#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/53/4025369.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_4025369
loop_
_publ_author_name
'Umesh A. Kshirsagar'
'Vedavati G. Puranik'
'Narshinha P. Argade'
_publ_section_title
;
 Total Synthesis of Proposed Auranthine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2702
_journal_page_last               2705
_journal_paper_doi               10.1021/jo100400z
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C19 H14 N4 O2. H2O'
_chemical_formula_sum            'C19 H16 N4 O3'
_chemical_formula_weight         348.36
_chemical_melting_point          461.6(5)
_chemical_name_common
'tetrahydroquinazolinopyridobenzodiazepindione '
_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                 93.5550(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5886(8)
_cell_length_b                   9.3268(6)
_cell_length_c                   14.0793(10)
_cell_measurement_reflns_used    3696
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.743
_cell_measurement_theta_min      2.62
_cell_volume                     1649.89(19)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    'SHELXTL, PyMOL and PLATON'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'Omega 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  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8047
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         2892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0389
_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)+(0.0450P)²+0.4353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2587
_reflns_number_total             2892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100400z_si_002.cif
_cod_data_source_block           C19H16N4O3compound1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '188-189 degree centigrade' was
changed to '461.6(5)' - it was converted from degrees Celsius(C) to
Kelvins(K), the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025369
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.00355(14) 0.50248(18) 0.37889(11) 0.0518(4) Uani 1 1 d . . .
H1 H 0.0454 0.5763 0.3735 0.062 Uiso 1 1 calc R . .
C2 C -0.10750(15) 0.5338(2) 0.39344(12) 0.0595(5) Uani 1 1 d . . .
H2 H -0.1290 0.6287 0.3987 0.071 Uiso 1 1 calc R . .
C3 C -0.18091(15) 0.4234(2) 0.40039(12) 0.0613(5) Uani 1 1 d . . .
H3 H -0.2516 0.4453 0.4099 0.074 Uiso 1 1 calc R . .
C4 C -0.15049(13) 0.2825(2) 0.39348(12) 0.0538(4) Uani 1 1 d . . .
H4 H -0.2003 0.2095 0.3974 0.065 Uiso 1 1 calc R . .
N5 N -0.01341(9) 0.10611(14) 0.37836(9) 0.0420(3) Uani 1 1 d . . .
C6 C 0.11884(12) -0.07684(16) 0.36191(11) 0.0430(4) Uani 1 1 d . . .
H6A H 0.1175 -0.1127 0.2972 0.052 Uiso 1 1 calc R . .
H6B H 0.0708 -0.1349 0.3971 0.052 Uiso 1 1 calc R . .
C7 C 0.23108(12) -0.08809(17) 0.40784(11) 0.0452(4) Uani 1 1 d . . .
H7B H 0.2337 -0.0471 0.4712 0.054 Uiso 1 1 calc R . .
H7C H 0.2522 -0.1879 0.4131 0.054 Uiso 1 1 calc R . .
C7A C 0.30585(11) -0.00764(16) 0.34654(10) 0.0389(3) Uani 1 1 d . . .
H7A H 0.3214 -0.0685 0.2924 0.047 Uiso 1 1 calc R . .
N8 N 0.40521(9) 0.02434(15) 0.40033(9) 0.0462(3) Uani 1 1 d . . .
H8 H 0.4075 0.0139 0.4611 0.055 Uiso 1 1 calc R . .
C9 C 0.49334(11) 0.06903(17) 0.36097(11) 0.0445(4) Uani 1 1 d . . .
C10 C 0.57596(12) 0.07338(18) 0.20791(12) 0.0489(4) Uani 1 1 d . . .
H10 H 0.6355 0.0338 0.2404 0.059 Uiso 1 1 calc R . .
C11 C 0.57866(13) 0.10149(18) 0.11230(12) 0.0520(4) Uani 1 1 d . . .
H11 H 0.6384 0.0772 0.0800 0.062 Uiso 1 1 calc R . .
C12 C 0.49223(13) 0.16599(18) 0.06430(12) 0.0511(4) Uani 1 1 d . . .
H12 H 0.4941 0.1860 -0.0003 0.061 Uiso 1 1 calc R . .
C13 C 0.40369(12) 0.20053(17) 0.11162(11) 0.0459(4) Uani 1 1 d . . .
H13 H 0.3471 0.2473 0.0793 0.055 Uiso 1 1 calc R . .
N14 N 0.30059(9) 0.20851(13) 0.24666(8) 0.0387(3) Uani 1 1 d . . .
N15 N 0.16029(9) 0.17831(13) 0.34369(8) 0.0370(3) Uani 1 1 d . . .
C16 C 0.14028(12) 0.32723(17) 0.35697(11) 0.0442(4) Uani 1 1 d . . .
C17 C 0.02934(12) 0.35991(16) 0.37217(10) 0.0415(4) Uani 1 1 d . . .
C18 C -0.04403(12) 0.24977(17) 0.38046(10) 0.0417(4) Uani 1 1 d . . .
C19 C 0.08310(11) 0.07561(15) 0.36138(10) 0.0370(3) Uani 1 1 d . . .
C20 C 0.25918(11) 0.13173(15) 0.30876(10) 0.0358(3) Uani 1 1 d . . .
C21 C 0.39726(11) 0.16645(15) 0.20784(10) 0.0378(3) Uani 1 1 d . . .
C22 C 0.48586(11) 0.10302(16) 0.25708(10) 0.0405(3) Uani 1 1 d . . .
O1 O 0.57928(8) 0.07995(14) 0.40812(8) 0.0584(3) Uani 1 1 d . . .
O2 O 0.21035(10) 0.41483(13) 0.35574(11) 0.0705(4) Uani 1 1 d . . .
O3 O 0.83424(13) 0.88144(16) 0.40013(12) 0.0724(4) Uani 1 1 d . . .
H1O H 0.795(2) 0.868(3) 0.342(2) 0.137(12) Uiso 1 1 d . . .
H2O H 0.881(2) 0.948(3) 0.3876(18) 0.105(9) Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C17 120.21(17) . . ?
C2 C1 H1 119.9 . . ?
C17 C1 H1 119.9 . . ?
C1 C2 C3 119.88(17) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.91(16) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C18 119.46(17) . . ?
C3 C4 H4 120.3 . . ?
C18 C4 H4 120.3 . . ?
C19 N5 C18 118.84(13) . . ?
C19 C6 C7 109.88(12) . . ?
C19 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
C19 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C7A C7 C6 108.50(12) . . ?
C7A C7 H7B 110.0 . . ?
C6 C7 H7B 110.0 . . ?
C7A C7 H7C 110.0 . . ?
C6 C7 H7C 110.0 . . ?
H7B C7 H7C 108.4 . . ?
N8 C7A C20 108.10(12) . . ?
N8 C7A C7 110.49(12) . . ?
C20 C7A C7 112.67(12) . . ?
N8 C7A H7A 108.5 . . ?
C20 C7A H7A 108.5 . . ?
C7 C7A H7A 108.5 . . ?
C9 N8 C7A 123.89(12) . . ?
C9 N8 H8 118.1 . . ?
C7A N8 H8 118.1 . . ?
O1 C9 N8 121.55(14) . . ?
O1 C9 C22 120.50(14) . . ?
N8 C9 C22 117.93(13) . . ?
C11 C10 C22 121.30(15) . . ?
C11 C10 H10 119.3 . . ?
C22 C10 H10 119.3 . . ?
C10 C11 C12 119.70(14) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.22(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C21 120.97(14) . . ?
C12 C13 H13 119.5 . . ?
C21 C13 H13 119.5 . . ?
C20 N14 C21 120.57(12) . . ?
C19 N15 C16 120.91(12) . . ?
C19 N15 C20 118.78(12) . . ?
C16 N15 C20 120.28(12) . . ?
O2 C16 N15 121.60(14) . . ?
O2 C16 C17 124.74(15) . . ?
N15 C16 C17 113.67(13) . . ?
C18 C17 C1 119.72(14) . . ?
C18 C17 C16 120.32(14) . . ?
C1 C17 C16 119.95(15) . . ?
C17 C18 N5 121.45(13) . . ?
C17 C18 C4 119.79(15) . . ?
N5 C18 C4 118.74(14) . . ?
N5 C19 N15 123.88(13) . . ?
N5 C19 C6 119.92(13) . . ?
N15 C19 C6 116.19(12) . . ?
N14 C20 N15 117.94(13) . . ?
N14 C20 C7A 124.19(12) . . ?
N15 C20 C7A 117.85(12) . . ?
C13 C21 C22 118.76(13) . . ?
C13 C21 N14 114.36(12) . . ?
C22 C21 N14 126.78(13) . . ?
C10 C22 C21 118.93(14) . . ?
C10 C22 C9 116.15(13) . . ?
C21 C22 C9 124.87(13) . . ?
H1O O3 H2O 104(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.369(2) . ?
C1 C17 1.398(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.391(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C18 1.398(2) . ?
C4 H4 0.9300 . ?
N5 C19 1.2845(18) . ?
N5 C18 1.395(2) . ?
C6 C19 1.491(2) . ?
C6 C7 1.521(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C7A 1.515(2) . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C7A N8 1.4524(18) . ?
C7A C20 1.510(2) . ?
C7A H7A 0.9800 . ?
N8 C9 1.3372(19) . ?
N8 H8 0.8600 . ?
C9 O1 1.2380(18) . ?
C9 C22 1.494(2) . ?
C10 C11 1.374(2) . ?
C10 C22 1.393(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(2) . ?
C12 H12 0.9300 . ?
C13 C21 1.399(2) . ?
C13 H13 0.9300 . ?
N14 C20 1.2671(18) . ?
N14 C21 1.4198(17) . ?
N15 C19 1.3978(18) . ?
N15 C16 1.4260(19) . ?
N15 C20 1.4340(17) . ?
C16 O2 1.2032(18) . ?
C16 C17 1.458(2) . ?
C17 C18 1.391(2) . ?
C21 C22 1.407(2) . ?
O3 H1O 0.94(3) . ?
O3 H2O 0.88(3) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C18 0.8(3) . . . . ?
C19 C6 C7 C7A -64.42(16) . . . . ?
C6 C7 C7A N8 161.81(12) . . . . ?
C6 C7 C7A C20 40.79(17) . . . . ?
C20 C7A N8 C9 -69.76(18) . . . . ?
C7 C7A N8 C9 166.54(14) . . . . ?
C7A N8 C9 O1 -171.99(15) . . . . ?
C7A N8 C9 C22 6.8(2) . . . . ?
C22 C10 C11 C12 2.8(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C21 -2.5(3) . . . . ?
C19 N15 C16 O2 168.88(15) . . . . ?
C20 N15 C16 O2 -13.2(2) . . . . ?
C19 N15 C16 C17 -10.8(2) . . . . ?
C20 N15 C16 C17 167.12(12) . . . . ?
C2 C1 C17 C18 -0.1(2) . . . . ?
C2 C1 C17 C16 -179.81(15) . . . . ?
O2 C16 C17 C18 -174.47(16) . . . . ?
N15 C16 C17 C18 5.2(2) . . . . ?
O2 C16 C17 C1 5.3(3) . . . . ?
N15 C16 C17 C1 -175.06(13) . . . . ?
C1 C17 C18 N5 -177.14(13) . . . . ?
C16 C17 C18 N5 2.6(2) . . . . ?
C1 C17 C18 C4 1.3(2) . . . . ?
C16 C17 C18 C4 -178.97(14) . . . . ?
C19 N5 C18 C17 -5.2(2) . . . . ?
C19 N5 C18 C4 176.35(14) . . . . ?
C3 C4 C18 C17 -1.7(2) . . . . ?
C3 C4 C18 N5 176.82(14) . . . . ?
C18 N5 C19 N15 -0.7(2) . . . . ?
C18 N5 C19 C6 177.98(13) . . . . ?
C16 N15 C19 N5 9.2(2) . . . . ?
C20 N15 C19 N5 -168.78(13) . . . . ?
C16 N15 C19 C6 -169.52(13) . . . . ?
C20 N15 C19 C6 12.53(18) . . . . ?
C7 C6 C19 N5 -140.74(14) . . . . ?
C7 C6 C19 N15 38.01(17) . . . . ?
C21 N14 C20 N15 -178.64(12) . . . . ?
C21 N14 C20 C7A -0.3(2) . . . . ?
C19 N15 C20 N14 141.38(14) . . . . ?
C16 N15 C20 N14 -36.59(19) . . . . ?
C19 N15 C20 C7A -37.09(17) . . . . ?
C16 N15 C20 C7A 144.94(13) . . . . ?
N8 C7A C20 N14 66.89(17) . . . . ?
C7 C7A C20 N14 -170.73(14) . . . . ?
N8 C7A C20 N15 -114.74(13) . . . . ?
C7 C7A C20 N15 7.64(18) . . . . ?
C12 C13 C21 C22 3.5(2) . . . . ?
C12 C13 C21 N14 -179.74(14) . . . . ?
C20 N14 C21 C13 144.43(14) . . . . ?
C20 N14 C21 C22 -39.2(2) . . . . ?
C11 C10 C22 C21 -1.7(2) . . . . ?
C11 C10 C22 C9 -179.37(15) . . . . ?
C13 C21 C22 C10 -1.4(2) . . . . ?
N14 C21 C22 C10 -177.71(14) . . . . ?
C13 C21 C22 C9 176.04(14) . . . . ?
N14 C21 C22 C9 -0.2(2) . . . . ?
O1 C9 C22 C10 32.5(2) . . . . ?
N8 C9 C22 C10 -146.32(15) . . . . ?
O1 C9 C22 C21 -145.04(16) . . . . ?
N8 C9 C22 C21 36.1(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091471
