Catalyst-controlled regioselectivity in phosphine catalysis: synthesis of spirocyclic benzofuranones via regiodivergent [3+2] annulations of aurones and an allenoateαα
Ni, Huanzhen; Yu, Zhaoyuan; Yao, Weijun; Lan, Yu; Ullah, Nisar; Lu, Yixin; Chem. Sci.  (2017) –; doi:10.1039/C7SC02176C

data_1546301
_publ_section_title
;
 Catalyst-controlled regioselectivity in phosphine catalysis: synthesis of
 spirocyclic benzofuranones via regiodivergent [3+2] annulations of
 aurones and an allenoate\a\a
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC02176C
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H21 Cl O4'
_chemical_formula_weight         396.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-11-17 deposited with the CCDC.
2017-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.1914(2)
_cell_length_b                   19.1212(5)
_cell_length_c                   33.9479(10)
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.93
_cell_measurement_theta_min      2.60
_cell_volume                     4019.0(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            31620
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.099
_diffrn_reflns_theta_min         2.603
_exptl_absorpt_coefficient_mu    1.898
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.115
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_refine_diff_density_max         0.235
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Flack x determined using 2671 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.016(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         7571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0262P)^2^+0.8078P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0709
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                6865
_reflns_number_total             7571
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc02176c2.cif
_cod_data_source_block           G495
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1546301
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.489
_shelx_estimated_absorpt_t_max   0.830
_shelx_res_checksum              70563