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_7053014
_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         'C13 H13 N O2'
_chemical_formula_sum            'C13 H13 N O2'
_chemical_formula_weight         215.24
_chemical_melting_point          409
_chemical_name_common            (4-Methoxyphenyl)(pyridine-2-yl)methanol
_chemical_name_systematic
;
(4-Methoxyphenyl)(pyridine-2-yl)methanol
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 110.610(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4890(3)
_cell_length_b                   17.2434(6)
_cell_length_c                   8.1339(3)
_cell_measurement_reflns_used    3092
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.1168
_cell_measurement_theta_min      2.6700
_cell_volume                     1114.43(7)
_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
;
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      150(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
1 omega -93.00 -64.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -17.3397 179.0000 0.0000 29

2 omega -69.00 12.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -17.3397 -77.0000 0.0000 81

3 omega -34.00 75.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 19.0585 0.0000 -180.0000 109

4 omega -7.00 18.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 19.0585 37.0000 -120.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0380675000
_diffrn_orient_matrix_UB_12      -0.0315719000
_diffrn_orient_matrix_UB_13      0.0276322000
_diffrn_orient_matrix_UB_21      0.0669432000
_diffrn_orient_matrix_UB_22      -0.0245235000
_diffrn_orient_matrix_UB_23      -0.0004905000
_diffrn_orient_matrix_UB_31      0.0451808000
_diffrn_orient_matrix_UB_32      0.0096611000
_diffrn_orient_matrix_UB_33      0.0890049000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4704
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.82
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.966
_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            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0338P)^2^+0.3186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                1693
_reflns_number_total             1965
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2nj40871f.txt
_cod_data_source_block           2a
_cod_database_code               7053014