Synergistic formal ring contraction for the enantioselective synthesis of spiropyrazolones.
Meazza, Marta; Kamlar, Martin; Jašíková, Lucie; Formánek, Bedřich; Mazzanti, Andrea; Roithová, Jana; Veselý, Jan; Rios, Ramon; Chemical science 9 (2018) 6368–6373; doi:10.1039/c8sc00913a

data_1549619
_publ_section_title
;
 Synergistic formal ring contraction for the enantioselective synthesis of
 spiropyrazolones.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              6368
_journal_page_last               6373
_journal_paper_doi               10.1039/c8sc00913a
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C24 H23 I N2 O3'
_chemical_formula_sum            'C24 H23 I N2 O3'
_chemical_formula_weight         514.34
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2017-09-20 deposited with the CCDC.
2018-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8489(2)
_cell_length_b                   15.7645(5)
_cell_length_c                   19.4642(5)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4528
_cell_measurement_theta_min      2.4595
_cell_volume                     2101.54(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26683
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         2.459
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.553
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_description       bar
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.099
_refine_diff_density_max         1.128
_refine_diff_density_min         -0.824
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 1827 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0308P)^2^+1.3209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0617
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4508
_reflns_number_total             4816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc00913a2.cif
_cod_data_source_block           mo_mk_1667_1_vesely
_cod_depositor_comments          'Adding full bibliography for 1549619.cif.'
_cod_database_code               1549619
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.623
_shelx_estimated_absorpt_t_max   0.861
_shelx_res_checksum              24563