Efficient dibenzo[c]acridine helicene-like synthesis and resolution: scaleup, structural control, and high chiroptical properties.
Jierry, Loïc; Harthong, Steven; Aronica, Christophe; Mulatier, Jean-Christophe; Guy, Laure; Guy, Stéphan; Organic letters 14 (2012) 288–291; doi:10.1021/ol202799j

data_1503477
_publ_section_title
;
 Efficient dibenzo[c]acridine helicene-like synthesis and resolution:
 scaleup, structural control, and high chiroptical properties.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              288
_journal_page_last               291
_journal_paper_doi               10.1021/ol202799j
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C47 H32 N2 O2, C H2 Cl2'
_chemical_formula_sum            'C48 H34 Cl2 N2 O2'
_chemical_formula_weight         741.71
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 124.556(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.248(5)
_cell_length_b                   12.589(5)
_cell_length_c                   20.845(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     7402(4)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       Unknown
_diffrn_measurement_device_type  Serial
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.056
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16054
_diffrn_reflns_theta_full        27.050
_diffrn_reflns_theta_max         27.886
_diffrn_reflns_theta_min         2.666
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            cube
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       white
_exptl_crystal_F_000             3088
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.88
_refine_diff_density_min         -1.02
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8814
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         3967
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1569
_refine_ls_R_factor_gt           0.0902
_refine_ls_shift/su_max          0.000426
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 2.09 2.00 1.07 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1907
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.0999
_reflns_limit_h_max              37
_reflns_limit_h_min              -44
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                4573
_reflns_number_total             8691
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0817
_oxford_refine_ls_scale          0.1881(7)
_oxford_reflns_number_all        8671
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            ol202799j_si_004.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

2017-03-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_original_formula_moiety     'C96 H68 Cl4 N4 O4'
_cod_original_formula_sum        'C96 H68 Cl4 N4 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1483.43
_cod_database_code               1503477