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_7224261
_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_formula_moiety         'C15 H14 N2 O2'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.29
_chemical_melting_point          441.15
_chemical_name_common            Acridine
_chemical_name_systematic        9,9-dimethyl-2-nitro-9,10-dihydroacridine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_date             2016-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-01-09 deposited with the CCDC.
2016-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   9.3070(3)
_cell_length_b                   16.5482(5)
_cell_length_c                   32.8832(9)
_cell_measurement_reflns_used    4653
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6653
_cell_measurement_theta_min      2.9870
_cell_volume                     5064.5(3)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.9854
_diffrn_measured_fraction_theta_max 0.9844
_diffrn_measurement_details
;
  1 omega   -4.00   32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   86.0000 -109.0000 36

  2 omega   -1.00   27.00   1.0000    3.0600
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000    0.0000 28

  3 omega  -59.00   19.00   1.0000    3.0600
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000 -150.0000 78

  4 omega   47.00   94.00   1.0000    3.0600
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 47

  5 omega   39.00   97.00   1.0000    3.0600
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  150.0000 58

  6 omega  -13.00   31.00   1.0000    3.0600
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000    0.0000 44

  7 omega  113.00  172.00   1.0000    3.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 59

  8 omega  138.00  175.00   1.0000    3.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 37

  9 omega   44.00   84.00   1.0000    3.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 40

 10 omega   38.00   75.00   1.0000    3.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 37

 11 omega  114.00  140.00   1.0000    3.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 26

 12 omega   41.00   76.00   1.0000    3.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 35

 13 omega   45.00   91.00   1.0000    3.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 46

 14 omega   39.00   99.00   1.0000    3.0600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -90.0000 60
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0493120000
_diffrn_orient_matrix_UB_12      0.0817132000
_diffrn_orient_matrix_UB_13      0.0176805000
_diffrn_orient_matrix_UB_21      0.1536438000
_diffrn_orient_matrix_UB_22      -0.0162413000
_diffrn_orient_matrix_UB_23      -0.0154096000
_diffrn_orient_matrix_UB_31      -0.0370367000
_diffrn_orient_matrix_UB_32      0.0415954000
_diffrn_orient_matrix_UB_33      -0.0405329000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            13211
_diffrn_reflns_theta_full        70.8012
_diffrn_reflns_theta_max         70.80
_diffrn_reflns_theta_min         5.35
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71411
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2150.9367
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.2578
_refine_diff_density_min         -0.1631
_refine_diff_density_rms         0.0383
_refine_ls_d_res_high            0.8163
_refine_ls_d_res_low             8.2741
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0667
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     351
_refine_ls_number_reflns         4806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0667
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0674P)^2^+0.7216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1424
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              39
_reflns_limit_l_min              0
_reflns_number_gt                3792
_reflns_number_total             4806
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6ra03447k2.cif
_cod_data_source_block           1
_cod_database_code               7224261
_chemical_oxdiff_formula         'C16 H18 O'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), N3(H3a), C20(H20), C18(H18), C17(H17), C3(H3), C11(H11), C29(H29),
 C2(H2), C28(H28), C14(H14), C26(H26), C13(H13), C12(H12), C27(H27)
2.b Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C23(H23a,H23b,H23c), C9(H9a,H9b,H9c), C24(H24a,H24b,H24c)
;
_olex2_submission_special_instructions 'No special instructions were received'