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_7242388
_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         '2(C28 H33 N3 O4 S2), F, C16 H36 N'
_chemical_formula_sum            'C72 H102 F N7 O8 S4'
_chemical_formula_weight         1340.84
_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             2019-12-24
_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                   16.4040(17)
_cell_length_b                   16.5999(19)
_cell_length_c                   29.998(4)
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      66.93
_cell_measurement_theta_min      2.95
_cell_volume                     8168.6(17)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_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  0.1695
_diffrn_reflns_av_unetI/netI     0.1056
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            100660
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.018
_diffrn_reflns_theta_max         67.018
_diffrn_reflns_theta_min         2.946
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.496
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1593 before and 0.0885 after correction.
The Ratio of minimum to maximum transmission is 0.7201.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_description       block
_exptl_crystal_F_000             2880
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 2762 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.076(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     906
_refine_ls_number_reflns         14480
_refine_ls_number_restraints     134
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1309
_refine_ls_R_factor_gt           0.0803
_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^)+(0.1441P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2048
_refine_ls_wR_factor_ref         0.2396
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                8879
_reflns_number_total             14480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra01285a2.cif
_cod_data_source_block           a_a_sq
_cod_original_cell_volume        8168.7(16)
_cod_database_code               7242388
_shelx_shelxl_version_number     2018/3
_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
 H2'B-H3B
 2.315 with sigma of 0.02
 H3B-H1'B
 2.96 with sigma of 0.02
 H1'B-H2'B
 2.404 with sigma of 0.02
 C68-C67 = C64-C63
 1.53 with sigma of 0.02
 C30-C29 \\sim C30-C31 \\sim C29-C31
 with sigma of 0.04
 C32-C33 \\sim C32-C30 \\sim C32-C29 \\sim C32-C31
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C17: within 1.8A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
1.8A
C32: within 1.8A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
1.8A
C69 \\sim C70 \\sim C71 \\sim C72: within 1.8A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 1.8A
C32 \\sim C30 \\sim C29' \\sim C31': within 1.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 1.8A
C1' \\sim C2' \\sim C3: within 1.8A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 1.8A
C4 \\sim C1' \\sim C2' \\sim C3: within 1.8A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 1.8A
C4 \\sim C1 \\sim C2 \\sim C10B: within 1.8A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 1.8A
Uanis(C2) \\sim Ueq, Uanis(C1') \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 C32, C29, C30, C31
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C4, C1, C2, C10B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1', C2', C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(C1')=Sof(H1'A)=Sof(H1'B)=Sof(H1'C)=Sof(C2')=Sof(H2'A)=Sof(H2'B)=Sof(H2'C)=
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C29')=Sof(H29D)=Sof(H29E)=Sof(H29F)=
 Sof(C30')=Sof(H30D)=Sof(H30E)=Sof(H30F)=Sof(C31')=Sof(H31D)=Sof(H31E)=
 Sof(H31F)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=
 Sof(C10B)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=
 FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C28(H28A,H28B), C49(H49A,H49B), C56(H56A,H56B), C57(H57A,
 H57B), C58(H58A,H58B), C59(H59A,H59B), C61(H61A,H61B), C62(H62A,H62B),
 C63(H63A,H63B), C65(H65A,H65B), C66(H66A,H66B), C67(H67A,H67B), C69(H69A,H69B),
  C70(H70A,H70B), C71(H71A,H71B)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), C6(H6), C10(H10), C14(H14), C16(H16), C23(H23),
 C24(H24), C25(H25), C27(H27), N4(H4), N5(H5), N6(H6A), C34(H34), C38(H38),
 C40(H40), C46(H46), C51(H51), C52(H52), C53(H53), C55(H55)
6.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C1(H1A,H1B,
 H1C), C2(H2A,H2B,H2C), C10B(H10A,H10B,H10C), C1'(H1'A,H1'B,H1'C), C2'(H2'A,
 H2'B,H2'C), C3(H3A,H3B,H3C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C),
 C45(H45A,H45B,H45C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C29'(H29D,H29E,H29F), C30'(H30D,H30E,H30F), C31'(H31D,H31E,H31F),
 C60(H60A,H60B,H60C), C64(H64A,H64B,H64C), C68(H68A,H68B,H68C), C72(H72A,H72B,
 H72C)
;
_shelx_res_checksum              88953
_shelx_fab_checksum              75978
_olex2_submission_special_instructions 'No special instructions were received'