Thermodynamics and kinetics of protonated merocyanine photoacids in water
Berton, Cesare; Busiello, Daniel Maria; Zamuner, Stefano; Solari, Euro; Scopelliti, Rosario; Fadaei-Tirani, Farzaneh; Severin, Kay; Pezzato, Cristian; Chemical Science  (2020) –; doi:10.1039/D0SC03152F

data_1558723
_publ_section_title
;
 Thermodynamics and kinetics of protonated merocyanine photoacids in water
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03152F
_journal_year                    2020
_chemical_formula_moiety         'C22 H25 N O4 S'
_chemical_formula_sum            'C22 H25 N O4 S'
_chemical_formula_weight         399.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-05-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-05-22 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.1075(3)
_cell_length_b                   6.98646(10)
_cell_length_c                   19.6635(2)
_cell_measurement_reflns_used    12532
_cell_measurement_temperature    139.99(10)
_cell_measurement_theta_max      72.4240
_cell_measurement_theta_min      4.4830
_cell_volume                     2350.20(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      139.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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   -105.00 -22.00   1.00    5.00    --  -40.85 -38.00  60.00   83
  2  \w   -103.00 -73.00   1.00    5.00    --  -40.85 -57.00 150.00   30
  3  \w    -66.00 -20.00   1.00    5.00    --  -40.85 -57.00 -60.00   46
  4  \w   -111.00 -13.00   1.00    5.00    --  -40.85 -57.00   0.00   98
  5  \w    -76.00 -51.00   1.00    5.00    --  -40.85 -57.00  60.00   25
  6  \w    -19.00  69.00   1.00    5.00    --   40.85 -77.00 -60.00   88
  7  \w      7.00  64.00   1.00    5.00    --   40.85 -99.00-150.00   57
  8  \w      7.00  80.00   1.00    5.00    --   40.85 -99.00-180.00   73
  9  \w     22.00  52.00   1.00    5.00    --   40.85  57.00 120.00   30
 10  \w     23.00  95.00   1.00   20.00    --  105.15 -94.00 -30.00   72
 11  \w     80.00 107.00   1.00   20.00    --  105.15  45.00  60.00   27
 12  \w     28.00 100.00   1.00   20.00    --  105.15 -94.00  30.00   72
 13  \w    114.00 177.00   1.00   20.00    --  105.15  61.00 120.00   63
 14  \w     76.00 105.00   1.00   20.00    --  105.15  61.00  90.00   29
 15  \w     78.00 168.00   1.00   20.00    --  105.15  54.00  76.20   90
 16  \w     79.00 120.00   1.00   20.00    --  105.15  49.00 119.85   41
 17  \w    104.00 160.00   1.00   20.00    --  105.15 111.00-150.00   56
 18  \w     76.00 103.00   1.00   20.00    --  105.15  61.00  60.00   27
 19  \w    122.00 158.00   1.00   20.00    --  105.15  45.00 150.00   36
 20  \w     78.00 104.00   1.00   20.00    --  105.15  53.00 125.02   26
 21  \w     79.00 106.00   1.00   20.00    --  105.15  45.00 150.00   27
 22  \w     77.00 136.00   1.00   20.00    --  105.15  61.00   0.00   59
 23  \w    142.00 171.00   1.00   20.00    --  105.15  61.00  30.00   29
 24  \w     79.00 111.00   1.00   20.00    --  105.15  45.00   0.00   32
 25  \w     80.00 106.00   1.00   20.00    --  105.15  45.00 120.00   26
 26  \w     79.00 106.00   1.00   20.00    --  105.15  61.00 120.00   27
 27  \w     24.00  96.00   1.00   20.00    --  105.15 -94.00-150.00   72
 28  \w     76.00 102.00   1.00   20.00    --  105.15  61.00  30.00   26
 29  \w     81.00 108.00   1.00   20.00    --  105.15  30.00  60.00   27
 30  \w     81.00 108.00   1.00   20.00    --  105.15  45.00  30.00   27
 31  \w     76.00 102.00   1.00   20.00    --  105.15  60.00  -5.57   26
 32  \w    125.00 174.00   1.00   20.00    --  105.15  62.00  11.16   49
 33  \w     77.00 102.00   1.00   20.00    --  105.15  62.00  11.16   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0150368000
_diffrn_orient_matrix_UB_12      -0.0641668000
_diffrn_orient_matrix_UB_13      -0.1209715000
_diffrn_orient_matrix_UB_21      0.0200684000
_diffrn_orient_matrix_UB_22      0.0449382000
_diffrn_orient_matrix_UB_23      -0.1738763000
_diffrn_orient_matrix_UB_31      0.0864891000
_diffrn_orient_matrix_UB_32      0.0007047000
_diffrn_orient_matrix_UB_33      0.0613503000
_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  0.0193
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19755
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.568
_diffrn_reflns_theta_min         5.171
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.422
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.161
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       0.00076(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4466
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0507P)^2^+0.3364P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                4388
_reflns_number_total             4466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc03152f2.cif
_cod_data_source_block           cp38
_cod_original_cell_volume        2350.19(6)
_cod_database_code               1558723
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C24 H33 N1 O6 S1'
_shelx_estimated_absorpt_t_max   0.803
_shelx_estimated_absorpt_t_min   0.733
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.96(2)
 0.04(2)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5), C6(H6), C7(H7), C15(H15), C16(H16), C18(H18), C19(H19),
 C20(H20), C21(H21)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              31311
_shelx_fab_checksum              72911
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.542
_oxdiff_exptl_absorpt_empirical_full_min 0.494