Reversible trans-to-cis photoisomerization and irreversible photocyclization reactions of a Co-coordinated stilbene derivative on chiral di-β-diketonate lanthanide complexes
Hou, Ziting; Huang, Yanji; Ruan, Yushan; Xu, Han; Tan, Yu; Lin, Li-Rong; Wu, Zhen-yi; RSC Advances 13 (2023) 2269–2282; doi:10.1039/D2RA07133A

data_7246135
_publ_section_title
;
 Reversible trans-to-cis photoisomerization and irreversible
 photocyclization reactions of a Co-coordinated stilbene derivative on
 chiral di-\b-diketonate lanthanide complexes
;
_journal_issue                   4
_journal_name_full               'RSC Advances'
_journal_page_first              2269
_journal_page_last               2282
_journal_paper_doi               10.1039/D2RA07133A
_journal_volume                  13
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C57 H52 F17 La N4 O7, H2 O'
_chemical_formula_sum            'C57 H54 F17 La N4 O8'
_chemical_formula_weight         1384.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-16
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-09-16 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.312(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.7500(6)
_cell_length_b                   20.1395(5)
_cell_length_c                   20.6309(4)
_cell_measurement_reflns_used    17836
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.1910
_cell_measurement_theta_min      2.6840
_cell_volume                     11735.0(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.929
_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   -122.00 -43.00   0.50    5.00    --  -43.09-173.00  79.00  158
  2  \w    -80.00 -53.00   0.50    5.00    --  -43.09 114.00 -49.00   54
  3  \w    -43.00  -6.00   0.50    5.00    --  -43.09 114.00 -49.00   74
  4  \w     34.00  59.00   0.50    5.00    --   43.09-114.00-140.00   50
  5  \w   -155.00 -77.00   0.50   20.00    --  -96.00-114.00-140.00  156
  6  \w   -102.00 -77.00   0.50   20.00    --  -96.00 173.00  90.00   50
  7  \w     54.00 112.00   0.50   20.00    --  109.59-114.00-140.00  116
  8  \w    113.00 151.00   0.50   20.00    --  109.59-173.00  79.00   76
  9  \w   -118.00 -19.00   0.50    5.00    --  -43.09 -57.00 -60.00  198
 10  \w    -69.00 -44.00   0.50    5.00    --  -43.09-178.00 -30.00   50
 11  \w    -99.00 -70.00   0.50    5.00    --  -43.09-178.00 -30.00   58
 12  \w     15.00  40.00   0.50    5.00    --   43.09 -37.00  90.00   50
 13  \w    -35.00  -3.00   0.50    5.00    --   43.09 -37.00  90.00   64
 14  \w    -91.00 -21.00   0.50   20.00    --  -96.00 125.00 -30.00  140
 15  \w    -47.00 -19.00   0.50   20.00    --  -96.00  45.00  90.00   56
 16  \w    -47.00 -19.00   0.50   20.00    --  -96.00  45.00 -90.00   56
 17  \w    -46.00 -19.00   0.50   20.00    --  -96.00  45.00-180.00   54
 18  \w    -50.00 -19.00   0.50   20.00    --  -96.00  45.00 150.00   62
 19  \w    -70.00 -29.00   0.50   20.00    --  -96.00  61.00 120.00   82
 20  \w    -49.00 -21.00   0.50   20.00    --  -96.00  61.00  60.00   56
 21  \w    -48.00 -19.00   0.50   20.00    --  -96.00  45.00  60.00   58
 22  \w    -51.00 -23.00   0.50   20.00    --  -96.00  45.00 -60.00   56
 23  \w    -50.00 -21.00   0.50   20.00    --  -96.00  45.00 120.00   58
 24  \w    -50.00 -20.00   0.50   20.00    --  -96.00  45.00-120.00   60
 25  \w     48.00  99.00   0.50   20.00    --  109.59 -94.00-120.00  102
 26  \w     36.00  61.00   0.50   20.00    --  109.59 -61.00-120.00   50
 27  \w     43.00  70.00   0.50   20.00    --  109.59 -61.00   0.00   54
 28  \w     95.00 167.00   0.50   20.00    --  109.59 125.00 -30.00  144
 29  \w     36.00  61.00   0.50   20.00    --  109.59 -61.00 -90.00   50
 30  \w     37.00  64.00   0.50   20.00    --  109.59 -61.00  90.00   54
 31  \w     36.00  77.00   0.50   20.00    --  109.59 -77.00 -90.00   82
 32  \w    114.00 139.00   0.50   20.00    --  109.59 114.00 -49.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0479598000
_diffrn_orient_matrix_UB_12      -0.0067505000
_diffrn_orient_matrix_UB_13      0.0566114000
_diffrn_orient_matrix_UB_21      -0.0086691000
_diffrn_orient_matrix_UB_22      -0.0751109000
_diffrn_orient_matrix_UB_23      0.0042973000
_diffrn_orient_matrix_UB_31      0.0244867000
_diffrn_orient_matrix_UB_32      -0.0129793000
_diffrn_orient_matrix_UB_33      -0.0543782000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40377
_diffrn_reflns_point_group_measured_fraction_full 0.814
_diffrn_reflns_point_group_measured_fraction_max 0.748
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.453
_diffrn_reflns_theta_min         2.695
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
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    1.568
_exptl_crystal_description       block
_exptl_crystal_F_000             5584
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.410
_refine_diff_density_min         -1.820
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 4881 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1832
_refine_ls_number_reflns         18230
_refine_ls_number_restraints     2483
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0919P)^2^+15.4408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1588
_reflns_Friedel_coverage         0.564
_reflns_Friedel_fraction_full    0.626
_reflns_Friedel_fraction_max     0.556
_reflns_number_gt                15710
_reflns_number_total             18230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra07133a2.cif
_cod_data_source_block           exp_9694_auto
_cod_original_cell_volume        11735.0(4)
_cod_database_code               7246135
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'La F18 O15 C60 N12'
_shelx_estimated_absorpt_t_max   0.351
_shelx_estimated_absorpt_t_min   0.177
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 F41-F40
 2.15 with sigma of 0.04
 F39-F40
 2.15 with sigma of 0.04
 F37-F38
 2.2 with sigma of 0.04
 F13A-F12A
 2.15 with sigma of 0.04
 F14A-F12A
 2.15 with sigma of 0.04
 F39-F41
 2.15 with sigma of 0.04
 F14A-F13A
 2.15 with sigma of 0.04
 O4A-C42A \\sim O4A-C118
 with sigma of 0.02
 F13A-F14A \\sim F39-F40
 with sigma of 0.04
 F9A-C43A \\sim F35-C115
 with sigma of 0.02
 F14A-F12A \\sim F40-F41
 with sigma of 0.04
 F14A-C45A \\sim F40-C117
 with sigma of 0.02
 F14A-C44A \\sim F40-C116
 with sigma of 0.04
 F10A-C45A \\sim F38-C117
 with sigma of 0.04
 F39-C117 \\sim F40-C117 \\sim F41-C117
 with sigma of 0.01
 F15-C57 \\sim F47-C57
 with sigma of 0.02
 F8A-C43A \\sim F36-C115
 with sigma of 0.02
 F11A-C44A \\sim F37-C116
 with sigma of 0.02
 F10A-C44A \\sim F38-C116
 with sigma of 0.02
 F13A-C44A \\sim F39-C116
 with sigma of 0.04
 F13A-C45A \\sim F39-C117
 with sigma of 0.02
 C51A-C43A \\sim C51A-C115
 with sigma of 0.04
 C42A-C51A \\sim C118-C51A
 with sigma of 0.02
 C42A-C43A \\sim C118-C115
 with sigma of 0.02
 C43A-C44A \\sim C115-C116
 with sigma of 0.02
 C57A-F15A \\sim C57A-F42
 with sigma of 0.02
 F17-C57 \\sim F46-C57
 with sigma of 0.02
 F16-C57 \\sim F45-C57
 with sigma of 0.02
 F10A-C43A \\sim F38-C115
 with sigma of 0.04
 F12A-C45A \\sim F41-C117
 with sigma of 0.02
 C44A-C45A \\sim C116-C117
 with sigma of 0.02
 F13A-F12A \\sim F39-F41
 with sigma of 0.04
 C42A-C44A \\sim C118-C116
 with sigma of 0.04
 O4A-C43A \\sim O4A-C115
 with sigma of 0.04
 F9A-F8A \\sim F35-F36
 with sigma of 0.04
 C43A-C45A \\sim C115-C117
 with sigma of 0.04
 F9A-C42A \\sim F35-C118
 with sigma of 0.04
 F9A-C44A \\sim F35-C116
 with sigma of 0.04
 F12A-C44A \\sim F41-C116
 with sigma of 0.04
 F8A-C42A \\sim F36-C118
 with sigma of 0.04
 F8A-C44A \\sim F36-C116
 with sigma of 0.04
 F16A-C57A \\sim F43-C57A
 with sigma of 0.02
 C57A-F17A \\sim C57A-F44
 with sigma of 0.02
 F11A-F10A \\sim F37-F38
 with sigma of 0.04
 F11A-C43A \\sim F37-C115
 with sigma of 0.04
 F11A-C45A \\sim F37-C117
 with sigma of 0.04
 C51A-C46A \\sim C127-C128
 with sigma of 0.02
 C51A-C50A \\sim C127-C126
 with sigma of 0.02
 C51A-C118 \\sim C127-C118
 with sigma of 0.02
 C47A-C54A \\sim C125-C123
 with sigma of 0.04
 C46A-C47A \\sim C128-C125
 with sigma of 0.02
 C50A-C54A \\sim C126-C123
 with sigma of 0.04
 C47A-C52A \\sim C125-C124
 with sigma of 0.02
 C47A-C53A \\sim C125-C121
 with sigma of 0.02
 C47A-C48A \\sim C125-C120
 with sigma of 0.02
 C50A-C53A \\sim C126-C121
 with sigma of 0.02
 C47A-C49A \\sim C125-C119
 with sigma of 0.04
 C50A-C49A \\sim C126-C119
 with sigma of 0.02
 C52A-C53A \\sim C124-C121
 with sigma of 0.04
 C50A-C48A \\sim C126-C120
 with sigma of 0.04
 C54A-C53A \\sim C123-C121
 with sigma of 0.02
 C53A-C48A \\sim C121-C120
 with sigma of 0.04
 C55A-C53A \\sim C122-C121
 with sigma of 0.02
 O5A-C46A \\sim O5A-C128
 with sigma of 0.02
 C47A-C50A \\sim C125-C126
 with sigma of 0.04
 C47A-C55A \\sim C125-C122
 with sigma of 0.04
 C48A-C49A \\sim C120-C119
 with sigma of 0.02
 C52A-C48A \\sim C124-C120
 with sigma of 0.04
 O5A-C51A \\sim O5A-C127
 with sigma of 0.04
 C50A-C55A \\sim C126-C122
 with sigma of 0.04
 O5A-C47A \\sim O5A-C125
 with sigma of 0.04
 C50A-C118 \\sim C126-C118
 with sigma of 0.04
 C42A-C46A \\sim C42A-C128
 with sigma of 0.04
 C42A-C50A \\sim C42A-C126
 with sigma of 0.04
 C54A-C55A \\sim C123-C122
 with sigma of 0.04
 C51A-C47A \\sim C127-C125
 with sigma of 0.04
 C51A-C53A \\sim C127-C121
 with sigma of 0.04
 C51A-C49A \\sim C127-C119
 with sigma of 0.04
 C53A-C49A \\sim C121-C119
 with sigma of 0.04
 C46A-C52A \\sim C128-C124
 with sigma of 0.04
 C46A-C50A \\sim C128-C126
 with sigma of 0.04
 C46A-C53A \\sim C128-C121
 with sigma of 0.04
 C46A-C48A \\sim C128-C120
 with sigma of 0.04
 C42A-C51A \\sim C42A-C127
 with sigma of 0.02
 C46A-C118 \\sim C128-C118
 with sigma of 0.04
 F14A-C45A \\sim F13A-C45A \\sim F12A-C45A
 with sigma of 0.01
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
Uanis(F13A) \\sim Ueq, Uanis(F40) \\sim Ueq: with sigma of 0.004 and sigma for
terminal atoms of 0.008
5. Others
 Sof(F35)=Sof(F36)=Sof(F37)=Sof(F38)=Sof(F39)=Sof(F40)=Sof(C115)=Sof(F41)=
 Sof(C116)=Sof(C117)=Sof(C118)=1-FVAR(1)
 Sof(F9A)=Sof(F8A)=Sof(F11A)=Sof(F10A)=Sof(F13A)=Sof(C42A)=Sof(F14A)=Sof(C43A)=
 Sof(F12A)=Sof(C44A)=Sof(C45A)=FVAR(1)
 Sof(F42)=Sof(F43)=Sof(F44)=1-FVAR(2)
 Sof(F16A)=Sof(F17A)=Sof(F15A)=FVAR(2)
 Sof(F45)=Sof(F46)=Sof(F47)=1-FVAR(3)
 Sof(F17)=Sof(F15)=Sof(F16)=FVAR(3)
 Sof(C119)=Sof(H11B)=Sof(H11C)=Sof(C120)=Sof(H12A)=Sof(H12B)=Sof(C121)=
 Sof(C122)=Sof(H12C)=Sof(H12D)=Sof(H12E)=Sof(C123)=Sof(H12F)=Sof(H12G)=
 Sof(H12H)=Sof(C124)=Sof(H12I)=Sof(H12J)=Sof(H12K)=Sof(C125)=Sof(C126)=
 Sof(H126)=Sof(C127)=Sof(C128)=1-FVAR(4)
 Sof(C51A)=Sof(C46A)=Sof(C47A)=Sof(C52A)=Sof(H52A)=Sof(H52B)=Sof(H52C)=
 Sof(C50A)=Sof(H50A)=Sof(C54A)=Sof(H54A)=Sof(H54B)=Sof(H54C)=Sof(C55A)=
 Sof(H55A)=Sof(H55B)=Sof(H55C)=Sof(C53A)=Sof(C48A)=Sof(H48A)=Sof(H48B)=
 Sof(C49A)=Sof(H49A)=Sof(H49B)=FVAR(4)
6.a Riding coordinates:
 OWA(HWAA,HWAB)
6.b Free rotating group:
 OW(HWA,HWB)
6.c Ternary CH refined with riding coordinates:
 C36A(H36A), C50(H50), C36(H36), C50A(H50A), C126(H126)
6.d Secondary CH2 refined with riding coordinates:
 C16(H16C,H16D), C35A(H35A,H35B), C22(H22A,H22B), C34A(H34A,H34B), C34(H34C,
 H34D), C48(H48C,H48D), C35(H35C,H35D), C16A(H16A,H16B), C49(H49C,H49D),
 C48A(H48A,H48B), C49A(H49A,H49B), C119(H11B,H11C), C120(H12A,H12B), C58(H58A,
 H58B)
6.e Aromatic/amide H refined with riding coordinates:
 N4(H4), C11(H11), N4A(H4A), C13A(H13A), C27A(H27A), C24(H24), C20(H20),
 C7A(H7A), C1(H1), C10A(H10A), C6(H6), C8A(H8A), C21(H21), C21A(H21A), C18(H18),
  C14A(H14A), C14(H14), C3A(H3A), C26A(H26A), C10(H10), C7(H7), C25(H25),
 C8(H8), C5A(H5A), C3(H3), C19A(H19A), C13(H13), C2(H2), C18A(H18A), C11A(H11A),
  C5(H5), C2A(H2A), C24A(H24A), C25A(H25A), C19(H19), C26(H26), C1A(H1A),
 C20A(H20A), C27(H27), C6A(H6A)
6.f Idealised Me refined as rotating group:
 C54(H54D,H54E,H54F), C55(H55D,H55E,H55F), C40A(H40A,H40B,H40C), C41(H41D,H41E,
 H41F), C52(H52D,H52E,H52F), C40(H40D,H40E,H40F), C41A(H41A,H41B,H41C),
 C39A(H39A,H39B,H39C), C39(H39D,H39E,H39F), C52A(H52A,H52B,H52C), C54A(H54A,
 H54B,H54C), C55A(H55A,H55B,H55C), C122(H12C,H12D,H12E), C123(H12F,H12G,H12H),
 C124(H12I,H12J,H12K)
;
_shelx_res_checksum              23430
_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 1.991
_oxdiff_exptl_absorpt_empirical_full_min 0.433