Anatomy of Phobanes. Diastereoselective Synthesis of the Three Isomers of n-Butylphobane and a Comparison of their Donor Properties
Monica Carreira; Manutsavin Charernsuk; Michael Eberhard; Natalie Fey; Roel van Ginkel; Alex Hamilton; Wilhelmus P. Mul; A. Guy Orpen; Hirihataya Phetmung; Paul G. Pringle; Journal of the American Chemical Society 131 (2009) 3078–3092; doi:10.1021/ja808807s

data_4103972
_publ_section_title
;
 Anatomy of Phobanes. Diastereoselective Synthesis of the Three Isomers of
 n-Butylphobane and a Comparison of their Donor Properties
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3078
_journal_page_last               3092
_journal_paper_doi               10.1021/ja808807s
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C10 H20 Cl O2 P'
_chemical_formula_weight         238.68
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.078(3)
_cell_length_b                   7.7656(12)
_cell_length_c                   11.962(2)
_cell_measurement_reflns_used    4078
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      50
_cell_measurement_theta_min      5
_cell_volume                     2329.5(6)
_computing_cell_refinement       'SAINT (Siemens, 1995b)'
_computing_data_collection       'SMART (Siemens, 1995b)'
_computing_data_reduction        'SAINT (Siemens, 1995b)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1995a)'
_computing_publication_material  'SHELXTL (Siemens, 1995a)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens SMART area detector'
_diffrn_measurement_method       'narrow frame \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18722
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.15(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4087
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+4.0136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                3713
_reflns_number_total             4087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja808807s_si_002.cif
_cod_data_source_block           bill
_cod_original_cell_volume        2329.5(7)
_cod_database_code               4103972