Copper Catalyzed Coupling of Protecting Group Free and Sterically Hindered 2-Bromobenzyl Tertiary Alcohols with Phenols and Anilines: Facile Synthesis of Xanthenes and Dihydroacridines
Gedu, Satyanarayana; Lodi, Mahendar; RSC Adv.  (2016) –; doi:10.1039/C6RA03447K

data_7224262
_publ_section_title
;
 Copper Catalyzed Coupling of Protecting Group Free and Sterically
 Hindered 2-Bromobenzyl Tertiary Alcohols with Phenols and Anilines:
 Facile Synthesis of Xanthenes and Dihydroacridines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA03447K
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H16 O'
_chemical_formula_sum            'C19 H16 O'
_chemical_formula_weight         260.32
_chemical_melting_point          373.15
_chemical_name_common            xanthene
_chemical_name_systematic        12,12-dimethyl-12H-benzo[a]xanthene
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-01-09
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_audit_update_record
;
2016-01-09 deposited with the CCDC.
2016-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            9
_cell_length_a                   20.6263(7)
_cell_length_b                   20.6263(7)
_cell_length_c                   8.4471(3)
_cell_measurement_reflns_used    2798
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2473
_cell_measurement_theta_min      4.2834
_cell_volume                     3112.30(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega  -46.00  -19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  130.0000  160.0000 27

  2 omega  -98.00  -71.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      -42.5000 -140.0000  -84.0000 27

  3 omega  -99.00  -17.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000   90.0000 82

  4 omega -102.00  -50.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000 -150.0000 52

  5 omega   39.00   87.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -30.0000  -40.0000 48

  6 omega   62.00  102.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      110.2786 -111.0000  -60.0000 40

  7 omega   40.00   85.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -50.0000   60.0000 45

  8 omega   46.00   87.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -25.0000   60.0000 41

  9 omega   42.00   92.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      110.2786  -38.0000  -90.0000 50

 10 omega   85.00  178.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      110.2786  140.0000  -25.0000 93
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0493071000
_diffrn_orient_matrix_UB_12      0.0818296000
_diffrn_orient_matrix_UB_13      -0.0538156000
_diffrn_orient_matrix_UB_21      0.0706691000
_diffrn_orient_matrix_UB_22      -0.0033730000
_diffrn_orient_matrix_UB_23      0.0445275000
_diffrn_orient_matrix_UB_31      0.0029361000
_diffrn_orient_matrix_UB_32      -0.0270360000
_diffrn_orient_matrix_UB_33      -0.1684992000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6975
_diffrn_reflns_theta_full        71.39
_diffrn_reflns_theta_max         71.39
_diffrn_reflns_theta_min         4.29
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'whitish colourless'
_exptl_crystal_colour_modifier   whitish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1242
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         4791
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0697P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                4195
_reflns_number_total             4791
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra03447k2.cif
_cod_data_source_block           exp_5911
_cod_original_cell_volume        3112.29(19)
_cod_database_code               7224262
_chemical_oxdiff_formula         'C19 H16 O'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97