#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/53/2005329.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_2005329 loop_ _publ_author_name 'Baouid, A.' 'Hasnaoui, A.' 'Benharref, A.' 'Giorgi, M.' 'Pierrot, M.' _publ_contact_author ; M. Pierrot Laboratoire de Cristallochimie Facult\'e des Sciences et Techniques de Saint J\'er\^ome Avenue Escadrille Normandie Niemen 13397 Marseille Cedex 20 France ; _publ_section_title 1-(4-Chlorophenyl)-3a-methyl-5-phenyl-3a,4-dihydro-1,2,4-oxadiazolo[4,5-a][1,5]benzodiazepine _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2281 _journal_page_last 2282 _journal_volume 52 _journal_year 1996 _chemical_formula_sum 'C23 H18 Cl N3 O' _chemical_formula_weight 387.87 _chemical_name_systematic ' ?' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_type_scat_source IntTabIV _audit_creation_method from_MolEN_master_file_using_cif_in _cell_angle_alpha 90.0(2) _cell_angle_beta 98.4(3) _cell_angle_gamma 90.0(3) _cell_formula_units_Z 4.00 _cell_length_a 19.685(1) _cell_length_b 11.023(2) _cell_length_c 8.881(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294 _cell_measurement_theta_max 17 _cell_measurement_theta_min 14 _cell_volume 1906.4(16) _computing_cell_refinement CAD4 _computing_data_collection CAD4_(Enraf-Nonius,_1989) _computing_data_reduction BEGIN_SDP-Plus_(Frenz,_1985) _computing_molecular_graphics ORTEPII_(Johnson,_1976) _computing_publication_material CIF_VAX_MolEN_(Fair,_1990) _computing_structure_refinement LSFM_SDP-Plus _computing_structure_solution Direct_methods_MULTAN80_(Main_et_al.,_1980) _diffrn_ambient_temperature 294 _diffrn_measurement_device Enraf_Nonius_CAD4 _diffrn_measurement_method \q/2\q _diffrn_radiation_type Mo-K\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3008 _diffrn_reflns_theta_max 23.96 _diffrn_reflns_theta_min 1.05 _diffrn_standards_decay_% -0.92 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.35 _exptl_crystal_density_meas none _exptl_crystal_description cube _exptl_crystal_F_000 808 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _refine_diff_density_max 0.50 _refine_diff_density_min -0.24 _refine_ls_abs_structure_details ; ? ; _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.941 _refine_ls_hydrogen_treatment included_not_refined _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 1995 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.090 _refine_ls_R_factor_obs 0.045 _refine_ls_shift/esd_max 0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme '4Fo^2^/[\s^2^(Fo^2^) + 0.0016 Fo^4^]' _refine_ls_wR_factor_obs 0.056 _reflns_number_observed 1995 _reflns_number_total 2752 _reflns_observed_criterion >3.0\s(I) _[local]_cod_data_source_file bm1067.cif _[local]_cod_data_source_block BENHARREF1 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _[local]_cod_chemical_formula_sum_orig 'C23 H18 Cl1 N3 O1' _cod_original_cell_volume 1907(2) _cod_database_code 2005329 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 Cl 0.98072(4) 0.2467(1) 0.0485(1) 0.0912(3) Uani ? O3 1.34408(9) -0.0883(2) 0.2441(2) 0.0434(5) Uani ? N2 1.2891(1) -0.0133(2) 0.1713(2) 0.0402(6) Uani ? N6 1.2894(1) 0.1202(2) 0.5546(2) 0.0380(6) Uani ? N11 1.2555(1) -0.0964(2) 0.3798(2) 0.0338(5) Uani ? C1 1.2415(1) -0.0193(2) 0.2563(3) 0.0342(6) Uani ? C3a 1.3293(1) -0.1225(2) 0.3926(3) 0.0375(7) Uani ? C4 1.3709(1) -0.0408(2) 0.5142(3) 0.0397(7) Uani ? C5 1.3455(1) 0.0892(2) 0.5081(2) 0.0350(7) Uani ? C6a 1.2474(1) 0.0294(2) 0.6057(3) 0.0363(7) Uani ? C7 1.2202(1) 0.0477(2) 0.7392(3) 0.0478(8) Uani ? C8 1.1766(1) -0.0375(3) 0.7885(3) 0.0510(8) Uani ? C9 1.1593(1) -0.1412(3) 0.7051(3) 0.0507(8) Uani ? C10 1.1864(1) -0.1609(2) 0.5713(3) 0.0424(7) Uani ? C10a 1.2290(1) -0.0754(2) 0.5207(2) 0.0355(7) Uani ? C12 1.3463(1) -0.2555(2) 0.4181(3) 0.0492(8) Uani ? C13 1.3880(1) 0.1866(2) 0.4508(3) 0.0362(7) Uani ? C14 1.4406(1) 0.1608(3) 0.3686(3) 0.0496(8) Uani ? C15 1.4796(2) 0.2534(3) 0.3192(3) 0.062(1) Uani ? C16 1.4663(2) 0.3727(3) 0.3529(3) 0.0634(9) Uani ? C17 1.4137(2) 0.3998(3) 0.4327(3) 0.0586(9) Uani ? C18 1.3747(1) 0.3073(2) 0.4822(3) 0.0476(8) Uani ? C19 1.1767(1) 0.0460(2) 0.2119(3) 0.0378(7) Uani ? C20 1.1776(1) 0.1535(2) 0.1304(3) 0.0481(8) Uani ? C21 1.1176(2) 0.2153(3) 0.0795(3) 0.0565(9) Uani ? C22 1.0562(1) 0.1694(3) 0.1130(3) 0.0571(9) Uani ? C23 1.0539(2) 0.0636(3) 0.1943(4) 0.064(1) Uani ? C24 1.1142(1) 0.0020(3) 0.2448(3) 0.0536(8) Uani ? H1 1.4511 0.0725 0.3443 0.0642 Uiso calc H2 1.5185 0.2334 0.2580 0.0794 Uiso calc H3 1.4960 0.4405 0.3181 0.0827 Uiso calc H4 1.4034 0.4880 0.4561 0.0762 Uiso calc H5 1.3358 0.3282 0.5421 0.0614 Uiso calc H6 1.1747 -0.2384 0.5101 0.0543 Uiso calc H7 1.1272 -0.2040 0.7414 0.0656 Uiso calc H8 1.1571 -0.0244 0.8874 0.0663 Uiso calc H9 1.2233 0.1870 0.1075 0.0628 Uiso calc H10 1.1184 0.2935 0.0187 0.0738 Uiso calc H11 1.0079 0.0301 0.2176 0.0821 Uiso calc H12 1.1129 -0.0763 0.3061 0.0693 Uiso calc H13 1.3669 -0.0757 0.6191 0.0515 Uiso calc H14 1.4209 -0.0416 0.4975 0.0515 Uiso calc H15 1.3177 -0.3059 0.3352 0.0639 Uiso calc H16 1.3971 -0.2691 0.4136 0.0639 Uiso calc H17 1.3351 -0.2813 0.5219 0.0639 Uiso calc H18 1.2324 0.1237 0.8014 0.0622 Uiso calc 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 Cl 0.0558(6) 0.1117(7) 0.1051(6) 0.0318(5) 0.0086(5) 0.0273(6) O3 0.0460(10) 0.0460(10) 0.0410(8) 0.0069(9) 0.0160(7) 0.0020(8) N2 0.0440(10) 0.0390(10) 0.0390(10) 0.0040(10) 0.0086(9) 0.0030(10) N6 0.0370(10) 0.0390(10) 0.0400(10) -0.0025(9) 0.0132(9) -0.0045(9) N11 0.0330(10) 0.0360(10) 0.0329(9) -0.0012(9) 0.0068(8) 0.0001(9) C1 0.0380(10) 0.0310(10) 0.0340(10) -0.0040(10) 0.0070(10) -0.0030(10) C3a 0.0400(10) 0.0340(10) 0.0410(10) 0.0020(10) 0.0120(10) 0.0010(10) C4 0.0340(10) 0.0380(10) 0.0460(10) 0.0020(10) 0.0040(10) -0.0010(10) C5 0.0370(10) 0.0350(10) 0.0330(10) -0.0010(10) 0.0030(10) -0.0040(10) C6a 0.0350(10) 0.0380(10) 0.0380(10) 0.0000(10) 0.0100(10) -0.0020(10) C7 0.050(2) 0.052(2) 0.0430(10) 0.0010(10) 0.0140(10) -0.0050(10) C8 0.053(2) 0.064(2) 0.0390(10) -0.0030(10) 0.0170(10) 0.0010(10) C9 0.049(2) 0.063(2) 0.0420(10) -0.0080(10) 0.0110(10) 0.0110(10) C10 0.043(2) 0.0440(10) 0.0400(10) -0.0080(10) 0.0060(10) 0.0020(10) C10a 0.0340(10) 0.0420(10) 0.0310(10) 0.0000(10) 0.0060(10) 0.0030(10) C12 0.058(2) 0.0350(10) 0.057(2) 0.0060(10) 0.0140(10) 0.0000(10) C13 0.0290(10) 0.0410(10) 0.0370(10) -0.0020(10) 0.0010(10) -0.0020(10) C14 0.044(2) 0.052(2) 0.0550(10) -0.0040(10) 0.0140(10) -0.0030(10) C15 0.051(2) 0.076(2) 0.061(2) -0.010(2) 0.0180(10) 0.004(2) C16 0.058(2) 0.068(2) 0.062(2) -0.022(2) 0.0010(10) 0.017(2) C17 0.059(2) 0.043(2) 0.072(2) -0.0080(10) 0.0050(10) 0.007(2) C18 0.045(2) 0.0400(10) 0.0570(10) -0.0020(10) 0.0050(10) -0.0030(10) C19 0.0390(10) 0.0410(10) 0.0350(10) -0.0040(10) 0.0070(10) -0.0050(10) C20 0.046(2) 0.044(2) 0.0550(10) 0.0010(10) 0.0100(10) 0.0080(10) C21 0.050(2) 0.053(2) 0.068(2) 0.0090(10) 0.0130(10) 0.0140(10) C22 0.043(2) 0.067(2) 0.061(2) 0.0100(10) 0.0030(10) 0.004(2) C23 0.044(2) 0.077(2) 0.070(2) 0.001(2) 0.0040(10) 0.020(2) C24 0.044(2) 0.057(2) 0.060(2) -0.0040(10) 0.0060(10) 0.0140(10) 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 N2 O3 C3a 108.8(2) yes O3 N2 C1 105.7(2) yes C5 N6 C6a 119.1(2) yes C1 N11 C3a 105.2(2) yes C1 N11 C10a 122.2(2) yes C3a N11 C10a 116.3(2) yes N2 C1 N11 114.7(2) yes N2 C1 C19 119.7(2) yes N11 C1 C19 125.4(2) yes O3 C3a N11 102.0(2) ? O3 C3a C4 109.3(2) ? O3 C3a C12 108.7(2) ? N11 C3a C4 110.9(2) ? N11 C3a C12 113.3(2) ? C4 C3a C12 112.1(2) ? C3a C4 C5 112.8(2) ? N6 C5 C4 122.4(2) ? N6 C5 C13 118.0(2) ? C4 C5 C13 119.6(2) ? N6 C6a C7 119.2(2) ? N6 C6a C10a 121.9(2) ? C7 C6a C10a 118.7(2) ? C6a C7 C8 120.4(2) ? C7 C8 C9 120.5(3) ? C8 C9 C10 119.7(3) ? C9 C10 C10a 120.0(2) ? N11 C10a C6a 120.2(2) ? N11 C10a C10 119.1(2) ? C6a C10a C10 120.7(2) ? C5 C13 C14 122.1(2) ? C5 C13 C18 119.2(2) ? C14 C13 C18 118.7(2) ? C13 C14 C15 120.6(3) ? C14 C15 C16 120.0(3) ? C15 C16 C17 120.0(3) ? C16 C17 C18 119.9(3) ? C13 C18 C17 120.7(3) ? C1 C19 C20 118.7(2) ? C1 C19 C24 122.2(2) ? C20 C19 C24 119.1(2) ? C19 C20 C21 121.0(3) ? C20 C21 C22 118.8(3) ? Cl C22 C21 118.8(2) ? Cl C22 C23 119.8(2) ? C21 C22 C23 121.4(3) ? C22 C23 C24 119.5(3) ? C19 C24 C23 120.2(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl C22 1.736(3) ? O3 N2 1.439(3) yes O3 C3a 1.441(3) yes N2 C1 1.287(3) yes N6 C5 1.281(3) yes N6 C6a 1.415(3) yes N11 C1 1.383(3) yes N11 C3a 1.469(3) yes N11 C10a 1.443(3) yes C1 C19 1.468(3) ? C3a C4 1.546(3) ? C3a C12 1.513(4) ? C4 C5 1.516(3) ? C5 C13 1.494(4) ? C6a C7 1.385(4) ? C6a C10a 1.398(3) ? C7 C8 1.386(4) ? C8 C9 1.377(4) ? C9 C10 1.388(4) ? C10 C10a 1.379(4) ? C13 C14 1.380(4) ? C13 C18 1.392(4) ? C14 C15 1.387(4) ? C15 C16 1.383(5) ? C16 C17 1.370(5) ? C17 C18 1.386(4) ? C19 C20 1.390(4) ? C19 C24 1.391(4) ? C20 C21 1.382(4) ? C21 C22 1.382(4) ? C22 C23 1.376(4) ? C23 C24 1.385(4) ? _cod_database_fobs_code 2005329