(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_7159393
_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         'C27 H29 N O6'
_chemical_formula_sum            'C27 H29 N O6'
_chemical_formula_weight         463.51
_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             2022-12-01
_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                90
_cell_angle_beta                 107.445(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7617(4)
_cell_length_b                   21.8252(8)
_cell_length_c                   9.9033(3)
_cell_measurement_reflns_used    9705
_cell_measurement_temperature    300.7
_cell_measurement_theta_max      26.0240
_cell_measurement_theta_min      2.0760
_cell_volume                     2425.26(15)
_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      300.7
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.943
_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     30.00  88.00   0.50    8.00    --   16.22  77.00  30.00  116
  2  \w    -36.00  19.00   0.50    8.00    --  -15.60 -94.00 -90.00  110
  3  \w    -37.00  -7.00   0.50    8.00    --   16.22 -94.00 -30.00   60
  4  \w    -90.00   2.00   0.50    8.00    --  -15.60 -13.00  34.00  184
  5  \w    -36.00  21.00   0.50    8.00    --  -15.60 -94.00 120.00  114
  6  \w    -90.00   2.00   0.50    8.00    --  -15.60 -13.00  34.00  184
  7  \w    -52.00 -11.00   0.50    8.00    --  -15.60 125.00  30.00   82
  8  \w    -66.00 -12.00   0.50    8.00    --  -15.60 125.00 -30.00  108
  9  \w    -37.00 -12.00   0.50    8.00    --  -15.60  13.00-153.00   50
 10  \w    -56.00  95.00   0.50    8.00    --   16.22  13.00-153.00  302
 11  \w     18.00  66.00   0.50    8.00    --   16.22-125.00-180.00   96
 12  \w    -57.00  41.00   0.50    8.00    --   16.22 -30.00-180.00  196
 13  \w    -70.00 -12.00   0.50    8.00    --  -15.60 125.00 120.00  116
;
_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      -0.0536506000
_diffrn_orient_matrix_UB_12      0.0035768000
_diffrn_orient_matrix_UB_13      -0.0560867000
_diffrn_orient_matrix_UB_21      -0.0333997000
_diffrn_orient_matrix_UB_22      -0.0047256000
_diffrn_orient_matrix_UB_23      0.0480582000
_diffrn_orient_matrix_UB_31      0.0010846000
_diffrn_orient_matrix_UB_32      0.0319541000
_diffrn_orient_matrix_UB_33      0.0133855000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27663
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.267
_diffrn_reflns_theta_min         2.041
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65072
_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    1.269
_exptl_crystal_description       needle
_exptl_crystal_F_000             984
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.040
_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     312
_refine_ls_number_reflns         5137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0744P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2963
_reflns_number_total             5137
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00597f2.cif
_cod_data_source_block           Compound4an
_cod_depositor_comments
'Adding full bibliography for 7159392--7159395.cif.'
_cod_database_code               7159393
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 99.67
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C2(H2), C19(H19), C15(H15), C17(H17), C3(H3), C5(H5), C4(H4),
 C16(H16)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              48013
_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 1.647
_oxdiff_exptl_absorpt_empirical_full_min 0.557