Introducing a new class of N-phosphoryl ynamides via Cu(I)-catalyzed amidations of alkynyl bromides.
DeKorver, Kyle A.; Walton, Mary C.; North, Troy D.; Hsung, Richard P.; Organic letters 13 (2011) 4862–4865; doi:10.1021/ol201947b

data_1502445
_publ_section_title
;
 Introducing a new class of N-phosphoryl ynamides via Cu(I)-catalyzed
 amidations of alkynyl bromides.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4862
_journal_page_last               4865
_journal_paper_doi               10.1021/ol201947b
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C22 H26 N O3 P'
_chemical_formula_sum            'C22 H26 N O3 P'
_chemical_formula_weight         383.41
_chemical_name_common            11111a
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 97.0450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.7595(15)
_cell_length_b                   5.8572(4)
_cell_length_c                   15.7081(11)
_cell_measurement_reflns_used    5081
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.75
_cell_measurement_theta_min      2.61
_cell_volume                     1986.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
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_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            19831
_diffrn_reflns_theta_full        26.24
_diffrn_reflns_theta_max         26.24
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.9460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008/1)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.219
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4003
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.6014P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                2863
_reflns_number_total             4003
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201947b_si_003.cif
_cod_data_source_block           11111a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               1502445