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_7159879
_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         'C17 H10 O2'
_chemical_formula_sum            'C17 H10 O2'
_chemical_formula_weight         246.25
_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             2023-10-17
_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                 95.5510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.12120(10)
_cell_length_b                   12.50200(10)
_cell_length_c                   12.82470(10)
_cell_measurement_reflns_used    8157
_cell_measurement_temperature    160.0(1)
_cell_measurement_theta_max      79.3150
_cell_measurement_theta_min      6.8450
_cell_volume                     1136.42(2)
_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 0.998
_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    -26.00   0.00   0.50    0.56    --  -10.00 -47.00-120.24   52
  2  \w      0.00  26.00   0.50    0.56    --   10.00  47.00  81.83   52
  3  \w      1.00  27.00   0.50    0.56    --   10.00  46.00-139.18   52
  4  \w    -31.00  -5.00   0.50    0.56    --  -14.00 -43.00 139.18   52
  5  \w    -45.00 -17.00   0.50    0.56    --  -26.00 -36.00  47.81   56
  6  \w      0.00  71.00   0.50    0.56    --   50.09 -77.00-120.00  142
  7  \w   -134.00 -54.00   0.50    0.56    --  -62.00 -30.00  63.65  160
  8  \w    -71.00 -18.00   0.50    2.22    --  -90.00  61.00-150.00  106
  9  \w   -161.00-122.00   0.50    2.22    --  -90.00 -45.00  60.00   78
 10  \w   -161.00-122.00   0.50    2.22    --  -90.00 -45.00  90.00   78
 11  \w     42.00 106.00   0.50    2.22    --  111.50 -97.00-163.27  128
 12  \w     41.00 105.00   0.50    2.22    --  111.50 -77.00 -60.00  128
 13  \w    104.00 178.00   0.50    2.22    --  111.50  15.00   0.00  148
 14  \w    127.00 178.00   0.50    2.22    --  111.50  61.00   0.00  102
 15  \w     41.00 105.00   0.50    2.22    --  111.50 -77.00  90.00  128
 16  \w     41.00  71.00   0.50    2.22    --  111.50 -61.00-120.00   60
 17  \w    127.00 178.00   0.50    2.22    --  111.50  61.00 120.00  102
 18  \w     41.00 105.00   0.50    2.22    --  111.50 -77.00 120.00  128
 19  \w     43.00 111.00   0.50    2.22    --  111.50-125.00-150.00  136
 20  \w     41.00  71.00   0.50    2.22    --  111.50 -61.00   0.00   60
 21  \w     66.00 105.00   0.50    2.22    --  111.50 -95.00 -90.00   78
 22  \w    132.00 178.00   0.50    2.22    --  111.50  77.00-150.00   92
 23  \w     41.00  66.00   0.50    2.22    --  111.50 -61.00-180.00   50
 24  \w     41.00  67.00   0.50    2.22    --  111.50 -61.00 -90.00   52
 25  \w    126.00 152.00   0.50    2.22    --  111.50  45.00 -60.00   52
 26  \w    126.00 163.00   0.50    2.22    --  111.50 101.00-123.00   74
 27  \w     42.00  68.00   0.50    2.22    --  111.50 -77.00 -90.00   52
 28  \w     44.00  70.00   0.50    2.22    --  111.50 -77.00-120.00   52
 29  \w     68.00 104.00   0.50    2.22    --  111.50 -77.00 150.00   72
 30  \w     57.00  91.00   0.50    2.22    --  111.50 -95.00 120.00   68
 31  \w    122.00 147.00   0.50    2.22    --  111.50  45.00 150.00   50
 32  \w    144.00 178.00   0.50    2.22    --  111.50  77.00 -60.00   68
 33  \w     81.00 135.00   0.50    2.22    --  111.50 -83.00-107.83  108
 34  \w    133.00 176.00   0.50    2.22    --  111.50 125.00 150.00   86
 35  \w    131.00 164.00   0.50    2.22    --  111.50  61.00-120.00   66
 36  \w    106.00 132.00   0.50    2.22    --  111.50 -79.00  -6.06   52
 37  \w     70.00 101.00   0.50    2.22    --  111.50 -95.00  90.00   62
 38  \w     73.00  98.00   0.50    2.22    --  111.50 -95.00 150.00   50
 39  \w     72.00  98.00   0.50    2.22    --  111.50-125.00  90.00   52
 40  \w    113.00 139.00   0.50    2.22    --  111.50  15.00  60.00   52
 41  \w     62.00  88.00   0.50    2.22    --  111.50 -79.00  -6.06   52
;
_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      -0.0116762000
_diffrn_orient_matrix_UB_12      0.1169436000
_diffrn_orient_matrix_UB_13      0.0366944000
_diffrn_orient_matrix_UB_21      0.2167075000
_diffrn_orient_matrix_UB_22      0.0083068000
_diffrn_orient_matrix_UB_23      0.0074865000
_diffrn_orient_matrix_UB_31      -0.0117082000
_diffrn_orient_matrix_UB_32      0.0378300000
_diffrn_orient_matrix_UB_33      -0.1147791000
_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  0.0160
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13198
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.513
_diffrn_reflns_theta_min         4.952
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.932
_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    1.439
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0021(3)
_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   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0554P)^2^+0.1638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2249
_reflns_number_total             2461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00093e2.cif
_cod_data_source_block           tham1110
_cod_depositor_comments
'Adding full bibliography for 7159879--7159880.cif.'
_cod_database_code               7159879
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.908
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_shelx_res_checksum              13100