Photoinduced and N-Bromosuccinimide-Mediated Cyclization of 2-Azido-N-phenylacetamides.
Li, Zhan-Shan; Wang, Wei-Xia; Yang, Ji-Dong; Wu, Yue-Wei; Zhang, Wei; Organic letters 15 (2013) 3820–3823; doi:10.1021/ol401338e

data_1512168
_publ_section_title
;
 Photoinduced and N-Bromosuccinimide-Mediated Cyclization of
 2-Azido-N-phenylacetamides.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3820
_journal_page_last               3823
_journal_paper_doi               10.1021/ol401338e
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C14 H11 Br3 N2 O'
_chemical_formula_sum            'C14 H11 Br3 N2 O'
_chemical_formula_weight         462.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-12-17
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.786(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5051(2)
_cell_length_b                   10.4063(2)
_cell_length_c                   14.7156(3)
_cell_measurement_reflns_used    4310
_cell_measurement_temperature    293.27(10)
_cell_measurement_theta_max      72.4649
_cell_measurement_theta_min      3.1512
_cell_volume                     1531.81(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293.27(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9650
_diffrn_measured_fraction_theta_max 0.9728
_diffrn_measurement_details
;
  1 omega  -22.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 61

  2 omega  -51.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 72

  3 omega -131.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000   30.0000 52

  4 omega  -41.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000   38.0000  150.0000 54

  5 omega   28.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000  -99.0000  -30.0000 69

  6 omega  -46.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   38.0000  120.0000 37

  7 omega -122.00  -51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  178.0000 -180.0000 71

  8 omega -132.00  -80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000 -111.0000  120.0000 52

  9 omega   45.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  150.0000 38

 10 omega   82.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000  -60.0000 26

 11 omega   45.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000 -180.0000 40

 12 omega   63.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000  -30.0000 26

 13 omega   49.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000  -60.0000 49

 14 omega  127.00  153.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000 -150.0000 26

 15 omega   92.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000  120.0000 47

 16 omega   46.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   90.0000 69

 17 omega  127.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000  -30.0000 43

 18 omega   71.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000   60.0000 76

 19 omega   92.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000 -180.0000 78

 20 omega   63.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  -60.0000 26

 21 omega  136.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000 -150.0000 39

 22 omega   97.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000    0.0000 38

 23 omega   78.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -150.0000 37

 24 omega   91.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000 -150.0000 26

 25 omega   45.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -140.0000  -58.0000 25

 26 omega   89.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000   60.0000 26

 27 omega   58.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000 -120.0000 31
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0752821000
_diffrn_orient_matrix_UB_12      -0.1286816000
_diffrn_orient_matrix_UB_13      0.0085472000
_diffrn_orient_matrix_UB_21      0.1299105000
_diffrn_orient_matrix_UB_22      0.0730667000
_diffrn_orient_matrix_UB_23      0.0062384000
_diffrn_orient_matrix_UB_31      0.0339120000
_diffrn_orient_matrix_UB_32      0.0058874000
_diffrn_orient_matrix_UB_33      0.1094405000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6967
_diffrn_reflns_theta_full        72.62
_diffrn_reflns_theta_max         72.62
_diffrn_reflns_theta_min         5.29
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    2.008
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.553
_refine_diff_density_min         -1.190
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.6607P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0877
_reflns_number_gt                2833
_reflns_number_total             3007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401338e_si_003.cif
_cod_data_source_block           lizhsh1213
_cod_original_cell_volume        1531.81(6)
_cod_database_code               1512168
_reflns_odcompleteness_completeness 96.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H3 of C3, H2 of C2, H1 of C1, H4 of C4, H5 of C5, H7 of C7, H14 of C14, H13
  of C13, H12 of C12, H11 of C11, H10 of C10
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
;