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_1575344
_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 Cl F N, Cl O4'
_chemical_formula_sum            'C17 H28 Cl2 F N O9'
_chemical_formula_weight         480.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-07-03
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8890(5)
_cell_length_b                   18.3681(5)
_cell_length_c                   15.1150(4)
_cell_measurement_reflns_used    16544
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      30.8990
_cell_measurement_theta_min      2.9130
_cell_volume                     4411.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.111a (Rigaku OD, 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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(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 0.824
_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     -8.00  33.00   0.50    0.59    --    5.26  24.00  33.00   82
  2  \w     55.00  80.00   0.50    0.59    --    5.26  24.00  33.00   50
  3  \w     51.00  76.00   0.50    0.59    --    5.26  38.00 -90.00   50
  4  \w     -8.00  22.00   0.50    0.59    --    5.26  38.00 -90.00   60
  5  \w     -6.00  38.00   0.50    0.59    --    5.26 -99.00-150.00   88
  6  \w     -5.00  21.00   0.50    0.59    --    5.26 -99.00-120.00   52
  7  \w     -9.00  27.00   0.50    0.59    --   -4.99 -99.00   0.00   72
;
_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      0.0303866000
_diffrn_orient_matrix_UB_12      -0.0270944000
_diffrn_orient_matrix_UB_13      0.0099077000
_diffrn_orient_matrix_UB_21      -0.0295487000
_diffrn_orient_matrix_UB_22      -0.0274901000
_diffrn_orient_matrix_UB_23      -0.0109953000
_diffrn_orient_matrix_UB_31      0.0140754000
_diffrn_orient_matrix_UB_32      0.0007730000
_diffrn_orient_matrix_UB_33      -0.0445225000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33823
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.762
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.005
_diffrn_reflns_theta_min         2.895
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66988
_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            yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             2016.0
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.016
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 3385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(18)
_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     617
_refine_ls_number_reflns         10717
_refine_ls_number_restraints     397
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0966P)^2^+0.2080P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1431
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.696
_reflns_number_gt                8631
_reflns_number_total             10717
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04125b2.cif
_cod_data_source_block           1-LTP
_cod_depositor_comments
'Adding full bibliography for 1575342--1575344.cif.'
_cod_database_code               1575344
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl F'
_diffrn_oxdiff_digest_frames
;
017e1fbe53dcd02289b5de455357e1768600032d1e4
;
_diffrn_oxdiff_digest_hkl
;
433c9c836e23e3657582979f4748f8d92e5979
;
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
 Cl4-O15 \\sim Cl4-O16 \\sim Cl4-O17 \\sim Cl4-O18
 with sigma of 0.02
 Cl4-O15A \\sim Cl4-O16A \\sim Cl4-O17A \\sim Cl4-O18A
 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
 Cl2-O9 \\sim Cl2-O7 \\sim Cl2-O8 \\sim Cl2-O6
 with sigma of 0.02
 Cl2-O9A \\sim Cl2-O7A \\sim Cl2-O8A \\sim Cl2-O6A
 with sigma of 0.02
 O6-O7 \\sim O6-O8 \\sim O6-O9 \\sim O7-O8 \\sim O7-O9 \\sim O8-O9
 with sigma of 0.02
 O6A-O7A \\sim O6A-O8A \\sim O6A-O9A \\sim O7A-O8A \\sim O7A-O9A \\sim O8A-O9A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O17 \\sim Cl4 \\sim O16 \\sim O15 \\sim O18 \\sim O17A \\sim O16A \\sim O15A
\\sim O18A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
O8A \\sim Cl2 \\sim O9 \\sim O7 \\sim O6 \\sim O8 \\sim O9A \\sim O7A \\sim
O6A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O17) \\sim Ueq, Uanis(Cl4) \\sim Ueq, Uanis(O16) \\sim Ueq, Uanis(O15)
\\sim Ueq, Uanis(O18) \\sim Ueq, Uanis(O17A) \\sim Ueq, Uanis(O16A) \\sim Ueq,
Uanis(O15A) \\sim Ueq, Uanis(O18A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O8A) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(O7)
\\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(O9A) \\sim Ueq,
Uanis(O7A) \\sim Ueq, Uanis(O6A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(O17A)=Sof(O16A)=Sof(O15A)=Sof(O18A)=1-FVAR(1)
 Sof(O17)=Sof(O16)=Sof(O15)=Sof(O18)=FVAR(1)
 Sof(O9A)=Sof(O7A)=Sof(O6A)=Sof(O8A)=1-FVAR(2)
 Sof(O9)=Sof(O7)=Sof(O6)=Sof(O8)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C10(H10A,H10B), C20(H20A,H20B), C4(H4A,H4B), C21(H21A,H21B),
 C24(H24A,H24B), C5(H5A,H5B), C23(H23A,H23B), C2(H2A,H2B), C22(H22A,H22B),
 C25(H25A,H25B), C27(H27A,H27B), C1(H1A,H1B), C17(H17A,H17B), C18(H18A,H18B),
 C3(H3A,H3B), C26(H26A,H26B), C7(H7A,H7B), C6(H6A,H6B), C8(H8A,H8B), C34(H34A,
 H34B), C9(H9A,H9B)
5.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C33(H33), C15(H15), C14(H14), C32(H32), C31(H31)
5.c Idealised Me refined as rotating group:
 N1(H1C,H1D,H1E), N2(H2C,H2D,H2E)
;
_shelx_res_checksum              12956
_shelx_hkl_checksum              54861
_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 1.329
_oxdiff_exptl_absorpt_empirical_full_min 0.551