Pd-Catalyzed Formal [3 + 3] Heteroannulation of Allylic gem-Diacetates: Synthesis of Chromene-Based Natural Products and Exploration of Photochromic Properties
Kumar, Prashant; Kumar, Pravesh; Venkataramani, Sugumar; Ramasastry, S. S. V.; ACS Catalysis  (2021) 963–970; doi:10.1021/acscatal.1c05450

data_4519240
_publ_section_title
;
 Pd-Catalyzed Formal [3 + 3] Heteroannulation of Allylic gem-Diacetates:
 Synthesis of Chromene-Based Natural Products and Exploration of
 Photochromic Properties
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              963
_journal_page_last               970
_journal_paper_doi               10.1021/acscatal.1c05450
_journal_year                    2021
_chemical_formula_moiety         'C22 H18 O'
_chemical_formula_sum            'C22 H18 O'
_chemical_formula_weight         298.36
_chemical_name_systematic        Cromin
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-09-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 114.810(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7358(18)
_cell_length_b                   10.5737(11)
_cell_length_c                   13.773(2)
_cell_measurement_reflns_used    1983
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.3680
_cell_measurement_theta_min      2.7590
_cell_volume                     1551.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXH-1997  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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     32.00 114.20   0.30   20.00    --   29.89  54.00-180.00  274
  2  \w    -68.00  18.10   0.30   20.00    --   29.89  54.00-180.00  287
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0573586000
_diffrn_orient_matrix_UB_12      -0.0319353000
_diffrn_orient_matrix_UB_13      -0.0112294000
_diffrn_orient_matrix_UB_21      0.0270445000
_diffrn_orient_matrix_UB_22      -0.0575050000
_diffrn_orient_matrix_UB_23      -0.0064688000
_diffrn_orient_matrix_UB_31      0.0202976000
_diffrn_orient_matrix_UB_32      -0.0131043000
_diffrn_orient_matrix_UB_33      0.0552870000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4094
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.71
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91193
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0725P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                2087
_reflns_number_total             2680
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs1c05450_si_002.cif
_cod_data_source_block           prsahantcromin
_cod_database_code               4519240
_chemical_oxdiff_formula         'C20 H18 O1'
_reflns_odcompleteness_completeness 96.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 Secondary CH2 refined with riding coordinates:
 C00B(H00d,H00e), C00G(H00i,H00j)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00D(H00f), C00E(H00g), C00F(H00h), C00H(H00k), C00I(H00l),
 C00J(H00m), C00K(H00n), C00L(H00o), C00M(H00p), C00N(H00q)
2.c Idealised Me refined as rotating group:
 C009(H00a,H00b,H00c)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.153
_oxdiff_exptl_absorpt_empirical_full_min 0.917