Friedel–Crafts hydroxyalkylation through activation of a carbonyl group using AlBr3: an easy access to pyridyl aryl/heteroaryl carbinols
Harikrishnan, Adhikesavan; Selvakumar, Jayaraman; Gnanamani, Elumalai; Bhattacharya, Suman; Ramanathan, Chinnasamy Ramaraj; New Journal of Chemistry 37 (2013) 563–; doi:10.1039/c2nj40871f

data_7053016
_publ_section_title
;
 Friedel--Crafts hydroxyalkylation through activation of a carbonyl group
 using AlBr3: an easy access to pyridyl aryl/heteroaryl carbinols
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              563
_journal_paper_doi               10.1039/c2nj40871f
_journal_volume                  37
_journal_year                    2013
_chemical_formula_moiety         'C21 H20 O2'
_chemical_formula_sum            'C21 H20 O2'
_chemical_formula_weight         304.37
_chemical_melting_point          352
_chemical_name_common            4,4'-(phenylmethylene)bis(methoxybenzene)
_chemical_name_systematic
;
4,4'-(phenylmethylene)bis(methoxybenzene)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9087(2)
_cell_length_b                   12.7700(5)
_cell_length_c                   21.8373(7)
_cell_measurement_reflns_used    3634
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.2097
_cell_measurement_theta_min      2.7927
_cell_volume                     1647.71(10)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_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      298(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
1 omega -92.00 -67.00 1.0000 35.0000
omega____ theta____ kappa____ phi______ frames
- -17.4960 167.0000 -113.0000 25

2 omega -5.00 92.00 1.0000 35.0000
omega____ theta____ kappa____ phi______ frames
- 19.2928 37.0000 0.0000 97

3 omega -2.00 48.00 1.0000 35.0000
omega____ theta____ kappa____ phi______ frames
- 19.2928 37.0000 90.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0152232000
_diffrn_orient_matrix_UB_12      0.0305054000
_diffrn_orient_matrix_UB_13      0.0268398000
_diffrn_orient_matrix_UB_21      0.0328676000
_diffrn_orient_matrix_UB_22      0.0455225000
_diffrn_orient_matrix_UB_23      -0.0163277000
_diffrn_orient_matrix_UB_31      -0.1144644000
_diffrn_orient_matrix_UB_32      0.0090390000
_diffrn_orient_matrix_UB_33      -0.0082414000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4917
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+0.2007P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0807
_reflns_number_gt                2506
_reflns_number_total             2795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2nj40871f.txt
_cod_data_source_block           6a
_cod_database_code               7053016