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_1512169
_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         'C18 H13 Br3 N2 O'
_chemical_formula_sum            'C18 H13 Br3 N2 O'
_chemical_formula_weight         513.03
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-22
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                74.383(8)
_cell_angle_beta                 86.920(6)
_cell_angle_gamma                81.255(8)
_cell_formula_units_Z            2
_cell_length_a                   8.1390(7)
_cell_length_b                   10.3526(11)
_cell_length_c                   11.1111(8)
_cell_measurement_reflns_used    1998
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8870
_cell_measurement_theta_min      3.8010
_cell_volume                     891.09(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.8768
_diffrn_measurement_details
;
  1 omega    1.00   27.40   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  -99.0000  -30.0000 22

  2 omega -103.00  -73.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  178.0000    0.0000 25

  3 omega  -12.00   93.60   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   77.0000  -30.0000 88

  4 omega  -40.00    9.20   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000 -180.0000 41

  5 omega   56.00  104.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000  -60.0000 40

  6 omega   38.00   64.40   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512 -178.0000  -30.0000 22

  7 omega  -23.00   97.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   19.0000  150.0000 100
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0130037000
_diffrn_orient_matrix_UB_12      0.0620283000
_diffrn_orient_matrix_UB_13      0.0110434000
_diffrn_orient_matrix_UB_21      0.0865920000
_diffrn_orient_matrix_UB_22      -0.0158512000
_diffrn_orient_matrix_UB_23      -0.0103381000
_diffrn_orient_matrix_UB_31      -0.0104276000
_diffrn_orient_matrix_UB_32      0.0326796000
_diffrn_orient_matrix_UB_33      -0.0645412000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6246
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
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    1.912
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0260P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0775
_reflns_number_gt                2668
_reflns_number_total             3639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401338e_si_004.cif
_cod_data_source_block           lizhsh0320
_cod_database_code               1512169
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H9 of C9, H1 of C1, H2 of C2, H3 of C3, H6 of C6, H5 of C5, H18 of C18, H15
  of C15, H16 of C16, H10 of C10, H13 of C13, H14 of C14, H17 of C17
2.a Ternary CH refined with riding coordinates:
 C9(H9), C1(H1), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C5(H5), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
;