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_1566201
_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         'C76 H80 O8, 3(C2 H3 N)'
_chemical_formula_sum            'C82 H89 N3 O8'
_chemical_formula_weight         1244.56
_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
_audit_creation_date             2020-10-05
_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                100.1450(10)
_cell_angle_beta                 96.3810(10)
_cell_angle_gamma                102.8310(10)
_cell_formula_units_Z            2
_cell_length_a                   11.9327(3)
_cell_length_b                   12.8148(3)
_cell_length_c                   24.0608(5)
_cell_measurement_reflns_used    9790
_cell_measurement_temperature    220
_cell_measurement_theta_max      62.34
_cell_measurement_theta_min      3.78
_cell_volume                     3487.76(14)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      220
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_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  0.0500
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            56675
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        62.594
_diffrn_reflns_theta_max         62.594
_diffrn_reflns_theta_min         1.888
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.6123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1033 before and 0.0625 after correction. The Ratio of minimum to maximum transmission is 0.8140. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       block
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         3.230
_refine_diff_density_min         -0.997
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.333
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     673
_refine_ls_number_reflns         10814
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      2.337
_refine_ls_R_factor_all          0.1700
_refine_ls_R_factor_gt           0.1539
_refine_ls_shift/su_max          0.955
_refine_ls_shift/su_mean         0.016
_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          0.4797
_refine_ls_wR_factor_ref         0.5052
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8708
_reflns_number_total             10814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc07041j2.cif
_cod_data_source_block           sm328first_a
_cod_database_code               1566201
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.965
_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
{C5S, C5T}
3. Restrained distances
 N2S-C3S = N3S-C5S = N3T-C5T
 1.15 with sigma of 0.02
 C3S-C4S = C5S-C6S = C5T-C6T
 1.4 with sigma of 0.02
 C6A-C7A = C6D-C7D
 1.5 with sigma of 0.001
 C1A-C6A = C1C-C6C
 1.4 with sigma of 0.001
4. Rigid bond restraints
 N1S, C1S, C2S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
N1S \\sim C1S \\sim C2S: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(N2S) \\sim Ueq, Uanis(C3S) \\sim Ueq, Uanis(C4S) \\sim Ueq, Uanis(N3S)
\\sim Ueq, Uanis(N3T) \\sim Ueq, Uanis(C5S) \\sim Ueq, Uanis(C5T) \\sim Ueq,
Uanis(C6S) \\sim Ueq, Uanis(C6T) \\sim Ueq: with sigma of 0.03 and sigma for
terminal atoms of 0.06
Uanis(N2S) = Uanis(C4S) = Uanis(C3S)
Uanis(C1A) = Uanis(C2A) = Uanis(C3A) = Uanis(C4A) = Uanis(C5A) = Uanis(C6A)
Uanis(C1B) = Uanis(C2B) = Uanis(C3B) = Uanis(C4B) = Uanis(C5B) = Uanis(C6B)
Uanis(C1C) = Uanis(C2C) = Uanis(C3C) = Uanis(C4C) = Uanis(C5C) = Uanis(C6C)
Uanis(C1D) = Uanis(C2D) = Uanis(C3D) = Uanis(C4D) = Uanis(C5D) = Uanis(C6D)
Uanis(C15D) = Uanis(C16D) = Uanis(C17D) = Uanis(C18D) = Uanis(C19D)
Uanis(N3S) = Uanis(N3T) = Uanis(C5S) = Uanis(C5T) = Uanis(C6S) = Uanis(C6T)
6. Others
 Sof(N3T)=Sof(C5T)=Sof(C6T)=Sof(H6TA)=Sof(H6TB)=Sof(H6TC)=1-FVAR(1)
 Sof(N3S)=Sof(C5S)=Sof(C6S)=Sof(H6SA)=Sof(H6SB)=Sof(H6SC)=FVAR(1)
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)
7.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1C(H1C), C1D(H1D), C2A(H2A), C2C(H2C), C2D(H2D), C3A(H3A),
 C1B(H1B), C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B), C3C(H3C), C3D(H3D), C4A(H4A),
  C4C(H4C), C4D(H4D), C5A(H5A), C5C(H5C), C5D(H5D), C10A(H10A), C10B(H10B),
 C10C(H10C), C10D(H10D)
7.d Fitted hexagon refined as free rotating group:
 C1B(C2B,C3B,C4B,C5B,C6B)
7.e 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), C6S(H6SA,H6SB,H6SC),
 C6T(H6TA,H6TB,H6TC)
;
_shelx_res_checksum              30646
_shelx_hkl_checksum              86988
_olex2_submission_special_instructions 'No special instructions were received'