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_1566199
_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, 4(C2 H3 N)'
_chemical_formula_sum            'C84 H80 F12 N4 O8'
_chemical_formula_weight         1501.52
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-29
_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                78.324(3)
_cell_angle_beta                 77.909(3)
_cell_angle_gamma                79.550(3)
_cell_formula_units_Z            2
_cell_length_a                   12.0029(7)
_cell_length_b                   12.9090(7)
_cell_length_c                   25.4812(14)
_cell_measurement_reflns_used    9698
_cell_measurement_temperature    210
_cell_measurement_theta_max      61.81
_cell_measurement_theta_min      3.53
_cell_volume                     3740.7(4)
_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      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 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.0621
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_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       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            62073
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        62.471
_diffrn_reflns_theta_max         62.471
_diffrn_reflns_theta_min         3.533
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  0.7371
_exptl_absorpt_correction_T_min  0.6068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1009 before and 0.0848 after correction. The Ratio of minimum to maximum transmission is 0.8232. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.556
_refine_diff_density_min         -1.256
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       0.0029(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   2.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     735
_refine_ls_number_reflns         11581
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      2.058
_refine_ls_R_factor_all          0.1853
_refine_ls_R_factor_gt           0.1597
_refine_ls_shift/su_max          2.452
_refine_ls_shift/su_mean         0.008
_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          0.4636
_refine_ls_wR_factor_ref         0.4950
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8224
_reflns_number_total             11581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc07041j2.cif
_cod_data_source_block           sm450a_first_a
_cod_database_code               1566199
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.940
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C16A, C16E}
{C2S, C2T}
{F1D, F1H}
{C6D, C6H}
{C5D, C5H}
{C4D, C4H}
{C3D, C3H}
{C2D, C2H}
{C1D, C1H}
{F1C, F1G}
{C5C, C5G}
{C4C, C4G}
{C3C, C3G}
{C2C, C2G}
{C1C, C1G}
{C6C, C6G}
{C1B, C1F}
{C2B, C2F}
{C3B, C3F}
{C4B, C4F}
{C5B, C5F}
{C6B, C6F}
{F1B, F1F}
{C1A, C1E}
{C2A, C2E}
{C3A, C3E}
{C4A, C4E}
{C5A, C5E}
{C6A, C6E}
{F1A, F1E}
3. Restrained distances
 C15C-C16C = C16C-C17C = C17C-C18C = C18C-C19C = C5S_$1-C6S_$1 = C7S_$2-C8S_$2
 1.5 with sigma of 0.01
 C1D-C6D = C1H-C6H = C4D-C5D = C4H-C5H
 1.4 with sigma of 0.01
 N3S-C5S = N4S_$3-C7S_$3
 1.2 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(N3S) \\sim Ueq, Uanis(C5S) \\sim Ueq, Uanis(C6S) \\sim Ueq, Uanis(N4S)
\\sim Ueq, Uanis(C7S) \\sim Ueq, Uanis(C8S) \\sim Ueq: with sigma of 0.02 and
sigma for terminal atoms of 0.04
Uanis(F1A) = Uanis(F1E) = Uanis(F2A) = Uanis(F2E) = Uanis(F3A) = Uanis(F3E)
Uanis(C6A) = Uanis(C6E) = Uanis(C5A) = Uanis(C5E) = Uanis(C4A) = Uanis(C4E) =
Uanis(C3A) = Uanis(C3E) = Uanis(C2A) = Uanis(C2E) = Uanis(C1A) = Uanis(C1E)
Uanis(F3B) = Uanis(F3F) = Uanis(F2B) = Uanis(F2F) = Uanis(F1B) = Uanis(F1F)
Uanis(C6B) = Uanis(C6F) = Uanis(C5B) = Uanis(C5F) = Uanis(C4B) = Uanis(C4F) =
Uanis(C3B) = Uanis(C3F) = Uanis(C2B) = Uanis(C2F) = Uanis(C1B) = Uanis(C1F)
Uanis(F3C) = Uanis(F3G) = Uanis(F2C) = Uanis(F2G) = Uanis(F1C) = Uanis(F1G)
Uanis(C6C) = Uanis(C6G) = Uanis(C5C) = Uanis(C5G) = Uanis(C4C) = Uanis(C4G) =
Uanis(C3C) = Uanis(C3G) = Uanis(C2C) = Uanis(C2G) = Uanis(C1C) = Uanis(C1G)
Uanis(F3D) = Uanis(F3H) = Uanis(F2D) = Uanis(F2H) = Uanis(F1D) = Uanis(F1H)
Uanis(C6D) = Uanis(C6H) = Uanis(C5D) = Uanis(C5H) = Uanis(C4D) = Uanis(C4H) =
Uanis(C3D) = Uanis(C3H) = Uanis(C2D) = Uanis(C2H) = Uanis(C1D) = Uanis(C1H)
Uanis(C2S) = Uanis(C2T) = Uanis(C1S) = Uanis(C1T) = Uanis(N1S) = Uanis(N1T)
Uanis(N2S) = Uanis(C3S) = Uanis(C4S)
Uanis(N3S) = Uanis(C5S) = Uanis(C6S) = Uanis(N4S) = Uanis(C7S) = Uanis(C8S)
Uanis(C15C) = Uanis(C16C) = Uanis(C17C) = Uanis(C18C) = Uanis(C19C)
Uanis(C15A) = Uanis(C16A) = Uanis(C16E) = Uanis(C17A) = Uanis(C17E) =
Uanis(C18A) = Uanis(C18E) = Uanis(C19A) = Uanis(C19E)
Uanis(C15B) = Uanis(C16B) = Uanis(C17B) = Uanis(C18B) = Uanis(C19B)
5. Others
 Sof(F3E)=Sof(F2E)=Sof(F1E)=Sof(C6E)=Sof(C5E)=Sof(H5E)=Sof(C4E)=Sof(H4E)=
 Sof(C3E)=Sof(C2E)=Sof(C1E)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=
 Sof(C4A)=Sof(C5A)=Sof(C6A)=FVAR(1)
 Sof(F3F)=Sof(F2F)=Sof(F1F)=Sof(C5F)=Sof(H5F)=Sof(C4F)=Sof(H4F)=Sof(C3F)=
 Sof(C2F)=Sof(C1F)=Sof(C6F)=1-FVAR(2)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(C1B)=Sof(H1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=
 Sof(C4B)=Sof(C5B)=Sof(C6B)=FVAR(2)
 Sof(F3G)=Sof(F2G)=Sof(F1G)=Sof(C5G)=Sof(H5G)=Sof(C4G)=Sof(H4G)=Sof(C3G)=
 Sof(C2G)=Sof(C1G)=Sof(C6G)=1-FVAR(3)
 Sof(F1C)=Sof(F2C)=Sof(F3C)=Sof(C1C)=Sof(H1C)=Sof(C2C)=Sof(H2C)=Sof(C3C)=
 Sof(C4C)=Sof(C5C)=Sof(C6C)=FVAR(3)
 Sof(F3H)=Sof(F2H)=Sof(F1H)=Sof(C5H)=Sof(H5H)=Sof(C4H)=Sof(H4H)=Sof(C3H)=
 Sof(C2H)=Sof(C1H)=Sof(C6H)=1-FVAR(4)
 Sof(F1D)=Sof(F2D)=Sof(F3D)=Sof(C1D)=Sof(H1D)=Sof(C2D)=Sof(H2D)=Sof(C3D)=
 Sof(C4D)=Sof(C5D)=Sof(C6D)=FVAR(4)
 Sof(C2T)=Sof(H2TA)=Sof(H2TB)=Sof(H2TC)=Sof(C1T)=Sof(N1T)=1-FVAR(5)
 Sof(N1S)=Sof(C1S)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=FVAR(5)
 Sof(H15C)=Sof(H15D)=Sof(C16E)=Sof(H16I)=Sof(H16J)=Sof(C17E)=Sof(H17I)=
 Sof(H17J)=Sof(C18E)=Sof(H18I)=Sof(H18J)=Sof(C19E)=Sof(H19M)=Sof(H19N)=
 Sof(H19O)=1-FVAR(6)
 Sof(H15A)=Sof(H15B)=Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(C17A)=Sof(H17A)=
 Sof(H17B)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(C19A)=Sof(H19A)=Sof(H19B)=
 Sof(H19C)=FVAR(6)
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), C15A(H15C,H15D), C15B(H15E,H15F), C15C(H15G,H15H), C15D(H15I,H15J),
 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), C16E(H16I,H16J), C17E(H17I,
 H17J), C18E(H18I,H18J)
6.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C1C(H1C), C1D(H1D), C2A(H2A), C2B(H2B), C2C(H2C),
 C2D(H2D), C10A(H10A), C10B(H10B), C10C(H10C), C10D(H10D), C5E(H5E), C4E(H4E),
 C5F(H5F), C4F(H4F), C5G(H5G), C4G(H4G), C5H(H5H), C4H(H4H)
6.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), C2T(H2TA,H2TB,H2TC),
 C19E(H19M,H19N,H19O), C6S(H6SA,H6SB,H6SC), C8S(H8SA,H8SB,H8SC)
;
_shelx_res_checksum              16699
_shelx_hkl_checksum              8697
_olex2_submission_special_instructions 'No special instructions were received'