Chromenes involving a two-photon absorbing moiety: photochromism via intramolecular resonance energy transfer
Bekere, Laura; Lokshin, Vladimir; Sigalov, Mark; Gvishi, Raz; Zhao, Peng; Hagan, David J.; Van Stryland, Eric W.; Khodorkovsky, Vladimir; New J. Chem. 40 (2016) 1143–; doi:10.1039/C5NJ02490K

data_7055175
_publ_section_title
;
 Chromenes involving a two-photon absorbing moiety: photochromism via
 intramolecular resonance energy transfer
;
_journal_issue                   2
_journal_name_full               'New J. Chem.'
_journal_page_first              1143
_journal_paper_doi               10.1039/C5NJ02490K
_journal_volume                  40
_journal_year                    2016
_chemical_formula_moiety         'C68 H50 N2 O3, C2 H3 N'
_chemical_formula_sum            'C70 H53 N3 O3'
_chemical_formula_weight         984.15
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date
;
'Wed Sep 17 11:18:06 2014'
;
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_audit_update_record
;
2014-11-10 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                93.7823(19)
_cell_angle_beta                 103.688(2)
_cell_angle_gamma                100.746(2)
_cell_formula_units_Z            2
_cell_length_a                   12.9850(3)
_cell_length_b                   13.0948(3)
_cell_length_c                   16.3926(4)
_cell_measurement_reflns_used    9708
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7210
_cell_measurement_theta_min      4.1770
_cell_volume                     2642.92(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.889
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_details
;
  1 omega   15.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867  -38.0000   60.0000 27

  2 omega    9.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867  -99.0000  120.0000 75

  3 omega   23.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867 -125.0000   60.0000 70

  4 omega   29.00   94.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -45.0000   60.0000 65

  5 omega   51.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -94.0000  120.0000 57

  6 omega   38.00   76.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -30.0000    0.0000 38

  7 omega  117.00  169.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698   30.0000  -60.0000 52

  8 omega  107.00  133.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -77.0000 -150.0000 26

  9 omega   84.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -94.0000  -60.0000 25

 10 omega   66.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -94.0000 -120.0000 42

 11 omega   36.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -94.0000 -180.0000 72

 12 omega   33.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867  -77.0000 -180.0000 37

 13 omega    9.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867  -99.0000  -60.0000 55

 14 omega    7.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867  -99.0000  -30.0000 34

 15 omega   19.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -77.0000 -150.0000 52

 16 omega   34.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -30.0000  -90.0000 54

 17 omega   29.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -45.0000 -150.0000 69

 18 omega   28.00   65.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -30.0000  -30.0000 37

 19 omega   59.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867   57.0000   90.0000 57

 20 omega   10.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867   57.0000   90.0000 34

 21 omega  -29.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867  -38.0000  150.0000 65

 22 omega   26.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698 -111.0000   30.0000 89

 23 omega   25.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.4698  -94.0000   60.0000 68

 24 omega  -45.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867  -57.0000 -150.0000 111

 25 omega  -43.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867  -38.0000   60.0000 38

 26 omega -105.00  -75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867 -125.0000  -30.0000 30

 27 omega -125.00  -95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867  -99.0000 -120.0000 30

 28 omega  -71.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867  -77.0000 -150.0000 47

 29 omega  -50.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.2867  -77.0000 -180.0000 78

 30 omega  -98.00  -73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.2867 -125.0000 -180.0000 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_UB_11      -0.1070538000
_diffrn_orient_matrix_UB_12      -0.0157684000
_diffrn_orient_matrix_UB_13      -0.0690368000
_diffrn_orient_matrix_UB_21      0.0407917000
_diffrn_orient_matrix_UB_22      0.1049954000
_diffrn_orient_matrix_UB_23      -0.0308402000
_diffrn_orient_matrix_UB_31      0.0496342000
_diffrn_orient_matrix_UB_32      -0.0570955000
_diffrn_orient_matrix_UB_33      -0.0613587000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.889
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17131
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         3.459
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     688
_refine_ls_number_reflns         8468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0734P)^2^+0.7715P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1534
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7162
_reflns_number_total             8468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5nj02490k1.cif
_cod_data_source_block           lb1a
_cod_depositor_comments
'Adding full bibliography for 7055175--7055176.cif.'
_cod_database_code               7055175
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 90.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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:
 C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C33(H33), C35(H35), C36(H36), C39(H39), C40(H40), C42(H42), C46(H46),
 C47(H47), C48(H48), C49(H49), C52(H52), C53(H53), C54(H54), C55(H55), C58(H58),
  C59(H59), C60(H60), C61(H61), C64(H64), C65(H65), C66(H66), C67(H67)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C44(H44A,H44B,H44C), C70(H70A,H70B,H70C)
;
_olex2_submission_special_instructions 'No special instructions were received'