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_4034206
_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 H18 Br4 N6 O12), 5(C8 H20 N), 3(C H2 Cl2), 5(Cl), 4(H2 O)'
_chemical_formula_sum            'C111 H150 Br8 Cl11 N17 O28'
_chemical_formula_weight         3199.70
_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   mixed
_audit_creation_date             2018-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.081(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3373(3)
_cell_length_b                   17.9188(4)
_cell_length_c                   57.9576(11)
_cell_measurement_reflns_used    34253
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.5470
_cell_measurement_theta_min      1.5400
_cell_volume                     13831.2(5)
_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, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1244
_diffrn_reflns_av_unetI/netI     0.1158
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       75
_diffrn_reflns_limit_l_min       -75
_diffrn_reflns_number            168152
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.550
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    2.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58891
_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    1.537
_exptl_crystal_description       plate
_exptl_crystal_F_000             6504
_exptl_crystal_size_max          0.086
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.877
_refine_diff_density_min         -1.083
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1889
_refine_ls_number_reflns         31757
_refine_ls_number_restraints     919
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1742
_refine_ls_R_factor_gt           0.0835
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0768P)^2^+37.6159P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.2234
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16024
_reflns_number_total             31757
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00561_si_002.cif
_cod_data_source_block           mx6757
_cod_database_code               4034206
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.807
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C68A-C67A
 1.55 with sigma of 0.01
 C54-C53 = C52-C51
 1.54 with sigma of 0.01
 N9-C53A = N9-C53 = N9-C57A = N9-C57 = N9-C55 = N9-C51A = N9-C51
 1.52 with sigma of 0.01
 C56-C55
 1.54 with sigma of 0.01
 N11-C63A = N11-C63 = N11-C61 = N11-C61A = N11-C59 = N11-C59A = N11-C65A = N11-
 C65
 1.52 with sigma of 0.01
 C62A-C61A = C60-C59 = C60A-C59A = C66A-C65A = C66-C65 = C64-C63 = C64A-C63A =
 C62-C61
 1.54 with sigma of 0.01
 C63A-C61A
 2.5 with sigma of 0.02
 C65A-C59A
 2.5 with sigma of 0.02
3. Rigid bond restraints
 C66, C65
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C69, C70
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Br3 \\sim C5 \\sim C6 \\sim C2AA \\sim C5AA \\sim Br5A \\sim O0AA \\sim Br4
\\sim C4 \\sim O5 \\sim C7 \\sim C8 \\sim C9 \\sim Br0A \\sim C0AA \\sim C1AA
\\sim C3AA \\sim C4AA: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C64A \\sim N11 \\sim C59A \\sim C63A \\sim C59 \\sim C61 \\sim C65A \\sim C63
\\sim C61A \\sim C65 \\sim C60A \\sim C60 \\sim C62 \\sim C66A \\sim C64 \\sim
C62A \\sim C66: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
C55 \\sim N9 \\sim C51 \\sim C53 \\sim C57 \\sim C53A \\sim C57A \\sim C51A
\\sim C52 \\sim C54 \\sim C56 \\sim C58A \\sim C54A \\sim C58 \\sim C52A \\sim
C56A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(Br3) \\sim Ueq, Uanis(Br4) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq,
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(Br0A) \\sim Ueq, Uanis(C0AA)
\\sim Ueq, Uanis(C1AA) \\sim Ueq, Uanis(C2AA) \\sim Ueq, Uanis(C3AA) \\sim Ueq,
Uanis(C4AA) \\sim Ueq, Uanis(C5AA) \\sim Ueq, Uanis(Br5A) \\sim Ueq,
Uanis(O0AA) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C68A) \\sim Ueq, Uanis(C67A) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C68)
\\sim Ueq, Uanis(C70A) \\sim Ueq, Uanis(C69A) \\sim Ueq, Uanis(C70) \\sim Ueq,
Uanis(C74) \\sim Ueq, Uanis(C74A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C64A) \\sim Ueq, Uanis(N11) \\sim Ueq, Uanis(C59A) \\sim Ueq, Uanis(C63A)
\\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C61) \\sim Ueq, Uanis(C65A) \\sim Ueq,
Uanis(C63) \\sim Ueq, Uanis(C61A) \\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C60A)
\\sim Ueq, Uanis(C60) \\sim Ueq, Uanis(C62) \\sim Ueq, Uanis(C66A) \\sim Ueq,
Uanis(C64) \\sim Ueq, Uanis(C62A) \\sim Ueq, Uanis(C66) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C56) \\sim Ueq, Uanis(N9) \\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C53)
\\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(C53A) \\sim Ueq,
Uanis(C57A) \\sim Ueq, Uanis(C51A) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C54)
\\sim Ueq, Uanis(C58A) \\sim Ueq, Uanis(C54A) \\sim Ueq, Uanis(C58) \\sim Ueq,
Uanis(C52A) \\sim Ueq, Uanis(C56A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Others
 Sof(Br0A)=Sof(C0AA)=Sof(C1AA)=Sof(C2AA)=Sof(H2AA)=Sof(C3AA)=Sof(H3AA)=
 Sof(C4AA)=Sof(H4AA)=Sof(C5AA)=Sof(Br5A)=Sof(O0AA)=1-FVAR(1)
 Sof(Br3)=Sof(Br4)=Sof(C4)=Sof(C5)=Sof(O5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=
 Sof(C8)=Sof(H8)=Sof(C9)=FVAR(1)
 Sof(C67A)=Sof(H67C)=Sof(H67D)=Sof(C68A)=Sof(H68D)=Sof(H68E)=Sof(H68F)=
 Sof(C73A)=Sof(H73C)=Sof(H73D)=Sof(C74A)=Sof(H74D)=Sof(H74E)=Sof(H74F)=
 Sof(C70A)=Sof(H70D)=Sof(H70E)=Sof(H70F)=Sof(C69A)=Sof(H69C)=Sof(H69D)=1-FVAR(2)
 Sof(C67)=Sof(H67A)=Sof(H67B)=Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(H68C)=Sof(C69)=
 Sof(H69A)=Sof(H69B)=Sof(C70)=Sof(H70A)=Sof(H70B)=Sof(H70C)=Sof(C73)=Sof(H73A)=
 Sof(H73B)=Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(H74C)=FVAR(2)
 Sof(C58A)=Sof(H58A)=Sof(H58B)=Sof(H58C)=Sof(C53A)=Sof(H53C)=Sof(H53D)=
 Sof(C54A)=Sof(H54D)=Sof(H54E)=Sof(H54F)=Sof(C57A)=Sof(H57C)=Sof(H57D)=
 Sof(C51A)=Sof(H51C)=Sof(H51D)=Sof(C52A)=Sof(H52D)=Sof(H52E)=Sof(H52F)=1-FVAR(3)
 Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=Sof(C53)=
 Sof(H53A)=Sof(H53B)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=Sof(C57)=Sof(H57A)=
 Sof(H57B)=Sof(C58)=Sof(H58D)=Sof(H58E)=Sof(H58F)=FVAR(3)
 Sof(H55C)=Sof(H55D)=Sof(C56A)=Sof(H56D)=Sof(H56E)=Sof(H56F)=1-FVAR(4)
 Sof(H55A)=Sof(H55B)=Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(H56C)=FVAR(4)
 Sof(C61A)=Sof(H61C)=Sof(H61D)=Sof(C62A)=Sof(H62D)=Sof(H62E)=Sof(H62F)=
 Sof(C63A)=Sof(H63C)=Sof(H63D)=Sof(C64A)=Sof(H64D)=Sof(H64E)=Sof(H64F)=
 Sof(C65A)=Sof(H65C)=Sof(H65D)=Sof(C66A)=Sof(H66D)=Sof(H66E)=Sof(H66F)=
 Sof(C59A)=Sof(H59C)=Sof(H59D)=Sof(C60A)=Sof(H60D)=Sof(H60E)=Sof(H60F)=1-FVAR(5)
 Sof(C59)=Sof(H59A)=Sof(H59B)=Sof(C61)=Sof(H61A)=Sof(H61B)=Sof(C62)=Sof(H62A)=
 Sof(H62B)=Sof(H62C)=Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(C64)=Sof(H64A)=Sof(H64B)=
 Sof(H64C)=Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=
 Sof(C60)=Sof(H60A)=Sof(H60B)=Sof(H60C)=FVAR(5)
 Fixed U11: C69(0.151704)
 Fixed X: C69A(0.473789)
 Fixed Y: C64A(0.39706) C59A(0.449769)
 Fixed Z: C63A(0.684) C64A(0.690371)
6.a Riding coordinates:
 O15(H15A,H15B)
6.b Free rotating group:
 O14(H14A,H14B), O13(H13B,H13C), O16(H16A,H16B)
6.c Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C37(H37A,H37B), C39(H39A,H39B), C41(H41A,H41B), C67(H67A,
 H67B), C69(H69A,H69B), C71(H71A,H71B), C73(H73A,H73B), C43(H43A,H43B),
 C45(H45A,H45B), C47(H47A,H47B), C49(H49A,H49B), C51(H51A,H51B), C53(H53A,H53B),
  C55(H55A,H55B), C55(H55C,H55D), C57(H57A,H57B), C59(H59A,H59B), C61(H61A,
 H61B), C63(H63A,H63B), C65(H65A,H65B), C75(H75A,H75B), C77(H77A,H77B),
 C76(H76A,H76B), C67A(H67C,H67D), C73A(H73C,H73D), C69A(H69C,H69D), C53A(H53C,
 H53D), C57A(H57C,H57D), C51A(H51C,H51D), C61A(H61C,H61D), C63A(H63C,H63D),
 C65A(H65C,H65D), C59A(H59C,H59D)
6.d Me refined with riding coordinates:
 C34(H34A,H34B,H34C), C58A(H58A,H58B,H58C), C58(H58D,H58E,H58F), C64A(H64D,
 H64E,H64F)
6.e Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C11(H11), C13(H13), C23(H23), C24(H24), C25(H25),
 C30(H30), C32(H32), C6A(H6AB), C7A(H7A), C8A(H8A), C11A(H11A), C13A(H13A),
 C23A(H23A), C24A(H24A), C25A(H25A), C30A(H30A), C32A(H32A), C2AA(H2AA),
 C3AA(H3AA), C4AA(H4AA)
6.f Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C17A(H17D,H17E,H17F), C34A(H34D,H34E,H34F), C35(H35A,
 H35B,H35C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C42(H42A,H42B,H42C),
 C68(H68A,H68B,H68C), C70(H70A,H70B,H70C), C72(H72A,H72B,H72C), C74(H74A,H74B,
 H74C), C44(H44A,H44B,H44C), C46(H46A,H46B,H46C), C48(H48A,H48B,H48C), C50(H50A,
 H50B,H50C), C52(H52A,H52B,H52C), C54(H54A,H54B,H54C), C56(H56A,H56B,H56C),
 C62(H62A,H62B,H62C), C64(H64A,H64B,H64C), C66(H66A,H66B,H66C), C60(H60A,H60B,
 H60C), C68A(H68D,H68E,H68F), C74A(H74D,H74E,H74F), C70A(H70D,H70E,H70F),
 C54A(H54D,H54E,H54F), C52A(H52D,H52E,H52F), C56A(H56D,H56E,H56F), C62A(H62D,
 H62E,H62F), C66A(H66D,H66E,H66F), C60A(H60D,H60E,H60F)
6.g Idealised tetrahedral OH refined as rotating group:
 O6(H6A), O10(H10), O6A(H6AA), O10A(H10A)
;
_shelx_res_checksum              92705
_shelx_hkl_checksum              58875
_olex2_submission_special_instructions 'No special instructions were received'