Versatile synthesis of phospholides from open-chain precursors. Application to annelated pyrrole- and silole-phosphole rings.
Xu, Youzhi; Wang, Zhihua; Gan, Zhenjie; Xi, Qiuzhen; Duan, Zheng; Mathey, François; Organic letters 17 (2015) 1732–1734; doi:10.1021/acs.orglett.5b00598

data_1518990
_publ_section_title
;
 Versatile synthesis of phospholides from open-chain precursors.
 Application to annelated pyrrole- and silole-phosphole rings.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1732
_journal_page_last               1734
_journal_paper_doi               10.1021/acs.orglett.5b00598
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H17 O P Si'
_chemical_formula_sum            'C17 H17 O P Si'
_chemical_formula_weight         296.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_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_date             2014-10-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4427(8)
_cell_length_b                   6.5207(4)
_cell_length_c                   16.6673(8)
_cell_measurement_reflns_used    1206
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      70.4720
_cell_measurement_theta_min      5.2910
_cell_volume                     1569.67(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   10.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -30.0000 29

  2 omega  -35.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   30.0000 49

  3 omega   37.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   30.0000 79

  4 omega   34.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000   90.0000 52

  5 omega  -12.00   16.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  -90.0000 28

  6 omega  -13.00   12.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000   90.0000 25

  7 omega   69.00  106.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 37

  8 omega  142.00  169.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 27

  9 omega  118.00  171.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -30.0000 53

 10 omega   94.00  139.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 45

 11 omega   53.00   80.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 27

 12 omega   46.00   90.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 44

 13 omega   61.00  120.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -150.0000 59

 14 omega  -73.00  -48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000   90.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0173977000
_diffrn_orient_matrix_UB_12      0.0205740000
_diffrn_orient_matrix_UB_13      -0.0908424000
_diffrn_orient_matrix_UB_21      0.0010687000
_diffrn_orient_matrix_UB_22      -0.2352347000
_diffrn_orient_matrix_UB_23      -0.0080496000
_diffrn_orient_matrix_UB_31      -0.1052735000
_diffrn_orient_matrix_UB_32      0.0013502000
_diffrn_orient_matrix_UB_33      -0.0151233000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3218
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         5.31
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2019
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0583P)^2^+0.0177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1053
_reflns_number_gt                1832
_reflns_number_total             2019
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00598_si_002.cif
_cod_data_source_block           201410206
_cod_original_cell_volume        1569.66(16)
_cod_database_code               1518990
_chemical_oxdiff_formula         C20H2ON4O4P1Si1
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'