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_7154230
_publ_section_title
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 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, 0.5(O), C7 H10 N'
_chemical_formula_sum            'C26 H36 Cl N12 O0.5 S2'
_chemical_formula_weight         624.24
_chemical_name_systematic
;
 ?
;
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                107.255(2)
_cell_angle_beta                 90.906(2)
_cell_angle_gamma                96.740(2)
_cell_formula_units_Z            4
_cell_length_a                   10.391(2)
_cell_length_b                   16.944(4)
_cell_length_c                   18.900(4)
_cell_measurement_reflns_used    6333
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.6
_cell_measurement_theta_min      1.9
_cell_volume                     3151.4(12)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_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 0.0350
_diffrn_detector_type            'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  CrystalLogic
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.688900
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_av_unetI/netI     0.1187
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29935
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         26.623
_diffrn_reflns_theta_min         1.095
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       plate
_exptl_crystal_F_000             1316
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DMSO'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.952
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     763
_refine_ls_number_reflns         13849
_refine_ls_number_restraints     65
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1459
_refine_ls_R_factor_gt           0.0832
_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^)+(0.1415P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2143
_refine_ls_wR_factor_ref         0.2721
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7931
_reflns_number_total             13849
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob02236j2.cif
_cod_data_source_block           2[6a_(C7H10N+)_(Cl-)]_H2O
_cod_depositor_comments
'Adding full bibliography for 7154229--7154231.cif.'
_cod_original_formula_sum        'C26 H36 Cl N12 O0.50 S2'
_cod_database_code               7154230
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C57, C56, N51, C55, C54, C53, C52, C51
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C57 \\sim C56 \\sim C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim N51:
within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(Cl1A) = Uanis(Cl1B)
4. Others
 Sof(Cl1B)=Sof(O1B)=1-FVAR(1)
 Sof(Cl1A)=Sof(O1A)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C108(H10D,H10E), C110(H11C,
 H11D), C111(H11E,H11F), C112(H11G,H11H), C113(H11I,H11J), C114(H11K,H11L),
 C115(H11M,H11N), C117(H11O,H11P), C56(H56A,H56B), C156(H15C,H15D)
5.b Aromatic/amide H refined with riding coordinates:
 N5(H5), N6(H6), N7(H7), N8(H8), C2(H2), C3(H3), C4(H4), C6(H6A), C19(H19),
 N105(H105), N106(H106), N107(H107), N108(H108), C102(H102), C103(H103),
 C104(H104), C106(H10C), C119(H119), C51(H51), C52(H52), C53(H53), C54(H54),
 C55(H55), C151(H151), C152(H152), C153(H153), C154(H154), C155(H155)
5.c Idealised Me refined as rotating group:
 C57(H57A,H57B,H57C), C157(H15E,H15F,H15G)
;
_shelx_res_checksum              88852
_shelx_hkl_checksum              31676