Photoactivation of Amino-Substituted 1,4-Benzoquinones for Release of Carboxylate and Phenolate Leaving Groups Using Visible Light
Yugang Chen; Mark G. Steinmetz; Journal of Organic Chemistry 71 (2006) 6053–6060; doi:10.1021/jo060790g

data_4021849
_publ_contact_author_address
;Dept. of Chemistry
Marquette University
P.O. Box 1881
Milwaukee, WI 53201-1881
;
_publ_contact_author_email       mark.steinmetz@marquette.edu
_publ_contact_author_name        'Mark G. Steinmetz'
_publ_contact_author_phone       '414 288-3535'
_publ_section_title
;
 Photoactivation of Amino-Substituted 1,4-Benzoquinones for Release
 of Carboxylate and Phenolate Leaving Groups Using Visible Light
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6053
_journal_page_last               6060
_journal_paper_doi               10.1021/jo060790g
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C11 H11 Cl2 N O2'
_chemical_formula_weight         260.11
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.9320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6303(6)
_cell_length_b                   7.5224(5)
_cell_length_c                   17.1285(12)
_cell_measurement_reflns_used    9572
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.5
_cell_measurement_theta_min      2.5
_cell_volume                     1098.51(13)
_computing_cell_refinement       'SAINT v7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 v1.0-27 (Bruker, 2005)'
_computing_data_reduction        'SADABS-2004/1 (Bruker, 2005)'
_computing_molecular_graphics    'XP v5.1 (Bruker, 1998)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX2 CCD detector'
_diffrn_measurement_method       'omega scan'
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            17715
_diffrn_reflns_theta_full        31.88
_diffrn_reflns_theta_max         31.88
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   'semi-empirical (SADABS procedure)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.1249P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0811
_reflns_number_gt                3225
_reflns_number_total             3582
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060790gsi20060602_105836.cif
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4021849