Tandem dihetero-Diels–Alder and Huisgen cycloaddition reactions. Synthesis, crystal structure and hydrolysis of the novel cage phosphoranes
Khasiyatullina, Nadezhda R.; Baronova, Tamara A.; Mironova, Ekaterina V.; Fayzullin, Robert R.; Litvinov, Igor A.; Efimov, Sergey V.; Musin, Rashid Z.; Klochkov, Vladimir V.; Mironov, Vladimir F.; Organic Chemistry Frontiers 5 (2018) 3113–; doi:10.1039/C8QO00915E

data_1554455
_publ_section_title
;
 Tandem dihetero-Diels--Alder and Huisgen cycloaddition reactions.
 Synthesis, crystal structure and hydrolysis of the novel cage
 phosphoranes
;
_journal_issue                   21
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3113
_journal_paper_doi               10.1039/C8QO00915E
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C6 H16 N 1+, C6 H4 O4 P 1-'
_chemical_formula_sum            'C12 H20 N O4 P'
_chemical_formula_weight         273.26
_chemical_melting_point          402
_chemical_name_systematic
'triethylammonium oxabenzo-1,3,2-dioxaphosphol-2-oate'
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-06-27 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.695(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.266(3)
_cell_length_b                   11.409(5)
_cell_length_c                   8.573(4)
_cell_measurement_reflns_used    1105
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.07
_cell_measurement_theta_min      2.39
_cell_volume                     705.8(5)
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'APEX2 v2014.11-0 (Bruker AXS)'
_computing_molecular_graphics
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_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       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5170
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.282
_diffrn_reflns_theta_min         2.392
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9182
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_recrystallization_method
'crystallized from diethyl ether solution'
_exptl_crystal_size_max          0.487
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 727 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2545
_refine_ls_number_restraints     200
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0341P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2011
_reflns_number_total             2545
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00915e2.cif
_cod_data_source_block           khas63
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554455
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.908
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              86100