Benzylamine cation-directed introduction of a polar structure in a stator-rotor crown ether system.
Liu, Feiyan; Wu, Yaozhen; Chen, Guoyong; Yan, Guobing; Li, Xiancai; Wei, Zhenhong; Chemical communications (Cambridge, England) 61 (2025) 13928–13931; doi:10.1039/d5cc04125b

data_1575342
_publ_section_title
;
 Benzylamine cation-directed introduction of a polar structure in a
 stator-rotor crown ether system.
;
_journal_issue                   73
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13928
_journal_page_last               13931
_journal_paper_doi               10.1039/d5cc04125b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C10 H20 O5, C7 H8 F2 N, Cl O4'
_chemical_formula_sum            'C17 H28 Cl F2 N O9'
_chemical_formula_weight         463.85
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-07-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-08-01 deposited with the CCDC.	2025-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.962(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.6646(2)
_cell_length_b                   15.03960(10)
_cell_length_c                   18.7902(2)
_cell_measurement_reflns_used    44648
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      77.0350
_cell_measurement_theta_min      2.8890
_cell_volume                     4303.49(10)
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.111a 64-bit (release 27-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -33.00  25.00   0.50    0.09    --  -47.40  43.00-113.00  116
  2  \w    -12.00  14.00   0.50    0.09    --  -47.40  19.00   0.00   52
  3  \w    -23.00  27.00   0.50    0.09    --  -47.40  19.00  30.00  100
  4  \w     66.00 104.00   0.50    0.09    --   47.40  43.00-113.00   76
  5  \w     25.00  62.00   0.50    0.09    --   47.40  77.00  30.00   74
  6  \w     35.00  60.00   0.50    0.09    --   47.40  38.00  60.00   50
  7  \w     87.00 113.00   0.50    0.09    --   47.40  38.00  60.00   52
  8  \w     95.00 120.00   0.50    0.09    --   47.40  77.00  30.00   50
  9  \w     85.00 158.00   0.50    0.09    --  107.16 125.00 150.00  146
 10  \w     80.00 140.00   0.50    0.09    --  107.16 125.00-150.00  120
 11  \w    150.00 176.00   0.50    0.09    --  107.16 125.00-150.00   52
 12  \w     94.00 138.00   0.50    0.09    --  107.16  43.00-113.00   88
 13  \w     43.00 108.00   0.50    0.09    --  107.16 -77.00 -30.00  130
 14  \w     35.00  67.00   0.50    0.09    --  107.16 -57.00  60.00   64
 15  \w     36.00  62.00   0.50    0.09    --  107.16 -57.00 150.00   52
 16  \w     11.00  42.00   0.50    0.09    --   47.40 -43.00  95.00   62
 17  \w     37.00  63.00   0.50    0.09    --  107.16 -57.00-120.00   52
 18  \w     43.00  68.00   0.50    0.09    --  107.16 -57.00-150.00   50
 19  \w     48.00  86.00   0.50    0.09    --  107.16 -99.00-150.00   76
 20  \w     37.00  88.00   0.50    0.09    --  107.16 -99.00 150.00  102
 21  \w     44.00 102.00   0.50    0.09    --  107.16 -99.00 120.00  116
 22  \w    -63.00 -31.00   0.50    0.09    -- -103.00  57.00-120.00   64
 23  \w    -63.00 -31.00   0.50    0.09    -- -103.00  57.00 -90.00   64
 24  \w    -60.00 -32.00   0.50    0.09    -- -103.00  57.00 -30.00   56
 25  \w    -63.00 -30.00   0.50    0.09    -- -103.00  57.00   0.00   66
 26  \w    -63.00 -31.00   0.50    0.09    -- -103.00  57.00  60.00   64
 27  \w    -62.00 -31.00   0.50    0.09    -- -103.00  57.00 120.00   62
 28  \w    -62.00 -37.00   0.50    0.09    -- -103.00  57.00  90.00   50
 29  \w    -91.00 -17.00   0.50    0.09    --  -47.40 125.00   0.00  148
 30  \w   -118.00 -35.00   0.50    0.09    --  -47.40 -43.00  95.00  166
 31  \w    -77.00 -50.00   0.50    0.09    --  -47.40 -57.00   0.00   54
 32  \w   -120.00 -37.00   0.50    0.09    --  -47.40 -38.00   0.00  166
 33  \w   -174.00-122.00   0.50    0.09    -- -103.00 -77.00  30.00  104
 34  \w   -105.00 -80.00   0.50    0.09    -- -103.00 -77.00   0.00   50
 35  \w   -106.00 -80.00   0.50    0.09    -- -103.00 -77.00 -30.00   52
 36  \w   -107.00 -82.00   0.50    0.09    -- -103.00 -72.00 -20.37   50
 37  \w   -107.00 -82.00   0.50    0.09    -- -103.00 -73.00  18.35   50
 38  \w   -105.00 -80.00   0.50    0.09    -- -103.00 -77.00  30.00   50
 39  \w   -105.00 -80.00   0.50    0.09    -- -103.00 -77.00  60.00   50
 40  \w   -109.00 -84.00   0.50    0.09    -- -103.00 -68.00  29.13   50
 41  \w   -111.00 -86.00   0.50    0.09    -- -103.00 -64.00  29.74   50
 42  \w   -174.00-113.00   0.50    0.09    -- -103.00 -77.00  60.00  122
 43  \w   -166.00 -83.00   0.50    0.09    -- -103.00 -71.00 -14.82  166
 44  \w   -115.00 -88.00   0.50    0.09    -- -103.00 -61.00   2.52   54
 45  \w   -154.00-128.00   0.50    0.09    -- -103.00 -61.00   2.52   52
 46  \w   -159.00-133.00   0.50    0.09    -- -103.00 -60.00  -6.08   52
 47  \w   -161.00-132.00   0.50    0.09    -- -103.00 -61.00 -27.66   58
 48  \w   -126.00 -87.00   0.50    0.09    -- -103.00 -61.00 -27.66   78
 49  \w   -123.00 -87.00   0.50    0.09    -- -103.00 -61.00 -39.65   72
 50  \w   -113.00 -88.00   0.50    0.09    -- -103.00 -60.00  -6.08   50
 51  \w   -112.00 -86.00   0.50    0.09    -- -103.00 -61.00  -3.17   52
 52  \w   -112.00 -87.00   0.50    0.09    -- -103.00 -60.00 -11.46   50
 53  \w   -114.00 -88.00   0.50    0.09    -- -103.00 -60.00 -13.28   52
 54  \w   -119.00 -89.00   0.50    0.09    -- -103.00 -58.00 -45.98   60
 55  \w   -160.00 -87.00   0.50    0.09    -- -103.00 -59.00 -34.45  146
 56  \w   -138.00 -88.00   0.50    0.09    -- -103.00 -57.00  12.77  100
 57  \w   -113.00 -88.00   0.50    0.09    -- -103.00 -57.00  30.00   50
 58  \w   -114.00 -89.00   0.50    0.09    -- -103.00 -55.00  24.66   50
 59  \w   -114.00 -88.00   0.50    0.09    -- -103.00 -56.00  31.46   52
 60  \w   -114.00 -89.00   0.50    0.09    -- -103.00 -54.00  43.21   50
 61  \w   -136.00 -88.00   0.50    0.09    -- -103.00 -57.00  60.00   96
 62  \w   -173.00-147.00   0.50    0.09    -- -103.00 -55.00  24.66   52
 63  \w   -171.00-145.00   0.50    0.09    -- -103.00 -54.00  43.21   52
 64  \w   -156.00-131.00   0.50    0.09    -- -103.00 -43.00  95.00   50
 65  \w   -115.00 -89.00   0.50    0.09    -- -103.00 -54.00  20.81   52
 66  \w   -135.00 -95.00   0.50    0.09    -- -103.00 -38.00  30.00   80
 67  \w   -174.00-121.00   0.50    0.09    -- -103.00 -44.00 -57.58  106
 68  \w   -136.00 -73.00   0.50    0.09    -- -103.00-125.00-120.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            71789
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.094
_diffrn_reflns_theta_min         2.902
_exptl_absorpt_coefficient_mu    2.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38527
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.111a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       block
_exptl_crystal_F_000             1952.0
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         8925
_refine_ls_number_restraints     332
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0973P)^2^+0.7190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1493
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7864
_reflns_number_total             8925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04125b2.cif
_cod_data_source_block           2-LTP
_cod_depositor_comments
'Adding full bibliography for 1575342--1575344.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1575342
_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,H) groups
2. Restrained distances
 Cl1-O7 \\sim Cl1-O8 \\sim Cl1-O9 \\sim Cl1-O6
 with sigma of 0.02
 Cl1-O7A \\sim Cl1-O8A \\sim Cl1-O9A \\sim Cl1-O6A
 with sigma of 0.02
 O6-O7 \\sim O6-O8 \\sim O6-O8 \\sim O7-O8 \\sim O7-O9 \\sim O8-O9
 with sigma of 0.01
 O6A-O7A \\sim O6A-O8A \\sim O6A-O8A \\sim O7A-O8A \\sim O7A-O9A \\sim O8A-O9A
 with sigma of 0.01
 Cl2-O15 \\sim Cl2-O18 \\sim Cl2-O16 \\sim Cl2-O17
 with sigma of 0.02
 Cl2-O15A \\sim Cl2-O18A \\sim Cl2-O16A \\sim Cl2-O17A
 with sigma of 0.02
 O15-O16 \\sim O15-O17 \\sim O15-O18 \\sim O16-O17 \\sim O16-O18 \\sim O17-O18
 with sigma of 0.02
 O15A-O16A \\sim O15A-O17A \\sim O15A-O18A \\sim O16A-O17A \\sim O16A-O18A
\\sim O17A-O18A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O7A \\sim Cl1 \\sim O7 \\sim O9 \\sim O6 \\sim O8 \\sim O9A \\sim O6A \\sim
O8A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
O16A \\sim Cl2 \\sim O17 \\sim O15 \\sim O18 \\sim O16 \\sim O17A \\sim O15A
\\sim O18A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O7A) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(O9)
\\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(O9A) \\sim Ueq,
Uanis(O6A) \\sim Ueq, Uanis(O8A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O16A) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(O17) \\sim Ueq, Uanis(O15)
\\sim Ueq, Uanis(O18) \\sim Ueq, Uanis(O16) \\sim Ueq, Uanis(O17A) \\sim Ueq,
Uanis(O15A) \\sim Ueq, Uanis(O18A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(O7A)=Sof(O9A)=Sof(O6A)=Sof(O8A)=1-FVAR(1)
 Sof(O7)=Sof(O9)=Sof(O6)=Sof(O8)=FVAR(1)
 Sof(O17A)=Sof(O15A)=Sof(O18A)=Sof(O16A)=1-FVAR(2)
 Sof(O17)=Sof(O15)=Sof(O18)=Sof(O16)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C24(H24a,H24b), C34(H34a,H34b), C23(H23a,H23b), C21(H21a,H21b), C26(H26a,
 H26b), C19(H19a,H19b), C25(H25a,H25b), C27(H27a,H27b), C22(H22a,H22b),
 C18(H18a,H18b), C20(H20a,H20b), C7(H7a,H7b), C8(H8a,H8b), C1(H1a,H1b), C2(H2a,
 H2b), C9(H9a,H9b), C5(H5a,H5b), C10(H10a,H10b), C4(H4a,H4b), C3(H3a,H3b),
 C6(H6a,H6b), C17(H17a,H17b)
5.b Aromatic/amide H refined with riding coordinates:
 C33(H33), C32(H32), C31(H31), C16(H16), C15(H15), C14(H14)
5.c Idealised Me refined as rotating group:
 N2(H2c,H2d,H2e), N1(H1c,H1d,H1e)
;
_shelx_res_checksum              13149
_shelx_hkl_checksum              11969
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;