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_7233540
_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 H2 O4, H O'
_chemical_formula_sum            'C11 H15.5 N O4.5'
_chemical_formula_weight         233.74
_chemical_name_common            'Synephrine-DL-Malic acid 1:0.5 salt'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_hydrogens   mixed
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_audit_update_record
;
2019-05-07 deposited with the CCDC.    2019-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                100.209(5)
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_cell_measurement_temperature    100(2)
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_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details
;
scan:
    Number of images: 200
               Slice: -30.0000 - 70.0000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 60.0000
                 Phi: 90.0000
                 XTD: 44.7188
              2theta: -19.6555
scan:
    Number of images: 200
               Slice: -30.0000 - 70.0000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 60.0000
                 Phi: 0.0000
                 XTD: 44.7188
              2theta: -19.6555
scan:
    Number of images: 200
               Slice: -110.0000 - -10.0000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -60.0000
                 Phi: 180.0000
                 XTD: 44.7188
              2theta: -19.6555
scan:
    Number of images: 200
               Slice: -110.0000 - -10.0000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -60.0000
                 Phi: 270.0000
                 XTD: 44.7188
              2theta: -19.6555

;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
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_diffrn_orient_matrix_UB_22      -0.089903
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_diffrn_radiation_type           'Mo K\a'
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_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6116
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.408
_diffrn_reflns_theta_min         2.405
_diffrn_reflns_transf_matrix_11  0.016942
_diffrn_reflns_transf_matrix_12  0.067569
_diffrn_reflns_transf_matrix_13  -0.167440
_diffrn_reflns_transf_matrix_21  -0.017320
_diffrn_reflns_transf_matrix_22  -0.089903
_diffrn_reflns_transf_matrix_23  -0.074463
_diffrn_reflns_transf_matrix_31  -0.086154
_diffrn_reflns_transf_matrix_32  0.005452
_diffrn_reflns_transf_matrix_33  -0.012759
_diffrn_source                   MicroMax003_Mo
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.464
_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    1.369
_exptl_crystal_description       Block
_exptl_crystal_F_000             249
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_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.451
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         3198
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0703
_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^)+(0.0817P)^2^+0.2703P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1913
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2321
_reflns_number_total             3198
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cp03164b2.cif
_cod_data_source_block           SD20170422io_100K
_cod_original_cell_volume        567.16(5)
_cod_original_formula_sum        'C11 H15.50 N O4.50'
_cod_database_code               7233540
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              67911