#------------------------------------------------------------------------------
#$Date: 2016-03-04 05:48:37 +0200 (Fri, 04 Mar 2016) $
#$Revision: 177219 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/18/4031871.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4031871
loop_
_publ_author_name
'Devi, Rajkumari Vijilata'
'Garande, Ashok M.'
'Maity, Dilip K.'
'Bhate, Prakash M.'
_publ_section_title
;
 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.
;
_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
_chemical_name_systematic
; 
 ? 
;
_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/[σ²(Fo²)+(0.0466P)²+2.1048P] where P=(Fo²+2Fc²)/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
;
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 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4031871
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.2743(5) 0.56295(15) 0.0325(2) 0.0155(7) Uani 1 1 d .
O2 O -0.0181(5) 0.38787(16) 0.1553(2) 0.0201(7) Uani 1 1 d .
H2C H -0.0647 0.3923 0.0921 0.030 Uiso 1 1 calc R
O3 O 0.4301(6) 0.30506(16) 0.0923(2) 0.0253(8) Uani 1 1 d .
N1 N 0.2149(7) 0.47700(18) 0.3399(3) 0.0178(8) Uani 1 1 d .
N2 N 0.3379(7) 0.46002(18) 0.1147(3) 0.0135(8) Uani 1 1 d .
H2D H 0.447(11) 0.450(3) 0.067(4) 0.050 Uiso 1 1 d .
C1 C 0.5818(8) 0.3262(2) 0.2771(3) 0.0170(10) Uani 1 1 d .
C2 C 0.7745(8) 0.2759(2) 0.3076(3) 0.0203(10) Uani 1 1 d .
H2A H 0.8214 0.2429 0.2602 0.024 Uiso 1 1 calc R
C3 C 0.8952(9) 0.2764(2) 0.4107(4) 0.0270(11) Uani 1 1 d .
H3 H 1.0248 0.2430 0.4334 0.032 Uiso 1 1 calc R
C4 C 0.8248(10) 0.3263(2) 0.4809(4) 0.0299(12) Uani 1 1 d .
H4 H 0.9061 0.3250 0.5502 0.036 Uiso 1 1 calc R
C5 C 0.6376(9) 0.3776(2) 0.4500(3) 0.0237(11) Uani 1 1 d .
H5 H 0.5953 0.4114 0.4971 0.028 Uiso 1 1 calc R
C6 C 0.5145(8) 0.3773(2) 0.3471(3) 0.0147(9) Uani 1 1 d .
C7 C 0.3137(8) 0.4258(2) 0.2943(3) 0.0155(9) Uani 1 1 d .
C8 C 0.0363(8) 0.5248(2) 0.2830(3) 0.0161(9) Uani 1 1 d .
C9 C -0.1442(9) 0.5559(2) 0.3422(3) 0.0226(11) Uani 1 1 d .
H9 H -0.1488 0.5409 0.4106 0.027 Uiso 1 1 calc R
C10 C -0.3159(8) 0.6086(2) 0.3009(3) 0.0230(11) Uani 1 1 d .
H10 H -0.4375 0.6278 0.3409 0.028 Uiso 1 1 calc R
C11 C -0.3073(8) 0.6326(2) 0.2007(3) 0.0195(10) Uani 1 1 d .
H11 H -0.4209 0.6684 0.1730 0.023 Uiso 1 1 calc R
C12 C -0.1271(8) 0.6028(2) 0.1415(3) 0.0174(10) Uani 1 1 d .
H12 H -0.1203 0.6196 0.0742 0.021 Uiso 1 1 calc R
C13 C 0.0429(8) 0.5489(2) 0.1796(3) 0.0138(9) Uani 1 1 d .
C14 C 0.2261(7) 0.5242(2) 0.1053(3) 0.0131(9) Uani 1 1 d .
C15 C 0.2535(8) 0.4053(2) 0.1796(3) 0.0131(9) Uani 1 1 d .
C16 C 0.4303(8) 0.3387(2) 0.1722(3) 0.0161(10) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C15 O2 H2C 109.5
C7 N1 C8 121.1(3)
C14 N2 C15 123.9(3)
C14 N2 H2D 115(3)
C15 N2 H2D 120(3)
C2 C1 C6 121.5(4)
C2 C1 C16 128.8(4)
C6 C1 C16 109.6(4)
C3 C2 C1 117.9(4)
C3 C2 H2A 121.1
C1 C2 H2A 121.1
C2 C3 C4 120.7(4)
C2 C3 H3 119.7
C4 C3 H3 119.7
C5 C4 C3 121.6(4)
C5 C4 H4 119.2
C3 C4 H4 119.2
C4 C5 C6 118.1(4)
C4 C5 H5 120.9
C6 C5 H5 120.9
C5 C6 C1 120.2(4)
C5 C6 C7 129.1(4)
C1 C6 C7 110.7(4)
N1 C7 C6 123.9(4)
N1 C7 C15 127.3(4)
C6 C7 C15 108.8(3)
C9 C8 N1 114.0(4)
C9 C8 C13 118.6(4)
N1 C8 C13 127.0(4)
C10 C9 C8 121.2(4)
C10 C9 H9 119.4
C8 C9 H9 119.4
C11 C10 C9 120.2(4)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C12 119.2(4)
C10 C11 H11 120.4
C12 C11 H11 120.4
C13 C12 C11 122.1(4)
C13 C12 H12 119.0
C11 C12 H12 119.0
C12 C13 C8 118.7(4)
C12 C13 C14 114.5(4)
C8 C13 C14 126.7(4)
O1 C14 N2 119.0(4)
O1 C14 C13 119.8(4)
N2 C14 C13 121.2(3)
O2 C15 N2 113.7(3)
O2 C15 C7 109.6(3)
N2 C15 C7 110.1(3)
O2 C15 C16 110.0(3)
N2 C15 C16 109.7(3)
C7 C15 C16 103.3(3)
O3 C16 C1 129.1(4)
O3 C16 C15 123.3(4)
C1 C16 C15 107.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C14 1.244(5)
O2 C15 1.403(5)
O2 H2C 0.8200
O3 C16 1.212(5)
N1 C7 1.276(5)
N1 C8 1.413(5)
N2 C14 1.345(5)
N2 C15 1.437(5)
N2 H2D 0.90(5)
C1 C2 1.382(6)
C1 C6 1.402(6)
C1 C16 1.476(6)
C2 C3 1.382(6)
C2 H2A 0.9300
C3 C4 1.392(7)
C3 H3 0.9300
C4 C5 1.379(6)
C4 H4 0.9300
C5 C6 1.383(6)
C5 H5 0.9300
C6 C7 1.466(6)
C7 C15 1.517(6)
C8 C9 1.399(6)
C8 C13 1.413(6)
C9 C10 1.383(6)
C9 H9 0.9300
C10 C11 1.375(6)
C10 H10 0.9300
C11 C12 1.387(6)
C11 H11 0.9300
C12 C13 1.383(6)
C12 H12 0.9300
C13 C14 1.496(5)
C15 C16 1.563(6)
