############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-Bis[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-1H-benzimidazol- 2(3H)-one ; _chemical_name_common ? _chemical_formula_moiety 'C17 H20 N4 O5' _chemical_formula_sum 'C17 H20 N4 O5' _chemical_formula_iupac 'C17 H20 N4 O5' _chemical_formula_weight 360.37 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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' _cell_length_a 10.5331(10) _cell_length_b 10.9647(10) _cell_length_c 14.5541(14) _cell_angle_alpha 90 _cell_angle_beta 103.258(5) _cell_angle_gamma 90 _cell_volume 1636.1(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9916 _cell_measurement_theta_min 4.0 _cell_measurement_theta_max 68.1 _cell_measurement_temperature 90.0(5) _exptl_crystal_description 'fragment' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.918 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2005)' _exptl_absorpt_correction_T_min 0.770 _exptl_absorpt_correction_T_max 0.852 _exptl_special_details ; ; _diffrn_ambient_temperature 90.0(5) _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15549 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_theta_min 4.3 _diffrn_reflns_theta_max 68.2 _diffrn_reflns_theta_full 68.22 _diffrn_measured_fraction_theta_max 0.970 _diffrn_measured_fraction_theta_full 0.970 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > \s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2914 _reflns_number_gt 2842 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_gt 0.0736 _refine_ls_wR_factor_ref 0.0741 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_number_reflns 2914 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0315P)^2^+0.8105P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.234 _refine_diff_density_min -0.193 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' loop_ _atom_site_type_symbol _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 O O1 0.51156(8) 0.90454(8) 0.65034(6) 0.01864(19) Uani d . 1 . . O O2 0.81349(8) 0.63845(8) 0.39970(6) 0.0221(2) Uani d . 1 . . O O3 0.61653(8) 0.68768(8) 0.42496(6) 0.0209(2) Uani d . 1 . . O O4 0.22108(8) 0.77982(8) 0.47938(6) 0.01792(19) Uani d . 1 . . O O5 0.18927(8) 0.77876(8) 0.62760(6) 0.0217(2) Uani d . 1 . . N N1 0.71846(9) 0.83091(9) 0.64775(7) 0.0145(2) Uani d . 1 . . N N2 0.58627(9) 0.71116(9) 0.70549(7) 0.0143(2) Uani d . 1 . . N N3 0.79091(9) 0.81926(9) 0.46197(7) 0.0149(2) Uani d . 1 . . N N4 0.33456(9) 0.64839(9) 0.58183(7) 0.0158(2) Uani d . 1 . . C C1 0.59511(11) 0.82469(11) 0.66601(8) 0.0143(2) Uani d . 1 . . C C2 0.78498(11) 0.72200(10) 0.67384(8) 0.0142(2) Uani d . 1 . . C C3 0.70112(11) 0.64616(11) 0.71027(7) 0.0137(2) Uani d . 1 . . C C4 0.73829(11) 0.52998(11) 0.74338(8) 0.0157(2) Uani d . 1 . . H H4 0.6828 0.4800 0.7679 0.019 Uiso calc R 1 . . C C5 0.86290(11) 0.49150(11) 0.73819(8) 0.0174(3) Uani d . 1 . . H H5 0.8907 0.4137 0.7591 0.021 Uiso calc R 1 . . C C6 0.94645(11) 0.56687(11) 0.70237(8) 0.0176(3) Uani d . 1 . . H H6 1.0288 0.5384 0.7000 0.021 Uiso calc R 1 . . C C7 0.90915(11) 0.68422(11) 0.66999(8) 0.0162(2) Uani d . 1 . . H H7 0.9653 0.7350 0.6468 0.019 Uiso calc R 1 . . C C8 0.76194(11) 0.93510(10) 0.60123(8) 0.0159(2) Uani d . 1 . . H H8A 0.8558 0.9432 0.6227 0.019 Uiso calc R 1 . . H H8B 0.7223 1.0086 0.6190 0.019 Uiso calc R 1 . . C C9 0.72673(11) 0.92265(11) 0.49385(8) 0.0162(2) Uani d . 1 . . H H9A 0.6330 0.9132 0.4724 0.019 Uiso calc R 1 . . H H9B 0.7516 0.9966 0.4659 0.019 Uiso calc R 1 . . C C10 0.72954(11) 0.71504(11) 0.42958(8) 0.0160(2) Uani d . 1 . . C C11 0.94356(12) 0.69048(12) 0.42409(9) 0.0210(3) Uani d . 1 . . H H11A 0.9846 0.6861 0.3709 0.025 Uiso calc R 1 . . H H11B 0.9977 0.6475 0.4771 0.025 Uiso calc R 1 . . C C12 0.92429(11) 0.82316(11) 0.45003(8) 0.0170(3) Uani d . 1 . . H H12A 0.9852 0.8466 0.5080 0.020 Uiso calc R 1 . . H H12B 0.9329 0.8785 0.3998 0.020 Uiso calc R 1 . . C C13 0.47432(11) 0.67173(11) 0.74094(8) 0.0156(2) Uani d . 1 . . H H13A 0.4262 0.7430 0.7533 0.019 Uiso calc R 1 . . H H13B 0.5050 0.6290 0.8002 0.019 Uiso calc R 1 . . C C14 0.38313(11) 0.58849(11) 0.67225(8) 0.0169(2) Uani d . 1 . . H H14A 0.4293 0.5147 0.6628 0.020 Uiso calc R 1 . . H H14B 0.3102 0.5655 0.6989 0.020 Uiso calc R 1 . . C C15 0.24555(11) 0.73773(11) 0.57032(8) 0.0159(2) Uani d . 1 . . C C16 0.31809(12) 0.72690(11) 0.43458(9) 0.0198(3) Uani d . 1 . . H H16A 0.3889 0.7837 0.4355 0.024 Uiso calc R 1 . . H H16B 0.2794 0.7048 0.3697 0.024 Uiso calc R 1 . . C C17 0.36658(12) 0.61423(11) 0.49327(8) 0.0197(3) Uani d . 1 . . H H17A 0.3204 0.5413 0.4665 0.024 Uiso calc R 1 . . H H17B 0.4596 0.6023 0.5006 0.024 Uiso calc R 1 . . 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 O1 0.0189(4) 0.0159(4) 0.0217(4) 0.0033(3) 0.0056(3) 0.0003(3) O2 0.0169(4) 0.0205(5) 0.0288(5) -0.0003(3) 0.0049(3) -0.0081(4) O3 0.0160(4) 0.0201(5) 0.0261(5) -0.0024(3) 0.0038(3) -0.0008(4) O4 0.0165(4) 0.0186(4) 0.0190(4) 0.0030(3) 0.0048(3) 0.0007(3) O5 0.0178(4) 0.0263(5) 0.0222(4) 0.0031(4) 0.0069(3) -0.0052(4) N1 0.0156(5) 0.0134(5) 0.0151(5) 0.0001(4) 0.0047(4) 0.0010(4) N2 0.0135(5) 0.0143(5) 0.0155(5) 0.0002(4) 0.0044(4) 0.0001(4) N3 0.0145(5) 0.0147(5) 0.0159(5) -0.0007(4) 0.0042(4) -0.0003(4) N4 0.0161(5) 0.0158(5) 0.0155(5) 0.0018(4) 0.0037(4) -0.0017(4) C1 0.0158(6) 0.0145(6) 0.0123(5) -0.0005(5) 0.0025(4) -0.0022(4) C2 0.0164(6) 0.0143(6) 0.0108(5) -0.0001(5) 0.0010(4) -0.0011(4) C3 0.0139(5) 0.0159(6) 0.0111(5) -0.0006(4) 0.0020(4) -0.0023(4) C4 0.0184(6) 0.0160(6) 0.0125(5) -0.0018(5) 0.0031(4) 0.0001(4) C5 0.0211(6) 0.0153(6) 0.0148(5) 0.0034(5) 0.0019(4) 0.0014(4) C6 0.0157(6) 0.0212(6) 0.0158(5) 0.0038(5) 0.0033(4) -0.0002(5) C7 0.0163(6) 0.0188(6) 0.0141(5) -0.0013(5) 0.0047(4) 0.0001(4) C8 0.0181(6) 0.0118(6) 0.0183(6) -0.0016(5) 0.0054(4) -0.0003(4) C9 0.0179(6) 0.0133(6) 0.0175(6) 0.0020(5) 0.0042(4) 0.0017(4) C10 0.0177(6) 0.0163(6) 0.0136(5) 0.0017(5) 0.0024(4) 0.0017(4) C11 0.0149(6) 0.0240(7) 0.0241(6) 0.0000(5) 0.0049(5) -0.0046(5) C12 0.0146(6) 0.0201(6) 0.0169(6) -0.0007(5) 0.0046(4) 0.0016(5) C13 0.0147(6) 0.0172(6) 0.0159(5) -0.0010(5) 0.0057(4) -0.0003(5) C14 0.0166(6) 0.0161(6) 0.0179(6) -0.0008(5) 0.0038(4) 0.0012(5) C15 0.0121(5) 0.0165(6) 0.0183(6) -0.0028(5) 0.0020(4) -0.0030(5) C16 0.0215(6) 0.0197(6) 0.0206(6) 0.0029(5) 0.0097(5) 0.0006(5) C17 0.0246(6) 0.0175(6) 0.0197(6) 0.0033(5) 0.0106(5) -0.0001(5) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ; 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 O1 C1 . 1.2252(14) ? O2 C10 . 1.3612(14) ? O2 C11 . 1.4510(15) ? O3 C10 . 1.2144(14) ? O4 C15 . 1.3692(14) ? O4 C16 . 1.4531(14) ? O5 C15 . 1.2147(14) ? N1 C1 . 1.3862(15) ? N1 C2 . 1.3926(15) ? N1 C8 . 1.4545(15) ? N2 C1 . 1.3831(15) ? N2 C3 . 1.3921(15) ? N2 C13 . 1.4570(14) ? N3 C10 . 1.3439(16) ? N3 C9 . 1.4496(15) ? N3 C12 . 1.4552(14) ? N4 C15 . 1.3396(15) ? N4 C17 . 1.4542(15) ? N4 C14 . 1.4546(15) ? C2 C7 . 1.3853(16) ? C2 C3 . 1.4027(16) ? C3 C4 . 1.3862(17) ? C4 C5 . 1.3971(17) ? C4 H4 . 0.9300 ? C5 C6 . 1.3927(17) ? C5 H5 . 0.9300 ? C6 C7 . 1.3955(17) ? C6 H6 . 0.9300 ? C7 H7 . 0.9300 ? C8 C9 . 1.5273(16) ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C11 C12 . 1.5282(17) ? C11 H11A . 0.9700 ? C11 H11B . 0.9700 ? C12 H12A . 0.9700 ? C12 H12B . 0.9700 ? C13 C14 . 1.5215(16) ? C13 H13A . 0.9700 ? C13 H13B . 0.9700 ? C14 H14A . 0.9700 ? C14 H14B . 0.9700 ? C16 C17 . 1.5220(17) ? C16 H16A . 0.9700 ? C16 H16B . 0.9700 ? C17 H17A . 0.9700 ? C17 H17B . 0.9700 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C10 O2 C11 . . 108.99(9) ? C15 O4 C16 . . 107.65(9) ? C1 N1 C2 . . 109.92(9) ? C1 N1 C8 . . 122.48(10) ? C2 N1 C8 . . 127.44(10) ? C1 N2 C3 . . 109.94(9) ? C1 N2 C13 . . 123.46(9) ? C3 N2 C13 . . 126.51(10) ? C10 N3 C9 . . 123.71(10) ? C10 N3 C12 . . 112.52(10) ? C9 N3 C12 . . 123.31(10) ? C15 N4 C17 . . 112.04(10) ? C15 N4 C14 . . 122.29(10) ? C17 N4 C14 . . 125.49(10) ? O1 C1 N2 . . 127.34(11) ? O1 C1 N1 . . 126.44(11) ? N2 C1 N1 . . 106.22(9) ? C7 C2 N1 . . 131.76(11) ? C7 C2 C3 . . 121.35(11) ? N1 C2 C3 . . 106.88(10) ? C4 C3 N2 . . 131.36(11) ? C4 C3 C2 . . 121.60(11) ? N2 C3 C2 . . 107.03(10) ? C3 C4 C5 . . 116.91(11) ? C3 C4 H4 . . 121.5 ? C5 C4 H4 . . 121.5 ? C6 C5 C4 . . 121.54(11) ? C6 C5 H5 . . 119.2 ? C4 C5 H5 . . 119.2 ? C5 C6 C7 . . 121.36(11) ? C5 C6 H6 . . 119.3 ? C7 C6 H6 . . 119.3 ? C2 C7 C6 . . 117.21(11) ? C2 C7 H7 . . 121.4 ? C6 C7 H7 . . 121.4 ? N1 C8 C9 . . 112.19(9) ? N1 C8 H8A . . 109.2 ? C9 C8 H8A . . 109.2 ? N1 C8 H8B . . 109.2 ? C9 C8 H8B . . 109.2 ? H8A C8 H8B . . 107.9 ? N3 C9 C8 . . 112.07(9) ? N3 C9 H9A . . 109.2 ? C8 C9 H9A . . 109.2 ? N3 C9 H9B . . 109.2 ? C8 C9 H9B . . 109.2 ? H9A C9 H9B . . 107.9 ? O3 C10 N3 . . 128.03(11) ? O3 C10 O2 . . 122.02(11) ? N3 C10 O2 . . 109.95(10) ? O2 C11 C12 . . 105.27(9) ? O2 C11 H11A . . 110.7 ? C12 C11 H11A . . 110.7 ? O2 C11 H11B . . 110.7 ? C12 C11 H11B . . 110.7 ? H11A C11 H11B . . 108.8 ? N3 C12 C11 . . 100.84(9) ? N3 C12 H12A . . 111.6 ? C11 C12 H12A . . 111.6 ? N3 C12 H12B . . 111.6 ? C11 C12 H12B . . 111.6 ? H12A C12 H12B . . 109.4 ? N2 C13 C14 . . 112.67(9) ? N2 C13 H13A . . 109.1 ? C14 C13 H13A . . 109.1 ? N2 C13 H13B . . 109.1 ? C14 C13 H13B . . 109.1 ? H13A C13 H13B . . 107.8 ? N4 C14 C13 . . 111.20(10) ? N4 C14 H14A . . 109.4 ? C13 C14 H14A . . 109.4 ? N4 C14 H14B . . 109.4 ? C13 C14 H14B . . 109.4 ? H14A C14 H14B . . 108.0 ? O5 C15 N4 . . 128.51(11) ? O5 C15 O4 . . 121.68(11) ? N4 C15 O4 . . 109.79(10) ? O4 C16 C17 . . 104.61(9) ? O4 C16 H16A . . 110.8 ? C17 C16 H16A . . 110.8 ? O4 C16 H16B . . 110.8 ? C17 C16 H16B . . 110.8 ? H16A C16 H16B . . 108.9 ? N4 C17 C16 . . 99.92(9) ? N4 C17 H17A . . 111.8 ? C16 C17 H17A . . 111.8 ? N4 C17 H17B . . 111.8 ? C16 C17 H17B . . 111.8 ? H17A C17 H17B . . 109.5 ? data_global _journal_date_recd_electronic 2010-12-03 _journal_date_accepted 2010-12-12 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2011 _journal_volume 67 _journal_issue 2 _journal_page_first o362 _journal_page_last o363 _journal_paper_category QO _journal_coeditor_code FJ2373 _publ_contact_author ; Essassi, El Mokhtar Laboratoire de Chimie Organique H\'et\'erocyclique, P\^ole de comp\'etences, Pharmacochimie, Av Ibn Battouta, BP. 1014, Facult\'e des Sciences, Universit\'e Mohammed V-Agdal, Rabat, Morocco ; _publ_contact_author_email 'emessassi@yahoo.fr' _publ_contact_author_fax '212 537 77 54 40' _publ_section_title ;\ 1,3-Bis[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-1H-benzimidazol-2(3H)\ -one ; loop_ _publ_author_name _publ_author_address 'Ouzidan, Younes' ; Laboratoire de Chimie Organique Appliqu\'ee Universit\'e Sidi Mohamed Ben Abdallah Facult\'e des Sciences et Techniques Route d'Immouzzer BP 2202 F\`es Morocco ; 'Kandri Rodi, Youssef' ; Laboratoire de Chimie Organique Appliqu\'ee Universit\'e Sidi Mohamed Ben Abdallah Facult\'e des Sciences et Techniques Route d'Immouzzer BP 2202 F\`es Morocco ; 'Fronczek, Frank R.' ; Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803 USA ; 'Venkatraman, Ramaiyer' ; Department of Chemistry and Biochemistry Jackson State University Jackson MS 39217 USA ; 'El Ammari, Lahcen' ; Laboratoire de Chimie du Solide Appliqu\'ee, Facult\'e des Sciences, Universit\'e Mohammed V-Agdal Avenue Ibn Battouta, BP 1014, Rabat, Morocco ; 'Essassi, El Mokhtar' ; INANOTECH (Institute of Nanomaterials and Nanotechnology), MASCiR, Avenue de l'Arm\'ee Royale, Rabat, Morocco ;