Deconstructive annulation mediated one-pot synthesis of xanthene derivatives.
Manikandan, Balasubramaniyam; Thamotharan, Subbiah; Blacque, Olivier; Selva Ganesan, Subramaniapillai; Organic & biomolecular chemistry 22 (2024) 3279–3286; doi:10.1039/d4ob00093e

data_7159880
_publ_section_title
;
 Deconstructive annulation mediated one-pot synthesis of xanthene
 derivatives.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3279
_journal_page_last               3286
_journal_paper_doi               10.1039/d4ob00093e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C26 H24 O3'
_chemical_formula_sum            'C26 H24 O3'
_chemical_formula_weight         384.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-18
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-13 deposited with the CCDC.	2024-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.5670(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.03740(10)
_cell_length_b                   12.74610(10)
_cell_length_c                   15.5693(2)
_cell_measurement_reflns_used    17882
_cell_measurement_temperature    160.0(1)
_cell_measurement_theta_max      79.5540
_cell_measurement_theta_min      4.4770
_cell_volume                     1988.04(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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      2.00  32.00   0.50    0.28    --   10.00  42.00-178.09   60
  2  \w     43.00  69.00   0.50    1.13    --  111.50 -77.00 -60.00   52
  3  \w     53.00 105.00   0.50    1.13    --  111.50 -77.00   0.00  104
  4  \w     42.00  99.00   0.50    1.13    --  111.50 -77.00  30.00  114
  5  \w     42.00  79.00   0.50    1.13    --  111.50 -77.00 120.00   74
  6  \w      1.00  26.00   0.50    0.28    --   10.00  45.00 133.00   50
  7  \w     -5.00  21.00   0.50    0.28    --    6.00  51.00  43.26   52
  8  \w     41.00  66.00   0.50    1.13    --  111.50 -61.00 120.00   50
  9  \w     77.00 103.00   0.50    1.13    --  111.50 -77.00 150.00   52
 10  \w     78.00 104.00   0.50    1.13    --  111.50 -77.00 -60.00   52
 11  \w     61.00  87.00   0.50    1.13    --  111.50 -77.00-150.00   52
 12  \w     46.00  72.00   0.50    1.13    --  111.50 -77.00-180.00   52
 13  \w     41.00  66.00   0.50    1.13    --  111.50 -61.00-180.00   50
 14  \w     44.00  71.00   0.50    1.13    --  111.50 -61.00-150.00   54
 15  \w     -6.00  20.00   0.50    0.28    --   50.11 -13.00-164.00   52
 16  \w     41.00  70.00   0.50    1.13    --  111.50 -61.00  30.00   58
 17  \w     41.00  66.00   0.50    1.13    --  111.50 -61.00  90.00   50
 18  \w     82.00 108.00   0.50    1.13    --  111.50 -82.00 -16.53   52
 19  \w     86.00 111.00   0.50    1.13    --  111.50-125.00   0.00   50
 20  \w     88.00 126.00   0.50    1.13    --  111.50-150.00  12.41   76
 21  \w     75.00 101.00   0.50    1.13    --  111.50-125.00 120.00   52
 22  \w     48.00  73.00   0.50    1.13    --  111.50-150.00  12.41   50
 23  \w     50.00 105.00   0.50    1.13    --  111.50 -95.00  90.00  110
 24  \w     76.00 101.00   0.50    1.13    --  111.50 -95.00 120.00   50
 25  \w     54.00  81.00   0.50    1.13    --  111.50 -86.00 167.82   54
 26  \w     45.00  75.00   0.50    1.13    --  111.50-125.00   0.00   60
 27  \w     49.00  75.00   0.50    1.13    --  111.50 -82.00 -16.53   52
 28  \w     49.00 100.00   0.50    1.13    --  111.50-125.00 -60.00  102
 29  \w     52.00  78.00   0.50    1.13    --  111.50 -95.00-180.00   52
 30  \w   -155.00-108.00   0.50    1.13    --  -90.00-125.00 -90.00   94
 31  \w   -159.00-134.00   0.50    1.13    --  -90.00-125.00 -30.00   50
 32  \w   -154.00-128.00   0.50    1.13    --  -90.00 -61.00 -30.00   52
 33  \w   -146.00-120.00   0.50    1.13    --  -90.00 -13.00-164.00   52
 34  \w   -121.00 -48.00   0.50    0.28    --  -50.11 -13.00-164.00  146
 35  \w    -26.00  -1.00   0.50    0.28    --  -10.00 -47.00-131.70   50
 36  \w    -47.00 -19.00   0.50    1.13    --  -90.00  45.00   0.00   56
 37  \w     -8.00  22.00   0.50    0.28    --  -50.11  13.00   6.00   60
 38  \w    127.00 153.00   0.50    1.13    --  111.50  77.00  60.00   52
 39  \w    143.00 177.00   0.50    1.13    --  111.50  77.00 120.00   68
 40  \w    152.00 178.00   0.50    1.13    --  111.50  77.00 150.00   52
 41  \w    123.00 149.00   0.50    1.13    --  111.50  30.00  90.00   52
 42  \w    130.00 155.00   0.50    1.13    --  111.50  61.00   0.00   50
 43  \w    122.00 178.00   0.50    1.13    --  111.50  45.00  30.00  112
 44  \w    152.00 177.00   0.50    1.13    --  111.50  30.00  90.00   50
 45  \w    104.00 168.00   0.50    1.13    --  111.50  13.00   6.00  128
 46  \w     43.00  69.00   0.50    0.28    --   50.11  13.00   6.00   52
 47  \w     76.00 115.00   0.50    0.28    --   50.11  13.00   6.00   78
 48  \w    137.00 175.00   0.50    1.13    --  111.50  45.00-150.00   76
 49  \w    122.00 171.00   0.50    1.13    --  111.50  45.00-180.00   98
 50  \w    118.00 146.00   0.50    1.13    --  111.50 125.00 -90.00   56
 51  \w    110.00 147.00   0.50    1.13    --  111.50 125.00-180.00   74
 52  \w    153.00 178.00   0.50    1.13    --  111.50 125.00 -90.00   50
 53  \w    108.00 173.00   0.50    1.13    --  111.50 125.00  30.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1496585000
_diffrn_orient_matrix_UB_12      -0.0048066000
_diffrn_orient_matrix_UB_13      0.0164459000
_diffrn_orient_matrix_UB_21      0.0333846000
_diffrn_orient_matrix_UB_22      0.0211044000
_diffrn_orient_matrix_UB_23      0.0963985000
_diffrn_orient_matrix_UB_31      -0.0119983000
_diffrn_orient_matrix_UB_32      0.1188715000
_diffrn_orient_matrix_UB_33      -0.0164148000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24751
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.834
_diffrn_reflns_theta_min         4.487
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.00121(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL (Sheldrick, 2015b)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0355P)^2^+0.6163P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4058
_reflns_number_total             4301
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00093e2.cif
_cod_data_source_block           tham1310
_cod_depositor_comments
'Adding full bibliography for 7159879--7159880.cif.'
_cod_database_code               7159880
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.880
_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:
 C2(H2A,H2B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17), C21(H21),
 C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              39291