Diastereomer-Differentiating Photochemistry of β-Arylbutyrophenones: Yang Cyclization versus Type II Elimination
Nidhi Singhal; Apurba L. Koner; Prasenjit Mal; Paloth Venugopalan; Werner M. Nau; Jarugu Narasimha Moorthy; Journal of the American Chemical Society 127 (2005) 14375–14382; doi:10.1021/ja0523643

data_4111995
_publ_contact_author
;
      Dr. J. Narasimha Moorthy
      Department of Chemistry
      Indian Institute of Technology
      Kanpur 208016
      India
;
_publ_contact_author_email       moorthy@iitk.ac.in
_publ_contact_author_fax         '091 512 2597436'
_publ_contact_author_phone       '091 512 2597438'
_publ_section_title
;
 Diastereomer-Differentiating Photochemistry of \b-Arylbutyrophenones:
 Yang Cyclization versus Type II Elimination
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14375
_journal_page_last               14382
_journal_paper_doi               10.1021/ja0523643
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C24 H24 O2'
_chemical_formula_weight         344.43
_chemical_melting_point          348
_chemical_name_common
Aplha-methyl-beta-anisyl-gamma-phenylbutyrophenone
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'Manual edit of SHELXL-97 CIF'
_cell_angle_alpha                90.00
_cell_angle_beta                 98.540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7600(10)
_cell_length_b                   17.916(2)
_cell_length_c                   19.174(4)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.586
_cell_measurement_theta_min      11.580
_cell_volume                     1956.7(6)
_computing_cell_refinement       'XSCANS (Siemens)'
_computing_data_collection       'XSCANS (Siemens)'
_computing_data_reduction        'XSCANS (Siemens)'
_computing_molecular_graphics    'XP (Siemens)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2\q/\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3252
_diffrn_reflns_theta_full        23.50
_diffrn_reflns_theta_max         23.50
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0.41
_diffrn_standards_interval_count 97
_diffrn_standards_number         40
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_preparation       'Chloroform: Hexane, 2:1, (v/v)'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -6(6)
_refine_ls_extinction_coef       0.031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0793
_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^)+(0.1236P)^2^+1.5752P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2097
_refine_ls_wR_factor_ref         0.2333
_reflns_number_gt                1958
_reflns_number_total             2917
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0523643rom20050412_080214.cif
_cod_data_source_block           3-syn
_cod_database_code               4111995