Self-assembly of achiral building blocks into chiral cyclophanes using non-directional interactions.
Zhang, Yuan; Ourri, Benjamin; Skowron, Pierre-Thomas; Jeamet, Emeric; Chetot, Titouan; Duchamp, Christian; Belenguer, Ana M.; Vanthuyne, Nicolas; Cala, Olivier; Dumont, Elise; Mandal, Pradeep K.; Huc, Ivan; Perret, Florent; Vial, Laurent; Leclaire, Julien; Chemical science 14 (2023) 7126–7135; doi:10.1039/d3sc01235b

data_1569202
_publ_section_title
;
 Self-assembly of achiral building blocks into chiral cyclophanes using
 non-directional interactions.
;
_journal_issue                   26
_journal_name_full               'Chemical science'
_journal_page_first              7126
_journal_page_last               7135
_journal_paper_doi               10.1039/d3sc01235b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C32 H15 O16 S8, 1.75(H2 O), C5 H14 N2'
_chemical_formula_sum            'C37 H32.5 N2 O17.75 S8'
_chemical_formula_weight         1045.63
_chemical_name_common            dyn[4]arene
_chemical_properties_physical    Air-sensitive,Moisture-sensitive,Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-05-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-12 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.589(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7495(18)
_cell_length_b                   11.9064(17)
_cell_length_c                   19.424(3)
_cell_measurement_reflns_used    12839
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      51.24
_cell_measurement_theta_min      2.30
_cell_volume                     2458.2(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku PILATUS 200K'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_unetI/netI     0.1149
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12376
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        51.238
_diffrn_reflns_theta_max         51.238
_diffrn_reflns_theta_min         3.712
_exptl_absorpt_coefficient_mu    3.906
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       prism
_exptl_crystal_F_000             1077
_exptl_crystal_recrystallization_method 'hanging drop vapor diffusion'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 955 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         5063
_refine_ls_number_restraints     486
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1547
_refine_ls_R_factor_gt           0.0917
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1626P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2248
_refine_ls_wR_factor_ref         0.2683
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                2853
_reflns_number_total             5063
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01235b2.cif
_cod_data_source_block           a4pentanediamine
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Empirical' was
changed to 'empirical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1569201--1569204.cif.
;
_cod_original_cell_volume        2458.2(6)
_cod_original_formula_sum        'C37 H32.50 N2 O17.75 S8'
_cod_database_code               1569202
_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,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 N2-C5D
 1.47 with sigma of 0.02
 C2D-C1D
 1.53 with sigma of 0.02
 C3D-C2D
 1.53 with sigma of 0.02
 C5D-C4D
 1.53 with sigma of 0.02
 C2D-N1
 2.45 with sigma of 0.02
 C4D-N2
 2.45 with sigma of 0.02
 C4D-C2D
 2.5 with sigma of 0.02
 C3D-C1D
 2.5 with sigma of 0.02
 C5D-C3D
 2.5 with sigma of 0.02
 N1-C1D
 1.47 with sigma of 0.02
 C8B-C24A
 1.54 with sigma of 0.02
 C2B-C6A
 1.54 with sigma of 0.02
 C6B-C17A
 1.54 with sigma of 0.02
 C4B-C11A
 1.54 with sigma of 0.02
 C1B-C3A
 1.54 with sigma of 0.02
 C3D-C4D
 1.53 with sigma of 0.02
 C2B-C6A = C1B-C3A
 1.53 with sigma of 0.02
 C3B-C8A
 1.53 with sigma of 0.02
 C7B-C21A
 1.53 with sigma of 0.02
 O8B-C4B
 1.43 with sigma of 0.02
 O2B-C2B
 1.43 with sigma of 0.02
 O1B-C2B
 1.21 with sigma of 0.02
 O3B-C1B
 1.43 with sigma of 0.02
 O6B-C3B
 1.43 with sigma of 0.02
 O5B-C3B
 1.21 with sigma of 0.02
 O9B-C5B
 1.21 with sigma of 0.02
 O10B-C5B
 1.43 with sigma of 0.02
 O12B-C6B
 1.43 with sigma of 0.02
 O11B-C6B
 1.21 with sigma of 0.02
 O16B-C8B
 1.43 with sigma of 0.02
 O15B-C8B
 1.21 with sigma of 0.02
3. Restrained planarity
 N2, C5D, C4D, C3D, C2D, C1D, N1
 with sigma of 0.1
 C23A, C24A, C19A, C20A, C21A, C7B
 with sigma of 0.1
 C7B, C21A, C22A, C23A, C24A, C19A, C20A
 with sigma of 0.1
4. Rigid bond restraints
 C9A, C8A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C21A, C7B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O6B, O5B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O11B, O12B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3B, C8A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
N1 \\sim C1D \\sim C2D \\sim C3D \\sim C4D \\sim C5D \\sim N2: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
O8B \\sim C4B \\sim O7B: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
O7B \\sim C4B \\sim O8B: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
O1B \\sim C2B \\sim O2B: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
O3B \\sim C1B \\sim O4B: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
O6B \\sim C3B \\sim O5B: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
O2B \\sim C2B \\sim O1B: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
C6A \\sim C2B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C24A \\sim C8B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C17A \\sim C6B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C14A \\sim C5B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C8A \\sim C3B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C11A \\sim C4B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C8B \\sim O15B \\sim O16B: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 1.7A
Uanis(N2) \\sim Ueq, Uanis(C5D) \\sim Ueq, Uanis(C4D) \\sim Ueq, Uanis(C3D)
\\sim Ueq, Uanis(C2D) \\sim Ueq, Uanis(C1D) \\sim Ueq, Uanis(N1) \\sim Ueq:
with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O2S) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O1B) \\sim Ueq, Uanis(O7B) \\sim Ueq, Uanis(O4B) \\sim Ueq, Uanis(O3B)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
6. Rigid body (RIGU) restrains
 N1, C1D, C2D, C3D, C4D, C5D, N2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C20A, C21A, C22A, C23A, C24A, C19A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C3A, C2A, C1A, C6A, C5A, C4A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, C5D, C4D, C3D, C2D, C1D, N1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C8A, C7A, C12A, C11A, C10A, C9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O10B, C5B, O9B, C14A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O4B, O3B, C1B, C3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O8B, C4B, O7B, C11A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C9A, C10A, C11A, C12A, C7A, C8A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C14A, C13A, C18A, C17A, C16A, C15A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C9A, C8A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C11A, C10A, C9A, C8A, C7A, C12A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C3D, C2D, C1D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C3D, C4D, C5D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C10A, C11A, C12A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12A, C11A, C10A, C9A, C8A, C7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1S, O2S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C24A, C8B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Fixed Sof: O2S(0.75) H2SA(0.75) H2SB(0.75)
8.a Free rotating group:
 O1S(H1SA,H1SB), O2S(H2SA,H2SB)
8.b Secondary CH2 refined with riding coordinates:
 C1D(H1DA,H1DB), C2D(H2DA,H2DB), C4D(H4DA,H4DB), C3D(H3DA,H3DB), C5D(H5DA,H5DB)
8.c Aromatic/amide H refined with riding coordinates:
 C22A(H22A), C19A(H19A), C10A(H10A), C7A(H7A), C16A(H16A), C13A(H13A),
 C4A(H4A), C1A(H1A)
8.d Fitted hexagon refined as free rotating group:
 C21A(C22A,C23A,C24A,C19A,C20A), C8A(C9A,C10A,C11A,C12A,C7A), C15A(C16A,C17A,
 C18A,C13A,C14A), C2A(C3A,C4A,C5A,C6A,C1A)
8.e X=CH2 refined with riding coordinates:
 N2(H2A,H2C), N1(H1B,H1C)
8.f Idealised tetrahedral OH refined as rotating group:
 O6B(H6B), O16B(H16B), O8B(H8B), O2B(H2B), O10B(H10B), O3B(H3B), O12B(H12B)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              5038
_shelx_hkl_checksum              1614
_shelx_fab_checksum              53867
_olex2_submission_special_instructions 'No special instructions were received'