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_1569201
_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 H9 O16 S8, 13.5(H2 O), H2 O0.5'
_chemical_formula_sum            'C32 H38 O30 S8'
_chemical_formula_weight         1159.10
_chemical_name_common            Dyn[4]arene
_chemical_properties_physical    Air-sensitive,Moisture-sensitive,Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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
;
2020-06-08 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.082(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2482(3)
_cell_length_b                   23.7215(5)
_cell_length_c                   11.0876(3)
_cell_measurement_reflns_used    15594
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.37
_cell_measurement_theta_min      4.74
_cell_volume                     2441.25(13)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.971
_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  0.0329
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17097
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.705
_diffrn_reflns_theta_min         3.727
_diffrn_source                   'Rigaku FRX'
_exptl_absorpt_coefficient_mu    4.242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57708
_exptl_absorpt_correction_type   multi-scan
_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    1.577
_exptl_crystal_description       prism
_exptl_crystal_F_000             1196
_exptl_crystal_recrystallization_method 'hanging drop vapor diffusion'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Flack x determined using 3653 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.0021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     712
_refine_ls_number_reflns         8784
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1035P)^2^+4.0402P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.1695
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.848
_reflns_Friedel_fraction_max     0.804
_reflns_number_gt                8635
_reflns_number_total             8784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01235b2.cif
_cod_data_source_block           A4-water
_cod_depositor_comments
'Adding full bibliography for 1569201--1569204.cif.'
_cod_original_cell_volume        2441.25(12)
_cod_database_code               1569201
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O014-H01M = O014-H01N
 0.96 with sigma of 0.02
 O01M-H01A
 0.96 with sigma of 0.02
 O01M-H01B
 0.96 with sigma of 0.02
 O1W-H1WB
 0.96 with sigma of 0.02
 O1W-H1WA
 0.96 with sigma of 0.02
 O2W-H1WB
 0.96 with sigma of 0.02
 O00N-H00D
 0.96 with sigma of 0.02
 O00N-H00C
 0.96 with sigma of 0.02
 O00P-H00F
 0.96 with sigma of 0.02
 O00P-H00E
 0.96 with sigma of 0.02
 O6B-C3B
 1.25 with sigma of 0.02
 O16B-C8B
 1.35 with sigma of 0.02
3. Rigid bond restraints
 O3B, O4B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O4B \\sim O3B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
Uanis(O01J) \\sim Ueq, Uanis(O1AA) \\sim Ueq, Uanis(O01Y) \\sim Ueq,
Uanis(O01V) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O4B) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
5. Others
 Fixed Sof: O0AA(0.5) H0AA(0.5) H0AB(0.5) O1W(0.5) O2(0.5) H2A(0.5) H2B(0.5)
 O2W(0.5) H2WA(0.5) H2WB(0.5) O3AA(0.5) H3AA(0.5) H3AB(0.5) O01Y(0.5) H01C(0.5)
 H01D(0.5) O01S(0.5) H01I(0.5) H01J(0.5) O1(0.5) H1B(0.5) H1C(0.5) O1AA(0.5)
 H1AA(0.5) H1AB(0.5) O2AA(0.5) H2AA(0.5) H2AB(0.5)
6.a Free rotating group:
 O0AA(H0AA,H0AB), O2(H2A,H2B), O2W(H2WA,H2WB), O00I(H00A,H00B), O3AA(H3AA,
 H3AB), O01Y(H01C,H01D), O01J(H01E,H01F), O01P(H01G,H01H), O01S(H01I,H01J),
 O1U(H1UA,H1UB), O01V(H01K,H01L), O1(H1B,H1C), O1AA(H1AA,H1AB), O2AA(H2AA,H2AB)
6.b Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C1A(H1A), C7A(H7A), C10A(H10A), C13A(H13A), C16A(H16A), C19A(H19A),
 C22A(H22A)
6.c Fitted hexagon refined as free rotating group:
 C4A(C3A,C2A,C1A,C6A,C5A), C12A(C7A,C8A,C9A,C10A,C11A), C13A(C18A,C17A,C16A,
 C15A,C14A), C23A(C24A,C19A,C20A,C21A,C22A)
6.d Idealised tetrahedral OH refined as rotating group:
 O16B(H16B)
;
_shelx_res_checksum              60192
_shelx_hkl_checksum              54414
_olex2_submission_special_instructions 'No special instructions were received'