Anionic modulation induces molecular polarity in a three-component crown ether system.
Liu, Feiyan; Chen, Guoyong; Liu, Xiao; Jiang, Ting; Guo, Wenjing; Li, Xiancai; Wei, Zhenhong; Dalton transactions (Cambridge, England : 2003) 54 (2025) 2793–2798; doi:10.1039/d4dt03466j

data_7717763
_publ_section_title
;
 Anionic modulation induces molecular polarity in a three-component crown
 ether system.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2793
_journal_page_last               2798
_journal_paper_doi               10.1039/d4dt03466j
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C10 H20 O5, C7 H7 F3 N, Cl O4'
_chemical_formula_sum            'C17 H27 Cl F3 N O9'
_chemical_formula_weight         481.85
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2lv8d4
_audit_creation_date             2024-10-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-12-09 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.895(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9120(11)
_cell_length_b                   9.6790(5)
_cell_length_c                   16.9652(12)
_cell_measurement_reflns_used    9231
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.3600
_cell_measurement_theta_min      3.1070
_cell_volume                     2272.0(3)
_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_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35422
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.923
_diffrn_reflns_theta_min         2.944
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             1008.0
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.236
_refine_diff_density_min         -0.907
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.924
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6094
_refine_ls_number_restraints     529
_refine_ls_restrained_S_all      2.081
_refine_ls_R_factor_all          0.2612
_refine_ls_R_factor_gt           0.1972
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4990
_refine_ls_wR_factor_ref         0.5429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2850
_reflns_number_total             7200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt03466j2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 7717762--7717764.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7717763
_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
 O5-C12 = C12-C13
 1.55 with sigma of 0.01
 C13-O6 = O6-C14
 1.55 with sigma of 0.01
 C14-C15 = C15-O7
 1.55 with sigma of 0.01
 O7-C16 = C16-C17
 1.55 with sigma of 0.01
 C17-O8 = O8-C8
 1.55 with sigma of 0.01
 C9-O9 = O9-C10
 1.55 with sigma of 0.01
 C10-C11 = C11-O5
 1.55 with sigma of 0.01
 O5-C13
 2.55 with sigma of 0.01
 C13-C14
 2.55 with sigma of 0.01
 C14-O7
 2.55 with sigma of 0.01
 O7-C17
 2.55 with sigma of 0.01
 C17-C8
 2.55 with sigma of 0.01
 C9-C10
 2.55 with sigma of 0.01
 C10-O5
 2.55 with sigma of 0.01
 Cl1-O3 \\sim Cl1-O1 \\sim Cl1-O4 \\sim Cl1-O2
 with sigma of 0.02
 O1-O2 \\sim O1-O3 \\sim O1-O4 \\sim O2-O3 \\sim O2-O4 \\sim O3-O4
 with sigma of 0.01
 Cl1-O3A \\sim Cl1-O1A \\sim Cl1-O4A \\sim Cl1-O2A
 with sigma of 0.02
 O1A-O2A \\sim O1A-O3A \\sim O1A-O4A \\sim O2A-O3A \\sim O2A-O4A \\sim O3A-O4A
 with sigma of 0.01
 F2A-C1 \\sim F2-C1 \\sim F3A-C1 \\sim F3-C1 \\sim F1-C1 \\sim F1A-C1
 with sigma of 0.02
3. Rigid bond restraints
 O5, C12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O5, C14
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O5, O6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
O4A \\sim Cl1 \\sim O4 \\sim O1 \\sim O1A \\sim O3 \\sim O3A \\sim O2 \\sim
O2A: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.02
C1 \\sim F1 \\sim F2 \\sim F3 \\sim F3A \\sim F2A \\sim F1A: within 2A with
sigma of 0.02 and sigma for terminal atoms of 0.02
O8 \\sim O5 \\sim C11 \\sim C12 \\sim C10 \\sim C13 \\sim O9 \\sim O6 \\sim C9
\\sim C14 \\sim C8 \\sim C15 \\sim O7 \\sim C17 \\sim C16: within 2A with sigma
of 0.02 and sigma for terminal atoms of 0.02
Uanis(O4A) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(O1)
\\sim Ueq, Uanis(O1A) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O3A) \\sim Ueq,
Uanis(O2) \\sim Ueq, Uanis(O2A) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.02
Uanis(C1) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim
Ueq, Uanis(F3A) \\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F1A) \\sim Ueq: with
sigma of 0.02 and sigma for terminal atoms of 0.02
Uanis(O8) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(O9) \\sim Ueq,
Uanis(O6) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(C15) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(C17) \\sim Ueq,
Uanis(C16) \\sim Ueq: with sigma of 0.02 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
5. Others
 Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(O3)=Sof(O4)=FVAR(1)
 Sof(F3A)=Sof(F2A)=Sof(F1A)=1-FVAR(2)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
6.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_shelx_res_checksum              35294
_olex2_submission_special_instructions 'No special instructions were received'