Three Different Dimerizations of 2-Bromo-3-methyl-1,4-naphthoquinones
Shuhei Azuma; Kazuyuki Nishio; Konomi Kubo; Takahiro Sasamori; Norihiro Tokitoh; Kouji Kuramochi; Kazunori Tsubaki; Journal of Organic Chemistry 77 (2012) 4812–4820; doi:10.1021/jo300696m

data_4027211
_publ_section_title
;
 Three Different Dimerizations of 2-Bromo-3-methyl-1,4-naphthoquinones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4812
_journal_page_last               4820
_journal_paper_doi               10.1021/jo300696m
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C22 H13 Br O4, C H4 O'
_chemical_formula_sum            'C23 H17 Br O5'
_chemical_formula_weight         453.28
_chemical_melting_point          439
_chemical_name_common            5a
_chemical_name_systematic
; 
 5a 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                99.9974(15)
_cell_angle_beta                 94.1978(14)
_cell_angle_gamma                98.252(2)
_cell_formula_units_Z            4
_cell_length_a                   7.4477(3)
_cell_length_b                   12.7681(5)
_cell_length_c                   19.9691(7)
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      1.77
_cell_volume                     1841.32(12)
_computing_cell_refinement       HKL2000
_computing_data_collection       CrystalClear
_computing_data_reduction        HKL2000
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
;
Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'rotating-anode x-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16263
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    2.267
_exptl_absorpt_correction_T_max  0.9777
_exptl_absorpt_correction_T_min  0.8394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Jacobson, R. (1998) Private communication
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_description       prism
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         6803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.2932P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                5042
_reflns_number_total             6803
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300696m_si_002.cif
_cod_data_source_block           5a
_cod_database_code               4027211