Ladder-Type Dye with Large Transition Dipole Moment for Solvatochromism and Microphase Visualization.
Cao, Jian; Liu, Qi-Ming; Bai, Si-Jie; Wang, Hua-Chun; Ren, Xiancheng; Xu, Yun-Xiang; ACS applied materials & interfaces 11 (2019) 29814–29820; doi:10.1021/acsami.9b07677

data_4514482
_publ_section_title
;
 Ladder-Type Dye with Large Transition Dipole Moment for Solvatochromism
 and Microphase Visualization.
;
_journal_issue                   33
_journal_name_full               'ACS applied materials &amp; interfaces'
_journal_page_first              29814
_journal_page_last               29820
_journal_paper_doi               10.1021/acsami.9b07677
_journal_volume                  11
_journal_year                    2019
_chemical_formula_moiety         'C44 H33 Br O3 Se'
_chemical_formula_sum            'C45 H0.25 Br O5 Se'
_chemical_formula_weight         779.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.263(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6254(9)
_cell_length_b                   16.0784(8)
_cell_length_c                   16.8019(11)
_cell_measurement_reflns_used    3952
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2440
_cell_measurement_theta_min      3.3480
_cell_volume                     3860.9(4)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details
;
  1 omega  -82.00  -44.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1231  -77.0000   30.0000 38

  2 omega  -83.00   11.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1231  -77.0000   90.0000 94

  3 omega  -13.00   21.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1231  -99.0000  -30.0000 34

  4 omega  -16.00   34.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  -57.0000  -90.0000 50

  5 omega   43.00   69.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  178.0000  -90.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0051806000
_diffrn_orient_matrix_UB_12      0.0306391000
_diffrn_orient_matrix_UB_13      -0.0290545000
_diffrn_orient_matrix_UB_21      -0.0102869000
_diffrn_orient_matrix_UB_22      0.0315124000
_diffrn_orient_matrix_UB_23      0.0263154000
_diffrn_orient_matrix_UB_31      0.0482992000
_diffrn_orient_matrix_UB_32      0.0034758000
_diffrn_orient_matrix_UB_33      0.0181819000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20681
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.305
_diffrn_reflns_theta_min         3.040
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.050
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1517
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_platon_squeeze_details
;
TITL CF solution in P21/n
CELL   14.6254   16.0784   16.8019     90.00    102.26     90.00
SPGR P21/n
C101 0.906 0.248 0.170 !       6.93 eA-3
C102 0.691 0.813 0.486 !       6.12 eA-3
C103 0.343 0.328 0.616 !       3.23 eA-3
C104 0.650 0.721 0.337 !       2.57 eA-3
Q105 0.755 0.164 0.070 !       1.58 eA-3
C106 0.610 0.781 0.384 !       1.41 eA-3
Q107 0.813 0.165 0.768 !       1.16 eA-3
Q108 0.840 0.153 0.376 !       1.13 eA-3
Q109 0.983 0.336 0.902 !       1.07 eA-3
C110 0.386 0.314 0.541 !       1.05 eA-3
Q111 0.533 0.957 0.051 !       1.04 eA-3
Q112 0.200 0.466 0.545 !       1.00 eA-3
Q113 0.065 0.253 0.625 !       0.98 eA-3
Q114 0.139 0.044 0.658 !       0.96 eA-3
Q115 0.638 0.653 0.083 !       0.95 eA-3
Q116 0.640 0.950 0.157 !       0.95 eA-3
C117 0.623 0.820 0.437 !       0.92 eA-3
Q118 0.720 0.920 0.691 !       0.88 eA-3
Q119 0.513 0.190 0.094 !       0.87 eA-3
Q120 0.516 0.504 0.343 !       0.87 eA-3
Q121 0.314 0.173 0.230 !       0.86 eA-3
Q122 0.544 0.912 0.093 !       0.85 eA-3
Q123 0.643 0.798 0.809 !       0.85 eA-3
Q124 0.599 0.295 0.198 !       0.85 eA-3
Q125 0.421 0.091 0.841 !       0.84 eA-3
Q126 0.608 0.905 0.126 !       0.84 eA-3
Q127 0.687 0.233 0.684 !       0.84 eA-3
Q128 0.237 1.001 0.933 !       0.83 eA-3
Q129 0.246 0.182 0.812 !       0.83 eA-3
Q130 0.347 0.333 0.222 !       0.82 eA-3
Q131 0.394 0.980 0.689 !       0.82 eA-3
Q132 0.064 0.694 0.560 !       0.82 eA-3
Q133 0.201 0.316 0.499 !       0.81 eA-3
Q134 0.624 1.000 0.373 !       0.80 eA-3
Q135 0.639 0.831 0.304 !       0.79 eA-3
Q136 0.657 0.188 0.003 !       0.79 eA-3
Q137 0.738 0.418 0.820 !       0.79 eA-3
Q138 0.747 0.403 0.847 !       0.78 eA-3
Q139 0.091 0.341 0.102 !       0.78 eA-3
Q140 0.098 0.891 0.119 !       0.77 eA-3
Q141 0.405 0.652 0.520 !       0.77 eA-3
C142 0.629 0.737 0.497 !       0.76 eA-3
Q143 0.593 0.200 0.798 !       0.76 eA-3
Q144 0.797 0.130 0.068 !       0.76 eA-3
Q145 0.562 0.204 0.903 !       0.76 eA-3
Q146 0.188 0.158 0.809 !       0.76 eA-3
Q147 0.423 0.431 0.225 !       0.75 eA-3
Q148 0.953 0.503 0.388 !       0.75 eA-3
Q149 0.759 0.781 0.362 !       0.75 eA-3
Q150 0.123 0.553 0.249 !       0.74 eA-3
Q151 0.376 0.344 0.494 !       0.74 eA-3
Q152 0.433 0.983 0.851 !       0.73 eA-3
Q153 0.094 0.089 0.428 !       0.72 eA-3
Q154 0.592 0.132 0.771 !       0.72 eA-3
Q155 0.669 0.966 0.343 !       0.72 eA-3
Q156 0.611 0.239 0.948 !       0.71 eA-3
Q157 0.748 0.096 0.263 !       0.70 eA-3
Q158 0.479 0.641 0.939 !       0.70 eA-3
Q159 0.534 0.098 0.523 !       0.70 eA-3
Q160 0.378 0.456 0.369 !       0.70 eA-3
Q161 0.324 0.594 0.705 !       0.70 eA-3
Q162 0.292 0.713 0.013 !       0.69 eA-3
Q163 0.017 0.421 0.548 !       0.69 eA-3
Q164 0.077 0.443 0.596 !       0.69 eA-3
Q165 0.746 0.657 0.621 !       0.69 eA-3
Q166 0.620 0.595 0.571 !       0.68 eA-3
Q167 0.768 0.147 0.776 !       0.68 eA-3
Q168 0.357 0.922 0.988 !       0.68 eA-3
Q169 0.364 0.038 0.954 !       0.68 eA-3
Q170 0.950 0.690 0.120 !       0.68 eA-3
Q171 0.083 0.368 0.029 !       0.68 eA-3
Q172 0.204 0.685 0.500 !       0.67 eA-3
Q173 0.932 0.351 0.409 !       0.67 eA-3
Q174 0.737 0.264 0.748 !       0.67 eA-3
Q175 0.497 0.827 0.137 !       0.67 eA-3
Q176 0.810 0.370 0.390 !       0.67 eA-3
Q177 0.843 0.513 0.777 !       0.67 eA-3
Q178 0.818 0.864 0.875 !       0.66 eA-3
Q179 0.918 0.753 0.984 !       0.66 eA-3
Q180 0.473 0.466 0.689 !       0.66 eA-3
Q181 0.981 0.779 0.583 !       0.66 eA-3
Q182 0.423 0.995 0.224 !       0.66 eA-3
Q183 0.751 0.342 0.749 !       0.66 eA-3
Q184 0.749 0.846 0.749 !       0.66 eA-3
Q185 0.806 0.082 0.467 !       0.66 eA-3
Q186 0.187 0.545 0.715 !       0.66 eA-3
Q187 0.264 0.032 0.284 !       0.65 eA-3
Q188 0.967 0.553 0.499 !       0.65 eA-3
Q189 0.425 0.921 0.217 !       0.65 eA-3
Q190 0.097 0.563 0.352 !       0.65 eA-3
Q191 0.441 0.627 0.904 !       0.65 eA-3
Q192 0.470 0.110 0.935 !       0.64 eA-3
Q193 0.177 0.516 0.188 !       0.64 eA-3
Q194 0.558 0.816 0.404 !       0.64 eA-3
Q195 0.846 0.187 0.230 !       0.64 eA-3
Q196 0.830 0.822 0.646 !       0.64 eA-3
Q197 0.782 0.503 0.028 !       0.64 eA-3
Q198 0.716 0.692 0.591 !       0.64 eA-3
Q199 0.858 0.180 0.314 !       0.64 eA-3
;
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         8949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0591
_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^)+(0.0677P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1559
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4582
_reflns_number_total             8949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            am9b07677_si_002.cif
_cod_data_source_block           180713_s1_cj_sq
_cod_database_code               4514482
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3br1se1
_shelx_estimated_absorpt_t_max   0.628
_shelx_estimated_absorpt_t_min   0.494
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C32(H32), C9(H9), C25(H25), C36(H36), C13(H13), C18(H18), C45(H45),
 C42(H42), C22(H22), C35(H35), C21(H21), C39(H39), C29(H29), C33(H33), C19(H19),
  C43(H43), C28(H28), C26(H26), C40(H40)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C30(H30A,H30B,H30C), C44(H44A,H44B,H44C), C37(H37A,H37B,
 H37C)
2.c Idealised tetrahedral OH refined as rotating group:
 O48(H48)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'