#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/57/7155754.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_7155754
loop_
_publ_author_name
'Dabiri, Minoo'
'Farajinia Lehi, Noushin'
'Kazemi Movahed, Siyavash'
'Khavasi, Hamid Reza'
_publ_section_title
;
 Pd-catalyzed regioselective C-H halogenation of quinazolinones and
 benzoxazinones
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01534H
_journal_year                    2017
_chemical_formula_sum            'C16 H11 Cl2 N O4'
_chemical_formula_weight         352.16
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-01-25 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                87.80(2)
_cell_angle_beta                 83.42(2)
_cell_angle_gamma                71.65(2)
_cell_formula_units_Z            2
_cell_length_a                   8.079(2)
_cell_length_b                   8.088(3)
_cell_length_c                   12.700(4)
_cell_measurement_reflns_used    6859
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.67
_cell_volume                     782.5(4)
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_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  0.0951
_diffrn_reflns_av_sigmaI/netI    0.1477
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6859
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.434
_exptl_absorpt_correction_T_max  0.8456
_exptl_absorpt_correction_T_min  0.5215
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1751
_reflns_number_gt                3030
_reflns_number_total             3387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob01534h2.cif
_cod_data_source_block           khd390
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C16 H11 Cl2 N1 O4'
_cod_database_code               7155754
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
C1 C 0.6339(16) 0.7441(14) 0.5166(8) 0.059(3) Uani 1 1 d .
C2 C 0.514(2) 0.7737(17) 0.6038(9) 0.079(4) Uani 1 1 d .
H2 H 0.5455 0.7940 0.6692 0.095 Uiso 1 1 calc R
C3 C 0.349(2) 0.7732(19) 0.5943(11) 0.084(4) Uani 1 1 d .
H3 H 0.2667 0.7883 0.6537 0.101 Uiso 1 1 calc R
C4 C 0.3038(18) 0.7504(17) 0.4976(11) 0.077(4) Uani 1 1 d .
H4 H 0.1896 0.7526 0.4914 0.093 Uiso 1 1 calc R
C5 C 0.4232(16) 0.7241(14) 0.4079(9) 0.062(3) Uani 1 1 d .
C6 C 0.5972(13) 0.7194(12) 0.4164(7) 0.050(2) Uani 1 1 d .
C7 C 0.7354(14) 0.6887(14) 0.3210(8) 0.054(3) Uani 1 1 d .
C8 C 0.9607(12) 0.5301(12) 0.2118(6) 0.042(2) Uani 1 1 d .
C9 C 1.0766(13) 0.3676(12) 0.1821(7) 0.047(2) Uani 1 1 d .
H9 H 1.0712 0.2690 0.2207 0.056 Uiso 1 1 calc R
C10 C 1.2000(12) 0.3528(12) 0.0952(7) 0.045(2) Uani 1 1 d .
C11 C 1.3089(17) 0.0488(15) 0.1075(10) 0.075(4) Uani 1 1 d .
H11A H 1.1949 0.0360 0.1066 0.090 Uiso 1 1 calc R
H11B H 1.3324 0.0537 0.1795 0.090 Uiso 1 1 calc R
H11C H 1.3960 -0.0489 0.0725 0.090 Uiso 1 1 calc R
C12 C 1.3533(13) 0.6247(13) -0.1028(7) 0.050(2) Uani 1 1 d .
H12A H 1.3833 0.6979 -0.0555 0.060 Uiso 1 1 calc R
H12B H 1.2446 0.6878 -0.1298 0.060 Uiso 1 1 calc R
H12C H 1.4443 0.5899 -0.1606 0.060 Uiso 1 1 calc R
C13 C 1.2120(12) 0.5038(12) 0.0348(7) 0.042(2) Uani 1 1 d .
C14 C 1.1005(14) 0.6656(12) 0.0702(7) 0.050(2) Uani 1 1 d .
H14 H 1.1111 0.7669 0.0370 0.060 Uiso 1 1 calc R
C15 C 0.9717(14) 0.6754(13) 0.1563(7) 0.051(3) Uani 1 1 d .
C16 C 0.8519(15) 0.8471(14) 0.1897(9) 0.064(3) Uani 1 1 d .
N1 N 0.8370(10) 0.5396(10) 0.3005(6) 0.0445(19) Uani 1 1 d .
O1 O 1.3140(9) 0.2028(8) 0.0547(5) 0.0541(18) Uani 1 1 d .
O2 O 1.3350(9) 0.4750(8) -0.0474(5) 0.0520(18) Uani 1 1 d .
O3 O 0.8492(13) 0.9847(10) 0.1537(7) 0.094(3) Uani 1 1 d .
O4 O 0.7305(10) 0.8430(9) 0.2757(6) 0.069(2) Uani 1 1 d .
Cl1 Cl 0.8455(5) 0.7392(7) 0.5344(3) 0.1195(18) Uani 1 1 d .
Cl2 Cl 0.3640(5) 0.6983(5) 0.2860(3) 0.0851(12) 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
C2 C1 C6 124.2(12)
C2 C1 Cl1 117.1(10)
C6 C1 Cl1 118.7(8)
C1 C2 C3 119.2(12)
C1 C2 H2 120.4
C3 C2 H2 120.4
C4 C3 C2 119.5(12)
C4 C3 H3 120.2
C2 C3 H3 120.3
C3 C4 C5 121.8(13)
C3 C4 H4 119.1
C5 C4 H4 119.1
C4 C5 C6 119.7(11)
C4 C5 Cl2 121.3(10)
C6 C5 Cl2 119.1(8)
C1 C6 C5 115.6(9)
C1 C6 C7 122.1(10)
C5 C6 C7 122.2(10)
N1 C7 O4 130.6(9)
N1 C7 C6 120.3(9)
O4 C7 C6 108.9(8)
C15 C8 C9 119.9(8)
C15 C8 N1 122.0(8)
C9 C8 N1 118.1(8)
C10 C9 C8 119.8(9)
C10 C9 H9 120.1
C8 C9 H9 120.1
O1 C10 C9 126.0(9)
O1 C10 C13 112.8(8)
C9 C10 C13 121.1(8)
O1 C11 H11A 109.5
O1 C11 H11B 109.5
H11A C11 H11B 109.5
O1 C11 H11C 109.4
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O2 C12 H12A 109.5
O2 C12 H12B 109.5
H12A C12 H12B 109.5
O2 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
O2 C13 C14 126.2(8)
O2 C13 C10 116.3(8)
C14 C13 C10 117.5(8)
C13 C14 C15 119.8(9)
C13 C14 H14 120.1
C15 C14 H14 120.1
C8 C15 C14 121.6(9)
C8 C15 C16 119.6(9)
C14 C15 C16 118.7(9)
O3 C16 O4 117.7(9)
O3 C16 C15 128.0(10)
O4 C16 C15 114.2(9)
C7 N1 C8 114.5(8)
C10 O1 C11 116.7(8)
C13 O2 C12 116.1(7)
C7 O4 C16 118.9(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.359(15)
C1 C6 1.375(15)
C1 Cl1 1.738(13)
C2 C3 1.36(2)
C2 H2 0.9300
C3 C4 1.354(19)
C3 H3 0.9300
C4 C5 1.383(16)
C4 H4 0.9300
C5 C6 1.410(16)
C5 Cl2 1.711(12)
C6 C7 1.521(13)
C7 N1 1.244(12)
C7 O4 1.345(12)
C8 C15 1.368(13)
C8 C9 1.388(13)
C8 N1 1.405(11)
C9 C10 1.382(13)
C9 H9 0.9300
C10 O1 1.350(11)
C10 C13 1.441(13)
C11 O1 1.402(13)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 O2 1.416(11)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 O2 1.329(10)
C13 C14 1.392(13)
C14 C15 1.407(13)
C14 H14 0.9300
C15 C16 1.466(14)
C16 O3 1.181(12)
C16 O4 1.389(12)
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
C6 C1 C2 C3 2.5(19)
Cl1 C1 C2 C3 -178.0(11)
C1 C2 C3 C4 -3(2)
C2 C3 C4 C5 1(2)
C3 C4 C5 C6 0.5(19)
C3 C4 C5 Cl2 -179.2(11)
C2 C1 C6 C5 -0.8(16)
Cl1 C1 C6 C5 179.7(8)
C2 C1 C6 C7 179.3(11)
Cl1 C1 C6 C7 -0.2(13)
C4 C5 C6 C1 -0.7(15)
Cl2 C5 C6 C1 179.0(8)
C4 C5 C6 C7 179.2(10)
Cl2 C5 C6 C7 -1.1(14)
C1 C6 C7 N1 84.6(13)
C5 C6 C7 N1 -95.3(13)
C1 C6 C7 O4 -91.2(12)
C5 C6 C7 O4 88.9(12)
C15 C8 C9 C10 -1.5(14)
N1 C8 C9 C10 179.8(9)
C8 C9 C10 O1 -176.4(9)
C8 C9 C10 C13 0.5(14)
O1 C10 C13 O2 -2.5(12)
C9 C10 C13 O2 -179.8(9)
O1 C10 C13 C14 -179.7(9)
C9 C10 C13 C14 3.0(14)
O2 C13 C14 C15 177.6(9)
C10 C13 C14 C15 -5.6(14)
C9 C8 C15 C14 -1.2(15)
N1 C8 C15 C14 177.4(9)
C9 C8 C15 C16 -178.4(10)
N1 C8 C15 C16 0.2(15)
C13 C14 C15 C8 4.8(16)
C13 C14 C15 C16 -177.9(10)
C8 C15 C16 O3 176.4(13)
C14 C15 C16 O3 -1(2)
C8 C15 C16 O4 -2.2(16)
C14 C15 C16 O4 -179.6(9)
O4 C7 N1 C8 -3.9(17)
C6 C7 N1 C8 -178.6(9)
C15 C8 N1 C7 2.7(14)
C9 C8 N1 C7 -178.6(9)
C9 C10 O1 C11 -1.7(15)
C13 C10 O1 C11 -178.8(9)
C14 C13 O2 C12 0.5(14)
C10 C13 O2 C12 -176.4(8)
N1 C7 O4 C16 1.8(18)
C6 C7 O4 C16 176.9(10)
O3 C16 O4 C7 -177.3(12)
C15 C16 O4 C7 1.5(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139193087
