#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/10/7151047.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_7151047
loop_
_publ_author_name
'Bowman, W. Russell'
'Elsegood, Mark R. J.'
'Stein, Tobias'
'Weaver, George W.'
_publ_section_title
;
 Radical reactions with 3H-quinazolin-4-ones: synthesis of
 deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and
 tryptanthrin.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              103
_journal_page_last               113
_journal_paper_doi               10.1039/b614075k
_journal_volume                  5
_journal_year                    2007
_chemical_formula_moiety         'C16 H10 N2 O3, C H Cl3'
_chemical_formula_sum            'C17 H11 Cl3 N2 O3'
_chemical_formula_weight         397.63
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   'geom except OH coords freely refined'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.123(2)
_cell_angle_beta                 94.525(3)
_cell_angle_gamma                99.594(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6511(3)
_cell_length_b                   8.6274(3)
_cell_length_c                   14.5395(7)
_cell_measurement_reflns_used    3181
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.0
_cell_volume                     819.97(6)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction        'DENZO & COLLECT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11250
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         3.12
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0071(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0353
_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)+(0.0492P)²+0.1456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                2898
_reflns_number_total             3715
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b614075k.txt
_cod_data_source_block           50
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151047
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.14244(19) 0.63569(15) 0.92173(9) 0.0146(3) Uani 1 1 d . . .
C1 C -0.0378(2) 0.66563(18) 0.87709(11) 0.0158(3) Uani 1 1 d . . .
N2 N -0.1702(2) 0.73348(15) 0.91529(9) 0.0166(3) Uani 1 1 d . . .
C2 C -0.1214(2) 0.79209(18) 1.00469(11) 0.0167(3) Uani 1 1 d . . .
C3 C -0.2519(2) 0.88209(19) 1.04353(12) 0.0196(4) Uani 1 1 d . . .
H3 H -0.3755 0.8971 1.0101 0.024 Uiso 1 1 calc R . .
C4 C -0.2003(3) 0.94848(19) 1.13003(12) 0.0222(4) Uani 1 1 d . . .
H4 H -0.2890 1.0090 1.1561 0.027 Uiso 1 1 calc R . .
C5 C -0.0183(3) 0.92780(19) 1.18015(12) 0.0213(4) Uani 1 1 d . . .
H5 H 0.0174 0.9763 1.2392 0.026 Uiso 1 1 calc R . .
C6 C 0.1089(2) 0.83740(19) 1.14387(11) 0.0192(4) Uani 1 1 d . . .
H6 H 0.2311 0.8218 1.1783 0.023 Uiso 1 1 calc R . .
C7 C 0.0580(2) 0.76842(18) 1.05619(11) 0.0158(3) Uani 1 1 d . . .
C8 C 0.1965(2) 0.67843(18) 1.01500(11) 0.0157(3) Uani 1 1 d . . .
O1 O 0.35078(17) 0.64334(14) 1.05530(8) 0.0212(3) Uani 1 1 d . . .
C9 C 0.3060(2) 0.58892(19) 0.86974(11) 0.0159(3) Uani 1 1 d . . .
H9 H 0.3919 0.5290 0.9111 0.019 Uiso 1 1 calc R . .
O2 O 0.42678(17) 0.72966(13) 0.84351(8) 0.0176(3) Uani 1 1 d . . .
H2 H 0.539(3) 0.723(2) 0.8595(14) 0.026 Uiso 1 1 d . . .
C10 C 0.2222(2) 0.49033(18) 0.78584(11) 0.0165(3) Uani 1 1 d . . .
C11 C 0.3409(3) 0.39065(19) 0.74902(11) 0.0197(4) Uani 1 1 d . . .
H11 H 0.4683 0.3786 0.7801 0.024 Uiso 1 1 calc R . .
C12 C 0.2740(3) 0.3093(2) 0.66742(12) 0.0243(4) Uani 1 1 d . . .
H12 H 0.3555 0.2411 0.6430 0.029 Uiso 1 1 calc R . .
C13 C 0.0874(3) 0.3263(2) 0.62048(12) 0.0266(4) Uani 1 1 d . . .
H13 H 0.0426 0.2703 0.5643 0.032 Uiso 1 1 calc R . .
C14 C -0.0312(3) 0.4249(2) 0.65622(12) 0.0238(4) Uani 1 1 d . . .
H14 H -0.1578 0.4374 0.6246 0.029 Uiso 1 1 calc R . .
C15 C 0.0355(2) 0.50622(19) 0.73902(11) 0.0174(3) Uani 1 1 d . . .
C16 C -0.0910(2) 0.61045(19) 0.77812(11) 0.0186(3) Uani 1 1 d . . .
O3 O -0.23696(18) 0.65190(16) 0.73531(8) 0.0282(3) Uani 1 1 d . . .
C17 C 0.4419(3) 0.8143(2) 0.62829(12) 0.0232(4) Uani 1 1 d . . .
H17 H 0.4644 0.7632 0.6891 0.028 Uiso 1 1 calc R . .
Cl1 Cl 0.46117(8) 0.68003(6) 0.53965(3) 0.03290(14) Uani 1 1 d . . .
Cl2 Cl 0.62940(7) 0.98375(6) 0.62257(4) 0.03665(15) Uani 1 1 d . . .
Cl3 Cl 0.19517(7) 0.86669(6) 0.62000(3) 0.03135(14) 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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C8 121.36(13) . . ?
C1 N1 C9 121.27(13) . . ?
C8 N1 C9 116.16(12) . . ?
N2 C1 N1 124.41(15) . . ?
N2 C1 C16 116.85(13) . . ?
N1 C1 C16 118.69(14) . . ?
C1 N2 C2 118.17(13) . . ?
N2 C2 C7 121.82(14) . . ?
N2 C2 C3 119.06(14) . . ?
C7 C2 C3 119.08(15) . . ?
C4 C3 C2 119.91(15) . . ?
C3 C4 C5 120.73(15) . . ?
C6 C5 C4 120.03(16) . . ?
C5 C6 C7 119.91(15) . . ?
C6 C7 C2 120.31(14) . . ?
C6 C7 C8 120.45(14) . . ?
C2 C7 C8 119.15(14) . . ?
O1 C8 N1 120.76(14) . . ?
O1 C8 C7 124.61(15) . . ?
N1 C8 C7 114.61(13) . . ?
O2 C9 N1 106.36(12) . . ?
O2 C9 C10 110.04(13) . . ?
N1 C9 C10 112.35(12) . . ?
C11 C10 C15 118.94(15) . . ?
C11 C10 C9 119.39(14) . . ?
C15 C10 C9 121.42(14) . . ?
C12 C11 C10 120.23(16) . . ?
C11 C12 C13 120.62(16) . . ?
C14 C13 C12 119.65(16) . . ?
C13 C14 C15 119.78(16) . . ?
C14 C15 C10 120.77(15) . . ?
C14 C15 C16 120.15(14) . . ?
C10 C15 C16 119.07(14) . . ?
O3 C16 C15 123.32(15) . . ?
O3 C16 C1 118.83(14) . . ?
C15 C16 C1 117.84(13) . . ?
Cl1 C17 Cl2 110.52(10) . . ?
Cl1 C17 Cl3 110.12(9) . . ?
Cl2 C17 Cl3 110.03(9) . . ?
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
N1 C1 1.3805(19) . ?
N1 C8 1.408(2) . ?
N1 C9 1.481(2) . ?
C1 N2 1.294(2) . ?
C1 C16 1.511(2) . ?
N2 C2 1.388(2) . ?
C2 C7 1.402(2) . ?
C2 C3 1.405(2) . ?
C3 C4 1.375(2) . ?
C4 C5 1.401(2) . ?
C5 C6 1.375(2) . ?
C6 C7 1.398(2) . ?
C7 C8 1.461(2) . ?
C8 O1 1.2237(18) . ?
C9 O2 1.4109(19) . ?
C9 C10 1.501(2) . ?
C10 C11 1.393(2) . ?
C10 C15 1.396(2) . ?
C11 C12 1.381(2) . ?
C12 C13 1.398(2) . ?
C13 C14 1.379(3) . ?
C14 C15 1.395(2) . ?
C15 C16 1.471(2) . ?
C16 O3 1.2161(19) . ?
C17 Cl1 1.7573(17) . ?
C17 Cl2 1.7629(18) . ?
C17 Cl3 1.7690(17) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N2 0.78(2) 2.02(2) 2.7935(17) 171(2) 1_655
O2 H2 O3 0.78(2) 2.57(2) 2.9963(17) 116.7(17) 1_655
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
C8 N1 C1 N2 -0.1(2) . . . . ?
C9 N1 C1 N2 -166.96(15) . . . . ?
C8 N1 C1 C16 -177.39(13) . . . . ?
C9 N1 C1 C16 15.7(2) . . . . ?
N1 C1 N2 C2 5.6(2) . . . . ?
C16 C1 N2 C2 -177.00(13) . . . . ?
C1 N2 C2 C7 -5.2(2) . . . . ?
C1 N2 C2 C3 172.63(15) . . . . ?
N2 C2 C3 C4 -176.39(15) . . . . ?
C7 C2 C3 C4 1.5(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C5 C6 C7 C2 0.5(2) . . . . ?
C5 C6 C7 C8 177.03(15) . . . . ?
N2 C2 C7 C6 175.98(14) . . . . ?
C3 C2 C7 C6 -1.9(2) . . . . ?
N2 C2 C7 C8 -0.6(2) . . . . ?
C3 C2 C7 C8 -178.38(14) . . . . ?
C1 N1 C8 O1 175.81(15) . . . . ?
C9 N1 C8 O1 -16.6(2) . . . . ?
C1 N1 C8 C7 -5.6(2) . . . . ?
C9 N1 C8 C7 161.98(13) . . . . ?
C6 C7 C8 O1 7.7(3) . . . . ?
C2 C7 C8 O1 -175.76(15) . . . . ?
C6 C7 C8 N1 -170.85(14) . . . . ?
C2 C7 C8 N1 5.7(2) . . . . ?
C1 N1 C9 O2 86.48(16) . . . . ?
C8 N1 C9 O2 -81.07(15) . . . . ?
C1 N1 C9 C10 -34.0(2) . . . . ?
C8 N1 C9 C10 158.48(13) . . . . ?
O2 C9 C10 C11 85.06(17) . . . . ?
N1 C9 C10 C11 -156.63(14) . . . . ?
O2 C9 C10 C15 -89.25(18) . . . . ?
N1 C9 C10 C15 29.1(2) . . . . ?
C15 C10 C11 C12 0.0(2) . . . . ?
C9 C10 C11 C12 -174.41(15) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C13 C14 C15 C16 -179.40(16) . . . . ?
C11 C10 C15 C14 -0.6(2) . . . . ?
C9 C10 C15 C14 173.78(15) . . . . ?
C11 C10 C15 C16 179.52(15) . . . . ?
C9 C10 C15 C16 -6.1(2) . . . . ?
C14 C15 C16 O3 -12.7(3) . . . . ?
C10 C15 C16 O3 167.21(16) . . . . ?
C14 C15 C16 C1 166.13(15) . . . . ?
C10 C15 C16 C1 -13.9(2) . . . . ?
N2 C1 C16 O3 10.8(2) . . . . ?
N1 C1 C16 O3 -171.71(15) . . . . ?
N2 C1 C16 C15 -168.14(14) . . . . ?
N1 C1 C16 C15 9.4(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190352
