Furan ring opening-pyrrole ring closure: a new synthetic route to aryl(heteroaryl)-annulated pyrrolo[1,2-a][1,4]diazepines.
Butin, Alexander V.; Nevolina, Tatyana A.; Shcherbinin, Vitaly A.; Trushkov, Igor V.; Cheshkov, Dmitry A.; Krapivin, Gennady D.; Organic & biomolecular chemistry 8 (2010) 3316–3327; doi:10.1039/c002994g

data_7153350
_publ_section_title
;
 Furan ring opening-pyrrole ring closure: a new synthetic route to
 aryl(heteroaryl)-annulated pyrrolo[1,2-a][1,4]diazepines.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3316
_journal_page_last               3327
_journal_paper_doi               10.1039/c002994g
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C13 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25
_chemical_melting_point          508.5(5)
_chemical_name_common
1-Methyl-4,5-dihydro-6H-pyrrolo(1,2-a)(1,4)benzodiazepin-6-one
_chemical_name_systematic
;
1-Methyl-4,5-dihydro-6H-pyrrolo[1,2-a][1,4]benzodiazepin-6-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.286(1)
_cell_length_b                   8.661(2)
_cell_length_c                   19.599(4)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.6
_cell_measurement_theta_min      9.7
_cell_volume                     1067.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       \w/2\t--scans
_diffrn_radiation_monochromator  'beta filter'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0872
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2284
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0.06
_diffrn_standards_interval_time  100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.097
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
Heavy atom types Z>Si no present in molecule, because refinement Flack
parameter "x" impossible, but ALL Friedel pairs were merged.
;
_refine_ls_extinction_coef       0.014(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   0.864
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.864
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0208
_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^)+(0.0283P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0493
_refine_ls_wR_factor_ref         0.0547
_reflns_number_gt                1045
_reflns_number_total             1980
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c002994g.txt
_cod_data_source_block           kr99
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '508-509' was changed to '508.5(5)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_database_code               7153350