Nucleophilic Halogenations of Diazo Compounds, a Complementary Principle for the Synthesis of Halodiazo Compounds: Experimental and Theoretical Studies
Christian Schnaars; Martin Hennum; Tore Bonge-Hansen; Journal of Organic Chemistry 78 (2013) 7488–7497; doi:10.1021/jo401050c

data_4028459
_publ_contact_author_address
;
Department of Chemistry, University of Oslo, PO Box 1033 Blindern, Oslo,
 Norway-0315
;
_publ_contact_author_email       Tore.Hansen@kjemi.uio.no
_publ_contact_author_name        'Tore Hansen'
_publ_section_title
;
 Nucleophilic Halogenations of Diazo Compounds, a Complementary Principle
 for the Synthesis of Halodiazo Compounds: Experimental and Theoretical
 Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7488
_journal_page_last               7497
_journal_paper_doi               10.1021/jo401050c
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C10 H20 N3 O2, C F3 O3 S'
_chemical_formula_sum            'C11 H20 F3 N3 O5 S'
_chemical_formula_weight         363.37
_chemical_name_common            'triethylammonium diazoacetate triflate'
_chemical_name_systematic
1-diazo-2-ethoxy-N,N,N-triethyl-2-oxoethanaminium
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-09-23 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.953(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9478(14)
_cell_length_b                   14.984(2)
_cell_length_c                   12.673(2)
_cell_measurement_reflns_used    5235
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.53
_cell_measurement_theta_min      2.65
_cell_volume                     1698.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13406
_diffrn_reflns_theta_full        26.70
_diffrn_reflns_theta_max         26.70
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       'Triethylammonium diazoacetate triflate'
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0665P)^2^+0.6978P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1391
_reflns_number_gt                3029
_reflns_number_total             3583
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401050c_si_003.cif
_cod_data_source_block           cs_teadaa
_cod_database_code               4028459