A mild and metal-free protocol towards the synthesis of triarylmethanes by reactions of (hetero)arylboronic acids and ortho-hydroxyarylaldehydes.
Jesin, Irfana; Mercy, A. Antony Haritha; S, Ravindra; Kataria, Ramesh; Nandi, Ganesh Chandra; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b02807

data_4037903
_publ_section_title
;
 A mild and metal-free protocol towards the synthesis of triarylmethanes
 by reactions of (hetero)arylboronic acids and ortho-hydroxyarylaldehydes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02807
_journal_year                    2020
_chemical_compound_source        Synthesize
_chemical_formula_moiety         'C25 H28 O'
_chemical_formula_sum            'C25 H28 O'
_chemical_formula_weight         344.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-29
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                82.501(6)
_cell_angle_beta                 89.134(6)
_cell_angle_gamma                82.478(6)
_cell_formula_units_Z            2
_cell_length_a                   7.6901(6)
_cell_length_b                   8.9590(6)
_cell_length_c                   15.0201(11)
_cell_measurement_reflns_used    3667
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.6200
_cell_measurement_theta_min      3.2900
_cell_volume                     1017.14(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.930
_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    -58.00 -33.00   0.50   20.91    --   -9.79 132.00  81.00   50
  2  \w    -62.00 -37.00   0.50   20.91    --   -9.79 138.00-103.00   50
  3  \w     14.00  39.00   0.50   20.91    --   10.07-138.00-164.00   50
  4  \w     11.00  36.00   0.50   20.91    --   10.07-132.00  11.00   50
  5  \w     -6.00  30.00   0.50   20.91    --   -9.79  38.00 120.00   72
  6  \w    -18.00  61.00   0.50   20.91    --   -9.79  19.00   0.00  158
  7  \w    -58.00  -6.00   0.50   20.91    --   -9.79 -57.00-180.00  104
  8  \w    -67.00   7.00   0.50   20.91    --   -9.79 -57.00   0.00  148
  9  \w     17.00  57.00   0.50   20.91    --   10.07-125.00  30.00   80
 10  \w    -19.00  38.00   0.50   20.91    --   10.07 -99.00 -60.00  114
 11  \w      3.00  57.00   0.50   20.91    --   10.07-125.00-150.00  108
 12  \w      4.00  33.00   0.50   20.91    --   10.07  19.00 -90.00   58
 13  \w    -36.00   0.00   0.50   20.91    --   10.07 122.00  68.67   72
 14  \w     47.00  80.00   0.50   20.91    --   10.07  19.00 -90.00   66
 15  \w      1.00  66.00   0.50   20.91    --   10.07  38.00-180.00  130
 16  \w    -28.00   1.00   0.50   20.91    --   10.07 121.00-137.57   58
 17  \w     44.00  79.00   0.50   20.91    --   10.07  19.00 120.00   70
 18  \w      2.00  27.00   0.50   20.91    --   10.07  19.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0640503000
_diffrn_orient_matrix_UB_12      0.0170904000
_diffrn_orient_matrix_UB_13      -0.0329154000
_diffrn_orient_matrix_UB_21      -0.0619563000
_diffrn_orient_matrix_UB_22      -0.0005606000
_diffrn_orient_matrix_UB_23      -0.0344230000
_diffrn_orient_matrix_UB_31      -0.0267325000
_diffrn_orient_matrix_UB_32      0.0787024000
_diffrn_orient_matrix_UB_33      0.0005825000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_av_unetI/netI     0.0898
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13978
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.418
_diffrn_reflns_theta_min         3.299
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_description       neddle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0685
_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^)+(0.1020P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1720
_refine_ls_wR_factor_ref         0.2100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2148
_reflns_number_total             4303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02807_si_002.cif
_cod_data_source_block           rk-apr-5p
_cod_database_code               4037903
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H O'
_diffrn_oxdiff_ac3_digest_frames
;
015b90d9fb6ed053a4aff98b61929408a400025806e
;
_diffrn_oxdiff_ac3_digest_hkl
;
01e87d918a47af8c043f1f4768fc25ed64973e
;
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00B(H00B), C00D(H00D), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K)
2.c Idealised Me refined as rotating group:
 C00L(H00C,H00E,H00F), C00M(H00G,H00L,H00M), C00N(H00N,H00O,H00P), C00O(H00Q,
 H00R,H00S), C00P(H00T,H00U,H00V), C00Q(H00W,H00X,H00Y)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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 1.466
_oxdiff_exptl_absorpt_empirical_full_min 0.748