Role of the solvent in optical resolution of trans-chrysanthemic acid via diastereomeric salt formation with (1R,2R)-1-(4-nitrophenyl)-2-dimethylaminopropane-1,3-diol
Kozsda-Kovács, Éva; Keserü, György Miklós; Böcskei, Zsolt; Szilágyi, Ildikó; Simon, Kálmán; Bertók, Béla; Fogassy, Elemér; Journal of the Chemical Society, Perkin Transactions 2  (2000) 149–; doi:10.1039/a904682h

data_7203859
_publ_contact_author             'Zsolt Bocskei'
_publ_section_title
;
 Role of the solvent in optical resolution of trans-chrysanthemic acid
 via diastereomeric salt formation with
 (1R,2R)-1-(4-nitrophenyl)-2-dimethylaminopropane-1,3-diol
;
_journal_issue                   1
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              149
_journal_paper_doi               10.1039/a904682h
_journal_year                    2000
_chemical_compound_source        preparation
_chemical_formula_sum            'C21 H32 N2 O6'
_chemical_formula_weight         408.49
_chemical_melting_point          387.95
_chemical_name_common            ' d-trans chrysanthemic acid DMAD salt'
_chemical_name_systematic
; 
(1R,3R)-2,2-dimethyl-3-(methylpropenyl)-cyclopropanecarboxylic 
acid (1R,2R)-1-(4-nitrophenyl)-
-2-dimethylamino-1,3-propanediol salt
;
_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
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 107.02(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.923(10)
_cell_length_b                   7.658(10)
_cell_length_c                   15.573(10)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1132(2)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan: PROCESS (MSC)'
_computing_publication_material  'teXsan: FINISH (MSC)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Rigaku Raxis-II'
_diffrn_measurement_method       'omega scans with profile analysis'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0905
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1269
_diffrn_reflns_theta_max         20.89
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       ' colourless plates'
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.131
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.64(613)
_refine_ls_extinction_coef       0.1589(369)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.017
_refine_ls_goodness_of_fit_obs   1.105
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         1269
_refine_ls_number_restraints     179
_refine_ls_restrained_S_all      0.941
_refine_ls_restrained_S_obs      0.973
_refine_ls_R_factor_all          0.1323
_refine_ls_R_factor_obs          0.0989
_refine_ls_shift/esd_max         0.026
_refine_ls_shift/esd_mean        0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2301P)^2^+0.0282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.3124
_refine_ls_wR_factor_obs         0.2649
_reflns_number_observed          849
_reflns_number_total             1269
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            a904682h.txt
_cod_data_source_block           a1146
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '114.8 C' was changed to '387.95' -
it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.2301P)^2^+0.0282P] 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^)+(0.2301P)^2^+0.0282P] 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        1131.6(20)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7203859