Chiral Resolution ofRS-Praziquantel via Diastereomeric Co-Crystal Pair Formation withl-Malic Acid
Sánchez-Guadarrama, Obdulia; Mendoza-Navarro, Fabiola; Cedillo-Cruz, Alberto; Jung-Cook, Helgi; Arenas-García, Jenniffer I.; Delgado-Díaz, Alejandra; Herrera-Ruiz, Dea; Morales-Rojas, Hugo; Höpfl, Herbert; Crystal Growth & Design 16 (2016) 307–; doi:10.1021/acs.cgd.5b01254

data_4513707
_publ_section_title
;
 Chiral Resolution ofRS-Praziquantel via Diastereomeric Co-Crystal Pair
 Formation withl-Malic Acid
;
_journal_issue                   1
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              307
_journal_paper_doi               10.1021/acs.cgd.5b01254
_journal_volume                  16
_journal_year                    2016
_chemical_formula_moiety         'C19 H24 N2 O2, C4 H6 O5'
_chemical_formula_sum            'C23 H30 N2 O7'
_chemical_formula_weight         446.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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
_audit_creation_date             2015-08-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.765(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6543(10)
_cell_length_b                   8.4144(7)
_cell_length_c                   13.5321(11)
_cell_measurement_reflns_used    6702
_cell_measurement_temperature    294.8(3)
_cell_measurement_theta_max      27.9970
_cell_measurement_theta_min      3.7980
_cell_volume                     1118.64(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.8(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0769
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega    6.00   84.00   1.0000   16.7700
omega____ theta____ kappa____ phi______ frames
    -       15.2374   38.0000  -30.0000 78

  2 omega    5.00   83.00   1.0000   16.7700
omega____ theta____ kappa____ phi______ frames
    -       15.2374   57.0000  120.0000 78

  3 omega    3.00   82.00   1.0000   16.7700
omega____ theta____ kappa____ phi______ frames
    -       15.2374   57.0000   30.0000 79

  4 omega   36.00   63.00   1.0000   16.7700
omega____ theta____ kappa____ phi______ frames
    -       15.2374  178.0000  -90.0000 27

  5 omega   -9.00   83.00   1.0000   16.7700
omega____ theta____ kappa____ phi______ frames
    -       15.2374   77.0000 -150.0000 92

  6 omega   41.00   67.00   1.0000   16.7700
omega____ theta____ kappa____ phi______ frames
    -       15.2374  178.0000 -150.0000 26

  7 omega  -66.00  -19.00   1.0000   16.7700
omega____ theta____ kappa____ phi______ frames
    -      -16.0187  118.0000 -140.9208 47

  8 omega  -75.00  -33.00   1.0000   16.7700
omega____ theta____ kappa____ phi______ frames
    -      -16.0187  134.0000   53.3464 42

  9 omega  -54.00   31.00   1.0000   16.7700
omega____ theta____ kappa____ phi______ frames
    -       15.2374  -38.0000  -60.0000 85

 10 omega  -20.00   54.00   1.0000   16.7700
omega____ theta____ kappa____ phi______ frames
    -       15.2374  -99.0000   60.0000 74

 11 omega  -33.00   32.00   1.0000   16.7700
omega____ theta____ kappa____ phi______ frames
    -       15.2374  -57.0000 -150.0000 65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0227200000
_diffrn_orient_matrix_UB_12      0.0502258000
_diffrn_orient_matrix_UB_13      0.0456278000
_diffrn_orient_matrix_UB_21      -0.0178146000
_diffrn_orient_matrix_UB_22      0.0675668000
_diffrn_orient_matrix_UB_23      -0.0338538000
_diffrn_orient_matrix_UB_31      -0.0662855000
_diffrn_orient_matrix_UB_32      -0.0010292000
_diffrn_orient_matrix_UB_33      0.0007420000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_laue_measured_fraction_full 0.996
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14331
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.825
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       prism
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1394 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3907
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0390P)^2^+0.3150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1028
_reflns_Friedel_coverage         0.862
_reflns_friedel_fraction_full    0.998
_reflns_friedel_fraction_max     0.998
_reflns_number_gt                3528
_reflns_number_total             3907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg5b01254_si_002.cif
_cod_data_source_block           osgzwei
_cod_depositor_comments
'Adding full bibliography for 4513706--4513707.cif.'
_cod_original_cell_volume        1118.64(18)
_cod_database_code               4513707
_chemical_oxdiff_formula         C23H30N2O7
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C14(H14), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6), O7(H7)
;
_shelx_res_checksum              260
_shelx_hkl_checksum              39689
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'