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_1566200
_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
'C H3 O3 S, C82.11 H77.75 F16 N0.38 O8, C2 H3 N, 0.62(C16 H36 N)'
_chemical_formula_sum            'C95 H106 F16 N2 O11 S'
_chemical_formula_weight         1787.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 94.056(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.7581(10)
_cell_length_b                   22.867(2)
_cell_length_c                   16.3241(14)
_cell_measurement_reflns_used    5713
_cell_measurement_temperature    110
_cell_measurement_theta_max      59.99
_cell_measurement_theta_min      2.71
_cell_volume                     4750.5(7)
_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      110
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.940
_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  0.0508
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30143
_diffrn_reflns_point_group_measured_fraction_full 0.832
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.854
_diffrn_reflns_theta_min         2.714
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.063
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0860 before and 0.0554 after correction. The Ratio of minimum to maximum transmission is 0.6878. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             1876
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.040
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.166
_refine_ls_abs_structure_details
;
 Flack x determined using 1695 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.50(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.482
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     630
_refine_ls_number_reflns         14968
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.485
_refine_ls_R_factor_all          0.2646
_refine_ls_R_factor_gt           0.1736
_refine_ls_shift/su_max          2.814
_refine_ls_shift/su_mean         0.092
_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          0.4253
_refine_ls_wR_factor_ref         0.4927
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_full    0.683
_reflns_Friedel_fraction_max     0.631
_reflns_number_gt                6284
_reflns_number_total             14968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc07041j2.cif
_cod_data_source_block           sm16ftbameso3b_second
_cod_database_code               1566200
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.929
_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
{C1, C1X}
3. Restrained distances
 C15A-C16A = C16A-C17A = C17A-C18A = C18A-C19A = C15C-C16C = C16C-C17C = C17C-
 C18C = C18C-C19C = C15B-C16B = C16B-C17B = 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
 N100-C101 = C101-C102 = C102-C103 = C103-C104 = N100-C105 = C105-C106 = C106-
 C107 = C107-C108 = N100-C113 = C113-C114 = C114-C115 = C115-C116 = N100-C109 =
 C109-C110 = C110-C111 = C111-C112
 1.5 with sigma of 0.01
 N200-C205 = C205-C206 = C206-C207 = C207-C208
 1.5 with sigma of 0.01
 N200-C209 = C209-C210 = C210-C211 = C211-C212
 1.5 with sigma of 0.01
 N200-C201 = C201-C202 = C202-C203 = C203-C204
 1.5 with sigma of 0.01
 N200-C213 = C213-C214 = C214-C215 = C215-C216
 1.5 with sigma of 0.01
 C14B-C16B = C202-C204 = C210-C212 = C214-C216 = C213-C201 = C116-C114 = C110-
 C112 = C211-C209 = C207-C205
 2.5 with sigma of 0.01
 C105-C107
 2.5 with sigma of 0.01
 C109-C111
 2.5 with sigma of 0.01
 C201-C203
 2.5 with sigma of 0.01
 C213-C215
 2.5 with sigma of 0.01
 C205-C213
 2.5 with sigma of 0.01
 C209-C213
 2.5 with sigma of 0.01
 C205-C201
 2.5 with sigma of 0.01
 C206-C208
 2.5 with sigma of 0.01
 O2X-O3X
 2.38 with sigma of 0.02
 O3X-O1X
 2.38 with sigma of 0.02
 O1X-O2X
 2.38 with sigma of 0.02
 C113-C115
 2.5 with sigma of 0.02
 C101-C113
 2.5 with sigma of 0.02
 C205-C209
 2.5 with sigma of 0.02
 C202-N200
 2.55 with sigma of 0.02
 N200-C210
 2.55 with sigma of 0.02
 N200-C206
 2.55 with sigma of 0.02
 C106-C108
 2.5 with sigma of 0.02
 C109-C105
 2.5 with sigma of 0.02
 C201-C209
 2.5 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(N100) = Uanis(N200) = Uanis(C113) = Uanis(C213) = Uanis(C114) =
Uanis(C214) = Uanis(C115) = Uanis(C215) = Uanis(C116) = Uanis(C216) =
Uanis(C109) = Uanis(C209) = Uanis(C110) = Uanis(C210) = Uanis(C111) =
Uanis(C211) = Uanis(C112) = Uanis(C212) = Uanis(C101) = Uanis(C201) =
Uanis(C102) = Uanis(C202) = Uanis(C103) = Uanis(C203) = Uanis(C104) =
Uanis(C204) = Uanis(C105) = Uanis(C205) = Uanis(C106) = Uanis(C206) =
Uanis(C107) = Uanis(C207) = Uanis(C108) = Uanis(C208)
Uanis(C1) = Uanis(C1X)
Uanis(S1) = Uanis(S1X)
Uanis(O1) = Uanis(O1X) = Uanis(O3) = Uanis(O3X) = Uanis(O2) = Uanis(O2X)
Uanis(N1S) = Uanis(C1S) = Uanis(C2S)
Uanis(C15A) = Uanis(C16A) = Uanis(C17A) = Uanis(C18A) = Uanis(C19A)
Uanis(C15D) = Uanis(C16D) = Uanis(C17D) = Uanis(C18D) = Uanis(C19D)
Uanis(C15B) = Uanis(C16B) = Uanis(C17B) = Uanis(C18B) = Uanis(C19B)
Uanis(C15C) = Uanis(C16C) = Uanis(C17C) = Uanis(C18C) = Uanis(C19C)
Uanis(C6A) = Uanis(C1A) = Uanis(C2A) = Uanis(C3A) = Uanis(C4A) = Uanis(C5A)
Uanis(C6D) = Uanis(C1D) = Uanis(C2D) = Uanis(C3D) = Uanis(C4D) = Uanis(C5D)
Uanis(C10D) = Uanis(C11D) = Uanis(C12D) = Uanis(C7D) = Uanis(C8D) = Uanis(C9D)
Uanis(C10A) = Uanis(C11A) = Uanis(C12A) = Uanis(C7A) = Uanis(C8A) = Uanis(C9A)
Uanis(C10C) = Uanis(C11C) = Uanis(C12C) = Uanis(C7C) = Uanis(C8C) = Uanis(C9C)
Uanis(C6C) = Uanis(C5C) = Uanis(C4C) = Uanis(C3C) = Uanis(C2C) = Uanis(C1C)
Uanis(C10B) = Uanis(C11B) = Uanis(C12B) = Uanis(C7B) = Uanis(C8B) = Uanis(C9B)
Uanis(C6B) = Uanis(C1B) = Uanis(C2B) = Uanis(C3B) = Uanis(C4B) = Uanis(C5B)
Uanis(F1C) = Uanis(F2C) = Uanis(F3C) = Uanis(F4C)
Uanis(F4D) = Uanis(F3D) = Uanis(F2D) = Uanis(F1D)
Uanis(F4A) = Uanis(F3A) = Uanis(F2A) = Uanis(F1A)
Uanis(F4B) = Uanis(F3B) = Uanis(F2B) = Uanis(F1B)
5. Others
 Sof(N200)=Sof(C201)=Sof(H20A)=Sof(H20B)=Sof(C202)=Sof(H20C)=Sof(H20D)=
 Sof(C203)=Sof(H20E)=Sof(H20F)=Sof(C204)=Sof(H20G)=Sof(H20H)=Sof(H20I)=
 Sof(C205)=Sof(H20J)=Sof(H20K)=Sof(C206)=Sof(H20L)=Sof(H20M)=Sof(C207)=
 Sof(H20N)=Sof(H20O)=Sof(C208)=Sof(H20P)=Sof(H20Q)=Sof(H20R)=Sof(C209)=
 Sof(H20S)=Sof(H20T)=Sof(C210)=Sof(H21A)=Sof(H21B)=Sof(C211)=Sof(H21C)=
 Sof(H21D)=Sof(C212)=Sof(H21E)=Sof(H21F)=Sof(H21G)=Sof(C213)=Sof(H21H)=
 Sof(H21I)=Sof(C214)=Sof(H21J)=Sof(H21K)=Sof(C215)=Sof(H21L)=Sof(H21M)=
 Sof(C216)=Sof(H21N)=Sof(H21O)=Sof(H21P)=1-FVAR(1)
 Sof(N100)=Sof(C101)=Sof(H10E)=Sof(H10F)=Sof(C102)=Sof(H10G)=Sof(H10H)=
 Sof(C103)=Sof(H10I)=Sof(H10J)=Sof(C104)=Sof(H10K)=Sof(H10L)=Sof(H10M)=
 Sof(C105)=Sof(H10N)=Sof(H10O)=Sof(C106)=Sof(H10P)=Sof(H10Q)=Sof(C107)=
 Sof(H10R)=Sof(H10S)=Sof(C108)=Sof(H10T)=Sof(H10U)=Sof(H10V)=Sof(C109)=
 Sof(H10W)=Sof(H10X)=Sof(C110)=Sof(H11A)=Sof(H11B)=Sof(C111)=Sof(H11C)=
 Sof(H11D)=Sof(C112)=Sof(H11E)=Sof(H11F)=Sof(H11G)=Sof(C113)=Sof(H11H)=
 Sof(H11I)=Sof(C114)=Sof(H11J)=Sof(H11K)=Sof(C115)=Sof(H11L)=Sof(H11M)=
 Sof(C116)=Sof(H11N)=Sof(H11O)=Sof(H11P)=FVAR(1)
 Sof(S1X)=Sof(O1X)=Sof(O2X)=Sof(O3X)=Sof(C1X)=Sof(H1XA)=Sof(H1XB)=Sof(H1XC)=1-
 FVAR(2)
 Sof(S1)=Sof(O1)=Sof(O2)=Sof(O3)=Sof(C1)=Sof(H1E)=Sof(H1F)=Sof(H1G)=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), C101(H10E,H10F), C102(H10G,H10H), C103(H10I,
 H10J), C105(H10N,H10O), C106(H10P,H10Q), C107(H10R,H10S), C109(H10W,H10X),
 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)
6.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C1C(H1C), C1D(H1D), C10A(H10A), C10B(H10B), C10C(H10C),
 C10D(H10D)
6.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)
6.e Idealised Me refined as rotating group:
 C1(H1E,H1F,H1G), C1X(H1XA,H1XB,H1XC), C19A(H19A,H19B,H19C), C19B(H19D,H19E,
 H19F), C19C(H19G,H19H,H19I), C19D(H19J,H19K,H19L), C2S(H2SA,H2SB,H2SC),
 C104(H10K,H10L,H10M), C108(H10T,H10U,H10V), 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              2940
_shelx_hkl_checksum              1405
_olex2_submission_special_instructions 'No special instructions were received'