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_1507813
_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 H15 Cl O4'
_chemical_formula_sum            'C17 H15 Cl O4'
_chemical_formula_weight         318.74
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.353(6)
_cell_angle_beta                 95.337(6)
_cell_angle_gamma                95.155(6)
_cell_formula_units_Z            2
_cell_length_a                   4.7913(4)
_cell_length_b                   9.2022(8)
_cell_length_c                   17.0967(13)
_cell_measurement_reflns_used    9394
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      30.27
_cell_measurement_theta_min      3.68
_cell_volume                     728.48(11)
_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_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      ' 374 frames, detector distance = 70 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12686
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.68
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.8735
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0579P)^2^+0.0083P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0913
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                2666
_reflns_number_total             3514
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol300948u_si_002.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 1507813--1507815.cif.'
_cod_original_cell_volume        728.48(10)
_cod_database_code               1507813