Synthesis of fused-pyran derivatives <i>via</i> a base-mediated annulation of bis-allenoates followed by auto-oxidation in air.
Zhao, Jun-Bo; Yang, Jing-Kui; Organic & biomolecular chemistry 22 (2024) 6543–6549; doi:10.1039/d4ob00835a

data_7160072
_publ_section_title
;
 Synthesis of fused-pyran derivatives <i>via</i> a base-mediated
 annulation of bis-allenoates followed by auto-oxidation in air.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6543
_journal_page_last               6549
_journal_paper_doi               10.1039/d4ob00835a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C23 H16 I2 O2, 0.8[CHCl3]'
_chemical_formula_sum            'C23 H18 I2 O2'
_chemical_formula_weight         580.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-01-15
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2024-01-27 deposited with the CCDC.	2024-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.605(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5721(19)
_cell_length_b                   8.3586(8)
_cell_length_c                   17.0294(19)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.39
_cell_volume                     2356.5(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0578
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            53896
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_min         1.677
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.682
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0926 before and 0.0632 after correction.
The Ratio of minimum to maximum transmission is 0.8211.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.781
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         5851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0787P)^2^+4.4748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1651
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4170
_reflns_number_total             5851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00835a2.cif
_cod_data_source_block           mo_zjb_285_a_0m
_cod_depositor_comments
'Adding full bibliography for 7160072--7160073.cif.'
_cod_database_code               7160072
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.616
_shelx_estimated_absorpt_t_min   0.500
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C22(H22), C23(H23)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              4064
_shelx_fab_checksum              29007
_olex2_submission_special_instructions 'No special instructions were received'