#------------------------------------------------------------------------------ #$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012266.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_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 none _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) _[local]_cod_data_source_file gg1067.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P21/n _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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_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_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_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) ?