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_4513706
_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     iterative
_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                 102.513(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0451(5)
_cell_length_b                   8.6712(5)
_cell_length_c                   12.9992(7)
_cell_measurement_reflns_used    3740
_cell_measurement_temperature    294.9(3)
_cell_measurement_theta_max      26.6900
_cell_measurement_theta_min      3.7100
_cell_volume                     1105.38(11)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0769
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   18.00   78.00   1.0000    5.4800
omega____ theta____ kappa____ phi______ frames
    -       15.2374   57.0000  -30.0000 60

  2 omega    0.00   83.00   1.0000    5.4800
omega____ theta____ kappa____ phi______ frames
    -       15.2374   57.0000  120.0000 83

  3 omega   38.00   64.00   1.0000    5.4800
omega____ theta____ kappa____ phi______ frames
    -       15.2374  178.0000  -90.0000 26

  4 omega  -23.00   16.00   1.0000    5.4800
omega____ theta____ kappa____ phi______ frames
    -      -16.0187   57.0000  -30.0000 39

  5 omega  -33.00   27.00   1.0000    5.4800
omega____ theta____ kappa____ phi______ frames
    -      -16.0187   57.0000  -90.0000 60

  6 omega  -20.00   54.00   1.0000    5.4800
omega____ theta____ kappa____ phi______ frames
    -       15.2374  -99.0000   90.0000 74

  7 omega   63.00   88.00   1.0000    5.4800
omega____ theta____ kappa____ phi______ frames
    -       15.2374 -178.0000   60.0000 25
;
_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      0.0205839000
_diffrn_orient_matrix_UB_12      -0.0584925000
_diffrn_orient_matrix_UB_13      -0.0314249000
_diffrn_orient_matrix_UB_21      -0.0161937000
_diffrn_orient_matrix_UB_22      0.0489801000
_diffrn_orient_matrix_UB_23      -0.0446684000
_diffrn_orient_matrix_UB_31      0.0673958000
_diffrn_orient_matrix_UB_32      0.0296064000
_diffrn_orient_matrix_UB_33      0.0118247000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7488
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.845
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85665
_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    1.341
_exptl_crystal_description       prism
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1410 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(6)
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         3891
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0393P)^2^+0.1533P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.864
_reflns_friedel_fraction_full    0.998
_reflns_friedel_fraction_max     0.998
_reflns_number_gt                3556
_reflns_number_total             3891
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg5b01254_si_003.cif
_cod_data_source_block           herbert
_cod_depositor_comments
'Adding full bibliography for 4513706--4513707.cif.'
_cod_database_code               4513706
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.83
_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. Restrained distances
 C7-C6A
 1.5 with sigma of 0.005
3. Same fragment restrains
{C5B, C6B} sigma for 1-2: 0.02, 1-3: 0.04
as
{C5A, C6A}
4. Others
 Sof(C5B)=Sof(H5BA)=Sof(H5BB)=Sof(C6B)=Sof(H6BA)=Sof(H6BB)=1-FVAR(1)
 Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C14(H14), C22(H22)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C5B(H5BA,H5BB),
 C6B(H6BA,H6BB), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B),
  C19(H19A,H19B), C21(H21A,H21B)
5.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
5.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6), O7(H7)
;
_shelx_res_checksum              28271
_shelx_hkl_checksum              25244
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'