), C15(H15), C15'(H15'), C18(H18), C18'(H18'),
 C17(H17), C17'(H17'), C20(H20), C20'(H20'), C21(H21), C21'(H21'), C27(H27),
 C28(H28), C29(H29), C30(H30), C30'(H30'), C31(H31), C31'(H31'), C32'(H32'),
 C33'(H33'), C34'(H34')
2.d Idealised Me refined as rotating group:
 C27'(H27A,H27B,H27C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              39553
_shelx_hkl_checksum              59049
_olex2_submission_special_instructions 'No special instructions were received'