Silver-promoted oxidative cyclization of 1,6-enynes: highly regioselective synthesis of phosphorated fluorene derivatives.
Zhou, Zhao-Zhao; Jin, Dong-Po; Li, Lian-Hua; He, Yu-Tao; Zhou, Ping-Xin; Yan, Xiao-Biao; Liu, Xue-Yuan; Liang, Yong-Min; Organic letters 16 (2014) 5616–5619; doi:10.1021/ol502397f

data_1518037
_publ_section_title
;
 Silver-promoted oxidative cyclization of 1,6-enynes: highly
 regioselective synthesis of phosphorated fluorene derivatives.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5616
_journal_page_last               5619
_journal_paper_doi               10.1021/ol502397f
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C31 H31 O5 P'
_chemical_formula_sum            'C31 H31 O5 P'
_chemical_formula_weight         514.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     iterative
_audit_creation_date             2013-11-27
_audit_creation_method
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Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4715)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.379(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5189(13)
_cell_length_b                   20.166(2)
_cell_length_c                   12.1082(10)
_cell_measurement_reflns_used    1411
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3190
_cell_measurement_theta_min      3.4870
_cell_volume                     2775.0(5)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0083045000
_diffrn_orient_matrix_UB_12      -0.0302299000
_diffrn_orient_matrix_UB_13      -0.0302751000
_diffrn_orient_matrix_UB_21      0.0605880000
_diffrn_orient_matrix_UB_22      -0.0075091000
_diffrn_orient_matrix_UB_23      0.0158154000
_diffrn_orient_matrix_UB_31      -0.0124734000
_diffrn_orient_matrix_UB_32      -0.0164070000
_diffrn_orient_matrix_UB_33      0.0485793000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_unetI/netI     0.1225
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10944
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.034
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0041(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         5444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1487
_refine_ls_R_factor_gt           0.0724
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0664P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_ref         0.2127
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2561
_reflns_number_total             5444
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502397f_si_002.cif
_cod_data_source_block           zhouzhzh1126
_cod_depositor_comments          'Adding full bibliography for 1518037.cif.'
_cod_database_code               1518037
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C22(H22), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C31(H31A,H31B,
 H31C)
;
_shelx_res_checksum              62491
_shelx_hkl_checksum              17193