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_1566196
_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         'C84 H72 F24 O8, 3(C2 H3 N)'
_chemical_formula_sum            'C90 H80.54 F24 N3 O8'
_chemical_formula_weight         1788.11
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
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2021-08-18 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.23
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.8730(5)
_cell_length_b                   15.4168(3)
_cell_length_c                   27.7277(6)
_cell_measurement_reflns_used    7611
_cell_measurement_temperature    210
_cell_measurement_theta_max      53.59
_cell_measurement_theta_min      3.29
_cell_volume                     8592.1(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 2014.9-0'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      210
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.797
_diffrn_measured_fraction_theta_max 0.797
_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  0.0836
_diffrn_reflns_av_unetI/netI     0.1397
_diffrn_reflns_Laue_measured_fraction_full 0.797
_diffrn_reflns_Laue_measured_fraction_max 0.797
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31927
_diffrn_reflns_point_group_measured_fraction_full 0.797
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_theta_full        53.709
_diffrn_reflns_theta_max         53.709
_diffrn_reflns_theta_min         3.350
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.073
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.6154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1361 before and 0.0763 after correction. The Ratio of minimum to maximum transmission is 0.8199. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             3686
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.491
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     724
_refine_ls_number_reflns         8191
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.490
_refine_ls_R_factor_all          0.2618
_refine_ls_R_factor_gt           0.1883
_refine_ls_shift/su_max          0.203
_refine_ls_shift/su_mean         0.006
_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          0.4423
_refine_ls_wR_factor_ref         0.4886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4116
_reflns_number_total             8191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc07041j2.cif
_cod_data_source_block           369_0ma_a
_cod_database_code               1566196
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
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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
{N1S, N1T}
{C4T, C4U}
{C4V, C4S}
3. Restrained distances
 C1S-C2S = C1T-C2T = C3T-C4T = C3U-C4U = C3S-C4S = C3V-C4V
 1.45 with sigma of 0.02
 N1S-C1S = N1T-C1T = N2S-C3S = N2U-C3U = N2T-C3T = N2V-C3V
 1.2 with sigma of 0.02
 C17A-C18A = C18A-C19A
 1.5 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C13A) \\sim Ueq, Uanis(C13B) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(F4B) = Uanis(F5B) = Uanis(F6B) = Uanis(F5A) = Uanis(F4A) = Uanis(F6A) =
Uanis(F4D) = Uanis(F6D) = Uanis(F5D) = Uanis(F5C) = Uanis(F4C) = Uanis(F6C) =
Uanis(F3C) = Uanis(F2C) = Uanis(F1C) = Uanis(F3B) = Uanis(F1B) = Uanis(F2B) =
Uanis(F1A) = Uanis(F2A) = Uanis(F3A) = Uanis(F3D) = Uanis(F1D) = Uanis(F2D)
Uanis(C21B) = Uanis(C20C) = Uanis(C21C) = Uanis(C20D) = Uanis(C21D) =
Uanis(C20A) = Uanis(C20B) = Uanis(C21A)
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(C14C) = Uanis(C15C) = Uanis(C16C) = Uanis(C17C) = Uanis(C18C) =
Uanis(C19C)
Uanis(C14A) = Uanis(C15A) = Uanis(C16A) = Uanis(C17A) = Uanis(C18A) =
Uanis(C19A)
Uanis(C14B) = Uanis(C15B) = Uanis(C16B) = Uanis(C17B) = Uanis(C18B) =
Uanis(C19B)
Uanis(N1S) = Uanis(N1T) = Uanis(C1S) = Uanis(C1T) = Uanis(C2S) = Uanis(C2T)
Uanis(N2S) = Uanis(C3S) = Uanis(C4S) = Uanis(N2U) = Uanis(C3U) = Uanis(C4U) =
Uanis(N2T) = Uanis(C3T) = Uanis(C4T) = Uanis(N2V) = Uanis(C3V) = Uanis(C4V)
5. Others
 Sof(N1T)=Sof(C1T)=Sof(C2T)=Sof(H2TA)=Sof(H2TB)=Sof(H2TC)=1-FVAR(1)
 Sof(N1S)=Sof(C1S)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=FVAR(1)
 Sof(N2T)=Sof(C3T)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=Sof(H4SC)=Sof(C4V)=Sof(H4VA)=
 Sof(H4VB)=Sof(H4VC)=Sof(C3V)=Sof(N2V)=1-FVAR(2)
 Sof(C4T)=Sof(H4TA)=Sof(H4TB)=Sof(H4TC)=Sof(N2S)=Sof(C3S)=Sof(N2U)=Sof(C3U)=
 Sof(C4U)=Sof(H4UA)=Sof(H4UB)=Sof(H4UC)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C14A(H14A), C14B(H14B), C14C(H14C), C14D(H14D)
6.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)
6.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C1C(H1C), C1D(H1D), C3A(H3A), C3B(H3B), C3C(H3C),
 C3D(H3D), C5A(H5A), C5B(H5B), C5C(H5C), C5D(H5D), C10A(H10A), C10B(H10B),
 C10C(H10C), C10D(H10D)
6.d Idealised Me refined as rotating group:
 C19A(H19A,H19B,H19C), C19B(H19D,H19E,H19F), C19C(H19G,H19H,H19I), C19D(H19J,
 H19K,H19L), C4T(H4TA,H4TB,H4TC), C2S(H2SA,H2SB,H2SC), C2T(H2TA,H2TB,H2TC),
 C4U(H4UA,H4UB,H4UC), C4S(H4SA,H4SB,H4SC), C4V(H4VA,H4VB,H4VC)
;
_shelx_res_checksum              19597
_shelx_hkl_checksum              60637
_olex2_submission_special_instructions 'No special instructions were received'