An unprecedented oxidised julolidine-BODIPY conjugate and its application in real-time ratiometric fluorescence sensing of sulfite.
Sirbu, D.; Zeng, L.; Waddell, P. G.; Benniston, A. C.; Organic & biomolecular chemistry 17 (2019) 7360–7368; doi:10.1039/c9ob01316d

data_7156982
_publ_section_title
;
 An unprecedented oxidised julolidine-BODIPY conjugate and its application
 in real-time ratiometric fluorescence sensing of sulfite.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7360
_journal_page_last               7368
_journal_paper_doi               10.1039/c9ob01316d
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety
'C7 H7 O3 S, C35 H27 B F2 N5, 4.625(H2 O), 0.375(O)'
_chemical_formula_sum            'C42 H43.25 B F2 N5 O8 S'
_chemical_formula_weight         826.93
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-22
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-04-11 deposited with the CCDC.    2019-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                109.598(3)
_cell_angle_beta                 95.323(2)
_cell_angle_gamma                99.3812(19)
_cell_formula_units_Z            4
_cell_length_a                   8.04807(16)
_cell_length_b                   20.9106(6)
_cell_length_c                   25.9109(8)
_cell_measurement_reflns_used    19848
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      66.7400
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_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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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)'
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;
  1 omega  -99.00  -18.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
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omega____ theta____ kappa____ phi______ frames
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omega____ theta____ kappa____ phi______ frames
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  4 omega   -3.00   96.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
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omega____ theta____ kappa____ phi______ frames
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  6 omega    9.00  133.00   1.0000   58.0000
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  7 omega    9.00  133.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega    9.00  133.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   19.00   50.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
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omega____ theta____ kappa____ phi______ frames
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 11 omega   78.00  112.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
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 12 omega  130.00  171.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  -90.0000 41

 13 omega   38.00   77.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  120.0000 39

 14 omega   20.00   46.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
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 15 omega   76.00  102.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  159.0057 26

 16 omega   97.00  150.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega   80.00  105.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
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 18 omega  129.00  154.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   17.00   62.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega  114.00  163.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
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 21 omega   20.00   78.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
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 22 omega   20.00   77.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -30.0000 57

 23 omega   16.00   41.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  150.0000 25

 24 omega   20.00   80.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  -90.0000 60

 25 omega   31.00   70.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000   90.0000 39

 26 omega   74.00  165.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
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 27 omega   45.00  113.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -90.0000 68

 28 omega   35.00   61.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000    0.0000 26

 29 omega   32.00   72.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000  -60.0000 40

 30 omega    9.00   61.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  159.0057 52

 31 omega  110.00  167.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -120.0000 57

 32 omega   70.00  124.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -30.0000 54

 33 omega   76.00  132.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  -52.5931 56

 34 omega   55.00   81.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000 -180.0000 26

 35 omega   74.00  152.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
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 36 omega  127.00  153.00   1.0000   58.0000
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 37 omega   21.00   47.00   1.0000   58.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  -52.5931 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0158558000
_diffrn_orient_matrix_UB_12      0.0194948000
_diffrn_orient_matrix_UB_13      -0.0518976000
_diffrn_orient_matrix_UB_21      0.0403268000
_diffrn_orient_matrix_UB_22      0.0775152000
_diffrn_orient_matrix_UB_23      0.0366603000
_diffrn_orient_matrix_UB_31      0.1916661000
_diffrn_orient_matrix_UB_32      -0.0009619000
_diffrn_orient_matrix_UB_33      0.0069764000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            56540
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.938
_diffrn_reflns_theta_min         2.370
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.310
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       prism
_exptl_crystal_F_000             1733
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1152
_refine_ls_number_reflns         14171
_refine_ls_number_restraints     949
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0635P)^2^+1.2959P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11195
_reflns_number_total             14171
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01316d2.cif
_cod_data_source_block           acb160026
_cod_depositor_comments          'Adding full bibliography for 7156982.cif.'
_cod_original_cell_volume        4001.65(19)
_cod_database_code               7156982
_chemical_oxdiff_formula         'C107 H90 Ag2 B3 F12 N15 O6 S2'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O10-H10A = O10-H10B = O9_$2-H9A_$2 = O9_$2-H9B_$2 = O7_$2-H7A_$2 = O7_$2-
 H7B_$2 = O8_$2-H8A_$2 = O8_$2-H8B_$2 = O11_$1-H11B_$1 = O11_$1-H11A_$1 =
 O13_$1-H13A_$1 = O13_$1-H13B_$1 = O14A_$1-H14B_$1 = O14A_$1-H14A_$1 = O16A_$3-
 H16A_$3 = O15A_$3-H15A_$3 = O16A_$3-H16B_$3 = O15A_$3-H15B_$3 = O12_$1-H12A_$1
 0.9 with sigma of 0.02
 O12-H12B
 0.9 with sigma of 0.02
 H14B-H14A
 1.34 with sigma of 0.04
 H13B-H13A
 1.34 with sigma of 0.04
 H15A-H15B
 1.34 with sigma of 0.04
 C72B-C71 \\sim C72A-C71
 with sigma of 0.02
 C72B-C73 \\sim C72A-C73
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C72A \\sim C72B: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(O15A) = Uanis(O16B)
Uanis(O16A) = Uanis(O15B)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: H71A(0.74626) H71B(0.74626) H71C(0.25374) H71D(0.25374)
 H73A(0.74626) H73B(0.74626) H73C(0.25374) H73D(0.25374) O15A(0.75) H15A(0.75)
 H15B(0.75) O15B(0.25) C72A(0.74626) H72A(0.74626) H72B(0.74626) O16A(0.75)
 H16A(0.75) H16B(0.75) O16B(0.25) C72B(0.25374) H72C(0.25374) H72D(0.25374)
 O14B(0.25) O14A(0.75) H14A(0.75) H14B(0.75)
6.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C71(H71A,H71B), C71(H71C,
 H71D), C73(H73A,H73B), C73(H73C,H73D), C72A(H72A,H72B), C72B(H72C,H72D)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26),
  C28(H28), C32(H32), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40),
 C44(H44), C45(H45), C49(H49), C50(H50), C52(H52), C53(H53), C55(H55), C56(H56),
  C57(H57), C58(H58), C60(H60), C61(H61), C63(H63), C64(H64), C66(H66),
 C70(H70), C74(H74), C75(H75), C76(H76), C78(H78), C79(H79), C81(H81), C82(H82),
  C85(H85), C86(H86), C88(H88), C89(H89)
6.c Idealised Me refined as rotating group:
 C83(H83A,H83B,H83C), C90(H90A,H90B,H90C)
;
_shelx_res_checksum              16092
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'