Synthesis of 1,3-diazepines and ring contraction to cyanopyrroles.
Reisinger, Ales; Bernhardt, Paul V.; Wentrup, Curt; Organic & biomolecular chemistry 2 (2004) 246–256; doi:10.1039/b311247k

data_7150317
_publ_section_title
;
 Synthesis of 1,3-diazepines and ring contraction to cyanopyrroles.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              246
_journal_page_last               256
_journal_paper_doi               10.1039/b311247k
_journal_volume                  2
_journal_year                    2004
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H17 N3 O1'
_chemical_formula_structural     'C10 H17 N3 O'
_chemical_formula_sum            'C10 H17 N3 O'
_chemical_formula_weight         195.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_date             2003-08-20T15:26:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 107.343(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.185(2)
_cell_length_b                   8.1266(4)
_cell_length_c                   12.711(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      14.234
_cell_measurement_theta_min      10.102
_cell_measurement_wavelength     0.71073
_cell_volume                     1102.9(3)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.74943E-1
_diffrn_orient_matrix_UB_12      0.16684E-1
_diffrn_orient_matrix_UB_13      0.65596E-1
_diffrn_orient_matrix_UB_21      -0.54992E-1
_diffrn_orient_matrix_UB_22      -0.2482E-2
_diffrn_orient_matrix_UB_23      0.49255E-1
_diffrn_orient_matrix_UB_31      0.11429E-1
_diffrn_orient_matrix_UB_32      -0.12194
_diffrn_orient_matrix_UB_33      0.7929E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.002
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3648
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.68
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_correction_T_min  0.9343
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   1
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.3197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                1510
_reflns_number_total             1939
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b311247k.txt
_cod_data_source_block           1411ar1
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7150317
_exptl_absorpt_factor_mur        0
_exptl_absorpt_correction_t_ave  0.9678
_diffrn_standards_decay_corr_max 1.03
_diffrn_standards_decay_corr_min 0.968