Coaxial assembly of helical aromatic foldamers by metal coordination.
Galan, Albano; Lulic, Kristijan; Wang, Jingqi; Wicher, Barbara; Huc, Ivan; Duhamel, Jean; Maurizot, Victor; Chemical communications (Cambridge, England) 59 (2023) 5253–5256; doi:10.1039/d3cc00866e

data_7131517
_publ_section_title
;
 Coaxial assembly of helical aromatic foldamers by metal coordination.
;
_journal_issue                   35
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5253
_journal_page_last               5256
_journal_paper_doi               10.1039/d3cc00866e
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety
'C225 H227 Cl3 N32 Na2 O40, 3(C H Cl3) [+solvent]'
_chemical_formula_sum            'C228 H230 Cl12 N32 Na2 O40'
_chemical_formula_weight         4529.81
_chemical_properties_physical    Air-sensitive,Light-sensitive
_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   geom
_audit_creation_date             2023-03-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-03-31 deposited with the CCDC.	2023-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.137(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   44.863(14)
_cell_length_b                   19.062(5)
_cell_length_c                   28.749(9)
_cell_measurement_reflns_used    8286
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      60.7
_cell_measurement_theta_min      18.9
_cell_volume                     23617(12)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b43, Rigaku 2015'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b43, Rigaku 2015'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b43, Rigaku 2015'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1260
_diffrn_reflns_av_unetI/netI     0.0914
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            90366
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        50.438
_diffrn_reflns_theta_max         50.438
_diffrn_reflns_theta_min         2.535
_exptl_absorpt_coefficient_mu    1.956
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 2.1 b43 (Rigaku, 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             9472
_exptl_crystal_recrystallization_method
'diffusion of n-hexane to a filtered solution of the complex in chloroform'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.076
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.673
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1888
_refine_ls_number_reflns         23448
_refine_ls_number_restraints     358
_refine_ls_restrained_S_all      1.664
_refine_ls_R_factor_all          0.2416
_refine_ls_R_factor_gt           0.1931
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4720
_refine_ls_wR_factor_ref         0.5113
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13209
_reflns_number_total             23448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00866e2.cif
_cod_data_source_block           q8_na_q8
_cod_depositor_comments
'Adding full bibliography for 7131515--7131517.cif.'
_cod_database_code               7131517
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.696
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C1_1-C2_1
 C1_2-C2_2
 C1_3-C2_3
 C1_4-C2_4
 C1_5-C2_5
 C1_6-C2_6
 C1_7-C2_7
 C1_8-C2_8
 C1_9-C2_9
 C1_10-C2_10
 C1_11-C2_11
 C1_12-C2_12
 C1_13-C2_13
 C1_14-C2_14
 C1_15-C2_15
 C1_16-C2_16
 1.51 with sigma of 0.001
 C2_1-C3_1 = C2_1-C4_1
 C2_2-C3_2 = C2_2-C4_2
 C2_3-C3_3 = C2_3-C4_3
 C2_4-C3_4 = C2_4-C4_4
 C2_5-C3_5 = C2_5-C4_5
 C2_6-C3_6 = C2_6-C4_6
 C2_7-C3_7 = C2_7-C4_7
 C2_8-C3_8 = C2_8-C4_8
 C2_9-C3_9 = C2_9-C4_9
 C2_10-C3_10 = C2_10-C4_10
 C2_11-C3_11 = C2_11-C4_11
 C2_12-C3_12 = C2_12-C4_12
 C2_13-C3_13 = C2_13-C4_13
 C2_14-C3_14 = C2_14-C4_14
 C2_15-C3_15 = C2_15-C4_15
 C2_16-C3_16 = C2_16-C4_16
 1.51 with sigma of 0.001
 C3_1-C4_1
 C3_2-C4_2
 C3_3-C4_3
 C3_4-C4_4
 C3_5-C4_5
 C3_6-C4_6
 C3_7-C4_7
 C3_8-C4_8
 C3_9-C4_9
 C3_10-C4_10
 C3_11-C4_11
 C3_12-C4_12
 C3_13-C4_13
 C3_14-C4_14
 C3_15-C4_15
 C3_16-C4_16
 2.5 with sigma of 0.02
 O1_1-C1_1
 O1_2-C1_2
 O1_3-C1_3
 O1_4-C1_4
 O1_5-C1_5
 O1_6-C1_6
 O1_7-C1_7
 O1_8-C1_8
 O1_9-C1_9
 O1_10-C1_10
 O1_11-C1_11
 O1_12-C1_12
 O1_13-C1_13
 O1_14-C1_14
 O1_15-C1_15
 O1_16-C1_16
 1.41 with sigma of 0.01
 C211_11-C1_11
 1.51 with sigma of 0.02
 C211_11-C411_11
 1.51 with sigma of 0.02
 C311_11-C211_11
 1.51 with sigma of 0.02
 C311_11-C411_11
 2.5 with sigma of 0.02
3. Rigid bond restraints
 N5C, C20C, O4C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N11A, C50A, O7A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N13A, C60A, O8A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C75A, C79A, N16A, C78A, C77A, C76A, C74A, C73A, C72A, C71A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C2A, N2A, C7A, C9A, C4A, C5A, C6A, C3A, C8A, C1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C59C, C56C, C58C, C52C, C54C, C53C, C57C, C55C, N12C, C51C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C25A, C27A, N6A, C23A, C21A, C22A, C28A, C29A, C26A, C24A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C39C, C36C, C38C, C32C, C34C, C33C, C37C, C35C, N8C, C31C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C33A, C31A, C39A, C34A, C32A, C35A, N8A, C38A, C37A, C36A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C49A, C41A, C43A, C46A, C48A, C47A, C42A, N10A, C44A, C45A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C72C, C71C, C73C, C79C, C74C, C75C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C69A, C61A, C63A, C66A, C68A, C67A, C62A, N14A, C64A, C65A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N3C, C10C, O3C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C25C, N6C, C26C, C21C, C23C, C22C, C27C, C24C, C0AA, C29C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C17A, C11A, C13A, N4A, C15A, C19A, C14A, C16A, C12A, C18A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uiso(O1_12) = Uiso(C2_12) = Uiso(C1_12) = Uiso(C4_12) = Uiso(C3_12)
Uanis(N12A) = Uanis(C58A) = Uanis(C57A) = Uanis(C56A) = Uanis(C55A) =
Uanis(C59A) = Uanis(C51A) = Uanis(C52A) = Uanis(C53A) = Uanis(C54A)
Uanis(N4C) = Uanis(C19C) = Uanis(C11C) = Uanis(C12C) = Uanis(C13C) =
Uanis(C14C) = Uanis(C15C) = Uanis(C16C) = Uanis(C17C) = Uanis(C18C)
Uiso(O1_13) = Uiso(C1_13) = Uiso(C2_13) = Uiso(C3_13) = Uiso(C4_13)
Uiso(C1_2) = Uiso(O1_2) = Uiso(C2_2) = Uiso(C3_2) = Uiso(C4_2)
Uanis(N1A) = Uanis(O1A) = Uanis(O2A)
5. Others
 Sof(C311)=Sof(C211)=Sof(C411)=1-FVAR(1)
 Sof(C2)=Sof(C4)=Sof(C3)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C2A(H2A), C3A(H3A), C4A(H4A), N3A(H3AA), C17A(H17A), C12A(H12A),
 C13A(H13A), C14A(H14A), N5A(H5A), C27A(H27A), C22A(H22A), C23A(H23A),
 C24A(H24A), N7A(H7AA), C37A(H37A), C32A(H32A), C33A(H33A), C34A(H34A),
 N9A(H9A), C47A(H47A), C42A(H42A), C43A(H43A), C44A(H44A), N11A(H11A),
 C57A(H57A), C52A(H52A), C53A(H53A), C54A(H54A), N13A(H13B), C67A(H67A),
 C62A(H62A), C63A(H63A), C64A(H64A), N15A(H15A), C77A(H77A), C72A(H72A),
 C73A(H73A), C74A(H74A), C2C(H2C), C3C(H3C), C4C(H4C), C7C(H7C), C12C(H12C),
 C13C(H13C), C14C(H14C), C17C(H17C), C22C(H22C), C23C(H23C), C24C(H24C),
 C26C(H26C), C32C(H32C), C33C(H33C), C34C(H34C), C37C(H37C), C42C(H42C),
 C43C(H43C), C44C(H44C), C47C(H47C), C52C(H52C), C53C(H53C), C54C(H54C),
 C57C(H57C), C62C(H62C), C63C(H63C), C64C(H64C), C67C(H67C), C72C(H72C),
 C73C(H73C), C74C(H74C), C77C(H77C), N3C(H3CA), N5C(H5C), N7C(H7CA), N9C(H9C),
 N11C(H11C), N13C(H13D), N15C(H15C)
6.b Naphthalene refined as free rotating group:
 N2A(C8A,C7A,C6A,C5A,C9A,C1A,C2A,C3A,C4A), N4A(C18A,C17A,C16A,C15A,C19A,C11A,
 C12A,C13A,C14A), N6A(C28A,C27A,C26A,C25A,C29A,C21A,C22A,C23A,C24A), N8A(C38A,
 C37A,C36A,C35A,C39A,C31A,C32A,C33A,C34A), N10A(C48A,C47A,C46A,C45A,C49A,C41A,
 C42A,C43A,C44A), N12A(C58A,C57A,C56A,C55A,C59A,C51A,C52A,C53A,C54A), N14A(C68A,
 C67A,C66A,C65A,C69A,C61A,C62A,C63A,C64A), N16A(C78A,C77A,C76A,C75A,C79A,C71A,
 C72A,C73A,C74A), C1C(C2C,C3C,C4C,C5C,C9C,N2C,C8C,C7C,C6C), C11C(C12C,C13C,C14C,
 C15C,C19C,N4C,C18C,C17C,C16C), C21C(C22C,C23C,C24C,C25C,C29C,N6C,C27C,C26C,
 C0AA), C31C(C32C,C33C,C34C,C35C,C39C,N8C,C38C,C37C,C36C), C41C(C42C,C43C,C44C,
 C45C,C49C,N10C,C48C,C47C,C46C), C51C(C52C,C53C,C54C,C55C,C59C,N12C,C58C,C57C,
 C56C), C61C(C62C,C63C,C64C,C65C,C69C,N14C,C68C,C67C,C66C)
;
_shelx_res_checksum              27735
_shelx_hkl_checksum              88183
_shelx_fab_checksum              92030
_olex2_submission_special_instructions 'No special instructions were received'