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_1566203
_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, C76 H68 F12 O8, C16 H36 N'
_chemical_formula_sum            'C93 H107 F12 N O11 S'
_chemical_formula_weight         1674.85
_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
_audit_creation_date             2020-10-23
_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                 94.6270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5311(2)
_cell_length_b                   20.5937(3)
_cell_length_c                   32.9760(5)
_cell_measurement_reflns_used    5405
_cell_measurement_temperature    220
_cell_measurement_theta_max      56.34
_cell_measurement_theta_min      2.53
_cell_volume                     8482.1(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 2014/5 (Sheldrick, 2014)'
_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 0.916
_diffrn_measured_fraction_theta_max 0.916
_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  0.0824
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_Laue_measured_fraction_full 0.916
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            39163
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        61.540
_diffrn_reflns_theta_max         61.540
_diffrn_reflns_theta_min         2.532
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.080
_exptl_absorpt_correction_T_max  0.7520
_exptl_absorpt_correction_T_min  0.6863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0649 before and 0.0490 after correction. The Ratio of minimum to maximum transmission is 0.9126. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             3536
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.992
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     962
_refine_ls_number_reflns         12068
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1497
_refine_ls_R_factor_gt           0.0810
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1120P)^2^+10.4406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2034
_refine_ls_wR_factor_ref         0.2458
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6714
_reflns_number_total             12068
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc07041j2.cif
_cod_data_source_block           sm342second_a
_cod_database_code               1566203
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.928
_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
{C1U, C0AA}
{C1V, C1W}
3. Restrained distances
 C1U-C2U = C2U-C3U = C3U-C4U = C0AA-C1AA = C1AA-C2AA = C2AA-C3AA = C1V-C2V =
 C2V-C3V = C3V-C4V = C1W-C2W = C2W-C3W = C3W-C4W
 1.52 with sigma of 0.02
4. Rigid bond restraints
 F1D, C2D, F2D, C3D, F3D, C4D, C14A, C15A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Uiso/Uaniso restraints and constraints
F1D \\sim C2D \\sim F2D \\sim C3D \\sim F3D \\sim C4D \\sim C14A \\sim C15A:
within 2A with sigma of 0.008 and sigma for terminal atoms of 0.015
Uanis(C1U) = Uanis(C0AA) = Uanis(C2U) = Uanis(C1AA) = Uanis(C3U) = Uanis(C2AA)
= Uanis(C4U) = Uanis(C3AA)
Uanis(F1D) = Uanis(F2D) = Uanis(F3D)
Uanis(C1D) = Uanis(C2D) = Uanis(C3D) = Uanis(C4D) = Uanis(C5D) = Uanis(C6D)
Uanis(C1V) = Uanis(C1W) = Uanis(C2V) = Uanis(C2W) = Uanis(C3V) = Uanis(C3W) =
Uanis(C4V) = Uanis(C4W)
Uanis(C1T) = Uanis(C2T) = Uanis(C3T) = Uanis(C4T)
Uanis(C15A) = Uanis(C16A) = Uanis(C17A) = Uanis(C18A) = Uanis(C19A)
6. Others
 Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(C1AA)=Sof(H1AA)=Sof(H1AB)=Sof(C2AA)=
 Sof(H2AA)=Sof(H2AB)=Sof(C3AA)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=1-FVAR(1)
 Sof(C1U)=Sof(H1UA)=Sof(H1UB)=Sof(C2U)=Sof(H2UA)=Sof(H2UB)=Sof(C3U)=Sof(H3UA)=
 Sof(H3UB)=Sof(C4U)=Sof(H4UA)=Sof(H4UB)=Sof(H4UC)=FVAR(1)
 Sof(C1W)=Sof(H1WA)=Sof(H1WB)=Sof(C2W)=Sof(H2WA)=Sof(H2WB)=Sof(C3W)=Sof(H3WA)=
 Sof(H3WB)=Sof(C4W)=Sof(H4WA)=Sof(H4WB)=Sof(H4WC)=1-FVAR(2)
 Sof(C1V)=Sof(H1VA)=Sof(H1VB)=Sof(C2V)=Sof(H2VA)=Sof(H2VB)=Sof(C3V)=Sof(H3VA)=
 Sof(H3VB)=Sof(C4V)=Sof(H4VA)=Sof(H4VB)=Sof(H4VC)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C14A(H14A), C14B(H14B), C14C(H14C), C14D(H14D)
7.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), C1S(H1SA,H1SB), C1T(H1TA,H1TB), C1U(H1UA,
 H1UB), C1V(H1VA,H1VB), C2S(H2SA,H2SB), C2T(H2TA,H2TB), C2U(H2UA,H2UB),
 C2V(H2VA,H2VB), C3S(H3SA,H3SB), C3T(H3TA,H3TB), C3U(H3UA,H3UB), C3V(H3VA,H3VB),
  C0AA(H0AA,H0AB), C1AA(H1AA,H1AB), C2AA(H2AA,H2AB), C1W(H1WA,H1WB), C2W(H2WA,
 H2WB), C3W(H3WA,H3WB)
7.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C1C(H1C), C1D(H1D), C5D(H5D), C5A(H5A), C5B(H5B),
 C5C(H5C), C10A(H10A), C10B(H10B), C10C(H10C), C10D(H10D)
7.d Fitted hexagon refined as free rotating group:
 C1D(C2D,C3D,C4D,C5D,C6D)
7.e Idealised Me refined as rotating group:
 C1(H1E,H1F,H1G), C19A(H19A,H19B,H19C), C19B(H19D,H19E,H19F), C19C(H19G,H19H,
 H19I), C19D(H19J,H19K,H19L), C4S(H4SA,H4SB,H4SC), C4T(H4TA,H4TB,H4TC),
 C4U(H4UA,H4UB,H4UC), C4V(H4VA,H4VB,H4VC), C3AA(H3AA,H3AB,H3AC), C4W(H4WA,H4WB,
 H4WC)
;
_shelx_res_checksum              49186
_shelx_hkl_checksum              52632
_olex2_submission_special_instructions 'No special instructions were received'