# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1892004'
loop_
_audit_author_name
_audit_author_address
'Andrzej Gzella'
;Poznan University of Medical Sciences
Poland
;
_audit_update_record             
;
2019-01-19 deposited with the CCDC.	2019-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
Imidazolium 2-hydroxybenzoate
;
_chemical_name_common            ?
_chemical_melting_point          401-403
_chemical_formula_moiety         'C7 H5 O3^-^, C3 H5 N2^+^'
_chemical_formula_sum            'C10 H10 N2 O3'
_chemical_formula_weight         206.20

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.0905(6)
_cell_length_b                   10.9922(5)
_cell_length_c                   16.1833(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1972.89(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    130.0(1)
_cell_measurement_reflns_used    6107
_cell_measurement_theta_min      4.28
_cell_measurement_theta_max      29.22

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62815
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3991
_diffrn_reflns_number            16447
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.517
_diffrn_reflns_theta_max         29.599
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2578
_reflns_number_gt                2173
_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    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
; 
WINGX (Farrugia, 2012), OLEX2 v1.2-alpha (Dolomanov et al., 2009), 
PLATON (Spek, 2009)
;

_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)+(0.0528P)²+0.9076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2578
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
C1B C 0.53970(11) 0.48454(11) 0.34064(7) 0.0205(3) Uani 1 1 d . . . . .
C2B C 0.57456(12) 0.36197(12) 0.33660(8) 0.0258(3) Uani 1 1 d . . . . .
C3B C 0.66407(14) 0.32533(14) 0.28155(9) 0.0326(3) Uani 1 1 d . . . . .
H3B H 0.6876 0.2423 0.2793 0.039 Uiso 1 1 calc R U . . .
C4B C 0.71830(13) 0.40890(15) 0.23058(9) 0.0338(3) Uani 1 1 d . . . . .
H4B H 0.7801 0.3834 0.1938 0.041 Uiso 1 1 calc R U . . .
C5B C 0.68377(14) 0.53014(14) 0.23218(9) 0.0318(3) Uani 1 1 d . . . . .
H5B H 0.7206 0.5872 0.1960 0.038 Uiso 1 1 calc R U . . .
C6B C 0.59513(13) 0.56722(12) 0.28698(8) 0.0262(3) Uani 1 1 d . . . . .
H6B H 0.5715 0.6503 0.2882 0.031 Uiso 1 1 calc R U . . .
C7B C 0.44551(11) 0.52569(11) 0.40040(7) 0.0207(3) Uani 1 1 d . . . . .
O8B O 0.42130(8) 0.63612(8) 0.40750(6) 0.0259(2) Uani 1 1 d . . . . .
O9B O 0.39079(8) 0.44320(8) 0.44189(6) 0.0244(2) Uani 1 1 d . . . . .
O10A O 0.52432(11) 0.27630(9) 0.38545(7) 0.0385(3) Uani 1 1 d . . . . .
H10A H 0.468(2) 0.323(2) 0.4174(14) 0.063(7) Uiso 1 1 d . . . . .
N1A N 0.20958(11) 0.55323(10) 0.52389(7) 0.0250(3) Uani 1 1 d . . . . .
H1A H 0.275(2) 0.5218(19) 0.4951(13) 0.054(6) Uiso 1 1 d . . . . .
N2A N 0.07870(11) 0.68284(11) 0.56675(7) 0.0280(3) Uani 1 1 d . . . . .
H2A H 0.034(2) 0.754(2) 0.5733(13) 0.056(6) Uiso 1 1 d . . . . .
C1A C 0.17534(12) 0.66830(12) 0.51944(9) 0.0257(3) Uani 1 1 d . . . . .
H1AA H 0.2135 0.7301 0.4878 0.031 Uiso 1 1 calc R U . . .
C3A C 0.13250(14) 0.49271(13) 0.57533(9) 0.0303(3) Uani 1 1 d . . . . .
H3A H 0.1359 0.4089 0.5895 0.036 Uiso 1 1 calc R U . . .
C2A C 0.05116(14) 0.57389(14) 0.60201(9) 0.0328(3) Uani 1 1 d . . . . .
H2AA H -0.0138 0.5583 0.6388 0.039 Uiso 1 1 calc R U . . .


_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
C1B C6B 1.3993(18) . ?
C1B C2B 1.4031(18) . ?
C1B C7B 1.4938(17) . ?
C2B O10A 1.3499(17) . ?
C2B C3B 1.3933(19) . ?
C3B C4B 1.373(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.387(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.385(2) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B O8B 1.2484(15) . ?
C7B O9B 1.2811(15) . ?
O10A H10A 0.96(2) . ?
N1A C1A 1.3227(17) . ?
N1A C3A 1.3661(19) . ?
N1A H1A 0.93(2) . ?
N2A C1A 1.3268(18) . ?
N2A C2A 1.361(2) . ?
N2A H2A 0.93(2) . ?
C1A H1AA 0.9500 . ?
C3A C2A 1.340(2) . ?
C3A H3A 0.9500 . ?
C2A H2AA 0.9500 . ?

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
C6B C1B C2B 118.28(12) . . ?
C6B C1B C7B 120.82(12) . . ?
C2B C1B C7B 120.91(11) . . ?
O10A C2B C3B 117.83(13) . . ?
O10A C2B C1B 121.93(12) . . ?
C3B C2B C1B 120.24(13) . . ?
C4B C3B C2B 120.18(14) . . ?
C4B C3B H3B 119.9 . . ?
C2B C3B H3B 119.9 . . ?
C3B C4B C5B 120.70(13) . . ?
C3B C4B H4B 119.6 . . ?
C5B C4B H4B 119.6 . . ?
C6B C5B C4B 119.38(13) . . ?
C6B C5B H5B 120.3 . . ?
C4B C5B H5B 120.3 . . ?
C5B C6B C1B 121.19(13) . . ?
C5B C6B H6B 119.4 . . ?
C1B C6B H6B 119.4 . . ?
O8B C7B O9B 122.55(12) . . ?
O8B C7B C1B 120.29(11) . . ?
O9B C7B C1B 117.14(11) . . ?
C2B O10A H10A 102.3(14) . . ?
C1A N1A C3A 108.62(12) . . ?
C1A N1A H1A 123.6(13) . . ?
C3A N1A H1A 127.8(13) . . ?
C1A N2A C2A 108.49(12) . . ?
C1A N2A H2A 126.4(14) . . ?
C2A N2A H2A 125.1(14) . . ?
N1A C1A N2A 108.40(12) . . ?
N1A C1A H1AA 125.8 . . ?
N2A C1A H1AA 125.8 . . ?
C2A C3A N1A 107.05(13) . . ?
C2A C3A H3A 126.5 . . ?
N1A C3A H3A 126.5 . . ?
C3A C2A N2A 107.44(13) . . ?
C3A C2A H2AA 126.3 . . ?
N2A C2A H2AA 126.3 . . ?

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
C6B C1B C2B O10A -179.10(13) . . . . ?
C7B C1B C2B O10A 0.6(2) . . . . ?
C6B C1B C2B C3B 1.4(2) . . . . ?
C7B C1B C2B C3B -178.86(12) . . . . ?
O10A C2B C3B C4B -179.87(14) . . . . ?
C1B C2B C3B C4B -0.3(2) . . . . ?
C2B C3B C4B C5B -1.0(2) . . . . ?
C3B C4B C5B C6B 1.2(2) . . . . ?
C4B C5B C6B C1B -0.1(2) . . . . ?
C2B C1B C6B C5B -1.17(19) . . . . ?
C7B C1B C6B C5B 179.08(12) . . . . ?
C6B C1B C7B O8B -5.30(18) . . . . ?
C2B C1B C7B O8B 174.95(12) . . . . ?
C6B C1B C7B O9B 173.51(11) . . . . ?
C2B C1B C7B O9B -6.23(17) . . . . ?
C3A N1A C1A N2A 0.12(16) . . . . ?
C2A N2A C1A N1A -0.03(16) . . . . ?
C1A N1A C3A C2A -0.16(17) . . . . ?
N1A C3A C2A N2A 0.15(17) . . . . ?
C1A N2A C2A C3A -0.08(17) . . . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: AcOEt'
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1892005'
loop_
_audit_author_name
_audit_author_address
'Andrzej Gzella'
;Poznan University of Medical Sciences
Poland
;
_audit_update_record             
;
2019-01-19 deposited with the CCDC.	2019-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
Imidazolium benzoate
;
_chemical_name_common            ?
_chemical_melting_point          372-374
_chemical_formula_moiety         'C7 H5 O2^-^, C3 H5 N2^+^'
_chemical_formula_sum            'C10 H10 N2 O2'
_chemical_formula_weight         190.20

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                   8.7106(6)
_cell_length_b                   12.3618(6)
_cell_length_c                   9.2744(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.594(8)
_cell_angle_gamma                90
_cell_volume                     928.56(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.0(1)
_cell_measurement_reflns_used    4317
_cell_measurement_theta_min      4.02
_cell_measurement_theta_max      29.02

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65459
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      130.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3991
_diffrn_reflns_number            10482
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.880
_diffrn_reflns_theta_max         29.680
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2348
_reflns_number_gt                2008
_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    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
; 
WINGX (Farrugia, 2012), OLEX2 v1.2-alpha (Dolomanov et al., 2009), 
PLATON (Spek, 2009)
;

_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)+(0.0472P)²+0.3804P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2348
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
N1A N 0.46680(13) 0.79324(9) 0.44285(12) 0.0227(2) Uani 1 1 d . . . . .
H1A H 0.456(2) 0.7288(17) 0.493(2) 0.054(5) Uiso 1 1 d . . . . .
N2A N 0.41949(14) 0.93034(9) 0.28853(12) 0.0254(3) Uani 1 1 d . . . . .
H2A H 0.366(2) 0.9784(15) 0.210(2) 0.043(5) Uiso 1 1 d . . . . .
C1A C 0.35215(16) 0.84425(10) 0.32725(14) 0.0251(3) Uani 1 1 d . . . . .
H1AA H 0.2400 0.8227 0.2798 0.030 Uiso 1 1 calc R U . . .
C2A C 0.58240(17) 0.93488(11) 0.38233(15) 0.0278(3) Uani 1 1 d . . . . .
H2AA H 0.6601 0.9881 0.3801 0.033 Uiso 1 1 calc R U . . .
C3A C 0.61174(16) 0.84912(11) 0.47886(15) 0.0269(3) Uani 1 1 d . . . . .
H3AA H 0.7144 0.8309 0.5575 0.032 Uiso 1 1 calc R U . . .
C1B C 0.33528(14) 0.46853(9) 0.65343(14) 0.0195(2) Uani 1 1 d . . . . .
C2B C 0.46518(16) 0.44705(12) 0.79164(17) 0.0316(3) Uani 1 1 d . . . . .
H2B H 0.5634 0.4889 0.8201 0.038 Uiso 1 1 calc R U . . .
C3B C 0.45256(17) 0.36488(13) 0.88848(18) 0.0384(4) Uani 1 1 d . . . . .
H3B H 0.5422 0.3508 0.9828 0.046 Uiso 1 1 calc R U . . .
C4B C 0.31032(17) 0.30331(11) 0.84869(17) 0.0303(3) Uani 1 1 d . . . . .
H4B H 0.3025 0.2467 0.9149 0.036 Uiso 1 1 calc R U . . .
C5B C 0.17947(17) 0.32471(10) 0.71188(15) 0.0275(3) Uani 1 1 d . . . . .
H5B H 0.0810 0.2832 0.6846 0.033 Uiso 1 1 calc R U . . .
C6B C 0.19191(16) 0.40694(10) 0.61423(14) 0.0234(3) Uani 1 1 d . . . . .
H6B H 0.1019 0.4211 0.5202 0.028 Uiso 1 1 calc R U . . .
C7B C 0.34874(14) 0.56146(9) 0.55342(13) 0.0189(2) Uani 1 1 d . . . . .
O8B O 0.23595(11) 0.57661(7) 0.42386(10) 0.0241(2) Uani 1 1 d . . . . .
O9B O 0.47260(10) 0.62274(7) 0.60953(10) 0.0250(2) Uani 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
N1A C1A 1.3253(16) . ?
N1A C3A 1.3683(16) . ?
N1A H1A 0.95(2) . ?
N2A C1A 1.3269(17) . ?
N2A C2A 1.3656(17) . ?
N2A H2A 0.920(19) . ?
C1A H1AA 0.9500 . ?
C2A C3A 1.3499(18) . ?
C2A H2AA 0.9500 . ?
C3A H3AA 0.9500 . ?
C1B C2B 1.3879(17) . ?
C1B C6B 1.3918(17) . ?
C1B C7B 1.5080(16) . ?
C2B C3B 1.3869(19) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.383(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.384(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3919(18) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B O8B 1.2551(14) . ?
C7B O9B 1.2631(14) . ?

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
C1A N1A C3A 108.06(11) . . ?
C1A N1A H1A 128.2(12) . . ?
C3A N1A H1A 123.8(12) . . ?
C1A N2A C2A 108.65(11) . . ?
C1A N2A H2A 125.8(11) . . ?
C2A N2A H2A 125.6(11) . . ?
N1A C1A N2A 108.90(11) . . ?
N1A C1A H1AA 125.5 . . ?
N2A C1A H1AA 125.5 . . ?
C3A C2A N2A 106.79(11) . . ?
C3A C2A H2AA 126.6 . . ?
N2A C2A H2AA 126.6 . . ?
C2A C3A N1A 107.59(11) . . ?
C2A C3A H3AA 126.2 . . ?
N1A C3A H3AA 126.2 . . ?
C2B C1B C6B 119.00(11) . . ?
C2B C1B C7B 119.49(11) . . ?
C6B C1B C7B 121.43(11) . . ?
C3B C2B C1B 120.41(13) . . ?
C3B C2B H2B 119.8 . . ?
C1B C2B H2B 119.8 . . ?
C4B C3B C2B 120.45(13) . . ?
C4B C3B H3B 119.8 . . ?
C2B C3B H3B 119.8 . . ?
C3B C4B C5B 119.61(12) . . ?
C3B C4B H4B 120.2 . . ?
C5B C4B H4B 120.2 . . ?
C4B C5B C6B 120.08(12) . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C1B C6B C5B 120.44(12) . . ?
C1B C6B H6B 119.8 . . ?
C5B C6B H6B 119.8 . . ?
O8B C7B O9B 123.64(11) . . ?
O8B C7B C1B 119.46(10) . . ?
O9B C7B C1B 116.84(10) . . ?

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
C3A N1A C1A N2A 0.15(14) . . . . ?
C2A N2A C1A N1A -0.10(14) . . . . ?
C1A N2A C2A C3A 0.01(15) . . . . ?
N2A C2A C3A N1A 0.08(15) . . . . ?
C1A N1A C3A C2A -0.14(15) . . . . ?
C6B C1B C2B C3B 0.5(2) . . . . ?
C7B C1B C2B C3B 177.27(13) . . . . ?
C1B C2B C3B C4B -0.1(2) . . . . ?
C2B C3B C4B C5B -0.6(2) . . . . ?
C3B C4B C5B C6B 0.7(2) . . . . ?
C2B C1B C6B C5B -0.33(18) . . . . ?
C7B C1B C6B C5B -177.03(11) . . . . ?
C4B C5B C6B C1B -0.28(19) . . . . ?
C2B C1B C7B O8B 175.45(12) . . . . ?
C6B C1B C7B O8B -7.86(17) . . . . ?
C2B C1B C7B O9B -7.24(17) . . . . ?
C6B C1B C7B O9B 169.46(11) . . . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: AcOEt'
