Anion binding and transport properties of cyclic 2,6-bis(1,2,3-triazol-1-yl)pyridines.
Merckx, Tamara; Haynes, Cally J. E.; Karagiannidis, Louise E.; Clarke, Harriet J.; Holder, Katie; Kelly, Alexandra; Tizzard, Graham J.; Coles, Simon J.; Verwilst, Peter; Gale, Philip A.; Dehaen, Wim; Organic & biomolecular chemistry 13 (2015) 1654–1661; doi:10.1039/c4ob02236j

data_7154231
_publ_section_title
;
 Anion binding and transport properties of cyclic
 2,6-bis(1,2,3-triazol-1-yl)pyridines.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1654
_journal_page_last               1661
_journal_paper_doi               10.1039/c4ob02236j
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'Cl, C19 H25 N11 S2, C6 H11 N2'
_chemical_formula_sum            'C25 H36 Cl N13 S2'
_chemical_formula_weight         618.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_audit_update_record
;
????
;
_cell_angle_alpha                91.480(5)
_cell_angle_beta                 97.780(5)
_cell_angle_gamma                94.128(5)
_cell_formula_units_Z            4
_cell_length_a                   10.1456(7)
_cell_length_b                   15.6738(11)
_cell_length_c                   19.0361(13)
_cell_measurement_reflns_used    38200
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      2.4
_cell_volume                     2989.5(4)
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38182
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.429
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.025
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     793
_refine_ls_number_reflns         13640
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0797
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1321P)^2^+3.3740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2159
_refine_ls_wR_factor_ref         0.2484
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8940
_reflns_number_total             13640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob02236j2.cif
_cod_data_source_block           2[6a_(C6H11N2+)_(Cl-)]
_cod_depositor_comments
'Adding full bibliography for 7154229--7154231.cif.'
_cod_database_code               7154231
_shelxl_version_number           2013-4
_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, All N(H) groups,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S2A-N7A
 2.702 with sigma of 0.04
 S2A-N8A
 2.649 with sigma of 0.04
 N108-C116 \\sim N108-C216
 with sigma of 0.02
 N107-C116 \\sim N207-C216
 with sigma of 0.02
 N107-C115 \\sim N207-C215
 with sigma of 0.02
 C115-C114 \\sim C214-C215
 with sigma of 0.02
 C114-C113 \\sim C213-C214
 with sigma of 0.02
 C113-C112 \\sim C212-C213
 with sigma of 0.02
 C112-C111 \\sim C211-C212
 with sigma of 0.02
 C111-C110 \\sim C210-C211
 with sigma of 0.02
 N106-C110 \\sim N206-C210
 with sigma of 0.02
 N106-C109 \\sim N206-C209
 with sigma of 0.02
 N8-C16 \\sim N8A-C16A
 with sigma of 0.02
 N7-C16 \\sim N7A-C16A
 with sigma of 0.02
 N7-C15 \\sim N7A-C15
 with sigma of 0.02
 N8-C17 \\sim N8A-C17
 with sigma of 0.02
3. Restrained angles
 S2A-C16A-N8
 fixed at 120 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(S102) = Uanis(S202)
Uanis(C116) = Uanis(C216)
Uanis(C109) = Uanis(C209)
Uanis(S101) = Uanis(S201)
Uanis(N107) = Uanis(N207)
Uanis(C115) = Uanis(C215)
Uanis(C114) = Uanis(C214)
Uanis(C113) = Uanis(C213)
Uanis(C112) = Uanis(C212)
Uanis(C111) = Uanis(C211)
Uanis(C110) = Uanis(C210)
Uanis(N106) = Uanis(N206)
Uanis(S2) = Uanis(S2A)
Uanis(C16) = Uanis(C16A)
Uanis(N7) = Uanis(N7A)
Uanis(N8) = Uanis(N8A)
5. Same fragment restrains
{S2, C16, N7}
as
{S2A, C16A, N7A}
6. Others
 Sof(S201)=Sof(S202)=Sof(H10A)=Sof(H10B)=Sof(N206)=Sof(H206)=Sof(N207)=
 Sof(H207)=Sof(C209)=Sof(C210)=Sof(H21A)=Sof(H21B)=Sof(C211)=Sof(H21C)=
 Sof(H21D)=Sof(C212)=Sof(H21E)=Sof(H21F)=Sof(C213)=Sof(H21G)=Sof(H21H)=
 Sof(C214)=Sof(H21I)=Sof(H21J)=Sof(C215)=Sof(H21K)=Sof(H21L)=Sof(C216)=1-FVAR(1)
 Sof(S101)=Sof(S102)=Sof(H105)=Sof(N106)=Sof(H106)=Sof(N107)=Sof(H107)=
 Sof(H108)=Sof(C109)=Sof(C110)=Sof(H11A)=Sof(H11B)=Sof(C111)=Sof(H11C)=
 Sof(H11D)=Sof(C112)=Sof(H11E)=Sof(H11F)=Sof(C113)=Sof(H11G)=Sof(H11H)=
 Sof(C114)=Sof(H11I)=Sof(H11J)=Sof(C115)=Sof(H11K)=Sof(H11L)=Sof(C116)=FVAR(1)
 Sof(S2A)=Sof(C16A)=Sof(N7A)=Sof(H7A)=Sof(N8A)=Sof(H8A)=Sof(H15C)=Sof(H15D)=
 Sof(H17C)=Sof(H17D)=1-FVAR(2)
 Sof(S2)=Sof(C16)=Sof(N7)=Sof(H7)=Sof(N8)=Sof(H8)=Sof(H15A)=Sof(H15B)=
 Sof(H17A)=Sof(H17B)=FVAR(2)
7.a Riding coordinates:
 N105(H10A), N108(H10B)
7.b Secondary CH2 refined with riding coordinates:
 C8(H8B,H8C), C10(H10F,H10G), C11(H11O,H11P), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C15(H15C,H15D), C17(H17A,H17B), C17(H17C,H17D),
  C108(H10D,H10E), C110(H11A,H11B), C111(H11C,H11D), C112(H11E,H11F), C113(H11G,
 H11H), C114(H11I,H11J), C115(H11K,H11L), C117(H11M,H11N), C210(H21A,H21B),
 C211(H21C,H21D), C212(H21E,H21F), C213(H21G,H21H), C214(H21I,H21J), C215(H21K,
 H21L), C54(H54A,H54B), C154(H15E,H15F)
7.c Aromatic/amide H refined with riding coordinates:
 N7(H7), N7A(H7A), N5(H5), N6(H6), N8(H8), N8A(H8A), C2(H2), C3(H3), C4(H4),
 C6(H6A), C19(H19), N105(H105), N106(H106), N107(H107), N108(H108), N206(H206),
 N207(H207), C102(H102), C103(H103), C104(H104), C106(H10C), C119(H119),
 C51(H51), C52(H52), C53(H53), C151(H151), C152(H152), C153(H153)
7.d Idealised Me refined as rotating group:
 C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C155(H15G,H15H,H15I), C156(H15J,
 H15K,H15L)
;
_shelx_res_checksum              31847
_shelx_hkl_checksum              4415