Ionic Pyridinium-Oxazole Dyads: Design, Synthesis, and Application in Mitochondrial Imaging.
Shaikh, Aslam C.; Varma, Mokshada E.; Mule, Ravindra D.; Banerjee, Somsuvra; Kulkarni, Prasad P.; Patil, Nitin T.; The Journal of organic chemistry 84 (2019) 1766–1777; doi:10.1021/acs.joc.8b02528

data_4033757
_publ_section_title
;
 Ionic Pyridinium-Oxazole Dyads: Design, Synthesis, and Application in
 Mitochondrial Imaging.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1766
_journal_page_last               1777
_journal_paper_doi               10.1021/acs.joc.8b02528
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C19 H11 F N O, C F3 O3 S'
_chemical_formula_sum            'C20 H11 F4 N O4 S'
_chemical_formula_weight         437.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-11-12
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.183(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2762(6)
_cell_length_b                   12.0264(5)
_cell_length_c                   15.3863(9)
_cell_measurement_reflns_used    3203
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.7870
_cell_measurement_theta_min      3.2400
_cell_volume                     1816.65(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.8430
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w      0.00  83.00   1.00    8.54    --   19.75  57.00 -30.00   83
  2  \w      3.00  85.00   1.00    8.54    --   19.75  77.00-150.00   82
  3  \w     29.00  68.00   1.00    8.54    --   19.75-107.00   3.00   39
  4  \w    -45.00 -13.00   1.00    8.54    --  -20.06 -19.00  90.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0672030000
_diffrn_orient_matrix_UB_12      -0.0090290000
_diffrn_orient_matrix_UB_13      -0.0287216000
_diffrn_orient_matrix_UB_21      0.0259025000
_diffrn_orient_matrix_UB_22      -0.0094032000
_diffrn_orient_matrix_UB_23      -0.0372871000
_diffrn_orient_matrix_UB_31      0.0063296000
_diffrn_orient_matrix_UB_32      -0.0575105000
_diffrn_orient_matrix_UB_33      0.0105312000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8096
_diffrn_reflns_theta_full        29.24
_diffrn_reflns_theta_max         29.24
_diffrn_reflns_theta_min         3.25
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.8041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1208
_reflns_number_gt                3228
_reflns_number_total             4158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02528_si_002.cif
_cod_data_source_block           aslam
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4033757
_chemical_oxdiff_formula         'C10 H10 N10 O10 S1 F1'
_chemical_oxdiff_usercomment     TEST
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.287
_oxdiff_exptl_absorpt_empirical_full_min 0.758