Colorimetric and Luminescent Sensors for Chloride: Hydrogen Bonding vs Deprotonation
Elmes, Robert B. P.; Turner, Peter; Jolliffe, Katrina A.; Organic Letters 15 (2013) 5638–; doi:10.1021/ol402500q

data_1513104
_publ_section_title
;
 Colorimetric and Luminescent Sensors for Chloride: Hydrogen Bonding vs
 Deprotonation
;
_journal_issue                   22
_journal_name_full               'Organic Letters'
_journal_page_first              5638
_journal_paper_doi               10.1021/ol402500q
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C29 H22 F6 N2 O3 S'
_chemical_formula_weight         592.54
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 97.803(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2357(6)
_cell_length_b                   8.6902(5)
_cell_length_c                   14.9501(9)
_cell_measurement_reflns_used    3936
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.92
_cell_measurement_theta_min      2.72
_cell_volume                     1317.50(13)
_computing_cell_refinement       'SAINT (Bruker-AXS,2012)'
_computing_data_collection       'APEX (Bruker-AXS,2012)'
_computing_data_reduction        'SAINT and XPREP (Bruker-AXS,2012)'
_computing_molecular_graphics
;
  xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999)
  ORTEPII  (Johnson,C.K., 1976). 
  WinGX (Farrugia, 1999)
  shelXle (H&#x00FC;bschle,C.B., et al., 2011)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_crystal_treatment
;
attached with Exxon Paratone N, to a short length 
of fibre supported on a thin piece of copper wire 
inserted in a copper mounting pin.  The crystal was 
quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream. 
;
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  APEXII-FR591
_diffrn_measurement_method       \w+\f
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30710
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.182
_diffrn_reflns_theta_min         2.008
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS (Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       blade
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
;
 Flack x determined using 2155 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.431
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         6414
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.431
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.05P)^2^+0.2P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                5263
_reflns_number_total             6414
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol402500q_si_002.cif
_cod_data_source_block           1_kaj13pt2
_cod_database_code               1513104