Remarkably selective NH4+ binding and fluorescence sensing by tripodal tris(pyrazolyl) receptors derived from 1,3,5-triethylbenzene: structural and theoretical insights on the role of ion pairing
Jonah, Tosin M.; Mathivathanan, Logesh; Morozov, Alexander N.; Mebel, Alexander M.; Raptis, Raphael G.; Kavallieratos, Konstantinos; New Journal of Chemistry 41 (2017) 14835–14838; doi:10.1039/C7NJ03213G

data_7056750
_publ_section_title
;
 Remarkably selective NH4+ binding and fluorescence sensing by tripodal
 tris(pyrazolyl) receptors derived from 1,3,5-triethylbenzene: structural
 and theoretical insights on the role of ion pairing
;
_journal_issue                   24
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14835
_journal_page_last               14838
_journal_paper_doi               10.1039/C7NJ03213G
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C60 H54 N6'
_chemical_formula_sum            'C60 H54 N6'
_chemical_formula_weight         859.09
_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     dual
_audit_creation_date             2017-05-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-08 deposited with the CCDC.
2017-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                94.8670(10)
_cell_angle_beta                 102.5260(10)
_cell_angle_gamma                106.6380(10)
_cell_formula_units_Z            2
_cell_length_a                   10.5434(4)
_cell_length_b                   12.4141(5)
_cell_length_c                   19.6118(8)
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.907
_cell_measurement_theta_min      2.970
_cell_volume                     2371.10(16)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297.01
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            41715
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.208
_diffrn_reflns_theta_min         2.938
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0548 before and 0.0493 after correction. The Ratio of minimum to maximum transmission is 0.9634. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     679
_refine_ls_number_reflns         9430
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1758
_refine_ls_R_factor_gt           0.0702
_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^)+(0.0827P)^2^+0.3177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1884
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4462
_reflns_number_total             9430
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj03213g2.cif
_cod_data_source_block           rgr536_a
_cod_database_code               7056750
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.977
_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
 C46-C55A
 1.452 with sigma of 0.02
 C49A-C48
 1.432 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C25A \\sim C30A \\sim C29A \\sim C28A \\sim C27A \\sim C26A: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Sof(C55A)=Sof(C56A)=Sof(H56A)=Sof(C57A)=Sof(H57A)=Sof(C58A)=Sof(H58A)=
 Sof(C59A)=Sof(H59A)=Sof(C60A)=Sof(H60A)=1-FVAR(1)
 Sof(C55)=Sof(C56)=Sof(H56)=Sof(C60)=Sof(H60)=Sof(C58)=Sof(H58)=Sof(C57)=
 Sof(H57)=Sof(C59)=Sof(H59)=FVAR(1)
 Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=
 Sof(H29A)=Sof(C30A)=Sof(H30A)=Sof(C25A)=1-FVAR(2)
 Sof(C25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=Sof(C28)=Sof(H28)=Sof(C29)=
 Sof(H29)=Sof(C30)=Sof(H30)=FVAR(2)
 Sof(C49A)=Sof(C54A)=Sof(H54A)=Sof(C53A)=Sof(H53A)=Sof(C52A)=Sof(H52A)=
 Sof(C51A)=Sof(H51A)=Sof(C50A)=Sof(H50A)=1-FVAR(3)
 Sof(C49)=Sof(C50)=Sof(H50)=Sof(C51)=Sof(H51)=Sof(C52)=Sof(H52)=Sof(C53)=
 Sof(H53)=Sof(C54)=Sof(H54)=FVAR(3)
 Fixed U11: C26A(0.07856) C27A(0.124329) C28A(0.077807) C29A(0.129327)
 C30A(0.078403) C25A(0.108908)
 Fixed U12: C26A(0.014776) C27A(0.032155) C28A(0.050463) C29A(0.083592)
 C30A(0.020021) C25A(-0.027533)
 Fixed U13: C26A(0.003795) C27A(-0.000069) C28A(0.04281) C29A(0.039736)
 C30A(0.027568) C25A(-0.017544)
 Fixed U22: C26A(0.054154) C27A(0.082015) C28A(0.038959) C29A(0.170653)
 C30A(0.129016) C25A(0.060862)
 Fixed U23: C26A(-0.05425) C27A(-0.058751) C28A(0.000887) C29A(0.112569)
 C30A(0.066167) C25A(-0.013322)
 Fixed U33: C26A(0.24135) C27A(0.26296) C28A(0.17978) C29A(0.11985)
 C30A(0.0675) C25A(0.04269)
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B)
5.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26),
 C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C35(H35), C36(H36), C37(H37),
  C38(H38), C39(H39), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45),
 C47(H47), C50(H50), C51(H51), C52(H52), C53(H53), C54(H54), C56(H56), C60(H60),
  C58(H58), C57(H57), C59(H59), C56A(H56A), C57A(H57A), C58A(H58A), C59A(H59A),
 C60A(H60A), C26A(H26A), C27A(H27A), C28A(H28A), C29A(H29A), C30A(H30A),
 C54A(H54A), C53A(H53A), C52A(H52A), C51A(H51A), C50A(H50A)
5.c Fitted hexagon refined as free rotating group:
 C25(C26,C27,C28,C29,C30), C49(C50,C51,C52,C53,C54), C55A(C56A,C57A,C58A,C59A,
 C60A), C26A(C27A,C28A,C29A,C30A,C25A)
5.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
6. Crystallographic disorder of two phenyl rings, which could not be modeled fully, 
generates Alerts level-A on C28A and C49A-C54A. The imperfect disorder modeling of C49-C54
causes accidental intermolecular H...H contact with a methylene proton.
;
_shelx_res_checksum              2528
_olex2_submission_special_instructions 'No special instructions were received'