Synthesis of highly functionalized 9,10-phenanthrenequinones by oxidative coupling using MoCl5.
Trosien, Simon; Waldvogel, Siegfried R.; Organic letters 14 (2012) 2976–2979; doi:10.1021/ol300948u

data_1507815
_publ_section_title
;
 Synthesis of highly functionalized 9,10-phenanthrenequinones by oxidative
 coupling using MoCl5.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2976
_journal_page_last               2979
_journal_paper_doi               10.1021/ol300948u
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C17 H13 I O5'
_chemical_formula_sum            'C17 H13 I O5'
_chemical_formula_weight         424.17
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.504(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.9470(15)
_cell_length_b                   3.9892(2)
_cell_length_c                   21.7053(19)
_cell_measurement_reflns_used    10398
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      3.61
_cell_volume                     1466.9(2)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SMART APEX2'
_diffrn_measurement_method       'CCD scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8373
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.61
_diffrn_source                   'sealed Tube'
_exptl_absorpt_coefficient_mu    2.208
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.347
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       0.0047(7)
_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   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0597P)^2^+0.7455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1014
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                2576
_reflns_number_total             3469
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol300948u_si_002.cif
_cod_data_source_block           str5l
_cod_depositor_comments
'Adding full bibliography for 1507813--1507815.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1507815