Stereoselective synthesis of spirocyclohexadiene-pyrazolones via organic base and/or hydrogen bonding assisted [3 + 3] annulation reactions
Sun, Bing-Bing; Zhang, Jun-Qi; Chen, Jun-Bo; Fan, Wei-Tai; Yu, Jie-Qiang; Hu, Jia-Ming; Wang, Xing-Wang; Organic Chemistry Frontiers 6 (2019) 1842–; doi:10.1039/C8QO01391H

data_1554581
_publ_section_title
;
 Stereoselective synthesis of spirocyclohexadiene-pyrazolones via organic
 base and/or hydrogen bonding assisted [3 + 3] annulation reactions
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1842
_journal_paper_doi               10.1039/C8QO01391H
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C33 H23 Cl N4 O'
_chemical_formula_weight         527
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-01-31 deposited with the CCDC.	2019-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                87.2370(10)
_cell_angle_beta                 78.6140(10)
_cell_angle_gamma                85.6810(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3289(4)
_cell_length_b                   10.9229(5)
_cell_length_c                   12.8668(6)
_cell_measurement_reflns_used    9468
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.23
_cell_volume                     1280.91(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            42789
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         1.615
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0629P)^2^+0.5001P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1242
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5029
_reflns_number_total             5906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01391h2.cif
_cod_data_source_block           1204-2
_cod_database_code               1554581
_shelxl_version_number           2013-2
_shelx_res_checksum              31133
_shelx_hkl_checksum              97698