Safe and reliable synthesis of diazoketones and quinoxalines in a continuous flow reactor.
Martin, Laetitia J.; Marzinzik, Andreas L.; Ley, Steven V.; Baxendale, Ian R.; Organic letters 13 (2011) 320–323; doi:10.1021/ol1027927

data_1501908
_publ_section_title
;
 Safe and reliable synthesis of diazoketones and quinoxalines in a
 continuous flow reactor.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              320
_journal_page_last               323
_journal_paper_doi               10.1021/ol1027927
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C15 H7 Br Cl F3 N2'
_chemical_formula_weight         387.59
_chemical_name_common            E-47209-EXP035
_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                87.975(8)
_cell_angle_beta                 87.647(8)
_cell_angle_gamma                88.540(8)
_cell_formula_units_Z            4
_cell_length_a                   9.740(2)
_cell_length_b                   10.580(2)
_cell_length_c                   13.367(3)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.31
_cell_volume                     1375.0(5)
_computing_cell_refinement       'Saint V7.36A (Bruker AXS, 2004)'
_computing_data_collection       'SMART V5.630 (Bruker AXS, 2003)'
_computing_data_reduction        'Saint V7.36A (Bruker AXS, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         microsource
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20949
_diffrn_reflns_theta_full        68.28
_diffrn_reflns_theta_max         68.28
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    6.177
_exptl_absorpt_correction_T_max  0.8864
_exptl_absorpt_correction_T_min  0.2966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.567
_refine_diff_density_min         -1.245
_refine_diff_density_rms         0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0939P)^2^+3.8375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1531
_reflns_number_gt                4490
_reflns_number_total             4900
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1027927_si_002.cif
_cod_data_source_block           AMA13a
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1501908
_chemical_source_common          DCE/CDCl3/ACN