Absolute configuration determination of the <i>anti</i>-head-to-head photocyclodimer of anthracene-2-carboxylic acid through cocrystallization with <small>L</small>-prolinol
Kawanami, Yuko; Tanaka, Hidekazu; Mizoguchi, Jun-ichi; Kanehisa, Nobuko; Fukuhara, Gaku; Nishijima, Masaki; Mori, Tadashi; Inoue, Yoshihisa; Acta Crystallographica Section C 69 (2013) 1411–1413; doi:10.1107/S0108270113028461

data_2019253
_publ_section_title
;
 Absolute configuration determination of the <i>anti</i>-head-to-head
 photocyclodimer of anthracene-2-carboxylic acid through cocrystallization
 with <small>L</small>-prolinol
;
_journal_coeditor_code           SK3506
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1411
_journal_page_last               1413
_journal_paper_doi               10.1107/S0108270113028461
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C5 H12 N O + , C30 H19 O4 - , C H2 Cl2'
_chemical_formula_moiety         'C5 H12 N O +, C30 H19 O4 -, C H2 Cl2'
_chemical_formula_sum            'C36 H33 Cl2 N O5'
_chemical_formula_weight         630.57
_chemical_name_common
;(<i>S</i>)-2-(Hydroxymethyl)pyrrolidin-1-ium
(5<i>R</i>,6<i>S</i>,11<i>R</i>,12<i>S</i>)-8-carboxy-5,6,11,12-tetrahydro-5,12:6,11-bis([1,2]benzeno)dibenzo[<i>a</i>,<i>e</i>][8]annulene-2-carboxylate
dichloromethane monosolvate
;
_chemical_name_systematic
;(<i>S</i>)-2-(Hydroxymethyl)pyrrolidin-1-ium
5-carboxyheptacyclo[8.6.6.6^2,9^.0^3,8^.0^11,16^.0^17,22^.0^23,28^]octacosa-2,4,6,8,11(16),12,14,17(22),18,20,23(28),24,26-tridecaene-13-carboxylate dichloromethane monosolvate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.6581(10)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   11.4579(2)
_cell_length_b                   9.83146(18)
_cell_length_c                   13.8027(3)
_cell_measurement_reflns_used    11621
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      3.22
_cell_volume                     1547.27(5)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2010)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2010)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17245
_diffrn_reflns_theta_full        68.19
_diffrn_reflns_theta_max         68.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.254
_exptl_absorpt_correction_T_max  0.798
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   '(Walker & Stuart, 1983)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             660.00
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.410
_refine_ls_abs_structure_details 'Flack (1983), with 2125 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5117
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0586P)^2^+0.8448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1371
_reflns_number_gt                4490
_reflns_number_total             5117
_reflns_threshold_expression     F^2^>2\s(F^2^)
_cod_data_source_file            sk3506.cif
_cod_data_source_block           I
_cod_original_cell_volume        1547.26(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2019253