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_1575343
_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         'Cl O4, C10 H20 O5, C7 H8 F2 N'
_chemical_formula_sum            'C17 H28 Cl F2 N O9'
_chemical_formula_weight         463.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-07-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-08-01 deposited with the CCDC.	2025-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.612(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4791(5)
_cell_length_b                   15.2313(11)
_cell_length_c                   17.2552(10)
_cell_measurement_reflns_used    8730
_cell_measurement_temperature    299.69(10)
_cell_measurement_theta_max      25.8430
_cell_measurement_theta_min      2.9480
_cell_volume                     2227.6(2)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.69(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -14.00  38.00   0.50    1.14    --    5.34 -99.00  60.00  104
  2  \w    -14.00  38.00   0.50    1.14    --    5.34 -99.00 -60.00  104
  3  \w    -29.00  -3.00   0.50    1.14    --    5.34 -38.00 -60.00   52
  4  \w     -7.00  64.00   0.50    1.14    --    5.34  38.00-180.00  142
  5  \w    -30.00  43.00   0.50    1.14    --   -5.07  83.00 -71.00  146
  6  \w    -37.00  21.00   0.50    1.14    --   -5.07 -83.00 167.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0602022000
_diffrn_orient_matrix_UB_12      -0.0280260000
_diffrn_orient_matrix_UB_13      0.0151369000
_diffrn_orient_matrix_UB_21      -0.0582265000
_diffrn_orient_matrix_UB_22      -0.0295847000
_diffrn_orient_matrix_UB_23      0.0128773000
_diffrn_orient_matrix_UB_31      0.0015740000
_diffrn_orient_matrix_UB_32      -0.0223707000
_diffrn_orient_matrix_UB_33      -0.0360396000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22957
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.966
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55268
_exptl_absorpt_correction_type   multi-scan
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             975.9
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     520
_refine_ls_number_reflns         4388
_refine_ls_number_restraints     1383
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0596
_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^)+(0.0969P)^2^+0.6485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1711
_refine_ls_wR_factor_ref         0.1818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3479
_reflns_number_total             4388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04125b2.cif
_cod_data_source_block           2-HTP
_cod_depositor_comments
'Adding full bibliography for 1575342--1575344.cif.'
_cod_original_sg_symbol_H-M      '	P 21/n'
_cod_database_code               1575343
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H N O F Cl'
_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
 O6-O7 \\sim O6-O8 \\sim O7-O8 \\sim O8-O9
 with sigma of 0.04
 Cl1-O6 \\sim Cl1-O7 \\sim Cl1-O8 \\sim Cl1-O9
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim O6 \\sim O7 \\sim O8 \\sim O9 \\sim O6C \\sim O7C \\sim O8C \\sim O9C
\\sim O6A \\sim O7A \\sim O8A \\sim O9A \\sim O6B \\sim O7B \\sim O8B \\sim
O9B: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
O1 \\sim O2 \\sim O3 \\sim O4 \\sim O5 \\sim C1 \\sim C2 \\sim C3 \\sim C4
\\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim O1A \\sim O2A
\\sim O3A \\sim O4A \\sim O5A \\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A
\\sim C6A \\sim C7A \\sim C8A \\sim C9A \\sim C10A: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 O1, O2, O3, O4, O5, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, O1A, O2A, O3A,
 O4A, O5A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.008
 Cl1, O6, O7, O8, O9, O6A, O7A, O8A, O9A, O6B, O7B, O8B, O9B, O6C, O7C, O8C, O9C
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{Cl1, O6B, O7B, O8B, O9B} sigma for 1-2: 0.01, 1-3: 0.04
{Cl1, O6A, O7A, O8A, O9A} sigma for 1-2: 0.01, 1-3: 0.04
{Cl1, O6C, O7C, O8C, O9C} sigma for 1-2: 0.01, 1-3: 0.04
as in
{Cl1, O6, O7, O8, O9}
{O1A, O2A, O3A, O4A, O5A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A}
sigma for 1-2: 0.01, 1-3: 0.04
as in
{O1, O2, O3, O4, O5, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10}
6. Others
 1*[Sof(O6)+Sof(O7)+Sof(O8)+Sof(O9)]+1*[Sof(O6A)+Sof(O7A)+Sof(O8A)+Sof(O9A)]+1*
 [Sof(O6B)+Sof(O7B)+Sof(O8B)+Sof(O9B)]+1*[Sof(O6C)+Sof(O7C)+Sof(O8C)+Sof(O9C)]=
 1 with esd of 0
 Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=Sof(O5A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=
 Sof(H4AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(C7A)=
 Sof(H7AA)=Sof(H7AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=
 Sof(C10A)=Sof(H10C)=Sof(H10D)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(O3)=Sof(O4)=Sof(O5)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=
 Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=
 Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=
 Sof(H8A)=Sof(H8B)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=
 FVAR(1)
 Sof(O6)=Sof(O7)=Sof(O8)=Sof(O9)=FVAR(2)
 Sof(O6A)=Sof(O7A)=Sof(O8A)=Sof(O9A)=FVAR(3)
 Sof(O6B)=Sof(O7B)=Sof(O8B)=Sof(O9B)=FVAR(4)
 Sof(O6C)=Sof(O7C)=Sof(O8C)=Sof(O9C)=FVAR(5)
7.a Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,
 H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B),
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB),
  C6A(H6AA,H6AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB), C9A(H9AA,H9AB), C10A(H10C,
 H10D)
7.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16)
7.c Idealised Me refined as rotating group:
 N1(H1C,H1D,H1E)
;
_shelx_res_checksum              10237
_shelx_hkl_checksum              44833
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.629
_oxdiff_exptl_absorpt_empirical_full_min 0.650