A Serendipitous Synthesis of 11a-Hydroxy-11,11a-dihydrobenzo[e]indeno[2,1-b][1,4]diazepine-10,12-dione Derivatives by Condensation of 2-Aminobenzamides with Ninhydrin in Water.
Devi, Rajkumari Vijilata; Garande, Ashok M.; Maity, Dilip K.; Bhate, Prakash M.; The Journal of organic chemistry 81 (2016) 1689–1695; doi:10.1021/acs.joc.5b02327

data_4031871
_publ_section_title
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 A Serendipitous Synthesis of
 11a-Hydroxy-11,11a-dihydrobenzo[e]indeno[2,1-b][1,4]diazepine-10,12-dione
 Derivatives by Condensation of 2-Aminobenzamides with Ninhydrin in Water.
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_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1689
_journal_page_last               1695
_journal_paper_doi               10.1021/acs.joc.5b02327
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C16 H10 N2 O3'
_chemical_formula_weight         278.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.003(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0458(8)
_cell_length_b                   19.062(3)
_cell_length_c                   12.879(2)
_cell_measurement_reflns_used    1257
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.93
_cell_measurement_theta_min      2.67
_cell_volume                     1226.7(3)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_sigmaI/netI    0.0760
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5995
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.230
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0899
_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^)+(0.0466P)^2^+2.1048P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1714
_reflns_number_gt                1718
_reflns_number_total             2146
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02327_si_003.cif
_cod_data_source_block           sq11m
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
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_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4031871