Efficient macrocyclization facilitated by skeleton preorganization
Xu, Rong-Yao; Liu, Xiu; Sun, Guang; Zhang, Zhi-Yuan; Dong, Ming; Zhao, Liya; Zhang, Si-Miao; Wang, Xi-Yang; Zhang, Hong-Xu; Yang, Shang-Jie; Wang, Xiuguang; Li, Bin; Li, Jian; Li, Chunju; RSC Advances 13 (2023) 30269–30272; doi:10.1039/D3RA05671F

data_7247575
_publ_section_title
;
 Efficient macrocyclization facilitated by skeleton preorganization
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              30269
_journal_page_last               30272
_journal_paper_doi               10.1039/D3RA05671F
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         '2(C34 H28 N2 O4), 0.125[]'
_chemical_formula_sum            'C68 H56 N4 O8'
_chemical_formula_weight         1057.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-08
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-10 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.958(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.9126(9)
_cell_length_b                   18.7706(7)
_cell_length_c                   24.7876(8)
_cell_measurement_reflns_used    8759
_cell_measurement_temperature    150
_cell_measurement_theta_max      58.49
_cell_measurement_theta_min      2.73
_cell_volume                     14792.7(8)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1370
_diffrn_reflns_av_unetI/netI     0.0908
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            46774
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        59.138
_diffrn_reflns_theta_max         59.138
_diffrn_reflns_theta_min         2.734
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1056 before and 0.0810 after correction.
The Ratio of minimum to maximum transmission is 0.7839.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.949
_exptl_crystal_description       block
_exptl_crystal_F_000             4448
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.00029(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.291
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     730
_refine_ls_number_reflns         10546
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.298
_refine_ls_R_factor_all          0.1722
_refine_ls_R_factor_gt           0.1283
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3731
_refine_ls_wR_factor_ref         0.4018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5607
_reflns_number_total             10546
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra05671f2.cif
_cod_data_source_block           zzy10111_0m_sq
_cod_database_code               7247575
_shelx_shelxl_version_number     2019/2
_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. Rigid bond restraints
 N2, C33
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C61, C62
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C25) \\sim Ueq, Uanis(C28) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C65(H65A,H65B)
4.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C3(H3), C01Q(H01Q), C21(H21), C14(H14), C10(H10), C32(H32), C7(H7),
 C18(H18), C30(H30), C13(H13), C25(H25), C33(H33), C31(H31), C53(H53), C36(H36),
  C56(H56), C50(H50), C64(H64), C51(H51), C47(H47), C55(H55), C40(H40),
 C61(H61), C58(H58), C44(H44), C43(H43), C57(H57)
4.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1A,H1B,H1C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C),
 C34(H34A,H34B,H34C), C67(H67A,H67B,H67C), C41(H41A,H41B,H41C), C66(H66A,H66B,
 H66C)
;
_shelx_res_checksum              44399
_shelx_fab_checksum              45809
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'