Gold(I)-Catalyzed Highly Enantioselective [4 + 2]-Annulations of Cyclopentadienes with Nitrosoarenes via Nitroso-Povarov versus Oxidative Nitroso-Povarov Reactions
Jadhav, Prakash D.; Chen, Jia-Xuan; Liu, Rai-Shung; ACS Catalysis  (2020) 5840–; doi:10.1021/acscatal.0c01293

data_4517641
_publ_section_title
;
 Gold(I)-Catalyzed Highly Enantioselective [4 + 2]-Annulations of
 Cyclopentadienes with Nitrosoarenes via Nitroso-Povarov versus Oxidative
 Nitroso-Povarov Reactions
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              5840
_journal_paper_doi               10.1021/acscatal.0c01293
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_sum            'C19 H16 Br N O2'
_chemical_formula_weight         370.24
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 99.293(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4745(5)
_cell_length_b                   6.9054(5)
_cell_length_c                   18.0777(14)
_cell_measurement_reflns_used    5348
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3616
_cell_measurement_theta_min      3.1633
_cell_volume                     797.63(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_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  0.0265
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6224
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_min         1.141
_exptl_absorpt_coefficient_mu    2.586
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1107 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2961
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0217
_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^)+0.3212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0518
_refine_ls_wR_factor_ref         0.0661
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.821
_reflns_Friedel_fraction_max     0.794
_reflns_number_gt                2849
_reflns_number_total             2961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c01293_si_003.cif
_cod_data_source_block           191224LT_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4517641
_shelxl_version_number           2014/6
_shelx_res_checksum              87726
_shelx_hkl_checksum              97882