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_1566521
_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         'C H2 Cl2, C63 H84 N6 O6'
_chemical_formula_sum            'C64 H86 Cl2 N6 O6'
_chemical_formula_weight         1106.28
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-12
_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                   20.2894(6)
_cell_length_b                   20.2894(6)
_cell_length_c                   13.6577(5)
_cell_measurement_reflns_used    9312
_cell_measurement_temperature    120.01
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.32
_cell_volume                     4869.1(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      120.01
_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  0.0667
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            63281
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         2.007
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1012 before and 0.0734 after correction.
The Ratio of minimum to maximum transmission is 0.9064.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_description       block
_exptl_crystal_F_000             1782
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 4366 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     731
_refine_ls_number_reflns         14887
_refine_ls_number_restraints     117
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0699
_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^)+(0.1295P)^2^+0.5763P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1820
_refine_ls_wR_factor_ref         0.2123
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                11228
_reflns_number_total             14887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00207h2.cif
_cod_data_source_block           P-TA
_cod_database_code               1566521
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.963
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9658(12)
 0.0342(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 Cl1-C63
 1.78 with sigma of 0.02
 Cl4-C63
 1.77 with sigma of 0.02
 Cl1-C63 = Cl4-C63
 1.771 with sigma of 0.01
 Cl2-Cl3
 2.916 with sigma of 0.03
 Cl1-Cl4
 2.916 with sigma of 0.03
 Cl2-C2
 1.78 with sigma of 0.02
 Cl3-C2
 1.77 with sigma of 0.02
 Cl2-C2 = Cl3-C2
 1.771 with sigma of 0.01
 Cl1-Cl4
 2.92 with sigma of 0.04
 Cl2-Cl3
 2.92 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
Cl1 \\sim Cl4 \\sim C63: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
Cl2 \\sim Cl3 \\sim C2: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
Cl1 \\sim Cl4 \\sim C63 \\sim Cl2 \\sim Cl3 \\sim C2 \\sim C61: within 3.8A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 3.8A
5. Rigid body (RIGU) restrains
 Cl1, Cl4, C63
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl2, Cl3, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: Cl1(0.75) Cl4(0.75) C63(0.75) H63A(0.75) H63B(0.75) Cl2(0.25)
 Cl3(0.25) C2(0.25) H2A(0.25) H2B(0.25)
7.a Ternary CH refined with riding coordinates:
 C1(H1), C8(H8), C18(H18), C26(H26), C28(H28), C54(H54)
7.b Secondary CH2 refined with riding coordinates:
 C63(H63A,H63B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C13(H13A,H13B), C17(H17A,H17B), C19(H19A,H19B),
 C21(H21A,H21B), C27(H27A,H27B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
  C35(H35A,H35B), C37(H37A,H37B), C39(H39A,H39B), C41(H41A,H41B), C43(H43A,
 H43B), C44(H44A,H44B), C46(H46A,H46B), C47(H47A,H47B), C49(H49A,H49B),
 C52(H52A,H52B), C55(H55A,H55B), C58(H58A,H58B), C60(H60A,H60B), C65(H65A,H65B)
7.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C15(H15), C22(H22), C23(H23), C24(H24), C25(H25),
 C29(H29), C42(H42), C45(H45), C48(H48)
7.d X=CH2 refined with riding coordinates:
 C31(H31A,H31B), C51(H51A,H51B), C53(H53A,H53B), C57(H57A,H57B), C59(H59A,
 H59B), C61(H61A,H61B)
;
_shelx_res_checksum              11345
_shelx_hkl_checksum              37812
_olex2_submission_special_instructions 'No special instructions were received'