Silver-catalyzed carbon-phosphorus functionalization of N-(p-methoxyaryl)propiolamides coupled with dearomatization: access to phosphorylated aza-decenones
Li-Jing Wang; An-Qi Wang; Yu Xia; Xin-Xing Wu; Xue-Yuan Liu; Yong-Min Liang; Chem.Commun. 50 (2014) 13998–; doi:10.1039/C4cc06923D

data_7115922
_publ_section_title
;
 Silver-catalyzed carbon-phosphorus functionalization of
 N-(p-methoxyaryl)propiolamides coupled with dearomatization: access to
 phosphorylated aza-decenones
;
_journal_name_full               Chem.Commun.
_journal_page_first              13998
_journal_paper_doi               10.1039/C4cc06923D
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C20 H22 N O5 P'
_chemical_formula_sum            'C20 H22 N O5 P'
_chemical_formula_weight         387.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.801(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3849(3)
_cell_length_b                   12.0609(4)
_cell_length_c                   19.3266(6)
_cell_measurement_reflns_used    2962
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.5530
_cell_measurement_theta_min      4.3240
_cell_volume                     1944.48(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega   24.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  120.0000 40

  2 omega   59.00  127.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000    0.0000 68

  3 omega   56.00   98.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -60.0000 42

  4 omega   51.00   79.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 28

  5 omega   35.00   87.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 52

  6 omega   71.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -90.0000 49

  7 omega   97.00  175.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   90.0000 78

  8 omega   90.00  177.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  150.0000 87

  9 omega   59.00   92.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 33

 10 omega   35.00   82.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 47

 11 omega   -2.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -60.0000 77

 12 omega   33.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 56

 13 omega   38.00  111.00   1.0000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 73

 14 omega   -3.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   58.0000  -44.0000 42

 15 omega  -39.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000    0.0000  150.0000 42

 16 omega  -15.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000 -120.0000 80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1235486000
_diffrn_orient_matrix_UB_12      0.0905302000
_diffrn_orient_matrix_UB_13      0.0232995000
_diffrn_orient_matrix_UB_21      -0.1141338000
_diffrn_orient_matrix_UB_22      0.0463577000
_diffrn_orient_matrix_UB_23      0.0505627000
_diffrn_orient_matrix_UB_31      0.0761785000
_diffrn_orient_matrix_UB_32      -0.0772889000
_diffrn_orient_matrix_UB_33      0.0576301000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7380
_diffrn_reflns_theta_full        69.88
_diffrn_reflns_theta_max         69.88
_diffrn_reflns_theta_min         4.33
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.519
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0834P)^2^+0.4835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1501
_reflns_number_gt                2887
_reflns_number_total             3611
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc06923d2.cif
_cod_data_source_block           wanglij0828
_cod_original_cell_volume        1944.50(12)
_cod_database_code               7115922
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'