#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/22/2012266.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_2012266 loop_ _publ_author_name 'Bruno, Giuseppe' 'Nicol\'o, Francesco' 'Rotondo, Archimede' 'Gitto, Rosaria' 'Zappal\'a, Maria' _publ_section_title ; 4,5-Dihydro-7,8-dimethoxy-1-phenyl-3H-2,3-benzodiazepin-4-one ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1225 _journal_page_last 1227 _journal_paper_doi 10.1107/S0108270101011805 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C17 H16 N2 O3' _chemical_formula_sum 'C17 H16 N2 O3' _chemical_formula_weight 296.32 _chemical_name_common 'Ortho dimethoxybenzo-phenyldiazotropone' _chemical_name_systematic ; 4,5-Dihydro-7,8-dimethoxy-1-phenyl-3H-2,3-benzodiazepin-4-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' _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 95.600(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.207(2) _cell_length_b 10.312(2) _cell_length_c 17.236(2) _cell_measurement_reflns_used 30 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 13.8 _cell_measurement_theta_min 6.43 _cell_volume 1451.7(5) _computing_cell_refinement P3/V _computing_data_collection 'P3/V (Siemens, 1989)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1990)' _computing_molecular_graphics 'XPW (Siemens, 1996)' _computing_publication_material 'PARST97 (Nardelli, 1995) and SHELXL97' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .008 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 2903 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 25.1 _diffrn_reflns_theta_min 2.3 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 197 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .094 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 624 _exptl_crystal_size_max .26 _exptl_crystal_size_mid .24 _exptl_crystal_size_min .12 _refine_diff_density_max .16 _refine_diff_density_min -.15 _refine_ls_extinction_coef .0045(9) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref .839 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 204 _refine_ls_number_reflns 2567 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .839 _refine_ls_R_factor_all .051 _refine_ls_R_factor_gt .032 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0519P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .080 _reflns_number_gt 1734 _reflns_number_total 2567 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gg1067.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 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 2012266 _cod_database_fobs_code 2012266 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_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 .44184(17) .62315(14) .58707(9) .0392(4) Uani d . 1 . . C O1 .56570(12) .64626(10) .55456(7) .0502(3) Uani d . 1 . . O N2 .33046(15) .53575(13) .55707(9) .0431(4) Uani d . 1 . . N H2 .360(2) .4848(18) .5208(11) .066(6) Uiso d . 1 . . H N3 .19281(14) .48951(12) .58928(8) .0418(3) Uani d . 1 . . N C4 .09083(17) .56974(14) .61556(9) .0349(4) Uani d . 1 . . C C5 .10517(16) .71263(13) .61856(8) .0324(3) Uani d . 1 . . C C6 .25402(16) .77126(14) .64210(8) .0329(3) Uani d . 1 . . C C7 .40348(16) .68860(15) .66093(9) .0398(4) Uani d . 1 . . C H7A .4951 .7419 .6814 .048 Uiso calc R 1 . . H H7B .383 .6243 .6999 .048 Uiso calc R 1 . . H C8 .26573(16) .90642(14) .64534(8) .0360(4) Uani d . 1 . . C H8 .3653 .9453 .662 .043 Uiso calc R 1 . . H C9 .13049(17) .98247(13) .62402(8) .0344(4) Uani d . 1 . . C C10 -.01944(15) .92377(14) .59857(8) .0318(3) Uani d . 1 . . C C11 -.03263(16) .79086(14) .59738(8) .0332(3) Uani d . 1 . . C H11 -.1333 .7523 .5825 .04 Uiso calc R 1 . . H C12 -.05541(16) .50662(13) .64471(9) .0361(4) Uani d . 1 . . C C13 -.11398(19) .38906(15) .61385(10) .0489(4) Uani d . 1 . . C H13 -.0617 .3488 .5748 .059 Uiso calc R 1 . . H C14 -.2495(2) .33216(17) .64108(12) .0632(5) Uani d . 1 . . C H14 -.2881 .2537 .62 .076 Uiso calc R 1 . . H C15 -.3284(2) .38962(17) .69880(11) .0574(5) Uani d . 1 . . C H15 -.4208 .3511 .7161 .069 Uiso calc R 1 . . H C16 -.26981(19) .50438(16) .73070(10) .0478(4) Uani d . 1 . . C H16 -.3209 .543 .7707 .057 Uiso calc R 1 . . H C17 -.13526(17) .56232(15) .70350(9) .0401(4) Uani d . 1 . . C H17 -.0972 .6406 .7251 .048 Uiso calc R 1 . . H O2 .12966(12) 1.11411(10) .62487(7) .0481(3) Uani d . 1 . . O C18 .27701(19) 1.17974(16) .65132(10) .0524(4) Uani d . 1 . . C H18A .259 1.2717 .6488 .079 Uiso calc R 1 . . H H18B .3611 1.1569 .6188 .079 Uiso calc R 1 . . H H18C .3105 1.155 .7042 .079 Uiso calc R 1 . . H O3 -.14385(11) 1.00856(9) .57731(6) .0418(3) Uani d . 1 . . O C19 -.30176(18) .95579(17) .55732(11) .0521(5) Uani d . 1 . . C H19A -.3779 1.0247 .5436 .078 Uiso calc R 1 . . H H19B -.336 .9088 .601 .078 Uiso calc R 1 . . H H19C -.2985 .8981 .5138 .078 Uiso calc R 1 . . H 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 .0325(8) .0317(9) .0543(10) .0061(7) .0089(7) .0012(7) O1 .0402(6) .0439(7) .0694(8) -.0028(5) .0198(5) -.0096(6) N2 .0391(7) .0366(8) .0565(9) -.0011(6) .0189(6) -.0107(7) N3 .0386(7) .0325(7) .0563(9) .0015(6) .0153(6) -.0026(6) C4 .0346(8) .0303(8) .0400(9) .0016(7) .0048(6) -.0014(7) C5 .0327(7) .0285(8) .0371(8) .0009(6) .0089(6) -.0010(7) C6 .0325(8) .0320(8) .0350(8) .0035(6) .0071(6) -.0019(7) C7 .0339(8) .0373(9) .0484(10) .0050(7) .0044(7) -.0028(7) C8 .0303(8) .0355(9) .0423(9) -.0029(6) .0045(6) -.0052(7) C9 .0374(8) .0266(8) .0399(9) .0002(6) .0076(7) -.0006(7) C10 .0296(7) .0318(8) .0346(8) .0035(6) .0061(6) .0016(6) C11 .0278(7) .0331(8) .0391(8) -.0023(6) .0055(6) -.0014(7) C12 .0346(8) .0285(8) .0451(9) .0018(6) .0039(7) .0052(7) C13 .0502(9) .0319(9) .0657(11) -.0016(8) .0117(8) -.0032(8) C14 .0595(11) .0369(10) .0941(15) -.0148(9) .0118(10) .0001(10) C15 .0476(10) .0467(11) .0797(14) -.0067(9) .0158(9) .0193(10) C16 .0443(9) .0513(11) .0494(11) .0034(8) .0126(8) .0121(8) C17 .0385(8) .0376(9) .0444(9) .0007(7) .0049(7) .0007(7) O2 .0446(6) .0258(6) .0725(8) -.0016(5) -.0011(5) -.0018(5) C18 .0522(10) .0334(9) .0703(12) -.0088(8) -.0006(8) -.0044(9) O3 .0332(5) .0333(6) .0583(7) .0049(5) .0008(5) .0039(5) C19 .0348(8) .0514(11) .0678(12) .0046(8) -.0058(8) -.0032(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .006 '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 _geom_angle_publ_flag O1 C1 N2 120.90(10) yes O1 C1 C7 123.40(10) yes N2 C1 C7 115.80(10) ? C1 N2 N3 128.50(10) yes C1 N2 H2 117.0(10) no N3 N2 H2 112.0(10) no N2 N3 C4 120.00(10) yes N3 C4 C5 126.80(10) yes N3 C4 C12 114.10(10) ? C5 C4 C12 119.10(10) ? C6 C5 C11 119.22(13) ? C4 C5 C6 120.60(10) yes C11 C5 C4 120.18(13) ? C5 C6 C8 120.08(13) ? C5 C6 C7 119.50(10) yes C8 C6 C7 120.36(13) ? C1 C7 C6 107.80(10) ? C1 C7 H7A 110.1 ? C6 C7 H7A 110.1 ? C1 C7 H7B 110.1 ? C6 C7 H7B 110.1 ? H7A C7 H7B 108.5 ? C9 C8 C6 120.39(13) ? C9 C8 H8 119.8 ? C6 C8 H8 119.8 ? O2 C9 C8 124.78(13) ? O2 C9 C10 115.45(12) ? C8 C9 C10 119.77(13) ? O3 C10 C11 125.31(12) ? O3 C10 C9 114.67(12) ? C11 C10 C9 120.01(13) ? C10 C11 C5 120.48(13) ? C10 C11 H11 119.8 ? C5 C11 H11 119.8 ? C17 C12 C13 118.11(14) ? C17 C12 C4 121.23(13) ? C13 C12 C4 120.66(14) ? C14 C13 C12 120.04(16) ? C14 C13 H13 120 ? C12 C13 H13 120 ? C15 C14 C13 121.04(17) ? C15 C14 H14 119.5 ? C13 C14 H14 119.5 ? C16 C15 C14 119.39(16) ? C16 C15 H15 120.3 ? C14 C15 H15 120.3 ? C15 C16 C17 119.95(16) ? C15 C16 H16 120 ? C17 C16 H16 120 ? C16 C17 C12 121.45(15) ? C16 C17 H17 119.3 ? C12 C17 H17 119.3 ? C9 O2 C18 118.30(10) yes O2 C18 H18A 109.5 ? O2 C18 H18B 109.5 ? H18A C18 H18B 109.5 ? O2 C18 H18C 109.5 ? H18A C18 H18C 109.5 ? H18B C18 H18C 109.5 ? C10 O3 C19 117.50(10) yes O3 C19 H19A 109.5 ? O3 C19 H19B 109.5 ? H19A C19 H19B 109.5 ? O3 C19 H19C 109.5 ? H19A C19 H19C 109.5 ? H19B C19 H19C 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 . 1.231(2) yes C1 N2 . 1.350(2) yes C1 C7 . 1.501(2) yes N2 N3 . 1.391(2) yes N3 C4 . 1.290(2) yes C4 C5 . 1.479(2) yes C4 C12 . 1.495(2) no C5 C6 . 1.388(2) yes C5 C11 . 1.4080(19) ? C6 C8 . 1.398(2) ? C6 C7 . 1.503(2) yes C8 C9 . 1.3793(19) ? O2 C9 . 1.358(2) yes O3 C10 . 1.367(2) yes O2 C18 . 1.421(2) yes O3 C19 . 1.417(2) yes C9 C10 . 1.4027(19) ? C10 C11 . 1.375(2) ? C12 C17 . 1.384(2) ? C12 C13 . 1.391(2) ? C13 C14 . 1.380(2) ? C14 C15 . 1.373(2) ? C15 C16 . 1.372(2) ? C16 C17 . 1.377(2) ? N2 H2 . .87(2) ? C7 H7A . .97 ? C7 H7B . .97 ? C8 H8 . .93 ? C11 H11 . .93 ? C13 H13 . .93 ? C14 H14 . .93 ? C15 H15 . .93 ? C16 H16 . .93 ? C17 H17 . .93 ? C18 H18A . .96 ? C18 H18B . .96 ? C18 H18C . .96 ? C19 H19A . .96 ? C19 H19B . .96 ? C19 H19C . .96 ? 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 N2 H2 O1 3_666 .87(2) 2.01(2) 2.876(2) 174(2) C18 H18A N3 1_565 .96 2.51 3.418(2) 158 C13 H13 N3 . .93 2.54 2.793(2) 96 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 _geom_torsion_publ_flag O1 C1 N2 N3 173.64(14) ? C7 C1 N2 N3 -6.6(2) ? C1 N2 N3 C4 50.0(2) ? N2 N3 C4 C5 -2.5(2) ? N2 N3 C4 C12 177.05(13) ? N3 C4 C5 C6 -42.8(2) ? C12 C4 C5 C6 137.75(14) ? N3 C4 C5 C11 137.15(16) ? C12 C4 C5 C11 -42.3(2) ? C11 C5 C6 C8 .6(2) ? C4 C5 C6 C8 -179.45(14) ? C11 C5 C6 C7 -176.94(12) ? C4 C5 C6 C7 3.0(2) ? O1 C1 C7 C6 113.45(16) ? N2 C1 C7 C6 -66.28(17) yes C5 C6 C7 C1 65.53(17) ? C8 C6 C7 C1 -112.03(15) ? C5 C6 C8 C9 -1.1(2) ? C7 C6 C8 C9 176.48(13) ? C6 C8 C9 O2 -179.73(14) ? C6 C8 C9 C10 -.3(2) ? O2 C9 C10 O3 .88(19) ? C8 C9 C10 O3 -178.59(12) ? O2 C9 C10 C11 -178.38(13) ? C8 C9 C10 C11 2.2(2) ? O3 C10 C11 C5 178.23(13) ? C9 C10 C11 C5 -2.6(2) ? C6 C5 C11 C10 1.2(2) ? C4 C5 C11 C10 -178.71(13) ? N3 C4 C12 C17 150.78(14) ? C5 C4 C12 C17 -29.7(2) yes N3 C4 C12 C13 -28.5(2) ? C5 C4 C12 C13 151.02(15) ? C17 C12 C13 C14 1.0(2) ? C4 C12 C13 C14 -179.72(15) ? C12 C13 C14 C15 -.2(3) ? C13 C14 C15 C16 -1.1(3) ? C14 C15 C16 C17 1.5(3) ? C15 C16 C17 C12 -.7(2) ? C13 C12 C17 C16 -.5(2) ? C4 C12 C17 C16 -179.83(13) ? C8 C9 O2 C18 -1.6(2) yes C10 C9 O2 C18 178.95(13) ? C11 C10 O3 C19 4.4(2) yes C9 C10 O3 C19 -174.81(13) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 8036671 2 PubChem 9860972