The charge-assisted hydrogen-bonded organic framework (CAHOF) self-assembled from the conjugated acid of tetrakis(4-aminophenyl)methane and 2,6-naphthalenedisulfonate as a new class of recyclable Brønsted acid catalysts
Kuznetsova, Svetlana A.; Gak, Alexander S.; Nelyubina, Yulia V.; Larionov, Vladimir A.; Li, Han; North, Michael; Zhereb, Vladimir P.; Smol'yakov, Alexander F.; Dmitrienko, Artem O.; Medvedev, Michael G.; Gerasimov, Igor S.; Saghyan, Ashot S.; Belokon, Yuri N.; Beilstein Journal of Organic Chemistry 16 (2020) 1124–1134; doi:10.3762/bjoc.16.99

data_4038412
_publ_section_title
;
 The charge-assisted hydrogen-bonded organic framework (CAHOF)
 self-assembled from the conjugated acid of tetrakis(4-aminophenyl)methane
 and 2,6-naphthalenedisulfonate as a new class of recyclable Br\/onsted
 acid catalysts
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              1124
_journal_page_last               1134
_journal_paper_doi               10.3762/bjoc.16.99
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         '4(C10 H6 O6 S2), 2(C25 H28 N4), 9(H2 O)'
_chemical_formula_sum            'C90 H98 N8 O33 S8'
_chemical_formula_weight         2076.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.9890(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.6034(8)
_cell_length_b                   20.1330(8)
_cell_length_c                   22.4357(8)
_cell_measurement_reflns_used    5457
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.44
_cell_volume                     9300.9(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            91375
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         0.989
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0763 before and 0.0540 after correction. The Ratio of minimum to maximum transmission is 0.8283. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       prism
_exptl_crystal_F_000             4344
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.367
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1416
_refine_ls_number_reflns         18284
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+15.2761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1719
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13065
_reflns_number_total             18284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-99-S2.cif
_cod_data_source_block           F1a
_cod_depositor_comments
'Adding full bibliography for 4038412--4038413.cif.'
_cod_database_code               4038412
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 S7-O20 = S7-O21 = S7'-O20' = S7'-O21'
 1.45 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C36A) \\sim Ueq, Uanis(C36B) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(O20) \\sim Ueq, Uanis(O20') \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(O21) \\sim Ueq, Uanis(O21') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(O21') \\sim Ueq, Uanis(O21) \\sim Ueq: with sigma of 0.006 and sigma for
terminal atoms of 0.006
Uanis(C31A) = Uanis(C31B)
Uanis(C32A) = Uanis(C32B)
Uanis(C33A) = Uanis(C33B)
Uanis(C34A) = Uanis(C34B)
Uanis(C35A) = Uanis(C35B)
Uanis(C36A) = Uanis(C36B)
Uanis(C37A) = Uanis(C37B)
Uanis(C38A) = Uanis(C38B)
Uanis(C39A) = Uanis(C39B)
Uanis(C40A) = Uanis(C40B)
Uanis(S7) = Uanis(S7')
Uanis(O20) = Uanis(O20')
Uanis(O21) = Uanis(O21')
4. Others
 Sof(O21')=Sof(O20')=Sof(C31B)=Sof(C32B)=Sof(H32B)=Sof(C33B)=Sof(C34B)=
 Sof(H34B)=Sof(C35B)=Sof(H35B)=Sof(C36B)=Sof(C37B)=Sof(H37B)=Sof(C38B)=
 Sof(C39B)=Sof(H39B)=Sof(C40B)=Sof(H40B)=1-FVAR(1)
 Sof(O20)=Sof(O21)=Sof(C31A)=Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33A)=Sof(C34A)=
 Sof(C35A)=Sof(H35A)=Sof(C36A)=Sof(C37A)=Sof(H37A)=Sof(C38A)=Sof(H38A)=
 Sof(C39A)=Sof(C40A)=Sof(H40A)=FVAR(1)
 Sof(S7')=1-FVAR(2)
 Sof(S7)=FVAR(2)
5.a Free rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB), O3W(H3WA,H3WB), O4W(H4WA,H4WB), O5W(H5WA,
 H5WB), O6W(H6WA,H6WB), O7W(H7WA,H7WB), O8W(H8WA,H8WB), O9W(H9WA,H9WB)
5.b Aromatic/amide H refined with riding coordinates:
 C2A(H2AA), C3A(H3AA), C5A(H5AA), C7A(H7AA), C8A(H8AA), C10A(H10A), C12A(H12A),
  C14A(H14A), C15A(H15A), C17A(H17A), C19A(H19A), C20A(H20A), C22A(H22A),
 C23A(H23A), C25A(H25A), C27A(H27A), C28A(H28A), C30A(H30A), C32B(H32B),
 C34B(H34B), C35B(H35B), C37B(H37B), C39B(H39B), C40B(H40B), C32A(H32A),
 C33A(H33A), C35A(H35A), C37A(H37A), C38A(H38A), C40A(H40A), C3C(H3CA),
 C4C(H4CA), C6C(H6C), C7C(H7C), C9C(H9C), C10C(H10C), C12C(H12C), C13C(H13C),
 C15C(H15C), C16C(H16C), C18C(H18C), C19C(H19C), C21C(H21C), C22C(H22C),
 C24C(H24C), C25C(H25C), C28C(H28C), C29C(H29C), C31C(H31C), C32C(H32C),
 C34C(H34C), C35C(H35C), C37C(H37C), C38C(H38C), C40C(H40C), C41C(H41C),
 C43C(H43C), C44C(H44C), C46C(H46C), C47C(H47C), C49C(H49C), C50C(H50C)
;
_shelx_res_checksum              31152
_shelx_hkl_checksum              11755
_olex2_submission_special_instructions 'No special instructions were received'