Access to Substituted Cyclobutenes by Tandem [3,3]-Sigmatropic Rearrangement/[2+2] Cycloaddition of Dipropargylphosphonates under Ag/Co Relay Catalysis
Ni, Qijian; Song, Xiaoxiao; Png, Chin Wen; Zhang, Yongliang; Zhao, Yu; Chemical Science  (2020) –; doi:10.1039/D0SC02972F

data_1559370
_publ_section_title
;
 Access to Substituted Cyclobutenes by Tandem [3,3]-Sigmatropic
 Rearrangement/[2+2] Cycloaddition of Dipropargylphosphonates under Ag/Co
 Relay Catalysis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02972F
_journal_year                    2020
_chemical_formula_moiety         'C24 H21 O3 P'
_chemical_formula_sum            'C24 H21 O3 P'
_chemical_formula_weight         388.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-05-26 deposited with the CCDC.	2020-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.178(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2565(10)
_cell_length_b                   9.4325(10)
_cell_length_c                   16.395(2)
_cell_measurement_reflns_used    2050
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.587
_cell_measurement_theta_min      2.495
_cell_volume                     961.9(2)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2016.5.0'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2016.5.0'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33800
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.587
_diffrn_reflns_theta_min         2.495
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044
_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   -0.013(12)
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5781
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0252
_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^)+(0.0475P)^2^+0.1011P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0685
_reflns_Friedel_coverage         0.957
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                5652
_reflns_number_total             5781
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02972f2.cif
_cod_data_source_block           g807
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               1559370
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_checksum              89485