Pillar[3]trianglamines: deeper cavity triangular macrocycles for selective hexene isomer separation
Ding, Yanjun; Alimi, Lukman O.; Du, Jing; Hua, Bin; Dey, Avishek; Yu, Pei; Khashab, Niveen M.; Chemical Science  (2022) –; doi:10.1039/D2SC00207H

data_1566522
_publ_section_title
;
 Pillar[3]trianglamines: deeper cavity triangular macrocycles for
 selective hexene isomer separation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00207H
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C63 H84 N6 O6, 1(C6 H12)'
_chemical_formula_sum            'C69 H96 N6 O6'
_chemical_formula_weight         1105.51
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-10-07
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2021-11-03 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   20.366
_cell_length_b                   20.366
_cell_length_c                   13.791
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    120.00
_cell_measurement_theta_max      65.024
_cell_measurement_theta_min      4.344
_cell_volume                     4953.793
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       '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      120.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16121
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        64.963
_diffrn_reflns_theta_max         64.963
_diffrn_reflns_theta_min         4.342
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0939 before and 0.0434 after correction.
The Ratio of minimum to maximum transmission is 0.9041.
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    1.112
_exptl_crystal_description       block
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1855 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3722
_refine_ls_number_restraints     1049
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0731P)^2^+2.0170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3721
_reflns_number_total             3722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00207h2.cif
_cod_data_source_block           1-He@P-TA
_cod_original_cell_volume        4953.9
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               1566522
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.937
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.880(2)
 0.120(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C13-C25 = C25-C3
 1.54 with sigma of 0.005
 C11-C23 = C23-C3
 1.54 with sigma of 0.005
 C23-C3 = C3-C25
 1.54 with sigma of 0.005
 C11-C21
 1.32 with sigma of 0.005
 C13-C3
 2.515 with sigma of 0.005
 C11-C3
 2.515 with sigma of 0.005
 C23-C25
 2.515 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10
\\sim C12 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20
\\sim C22 \\sim C24 \\sim C26 \\sim C27 \\sim C3 \\sim C11 \\sim C13 \\sim C21
\\sim C23 \\sim C25 \\sim N1 \\sim N2: within 5A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 5A
5. Others
 Fixed Sof: C3(0.33333) H3A(0.33333) H3B(0.33333) C11(0.33333) H11(0.33333)
 C13(0.33333) H13A(0.33333) H13B(0.33333) H13C(0.33333) C21(0.33333)
 H21A(0.33333) H21B(0.33333) C23(0.33333) H23A(0.33333) H23B(0.33333)
 C25(0.33333) H25A(0.33333) H25B(0.33333)
6.a Ternary CH refined with riding coordinates:
 C6(H6), C8(H8)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B), C3(H3A,H3B),
 C23(H23A,H23B), C25(H25A,H25B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C19(H19), C24(H24), C11(H11)
6.d X=CH2 refined with riding coordinates:
 C5(H5A,H5B), C17(H17A,H17B), C21(H21A,H21B)
6.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              70972
_shelx_hkl_checksum              15839
_olex2_submission_special_instructions 'No special instructions were received'