Photo-controlled bipolar absorption switches based on 5-dimethylamino substituted indoline spiropyrans with semipermanent merocyanines
Metelitsa, Anatoly V.; Chernyshev, Anatoly V.; Voloshin, Nikolai; Demidov, Oleg P.; Solov'eva, Ekaterina; Rostovtseva, Irina A.; Gaeva, Elena; New Journal of Chemistry 45 (2021) 13529–13538; doi:10.1039/D1NJ02371C

data_7060800
_publ_section_title
;
 Photo-controlled bipolar absorption switches based on 5-dimethylamino
 substituted indoline spiropyrans with semipermanent merocyanines
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13529
_journal_page_last               13538
_journal_paper_doi               10.1039/D1NJ02371C
_journal_volume                  45
_journal_year                    2021
_chemical_compound_source        'Rostov-on-Don, Russia'
_chemical_formula_moiety         'C40 H35 N3 O2'
_chemical_formula_sum            'C40 H35 N3 O2'
_chemical_formula_weight         589.71
_chemical_melting_point          478
_chemical_name_common
5-(4,5-Diphenyloxazol-2-yl)-N,N,1',3',3'-pentamethylspiro[benzo[f]chromene-3,2'-indolin]-5'-amine
_chemical_name_systematic
5-(4,5-Diphenyloxazol-2-yl)-N,N,1',3',3'-pentamethylspiro[benzo[f]chromene-3,2'-indolin]-5'-amine
_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_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-20 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                77.789(3)
_cell_angle_beta                 74.227(3)
_cell_angle_gamma                85.006(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5067(3)
_cell_length_b                   13.2176(5)
_cell_length_c                   14.2579(6)
_cell_measurement_reflns_used    8032
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.6250
_cell_measurement_theta_min      3.2820
_cell_volume                     1507.12(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    -65.00  30.00   1.00    3.81    --  -41.35  57.00   0.00   95
  2  \w    -58.00  33.00   1.00    3.81    --  -41.35  38.00 150.00   91
  3  \w   -112.00 -17.00   1.00    3.81    --  -41.35 -57.00-150.00   95
  4  \w     49.00  95.00   1.00    3.81    --   41.35-125.00-180.00   46
  5  \w      6.00  53.00   1.00    3.81    --   41.35 -99.00  60.00   47
  6  \w    108.00 135.00   1.00   15.25    --  112.00 -61.00-180.00   27
  7  \w     75.00 102.00   1.00   15.25    --  112.00 -61.00-180.00   27
  8  \w     31.00  56.00   1.00   15.25    --  112.00 -95.00-180.00   25
  9  \w     68.00  95.00   1.00   15.25    --  112.00-111.00 150.00   27
 10  \w    105.00 178.00   1.00   15.25    --  112.00 111.00 -90.00   73
 11  \w     62.00 109.00   1.00   15.25    --  112.00-111.00 -60.00   47
 12  \w    140.00 170.00   1.00   15.25    --  112.00  77.00 -30.00   30
 13  \w     85.00 177.00   1.00   15.25    --  112.00  30.00  30.00   92
 14  \w     53.00 106.00   1.00   15.25    --  112.00-111.00 -90.00   53
 15  \w     55.00  89.00   1.00   15.25    --  112.00 -45.00 -30.00   34
 16  \w     67.00 105.00   1.00   15.25    --  112.00-111.00-120.00   38
 17  \w     76.00 109.00   1.00   15.25    --  112.00-111.00  90.00   33
 18  \w    138.00 166.00   1.00   15.25    --  112.00  45.00 150.00   28
 19  \w     61.00  86.00   1.00   15.25    --  112.00 -95.00 -60.00   25
 20  \w     36.00 130.00   1.00   15.25    --  112.00 -30.00-180.00   94
 21  \w     83.00 109.00   1.00   15.25    --  112.00-111.00  30.00   26
 22  \w     37.00 107.00   1.00   15.25    --  112.00-111.00  60.00   70
 23  \w     51.00  78.00   1.00   15.25    --  112.00 -95.00 120.00   27
 24  \w     81.00 106.00   1.00   15.25    --  112.00 -95.00 120.00   25
 25  \w     36.00 109.00   1.00   15.25    --  112.00-111.00-150.00   73
 26  \w    104.00 148.00   1.00   15.25    --  112.00 111.00-150.00   44
 27  \w     36.00  73.00   1.00   15.25    --  112.00-111.00  90.00   37
 28  \w    111.00 141.00   1.00   15.25    --  112.00 -61.00-120.00   30
 29  \w     40.00 100.00   1.00   15.25    --  112.00 -95.00  90.00   60
 30  \w     58.00 116.00   1.00   15.25    --  112.00 -45.00 120.00   58
 31  \w     44.00  69.00   1.00   15.25    --  112.00 -61.00-120.00   25
 32  \w     95.00 122.00   1.00   15.25    --  112.00 178.00  60.00   27
 33  \w     85.00 160.00   1.00   15.25    --  112.00  61.00  90.00   75
 34  \w     36.00  75.00   1.00   15.25    --  112.00 -95.00 -30.00   39
 35  \w     78.00 103.00   1.00   15.25    --  112.00 -95.00 -30.00   25
 36  \w     31.00  71.00   1.00   15.25    --  112.00 -15.00 -90.00   40
 37  \w    132.00 159.00   1.00   15.25    --  112.00 -15.00 -90.00   27
 38  \w     82.00 107.00   1.00   15.25    --  112.00-111.00 -30.00   25
 39  \w     98.00 137.00   1.00   15.25    --  112.00  45.00 150.00   39
 40  \w     42.00  69.00   1.00   15.25    --  112.00   0.00 120.00   27
 41  \w     90.00 137.00   1.00   15.25    --  112.00 178.00-150.00   47
 42  \w     67.00 138.00   1.00   15.25    --  112.00 178.00 -60.00   71
 43  \w     70.00  95.00   1.00   15.25    --  112.00 178.00   0.00   25
 44  \w    116.00 141.00   1.00   15.25    --  112.00 -61.00   0.00   25
 45  \w     87.00 112.00   1.00   15.25    --  112.00 -87.00 -31.66   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0968964000
_diffrn_orient_matrix_UB_12      -0.0675522000
_diffrn_orient_matrix_UB_13      0.0685751000
_diffrn_orient_matrix_UB_21      0.0576676000
_diffrn_orient_matrix_UB_22      -0.0724937000
_diffrn_orient_matrix_UB_23      -0.0751425000
_diffrn_orient_matrix_UB_31      0.1507786000
_diffrn_orient_matrix_UB_32      0.0664562000
_diffrn_orient_matrix_UB_33      -0.0525403000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18481
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.515
_diffrn_reflns_theta_min         3.285
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: o-xylene'
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         6281
_refine_ls_number_restraints     157
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0914P)^2^+0.4495P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1606
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5180
_reflns_number_total             6281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj02371c2.cif
_cod_data_source_block           631_100
_cod_database_code               7060800
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C40 H35 N3 O2'
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.809
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H11(0.04) H31(0.042) H32(0.046) H29(0.044) H35(0.046) H25(0.047)
 H3(0.05) H6(0.05) H28(0.05) H9(0.053) H33(0.054) H20(0.041) H17(0.043)
 H26(0.056) H18(0.044) H2(0.053) H8(0.061) H27(0.056) H34(0.057) H7(0.058)
 H38A(0.064) H38B(0.064) H38C(0.064) H37A(0.054) H37B(0.054) H37C(0.054)
 H36A(0.06) H36B(0.06) H36C(0.06) H39A(0.069) H39B(0.069) H39C(0.069)
 H40A(0.079) H40B(0.079) H40C(0.079) H20'(0.115) H17'(0.125) H18'(0.141)
 H38D(0.186) H38E(0.186) H38F(0.186) H37D(0.155) H37E(0.155) H37F(0.155)
 H36D(0.152) H36E(0.152) H36F(0.152) H40D(0.217) H40E(0.217) H40F(0.217)
 H39D(0.195) H39E(0.195) H39F(0.195)
 Fixed X: H11(0.2456) H31(0.4135) H32(0.3086) H29(0.2565) H35(0.0892)
 H25(0.6718) H3(0.5778) H6(0.433) H28(0.3188) H9(0.1443) H33(0.0936)
 H20(0.8134) H17(1.116) H26(0.7329) H18(1.1816) H2(0.7356) H8(0.1264)
 H27(0.5549) H34(-0.0143) H7(0.267) H38A(0.8907) H38B(0.8737) H38C(1.0439)
 H37A(0.5428) H37B(0.4598) H37C(0.5136) H36A(0.8694) H36B(0.6827) H36C(0.7815)
 H39A(1.2626) H39B(1.1545) H39C(1.1181) H40A(0.999) H40B(1.0946) H40C(1.1883)
 H20'(1.0647) H17'(0.7239) H18'(0.9144) H38D(0.4757) H38E(0.583) H38F(0.5717)
 H37D(1.0129) H37E(1.1328) H37F(1.0158) H36D(0.8161) H36E(0.9943) H36F(0.8357)
 H40D(1.0908) H40E(1.1792) H40F(1.2783) H39D(1.0756) H39E(1.1972) H39F(1.0058)
 Fixed Y: H11(0.4979) H31(0.4828) H32(0.6101) H29(0.3128) H35(0.5769)
 H25(0.2233) H3(0.1891) H6(0.2987) H28(0.1939) H9(0.5661) H33(0.7205) H20(-
 0.0017) H17(0.2707) H26(0.1048) H18(0.1998) H2(0.0821) H8(0.551) H27(0.0881)
 H34(0.7039) H7(0.4154) H38A(0.3523) H38B(0.2977) H38C(0.2903) H37A(-0.0129)
 H37B(0.0464) H37C(0.1101) H36A(-0.0242) H36B(-0.0545) H36C(-0.0909)
 H39A(0.0991) H39B(0.0754) H39C(0.1783) H40A(-0.0978) H40B(-0.087) H40C(-
 0.0704) H20'(0.2365) H17'(-0.0526) H18'(-0.0157) H38D(0.0389) H38E(-0.0612)
 H38F(-0.0285) H37D(0.0924) H37E(0.1758) H37F(0.2066) H36D(0.3506) H36E(0.3472)
 H36F(0.3391) H40D(-0.0095) H40E(0.0696) H40F(0.0166) H39D(0.2784) H39E(0.2525)
 H39F(0.234)
 Fixed Z: H11(0.5281) H31(0.9424) H32(1.0354) H29(0.9909) H35(0.7774)
 H25(0.8046) H3(0.3061) H6(0.2273) H28(1.1232) H9(0.3802) H33(1.0008)
 H20(0.7758) H17(0.5519) H26(0.9373) H18(0.7029) H2(0.39) H8(0.2242)
 H27(1.0961) H34(0.8706) H7(0.1502) H38A(0.4487) H38B(0.362) H38C(0.3911)
 H37A(0.7209) H37B(0.6356) H37C(0.7049) H36A(0.5065) H36B(0.5298) H36C(0.6126)
 H39A(0.8334) H39B(0.9461) H39C(0.8719) H40A(0.8477) H40B(0.9274) H40C(0.8118)
 H20'(0.6255) H17'(0.7518) H18'(0.8308) H38D(0.6071) H38E(0.6398) H38F(0.5271)
 H37D(0.4145) H37E(0.4214) H37F(0.3482) H36D(0.4385) H36E(0.4565) H36F(0.5487)
 H40D(0.8782) H40E(0.9165) H40F(0.8258) H39D(0.7485) H39E(0.8192) H39F(0.8649)
;
_shelx_res_checksum              45553
_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 1.542
_oxdiff_exptl_absorpt_empirical_full_min 0.708