Iron(ii)-chloride-catalyzed regioselective azidation of allenamides with TMSN<sub>3</sub>.
Liu, Yongchun; Ding, Na; Tan, Xiaoju; Li, Xiaoxiao; Zhao, Zhigang; Chemical communications (Cambridge, England) 56 (2020) 7507–7510; doi:10.1039/c9cc10056c

data_7126633
_publ_section_title
;
 Iron(ii)-chloride-catalyzed regioselective azidation of allenamides with
 TMSN<sub>3</sub>.
;
_journal_issue                   54
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7507
_journal_page_last               7510
_journal_paper_doi               10.1039/c9cc10056c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C16 H15 Cl F N4 O2'
_chemical_formula_sum            'C16 H15 Cl F N4 O2'
_chemical_formula_weight         349.77
_chemical_name_systematic
;
 (E)-N-(3-azidoprop-1-en-1-yl)-N-(4-fluorophenyl)-4-methylbenzenesulfonamide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-12-10 deposited with the CCDC.	2020-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                75.573(7)
_cell_angle_beta                 74.716(6)
_cell_angle_gamma                70.172(6)
_cell_formula_units_Z            2
_cell_length_a                   8.6867(5)
_cell_length_b                   8.7858(7)
_cell_length_c                   12.2020(10)
_cell_measurement_reflns_used    2776
_cell_measurement_temperature    295.0(4)
_cell_measurement_theta_max      72.2740
_cell_measurement_theta_min      5.4290
_cell_volume                     831.86(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.0(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      1.00  75.00   1.00    1.00    --   36.04 -99.00-180.00   74
  2  \w      7.00 107.00   1.00    1.00    --   36.04  19.00 -60.00  100
  3  \w     19.00 103.00   1.00    1.00    --   36.04  57.00 120.00   84
  4  \w     23.00  89.00   1.00    1.00    --   36.04-125.00 -30.00   66
  5  \w     39.00 109.00   1.00    1.00    --  108.00 -94.00  30.00   70
  6  \w     38.00  91.00   1.00    1.00    --  108.00 -30.00 120.00   53
  7  \w     91.00 176.00   1.00    1.00    --  108.00  45.00-120.00   85
  8  \w     38.00  91.00   1.00    1.00    --  108.00 -30.00  90.00   53
  9  \w     38.00  91.00   1.00    1.00    --  108.00 -30.00-150.00   53
 10  \w     38.00  91.00   1.00    1.00    --  108.00 -30.00   0.00   53
 11  \w     38.00  91.00   1.00    1.00    --  108.00 -30.00-120.00   53
 12  \w     38.00  91.00   1.00    1.00    --  108.00 -30.00 -90.00   53
 13  \w     40.00  98.00   1.00    1.00    --  108.00 -45.00  60.00   58
 14  \w     40.00  98.00   1.00    1.00    --  108.00 -45.00  90.00   58
 15  \w     38.00 116.00   1.00    1.00    --  108.00-111.00 -90.00   78
 16  \w    -33.00  55.00   1.00    1.00    --   36.04 -38.00 -30.00   88
 17  \w    -33.00  55.00   1.00    1.00    --   36.04 -38.00-150.00   88
 18  \w     17.00 105.00   1.00    1.00    --   36.04  38.00  30.00   88
 19  \w     28.00  53.00   1.00    1.00    --   36.67 -57.00  60.00   25
 20  \w    -17.00  24.00   1.00    1.00    --   36.67 -19.00  90.00   41
 21  \w     44.00  82.00   1.00    1.00    --   36.67-125.00  90.00   38
 22  \w    -10.00  16.00   1.00    1.00    --   36.67 -57.00  60.00   26
 23  \w     37.00  64.00   1.00    1.00    --   36.67 -99.00 -60.00   27
 24  \w     41.00  66.00   1.00    1.00    --   36.67 -19.00  90.00   25
 25  \w    103.00 142.00   1.00    1.00    --  108.00 111.00-180.00   39
 26  \w     76.00 106.00   1.00    1.00    --  108.00 -94.00  90.00   30
 27  \w     44.00 104.00   1.00    1.00    --  108.00 -94.00 -60.00   60
 28  \w     51.00  86.00   1.00    1.00    --  108.00 -45.00 -60.00   35
 29  \w    103.00 146.00   1.00    1.00    --  108.00 178.00 -60.00   43
 30  \w     46.00  72.00   1.00    1.00    --  108.00 -94.00  90.00   26
 31  \w     56.00  82.00   1.00    1.00    --  108.00 -45.00-180.00   26
 32  \w    109.00 173.00   1.00    1.00    --  108.00  15.00-180.00   64
 33  \w     73.00  99.00   1.00    1.00    --  108.00  15.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0016526000
_diffrn_orient_matrix_UB_12      0.1520514000
_diffrn_orient_matrix_UB_13      -0.0960141000
_diffrn_orient_matrix_UB_21      0.0524458000
_diffrn_orient_matrix_UB_22      -0.1100302000
_diffrn_orient_matrix_UB_23      -0.0919565000
_diffrn_orient_matrix_UB_31      -0.1849794000
_diffrn_orient_matrix_UB_32      0.0250738000
_diffrn_orient_matrix_UB_33      0.0019522000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6881
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.547
_diffrn_reflns_theta_min         5.437
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.281
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0671
_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^)+(0.1510P)^2^+0.1643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1995
_refine_ls_wR_factor_ref         0.2093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2835
_reflns_number_total             3217
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc10056c2.cif
_cod_data_source_block           lxx-lyc-1-2
_cod_depositor_comments          'Adding full bibliography for 7126633.cif.'
_cod_original_cell_volume        831.85(11)
_cod_database_code               7126633
_reflns_odcompleteness_completeness 99.87
_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 Secondary CH2 refined with riding coordinates:
 C00O(H00K,H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00G)
;
_shelx_res_checksum              72389
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-04-17
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.868
_oxdiff_exptl_absorpt_empirical_full_min 0.674