N-Heterocyclic carbene-catalyzed [3 + 3] cyclocondensation of bromoenals with hydrazones: highly enantioselective synthesis of dihydropyridazones.
Zhang, Chun-Lin; Wang, Dong-Ling; Chen, Kun-Quan; Ye, Song; Organic & biomolecular chemistry 13 (2015) 11255–11262; doi:10.1039/c5ob01748c

data_7154724
_publ_section_title
;
 N-Heterocyclic carbene-catalyzed [3 + 3] cyclocondensation of bromoenals
 with hydrazones: highly enantioselective synthesis of dihydropyridazones.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              11255
_journal_page_last               11262
_journal_paper_doi               10.1039/c5ob01748c
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H19 Cl N2 O4'
_chemical_formula_sum            'C20 H19 Cl N2 O4'
_chemical_formula_weight         386.82
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-08-14 deposited with the CCDC.
2015-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.583(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.708(4)
_cell_length_b                   6.286(3)
_cell_length_c                   17.049(8)
_cell_measurement_reflns_used    3008
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4757
_cell_measurement_theta_min      2.3917
_cell_volume                     932.3(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 14.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 45.0740
              2theta: -19.8628
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 14.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 45.0740
              2theta: -19.8628
scan:
    Number of images: 344
               Slice: -110.0000 - 62.0000
         Image width: 0.5000
            Exp time: 14.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 45.0740
              2theta: -19.8628
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0597
_diffrn_orient_matrix_UB_12      -0.0440
_diffrn_orient_matrix_UB_13      -0.0878
_diffrn_orient_matrix_UB_21      0.0052
_diffrn_orient_matrix_UB_22      0.1435
_diffrn_orient_matrix_UB_23      -0.0684
_diffrn_orient_matrix_UB_31      0.0515
_diffrn_orient_matrix_UB_32      0.0106
_diffrn_orient_matrix_UB_33      0.0262
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10792
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.677
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.84498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       rod
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1417 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4151
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0452
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                3887
_reflns_number_total             4151
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01748c2.cif
_cod_data_source_block           sa4165
_cod_depositor_comments          'Adding full bibliography for 7154724.cif.'
_cod_database_code               7154724
_diffrn_number_total             2326
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C15(H15), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              96416
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'