############################################################################## ### ### ### 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_global _audit_creation_method 'WinGX routine-INITIALISE' _journal_date_recd_electronic 2009-08-14 _journal_date_accepted 2009-08-22 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2009 _journal_volume 65 _journal_issue 9 _journal_page_first o2264 _journal_page_last o2265 _journal_paper_category QO _journal_coeditor_code AT2865 _publ_contact_author_name 'Lamia, Bendjeddou' _publ_contact_author_address ; Laboratoire de Chimie Mol\'eculaire, du Contr\^ole de l'Environnement et des Mesures Physico-Chimiques Facult\'e des Sciences Exactes, D\'epartement de Chimie, Universit\'e Mentouri de Constantine 25000 Constantine Alg\'erie ; _publ_contact_author_email 'lamiabendjeddou@yahoo.fr' _publ_contact_author_fax '00 (213) 31 61 46 44' _publ_contact_author_phone '00 (213) 31 61 46 44' _publ_section_title ; DL-Asparaginium perchlorate at 100 K ; loop_ _publ_author_name _publ_author_address 'Guenifa, Fatiha' ; Laboratoire de Chimie Mol\'eculaire, du Contr\^ole de l'Environnement et des Mesures Physico-Chimiques Facult\'e des Sciences Exactes, D\'epartement de Chimie, Universit\'e Mentouri de Constantine 25000 Constantine Algeria ; 'Bendjeddou, Lamia' ; Laboratoire de Chimie Mol\'eculaire, du Contr\^ole de l'Environnement et des Mesures Physico-Chimiques Facult\'e des Sciences Exactes, D\'epartement de Chimie, Universit\'e Mentouri de Constantine 25000 Constantine Algeria ; 'Cherouana, Aouatef' ; Laboratoire de Chimie Mol\'eculaire, du Contr\^ole de l'Environnement et des Mesures Physico-Chimiques Facult\'e des Sciences Exactes, D\'epartement de Chimie, Universit\'e Mentouri de Constantine 25000 Constantine Algeria ; 'Dahaoui, Slimane' ; Laboratoire de Cristallographie et Mod\'elisation, des Mat\'eriaux Min\'eraux et Biologiques (LCM3B), Universit\'e Henri Poincar\'e Nancy I, UPRESA CNRS 7036, BP 239, 54506 Vandoeuvre les Nancy France ; 'Lecomte, Claude' ; Laboratoire de Cristallographie et Mod\'elisation, des Mat\'e riaux Min\'e raux et Biologiques (LCM3B), Universit\'e Henri Poincar\'e Nancy I, UPRESA CNRS 7036, BP 239, 54506 Vandoeuvre les Nancy France ; data_I _chemical_name_systematic ; DL-Asparaginium perchlorate ; _chemical_name_common 'DL-asparaginium perchlorate ' _chemical_formula_moiety 'C4 H9 N2 O3, Cl O4' _chemical_formula_sum 'C4 H9 Cl N2 O7' _chemical_formula_structural 'C4 H9 Cl N2 O7' _chemical_formula_iupac 'C4 H9 N2 O3 +, Cl O4 -' _chemical_formula_weight 232.58 _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z 5 -x,-y,-z 6 1/2+x,y,1/2-z 7 1/2-x,1/2+y,z 8 x,1/2-y,1/2+z _cell_length_a 9.861(5) _cell_length_b 10.289(4) _cell_length_c 16.700(5) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 1694.4(12) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2818 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 31.5 _cell_measurement_temperature 100(2) _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.823 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.47 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 100(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Oxford Diffraction Xcalibur Saphire2 CCD' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 45509 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 31.5 _diffrn_reflns_theta_full 31.5 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _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 2818 _reflns_number_gt 2205 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.046 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_gt 0.09 _refine_ls_wR_factor_ref 0.0997 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_number_reflns 2818 _refine_ls_number_parameters 127 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.6998P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.676 _refine_diff_density_min -0.379 _refine_ls_extinction_method none loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2008)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2008)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material ; WinGX (Farrugia, 1999), PARST97 (Nardelli, 1995) and Mercury (Macrae et al., 2006) ; 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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy O O1 0.58079(10) 0.69351(10) 0.73615(6) 0.0162(3) Uani . . 1.000 O O2 0.45528(9) 0.59815(10) 0.63971(6) 0.0139(3) Uani . . 1.000 O O3 0.61640(11) 0.32442(10) 0.70705(6) 0.0158(3) Uani . . 1.000 N N1 0.67333(11) 0.48834(11) 0.57093(6) 0.0115(3) Uani . . 1.000 N N2 0.71473(14) 0.37342(13) 0.82581(7) 0.0204(4) Uani . . 1.000 C C1 0.56293(14) 0.62144(13) 0.67245(8) 0.0117(3) Uani . . 1.000 C C2 0.69857(13) 0.56919(13) 0.64328(8) 0.0111(3) Uani . . 1.000 C C3 0.77716(13) 0.49753(13) 0.70849(8) 0.0126(3) Uani . . 1.000 C C4 0.69625(14) 0.39103(13) 0.74834(8) 0.0127(3) Uani . . 1.000 Cl Cl 0.47309(3) 0.19831(3) 0.51836(2) 0.01270(10) Uani . . 1.000 O O4 0.40552(10) 0.17287(10) 0.44286(6) 0.0158(3) Uani . . 1.000 O O5 0.43440(10) 0.32809(10) 0.54535(6) 0.0145(3) Uani . . 1.000 O O6 0.43348(15) 0.10450(12) 0.57652(7) 0.0315(4) Uani . . 1.000 O O7 0.61761(11) 0.19650(11) 0.50614(7) 0.0226(3) Uani . . 1.000 H H1 0.50733 0.72120 0.75158 0.0243 Uiso . . 1.000 H H1A 0.75164 0.45681 0.55290 0.0172 Uiso . . 1.000 H H1B 0.63499 0.53694 0.53310 0.0172 Uiso . . 1.000 H H1C 0.61828 0.42291 0.58350 0.0172 Uiso . . 1.000 H H2 0.75352 0.64382 0.62663 0.0133 Uiso . . 1.000 H H3A 0.85826 0.46000 0.68513 0.0151 Uiso . . 1.000 H H3B 0.80548 0.55964 0.74887 0.0151 Uiso . . 1.000 H H4N 0.67437 0.31063 0.84737 0.0246 Uiso . . 1.000 H H5N 0.77523 0.41807 0.84813 0.0246 Uiso . . 1.000 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 0.0144(5) 0.0187(5) 0.0156(5) 0.0014(4) 0.0022(4) -0.0059(4) O2 0.0116(4) 0.0155(5) 0.0146(5) 0.0008(3) 0.0014(3) 0.0001(4) O3 0.0162(5) 0.0177(5) 0.0135(4) -0.0048(4) -0.0012(4) 0.0035(4) N1 0.0113(5) 0.0127(5) 0.0104(5) 0.0015(4) 0.0010(4) 0.0002(4) N2 0.0253(7) 0.0250(7) 0.0110(5) 0.0020(5) -0.0013(4) 0.0023(5) C1 0.0134(6) 0.0092(5) 0.0125(6) -0.0007(4) 0.0028(4) 0.0024(5) C2 0.0104(5) 0.0108(5) 0.0120(5) -0.0010(4) 0.0013(4) -0.0014(4) C3 0.0102(5) 0.0141(6) 0.0135(6) -0.0005(4) -0.0017(4) -0.0010(5) C4 0.0128(5) 0.0133(6) 0.0119(6) 0.0045(5) 0.0010(4) -0.0002(5) Cl 0.0164(2) 0.0106(2) 0.0112(2) -0.00030(10) -0.00210(10) 0.00040(10) O4 0.0155(5) 0.0178(5) 0.0142(5) -0.0034(4) -0.0043(4) -0.0027(4) O5 0.0165(5) 0.0125(5) 0.0145(5) 0.0006(3) -0.0008(4) -0.0023(4) O6 0.0588(9) 0.0177(5) 0.0179(6) -0.0056(5) 0.0043(5) 0.0082(4) O7 0.0145(5) 0.0267(6) 0.0265(6) 0.0061(4) -0.0080(4) -0.0079(4) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl O5 . . 1.4601(13) no Cl O6 . . 1.4239(15) no Cl O4 . . 1.4499(13) no Cl O7 . . 1.4398(13) no O1 C1 . . 1.3086(18) no O2 C1 . . 1.2179(18) no O3 C4 . . 1.2511(18) no O1 H1 . . 0.8200 no N1 C2 . . 1.4879(19) no N2 C4 . . 1.3190(19) no N1 H1A . . 0.8900 no N1 H1C . . 0.8900 no N1 H1B . . 0.8900 no N2 H4N . . 0.8400 no N2 H5N . . 0.8400 no C1 C2 . . 1.522(2) no C2 C3 . . 1.527(2) no C3 C4 . . 1.510(2) no C2 H2 . . 0.9800 no C3 H3A . . 0.9700 no C3 H3B . . 0.9700 no 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_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O5 Cl O6 . . . 109.74(7) no O5 Cl O7 . . . 108.32(6) no O6 Cl O7 . . . 111.07(8) no O4 Cl O5 . . . 108.27(6) no O4 Cl O6 . . . 110.17(7) no O4 Cl O7 . . . 109.23(6) no C1 O1 H1 . . . 109.00 no C2 N1 H1A . . . 109.00 no C2 N1 H1B . . . 109.00 no H1B N1 H1C . . . 109.00 no H1A N1 H1C . . . 109.00 no C2 N1 H1C . . . 109.00 no H1A N1 H1B . . . 109.00 no C4 N2 H5N . . . 117.00 no H4N N2 H5N . . . 125.00 no C4 N2 H4N . . . 117.00 no O2 C1 C2 . . . 123.57(12) no O1 C1 C2 . . . 110.01(11) no O1 C1 O2 . . . 126.42(13) no N1 C2 C3 . . . 113.22(11) no N1 C2 C1 . . . 108.09(10) no C1 C2 C3 . . . 112.86(11) no C2 C3 C4 . . . 113.37(11) no N2 C4 C3 . . . 117.32(12) no O3 C4 N2 . . . 123.53(13) no O3 C4 C3 . . . 119.16(12) no N1 C2 H2 . . . 107.00 no C1 C2 H2 . . . 107.00 no C3 C2 H2 . . . 107.00 no H3A C3 H3B . . . 108.00 no C2 C3 H3A . . . 109.00 no C2 C3 H3B . . . 109.00 no C4 C3 H3A . . . 109.00 no C4 C3 H3B . . . 109.00 no 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 _geom_hbond_publ_flag O1 H1 O3 4_656 0.8200 1.7600 2.5485(19) 161.00 yes N1 H1A O4 3_556 0.8900 2.0200 2.837(2) 152.00 yes N1 H1B O5 5_666 0.8900 2.0300 2.910(2) 171.00 yes N1 H1C O3 . 0.8900 2.3000 2.886(2) 123.00 yes N1 H1C O5 . 0.8900 2.1600 2.907(2) 142.00 yes N2 H4N O2 4_646 0.8400 2.5400 3.341(2) 159.00 yes N2 H5N O2 6_556 0.8400 2.5700 3.362(2) 157.00 yes N2 H5N O5 6_556 0.8400 2.5500 3.089(2) 123.00 yes C2 H2 O7 7_655 0.9800 2.4400 3.201(2) 134.00 yes C3 H3A O4 3_556 0.9700 2.5800 3.326(2) 134.00 yes C3 H3B O2 6_556 0.9700 2.4100 3.253(2) 145.00 yes