# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1d
_database_code_depnum_ccdc_archive 'CCDC 1535422'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(+/-)-Synephrine Succinic Acid (1:0.5) Salt'
_chemical_name_common            '(+/-)-Synephrine Succinic Acid (1:0.5) Salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H14 N O2, 0.5(C4 H4 O4)'
_chemical_formula_sum            'C11 H16 N O4'
_chemical_formula_weight         226.25

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8474(10)
_cell_length_b                   8.9093(15)
_cell_length_c                   11.586(2)
_cell_angle_alpha                99.477(7)
_cell_angle_beta                 93.462(7)
_cell_angle_gamma                107.504(8)
_cell_volume                     563.89(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3400
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             242
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.557
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_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_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_orient_matrix_type       XPlain
_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_reflns_number            4544
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.443
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             2453
_reflns_number_gt                1539
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0676P)²+0.1458P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2453
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1628
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methnol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1c
_database_code_depnum_ccdc_archive 'CCDC 1535425'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        '(+/-)-Synephrine Fumaric Acid (1:0.5) Salt'
_chemical_name_common            '(+/-)-Synephrine Fumaric Acid (1:0.5) Salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H14 N O2, 0.5(C4 H2 O4)'
_chemical_formula_sum            'C11 H15 N O4'
_chemical_formula_weight         225.24

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.045(2)
_cell_length_b                   5.6577(8)
_cell_length_c                   16.169(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.412(17)
_cell_angle_gamma                90
_cell_volume                     1138.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2133
_cell_measurement_theta_min      3.2360
_cell_measurement_theta_max      28.6380

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_T_min  0.84082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_details      
;
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 0.0000
	             XTD: 44.6531
	          2theta: -19.6489
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 90.0000
	             XTD: 44.6531
	          2theta: -19.6489
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 180.0000
	             XTD: 44.6531
	          2theta: -19.6489
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 270.0000
	             XTD: 44.6531
	          2theta: -19.6489

;
_diffrn_orient_matrix_UB_11      0.018458
_diffrn_orient_matrix_UB_12      0.078145
_diffrn_orient_matrix_UB_13      -0.003504
_diffrn_orient_matrix_UB_21      -0.066555
_diffrn_orient_matrix_UB_22      0.022976
_diffrn_orient_matrix_UB_23      0.161832
_diffrn_orient_matrix_UB_31      0.059878
_diffrn_orient_matrix_UB_32      0.006831
_diffrn_orient_matrix_UB_33      0.023656
_diffrn_orient_matrix_type       XPlain
_diffrn_reflns_transf_matrix_11  0.018458
_diffrn_reflns_transf_matrix_12  0.078145
_diffrn_reflns_transf_matrix_13  -0.003504
_diffrn_reflns_transf_matrix_21  -0.066555
_diffrn_reflns_transf_matrix_22  0.022976
_diffrn_reflns_transf_matrix_23  0.161832
_diffrn_reflns_transf_matrix_31  0.059878
_diffrn_reflns_transf_matrix_32  0.006831
_diffrn_reflns_transf_matrix_33  0.023656
_diffrn_reflns_number            11372
_diffrn_reflns_av_unetI/netI     0.1084
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.273
_diffrn_reflns_theta_max         31.329
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3423
_reflns_number_gt                1954
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+0.5773P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3423
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1560
_refine_ls_R_factor_gt           0.0874
_refine_ls_wR_factor_ref         0.1897
_refine_ls_wR_factor_gt          0.1534
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8846(2) 0.0744(5) 0.85619(16) 0.0237(6) Uani 1 1 d . . . . .
C2 C 0.9326(2) -0.1095(5) 0.82478(17) 0.0284(6) Uani 1 1 d . . . . .
H2 H 0.888753 -0.221264 0.786210 0.034 Uiso 1 1 calc R U . . .
C3 C 1.0434(2) -0.1336(6) 0.84852(19) 0.0319(7) Uani 1 1 d . . . . .
H3 H 1.074735 -0.263306 0.827575 0.038 Uiso 1 1 calc R U . . .
C4 C 1.1084(2) 0.0317(5) 0.90285(17) 0.0268(6) Uani 1 1 d . . . . .
C5 C 1.0615(2) 0.2188(5) 0.93288(18) 0.0321(7) Uani 1 1 d . . . . .
H5 H 1.105434 0.334805 0.969188 0.039 Uiso 1 1 calc R U . . .
C6 C 0.9509(2) 0.2378(5) 0.91029(18) 0.0314(7) Uani 1 1 d . . . . .
H6 H 0.919754 0.365670 0.932357 0.038 Uiso 1 1 calc R U . . .
C7 C 0.7641(2) 0.1101(5) 0.82936(17) 0.0256(6) Uani 1 1 d . . . . .
H7 H 0.744483 0.180677 0.879287 0.031 Uiso 1 1 calc R U . . .
C8 C 0.7312(2) 0.2805(5) 0.75406(16) 0.0247(6) Uani 1 1 d . . . . .
H8A H 0.770388 0.431481 0.770542 0.030 Uiso 1 1 calc R U . . .
H8B H 0.750562 0.213970 0.704106 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5769(2) 0.5017(5) 0.65825(17) 0.0283(6) Uani 1 1 d . . . . .
H9A H 0.608891 0.655864 0.678625 0.042 Uiso 1 1 calc R U . . .
H9B H 0.498458 0.514213 0.641365 0.042 Uiso 1 1 calc R U . . .
H9C H 0.599169 0.451760 0.608163 0.042 Uiso 1 1 calc R U . . .
C10 C 0.5965(2) 0.5734(5) 0.93234(17) 0.0216(6) Uani 1 1 d . . . . .
C11 C 0.55031(19) 0.5334(5) 1.00560(17) 0.0220(6) Uani 1 1 d . . . . .
H11 H 0.595530 0.557182 1.063110 0.026 Uiso 1 1 calc R U . . .
N3 N 0.61374(17) 0.3252(4) 0.72878(15) 0.0227(5) Uani 1 1 d . . . . .
O1 O 1.21703(16) 0.0023(4) 0.92499(14) 0.0379(6) Uani 1 1 d . . . . .
O2 O 0.70385(15) -0.0993(4) 0.80385(13) 0.0316(5) Uani 1 1 d . . . . .
O4 O 0.54269(14) 0.4996(3) 0.85794(11) 0.0231(4) Uani 1 1 d . . . . .
O5 O 0.68503(14) 0.6773(4) 0.94891(11) 0.0296(5) Uani 1 1 d . . . . .
H3A H 0.574(2) 0.192(5) 0.7103(16) 0.018(7) Uiso 1 1 d . . . . .
H3B H 0.595(2) 0.383(6) 0.781(2) 0.045(9) Uiso 1 1 d . . . . .
H1A H 1.252(3) 0.121(7) 0.964(2) 0.071(13) Uiso 1 1 d . . . . .
H2A H 0.700(3) -0.206(7) 0.859(2) 0.073(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.384(4) . ?
C1 C2 1.387(4) . ?
C1 C7 1.514(4) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 O1 1.365(3) . ?
C4 C5 1.381(4) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O2 1.413(3) . ?
C7 C8 1.511(4) . ?
C7 H7 1.0000 . ?
C8 N3 1.485(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.483(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 O5 1.252(3) . ?
C10 O4 1.268(3) . ?
C10 C11 1.498(3) . ?
C11 C11 1.325(5) 3_667 ?
C11 H11 0.9500 . ?
N3 H3A 0.92(3) . ?
N3 H3B 1.00(3) . ?
O1 H1A 0.94(4) . ?
O2 H2A 1.09(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
_geom_angle_publ_flag
C6 C1 C2 117.8(2) . . ?
C6 C1 C7 119.4(2) . . ?
C2 C1 C7 122.7(2) . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
O1 C4 C5 122.4(3) . . ?
O1 C4 C3 118.3(3) . . ?
C5 C4 C3 119.3(3) . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O2 C7 C8 107.5(2) . . ?
O2 C7 C1 114.2(2) . . ?
C8 C7 C1 109.6(2) . . ?
O2 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
C1 C7 H7 108.4 . . ?
N3 C8 C7 110.6(2) . . ?
N3 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
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 . . ?
O5 C10 O4 124.8(2) . . ?
O5 C10 C11 117.7(2) . . ?
O4 C10 C11 117.5(2) . . ?
C11 C11 C10 123.4(3) 3_667 . ?
C11 C11 H11 118.3 3_667 . ?
C10 C11 H11 118.3 . . ?
C9 N3 C8 113.3(2) . . ?
C9 N3 H3A 106.4(16) . . ?
C8 N3 H3A 113.0(16) . . ?
C9 N3 H3B 108.8(18) . . ?
C8 N3 H3B 108.6(17) . . ?
H3A N3 H3B 106(2) . . ?
C4 O1 H1A 110(2) . . ?
C7 O2 H2A 112(2) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.8(4) . . . . ?
C7 C1 C2 C3 178.0(3) . . . . ?
C1 C2 C3 C4 -1.8(4) . . . . ?
C2 C3 C4 O1 179.9(3) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
O1 C4 C5 C6 -178.4(3) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C4 C5 C6 C1 -1.2(4) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C7 C1 C6 C5 -176.6(3) . . . . ?
C6 C1 C7 O2 -156.9(2) . . . . ?
C2 C1 C7 O2 26.9(4) . . . . ?
C6 C1 C7 C8 82.4(3) . . . . ?
C2 C1 C7 C8 -93.8(3) . . . . ?
O2 C7 C8 N3 57.4(3) . . . . ?
C1 C7 C8 N3 -177.9(2) . . . . ?
O5 C10 C11 C11 167.0(3) . . . 3_667 ?
O4 C10 C11 C11 -12.8(5) . . . 3_667 ?
C7 C8 N3 C9 176.8(2) . . . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.068


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methnol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1e
_database_code_depnum_ccdc_archive 'CCDC 1535424'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(+/-)-Synephrine Glutaric acid (1:0.5) Salt'
_chemical_name_common            '(+/-)-Synephrine Glutaric acid (1:0.5) Salt'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H14 N O2), C5 H6 O4'
_chemical_formula_sum            'C23 H34 N2 O8'
_chemical_formula_weight         466.52

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.704(7)
_cell_length_b                   6.200(3)
_cell_length_c                   21.990(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.751(11)
_cell_angle_gamma                90
_cell_volume                     2385.6(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1745
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.471
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_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: 44.7275
	          2theta: -19.6260
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: 44.7275
	          2theta: -19.6260
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: 44.7275
	          2theta: -19.6260
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: 44.7275
	          2theta: -19.6260

;
_diffrn_orient_matrix_UB_11      0.049818
_diffrn_orient_matrix_UB_12      -0.006174
_diffrn_orient_matrix_UB_13      0.027313
_diffrn_orient_matrix_UB_21      0.029085
_diffrn_orient_matrix_UB_22      -0.134874
_diffrn_orient_matrix_UB_23      -0.083537
_diffrn_orient_matrix_UB_31      0.026820
_diffrn_orient_matrix_UB_32      0.023694
_diffrn_orient_matrix_UB_33      -0.028918
_diffrn_orient_matrix_type       XPlain
_diffrn_reflns_transf_matrix_11  0.049818
_diffrn_reflns_transf_matrix_12  -0.006174
_diffrn_reflns_transf_matrix_13  0.027313
_diffrn_reflns_transf_matrix_21  0.029085
_diffrn_reflns_transf_matrix_22  -0.134874
_diffrn_reflns_transf_matrix_23  -0.083537
_diffrn_reflns_transf_matrix_31  0.026820
_diffrn_reflns_transf_matrix_32  0.023694
_diffrn_reflns_transf_matrix_33  -0.028918
_diffrn_reflns_number            9084
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.204
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2682
_reflns_number_gt                2100
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2682
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1203
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.35439(8) 0.9024(2) 0.44664(7) 0.0207(3) Uani 1 1 d . . . . .
C6 C 0.40591(9) 0.7457(2) 0.47230(7) 0.0263(3) Uani 1 1 d . . . . .
H6 H 0.4137 0.6211 0.4489 0.032 Uiso 1 1 calc R U . . .
C5 C 0.44603(8) 0.7674(2) 0.53116(7) 0.0254(3) Uani 1 1 d . . . . .
H5 H 0.4805 0.6578 0.5479 0.030 Uiso 1 1 calc R U . . .
C4 C 0.43562(8) 0.9505(2) 0.56568(7) 0.0212(3) Uani 1 1 d . . . . .
C3 C 0.38247(8) 1.1054(2) 0.54156(7) 0.0244(3) Uani 1 1 d . . . . .
H3 H 0.3736 1.2277 0.5655 0.029 Uiso 1 1 calc R U . . .
C2 C 0.34229(8) 1.0815(2) 0.48250(7) 0.0234(3) Uani 1 1 d . . . . .
H2 H 0.3062 1.1882 0.4664 0.028 Uiso 1 1 calc R U . . .
C7 C 0.31655(8) 0.8782(2) 0.38038(7) 0.0214(3) Uani 1 1 d . . . . .
H7 H 0.3564 0.8333 0.3553 0.026 Uiso 1 1 calc R U . . .
C8 C 0.25441(8) 0.7065(2) 0.37364(7) 0.0230(3) Uani 1 1 d . . . . .
H8A H 0.2749 0.5710 0.3935 0.028 Uiso 1 1 calc R U . . .
H8B H 0.2113 0.7550 0.3941 0.028 Uiso 1 1 calc R U . . .
C9 C 0.16678(8) 0.4997(2) 0.29551(7) 0.0231(3) Uani 1 1 d . . . . .
H9A H 0.1877 0.3607 0.3113 0.035 Uiso 1 1 calc R U . . .
H9B H 0.1490 0.4879 0.2512 0.035 Uiso 1 1 calc R U . . .
H9C H 0.1238 0.5396 0.3165 0.035 Uiso 1 1 calc R U . . .
C10 C 0.91225(8) 0.9301(2) 0.30357(7) 0.0211(3) Uani 1 1 d . . . . .
C11 C 0.99020(8) 1.0365(2) 0.30604(7) 0.0233(3) Uani 1 1 d . . . . .
H11A H 0.9993 1.1304 0.3429 0.028 Uiso 1 1 calc R U . . .
H11B H 1.0298 0.9226 0.3112 0.028 Uiso 1 1 calc R U . . .
C12 C 1.0000 1.1707(3) 0.2500 0.0242(4) Uani 1 2 d S T P . .
H12A H 1.0453 1.2648 0.2604 0.029 Uiso 0.5 1 calc R U P . .
H12B H 0.9547 1.2648 0.2396 0.029 Uiso 0.5 1 calc R U P . .
N3 N 0.22729(7) 0.66808(19) 0.30692(6) 0.0202(3) Uani 1 1 d . . . . .
O1 O 0.47599(6) 0.98313(17) 0.62287(5) 0.0273(3) Uani 1 1 d . . . . .
O2 O 0.28107(6) 1.06985(16) 0.35411(5) 0.0245(3) Uani 1 1 d . . . . .
O3 O 0.90728(6) 0.78331(19) 0.34279(5) 0.0322(3) Uani 1 1 d . . . . .
O4 O 0.85633(5) 0.99517(15) 0.26557(5) 0.0222(2) Uani 1 1 d . . . . .
H1A H 0.5139(13) 0.881(3) 0.6324(10) 0.054(6) Uiso 1 1 d . . . . .
H2A H 0.3252(14) 1.166(4) 0.3515(11) 0.068(7) Uiso 1 1 d . . . . .
H3A H 0.2061(10) 0.788(3) 0.2850(9) 0.042(5) Uiso 1 1 d . . . . .
H3B H 0.2694(9) 0.621(2) 0.2878(7) 0.019(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.392(2) . ?
C1 C2 1.397(2) . ?
C1 C7 1.516(2) . ?
C6 C5 1.385(2) . ?
C6 H6 0.9500 . ?
C5 C4 1.393(2) . ?
C5 H5 0.9500 . ?
C4 O1 1.3638(18) . ?
C4 C3 1.392(2) . ?
C3 C2 1.391(2) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C7 O2 1.4249(17) . ?
C7 C8 1.5216(19) . ?
C7 H7 1.0000 . ?
C8 N3 1.4918(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.4898(18) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 O4 1.2607(18) . ?
C10 O3 1.2663(18) . ?
C10 C11 1.523(2) . ?
C11 C12 1.5183(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C11 1.5184(18) 2_755 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
N3 H3A 0.93(2) . ?
N3 H3B 0.956(15) . ?
O1 H1A 0.92(2) . ?
O2 H2A 0.99(2) . ?

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
_geom_angle_publ_flag
C6 C1 C2 118.24(14) . . ?
C6 C1 C7 119.14(12) . . ?
C2 C1 C7 122.56(13) . . ?
C5 C6 C1 121.49(14) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C6 C5 C4 119.78(14) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
O1 C4 C3 118.55(13) . . ?
O1 C4 C5 121.95(13) . . ?
C3 C4 C5 119.50(14) . . ?
C2 C3 C4 120.17(13) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C2 C1 120.74(13) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
O2 C7 C1 114.21(11) . . ?
O2 C7 C8 106.04(12) . . ?
C1 C7 C8 111.74(11) . . ?
O2 C7 H7 108.2 . . ?
C1 C7 H7 108.2 . . ?
C8 C7 H7 108.2 . . ?
N3 C8 C7 109.10(11) . . ?
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 O3 123.54(13) . . ?
O4 C10 C11 120.07(13) . . ?
O3 C10 C11 116.33(13) . . ?
C12 C11 C10 115.02(11) . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 C11 113.59(16) . 2_755 ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 2_755 . ?
C11 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 2_755 . ?
H12A C12 H12B 107.7 . . ?
C9 N3 C8 113.15(11) . . ?
C9 N3 H3A 104.4(12) . . ?
C8 N3 H3A 115.2(12) . . ?
C9 N3 H3B 107.6(9) . . ?
C8 N3 H3B 109.0(10) . . ?
H3A N3 H3B 107.1(14) . . ?
C4 O1 H1A 111.6(14) . . ?
C7 O2 H2A 102.8(14) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C6 C5 -1.7(2) . . . . ?
C7 C1 C6 C5 175.48(13) . . . . ?
C1 C6 C5 C4 -0.6(2) . . . . ?
C6 C5 C4 O1 -177.38(13) . . . . ?
C6 C5 C4 C3 2.8(2) . . . . ?
O1 C4 C3 C2 177.61(12) . . . . ?
C5 C4 C3 C2 -2.5(2) . . . . ?
C4 C3 C2 C1 0.2(2) . . . . ?
C6 C1 C2 C3 1.9(2) . . . . ?
C7 C1 C2 C3 -175.14(13) . . . . ?
C6 C1 C7 O2 -164.61(13) . . . . ?
C2 C1 C7 O2 12.44(18) . . . . ?
C6 C1 C7 C8 75.03(16) . . . . ?
C2 C1 C7 C8 -107.92(15) . . . . ?
O2 C7 C8 N3 63.02(14) . . . . ?
C1 C7 C8 N3 -171.95(11) . . . . ?
O4 C10 C11 C12 -16.98(19) . . . . ?
O3 C10 C11 C12 165.79(13) . . . . ?
C10 C11 C12 C11 -74.59(11) . . . 2_755 ?
C7 C8 N3 C9 179.26(11) . . . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.063


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methnol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1f
_database_code_depnum_ccdc_archive 'CCDC 1535428'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(+/-)-Synephrine adipic acid (1:0.5) Salt Monohydrate'
_chemical_name_common            
'(+/-)-Synephrine adipic acid (1:0.5) Salt Monohydrate'
_chemical_melting_point          ?
_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

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.0334(19)
_cell_length_b                   5.4264(2)
_cell_length_c                   18.2828(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.968(7)
_cell_angle_gamma                90
_cell_volume                     2739.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10370
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.6

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_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_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_orient_matrix_type       XPlain
_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_reflns_number            11505
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.907
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3126
_reflns_number_gt                1833
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²+2.3183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3126
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.1842
_refine_ls_wR_factor_gt          0.1580
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
O4A O 0.6398(2) 0.1582(14) 0.0749(2) 0.0495(18) Uiso 0.483(14) 1 d . . P A 2
O4B O 0.65170(18) 0.2581(13) 0.0717(2) 0.0500(16) Uiso 0.517(14) 1 d . . P A 1
C1 C 0.52740(9) 0.5684(5) 0.12881(13) 0.0442(6) Uani 1 1 d . . . . .
C2 C 0.49989(10) 0.3813(6) 0.14903(17) 0.0629(8) Uani 1 1 d . . . . .
H2 H 0.5144 0.2632 0.1825 0.076 Uiso 1 1 calc R U . . .
C3 C 0.45120(10) 0.3628(6) 0.12116(19) 0.0698(9) Uani 1 1 d . . . . .
H3 H 0.4334 0.2329 0.1359 0.084 Uiso 1 1 calc R U . . .
C4 C 0.42878(9) 0.5336(5) 0.07204(15) 0.0531(7) Uani 1 1 d . . . . .
C5 C 0.45541(11) 0.7219(6) 0.05144(17) 0.0699(9) Uani 1 1 d . . . . .
H5 H 0.4407 0.8409 0.0185 0.084 Uiso 1 1 calc R U . . .
C6 C 0.50439(11) 0.7371(6) 0.07933(17) 0.0697(9) Uani 1 1 d . . . . .
H6 H 0.5222 0.8658 0.0640 0.084 Uiso 1 1 calc R U . . .
C7 C 0.58123(9) 0.5880(5) 0.15815(14) 0.0471(6) Uani 1 1 d . . . . .
H7 H 0.5973 0.6544 0.1189 0.056 Uiso 1 1 calc R U . . .
C8 C 0.59106(9) 0.7578(5) 0.22480(15) 0.0521(7) Uani 1 1 d . . . . .
H8A H 0.5773 0.9191 0.2116 0.062 Uiso 1 1 calc R U . . .
H8B H 0.5761 0.6921 0.2647 0.062 Uiso 1 1 calc R U . . .
C9 C 0.65854(11) 0.9009(7) 0.32301(16) 0.0732(9) Uani 1 1 d . . . . .
H9A H 0.6454 0.8101 0.3600 0.110 Uiso 1 1 calc R U . . .
H9B H 0.6461 1.0661 0.3205 0.110 Uiso 1 1 calc R U . . .
H9C H 0.6932 0.9049 0.3360 0.110 Uiso 1 1 calc R U . . .
C10 C 0.68128(9) 0.0666(5) 0.08701(14) 0.0516(7) Uani 1 1 d . . . . .
C11 C 0.70129(9) -0.0243(5) 0.02139(14) 0.0564(7) Uani 1 1 d . . . . .
H11A H 0.6749 -0.0976 -0.0131 0.068 Uiso 1 1 calc R U . . .
H11B H 0.7125 0.1173 -0.0032 0.068 Uiso 1 1 calc R U . . .
C12 C 0.74157(10) -0.2067(5) 0.03524(14) 0.0551(7) Uani 1 1 d . . . . .
H12A H 0.7310 -0.3486 0.0605 0.066 Uiso 1 1 calc R U . . .
H12B H 0.7688 -0.1333 0.0680 0.066 Uiso 1 1 calc R U . . .
N3 N 0.64446(8) 0.7796(5) 0.24979(13) 0.0511(6) Uani 1 1 d . . . . .
O1 O 0.38042(8) 0.5059(5) 0.04571(15) 0.0771(7) Uani 1 1 d . . . . .
O2 O 0.60249(7) 0.3581(3) 0.18170(11) 0.0562(5) Uani 1 1 d . . . . .
O5 O 0.69828(6) -0.0024(4) 0.15133(9) 0.0576(5) Uani 1 1 d . . . . .
O6 O 0.71227(9) 0.4013(5) 0.26088(17) 0.0842(8) Uani 1 1 d . . . . .
H1A H 0.3734(13) 0.612(7) 0.014(2) 0.093(14) Uiso 1 1 d . . . . .
H2A H 0.6200(12) 0.294(7) 0.143(2) 0.101(12) Uiso 1 1 d . . . . .
H3A H 0.6639(13) 0.621(8) 0.251(2) 0.111(13) Uiso 1 1 d . . . . .
H6A H 0.7399(15) 0.412(7) 0.293(2) 0.106(13) Uiso 1 1 d . . . . .
H3B H 0.6575(9) 0.862(5) 0.2153(15) 0.053(8) Uiso 1 1 d . . . . .
H6B H 0.7142(15) 0.303(8) 0.227(2) 0.125(18) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4A C10 1.249(4) . ?
O4B C10 1.329(5) . ?
C1 C2 1.364(4) . ?
C1 C6 1.368(4) . ?
C1 C7 1.515(3) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(4) . ?
C4 O1 1.366(3) . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O2 1.418(3) . ?
C7 C8 1.514(4) . ?
C7 H7 0.9800 . ?
C8 N3 1.492(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N3 1.483(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O5 1.247(3) . ?
C10 C11 1.493(3) . ?
C11 C12 1.490(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C12 1.522(5) 7_645 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
N3 H3A 1.01(4) . ?
N3 H3B 0.90(3) . ?
O1 H1A 0.82(4) . ?
O2 H2A 1.00(4) . ?
O6 H6A 0.89(4) . ?
O6 H6B 0.82(5) . ?

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
_geom_angle_publ_flag
C2 C1 C6 117.0(2) . . ?
C2 C1 C7 122.1(2) . . ?
C6 C1 C7 120.9(2) . . ?
C1 C2 C3 121.7(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 O1 123.1(3) . . ?
C3 C4 O1 118.2(3) . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 121.9(3) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
O2 C7 C8 106.4(2) . . ?
O2 C7 C1 112.7(2) . . ?
C8 C7 C1 111.05(19) . . ?
O2 C7 H7 108.9 . . ?
C8 C7 H7 108.9 . . ?
C1 C7 H7 108.9 . . ?
N3 C8 C7 109.1(2) . . ?
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 . . ?
O5 C10 O4A 118.6(3) . . ?
O5 C10 O4B 123.8(3) . . ?
O5 C10 C11 121.5(2) . . ?
O4A C10 C11 117.2(3) . . ?
O4B C10 C11 113.3(3) . . ?
C12 C11 C10 117.5(2) . . ?
C12 C11 H11A 107.9 . . ?
C10 C11 H11A 107.9 . . ?
C12 C11 H11B 107.9 . . ?
C10 C11 H11B 107.9 . . ?
H11A C11 H11B 107.2 . . ?
C11 C12 C12 113.5(3) . 7_645 ?
C11 C12 H12A 108.9 . . ?
C12 C12 H12A 108.9 7_645 . ?
C11 C12 H12B 108.9 . . ?
C12 C12 H12B 108.9 7_645 . ?
H12A C12 H12B 107.7 . . ?
C9 N3 C8 114.1(2) . . ?
C9 N3 H3A 107(2) . . ?
C8 N3 H3A 117(2) . . ?
C9 N3 H3B 109.5(17) . . ?
C8 N3 H3B 109.3(16) . . ?
H3A N3 H3B 99(3) . . ?
C4 O1 H1A 106(3) . . ?
C7 O2 H2A 109(2) . . ?
H6A O6 H6B 112(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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(4) . . . . ?
C7 C1 C2 C3 -178.9(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C2 C3 C4 O1 179.6(3) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
O1 C4 C5 C6 -179.0(3) . . . . ?
C2 C1 C6 C5 0.7(5) . . . . ?
C7 C1 C6 C5 179.6(3) . . . . ?
C4 C5 C6 C1 -1.1(5) . . . . ?
C2 C1 C7 O2 23.8(3) . . . . ?
C6 C1 C7 O2 -155.0(3) . . . . ?
C2 C1 C7 C8 -95.5(3) . . . . ?
C6 C1 C7 C8 85.7(3) . . . . ?
O2 C7 C8 N3 59.3(3) . . . . ?
C1 C7 C8 N3 -177.7(2) . . . . ?
O5 C10 C11 C12 1.7(4) . . . . ?
O4A C10 C11 C12 -159.4(5) . . . . ?
O4B C10 C11 C12 169.0(4) . . . . ?
C10 C11 C12 C12 178.4(3) . . . 7_645 ?
C7 C8 N3 C9 -168.7(2) . . . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methnol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1b
_database_code_depnum_ccdc_archive 'CCDC 1535423'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(+/-)-Synephrine Oxalic Acid (1:0.5) Salt'
_chemical_name_common            '(+/-)-Synephrine Oxalic Acid (1:0.5) Salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H14 N O2, 0.5(C2 O4)'
_chemical_formula_sum            'C10 H14 N O4'
_chemical_formula_weight         212.22

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.997(7)
_cell_length_b                   7.236(4)
_cell_length_c                   12.376(6)
_cell_angle_alpha                90
_cell_angle_beta                 116.81(2)
_cell_angle_gamma                90
_cell_volume                     1038.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    895
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      25.4

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_details      
;
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 0.0000
	             XTD: 45.0222
	          2theta: -19.6851
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 90.0000
	             XTD: 45.0222
	          2theta: -19.6851
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 180.0000
	             XTD: 45.0222
	          2theta: -19.6851
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 16.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 270.0000
	             XTD: 45.0222
	          2theta: -19.6851

;
_diffrn_orient_matrix_UB_11      -0.017122
_diffrn_orient_matrix_UB_12      0.037259
_diffrn_orient_matrix_UB_13      0.065417
_diffrn_orient_matrix_UB_21      -0.134388
_diffrn_orient_matrix_UB_22      -0.024008
_diffrn_orient_matrix_UB_23      -0.021499
_diffrn_orient_matrix_UB_31      0.010603
_diffrn_orient_matrix_UB_32      -0.038896
_diffrn_orient_matrix_UB_33      -0.022839
_diffrn_orient_matrix_type       XPlain
_diffrn_reflns_transf_matrix_11  -0.017122
_diffrn_reflns_transf_matrix_12  0.037259
_diffrn_reflns_transf_matrix_13  0.065417
_diffrn_reflns_transf_matrix_21  -0.134388
_diffrn_reflns_transf_matrix_22  -0.024008
_diffrn_reflns_transf_matrix_23  -0.021499
_diffrn_reflns_transf_matrix_31  0.010603
_diffrn_reflns_transf_matrix_32  -0.038896
_diffrn_reflns_transf_matrix_33  -0.022839
_reflns_shell_number_unique_all  3718
_diffrn_reflns_number            5675
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.294
_diffrn_reflns_theta_max         25.412
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             1856
_reflns_number_gt                1099
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1115P)²+0.0316P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1856
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2064
_refine_ls_wR_factor_gt          0.1810
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6022(3) 0.3849(5) 0.8885(3) 0.0343(9) Uani 1 1 d . . . . .
C2 C 0.5128(3) 0.4571(5) 0.7853(3) 0.0376(9) Uani 1 1 d . . . . .
H2 H 0.5298 0.5228 0.7308 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3986(3) 0.4337(5) 0.7612(3) 0.0363(9) Uani 1 1 d . . . . .
H3 H 0.3397 0.4808 0.6904 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3726(3) 0.3399(5) 0.8431(3) 0.0311(9) Uani 1 1 d . . . . .
C5 C 0.4608(3) 0.2641(5) 0.9464(3) 0.0373(9) Uani 1 1 d . . . . .
H5 H 0.4440 0.1989 1.0012 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5731(3) 0.2861(5) 0.9671(3) 0.0371(10) Uani 1 1 d . . . . .
H6 H 0.6316 0.2331 1.0358 0.045 Uiso 1 1 calc R U . . .
C7 C 0.7270(3) 0.4170(6) 0.9175(4) 0.0436(10) Uani 1 1 d . . . . .
H7 H 0.7732 0.3233 0.9768 0.052 Uiso 1 1 calc R U . . .
C8 C 0.7513(3) 0.3997(5) 0.8110(3) 0.0353(9) Uani 1 1 d . . . . .
H8A H 0.7302 0.2768 0.7766 0.042 Uiso 1 1 calc R U . . .
H8B H 0.7049 0.4883 0.7495 0.042 Uiso 1 1 calc R U . . .
C9 C 0.9066(4) 0.4158(6) 0.7457(4) 0.0510(12) Uani 1 1 d . . . . .
H9A H 0.8644 0.5053 0.6843 0.076 Uiso 1 1 calc R U . . .
H9B H 0.8881 0.2938 0.7119 0.076 Uiso 1 1 calc R U . . .
H9C H 0.9878 0.4373 0.7757 0.076 Uiso 1 1 calc R U . . .
C10 C 0.9619(3) 0.9374(5) 0.9446(3) 0.0323(9) Uani 1 1 d . . . . .
N3 N 0.8750(3) 0.4330(5) 0.8465(3) 0.0333(8) Uani 1 1 d . . . . .
O1 O 0.2611(2) 0.3193(4) 0.8261(3) 0.0391(7) Uani 1 1 d . . . . .
O2 O 0.7691(3) 0.5899(5) 0.9681(3) 0.0798(12) Uani 1 1 d . . . . .
H2A H 0.7497 0.6117 1.0213 0.120 Uiso 1 1 calc R U . . .
O4 O 0.9856(2) 0.7707(3) 0.9509(2) 0.0465(8) Uani 1 1 d . . . . .
O5 O 0.8831(2) 1.0165(4) 0.8571(2) 0.0448(8) Uani 1 1 d . . . . .
H1A H 0.216(4) 0.389(6) 0.761(4) 0.059(14) Uiso 1 1 d . . . . .
H3B H 0.924(4) 0.353(6) 0.904(4) 0.048(12) Uiso 1 1 d . . . . .
H3A H 0.898(3) 0.544(5) 0.885(3) 0.035(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(5) . ?
C1 C6 1.389(5) . ?
C1 C7 1.513(5) . ?
C2 C3 1.387(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C4 O1 1.376(4) . ?
C4 C5 1.388(5) . ?
C5 C6 1.372(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O2 1.395(5) . ?
C7 C8 1.494(5) . ?
C7 H7 0.9800 . ?
C8 N3 1.483(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N3 1.484(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O4 1.239(4) . ?
C10 O5 1.244(4) . ?
C10 C10 1.567(7) 3_777 ?
N3 H3B 0.91(5) . ?
N3 H3A 0.91(4) . ?
O1 H1A 0.90(5) . ?
O2 H2A 0.8200 . ?

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
_geom_angle_publ_flag
C2 C1 C6 117.4(4) . . ?
C2 C1 C7 121.7(4) . . ?
C6 C1 C7 120.9(3) . . ?
C1 C2 C3 121.6(4) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O1 C4 C3 122.0(3) . . ?
O1 C4 C5 118.3(3) . . ?
C3 C4 C5 119.7(3) . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 122.1(3) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
O2 C7 C8 106.0(3) . . ?
O2 C7 C1 113.9(3) . . ?
C8 C7 C1 114.1(3) . . ?
O2 C7 H7 107.5 . . ?
C8 C7 H7 107.5 . . ?
C1 C7 H7 107.5 . . ?
N3 C8 C7 110.9(3) . . ?
N3 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
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 125.9(3) . . ?
O4 C10 C10 117.8(4) . 3_777 ?
O5 C10 C10 116.3(4) . 3_777 ?
C8 N3 C9 114.3(3) . . ?
C8 N3 H3B 114(3) . . ?
C9 N3 H3B 105(3) . . ?
C8 N3 H3A 111(2) . . ?
C9 N3 H3A 111(2) . . ?
H3B N3 H3A 102(3) . . ?
C4 O1 H1A 107(3) . . ?
C7 O2 H2A 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.6(5) . . . . ?
C7 C1 C2 C3 -177.4(4) . . . . ?
C1 C2 C3 C4 1.5(6) . . . . ?
C2 C3 C4 O1 177.3(3) . . . . ?
C2 C3 C4 C5 -2.4(6) . . . . ?
O1 C4 C5 C6 -178.6(3) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C4 C5 C6 C1 1.0(6) . . . . ?
C2 C1 C6 C5 -1.9(5) . . . . ?
C7 C1 C6 C5 176.2(3) . . . . ?
C2 C1 C7 O2 79.6(5) . . . . ?
C6 C1 C7 O2 -98.4(4) . . . . ?
C2 C1 C7 C8 -42.3(5) . . . . ?
C6 C1 C7 C8 139.7(4) . . . . ?
O2 C7 C8 N3 53.8(4) . . . . ?
C1 C7 C8 N3 180.0(3) . . . . ?
C7 C8 N3 C9 179.2(4) . . . . ?

_refine_diff_density_max         0.634
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methnol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1a
_database_code_depnum_ccdc_archive 'CCDC 1535427'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        (+/-)-Synephrine
_chemical_name_common            (+/-)-Synephrine
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H13 N O2'
_chemical_formula_sum            'C9 H13 N O2'
_chemical_formula_weight         167.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.869(5)
_cell_length_b                   12.103(6)
_cell_length_c                   9.009(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.400(8)
_cell_angle_gamma                90
_cell_volume                     887.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    890
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.3

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_details      
;
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 14.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 0.0000
	             XTD: 44.9750
	          2theta: -19.7106
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 14.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 90.0000
	             XTD: 44.9750
	          2theta: -19.7106
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 14.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 180.0000
	             XTD: 44.9750
	          2theta: -19.7106
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 14.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 270.0000
	             XTD: 44.9750
	          2theta: -19.7106

;
_diffrn_orient_matrix_UB_11      -0.065392
_diffrn_orient_matrix_UB_12      0.104006
_diffrn_orient_matrix_UB_13      -0.000767
_diffrn_orient_matrix_UB_21      0.034329
_diffrn_orient_matrix_UB_22      0.021052
_diffrn_orient_matrix_UB_23      -0.072144
_diffrn_orient_matrix_UB_31      -0.107439
_diffrn_orient_matrix_UB_32      -0.011213
_diffrn_orient_matrix_UB_33      -0.054397
_diffrn_orient_matrix_type       XPlain
_diffrn_reflns_transf_matrix_11  -0.065392
_diffrn_reflns_transf_matrix_12  0.104006
_diffrn_reflns_transf_matrix_13  -0.000767
_diffrn_reflns_transf_matrix_21  0.034329
_diffrn_reflns_transf_matrix_22  0.021052
_diffrn_reflns_transf_matrix_23  -0.072144
_diffrn_reflns_transf_matrix_31  -0.107439
_diffrn_reflns_transf_matrix_32  -0.011213
_diffrn_reflns_transf_matrix_33  -0.054397
_diffrn_reflns_number            5293
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.016
_diffrn_reflns_theta_max         25.309
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             1577
_reflns_number_gt                987
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0696P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1577
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1363
_refine_ls_wR_factor_gt          0.1217
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7012(2) 0.31986(19) 0.2450(2) 0.0358(6) Uani 1 1 d . . . . .
C2 C 0.6506(3) 0.3945(2) 0.1176(3) 0.0437(6) Uani 1 1 d . . . . .
H2 H 0.5918 0.4567 0.1236 0.052 Uiso 1 1 calc R U . . .
C3 C 0.6845(3) 0.3793(2) -0.0177(3) 0.0443(6) Uani 1 1 d . . . . .
H3 H 0.6475 0.4302 -0.1018 0.053 Uiso 1 1 calc R U . . .
C4 C 0.7740(3) 0.28774(19) -0.0279(3) 0.0393(6) Uani 1 1 d . . . . .
C5 C 0.8258(3) 0.2130(2) 0.0990(3) 0.0512(7) Uani 1 1 d . . . . .
H5 H 0.8862 0.1512 0.0943 0.061 Uiso 1 1 calc R U . . .
C6 C 0.7888(3) 0.2293(2) 0.2322(3) 0.0482(7) Uani 1 1 d . . . . .
H6 H 0.8240 0.1777 0.3156 0.058 Uiso 1 1 calc R U . . .
C7 C 0.6710(3) 0.3425(2) 0.3962(3) 0.0386(6) Uani 1 1 d . . . . .
H7 H 0.6681 0.2722 0.4490 0.046 Uiso 1 1 calc R U . . .
C8 C 0.8080(3) 0.4133(2) 0.5113(3) 0.0456(6) Uani 1 1 d . . . . .
H8A H 0.9114 0.3740 0.5422 0.055 Uiso 1 1 calc R U . . .
H8B H 0.8160 0.4807 0.4566 0.055 Uiso 1 1 calc R U . . .
C9 C 0.9068(3) 0.5185(3) 0.7613(3) 0.0655(8) Uani 1 1 d . . . . .
H9A H 0.9156 0.5801 0.6980 0.079 Uiso 1 1 calc R U . . .
H9B H 1.0107 0.4811 0.8074 0.079 Uiso 1 1 calc R U . . .
H9C H 0.8766 0.5446 0.8463 0.079 Uiso 1 1 calc R U . . .
N3 N 0.7810(2) 0.44171(19) 0.6575(2) 0.0442(5) Uani 1 1 d . . . . .
O1 O 0.8110(2) 0.26936(17) -0.1590(2) 0.0550(5) Uani 1 1 d . . . . .
O2 O 0.52019(17) 0.40022(13) 0.36163(18) 0.0462(5) Uani 1 1 d . . . . .
H2A H 0.4450 0.3556 0.3408 0.055 Uiso 1 1 calc R U . . .
H1A H 0.789(4) 0.336(3) -0.227(4) 0.105(12) Uiso 1 1 d . . . . .
H3A H 0.689(3) 0.470(2) 0.624(3) 0.048(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.374(3) . ?
C1 C2 1.387(3) . ?
C1 C7 1.514(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 O1 1.364(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O2 1.429(3) . ?
C7 C8 1.513(3) . ?
C7 H7 0.9800 . ?
C8 N3 1.470(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N3 1.468(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N3 H3A 0.83(2) . ?
O1 H1A 0.99(4) . ?
O2 H2A 0.8200 . ?

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
_geom_angle_publ_flag
C6 C1 C2 117.3(2) . . ?
C6 C1 C7 121.8(2) . . ?
C2 C1 C7 120.8(2) . . ?
C3 C2 C1 122.1(2) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
O1 C4 C5 119.5(2) . . ?
O1 C4 C3 121.9(2) . . ?
C5 C4 C3 118.6(2) . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C1 C6 C5 121.7(2) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
O2 C7 C8 107.44(19) . . ?
O2 C7 C1 112.16(16) . . ?
C8 C7 C1 109.76(17) . . ?
O2 C7 H7 109.1 . . ?
C8 C7 H7 109.1 . . ?
C1 C7 H7 109.1 . . ?
N3 C8 C7 111.96(18) . . ?
N3 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N3 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
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 . . ?
C9 N3 C8 111.41(19) . . ?
C9 N3 H3A 111.1(17) . . ?
C8 N3 H3A 104.9(17) . . ?
C4 O1 H1A 110.6(19) . . ?
C7 O2 H2A 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.5(3) . . . . ?
C7 C1 C2 C3 176.3(2) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C3 C4 O1 -179.8(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
O1 C4 C5 C6 -179.5(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
C7 C1 C6 C5 -175.5(2) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C6 C1 C7 O2 -150.4(2) . . . . ?
C2 C1 C7 O2 34.1(3) . . . . ?
C6 C1 C7 C8 90.3(3) . . . . ?
C2 C1 C7 C8 -85.3(3) . . . . ?
O2 C7 C8 N3 55.4(3) . . . . ?
C1 C7 C8 N3 177.56(19) . . . . ?
C7 C8 N3 C9 -174.9(2) . . . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methnol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1g
_database_code_depnum_ccdc_archive 'CCDC 1535426'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(+/-)-Synephrine adipic acid (1:0.5) Salt monolhydrate'
_chemical_name_common            
'(+/-)-Synephrine adipic acid (1:0.5) Salt monolhydrate'
_chemical_melting_point          ?
_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

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.333(10)
_cell_length_b                   5.2410(15)
_cell_length_c                   18.325(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.435(5)
_cell_angle_gamma                90
_cell_volume                     2676.1(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2871
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.4

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.384
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_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: 44.7382
	          2theta: -19.6635
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: 44.7382
	          2theta: -19.6635
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: 44.7382
	          2theta: -19.6635
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: 44.7382
	          2theta: -19.6635

;
_diffrn_orient_matrix_UB_11      0.075116
_diffrn_orient_matrix_UB_12      0.000994
_diffrn_orient_matrix_UB_13      -0.061498
_diffrn_orient_matrix_UB_21      -0.034130
_diffrn_orient_matrix_UB_22      0.008468
_diffrn_orient_matrix_UB_23      -0.062572
_diffrn_orient_matrix_UB_31      -0.001038
_diffrn_orient_matrix_UB_32      0.055370
_diffrn_orient_matrix_UB_33      -0.003469
_diffrn_orient_matrix_type       XPlain
_diffrn_reflns_transf_matrix_11  0.075116
_diffrn_reflns_transf_matrix_12  0.000994
_diffrn_reflns_transf_matrix_13  -0.061498
_diffrn_reflns_transf_matrix_21  -0.034130
_diffrn_reflns_transf_matrix_22  0.008468
_diffrn_reflns_transf_matrix_23  -0.062572
_diffrn_reflns_transf_matrix_31  -0.001038
_diffrn_reflns_transf_matrix_32  0.055370
_diffrn_reflns_transf_matrix_33  -0.003469
_diffrn_reflns_number            7998
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.956
_diffrn_reflns_theta_max         25.415
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             2397
_reflns_number_gt                1894
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0701P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2397
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C2A C 0.50342(15) 0.4373(12) 0.6700(4) 0.0243(12) Uani 0.490(11) 1 d . . P A 2
H2A H 0.5196 0.3547 0.7135 0.029 Uiso 0.490(11) 1 calc R U P A 2
C3A C 0.45453(16) 0.4045(12) 0.6461(4) 0.0267(12) Uani 0.490(11) 1 d . . P A 2
H3A H 0.4371 0.2997 0.6743 0.032 Uiso 0.490(11) 1 calc R U P A 2
C5A C 0.45775(16) 0.6723(12) 0.5410(3) 0.0236(12) Uani 0.490(11) 1 d . . P A 2
H5A H 0.4433 0.7537 0.4962 0.028 Uiso 0.490(11) 1 calc R U P A 2
C6A C 0.50699(16) 0.7039(12) 0.5660(3) 0.0220(11) Uani 0.490(11) 1 d . . P A 2
H6A H 0.5254 0.8042 0.5383 0.026 Uiso 0.490(11) 1 calc R U P A 2
C2B C 0.50239(15) 0.3679(11) 0.6393(4) 0.0269(11) Uani 0.510(11) 1 d . . P A 1
H2B H 0.5197 0.2289 0.6645 0.032 Uiso 0.510(11) 1 calc R U P A 1
C3B C 0.45371(14) 0.3383(11) 0.6148(4) 0.0259(11) Uani 0.510(11) 1 d . . P A 1
H3B H 0.4382 0.1838 0.6237 0.031 Uiso 0.510(11) 1 calc R U P A 1
C5B C 0.44926(17) 0.7623(12) 0.5649(3) 0.0305(12) Uani 0.510(11) 1 d . . P A 1
H5B H 0.4304 0.8962 0.5396 0.037 Uiso 0.510(11) 1 calc R U P A 1
C6B C 0.49823(17) 0.7891(12) 0.5901(3) 0.0285(12) Uani 0.510(11) 1 d . . P A 1
H6B H 0.5129 0.9460 0.5811 0.034 Uiso 0.510(11) 1 calc R U P A 1
O2 O 0.60501(4) 0.3884(2) 0.67768(6) 0.0286(3) Uani 1 1 d . . . . .
O1 O 0.38081(4) 0.4878(3) 0.55651(7) 0.0348(3) Uani 1 1 d . . . . .
N3 N 0.64472(5) 0.8220(3) 0.74855(7) 0.0262(3) Uani 1 1 d . . . . .
C7 C 0.58171(5) 0.6242(3) 0.65601(8) 0.0248(4) Uani 1 1 d . . . . .
H7 H 0.5962 0.7019 0.6154 0.030 Uiso 1 1 calc R U . . .
C4 C 0.42912(6) 0.5271(4) 0.57885(9) 0.0273(4) Uani 1 1 d . . . . .
C8 C 0.59174(5) 0.7960(4) 0.72408(9) 0.0278(4) Uani 1 1 d . . . . .
H8A H 0.5772 0.9660 0.7119 0.033 Uiso 1 1 calc R U . . .
H8B H 0.5773 0.7214 0.7646 0.033 Uiso 1 1 calc R U . . .
C1 C 0.52799(5) 0.5915(3) 0.62930(8) 0.0240(4) Uani 1 1 d . . . . .
C9 C 0.65888(7) 0.9390(4) 0.82344(9) 0.0371(5) Uani 1 1 d . . . . .
H9A H 0.6476 0.8312 0.8605 0.056 Uiso 1 1 calc R U . . .
H9B H 0.6444 1.1089 0.8236 0.056 Uiso 1 1 calc R U . . .
H9C H 0.6939 0.9539 0.8355 0.056 Uiso 1 1 calc R U . . .
O3 O 0.69971(4) 1.0307(2) 0.64889(6) 0.0280(3) Uani 1 1 d . . . . .
O5 O 0.78796(5) 0.9329(3) 0.74010(8) 0.0414(4) Uani 1 1 d . . . . .
O4 O 0.64925(4) 1.2635(3) 0.56878(6) 0.0464(4) Uani 1 1 d . . . . .
C10 C 0.68263(5) 1.1021(4) 0.58360(8) 0.0272(4) Uani 1 1 d . . . . .
C12 C 0.74265(5) 0.8021(3) 0.53538(8) 0.0246(4) Uani 1 1 d . . . . .
H12A H 0.7330 0.6584 0.5645 0.029 Uiso 1 1 calc R U . . .
H12B H 0.7706 0.8873 0.5661 0.029 Uiso 1 1 calc R U . . .
C11 C 0.70138(5) 0.9908(3) 0.51801(8) 0.0244(4) Uani 1 1 d . . . . .
H11A H 0.7118 1.1337 0.4894 0.029 Uiso 1 1 calc R U . . .
H11B H 0.6744 0.9048 0.4854 0.029 Uiso 1 1 calc R U . . .
H3D H 0.6578(6) 0.916(4) 0.7159(10) 0.028(5) Uiso 1 1 d . . . . .
H2 H 0.6218(8) 0.346(5) 0.6388(14) 0.069(7) Uiso 1 1 d . . . . .
H1 H 0.3731(8) 0.578(5) 0.5156(13) 0.055(7) Uiso 1 1 d . . . . .
H3C H 0.6598(8) 0.661(5) 0.7464(12) 0.062(7) Uiso 1 1 d . . . . .
H5C H 0.7611(10) 0.927(5) 0.7101(14) 0.065(8) Uiso 1 1 d . . . . .
H5D H 0.7866(8) 0.813(5) 0.7746(14) 0.062(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2A C1 1.371(5) . ?
C2A C3A 1.386(6) . ?
C2A H2A 0.9500 . ?
C3A C4 1.459(6) . ?
C3A H3A 0.9500 . ?
C5A C4 1.386(5) . ?
C5A C6A 1.397(5) . ?
C5A H5A 0.9500 . ?
C6A C1 1.341(4) . ?
C6A H6A 0.9500 . ?
C2B C3B 1.380(6) . ?
C2B C1 1.407(5) . ?
C2B H2B 0.9500 . ?
C3B C4 1.316(5) . ?
C3B H3B 0.9500 . ?
C5B C6B 1.388(6) . ?
C5B C4 1.401(5) . ?
C5B H5B 0.9500 . ?
C6B C1 1.442(5) . ?
C6B H6B 0.9500 . ?
O2 C7 1.424(2) . ?
O2 H2 0.95(3) . ?
O1 C4 1.371(2) . ?
O1 H1 0.88(2) . ?
N3 C9 1.490(2) . ?
N3 C8 1.493(2) . ?
N3 H3D 0.90(2) . ?
N3 H3C 0.95(3) . ?
C7 C1 1.522(2) . ?
C7 C8 1.523(2) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O3 C10 1.2633(19) . ?
O5 H5C 0.86(3) . ?
O5 H5D 0.90(3) . ?
O4 C10 1.261(2) . ?
C10 C11 1.516(2) . ?
C12 C11 1.521(2) . ?
C12 C12 1.532(3) 7_666 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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
_geom_angle_publ_flag
C1 C2A C3A 118.6(4) . . ?
C1 C2A H2A 120.7 . . ?
C3A C2A H2A 120.7 . . ?
C2A C3A C4 121.6(4) . . ?
C2A C3A H3A 119.2 . . ?
C4 C3A H3A 119.2 . . ?
C4 C5A C6A 122.8(3) . . ?
C4 C5A H5A 118.6 . . ?
C6A C5A H5A 118.6 . . ?
C1 C6A C5A 119.5(4) . . ?
C1 C6A H6A 120.3 . . ?
C5A C6A H6A 120.3 . . ?
C3B C2B C1 124.0(4) . . ?
C3B C2B H2B 118.0 . . ?
C1 C2B H2B 118.0 . . ?
C4 C3B C2B 119.1(4) . . ?
C4 C3B H3B 120.5 . . ?
C2B C3B H3B 120.5 . . ?
C6B C5B C4 116.3(4) . . ?
C6B C5B H5B 121.8 . . ?
C4 C5B H5B 121.8 . . ?
C5B C6B C1 123.5(4) . . ?
C5B C6B H6B 118.2 . . ?
C1 C6B H6B 118.2 . . ?
C7 O2 H2 105.3(15) . . ?
C4 O1 H1 104.7(14) . . ?
C9 N3 C8 113.74(13) . . ?
C9 N3 H3D 108.3(12) . . ?
C8 N3 H3D 111.2(11) . . ?
C9 N3 H3C 110.8(14) . . ?
C8 N3 H3C 110.0(14) . . ?
H3D N3 H3C 102.3(17) . . ?
O2 C7 C1 112.22(14) . . ?
O2 C7 C8 106.05(13) . . ?
C1 C7 C8 110.95(12) . . ?
O2 C7 H7 109.2 . . ?
C1 C7 H7 109.2 . . ?
C8 C7 H7 109.2 . . ?
C3B C4 O1 116.5(3) . . ?
O1 C4 C5A 125.2(2) . . ?
C3B C4 C5B 123.8(3) . . ?
O1 C4 C5B 119.7(2) . . ?
O1 C4 C3A 119.9(2) . . ?
C5A C4 C3A 114.9(3) . . ?
N3 C8 C7 109.18(13) . . ?
N3 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
N3 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C6A C1 C2A 122.7(3) . . ?
C2B C1 C6B 113.2(3) . . ?
C6A C1 C7 119.3(2) . . ?
C2A C1 C7 117.9(2) . . ?
C2B C1 C7 124.1(2) . . ?
C6B C1 C7 122.7(2) . . ?
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 . . ?
H5C O5 H5D 106(2) . . ?
O4 C10 O3 123.12(14) . . ?
O4 C10 C11 116.36(13) . . ?
O3 C10 C11 120.51(15) . . ?
C11 C12 C12 111.79(15) . 7_666 ?
C11 C12 H12A 109.3 . . ?
C12 C12 H12A 109.3 7_666 . ?
C11 C12 H12B 109.3 . . ?
C12 C12 H12B 109.3 7_666 . ?
H12A C12 H12B 107.9 . . ?
C10 C11 C12 116.80(12) . . ?
C10 C11 H11A 108.1 . . ?
C12 C11 H11A 108.1 . . ?
C10 C11 H11B 108.1 . . ?
C12 C11 H11B 108.1 . . ?
H11A C11 H11B 107.3 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2A C3A C4 0.8(7) . . . . ?
C4 C5A C6A C1 -0.3(6) . . . . ?
C1 C2B C3B C4 0.9(6) . . . . ?
C4 C5B C6B C1 -0.5(6) . . . . ?
C2B C3B C4 O1 -179.3(3) . . . . ?
C2B C3B C4 C5B -1.4(5) . . . . ?
C6A C5A C4 O1 -179.3(3) . . . . ?
C6A C5A C4 C3A -1.3(5) . . . . ?
C6B C5B C4 C3B 1.2(5) . . . . ?
C6B C5B C4 O1 179.1(3) . . . . ?
C2A C3A C4 O1 179.2(3) . . . . ?
C2A C3A C4 C5A 1.1(6) . . . . ?
C9 N3 C8 C7 -167.63(15) . . . . ?
O2 C7 C8 N3 57.67(17) . . . . ?
C1 C7 C8 N3 179.78(14) . . . . ?
C5A C6A C1 C2A 2.4(6) . . . . ?
C5A C6A C1 C7 179.4(3) . . . . ?
C3A C2A C1 C6A -2.6(6) . . . . ?
C3A C2A C1 C7 -179.7(3) . . . . ?
C3B C2B C1 C6B -0.3(5) . . . . ?
C3B C2B C1 C7 -179.7(3) . . . . ?
C5B C6B C1 C2B 0.1(5) . . . . ?
C5B C6B C1 C7 179.6(3) . . . . ?
O2 C7 C1 C6A -132.8(4) . . . . ?
C8 C7 C1 C6A 108.8(4) . . . . ?
O2 C7 C1 C2A 44.3(4) . . . . ?
C8 C7 C1 C2A -74.1(4) . . . . ?
O2 C7 C1 C2B 12.8(4) . . . . ?
C8 C7 C1 C2B -105.7(4) . . . . ?
O2 C7 C1 C6B -166.6(4) . . . . ?
C8 C7 C1 C6B 74.9(4) . . . . ?
O4 C10 C11 C12 178.22(16) . . . . ?
O3 C10 C11 C12 -2.8(2) . . . . ?
C12 C12 C11 C10 178.40(17) 7_666 . . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methnol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SD20170422io_100K
_database_code_depnum_ccdc_archive 'CCDC 1914541'
loop_
_audit_author_name
_audit_author_address
'Tejender S.Thakur'
;Central Drug Research Institute
India
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            'Synephrine-DL-Malic acid 1:0.5 salt'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H14 N O2), C4 H2 O4, H O'
_chemical_formula_sum            'C11 H15.50 N O4.50'
_chemical_formula_weight         233.74

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7487(3)
_cell_length_b                   8.9795(5)
_cell_length_c                   11.6493(6)
_cell_angle_alpha                100.209(5)
_cell_angle_beta                 90.688(4)
_cell_angle_gamma                106.188(5)
_cell_volume                     567.16(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2839
_cell_measurement_theta_min      2.4330
_cell_measurement_theta_max      30.5800

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             249
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.464
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_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_detector_area_resol_mean 28.5714
_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_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_orient_matrix_type       XPlain
_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_reflns_number            6116
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.405
_diffrn_reflns_theta_max         31.408
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3198
_reflns_number_gt                2321
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0817P)²+0.2703P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3198
_refine_ls_number_parameters     188
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.1913
_refine_ls_wR_factor_gt          0.1675
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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 ?

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.065

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1914551'
loop_
_audit_author_name
_audit_author_address
'Tejender S.Thakur'
;Central Drug Research Institute
India
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            'Synephrine-DL-Tartaric acid 2:1 salt'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H14 N O2), C4 H4 O6'
_chemical_formula_sum            'C22 H32 N2 O10'
_chemical_formula_weight         484.49

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5357(3)
_cell_length_b                   11.1714(3)
_cell_length_c                   11.4964(3)
_cell_angle_alpha                89.067(2)
_cell_angle_beta                 70.401(3)
_cell_angle_gamma                79.552(2)
_cell_volume                     1133.28(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7743
_cell_measurement_theta_min      2.4920
_cell_measurement_theta_max      31.4120

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_T_min  0.76792
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_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: 44.6998
	          2theta: -19.6510
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: 44.6998
	          2theta: -19.6510
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: 44.6998
	          2theta: -19.6510
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: 44.6998
	          2theta: -19.6510

;
_diffrn_orient_matrix_UB_11      0.012691
_diffrn_orient_matrix_UB_12      -0.086409
_diffrn_orient_matrix_UB_13      0.072047
_diffrn_orient_matrix_UB_21      0.031988
_diffrn_orient_matrix_UB_22      0.068949
_diffrn_orient_matrix_UB_23      0.050138
_diffrn_orient_matrix_UB_31      -0.083910
_diffrn_orient_matrix_UB_32      0.037100
_diffrn_orient_matrix_UB_33      0.010423
_diffrn_orient_matrix_type       XPlain
_diffrn_reflns_transf_matrix_11  0.012691
_diffrn_reflns_transf_matrix_12  -0.086409
_diffrn_reflns_transf_matrix_13  0.072047
_diffrn_reflns_transf_matrix_21  0.031988
_diffrn_reflns_transf_matrix_22  0.068949
_diffrn_reflns_transf_matrix_23  0.050138
_diffrn_reflns_transf_matrix_31  -0.083910
_diffrn_reflns_transf_matrix_32  0.037100
_diffrn_reflns_transf_matrix_33  0.010423
_diffrn_reflns_number            12190
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.883
_diffrn_reflns_theta_max         31.226
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             6414
_reflns_number_gt                5264
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0580P)²+0.3864P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6414
_refine_ls_number_parameters     435
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.73385(14) 1.09231(12) 0.10382(13) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.71846(15) 1.01912(13) 0.01400(13) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.79699(15) 0.89904(13) -0.01084(13) 0.0185(3) Uani 1 1 d . . . . .
C4 C 0.89031(14) 0.85192(11) 0.05604(13) 0.0155(3) Uani 1 1 d . . . . .
C5 C 0.90559(15) 0.92408(12) 0.14699(13) 0.0177(3) Uani 1 1 d . . . . .
C6 C 0.82824(15) 1.04361(13) 0.16944(14) 0.0193(3) Uani 1 1 d . . . . .
C7 C 0.65198(15) 1.22409(12) 0.13358(13) 0.0184(3) Uani 1 1 d . . . . .
C8 C 0.52512(16) 1.23286(12) 0.25800(14) 0.0195(3) Uani 1 1 d . . . . .
C9 C 0.34250(16) 1.37585(14) 0.42585(14) 0.0211(3) Uani 1 1 d . . . . .
C10 C 0.68064(14) 0.12258(12) 0.63662(13) 0.0163(3) Uani 1 1 d . . . . .
C11 C 0.65950(16) 0.06021(13) 0.54165(14) 0.0204(3) Uani 1 1 d . . . . .
C12 C 0.74596(16) -0.05398(13) 0.49610(14) 0.0202(3) Uani 1 1 d . . . . .
C13 C 0.85509(14) -0.10801(12) 0.54601(13) 0.0165(3) Uani 1 1 d . . . . .
C14 C 0.87575(15) -0.04792(13) 0.64228(13) 0.0184(3) Uani 1 1 d . . . . .
C15 C 0.78953(15) 0.06698(12) 0.68586(13) 0.0181(3) Uani 1 1 d . . . . .
C16 C 0.58699(15) 0.24763(12) 0.68569(13) 0.0173(3) Uani 1 1 d . . . . .
C17 C 0.42641(15) 0.23399(12) 0.76174(14) 0.0187(3) Uani 1 1 d . . . . .
C18 C 0.35676(16) 0.41062(14) 0.91634(14) 0.0210(3) Uani 1 1 d . . . . .
C19 C 0.84302(14) 0.40165(12) 0.33051(13) 0.0163(3) Uani 1 1 d . . . . .
C20 C 0.98829(15) 0.43873(12) 0.23990(13) 0.0166(3) Uani 1 1 d . . . . .
C21 C 1.02325(14) 0.54996(12) 0.29312(13) 0.0161(3) Uani 1 1 d . . . . .
C22 C 1.17210(14) 0.58001(12) 0.20116(13) 0.0163(3) Uani 1 1 d . . . . .
N3 N 0.46423(12) 1.36205(10) 0.30322(11) 0.0167(2) Uani 1 1 d . . . . .
N6 N 0.32461(13) 0.35292(11) 0.81439(11) 0.0170(2) Uani 1 1 d . . . . .
O1 O 0.96213(11) 0.73252(9) 0.03343(10) 0.0200(2) Uani 1 1 d . . . . .
O2 O 0.58569(11) 1.27285(9) 0.04590(10) 0.0219(2) Uani 1 1 d . . . . .
O4 O 0.93885(11) -0.21895(9) 0.49590(10) 0.0210(2) Uani 1 1 d . . . . .
O5 O 0.57289(11) 0.32715(9) 0.59062(10) 0.0234(2) Uani 1 1 d . . . . .
O7 O 0.72059(11) 0.43683(9) 0.31185(10) 0.0215(2) Uani 1 1 d . . . . .
O8 O 0.85728(11) 0.33750(9) 0.41827(10) 0.0218(2) Uani 1 1 d . . . . .
O9 O 0.97343(11) 0.47280(9) 0.12474(9) 0.0185(2) Uani 1 1 d . . . . .
O10 O 0.89657(11) 0.64630(9) 0.31352(10) 0.0183(2) Uani 1 1 d . . . . .
O11 O 1.16401(11) 0.67485(9) 0.14000(10) 0.0200(2) Uani 1 1 d . . . . .
O12 O 1.29068(11) 0.50921(9) 0.19491(10) 0.0226(2) Uani 1 1 d . . . . .
H1A H 1.025(3) 0.713(2) 0.081(2) 0.048(6) Uiso 1 1 d . . . . .
H2 H 0.653(2) 1.0515(16) -0.0336(17) 0.024(4) Uiso 1 1 d . . . . .
H2A H 0.663(2) 1.2965(19) -0.021(2) 0.044(6) Uiso 1 1 d . . . . .
H3 H 0.789(2) 0.8500(17) -0.0729(18) 0.030(5) Uiso 1 1 d . . . . .
H3A H 0.421(2) 1.4071(18) 0.2499(19) 0.035(5) Uiso 1 1 d . . . . .
H3N H 0.545(2) 1.3954(18) 0.3106(18) 0.031(5) Uiso 1 1 d . . . . .
H4A H 1.002(3) -0.250(2) 0.534(2) 0.052(7) Uiso 1 1 d . . . . .
H5 H 0.972(2) 0.8894(16) 0.1929(17) 0.024(4) Uiso 1 1 d . . . . .
H5A H 0.666(3) 0.330(2) 0.536(2) 0.046(6) Uiso 1 1 d . . . . .
H6 H 0.840(2) 1.0918(17) 0.2351(17) 0.027(5) Uiso 1 1 d . . . . .
H6A H 0.228(2) 0.3412(16) 0.8452(16) 0.023(4) Uiso 1 1 d . . . . .
H6B H 0.327(2) 0.4098(19) 0.7512(19) 0.036(5) Uiso 1 1 d . . . . .
H7 H 0.7229(18) 1.2770(14) 0.1347(15) 0.013(4) Uiso 1 1 d . . . . .
H8A H 0.4405(18) 1.1987(15) 0.2539(15) 0.015(4) Uiso 1 1 d . . . . .
H8B H 0.559(2) 1.1914(16) 0.3213(16) 0.022(4) Uiso 1 1 d . . . . .
H9 H 0.990(2) 0.407(2) 0.080(2) 0.043(6) Uiso 1 1 d . . . . .
H9A H 0.2606(19) 1.3407(15) 0.4197(15) 0.017(4) Uiso 1 1 d . . . . .
H9B H 0.306(2) 1.4619(19) 0.4454(18) 0.036(5) Uiso 1 1 d . . . . .
H9C H 0.382(2) 1.3403(19) 0.486(2) 0.039(6) Uiso 1 1 d . . . . .
H10 H 0.904(2) 0.697(2) 0.363(2) 0.045(6) Uiso 1 1 d . . . . .
H11 H 0.584(2) 0.0965(16) 0.5048(17) 0.025(5) Uiso 1 1 d . . . . .
H12 H 0.730(2) -0.0946(17) 0.4292(18) 0.029(5) Uiso 1 1 d . . . . .
H14 H 0.9511(19) -0.0852(15) 0.6773(16) 0.018(4) Uiso 1 1 d . . . . .
H15 H 0.805(2) 0.1102(17) 0.7503(17) 0.025(5) Uiso 1 1 d . . . . .
H16 H 0.6301(18) 0.2847(15) 0.7386(15) 0.016(4) Uiso 1 1 d . . . . .
H17A H 0.380(2) 0.2024(17) 0.7070(17) 0.028(5) Uiso 1 1 d . . . . .
H17B H 0.4282(19) 0.1837(16) 0.8318(17) 0.024(4) Uiso 1 1 d . . . . .
H18A H 0.284(2) 0.4848(19) 0.9433(18) 0.036(5) Uiso 1 1 d . . . . .
H18B H 0.458(2) 0.4276(16) 0.8834(16) 0.025(5) Uiso 1 1 d . . . . .
H18C H 0.347(2) 0.3543(17) 0.9813(18) 0.026(5) Uiso 1 1 d . . . . .
H20 H 1.077(2) 0.3707(16) 0.2286(16) 0.022(4) Uiso 1 1 d . . . . .
H21 H 1.0387(18) 0.5257(15) 0.3736(15) 0.015(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.389(2) . ?
C1 C6 1.393(2) . ?
C1 C7 1.5213(18) . ?
C2 C3 1.3952(18) . ?
C2 H2 0.982(19) . ?
C3 C4 1.3915(19) . ?
C3 H3 0.94(2) . ?
C4 O1 1.3697(15) . ?
C4 C5 1.3916(19) . ?
C5 C6 1.3856(18) . ?
C5 H5 0.979(19) . ?
C6 H6 0.984(19) . ?
C7 O2 1.4131(17) . ?
C7 C8 1.5231(19) . ?
C7 H7 0.979(16) . ?
C8 N3 1.4861(17) . ?
C8 H8A 0.968(17) . ?
C8 H8B 0.971(19) . ?
C9 N3 1.4842(18) . ?
C9 H9A 0.958(17) . ?
C9 H9B 0.96(2) . ?
C9 H9C 0.95(2) . ?
C10 C15 1.3905(19) . ?
C10 C11 1.393(2) . ?
C10 C16 1.5174(18) . ?
C11 C12 1.3899(19) . ?
C11 H11 0.975(19) . ?
C12 C13 1.3921(19) . ?
C12 H12 0.967(19) . ?
C13 O4 1.3643(15) . ?
C13 C14 1.3903(19) . ?
C14 C15 1.3916(18) . ?
C14 H14 0.965(18) . ?
C15 H15 0.956(19) . ?
C16 O5 1.4231(17) . ?
C16 C17 1.5213(18) . ?
C16 H16 0.974(17) . ?
C17 N6 1.4961(17) . ?
C17 H17A 0.984(19) . ?
C17 H17B 0.977(19) . ?
C18 N6 1.4902(19) . ?
C18 H18A 0.96(2) . ?
C18 H18B 0.965(18) . ?
C18 H18C 0.960(19) . ?
C19 O7 1.2499(16) . ?
C19 O8 1.2582(17) . ?
C19 C20 1.5496(18) . ?
C20 O9 1.4170(17) . ?
C20 C21 1.5302(18) . ?
C20 H20 1.001(18) . ?
C21 O10 1.4210(15) . ?
C21 C22 1.5491(18) . ?
C21 H21 1.010(17) . ?
C22 O12 1.2378(16) . ?
C22 O11 1.2670(17) . ?
N3 H3A 0.94(2) . ?
N3 H3N 0.94(2) . ?
N6 H6A 0.904(18) . ?
N6 H6B 0.95(2) . ?
O1 H1A 0.93(2) . ?
O2 H2A 0.95(2) . ?
O4 H4A 0.88(3) . ?
O5 H5A 0.91(2) . ?
O9 H9 0.86(2) . ?
O10 H10 0.84(2) . ?

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
_geom_angle_publ_flag
C2 C1 C6 118.91(12) . . ?
C2 C1 C7 122.70(13) . . ?
C6 C1 C7 118.39(12) . . ?
C1 C2 C3 120.64(13) . . ?
C1 C2 H2 120.4(10) . . ?
C3 C2 H2 119.0(10) . . ?
C4 C3 C2 119.59(13) . . ?
C4 C3 H3 119.6(12) . . ?
C2 C3 H3 120.9(12) . . ?
O1 C4 C3 118.71(12) . . ?
O1 C4 C5 120.98(12) . . ?
C3 C4 C5 120.27(12) . . ?
C6 C5 C4 119.40(13) . . ?
C6 C5 H5 121.5(11) . . ?
C4 C5 H5 119.1(11) . . ?
C5 C6 C1 121.19(13) . . ?
C5 C6 H6 117.3(11) . . ?
C1 C6 H6 121.5(11) . . ?
O2 C7 C1 114.02(12) . . ?
O2 C7 C8 107.23(11) . . ?
C1 C7 C8 109.21(11) . . ?
O2 C7 H7 105.1(10) . . ?
C1 C7 H7 110.5(9) . . ?
C8 C7 H7 110.7(9) . . ?
N3 C8 C7 110.85(11) . . ?
N3 C8 H8A 106.7(10) . . ?
C7 C8 H8A 112.5(10) . . ?
N3 C8 H8B 106.8(10) . . ?
C7 C8 H8B 112.3(10) . . ?
H8A C8 H8B 107.4(14) . . ?
N3 C9 H9A 108.7(10) . . ?
N3 C9 H9B 107.3(12) . . ?
H9A C9 H9B 108.3(15) . . ?
N3 C9 H9C 109.6(13) . . ?
H9A C9 H9C 113.0(16) . . ?
H9B C9 H9C 109.8(17) . . ?
C15 C10 C11 118.25(12) . . ?
C15 C10 C16 120.73(12) . . ?
C11 C10 C16 121.02(12) . . ?
C12 C11 C10 121.05(13) . . ?
C12 C11 H11 118.5(11) . . ?
C10 C11 H11 120.5(11) . . ?
C11 C12 C13 119.94(13) . . ?
C11 C12 H12 119.3(12) . . ?
C13 C12 H12 120.7(12) . . ?
O4 C13 C14 122.87(12) . . ?
O4 C13 C12 117.40(12) . . ?
C14 C13 C12 119.72(12) . . ?
C13 C14 C15 119.63(12) . . ?
C13 C14 H14 120.0(10) . . ?
C15 C14 H14 120.4(10) . . ?
C10 C15 C14 121.39(13) . . ?
C10 C15 H15 118.2(11) . . ?
C14 C15 H15 120.4(11) . . ?
O5 C16 C10 113.23(11) . . ?
O5 C16 C17 105.84(11) . . ?
C10 C16 C17 109.00(11) . . ?
O5 C16 H16 110.0(10) . . ?
C10 C16 H16 110.0(10) . . ?
C17 C16 H16 108.7(9) . . ?
N6 C17 C16 113.10(11) . . ?
N6 C17 H17A 104.4(11) . . ?
C16 C17 H17A 108.8(10) . . ?
N6 C17 H17B 106.6(10) . . ?
C16 C17 H17B 109.7(10) . . ?
H17A C17 H17B 114.2(15) . . ?
N6 C18 H18A 107.4(12) . . ?
N6 C18 H18B 107.8(11) . . ?
H18A C18 H18B 110.6(16) . . ?
N6 C18 H18C 107.6(11) . . ?
H18A C18 H18C 111.5(16) . . ?
H18B C18 H18C 111.9(16) . . ?
O7 C19 O8 124.52(12) . . ?
O7 C19 C20 118.35(12) . . ?
O8 C19 C20 117.13(11) . . ?
O9 C20 C21 105.88(11) . . ?
O9 C20 C19 112.62(11) . . ?
C21 C20 C19 110.42(11) . . ?
O9 C20 H20 111.2(10) . . ?
C21 C20 H20 107.1(10) . . ?
C19 C20 H20 109.5(10) . . ?
O10 C21 C20 107.80(11) . . ?
O10 C21 C22 113.42(11) . . ?
C20 C21 C22 108.16(11) . . ?
O10 C21 H21 110.9(9) . . ?
C20 C21 H21 106.7(9) . . ?
C22 C21 H21 109.5(9) . . ?
O12 C22 O11 125.17(12) . . ?
O12 C22 C21 116.60(12) . . ?
O11 C22 C21 118.22(11) . . ?
C9 N3 C8 113.15(11) . . ?
C9 N3 H3A 105.5(12) . . ?
C8 N3 H3A 112.0(12) . . ?
C9 N3 H3N 108.1(12) . . ?
C8 N3 H3N 107.5(12) . . ?
H3A N3 H3N 110.6(17) . . ?
C18 N6 C17 114.96(11) . . ?
C18 N6 H6A 106.9(11) . . ?
C17 N6 H6A 109.0(11) . . ?
C18 N6 H6B 108.7(12) . . ?
C17 N6 H6B 110.9(12) . . ?
H6A N6 H6B 105.9(17) . . ?
C4 O1 H1A 110.7(14) . . ?
C7 O2 H2A 107.5(14) . . ?
C13 O4 H4A 113.3(16) . . ?
C16 O5 H5A 109.5(14) . . ?
C20 O9 H9 107.7(15) . . ?
C21 O10 H10 106.3(16) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(2) . . . . ?
C7 C1 C2 C3 179.40(12) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C2 C3 C4 O1 177.66(12) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
O1 C4 C5 C6 -178.39(12) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 C1 0.9(2) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
C7 C1 C6 C5 179.79(12) . . . . ?
C2 C1 C7 O2 -12.66(18) . . . . ?
C6 C1 C7 O2 167.19(12) . . . . ?
C2 C1 C7 C8 107.26(15) . . . . ?
C6 C1 C7 C8 -72.89(16) . . . . ?
O2 C7 C8 N3 -68.25(15) . . . . ?
C1 C7 C8 N3 167.74(11) . . . . ?
C15 C10 C11 C12 -0.7(2) . . . . ?
C16 C10 C11 C12 179.56(13) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C11 C12 C13 O4 -178.60(13) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
O4 C13 C14 C15 177.81(12) . . . . ?
C12 C13 C14 C15 -1.5(2) . . . . ?
C11 C10 C15 C14 0.0(2) . . . . ?
C16 C10 C15 C14 179.66(12) . . . . ?
C13 C14 C15 C10 1.2(2) . . . . ?
C15 C10 C16 O5 135.55(13) . . . . ?
C11 C10 C16 O5 -44.76(17) . . . . ?
C15 C10 C16 C17 -106.94(15) . . . . ?
C11 C10 C16 C17 72.75(16) . . . . ?
O5 C16 C17 N6 -57.86(15) . . . . ?
C10 C16 C17 N6 -179.96(11) . . . . ?
O7 C19 C20 O9 -20.16(17) . . . . ?
O8 C19 C20 O9 159.74(11) . . . . ?
O7 C19 C20 C21 97.97(14) . . . . ?
O8 C19 C20 C21 -82.14(14) . . . . ?
O9 C20 C21 O10 63.20(13) . . . . ?
C19 C20 C21 O10 -58.97(14) . . . . ?
O9 C20 C21 C22 -59.80(13) . . . . ?
C19 C20 C21 C22 178.02(11) . . . . ?
O10 C21 C22 O12 168.30(12) . . . . ?
C20 C21 C22 O12 -72.17(15) . . . . ?
O10 C21 C22 O11 -10.71(17) . . . . ?
C20 C21 C22 O11 108.81(14) . . . . ?
C7 C8 N3 C9 -178.63(12) . . . . ?
C16 C17 N6 C18 -71.13(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O11 0.93(2) 1.67(2) 2.5940(15) 169(2) .
O2 H2A O11 0.95(2) 1.83(2) 2.7657(14) 170(2) 2_775
N3 H3A O12 0.94(2) 1.80(2) 2.7058(16) 161.3(18) 1_465
N3 H3N O7 0.94(2) 1.82(2) 2.7549(15) 170.6(17) 1_565
O4 H4A O8 0.88(3) 1.75(3) 2.6110(15) 167(2) 2_756
O5 H5A O8 0.91(2) 1.88(2) 2.7920(14) 178(2) .
N6 H6A O1 0.904(18) 2.172(18) 3.0218(16) 156.5(16) 2_666
N6 H6A O9 0.904(18) 2.501(18) 3.0100(15) 116.1(13) 2_666
N6 H6A O10 0.904(18) 2.479(19) 2.9469(16) 112.6(14) 2_666
N6 H6B O7 0.95(2) 1.89(2) 2.7839(16) 155.3(18) 2_666
O9 H9 O1 0.86(2) 1.94(2) 2.7965(14) 174(2) 2_765
C9 H9A O4 0.958(17) 2.463(17) 3.3339(18) 151.0(14) 2_666
C9 H9C O5 0.95(2) 2.48(2) 3.322(2) 148.8(17) 1_565
O10 H10 O4 0.84(2) 1.95(2) 2.7776(14) 167(2) 1_565
C18 H18B O12 0.965(18) 2.489(18) 3.4512(18) 174.9(15) 2_766
C18 H18C O2 0.960(19) 2.630(19) 3.2001(18) 118.4(13) 1_546
O1 H1A O11 0.93(2) 1.67(2) 2.5940(15) 169(2) .
O2 H2A O11 0.95(2) 1.83(2) 2.7657(14) 170(2) 2_775
N3 H3A O12 0.94(2) 1.80(2) 2.7058(16) 161.3(18) 1_465
N3 H3N O7 0.94(2) 1.82(2) 2.7549(15) 170.6(17) 1_565
O4 H4A O8 0.88(3) 1.75(3) 2.6110(15) 167(2) 2_756
O5 H5A O8 0.91(2) 1.88(2) 2.7920(14) 178(2) .
N6 H6A O1 0.904(18) 2.172(18) 3.0218(16) 156.5(16) 2_666
N6 H6A O9 0.904(18) 2.501(18) 3.0100(15) 116.1(13) 2_666
N6 H6A O10 0.904(18) 2.479(19) 2.9469(16) 112.6(14) 2_666
N6 H6B O7 0.95(2) 1.89(2) 2.7839(16) 155.3(18) 2_666
O9 H9 O1 0.86(2) 1.94(2) 2.7965(14) 174(2) 2_765
C9 H9A O4 0.958(17) 2.463(17) 3.3339(18) 151.0(14) 2_666
C9 H9C O5 0.95(2) 2.48(2) 3.322(2) 148.8(17) 1_565
O10 H10 O4 0.84(2) 1.95(2) 2.7776(14) 167(2) 1_565
C18 H18B O12 0.965(18) 2.489(18) 3.4512(18) 174.9(15) 2_766
C18 H18C O2 0.960(19) 2.630(19) 3.2001(18) 118.4(13) 1_546

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.056

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SD20170302CM1_RT
_database_code_depnum_ccdc_archive 'CCDC 1914567'
loop_
_audit_author_name
_audit_author_address
'Tejender S.Thakur'
;Central Drug Research Institute
India
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            '(+/-) Synephrine L-tarataric acid salt (2:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H14 N O2), C4 H4 O6'
_chemical_formula_sum            'C22 H32 N2 O10'
_chemical_formula_weight         484.49

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.6127(4)
_cell_length_b                   9.3029(7)
_cell_length_c                   11.6456(6)
_cell_angle_alpha                101.243(5)
_cell_angle_beta                 91.903(5)
_cell_angle_gamma                105.888(6)
_cell_volume                     571.19(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3604
_cell_measurement_theta_min      2.3610
_cell_measurement_theta_max      30.9960

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             258
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81632
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   MicroMax003_Mo
_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_detector_area_resol_mean 28.5714
_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_orient_matrix_UB_11      0.105599
_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_orient_matrix_type       XPlain
_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_reflns_number            6247
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.620
_diffrn_reflns_theta_max         31.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3932
_reflns_number_gt                3142
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_max     0.863
_reflns_Friedel_fraction_full    0.974

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+0.0886P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   2.5(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3932
_refine_ls_number_parameters     346
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C19 C 0.7120(8) 0.8315(4) 0.6218(3) 0.0427(8) Uani 1 1 d . . . . .
C20 C 0.7643(7) 0.6925(4) 0.6588(3) 0.0375(7) Uani 1 1 d . . . . .
H20 H 0.715797 0.604962 0.591966 0.045 Uiso 1 1 calc R U . . .
C21 C 0.6152(6) 0.6526(4) 0.7610(3) 0.0343(6) Uani 1 1 d . . . . .
H21 H 0.438075 0.630878 0.736400 0.041 Uiso 1 1 calc R U . . .
C22 C 0.6594(6) 0.5093(3) 0.7921(3) 0.0326(6) Uani 1 1 d . . . . .
O7 O 0.5071(6) 0.8078(3) 0.5644(3) 0.0671(10) Uani 1 1 d . . . . .
O8 O 0.8710(6) 0.9575(3) 0.6506(2) 0.0550(7) Uani 1 1 d . . . . .
O9 O 1.0171(5) 0.7198(3) 0.6966(2) 0.0504(6) Uani 1 1 d . . . . .
H9 H 1.102084 0.735569 0.641969 0.089(18) Uiso 1 1 calc R . . . .
O10 O 0.6834(5) 0.7813(2) 0.85645(19) 0.0403(5) Uani 1 1 d . . . . .
O11 O 0.5397(5) 0.3855(3) 0.7284(2) 0.0454(6) Uani 1 1 d . . . . .
O12 O 0.8122(5) 0.5237(3) 0.8778(2) 0.0439(6) Uani 1 1 d . . . . .
C10 C 0.2423(6) -0.0500(4) 0.3068(3) 0.0342(7) Uani 1 1 d . . . . .
C11 C 0.0209(6) -0.1512(4) 0.2475(3) 0.0401(8) Uani 1 1 d . . . . .
H11 H -0.120981 -0.172008 0.287507 0.048 Uiso 1 1 calc R U . . .
C12 C 0.0094(6) -0.2205(4) 0.1309(3) 0.0390(7) Uani 1 1 d . . . . .
H12 H -0.139462 -0.287056 0.092592 0.047 Uiso 1 1 calc R U . . .
C13 C 0.2194(6) -0.1911(4) 0.0710(2) 0.0326(6) Uani 1 1 d . . . . .
C14 C 0.4393(6) -0.0913(4) 0.1286(3) 0.0403(8) Uani 1 1 d . . . . .
H14 H 0.581698 -0.071634 0.088711 0.048 Uiso 1 1 calc R U . . .
C15 C 0.4481(6) -0.0206(4) 0.2451(3) 0.0400(8) Uani 1 1 d . . . . .
H15 H 0.596122 0.048121 0.282503 0.048 Uiso 1 1 calc R U . . .
C16 C 0.2474(7) 0.0226(4) 0.4350(3) 0.0372(7) Uani 1 1 d . . . . .
H16 H 0.141547 -0.052860 0.473609 0.045 Uiso 1 1 calc R U . . .
C17 C 0.1497(7) 0.1596(4) 0.4497(3) 0.0395(7) Uani 1 1 d . . . . .
H17A H 0.260439 0.238973 0.417767 0.047 Uiso 1 1 calc R U . . .
H17B H -0.012824 0.131347 0.406442 0.047 Uiso 1 1 calc R U . . .
C18 C 0.0118(8) 0.3430(5) 0.5967(3) 0.0520(9) Uani 1 1 d . . . . .
H18A H 0.093352 0.421687 0.557027 0.078 Uiso 1 1 calc R U . . .
H18B H 0.025302 0.384778 0.679621 0.078 Uiso 1 1 calc R U . . .
H18C H -0.160612 0.303757 0.567476 0.078 Uiso 1 1 calc R U . . .
N6 N 0.1300(6) 0.2187(3) 0.5753(2) 0.0358(6) Uani 1 1 d . . . . .
O4 O 0.2178(5) -0.2543(3) -0.04505(19) 0.0445(6) Uani 1 1 d . . . . .
O5 O 0.4893(5) 0.0726(3) 0.4942(2) 0.0453(6) Uani 1 1 d . . . . .
C1 C 0.1314(7) 0.3724(4) 0.0967(3) 0.0413(8) Uani 1 1 d . . . . .
C2 C 0.3420(7) 0.4795(4) 0.1554(3) 0.0475(9) Uani 1 1 d . . . . .
H2 H 0.487671 0.498552 0.117972 0.057 Uiso 1 1 calc R U . . .
C3 C 0.3424(8) 0.5597(4) 0.2690(3) 0.0518(10) Uani 1 1 d . . . . .
H3 H 0.486849 0.632002 0.306612 0.062 Uiso 1 1 calc R U . . .
C4 C 0.1299(8) 0.5324(4) 0.3257(3) 0.0474(9) Uani 1 1 d . . . . .
C5 C -0.0840(8) 0.4243(5) 0.2675(4) 0.0591(11) Uani 1 1 d . . . . .
H5 H -0.229466 0.404167 0.305107 0.071 Uiso 1 1 calc R U . . .
C6 C -0.0809(7) 0.3477(5) 0.1552(4) 0.0554(10) Uani 1 1 d . . . . .
H6 H -0.226155 0.276813 0.117019 0.067 Uiso 1 1 calc R U . . .
C7 C 0.1397(7) 0.2823(4) -0.0249(3) 0.0440(8) Uani 1 1 d . . . . .
H7 H 0.291098 0.332242 -0.057909 0.053 Uiso 1 1 calc R U . . .
C8 C 0.1434(8) 0.1229(4) -0.0161(3) 0.0476(9) Uani 1 1 d . . . . .
H8A H 0.287821 0.130023 0.035140 0.057 Uiso 1 1 calc R U . . .
H8B H -0.003598 0.075585 0.019423 0.057 Uiso 1 1 calc R U . . .
C9 C 0.3941(8) 0.0610(5) -0.1818(4) 0.0628(11) Uani 1 1 d . . . . .
H9A H 0.444993 0.167483 -0.184365 0.094 Uiso 1 1 calc R U . . .
H9B H 0.378699 0.000358 -0.259893 0.094 Uiso 1 1 calc R U . . .
H9C H 0.516021 0.039113 -0.133456 0.094 Uiso 1 1 calc R U . . .
N3 N 0.1508(6) 0.0239(3) -0.1316(3) 0.0432(7) Uani 1 1 d . . . . .
O1 O 0.1174(7) 0.6107(4) 0.4362(2) 0.0670(9) Uani 1 1 d . . . . .
H1A H 0.258022 0.660106 0.465469 0.12(3) Uiso 1 1 calc R . . . .
O2 O -0.0680(6) 0.2612(3) -0.1037(3) 0.0670(10) Uani 1 1 d . . . . .
H4A H 0.069(7) -0.336(4) -0.069(3) 0.045(10) Uiso 1 1 d . . . . .
H5A H 0.475(13) -0.031(8) 0.521(6) 0.13(2) Uiso 1 1 d . . . . .
H6A H 0.035(8) 0.142(5) 0.605(3) 0.050(11) Uiso 1 1 d . . . . .
H6B H 0.264(8) 0.246(4) 0.612(3) 0.038(10) Uiso 1 1 d . . . . .
H3B H 0.123(8) -0.080(5) -0.122(3) 0.058(12) Uiso 1 1 d . . . . .
H3A H 0.013(11) 0.023(5) -0.194(4) 0.082(15) Uiso 1 1 d . . . . .
H10 H 0.527(12) 0.768(7) 0.905(5) 0.12(2) Uiso 1 1 d . . . . .
H2A H -0.106(10) 0.342(6) -0.118(4) 0.079(16) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C19 O8 1.240(4) . ?
C19 O7 1.253(5) . ?
C19 C20 1.536(4) . ?
C20 O9 1.410(4) . ?
C20 C21 1.525(4) . ?
C21 O10 1.420(4) . ?
C21 C22 1.527(4) . ?
C22 O11 1.241(4) . ?
C22 O12 1.256(4) . ?
C10 C15 1.373(5) . ?
C10 C11 1.399(4) . ?
C10 C16 1.510(4) . ?
C11 C12 1.376(4) . ?
C12 C13 1.379(5) . ?
C13 O4 1.363(4) . ?
C13 C14 1.382(4) . ?
C14 C15 1.381(4) . ?
C16 O5 1.415(4) . ?
C16 C17 1.503(5) . ?
C17 N6 1.479(4) . ?
C18 N6 1.469(5) . ?
C1 C2 1.376(5) . ?
C1 C6 1.379(6) . ?
C1 C7 1.508(5) . ?
C2 C3 1.385(5) . ?
C3 C4 1.369(6) . ?
C4 O1 1.364(4) . ?
C4 C5 1.390(6) . ?
C5 C6 1.365(6) . ?
C7 O2 1.405(4) . ?
C7 C8 1.512(5) . ?
C8 N3 1.483(5) . ?
C9 N3 1.483(5) . ?

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
_geom_angle_publ_flag
O8 C19 O7 124.7(3) . . ?
O8 C19 C20 118.8(3) . . ?
O7 C19 C20 116.4(3) . . ?
O9 C20 C21 106.9(2) . . ?
O9 C20 C19 112.4(3) . . ?
C21 C20 C19 110.3(3) . . ?
O10 C21 C20 108.6(2) . . ?
O10 C21 C22 113.1(2) . . ?
C20 C21 C22 109.4(3) . . ?
O11 C22 O12 124.7(3) . . ?
O11 C22 C21 116.2(3) . . ?
O12 C22 C21 119.0(3) . . ?
C15 C10 C11 118.1(3) . . ?
C15 C10 C16 122.4(3) . . ?
C11 C10 C16 119.5(3) . . ?
C12 C11 C10 121.2(3) . . ?
C11 C12 C13 119.8(3) . . ?
O4 C13 C12 122.4(3) . . ?
O4 C13 C14 118.0(3) . . ?
C12 C13 C14 119.6(3) . . ?
C15 C14 C13 120.1(3) . . ?
C10 C15 C14 121.2(3) . . ?
O5 C16 C17 107.0(3) . . ?
O5 C16 C10 113.0(3) . . ?
C17 C16 C10 111.3(2) . . ?
N6 C17 C16 110.5(2) . . ?
C18 N6 C17 114.0(3) . . ?
C2 C1 C6 117.4(4) . . ?
C2 C1 C7 120.4(4) . . ?
C6 C1 C7 122.2(3) . . ?
C1 C2 C3 121.7(4) . . ?
C4 C3 C2 119.9(3) . . ?
O1 C4 C3 122.5(4) . . ?
O1 C4 C5 118.4(4) . . ?
C3 C4 C5 119.0(4) . . ?
C6 C5 C4 120.0(4) . . ?
C5 C6 C1 122.0(3) . . ?
O2 C7 C1 114.8(4) . . ?
O2 C7 C8 105.2(3) . . ?
C1 C7 C8 108.7(3) . . ?
N3 C8 C7 113.1(3) . . ?
C9 N3 C8 114.5(3) . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SD20170324cx
_database_code_depnum_ccdc_archive 'CCDC 1914542'
loop_
_audit_author_name
_audit_author_address
'Tejender S.Thakur'
;Central Drug Research Institute
India
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            
'(+/-)Synephrine Terephthalic acid (1:0.5) monohydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H14 N O2, 0.5(C8 H4 O4), H2 O'
_chemical_formula_sum            'C13 H18 N O5'
_chemical_formula_weight         268.28

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   15.4695(12)
_cell_length_b                   11.6758(5)
_cell_length_c                   15.9648(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.858(8)
_cell_angle_gamma                90
_cell_volume                     2657.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6276
_cell_measurement_theta_min      2.7700
_cell_measurement_theta_max      31.2360

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79945
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_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_detector_area_resol_mean 28.5714
_diffrn_reflns_number            14028
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_measurement_details      
;
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 0.0000
	             XTD: 44.7862
	          2theta: -19.6652
scan:
	Number of images: 200
	           Slice: -30.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 60.0000
	             Phi: 90.0000
	             XTD: 44.7862
	          2theta: -19.6652
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 180.0000
	             XTD: 44.7862
	          2theta: -19.6652
scan:
	Number of images: 200
	           Slice: -110.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -60.0000
	             Phi: 270.0000
	             XTD: 44.7862
	          2theta: -19.6652

;
_diffrn_orient_matrix_UB_11      -0.055470
_diffrn_orient_matrix_UB_12      0.028138
_diffrn_orient_matrix_UB_13      0.044058
_diffrn_orient_matrix_UB_21      -0.005486
_diffrn_orient_matrix_UB_22      0.068607
_diffrn_orient_matrix_UB_23      -0.050722
_diffrn_orient_matrix_UB_31      0.042526
_diffrn_orient_matrix_UB_32      -0.068355
_diffrn_orient_matrix_UB_33      -0.097056
_diffrn_orient_matrix_type       XPlain
_diffrn_reflns_transf_matrix_11  -0.055470
_diffrn_reflns_transf_matrix_12  0.028138
_diffrn_reflns_transf_matrix_13  0.044058
_diffrn_reflns_transf_matrix_21  -0.005486
_diffrn_reflns_transf_matrix_22  0.068607
_diffrn_reflns_transf_matrix_23  -0.050722
_diffrn_reflns_transf_matrix_31  0.042526
_diffrn_reflns_transf_matrix_32  -0.068355
_diffrn_reflns_transf_matrix_33  -0.097056
_diffrn_reflns_theta_min         2.255
_diffrn_reflns_theta_max         31.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3993
_reflns_number_gt                2731
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0629P)²+1.3004P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3993
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1606
_refine_ls_wR_factor_gt          0.1360
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.94602(12) 0.83934(13) 0.83762(10) 0.0404(4) Uani 1 1 d . . . . .
C2 C 0.98875(13) 0.93598(15) 0.88723(11) 0.0471(4) Uani 1 1 d . . . . .
H2 H 1.035894 0.926876 0.944692 0.057 Uiso 1 1 calc R U . . .
C3 C 0.96325(14) 1.04454(15) 0.85371(12) 0.0517(4) Uani 1 1 d . . . . .
H3 H 0.992900 1.107705 0.888506 0.062 Uiso 1 1 calc R U . . .
C4 C 0.89333(13) 1.06023(14) 0.76802(11) 0.0465(4) Uani 1 1 d . . . . .
C5 C 0.85053(13) 0.96563(15) 0.71700(11) 0.0477(4) Uani 1 1 d . . . . .
H5 H 0.804079 0.975090 0.659201 0.057 Uiso 1 1 calc R U . . .
C6 C 0.87674(13) 0.85619(14) 0.75187(11) 0.0467(4) Uani 1 1 d . . . . .
H6 H 0.847226 0.793035 0.716985 0.056 Uiso 1 1 calc R U . . .
C7 C 0.97801(13) 0.72285(14) 0.88080(11) 0.0436(4) Uani 1 1 d . . . . .
H7 H 1.043904 0.714202 0.889266 0.052 Uiso 1 1 calc R U . . .
C8 C 0.92477(13) 0.62420(14) 0.82182(11) 0.0460(4) Uani 1 1 d . . . . .
H8A H 0.857877 0.636395 0.803360 0.055 Uiso 1 1 calc R U . . .
H8B H 0.938378 0.620475 0.767474 0.055 Uiso 1 1 calc R U . . .
C9 C 0.91513(16) 0.41085(16) 0.81646(13) 0.0584(5) Uani 1 1 d . . . . .
H9A H 0.940338 0.406384 0.770286 0.088 Uiso 1 1 calc R U . . .
H9B H 0.847947 0.415122 0.788391 0.088 Uiso 1 1 calc R U . . .
H9C H 0.933168 0.343963 0.854290 0.088 Uiso 1 1 calc R U . . .
C10 C 0.750000 0.90048(17) 1.000000 0.0364(5) Uani 1 2 d S T P . .
C11 C 0.77033(12) 0.96056(13) 0.93465(11) 0.0413(4) Uani 1 1 d . . . . .
H11 H 0.784957 0.920884 0.891358 0.050 Uiso 1 1 calc R U . . .
C12 C 0.76889(12) 1.07953(12) 0.93369(10) 0.0392(4) Uani 1 1 d . . . . .
H12 H 0.780573 1.119279 0.888697 0.047 Uiso 1 1 calc R U . . .
C13 C 0.750000 1.13910(16) 1.000000 0.0340(4) Uani 1 2 d S T P . .
C14 C 0.750000 0.77090(17) 1.000000 0.0407(5) Uani 1 2 d S T P . .
C15 C 0.750000 1.26796(16) 1.000000 0.0369(5) Uani 1 2 d S T P . .
N3 N 0.95212(12) 0.51453(11) 0.87275(10) 0.0425(3) Uani 1 1 d . . . . .
O1 O 0.87008(13) 1.16971(11) 0.73831(10) 0.0664(4) Uani 1 1 d . . . . .
O2 O 0.97451(11) 0.71568(10) 0.96858(8) 0.0496(3) Uani 1 1 d . . . . .
O4 O 0.79402(10) 0.72071(9) 0.95936(10) 0.0565(4) Uani 1 1 d . . . . .
O5 O 0.75574(10) 1.31915(9) 0.93300(8) 0.0504(3) Uani 1 1 d . . . . .
O6 O 0.86461(9) 0.50725(10) 0.99677(9) 0.0442(3) Uani 1 1 d . . . . .
H1A H 0.8277(18) 1.172(2) 0.6841(18) 0.079(8) Uiso 1 1 d . . . . .
H2A H 0.9143(19) 0.736(2) 0.9616(16) 0.087(9) Uiso 1 1 d . . . . .
H3A H 0.9269(17) 0.5151(17) 0.9204(16) 0.067(6) Uiso 1 1 d . . . . .
H3B H 1.0147(17) 0.5100(16) 0.9003(14) 0.058(6) Uiso 1 1 d . . . . .
H6A H 0.8323(16) 0.571(2) 0.9871(15) 0.068(7) Uiso 1 1 d . . . . .
H6B H 0.8203(18) 0.450(2) 0.9767(16) 0.077(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.386(2) . ?
C1 C2 1.390(2) . ?
C1 C7 1.518(2) . ?
C2 C3 1.373(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 O1 1.362(2) . ?
C4 C5 1.379(2) . ?
C5 C6 1.390(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O2 1.4257(19) . ?
C7 C8 1.513(2) . ?
C7 H7 0.9800 . ?
C8 N3 1.487(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N3 1.484(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.3908(18) 2_657 ?
C10 C11 1.3909(18) . ?
C10 C14 1.513(3) . ?
C11 C12 1.389(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.3892(17) . ?
C12 H12 0.9300 . ?
C13 C15 1.505(3) . ?
C14 O4 1.2535(15) 2_657 ?
C14 O4 1.2535(15) . ?
C15 O5 1.2581(14) 2_657 ?
C15 O5 1.2582(14) . ?
N3 H3A 0.98(2) . ?
N3 H3B 0.90(2) . ?
O1 H1A 0.86(3) . ?
O2 H2A 0.93(3) . ?
O6 H6A 0.87(2) . ?
O6 H6B 0.92(3) . ?

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
_geom_angle_publ_flag
C6 C1 C2 117.50(15) . . ?
C6 C1 C7 124.49(15) . . ?
C2 C1 C7 118.01(14) . . ?
C3 C2 C1 121.77(16) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 120.14(16) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
O1 C4 C5 122.99(16) . . ?
O1 C4 C3 117.80(16) . . ?
C5 C4 C3 119.21(16) . . ?
C4 C5 C6 120.08(16) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 121.30(15) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O2 C7 C8 110.34(14) . . ?
O2 C7 C1 111.64(13) . . ?
C8 C7 C1 113.37(14) . . ?
O2 C7 H7 107.0 . . ?
C8 C7 H7 107.0 . . ?
C1 C7 H7 107.0 . . ?
N3 C8 C7 110.16(13) . . ?
N3 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
N3 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
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 . . ?
C11 C10 C11 119.42(18) 2_657 . ?
C11 C10 C14 120.29(9) 2_657 . ?
C11 C10 C14 120.29(9) . . ?
C12 C11 C10 120.34(15) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.96(14) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C12 119.92(18) 2_657 . ?
C12 C13 C15 120.04(9) 2_657 . ?
C12 C13 C15 120.04(9) . . ?
O4 C14 O4 124.26(19) 2_657 . ?
O4 C14 C10 117.87(10) 2_657 . ?
O4 C14 C10 117.87(10) . . ?
O5 C15 O5 123.27(19) 2_657 . ?
O5 C15 C13 118.37(9) 2_657 . ?
O5 C15 C13 118.37(9) . . ?
C9 N3 C8 114.23(14) . . ?
C9 N3 H3A 107.4(13) . . ?
C8 N3 H3A 107.7(12) . . ?
C9 N3 H3B 109.8(12) . . ?
C8 N3 H3B 110.1(13) . . ?
H3A N3 H3B 107.4(19) . . ?
C4 O1 H1A 112.1(17) . . ?
C7 O2 H2A 106.7(15) . . ?
H6A O6 H6B 105(2) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.7(3) . . . . ?
C7 C1 C2 C3 -179.21(16) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 O1 179.40(17) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
O1 C4 C5 C6 -179.15(18) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C7 C1 C6 C5 179.46(17) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C6 C1 C7 O2 -126.92(18) . . . . ?
C2 C1 C7 O2 52.9(2) . . . . ?
C6 C1 C7 C8 -1.5(2) . . . . ?
C2 C1 C7 C8 178.32(16) . . . . ?
O2 C7 C8 N3 -47.4(2) . . . . ?
C1 C7 C8 N3 -173.42(14) . . . . ?
C11 C10 C11 C12 -1.03(12) 2_657 . . . ?
C14 C10 C11 C12 178.98(11) . . . . ?
C10 C11 C12 C13 2.0(2) . . . . ?
C11 C12 C13 C12 -1.02(11) . . . 2_657 ?
C11 C12 C13 C15 178.98(11) . . . . ?
C11 C10 C14 O4 20.53(11) 2_657 . . 2_657 ?
C11 C10 C14 O4 -159.47(11) . . . 2_657 ?
C11 C10 C14 O4 -159.47(11) 2_657 . . . ?
C11 C10 C14 O4 20.53(11) . . . . ?
C12 C13 C15 O5 8.70(11) 2_657 . . 2_657 ?
C12 C13 C15 O5 -171.30(11) . . . 2_657 ?
C12 C13 C15 O5 -171.30(11) 2_657 . . . ?
C12 C13 C15 O5 8.70(11) . . . . ?
C7 C8 N3 C9 -170.94(15) . . . . ?

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.044

