Nonspherical anion sequestration by C–H hydrogen bonding
Mirzaei, Saber; Espinoza Castro, Victor M.; Hernández Sánchez, Raúl; Chemical Science  (2022) –; doi:10.1039/D1SC07041J

data_1566207
_publ_section_title
;
 Nonspherical anion sequestration by C--H hydrogen bonding
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC07041J
_journal_year                    2022
_chemical_formula_moiety         'C76 H68 F12 O8, C2 H3 N'
_chemical_formula_sum            'C78 H71 F12 N O8'
_chemical_formula_weight         1371.34
_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
_audit_creation_date             2021-01-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-18 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.928(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.7987(9)
_cell_length_b                   33.3050(13)
_cell_length_c                   21.4220(8)
_cell_measurement_reflns_used    7690
_cell_measurement_temperature    200
_cell_measurement_theta_max      35.15
_cell_measurement_theta_min      2.46
_cell_volume                     16205.8(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 v2014.9-0'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.5418
_diffrn_reflns_av_unetI/netI     0.1602
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            295972
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        62.682
_diffrn_reflns_theta_max         62.682
_diffrn_reflns_theta_min         2.653
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.6062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0836 before and 0.0679 after correction. The Ratio of minimum to maximum transmission is 0.8059. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_description       block
_exptl_crystal_F_000             5712
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.930
_refine_diff_density_min         -0.884
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.363
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     740
_refine_ls_number_reflns         25677
_refine_ls_number_restraints     80
_refine_ls_restrained_S_all      1.362
_refine_ls_R_factor_all          0.3687
_refine_ls_R_factor_gt           0.2069
_refine_ls_shift/su_max          2.138
_refine_ls_shift/su_mean         0.015
_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          0.4897
_refine_ls_wR_factor_ref         0.5748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6899
_reflns_number_total             25677
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc07041j2.cif
_cod_data_source_block           sm320g_first_a
_cod_depositor_comments
;

2022-05-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C155 H140 F24 N2 O16'
_cod_original_formula_weight         2742.68
_cod_original_formula_moiety      'C75 H66 F12 O8, C76 H68 F12 O8, 2(C2 H3 N)'
_cod_original_formula_units_Z            4
_cod_database_code               1566207
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14A-C15A = C15A-C16A = C16A-C17A = C17A-C18A = C18A-C19A = C14B-C15B = C15B-
 C16B = C16B-C17B = C17B-C18B = C14C-C15C = C15C-C16C = C16C-C17C = C17C-C18C =
 C18C-C19C = C14D-C15D = C15D-C16D = C16D-C17D = C17D-C18D = C18D-C19D = C1S-
 C2S = C3S-C4S
 1.5 with sigma of 0.01
 C14E-C15E = C15E-C16E = C16E-C17E = C17E-C18E = C18E-C19E = C15F-C16F = C16F-
 C17F = C17F-C18F = C18F-C19F = C14G-C15G = C15G-C16G = C16G-C17G = C17G-C18G =
 C18G-C19G = C14H-C15H = C15H-C16H = C16H-C17H = C17H-C18H = C18H-C19H
 1.5 with sigma of 0.01
 C11E-C14E = C9F-C14E
 1.5 with sigma of 0.01
 N1S-C1S = N2S-C3S
 1.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N1S) \\sim Ueq, Uanis(C1S) \\sim Ueq, Uanis(C2S) \\sim Ueq, Uanis(N2S)
\\sim Ueq, Uanis(C3S) \\sim Ueq, Uanis(C4S) \\sim Ueq: with sigma of 0.03 and
sigma for terminal atoms of 0.06
Uanis(C14E) = Uanis(C15E) = Uanis(C16E) = Uanis(C17E) = Uanis(C18E) =
Uanis(C19E) = Uanis(C14F) = Uanis(C15F) = Uanis(C16F) = Uanis(C17F) =
Uanis(C18F) = Uanis(C19F) = Uanis(C14G) = Uanis(C15G) = Uanis(C16G) =
Uanis(C17G) = Uanis(C18G) = Uanis(C19G) = Uanis(C14H) = Uanis(C15H) =
Uanis(C16H) = Uanis(C17H) = Uanis(C18H) = Uanis(C19H)
Uanis(C1A) = Uanis(C2A) = Uanis(C3A) = Uanis(C4A) = Uanis(C5A) = Uanis(C6A) =
Uanis(C1B) = Uanis(C2B) = Uanis(C3B) = Uanis(C4B) = Uanis(C5B) = Uanis(C6B) =
Uanis(C1C) = Uanis(C2C) = Uanis(C3C) = Uanis(C4C) = Uanis(C5C) = Uanis(C6C) =
Uanis(C1D) = Uanis(C2D) = Uanis(C3D) = Uanis(C4D) = Uanis(C5D) = Uanis(C6D)
Uanis(C7A) = Uanis(C8A) = Uanis(C9A) = Uanis(C10A) = Uanis(C11A) = Uanis(C12A)
Uanis(C7B) = Uanis(C8B) = Uanis(C9B) = Uanis(C10B) = Uanis(C11B) = Uanis(C12B)
Uanis(C7C) = Uanis(C8C) = Uanis(C9C) = Uanis(C10C) = Uanis(C11C) = Uanis(C12C)
Uanis(C7D) = Uanis(C8D) = Uanis(C9D) = Uanis(C10D) = Uanis(C11D) = Uanis(C12D)
Uanis(C1E) = Uanis(C2E) = Uanis(C3E) = Uanis(C4E) = Uanis(C5E) = Uanis(C6E) =
Uanis(C1F) = Uanis(C2F) = Uanis(C3F) = Uanis(C4F) = Uanis(C5F) = Uanis(C6F) =
Uanis(C1G) = Uanis(C2G) = Uanis(C3G) = Uanis(C4G) = Uanis(C5G) = Uanis(C6G) =
Uanis(C1H) = Uanis(C2H) = Uanis(C3H) = Uanis(C4H) = Uanis(C5H) = Uanis(C6H)
Uanis(C7E) = Uanis(C8E) = Uanis(C9E) = Uanis(C10E) = Uanis(C11E) = Uanis(C12E)
Uanis(C7F) = Uanis(C8F) = Uanis(C9F) = Uanis(C10F) = Uanis(C11F) = Uanis(C12F)
Uanis(C7G) = Uanis(C8G) = Uanis(C9G) = Uanis(C10G) = Uanis(C11G) = Uanis(C12G)
Uanis(C7H) = Uanis(C8H) = Uanis(C9H) = Uanis(C10H) = Uanis(C11H) = Uanis(C12H)
Uanis(C14A) = Uanis(C15A) = Uanis(C16A) = Uanis(C17A) = Uanis(C18A) =
Uanis(C19A) = Uanis(C14B) = Uanis(C15B) = Uanis(C16B) = Uanis(C17B) =
Uanis(C18B) = Uanis(C14C) = Uanis(C15C) = Uanis(C16C) = Uanis(C17C) =
Uanis(C18C) = Uanis(C19C) = Uanis(C14D) = Uanis(C15D) = Uanis(C16D) =
Uanis(C17D) = Uanis(C18D) = Uanis(C19D)
Uanis(F1A) = Uanis(F2A) = Uanis(F3A) = Uanis(F1B) = Uanis(F2B) = Uanis(F3B) =
Uanis(F1C) = Uanis(F2C) = Uanis(F3C) = Uanis(F1D) = Uanis(F2D) = Uanis(F3D)
Uanis(F1E) = Uanis(F2E) = Uanis(F3E) = Uanis(F1F) = Uanis(F2F) = Uanis(F3F) =
Uanis(F1G) = Uanis(F2G) = Uanis(F3G) = Uanis(F1H) = Uanis(F2H) = Uanis(F3H)
Uanis(N1S) = Uanis(C1S) = Uanis(C2S) = Uanis(N2S) = Uanis(C3S) = Uanis(C4S)
4.a Ternary CH refined with riding coordinates:
 C14A(H14A), C14B(H14B), C14C(H14C), C14D(H14D), C14E(H14E), C14F(H14F),
 C14G(H14G), C14H(H14H)
4.b Secondary CH2 refined with riding coordinates:
 C13A(H13I,H13J), C13B(H13K,H13L), C13C(H13M,H13N), C13D(H13O,H13P), C15A(H15I,
 H15J), C15B(H15K,H15L), C15C(H15M,H15N), C15D(H15O,H15P), C16A(H16I,H16J),
 C16B(H16K,H16L), C16C(H16M,H16N), C16D(H16O,H16P), C17A(H17I,H17J), C17B(H17K,
 H17L), C17C(H17M,H17N), C17D(H17O,H17P), C18A(H18I,H18J), C18C(H18N,H18O),
 C18D(H18P,H18Q), C13E(H13A,H13B), C13F(H13C,H13D), C13G(H13E,H13F), C13H(H13G,
 H13H), C15E(H15A,H15B), C15G(H15C,H15D), C15H(H15E,H15F), C16E(H16A,H16B),
 C15F(H15G,H15H), C16G(H16C,H16D), C16H(H16E,H16F), C17E(H17A,H17B), C16F(H16G,
 H16H), C17H(H17C,H17D), C18H(H18A,H18B), C17G(H17E,H17F), C18E(H18C,H18D),
 C17F(H17G,H17H), C18G(H18E,H18F), C18F(H18G,H18H)
4.c Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C1A(H1A), C1B(H1B), C5B(H5B), C1C(H1C), C5C(H5C), C5D(H5D),
 C1D(H1D), C10A(H10A), C10B(H10B), C10C(H10C), C10D(H10D), C1E(H1E), C5E(H5E),
 C5F(H5F), C1F(H1F), C5G(H5G), C1G(H1G), C1H(H1H), C5H(H5H), C10E(H10E),
 C10F(H10F), C10G(H10G), C10H(H10H)
4.d Fitted hexagon refined as free rotating group:
 C6A(C5A,C4A,C3A,C2A,C1A), C6B(C1B,C2B,C3B,C4B,C5B), C6C(C1C,C2C,C3C,C4C,C5C),
 C6D(C5D,C4D,C3D,C2D,C1D), C6E(C1E,C2E,C3E,C4E,C5E), C6F(C5F,C4F,C3F,C2F,C1F),
 C6G(C5G,C4G,C3G,C2G,C1G), C6H(C1H,C2H,C3H,C4H,C5H)
4.e Idealised Me refined as rotating group:
 C18B(H18K,H18L,H18M), C19A(H19M,H19N,H19O), C19C(H19P,H19Q,H19R), C19D(H19S,
 H19T,H19U), C4S(H4SA,H4SB,H4SC), C2S(H2SA,H2SB,H2SC), C19E(H19A,H19B,H19C),
 C19H(H19D,H19E,H19F), C19G(H19G,H19H,H19I), C19F(H19J,H19K,H19L)
;
_shelx_res_checksum              11874
_shelx_hkl_checksum              11368
_shelx_fab_checksum              92815
_olex2_submission_special_instructions 'No special instructions were received'