Quaternary Carbon Center Forming [3 + 2] Cyclization Reaction by Adjusting the Substituents of Substrates.
Yang, Xie-Chao; Liu, Jin-Yu; Liu, Zhen; Hu, Xiu-Qin; Xu, Peng-Fei; The Journal of organic chemistry 84 (2019) 13871–13880; doi:10.1021/acs.joc.9b02041

data_4034515
_publ_section_title
;
 Quaternary Carbon Center Forming [3 + 2] Cyclization Reaction by
 Adjusting the Substituents of Substrates.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13871
_journal_page_last               13880
_journal_paper_doi               10.1021/acs.joc.9b02041
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C29 H31 F3 N2 O8'
_chemical_formula_sum            'C29 H31 F3 N2 O8'
_chemical_formula_weight         592.56
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.830(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0658(8)
_cell_length_b                   12.6324(7)
_cell_length_c                   18.3843(11)
_cell_measurement_reflns_used    2100
_cell_measurement_temperature    295.10(18)
_cell_measurement_theta_max      25.5850
_cell_measurement_theta_min      3.6160
_cell_volume                     2888.6(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      295.10(18)
_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   -8.00   25.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000 -120.0000 33

  2 omega  -44.00   36.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  -60.0000 80

  3 omega  -48.00  -22.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -180.0000 26

  4 omega   -1.00   45.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000   60.0000 46

  5 omega   64.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  168.0000 -171.0000 31

  6 omega  -10.00   27.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000 -150.0000 37
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0248313000
_diffrn_orient_matrix_UB_12      0.0055184000
_diffrn_orient_matrix_UB_13      0.0399104000
_diffrn_orient_matrix_UB_21      0.0328439000
_diffrn_orient_matrix_UB_22      -0.0446564000
_diffrn_orient_matrix_UB_23      -0.0002605000
_diffrn_orient_matrix_UB_31      0.0394521000
_diffrn_orient_matrix_UB_32      0.0336193000
_diffrn_orient_matrix_UB_33      -0.0069713000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11643
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.373
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78112
_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    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5682
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0667P)^2^+1.7782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1807
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3585
_reflns_number_total             5682
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02041_si_002.cif
_cod_data_source_block           liujy_0528
_cod_database_code               4034515
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.71
_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. Restrained distances
 C19-C20
 1.55 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.008
4.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4A), C5(H5), C25(H25), C26(H26), C27(H27), C28(H28)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C20(H20A,H20B,
 H20C), C23(H23A,H23B,H23C)
;
_olex2_date_sample_data_collection 2018-05-28
_olex2_submission_special_instructions 'No special instructions were received'