# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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 1884399'
loop_
_audit_author_name
_audit_author_address
'Fabio Marchetti'
;Dipartimento di Chimica e Chimica Industriale, Universit? di Pisa, via Giuseppe Moruzzi 13, I-56124
Italy
;
_audit_update_record             
;
2018-12-11 deposited with the CCDC.	2019-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'dibuthylammonium terephtalate terephtalic acid solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H4 O4, C8 H6 O4, 2(C8 H20 N)'
_chemical_formula_sum            'C32 H50 N2 O8'
_chemical_formula_weight         590.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   22.420(5)
_cell_length_b                   11.633(2)
_cell_length_c                   13.542(3)
_cell_angle_alpha                90


_cell_angle_beta                 102.187(6)
_cell_angle_gamma                90
_cell_volume                     3452.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3354
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      24.23

_exptl_crystal_description       Prism
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6843
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11993
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.627
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2989
_reflns_number_gt                2130
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.1333P)²+1.4323P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2989
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.2078
_refine_ls_wR_factor_gt          0.1821
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.76201(9) 0.49795(19) 0.51682(17) 0.0457(5) Uani 1 1 d . . . . .
C2 C 0.75659(9) 0.36932(18) 0.50829(16) 0.0432(5) Uani 1 1 d . . . . .
C3 C 0.80760(9) 0.2981(2) 0.52404(18) 0.0515(6) Uani 1 1 d . . . . .
H3 H 0.8465 0.3300 0.5403 0.062 Uiso 1 1 calc R U . . .
C4 C 0.80080(10) 0.1810(2) 0.51567(19) 0.0519(6) Uani 1 1 d . . . . .
H4 H 0.8345(12) 0.131(2) 0.5192(19) 0.070(8) Uiso 1 1 d . . . . .
C5 C 0.88978(11) 0.4732(2) 0.3278(2) 0.0537(6) Uani 1 1 d . . . . .
C6 C 0.94734(10) 0.46326(19) 0.28885(18) 0.0498(6) Uani 1 1 d . . . . .
C7 C 0.94341(11) 0.4621(2) 0.1854(2) 0.0604(7) Uani 1 1 d . . . . .
H7 H 0.9053 0.4622 0.1417 0.072 Uiso 1 1 calc R U . . .
C8 C 0.99565(11) 0.4610(2) 0.1466(2) 0.0594(7) Uani 1 1 d . . . . .
H8 H 0.9935(13) 0.458(2) 0.078(2) 0.070(8) Uiso 1 1 d . . . . .
C9 C 0.65439(14) 0.7286(3) 0.6714(3) 0.0777(9) Uani 1 1 d . . . . .
H9A H 0.6466 0.7911 0.7145 0.093 Uiso 1 1 calc R U . . .
H9B H 0.6604 0.6591 0.7118 0.093 Uiso 1 1 calc R U . . .
C10 C 0.60015(13) 0.7135(3) 0.5875(3) 0.0860(10) Uani 1 1 d . . . . .
H10A H 0.6061 0.6462 0.5483 0.103 Uiso 1 1 calc R U . . .
H10B H 0.5964 0.7798 0.5431 0.103 Uiso 1 1 calc R U . . .
C11 C 0.54121(17) 0.6995(4) 0.6260(4) 0.1368(19) Uani 1 1 d . . . . .
H11A H 0.5454 0.6335 0.6707 0.164 Uiso 1 1 calc R U . . .
H11B H 0.5358 0.7669 0.6654 0.164 Uiso 1 1 calc R U . . .
C12 C 0.48599(19) 0.6841(5) 0.5457(5) 0.189(3) Uani 1 1 d . . . . .
H12A H 0.4510 0.6759 0.5756 0.284 Uiso 1 1 calc R U . . .
H12B H 0.4807 0.7499 0.5019 0.284 Uiso 1 1 calc R U . . .
H12C H 0.4904 0.6164 0.5073 0.284 Uiso 1 1 calc R U . . .
C13 C 0.76351(15) 0.7801(3) 0.7217(3) 0.0903(10) Uani 1 1 d . . . . .
H13A H 0.7537 0.8470 0.7580 0.108 Uiso 1 1 calc R U . . .
H13B H 0.7698 0.7157 0.7682 0.108 Uiso 1 1 calc R U . . .
C14 C 0.81958(16) 0.8019(4) 0.6858(3) 0.1058(12) Uani 1 1 d . . . . .
H14A H 0.8118 0.8588 0.6323 0.127 Uiso 1 1 calc R U . . .
H14B H 0.8329 0.7316 0.6585 0.127 Uiso 1 1 calc R U . . .
C15 C 0.8705(2) 0.8460(5) 0.7740(4) 0.1412(18) Uani 1 1 d . . . . .
H15A H 0.8551 0.9091 0.8082 0.169 Uiso 1 1 calc R U . . .
H15B H 0.8829 0.7847 0.8226 0.169 Uiso 1 1 calc R U . . .
C16 C 0.9224(3) 0.8841(7) 0.7348(6) 0.221(3) Uani 1 1 d . . . . .
H16A H 0.9537 0.9113 0.7894 0.331 Uiso 1 1 calc R U . . .
H16B H 0.9378 0.8212 0.7017 0.331 Uiso 1 1 calc R U . . .
H16C H 0.9100 0.9453 0.6873 0.331 Uiso 1 1 calc R U . . .
O01 O 0.80852(7) 0.54585(12) 0.49566(12) 0.0523(5) Uani 1 1 d . . . . .
O02 O 0.71960(8) 0.55068(13) 0.54295(16) 0.0681(6) Uani 1 1 d . . . . .
O03 O 0.89899(8) 0.47321(17) 0.42688(14) 0.0662(6) Uani 1 1 d . . . . .
H03 H 0.8670 0.4885 0.4442 0.099 Uiso 1 1 calc R U . . .
O04 O 0.84019(8) 0.4842(2) 0.27296(16) 0.0833(7) Uani 1 1 d . . . . .
N1 N 0.71075(9) 0.75385(16) 0.63504(17) 0.0610(6) Uani 1 1 d . . . . .
H1A H 0.7043 0.8137 0.5933 0.073 Uiso 1 1 calc R U . . .
H1B H 0.7202 0.6937 0.6007 0.073 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
C1 O02 1.244(2) . ?
C1 O01 1.267(2) . ?
C1 C2 1.504(3) . ?
C2 C4 1.388(3) 7_656 ?
C2 C3 1.392(3) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C2 1.388(3) 7_656 ?
C4 H4 0.95(3) . ?
C5 O04 1.206(3) . ?
C5 O03 1.314(3) . ?
C5 C6 1.498(3) . ?
C6 C7 1.386(3) . ?
C6 C8 1.388(3) 2_755 ?
C7 C8 1.381(4) . ?
C7 H7 0.9300 . ?
C8 C6 1.388(3) 2_755 ?
C8 H8 0.92(3) . ?
C9 N1 1.479(3) . ?
C9 C10 1.489(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.529(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.476(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.462(5) . ?
C13 N1 1.511(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.555(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.446(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O03 H03 0.8200 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?

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
O02 C1 O01 124.2(2) . . ?
O02 C1 C2 117.28(18) . . ?
O01 C1 C2 118.50(17) . . ?
C4 C2 C3 118.4(2) 7_656 . ?
C4 C2 C1 119.56(18) 7_656 . ?
C3 C2 C1 122.00(19) . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C2 121.3(2) . 7_656 ?
C3 C4 H4 122.1(16) . . ?
C2 C4 H4 116.3(16) 7_656 . ?
O04 C5 O03 123.6(2) . . ?
O04 C5 C6 122.9(2) . . ?
O03 C5 C6 113.4(2) . . ?
C7 C6 C8 119.3(2) . 2_755 ?
C7 C6 C5 118.7(2) . . ?
C8 C6 C5 121.8(2) 2_755 . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C6 120.2(2) . 2_755 ?
C7 C8 H8 121.0(18) . . ?
C6 C8 H8 118.8(18) 2_755 . ?
N1 C9 C10 112.7(3) . . ?
N1 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N1 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 112.2(3) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 114.3(5) . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N1 111.3(3) . . ?
C14 C13 H13A 109.4 . . ?
N1 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
N1 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.2(3) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 109.7(5) . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 O03 H03 109.5 . . ?
C9 N1 C13 111.4(2) . . ?
C9 N1 H1A 109.3 . . ?
C13 N1 H1A 109.3 . . ?
C9 N1 H1B 109.3 . . ?
C13 N1 H1B 109.3 . . ?
H1A N1 H1B 108.0 . . ?

_refine_diff_density_max         0.549
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.040

