Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes
Moglie, Yanina; González-Soria, María José; Martín-García, Iris; Radivoy, Gabriel; Alonso, Francisco; Green Chem. 18 (2016) 4896–; doi:10.1039/C6GC00903D

data_7226727
_publ_section_title
;
 Catalyst- and solvent-free hydrophosphination and multicomponent
 hydrothiophosphination of alkenes and alkynes
;
_journal_issue                   18
_journal_name_full               'Green Chem.'
_journal_page_first              4896
_journal_paper_doi               10.1039/C6GC00903D
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_sum            'C22 H27 O P'
_chemical_formula_weight         338.40
_chemical_melting_point          388(3)
_chemical_name_systematic
'(S)-[(4-Isopropylcyclohex-1-en-1-yl)methyl]diphenylphosphine oxide '
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-03-15 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.0333(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7190(3)
_cell_length_b                   17.9432(10)
_cell_length_c                   9.0209(5)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.533
_cell_measurement_theta_min      4.929
_cell_volume                     914.22(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2011)'
_computing_data_collection       'APEX2 2014.1-1 (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\w-scans and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19038
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.594
_diffrn_reflns_theta_min         4.929
_diffrn_source                   'high brilliance microfocus sealed tube '
_exptl_absorpt_coefficient_mu    1.352
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/2
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.023(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3750
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0505P)^2^+0.0743P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0744
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3699
_reflns_number_total             3750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6gc00903d3.cif
_cod_data_source_block           irr466d_0msp
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '386-391' was changed to '388(3)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7226727
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.764
_shelx_estimated_absorpt_t_max   0.935
_shelx_res_checksum              29869
_shelx_hkl_checksum              27126
_solvent_exptl_crystal_recrystallization_method 'hexane/ethyl acetate'