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_1516477
_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         'C18 H18 Br N O4 S'
_chemical_formula_sum            'C18 H18 Br N O4 S'
_chemical_formula_weight         424.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-04-10
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Mar 21 2013 11:17:50, GUI svn.r4446)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.3759(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.50619(17)
_cell_length_b                   11.55718(16)
_cell_length_c                   12.58675(17)
_cell_measurement_reflns_used    4070
_cell_measurement_temperature    201(5)
_cell_measurement_theta_max      73.1220
_cell_measurement_theta_min      5.1930
_cell_volume                     1804.19(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      201(5)
_diffrn_detector_area_resol_mean 10.4679
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9691
_diffrn_measurement_details
;
  1 omega -123.00  -79.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000 -120.0000 88

  2 omega -119.00  -93.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000   30.0000 52

  3 omega  -97.00  -11.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -38.0000   90.0000 172

  4 omega -124.00  -90.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -99.0000  -60.0000 68

  5 omega -132.00  -79.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365 -178.0000    0.0000 106

  6 omega  -41.00   -5.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      -68.5000   30.0000   30.0000 72

  7 omega   41.00   99.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000 -150.0000 116

  8 omega   52.00   90.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -45.0000   60.0000 76

  9 omega   29.00   91.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -30.0000  150.0000 124

 10 omega   32.00   95.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -45.0000  -90.0000 126

 11 omega   58.00   84.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -30.0000 -150.0000 52

 12 omega   74.00  176.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   30.0000   60.0000 204

 13 omega   56.00  103.00   0.5000    0.8000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000  -60.0000 94
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0346776000
_diffrn_orient_matrix_UB_12      0.0603227000
_diffrn_orient_matrix_UB_13      -0.1080772000
_diffrn_orient_matrix_UB_21      0.1190319000
_diffrn_orient_matrix_UB_22      0.0111810000
_diffrn_orient_matrix_UB_23      -0.0181089000
_diffrn_orient_matrix_UB_31      -0.0064702000
_diffrn_orient_matrix_UB_32      -0.1184083000
_diffrn_orient_matrix_UB_33      -0.0567721000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6236
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.176
_diffrn_reflns_theta_min         3.564
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.387
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.280
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

followed by a multu-scan correction (ABSPACK)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.4117
_exptl_crystal_size_mid          0.3699
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+0.9475P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0891
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3224
_reflns_number_total             3509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5012532_si_003.cif
_cod_data_source_block           fm127-1
_cod_depositor_comments
'Adding full bibliography for 1516477--1516478.cif.'
_cod_database_code               1516477
_chemical_oxdiff_formula         'C18 H18 Br1 S1 O4 N1'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C5(H5), C16(H16), C15(H15), C22(H22), C20(H20), C17(H17), C14(H14),
 C23(H23), C13(H13)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelxl_version_number           2013-2