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_7233542
_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         '2(C9 H14 N O2), C4 H4 O6'
_chemical_formula_sum            'C22 H32 N2 O10'
_chemical_formula_weight         484.49
_chemical_name_common            '(+/-) Synephrine L-tarataric acid salt (2:1)'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-05-07 deposited with the CCDC.    2019-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                101.243(5)
_cell_angle_beta                 91.903(5)
_cell_angle_gamma                105.888(6)
_cell_formula_units_Z            1
_cell_length_a                   5.6127(4)
_cell_length_b                   9.3029(7)
_cell_length_c                   11.6456(6)
_cell_measurement_reflns_used    3604
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.9960
_cell_measurement_theta_min      2.3610
_cell_volume                     571.19(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_details
;
scan:
    Number of images: 200
               Slice: -30.0000 - 70.0000
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 60.0000
                 Phi: 0.0000
                 XTD: 44.6323
              2theta: -19.6867
scan:
    Number of images: 200
               Slice: -30.0000 - 70.0000
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 60.0000
                 Phi: 90.0000
                 XTD: 44.6323
              2theta: -19.6867
scan:
    Number of images: 200
               Slice: -110.0000 - -10.0000
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -60.0000
                 Phi: 180.0000
                 XTD: 44.6323
              2theta: -19.6867
scan:
    Number of images: 200
               Slice: -110.0000 - -10.0000
         Image width: 0.5000
            Exp time: 6.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -60.0000
                 Phi: 270.0000
                 XTD: 44.6323
              2theta: -19.6867

;
_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'
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_diffrn_orient_matrix_UB_12      0.145877
_diffrn_orient_matrix_UB_13      0.043558
_diffrn_orient_matrix_UB_21      -0.069113
_diffrn_orient_matrix_UB_22      0.077660
_diffrn_orient_matrix_UB_23      0.047745
_diffrn_orient_matrix_UB_31      0.005853
_diffrn_orient_matrix_UB_32      -0.019390
_diffrn_orient_matrix_UB_33      0.085635
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6247
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.373
_diffrn_reflns_theta_min         2.620
_diffrn_reflns_transf_matrix_11  0.105599
_diffrn_reflns_transf_matrix_12  0.145877
_diffrn_reflns_transf_matrix_13  0.043558
_diffrn_reflns_transf_matrix_21  -0.069113
_diffrn_reflns_transf_matrix_22  0.077660
_diffrn_reflns_transf_matrix_23  0.047745
_diffrn_reflns_transf_matrix_31  0.005853
_diffrn_reflns_transf_matrix_32  -0.019390
_diffrn_reflns_transf_matrix_33  0.085635
_diffrn_source                   MicroMax003_Mo
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       Block
_exptl_crystal_F_000             258
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   2.5(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         3932
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0518P)^2^+0.0886P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                3142
_reflns_number_total             3932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cp03164b2.cif
_cod_data_source_block           SD20170302CM1_RT
_cod_database_code               7233542
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              76427