Anion Transporters Based on Noncovalent Balance including Anion-π, Hydrogen, and Halogen Bonding.
Huang, Wen-Long; Wang, Xu-Dong; Li, Sen; Zhang, Rui; Ao, Yu-Fei; Tang, Jun; Wang, Qi-Qiang; Wang, De-Xian; The Journal of organic chemistry 84 (2019) 8859–8869; doi:10.1021/acs.joc.9b00561

data_4034205
_publ_section_title
;
 Anion Transporters Based on Noncovalent Balance including Anion-\p,
 Hydrogen, and Halogen Bonding.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8859
_journal_page_last               8869
_journal_paper_doi               10.1021/acs.joc.9b00561
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety
'2(C34 H20 I2 N6 O12), 2.5(C8 H20 N), C4 H8 O2, 2.5(Cl)'
_chemical_formula_sum            'C92 H98 Cl2.5 I4 N14.5 O26'
_chemical_formula_weight         2419.07
_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             2018-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                106.007(2)
_cell_angle_beta                 108.730(2)
_cell_angle_gamma                92.977(2)
_cell_formula_units_Z            2
_cell_length_a                   15.6454(3)
_cell_length_b                   15.8125(3)
_cell_length_c                   23.8504(5)
_cell_measurement_reflns_used    40700
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.3100
_cell_measurement_theta_min      1.7460
_cell_volume                     5306.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            73041
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.787
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    1.314
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       block
_exptl_crystal_F_000             2428
_exptl_crystal_size_max          0.578
_exptl_crystal_size_mid          0.277
_exptl_crystal_size_min          0.262
_refine_diff_density_max         4.505
_refine_diff_density_min         -3.957
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1314
_refine_ls_number_reflns         24310
_refine_ls_number_restraints     153
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0706
_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^)+(0.0969P)^2^+17.1853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.2013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18912
_reflns_number_total             24310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00561_si_003.cif
_cod_data_source_block           mx6741e_sq
_cod_original_formula_sum        'C92 H98 Cl2.50 I4 N14.50 O26'
_cod_database_code               4034205
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.725
_shelx_estimated_absorpt_t_min   0.517
_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, All O(H) groups
2. Restrained distances
 N9-C51 = N9-C53 = N9-C55 = N9-C57
 1.52 with sigma of 0.01
 C58-C57 = C52-C51 = C54-C53 = C56-C55
 1.54 with sigma of 0.01
 C60-C59 = C62-C61
 1.54 with sigma of 0.01
 O14-C60 = O14-C61 = O13-C62 = O13-C59
 1.47 with sigma of 0.01
 N9-C52
 2.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N9 \\sim C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56 \\sim C57 \\sim
C58: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C58) \\sim Ueq, Uanis(N9) \\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C53)
\\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(C52) \\sim Ueq,
Uanis(C54) \\sim Ueq, Uanis(C56) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C60) \\sim Ueq, Uanis(O13) \\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C62)
\\sim Ueq, Uanis(C61) \\sim Ueq, Uanis(O14) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: N9(0.5) C51(0.5) H51A(0.5) H51B(0.5) C52(0.5) H52A(0.5) H52B(0.5)
 H52C(0.5) C53(0.5) H53A(0.5) H53B(0.5) C54(0.5) H54A(0.5) H54B(0.5) H54C(0.5)
 C55(0.5) H55A(0.5) H55B(0.5) C56(0.5) H56A(0.5) H56B(0.5) H56C(0.5) C57(0.5)
 H57A(0.5) H57B(0.5) C58(0.5) H58A(0.5) H58B(0.5) H58C(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C51(H51A,H51B), C53(H53A,H53B), C55(H55A,H55B), C57(H57A,H57B), C35(H35A,
 H35B), C37(H37A,H37B), C39(H39A,H39B), C41(H41A,H41B), C43(H43A,H43B),
 C45(H45A,H45B), C47(H47A,H47B), C49(H49A,H49B), C59(H59A,H59B), C60(H60A,H60B),
  C61(H61A,H61B), C62(H62A,H62B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C23(H23), C24(H24),
 C25(H25), C26(H26), C28(H28), C30(H30), C6A(H6AB), C7A(H7A), C8A(H8A),
 C9A(H9A), C11A(H11A), C13A(H13A), C23A(H23A), C24A(H24A), C25A(H25A),
 C26A(H26A), C28A(H28A), C30A(H30A)
5.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C), C17A(H17D,H17E,H17F), C34A(H34D,
 H34E,H34F), C52(H52A,H52B,H52C), C54(H54A,H54B,H54C), C56(H56A,H56B,H56C),
 C58(H58A,H58B,H58C), C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C40(H40A,H40B,
 H40C), C42(H42A,H42B,H42C), C44(H44A,H44B,H44C), C46(H46A,H46B,H46C), C48(H48A,
 H48B,H48C), C50(H50A,H50B,H50C)
5.d Idealised tetrahedral OH refined as rotating group:
 O6(H6A), O10(H10), O6A(H6AA), O10A(H10A)
;
_shelx_res_checksum              67638
_shelx_hkl_checksum              13526
_shelx_fab_checksum              96461
_olex2_submission_special_instructions 'No special instructions were received'