#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/03/2010315.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_2010315 loop_ _publ_author_name 'Ianelli, Sandra' 'Nardelli, Mario' 'Belletti, Daniele' 'Caub\`ere, Caterine' 'Caub\`ere, Paul' 'Jamart-Gr\'egoire, Brigitte' _publ_section_title ; 1,2-Dihydro-8-methyl-4(3H)-carbazolone prepared by a new arynic cyclization reaction ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1919 _journal_page_last 1922 _journal_paper_doi 10.1107/S0108270194002611 _journal_volume 50 _journal_year 1994 _chemical_formula_analytical 'C13 H13 N O' _chemical_formula_sum 'C13 H13 N O' _chemical_formula_weight 199.25 _chemical_name_systematic ; 1,2-Dihydro-8-methyl-9H-carbazol-4(3H)-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90. _cell_angle_beta 105.29(3) _cell_angle_gamma 90. _cell_formula_units_Z 4 _cell_length_a 13.706(6) _cell_length_b 9.908(4) _cell_length_c 8.126(3) _cell_measurement_reflns_used 29 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 45 _cell_measurement_theta_min 25 _cell_volume 1064.4(8) _computing_cell_refinement 'LQPARM (Nardelli & Mangia, 1984)' _computing_data_collection 'local programs' _computing_data_reduction 'local programs' _computing_molecular_graphics ORTEP _computing_publication_material ; PARST (Nardelli, 1983); PARSTCIF (Nardelli, 1991) ; _computing_structure_refinement 'SHELXL93 (Sheldrick, 1994)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Siemens-AED diffractometer' _diffrn_measurement_method \q-2\q _diffrn_radiation_monochromator Ni-filter _diffrn_radiation_source 'fine focus sealed X-ray tube' _diffrn_radiation_type 'Cu K-\a~1~' _diffrn_radiation_wavelength 1.5405620 _diffrn_reflns_av_R_equivalents 0.0675 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 3916 _diffrn_reflns_reduction_process ; Standard Lp correction. ; _diffrn_reflns_theta_max 70.49 _diffrn_reflns_theta_min 5.58 _diffrn_standards_decay_% 'within statistical fluctuation' _diffrn_standards_interval_count 50 _diffrn_standards_number 1 _exptl_absorpt_coefficient_mu 0.622 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_meas ? _exptl_crystal_description ; small prisms ; _exptl_crystal_F_000 424 _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.29 _refine_diff_density_max 0.278 _refine_diff_density_min -0.215 _refine_ls_extinction_coef 0.010(3) _refine_ls_extinction_method 'F~c~^*^ = kF~c~[1+0.001xF~c~^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_goodness_of_fit_all 1.074 _refine_ls_goodness_of_fit_obs 1.114 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 189 _refine_ls_number_reflns 1988 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.434 _refine_ls_restrained_S_obs 1.114 _refine_ls_R_factor_all 0.1160 _refine_ls_R_factor_obs 0.0830 _refine_ls_shift/esd_max 0.011 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ;calc w = 1/[\s^2^(F~o~^2^)+(0.1742P)^2^+0.2112P] where P = (F~o~^2^+2F~c~^2^)/3 ; _refine_ls_wR_factor_all 0.3721 _refine_ls_wR_factor_obs 0.2314 _reflns_number_observed 1317 _reflns_number_total 2025 _reflns_observed_criterion I>2\s(I) _cod_data_source_file li1111.cif _cod_data_source_block 2CC1dat _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2010315 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' 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 N1 0.0696(17) 0.0505(12) 0.0765(14) 0.0036(10) -0.0253(12) -0.0015(10) O1 0.0734(16) 0.0781(16) 0.1158(19) 0.0147(13) -0.0347(13) 0.0064(11) C1 0.0679(18) 0.0503(14) 0.0657(14) -0.0010(11) -0.0205(12) -0.0011(11) C2 0.074(2) 0.0613(16) 0.0713(16) 0.0071(12) -0.0178(14) 0.0027(13) C3 0.084(3) 0.069(2) 0.111(3) 0.0312(19) -0.016(2) 0.0051(16) C4 0.089(3) 0.0521(17) 0.135(3) 0.0162(18) -0.009(2) -0.0032(16) C5 0.081(2) 0.0579(17) 0.107(3) 0.0138(16) -0.022(2) -0.0106(15) C6 0.0706(19) 0.0509(15) 0.0691(15) 0.0023(11) -0.0181(13) -0.0041(11) C7 0.0703(18) 0.0457(13) 0.0643(14) -0.0033(10) -0.0170(12) -0.0003(11) C8 0.0656(18) 0.0483(14) 0.0634(14) -0.0050(10) -0.0165(12) -0.0003(10) C9 0.069(2) 0.0573(15) 0.0794(18) -0.0038(13) -0.0168(15) -0.0075(12) C10 0.085(2) 0.0562(16) 0.090(2) -0.0061(14) -0.0091(17) -0.0155(14) C11 0.094(3) 0.0457(14) 0.0824(19) -0.0038(12) -0.0070(16) -0.0021(13) C12 0.083(2) 0.0474(14) 0.0702(16) -0.0004(11) -0.0124(14) 0.0044(12) C13 0.089(3) 0.0624(19) 0.105(3) 0.0173(18) -0.011(2) 0.0133(16) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol N1 0.3825(2) 0.1382(2) 0.1005(3) 0.0740(9) aniso . . N O1 0.0753(2) 0.3105(2) -0.1900(3) 0.1004(11) aniso . . O C1 0.2332(2) 0.2279(3) -0.0386(3) 0.0685(9) aniso . . C C2 0.1668(3) 0.3310(3) -0.1274(4) 0.0760(11) aniso . . C C3 0.2136(3) 0.4655(4) -0.1442(6) 0.0957(16) aniso . . C C4 0.3139(3) 0.4930(4) -0.0205(6) 0.0994(17) aniso . . C C5 0.3886(3) 0.3795(3) 0.0082(6) 0.0906(14) aniso . . C C6 0.3363(2) 0.2512(3) 0.0247(3) 0.0704(10) aniso . . C C7 0.3103(2) 0.0380(2) 0.0910(3) 0.0667(11) aniso . . C C8 0.2151(2) 0.0912(3) 0.0033(3) 0.0654(11) aniso . . C C9 0.1292(3) 0.0084(3) -0.0248(4) 0.0755(11) aniso . . C C10 0.1426(3) -0.1227(3) 0.0316(4) 0.0833(14) aniso . . C C11 0.2374(3) -0.1737(3) 0.1169(4) 0.0798(12) aniso . . C C12 0.3240(3) -0.0953(3) 0.1479(4) 0.0730(11) aniso . . C C13 0.4269(3) -0.1491(4) 0.2372(6) 0.0924(16) aniso . . C H1N 0.450(3) 0.136(3) 0.170(4) 0.075(9) iso . N1 H H31 0.166(5) 0.531(5) -0.151(7) 0.145(19) iso . C3 H H32 0.229(4) 0.462(6) -0.268(7) 0.144(19) iso . C3 H H41 0.342(3) 0.582(5) -0.054(5) 0.105(12) iso . C4 H H42 0.305(5) 0.499(7) 0.110(9) 0.19(3) iso . C4 H H51 0.425(4) 0.373(5) -0.094(7) 0.15(2) iso . C5 H H52 0.451(3) 0.397(4) 0.101(5) 0.097(11) iso . C5 H H9 0.066(3) 0.044(4) -0.094(4) 0.078(9) iso . C9 H H10 0.082(3) -0.180(4) 0.016(5) 0.105(12) iso . C10 H H11 0.242(3) -0.281(4) 0.156(4) 0.079(9) iso . C11 H H131 0.472(4) -0.144(5) 0.169(7) 0.13(2) iso . C13 H H132 0.420(4) -0.235(5) 0.276(6) 0.128(16) iso . C13 H H133 0.450(4) -0.102(6) 0.364(8) 0.153(19) iso . C13 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'N ' 'Nitrogen ' 0.0311 0.0180 'Int. Tab. C, 4.2.6.8, 6.1.1.4' 'O ' 'Oxygen ' 0.0492 0.0322 'Int. Tab. C, 4.2.6.8, 6.1.1.4' 'C ' 'Carbon ' 0.0181 0.0091 'Int. Tab. C, 4.2.6.8, 6.1.1.4' 'H ' 'Hydrogen ' 0.0000 0.0000 'Int. Tab. C, 4.2.6.8, 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 6 1 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C7 N1 H1N 126(2) no C6 N1 H1N 124(2) no C6 N1 C7 108.9(2) no C6 C1 C8 106.9(3) no C2 C1 C8 131.8(3) no C2 C1 C6 121.2(3) no O1 C2 C1 122.1(3) no C1 C2 C3 116.7(3) no O1 C2 C3 121.3(3) no C2 C3 H32 104(3) no C2 C3 H31 109(3) no C2 C3 C4 116.1(3) no H31 C3 H32 106(5) no C4 C3 H32 105(3) no C4 C3 H31 115(4) no C3 C4 H42 110(4) no C3 C4 H41 109(2) no C3 C4 C5 115.8(4) no H41 C4 H42 111(4) no C5 C4 H42 98(4) no C5 C4 H41 113(3) no C4 C5 H52 113(2) no C4 C5 H51 111(3) no C4 C5 C6 109.4(3) no H51 C5 H52 97(4) no C6 C5 H52 115(2) no C6 C5 H51 111(3) no C1 C6 C5 125.3(3) no N1 C6 C5 124.8(2) no N1 C6 C1 109.9(3) no N1 C7 C12 128.8(2) no N1 C7 C8 108.1(3) no C8 C7 C12 123.1(2) no C1 C8 C7 106.1(2) no C7 C8 C9 119.2(3) no C1 C8 C9 134.8(3) no C8 C9 H9 118(2) no C8 C9 C10 117.8(3) no C10 C9 H9 124(2) no C9 C10 H10 118(2) no C9 C10 C11 122.2(3) no C11 C10 H10 120(3) no C10 C11 H11 118(2) no C10 C11 C12 121.9(3) no C12 C11 H11 120(2) no C7 C12 C11 115.9(3) no C11 C12 C13 122.6(3) no C7 C12 C13 121.5(3) no C12 C13 H133 108(3) no C12 C13 H132 109(3) no C12 C13 H131 112(3) no H132 C13 H133 96(4) no H131 C13 H133 118(4) no H131 C13 H132 114(4) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C6 1.352(3) no N1 C7 1.389(4) no N1 H1N 0.95(3) no O1 C2 1.239(4) no C1 C2 1.430(4) no C1 C6 1.389(4) no C1 C8 1.434(4) no C2 C3 1.501(5) no C3 C4 1.499(6) no C3 H31 0.92(5) no C3 H32 1.08(6) no C4 C5 1.497(5) no C4 H41 1.03(4) no C4 H42 1.10(7) no C5 C6 1.483(5) no C5 H51 1.08(6) no C5 H52 0.99(3) no C7 C8 1.414(4) no C7 C12 1.396(4) no C8 C9 1.403(4) no C9 C10 1.374(4) no C9 H9 0.96(3) no C10 C11 1.396(5) no C10 H10 0.98(4) no C11 C12 1.385(5) no C11 H11 1.11(3) no C12 C13 1.503(5) no C13 H131 0.94(6) no C13 H132 0.92(5) no C13 H133 1.10(5) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance N1 C1 2.244(4) N1 C5 2.513(4) N1 C8 2.270(4) N1 C12 2.512(4) O1 C1 2.338(4) O1 C3 2.391(5) C1 C3 2.495(5) C1 C4 2.838(5) C1 C5 2.550(5) C1 C7 2.276(4) C1 C9 2.619(4) C2 C4 2.545(5) C2 C5 2.987(5) C2 C6 2.457(4) C2 C8 2.615(4) C3 C5 2.538(6) C3 C6 2.829(5) C4 C6 2.431(4) C6 C7 2.231(4) C6 C8 2.269(4) C7 C9 2.429(5) C7 C10 2.733(5) C7 C11 2.357(4) C7 C13 2.530(5) C8 C10 2.378(4) C8 C11 2.773(4) C8 C12 2.470(4) C9 C11 2.425(4) C9 C12 2.860(5) C10 C12 2.431(5) C11 C13 2.534(6) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 11830419