The synthesis of new fluorescent bichromophoric compounds as ratiometric pH probes for intracellular measurements.
Saura, A. Vanessa; Marín, María J; Burguete, M. Isabel; Russell, David A.; Galindo, Francisco; Luis, Santiago V.; Organic & biomolecular chemistry 13 (2015) 7736–7749; doi:10.1039/c5ob00704f

data_7154545
_publ_section_title
;
 The synthesis of new fluorescent bichromophoric compounds as ratiometric
 pH probes for intracellular measurements.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7736
_journal_page_last               7749
_journal_paper_doi               10.1039/c5ob00704f
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H38 N4 O3 S'
_chemical_formula_sum            'C34 H38 N4 O3 S'
_chemical_formula_weight         582.74
_chemical_name_common            AntValA2DNS
_chemical_properties_physical    Photo-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-08
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Apr 20 2012 13:29:48, GUI svn.r4208)
;
_audit_update_record
;
2015-03-30 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7342(2)
_cell_length_b                   12.9336(3)
_cell_length_c                   27.4037(5)
_cell_measurement_reflns_used    29137
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.4390
_cell_measurement_theta_min      3.7120
_cell_volume                     3095.65(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9911
_diffrn_measurement_details
;
  1 omega  -50.00   36.00   0.4000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680   38.0000    0.0000 215

  2 omega  -50.00   36.00   0.4000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680   38.0000  150.0000 215

  3 omega -124.00  -78.00   0.4000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -87.0000   44.0000 115

  4 omega -116.00  -14.00   0.4000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -38.0000 -120.0000 255

  5 omega  -50.00   36.00   0.4000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680   38.0000   60.0000 215

  6 omega   55.00  127.00   0.4000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0680 -178.0000  -30.0000 180

  7 omega   57.00  129.00   0.4000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0680  178.0000   90.0000 180

  8 omega   31.00  121.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400 -125.0000 -150.0000 225

  9 omega   94.00  178.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  125.0000 -180.0000 210

 10 omega   94.00  178.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  125.0000   90.0000 210

 11 omega   21.00  107.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -94.0000   90.0000 215

 12 omega   78.00  178.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   45.0000  -30.0000 250

 13 omega   75.00  177.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   30.0000 -120.0000 255

 14 omega   31.00  121.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400 -125.0000   60.0000 225

 15 omega   28.00   90.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000  -60.0000 155

 16 omega   31.00   99.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -45.0000 -150.0000 170

 17 omega   75.00  177.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   30.0000  -60.0000 255

 18 omega   28.00   90.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000   60.0000 155

 19 omega   31.00   99.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -45.0000  120.0000 170

 20 omega   75.00  177.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   30.0000  150.0000 255

 21 omega -114.00  -10.00   0.4000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -57.0000   60.0000 260

 22 omega -119.00   -7.00   0.4000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -77.0000  -90.0000 280

 23 omega -119.00   -7.00   0.4000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -77.0000 -180.0000 280

 24 omega  -50.00   36.00   0.4000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680   38.0000  -60.0000 215

 25 omega -119.00   -7.00   0.4000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -77.0000   90.0000 280

 26 omega -119.00   -7.00   0.4000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -77.0000    0.0000 280

 27 omega   75.00  177.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   30.0000   60.0000 255

 28 omega   75.00  177.00   0.4000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   61.0000    0.0000 255
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0247603000
_diffrn_orient_matrix_UB_12      0.0194976000
_diffrn_orient_matrix_UB_13      -0.0549010000
_diffrn_orient_matrix_UB_21      -0.0739809000
_diffrn_orient_matrix_UB_22      -0.1052842000
_diffrn_orient_matrix_UB_23      -0.0117424000
_diffrn_orient_matrix_UB_31      -0.1580821000
_diffrn_orient_matrix_UB_32      0.0522738000
_diffrn_orient_matrix_UB_33      -0.0031358000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            44978
_diffrn_reflns_theta_full        72.58
_diffrn_reflns_theta_max         72.58
_diffrn_reflns_theta_min         3.23
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.248
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.2286
_exptl_crystal_size_mid          0.2012
_exptl_crystal_size_min          0.0696
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         6093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.5172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                5949
_reflns_number_total             6093
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00704f2.cif
_cod_data_source_block           str1636
_cod_depositor_comments          'Adding full bibliography for 7154545.cif.'
_cod_database_code               7154545
_chemical_oxdiff_formula         'C34 H38 N4 O3 S '
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97