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_1559824
_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 H64 N8, 4(F6 P)'
_chemical_formula_sum            'C56 H64 F24 N8 P4'
_chemical_formula_weight         1429.03
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                103.060(3)
_cell_angle_beta                 94.575(3)
_cell_angle_gamma                103.138(3)
_cell_formula_units_Z            1
_cell_length_a                   8.8950(8)
_cell_length_b                   12.0690(10)
_cell_length_c                   15.1617(15)
_cell_measurement_reflns_used    5591
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.74
_cell_measurement_theta_min      2.53
_cell_volume                     1529.2(2)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      180.01
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0408
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17745
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.034
_diffrn_reflns_theta_max         25.034
_diffrn_reflns_theta_min         2.581
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1179 before and 0.0402 after correction.
The Ratio of minimum to maximum transmission is 0.9101.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.914
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     626
_refine_ls_number_reflns         5369
_refine_ls_number_restraints     316
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0814
_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^)+(0.1019P)^2^+2.3943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2030
_refine_ls_wR_factor_ref         0.2294
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3703
_reflns_number_total             5369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06017h2.cif
_cod_data_source_block           mo_h2020082306_0m_a
_cod_depositor_comments
;Adding full bibliography for 1559823--1559829.cif.

 Adding full bibliography for 1559823--1559829.cif.
;
_cod_database_code               1559824
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.944
_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
 P1-F4A \\sim P1-F3B
 with sigma of 0.02
 P2B-F9B \\sim P2A-F9A
 with sigma of 0.02
 P2B-F8B \\sim P2A-F8A
 with sigma of 0.02
 P1-F2A \\sim P1-F2B
 with sigma of 0.02
 F9B-F12B \\sim F9A-F12A
 with sigma of 0.04
 P2B-F10B \\sim P2A-F10A
 with sigma of 0.02
 P2B-F12B \\sim P2A-F12A
 with sigma of 0.02
 F10B-F7B \\sim F10A-F7A
 with sigma of 0.04
 F8B-F12B \\sim F8A-F12A
 with sigma of 0.04
 P2B-F7B \\sim P2A-F7A
 with sigma of 0.02
 P1-F6A \\sim P1-F5B
 with sigma of 0.02
 P2B-F11B \\sim P2A-F11A
 with sigma of 0.02
 F9B-F11B \\sim F9A-F11A
 with sigma of 0.04
 P1-F3A \\sim P1-F6B
 with sigma of 0.02
 F8B-F11B \\sim F8A-F11A
 with sigma of 0.04
 F12B-F7B \\sim F12A-F7A
 with sigma of 0.04
 P1-F1A \\sim P1-F1B
 with sigma of 0.02
 F7B-F11B \\sim F7A-F11A
 with sigma of 0.04
 F9B-F10B \\sim F9A-F10A
 with sigma of 0.04
 P1-F5A \\sim P1-F4B
 with sigma of 0.02
 F9B-F7B \\sim F9A-F7A
 with sigma of 0.04
 F8B-F10B \\sim F8A-F10A
 with sigma of 0.04
 F8B-F7B \\sim F8A-F7A
 with sigma of 0.04
 F10B-F12B \\sim F10A-F12A
 with sigma of 0.04
 F10B-F11B \\sim F10A-F11A
 with sigma of 0.04
 F12B-F11B \\sim F12A-F11A
 with sigma of 0.04
 F9B-F8B \\sim F9A-F8A
 with sigma of 0.04
 N1-C24A \\sim N1-C24B
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
P2B \\sim P2A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 P2A, F9A, F8A, F10A, F12A, F7A, F11A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 P2B, F9B, F8B, F10B, F12B, F7B, F11B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F4B, P1, F5B, F4A, F6B, F3A, F3B, F2A, F6A, F1A, F1B, F2B, F5A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N1, C24A, C25A, C26A, C27A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C27B, C26B, C25B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(F2B)=Sof(F3B)=Sof(F5B)=Sof(F6B)=Sof(F1B)=Sof(F4B)=1-FVAR(1)
 Sof(F2A)=Sof(F4A)=Sof(F6A)=Sof(F3A)=Sof(F1A)=Sof(F5A)=FVAR(1)
 Fixed Sof: H19(0.7) H19A(0.3) N4B(0.7) C28A(0.7) H28A(0.7) H22A(0.7)
 H22B(0.7) H22C(0.3) H22D(0.3) C24A(0.7) H24A(0.7) H24B(0.7) C20B(0.7)
 H20A(0.7) H20B(0.7) C21B(0.7) H21A(0.7) H21B(0.7) C25A(0.7) H25A(0.7)
 H25B(0.7) C26B(0.3) H26A(0.3) H26B(0.3) C27A(0.7) H27A(0.7) H27B(0.7)
 H27C(0.7) P2B(0.5) F9B(0.5) F8B(0.5) F10B(0.5) F12B(0.5) F7B(0.5) F11B(0.5)
 P2A(0.5) F9A(0.5) F8A(0.5) F10A(0.5) F12A(0.5) F7A(0.5) F11A(0.5) C25B(0.3)
 H25C(0.3) H25D(0.3) C24B(0.3) H24C(0.3) H24D(0.3) C27B(0.3) H27D(0.3)
 H27E(0.3) H27F(0.3) C26A(0.7) H26C(0.7) H26D(0.7) C20A(0.3) H20C(0.3)
 H20D(0.3) C21A(0.3) H21C(0.3) H21D(0.3) N4A(0.3) C28B(0.3) H28B(0.3)
6.a Ternary CH refined with riding coordinates:
 C8(H8), C15(H15)
6.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C22(H22C,H22D), C24A(H24A,H24B), C20B(H20A,H20B), C21B(H21A,
 H21B), C25A(H25A,H25B), C26B(H26A,H26B), C25B(H25C,H25D), C24B(H24C,H24D),
 C26A(H26C,H26D), C20A(H20C,H20D), C21A(H21C,H21D)
6.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C6(H6), C10(H10), C13(H13), C5(H5), C12(H12), C3(H3), C1(H1),
 C18(H18), C19(H19), C19(H19A), C2(H2), C28A(H28A), C28B(H28B)
6.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C27A(H27A,H27B,H27C), C27B(H27D,H27E,H27F)
;
_shelx_res_checksum              42060
_olex2_submission_special_instructions 'No special instructions were received'