Multiple yet Controllable Photoswitching in a Single AIEgen System.
Wei, Peifa; Zhang, Jing-Xuan; Zhao, Zheng; Chen, Yuncong; He, Xuewen; Chen, Ming; Gong, Junyi; Sung, Herman H.-Y.; Williams, Ian D.; Lam, Jacky W. Y.; Tang, Ben Zhong; Journal of the American Chemical Society  (2018) –; doi:10.1021/jacs.7b13364

data_4127094
_publ_section_title
;
 Multiple yet Controllable Photoswitching in a Single AIEgen System.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b13364
_journal_year                    2018
_chemical_formula_moiety         '2(F6 P), C52 H42 N4 O2, 1.75(C2 H3 N)'
_chemical_formula_sum            'C55.5 H47.25 F12 N5.75 O2 P2'
_chemical_formula_weight         1116.68
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.1183(6)
_cell_length_b                   14.0176(4)
_cell_length_c                   19.1001(6)
_cell_measurement_reflns_used    4205
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.3150
_cell_measurement_theta_min      4.3740
_cell_volume                     5386.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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     36.00  95.00   1.00   45.00    --  110.57 -45.00 -90.00   59
  2  \w     14.00  83.00   1.00    8.00    --   40.57 -99.00-120.00   69
  3  \w    -96.00 -29.00   1.00    8.00    --  -40.57 125.00  30.00   67
  4  \w   -130.00  49.00   1.00    8.00    --  -40.57   0.00 150.00  179
  5  \w    109.00 138.00   1.00   45.00    --  110.57 -45.00 -90.00   29
  6  \w     65.00 108.00   1.00   45.00    --  110.57 -94.00-180.00   43
  7  \w     50.00 170.00   1.00   45.00    --  110.57  15.00-180.00  120
  8  \w     81.00 168.00   1.00   45.00    --  110.57  61.00-150.00   87
  9  \w     97.00 176.00   1.00   45.00    --  110.57  77.00  60.00   79
 10  \w     33.00 143.00   1.00   45.00    --  110.57 -77.00  60.00  110
 11  \w     39.00 122.00   1.00   45.00    --  110.57-125.00  60.00   83
 12  \w     26.00 108.00   1.00   45.00    --  110.57 -94.00 -90.00   82
 13  \w     30.00  55.00   1.00   45.00    --  110.57 -94.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0297502000
_diffrn_orient_matrix_UB_12      -0.0486997000
_diffrn_orient_matrix_UB_13      -0.0651850000
_diffrn_orient_matrix_UB_21      0.0108810000
_diffrn_orient_matrix_UB_22      -0.0920790000
_diffrn_orient_matrix_UB_23      0.0425457000
_diffrn_orient_matrix_UB_31      -0.0697251000
_diffrn_orient_matrix_UB_32      -0.0350526000
_diffrn_orient_matrix_UB_33      -0.0210837000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29379
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_min         3.843
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.512
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2298
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1416
_refine_ls_number_reflns         8349
_refine_ls_number_restraints     1329
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0880
_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^)+(0.0980P)^2^+7.5020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2059
_refine_ls_wR_factor_ref         0.2296
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    0.719
_reflns_Friedel_fraction_max     0.714
_reflns_number_gt                5109
_reflns_number_total             8349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d-MPPMNAN.cif
_cod_data_source_block           peifa11i
_cod_original_formula_sum        'C55.50 H47.25 F12 N5.75 O2 P2'
_cod_database_code               4127094
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'P2 F12 C50 H48 N2 O2'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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
2. Restrained distances
 C6S-C5S = C6SA-C5SA
 1.52 with sigma of 0.02
 N4S-C5S = N4SA-C5SA
 1.1 with sigma of 0.02
 F2-F5
 2.15 with sigma of 0.04
 C6SA-N4SA
 2.75 with sigma of 0.04
 C21-C26 \\sim C25-C26 \\sim C24-C25 \\sim C24-C23
 with sigma of 0.02
 C22-C21 \\sim C22-C23 \\sim C24-C23 \\sim C24-C25 \\sim C25-C26 \\sim C21-C26
 with sigma of 0.02
 P1-F6 \\sim P1-F3 \\sim P1-F2 \\sim P1-F5 \\sim P1-F1 \\sim P1-F4
 with sigma of 0.02
 C12-C11 \\sim C12-C13 \\sim C13-C14 \\sim C19-C14 \\sim C20-C19 \\sim C20-C11
\\sim C14-C15 \\sim C16-C15
 \\sim C16-C17 \\sim C18-C17 \\sim C18-C19
 with sigma of 0.02
 P2-F12 \\sim P2-F15 \\sim P2-F14 \\sim P2-F13 \\sim P2-F11 \\sim P2-F16
 with sigma of 0.02
 C26A-C21A \\sim C26A-C25A \\sim C24A-C25A \\sim C24A-C23A
 with sigma of 0.02
 C26A-C21A \\sim C26A-C25A \\sim C24A-C25A \\sim C24A-C23A \\sim C22A-C23A
\\sim C22A-C21A
 with sigma of 0.02
 C12A-C11A \\sim C12A-C13A \\sim C13A-C14A \\sim C19A-C14A \\sim C20A-C19A
\\sim C20A-C11A \\sim C14A-
 C15A \\sim C16A-C15A \\sim C16A-C17A \\sim C18A-C17A \\sim C18A-C19A
 with sigma of 0.02
 P1A-F6A \\sim P1A-F1A \\sim P1A-F3A \\sim P1A-F2A \\sim P1A-F5A \\sim P1A-F4A
 with sigma of 0.02
 P2A-F16A \\sim P2A-F13A \\sim P2A-F11A \\sim P2A-F15A \\sim P2A-F12A \\sim
P2A-F14A
 with sigma of 0.02
 C2-C5 \\sim C5A-C2A \\sim C4A-C6A \\sim C4-C6
 with sigma of 0.02
 N1-C5 \\sim N1A-C5A \\sim N2A-C6A \\sim N2-C6
 with sigma of 0.02
3. Restrained planarity
 C21, C22, C23, C24, C25, C26
 with sigma of 0.1
 N51, C50, C52, C53, C54, C55, C56
 with sigma of 0.05
 C11, C12, C13, C14, C15, C16, C17, C18, C19, C20
 with sigma of 0.1
 C21A, C22A, C23A, C24A, C25A, C26A
 with sigma of 0.1
 N51A, C50A, C52A, C53A, C54A, C55A, C56A
 with sigma of 0.03
4. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.002
Uanis(C3SA) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.001
Uanis(C5) \\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(N1A) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.003
Uanis(N4SA) \\sim Ueq, Uanis(C5SA) \\sim Ueq, Uanis(C6SA) \\sim Ueq: with sigma
of 0.003 and sigma for terminal atoms of 0.002
Uanis(N4S) \\sim Ueq, Uanis(C5S) \\sim Ueq, Uanis(C6S) \\sim Ueq: with sigma of
0.003 and sigma for terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 N51, C50, C52, C53, C54, C55, C56
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C21, C22, C23, C24, C25, C26
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O1, C10, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N1S, C2S, C3S
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 P1, F1, F2, F3, F4, F5, F6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N61, C62, C63, C64, C65, C66
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 P2, F11, F12, F13, F14, F15, F16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C21A, C22A, C23A, C24A, C25A, C26A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O1A, C10A, C11A, C12A, C13A, C14A, C15A, C16A, C17A, C18A, C19A, C20A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O1A, C10A, C16A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N1SA, C2SA, C3SA
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 P1A, F1A, F2A, F3A, F4A, F5A, F6A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N61A, C41A, C42A, C43A, C44A, C45A, C46A, C60A, C62A, C63A, C64A, C65A, C66A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N61, C41, C42, C43, C44, C45, C46, C60, C62, C63, C64, C65, C66
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N61A, C62A, C63A, C64A, C65A, C66A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N2A, C1A, C2A, C3A, C4A, C6A, C11A, C41A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O2, C30, C31, C32, C33, C34, C35, C36, C37, C38, C39, C40
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O2A, C30A, C31A, C32A, C33A, C34A, C35A, C36A, C37A, C38A, C39A, C40A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N51, C21, C22, C23, C24, C25, C26, C50, C52, C54, C55, C56, C53A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 P2A, F11A, F12A, F13A, F14A, F15A, F16A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N51A, C50A, C52A, C53A, C54A, C55A, C56A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N4SA, C5SA, C6SA
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N4S, C5S, C6S
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N1, C1, C1, C2, C3, C4, C11, C41
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Fixed Sof: P1(0.5) F1(0.5) F2(0.5) F3(0.5) F4(0.5) F5(0.5) F6(0.5) P1A(0.5)
 F1A(0.5) F2A(0.5) F3A(0.5) F4A(0.5) F5A(0.5) F6A(0.5) P2A(0.5) F11A(0.5)
 F12A(0.5) F13A(0.5) F14A(0.5) F15A(0.5) F16A(0.5) P2(0.5) F11(0.5) F12(0.5)
 F13(0.5) F14(0.5) F15(0.5) F16(0.5) O1(0.5) O2(0.5) N1(0.5) N2(0.5) N51(0.5)
 N61(0.5) C1(0.5) H1(0.5) C2(0.5) C3(0.5) H3(0.5) C4(0.5) C5(0.5) C6(0.5)
 C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C11(0.5) C12(0.5) H12(0.5) C13(0.5)
 H13(0.5) C14(0.5) C15(0.5) H15(0.5) C16(0.5) C17(0.5) H17(0.5) C18(0.5)
 H18(0.5) C19(0.5) C20(0.5) H20(0.5) C21(0.5) C22(0.5) H22(0.5) C23(0.5)
 H23(0.5) C24(0.5) C25(0.5) H25(0.5) C26(0.5) H26(0.5) C30(0.5) H30A(0.5)
 H30B(0.5) H30C(0.5) C31(0.5) C32(0.5) H32(0.5) C33(0.5) H33(0.5) C34(0.5)
 C35(0.5) H35(0.5) C36(0.5) C37(0.5) H37(0.5) C38(0.5) H38(0.5) C39(0.5)
 C40(0.5) H40(0.5) C41(0.5) C42(0.5) H42(0.5) C43(0.5) H43(0.5) C44(0.5)
 C45(0.5) H45(0.5) C46(0.5) H46(0.5) C50(0.5) H50A(0.5) H50B(0.5) H50C(0.5)
 C52(0.5) H52(0.5) C53(0.5) H53(0.5) C54(0.5) C55(0.5) H55(0.5) C56(0.5)
 H56(0.5) C60(0.5) H60A(0.5) H60B(0.5) H60C(0.5) C62(0.5) H62(0.5) C63(0.5)
 H63(0.5) C64(0.5) C65(0.5) H65(0.5) C66(0.5) H66(0.5) O1A(0.5) O2A(0.5)
 N1A(0.5) N2A(0.5) N51A(0.5) N61A(0.5) C1A(0.5) H1A(0.5) C2A(0.5) C3A(0.5)
 H3A(0.5) C4A(0.5) C5A(0.5) C6A(0.5) C10A(0.5) H10D(0.5) H10E(0.5) H10F(0.5)
 C11A(0.5) C12A(0.5) H12A(0.5) C13A(0.5) H13A(0.5) C14A(0.5) C15A(0.5)
 H15A(0.5) C16A(0.5) C17A(0.5) H17A(0.5) C18A(0.5) H18A(0.5) C19A(0.5)
 C20A(0.5) H20A(0.5) C21A(0.5) C22A(0.5) H22A(0.5) C23A(0.5) H23A(0.5)
 C24A(0.5) C25A(0.5) H25A(0.5) C26A(0.5) H26A(0.5) C30A(0.5) H30D(0.5)
 H30E(0.5) H30F(0.5) C31A(0.5) C32A(0.5) H32A(0.5) C33A(0.5) H33A(0.5)
 C34A(0.5) C35A(0.5) H35A(0.5) C36A(0.5) C37A(0.5) H37A(0.5) C38A(0.5)
 H38A(0.5) C39A(0.5) C40A(0.5) H40A(0.5) C41A(0.5) C42A(0.5) H42A(0.5)
 C43A(0.5) H43A(0.5) C44A(0.5) C45A(0.5) H45A(0.5) C46A(0.5) H46A(0.5)
 C50A(0.5) H50D(0.5) H50E(0.5) H50F(0.5) C52A(0.5) H52A(0.5) C53A(0.5)
 H53A(0.5) C54A(0.5) C55A(0.5) H55A(0.5) C56A(0.5) H56A(0.5) C60A(0.5)
 H60D(0.5) H60E(0.5) H60F(0.5) C62A(0.5) H62A(0.5) C63A(0.5) H63A(0.5)
 C64A(0.5) C65A(0.5) H65A(0.5) C66A(0.5) H66A(0.5) N4SA(0.3) C5SA(0.3)
 C6SA(0.3) H6SA(0.3) H6SB(0.3) H6SC(0.3) N1SA(0.33333) C2SA(0.33333)
 C3SA(0.33333) H3SA(0.33333) H3SB(0.33333) H3SC(0.33333) N4S(0.45) C5S(0.45)
 C6S(0.45) H6SD(0.45) H6SE(0.45) H6SF(0.45) N1S(0.66667) C2S(0.66667)
 C3S(0.66667) H3SD(0.66667) H3SE(0.66667) H3SF(0.66667)
7.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C1A(H1A), C3A(H3A)
7.b Me refined with riding coordinates:
 C50A(H50D,H50E,H50F)
7.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C17(H17), C18(H18), C20(H20), C22(H22),
 C23(H23), C25(H25), C26(H26), C32(H32), C33(H33), C35(H35), C37(H37), C38(H38),
  C40(H40), C42(H42), C43(H43), C45(H45), C46(H46), C52(H52), C53(H53),
 C55(H55), C56(H56), C62(H62), C63(H63), C65(H65), C66(H66), C12A(H12A),
 C13A(H13A), C15A(H15A), C17A(H17A), C18A(H18A), C20A(H20A), C22A(H22A),
 C23A(H23A), C25A(H25A), C26A(H26A), C32A(H32A), C33A(H33A), C35A(H35A),
 C37A(H37A), C38A(H38A), C40A(H40A), C42A(H42A), C43A(H43A), C45A(H45A),
 C46A(H46A), C52A(H52A), C53A(H53A), C55A(H55A), C56A(H56A), C62A(H62A),
 C63A(H63A), C65A(H65A), C66A(H66A)
7.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C30(H30A,H30B,H30C), C50(H50A,H50B,H50C), C60(H60A,H60B,
 H60C), C10A(H10D,H10E,H10F), C30A(H30D,H30E,H30F), C60A(H60D,H60E,H60F),
 C6SA(H6SA,H6SB,H6SC), C3SA(H3SA,H3SB,H3SC), C6S(H6SD,H6SE,H6SF), C3S(H3SD,H3SE,
 H3SF)
;
_olex2_date_sample_data_collection 2017-10-06
_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 1.155
_oxdiff_exptl_absorpt_empirical_full_min 0.874