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_1566197
_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         '2(C H2 Cl2), C76 H72 F8 O8, C4 H6 N2'
_chemical_formula_sum            'C82 H82 Cl4 F8 N2 O8'
_chemical_formula_weight         1517.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-02-25
_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                 131.7640(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.1351(6)
_cell_length_b                   12.8854(2)
_cell_length_c                   23.6066(7)
_cell_measurement_reflns_used    9740
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      70.18
_cell_measurement_theta_min      3.58
_cell_volume                     7517.9(3)
_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      230.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_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  0.0357
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            48517
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.169
_diffrn_reflns_theta_min         3.577
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.083
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0685 before and 0.0528 after correction. The Ratio of minimum to maximum transmission is 0.8832. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             3168
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.655
_refine_diff_density_min         -2.868
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       0.00015(13)
_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   2.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         7100
_refine_ls_number_restraints     80
_refine_ls_restrained_S_all      2.186
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.1332
_refine_ls_shift/su_max          0.444
_refine_ls_shift/su_mean         0.010
_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          0.4235
_refine_ls_wR_factor_ref         0.4483
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5926
_reflns_number_total             7100
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc07041j2.cif
_cod_data_source_block           sm341first_a
_cod_database_code               1566197
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.868
_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. Restrained distances
 N1S-C1S = N2S-C3S
 1.14 with sigma of 0.01
 C1S-C2S = C3S-C4S
 1.45 with sigma of 0.02
3. Rigid bond restraints
 C2A, F1A, C4A, F2A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C2B, F1B, C4B, F2B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C2A \\sim F1A \\sim C4A \\sim F2A: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04
C2B \\sim F1B \\sim C4B \\sim F2B: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(C18B) \\sim Ueq, Uanis(C19B) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(Cl1S) \\sim Ueq, Uanis(Cl2S) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N1S) \\sim Ueq, Uanis(C4S) \\sim Ueq: with sigma of 0.004 and sigma for
terminal atoms of 0.015
Uanis(F1A) \\sim Ueq, Uanis(F2A) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.006
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(Cl1S) = Uanis(Cl2S)
5. Others
 Fixed Sof: H2SA(0.5) H2SB(0.5) H2SC(0.5) H4SA(0.5) H4SB(0.5) H4SC(0.5)
6.a Ternary CH refined with riding coordinates:
 C14A(H14A), C14B(H14B)
6.b Secondary CH2 refined with riding coordinates:
 C5S(H5SA,H5SB), C13B(H13C,H13D), C15A(H15A,H15B), C15B(H15C,H15D), C16A(H16A,
 H16B), C16B(H16C,H16D), C17A(H17A,H17B), C17B(H17C,H17D), C18A(H18A,H18B),
 C18B(H18C,H18D)
6.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C1B(H1B), C3A(H3A), C3B(H3B), C5A(H5A), C5B(H5B), C10A(H10A),
 C10B(H10B)
6.d Idealised Me refined as rotating group:
 C19A(H19A,H19B,H19C), C19B(H19D,H19E,H19F), C2S(H2SA,H2SB,H2SC), C4S(H4SA,
 H4SB,H4SC)
;
_shelx_res_checksum              76879
_shelx_hkl_checksum              87366
_olex2_submission_special_instructions 'No special instructions were received'