C–P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds
Oßwald, Simon; Zippel, Christoph; Hassan, Zahid; Nieger, Martin; Bräse, Stefan; RSC Advances 12 (2022) 3309–3312; doi:10.1039/D2RA00094F

data_7244298
_publ_section_title
;
 C--P bond formation of cyclophanyl-, and aryl halides via a UV-induced
 photo Arbuzov reaction: a versatile portal to phosphonate-grafted
 scaffolds
;
_journal_issue                   6
_journal_name_full               'RSC Advances'
_journal_page_first              3309
_journal_page_last               3312
_journal_paper_doi               10.1039/D2RA00094F
_journal_volume                  12
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H26 O6 P2'
_chemical_formula_sum            'C20 H26 O6 P2'
_chemical_formula_weight         424.35
_chemical_name_systematic
;
tetramethyl 1,4(1,4)-dibenzenacyclohexaphane-1^2^,1^5^-diylbis(phosphonate)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-08-16 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.1103(13)
_cell_length_b                   21.6232(14)
_cell_length_c                   8.7121(6)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.2
_cell_measurement_theta_min      4.1
_cell_volume                     3976.8(4)
_computing_cell_refinement       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2016)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker D8 VENTURE with PhotonII CPAD detector'
_diffrn_measurement_method       'rotation in \f and \w, 1\%, shutterless'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16792
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.199
_diffrn_reflns_theta_min         5.858
_diffrn_source                   'INCOATEC microfocus sealed tube'
_exptl_absorpt_coefficient_mu    2.293
_exptl_absorpt_correction_T_max  0.8894
_exptl_absorpt_correction_T_min  0.7534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       plates
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 906 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1959
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0213
_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^)+(0.0336P)^2^+3.5595P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0599
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1954
_reflns_number_total             1959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra00094f2.cif
_cod_data_source_block           sb1390_hy_compound_3b
_cod_database_code               7244298
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.657
_shelx_estimated_absorpt_t_max   0.914
_shelx_res_checksum              56406