Asymmetric Intramolecular Rauhut–Currier Reaction and Its Desymmetric Version via Double Thiol/Phase-Transfer Catalysis
Jiang, Ying; Yang, Yang; He, Qing; Du, Wei; Chen, Ying-Chun; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c01293

data_4038686
_publ_section_title
;
 Asymmetric Intramolecular Rauhut--Currier Reaction and Its Desymmetric
 Version via Double Thiol/Phase-Transfer Catalysis
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01293
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H27 N O4'
_chemical_formula_sum            'C27 H27 N O4'
_chemical_formula_weight         429.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
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_cell_formula_units_Z            4
_cell_length_a                   10.3861(2)
_cell_length_b                   11.8749(3)
_cell_length_c                   19.6542(5)
_cell_measurement_reflns_used    4956
_cell_measurement_temperature    295.8(5)
_cell_measurement_theta_max      72.2790
_cell_measurement_theta_min      6.1280
_cell_volume                     2424.03(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.8(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -99.0000  -90.0000 74

  2 omega    9.00  104.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000 -150.0000 95

  3 omega  -31.00   53.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000 -180.0000 84

  4 omega  -31.00   53.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000    0.0000 84

  5 omega   23.00   90.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000 -180.0000 67

  6 omega   17.00  105.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -       36.1671   38.0000 -120.0000 88

  7 omega   40.00  135.00   1.0000    8.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 95

  8 omega   39.00  109.00   1.0000    8.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

  9 omega   40.00   98.00   1.0000    8.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 10 omega   91.00  176.00   1.0000    8.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 85

 11 omega   38.00   91.00   1.0000    8.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 12 omega   38.00   91.00   1.0000    8.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 13 omega   39.00  109.00   1.0000    8.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

 14 omega  100.00  150.00   1.0000    8.4800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0196338000
_diffrn_orient_matrix_UB_12      0.0236532000
_diffrn_orient_matrix_UB_13      0.0763735000
_diffrn_orient_matrix_UB_21      -0.0376210000
_diffrn_orient_matrix_UB_22      0.1240755000
_diffrn_orient_matrix_UB_23      -0.0113377000
_diffrn_orient_matrix_UB_31      -0.1421263000
_diffrn_orient_matrix_UB_32      -0.0296170000
_diffrn_orient_matrix_UB_33      0.0134984000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11446
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.604
_diffrn_reflns_theta_min         4.816
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.177
_exptl_crystal_description       needle
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 1714 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0646
_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^)+(0.1229P)^2^+0.0866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.1702
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_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                4365
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01293_si_002.cif
_cod_data_source_block           8
_cod_original_cell_volume        2424.03(11)
_cod_database_code               4038686
_reflns_odcompleteness_completeness 99.80
_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 Ternary CH refined with riding coordinates:
 C00D(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00G(H00C,H00E), C00I(H00F,H00G)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00V(H00W)
2.d Idealised Me refined as rotating group:
 C00T(H00H,H00I,H00M), C00U(H00T,H00U,H00V), C00W(H00X,H00Y,H)
;
_shelx_res_checksum              42698
_shelx_hkl_checksum              85965
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-04-19
_olex2_submission_special_instructions 'No special instructions were received'