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_1512170
_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         'C11 H10 N2 O4'
_chemical_formula_sum            'C11 H10 N2 O4'
_chemical_formula_weight         234.21
_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             2013-01-14
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.020(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2524(11)
_cell_length_b                   10.756(2)
_cell_length_c                   14.1658(19)
_cell_measurement_reflns_used    1237
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6362
_cell_measurement_theta_min      3.2989
_cell_volume                     1098.9(3)
_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(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9819
_diffrn_measured_fraction_theta_max 0.9705
_diffrn_measurement_details
;
  1 omega  -93.00  -59.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  178.0000  150.0000 34

  2 omega  -48.00   -1.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  120.0000 47

  3 omega  -47.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000  120.0000 140
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0874692000
_diffrn_orient_matrix_UB_12      -0.0234648000
_diffrn_orient_matrix_UB_13      -0.0100360000
_diffrn_orient_matrix_UB_21      -0.0428190000
_diffrn_orient_matrix_UB_22      -0.0275158000
_diffrn_orient_matrix_UB_23      -0.0422867000
_diffrn_orient_matrix_UB_31      0.0163506000
_diffrn_orient_matrix_UB_32      0.0552375000
_diffrn_orient_matrix_UB_33      -0.0249026000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.2290
_diffrn_reflns_av_unetI/netI     0.1853
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3916
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02158
_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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.181
_refine_ls_extinction_coef       0.08(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.495
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.495
_refine_ls_R_factor_all          0.2579
_refine_ls_R_factor_gt           0.1830
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4421
_refine_ls_wR_factor_ref         0.5458
_reflns_number_gt                1005
_reflns_number_total             2431
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401338e_si_005.cif
_cod_data_source_block           lizhsh0113
_cod_original_cell_volume        1099.0(3)
_cod_database_code               1512170
_reflns_odcompleteness_completeness 98.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H3 of C3, H10 of C10, H5 of C5, H2 of C2
 At 1.5 times of:
  {H8A,H8B,H8C} of C8, {H12A,H12B,H12C} of C12
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C2(H2), C5(H5), C3(H3)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C)
;