Utility of Bifunctional N-Heterocyclic Phosphine (NHP)-Thioureas for Metal-Free Carbon-Phosphorus Bond Construction toward Regio- and Stereoselective Formation of Vinylphosphonates.
Mulla, Karimulla; Aleshire, Kyle L.; Forster, Paul M.; Kang, Jun Yong; The Journal of organic chemistry 81 (2016) 77–88; doi:10.1021/acs.joc.5b02184

data_4036480
_publ_section_title
;
 Utility of Bifunctional N-Heterocyclic Phosphine (NHP)-Thioureas for
 Metal-Free Carbon-Phosphorus Bond Construction toward Regio- and
 Stereoselective Formation of Vinylphosphonates.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              77
_journal_page_last               88
_journal_paper_doi               10.1021/acs.joc.5b02184
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C23 H25 N4 O P S'
_chemical_formula_sum            'C23 H25 N4 O P S'
_chemical_formula_weight         436.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
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_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
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_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
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_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
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_diffrn_reflns_limit_l_min       -20
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_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         1.420
_diffrn_standards_number         0
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_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1166 before and 0.0362 after correction. The Ratio of minimum to maximum transmission is 0.8704. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
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_exptl_crystal_description       plate
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_exptl_crystal_size_min          0.05
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_refine_ls_R_factor_all          0.0385
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.3176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4630
_reflns_number_total             5410
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           kang4_0m_a
_cod_original_cell_volume        1093.6(3)
_cod_database_code               4036480
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H6,H7), C8(H8,H9), C15(H15,H16), C16(H17,H18)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H19), N4(H20), C2(H1), C3(H2), C4(H3), C5(H4), C6(H5), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14), C19(H21), C20(H22), C21(H23), C22(H24), C23(H25)
;
_olex2_submission_special_instructions 'No special instructions were received'