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_1559825
_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         '4(F6 P), C56 H64 N8'
_chemical_formula_sum            'C56 H64 F24 N8 P4'
_chemical_formula_weight         1429.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 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                90
_cell_angle_beta                 103.355(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.1270(9)
_cell_length_b                   8.8196(4)
_cell_length_c                   21.3425(12)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.85
_cell_measurement_theta_min      2.31
_cell_volume                     3136.7(3)
_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      153.01
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0582
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            59699
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.097
_diffrn_reflns_theta_min         2.509
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1220 before and 0.0675 after correction.
The Ratio of minimum to maximum transmission is 0.9154.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       block
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         6930
_refine_ls_number_restraints     248
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0634
_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^)+(0.0743P)^2^+3.8057P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4883
_reflns_number_total             6930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06017h2.cif
_cod_data_source_block           mo_h19062302_0m_a
_cod_depositor_comments
;Adding full bibliography for 1559823--1559829.cif.

 Adding full bibliography for 1559823--1559829.cif.
;
_cod_database_code               1559825
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.952
_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,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 P1-F3B \\sim P1-F3A
 with sigma of 0.02
 P1-F6B \\sim P1-F6A
 with sigma of 0.02
 P1-F5B \\sim P1-F5A
 with sigma of 0.02
 P1-F4B \\sim P1-F4A
 with sigma of 0.02
 P2-F9B \\sim P2-F9A
 with sigma of 0.02
 P2-F12B \\sim P2-F12A
 with sigma of 0.02
 P2-F11B \\sim P2-F11A
 with sigma of 0.02
 P2-F10B \\sim P2-F10A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F4B) \\sim Ueq, Uanis(F5B) \\sim Ueq, Uanis(F6B) \\sim Ueq, Uanis(F3B)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C26C) = Uanis(C26B)
4. Rigid body (RIGU) restrains
 P1, F3B, F3A, F6B, F6A, F5B, F5A, F4B, F4A, F1, F2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 P2, F10B, F10A, F9B, F9A, F12B, F12A, F11B, F11A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C25, C26B, C27B, C28B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C26A, C27A, C28A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C25, C26C, C27C, C28C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(F6B)=Sof(F5B)=Sof(F4B)=Sof(F3B)=1-FVAR(1)
 Sof(F4A)=Sof(F3A)=Sof(F5A)=Sof(F6A)=FVAR(1)
 Sof(F11B)=Sof(F9B)=Sof(F12B)=Sof(F10B)=1-FVAR(2)
 Sof(F11A)=Sof(F10A)=Sof(F9A)=Sof(F12A)=FVAR(2)
 Fixed Sof: H25E(0.4) H25F(0.4) H25A(0.4) H25B(0.4) H25C(0.2) H25D(0.2)
 C26A(0.4) H26A(0.4) H26B(0.4) C27A(0.4) H27A(0.4) H27B(0.4) C28A(0.4)
 H28A(0.4) H28B(0.4) H28C(0.4) C26C(0.4) H26C(0.4) H26D(0.4) C27C(0.4)
 H27C(0.4) H27D(0.4) C27B(0.2) H27E(0.2) H27F(0.2) C26B(0.2) H26E(0.2)
 H26F(0.2) C28B(0.2) H28D(0.2) H28E(0.2) H28F(0.2) C28C(0.4) H28G(0.4)
 H28H(0.4) H28I(0.4)
6.a Ternary CH refined with riding coordinates:
 C14(H14), C7(H7)
6.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C21(H21A,H21B), C25(H25E,H25F), C25(H25A,H25B), C25(H25C,
 H25D), C23(H23A,H23B), C26A(H26A,H26B), C27A(H27A,H27B), C26C(H26C,H26D),
 C27C(H27C,H27D), C27B(H27E,H27F), C26B(H26E,H26F)
6.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C16(H16), C17(H17), C12(H12), C9(H9), C10(H10), C19(H19), C18(H18),
 C1(H1), C20(H20), C3(H3), C2(H2)
6.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C28A(H28A,H28B,H28C), C28B(H28D,H28E,H28F), C28C(H28G,
 H28H,H28I)
;
_shelx_res_checksum              10167
_olex2_submission_special_instructions 'No special instructions were received'