# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1998492'
loop_
_audit_author_name
_audit_author_address
'Delia Haynes'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2020-05-27 deposited with the CCDC.	2020-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'dicyclohexylammonium formate hydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 N +, C H O2 -, 2(H2 O)'
_chemical_formula_sum            'C13 H29 N O4'
_chemical_formula_weight         263.37

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                   5.1775(7)
_cell_length_b                   17.585(2)
_cell_length_c                   16.534(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.783(2)
_cell_angle_gamma                90
_cell_volume                     1497.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2487
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.21

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   '(SADABS, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9233
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.695
_diffrn_reflns_theta_max         28.267
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3496
_reflns_number_gt                2816
_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       'APEX II, Bruker 2007'
_computing_cell_refinement       'APEX II, Bruker 2007'
_computing_data_reduction        'APEX II, Bruker 2007'
_computing_structure_solution    'SHELXS (Sheldrick 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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+0.3433P] 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         3496
_refine_ls_number_parameters     187
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1317
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
O1 O 1.1000(2) 0.22286(7) 0.76376(7) 0.0300(3) Uani 1 1 d . . . . .
O2 O 0.8176(2) 0.16254(7) 0.83082(8) 0.0355(3) Uani 1 1 d . . . . .
C1 C 1.0425(3) 0.17778(8) 0.81705(9) 0.0223(3) Uani 1 1 d . . . . .
H1 H 1.177491 0.153906 0.848701 0.027 Uiso 1 1 calc R U . . .
N1 N 0.5554(3) 0.26266(7) 0.70319(8) 0.0204(3) Uani 1 1 d . . . . .
H1N H 0.693(4) 0.2417(11) 0.7309(13) 0.036(5) Uiso 1 1 d . . . . .
H2N H 0.410(4) 0.2453(11) 0.7288(12) 0.033(5) Uiso 1 1 d . . . . .
C2 C 0.5757(3) 0.34751(8) 0.71214(9) 0.0185(3) Uani 1 1 d . . . . .
H2 H 0.711128 0.365982 0.679709 0.022 Uiso 1 1 calc R U . . .
C3 C 0.6544(3) 0.36579(9) 0.80112(10) 0.0249(4) Uani 1 1 d . . . . .
H3A H 0.819907 0.341978 0.818297 0.030 Uiso 1 1 calc R U . . .
H3B H 0.526116 0.345450 0.834156 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6767(3) 0.45164(9) 0.81365(10) 0.0264(4) Uani 1 1 d . . . . .
H4A H 0.718658 0.462348 0.871018 0.032 Uiso 1 1 calc R U . . .
H4B H 0.816769 0.471053 0.784736 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4257(3) 0.49190(8) 0.78341(10) 0.0214(3) Uani 1 1 d . . . . .
H5A H 0.450108 0.546447 0.788374 0.026 Uiso 1 1 calc R U . . .
H5B H 0.290185 0.477279 0.816808 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3421(3) 0.47178(8) 0.69503(10) 0.0222(3) Uani 1 1 d . . . . .
H6A H 0.467400 0.492160 0.660928 0.027 Uiso 1 1 calc R U . . .
H6B H 0.175427 0.495165 0.678529 0.027 Uiso 1 1 calc R U . . .
C7 C 0.3205(3) 0.38587(8) 0.68240(9) 0.0191(3) Uani 1 1 d . . . . .
H7A H 0.182764 0.365938 0.711982 0.023 Uiso 1 1 calc R U . . .
H7B H 0.277193 0.374947 0.625130 0.023 Uiso 1 1 calc R U . . .
C8 C 0.5302(3) 0.23064(8) 0.61854(9) 0.0168(3) Uani 1 1 d . . . . .
H8 H 0.383324 0.255349 0.586905 0.020 Uiso 1 1 calc R U . . .
C9 C 0.4728(3) 0.14583(8) 0.62424(10) 0.0219(3) Uani 1 1 d . . . . .
H9A H 0.312004 0.138671 0.648752 0.026 Uiso 1 1 calc R U . . .
H9B H 0.611008 0.121341 0.658732 0.026 Uiso 1 1 calc R U . . .
C10 C 0.4495(3) 0.10913(8) 0.54016(10) 0.0226(3) Uani 1 1 d . . . . .
H10A H 0.422569 0.054855 0.545538 0.027 Uiso 1 1 calc R U . . .
H10B H 0.299949 0.129994 0.507555 0.027 Uiso 1 1 calc R U . . .
C11 C 0.6914(3) 0.12279(9) 0.49743(10) 0.0229(3) Uani 1 1 d . . . . .
H11A H 0.667394 0.101540 0.443051 0.027 Uiso 1 1 calc R U . . .
H11B H 0.838498 0.097537 0.526983 0.027 Uiso 1 1 calc R U . . .
C12 C 0.7456(3) 0.20763(9) 0.49257(10) 0.0253(4) Uani 1 1 d . . . . .
H12A H 0.604749 0.231955 0.459029 0.030 Uiso 1 1 calc R U . . .
H12B H 0.904062 0.215448 0.466989 0.030 Uiso 1 1 calc R U . . .
C13 C 0.7735(3) 0.24436(9) 0.57663(10) 0.0229(3) Uani 1 1 d . . . . .
H13A H 0.922470 0.222985 0.609072 0.027 Uiso 1 1 calc R U . . .
H13B H 0.801664 0.298599 0.571410 0.027 Uiso 1 1 calc R U . . .
O1W O 0.7473(3) 0.08984(8) 0.96805(9) 0.0365(3) Uani 1 1 d D . . . .
H1W H 0.763(5) 0.1164(13) 0.9227(12) 0.050(6) Uiso 1 1 d D . . . .
O2W O 1.2677(2) 0.06843(7) 1.03228(8) 0.0332(3) Uani 1 1 d D . . . .
H3W H 1.265(5) 0.0174(11) 1.0358(15) 0.060(7) Uiso 1 1 d D . . . .
H2W H 0.917(5) 0.087(3) 0.992(3) 0.17(2) Uiso 1 1 d D . . . .
H4W H 1.406(7) 0.083(3) 1.007(3) 0.18(2) Uiso 1 1 d 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
O1 C1 1.2436(18) . ?
O2 C1 1.238(2) . ?
N1 C8 1.5021(19) . ?
N1 C2 1.5020(18) . ?
C2 C7 1.520(2) . ?
C2 C3 1.521(2) . ?
C3 C4 1.527(2) . ?
C4 C5 1.520(2) . ?
C5 C6 1.523(2) . ?
C6 C7 1.528(2) . ?
C8 C13 1.517(2) . ?
C8 C9 1.525(2) . ?
C9 C10 1.526(2) . ?
C10 C11 1.518(2) . ?
C11 C12 1.522(2) . ?
C12 C13 1.526(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
O2 C1 O1 124.41(15) . . ?
C8 N1 C2 117.57(12) . . ?
N1 C2 C7 111.03(12) . . ?
N1 C2 C3 108.33(12) . . ?
C7 C2 C3 111.01(12) . . ?
C2 C3 C4 110.46(13) . . ?
C5 C4 C3 111.45(13) . . ?
C4 C5 C6 110.99(12) . . ?
C5 C6 C7 111.76(12) . . ?
C2 C7 C6 110.20(12) . . ?
N1 C8 C13 111.58(12) . . ?
N1 C8 C9 107.95(12) . . ?
C13 C8 C9 111.09(12) . . ?
C8 C9 C10 110.80(12) . . ?
C11 C10 C9 111.35(13) . . ?
C10 C11 C12 110.17(12) . . ?
C11 C12 C13 111.59(13) . . ?
C8 C13 C12 110.00(12) . . ?

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.053




#=== END
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1998498'
loop_
_audit_author_name
_audit_author_address
'Delia Haynes'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'dicyclohexylammonium phenylacetate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 N +, C8 H7 O2 -'
_chemical_formula_sum            'C20 H31 N O2'
_chemical_formula_weight         317.46

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                   5.5919(10)
_cell_length_b                   10.782(2)
_cell_length_c                   15.271(3)
_cell_angle_alpha                93.444(3)
_cell_angle_beta                 93.522(3)
_cell_angle_gamma                94.507(3)
_cell_volume                     914.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3102
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.01

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.26
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_max          1.05
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.738
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   '(SADABS, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_reflns_number            8842
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.339
_diffrn_reflns_theta_max         25.085
_diffrn_reflns_theta_full        25.085
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3227
_reflns_number_gt                2684
_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       'APEX II, Bruker 2007'
_computing_cell_refinement       'APEX II, Bruker 2007'
_computing_data_reduction        'APEX II, Bruker 2007'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Ammonium H atoms were located in the difference map.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+0.1920P] 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         3227
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1 O 0.59834(17) 1.07517(9) 0.27879(7) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.87133(17) 0.94102(9) 0.30171(7) 0.0276(3) Uani 1 1 d . . . . .
C1 C 0.8101(2) 1.04944(13) 0.29508(9) 0.0213(3) Uani 1 1 d . . . . .
C2 C 1.0042(3) 1.15806(14) 0.31117(10) 0.0263(4) Uani 1 1 d . . . . .
H2A H 1.005913 1.189965 0.373378 0.032 Uiso 1 1 calc R U . . .
H2B H 1.162540 1.126041 0.302060 0.032 Uiso 1 1 calc R U . . .
C3 C 0.9739(2) 1.26477(13) 0.25376(10) 0.0230(3) Uani 1 1 d . . . . .
C4 C 0.7807(3) 1.33797(13) 0.25999(10) 0.0260(4) Uani 1 1 d . . . . .
H4 H 0.666432 1.321136 0.302152 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7525(3) 1.43414(15) 0.20621(11) 0.0323(4) Uani 1 1 d . . . . .
H5 H 0.619165 1.482884 0.211428 0.039 Uiso 1 1 calc R U . . .
C6 C 0.9174(3) 1.46048(15) 0.14441(11) 0.0346(4) Uani 1 1 d . . . . .
H6 H 0.897237 1.526499 0.106837 0.042 Uiso 1 1 calc R U . . .
C7 C 1.1108(3) 1.38980(15) 0.13818(10) 0.0351(4) Uani 1 1 d . . . . .
H7 H 1.225897 1.407821 0.096521 0.042 Uiso 1 1 calc R U . . .
C8 C 1.1388(3) 1.29259(14) 0.19216(10) 0.0295(4) Uani 1 1 d . . . . .
H8 H 1.272762 1.244297 0.186915 0.035 Uiso 1 1 calc R U . . .
N1 N 0.3028(2) 0.86265(11) 0.26765(7) 0.0193(3) Uani 1 1 d . . . . .
H1N H 0.156(3) 0.8976(15) 0.2824(11) 0.034(4) Uiso 1 1 d . . . . .
H2N H 0.419(3) 0.9351(16) 0.2727(10) 0.033(4) Uiso 1 1 d . . . . .
C9 C 0.3676(2) 0.77493(13) 0.33572(9) 0.0215(3) Uani 1 1 d . . . . .
H9 H 0.529591 0.746592 0.324504 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3833(3) 0.84444(14) 0.42560(9) 0.0266(4) Uani 1 1 d . . . . .
H10A H 0.226987 0.877646 0.436459 0.032 Uiso 1 1 calc R U . . .
H10B H 0.506833 0.915715 0.427296 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4485(3) 0.75770(16) 0.49709(10) 0.0338(4) Uani 1 1 d . . . . .
H11A H 0.612098 0.731426 0.489579 0.041 Uiso 1 1 calc R U . . .
H11B H 0.449305 0.803031 0.555451 0.041 Uiso 1 1 calc R U . . .
C12 C 0.2705(3) 0.64306(16) 0.49323(10) 0.0366(4) Uani 1 1 d . . . . .
H12A H 0.322120 0.586289 0.538044 0.044 Uiso 1 1 calc R U . . .
H12B H 0.110025 0.668608 0.506947 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2536(3) 0.57465(15) 0.40282(11) 0.0376(4) Uani 1 1 d . . . . .
H13A H 0.129887 0.503472 0.400971 0.045 Uiso 1 1 calc R U . . .
H13B H 0.409663 0.541226 0.391731 0.045 Uiso 1 1 calc R U . . .
C14 C 0.1888(3) 0.66122(14) 0.33145(10) 0.0280(4) Uani 1 1 d . . . . .
H14A H 0.187881 0.615968 0.273058 0.034 Uiso 1 1 calc R U . . .
H14B H 0.025511 0.687868 0.338980 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2763(3) 0.81194(13) 0.17397(9) 0.0210(3) Uani 1 1 d . . . . .
H15 H 0.137346 0.747075 0.167222 0.025 Uiso 1 1 calc R U . . .
C16 C 0.4990(3) 0.75198(15) 0.14664(10) 0.0283(4) Uani 1 1 d . . . . .
H16A H 0.528608 0.681983 0.183885 0.034 Uiso 1 1 calc R U . . .
H16B H 0.640227 0.813870 0.155396 0.034 Uiso 1 1 calc R U . . .
C17 C 0.4675(3) 0.70381(15) 0.05033(10) 0.0322(4) Uani 1 1 d . . . . .
H17A H 0.617112 0.668570 0.032967 0.039 Uiso 1 1 calc R U . . .
H17B H 0.336042 0.636187 0.042914 0.039 Uiso 1 1 calc R U . . .
C18 C 0.4093(3) 0.80665(14) -0.00916(10) 0.0289(4) Uani 1 1 d . . . . .
H18A H 0.548672 0.869570 -0.007256 0.035 Uiso 1 1 calc R U . . .
H18B H 0.378609 0.771181 -0.070497 0.035 Uiso 1 1 calc R U . . .
C19 C 0.1906(3) 0.86867(15) 0.01939(10) 0.0298(4) Uani 1 1 d . . . . .
H19A H 0.047536 0.808034 0.010349 0.036 Uiso 1 1 calc R U . . .
H19B H 0.163290 0.939154 -0.017651 0.036 Uiso 1 1 calc R U . . .
C20 C 0.2203(3) 0.91675(14) 0.11578(9) 0.0256(3) Uani 1 1 d . . . . .
H20A H 0.352257 0.984020 0.123910 0.031 Uiso 1 1 calc R U . . .
H20B H 0.070448 0.951938 0.133008 0.031 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
O1 C1 1.2511(17) . ?
O2 C1 1.2518(17) . ?
C1 C2 1.531(2) . ?
C2 C3 1.502(2) . ?
C3 C8 1.386(2) . ?
C3 C4 1.392(2) . ?
C4 C5 1.374(2) . ?
C5 C6 1.386(2) . ?
C6 C7 1.376(2) . ?
C7 C8 1.384(2) . ?
N1 C15 1.4950(18) . ?
N1 C9 1.4939(17) . ?
C9 C14 1.515(2) . ?
C9 C10 1.5181(19) . ?
C10 C11 1.525(2) . ?
C11 C12 1.521(2) . ?
C12 C13 1.520(2) . ?
C13 C14 1.522(2) . ?
C15 C16 1.517(2) . ?
C15 C20 1.5189(19) . ?
C16 C17 1.525(2) . ?
C17 C18 1.517(2) . ?
C18 C19 1.514(2) . ?
C19 C20 1.526(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
O1 C1 O2 124.09(13) . . ?
O1 C1 C2 117.63(13) . . ?
O2 C1 C2 118.24(12) . . ?
C3 C2 C1 115.02(12) . . ?
C8 C3 C4 117.99(14) . . ?
C8 C3 C2 120.46(14) . . ?
C4 C3 C2 121.56(13) . . ?
C5 C4 C3 121.13(15) . . ?
C4 C5 C6 120.38(15) . . ?
C7 C6 C5 119.14(15) . . ?
C6 C7 C8 120.48(15) . . ?
C7 C8 C3 120.88(15) . . ?
C15 N1 C9 117.32(11) . . ?
N1 C9 C14 111.48(11) . . ?
N1 C9 C10 108.79(11) . . ?
C14 C9 C10 111.43(12) . . ?
C9 C10 C11 110.37(12) . . ?
C12 C11 C10 111.16(13) . . ?
C13 C12 C11 111.05(14) . . ?
C12 C13 C14 110.98(13) . . ?
C9 C14 C13 110.77(13) . . ?
N1 C15 C16 111.98(11) . . ?
N1 C15 C20 108.80(11) . . ?
C16 C15 C20 110.93(12) . . ?
C15 C16 C17 110.48(12) . . ?
C18 C17 C16 111.55(12) . . ?
C19 C18 C17 110.77(13) . . ?
C18 C19 C20 111.86(13) . . ?
C15 C20 C19 110.49(12) . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.194
_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_4
_database_code_depnum_ccdc_archive 'CCDC 1998497'
loop_
_audit_author_name
_audit_author_address
'Delia Haynes'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'dicyclohexylammonium formate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 N + , C H O2 -'
_chemical_formula_sum            'C13 H25 N O2'
_chemical_formula_weight         227.34

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                   19.216(3)
_cell_length_b                   8.1118(9)
_cell_length_c                   16.8987(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.372(4)
_cell_angle_gamma                90
_cell_volume                     2626.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2611
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      28.16

_exptl_crystal_description       shard
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.45
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_max          0.60
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   '(SADABS, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_reflns_number            8059
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.126
_diffrn_reflns_theta_max         28.305
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3060
_reflns_number_gt                2566
_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       'APEX II, Bruker 2007'
_computing_cell_refinement       'APEX II, Bruker 2007'
_computing_data_reduction        'APEX II, Bruker 2007'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0730P)²+0.9598P] 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         3060
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
O1 O 0.24517(5) 0.36083(11) 0.13998(5) 0.0285(2) Uani 1 1 d . . . . .
O2 O 0.31413(5) 0.52630(11) 0.07455(5) 0.0259(2) Uani 1 1 d . . . . .
C1 C 0.28536(7) 0.47898(15) 0.13394(7) 0.0211(3) Uani 1 1 d . . . . .
H1 H 0.295512 0.541605 0.180914 0.025 Uiso 1 1 calc R U . . .
N1 N 0.22591(5) 0.05465(12) 0.07775(6) 0.0147(2) Uani 1 1 d . . . . .
C2 C 0.29363(6) -0.03495(14) 0.09699(7) 0.0156(2) Uani 1 1 d . . . . .
H2 H 0.288853 -0.150338 0.076464 0.019 Uiso 1 1 calc R U . . .
C3 C 0.34936(6) 0.05372(15) 0.05326(7) 0.0182(3) Uani 1 1 d . . . . .
H3A H 0.351326 0.171055 0.069394 0.022 Uiso 1 1 calc R U . . .
H3B H 0.336800 0.049099 -0.004611 0.022 Uiso 1 1 calc R U . . .
C4 C 0.42103(6) -0.02550(16) 0.07168(7) 0.0214(3) Uani 1 1 d . . . . .
H4A H 0.420718 -0.138248 0.049226 0.026 Uiso 1 1 calc R U . . .
H4B H 0.456749 0.039436 0.046138 0.026 Uiso 1 1 calc R U . . .
C5 C 0.44022(6) -0.03396(15) 0.16073(7) 0.0209(3) Uani 1 1 d . . . . .
H5A H 0.446117 0.079131 0.182235 0.025 Uiso 1 1 calc R U . . .
H5B H 0.485165 -0.092785 0.170766 0.025 Uiso 1 1 calc R U . . .
C6 C 0.38383(6) -0.12309(16) 0.20297(7) 0.0217(3) Uani 1 1 d . . . . .
H6A H 0.396432 -0.122646 0.260878 0.026 Uiso 1 1 calc R U . . .
H6B H 0.381045 -0.239257 0.185056 0.026 Uiso 1 1 calc R U . . .
C7 C 0.31283(6) -0.04085(15) 0.18601(7) 0.0191(3) Uani 1 1 d . . . . .
H7A H 0.276879 -0.103444 0.212352 0.023 Uiso 1 1 calc R U . . .
H7B H 0.314343 0.072530 0.207753 0.023 Uiso 1 1 calc R U . . .
C8 C 0.16390(6) 0.00107(14) 0.11978(7) 0.0161(2) Uani 1 1 d . . . . .
H8 H 0.173713 0.021767 0.177898 0.019 Uiso 1 1 calc R U . . .
C9 C 0.10183(6) 0.10669(15) 0.08945(7) 0.0196(3) Uani 1 1 d . . . . .
H9A H 0.093915 0.094116 0.031182 0.024 Uiso 1 1 calc R U . . .
H9B H 0.112206 0.224137 0.101076 0.024 Uiso 1 1 calc R U . . .
C10 C 0.03596(6) 0.05613(16) 0.12859(8) 0.0249(3) Uani 1 1 d . . . . .
H10A H 0.042106 0.079637 0.186182 0.030 Uiso 1 1 calc R U . . .
H10B H -0.004138 0.121772 0.105803 0.030 Uiso 1 1 calc R U . . .
C11 C 0.02071(6) -0.12650(17) 0.11592(9) 0.0283(3) Uani 1 1 d . . . . .
H11A H 0.009842 -0.148012 0.058638 0.034 Uiso 1 1 calc R U . . .
H11B H -0.020602 -0.157618 0.144192 0.034 Uiso 1 1 calc R U . . .
C12 C 0.08296(6) -0.23109(17) 0.14631(9) 0.0280(3) Uani 1 1 d . . . . .
H12A H 0.072611 -0.348728 0.135125 0.034 Uiso 1 1 calc R U . . .
H12B H 0.090884 -0.217716 0.204530 0.034 Uiso 1 1 calc R U . . .
C13 C 0.14888(6) -0.18175(14) 0.10723(8) 0.0209(3) Uani 1 1 d . . . . .
H13A H 0.188913 -0.247261 0.130276 0.025 Uiso 1 1 calc R U . . .
H13B H 0.142840 -0.205683 0.049666 0.025 Uiso 1 1 calc R U . . .
H2N H 0.2168(8) 0.0415(19) 0.0238(10) 0.030(4) Uiso 1 1 d . . . . .
H1N H 0.2327(7) 0.167(2) 0.0900(8) 0.024(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
O1 C1 1.2400(15) . ?
O2 C1 1.2429(14) . ?
N1 C8 1.4975(14) . ?
N1 C2 1.5042(14) . ?
C2 C7 1.5220(16) . ?
C2 C3 1.5268(15) . ?
C3 C4 1.5300(16) . ?
C4 C5 1.5234(18) . ?
C5 C6 1.5246(16) . ?
C6 C7 1.5261(16) . ?
C8 C13 1.5226(17) . ?
C8 C9 1.5252(16) . ?
C9 C10 1.5283(16) . ?
C10 C11 1.5221(19) . ?
C11 C12 1.5234(18) . ?
C12 C13 1.5261(17) . ?

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
O1 C1 O2 128.56(12) . . ?
C8 N1 C2 117.63(9) . . ?
N1 C2 C7 111.68(9) . . ?
N1 C2 C3 107.15(9) . . ?
C7 C2 C3 111.53(9) . . ?
C2 C3 C4 110.94(10) . . ?
C5 C4 C3 111.48(10) . . ?
C4 C5 C6 110.90(10) . . ?
C5 C6 C7 111.22(10) . . ?
C2 C7 C6 110.20(10) . . ?
N1 C8 C13 111.46(9) . . ?
N1 C8 C9 107.92(9) . . ?
C13 C8 C9 111.42(9) . . ?
C8 C9 C10 110.86(10) . . ?
C11 C10 C9 110.93(10) . . ?
C10 C11 C12 110.91(11) . . ?
C11 C12 C13 111.37(10) . . ?
C8 C13 C12 110.48(10) . . ?

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1998494'
loop_
_audit_author_name
_audit_author_address
'Delia Haynes'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'dicyclohexylammonium diphenylacetete'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 N +, C14 H11 O2 -'
_chemical_formula_sum            'C26 H35 N O2'
_chemical_formula_weight         393.55

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                   5.7270(7)
_cell_length_b                   9.4987(12)
_cell_length_c                   10.4310(13)
_cell_angle_alpha                95.286(2)
_cell_angle_beta                 90.783(2)
_cell_angle_gamma                103.644(2)
_cell_volume                     548.71(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3156
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.33

_exptl_crystal_description       shard
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_F_000             214
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   '(SADABS, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6017
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.962
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4351
_reflns_number_gt                4107
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.961
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.968

_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       'APEX II, Bruker 2007'
_computing_cell_refinement       'APEX II, Bruker 2007'
_computing_data_reduction        'APEX II, Bruker 2007'
_computing_structure_solution    'SHELXS-97 (Sheldrick)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Ammonium H atoms were located in the difference map.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0735P)²+0.1524P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   diffmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4351
_refine_ls_number_parameters     270
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.951
_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
O1 O 0.5409(3) 0.2137(2) 0.22738(18) 0.0285(4) Uani 1 1 d . . . . .
O2 O 0.8215(3) 0.2103(2) 0.08344(18) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.7477(4) 0.2047(3) 0.1957(3) 0.0212(5) Uani 1 1 d . . . . .
C2 C 0.9250(4) 0.1844(3) 0.3019(2) 0.0216(5) Uani 1 1 d . . . . .
H2 H 1.086297 0.197851 0.262862 0.026 Uiso 1 1 calc R U . . .
C3 C 0.8575(5) 0.0284(3) 0.3397(2) 0.0246(6) Uani 1 1 d . . . . .
C4 C 1.0143(6) -0.0603(3) 0.3167(3) 0.0337(7) Uani 1 1 d . . . . .
H4 H 1.160252 -0.024764 0.275271 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9617(7) -0.2010(4) 0.3532(3) 0.0432(8) Uani 1 1 d . . . . .
H5 H 1.071317 -0.260813 0.335740 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7549(7) -0.2543(4) 0.4138(4) 0.0472(9) Uani 1 1 d . . . . .
H6 H 0.720157 -0.350190 0.439569 0.057 Uiso 1 1 calc R U . . .
C7 C 0.5986(7) -0.1671(6) 0.4367(6) 0.0755(17) Uani 1 1 d . . . . .
H7 H 0.453959 -0.202751 0.479192 0.091 Uiso 1 1 calc R U . . .
C8 C 0.6474(6) -0.0279(5) 0.3991(5) 0.0574(12) Uani 1 1 d . . . . .
H8 H 0.534230 0.029991 0.414386 0.069 Uiso 1 1 calc R U . . .
C9 C 0.9520(5) 0.2982(3) 0.4172(2) 0.0246(6) Uani 1 1 d . . . . .
C10 C 1.1759(6) 0.3887(3) 0.4495(3) 0.0327(6) Uani 1 1 d . . . . .
H10 H 1.308921 0.380191 0.398429 0.039 Uiso 1 1 calc R U . . .
C11 C 1.2087(7) 0.4919(3) 0.5558(3) 0.0433(8) Uani 1 1 d . . . . .
H11 H 1.363320 0.554011 0.576084 0.052 Uiso 1 1 calc R U . . .
C12 C 1.0195(8) 0.5046(4) 0.6316(3) 0.0488(10) Uani 1 1 d . . . . .
H12 H 1.042791 0.573621 0.705401 0.059 Uiso 1 1 calc R U . . .
C13 C 0.7972(8) 0.4168(7) 0.5996(4) 0.0746(16) Uani 1 1 d . . . . .
H13 H 0.664693 0.425422 0.651042 0.090 Uiso 1 1 calc R U . . .
C14 C 0.7637(6) 0.3156(5) 0.4931(4) 0.0575(12) Uani 1 1 d . . . . .
H14 H 0.607148 0.256577 0.471576 0.069 Uiso 1 1 calc R U . . .
N1 N 0.2894(4) 0.2684(2) 0.0168(2) 0.0204(5) Uani 1 1 d . . . . .
C15 C 0.3053(5) 0.1638(3) -0.0980(2) 0.0225(5) Uani 1 1 d . . . . .
H15 H 0.474039 0.186957 -0.127835 0.027 Uiso 1 1 calc R U . . .
C16 C 0.2470(5) 0.0101(3) -0.0578(3) 0.0273(6) Uani 1 1 d . . . . .
H16A H 0.082458 -0.013483 -0.024758 0.033 Uiso 1 1 calc R U . . .
H16B H 0.361014 0.003065 0.012186 0.033 Uiso 1 1 calc R U . . .
C17 C 0.2646(6) -0.0977(3) -0.1725(3) 0.0333(7) Uani 1 1 d . . . . .
H17A H 0.221896 -0.197775 -0.146108 0.040 Uiso 1 1 calc R U . . .
H17B H 0.432389 -0.078139 -0.201067 0.040 Uiso 1 1 calc R U . . .
C18 C 0.0975(7) -0.0865(3) -0.2841(3) 0.0381(7) Uani 1 1 d . . . . .
H18A H 0.118260 -0.154380 -0.358646 0.046 Uiso 1 1 calc R U . . .
H18B H -0.071541 -0.114809 -0.258327 0.046 Uiso 1 1 calc R U . . .
C19 C 0.1520(7) 0.0676(4) -0.3227(3) 0.0414(8) Uani 1 1 d . . . . .
H19A H 0.035692 0.074099 -0.391772 0.050 Uiso 1 1 calc R U . . .
H19B H 0.315165 0.091742 -0.357411 0.050 Uiso 1 1 calc R U . . .
C20 C 0.1375(6) 0.1777(3) -0.2085(3) 0.0326(7) Uani 1 1 d . . . . .
H20A H 0.183436 0.277548 -0.235315 0.039 Uiso 1 1 calc R U . . .
H20B H -0.029678 0.160327 -0.179208 0.039 Uiso 1 1 calc R U . . .
C21 C 0.3519(5) 0.4266(3) -0.0041(3) 0.0224(5) Uani 1 1 d . . . . .
H21 H 0.233662 0.442805 -0.069262 0.027 Uiso 1 1 calc R U . . .
C22 C 0.3281(6) 0.5172(3) 0.1205(3) 0.0351(7) Uani 1 1 d . . . . .
H22A H 0.444057 0.503495 0.186760 0.042 Uiso 1 1 calc R U . . .
H22B H 0.163911 0.484992 0.152481 0.042 Uiso 1 1 calc R U . . .
C23 C 0.3771(7) 0.6781(3) 0.0972(3) 0.0425(8) Uani 1 1 d . . . . .
H23A H 0.249811 0.692568 0.038224 0.051 Uiso 1 1 calc R U . . .
H23B H 0.370939 0.736972 0.179931 0.051 Uiso 1 1 calc R U . . .
C24 C 0.6196(6) 0.7304(3) 0.0397(4) 0.0426(8) Uani 1 1 d . . . . .
H24A H 0.636932 0.831530 0.017917 0.051 Uiso 1 1 calc R U . . .
H24B H 0.748048 0.730726 0.104287 0.051 Uiso 1 1 calc R U . . .
C25 C 0.6493(6) 0.6350(3) -0.0800(4) 0.0416(8) Uani 1 1 d . . . . .
H25A H 0.814981 0.666952 -0.109963 0.050 Uiso 1 1 calc R U . . .
H25B H 0.536689 0.646194 -0.149017 0.050 Uiso 1 1 calc R U . . .
C26 C 0.6013(6) 0.4749(3) -0.0552(4) 0.0431(9) Uani 1 1 d . . . . .
H26A H 0.614624 0.414848 -0.136226 0.052 Uiso 1 1 calc R U . . .
H26B H 0.722446 0.461550 0.008288 0.052 Uiso 1 1 calc R U . . .
H2N H 0.144(6) 0.244(3) 0.040(3) 0.012(7) Uiso 1 1 d . . . . .
H1N H 0.387(5) 0.253(3) 0.085(3) 0.018(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
O1 C1 1.254(3) . ?
O2 C1 1.252(3) . ?
C1 C2 1.548(3) . ?
C2 C9 1.521(4) . ?
C2 C3 1.530(4) . ?
C3 C8 1.377(4) . ?
C3 C4 1.378(4) . ?
C4 C5 1.389(4) . ?
C5 C6 1.362(5) . ?
C6 C7 1.366(6) . ?
C7 C8 1.380(5) . ?
C9 C10 1.382(4) . ?
C9 C14 1.379(4) . ?
C10 C11 1.390(5) . ?
C11 C12 1.372(6) . ?
C12 C13 1.365(6) . ?
C13 C14 1.381(5) . ?
N1 C21 1.497(3) . ?
N1 C15 1.502(3) . ?
C15 C16 1.518(4) . ?
C15 C20 1.525(4) . ?
C16 C17 1.522(4) . ?
C17 C18 1.524(4) . ?
C18 C19 1.516(4) . ?
C19 C20 1.528(4) . ?
C21 C26 1.514(4) . ?
C21 C22 1.518(4) . ?
C22 C23 1.530(4) . ?
C23 C24 1.512(5) . ?
C24 C25 1.510(5) . ?
C25 C26 1.527(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
O1 C1 O2 124.5(2) . . ?
O1 C1 C2 118.2(2) . . ?
O2 C1 C2 117.3(2) . . ?
C9 C2 C3 112.9(2) . . ?
C9 C2 C1 113.0(2) . . ?
C3 C2 C1 110.4(2) . . ?
C8 C3 C4 117.6(3) . . ?
C8 C3 C2 122.9(3) . . ?
C4 C3 C2 119.4(2) . . ?
C3 C4 C5 120.8(3) . . ?
C6 C5 C4 120.8(3) . . ?
C7 C6 C5 118.6(3) . . ?
C6 C7 C8 121.0(4) . . ?
C7 C8 C3 121.0(3) . . ?
C10 C9 C14 117.6(3) . . ?
C10 C9 C2 119.1(2) . . ?
C14 C9 C2 123.3(3) . . ?
C9 C10 C11 120.8(3) . . ?
C12 C11 C10 120.5(3) . . ?
C11 C12 C13 119.1(3) . . ?
C12 C13 C14 120.5(4) . . ?
C13 C14 C9 121.5(3) . . ?
C21 N1 C15 116.25(19) . . ?
N1 C15 C16 109.0(2) . . ?
N1 C15 C20 111.2(2) . . ?
C16 C15 C20 111.2(2) . . ?
C15 C16 C17 109.9(2) . . ?
C16 C17 C18 111.3(2) . . ?
C19 C18 C17 110.5(3) . . ?
C18 C19 C20 111.5(3) . . ?
C15 C20 C19 110.2(2) . . ?
N1 C21 C26 112.4(2) . . ?
N1 C21 C22 109.7(2) . . ?
C26 C21 C22 110.5(3) . . ?
C21 C22 C23 109.7(2) . . ?
C24 C23 C22 111.9(3) . . ?
C25 C24 C23 111.7(3) . . ?
C24 C25 C26 111.7(3) . . ?
C21 C26 C25 109.7(2) . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038



####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1998495'
loop_
_audit_author_name
_audit_author_address
'Delia Haynes'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'dibutylammonium diphenylacetate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H20 N +, C14 H11 O2 -'
_chemical_formula_sum            'C22 H31 N O2'
_chemical_formula_weight         341.48

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   21.610(3)
_cell_length_b                   8.5291(11)
_cell_length_c                   21.825(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4022.6(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1894
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      17.92

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9976
_exptl_absorpt_correction_T_max  0.9994
_exptl_absorpt_process_details   '(SADABS, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23175
_diffrn_reflns_av_unetI/netI     0.0955
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.866
_diffrn_reflns_theta_max         28.292
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_point_group_measured_fraction_full 0.868
_reflns_number_total             7928
_reflns_number_gt                5873
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.634
_reflns_Friedel_fraction_max     0.632
_reflns_Friedel_fraction_full    0.727

_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       'APEX II, Bruker 2007'
_computing_cell_refinement       'APEX II, Bruker 2007'
_computing_data_reduction        'APEX II, Bruker 2007'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Ammonium H atoms on both N atoms were located in the difference map.
Those on N1 did not refine well so were added in fixed positions.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+0.7571P] 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_abs_structure_details 
;
 Flack x determined using 1587 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.1(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7928
_refine_ls_number_parameters     463
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0745
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
O1A O 0.63984(15) 0.4125(3) 0.21479(14) 0.0241(8) Uani 1 1 d . . . . .
O2A O 0.59503(15) 0.6281(4) 0.25282(16) 0.0279(8) Uani 1 1 d . . . . .
C1A C 0.6365(2) 0.5232(5) 0.2529(2) 0.0194(10) Uani 1 1 d . . . . .
C2A C 0.6855(2) 0.5366(5) 0.3031(2) 0.0188(10) Uani 1 1 d . . . . .
H2A H 0.666441 0.596914 0.337567 0.023 Uiso 1 1 calc R U . . .
C3A C 0.7048(2) 0.3783(5) 0.3289(2) 0.0200(10) Uani 1 1 d . . . . .
C4A C 0.7391(2) 0.2740(5) 0.2942(2) 0.0229(11) Uani 1 1 d . . . . .
H4A H 0.750674 0.301211 0.253601 0.027 Uiso 1 1 calc R U . . .
C5A C 0.7568(2) 0.1286(5) 0.3184(2) 0.0261(12) Uani 1 1 d . . . . .
H5A H 0.780019 0.057186 0.294182 0.031 Uiso 1 1 calc R U . . .
C6A C 0.7403(2) 0.0894(6) 0.3776(2) 0.0299(12) Uani 1 1 d . . . . .
H6A H 0.752657 -0.008735 0.394148 0.036 Uiso 1 1 calc R U . . .
C7A C 0.7060(2) 0.1920(6) 0.4129(2) 0.0275(12) Uani 1 1 d . . . . .
H7A H 0.694553 0.165070 0.453605 0.033 Uiso 1 1 calc R U . . .
C8A C 0.6884(2) 0.3362(5) 0.3877(2) 0.0228(11) Uani 1 1 d . . . . .
H8A H 0.664627 0.406860 0.411772 0.027 Uiso 1 1 calc R U . . .
C9A C 0.7420(2) 0.6287(5) 0.2822(2) 0.0188(10) Uani 1 1 d . . . . .
C10A C 0.7551(2) 0.6556(5) 0.2211(2) 0.0236(11) Uani 1 1 d . . . . .
H10A H 0.727256 0.619413 0.190457 0.028 Uiso 1 1 calc R U . . .
C11A C 0.8089(2) 0.7356(5) 0.2039(2) 0.0260(11) Uani 1 1 d . . . . .
H11A H 0.817142 0.753456 0.161773 0.031 Uiso 1 1 calc R U . . .
C12A C 0.8500(2) 0.7888(5) 0.2475(2) 0.0247(11) Uani 1 1 d . . . . .
H12A H 0.886692 0.842174 0.235715 0.030 Uiso 1 1 calc R U . . .
C13A C 0.8368(2) 0.7630(5) 0.3083(2) 0.0241(11) Uani 1 1 d . . . . .
H13A H 0.864272 0.800986 0.338932 0.029 Uiso 1 1 calc R U . . .
C14A C 0.7838(2) 0.6822(5) 0.3255(2) 0.0222(11) Uani 1 1 d . . . . .
H14A H 0.776089 0.663122 0.367654 0.027 Uiso 1 1 calc R U . . .
N1A N 0.59268(17) 0.1116(4) 0.22663(17) 0.0190(8) Uani 1 1 d . . . . .
H1NA H 0.608871 0.209875 0.224064 0.023 Uiso 1 1 calc R U . . .
H2NA H 0.556151 0.111963 0.205881 0.023 Uiso 1 1 calc R U . . .
C15A C 0.6356(2) 0.0012(5) 0.1955(2) 0.0223(11) Uani 1 1 d . . . . .
H15A H 0.618202 -0.106136 0.196767 0.027 Uiso 1 1 calc R U . . .
H15B H 0.675858 0.000156 0.217078 0.027 Uiso 1 1 calc R U . . .
C16A C 0.6451(2) 0.0502(5) 0.1299(2) 0.0254(11) Uani 1 1 d . . . . .
H16A H 0.666253 0.153084 0.129317 0.031 Uiso 1 1 calc R U . . .
H16B H 0.604115 0.063823 0.110313 0.031 Uiso 1 1 calc R U . . .
C17A C 0.6827(2) -0.0657(5) 0.0923(2) 0.0263(11) Uani 1 1 d . . . . .
H17A H 0.725400 -0.070097 0.108722 0.032 Uiso 1 1 calc R U . . .
H17B H 0.664315 -0.171416 0.096420 0.032 Uiso 1 1 calc R U . . .
C18A C 0.6852(3) -0.0218(7) 0.0253(3) 0.0419(15) Uani 1 1 d . . . . .
H18A H 0.642999 -0.015873 0.008927 0.063 Uiso 1 1 calc R U . . .
H18B H 0.708618 -0.101389 0.002715 0.063 Uiso 1 1 calc R U . . .
H18C H 0.705456 0.080294 0.020763 0.063 Uiso 1 1 calc R U . . .
C19A C 0.5797(2) 0.0771(5) 0.2918(2) 0.0207(10) Uani 1 1 d . . . . .
H19A H 0.619147 0.071845 0.314856 0.025 Uiso 1 1 calc R U . . .
H19B H 0.559024 -0.026102 0.295229 0.025 Uiso 1 1 calc R U . . .
C20A C 0.5385(2) 0.2035(6) 0.3194(2) 0.0248(11) Uani 1 1 d . . . . .
H20A H 0.559687 0.306041 0.316093 0.030 Uiso 1 1 calc R U . . .
H20B H 0.499679 0.209897 0.295373 0.030 Uiso 1 1 calc R U . . .
C21A C 0.5227(2) 0.1736(5) 0.3855(2) 0.0274(12) Uani 1 1 d . . . . .
H21A H 0.561138 0.151743 0.408593 0.033 Uiso 1 1 calc R U . . .
H21B H 0.495870 0.079660 0.388307 0.033 Uiso 1 1 calc R U . . .
C22A C 0.4893(2) 0.3137(6) 0.4147(2) 0.0311(12) Uani 1 1 d . . . . .
H22A H 0.517503 0.403482 0.416595 0.047 Uiso 1 1 calc R U . . .
H22B H 0.476011 0.285821 0.456275 0.047 Uiso 1 1 calc R U . . .
H22C H 0.453011 0.341179 0.390018 0.047 Uiso 1 1 calc R U . . .
O1B O 0.48107(15) 0.1088(3) 0.16968(15) 0.0224(7) Uani 1 1 d . . . . .
O2B O 0.50581(14) -0.1182(3) 0.12512(15) 0.0226(8) Uani 1 1 d . . . . .
C1B C 0.4698(2) -0.0055(5) 0.1349(2) 0.0158(10) Uani 1 1 d . . . . .
C2B C 0.4074(2) 0.0013(5) 0.1007(2) 0.0185(10) Uani 1 1 d . . . . .
H2B H 0.378244 0.062659 0.127021 0.022 Uiso 1 1 calc R U . . .
C3B C 0.3777(2) -0.1596(5) 0.0901(2) 0.0185(10) Uani 1 1 d . . . . .
C4B C 0.3235(2) -0.1991(5) 0.1195(2) 0.0224(11) Uani 1 1 d . . . . .
H4B H 0.304969 -0.126494 0.146944 0.027 Uiso 1 1 calc R U . . .
C5B C 0.2953(2) -0.3439(6) 0.1096(2) 0.0297(13) Uani 1 1 d . . . . .
H5B H 0.257917 -0.369683 0.130254 0.036 Uiso 1 1 calc R U . . .
C6B C 0.3219(2) -0.4494(6) 0.0698(2) 0.0310(13) Uani 1 1 d . . . . .
H6B H 0.302688 -0.547848 0.062666 0.037 Uiso 1 1 calc R U . . .
C7B C 0.3763(2) -0.4128(5) 0.0402(2) 0.0247(11) Uani 1 1 d . . . . .
H7B H 0.395045 -0.486525 0.013306 0.030 Uiso 1 1 calc R U . . .
C8B C 0.4039(2) -0.2665(5) 0.0499(2) 0.0209(11) Uani 1 1 d . . . . .
H8B H 0.440954 -0.240235 0.028823 0.025 Uiso 1 1 calc R U . . .
C9B C 0.4142(2) 0.0908(5) 0.0407(2) 0.0189(10) Uani 1 1 d . . . . .
C10B C 0.3614(2) 0.1299(5) 0.0079(2) 0.0282(12) Uani 1 1 d . . . . .
H10B H 0.321975 0.102828 0.024043 0.034 Uiso 1 1 calc R U . . .
C11B C 0.3648(2) 0.2077(6) -0.0479(2) 0.0308(13) Uani 1 1 d . . . . .
H11B H 0.328047 0.234068 -0.069379 0.037 Uiso 1 1 calc R U . . .
C12B C 0.4215(3) 0.2464(5) -0.0718(2) 0.0277(12) Uani 1 1 d . . . . .
H12B H 0.424190 0.297052 -0.110522 0.033 Uiso 1 1 calc R U . . .
C13B C 0.4744(2) 0.2115(5) -0.0395(2) 0.0258(11) Uani 1 1 d . . . . .
H13B H 0.513661 0.241166 -0.055237 0.031 Uiso 1 1 calc R U . . .
N1B N 0.50936(18) -0.4268(4) 0.1630(2) 0.0201(9) Uani 1 1 d . . . . .
C14B C 0.4705(2) 0.1332(5) 0.0160(2) 0.0249(11) Uani 1 1 d . . . . .
H14B H 0.507376 0.108200 0.037486 0.030 Uiso 1 1 calc R U . . .
C15B C 0.5308(2) -0.5231(5) 0.1104(2) 0.0220(11) Uani 1 1 d . . . . .
H15C H 0.496493 -0.535061 0.080686 0.026 Uiso 1 1 calc R U . . .
H15D H 0.542248 -0.628932 0.125195 0.026 Uiso 1 1 calc R U . . .
C16B C 0.5863(2) -0.4500(5) 0.0780(2) 0.0246(11) Uani 1 1 d . . . . .
H16C H 0.574852 -0.344402 0.062968 0.030 Uiso 1 1 calc R U . . .
H16D H 0.620622 -0.437792 0.107668 0.030 Uiso 1 1 calc R U . . .
C17B C 0.6078(3) -0.5494(6) 0.0247(2) 0.0342(13) Uani 1 1 d . . . . .
H17C H 0.572943 -0.563880 -0.004177 0.041 Uiso 1 1 calc R U . . .
H17D H 0.619959 -0.654124 0.040120 0.041 Uiso 1 1 calc R U . . .
C18B C 0.6624(3) -0.4770(7) -0.0096(3) 0.0459(15) Uani 1 1 d . . . . .
H18D H 0.650436 -0.374073 -0.025646 0.069 Uiso 1 1 calc R U . . .
H18E H 0.674346 -0.545604 -0.043611 0.069 Uiso 1 1 calc R U . . .
H18F H 0.697470 -0.464885 0.018496 0.069 Uiso 1 1 calc R U . . .
C19B C 0.4526(2) -0.4911(5) 0.1928(2) 0.0250(11) Uani 1 1 d . . . . .
H19C H 0.456538 -0.606497 0.196017 0.030 Uiso 1 1 calc R U . . .
H19D H 0.416341 -0.468075 0.166617 0.030 Uiso 1 1 calc R U . . .
C20B C 0.4418(2) -0.4239(5) 0.2557(2) 0.0283(12) Uani 1 1 d . . . . .
H20C H 0.405963 -0.478415 0.274343 0.034 Uiso 1 1 calc R U . . .
H20D H 0.478431 -0.446631 0.281428 0.034 Uiso 1 1 calc R U . . .
C21B C 0.4297(3) -0.2502(6) 0.2575(2) 0.0326(13) Uani 1 1 d . . . . .
H21C H 0.391913 -0.226589 0.233582 0.039 Uiso 1 1 calc R U . . .
H21D H 0.464771 -0.194456 0.238006 0.039 Uiso 1 1 calc R U . . .
C22B C 0.4216(3) -0.1905(7) 0.3226(3) 0.0409(14) Uani 1 1 d . . . . .
H22D H 0.387016 -0.245712 0.342116 0.061 Uiso 1 1 calc R U . . .
H22E H 0.412921 -0.077784 0.321815 0.061 Uiso 1 1 calc R U . . .
H22F H 0.459593 -0.209709 0.345965 0.061 Uiso 1 1 calc R U . . .
H1NB H 0.545(2) -0.409(5) 0.196(2) 0.016(12) Uiso 1 1 d . . . . .
H2NB H 0.501(2) -0.332(6) 0.146(2) 0.040(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
O1A C1A 1.260(5) . ?
O2A C1A 1.266(5) . ?
C1A C2A 1.530(6) . ?
C2A C3A 1.521(6) . ?
C2A C9A 1.522(6) . ?
C3A C8A 1.380(6) . ?
C3A C4A 1.383(6) . ?
C4A C5A 1.402(6) . ?
C5A C6A 1.381(7) . ?
C6A C7A 1.382(7) . ?
C7A C8A 1.400(6) . ?
C9A C10A 1.382(6) . ?
C9A C14A 1.384(7) . ?
C10A C11A 1.399(6) . ?
C11A C12A 1.378(7) . ?
C12A C13A 1.376(7) . ?
C13A C14A 1.388(6) . ?
N1A C19A 1.479(6) . ?
N1A C15A 1.486(6) . ?
C15A C16A 1.504(6) . ?
C16A C17A 1.521(6) . ?
C17A C18A 1.510(7) . ?
C19A C20A 1.524(6) . ?
C20A C21A 1.505(7) . ?
C21A C22A 1.535(7) . ?
O1B C1B 1.260(5) . ?
O2B C1B 1.256(5) . ?
C1B C2B 1.542(6) . ?
C2B C9B 1.523(6) . ?
C2B C3B 1.532(6) . ?
C3B C4B 1.379(6) . ?
C3B C8B 1.386(6) . ?
C4B C5B 1.393(6) . ?
C5B C6B 1.378(7) . ?
C6B C7B 1.377(7) . ?
C7B C8B 1.399(6) . ?
C9B C14B 1.379(7) . ?
C9B C10B 1.387(6) . ?
C10B C11B 1.389(7) . ?
C11B C12B 1.372(7) . ?
C12B C13B 1.376(7) . ?
C13B C14B 1.385(7) . ?
N1B C15B 1.487(6) . ?
N1B C19B 1.492(6) . ?
C15B C16B 1.524(6) . ?
C16B C17B 1.513(7) . ?
C17B C18B 1.528(7) . ?
C19B C20B 1.507(7) . ?
C20B C21B 1.505(6) . ?
C21B C22B 1.520(7) . ?

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
O1A C1A O2A 124.8(4) . . ?
O1A C1A C2A 119.2(4) . . ?
O2A C1A C2A 116.0(4) . . ?
C3A C2A C9A 110.5(4) . . ?
C3A C2A C1A 112.9(4) . . ?
C9A C2A C1A 112.3(4) . . ?
C8A C3A C4A 118.7(4) . . ?
C8A C3A C2A 120.3(4) . . ?
C4A C3A C2A 121.0(4) . . ?
C3A C4A C5A 120.6(5) . . ?
C6A C5A C4A 119.7(4) . . ?
C5A C6A C7A 120.5(4) . . ?
C6A C7A C8A 118.9(5) . . ?
C3A C8A C7A 121.6(5) . . ?
C10A C9A C14A 118.1(4) . . ?
C10A C9A C2A 122.6(4) . . ?
C14A C9A C2A 119.2(4) . . ?
C9A C10A C11A 120.5(4) . . ?
C12A C11A C10A 120.8(5) . . ?
C13A C12A C11A 118.7(4) . . ?
C12A C13A C14A 120.6(5) . . ?
C9A C14A C13A 121.2(5) . . ?
C19A N1A C15A 115.6(3) . . ?
N1A C15A C16A 110.2(4) . . ?
C15A C16A C17A 114.0(4) . . ?
C18A C17A C16A 112.4(4) . . ?
N1A C19A C20A 110.5(4) . . ?
C21A C20A C19A 113.0(4) . . ?
C20A C21A C22A 111.9(4) . . ?
O2B C1B O1B 125.1(4) . . ?
O2B C1B C2B 119.3(4) . . ?
O1B C1B C2B 115.6(4) . . ?
C9B C2B C3B 111.0(4) . . ?
C9B C2B C1B 110.5(4) . . ?
C3B C2B C1B 113.9(4) . . ?
C4B C3B C8B 118.7(4) . . ?
C4B C3B C2B 120.3(4) . . ?
C8B C3B C2B 121.0(4) . . ?
C3B C4B C5B 121.1(5) . . ?
C6B C5B C4B 119.6(5) . . ?
C7B C6B C5B 120.4(5) . . ?
C6B C7B C8B 119.6(5) . . ?
C3B C8B C7B 120.6(5) . . ?
C14B C9B C10B 117.4(5) . . ?
C14B C9B C2B 123.6(4) . . ?
C10B C9B C2B 119.0(4) . . ?
C9B C10B C11B 121.5(5) . . ?
C12B C11B C10B 119.8(5) . . ?
C11B C12B C13B 119.6(5) . . ?
C12B C13B C14B 120.1(5) . . ?
C15B N1B C19B 112.9(3) . . ?
C9B C14B C13B 121.5(5) . . ?
N1B C15B C16B 112.1(4) . . ?
C17B C16B C15B 111.6(4) . . ?
C16B C17B C18B 112.8(5) . . ?
N1B C19B C20B 112.6(4) . . ?
C21B C20B C19B 115.1(4) . . ?
C20B C21B C22B 111.9(4) . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.230
_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_3
_database_code_depnum_ccdc_archive 'CCDC 1998496'
loop_
_audit_author_name
_audit_author_address
'Delia Haynes'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'dihexylammonium phenylacetate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H28 N +, C8 H7 O2 -'
_chemical_formula_sum            'C20 H35 N O2'
_chemical_formula_weight         321.49

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           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                   8.5570(14)
_cell_length_b                   9.8287(16)
_cell_length_c                   12.292(2)
_cell_angle_alpha                77.147(3)
_cell_angle_beta                 75.054(3)
_cell_angle_gamma                83.311(3)
_cell_volume                     971.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2203
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.71

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.47
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   '(SADABS, 2002)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11235
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.750
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4442
_reflns_number_gt                3363
_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       'APEX II, Bruker 2007'
_computing_cell_refinement       'APEX II, Bruker 2007'
_computing_data_reduction        'APEX II, Bruker 2007'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Ammonium H atoms were located in the difference map.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+0.2358P] 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         4442
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1426
_refine_ls_wR_factor_gt          0.1324
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
O1 O 0.28661(13) 0.51409(11) 0.06950(10) 0.0193(3) Uani 1 1 d . . . . .
O2 O 0.13744(14) 0.69595(12) 0.13039(10) 0.0232(3) Uani 1 1 d . . . . .
C1 C 0.16296(19) 0.56994(16) 0.13113(13) 0.0150(3) Uani 1 1 d . . . . .
C2 C 0.0380(2) 0.47073(17) 0.21117(15) 0.0229(4) Uani 1 1 d . . . . .
H2A H 0.038631 0.471855 0.291395 0.027 Uiso 1 1 calc R U . . .
H2B H -0.070483 0.508357 0.200106 0.027 Uiso 1 1 calc R U . . .
C3 C 0.06000(19) 0.32080(17) 0.19705(14) 0.0169(4) Uani 1 1 d . . . . .
C4 C 0.1200(2) 0.21507(18) 0.27372(15) 0.0241(4) Uani 1 1 d . . . . .
H4 H 0.151516 0.237538 0.335973 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1348(2) 0.07717(19) 0.26112(17) 0.0299(5) Uani 1 1 d . . . . .
H5 H 0.175059 0.006185 0.315184 0.036 Uiso 1 1 calc R U . . .
C6 C 0.0916(2) 0.04217(18) 0.17055(17) 0.0293(5) Uani 1 1 d . . . . .
H6 H 0.101986 -0.052369 0.161884 0.035 Uiso 1 1 calc R U . . .
C7 C 0.0330(2) 0.14664(18) 0.09260(16) 0.0254(4) Uani 1 1 d . . . . .
H7 H 0.003582 0.124072 0.029578 0.031 Uiso 1 1 calc R U . . .
C8 C 0.0171(2) 0.28370(17) 0.10630(14) 0.0198(4) Uani 1 1 d . . . . .
H8 H -0.024061 0.354299 0.052466 0.024 Uiso 1 1 calc R U . . .
N1 N 0.51177(18) 0.29382(14) 0.06501(12) 0.0154(3) Uani 1 1 d . . . . .
H1N H 0.415(3) 0.350(2) 0.0820(18) 0.035(6) Uiso 1 1 d . . . . .
H2N H 0.590(3) 0.363(2) 0.015(2) 0.047(6) Uiso 1 1 d . . . . .
C9 C 0.5672(2) 0.22310(16) 0.16934(13) 0.0171(3) Uani 1 1 d . . . . .
H9A H 0.675131 0.174935 0.146183 0.021 Uiso 1 1 calc R U . . .
H9B H 0.491064 0.151331 0.215074 0.021 Uiso 1 1 calc R U . . .
C10 C 0.5781(2) 0.32427(16) 0.24335(14) 0.0187(4) Uani 1 1 d . . . . .
H10A H 0.469597 0.370361 0.268889 0.022 Uiso 1 1 calc R U . . .
H10B H 0.652064 0.397587 0.197397 0.022 Uiso 1 1 calc R U . . .
C11 C 0.6402(2) 0.24887(17) 0.34849(14) 0.0183(4) Uani 1 1 d . . . . .
H11A H 0.564804 0.176583 0.394372 0.022 Uiso 1 1 calc R U . . .
H11B H 0.747117 0.200691 0.322173 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6572(2) 0.34555(17) 0.42521(14) 0.0194(4) Uani 1 1 d . . . . .
H12A H 0.548537 0.386454 0.457919 0.023 Uiso 1 1 calc R U . . .
H12B H 0.723840 0.423240 0.377754 0.023 Uiso 1 1 calc R U . . .
C13 C 0.7346(2) 0.27218(18) 0.52325(15) 0.0211(4) Uani 1 1 d . . . . .
H13A H 0.664446 0.198381 0.573644 0.025 Uiso 1 1 calc R U . . .
H13B H 0.840438 0.226311 0.490939 0.025 Uiso 1 1 calc R U . . .
C14 C 0.7603(2) 0.3712(2) 0.59474(16) 0.0297(4) Uani 1 1 d . . . . .
H14A H 0.835755 0.440790 0.546529 0.045 Uiso 1 1 calc R U . . .
H14B H 0.805427 0.318243 0.658403 0.045 Uiso 1 1 calc R U . . .
H14C H 0.656362 0.418743 0.625507 0.045 Uiso 1 1 calc R U . . .
C15 C 0.4895(2) 0.19510(16) -0.00455(14) 0.0169(3) Uani 1 1 d . . . . .
H15A H 0.414655 0.124008 0.044585 0.020 Uiso 1 1 calc R U . . .
H15B H 0.595065 0.146089 -0.032829 0.020 Uiso 1 1 calc R U . . .
C16 C 0.4219(2) 0.26983(16) -0.10591(14) 0.0178(4) Uani 1 1 d . . . . .
H16A H 0.497548 0.339703 -0.156083 0.021 Uiso 1 1 calc R U . . .
H16B H 0.316976 0.319967 -0.077999 0.021 Uiso 1 1 calc R U . . .
C17 C 0.3976(2) 0.16653(16) -0.17453(14) 0.0183(4) Uani 1 1 d . . . . .
H17A H 0.333373 0.090548 -0.121408 0.022 Uiso 1 1 calc R U . . .
H17B H 0.504825 0.124152 -0.208535 0.022 Uiso 1 1 calc R U . . .
C18 C 0.3128(2) 0.23020(17) -0.27015(14) 0.0193(4) Uani 1 1 d . . . . .
H18A H 0.203881 0.269699 -0.236337 0.023 Uiso 1 1 calc R U . . .
H18B H 0.375114 0.307852 -0.322514 0.023 Uiso 1 1 calc R U . . .
C19 C 0.2954(2) 0.12468(17) -0.33889(14) 0.0200(4) Uani 1 1 d . . . . .
H19A H 0.235844 0.045912 -0.285900 0.024 Uiso 1 1 calc R U . . .
H19B H 0.404724 0.086893 -0.373882 0.024 Uiso 1 1 calc R U . . .
C20 C 0.2074(2) 0.1848(2) -0.43326(17) 0.0314(5) Uani 1 1 d . . . . .
H20A H 0.098678 0.221881 -0.399408 0.047 Uiso 1 1 calc R U . . .
H20B H 0.198718 0.111173 -0.473196 0.047 Uiso 1 1 calc R U . . .
H20C H 0.268066 0.260295 -0.488086 0.047 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
O1 C1 1.2771(19) . ?
O2 C1 1.2307(18) . ?
C1 C2 1.528(2) . ?
C2 C3 1.506(2) . ?
C3 C4 1.386(2) . ?
C3 C8 1.391(2) . ?
C4 C5 1.386(3) . ?
C5 C6 1.381(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.381(2) . ?
N1 C9 1.481(2) . ?
N1 C15 1.485(2) . ?
C9 C10 1.514(2) . ?
C10 C11 1.529(2) . ?
C11 C12 1.521(2) . ?
C12 C13 1.525(2) . ?
C13 C14 1.516(2) . ?
C15 C16 1.514(2) . ?
C16 C17 1.519(2) . ?
C17 C18 1.519(2) . ?
C18 C19 1.517(2) . ?
C19 C20 1.518(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
O2 C1 O1 125.15(15) . . ?
O2 C1 C2 118.33(14) . . ?
O1 C1 C2 116.52(14) . . ?
C3 C2 C1 116.80(14) . . ?
C4 C3 C8 117.61(16) . . ?
C4 C3 C2 122.02(16) . . ?
C8 C3 C2 120.35(15) . . ?
C3 C4 C5 121.14(17) . . ?
C6 C5 C4 120.48(17) . . ?
C5 C6 C7 119.11(17) . . ?
C8 C7 C6 120.09(17) . . ?
C7 C8 C3 121.56(16) . . ?
C9 N1 C15 113.10(12) . . ?
N1 C9 C10 112.33(13) . . ?
C9 C10 C11 111.09(13) . . ?
C12 C11 C10 113.66(13) . . ?
C11 C12 C13 113.32(13) . . ?
C14 C13 C12 112.85(14) . . ?
N1 C15 C16 111.67(13) . . ?
C15 C16 C17 110.69(13) . . ?
C16 C17 C18 114.22(13) . . ?
C19 C18 C17 112.60(13) . . ?
C18 C19 C20 113.67(14) . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1998493'
loop_
_audit_author_name
_audit_author_address
'Delia Haynes'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'diethylammonium diphenylacetate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H12 N +, C14 H11 O2 -'
_chemical_formula_sum            'C18 H23 N O2'
_chemical_formula_weight         285.37


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                   8.3067(7)
_cell_length_b                   16.4097(13)
_cell_length_c                   11.4319(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.3880(10)
_cell_angle_gamma                90
_cell_volume                     1548.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3681
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      28.36

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9976
_exptl_absorpt_correction_T_max  0.9994
_exptl_absorpt_process_details   '(SADABS, 2002)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17669
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.180
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3681
_reflns_number_gt                3213
_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       'APEX II, Bruker 2007'
_computing_cell_refinement       'APEX II, Bruker 2007'
_computing_data_reduction        'APEX II, Bruker 2007'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Ammonium H atoms were located in the difference map.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²+0.5973P] 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         3681
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
O1 O 0.67057(10) 0.20904(6) 0.47541(7) 0.0211(2) Uani 1 1 d . . . . .
O2 O 0.84502(10) 0.21318(6) 0.34200(7) 0.0216(2) Uani 1 1 d . . . . .
C1 C 0.81104(14) 0.21445(7) 0.44603(10) 0.0153(2) Uani 1 1 d . . . . .
C2 C 0.95356(14) 0.22419(7) 0.54446(10) 0.0149(2) Uani 1 1 d . . . . .
H2 H 0.905801 0.222290 0.620936 0.018 Uiso 1 1 calc R U . . .
C3 C 1.06844(14) 0.15158(7) 0.54417(10) 0.0157(2) Uani 1 1 d . . . . .
C4 C 1.04887(15) 0.08689(8) 0.62002(11) 0.0191(3) Uani 1 1 d . . . . .
H4 H 0.967797 0.090072 0.672270 0.023 Uiso 1 1 calc R U . . .
C5 C 1.14552(16) 0.01774(8) 0.62087(11) 0.0221(3) Uani 1 1 d . . . . .
H5 H 1.129257 -0.026044 0.672643 0.026 Uiso 1 1 calc R U . . .
C6 C 1.26549(16) 0.01262(8) 0.54630(11) 0.0231(3) Uani 1 1 d . . . . .
H6 H 1.331655 -0.034605 0.546333 0.028 Uiso 1 1 calc R U . . .
C7 C 1.28803(16) 0.07715(8) 0.47157(12) 0.0239(3) Uani 1 1 d . . . . .
H7 H 1.371373 0.074390 0.421141 0.029 Uiso 1 1 calc R U . . .
C8 C 1.18989(15) 0.14588(8) 0.46971(11) 0.0205(3) Uani 1 1 d . . . . .
H8 H 1.205750 0.189309 0.417245 0.025 Uiso 1 1 calc R U . . .
C9 C 1.03488(14) 0.30716(7) 0.53867(10) 0.0158(2) Uani 1 1 d . . . . .
C10 C 1.05596(14) 0.35434(7) 0.64096(10) 0.0170(2) Uani 1 1 d . . . . .
H10 H 1.019622 0.334168 0.711363 0.020 Uiso 1 1 calc R U . . .
C11 C 1.12946(14) 0.43044(8) 0.64094(11) 0.0192(3) Uani 1 1 d . . . . .
H11 H 1.142548 0.461957 0.711070 0.023 Uiso 1 1 calc R U . . .
C12 C 1.18357(15) 0.46044(8) 0.53937(11) 0.0206(3) Uani 1 1 d . . . . .
H12 H 1.233813 0.512450 0.539382 0.025 Uiso 1 1 calc R U . . .
C13 C 1.16396(15) 0.41405(8) 0.43741(11) 0.0212(3) Uani 1 1 d . . . . .
H13 H 1.202269 0.434177 0.367660 0.025 Uiso 1 1 calc R U . . .
C14 C 1.08889(15) 0.33852(8) 0.43637(10) 0.0188(3) Uani 1 1 d . . . . .
H14 H 1.074087 0.307870 0.365491 0.023 Uiso 1 1 calc R U . . .
N1 N 0.58104(12) 0.25010(6) 0.69007(9) 0.0165(2) Uani 1 1 d . . . . .
H1N H 0.6173(19) 0.2324(9) 0.6189(15) 0.026(4) Uiso 1 1 d . . . . .
H2N H 0.671(2) 0.2627(10) 0.7435(14) 0.027(4) Uiso 1 1 d . . . . .
C15 C 0.48994(15) 0.18366(8) 0.74141(11) 0.0216(3) Uani 1 1 d . . . . .
H15A H 0.389191 0.172040 0.689349 0.026 Uiso 1 1 calc R U . . .
H15B H 0.459765 0.200754 0.819114 0.026 Uiso 1 1 calc R U . . .
C16 C 0.59367(18) 0.10777(8) 0.75522(13) 0.0295(3) Uani 1 1 d . . . . .
H16A H 0.621713 0.090534 0.677947 0.044 Uiso 1 1 calc R U . . .
H16B H 0.533492 0.064137 0.789570 0.044 Uiso 1 1 calc R U . . .
H16C H 0.692998 0.119470 0.807087 0.044 Uiso 1 1 calc R U . . .
C17 C 0.48670(15) 0.32618(8) 0.66722(11) 0.0215(3) Uani 1 1 d . . . . .
H17A H 0.452461 0.347045 0.741851 0.026 Uiso 1 1 calc R U . . .
H17B H 0.388194 0.314832 0.612623 0.026 Uiso 1 1 calc R U . . .
C18 C 0.58851(17) 0.38949(8) 0.61406(13) 0.0271(3) Uani 1 1 d . . . . .
H18A H 0.685876 0.400606 0.668309 0.041 Uiso 1 1 calc R U . . .
H18B H 0.525699 0.439782 0.600079 0.041 Uiso 1 1 calc R U . . .
H18C H 0.620063 0.369176 0.539284 0.041 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
O1 C1 1.2528(14) . ?
O2 C1 1.2526(14) . ?
C1 C2 1.5481(16) . ?
C2 C9 1.5246(16) . ?
C2 C3 1.5267(16) . ?
C3 C4 1.3917(17) . ?
C3 C8 1.3936(17) . ?
C4 C5 1.3895(18) . ?
C5 C6 1.3841(19) . ?
C6 C7 1.3864(19) . ?
C7 C8 1.3904(18) . ?
C9 C14 1.3967(16) . ?
C9 C10 1.3971(16) . ?
C10 C11 1.3902(17) . ?
C11 C12 1.3816(17) . ?
C12 C13 1.3865(18) . ?
C13 C14 1.3869(18) . ?
N1 C17 1.4817(16) . ?
N1 C15 1.4847(16) . ?
C15 C16 1.5126(19) . ?
C17 C18 1.5093(18) . ?

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
O2 C1 O1 124.63(11) . . ?
O2 C1 C2 117.19(10) . . ?
O1 C1 C2 118.18(10) . . ?
C9 C2 C3 114.63(9) . . ?
C9 C2 C1 111.55(9) . . ?
C3 C2 C1 110.21(9) . . ?
C4 C3 C8 118.17(11) . . ?
C4 C3 C2 118.52(10) . . ?
C8 C3 C2 123.29(11) . . ?
C5 C4 C3 121.32(12) . . ?
C6 C5 C4 120.02(12) . . ?
C5 C6 C7 119.27(12) . . ?
C6 C7 C8 120.66(12) . . ?
C7 C8 C3 120.54(12) . . ?
C14 C9 C10 118.34(11) . . ?
C14 C9 C2 123.41(11) . . ?
C10 C9 C2 118.26(10) . . ?
C11 C10 C9 120.79(11) . . ?
C12 C11 C10 120.27(11) . . ?
C11 C12 C13 119.48(12) . . ?
C12 C13 C14 120.56(12) . . ?
C13 C14 C9 120.54(11) . . ?
C17 N1 C15 113.93(10) . . ?
N1 C15 C16 109.65(11) . . ?
N1 C17 C18 109.99(10) . . ?

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.051



