Intramolecular Schmidt reaction of acyl chlorides with alkyl azides: rapid access to fused polycyclic nitrogen-containing heterocycles via a multistep one-pot transformation.
Gu, Peiming; Kang, Xiao-Yan; Sun, Jian; Wang, Bao-Juan; Yi, Ming; Li, Xue-Qiang; Xue, Ping; Li, Rui; Organic letters 14 (2012) 5796–5799; doi:10.1021/ol302890a

data_1508776
_publ_section_title
;
 Intramolecular Schmidt reaction of acyl chlorides with alkyl azides:
 rapid access to fused polycyclic nitrogen-containing heterocycles via a
 multistep one-pot transformation.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5796
_journal_page_last               5799
_journal_paper_doi               10.1021/ol302890a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C13 H15 N O'
_chemical_formula_weight         201.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.556(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.303(4)
_cell_length_b                   11.685(5)
_cell_length_c                   11.372(5)
_cell_measurement_reflns_used    1644
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.30
_cell_measurement_theta_min      2.79
_cell_volume                     1081.0(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6998
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9777
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.003(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   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0629
_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^)+(0.1125P)^2^+0.4048P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1850
_refine_ls_wR_factor_ref         0.2215
_reflns_number_gt                1266
_reflns_number_total             1995
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302890a_si_001.cif
_cod_data_source_block           p21n
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1080.9(8)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1508776