Visible colorimetric fluoride and hydroxide sensing by asymmetric tris-urea receptors: combined experimental and theoretical studies
Wang, Ruyu; Shu, Xi; Fan, Yu; Li, Shoujian; Jin, Yongdong; Huang, Chao; RSC Advances 8 (2018) 39394–; doi:10.1039/C8RA07495J

data_7231875
_publ_section_title
;
 Visible colorimetric fluoride and hydroxide sensing by asymmetric
 tris-urea receptors: combined experimental and theoretical studies
;
_journal_issue                   69
_journal_name_full               'RSC Advances'
_journal_page_first              39394
_journal_paper_doi               10.1039/C8RA07495J
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C25 H23.22 N9 O9, C2 H5 O0.5'
_chemical_formula_sum            'C27 H29.41 N9 O9.5'
_chemical_formula_weight         632.01
_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     direct
_audit_creation_date             2017-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-09-13 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                95.365(4)
_cell_angle_beta                 90.472(4)
_cell_angle_gamma                101.742(4)
_cell_formula_units_Z            2
_cell_length_a                   7.1240(4)
_cell_length_b                   12.8626(5)
_cell_length_c                   16.0430(7)
_cell_measurement_reflns_used    5150
_cell_measurement_temperature    296.31(10)
_cell_measurement_theta_max      72.5900
_cell_measurement_theta_min      4.2670
_cell_volume                     1432.44(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      air
_diffrn_ambient_temperature      296.31(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -90.0000 84

  2 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000    0.0000 84

  3 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   30.0000 94

  4 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -60.0000 94

  5 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -180.0000 67

  6 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000 -150.0000 88

  7 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  120.0000 88

  8 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -150.0000 67

  9 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   60.0000 74

 10 omega   38.00   91.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 11 omega   38.00   91.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 12 omega   39.00  109.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

 13 omega   91.00  176.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

 14 omega   38.00  116.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 78

 15 omega   41.00  126.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 85

 16 omega   38.00   91.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 17 omega   38.00  116.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 18 omega   38.00   91.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 19 omega   37.00  146.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -150.0000 109

 20 omega   40.00   98.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 21 omega   40.00   98.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

 22 omega   91.00  176.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 85

 23 omega   41.00  126.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -30.0000 85

 24 omega   39.00  109.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 25 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -180.0000 84

 26 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -150.0000 94

 27 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  -90.0000 88

 28 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   90.0000 84

 29 omega    1.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   93.0000   25.7650 26

 30 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  120.0000 94

 31 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000    0.0000 88

 32 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -60.0000 74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1730625000
_diffrn_orient_matrix_UB_12      0.0880222000
_diffrn_orient_matrix_UB_13      0.0316140000
_diffrn_orient_matrix_UB_21      0.0054810000
_diffrn_orient_matrix_UB_22      -0.0518964000
_diffrn_orient_matrix_UB_23      0.0824881000
_diffrn_orient_matrix_UB_31      0.1372642000
_diffrn_orient_matrix_UB_32      -0.0683111000
_diffrn_orient_matrix_UB_33      -0.0388075000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15706
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.654
_diffrn_reflns_theta_min         4.692
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.962
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       block
_exptl_crystal_F_000             661
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         5559
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0751
_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^)+(0.1442P)^2^+0.5633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2198
_refine_ls_wR_factor_ref         0.2378
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4365
_reflns_number_total             5559
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra07495j2.cif
_cod_data_source_block           hc-wry-15-2
_cod_original_cell_volume        1432.45(11)
_cod_original_formula_sum        'C27 H29.41 N9 O9.50'
_cod_database_code               7231875
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 C4-C2
 1.53 with sigma of 0.02
 H2A-C2
 0.96 with sigma of 0.02
 H2B-C2
 0.96 with sigma of 0.02
 H2C-C2
 0.96 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C1AB)=Sof(H1AC)=Sof(H1AD)=1-FVAR(1)
 Sof(C1AA)=Sof(H1AA)=Sof(H1AB)=FVAR(1)
 Sof(C0AB)=1-FVAR(2)
 Sof(C2AA)=Sof(H2AA)=Sof(H2AB)=FVAR(2)
 Sof(N00Z)=1-FVAR(3)
 Sof(N00Y)=FVAR(3)
5.a Secondary CH2 refined with riding coordinates:
 C00S(H00B,H00C), C012(H01A,H01B), C2AA(H2AA,H2AB), C1AA(H1AA,H1AB), C1AB(H1AC,
 H1AD), C4(H4A,H4B)
5.b Aromatic/amide H refined with riding coordinates:
 N003(H003), N007(H007), N008(H008), N00A(H00A), C00I(H00I), C00J(H00J),
 C00K(H00K), C00M(H00M), C00O(H00O), C00R(H00R), C00T(H00T), C00W(H00W),
 C00Z(H00Z), C010(H010), C011(H011), C014(H014)
5.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_shelx_res_checksum              79250
_olex2_date_sample_data_collection 2017-06-19
_olex2_submission_special_instructions 'No special instructions were received'