Triggering the Antitumor Activity of Acyclic Enediyne through Maleimide Assisted Rearrangement and Cycloaromatization.
Zhang, Mengsi; Li, Baojun; Chen, Huimin; Lu, Haotian; Ma, Hailong; Cheng, Xiaoyu; Wang, Wenbo; Wang, Yue; Ding, Yun; Hu, Aiguo; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01124

data_4038597
_publ_section_title
;
 Triggering the Antitumor Activity of Acyclic Enediyne through Maleimide
 Assisted Rearrangement and Cycloaromatization.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01124
_journal_year                    2020
_chemical_formula_moiety         'C30 H43 N3 O8'
_chemical_formula_sum            'C30 H43 N3 O8'
_chemical_formula_weight         573.67
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.8334(3)
_cell_length_b                   17.4964(3)
_cell_length_c                   19.2021(3)
_cell_measurement_reflns_used    9835
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      54.94
_cell_measurement_theta_min      4.835
_cell_volume                     6327.41(18)
_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      302.61
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0392
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            56518
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.943
_diffrn_reflns_theta_min         4.084
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1294 before and 0.0530 after correction. The Ratio of minimum to maximum transmission is 0.6433. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0600P)^2^+1.6034P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4848
_reflns_number_total             5984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01124_si_002.cif
_cod_data_source_block           mjr18069
_cod_database_code               4038597
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.914
_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.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C20(H20A,H20B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C24(H24A,
 H24B,H24C), C25(H25A,H25B,H25C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C),
 C30(H30A,H30B,H30C)
;
_shelx_res_checksum              92977
_shelx_hkl_checksum              13025
_olex2_submission_special_instructions 'No special instructions were received'