#------------------------------------------------------------------------------
#$Date: 2019-08-29 06:09:46 +0300 (Thu, 29 Aug 2019) $
#$Revision: 217820 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/35/7233533.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7233533
loop_
_publ_author_name
'Dash, Sibananda G.'
'Thakur, Tejender S.'
_publ_section_title
;
 Cation∙∙∙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(C4 H4 O4)'
_chemical_formula_sum            'C11 H16 N O4'
_chemical_formula_weight         226.25
_chemical_name_common            '(+/-)-Synephrine Succinic Acid (1:0.5) Salt'
_chemical_name_systematic        '(+/-)-Synephrine Succinic 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'
_symmetry_space_group_name_H-M   'P -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                99.477(7)
_cell_angle_beta                 93.462(7)
_cell_angle_gamma                107.504(8)
_cell_formula_units_Z            2
_cell_length_a                   5.8474(10)
_cell_length_b                   8.9093(15)
_cell_length_c                   11.586(2)
_cell_measurement_reflns_used    3400
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     563.89(17)
_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 0.963
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details
;
scan:
    Number of images: 200
               Slice: -30.0000 - 70.0000
         Image width: 0.5000
            Exp time: 4.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 60.0000
                 Phi: 0.0000
                 XTD: 44.7431
              2theta: -19.6764
scan:
    Number of images: 200
               Slice: -30.0000 - 70.0000
         Image width: 0.5000
            Exp time: 4.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 60.0000
                 Phi: 90.0000
                 XTD: 44.7431
              2theta: -19.6764
scan:
    Number of images: 200
               Slice: -110.0000 - -10.0000
         Image width: 0.5000
            Exp time: 4.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -60.0000
                 Phi: 180.0000
                 XTD: 44.7431
              2theta: -19.6764
scan:
    Number of images: 200
               Slice: -110.0000 - -10.0000
         Image width: 0.5000
            Exp time: 4.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -60.0000
                 Phi: 270.0000
                 XTD: 44.7431
              2theta: -19.6764

;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       XPlain
_diffrn_orient_matrix_UB_11      0.133807
_diffrn_orient_matrix_UB_12      -0.045520
_diffrn_orient_matrix_UB_13      0.013956
_diffrn_orient_matrix_UB_21      -0.057890
_diffrn_orient_matrix_UB_22      -0.077897
_diffrn_orient_matrix_UB_23      -0.076402
_diffrn_orient_matrix_UB_31      0.106511
_diffrn_orient_matrix_UB_32      0.079005
_diffrn_orient_matrix_UB_33      -0.041607
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4544
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.443
_diffrn_reflns_transf_matrix_11  0.133807
_diffrn_reflns_transf_matrix_12  -0.045520
_diffrn_reflns_transf_matrix_13  0.013956
_diffrn_reflns_transf_matrix_21  -0.057890
_diffrn_reflns_transf_matrix_22  -0.077897
_diffrn_reflns_transf_matrix_23  -0.076402
_diffrn_reflns_transf_matrix_31  0.106511
_diffrn_reflns_transf_matrix_32  0.079005
_diffrn_reflns_transf_matrix_33  -0.041607
_diffrn_source                   MicroMax003_Mo
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       Block
_exptl_crystal_F_000             242
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methnol'
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0604
_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/[σ²(Fo²)+(0.0676P)²+0.1458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1628
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1539
_reflns_number_total             2453
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cp03164b2.cif
_cod_data_source_block           1d
_cod_database_code               7233533
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.2228(4) 0.2795(3) 0.5800(2) 0.0390(6) Uani 1 1 d . .
C2 C 0.0357(5) 0.3014(3) 0.5134(2) 0.0447(6) Uani 1 1 d . .
H2 H -0.0430 0.3714 0.5468 0.054 Uiso 1 1 calc R U
C3 C -0.0368(5) 0.2211(3) 0.3981(2) 0.0505(7) Uani 1 1 d . .
H3 H -0.1625 0.2381 0.3546 0.061 Uiso 1 1 calc R U
C4 C 0.0760(4) 0.1160(3) 0.3473(2) 0.0402(6) Uani 1 1 d . .
C5 C 0.2702(5) 0.0988(3) 0.4109(2) 0.0521(7) Uani 1 1 d . .
H5 H 0.3539 0.0330 0.3760 0.062 Uiso 1 1 calc R U
C6 C 0.3410(5) 0.1784(3) 0.5257(2) 0.0511(7) Uani 1 1 d . .
H6 H 0.4709 0.1642 0.5679 0.061 Uiso 1 1 calc R U
C7 C 0.2957(4) 0.3536(3) 0.7098(2) 0.0412(6) Uani 1 1 d . .
H7 H 0.3098 0.2690 0.7516 0.049 Uiso 1 1 calc R U
C8 C 0.5365(4) 0.4852(3) 0.7317(2) 0.0404(6) Uani 1 1 d . .
H8A H 0.6580 0.4454 0.6960 0.049 Uiso 1 1 calc R U
H8B H 0.5243 0.5745 0.6966 0.049 Uiso 1 1 calc R U
C9 C 0.8516(5) 0.6559(3) 0.8960(2) 0.0513(7) Uani 1 1 d . .
H9A H 0.8649 0.7488 0.8619 0.062 Uiso 1 1 calc R U
H9B H 0.9696 0.6075 0.8688 0.062 Uiso 1 1 calc R U
H9C H 0.8791 0.6869 0.9803 0.062 Uiso 1 1 calc R U
C10 C 0.6475(4) 0.1691(3) 0.91383(19) 0.0343(5) Uani 1 1 d . .
C11 C 0.5763(5) 0.0083(3) 0.9509(2) 0.0479(7) Uani 1 1 d . .
H11A H 0.4906 -0.0727 0.8829 0.057 Uiso 1 1 calc R U
H11B H 0.7227 -0.0148 0.9737 0.057 Uiso 1 1 calc R U
N3 N 0.6071(4) 0.5393(2) 0.86076(17) 0.0375(5) Uani 1 1 d . .
O1 O -0.0081(4) 0.0323(2) 0.23533(16) 0.0554(5) Uani 1 1 d . .
O2 O 0.1272(3) 0.4213(2) 0.76191(16) 0.0502(5) Uani 1 1 d . .
O4 O 0.5796(3) 0.28006(18) 0.96484(14) 0.0444(5) Uani 1 1 d . .
O5 O 0.7752(3) 0.18259(19) 0.82949(15) 0.0509(5) Uani 1 1 d . .
H1A H 0.087(6) -0.028(4) 0.219(3) 0.081(11) Uiso 1 1 d . .
H2A H 0.015(8) 0.335(5) 0.781(4) 0.125(16) Uiso 1 1 d . .
H3A H 0.498(5) 0.587(3) 0.892(3) 0.061(8) Uiso 1 1 d . .
H3B H 0.596(5) 0.447(3) 0.895(2) 0.052(7) Uiso 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C2 C1 C6 117.6(2) .
C2 C1 C7 123.3(2) .
C6 C1 C7 119.0(2) .
C1 C2 C3 121.2(2) .
C1 C2 H2 119.4 .
C3 C2 H2 119.4 .
C4 C3 C2 120.4(2) .
C4 C3 H3 119.8 .
C2 C3 H3 119.8 .
O1 C4 C3 118.9(2) .
O1 C4 C5 122.1(2) .
C3 C4 C5 119.0(2) .
C6 C5 C4 120.3(2) .
C6 C5 H5 119.8 .
C4 C5 H5 119.8 .
C5 C6 C1 121.4(2) .
C5 C6 H6 119.3 .
C1 C6 H6 119.3 .
O2 C7 C8 106.59(19) .
O2 C7 C1 113.6(2) .
C8 C7 C1 112.36(19) .
O2 C7 H7 108.0 .
C8 C7 H7 108.0 .
C1 C7 H7 108.0 .
N3 C8 C7 109.08(19) .
N3 C8 H8A 109.9 .
C7 C8 H8A 109.9 .
N3 C8 H8B 109.9 .
C7 C8 H8B 109.9 .
H8A C8 H8B 108.3 .
N3 C9 H9A 109.5 .
N3 C9 H9B 109.5 .
H9A C9 H9B 109.5 .
N3 C9 H9C 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
O4 C10 O5 123.2(2) .
O4 C10 C11 120.3(2) .
O5 C10 C11 116.46(19) .
C11 C11 C10 116.5(2) 2_657
C11 C11 H11A 108.2 2_657
C10 C11 H11A 108.2 .
C11 C11 H11B 108.2 2_657
C10 C11 H11B 108.2 .
H11A C11 H11B 107.3 .
C9 N3 C8 115.3(2) .
C9 N3 H3A 107.7(18) .
C8 N3 H3A 108.4(18) .
C9 N3 H3B 108.9(16) .
C8 N3 H3B 108.3(15) .
H3A N3 H3B 108(2) .
C4 O1 H1A 105(2) .
C7 O2 H2A 103(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.380(3) .
C1 C6 1.388(3) .
C1 C7 1.519(3) .
C2 C3 1.382(3) .
C2 H2 0.9300 .
C3 C4 1.376(3) .
C3 H3 0.9300 .
C4 O1 1.366(3) .
C4 C5 1.377(4) .
C5 C6 1.375(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 O2 1.417(3) .
C7 C8 1.513(3) .
C7 H7 0.9800 .
C8 N3 1.485(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 N3 1.479(3) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 O4 1.248(2) .
C10 O5 1.265(3) .
C10 C11 1.508(3) .
C11 C11 1.487(5) 2_657
C11 H11A 0.9700 .
C11 H11B 0.9700 .
N3 H3A 0.93(3) .
N3 H3B 0.96(3) .
O1 H1A 0.89(3) .
O2 H2A 0.92(4) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 2.3(4) .
C7 C1 C2 C3 -174.6(2) .
C1 C2 C3 C4 0.5(4) .
C2 C3 C4 O1 176.7(2) .
C2 C3 C4 C5 -3.5(4) .
O1 C4 C5 C6 -176.4(2) .
C3 C4 C5 C6 3.8(4) .
C4 C5 C6 C1 -1.0(4) .
C2 C1 C6 C5 -2.0(4) .
C7 C1 C6 C5 175.1(2) .
C2 C1 C7 O2 11.4(3) .
C6 C1 C7 O2 -165.4(2) .
C2 C1 C7 C8 -109.7(3) .
C6 C1 C7 C8 73.4(3) .
O2 C7 C8 N3 60.9(2) .
C1 C7 C8 N3 -174.04(19) .
O4 C10 C11 C11 0.2(4) 2_657
O5 C10 C11 C11 -179.3(3) 2_657
C7 C8 N3 C9 173.7(2) .
