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_1559827
_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
'3.5(C F3 O3 S), 0.5(H4 O2), C56 H39.5 N8, 0.5(C4 H6 N2)'
_chemical_formula_sum            'C61.5 H44.5 F10.5 N9 O11.5 S3.5'
_chemical_formula_weight         1405.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-12-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-14 deposited with the CCDC.	2020-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.970(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0294(8)
_cell_length_b                   19.1408(16)
_cell_length_c                   19.9693(18)
_cell_measurement_reflns_used    8437
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.93
_cell_measurement_theta_min      2.31
_cell_volume                     3057.5(5)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.01
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0563
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            36901
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.389
_diffrn_reflns_theta_min         2.307
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0929 before and 0.0505 after correction.
The Ratio of minimum to maximum transmission is 0.9057.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_description       block
_exptl_crystal_F_000             1438
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         5783
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0686
_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^)+(0.1135P)^2^+3.7930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1876
_refine_ls_wR_factor_ref         0.2131
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4121
_reflns_number_total             5783
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06017h2.cif
_cod_data_source_block           h19111702_a
_cod_depositor_comments
;Adding full bibliography for 1559823--1559829.cif.

 Adding full bibliography for 1559823--1559829.cif.
;
_cod_original_formula_sum        'C61.50 H44.50 F10.50 N9 O11.50 S3.50'
_cod_database_code               1559827
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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
 F4A-C30 \\sim F4B-C30
 with sigma of 0.02
 F2A-C29 \\sim F2B-C29
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F4A \\sim F4B: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
O8A \\sim O8B: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O6A) = Uanis(O6B)
Uanis(O7A) = Uanis(O7B)
4. Others
 Fixed Sof: S3(0.35) S4B(0.15) H1B(0.5) H4(0.75) F4A(0.3) F2B(0.5) F7(0.8)
 F8(0.4) O8A(0.5) C32(0.4) O9A(0.25) O9B(0.15) S4A(0.25) O8B(0.3) H34B(0.5)
 H34C(0.5) F2A(0.5) F4B(0.2) O7A(0.28) O6A(0.56) C31(0.35) F6(0.35) F5(0.7)
 O6B(0.07) O7B(0.14)
5.a Free rotating group:
 O1(H1B,H1C)
5.b Ternary CH refined with riding coordinates:
 C12(H12), C19(H19)
5.c Me refined with riding coordinates:
 C34(H34A,H34B,H34C)
5.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C14(H14), N4(H4), C17(H17), C10(H10), C21(H21), C1(H1A), C16(H16),
 C9(H9), C24(H24), C22(H22), C6(H6), C3(H3), C25(H25), C27(H27), C5(H5),
 C26(H26), C4(H4A)
;
_shelx_res_checksum              33199
_olex2_submission_special_instructions 'No special instructions were received'