The Butterfly Effect in Bisfluorenylidene-based Dihydroacenes: Aggregation Induced Emission and Spin Switching
Yin, Xiaodong; Low, Jonathan Z.; Fallon, Kealan; Paley, Daniel W.; Campos, Luis; Chemical Science  (2019) –; doi:10.1039/C9SC04096J

data_1552380
_publ_section_title
;
 The Butterfly Effect in Bisfluorenylidene-based Dihydroacenes:
 Aggregation Induced Emission and Spin Switching
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC04096J
_journal_year                    2019
_chemical_formula_moiety         'C48 H28, 0.5(C H Cl3)'
_chemical_formula_sum            'C48.5 H28.5 Cl1.5'
_chemical_formula_weight         664.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2019-08-15 deposited with the CCDC.    2019-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.2024(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.38224(13)
_cell_length_b                   15.79468(12)
_cell_length_c                   24.01834(18)
_cell_measurement_reflns_used    26959
_cell_measurement_temperature    104(7)
_cell_measurement_theta_max      71.3700
_cell_measurement_theta_min      4.2110
_cell_volume                     6589.29(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      104(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega    9.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   77.0000   60.0000 94

  2 omega  -32.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -57.0000   30.0000 84

  3 omega  -34.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -37.0000   60.0000 89

  4 omega    1.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -99.0000 -180.0000 73

  5 omega    1.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -99.0000   90.0000 73

  6 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   57.0000 -120.0000 84

  7 omega    1.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -99.0000  -60.0000 73

  8 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   57.0000  -60.0000 84

  9 omega    6.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   19.0000 -120.0000 101

 10 omega    9.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   77.0000    0.0000 94

 11 omega   39.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

 12 omega   37.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -24.0000  126.8798 58

 13 omega   40.00   99.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 59

 14 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 15 omega   90.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 85

 16 omega   90.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 85

 17 omega   39.00   94.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -40.0000  -76.9681 55

 18 omega   37.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -23.0000  -82.6395 60

 19 omega   39.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

 20 omega   38.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 78

 21 omega   38.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 78

 22 omega   87.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 91

 23 omega   39.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 24 omega  100.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 78

 25 omega   40.00  135.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 95

 26 omega   87.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 91

 27 omega   38.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 78

 28 omega   38.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 78

 29 omega   70.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 108

 30 omega   87.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 91

 31 omega   40.00  138.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -83.0000 -155.3576 98

 32 omega  100.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 78

 33 omega   38.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 34 omega   39.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 35 omega   38.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 36 omega   40.00  135.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 95

 37 omega   90.00  161.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0722860000
_diffrn_orient_matrix_UB_12      -0.0565157000
_diffrn_orient_matrix_UB_13      -0.0007348000
_diffrn_orient_matrix_UB_21      -0.0343572000
_diffrn_orient_matrix_UB_22      0.0505383000
_diffrn_orient_matrix_UB_23      -0.0498688000
_diffrn_orient_matrix_UB_31      0.0383224000
_diffrn_orient_matrix_UB_32      -0.0613116000
_diffrn_orient_matrix_UB_33      -0.0403899000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            47924
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.585
_diffrn_reflns_theta_min         4.165
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.668
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2760
_exptl_crystal_size_max          0.4292
_exptl_crystal_size_mid          0.1441
_exptl_crystal_size_min          0.0904
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0770P)^2^+9.6540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1415
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6166
_reflns_number_total             6423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04096j2.cif
_cod_data_source_block           bFP
_cod_original_formula_sum        'C48.50 H28.50 Cl1.50'
_cod_database_code               1552380
_chemical_oxdiff_formula         'c48.5 h28.5 cl1.5'
_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
2. Others
 Fixed Sof: C51(0.5) H51(0.5) Cl52(0.5) Cl53(0.5) Cl54(0.5)
3.a Ternary CH refined with riding coordinates:
 C51(H51)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C21(H21), C25(H25), C26(H26), C27(H27), C28(H28),
  C31(H31), C32(H32), C33(H33), C34(H34), C38(H38), C39(H39), C40(H40),
 C41(H41), C44(H44), C45(H45), C46(H46), C47(H47)
;
_shelx_res_checksum              37364
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'