(3 + 3) Annulation of acetoxy allenoates with enolisable carbonyl substrates leading to fused pyrans.
Debnath, Shubham; Chauhan, Sachin; Kumara Swamy, K. C.; Organic & biomolecular chemistry 21 (2023) 5021–5032; doi:10.1039/d3ob00597f

data_7159394
_publ_section_title
;
 (3 + 3) Annulation of acetoxy allenoates with enolisable carbonyl
 substrates leading to fused pyrans.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5021
_journal_page_last               5032
_journal_paper_doi               10.1039/d3ob00597f
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C21 H18 O4'
_chemical_formula_sum            'C21 H18 O4'
_chemical_formula_weight         334.35
_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             2022-09-30
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2023-04-18 deposited with the CCDC.	2023-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                72.914(2)
_cell_angle_beta                 83.275(2)
_cell_angle_gamma                75.314(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2390(2)
_cell_length_b                   8.5305(2)
_cell_length_c                   12.8575(3)
_cell_measurement_reflns_used    9225
_cell_measurement_temperature    297.1
_cell_measurement_theta_max      25.9430
_cell_measurement_theta_min      2.5520
_cell_volume                     834.67(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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_environment      air
_diffrn_ambient_temperature      297.1
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -42.00  54.00   0.50    3.20    --  -15.60  51.00 -18.00  192
  2  \w    -10.00  86.00   0.50    3.20    --   16.22  51.00 -18.00  192
  3  \w    -37.00  21.00   0.50    3.20    --  -15.60 -94.00   0.00  116
  4  \w    -37.00  21.00   0.50    3.20    --  -15.60 -94.00 -30.00  116
  5  \w    -37.00  53.00   0.50    3.20    --   16.22 -94.00 -90.00  180
  6  \w    -37.00  21.00   0.50    3.20    --  -15.60 -94.00-150.00  116
  7  \w    -53.00  42.00   0.50    3.20    --   16.22 -51.00-164.00  190
  8  \w    -47.00  57.00   0.50    3.20    --  -15.60  77.00-180.00  208
  9  \w    -70.00 -10.00   0.50    3.20    --  -15.60 125.00 -60.00  120
 10  \w    -89.00   9.00   0.50    3.20    --  -15.60 -30.00-150.00  196
 11  \w    -85.00  11.00   0.50    3.20    --  -15.60 -51.00-164.00  192
 12  \w    -70.00 -10.00   0.50    3.20    --  -15.60 125.00-180.00  120
 13  \w    -85.00  12.00   0.50    3.20    --  -15.60 -61.00  30.00  194
 14  \w    -37.00  53.00   0.50    3.20    --   16.22 -94.00  60.00  180
 15  \w    -37.00  21.00   0.50    3.20    --  -15.60 -94.00  90.00  116
 16  \w    -37.00  21.00   0.50    3.20    --  -15.60 -94.00 120.00  116
 17  \w     10.00  71.00   0.50    3.20    --   16.22-125.00 150.00  122
 18  \w    -40.00  55.00   0.50    3.20    --  -15.60  45.00  90.00  190
 19  \w    -54.00  41.00   0.50    3.20    --   16.22 -45.00 120.00  190
 20  \w    -88.00  16.00   0.50    3.20    --  -15.60 -77.00 150.00  208
 21  \w    -95.00  43.00   0.50    3.20    --  -15.60 -15.00  60.00  276
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0188643000
_diffrn_orient_matrix_UB_12      0.0770312000
_diffrn_orient_matrix_UB_13      -0.0008776000
_diffrn_orient_matrix_UB_21      0.0704917000
_diffrn_orient_matrix_UB_22      -0.0158739000
_diffrn_orient_matrix_UB_23      -0.0359305000
_diffrn_orient_matrix_UB_31      -0.0511139000
_diffrn_orient_matrix_UB_32      0.0425074000
_diffrn_orient_matrix_UB_33      -0.0452344000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19973
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.218
_diffrn_reflns_theta_min         2.558
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0586P)^2^+0.0914P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1170
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2781
_reflns_number_total             3575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00597f2.cif
_cod_data_source_block           Compound6aa
_cod_depositor_comments
'Adding full bibliography for 7159392--7159395.cif.'
_cod_database_code               7159394
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C1(H1), C15(H15), C5(H5), C4(H4), C14(H14), C2(H2),
 C13(H13), C3(H3)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              38502
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.401
_oxdiff_exptl_absorpt_empirical_full_min 0.537