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_1566204
_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
'C H3 O3 S, C75 H70 F8 O8, C2 H3 N, C16 H36 N'
_chemical_formula_sum            'C94 H112 F8 N2 O11 S'
_chemical_formula_weight         1629.91
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-18
_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            8
_cell_length_a                   23.0191(11)
_cell_length_b                   22.9578(11)
_cell_length_c                   32.8882(19)
_cell_measurement_reflns_used    8169
_cell_measurement_temperature    150
_cell_measurement_theta_max      47.35
_cell_measurement_theta_min      2.34
_cell_volume                     17380.4(15)
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_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_unetI/netI     0.1439
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            23869
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        61.162
_diffrn_reflns_theta_max         61.162
_diffrn_reflns_theta_min         2.343
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.974
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.4997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1292 before and 0.0965 after correction. The Ratio of minimum to maximum transmission is 0.6640. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       block
_exptl_crystal_F_000             6928
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.877
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details
;
 Flack x determined using 4092 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     910
_refine_ls_number_reflns         23869
_refine_ls_number_restraints     507
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.1845
_refine_ls_R_factor_gt           0.1334
_refine_ls_shift/su_max          0.557
_refine_ls_shift/su_mean         0.011
_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          0.3413
_refine_ls_wR_factor_ref         0.3788
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.823
_reflns_Friedel_fraction_max     0.823
_reflns_number_gt                14408
_reflns_number_total             23869
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc07041j2.cif
_cod_data_source_block           sm8f_ninth2
_cod_database_code               1566204
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.935
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.655(3)
 0.345(3)
2. 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
3. Restrained distances
 C16H-C17H = C17H-C18H
 1.5 with sigma of 0.01
 C104-C103 = C103-C102
 1.5 with sigma of 0.01
 C14F-C15F = C15F-C16F = C16F-C17F = C17F-C18F
 1.5 with sigma of 0.01
 C14E-C15E = C15E-C16E = C16E-C17E = C17E-C18E = C18E-C19E
 1.5 with sigma of 0.01
 C17G-C18G = C18G-C19G
 1.5 with sigma of 0.01
 C17B-C18B = C18B-C19B
 1.5 with sigma of 0.01
 C15D-C16D = C16D-C17D = C17D-C18D = C18D-C19D
 1.5 with sigma of 0.01
 C15C-C16C = C16C-C17C = C17C-C18C
 1.5 with sigma of 0.01
 C15C-C17C = C16C-C18C
 2.5 with sigma of 0.01
 C15A-C16A = C16A-C17A = C17A-C18A = C18A-C19A
 1.5 with sigma of 0.01
 C18F-C19F
 1.5 with sigma of 0.01
 C15A-C17A = C16A-C18A = C17A-C19A
 2.5 with sigma of 0.01
 N2S-C3S
 1.16 with sigma of 0.01
 N2S-C4S
 2.61 with sigma of 0.01
 C3S-C4S
 1.45 with sigma of 0.01
 N1S-C1S
 1.16 with sigma of 0.01
 N1S-C2S
 2.61 with sigma of 0.01
 C1S-C2S
 1.45 with sigma of 0.01
 O6-O5 = O5-O4 = O4-O6
 2.37 with sigma of 0.01
 S2-O6 = S2-O5 = S2-O4
 1.43 with sigma of 0.01
 O3-O2 = O2-O1 = O1-O3
 2.37 with sigma of 0.01
 S1-O3 = S1-O2 = S1-O1
 1.43 with sigma of 0.01
 C7F-C6F
 1.5 with sigma of 0.01
 C7E-C6E
 1.5 with sigma of 0.01
 C7C-C6C
 1.5 with sigma of 0.01
 C212-C211
 1.5 with sigma of 0.01
 C211-C210
 1.5 with sigma of 0.01
 C210-C209
 1.5 with sigma of 0.01
 C209-N200
 1.5 with sigma of 0.01
 C112-C111
 1.5 with sigma of 0.01
 C111-C110
 1.5 with sigma of 0.01
 C110-C109
 1.5 with sigma of 0.01
 C109-N100
 1.5 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(S2) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(C1) \\sim
Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C15A) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C17A) \\sim Ueq,
Uanis(C18A) \\sim Ueq, Uanis(C19A) \\sim Ueq: with sigma of 0.03 and sigma for
terminal atoms of 0.06
Uanis(C15C) \\sim Ueq, Uanis(C16C) \\sim Ueq, Uanis(C17C) \\sim Ueq,
Uanis(C18C) \\sim Ueq: with sigma of 0.03 and sigma for terminal atoms of 0.06
Uanis(C15B) \\sim Ueq, Uanis(C16B) \\sim Ueq, Uanis(C17B) \\sim Ueq,
Uanis(C18B) \\sim Ueq, Uanis(C19B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C6B) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C2B) \\sim Ueq, Uanis(C3B)
\\sim Ueq, Uanis(C4B) \\sim Ueq, Uanis(C5B) \\sim Ueq: with sigma of 0.02 and
sigma for terminal atoms of 0.04
Uanis(C15F) \\sim Ueq, Uanis(C16F) \\sim Ueq, Uanis(C17F) \\sim Ueq,
Uanis(C18F) \\sim Ueq, Uanis(C19F) \\sim Ueq: with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(O6) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of
0.02 and sigma for terminal atoms of 0.04
Uanis(C1S) \\sim Ueq, Uanis(N1S) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N2S) \\sim Ueq, Uanis(C3S) \\sim Ueq, Uanis(C4S) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C15H) \\sim Ueq, Uanis(C16H) \\sim Ueq, Uanis(C17H) \\sim Ueq,
Uanis(C18H) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C15G) \\sim Ueq, Uanis(C16G) \\sim Ueq, Uanis(C17G) \\sim Ueq,
Uanis(C18G) \\sim Ueq, Uanis(C19G) \\sim Ueq, Uanis(C15E) \\sim Ueq,
Uanis(C16E) \\sim Ueq, Uanis(C17E) \\sim Ueq, Uanis(C18E) \\sim Ueq,
Uanis(C19E) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C6F) \\sim Ueq, Uanis(C5F) \\sim Ueq, Uanis(C4F) \\sim Ueq, Uanis(C3F)
\\sim Ueq, Uanis(C2F) \\sim Ueq, Uanis(C1F) \\sim Ueq: with sigma of 0.02 and
sigma for terminal atoms of 0.04
Uanis(C14H) \\sim Ueq, Uanis(C14E) \\sim Ueq, Uanis(C14G) \\sim Ueq,
Uanis(C14F) \\sim Ueq: with sigma of 0.015 and sigma for terminal atoms of 0.03
Uanis(F1F) \\sim Ueq, Uanis(F2F) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(O2) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of
0.015 and sigma for terminal atoms of 0.03
Uanis(F2C) \\sim Ueq, Uanis(F1C) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C11D) \\sim Ueq, Uanis(C12D) \\sim Ueq, Uanis(C7D) \\sim Ueq, Uanis(C8D)
\\sim Ueq, Uanis(C9D) \\sim Ueq, Uanis(C10D) \\sim Ueq: with sigma of 0.015 and
sigma for terminal atoms of 0.03
Uanis(C15G) = Uanis(C16G) = Uanis(C17G) = Uanis(C18G) = Uanis(C19G)
Uanis(C19F) = Uanis(C18F) = Uanis(C17F) = Uanis(C16F) = Uanis(C15F)
Uanis(C15E) = Uanis(C16E) = Uanis(C17E) = Uanis(C18E) = Uanis(C19E)
Uanis(C15H) = Uanis(C16H) = Uanis(C17H) = Uanis(C18H)
Uanis(C15A) = Uanis(C16A) = Uanis(C17A) = Uanis(C18A) = Uanis(C19A)
Uanis(C15D) = Uanis(C16D) = Uanis(C17D) = Uanis(C18D) = Uanis(C19D)
Uanis(C15C) = Uanis(C16C) = Uanis(C17C) = Uanis(C18C)
Uanis(C15B) = Uanis(C16B) = Uanis(C17B) = Uanis(C18B) = Uanis(C19B)
Uanis(C4S) = Uanis(C3S) = Uanis(N2S)
Uanis(N100) = Uanis(C105) = Uanis(C109) = Uanis(C113) = Uanis(C101) =
Uanis(C107) = Uanis(C115) = Uanis(C102) = Uanis(C114) = Uanis(C111) =
Uanis(C110) = Uanis(C104) = Uanis(C106) = Uanis(C116) = Uanis(C103) =
Uanis(C108) = Uanis(C112)
Uanis(C201) = Uanis(C215) = Uanis(C209) = Uanis(C213) = Uanis(C214) =
Uanis(C202) = Uanis(N200) = Uanis(C210) = Uanis(C203) = Uanis(C207) =
Uanis(C205) = Uanis(C211) = Uanis(C212) = Uanis(C206) = Uanis(C216) =
Uanis(C204) = Uanis(C208)
Uanis(O4) = Uanis(O5) = Uanis(O6)
Uanis(C6D) = Uanis(C1D) = Uanis(C2D) = Uanis(C3D) = Uanis(C4D) = Uanis(C5D)
Uanis(C6B) = Uanis(C1B) = Uanis(C5B) = Uanis(C4B) = Uanis(C3B) = Uanis(C2B)
Uanis(F2B) = Uanis(F1B)
Uanis(F1D) = Uanis(F2D)
Uanis(C6C) = Uanis(C1C) = Uanis(C2C) = Uanis(C3C) = Uanis(C4C) = Uanis(C5C)
Uanis(F2C) = Uanis(F1C)
Uanis(C6A) = Uanis(C1A) = Uanis(C2A) = Uanis(C3A) = Uanis(C4A) = Uanis(C5A)
Uanis(F1A) = Uanis(F2A)
Uanis(O2) = Uanis(O3) = Uanis(O1)
Uanis(C12D) = Uanis(C7D) = Uanis(C8D) = Uanis(C9D) = Uanis(C10D) = Uanis(C11D)
Uanis(C10A) = Uanis(C9A) = Uanis(C8A) = Uanis(C7A) = Uanis(C12A) = Uanis(C11A)
Uanis(C13D) = Uanis(C13A) = Uanis(C13C) = Uanis(C13B)
Uanis(O2A) = Uanis(O1A) = Uanis(O2D) = Uanis(O1D) = Uanis(O2C) = Uanis(O1C) =
Uanis(O2B) = Uanis(O1B)
Uanis(C10C) = Uanis(C11C) = Uanis(C12C) = Uanis(C7C) = Uanis(C8C) = Uanis(C9C)
Uanis(C14C) = Uanis(C14D) = Uanis(C14A) = Uanis(C14B)
Uanis(C10B) = Uanis(C9B) = Uanis(C8B) = Uanis(C7B) = Uanis(C12B) = Uanis(C11B)
Uanis(N1S) = Uanis(C1S) = Uanis(C2S)
Uanis(C14F) = Uanis(C14E) = Uanis(C14H) = Uanis(C14G)
Uanis(C6F) = Uanis(C5F) = Uanis(C4F) = Uanis(C3F) = Uanis(C2F) = Uanis(C1F)
Uanis(C7F) = Uanis(C8F) = Uanis(C9F) = Uanis(C10F) = Uanis(C11F) = Uanis(C12F)
Uanis(F1F) = Uanis(F2F)
Uanis(C10E) = Uanis(C11E) = Uanis(C12E) = Uanis(C7E) = Uanis(C8E) = Uanis(C9E)
Uanis(C6E) = Uanis(C1E) = Uanis(C2E) = Uanis(C3E) = Uanis(C4E) = Uanis(C5E)
Uanis(F1E) = Uanis(F2E)
Uanis(O1H) = Uanis(O2H) = Uanis(O1E) = Uanis(O2G) = Uanis(O1G) = Uanis(O2E) =
Uanis(O2F) = Uanis(O1F)
Uanis(C13G) = Uanis(C13E) = Uanis(C13F) = Uanis(C13H)
Uanis(C6G) = Uanis(C1G) = Uanis(C2G) = Uanis(C3G) = Uanis(C4G) = Uanis(C5G)
Uanis(F1G) = Uanis(F2G)
Uanis(C10G) = Uanis(C11G) = Uanis(C12G) = Uanis(C7G) = Uanis(C8G) = Uanis(C9G)
Uanis(C7H) = Uanis(C8H) = Uanis(C9H) = Uanis(C10H) = Uanis(C11H) = Uanis(C12H)
Uanis(C6H) = Uanis(C5H) = Uanis(C4H) = Uanis(C3H) = Uanis(C2H) = Uanis(C1H)
Uanis(F1H) = Uanis(F2H)
5.a Ternary CH refined with riding coordinates:
 C14A(H14A), C14B(H14B), C14C(H14C), C14D(H14D), C14E(H14E), C14F(H14F),
 C14G(H14G), C14H(H14H)
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),
 C18D(H18H,H18I), C13E(H13I,H13J), C13F(H13K,H13L), C13G(H13M,H13N), C13H(H13O,
 H13P), C15E(H15I,H15J), C15F(H15K,H15L), C15G(H15M,H15N), C15H(H15O,H15P),
 C16E(H16I,H16J), C16F(H16K,H16L), C16G(H16M,H16N), C16H(H16O,H16P), C17E(H17I,
 H17J), C17F(H17K,H17L), C17G(H17M,H17N), C17H(H17O,H17P), C18E(H18J,H18K),
 C18F(H18L,H18M), C18G(H18N,H18O), C101(H10I,H10J), C102(H10K,H10L), C103(H10M,
 H10N), C105(H10R,H10S), C106(H10T,H10U), C107(H10V,H10W), C109(H10Z,HA),
 C110(H11A,H11B), C111(H11C,H11D), C113(H11H,H11I), C114(H11J,H11K), C115(H11L,
 H11M), C201(H20A,H20B), C202(H20C,H20D), C203(H20E,H20F), C205(H20J,H20K),
 C206(H20L,H20M), C207(H20N,H20O), C209(H20S,H20T), C210(H21A,H21B), C211(H21C,
 H21D), C213(H21H,H21I), C214(H21J,H21K), C215(H21L,H21M)
5.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C3A(H3A), C5A(H5A), C1B(H1B), C3B(H3B), C5B(H5B), C5C(H5C),
 C3C(H3C), C1C(H1C), C5D(H5D), C3D(H3D), C1D(H1D), C10A(H10A), C10B(H10B),
 C10C(H10C), C10D(H10D), C1E(H1E), C3E(H3E), C5E(H5E), C5F(H5F), C3F(H3F),
 C1F(H1F), C5G(H5G), C3G(H3G), C1G(H1G), C1H(H1H), C3H(H3H), C5H(H5H),
 C10E(H10E), C10F(H10F), C10G(H10G), C10H(H10H)
5.d Fitted hexagon refined as free rotating group:
 C6A(C1A,C2A,C3A,C4A,C5A), C6B(C1B,C2B,C3B,C4B,C5B), C6C(C5C,C4C,C3C,C2C,C1C),
 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)
5.e Idealised Me refined as rotating group:
 C1(H1I,H1J,H1K), C2(H2A,H2B,H2C), C18C(H18E,H18F,H18G), C19A(H19A,H19B,H19C),
 C19B(H19D,H19E,H19F), C19D(H19G,H19H,H19I), C18H(H18P,H18Q,H18R), C19E(H19J,
 H19K,H19L), C19F(H19M,H19N,H19O), C19G(H19P,H19Q,H19R), C2S(H2SA,H2SB,H2SC),
 C4S(H4SA,H4SB,H4SC), C104(H10O,H10P,H10Q), C108(H10X,H10Y,H), C112(H11E,H11F,
 H11G), C116(H11N,H11O,H11P), C204(H20G,H20H,H20I), C208(H20P,H20Q,H20R),
 C212(H21E,H21F,H21G), C216(H21N,H21O,H21P)
;
_shelx_res_checksum              97027
_shelx_hkl_checksum              71495
_olex2_submission_special_instructions 'No special instructions were received'