#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/62/2226204.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226204
loop_
_publ_author_name
'Grundt, Peter'
'Douglas, Kelsi A.'
'Krivogorsky, Bogdana'
'Nemykin, Victor N.'
_publ_section_title
;
 7,9-Dichloro-6H,12H-indolo[2,1-b]quinazoline-6,12-dione
;
_journal_coeditor_code           JJ2032
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1474
_journal_page_last               o1475
_journal_paper_doi               10.1107/S1600536810018969
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H6 Cl2 N2 O2'
_chemical_formula_moiety         'C15 H6 Cl2 N2 O2'
_chemical_formula_sum            'C15 H6 Cl2 N2 O2'
_chemical_formula_weight         317.13
_chemical_melting_point          200
_chemical_name_systematic
;
7,9-Dichloro-6H,12H-indolo[2,1-b]quinazoline-6,12-dione
;
_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
_cell_angle_alpha                94.908(7)
_cell_angle_beta                 96.709(7)
_cell_angle_gamma                107.395(8)
_cell_formula_units_Z            4
_cell_length_a                   7.0179(2)
_cell_length_b                   10.7276(3)
_cell_length_c                   17.2338(12)
_cell_measurement_pressure       101.3
_cell_measurement_reflns_used    28356
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.08
_cell_volume                     1219.66(12)
_computing_cell_refinement       'HKL-2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'CrystalClear (Rigaku Americas, 2009)'
_computing_data_reduction        'CrystalClear (Rigaku Americas, 2009)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material
'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement
'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID-II imaging plate'
_diffrn_measurement_method       'ω  scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed tube (Mo)'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31502
_diffrn_reflns_theta_full        27.486
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         3.077
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  4
_diffrn_standards_number         31502
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.350
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.36
_refine_ls_extinction_coef       43(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5571
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.0012219
_refine_ls_shift/su_mean         0.9049609
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[σ²(F²) + (0.02P)² + 2.09P], where P=[max(Fo²,0) + 2Fc²]/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0815
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0815
_reflns_number_gt                4830
_reflns_number_total             5585
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jj2032.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               2226204
_cod_database_fobs_code          2226204
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_type_symbol
_atom_site_label
_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_disorder_assembly
_atom_site_disorder_group
Cl Cl1A 0.12767(7) 0.19849(5) -0.30745(3) 0.0154 Uani 1.0000 . .
Cl Cl2A 0.22470(8) -0.16786(5) -0.51632(3) 0.0203 Uani 1.0000 . .
O O1A 0.5092(2) 0.25603(14) -0.16905(8) 0.0172 Uani 1.0000 . .
O O2A 0.8111(2) -0.15104(14) -0.30107(8) 0.0181 Uani 1.0000 . .
C C1A 1.1319(3) -0.08669(19) -0.17069(12) 0.0162 Uani 1.0000 . .
C C2A 1.2819(3) -0.0485(2) -0.10617(12) 0.0183 Uani 1.0000 . .
C C3A 1.2850(3) 0.0523(2) -0.04843(12) 0.0208 Uani 1.0000 . .
C C4A 1.1391(3) 0.1145(2) -0.05462(12) 0.0185 Uani 1.0000 . .
N N5A 0.8403(2) 0.14280(16) -0.12490(10) 0.0151 Uani 1.0000 . .
C C6A 0.5402(3) 0.16629(19) -0.20790(11) 0.0137 Uani 1.0000 . .
C C7A 0.2640(3) 0.09548(18) -0.33341(11) 0.0137 Uani 1.0000 . .
C C8A 0.1974(3) 0.01396(19) -0.40464(11) 0.0154 Uani 1.0000 . .
C C9A 0.3055(3) -0.06961(19) -0.42595(11) 0.0151 Uani 1.0000 . .
C C10A 0.4729(3) -0.07980(19) -0.37831(11) 0.0146 Uani 1.0000 . .
N N11A 0.6952(2) 0.01079(16) -0.24828(9) 0.0130 Uani 1.0000 . .
C C12A 0.8273(3) -0.06404(19) -0.24787(11) 0.0140 Uani 1.0000 . .
C C13A 0.9855(3) 0.07665(19) -0.11960(11) 0.0142 Uani 1.0000 . .
C C14A 0.7090(3) 0.10816(18) -0.18691(11) 0.0134 Uani 1.0000 . .
C C15A 0.4331(3) 0.09159(18) -0.28464(11) 0.0129 Uani 1.0000 . .
C C16A 0.5321(3) 0.00196(19) -0.30772(11) 0.0141 Uani 1.0000 . .
C C17A 0.9828(3) -0.02472(18) -0.17809(11) 0.0139 Uani 1.0000 . .
Cl Cl1B 0.89170(7) 0.34858(5) 0.34019(3) 0.0173 Uani 1.0000 . .
Cl Cl2B 0.70190(7) 0.70635(5) 0.52404(3) 0.0192 Uani 1.0000 . .
O O1B 0.5337(2) 0.26130(14) 0.19080(9) 0.0189 Uani 1.0000 . .
O O2B 0.1512(2) 0.64871(14) 0.28391(8) 0.0169 Uani 1.0000 . .
C C1B -0.1458(3) 0.55847(19) 0.14382(12) 0.0163 Uani 1.0000 . .
C C2B -0.2819(3) 0.5080(2) 0.07583(12) 0.0193 Uani 1.0000 . .
C C3B -0.2635(3) 0.4038(2) 0.02547(12) 0.0192 Uani 1.0000 . .
C C4B -0.1086(3) 0.3521(2) 0.04302(12) 0.0176 Uani 1.0000 . .
N N5B 0.1872(3) 0.34718(16) 0.12667(10) 0.0153 Uani 1.0000 . .
C C6B 0.4831(3) 0.34864(19) 0.22288(11) 0.0148 Uani 1.0000 . .
C C7B 0.7333(3) 0.44170(19) 0.35489(12) 0.0146 Uani 1.0000 . .
C C8B 0.7737(3) 0.5271(2) 0.42418(12) 0.0165 Uani 1.0000 . .
C C9B 0.6463(3) 0.60188(19) 0.43630(11) 0.0151 Uani 1.0000 . .
C C10B 0.4808(3) 0.59806(19) 0.38219(11) 0.0144 Uani 1.0000 . .
N N11B 0.2930(2) 0.49043(16) 0.24801(9) 0.0130 Uani 1.0000 . .
C C12B 0.1523(3) 0.55777(19) 0.23644(11) 0.0138 Uani 1.0000 . .
C C13B 0.0312(3) 0.40238(18) 0.11173(11) 0.0139 Uani 1.0000 . .
C C14B 0.3049(3) 0.39217(19) 0.19191(11) 0.0140 Uani 1.0000 . .
C C15B 0.5689(3) 0.43274(19) 0.29911(11) 0.0139 Uani 1.0000 . .
C C16B 0.4478(3) 0.51304(19) 0.31342(11) 0.0135 Uani 1.0000 . .
C C17B 0.0111(3) 0.50602(19) 0.16292(11) 0.0141 Uani 1.0000 . .
H H1A 1.130(2) -0.1539(13) -0.2094(9) 0.0204 Uiso 1.0000 . .
H H2A 1.380(2) -0.0909(13) -0.1021(9) 0.0206 Uiso 1.0000 . .
H H3A 1.388(2) 0.0793(14) -0.0051(9) 0.0251 Uiso 1.0000 . .
H H4A 1.142(2) 0.1815(13) -0.0153(9) 0.0215 Uiso 1.0000 . .
H H5A 0.083(2) 0.0145(13) -0.4368(9) 0.0178 Uiso 1.0000 . .
H H6A 0.541(2) -0.1385(13) -0.3938(9) 0.0187 Uiso 1.0000 . .
H H1B -0.159(2) 0.6286(13) 0.1773(9) 0.0204 Uiso 1.0000 . .
H H2B -0.388(2) 0.5439(14) 0.0634(9) 0.0248 Uiso 1.0000 . .
H H3B -0.355(2) 0.3688(14) -0.0209(9) 0.0224 Uiso 1.0000 . .
H H4B -0.094(2) 0.2847(13) 0.0083(9) 0.0208 Uiso 1.0000 . .
H H5B 0.885(2) 0.5353(13) 0.4615(9) 0.0195 Uiso 1.0000 . .
H H6B 0.398(2) 0.6491(12) 0.3915(9) 0.0160 Uiso 1.0000 . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 'International Tables Vol C 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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1A C7A C15A . . . 121.65(15) no
Cl1A C7A C8A . . . 118.05(15) no
C15A C7A C8A . . . 120.30(18) no
C7A C15A C6A . . . 132.59(18) no
C7A C15A C16A . . . 118.79(17) no
C6A C15A C16A . . . 108.62(16) no
C15A C6A O1A . . . 129.87(18) no
C15A C6A C14A . . . 104.37(15) no
O1A C6A C14A . . . 125.75(17) no
C6A C14A N5A . . . 126.26(17) no
C6A C14A N11A . . . 107.38(16) no
N5A C14A N11A . . . 126.35(17) no
C14A N5A C13A . . . 115.81(17) no
N5A C13A C4A . . . 118.48(17) no
N5A C13A C17A . . . 122.13(17) no
C4A C13A C17A . . . 119.38(18) no
C13A C4A C3A . . . 119.69(19) no
C13A C4A H4A . . . 120.2(10) no
C3A C4A H4A . . . 120.2(10) no
C4A C3A C2A . . . 120.96(19) no
C4A C3A H3A . . . 119.0(10) no
C2A C3A H3A . . . 120.0(10) no
C3A C2A C1A . . . 120.04(19) no
C3A C2A H2A . . . 121.2(10) no
C1A C2A H2A . . . 118.8(10) no
C2A C1A C17A . . . 119.86(19) no
C2A C1A H1A . . . 119.9(10) no
C17A C1A H1A . . . 120.2(10) no
C13A C17A C1A . . . 120.07(18) no
C13A C17A C12A . . . 120.66(17) no
C1A C17A C12A . . . 119.26(17) no
C17A C12A N11A . . . 112.36(16) no
C17A C12A O2A . . . 125.53(18) no
N11A C12A O2A . . . 122.11(17) no
C12A N11A C14A . . . 122.65(16) no
C12A N11A C16A . . . 127.27(16) no
C14A N11A C16A . . . 110.08(15) no
N11A C16A C15A . . . 109.50(16) no
N11A C16A C10A . . . 127.57(18) no
C15A C16A C10A . . . 122.93(18) no
C16A C10A C9A . . . 115.95(18) no
C16A C10A H6A . . . 122.5(10) no
C9A C10A H6A . . . 121.5(10) no
C10A C9A C8A . . . 123.45(18) no
C10A C9A Cl2A . . . 118.47(15) no
C8A C9A Cl2A . . . 118.07(15) no
C9A C8A C7A . . . 118.51(17) no
C9A C8A H5A . . . 120.8(10) no
C7A C8A H5A . . . 120.6(10) no
Cl1B C7B C15B . . . 121.43(15) no
Cl1B C7B C8B . . . 118.59(15) no
C15B C7B C8B . . . 119.98(18) no
C7B C15B C6B . . . 132.47(18) no
C7B C15B C16B . . . 118.96(18) no
C6B C15B C16B . . . 108.54(16) no
C15B C6B O1B . . . 130.04(18) no
C15B C6B C14B . . . 104.47(16) no
O1B C6B C14B . . . 125.46(18) no
C6B C14B N11B . . . 107.35(16) no
C6B C14B N5B . . . 126.40(17) no
N11B C14B N5B . . . 126.25(17) no
C14B N11B C16B . . . 110.20(15) no
C14B N11B C12B . . . 122.59(16) no
C16B N11B C12B . . . 127.14(16) no
N11B C16B C15B . . . 109.35(16) no
N11B C16B C10B . . . 127.71(17) no
C15B C16B C10B . . . 122.94(18) no
C16B C10B C9B . . . 115.54(18) no
C16B C10B H6B . . . 122.2(10) no
C9B C10B H6B . . . 122.3(10) no
C10B C9B C8B . . . 123.79(18) no
C10B C9B Cl2B . . . 119.12(15) no
C8B C9B Cl2B . . . 117.08(15) no
C9B C8B C7B . . . 118.75(18) no
C9B C8B H5B . . . 120.6(10) no
C7B C8B H5B . . . 120.6(10) no
N11B C12B O2B . . . 121.91(17) no
N11B C12B C17B . . . 112.41(16) no
O2B C12B C17B . . . 125.68(17) no
C12B C17B C13B . . . 120.36(17) no
C12B C17B C1B . . . 119.93(17) no
C13B C17B C1B . . . 119.70(18) no
C17B C13B N5B . . . 122.53(17) no
C17B C13B C4B . . . 119.38(18) no
N5B C13B C4B . . . 118.09(17) no
C13B N5B C14B . . . 115.64(16) no
C13B C4B C3B . . . 120.22(19) no
C13B C4B H4B . . . 119.5(10) no
C3B C4B H4B . . . 120.2(10) no
C4B C3B C2B . . . 120.39(19) no
C4B C3B H3B . . . 118.8(10) no
C2B C3B H3B . . . 120.8(10) no
C3B C2B C1B . . . 120.12(19) no
C3B C2B H2B . . . 120.2(10) no
C1B C2B H2B . . . 119.6(10) no
C17B C1B C2B . . . 120.18(18) no
C17B C1B H1B . . . 120.2(10) no
C2B C1B H1B . . . 119.6(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1A C7A . . 1.7272(19) yes
Cl2A C9A . . 1.7358(19) yes
Cl1B C7B . . 1.7276(19) yes
Cl2B C9B . . 1.734(2) yes
O1A C6A . . 1.213(2) yes
O2A C12A . . 1.221(2) yes
O1B C6B . . 1.211(2) yes
O2B C12B . . 1.221(2) yes
N5A C13A . . 1.405(2) yes
N5A C14A . . 1.275(2) yes
N11A C16A . . 1.419(2) yes
N11A C12A . . 1.396(2) yes
N11A C14A . . 1.395(2) yes
N5B C13B . . 1.401(2) yes
N5B C14B . . 1.277(3) yes
N11B C16B . . 1.421(2) yes
N11B C12B . . 1.394(2) yes
N11B C14B . . 1.396(2) yes
C15A C7A . . 1.386(3) n
C15A C16A . . 1.401(3) n
C15A C6A . . 1.477(3) n
C7A C8A . . 1.389(3) n
C8A C9A . . 1.389(3) n
C8A H5A . . 0.925(15) no
C9A C10A . . 1.390(3) n
C10A C16A . . 1.380(3) n
C10A H6A . . 0.938(15) no
C12A C17A . . 1.465(3) n
C17A C1A . . 1.397(3) n
C17A C13A . . 1.412(3) n
C1A C2A . . 1.379(3) n
C1A H1A . . 0.937(15) no
C2A C3A . . 1.399(3) n
C2A H2A . . 0.929(16) no
C3A C4A . . 1.379(3) n
C3A H3A . . 0.937(16) no
C4A C13A . . 1.399(3) n
C4A H4A . . 0.937(15) no
C14A C6A . . 1.518(3) n
C15B C7B . . 1.387(3) n
C15B C16B . . 1.405(3) no
C15B C6B . . 1.480(3) no
C7B C8B . . 1.387(3) no
C8B C9B . . 1.389(3) n
C8B H5B . . 0.931(15) no
C9B C10B . . 1.390(3) no
C10B C16B . . 1.384(3) no
C10B H6B . . 0.930(15) no
C12B C17B . . 1.467(3) no
C17B C1B . . 1.399(3) no
C17B C13B . . 1.410(3) no
C1B C2B . . 1.378(3) no
C1B H1B . . 0.942(15) no
C2B C3B . . 1.402(3) no
C2B H2B . . 0.947(16) no
C3B C4B . . 1.377(3) no
C3B H3B . . 0.937(16) no
C4B C13B . . 1.399(3) no
C4B H4B . . 0.936(16) no
C14B C6B . . 1.517(3) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1B H1B Cl1A 2_565 0.942(15) 2.729(15) 3.637(2) 162.0(12)
C2A H2A O1B 2_755 0.929(16) 2.539(15) 3.264(3) 134.9(12)
C4B H4B N5A 1_455 0.936(16) 2.556(15) 3.422(3) 153.9(12)
C10A H6A Cl2B 1_544 0.938(15) 2.673(15) 3.585(2) 164.8(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139078962
