Spirocyclic rhodamine B benzoisothiazole derivative: a multi-stimuli fluorescent switch manifesting ethanol-responsiveness, photo responsiveness, and acidochromism.
Battula, Himabindu; Nath, Moromi; Mishra, Sabyashachi; Jayanty, Subbalakshmi; RSC advances 13 (2023) 5134–5148; doi:10.1039/d2ra08022b

data_7246292
_publ_section_title
;
 Spirocyclic rhodamine B benzoisothiazole derivative: a multi-stimuli
 fluorescent switch manifesting ethanol-responsiveness, photo
 responsiveness, and acidochromism.
;
_journal_issue                   8
_journal_name_full               'RSC advances'
_journal_page_first              5134
_journal_page_last               5148
_journal_paper_doi               10.1039/d2ra08022b
_journal_volume                  13
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C35 H33 N5 O4 S'
_chemical_formula_sum            'C35 H33 N5 O4 S'
_chemical_formula_weight         619.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-08-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-18 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.908(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.65490(10)
_cell_length_b                   24.1161(3)
_cell_length_c                   12.8100(2)
_cell_measurement_reflns_used    18772
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.7700
_cell_measurement_theta_min      4.1400
_cell_volume                     3053.88(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_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     -5.00  46.00   0.50    5.09    --    0.00   0.00  60.00  102
  2  \w     63.00  88.00   0.50    5.09    --    0.00  77.00 150.00   50
  3  \w    -30.00  56.00   0.50    5.09    --    0.00  77.00 150.00  172
  4  \w    -29.00  84.00   0.50    5.09    --    0.00  82.00   0.00  226
  5  \w    -88.00 -25.00   0.50    5.09    --    0.00   0.00  60.00  126
  6  \w     50.00  89.00   0.50    5.09    --    0.00  57.00  60.00   78
  7  \w     19.00 139.00   0.50   20.35    --  107.20 -82.00-150.00  240
  8  \w     48.00 140.00   0.50   20.35    --  107.20 -82.00  60.00  184
  9  \w     80.00 197.00   0.50   20.35    --  107.20  15.00 150.00  234
 10  \w     48.00 110.00   0.50   20.35    --  107.20 -82.00   0.00  124
 11  \w    112.00 138.00   0.50   20.35    --  107.20 -82.00   0.00   52
 12  \w     19.00  89.00   0.50   20.35    --  107.20 -30.00  90.00  140
 13  \w     19.00 125.00   0.50   20.35    --  107.20 -61.00-150.00  212
 14  \w     19.00  79.00   0.50   20.35    --  107.20 -15.00 -90.00  120
 15  \w    160.00 186.00   0.50   20.35    --  107.20  82.00  30.00   52
 16  \w     69.00 114.00   0.50   20.35    --  107.20 -82.00 -60.00   90
 17  \w     45.00 104.00   0.50   20.35    --  107.20 -82.00 150.00  118
 18  \w     93.00 183.00   0.50   20.35    --  107.20  61.00  60.00  180
 19  \w    103.00 135.00   0.50   20.35    --  107.20 -15.00 150.00   64
 20  \w     99.00 125.00   0.50   20.35    --  107.20 -15.00 -90.00   52
 21  \w     19.00  98.00   0.50   20.35    --  107.20 -15.00 150.00  158
 22  \w     18.00 131.00   0.50   20.35    --  107.20 -61.00   0.00  226
 23  \w     20.00  45.00   0.50   20.35    --  107.20 -15.00  60.00   50
 24  \w     87.00 112.00   0.50   20.35    --  107.20 -15.00  60.00   50
 25  \w     79.00 104.00   0.50   20.35    --  107.20 -82.00 120.00   50
 26  \w    100.00 125.00   0.50   20.35    --  107.20 -61.00-120.00   50
 27  \w     82.00 107.00   0.50   20.35    --  107.20 -82.00-180.00   50
 28  \w    103.00 143.00   0.50   20.35    --  107.20  82.00  30.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0645767000
_diffrn_orient_matrix_UB_12      0.0573474000
_diffrn_orient_matrix_UB_13      -0.0023802000
_diffrn_orient_matrix_UB_21      0.1415841000
_diffrn_orient_matrix_UB_22      0.0266384000
_diffrn_orient_matrix_UB_23      0.0452514000
_diffrn_orient_matrix_UB_31      -0.0080679000
_diffrn_orient_matrix_UB_32      0.0088291000
_diffrn_orient_matrix_UB_33      -0.1215353000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37072
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.782
_diffrn_reflns_theta_min         3.719
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.339
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 5220 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.174(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     819
_refine_ls_number_reflns         12789
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0910P)^2^+0.8800P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1437
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                11761
_reflns_number_total             12789
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra08022b2.cif
_cod_data_source_block           exp_965_rh-bit-2f
_cod_database_code               7246292
_shelxl_version_number           2012-9
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.776
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C18(H18A,H18B), C20(H20A,H20B), C49(H49A,
 H49B), C51(H51A,H51B), C53(H53A,H53B), C55(H55A,H55B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C23(H23), C24(H24),
 C25(H25), C26(H26), C31(H31), C33(H33), C34(H34), C37(H37), C40(H40), C44(H44),
  C45(H45), C47(H47), C58(H58), C59(H59), C60(H60), C61(H61), C66(H66),
 C68(H68), C69(H69), C39(H39)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C), C50(H50A,H50B,H50C), C52(H52A,H52B,H52C), C54(H54A,H54B,H54C), C56(H56A,
 H56B,H56C)
;
_shelx_res_checksum              72476
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.597
_oxdiff_exptl_absorpt_empirical_full_min 0.585