Carbene-Catalyzed Enantioselective Annulation of Dinucleophilic Hydrazones and Bromoenals for Access to Aryl-Dihydropyridazinones and Related Drugs
Mondal, Bivas; Maiti, Rakesh; Yang, Xing; Xu, Jun; Tian, Weiyi; Yan, Jialei; Li, Xiangyang; Chi, Yonggui Robin; Chemical Science  (2021) –; doi:10.1039/D1SC01891D

data_1562619
_publ_section_title
;
 Carbene-Catalyzed Enantioselective Annulation of Dinucleophilic
 Hydrazones and Bromoenals for Access to Aryl-Dihydropyridazinones and
 Related Drugs
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01891D
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H16 N4 O5 S'
_chemical_formula_weight         436.44
_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
_audit_update_record
;
2021-02-12 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3450(4)
_cell_length_b                   11.5313(8)
_cell_length_c                   23.7692(18)
_cell_measurement_reflns_used    2994
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      27.0221
_cell_measurement_theta_min      2.4610
_cell_volume                     2013.2(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'APEX3 (Ver 2019.11, Bruker AXS Inc., 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_publication_material  'APEX3 (Ver 2019.11,Bruker AXS Inc., 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      200.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'APEX II CCD'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12314
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.71
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.50
_diffrn_source_type              'Bruker X8APEX'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.302
_refine_ls_abs_structure_details
;

Flack x determined using 1080 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(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     329
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     371
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0325P)^2^+0.2860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3167
_reflns_number_total             3942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01891d2.cif
_cod_data_source_block           cyg380
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1562619
_shelx_res_checksum              9521
_shelx_hkl_checksum              55721