Asymmetric Synthesis of (-)-Pterocarine and (-)-Galeon via Chiral Phase Transfer-Catalyzed Atropselective Formation of Diarylether Cyclophane Skeleton.
Ding, Qiang; Wang, Qiuyan; He, Huan; Cai, Qian; Organic letters 19 (2017) 1804–1807; doi:10.1021/acs.orglett.7b00570

data_1545939
_publ_section_title
;
 Asymmetric Synthesis of (-)-Pterocarine and (-)-Galeon via Chiral Phase
 Transfer-Catalyzed Atropselective Formation of Diarylether Cyclophane
 Skeleton.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1804
_journal_page_last               1807
_journal_paper_doi               10.1021/acs.orglett.7b00570
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H23 N O3'
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90.00
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_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.69815(8)
_cell_length_b                   8.99657(8)
_cell_length_c                   11.23680(11)
_cell_measurement_reflns_used    10082
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.5910
_cell_measurement_theta_min      4.8670
_cell_volume                     867.365(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
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_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -97.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3507  125.0000 -120.0000 79

  2 omega  -33.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3507  -38.0000  -30.0000 99

  3 omega   17.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3507   38.0000  150.0000 99

  4 omega   17.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3507   38.0000   30.0000 99

  5 omega   51.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3507  158.0000 -116.0000 66

  6 omega    9.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -90.0000  171.5253 121

  7 omega    9.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -92.0000  -24.5482 122

  8 omega   16.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000    0.0000 109

  9 omega   16.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000 -150.0000 53

 10 omega   16.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000  -60.0000 53

 11 omega   16.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000  150.0000 53

 12 omega   20.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000   90.0000 102

 13 omega   19.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000 -150.0000 58

 14 omega    9.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000 -132.7672 122

 15 omega   18.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -158.0000 -149.0000 96

 16 omega   67.00  166.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000 -180.0000 99

 17 omega   10.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000  -60.0000 73

 18 omega   64.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000 -150.0000 105

 19 omega   63.00  165.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000   90.0000 102

 20 omega   19.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000   90.0000 58

 21 omega   20.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000 -150.0000 102

 22 omega   20.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000    0.0000 102

 23 omega   19.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000   30.0000 77

 24 omega   16.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000  -30.0000 53

 25 omega   19.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000 -120.0000 58

 26 omega    9.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000   73.2435 122

 27 omega   60.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -150.0000 109

 28 omega    9.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3507   77.0000   30.0000 109

 29 omega    9.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3507   77.0000  150.0000 109

 30 omega   13.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3507   57.0000  -90.0000 102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
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_diffrn_orient_matrix_UB_11      -0.0688551000
_diffrn_orient_matrix_UB_12      -0.1135501000
_diffrn_orient_matrix_UB_13      -0.0968678000
_diffrn_orient_matrix_UB_21      0.0328177000
_diffrn_orient_matrix_UB_22      -0.1261761000
_diffrn_orient_matrix_UB_23      0.0934439000
_diffrn_orient_matrix_UB_31      -0.1625487000
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_diffrn_orient_matrix_UB_33      0.0346608000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15171
_diffrn_reflns_theta_full        66.79
_diffrn_reflns_theta_max         66.79
_diffrn_reflns_theta_min         5.16
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0576P)^2^+0.0378P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                2898
_reflns_number_total             3049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00570_si_002.cif
_cod_data_source_block           exp_869
_cod_original_cell_volume        867.366(14)
_cod_database_code               1545939
_reflns_odcompleteness_completeness 98.74
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N19(H19A,H19B)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C23(H23A,
 H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C10(H10), C12(H12), C14(H14)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'