Base promoted direct difunctionalization/cascade cyclization of 1,6-enynes.
Li, Ming; Wang, Cui-Tian; Qiu, Yi-Feng; Zhu, Xin-Yu; Han, Ya-Ping; Xia, Yu; Li, Xue-Song; Liang, Yong-Min; Chemical communications (Cambridge, England) 54 (2018) 5334–5337; doi:10.1039/c8cc03280g

data_7121564
_publ_section_title
;
 Base promoted direct difunctionalization/cascade cyclization of
 1,6-enynes.
;
_journal_issue                   42
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5334
_journal_page_last               5337
_journal_paper_doi               10.1039/c8cc03280g
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C30 H31 F2 N O4 S'
_chemical_formula_sum            'C30 H31 F2 N O4 S'
_chemical_formula_weight         539.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                65.506(5)
_cell_angle_beta                 85.068(4)
_cell_angle_gamma                61.827(5)
_cell_formula_units_Z            4
_cell_length_a                   13.8373(7)
_cell_length_b                   14.6324(8)
_cell_length_c                   16.7936(8)
_cell_measurement_reflns_used    4073
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      26.7990
_cell_measurement_theta_min      3.6030
_cell_volume                     2702.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -11.00   15.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.1983  -99.0000 -180.0000 26

  2 omega  -55.00   -4.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.1983   77.0000  -60.0000 51

  3 omega  -50.00   37.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9327  -77.0000   90.0000 87

  4 omega   35.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9327  178.0000  120.0000 81

  5 omega  -40.00   73.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9327  -19.0000 -120.0000 113

  6 omega   -6.00  101.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9327   57.0000 -150.0000 107
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0138555000
_diffrn_orient_matrix_UB_12      -0.0270343000
_diffrn_orient_matrix_UB_13      0.0465973000
_diffrn_orient_matrix_UB_21      0.0314654000
_diffrn_orient_matrix_UB_22      -0.0539222000
_diffrn_orient_matrix_UB_23      -0.0015152000
_diffrn_orient_matrix_UB_31      0.0475796000
_diffrn_orient_matrix_UB_32      0.0074327000
_diffrn_orient_matrix_UB_33      -0.0046571000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18472
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.27
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75421
_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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     744
_refine_ls_number_reflns         10621
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0594
_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^)+(0.0619P)^2^+0.8691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1599
_reflns_number_gt                7033
_reflns_number_total             10621
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc03280g2.cif
_cod_data_source_block           lim_3a
_cod_depositor_comments
'Adding full bibliography for 7121564--7121565.cif.'
_cod_original_cell_volume        2702.0(2)
_cod_database_code               7121564
_reflns_odcompleteness_completeness 99.78
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F3') \\sim Ueq, Uanis(C37') \\sim Ueq, Uanis(O5') \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: H36A(0.65) H36B(0.65) H36C(0.35) H36D(0.35) H40A(0.65) H40B(0.65)
 H40C(0.65) H40D(0.35) H40E(0.35) H40F(0.35) F3(0.65) F4(0.65) O5(0.65)
 C37(0.65) C38(0.65) C39(0.65) H39A(0.65) H39B(0.65) F3'(0.35) F4'(0.35)
 O5'(0.35) C37'(0.35) C38'(0.35) C39'(0.35) H39C(0.35) H39D(0.35)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C6(H6A,H6B), C9(H9A,H9B), C31(H31A,H31B), C34(H34A,
 H34B), C36(H36A,H36B), C36(H36C,H36D), C39(H39A,H39B), C39'(H39C,H39D)
4.b Me refined with riding coordinates:
 C40(H40A,H40B,H40C), C40(H40D,H40E,H40F)
4.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29), C43(H43),
  C44(H44), C45(H45), C46(H46), C47(H47), C49(H49), C50(H50), C51(H51),
 C52(H52), C53(H53), C55(H55), C56(H56), C58(H58), C59(H59)
4.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C30(H30A,H30B,H30C), C35(H35A,H35B,
 H35C), C60(H60A,H60B,H60C)
;
_olex2_date_sample_data_collection 2018-04-20
_olex2_submission_special_instructions 'No special instructions were received'