Zinc acetate-catalyzed, green and efficient synthesis of xanthene derivatives under ultrasound irradiation: X-ray crystallographic analysis and <i>in silico</i> study.
Sayad, Rayene; Bouzina, Abdeslem; Bouone, Yousra Ouafa; Beldjezzia, Dounia; Djemel, Abdelhak; Ibrahim-Ouali, Malika; Aouf, Nour-Eddine; Aouf, Zineb; RSC advances 14 (2024) 24585–24603; doi:10.1039/d4ra04135f

data_7249184
_publ_section_title
;
 Zinc acetate-catalyzed, green and efficient synthesis of xanthene
 derivatives under ultrasound irradiation: X-ray crystallographic analysis
 and <i>in silico</i> study.
;
_journal_issue                   34
_journal_name_full               'RSC advances'
_journal_page_first              24585
_journal_page_last               24603
_journal_paper_doi               10.1039/d4ra04135f
_journal_volume                  14
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H20 O3'
_chemical_formula_sum            'C20 H20 O3'
_chemical_formula_weight         308.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2hh203
_audit_creation_date             2023-11-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-16 deposited with the CCDC.	2024-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.2645(5)
_cell_length_b                   9.2078(2)
_cell_length_c                   9.6666(2)
_cell_measurement_reflns_used    1770
_cell_measurement_temperature    295
_cell_measurement_theta_max      74.5100
_cell_measurement_theta_min      4.7920
_cell_volume                     1625.69(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6091
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_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   -108.00 -40.00   0.50    2.50    --  -41.15 -71.00 -65.00  136
  2  \w    118.00 160.00   0.50   25.00    --  107.24  54.00-135.00   84
  3  \w     56.00 138.00   0.50   25.00    --  107.24 -71.00 -65.00  164
  4  \w     32.00 108.00   0.50   25.00    --  107.24-107.00-149.00  152
  5  \w    -39.00  -9.00   0.50    2.50    --  -41.15 125.00  60.00   60
  6  \w    -85.00 -44.00   0.50    2.50    --  -41.15 125.00  60.00   82
  7  \w     29.00  87.00   0.50    2.50    --   41.15-125.00 -30.00  116
  8  \w     24.00  65.00   0.50    2.50    --   41.15 -99.00 150.00   82
  9  \w    119.00 175.00   0.50   25.00    --  107.24 111.00 -90.00  112
 10  \w     34.00 136.00   0.50   25.00    --  107.24 -30.00 -90.00  204
 11  \w     40.00 107.00   0.50   25.00    --  107.24-111.00 120.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1330825000
_diffrn_orient_matrix_UB_12      0.0487322000
_diffrn_orient_matrix_UB_13      0.0291548000
_diffrn_orient_matrix_UB_21      0.0005297000
_diffrn_orient_matrix_UB_22      -0.0250874000
_diffrn_orient_matrix_UB_23      0.1521296000
_diffrn_orient_matrix_UB_31      0.1014306000
_diffrn_orient_matrix_UB_32      0.0641229000
_diffrn_orient_matrix_UB_33      0.0373381000
_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  0.0363
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6225
_diffrn_reflns_point_group_measured_fraction_full 0.738
_diffrn_reflns_point_group_measured_fraction_max 0.716
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.512
_diffrn_reflns_theta_min         4.803
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 427 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2390
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0524P)^2^+0.0249P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.376
_reflns_Friedel_fraction_full    0.438
_reflns_Friedel_fraction_max     0.418
_reflns_number_gt                1973
_reflns_number_total             2390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra04135f2.cif
_cod_data_source_block           br26
_cod_database_code               7249184
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'c20 h20 o3'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.867
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C19(H19)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              36718
_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 1.251
_oxdiff_exptl_absorpt_empirical_full_min 0.675