#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:08:38 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298905 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/77/7717764.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7717764
loop_
_publ_author_name
'Liu, Feiyan'
'Chen, Guoyong'
'Liu, Xiao'
'Jiang, Ting'
'Guo, Wenjing'
'Li, Xiancai'
'Wei, Zhenhong'
_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, F6 P, C7 H7 F3 N'
_chemical_formula_sum            'C17 H27 F9 N O5 P'
_chemical_formula_weight         527.37
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2lv8f5
_audit_creation_date             2024-12-09
_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                 93.642(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5818(4)
_cell_length_b                   15.9181(6)
_cell_length_c                   13.8015(5)
_cell_measurement_reflns_used    12077
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.1190
_cell_measurement_theta_min      2.9510
_cell_volume                     2320.06(15)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.845
_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  0.0419
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28272
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.838
_diffrn_reflns_theta_min         2.956
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             1088.0
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         6169
_refine_ls_number_restraints     282
_refine_ls_restrained_S_all      1.191
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0724
_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/[σ²(Fo²)+(0.0885P)²+2.0169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1939
_refine_ls_wR_factor_ref         0.2116
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4128
_reflns_number_total             6169
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt03466j2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7717762--7717764.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7717764
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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
 P1-F4 \\sim P1-F5 \\sim P1-F2 \\sim P1-F3 \\sim P1-F1 \\sim P1-F6
 with sigma of 0.02
 P1-F4A \\sim P1-F5A \\sim P1-F2A \\sim P1-F3A \\sim P1-F1A \\sim P1-F6A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F6A \\sim P1 \\sim F6 \\sim F4 \\sim F4A \\sim F5 \\sim F5A \\sim F1 \\sim F1A
\\sim F3A \\sim F3 \\sim F2A \\sim F2: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(F6A) \\sim Ueq, Uanis(P1) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F4) \\sim
Ueq, Uanis(F4A) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F1)
\\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F3) \\sim Ueq,
Uanis(F2A) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(F6A)=Sof(F4A)=Sof(F5A)=Sof(F1A)=Sof(F3A)=Sof(F2A)=1-FVAR(1)
 Sof(F5)=Sof(F6)=Sof(F2)=Sof(F4)=Sof(F3)=Sof(F1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B),
 C1(H1A,H1B), C2(H2A,H2B), C9(H9A,H9B), C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C12(H12), C15(H15), C13(H13)
5.c Idealised Me refined as rotating group:
 N1(H1C,H1D,H1E)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.75975(8) 0.32082(7) 0.42612(6) 0.0647(3) Uani 1 1 d D U . . .
O2 O 0.79158(18) 0.32677(10) 0.77443(14) 0.0418(4) Uani 1 1 d . . . . .
O1 O 0.53548(18) 0.35178(12) 0.70024(14) 0.0446(4) Uani 1 1 d . . . . .
O3 O 0.96403(19) 0.45670(11) 0.76052(15) 0.0455(5) Uani 1 1 d . . . . .
O4 O 0.7797(2) 0.55764(12) 0.84328(14) 0.0483(5) Uani 1 1 d . . . . .
O5 O 0.5277(2) 0.51247(13) 0.77977(16) 0.0515(5) Uani 1 1 d . . . . .
N1 N 0.7730(2) -0.02747(12) 0.84594(14) 0.0350(4) Uani 1 1 d . . . . .
H1C H 0.700295 -0.033965 0.807850 0.042 Uiso 1 1 calc GR . . . .
H1D H 0.782219 -0.071394 0.887998 0.042 Uiso 1 1 calc GR . . . .
H1E H 0.840206 -0.025872 0.807950 0.042 Uiso 1 1 calc GR . . . .
F8 F 0.6828(3) 0.33661(14) 1.00722(17) 0.1012(10) Uani 1 1 d . . . . .
F9 F 0.6913(4) 0.27181(16) 1.13623(18) 0.1202(12) Uani 1 1 d . . . . .
C11 C 0.7672(2) 0.05090(14) 0.90055(15) 0.0299(5) Uani 1 1 d . . . . .
C16 C 0.6520(2) 0.07890(16) 0.92913(18) 0.0370(5) Uani 1 1 d . . . . .
H16 H 0.577120 0.047414 0.913944 0.044 Uiso 1 1 calc R . . . .
C12 C 0.8774(2) 0.09483(16) 0.92261(18) 0.0361(5) Uani 1 1 d . . . . .
H12 H 0.956132 0.074200 0.903061 0.043 Uiso 1 1 calc R . . . .
C15 C 0.6471(2) 0.15316(17) 0.98000(19) 0.0392(6) Uani 1 1 d . . . . .
H15 H 0.568476 0.173248 1.000258 0.047 Uiso 1 1 calc R . . . .
C13 C 0.8720(2) 0.16954(16) 0.97370(19) 0.0395(5) Uani 1 1 d . . . . .
H13 H 0.947041 0.200726 0.989493 0.047 Uiso 1 1 calc R . . . .
C14 C 0.7567(2) 0.19830(15) 1.00148(18) 0.0363(5) Uani 1 1 d . . . . .
F7 F 0.8566(3) 0.3114(2) 1.0816(3) 0.160(2) Uani 1 1 d . . . . .
F5 F 0.6932(12) 0.2726(8) 0.3472(10) 0.113(4) Uani 0.334(4) 1 d D U P A 1
F6 F 0.8447(12) 0.3828(7) 0.3835(8) 0.080(3) Uani 0.334(4) 1 d D U P A 1
C4 C 0.7094(3) 0.26130(16) 0.7399(2) 0.0445(6) Uani 1 1 d . . . . .
H4A H 0.734168 0.207768 0.772326 0.053 Uiso 1 1 calc R . . . .
H4B H 0.715216 0.254069 0.669107 0.053 Uiso 1 1 calc R . . . .
C17 C 0.7482(3) 0.27926(19) 1.0553(2) 0.0512(7) Uani 1 1 d . . . . .
C3 C 0.5777(3) 0.28347(18) 0.7611(2) 0.0490(7) Uani 1 1 d . . . . .
H3A H 0.521579 0.234338 0.749012 0.059 Uiso 1 1 calc R . . . .
H3B H 0.574769 0.299714 0.830196 0.059 Uiso 1 1 calc R . . . .
F2 F 0.6782(8) 0.3343(8) 0.5106(5) 0.092(2) Uani 0.334(4) 1 d D U P A 1
C5 C 0.9203(3) 0.31041(17) 0.7580(2) 0.0491(7) Uani 1 1 d . . . . .
H5A H 0.932420 0.309677 0.687486 0.059 Uiso 1 1 calc R . . . .
H5B H 0.945950 0.255081 0.785497 0.059 Uiso 1 1 calc R . . . .
C6 C 0.9985(3) 0.37860(18) 0.8063(3) 0.0564(8) Uani 1 1 d . . . . .
H6A H 0.982925 0.381094 0.876259 0.068 Uiso 1 1 calc R . . . .
H6B H 1.089569 0.367221 0.800083 0.068 Uiso 1 1 calc R . . . .
C7 C 0.9943(3) 0.52802(19) 0.8194(2) 0.0542(7) Uani 1 1 d . . . . .
H7A H 0.998769 0.578237 0.777409 0.065 Uiso 1 1 calc R . . . .
H7B H 1.078704 0.519828 0.853210 0.065 Uiso 1 1 calc R . . . .
C8 C 0.8991(3) 0.5429(2) 0.8928(2) 0.0591(8) Uani 1 1 d . . . . .
H8A H 0.894295 0.493323 0.935657 0.071 Uiso 1 1 calc R . . . .
H8B H 0.924274 0.592147 0.933408 0.071 Uiso 1 1 calc R . . . .
C1 C 0.4439(3) 0.4495(2) 0.8103(3) 0.0593(8) Uani 1 1 d . . . . .
H1A H 0.362973 0.475113 0.827256 0.071 Uiso 1 1 calc R . . . .
H1B H 0.481882 0.420067 0.868301 0.071 Uiso 1 1 calc R . . . .
C2 C 0.4213(3) 0.3890(2) 0.7283(3) 0.0585(8) Uani 1 1 d . . . . .
H2A H 0.363155 0.344260 0.748011 0.070 Uiso 1 1 calc R . . . .
H2B H 0.379659 0.418785 0.671978 0.070 Uiso 1 1 calc R . . . .
C9 C 0.6793(4) 0.5592(2) 0.9070(2) 0.0607(8) Uani 1 1 d . . . . .
H9A H 0.695044 0.603439 0.956738 0.073 Uiso 1 1 calc R . . . .
H9B H 0.673840 0.504445 0.940527 0.073 Uiso 1 1 calc R . . . .
F4 F 0.6931(9) 0.4089(7) 0.3863(9) 0.122(3) Uani 0.334(4) 1 d D U P A 1
C10 C 0.5584(4) 0.5766(2) 0.8489(3) 0.0645(9) Uani 1 1 d . . . . .
H10A H 0.488885 0.581774 0.893279 0.077 Uiso 1 1 calc R . . . .
H10B H 0.565741 0.630878 0.814665 0.077 Uiso 1 1 calc R . . . .
F3 F 0.8595(6) 0.3912(6) 0.4859(7) 0.086(2) Uani 0.334(4) 1 d D U P A 1
F1 F 0.8495(8) 0.2586(6) 0.4782(9) 0.096(3) Uani 0.334(4) 1 d D U P A 1
F6A F 0.8596(7) 0.3508(5) 0.3553(6) 0.116(2) Uani 0.666(4) 1 d D U P A 2
F4A F 0.6707(3) 0.3912(3) 0.4634(4) 0.0908(14) Uani 0.666(4) 1 d D U P A 2
F5A F 0.6598(5) 0.3131(4) 0.3377(3) 0.0907(16) Uani 0.666(4) 1 d D U P A 2
F1A F 0.8413(5) 0.2396(3) 0.4057(5) 0.127(2) Uani 0.666(4) 1 d D U P A 2
F3A F 0.8376(3) 0.3304(4) 0.5275(3) 0.0923(14) Uani 0.666(4) 1 d D U P A 2
F2A F 0.6650(3) 0.2521(2) 0.4812(2) 0.0718(10) Uani 0.666(4) 1 d D U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F5 P1 F6 109.1(7) . . ?
F5 P1 F2 112.0(7) . . ?
F5 P1 F4 91.3(6) . . ?
F5 P1 F3 161.1(7) . . ?
F5 P1 F1 105.3(7) . . ?
F6 P1 F2 127.1(6) . . ?
F6 P1 F4 63.8(7) . . ?
F6 P1 F3 52.0(6) . . ?
F6 P1 F1 104.2(6) . . ?
F2 P1 F4 83.3(6) . . ?
F2 P1 F3 84.3(5) . . ?
F2 P1 F1 95.6(6) . . ?
F4 P1 F3 80.9(5) . . ?
F1 P1 F4 162.3(6) . . ?
F1 P1 F3 81.4(5) . . ?
F6A P1 F4A 115.6(4) . . ?
F6A P1 F5A 89.2(4) . . ?
F6A P1 F1A 74.9(4) . . ?
F6A P1 F3A 100.9(4) . . ?
F6A P1 F2A 157.2(3) . . ?
F4A P1 F1A 169.0(3) . . ?
F4A P1 F3A 86.1(3) . . ?
F4A P1 F2A 86.0(2) . . ?
F5A P1 F4A 85.5(3) . . ?
F5A P1 F1A 98.4(3) . . ?
F5A P1 F3A 168.9(3) . . ?
F5A P1 F2A 84.8(3) . . ?
F1A P1 F2A 84.1(2) . . ?
F3A P1 F1A 88.7(3) . . ?
F3A P1 F2A 87.4(2) . . ?
C5 O2 C4 112.7(2) . . ?
C2 O1 C3 113.4(2) . . ?
C7 O3 C6 113.6(2) . . ?
C8 O4 C9 112.5(2) . . ?
C1 O5 C10 115.4(2) . . ?
C16 C11 N1 119.4(2) . . ?
C12 C11 N1 119.0(2) . . ?
C12 C11 C16 121.6(2) . . ?
C15 C16 C11 119.1(2) . . ?
C11 C12 C13 119.1(2) . . ?
C16 C15 C14 119.9(2) . . ?
C14 C13 C12 119.5(2) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 C17 118.7(2) . . ?
C13 C14 C17 120.4(2) . . ?
O2 C4 C3 108.8(2) . . ?
F8 C17 F9 103.9(3) . . ?
F8 C17 C14 113.5(2) . . ?
F9 C17 C14 113.1(3) . . ?
F7 C17 F8 107.5(3) . . ?
F7 C17 F9 104.2(3) . . ?
F7 C17 C14 113.8(3) . . ?
O1 C3 C4 109.1(2) . . ?
O2 C5 C6 107.8(2) . . ?
O3 C6 C5 108.4(2) . . ?
O3 C7 C8 112.2(3) . . ?
O4 C8 C7 108.6(2) . . ?
O5 C1 C2 107.7(3) . . ?
O1 C2 C1 112.1(3) . . ?
O4 C9 C10 108.6(3) . . ?
O5 C10 C9 112.3(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F5 1.475(9) . ?
P1 F6 1.482(9) . ?
P1 F2 1.509(6) . ?
P1 F4 1.648(9) . ?
P1 F3 1.714(6) . ?
P1 F1 1.521(7) . ?
P1 F6A 1.559(6) . ?
P1 F4A 1.572(4) . ?
P1 F5A 1.568(4) . ?
P1 F1A 1.590(4) . ?
P1 F3A 1.585(3) . ?
P1 F2A 1.696(3) . ?
O2 C4 1.420(3) . ?
O2 C5 1.419(3) . ?
O1 C3 1.429(3) . ?
O1 C2 1.422(4) . ?
O3 C6 1.431(3) . ?
O3 C7 1.421(3) . ?
O4 C8 1.417(4) . ?
O4 C9 1.422(4) . ?
O5 C1 1.420(4) . ?
O5 C10 1.421(4) . ?
N1 C11 1.461(3) . ?
F8 C17 1.302(4) . ?
F9 C17 1.308(4) . ?
C11 C16 1.379(3) . ?
C11 C12 1.377(3) . ?
C16 C15 1.378(4) . ?
C12 C13 1.386(3) . ?
C15 C14 1.380(4) . ?
C13 C14 1.380(4) . ?
C14 C17 1.493(3) . ?
F7 C17 1.287(4) . ?
C4 C3 1.484(4) . ?
C5 C6 1.496(4) . ?
C7 C8 1.492(5) . ?
C1 C2 1.493(5) . ?
C9 C10 1.492(5) . ?
