N-Heterocyclic Carbene-Catalyzed Oxidative Annulations of α,β-Unsaturated Aldehydes with Hydrazones: Selective Synthesis of Optically Active 4,5-Dihydropyridazin-3-ones and Pyridazin-3-ones.
Mao, Jian-Hui; Wang, Zi-Tian; Wang, Zhan-Yong; Cheng, Ying; The Journal of organic chemistry 80 (2015) 6350–6359; doi:10.1021/acs.joc.5b00784

data_4031074
_publ_section_title
;
 N-Heterocyclic Carbene-Catalyzed Oxidative Annulations of
 \a,\b-Unsaturated Aldehydes with Hydrazones: Selective Synthesis of
 Optically Active 4,5-Dihydropyridazin-3-ones and Pyridazin-3-ones.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6350
_journal_page_last               6359
_journal_paper_doi               10.1021/acs.joc.5b00784
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H17 Br N2 O3'
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_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
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_cell_angle_beta                 110.3164(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3611(12)
_cell_length_b                   6.3270(8)
_cell_length_c                   14.2252(17)
_cell_measurement_reflns_used    3825
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.99
_cell_volume                     874.52(18)
_computing_cell_refinement       'Bruker SAINT'
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_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
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_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
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_diffrn_reflns_limit_l_min       -14
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_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.894
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_diffrn_reflns_theta_max         27.587
_diffrn_reflns_theta_min         2.096
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_exptl_absorpt_correction_T_max  0.75
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_exptl_absorpt_correction_type   multi-scan
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_refine_diff_density_min         -0.338
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_refine_ls_abs_structure_details
; 
 Flack x determined using 1259 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.026(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.855
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3636
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.855
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0233
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0529
_refine_ls_wR_factor_ref         0.0538
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_reflns_Friedel_fraction_full    0.799
_reflns_Friedel_fraction_max     0.770
_reflns_number_gt                3416
_reflns_number_total             3636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00784_si_003.cif
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_cod_depositor_comments          'Adding full bibliography for 4031074.cif.'
_cod_database_code               4031074
_shelx_estimated_absorpt_t_min   0.436
_shelx_estimated_absorpt_t_max   0.567
_shelxl_version_number           2014-3
_shelx_res_checksum              6593
_shelx_hkl_checksum              81919