Carbazole sulfonamide-based macrocyclic receptors capable of selective complexation of fluoride ion
Luo, Na; Li, Junhong; Sun, Tao; Wan, Suran; Li, Peijia; Wu, Nan; Yan, Ya; Bao, Xiaoping; RSC Advances 11 (2021) 10203–10211; doi:10.1039/D1RA01285A

data_7242389
_publ_section_title
;
 Carbazole sulfonamide-based macrocyclic receptors capable of selective
 complexation of fluoride ion
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              10203
_journal_page_last               10211
_journal_paper_doi               10.1039/D1RA01285A
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C28 H33 N3 O4 S2'
_chemical_formula_sum            'C28 H33 N3 O4 S2'
_chemical_formula_weight         539.69
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-01-10
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-01-10 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5696(4)
_cell_length_b                   26.4247(6)
_cell_length_c                   6.52480(10)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    150.03
_cell_measurement_theta_max      74.50
_cell_measurement_theta_min      2.91
_cell_volume                     3201.69(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.03
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            21398
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.118
_diffrn_reflns_theta_min         2.908
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.776
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1218 before and 0.0665 after correction.
The Ratio of minimum to maximum transmission is 0.1112.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 1989 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.439(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6171
_refine_ls_number_restraints     135
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0834
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1465P)^2^+0.8859P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2191
_refine_ls_wR_factor_ref         0.2240
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                5533
_reflns_number_total             6171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra01285a2.cif
_cod_data_source_block           cu_1115_7_0ma_sq
_cod_database_code               7242389
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.729
_shelx_estimated_absorpt_t_min   0.675
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C22-C20 \\sim C22-C18 \\sim C20-C18 \\sim C23-C21 \\sim C23-C19 \\sim C21-C19
 with sigma of 0.04
 C17-C14 \\sim C17-C22 \\sim C17-C20 \\sim C17-C18 \\sim C17-C23 \\sim C17-C21
\\sim C17-C19
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C21) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23)
\\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C17) \\sim Ueq:
with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 C18, C22, C17, C20, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C19, C21, C23, C17, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=1-FVAR(1)
 Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C31(H31A,H31B)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), C6(H6), C10(H10), C13(H13), C15(H15), C26(H26),
 C27(H27), C28(H28), C30(H30)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C18(H18A,H18B,H18C),
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              27434
_shelx_fab_checksum              73826
_olex2_submission_special_instructions 'No special instructions were received'