(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_7159395
_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         'C36 H28 N2 O3'
_chemical_formula_sum            'C36 H28 N2 O3'
_chemical_formula_weight         536.60
_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             2023-03-10
_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                100.268(3)
_cell_angle_beta                 113.577(3)
_cell_angle_gamma                98.024(3)
_cell_formula_units_Z            2
_cell_length_a                   10.5236(3)
_cell_length_b                   11.4554(5)
_cell_length_c                   12.9859(4)
_cell_measurement_reflns_used    4826
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      21.3200
_cell_measurement_theta_min      2.1110
_cell_volume                     1372.68(10)
_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      298.0
_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 0.999
_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    -63.00  98.00   0.50    4.00    --   16.22   9.00  -0.00  322
  2  \w     13.00  43.00   0.50    4.00    --  -15.60-131.00 -19.25   60
  3  \w     10.00  71.00   0.50    4.00    --   16.22-125.00   0.00  122
  4  \w    -37.00  21.00   0.50    4.00    --  -15.60 -94.00  60.00  116
  5  \w    -37.00  21.00   0.50    4.00    --  -15.60 -94.00 120.00  116
  6  \w    -54.00  41.00   0.50    4.00    --   16.22 -45.00  90.00  190
  7  \w     -8.00  86.00   0.50    4.00    --   16.22  45.00  60.00  188
  8  \w    -37.00  21.00   0.50    4.00    --  -15.60 -94.00 -60.00  116
  9  \w     10.00  71.00   0.50    4.00    --   16.22-125.00-120.00  122
 10  \w    -37.00  21.00   0.50    4.00    --  -15.60 -94.00-150.00  116
 11  \w    -65.00  95.00   0.50    4.00    --   16.22  -9.00-175.00  320
 12  \w    -70.00 -10.00   0.50    4.00    --  -15.60 125.00 -60.00  120
 13  \w    -70.00 -10.00   0.50    4.00    --  -15.60 125.00-120.00  120
 14  \w    -70.00 -10.00   0.50    4.00    --  -15.60 125.00-150.00  120
 15  \w    -97.00  63.00   0.50    4.00    --  -15.60  -9.00-175.00  320
 16  \w    -70.00 -10.00   0.50    4.00    --  -15.60 125.00 -30.00  120
 17  \w    -70.00 -10.00   0.50    4.00    --  -15.60 125.00   0.00  120
 18  \w    -70.00 -10.00   0.50    4.00    --  -15.60 125.00  60.00  120
 19  \w    -95.00  66.00   0.50    4.00    --  -15.60   9.00  -0.00  322
 20  \w    -86.00   9.00   0.50    4.00    --  -15.60 -45.00 150.00  190
 21  \w    -89.00   9.00   0.50    4.00    --  -15.60 -30.00   0.00  196
;
_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      0.0556001000
_diffrn_orient_matrix_UB_12      -0.0276897000
_diffrn_orient_matrix_UB_13      -0.0016998000
_diffrn_orient_matrix_UB_21      -0.0411481000
_diffrn_orient_matrix_UB_22      -0.0575873000
_diffrn_orient_matrix_UB_23      -0.0061077000
_diffrn_orient_matrix_UB_31      -0.0306018000
_diffrn_orient_matrix_UB_32      -0.0102828000
_diffrn_orient_matrix_UB_33      -0.0613562000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2935
_diffrn_reflns_av_unetI/netI     0.2577
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29773
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.121
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36531
_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            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       plate
_exptl_crystal_F_000             564
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.2760
_refine_ls_R_factor_gt           0.1228
_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^)+(0.0635P)^2^+3.2528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2528
_refine_ls_wR_factor_ref         0.4444
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1591
_reflns_number_total             4864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00597f2.cif
_cod_data_source_block           Compound8al
_cod_depositor_comments
'Adding full bibliography for 7159392--7159395.cif.'
_cod_original_cell_volume        1372.67(9)
_cod_database_code               7159395
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.984
_reflns_odcompleteness_completeness 99.98
_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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C4(H4), C27(H27), C30(H30), C12(H12), C20(H20), C11(H11), C28(H28),
 C23(H23), C22(H22), C8(H8), C29(H29), C21(H21), C14(H14), C10(H10), C18(H18),
 C15(H15), C9(H9), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C)
;
_shelx_res_checksum              92993
_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 4.910
_oxdiff_exptl_absorpt_empirical_full_min 0.291