#------------------------------------------------------------------------------ #$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/1000006.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_tiny3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H25 Cl N2 O8' _chemical_formula_weight 480.89 _publ_contact_author_name 'Armel Le Bail' _publ_contact_author_address ; Laboratoire des Fluorures - UPRES-A 6010 Facult\'e des Sciences, Universit\'e du Maine, Avenue Olivier-Messiaen, 72085 LE MANS Cedex 9, FRANCE ; 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' 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.9300(9) _cell_length_b 12.7162(11) _cell_length_c 15.7085(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2183.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6452 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 29.20 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6883 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 15 _diffrn_reflns_number 8955 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0794 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 29.26 _reflns_number_total 4915 _reflns_number_gt 3937 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^ > 2sigma(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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0038(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(8) _refine_ls_number_reflns 4915 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1161 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.92963(7) 0.41939(6) -0.00197(4) 0.01949(17) Uani 1 1 d . . . O1 O 0.0086(3) 0.3656(3) 0.43967(14) 0.0392(7) Uani 1 1 d . . . H1 H 0.039(4) 0.433(4) 0.435(2) 0.047(13) Uiso 1 1 d . . . O6 O 0.1453(2) 0.46012(16) 0.12979(12) 0.0194(5) Uani 1 1 d . . . H6 H 0.086(4) 0.449(3) 0.088(2) 0.045(12) Uiso 1 1 d . . . O11 O 0.7514(2) 0.64335(19) 0.07408(14) 0.0268(5) Uani 1 1 d . . . O13 O 0.3634(2) 0.71743(18) 0.18883(13) 0.0250(5) Uani 1 1 d . . . O14 O 0.5800(2) 0.60174(18) 0.29547(12) 0.0212(5) Uani 1 1 d . . . H14 H 0.565(4) 0.614(3) 0.338(2) 0.033(11) Uiso 1 1 d . . . O15 O 0.3506(2) 0.60822(17) 0.35612(12) 0.0198(5) Uani 1 1 d . . . H15 H 0.283(4) 0.580(4) 0.385(2) 0.045(12) Uiso 1 1 d . . . O17 O 0.1647(2) 0.50211(18) 0.38835(12) 0.0234(5) Uani 1 1 d . . . O19 O 0.6623(3) 0.81863(18) 0.04211(13) 0.0269(6) Uani 1 1 d . . . H19 H 0.734(5) 0.757(4) 0.055(3) 0.061(14) Uiso 1 1 d . . . N10 N 0.7465(3) 0.4488(2) 0.14281(16) 0.0193(6) Uani 1 1 d . . . H10 H 0.793(4) 0.464(3) 0.100(2) 0.035(11) Uiso 1 1 d . . . N19 N 0.4694(3) 0.8551(2) 0.08138(17) 0.0288(7) Uani 1 1 d . . . H19A H 0.475(4) 0.921(3) 0.058(2) 0.034(10) Uiso 1 1 d . . . H19B H 0.408(4) 0.833(4) 0.112(2) 0.049(14) Uiso 1 1 d . . . C1 C 0.0207(3) 0.3204(3) 0.36224(18) 0.0272(8) Uani 1 1 d . . . C2 C -0.0525(4) 0.2345(3) 0.3435(2) 0.0314(9) Uani 1 1 d . . . H2 H -0.111(3) 0.211(3) 0.388(2) 0.026(9) Uiso 1 1 d . . . C3 C -0.0436(4) 0.1888(3) 0.2657(2) 0.0302(8) Uani 1 1 d . . . H3 H -0.084(4) 0.134(3) 0.253(2) 0.040(12) Uiso 1 1 d . . . C4 C 0.0378(3) 0.2253(3) 0.2036(2) 0.0240(7) Uani 1 1 d . . . H4 H 0.038(3) 0.189(3) 0.148(2) 0.028(9) Uiso 1 1 d . . . C5 C 0.1113(3) 0.3105(2) 0.22057(18) 0.0183(7) Uani 1 1 d . . . C6 C 0.1962(3) 0.3609(2) 0.15436(17) 0.0178(7) Uani 1 1 d . . . C7 C 0.3178(3) 0.3872(2) 0.19906(16) 0.0145(6) Uani 1 1 d . . . H7 H 0.337(4) 0.318(3) 0.222(2) 0.028(9) Uiso 1 1 d . . . C8 C 0.4148(3) 0.4314(2) 0.13903(16) 0.0170(6) Uani 1 1 d . . . H8A H 0.378(4) 0.486(3) 0.107(2) 0.035(10) Uiso 1 1 d . . . H8B H 0.444(3) 0.378(3) 0.1001(19) 0.025(9) Uiso 1 1 d . . . C9 C 0.5241(3) 0.4766(2) 0.18811(16) 0.0141(6) Uani 1 1 d . . . H9 H 0.554(3) 0.423(3) 0.2292(18) 0.020(8) Uiso 1 1 d . . . C10 C 0.6283(3) 0.5041(2) 0.12622(17) 0.0156(6) Uani 1 1 d . . . H10A H 0.615(3) 0.482(2) 0.0715(17) 0.007(7) Uiso 1 1 d . . . C11 C 0.6526(3) 0.6204(2) 0.11090(16) 0.0180(6) Uani 1 1 d . . . C12 C 0.5579(3) 0.6923(2) 0.12673(16) 0.0170(6) Uani 1 1 d . . . C13 C 0.4588(3) 0.6663(2) 0.18199(15) 0.0171(7) Uani 1 1 d . . . C14 C 0.4828(3) 0.5705(2) 0.24083(15) 0.0150(6) Uani 1 1 d . . . C15 C 0.3690(3) 0.5439(2) 0.29061(15) 0.0158(6) Uani 1 1 d . . . C16 C 0.2940(3) 0.4624(2) 0.27178(16) 0.0149(6) Uani 1 1 d . . . C17 C 0.1867(3) 0.4446(2) 0.32353(16) 0.0184(7) Uani 1 1 d . . . C18 C 0.1060(3) 0.3578(3) 0.30253(17) 0.0187(7) Uani 1 1 d . . . C19 C 0.5622(3) 0.7911(2) 0.08265(16) 0.0204(7) Uani 1 1 d . . . C20 C 0.2161(4) 0.2919(3) 0.0769(2) 0.0246(8) Uani 1 1 d . . . H20A H 0.135(3) 0.284(3) 0.0479(18) 0.015(8) Uiso 1 1 d . . . H20B H 0.245(4) 0.225(4) 0.090(2) 0.038(11) Uiso 1 1 d . . . H20C H 0.259(3) 0.329(3) 0.034(2) 0.025(9) Uiso 1 1 d . . . C21 C 0.7318(4) 0.3324(3) 0.1384(2) 0.0259(8) Uani 1 1 d . . . H21A H 0.688(4) 0.311(3) 0.184(2) 0.041(11) Uiso 1 1 d . . . H21B H 0.810(4) 0.303(3) 0.1312(19) 0.019(9) Uiso 1 1 d . . . H21C H 0.698(3) 0.321(3) 0.085(2) 0.028(10) Uiso 1 1 d . . . C22 C 0.8096(4) 0.4811(3) 0.2228(2) 0.0308(9) Uani 1 1 d . . . H22A H 0.820(3) 0.559(3) 0.223(2) 0.028(9) Uiso 1 1 d . . . H22B H 0.885(4) 0.458(4) 0.222(2) 0.039(12) Uiso 1 1 d . . . H22C H 0.761(4) 0.457(3) 0.269(2) 0.030(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0148(4) 0.0225(3) 0.0212(3) 0.0011(3) 0.0017(3) -0.0031(3) O1 0.0359(18) 0.0553(19) 0.0265(11) 0.0003(11) 0.0098(10) -0.0166(16) O6 0.0161(13) 0.0172(11) 0.0248(10) 0.0008(8) -0.0052(9) 0.0042(11) O11 0.0167(14) 0.0226(12) 0.0412(11) 0.0072(10) 0.0086(10) -0.0041(11) O13 0.0229(15) 0.0233(12) 0.0288(10) 0.0014(9) 0.0041(9) 0.0096(12) O14 0.0140(13) 0.0322(13) 0.0174(9) -0.0005(8) -0.0032(8) -0.0055(11) O15 0.0154(13) 0.0240(12) 0.0200(9) -0.0047(8) 0.0013(8) 0.0000(11) O17 0.0180(13) 0.0292(12) 0.0229(9) -0.0026(9) 0.0037(8) 0.0002(12) O19 0.0310(16) 0.0199(12) 0.0297(11) 0.0052(9) -0.0002(10) -0.0075(13) N10 0.0132(15) 0.0194(13) 0.0254(11) 0.0042(10) 0.0046(10) -0.0001(12) N19 0.038(2) 0.0166(14) 0.0319(14) 0.0069(11) -0.0021(13) 0.0056(15) C1 0.020(2) 0.0351(19) 0.0262(14) 0.0090(13) 0.0011(13) -0.0004(17) C2 0.017(2) 0.041(2) 0.0364(16) 0.0125(15) -0.0011(14) -0.0087(19) C3 0.017(2) 0.0267(19) 0.0466(18) 0.0057(15) -0.0042(14) -0.0080(19) C4 0.013(2) 0.0218(17) 0.0373(16) -0.0007(13) -0.0020(13) 0.0003(15) C5 0.0084(18) 0.0178(15) 0.0287(13) 0.0034(11) -0.0015(11) 0.0039(14) C6 0.0169(18) 0.0154(14) 0.0211(12) -0.0015(10) -0.0004(11) 0.0025(14) C7 0.0061(16) 0.0135(14) 0.0237(12) -0.0006(10) 0.0003(10) 0.0009(13) C8 0.0124(17) 0.0177(15) 0.0209(11) -0.0034(11) 0.0022(11) 0.0008(15) C9 0.0079(16) 0.0132(14) 0.0211(11) 0.0015(10) 0.0011(10) 0.0007(13) C10 0.0074(16) 0.0173(15) 0.0220(12) 0.0011(11) -0.0008(10) 0.0014(14) C11 0.0153(18) 0.0184(15) 0.0202(12) 0.0031(11) -0.0013(11) -0.0003(15) C12 0.0172(18) 0.0133(13) 0.0206(12) 0.0006(9) -0.0011(11) -0.0003(15) C13 0.018(2) 0.0167(14) 0.0161(11) -0.0034(10) -0.0013(11) 0.0002(15) C14 0.0119(16) 0.0151(14) 0.0181(11) -0.0005(10) -0.0024(10) -0.0015(14) C15 0.0135(17) 0.0170(15) 0.0170(11) 0.0015(10) -0.0036(10) 0.0046(14) C16 0.0123(17) 0.0153(14) 0.0172(11) 0.0024(10) -0.0009(10) 0.0040(14) C17 0.0151(18) 0.0210(16) 0.0190(12) 0.0038(10) -0.0009(10) 0.0052(15) C18 0.0111(18) 0.0209(16) 0.0240(13) 0.0045(11) -0.0007(11) 0.0031(14) C19 0.026(2) 0.0143(14) 0.0209(12) 0.0000(10) -0.0036(12) -0.0055(17) C20 0.019(2) 0.0250(19) 0.0299(15) -0.0109(13) 0.0012(13) -0.0014(18) C21 0.024(2) 0.0177(17) 0.0366(17) 0.0046(13) 0.0117(15) 0.0050(17) C22 0.017(2) 0.038(2) 0.0367(18) 0.0019(15) -0.0056(15) 0.002(2) _diffrn_measured_fraction_theta_max 0.807 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.915 _refine_diff_density_max 0.572 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.064