Synthesis, Structures, and Photophysical Properties of Optically Stable 1,16-Diphenyl-3,14-diaryl-Substituted Tetrahydrobenzo[5]helicenediol Derivatives: Enantioselective Recognition toward Tryptophan Methyl Esters.
Fang, Lei; Li, Meng; Lin, Wei-Bin; Shen, Yun; Chen, Chuan-Feng; The Journal of organic chemistry 82 (2017) 7402–7409; doi:10.1021/acs.joc.7b01087

data_4032618
_publ_section_title
;
 Synthesis, Structures, and Photophysical Properties of Optically Stable
 1,16-Diphenyl-3,14-diaryl-Substituted Tetrahydrobenzo[5]helicenediol
 Derivatives: Enantioselective Recognition toward Tryptophan Methyl
 Esters.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7402
_journal_page_last               7409
_journal_paper_doi               10.1021/acs.joc.7b01087
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C38 H28 O2, C H2 Cl2'
_chemical_formula_sum            'C39 H30 Cl2 O2'
_chemical_formula_weight         601.53
_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   mixed
_audit_creation_date             2015-08-03
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                103.61(3)
_cell_angle_beta                 95.99(3)
_cell_angle_gamma                96.67(3)
_cell_formula_units_Z            2
_cell_length_a                   10.233(2)
_cell_length_b                   11.859(2)
_cell_length_c                   12.572(3)
_cell_measurement_reflns_used    4376
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4809
_cell_measurement_theta_min      1.6824
_cell_volume                     1459.0(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 11.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 40.0453
              2theta: -20.0683
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 11.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 40.0453
              2theta: -20.0683
scan:
    Number of images: 274
               Slice: -110.0000 - 27.0000
         Image width: 0.5000
            Exp time: 11.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 40.0453
              2theta: -20.0683
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0901
_diffrn_orient_matrix_UB_12      -0.0011
_diffrn_orient_matrix_UB_13      -0.0418
_diffrn_orient_matrix_UB_21      -0.0229
_diffrn_orient_matrix_UB_22      -0.0308
_diffrn_orient_matrix_UB_23      -0.0789
_diffrn_orient_matrix_UB_31      -0.0085
_diffrn_orient_matrix_UB_32      0.0675
_diffrn_orient_matrix_UB_33      -0.0469
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15342
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.196
_diffrn_reflns_theta_max         25.196
_diffrn_reflns_theta_min         1.682
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       Plate
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.975
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5239
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.1211
_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^)+(0.1433P)^2^+2.5500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3053
_refine_ls_wR_factor_ref         0.3223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4158
_reflns_number_total             5239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01087_si_002.cif
_cod_data_source_block           mx4004
_cod_depositor_comments          'Adding full bibliography for 4032618.cif.'
_cod_original_cell_volume        1458.9(5)
_cod_database_code               4032618
_diffrn_number_total             6653
_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
2. Restrained distances
 Cl2A-C39 = Cl2-C39
 1.79 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Cl2 \\sim Cl2A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
Uanis(Cl2) \\sim Ueq, Uanis(Cl2A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(H39C)=Sof(H39D)=Sof(Cl2A)=1-FVAR(1)
 Sof(Cl2)=Sof(H39A)=Sof(H39B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C25(H25A,H25B), C26(H26A,H26B), C39(H39A,
 H39B), C39(H39C,H39D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24), C31(H31), C32(H32), C34(H34), C35(H35), C36(H36),
  C37(H37), C38(H38)
;
_shelx_res_checksum              79022
_shelx_hkl_checksum              3718
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'