Fluorescence switching of imidazo[1,5-a]pyridinium ions: pH-sensors with dual emission pathways.
Hutt, Johnathon T.; Jo, Junyong; Olasz, András; Chen, Chun-Hsing; Lee, Dongwhan; Aron, Zachary D.; Organic letters 14 (2012) 3162–3165; doi:10.1021/ol3012524

data_1507837
_publ_section_title
;
 Fluorescence switching of imidazo[1,5-a]pyridinium ions: pH-sensors with
 dual emission pathways.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3162
_journal_page_last               3165
_journal_paper_doi               10.1021/ol3012524
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C17 H20 F6 N3 P1'
_chemical_formula_sum            'C17 H20 F6 N3 P'
_chemical_formula_weight         411.33
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             12-02-28
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                90
_cell_angle_beta                 99.3450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.3719(19)
_cell_length_b                   10.2345(7)
_cell_length_c                   14.8466(11)
_cell_measurement_reflns_used    7008
_cell_measurement_temperature    150
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     3654.1(5)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20229
_diffrn_reflns_theta_full        30.028
_diffrn_reflns_theta_max         30.028
_diffrn_reflns_theta_min         2.163
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1696.000
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.174
_refine_diff_density_max         0.83
_refine_diff_density_min         -0.83
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         5255
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0877
_refine_ls_shift/su_max          0.0178595
_refine_ls_shift/su_mean         0.0018080
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.11P)^2^ + 9.60P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2454
_refine_ls_wR_factor_gt          0.2263
_refine_ls_wR_factor_ref         0.2412
_reflns_limit_h_max              33
_reflns_limit_h_min              -34
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                4627
_reflns_number_total             5333
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0960
_oxford_refine_ls_scale          0.07627(4)
_oxford_reflns_number_all        5320
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_oxford_structure_analysis_title 'mo_12023_0m in C2/c'
_cod_data_source_file            ol3012524_si_001.cif
_cod_data_source_block           12023
_cod_depositor_comments          'Adding full bibliography for 1507837.cif.'
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_original_formula_sum        'C17 H20 F6 N3 P1'
_cod_database_code               1507837
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT P    (    1 ,X'S,U'S) 
CONT F    (    1 ,X'S,U'S)  UNTIL F    (   6 ) 
CONT F    (    11 ,X'S,U[ISO])  UNTIL F    (   61 ) 
CONT N    (    1 ,X'S,U'S)  UNTIL N    (   31 ) 
CONT C    (    1 ,X'S,U'S)  UNTIL C    (   13 ) 
CONT C    (    14 ,X'S,U'S)  UNTIL C    (   17 ) 
CONT C    (    18 ,X'S,U[ISO])  UNTIL C    (   21 ) 
SUMFIX PART(1001,OCC) AND PART(1002,OCC) 
SUMFIX PART(1003,OCC) AND PART(1004,OCC) 
SUMFIX PART(2001,OCC) AND PART(2002,OCC) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) H   ( 153,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) H   ( 173,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ)'S  0.0, 0.010000 = F(1) TO F(3) 
DISTANCE 1.540000 , 0.050000 = C(20) TO C(21) 
END                                                                             
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