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_1566198
_publ_section_title
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 Nonspherical anion sequestration by C--H hydrogen bonding
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_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC07041J
_journal_year                    2022
_chemical_formula_moiety         'C68 H48 F16 O8'
_chemical_formula_sum            'C68 H48 F16 O8'
_chemical_formula_weight         1297.06
_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_Hall           '-F 2uv 2vw'
_space_group_name_H-M_alt        'F d d d :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-06
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   28.0557(13)
_cell_length_b                   31.8586(13)
_cell_length_c                   36.4490(12)
_cell_measurement_reflns_used    5091
_cell_measurement_temperature    220
_cell_measurement_theta_max      57.92
_cell_measurement_theta_min      2.42
_cell_volume                     32579(2)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      220
_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  0.0429
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            25587
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        55.088
_diffrn_reflns_theta_max         55.088
_diffrn_reflns_theta_min         4.614
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0391 before and 0.0265 after correction. The Ratio of minimum to maximum transmission is 0.8495. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.058
_exptl_crystal_description       block
_exptl_crystal_F_000             10624
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.369
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         5085
_refine_ls_number_restraints     290
_refine_ls_restrained_S_all      2.395
_refine_ls_R_factor_all          0.3117
_refine_ls_R_factor_gt           0.2524
_refine_ls_shift/su_max          1.751
_refine_ls_shift/su_mean         0.050
_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          0.5948
_refine_ls_wR_factor_ref         0.6582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2316
_reflns_number_total             5085
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc07041j2.cif
_cod_data_source_block           ve51_second_a
_cod_original_sg_symbol_H-M      'F d d d'
_cod_database_code               1566198
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.945
_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
{C15A, C15H}
{C15B, C15G}
3. Restrained distances
 C16A-C17A = C15A-C16A = C15A-C14A = C15B-C16B = C16B-C17B = C14A-C15H = C15H-
 C16H = C16H-C17H = C14B-C15G = C15G-C16G = C16G-C17G
 1.5 with sigma of 0.01
 C2B-F4B = C3B-F3B = C5B-F1B
 1.36 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C1A) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C4A)
\\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C7A) \\sim Ueq,
Uanis(C8A) \\sim Ueq, Uanis(C9A) \\sim Ueq, Uanis(C10A) \\sim Ueq, Uanis(C11A)
\\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C14A) \\sim Ueq,
Uanis(C15A) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C17A) \\sim Ueq, Uanis(O1A)
\\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2A) \\sim Ueq,
Uanis(F3A) \\sim Ueq, Uanis(F4A) \\sim Ueq: with sigma of 0.03 and sigma for
terminal atoms of 0.06
Uanis(C1B) \\sim Ueq, Uanis(C2B) \\sim Ueq, Uanis(C3B) \\sim Ueq, Uanis(C4B)
\\sim Ueq, Uanis(C5B) \\sim Ueq, Uanis(C6B) \\sim Ueq, Uanis(C7B) \\sim Ueq,
Uanis(C8B) \\sim Ueq, Uanis(C9B) \\sim Ueq, Uanis(C10B) \\sim Ueq, Uanis(C11B)
\\sim Ueq, Uanis(C12B) \\sim Ueq, Uanis(C13B) \\sim Ueq, Uanis(C14B) \\sim Ueq,
Uanis(C15B) \\sim Ueq, Uanis(C16B) \\sim Ueq, Uanis(C17B) \\sim Ueq, Uanis(O1B)
\\sim Ueq, Uanis(O2B) \\sim Ueq, Uanis(F1B) \\sim Ueq, Uanis(F2B) \\sim Ueq,
Uanis(F3B) \\sim Ueq, Uanis(F4B) \\sim Ueq: with sigma of 0.03 and sigma for
terminal atoms of 0.06
Uanis(C15A) = Uanis(C15H) = Uanis(C16A) = Uanis(C16H) = Uanis(C17A) =
Uanis(C17H)
Uanis(C15B) = Uanis(C15G) = Uanis(C16B) = Uanis(C16G) = Uanis(C17B) =
Uanis(C17G)
Uanis(F4A) = Uanis(F3A) = Uanis(F2A) = Uanis(F1A) = Uanis(F1B) = Uanis(F2B) =
Uanis(F3B) = Uanis(F4B)
Uanis(C6A) = Uanis(C5A) = Uanis(C4A) = Uanis(C3A) = Uanis(C2A) = Uanis(C1A)
Uanis(C7B) = Uanis(C8B) = Uanis(C9B) = Uanis(C10B) = Uanis(C11B) = Uanis(C12B)
Uanis(C5B) = Uanis(C4B) = Uanis(C3B) = Uanis(C2B) = Uanis(C1B) = Uanis(C6B)
Uanis(C7A) = Uanis(C8A) = Uanis(C9A) = Uanis(C11A) = Uanis(C10A) = Uanis(C12A)
Uanis(C14A) = Uanis(C13A) = Uanis(C13B) = Uanis(C14B)
Uanis(O2A) = Uanis(O1A) = Uanis(O2B) = Uanis(O1B)
5. Others
 Sof(H14B)=Sof(C15H)=Sof(H15E)=Sof(H15F)=Sof(C16H)=Sof(H16E)=Sof(H16F)=
 Sof(C17H)=Sof(H17G)=Sof(H17H)=Sof(H17I)=1-FVAR(1)
 Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(C16A)=Sof(H16C)=Sof(H16D)=
 Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=FVAR(1)
 Sof(H14D)=Sof(C15G)=Sof(H15G)=Sof(H15H)=Sof(C16G)=Sof(H16G)=Sof(H16H)=
 Sof(C17G)=Sof(H17J)=Sof(H17K)=Sof(H17L)=1-FVAR(2)
 Sof(H14C)=Sof(C15B)=Sof(H15C)=Sof(H15D)=Sof(C16B)=Sof(H16A)=Sof(H16B)=
 Sof(C17B)=Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C14A(H14A), C14A(H14B), C14B(H14C), C14B(H14D)
6.b Secondary CH2 refined with riding coordinates:
 C13A(H13A,H13B), C13B(H13C,H13D), C15A(H15A,H15B), C15B(H15C,H15D), C16B(H16A,
 H16B), C16A(H16C,H16D), C15H(H15E,H15F), C16H(H16E,H16F), C15G(H15G,H15H),
 C16G(H16G,H16H)
6.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C10A(H10A), C10B(H10B)
6.d Fitted hexagon refined as free rotating group:
 C6A(C5A,C4A,C3A,C2A,C1A), C6B(C1B,C2B,C3B,C4B,C5B)
6.e Idealised Me refined as rotating group:
 C17B(H17A,H17B,H17C), C17A(H17D,H17E,H17F), C17H(H17G,H17H,H17I), C17G(H17J,
 H17K,H17L)
;
_shelx_res_checksum              69763
_shelx_hkl_checksum              96702
_shelx_fab_checksum              59274
_olex2_submission_special_instructions 'No special instructions were received'