Cation∙∙∙Cation Hydrogen Bonds in Synephrine Salts: A Typical Interaction in an Unusual Environment.
Dash, Sibananda G.; Thakur, Tejender S.; Physical Chemistry Chemical Physics  (2019) –; doi:10.1039/C9CP03164B

data_7233537
_publ_section_title
;
 Cation&#x2219;&#x2219;&#x2219;Cation Hydrogen Bonds in Synephrine Salts:
 A Typical Interaction in an Unusual Environment.
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/C9CP03164B
_journal_year                    2019
_chemical_formula_moiety         'C9 H14 N O2, 0.5(C2 O4)'
_chemical_formula_sum            'C10 H14 N O4'
_chemical_formula_weight         212.22
_chemical_name_common            '(+/-)-Synephrine Oxalic Acid (1:0.5) Salt'
_chemical_name_systematic        '(+/-)-Synephrine Oxalic Acid (1:0.5) Salt'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-01 deposited with the CCDC.    2019-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.81(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.997(7)
_cell_length_b                   7.236(4)
_cell_length_c                   12.376(6)
_cell_measurement_reflns_used    895
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      3.3
_cell_volume                     1038.8(10)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
scan:
    Number of images: 200
               Slice: -30.0000 - 70.0000
         Image width: 0.5000
            Exp time: 16.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 60.0000
                 Phi: 0.0000
                 XTD: 45.0222
              2theta: -19.6851
scan:
    Number of images: 200
               Slice: -30.0000 - 70.0000
         Image width: 0.5000
            Exp time: 16.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 60.0000
                 Phi: 90.0000
                 XTD: 45.0222
              2theta: -19.6851
scan:
    Number of images: 200
               Slice: -110.0000 - -10.0000
         Image width: 0.5000
            Exp time: 16.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -60.0000
                 Phi: 180.0000
                 XTD: 45.0222
              2theta: -19.6851
scan:
    Number of images: 200
               Slice: -110.0000 - -10.0000
         Image width: 0.5000
            Exp time: 16.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -60.0000
                 Phi: 270.0000
                 XTD: 45.0222
              2theta: -19.6851

;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       XPlain
_diffrn_orient_matrix_UB_11      -0.017122
_diffrn_orient_matrix_UB_12      0.037259
_diffrn_orient_matrix_UB_13      0.065417
_diffrn_orient_matrix_UB_21      -0.134388
_diffrn_orient_matrix_UB_22      -0.024008
_diffrn_orient_matrix_UB_23      -0.021499
_diffrn_orient_matrix_UB_31      0.010603
_diffrn_orient_matrix_UB_32      -0.038896
_diffrn_orient_matrix_UB_33      -0.022839
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5675
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.412
_diffrn_reflns_theta_min         3.294
_diffrn_reflns_transf_matrix_11  -0.017122
_diffrn_reflns_transf_matrix_12  0.037259
_diffrn_reflns_transf_matrix_13  0.065417
_diffrn_reflns_transf_matrix_21  -0.134388
_diffrn_reflns_transf_matrix_22  -0.024008
_diffrn_reflns_transf_matrix_23  -0.021499
_diffrn_reflns_transf_matrix_31  0.010603
_diffrn_reflns_transf_matrix_32  -0.038896
_diffrn_reflns_transf_matrix_33  -0.022839
_diffrn_source                   MicroMax003_Mo
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       Block
_exptl_crystal_F_000             452
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methnol'
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0719
_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^)+(0.1115P)^2^+0.0316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1810
_refine_ls_wR_factor_ref         0.2064
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1099
_reflns_number_total             1856
_reflns_shell_number_unique_all  3718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cp03164b2.cif
_cod_data_source_block           1b
_cod_database_code               7233537
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              47637