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_7150316
_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         'C6 H7 Cl1 N4 O1'
_chemical_formula_structural     'C6 H7 CL N4 O'
_chemical_formula_sum            'C7 H7 Cl N4 O'
_chemical_formula_weight         198.62
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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             2003-08-20T12:19:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                105.66(2)
_cell_angle_beta                 94.91(3)
_cell_angle_gamma                102.04(2)
_cell_formula_units_Z            4
_cell_length_a                   7.792(1)
_cell_length_b                   10.213(2)
_cell_length_c                   11.809(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      14.048
_cell_measurement_theta_min      9.787
_cell_measurement_wavelength     0.71073
_cell_volume                     874.9(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.75463E-1
_diffrn_orient_matrix_UB_12      0.74551E-1
_diffrn_orient_matrix_UB_13      -0.26687E-1
_diffrn_orient_matrix_UB_21      -0.109091
_diffrn_orient_matrix_UB_22      0.24029E-1
_diffrn_orient_matrix_UB_23      -0.31111E-1
_diffrn_orient_matrix_UB_31      0.5172E-2
_diffrn_orient_matrix_UB_32      0.06959
_diffrn_orient_matrix_UB_33      0.79047E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3313
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.81
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.9588
_exptl_absorpt_correction_T_min  0.917
_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   5
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.015(2)
_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   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0546P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1235
_reflns_number_gt                1429
_reflns_number_total             3068
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b311247k.txt
_cod_data_source_block           cw17298
_cod_database_code               7150316
_exptl_absorpt_factor_mur        0.039
_exptl_absorpt_correction_t_ave  0.9334
_diffrn_standards_decay_corr_max 1.009
_diffrn_standards_decay_corr_min 0.963