High-Yield and Sustainable Synthesis of Quinoidal Compounds Assisted by Keto-Enol Tautomerism
Wang, Cheng; Li, Rongjin; Dang, Yanfeng; Wei, Haipeng; Jiang, Yu; Zhao, Xuxia; Geng, Yanhou; Yao, Jiarong; Deng, Yunfeng; Du, Tian; Li, Riqing; Chemical Science  (2021) –; doi:10.1039/D1SC01685G

data_1563270
_publ_section_title
;
 High-Yield and Sustainable Synthesis of Quinoidal Compounds Assisted by
 Keto-Enol Tautomerism
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01685G
_journal_year                    2021
_chemical_formula_moiety         'C64 H78 N2 O6 S2'
_chemical_formula_sum            'C64 H78 N2 O6 S2'
_chemical_formula_weight         1035.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-12 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.923(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.8786(11)
_cell_length_b                   5.1836(3)
_cell_length_c                   27.5685(17)
_cell_measurement_reflns_used    5190
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.58
_cell_measurement_theta_min      2.79
_cell_volume                     2840.4(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      170.01
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            19822
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.037
_diffrn_reflns_theta_min         2.789
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.818
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1684 before and 0.0604 after correction. The Ratio of minimum to maximum transmission is 0.7810. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       needle
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.886
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5234
_refine_ls_number_restraints     83
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.0946
_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^)+(0.1000P)^2^+10.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2388
_refine_ls_wR_factor_ref         0.2707
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3144
_reflns_number_total             5234
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01685g2.cif
_cod_data_source_block           190708dyf_2_0m
_cod_database_code               1563270
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.923
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C28-C27 = C29-C28 = C29-C30 = C31-C30 = C32-C31 = C20-C19 = C21-C20 = C21-C22
 = C23-C22 = C24-C23
 1.53 with sigma of 0.02
 C29-C28
 1.53 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
C25 \\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C18(H18)
4.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B),
 C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14)
4.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              3721
_olex2_submission_special_instructions 'No special instructions were received'