Diastereoselective Photochromism of an (R)-Binaphthol-Condensed Indolylfulgide
Yasushi Yokoyama; Soichi Uchida; Yayoi Yokoyama; Yoko Sugawara; Yukio Kurita; Journal of the American Chemical Society 118 (1996) 3100–3107; doi:10.1021/ja9523045

data_4117115
_publ_contact_author             'Yasushi Yokoyama'
_publ_contact_author_email       yokoyama@materials.bsk.ynu.ac.jp
_publ_contact_author_fax         +81-45-338-3121
_publ_contact_author_phone       '+81-45-335-1451 ext.2718'
_publ_section_title
;
 Diastereoselective Photochromism of an (R)-Binaphthol-Condensed
 Indolylfulgide
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3100
_journal_page_last               3107
_journal_paper_doi               10.1021/ja9523045
_journal_volume                  118
_journal_year                    1996
_chemical_formula_moiety         '(C41 H35 N O4)  2(C3 O H6)'
_chemical_formula_sum            'C47 H47 N O6'
_chemical_formula_weight         721.86
_chemical_melting_point          535(1)
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens
;
>From a difference Fourier map except hydrogen atoms of acetone group. 
H's of acetone are not included in the calculations.
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 99.89(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.941(9)
_cell_length_b                   13.861(10)
_cell_length_c                   13.141(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      14.0
_cell_measurement_theta_min      13.5
_cell_volume                     1963(2)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'MSC/AFC Diffractometer Control'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measurement_device       'RIGAKU AFC7R'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoKalpha
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.04
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4924
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.0
_diffrn_standards_decay_%        'less than 1%'
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       cube
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
The absolute configuration at the quaternary carbon atom induced
by the photocylcization was determined in reference to that of 
(R)-2,2'-binaphtyl group.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.018
_refine_ls_goodness_of_fit_obs   1.040
_refine_ls_hydrogen_treatment
;
Ref U except H51, H52, and H53.   U's of H51, H52, and H53 are 
setted to be two times Ueq of C17.
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         4675
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_restrained_S_obs      1.040
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_obs          0.0494
_refine_ls_shift/esd_max         0.159
_refine_ls_shift/esd_mean        0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1135P)^2^+0.0420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1634
_refine_ls_wR_factor_obs         0.1459
_reflns_number_observed          3682
_reflns_number_total             4676
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja9523045.cif
_cod_data_source_block           C47H47NO6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1135P)^2^+0.0420P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1135P)^2^+0.0420P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1963.3(25)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4117115