Supramolecular-induced regiocontrol over the photochemical [4 + 4] cyclodimerization of NHC- or azole-substituted anthracenes.
Bai, Sha; Ma, Li-Li; Yang, Tao; Wang, Fang; Wang, Li-Feng; Hahn, F. Ekkehardt; Wang, Yao-Yu; Han, Ying-Feng; Chemical science 12 (2020) 2165–2171; doi:10.1039/d0sc06017h

data_1559826
_publ_section_title
;
 Supramolecular-induced regiocontrol over the photochemical [4 + 4]
 cyclodimerization of NHC- or azole-substituted anthracenes.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2165
_journal_page_last               2171
_journal_paper_doi               10.1039/d0sc06017h
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C56 H60 Ag2 N8, 2(C24 H20 B)'
_chemical_formula_sum            'C104 H100 Ag2 B2 N8'
_chemical_formula_weight         1699.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_Hall           'A 2 -2ab'
_space_group_name_H-M_alt        'A e a 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-24 deposited with the CCDC.	2020-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9095(4)
_cell_length_b                   41.3302(17)
_cell_length_c                   26.6661(11)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.52
_cell_measurement_theta_min      2.46
_cell_volume                     9819.3(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200.02
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            81378
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.489
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_T_max  0.4912
_exptl_absorpt_correction_T_min  0.4570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1149 before and 0.0501 after correction.
The Ratio of minimum to maximum transmission is 0.9304.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       block
_exptl_crystal_F_000             3536
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.829
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 4091 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(6)
_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     562
_refine_ls_number_reflns         10808
_refine_ls_number_restraints     88
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0438P)^2^+11.5943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.952
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                9461
_reflns_number_total             10808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06017h2.cif
_cod_data_source_block           mo_h19123004_0m_a_sq
_cod_depositor_comments
;Adding full bibliography for 1559823--1559829.cif.

 Adding full bibliography for 1559823--1559829.cif.
;
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_database_code               1559826
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.885
_shelx_estimated_absorpt_t_min   0.870
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C50B-C48 \\sim C50A-C48 \\sim C52A-C49 \\sim C49-C52B
 with sigma of 0.02
 C51A-C52A \\sim C51B-C52B \\sim C50B-C51B \\sim C51A-C50A
 with sigma of 0.02
 C26A-C25 \\sim C25-C26B
 with sigma of 0.02
 C27B-C26B \\sim C27A-C26A
 with sigma of 0.02
 C28B-C27B \\sim C28A-C27A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C27A \\sim C27B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
C28A \\sim C28B: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
4. Rigid body (RIGU) restrains
 C48, C50A, C50B, C51A, C51B, C52A, C52B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C27A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C25, C26A, C26B, C27A, C27B, C28A, C28B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(H25C)=Sof(H25D)=Sof(C27B)=Sof(H27C)=Sof(H27D)=Sof(C26B)=Sof(H26C)=
 Sof(H26D)=Sof(C28B)=Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(H25A)=Sof(H25B)=Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(C27A)=Sof(H27A)=
 Sof(H27B)=Sof(C28A)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(1)
 Fixed Sof: H48(0.4) H48A(0.6) H49(0.4) H49A(0.6) C50A(0.4) H50A(0.4)
 C52A(0.4) H52A(0.4) C51A(0.4) H51A(0.4) C51B(0.6) H51B(0.6) C52B(0.6)
 H52B(0.6) C50B(0.6) H50B(0.6)
6.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C21(H21A,H21B), C23(H23A,H23B), C25(H25A,H25B), C25(H25C,
 H25D), C26A(H26A,H26B), C27A(H27A,H27B), C27B(H27C,H27D), C26B(H26C,H26D)
6.b Me refined with riding coordinates:
 C28B(H28D,H28E,H28F)
6.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C19(H19), C46(H46), C14(H14), C7(H7), C42(H42), C12(H12), C9(H9),
 C10(H10), C16(H16), C45(H45), C2(H2), C3(H3), C17(H17), C5(H5), C30(H30),
 C48(H48), C48(H48A), C31(H31), C38(H38), C40(H40), C34(H34), C44(H44),
 C36(H36), C39(H39), C32(H32), C37(H37), C49(H49), C49(H49A), C43(H43),
 C33(H33), C50A(H50A), C52A(H52A), C51A(H51A), C51B(H51B), C52B(H52B),
 C50B(H50B)
6.d Fitted pentagon refined as free rotating group:
 C18(N4,C20,C19,N3), C2(C3,N2,C1,N1)
6.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C28A(H28A,H28B,H28C)
;
_shelx_res_checksum              2544
_shelx_fab_checksum              56523
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'