Acceptor–donor–acceptor-linked triphenylamine and phenothiazine motifs as cousin molecules: the methyl effect on stimuli-responsiveness, crystallochromism, and dual-state emission
Bhuin, Shouvik; Bhattacharya, Suman; Chakravarty, Manab; New Journal of Chemistry 45 (2021) 21236–21247; doi:10.1039/D1NJ04190H

data_7061040
_publ_section_title
;
 Acceptor--donor--acceptor-linked triphenylamine and phenothiazine motifs
 as cousin molecules: the methyl effect on stimuli-responsiveness,
 crystallochromism, and dual-state emission
;
_journal_issue                   45
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              21236
_journal_page_last               21247
_journal_paper_doi               10.1039/D1NJ04190H
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C26 H24 N4 S'
_chemical_formula_sum            'C26 H24 N4 S'
_chemical_formula_weight         424.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc26jlkx
_audit_creation_date             2020-05-23
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.05.07 svn.rd67b107b for OlexSys, GUI svn.r6105)
;
_audit_update_record
;
2020-10-31 deposited with the CCDC.	2021-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                91.003(3)
_cell_angle_beta                 95.825(4)
_cell_angle_gamma                106.344(4)
_cell_formula_units_Z            4
_cell_length_a                   8.9131(4)
_cell_length_b                   11.8184(4)
_cell_length_c                   21.8914(9)
_cell_measurement_reflns_used    6097
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      78.7250
_cell_measurement_theta_min      3.9070
_cell_volume                     2198.83(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_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    -69.00 -42.00   0.50    2.45    --    0.00 -57.00-180.00   54
  2  \w    -44.00 -16.00   0.50    2.45    --    0.00 -37.00 -30.00   56
  3  \w    -89.00 -35.00   0.50    2.45    --    0.00 -57.00  60.00  108
  4  \w    -10.00  16.00   0.50    2.45    --    0.00 -57.00-180.00   52
  5  \w     -6.00  19.00   0.50    2.45    --    0.00 -37.00 -30.00   50
  6  \w    -19.00  88.00   0.50    2.45    --    0.00  37.00 -60.00  214
  7  \w    -31.00  22.00   0.50    2.45    --    0.00 -57.00  60.00  106
  8  \w    -18.00  85.00   0.50    2.45    --    0.00  37.00 150.00  206
  9  \w    -33.00  -6.00   0.50    2.45    --    0.00 -77.00 -60.00   54
 10  \w     55.00 139.00   0.50    9.80    --  107.20 -82.00-180.00  168
 11  \w     39.00 131.00   0.50    9.80    --  107.20 -61.00 -30.00  184
 12  \w    100.00 126.00   0.50    9.80    --  107.20 -82.00 -60.00   52
 13  \w     27.00 133.00   0.50    9.80    --  107.20 -15.00-180.00  212
 14  \w     96.00 123.00   0.50    9.80    --  107.20 -82.00-120.00   54
 15  \w     80.00 106.00   0.50    9.80    --  107.20 -45.00  60.00   52
 16  \w     87.00 188.00   0.50    9.80    --  107.20  45.00 150.00  202
 17  \w     26.00 126.00   0.50    9.80    --  107.20 -30.00-150.00  200
 18  \w     21.00 116.00   0.50    9.80    --  107.20 -82.00   0.00  190
 19  \w     50.00 112.00   0.50    9.80    --  107.20 -82.00 -30.00  124
 20  \w     50.00 130.00   0.50    9.80    --  107.20 -61.00-180.00  160
 21  \w     93.00 196.00   0.50    9.80    --  107.20  45.00-180.00  206
 22  \w     19.00 139.00   0.50    9.80    --  107.20 -82.00  90.00  240
 23  \w     94.00 185.00   0.50    9.80    --  107.20  30.00-150.00  182
 24  \w     19.00 110.00   0.50    9.80    --  107.20 -61.00  90.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): 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      -0.0927098000
_diffrn_orient_matrix_UB_12      -0.0275431000
_diffrn_orient_matrix_UB_13      -0.0644160000
_diffrn_orient_matrix_UB_21      -0.1130728000
_diffrn_orient_matrix_UB_22      -0.1102448000
_diffrn_orient_matrix_UB_23      0.0237028000
_diffrn_orient_matrix_UB_31      -0.1070843000
_diffrn_orient_matrix_UB_32      0.0747238000
_diffrn_orient_matrix_UB_33      0.0174455000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10060
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.047
_diffrn_reflns_theta_min         3.902
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.458
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.984
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     562
_refine_ls_number_reflns         10060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0671
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1415P)^2^+0.4708P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1872
_refine_ls_wR_factor_ref         0.1933
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8733
_reflns_number_total             10060
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9674\% 
 around [-0.00 0.00 1.00] (reciprocal) or [0.27 0.09 0.96] (direct)
;
_cod_data_source_file            d1nj04190h2.cif
_cod_data_source_block           exp_530_ptz-cnc_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 7061040--7061042.cif.'
_cod_original_cell_volume        2198.84(16)
_cod_database_code               7061040
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H12 N2 O2 S1'
_shelx_estimated_absorpt_t_max   0.868
_shelx_estimated_absorpt_t_min   0.759
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C49B)=Sof(H49A)=Sof(H49B)=Sof(C50B)=Sof(H50A)=Sof(H50B)=Sof(C48B)=
 Sof(H48A)=Sof(H48B)=Sof(C51B)=Sof(H51A)=Sof(H51B)=Sof(C52B)=Sof(H52A)=
 Sof(H52B)=Sof(H52C)=1-FVAR(1)
 Sof(C48A)=Sof(H48C)=Sof(H48D)=Sof(C49A)=Sof(H49C)=Sof(H49D)=Sof(C50A)=
 Sof(H50C)=Sof(H50D)=Sof(C51A)=Sof(H51C)=Sof(H51D)=Sof(C52A)=Sof(H52D)=
 Sof(H52E)=Sof(H52F)=FVAR(1)
3.a Rotating group:
 N5(H5A,H5B), N37(H37A,H37B)
3.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C49B(H49A,H49B), C24(H24A,H24B), C50B(H50A,H50B), C48B(H48A,
 H48B), C23(H23A,H23B), C25(H25A,H25B), C51B(H51A,H51B), C48A(H48C,H48D),
 C49A(H49C,H49D), C50A(H50C,H50D), C51A(H51C,H51D)
3.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C5(H5), C31(H31), C11(H11), C14(H14), C38(H38), C41(H41), C37(H37),
 C21(H21), C18(H18), C19(H19), C43(H43), C46(H46), C20(H20), C45(H45), C44(H44)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C33(H33A,H33B,H33C), C26(H26A,H26B,H26C), C52B(H52A,H52B,
 H52C), C52A(H52D,H52E,H52F)
;
_shelx_res_checksum              54408
_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 2.248
_oxdiff_exptl_absorpt_empirical_full_min 0.655
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2