Bis(imido)vanadium(V)-Catalyzed [2+2+1] Coupling of Alkynes and Azobenzenes Giving Multisubstituted Pyrroles.
Kawakita, Kento; Beaumier, Evan P.; Kakiuchi, Yuya; Tsurugi, Hayato; Tonks, Ian A.; Mashima, Kazushi; Journal of the American Chemical Society 141 (2019) 4194–4198; doi:10.1021/jacs.8b13390

data_4127484
_publ_section_title
;
 Bis(imido)vanadium(V)-Catalyzed [2+2+1] Coupling of Alkynes and
 Azobenzenes Giving Multisubstituted Pyrroles.
;
_journal_issue                   10
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4194
_journal_page_last               4198
_journal_paper_doi               10.1021/jacs.8b13390
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C18 H28 Cl N2 P2 V'
_chemical_formula_sum            'C18 H28 Cl N2 P2 V'
_chemical_formula_weight         420.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 131.204(9)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   17.735(10)
_cell_length_b                   12.563(6)
_cell_length_c                   13.175(8)
_cell_measurement_reflns_used    1756
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.10
_cell_volume                     2209(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      113
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25134
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.538
_diffrn_reflns_theta_min         3.053
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880.00
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.25
_refine_ls_abs_structure_details
;
 Flack x determined using 1719 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.027(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     219
_refine_ls_number_reflns         5071
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0181P)^2^+1.1960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0548
_refine_ls_wR_factor_ref         0.0592
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4298
_reflns_number_total             5071
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja8b13390_si_002.cif
_cod_data_source_block           complex7
_cod_database_code               4127484
_shelx_res_checksum              29650
_shelx_hkl_checksum              62287