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_4037641
_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 H29 N3 O4'
_chemical_formula_sum            'C34 H29 N3 O4'
_chemical_formula_weight         543.60
_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
_audit_creation_date             2019-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7086(3)
_cell_length_b                   15.3363(4)
_cell_length_c                   19.0255(5)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      66.724
_cell_measurement_theta_min      4.739
_cell_volume                     3124.56(15)
_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      153.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0327
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32758
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.552
_diffrn_reflns_theta_max         66.552
_diffrn_reflns_theta_min         4.738
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1145 before and 0.0603 after correction. The Ratio of minimum to maximum transmission is 0.9135. 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    1.156
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 2333 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0296
_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^)+(0.0379P)^2^+0.5019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0761
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5396
_reflns_number_total             5483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02684_si_003.cif
_cod_data_source_block           20190429_tchy_chons_0m_a
_cod_database_code               4037641
_shelx_shelxl_version_number     2018/3
_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:
 C3AA(H3AA), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C4AA(H4AA,H4AB), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27),
  C28(H28), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_shelx_res_checksum              77767
_shelx_hkl_checksum              85387
_shelx_fab_checksum              54385
_olex2_submission_special_instructions 'No special instructions were received'