Effect of carbon-skeleton isomerism on the dielectric properties and proton conduction of organic cocrystal compounds assembled from 1,2,4,5-benzenetetracarboxylic acid and piperazine derivatives
Liang, Xiaoqiang; Chen, Yixiang; Wang, Li; Zhang, Feng; Fan, Zenglu; Cao, Tingting; Cao, Yaya; Zhu, Huifang; He, Xinyue; Deng, Bolin; You, Yazhi; Dong, Yu; Zhao, Yamei; New Journal of Chemistry 43 (2019) 11099–; doi:10.1039/C9NJ01412H

data_7058453
_publ_section_title
;
 Effect of carbon-skeleton isomerism on the dielectric properties and
 proton conduction of organic cocrystal compounds assembled from
 1,2,4,5-benzenetetracarboxylic acid and piperazine derivatives
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11099
_journal_paper_doi               10.1039/C9NJ01412H
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         '2(C10 H5 O8), 2(H2 O), C5 H14 N2'
_chemical_formula_sum            'C25 H28 N2 O18'
_chemical_formula_weight         644.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-05-01
_audit_creation_method
;
Olex2 1.3-dev
(compiled 2019.03.18 svn.r3573 for OlexSys, GUI svn.r5585)
;
_audit_update_record
;
2019-05-20 deposited with the CCDC.    2019-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                84.792(3)
_cell_angle_beta                 88.545(2)
_cell_angle_gamma                68.948(2)
_cell_formula_units_Z            1
_cell_length_a                   8.5370(12)
_cell_length_b                   8.7025(12)
_cell_length_c                   9.7295(18)
_cell_measurement_reflns_used    1696
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      3.14
_cell_volume                     671.79(18)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXTL (Bruker, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4326
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         2.102
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_preparation
'Dielectric Response and Proton Conduction,Dielectric Property and Proton Conduction'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2762
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0509P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2274
_reflns_number_total             2762
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj01412h2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7058453--7058454.cif.'
_cod_database_code               7058453
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups, All O(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1W-H1WA = O1W-H1WB
 0.85 with sigma of 0.02
 H1WA-H1WB
 1.34 with sigma of 0.04
 N14-C11 \\sim C13-C11 \\sim C15-N12
 with sigma of 0.01
 C14-N12 \\sim C14-C13 \\sim C12-C15 \\sim C12-N14
 with sigma of 0.01
 C15-C11 \\sim C11-N12
 with sigma of 0.01
3. Rigid body (RIGU) restrains
 N14, N12, C14, C15, C13, C12, C11
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: N12(0.5) H12A(0.5) H12B(0.5) C14(0.5) H14A(0.5) H14B(0.5) C13(0.5)
 H13A(0.5) H13B(0.5) C11(0.5) H11A(0.5) H11B(0.5) N14(0.5) H14C(0.5) H14D(0.5)
 C12(0.5) H12C(0.5) H12D(0.5) C15(0.5) H15A(0.5) H15B(0.5)
5.a Riding coordinates:
 O2(H2), O4(H4A), O7(H7)
5.b Secondary CH2 refined with riding coordinates:
 N12(H12A,H12B), C14(H14A,H14B), C13(H13A,H13B), C11(H11A,H11B), N14(H14C,
 H14D), C12(H12C,H12D), C15(H15A,H15B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4)
;
_shelx_res_checksum              2926
_olex2_submission_special_instructions 'No special instructions were received'