Transition-metal-catalyzed arylation of nitroimidazoles and further transformations of manipulable nitro group.
Iaroshenko, Viktor O.; Gevorgyan, Ashot; Mkrtchyan, Satenik; Arakelyan, Knar; Grigoryan, Tatevik; Yedoyan, Julietta; Villinger, Alexander; Langer, Peter; The Journal of organic chemistry 80 (2015) 2103–2119; doi:10.1021/jo5025927

data_4030654
_publ_section_title
;
 Transition-metal-catalyzed arylation of nitroimidazoles and further
 transformations of manipulable nitro group.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2103
_journal_page_last               2119
_journal_paper_doi               10.1021/jo5025927
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C12 H12 Br N3 O2'
_chemical_formula_sum            'C12 H12 Br N3 O2'
_chemical_formula_weight         310.16
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0209(2)
_cell_length_b                   7.6049(2)
_cell_length_c                   23.4143(5)
_cell_measurement_reflns_used    5066
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      55.122
_cell_measurement_theta_min      5.632
_cell_volume                     1250.17(6)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            16351
_diffrn_reflns_theta_full        31.50
_diffrn_reflns_theta_max         31.50
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    3.286
_exptl_absorpt_correction_T_max  0.7790
_exptl_absorpt_correction_T_min  0.5741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.984
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         4127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0242P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0645
_reflns_number_gt                3472
_reflns_number_total             4127
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            10a-is_sm6002.cif
_cod_data_source_block           is_sm6002
_cod_depositor_comments
'Adding full bibliography for 4030648--4030655.cif.'
_cod_database_code               4030654