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_7233536
_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(C6 H8 O4), H2 O'
_chemical_formula_sum            'C12 H20 N O5'
_chemical_formula_weight         258.29
_chemical_name_common
'(+/-)-Synephrine adipic acid (1:0.5) Salt Monohydrate'
_chemical_name_systematic
'(+/-)-Synephrine adipic acid (1:0.5) Salt Monohydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 99.968(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.0334(19)
_cell_length_b                   5.4264(2)
_cell_length_c                   18.2828(10)
_cell_measurement_reflns_used    10370
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      2.9
_cell_volume                     2739.2(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
scan:
    Number of images: 100
               Slice: -30.0000 - 70.0000
         Image width: 1.0000
            Exp time: 4.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 60.0000
                 Phi: 0.0000
                 XTD: 44.5925
              2theta: -19.7185
scan:
    Number of images: 100
               Slice: -30.0000 - 70.0000
         Image width: 1.0000
            Exp time: 4.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 60.0000
                 Phi: 90.0000
                 XTD: 44.5925
              2theta: -19.7185
scan:
    Number of images: 100
               Slice: -110.0000 - -10.0000
         Image width: 1.0000
            Exp time: 4.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -60.0000
                 Phi: 180.0000
                 XTD: 44.5925
              2theta: -19.7185
scan:
    Number of images: 100
               Slice: -110.0000 - -10.0000
         Image width: 1.0000
            Exp time: 4.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -60.0000
                 Phi: 270.0000
                 XTD: 44.5925
              2theta: -19.7185

;
_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      -0.001594
_diffrn_orient_matrix_UB_12      -0.161054
_diffrn_orient_matrix_UB_13      -0.017487
_diffrn_orient_matrix_UB_21      0.053359
_diffrn_orient_matrix_UB_22      0.020222
_diffrn_orient_matrix_UB_23      -0.003055
_diffrn_orient_matrix_UB_31      0.015309
_diffrn_orient_matrix_UB_32      -0.087253
_diffrn_orient_matrix_UB_33      0.031570
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11505
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         2.907
_diffrn_reflns_transf_matrix_11  -0.001594
_diffrn_reflns_transf_matrix_12  -0.161054
_diffrn_reflns_transf_matrix_13  -0.017487
_diffrn_reflns_transf_matrix_21  0.053359
_diffrn_reflns_transf_matrix_22  0.020222
_diffrn_reflns_transf_matrix_23  -0.003055
_diffrn_reflns_transf_matrix_31  0.015309
_diffrn_reflns_transf_matrix_32  -0.087253
_diffrn_reflns_transf_matrix_33  0.031570
_diffrn_source                   MicroMax003_Mo
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       Block
_exptl_crystal_F_000             1112
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methnol'
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0674
_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^)+(0.0679P)^2^+2.3183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1833
_reflns_number_total             3126
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cp03164b2.cif
_cod_data_source_block           1f
_cod_database_code               7233536
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              91938