#------------------------------------------------------------------------------
#$Date: 2019-08-29 06:09:46 +0300 (Thu, 29 Aug 2019) $
#$Revision: 217820 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/35/7233540.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_7233540
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         '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'
_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                100.209(5)
_cell_angle_beta                 90.688(4)
_cell_angle_gamma                106.188(5)
_cell_formula_units_Z            2
_cell_length_a                   5.7487(3)
_cell_length_b                   8.9795(5)
_cell_length_c                   11.6493(6)
_cell_measurement_reflns_used    2839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.5800
_cell_measurement_theta_min      2.4330
_cell_volume                     567.16(6)
_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      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)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_orient_matrix_type       XPlain
_diffrn_orient_matrix_UB_11      0.016942
_diffrn_orient_matrix_UB_12      0.067569
_diffrn_orient_matrix_UB_13      -0.167440
_diffrn_orient_matrix_UB_21      -0.017320
_diffrn_orient_matrix_UB_22      -0.089903
_diffrn_orient_matrix_UB_23      -0.074463
_diffrn_orient_matrix_UB_31      -0.086154
_diffrn_orient_matrix_UB_32      0.005452
_diffrn_orient_matrix_UB_33      -0.012759
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0583
_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
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.065
_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         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/[σ²(Fo²)+(0.0817P)²+0.2703P] where P=(Fo²+2Fc²)/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 > 2σ(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_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   0.960
_shelx_estimated_absorpt_t_max   0.989
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
_atom_site_refinement_flags_occupancy
C1 C 0.7175(4) 0.7745(2) 0.58075(18) 0.0272(4) Uani 1 1 d . . .
C2 C 0.5305(4) 0.8061(2) 0.52112(19) 0.0311(4) Uani 1 1 d . . .
H2 H 0.454011 0.880663 0.559348 0.037 Uiso 1 1 calc R U .
C3 C 0.4544(4) 0.7309(3) 0.40743(19) 0.0323(5) Uani 1 1 d . . .
H3 H 0.327007 0.754175 0.367931 0.039 Uiso 1 1 calc R U .
C4 C 0.5639(4) 0.6217(2) 0.35103(17) 0.0272(4) Uani 1 1 d . . .
C5 C 0.7584(4) 0.5942(2) 0.40644(19) 0.0331(5) Uani 1 1 d . . .
H5 H 0.840411 0.524001 0.366514 0.040 Uiso 1 1 calc R U .
C6 C 0.8321(4) 0.6703(3) 0.52097(19) 0.0338(5) Uani 1 1 d . . .
H6 H 0.964166 0.650461 0.559208 0.041 Uiso 1 1 calc R U .
C7 C 0.7903(4) 0.8438(2) 0.70865(18) 0.0293(4) Uani 1 1 d . . .
H7 H 0.817061 0.758924 0.747892 0.035 Uiso 1 1 calc R U .
C8 C 1.0239(4) 0.9798(2) 0.72534(18) 0.0296(4) Uani 1 1 d . . .
H8A H 1.155982 0.944016 0.686254 0.036 Uiso 1 1 calc R U .
H8B H 0.999544 1.067370 0.690104 0.036 Uiso 1 1 calc R U .
C9 C 1.3299(4) 1.1543(3) 0.8815(2) 0.0358(5) Uani 1 1 d . . .
H9A H 1.457005 1.110724 0.846827 0.054 Uiso 1 1 calc R U .
H9B H 1.360885 1.181852 0.966654 0.054 Uiso 1 1 calc R U .
H9C H 1.330212 1.249022 0.850725 0.054 Uiso 1 1 calc R U .
C10 C 0.1718(4) 0.6796(2) -0.0667(2) 0.0316(5) Uani 1 1 d . . .
C11A C 0.1242(5) 0.5597(3) 0.0179(3) 0.0276(6) Uani 0.75 1 d . . P
C11B C 0.0765(16) 0.5022(10) -0.0503(8) 0.0291(16) Uani 0.25 1 d . . P
N3 N 1.0902(3) 1.0349(2) 0.85186(16) 0.0289(4) Uani 1 1 d . . .
O1 O 0.4735(3) 0.54215(18) 0.24048(14) 0.0354(4) Uani 1 1 d . . .
O2 O 0.6121(3) 0.90492(19) 0.76762(14) 0.0363(4) Uani 1 1 d . . .
O4 O 0.2919(3) 0.66307(19) -0.15492(14) 0.0417(4) Uani 1 1 d . . .
O5 O 0.0966(3) 0.79598(18) -0.03263(14) 0.0368(4) Uani 1 1 d . . .
O6 O 0.1026(7) 0.6409(4) 0.1399(3) 0.0434(9) Uani 0.5 1 d D . P
H1A H 0.566(7) 0.478(5) 0.204(3) 0.088(12) Uiso 1 1 d . . .
H2A H 0.497(5) 0.819(4) 0.793(3) 0.053(8) Uiso 1 1 d . . .
H3A H 1.084(5) 0.954(3) 0.883(2) 0.036(7) Uiso 1 1 d . . .
H3B H 0.975(5) 1.081(3) 0.888(2) 0.036(7) Uiso 1 1 d . . .
H11A H 0.245(5) 0.496(3) -0.003(2) 0.039(7) Uiso 1 1 d . . .
H6A H 0.212(11) 0.608(9) 0.181(6) 0.10(3) Uiso 0.5 1 d D . P
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
_geom_angle_site_symmetry_3
C6 C1 C2 118.01(19) . .
C6 C1 C7 119.52(18) . .
C2 C1 C7 122.41(18) . .
C3 C2 C1 121.10(19) . .
C2 C3 C4 119.94(19) . .
O1 C4 C3 118.28(18) . .
O1 C4 C5 121.74(18) . .
C3 C4 C5 119.98(19) . .
C4 C5 C6 119.25(19) . .
C1 C6 C5 121.56(19) . .
O2 C7 C1 113.08(17) . .
O2 C7 C8 106.17(16) . .
C1 C7 C8 112.04(17) . .
N3 C8 C7 108.80(16) . .
O5 C10 O4 124.8(2) . .
O5 C10 C11A 113.3(2) . .
O4 C10 C11A 121.7(2) . .
O5 C10 C11B 131.5(4) . .
O4 C10 C11B 100.1(4) . .
C11A C10 C11B 31.9(3) . .
C11B C11A C11B 87.7(8) . 2_565
C11B C11A O6 157.6(7) . .
C11B C11A O6 70.9(5) 2_565 .
C11B C11A C11A 53.4(6) . 2_565
C11B C11A C11A 34.3(4) 2_565 2_565
O6 C11A C11A 105.0(3) . 2_565
C11B C11A C10 75.6(6) . .
C11B C11A C10 124.5(5) 2_565 .
O6 C11A C10 110.5(2) . .
C11A C11A C10 108.3(3) 2_565 .
C11A C11B C11A 92.3(8) . 2_565
C11A C11B C11B 56.5(7) . 2_565
C11A C11B C11B 35.8(4) 2_565 2_565
C11A C11B C10 72.5(6) . .
C11A C11B C10 125.3(7) 2_565 .
C11B C11B C10 107.9(8) 2_565 .
C11A C11B O6 153.9(9) . 2_565
C11A C11B O6 62.5(5) 2_565 2_565
C11B C11B O6 98.1(8) 2_565 2_565
C10 C11B O6 126.4(6) . 2_565
C8 N3 C9 114.94(17) . .
C11A O6 C11B 46.6(3) . 2_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.385(3) .
C1 C2 1.393(3) .
C1 C7 1.514(3) .
C2 C3 1.380(3) .
C3 C4 1.384(3) .
C4 O1 1.375(2) .
C4 C5 1.386(3) .
C5 C6 1.389(3) .
C7 O2 1.421(2) .
C7 C8 1.526(3) .
C8 N3 1.478(3) .
C9 N3 1.484(3) .
C10 O5 1.243(3) .
C10 O4 1.254(3) .
C10 C11A 1.557(3) .
C10 C11B 1.581(8) .
C11A C11B 0.862(9) .
C11A C11B 1.229(9) 2_565
C11A O6 1.501(5) .
C11A C11A 1.529(5) 2_565
C11B C11B 1.473(18) 2_565
C11B O6 1.600(10) 2_565
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_1
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 2.7(3) . .
C7 C1 C2 C3 -174.45(19) . .
C1 C2 C3 C4 0.2(3) . .
C2 C3 C4 O1 176.07(19) . .
C2 C3 C4 C5 -3.5(3) . .
O1 C4 C5 C6 -175.83(19) . .
C3 C4 C5 C6 3.7(3) . .
C2 C1 C6 C5 -2.4(3) . .
C7 C1 C6 C5 174.8(2) . .
C4 C5 C6 C1 -0.7(3) . .
C6 C1 C7 O2 -160.71(19) . .
C2 C1 C7 O2 16.4(3) . .
C6 C1 C7 C8 79.4(2) . .
C2 C1 C7 C8 -103.5(2) . .
O2 C7 C8 N3 59.3(2) . .
C1 C7 C8 N3 -176.84(16) . .
O5 C10 C11A C11B 132.5(7) . .
O4 C10 C11A C11B -52.9(7) . .
O5 C10 C11A C11B 55.5(7) . 2_565
O4 C10 C11A C11B -129.8(6) . 2_565
C11B C10 C11A C11B -77.0(10) . 2_565
O5 C10 C11A O6 -25.0(3) . .
O4 C10 C11A O6 149.7(3) . .
C11B C10 C11A O6 -157.4(7) . .
O5 C10 C11A C11A 89.6(3) . 2_565
O4 C10 C11A C11A -95.7(3) . 2_565
C11B C10 C11A C11A -42.9(6) . 2_565
C11B C11A C11B C11A 0.001(1) 2_565 2_565
O6 C11A C11B C11A -17.4(19) . 2_565
C10 C11A C11B C11A -126.5(5) . 2_565
O6 C11A C11B C11B -17.4(19) . 2_565
C11A C11A C11B C11B -0.001(1) 2_565 2_565
C10 C11A C11B C11B -126.5(5) . 2_565
C11B C11A C11B C10 126.5(6) 2_565 .
O6 C11A C11B C10 109.1(15) . .
C11A C11A C11B C10 126.5(5) 2_565 .
C11B C11A C11B O6 -14.0(16) 2_565 2_565
O6 C11A C11B O6 -31(3) . 2_565
C11A C11A C11B O6 -14.0(16) 2_565 2_565
C10 C11A C11B O6 -141(2) . 2_565
O5 C10 C11B C11A -64.9(8) . .
O4 C10 C11B C11A 136.5(5) . .
O5 C10 C11B C11A 15.2(12) . 2_565
O4 C10 C11B C11A -143.5(8) . 2_565
C11A C10 C11B C11A 80.0(10) . 2_565
O5 C10 C11B C11B -20.1(12) . 2_565
O4 C10 C11B C11B -178.8(8) . 2_565
C11A C10 C11B C11B 44.7(6) . 2_565
O5 C10 C11B O6 94.8(8) . 2_565
O4 C10 C11B O6 -63.9(7) . 2_565
C11A C10 C11B O6 159.7(12) . 2_565
C7 C8 N3 C9 172.89(18) . .
C11B C11A O6 C11B 18(2) . 2_565
C11A C11A O6 C11B 4.0(4) 2_565 2_565
C10 C11A O6 C11B 120.7(5) . 2_565
