Two carbazole disulfonamide-diamide macrocycles with semi-flexible meta-xylyl linkages for anion recognition
Li, Junhong; Yuan, Lisha; Yang, Qinrong; Zhang, Ningjin; Bao, Xiaoping; New Journal of Chemistry 47 (2023) 2343–2349; doi:10.1039/D2NJ04412A

data_7062164
_publ_section_title
;
 Two carbazole disulfonamide-diamide macrocycles with semi-flexible
 meta-xylyl linkages for anion recognition
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2343
_journal_page_last               2349
_journal_paper_doi               10.1039/D2NJ04412A
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C43 H46 N6 O6 S2, C2 H6 O S, 2[SOC2H6]'
_chemical_formula_sum            'C45 H52 N6 O7 S3'
_chemical_formula_weight         885.10
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-21 deposited with the CCDC.	2022-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.5150(13)
_cell_length_b                   19.552(3)
_cell_length_c                   57.266(8)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.20
_cell_volume                     10654(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       65
_diffrn_reflns_limit_l_min       -68
_diffrn_reflns_number            182795
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.201
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1226 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.9308.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_description       block
_exptl_crystal_F_000             3744
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     634
_refine_ls_number_reflns         9401
_refine_ls_number_restraints     282
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0687P)^2^+6.1579P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1455
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7650
_reflns_number_total             9401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04412a2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 7062164.cif.'
_cod_database_code               7062164
_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
 C17A-C18A \\sim C17B-C19B
 with sigma of 0.02
 C4A-C3A \\sim C4B-C1B
 with sigma of 0.02
 C4A-C2A \\sim C4B-C3B
 with sigma of 0.02
 C19A-C18A \\sim C20B-C19B
 with sigma of 0.04
 C2A-C3A \\sim C3B-C1B
 with sigma of 0.04
 C13-C19A \\sim C13-C20B
 with sigma of 0.04
 C4A-C1A \\sim C4B-C2B
 with sigma of 0.02
 C17A-C19A \\sim C17B-C20B
 with sigma of 0.02
 C2A-C1A \\sim C3B-C2B
 with sigma of 0.04
 C13-C18A \\sim C13-C19B
 with sigma of 0.04
 C17A-C20A \\sim C17B-C18B
 with sigma of 0.02
 C3A-C1A \\sim C1B-C2B
 with sigma of 0.04
 C13-C20A \\sim C13-C18B
 with sigma of 0.04
 C19A-C20A \\sim C20B-C18B
 with sigma of 0.04
 C5-C2A \\sim C5-C3B
 with sigma of 0.04
 C5-C3A \\sim C5-C1B
 with sigma of 0.04
 C20A-C18A \\sim C18B-C19B
 with sigma of 0.04
 C5-C1A \\sim C5-C2B
 with sigma of 0.04
 C5-C4A \\sim C5-C4B
 with sigma of 0.02
 C13-C17A \\sim C13-C17B
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Rigid body (RIGU) restrains
 C17A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C17A, C19A, C20A, C18A, C19B, C20B, C18B, C17B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4A, C2A, C3A, C1A, C1B, C4B, C2B, C3B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C1B)=Sof(H1Ba)=Sof(H1Bb)=Sof(H1Bc)=Sof(C4B)=Sof(C2B)=Sof(H2Ba)=Sof(H2Bb)=
 Sof(H2Bc)=Sof(C3B)=Sof(H3Ba)=Sof(H3Bb)=Sof(H3Bc)=1-FVAR(1)
 Sof(C4A)=Sof(C2A)=Sof(H2Aa)=Sof(H2Ab)=Sof(H2Ac)=Sof(C3A)=Sof(H3Aa)=Sof(H3Ab)=
 Sof(H3Ac)=Sof(C1A)=Sof(H1Aa)=Sof(H1Ab)=Sof(H1Ac)=FVAR(1)
 Sof(C19B)=Sof(H19d)=Sof(H19e)=Sof(H19f)=Sof(C20B)=Sof(H20d)=Sof(H20e)=
 Sof(H20f)=Sof(C18B)=Sof(H18d)=Sof(H18e)=Sof(H18f)=Sof(C17B)=1-FVAR(2)
 Sof(C17A)=Sof(C19A)=Sof(H19a)=Sof(H19b)=Sof(H19c)=Sof(C20A)=Sof(H20a)=
 Sof(H20b)=Sof(H20c)=Sof(C18A)=Sof(H18a)=Sof(H18b)=Sof(H18c)=FVAR(2)
6.a Riding coordinates:
 C2A(H2Aa,H2Ab,H2Ac), C3A(H3Aa,H3Ab,H3Ac), C1A(H1Aa,H1Ab,H1Ac), C1B(H1Ba,H1Bb,
 H1Bc), C2B(H2Ba,H2Bb,H2Bc), C3B(H3Ba,H3Bb,H3Bc), C19A(H19a,H19b,H19c),
 C20A(H20a,H20b,H20c), C18A(H18a,H18b,H18c), C19B(H19d,H19e,H19f), C20B(H20d,
 H20e,H20f), C18B(H18d,H18e,H18f)
6.b Secondary CH2 refined with riding coordinates:
 C36(H36a,H36b), C28(H28a,H28b), C21(H21a,H21b), C43(H43a,H43b)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N6(H6), C27(H27), C33(H33), C14(H14), C6(H6a), C12(H12),
 C42(H42), C31(H31), C10(H10), C38(H38), C32(H32), C25(H25), C40(H40), C39(H39),
  C24(H24), C23(H23)
6.d Idealised Me refined as rotating group:
 C44(H44a,H44b,H44c), C45(H45a,H45b,H45c)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              11444
_shelx_fab_checksum              86094
_olex2_submission_special_instructions 'No special instructions were received'