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_1566205
_publ_section_title
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 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 H76 F4 O8, 3(C2 H3 N)'
_chemical_formula_sum            'C82 H85 F4 N3 O8'
_chemical_formula_weight         1316.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-10-12
_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                99.8320(10)
_cell_angle_beta                 96.5290(10)
_cell_angle_gamma                101.9540(10)
_cell_formula_units_Z            2
_cell_length_a                   11.9504(3)
_cell_length_b                   12.9188(3)
_cell_length_c                   24.0391(7)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    220
_cell_measurement_theta_max      61.352
_cell_measurement_theta_min      3.569
_cell_volume                     3534.42(16)
_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      220
_diffrn_detector                 'Bruker APEX2 CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f 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  0.0695
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            57393
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        62.540
_diffrn_reflns_theta_max         62.540
_diffrn_reflns_theta_min         1.888
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.6513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0868 before and 0.0689 after correction.
The Ratio of minimum to maximum transmission is 0.8659.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             1396
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.668
_refine_diff_density_min         -1.167
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     781
_refine_ls_number_reflns         10927
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0979
_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^)+(0.1271P)^2^+6.2782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2581
_refine_ls_wR_factor_ref         0.2819
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7787
_reflns_number_total             10927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc07041j2.cif
_cod_data_source_block           sm335first_a
_cod_database_code               1566205
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.953
_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. Shared sites
{C6B, C2BA}
{C1B, C3BA}
{C5B, C4BA}
{C4B, C5BA}
{C3B, C6BA}
{C2B, C7BA}
{C6C, C6AA}
{C5C, C7AA}
{C4C, C8AA}
{C3C, C9AA}
{C2C, C0BA}
{C1C, C1BA}
{C2S, C2T}
{C6A, C0AA}
{C5A, C1AA}
{C4A, C2AA}
{C3A, C3AA}
{C2A, C4AA}
{C1A, C5AA}
3. Uiso/Uaniso restraints and constraints
Uanis(N3S) \\sim Ueq, Uanis(C5S) \\sim Ueq, Uanis(C6S) \\sim Ueq, Uanis(N2S)
\\sim Ueq, Uanis(C3S) \\sim Ueq, Uanis(C4S) \\sim Ueq: with sigma of 0.04 and
sigma for terminal atoms of 0.08
Uanis(N3S) = Uanis(C5S) = Uanis(C6S) = Uanis(N2S) = Uanis(C3S) = Uanis(C4S)
Uanis(C1D) = Uanis(C2D) = Uanis(C3D) = Uanis(C4D) = Uanis(C5D) = Uanis(C6D)
Uanis(C6A) = Uanis(C0AA)
Uanis(C5A) = Uanis(C1AA)
Uanis(C4A) = Uanis(C2AA)
Uanis(C3A) = Uanis(C3AA)
Uanis(C2A) = Uanis(C4AA)
Uanis(C1A) = Uanis(C5AA)
Uanis(F1A) = Uanis(F0AA)
Uanis(C2S) = Uanis(C2T)
Uanis(C1S) = Uanis(C1T)
Uanis(N1S) = Uanis(N1T)
Uanis(C6C) = Uanis(C6AA) = Uanis(C5C) = Uanis(C7AA) = Uanis(C4C) = Uanis(C8AA)
= Uanis(C3C) = Uanis(C9AA) = Uanis(C2C) = Uanis(C0BA) = Uanis(C1C) = Uanis(C1BA)
Uanis(F1C) = Uanis(F1AA)
Uanis(C6B) = Uanis(C2BA) = Uanis(C1B) = Uanis(C3BA) = Uanis(C5B) = Uanis(C4BA)
= Uanis(C4B) = Uanis(C5BA) = Uanis(C3B) = Uanis(C6BA) = Uanis(C2B) = Uanis(C7BA)
Uanis(F1B) = Uanis(F2AA)
4. Others
 Sof(C0AA)=Sof(C1AA)=Sof(H1AA)=Sof(C2AA)=Sof(C3AA)=Sof(H3AA)=Sof(C4AA)=
 Sof(H4AA)=Sof(C5AA)=Sof(H5AA)=Sof(F0AA)=1-FVAR(1)
 Sof(F1A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=FVAR(1)
 Sof(C2T)=Sof(H2TA)=Sof(H2TB)=Sof(H2TC)=Sof(C1T)=Sof(N1T)=1-FVAR(2)
 Sof(N1S)=Sof(C1S)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=FVAR(2)
 Sof(C6AA)=Sof(C7AA)=Sof(H7AA)=Sof(C8AA)=Sof(C9AA)=Sof(H9AA)=Sof(C0BA)=
 Sof(H0BA)=Sof(C1BA)=Sof(H1BA)=Sof(F1AA)=1-FVAR(3)
 Sof(F1C)=Sof(C1C)=Sof(H1C)=Sof(C2C)=Sof(C3C)=Sof(H3C)=Sof(C4C)=Sof(H4C)=
 Sof(C5C)=Sof(H5C)=Sof(C6C)=FVAR(3)
 Sof(C2BA)=Sof(C3BA)=Sof(H3BA)=Sof(C4BA)=Sof(H4BA)=Sof(C5BA)=Sof(C6BA)=
 Sof(H6BA)=Sof(C7BA)=Sof(H7BA)=Sof(F2AA)=1-FVAR(4)
 Sof(F1B)=Sof(C1B)=Sof(H1B)=Sof(C2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=
 Sof(C5B)=Sof(H5B)=Sof(C6B)=FVAR(4)
5.a Ternary CH refined with riding coordinates:
 C14A(H14A), C14B(H14B), C14C(H14C), C14D(H14D)
5.b Secondary CH2 refined with riding coordinates:
 C13A(H13A,H13B), C13B(H13C,H13D), C13C(H13E,H13F), C13D(H13G,H13H), C15A(H15A,
 H15B), C15B(H15C,H15D), C15C(H15E,H15F), C15D(H15G,H15H), C16A(H16A,H16B),
 C16B(H16C,H16D), C16C(H16E,H16F), C16D(H16G,H16H), C17A(H17A,H17B), C17B(H17C,
 H17D), C17C(H17E,H17F), C17D(H17G,H17H), C18A(H18A,H18B), C18B(H18C,H18D),
 C18C(H18E,H18F), C18D(H18G,H18H)
5.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C1C(H1C), C1D(H1D), C3A(H3A), C3B(H3B), C3C(H3C),
 C3D(H3D), C4A(H4A), C4B(H4B), C4C(H4C), C4D(H4D), C5A(H5A), C5B(H5B), C5C(H5C),
  C5D(H5D), C10A(H10A), C10B(H10B), C10C(H10C), C10D(H10D), C1AA(H1AA),
 C3AA(H3AA), C4AA(H4AA), C5AA(H5AA), C7AA(H7AA), C9AA(H9AA), C0BA(H0BA),
 C1BA(H1BA), C3BA(H3BA), C4BA(H4BA), C6BA(H6BA), C7BA(H7BA)
5.d Idealised Me refined as rotating group:
 C19A(H19A,H19B,H19C), C19B(H19D,H19E,H19F), C19C(H19G,H19H,H19I), C19D(H19J,
 H19K,H19L), C2S(H2SA,H2SB,H2SC), C4S(H4SA,H4SB,H4SC), C6S(H6SA,H6SB,H6SC),
 C2T(H2TA,H2TB,H2TC)
;
_shelx_res_checksum              27939
_shelx_hkl_checksum              88280
_olex2_submission_special_instructions 'No special instructions were received'