Intramolecular Schmidt reaction of acyl chlorides with alkyl azides: preparation of pyrrolizine by intramolecular capture of intermediates with alkenes or alkynes.
Wang, Bao-Juan; Xue, Ping; Gu, Peiming; Chemical communications (Cambridge, England) 51 (2015) 2277–2279; doi:10.1039/c4cc07166b

data_7116271
_publ_section_title
;
 Intramolecular Schmidt reaction of acyl chlorides with alkyl azides:
 preparation of pyrrolizine by intramolecular capture of intermediates
 with alkenes or alkynes.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2277
_journal_page_last               2279
_journal_paper_doi               10.1039/c4cc07166b
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C14 H14 Cl N O'
_chemical_formula_sum            'C14 H14 Cl N O'
_chemical_formula_weight         247.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-08-26
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2014-08-26 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.808(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.485(2)
_cell_length_b                   10.6501(11)
_cell_length_c                   13.4479(14)
_cell_measurement_reflns_used    1770
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.7010
_cell_measurement_theta_min      5.7140
_cell_volume                     2481.0(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
  1 omega   39.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 51

  2 omega   36.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 49

  3 omega   64.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 26

  4 omega   98.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -120.0000 71

  5 omega  126.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -180.0000 52

  6 omega  106.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 27

  7 omega   86.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 29

  8 omega  129.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 45

  9 omega   96.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -180.0000 26

 10 omega   58.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 25

 11 omega   41.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 52

 12 omega   37.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   19.0000  -30.0000 90

 13 omega   40.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   30.0000 77

 14 omega   34.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 25

 15 omega  -12.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   60.0000 62

 16 omega  -32.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000    0.0000 25

 17 omega  -63.00  -27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -60.0000 36

 18 omega  -72.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000    0.0000 36

 19 omega    1.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000 -180.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0776428000
_diffrn_orient_matrix_UB_12      -0.0628371000
_diffrn_orient_matrix_UB_13      0.0116457000
_diffrn_orient_matrix_UB_21      0.0059043000
_diffrn_orient_matrix_UB_22      -0.0802405000
_diffrn_orient_matrix_UB_23      -0.0939698000
_diffrn_orient_matrix_UB_31      0.0428510000
_diffrn_orient_matrix_UB_32      -0.1026373000
_diffrn_orient_matrix_UB_33      0.0665381000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4308
_diffrn_reflns_theta_full        69.82
_diffrn_reflns_theta_max         69.82
_diffrn_reflns_theta_min         5.11
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0527
_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^)+(0.1518P)^2^+0.4120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1953
_refine_ls_wR_factor_ref         0.2273
_reflns_number_gt                1840
_reflns_number_total             2275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc07166b2.cif
_cod_data_source_block           gupm0821
_cod_depositor_comments
'Adding full bibliography for 7116270--7116271.cif.'
_cod_original_cell_volume        2480.9(5)
_cod_database_code               7116271
_reflns_odcompleteness_completeness 98.64
_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, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H10A(0.75) H10B(0.75) H10C(0.25) H10D(0.25) H11A(0.75) H11B(0.75)
 H11C(0.25) H11D(0.25) H14A(0.75) H14B(0.75) H14C(0.25) H14D(0.25) N1(0.75)
 C12(0.75) H12A(0.75) H12B(0.75) C13(0.75) H13(0.75) N1'(0.25) C12'(0.25)
 H12C(0.25) H12D(0.25) C13'(0.25) H13'(0.25)
3.a Ternary CH refined with riding coordinates:
 C13(H13), C13'(H13')
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10C,H10D), C11(H11A,H11B), C11(H11C,H11D), C14(H14A,
 H14B), C14(H14C,H14D), C12(H12A,H12B), C12'(H12C,H12D)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'