One-Step Synthesis of Nitrogen-Containing Medium-Sized Rings via α-Imino Diazo Intermediates.
Medina, Florian; Besnard, Céline; Lacour, Jérôme; Organic letters 16 (2014) 3232–3235; doi:10.1021/ol5012532

data_1516478
_publ_section_title
;
 One-Step Synthesis of Nitrogen-Containing Medium-Sized Rings via \a-Imino
 Diazo Intermediates.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3232
_journal_page_last               3235
_journal_paper_doi               10.1021/ol5012532
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C17 H16 Br N O4 S'
_chemical_formula_sum            'C17 H16 Br N O4 S'
_chemical_formula_weight         410.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-07
_audit_creation_method
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.363(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4111(4)
_cell_length_b                   11.2306(4)
_cell_length_c                   12.7572(4)
_cell_measurement_reflns_used    3841
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.1384
_cell_measurement_theta_min      3.0640
_cell_volume                     1759.24(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      180
_diffrn_detector_area_resol_mean 10.4679
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9757
_diffrn_measurement_details
;
  1 omega  -20.00    6.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.2297  -99.0000  -60.0000 52

  2 omega   37.00   81.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.1672 -178.0000  -90.0000 88

  3 omega  -48.00   39.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.1672  -38.0000 -120.0000 174

  4 omega   36.00   89.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.1672  178.0000 -180.0000 106
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0369669000
_diffrn_orient_matrix_UB_12      0.0386038000
_diffrn_orient_matrix_UB_13      -0.0311518000
_diffrn_orient_matrix_UB_21      0.0081290000
_diffrn_orient_matrix_UB_22      0.0435381000
_diffrn_orient_matrix_UB_23      0.0406652000
_diffrn_orient_matrix_UB_31      0.0436370000
_diffrn_orient_matrix_UB_32      0.0245862000
_diffrn_orient_matrix_UB_33      -0.0230984000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7974
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         3.07
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    2.475
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.6862
_exptl_crystal_size_mid          0.3013
_exptl_crystal_size_min          0.0541
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0313P)^2^+0.6081P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                3141
_reflns_number_total             3673
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5012532_si_002.cif
_cod_data_source_block           fm98
_cod_depositor_comments
'Adding full bibliography for 1516477--1516478.cif.'
_cod_database_code               1516478
_chemical_oxdiff_formula         'Br1 S1 O4 C17 N1'
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H17 of C17, H14 of C14, H23 of C23, H20 of C20, H15 of C15, H13 of C13, H19
  of C19, {H8A,H8B} of C8, {H11A,H11B} of C11, H16 of C16, H5 of C5, {H9A,H9B}
  of C9, H22 of C22
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C20(H20), C23(H23), C14(H14), C13(H13), C15(H15), C16(H16), C5(H5),
 C22(H22), C19(H19)
;