A Route to (Het)arene-Annulated Pyrrolo[1,2-<i>d</i>][1,4]diazepines via the Expanded Intramolecular Paal-Knorr Reaction: Nitro Group and Furan Ring as Equivalents of Amino Group and 1,4-Diketone.
Zelina, Elena Y.; Nevolina, Tatyana A.; Skvortsov, Dmitry A.; Trushkov, Igor V.; Uchuskin, Maxim G.; The Journal of organic chemistry 84 (2019) 13707–13720; doi:10.1021/acs.joc.9b01925

data_4034542
_publ_section_title
;
 A Route to (Het)arene-Annulated Pyrrolo[1,2-<i>d</i>][1,4]diazepines via
 the Expanded Intramolecular Paal-Knorr Reaction: Nitro Group and Furan
 Ring as Equivalents of Amino Group and 1,4-Diketone.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13707
_journal_page_last               13720
_journal_paper_doi               10.1021/acs.joc.9b01925
_journal_volume                  84
_journal_year                    2019
_chemical_compound_source        'oganic synthesis'
_chemical_formula_moiety         C27H24N2O1*H2O
_chemical_formula_sum            'C27 H26 N2 O2'
_chemical_formula_weight         410.50
_chemical_melting_point          418
_chemical_name_systematic
(10-ethyl-7-phenyl-6,7-dihydro-5H-benzo[b]pyrrolo[1,2-d][1,4]diazepin-5-yl)(phenyl)methanone
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-06-07 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.095(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4256(14)
_cell_length_b                   12.6372(14)
_cell_length_c                   16.616(2)
_cell_measurement_reflns_used    6619
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1940
_cell_measurement_theta_min      3.7770
_cell_volume                     2176.8(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
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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_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20611
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.439
_diffrn_reflns_theta_min         3.224
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62043
_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_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: PE:EA'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.056
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         5390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1070P)^2^+0.6963P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1833
_refine_ls_wR_factor_ref         0.1970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4160
_reflns_number_total             5390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01925_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034542
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              78018