#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226692.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_2226692
loop_
_publ_author_name
'Vennila, K. N.'
'Prabha, K.'
'Manoj, M.'
'Prasad, K. J. Rajendra'
'Velmurugan, D.'
_publ_section_title
;
 2-Chloro-7-methyl-12-phenyldibenzo[b,g][1,8]naphthyridin-11(6H)-one
;
_journal_coeditor_code           SU2185
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1823
_journal_paper_doi               10.1107/S160053681002430X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C23 H15 Cl N2 O'
_chemical_formula_moiety         'C23 H15 Cl N2 O'
_chemical_formula_sum            'C23 H15 Cl N2 O'
_chemical_formula_weight         370.82
_chemical_name_common
;
9-Chloro-4-methyl-11-phenyl-5,6-diazatetracen-12(5H)-one
;
_chemical_name_systematic
;
2-Chloro-7-methyl-12-phenyldibenzo[b,g][1,8]naphthyridin-
11(6H)-one
;
_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
_cell_angle_alpha                89.4460(10)
_cell_angle_beta                 74.3620(10)
_cell_angle_gamma                77.6720(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2434(2)
_cell_length_b                   8.5528(2)
_cell_length_c                   13.0740(3)
_cell_measurement_reflns_used    5019
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      1.62
_cell_volume                     866.06(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21083
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.44
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.345
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         5019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0436
_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)+(0.0812P)²+0.1735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                4047
_reflns_number_total             5019
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2185.cif
_cod_data_source_block           I
_cod_database_code               2226692
_cod_database_fobs_code          2226692
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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.43107(6) 0.82442(6) 0.41605(3) 0.06692(16) Uani d . 1 . .
C C8 0.97978(14) 0.28540(13) 0.08976(9) 0.0295(2) Uani d . 1 . .
N N1 0.75659(13) 0.43848(12) 0.01596(8) 0.0347(2) Uani d . 1 . .
C C6 0.75767(14) 0.49589(13) 0.19809(9) 0.0321(2) Uani d . 1 . .
C C7 0.91173(14) 0.37615(13) 0.18528(9) 0.0303(2) Uani d . 1 . .
C C11 1.19508(14) 0.07433(13) -0.03719(9) 0.0318(2) Uani d . 1 . .
N N2 0.96411(13) 0.24442(12) -0.08970(8) 0.0349(2) Uani d . 1 . .
H H2 0.9104 0.2694 -0.1376 0.042 Uiso calc R 1 . .
C C5 0.68564(14) 0.52218(14) 0.11069(9) 0.0329(2) Uani d . 1 . .
C C9 0.89694(14) 0.32538(13) 0.00739(9) 0.0298(2) Uani d . 1 . .
O O1 1.18861(13) 0.08963(12) 0.14332(7) 0.0456(2) Uani d . 1 . .
C C16 1.17758(17) 0.05651(15) -0.22018(10) 0.0375(3) Uani d . 1 . .
C C12 1.12754(15) 0.14578(14) 0.07187(9) 0.0318(2) Uani d . 1 . .
C C10 1.11201(14) 0.12564(13) -0.11549(9) 0.0317(2) Uani d . 1 . .
C C15 1.32690(18) -0.06129(16) -0.24169(11) 0.0443(3) Uani d . 1 . .
H H15 1.3730 -0.1075 -0.3103 0.053 Uiso calc R 1 . .
C C19 1.15161(16) 0.40958(15) 0.25824(10) 0.0390(3) Uani d . 1 . .
H H19 1.1985 0.4551 0.1953 0.047 Uiso calc R 1 . .
C C18 0.99944(15) 0.35745(14) 0.27169(9) 0.0334(2) Uani d . 1 . .
C C13 1.34488(16) -0.04709(15) -0.06305(11) 0.0392(3) Uani d . 1 . .
H H13 1.3998 -0.0829 -0.0110 0.047 Uiso calc R 1 . .
C C1 0.67473(16) 0.59156(15) 0.29368(10) 0.0388(3) Uani d . 1 . .
H H1 0.7190 0.5754 0.3522 0.047 Uiso calc R 1 . .
C C4 0.53475(16) 0.64433(16) 0.12077(12) 0.0423(3) Uani d . 1 . .
H H4 0.4868 0.6619 0.0638 0.051 Uiso calc R 1 . .
C C23 0.92949(19) 0.29264(18) 0.36673(11) 0.0451(3) Uani d . 1 . .
H H23 0.8252 0.2611 0.3775 0.054 Uiso calc R 1 . .
C C17 1.0871(2) 0.11093(18) -0.30353(10) 0.0472(3) Uani d . 1 . .
H H17A 1.1601 0.0680 -0.3721 0.071 Uiso calc R 1 . .
H H17B 1.0616 0.2259 -0.3030 0.071 Uiso calc R 1 . .
H H17C 0.9815 0.0738 -0.2890 0.071 Uiso calc R 1 . .
C C2 0.53032(17) 0.70682(16) 0.29904(11) 0.0424(3) Uani d . 1 . .
C C20 1.23394(19) 0.39418(18) 0.33819(12) 0.0494(3) Uani d . 1 . .
H H20 1.3351 0.4308 0.3293 0.059 Uiso calc R 1 . .
C C21 1.1663(2) 0.3246(2) 0.43107(12) 0.0584(4) Uani d . 1 . .
H H21 1.2237 0.3114 0.4839 0.070 Uiso calc R 1 . .
C C14 1.41133(18) -0.11368(17) -0.16453(12) 0.0465(3) Uani d . 1 . .
H H14 1.5121 -0.1933 -0.1818 0.056 Uiso calc R 1 . .
C C22 1.0139(2) 0.2747(2) 0.44566(12) 0.0584(4) Uani d . 1 . .
H H22 0.9678 0.2288 0.5086 0.070 Uiso calc R 1 . .
C C3 0.45924(17) 0.73618(17) 0.21266(13) 0.0468(3) Uani d . 1 . .
H H3 0.3618 0.8174 0.2181 0.056 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 C8 C9 . . 117.71(10) ?
C7 C8 C12 . . 123.22(9) ?
C9 C8 C12 . . 119.00(10) ?
C9 N1 C5 . . 117.25(10) ?
C5 C6 C1 . . 118.78(10) ?
C5 C6 C7 . . 118.27(10) ?
C1 C6 C7 . . 122.95(10) ?
C8 C7 C6 . . 118.53(10) ?
C8 C7 C18 . . 122.12(10) ?
C6 C7 C18 . . 119.28(10) ?
C10 C11 C13 . . 119.38(11) ?
C10 C11 C12 . . 121.14(10) ?
C13 C11 C12 . . 119.48(11) ?
C9 N2 C10 . . 124.08(10) ?
C9 N2 H2 . . 118.0 ?
C10 N2 H2 . . 118.0 ?
N1 C5 C6 . . 123.07(10) ?
N1 C5 C4 . . 117.74(11) ?
C6 C5 C4 . . 119.16(11) ?
N1 C9 N2 . . 115.15(10) ?
N1 C9 C8 . . 125.05(10) ?
N2 C9 C8 . . 119.80(10) ?
C15 C16 C10 . . 117.34(11) ?
C15 C16 C17 . . 122.02(12) ?
C10 C16 C17 . . 120.64(11) ?
O1 C12 C11 . . 121.25(11) ?
O1 C12 C8 . . 122.72(11) ?
C11 C12 C8 . . 116.02(9) ?
N2 C10 C11 . . 119.27(10) ?
N2 C10 C16 . . 119.86(11) ?
C11 C10 C16 . . 120.87(11) ?
C16 C15 C14 . . 122.47(12) ?
C16 C15 H15 . . 118.8 ?
C14 C15 H15 . . 118.8 ?
C20 C19 C18 . . 120.20(13) ?
C20 C19 H19 . . 119.9 ?
C18 C19 H19 . . 119.9 ?
C23 C18 C19 . . 119.24(11) ?
C23 C18 C7 . . 121.22(11) ?
C19 C18 C7 . . 119.52(10) ?
C14 C13 C11 . . 120.42(12) ?
C14 C13 H13 . . 119.8 ?
C11 C13 H13 . . 119.8 ?
C2 C1 C6 . . 119.61(12) ?
C2 C1 H1 . . 120.2 ?
C6 C1 H1 . . 120.2 ?
C3 C4 C5 . . 120.95(12) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C22 C23 C18 . . 120.35(13) ?
C22 C23 H23 . . 119.8 ?
C18 C23 H23 . . 119.8 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C1 C2 C3 . . 122.28(12) ?
C1 C2 Cl1 . . 119.20(11) ?
C3 C2 Cl1 . . 118.51(10) ?
C21 C20 C19 . . 120.08(13) ?
C21 C20 H20 . . 120.0 ?
C19 C20 H20 . . 120.0 ?
C22 C21 C20 . . 120.06(13) ?
C22 C21 H21 . . 120.0 ?
C20 C21 H21 . . 120.0 ?
C13 C14 C15 . . 119.50(12) ?
C13 C14 H14 . . 120.3 ?
C15 C14 H14 . . 120.3 ?
C21 C22 C23 . . 120.02(14) ?
C21 C22 H22 . . 120.0 ?
C23 C22 H22 . . 120.0 ?
C4 C3 C2 . . 119.20(12) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 . 1.7392(14) ?
C8 C7 . 1.3899(15) ?
C8 C9 . 1.4256(14) ?
C8 C12 . 1.4816(15) ?
N1 C9 . 1.3196(14) ?
N1 C5 . 1.3551(15) ?
C6 C5 . 1.4187(16) ?
C6 C1 . 1.4210(16) ?
C6 C7 . 1.4223(15) ?
C7 C18 . 1.4873(15) ?
C11 C10 . 1.3965(16) ?
C11 C13 . 1.3971(16) ?
C11 C12 . 1.4697(16) ?
N2 C9 . 1.3681(15) ?
N2 C10 . 1.3741(15) ?
N2 H2 . 0.8600 ?
C5 C4 . 1.4197(16) ?
O1 C12 . 1.2240(14) ?
C16 C15 . 1.3780(18) ?
C16 C10 . 1.4126(16) ?
C16 C17 . 1.4970(18) ?
C15 C14 . 1.393(2) ?
C15 H15 . 0.9300 ?
C19 C20 . 1.3828(18) ?
C19 C18 . 1.3863(17) ?
C19 H19 . 0.9300 ?
C18 C23 . 1.3859(18) ?
C13 C14 . 1.3690(19) ?
C13 H13 . 0.9300 ?
C1 C2 . 1.3598(18) ?
C1 H1 . 0.9300 ?
C4 C3 . 1.362(2) ?
C4 H4 . 0.9300 ?
C23 C22 . 1.3824(19) ?
C23 H23 . 0.9300 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C2 C3 . 1.404(2) ?
C20 C21 . 1.379(2) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.376(2) ?
C21 H21 . 0.9300 ?
C14 H14 . 0.9300 ?
C22 H22 . 0.9300 ?
C3 H3 . 0.9300 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 C8 C7 C6 . . . . 4.14(15) ?
C12 C8 C7 C6 . . . . -172.83(10) ?
C9 C8 C7 C18 . . . . -172.72(10) ?
C12 C8 C7 C18 . . . . 10.31(17) ?
C5 C6 C7 C8 . . . . -3.06(16) ?
C1 C6 C7 C8 . . . . 177.96(10) ?
C5 C6 C7 C18 . . . . 173.90(10) ?
C1 C6 C7 C18 . . . . -5.09(17) ?
C9 N1 C5 C6 . . . . 1.61(17) ?
C9 N1 C5 C4 . . . . 179.91(10) ?
C1 C6 C5 N1 . . . . 179.14(11) ?
C7 C6 C5 N1 . . . . 0.11(17) ?
C1 C6 C5 C4 . . . . 0.86(17) ?
C7 C6 C5 C4 . . . . -178.16(10) ?
C5 N1 C9 N2 . . . . -179.86(10) ?
C5 N1 C9 C8 . . . . -0.39(17) ?
C10 N2 C9 N1 . . . . 178.18(10) ?
C10 N2 C9 C8 . . . . -1.32(17) ?
C7 C8 C9 N1 . . . . -2.55(17) ?
C12 C8 C9 N1 . . . . 174.55(10) ?
C7 C8 C9 N2 . . . . 176.90(10) ?
C12 C8 C9 N2 . . . . -6.00(16) ?
C10 C11 C12 O1 . . . . 171.91(11) ?
C13 C11 C12 O1 . . . . -8.05(17) ?
C10 C11 C12 C8 . . . . -6.49(16) ?
C13 C11 C12 C8 . . . . 173.55(10) ?
C7 C8 C12 O1 . . . . 8.09(18) ?
C9 C8 C12 O1 . . . . -168.84(11) ?
C7 C8 C12 C11 . . . . -173.54(10) ?
C9 C8 C12 C11 . . . . 9.53(15) ?
C9 N2 C10 C11 . . . . 4.61(17) ?
C9 N2 C10 C16 . . . . -175.71(10) ?
C13 C11 C10 N2 . . . . 179.62(11) ?
C12 C11 C10 N2 . . . . -0.34(17) ?
C13 C11 C10 C16 . . . . -0.06(17) ?
C12 C11 C10 C16 . . . . 179.99(10) ?
C15 C16 C10 N2 . . . . 179.56(11) ?
C17 C16 C10 N2 . . . . -0.24(17) ?
C15 C16 C10 C11 . . . . -0.77(17) ?
C17 C16 C10 C11 . . . . 179.43(11) ?
C10 C16 C15 C14 . . . . 0.73(19) ?
C17 C16 C15 C14 . . . . -179.47(13) ?
C20 C19 C18 C23 . . . . 1.18(19) ?
C20 C19 C18 C7 . . . . 179.49(12) ?
C8 C7 C18 C23 . . . . -111.25(14) ?
C6 C7 C18 C23 . . . . 71.91(15) ?
C8 C7 C18 C19 . . . . 70.48(15) ?
C6 C7 C18 C19 . . . . -106.37(13) ?
C10 C11 C13 C14 . . . . 0.97(19) ?
C12 C11 C13 C14 . . . . -179.07(11) ?
C5 C6 C1 C2 . . . . -0.80(18) ?
C7 C6 C1 C2 . . . . 178.18(11) ?
N1 C5 C4 C3 . . . . -178.17(12) ?
C6 C5 C4 C3 . . . . 0.19(19) ?
C19 C18 C23 C22 . . . . -2.4(2) ?
C7 C18 C23 C22 . . . . 179.30(13) ?
C6 C1 C2 C3 . . . . -0.3(2) ?
C6 C1 C2 Cl1 . . . . -179.41(9) ?
C18 C19 C20 C21 . . . . 1.0(2) ?
C19 C20 C21 C22 . . . . -1.9(2) ?
C11 C13 C14 C15 . . . . -1.0(2) ?
C16 C15 C14 C13 . . . . 0.2(2) ?
C20 C21 C22 C23 . . . . 0.7(3) ?
C18 C23 C22 C21 . . . . 1.5(2) ?
C5 C4 C3 C2 . . . . -1.3(2) ?
C1 C2 C3 C4 . . . . 1.4(2) ?
Cl1 C2 C3 C4 . . . . -179.52(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745398
2 PubChem 139079198
