#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202125.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_2202125 loop_ _publ_author_name 'Cheng, Xin-Guo' 'Li, Yi-Zhi' 'Fu, Xing-Guo' 'Cao, Lei' 'Hu, Zhi-De' _publ_section_title ; 3-Carbazoyl-5-methylpyridazin-6(1H)-one ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o601 _journal_page_last o602 _journal_paper_doi 10.1107/S1600536803007165 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C6 H8 N4 O2' _chemical_formula_moiety 'C6 H8 N4 O2' _chemical_formula_sum 'C6 H8 N4 O2' _chemical_formula_weight 168.16 _chemical_name_systematic ; 3-Carbazoyl-5-methylpyridazin-6(1H)-one ; _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 _cell_angle_alpha 90.00 _cell_angle_beta 101.300(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.3590(10) _cell_length_b 10.2610(10) _cell_length_c 10.0050(10) _cell_measurement_reflns_used 2289 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.90 _cell_measurement_theta_min 2.87 _cell_volume 740.84(15) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 2000)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 3540 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.82 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.185 _refine_diff_density_min -0.313 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 110 _refine_ls_number_reflns 1288 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.089 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0394 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.05P)^2^+0.2P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1005 _refine_ls_wR_factor_ref 0.1024 _reflns_number_gt 1190 _reflns_number_total 1288 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6228.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2202125 _cod_database_fobs_code 2202125 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_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 _atom_site_type_symbol C1 0.6462(2) 1.10492(15) 0.93705(15) 0.0331(4) Uani d . 1 . . C C2 0.6365(2) 1.01960(15) 0.82030(15) 0.0335(4) Uani d . 1 . . C C3 0.7220(2) 0.90300(16) 0.83869(14) 0.0330(4) Uani d . 1 . . C H3 0.7144 0.8457 0.7658 0.040 Uiso calc R 1 . . H C4 0.82370(19) 0.86762(14) 0.96930(14) 0.0294(4) Uani d . 1 . . C C5 0.9347(2) 0.74530(14) 0.99118(14) 0.0309(4) Uani d . 1 . . C C6 0.5319(3) 1.06692(19) 0.68705(17) 0.0518(5) Uani d . 1 . . C H6A 0.5947 1.1406 0.6581 0.078 Uiso calc R 1 . . H H6B 0.4094 1.0922 0.6963 0.078 Uiso calc R 1 . . H H6C 0.5240 0.9986 0.6206 0.078 Uiso calc R 1 . . H N1 0.74384(17) 1.05510(12) 1.05700(12) 0.0332(3) Uani d . 1 . . N H1 0.7475 1.1025 1.1284 0.040 Uiso d R 1 . . H N2 0.83389(17) 0.94146(12) 1.07576(12) 0.0317(3) Uani d . 1 . . N N3 1.00494(19) 0.71739(13) 1.12063(12) 0.0380(4) Uani d . 1 . . N H3A 0.9698 0.7623 1.1836 0.046 Uiso d R 1 . . H N4 1.1351(2) 0.61732(13) 1.15884(13) 0.0418(4) Uani d . 1 . . N H4A 1.0803 0.5406 1.1383 0.063 Uiso d R 1 . . H H4C 1.2273 0.6266 1.1138 0.063 Uiso d R 1 . . H O1 0.57526(16) 1.21336(11) 0.93482(12) 0.0454(3) Uani d . 1 . . O O2 0.96260(16) 0.67886(11) 0.89503(11) 0.0419(3) Uani d . 1 . . O loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0318(8) 0.0322(9) 0.0356(8) -0.0042(6) 0.0072(6) 0.0007(6) C2 0.0347(8) 0.0364(9) 0.0285(8) -0.0040(7) 0.0041(6) 0.0024(6) C3 0.0391(8) 0.0342(9) 0.0256(8) -0.0042(7) 0.0062(6) -0.0026(6) C4 0.0323(8) 0.0305(8) 0.0256(7) -0.0052(6) 0.0061(6) -0.0004(6) C5 0.0386(8) 0.0286(8) 0.0257(8) -0.0058(6) 0.0067(6) 0.0004(6) C6 0.0660(12) 0.0495(11) 0.0353(9) 0.0054(9) -0.0014(8) 0.0059(8) N1 0.0394(7) 0.0314(7) 0.0282(7) 0.0001(5) 0.0050(5) -0.0068(5) N2 0.0354(7) 0.0310(7) 0.0284(7) -0.0026(5) 0.0051(5) -0.0010(5) N3 0.0525(8) 0.0357(8) 0.0258(7) 0.0094(6) 0.0077(6) 0.0023(5) N4 0.0569(9) 0.0336(8) 0.0334(7) 0.0083(6) 0.0054(6) 0.0069(6) O1 0.0493(7) 0.0344(7) 0.0509(7) 0.0067(5) 0.0060(5) -0.0015(5) O2 0.0611(8) 0.0348(6) 0.0288(6) 0.0063(5) 0.0062(5) -0.0022(5) 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 O1 C1 N1 120.13(14) O1 C1 C2 125.38(14) N1 C1 C2 114.50(13) C3 C2 C1 118.56(13) C3 C2 C6 124.00(15) C1 C2 C6 117.44(15) C2 C3 C4 120.03(14) C2 C3 H3 120.0 C4 C3 H3 120.0 N2 C4 C3 122.79(14) N2 C4 C5 115.44(12) C3 C4 C5 121.70(13) O2 C5 N3 123.44(14) O2 C5 C4 121.55(13) N3 C5 C4 114.97(13) C2 C6 H6A 109.5 C2 C6 H6B 109.5 H6A C6 H6B 109.5 C2 C6 H6C 109.5 H6A C6 H6C 109.5 H6B C6 H6C 109.5 N2 N1 C1 127.49(12) N2 N1 H1 116.3 C1 N1 H1 116.2 C4 N2 N1 116.56(12) C5 N3 N4 122.48(13) C5 N3 H3A 118.9 N4 N3 H3A 118.6 N3 N4 H4A 109.2 N3 N4 H4C 109.3 H4A N4 H4C 109.5 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 C1 O1 . 1.2275(19) yes C1 N1 . 1.3711(19) yes C1 C2 . 1.450(2) yes C2 C3 . 1.348(2) yes C2 C6 . 1.484(2) ? C3 C4 . 1.420(2) yes C3 H3 . 0.9300 ? C4 N2 . 1.2972(19) yes C4 C5 . 1.490(2) yes C5 O2 . 1.2286(18) yes C5 N3 . 1.3281(19) yes C6 H6A . 0.9600 ? C6 H6B . 0.9600 ? C6 H6C . 0.9600 ? N1 N2 . 1.3362(18) yes N1 H1 . 0.8600 ? N3 N4 . 1.4054(19) yes N3 H3A . 0.8600 ? N4 H4A . 0.8900 ? N4 H4C . 0.8900 ? 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 N1 H1 N4 2_757 0.86 2.14 2.8794(17) 144 N3 H3A O2 4_576 0.86 2.21 3.0171(17) 156 N4 H4A O2 3_767 0.89 2.29 3.1452(19) 161 N4 H4C O1 3_777 0.89 2.31 3.037(2) 139 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 2288586 2 PubChem 3021998