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_7160073
_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         'C25 H19 F3 O4'
_chemical_formula_sum            'C25 H19 F3 O4'
_chemical_formula_weight         440.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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                97.196(6)
_cell_angle_beta                 113.780(6)
_cell_angle_gamma                92.477(6)
_cell_formula_units_Z            2
_cell_length_a                   9.6264(17)
_cell_length_b                   10.7417(18)
_cell_length_c                   11.025(2)
_cell_measurement_reflns_used    9609
_cell_measurement_temperature    300
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.32
_cell_volume                     1029.5(3)
_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      300
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_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  0.0598
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            38754
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_min         2.044
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1164 before and 0.0656 after correction.
The Ratio of minimum to maximum transmission is 0.9378.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5079
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0815
_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^)+(0.1345P)^2^+0.4503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2446
_refine_ls_wR_factor_ref         0.2684
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3595
_reflns_number_total             5079
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00835a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7160072--7160073.cif.'
_cod_database_code               7160073
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.956
_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
 C2, F1, F2, F3, F1A, F2A, F3A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C2 \\sim F1 \\sim F2 \\sim F3 \\sim F1A \\sim F2A \\sim F3A: within 1.7A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
4. Rigid body (RIGU) restrains
 C2, F1, F2, F3, F1A, F2A, F3A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C12(H12), C13(H13), C16(H16), C23(H23), C24(H24),
 C28(H28), C29(H29)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              81726
_olex2_submission_special_instructions 'No special instructions were received'