Rhodium-catalyzed double [2 + 2 + 2] cycloaddition of 1,4-bis(diphenylphosphinoyl)buta-1,3-diyne with tethered diynes: a modular, highly versatile single-pot synthesis of NU-BIPHEP biaryl diphosphines.
Doherty, Simon; Knight, Julian G.; Smyth, Catherine H.; Harrington, Ross W.; Clegg, William; Organic letters 9 (2007) 4925–4928; doi:10.1021/ol702390p

data_1505640
_publ_section_title
;
 Rhodium-catalyzed double [2 + 2 + 2] cycloaddition of
 1,4-bis(diphenylphosphinoyl)buta-1,3-diyne with tethered diynes: a
 modular, highly versatile single-pot synthesis of NU-BIPHEP biaryl
 diphosphines.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              4925
_journal_page_last               4928
_journal_paper_doi               10.1021/ol702390p
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C44 H40 P2, 0.5 C H Cl3'
_chemical_formula_sum            'C44.5 H40.5 Cl1.5 P2'
_chemical_formula_weight         690.38
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.279(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.4452(9)
_cell_length_b                   26.656(2)
_cell_length_c                   26.723(2)
_cell_measurement_reflns_used    7021
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.30
_cell_volume                     7408.9(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'thin-slice \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            33049
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             2904
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.48(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     885
_refine_ls_number_reflns         16894
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+3.6655P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                15253
_reflns_number_total             16894
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol702390p-file003.cif
_cod_data_source_block           sd239_compound_4a
_cod_original_cell_volume        7409.0(11)
_cod_original_sg_symbol_H-M      'C c'
_cod_original_formula_sum        'C44.50 H40.50 Cl1.50 P2'
_cod_database_code               1505640