Synthesis of 4-Arylidenepyrazolones by a Gold-Catalyzed Cyclization/Arylidene Group Transfer Cascade of N-Propioloyl Hydrazones.
Ding, Zong-Cang; Tang, Hai-Tao; Li, Ren-Hao; Ju, Lu-Chuan; Zhan, Zhuang-Ping; The Journal of organic chemistry 80 (2015) 9307–9313; doi:10.1021/acs.joc.5b01366

data_4036273
_publ_section_title
;
 Synthesis of 4-Arylidenepyrazolones by a Gold-Catalyzed
 Cyclization/Arylidene Group Transfer Cascade of N-Propioloyl Hydrazones.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9307
_journal_page_last               9313
_journal_paper_doi               10.1021/acs.joc.5b01366
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C22 H15 Br N2 O'
_chemical_formula_sum            'C22 H15 Br N2 O'
_chemical_formula_weight         403.27
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4975)
;
_cell_angle_alpha                73.24(3)
_cell_angle_beta                 86.19(3)
_cell_angle_gamma                71.15(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1795(14)
_cell_length_b                   10.267(2)
_cell_length_c                   13.022(3)
_cell_measurement_temperature    183
_cell_volume                     869.4(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      183
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_av_unetI/netI     0.1268
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7507
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         2.999
_exptl_absorpt_coefficient_mu    2.377
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.0389
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.586
_refine_diff_density_min         -1.893
_refine_diff_density_rms         0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.435
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.435
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0962
_refine_ls_shift/su_max          0.000
_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          0.2231
_refine_ls_wR_factor_ref         0.2897
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2224
_reflns_number_total             3399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01366_si_001.cif
_cod_data_source_block           p
_cod_database_code               4036273
_shelx_estimated_absorpt_t_max   0.648
_shelx_estimated_absorpt_t_min   0.536
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C6(H6), C22(H22), C9(H9), C4(H4), C18(H18), C7(H7),
 C20(H20), C19(H19), C15(H15), C12(H12), C13(H13), C21(H21), C14(H14)
;
_shelx_res_checksum              62155
_shelx_hkl_checksum              90682
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'