Reactivity of Vinyl Epoxides/Oxetanes/Cyclopropanes toward Arynes: Access to Functionalized Phenanthrenes
Liu, Jiupeng; Tang, Shuo; Zhao, Mengyao; Huai, Jianing; Yu, Jingya; Zhao, Jingjing; Li, Pan; ACS Omega 6 (2021) 35852–35865; doi:10.1021/acsomega.1c06166

data_4519255
_publ_section_title
;
 Reactivity of Vinyl Epoxides/Oxetanes/Cyclopropanes toward Arynes: Access
 to Functionalized Phenanthrenes
;
_journal_issue                   51
_journal_name_full               'ACS Omega'
_journal_page_first              35852
_journal_page_last               35865
_journal_paper_doi               10.1021/acsomega.1c06166
_journal_volume                  6
_journal_year                    2021
_chemical_formula_moiety         'C24 H22 O'
_chemical_formula_sum            'C24 H22 O'
_chemical_formula_weight         326.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.475(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.34(2)
_cell_length_b                   9.228(6)
_cell_length_c                   16.238(11)
_cell_measurement_reflns_used    8915
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.299
_cell_measurement_theta_min      2.505
_cell_volume                     3494(4)
_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
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Helios multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24768
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.374
_diffrn_source_type              Microfocus
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1346 before and 0.0655 after correction. The Ratio of minimum to maximum transmission is 0.8789. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0779
_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^)+(0.0708P)^2^+7.5767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2030
_refine_ls_wR_factor_ref         0.2132
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5460
_reflns_number_total             6817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c06166_si_002.cif
_cod_data_source_block           m7993_0m_a
_cod_depositor_comments
;

2025-07-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H44 O2'
_cod_original_formula_weight         652.83
_cod_original_formula_moiety         '2(C24 H22 O)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        3493(4)
_cod_database_code               4519255
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.988
_diffrn_source_source            'Incoatc Ius 3.0 '
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C17(H17), C39(H39), C40(H40)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C29(H29), C30(H30),
  C31(H31), C32(H32), C34(H34), C36(H36), C37(H37), C43(H43), C44(H44),
 C45(H45), C46(H46), C47(H47)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C38(H38A,H38B,H38C), C41(H41A,H41B,
 H41C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2A)
;
_shelx_res_checksum              78990
_shelx_hkl_checksum              2326
_olex2_submission_special_instructions 'No special instructions were received'