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_7055176
_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'
_chemical_formula_sum            'C68 H50 N2 O3'
_chemical_formula_weight         943.10
_chemical_name_systematic
'3-(2,7-di(9H-carbazol-9-yl)-9-methyl-9H-fluoren-9-yl)propyl 8-methyl-2,2-diphenyl-2H-benzo[h]chromene-5-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date
;
'Tue Sep 16 07:40:17 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                90.0
_cell_angle_beta                 134.348(9)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   13.2538(6)
_cell_length_b                   21.2051(4)
_cell_length_c                   25.4117(13)
_cell_measurement_reflns_used    8333
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.4070
_cell_measurement_theta_min      4.2400
_cell_volume                     5107.2(9)
_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    'ShelXS (Sheldrick, 2008)'
_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 0.977
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   10.00   42.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  150.0000 32

  2 omega  -14.00   62.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 76

  3 omega  -69.00   -3.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -59.0000  125.0000  -90.0000 66

  4 omega  -95.00  -62.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -59.0000  125.0000 -180.0000 33

  5 omega  -50.00   -3.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -59.0000  125.0000 -180.0000 47

  6 omega  116.00  141.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       59.0000  125.0000  -90.0000 25

  7 omega  106.00  141.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       59.0000  125.0000  150.0000 35

  8 omega  104.00  140.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       59.0000  125.0000  -30.0000 36

  9 omega   22.00  140.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       59.0000   38.0000   90.0000 118

 10 omega  103.00  178.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      118.0000  111.0000  -30.0000 75

 11 omega   34.00   99.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      118.0000 -111.0000  150.0000 65

 12 omega   31.00   89.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      118.0000  -25.0000  -60.0000 58

 13 omega   39.00   65.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      118.0000  -50.0000  -60.0000 26

 14 omega   39.00  133.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      118.0000  -63.0000  -60.0000 94

 15 omega   97.00  173.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      118.0000   63.0000   60.0000 76

 16 omega   43.00  100.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      118.0000  -50.0000 -150.0000 57

 17 omega  110.00  178.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      118.0000  111.0000    0.0000 68
;
_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      0.0827251000
_diffrn_orient_matrix_UB_12      0.0617964000
_diffrn_orient_matrix_UB_13      0.0382217000
_diffrn_orient_matrix_UB_21      -0.0594302000
_diffrn_orient_matrix_UB_22      0.0053638000
_diffrn_orient_matrix_UB_23      0.0345964000
_diffrn_orient_matrix_UB_31      0.1266515000
_diffrn_orient_matrix_UB_32      -0.0378147000
_diffrn_orient_matrix_UB_33      0.0672816000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            22894
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         65.081
_diffrn_reflns_theta_min         3.701
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81010
_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    1.227
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.839
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     570
_refine_ls_number_reflns         8706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0961
_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^)+(0.1500P)^2^+4.7026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2824
_refine_ls_wR_factor_ref         0.3022
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6718
_reflns_number_total             8706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5nj02490k1.cif
_cod_data_source_block           lb1alpha
_cod_depositor_comments
'Adding full bibliography for 7055175--7055176.cif.'
_cod_original_cell_volume        5107.3(4)
_cod_database_code               7055176
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Uiso/Uaniso restraints and constraints
Uanis(C57) = Uanis(C68) = Uanis(C63) = Uanis(C67) = Uanis(C62) = Uanis(C65) =
Uanis(C64) = Uanis(C59) = Uanis(C58) = Uanis(C66) = Uanis(C61) = Uanis(C60)
3.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B)
3.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), C67(H67), C66(H66), C65(H65), C64(H64)
3.c Fitted hexagon refined as free rotating group:
 C57(C58,C59,C60,C61,C62), C68(C67,C66,C65,C64,C63)
3.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C44(H44A,H44B,H44C)
;
_olex2_submission_special_instructions 'No special instructions were received'