# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Biserka Kojic-Prodic' _publ_contact_author_email KOJIC@IRB.HR _publ_section_title ; Salts and cocrystals of chloranilic acid with organic bases; is it possible to predict a proton transfer in a crystal? ; loop_ _publ_author_name 'Biserka Kojic-Prodic' 'Kresimir Molcanov' # Attachment '_2-MePy_2CA1.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-02-29 at 12:10:54 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : f:\programs\wingx\files\cifdoc.dat # CIF files read : 2-mepy-9 2-mepy-9-teh struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_(2-MePy)2CA _database_code_depnum_ccdc_archive 'CCDC 729420' _audit_creation_date 2008-02-29T12:10:54-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C6 H8 N, 0.5(C6 Cl2 O4)' _chemical_formula_sum 'C9 H8 Cl N O2' _chemical_formula_weight 197.61 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 6.4228(3) _cell_length_b 8.6856(4) _cell_length_c 16.7228(8) _cell_angle_alpha 90 _cell_angle_beta 101.002(6) _cell_angle_gamma 90 _cell_volume 915.75(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1434 _cell_measurement_theta_min 2.6873 _cell_measurement_theta_max 75.9566 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 3.422 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4630 _exptl_absorpt_correction_T_max 0.7100 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_measurement_device_type 'Oxford Xcalibur Nova' _diffrn_measurement_method ; CCD detector ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4323 _diffrn_reflns_number 3358 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 5.76 _diffrn_reflns_theta_max 68 _diffrn_reflns_theta_full 68 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measured_fraction_theta_full 0.975 _reflns_number_total 1624 _reflns_number_gt 1198 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0749P)^2^+0.1642P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1624 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1457 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.163 _refine_diff_density_min -0.172 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Cl1 Cl 0.13615(12) 0.75049(9) 0.45647(4) 0.0836(3) Uani 1 d . . . O1 O 0.7031(3) 1.1027(2) 0.38276(10) 0.0757(6) Uani 1 d . . . N1 N 0.2969(3) 1.4581(3) 0.25871(12) 0.0647(6) Uani 1 d . . . H1 H 0.337 1.5044 0.2188 0.078 Uiso 1 calc R . . O2 O 0.3913(3) 0.8972(2) 0.34634(10) 0.0798(6) Uani 1 d . . . C2 C 0.4359(4) 0.9403(3) 0.41807(14) 0.0592(6) Uani 1 d . . . C1 C 0.6151(4) 1.0583(3) 0.43959(13) 0.0593(6) Uani 1 d . . . C4 C 0.4253(4) 1.4626(3) 0.33100(15) 0.0654(6) Uani 1 d . . . C3 C 0.3346(4) 0.8887(3) 0.48078(13) 0.0596(6) Uani 1 d . . . C6 C 0.1599(10) 1.3062(5) 0.3761(4) 0.1211(18) Uani 1 d . . . H6 H 0.1129 1.2506 0.4167 0.145 Uiso 1 calc R . . C5 C 0.3524(8) 1.3817(4) 0.39330(18) 0.1002(12) Uani 1 d . . . H5 H 0.4334 1.3792 0.4457 0.12 Uiso 1 calc R . . C8 C 0.1111(5) 1.3869(4) 0.2442(2) 0.0891(9) Uani 1 d . . . H8 H 0.0287 1.39 0.1921 0.107 Uiso 1 calc R . . C7 C 0.0415(7) 1.3125(5) 0.3018(4) 0.1134(14) Uani 1 d . . . H7 H -0.0902 1.2642 0.2909 0.136 Uiso 1 calc R . . C9 C 0.6242(6) 1.5487(5) 0.3404(3) 0.1156(14) Uani 1 d . . . H9C H 0.6369 1.5936 0.2891 0.173 Uiso 1 calc R . . H9A H 0.7413 1.4803 0.3582 0.173 Uiso 1 calc R . . H9B H 0.625 1.6286 0.3801 0.173 Uiso 1 calc R . . 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 0.0929(6) 0.0977(6) 0.0634(4) -0.0070(3) 0.0230(4) -0.0312(4) O1 0.0891(12) 0.0938(13) 0.0524(9) -0.0064(9) 0.0340(9) -0.0176(11) N1 0.0723(13) 0.0775(13) 0.0499(10) 0.0048(10) 0.0257(10) 0.0036(11) O2 0.0881(13) 0.1066(15) 0.0491(9) -0.0147(9) 0.0245(9) -0.0196(12) C2 0.0640(14) 0.0701(13) 0.0472(11) -0.0029(11) 0.0202(11) 0.0012(12) C1 0.0638(14) 0.0702(14) 0.0478(11) -0.0017(11) 0.0206(11) 0.0023(12) C4 0.0698(14) 0.0708(15) 0.0567(13) -0.0073(12) 0.0150(12) 0.0147(13) C3 0.0646(14) 0.0683(14) 0.0484(12) -0.0014(11) 0.0175(11) -0.0039(12) C6 0.160(4) 0.083(2) 0.153(4) 0.038(3) 0.111(4) 0.021(3) C5 0.146(3) 0.103(2) 0.0538(15) 0.0163(16) 0.0242(19) 0.050(3) C8 0.0706(18) 0.100(2) 0.099(2) -0.0139(19) 0.0218(18) 0.0007(18) C7 0.100(3) 0.086(2) 0.173(5) 0.001(3) 0.074(3) -0.003(2) C9 0.083(2) 0.114(3) 0.148(4) -0.045(3) 0.019(2) -0.009(2) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C3 1.741(3) . ? O1 C1 1.256(3) . ? N1 C8 1.325(4) . ? N1 C4 1.327(3) . ? N1 H1 0.86 . ? O2 C2 1.237(3) . ? C2 C3 1.409(3) . ? C2 C1 1.531(4) . ? C1 C3 1.388(3) 3_676 ? C4 C5 1.408(5) . ? C4 C9 1.463(5) . ? C3 C1 1.388(3) 3_676 ? C6 C7 1.327(7) . ? C6 C5 1.380(7) . ? C6 H6 0.93 . ? C5 H5 0.93 . ? C8 C7 1.309(6) . ? C8 H8 0.93 . ? C7 H7 0.93 . ? C9 H9C 0.96 . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 C4 124.2(3) . . ? C8 N1 H1 117.9 . . ? C4 N1 H1 117.9 . . ? O2 C2 C3 124.8(2) . . ? O2 C2 C1 117.1(2) . . ? C3 C2 C1 118.1(2) . . ? O1 C1 C3 124.6(2) . 3_676 ? O1 C1 C2 117.0(2) . . ? C3 C1 C2 118.3(2) 3_676 . ? N1 C4 C5 115.0(3) . . ? N1 C4 C9 119.4(3) . . ? C5 C4 C9 125.6(3) . . ? C1 C3 C2 123.5(2) 3_676 . ? C1 C3 Cl1 118.62(18) 3_676 . ? C2 C3 Cl1 117.85(17) . . ? C7 C6 C5 120.4(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C5 C4 119.6(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C7 C8 N1 121.2(4) . . ? C7 C8 H8 119.4 . . ? N1 C8 H8 119.4 . . ? C8 C7 C6 119.6(4) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C4 C9 H9C 109.5 . . ? C4 C9 H9A 109.5 . . ? H9C C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9C C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C2 C1 O1 0.1(4) . . . . ? C3 C2 C1 O1 180.0(2) . . . . ? O2 C2 C1 C3 178.6(2) . . . 3_676 ? C3 C2 C1 C3 -1.6(4) . . . 3_676 ? C8 N1 C4 C5 1.3(4) . . . . ? C8 N1 C4 C9 -178.2(3) . . . . ? O2 C2 C3 C1 -178.5(3) . . . 3_676 ? C1 C2 C3 C1 1.6(4) . . . 3_676 ? O2 C2 C3 Cl1 1.6(4) . . . . ? C1 C2 C3 Cl1 -178.20(17) . . . . ? C7 C6 C5 C4 -1.6(6) . . . . ? N1 C4 C5 C6 -0.1(4) . . . . ? C9 C4 C5 C6 179.4(3) . . . . ? C4 N1 C8 C7 -0.9(5) . . . . ? N1 C8 C7 C6 -0.9(6) . . . . ? C5 C6 C7 C8 2.1(6) . . . . ? # Attachment '_5,6-phen_2H2CA.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-02-29 at 12:38:55 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : f:\programs\wingx\files\cifdoc.dat # CIF files read : pbf079 dreduc psi_scan struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_(5,6-phen)2H2CA _database_code_depnum_ccdc_archive 'CCDC 729421' _audit_creation_date 2008-02-29T12:38:55-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C15 H9 Cl1 N2 O2' _chemical_formula_sum 'C15 H9 Cl N2 O2' _chemical_formula_weight 284.69 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' 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' _cell_length_a 8.8242(5) _cell_length_b 11.6495(13) _cell_length_c 12.8506(12) _cell_angle_alpha 90 _cell_angle_beta 104.574(6) _cell_angle_gamma 90 _cell_volume 1278.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.2 _cell_measurement_theta_max 18.5 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 2.674 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.6387 _exptl_absorpt_correction_T_max 0.7633 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.54179 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 3 -1 1 2 4 0 3 2 _diffrn_reflns_number 2806 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.2 _diffrn_reflns_theta_max 76.45 _diffrn_reflns_theta_full 76.45 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 2688 _reflns_number_gt 2182 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0460P)^2^+0.3324P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0046(4) _refine_ls_number_reflns 2688 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0983 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.234 _refine_diff_density_min -0.254 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly H11 H 0.009(2) 0.7618(17) 1.1786(16) 0.052(6) Uiso 1 d . . . H5 H 0.090(2) 0.9678(17) 0.7659(18) 0.060(6) Uiso 1 d . . . H7 H 0.393(3) 0.941(2) 1.062(2) 0.080(7) Uiso 1 d . . . H14 H -0.450(3) 0.724(2) 0.914(2) 0.086(8) Uiso 1 d . . . H8 H 0.209(2) 0.8475(19) 1.1278(18) 0.063(6) Uiso 1 d . . . H6 H 0.333(3) 1.003(2) 0.8775(19) 0.070(7) Uiso 1 d . . . H13 H -0.436(3) 0.657(2) 1.094(2) 0.101(9) Uiso 1 d . . . H12 H -0.197(3) 0.683(2) 1.226(2) 0.077(7) Uiso 1 d . . . H1 H -0.302(3) 0.414(2) 0.831(2) 0.091(9) Uiso 1 d . . . Cl1 Cl 0.21531(6) 0.61618(4) 0.86775(4) 0.05591(17) Uani 1 d . . . O1 O -0.29158(15) 0.41914(14) 0.89609(11) 0.0555(4) Uani 1 d . . . O2 O -0.10801(16) 0.53172(13) 0.79038(10) 0.0603(4) Uani 1 d . . . C4 C 0.00304(18) 0.88419(14) 0.88061(12) 0.0378(3) Uani 1 d . . . N1 N -0.14043(17) 0.86413(13) 0.80923(11) 0.0448(3) Uani 1 d . . . C2 C -0.05383(19) 0.51577(14) 0.88558(12) 0.0395(4) Uani 1 d . . . C1 C -0.15383(18) 0.45719(15) 0.94949(13) 0.0395(4) Uani 1 d . . . N2 N -0.25180(17) 0.81271(14) 0.83817(12) 0.0506(4) Uani 1 d . . . C10 C -0.08900(18) 0.79262(14) 1.02184(12) 0.0380(3) Uani 1 d . . . C3 C 0.10209(19) 0.55255(14) 0.94295(13) 0.0389(4) Uani 1 d . . . C9 C 0.03539(17) 0.84824(14) 0.98833(12) 0.0364(3) Uani 1 d . . . C15 C -0.2304(2) 0.77794(16) 0.94355(14) 0.0446(4) Uani 1 d . . . C5 C 0.1154(2) 0.94241(16) 0.84064(16) 0.0484(4) Uani 1 d . . . C11 C -0.0801(2) 0.75390(17) 1.12713(14) 0.0494(4) Uani 1 d . . . C8 C 0.1851(2) 0.87130(17) 1.05528(15) 0.0495(4) Uani 1 d . . . C6 C 0.2590(2) 0.9627(2) 0.9071(2) 0.0609(5) Uani 1 d . . . C12 C -0.2085(3) 0.7059(2) 1.15108(19) 0.0648(6) Uani 1 d . . . C14 C -0.3604(2) 0.7275(2) 0.9704(2) 0.0637(6) Uani 1 d . . . C7 C 0.2930(2) 0.9275(2) 1.01459(19) 0.0625(6) Uani 1 d . . . C13 C -0.3493(3) 0.6938(2) 1.0737(2) 0.0714(7) Uani 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 0.0610(3) 0.0664(3) 0.0467(3) -0.0033(2) 0.0255(2) -0.0156(2) O1 0.0414(7) 0.0847(10) 0.0382(7) -0.0089(6) 0.0060(5) -0.0157(6) O2 0.0620(8) 0.0809(10) 0.0323(6) 0.0064(6) 0.0010(6) -0.0135(7) C4 0.0363(8) 0.0419(8) 0.0346(8) -0.0044(6) 0.0075(6) 0.0030(7) N1 0.0414(7) 0.0573(9) 0.0313(7) 0.0025(6) 0.0011(6) 0.0001(6) C2 0.0445(9) 0.0429(9) 0.0299(7) -0.0030(6) 0.0072(6) -0.0002(7) C1 0.0370(8) 0.0460(9) 0.0351(8) -0.0059(7) 0.0084(6) -0.0021(7) N2 0.0386(7) 0.0646(10) 0.0417(8) 0.0049(7) -0.0028(6) -0.0035(7) C10 0.0380(8) 0.0409(8) 0.0348(8) -0.0008(6) 0.0085(6) 0.0067(6) C3 0.0399(8) 0.0435(9) 0.0354(8) -0.0026(6) 0.0137(6) -0.0025(7) C9 0.0334(8) 0.0410(8) 0.0327(7) -0.0054(6) 0.0045(6) 0.0052(6) C15 0.0371(8) 0.0510(10) 0.0438(9) 0.0033(8) 0.0068(7) 0.0013(7) C5 0.0499(10) 0.0512(10) 0.0484(10) -0.0026(8) 0.0202(8) -0.0001(8) C11 0.0574(11) 0.0532(11) 0.0374(9) 0.0036(8) 0.0115(8) 0.0090(9) C8 0.0379(9) 0.0613(12) 0.0424(10) -0.0065(8) -0.0025(7) 0.0028(8) C6 0.0440(10) 0.0653(13) 0.0778(14) -0.0088(11) 0.0234(10) -0.0108(9) C12 0.0850(16) 0.0630(13) 0.0562(12) 0.0134(10) 0.0363(12) 0.0074(11) C14 0.0426(10) 0.0716(14) 0.0760(15) 0.0130(12) 0.0132(10) -0.0049(10) C7 0.0342(9) 0.0734(14) 0.0724(14) -0.0133(11) -0.0005(9) -0.0046(9) C13 0.0631(14) 0.0720(15) 0.0897(17) 0.0165(12) 0.0389(13) -0.0027(11) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C3 1.7226(16) . ? O1 C1 1.313(2) . ? O1 H1 0.82(3) . ? O2 C2 1.2105(19) . ? C4 N1 1.384(2) . ? C4 C5 1.401(2) . ? C4 C9 1.405(2) . ? N1 N2 1.283(2) . ? C2 C3 1.452(2) . ? C2 C1 1.511(2) . ? C1 C3 1.347(2) 3_567 ? N2 C15 1.380(2) . ? C10 C15 1.402(2) . ? C10 C11 1.409(2) . ? C10 C9 1.431(2) . ? C3 C1 1.347(2) 3_567 ? C9 C8 1.409(2) . ? C15 C14 1.407(3) . ? C5 C6 1.359(3) . ? C5 H5 0.98(2) . ? C11 C12 1.366(3) . ? C11 H11 0.89(2) . ? C8 C7 1.364(3) . ? C8 H8 0.94(2) . ? C6 C7 1.399(3) . ? C6 H6 0.96(2) . ? C12 C13 1.389(4) . ? C12 H12 0.98(2) . ? C14 C13 1.364(3) . ? C14 H14 0.93(3) . ? C7 H7 0.95(3) . ? C13 H13 0.97(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 114.4(19) . . ? N1 C4 C5 116.91(15) . . ? N1 C4 C9 121.87(15) . . ? C5 C4 C9 121.22(15) . . ? N2 N1 C4 121.77(14) . . ? O2 C2 C3 123.39(16) . . ? O2 C2 C1 118.85(15) . . ? C3 C2 C1 117.74(14) . . ? O1 C1 C3 122.54(16) . 3_567 ? O1 C1 C2 117.30(14) . . ? C3 C1 C2 120.15(15) 3_567 . ? N1 N2 C15 119.70(14) . . ? C15 C10 C11 118.32(16) . . ? C15 C10 C9 116.78(14) . . ? C11 C10 C9 124.88(16) . . ? C1 C3 C2 121.95(15) 3_567 . ? C1 C3 Cl1 121.14(13) 3_567 . ? C2 C3 Cl1 116.83(12) . . ? C4 C9 C8 118.14(16) . . ? C4 C9 C10 116.76(14) . . ? C8 C9 C10 125.08(15) . . ? N2 C15 C10 123.07(16) . . ? N2 C15 C14 116.39(17) . . ? C10 C15 C14 120.54(18) . . ? C6 C5 C4 119.21(18) . . ? C6 C5 H5 120.8(13) . . ? C4 C5 H5 120.0(13) . . ? C12 C11 C10 119.86(19) . . ? C12 C11 H11 119.9(13) . . ? C10 C11 H11 120.2(13) . . ? C7 C8 C9 119.69(18) . . ? C7 C8 H8 121.1(13) . . ? C9 C8 H8 119.2(13) . . ? C5 C6 C7 120.25(19) . . ? C5 C6 H6 117.3(14) . . ? C7 C6 H6 122.4(14) . . ? C11 C12 C13 121.6(2) . . ? C11 C12 H12 116.7(14) . . ? C13 C12 H12 121.7(14) . . ? C13 C14 C15 119.7(2) . . ? C13 C14 H14 125.5(17) . . ? C15 C14 H14 114.7(17) . . ? C8 C7 C6 121.48(18) . . ? C8 C7 H7 117.5(15) . . ? C6 C7 H7 121.1(15) . . ? C14 C13 C12 120.0(2) . . ? C14 C13 H13 121.6(18) . . ? C12 C13 H13 118.4(17) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C4 N1 N2 -179.17(16) . . . . ? C9 C4 N1 N2 0.7(3) . . . . ? O2 C2 C1 O1 4.7(3) . . . . ? C3 C2 C1 O1 -176.70(15) . . . . ? O2 C2 C1 C3 -174.08(17) . . . 3_567 ? C3 C2 C1 C3 4.5(3) . . . 3_567 ? C4 N1 N2 C15 1.2(3) . . . . ? O2 C2 C3 C1 173.93(18) . . . 3_567 ? C1 C2 C3 C1 -4.6(3) . . . 3_567 ? O2 C2 C3 Cl1 -2.9(2) . . . . ? C1 C2 C3 Cl1 178.58(12) . . . . ? N1 C4 C9 C8 179.45(16) . . . . ? C5 C4 C9 C8 -0.6(2) . . . . ? N1 C4 C9 C10 -1.8(2) . . . . ? C5 C4 C9 C10 178.13(15) . . . . ? C15 C10 C9 C4 0.9(2) . . . . ? C11 C10 C9 C4 -178.00(16) . . . . ? C15 C10 C9 C8 179.56(16) . . . . ? C11 C10 C9 C8 0.7(3) . . . . ? N1 N2 C15 C10 -2.1(3) . . . . ? N1 N2 C15 C14 176.81(18) . . . . ? C11 C10 C15 N2 179.98(17) . . . . ? C9 C10 C15 N2 1.0(3) . . . . ? C11 C10 C15 C14 1.1(3) . . . . ? C9 C10 C15 C14 -177.90(18) . . . . ? N1 C4 C5 C6 -179.03(18) . . . . ? C9 C4 C5 C6 1.1(3) . . . . ? C15 C10 C11 C12 -1.5(3) . . . . ? C9 C10 C11 C12 177.38(18) . . . . ? C4 C9 C8 C7 0.3(3) . . . . ? C10 C9 C8 C7 -178.40(18) . . . . ? C4 C5 C6 C7 -1.1(3) . . . . ? C10 C11 C12 C13 0.1(3) . . . . ? N2 C15 C14 C13 -178.3(2) . . . . ? C10 C15 C14 C13 0.7(3) . . . . ? C9 C8 C7 C6 -0.3(3) . . . . ? C5 C6 C7 C8 0.7(3) . . . . ? C15 C14 C13 C12 -2.1(4) . . . . ? C11 C12 C13 C14 1.7(4) . . . . ? # Attachment '_Me2NH2_2CA1.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-02-29 at 12:05:50 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : f:\programs\wingx\files\cifdoc.dat # CIF files read : gvanozin-ca-1 gvanozin-ca-1-teh struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_(Me2NH2)2CA _database_code_depnum_ccdc_archive 'CCDC 729422' _audit_creation_date 2008-02-29T12:05:50-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C6 Cl2 O4, 2(C2 H8 N)' _chemical_formula_sum 'C10 H16 Cl2 N2 O4' _chemical_formula_weight 299.15 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' 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' _cell_length_a 8.59030(10) _cell_length_b 9.11280(10) _cell_length_c 9.31810(10) _cell_angle_alpha 90 _cell_angle_beta 105.7360(10) _cell_angle_gamma 90 _cell_volume 702.098(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4764 _cell_measurement_theta_min 4.8533 _cell_measurement_theta_max 76.214 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 4.259 _exptl_absorpt_correction_T_min 0.2926 _exptl_absorpt_correction_T_max 0.5500 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_measurement_device_type 'Oxford Xcalibur Nova R' _diffrn_measurement_method ; CCD detector ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4323 _diffrn_reflns_number 7199 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 6.22 _diffrn_reflns_theta_max 76.34 _diffrn_reflns_theta_full 76.34 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measured_fraction_theta_full 0.983 _reflns_number_total 1448 _reflns_number_gt 1335 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^+0.1919P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.031(2) _refine_ls_number_reflns 1448 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1088 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.259 _refine_diff_density_min -0.465 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Cl1 Cl 0.24290(6) 0.28768(7) 0.29357(5) 0.0700(3) Uani 1 d . . . O1 O 0.50913(15) 0.52402(14) 0.79233(12) 0.0499(3) Uani 1 d . . . C2 C 0.38963(19) 0.41268(17) 0.55761(17) 0.0414(4) Uani 1 d . . . C1 C 0.51324(18) 0.51659(17) 0.65880(16) 0.0393(4) Uani 1 d . . . N1 N 0.32261(19) 0.36307(19) -0.06322(16) 0.0571(4) Uani 1 d . . . H1A H 0.3712 0.4055 -0.1269 0.068 Uiso 1 calc R . . H1B H 0.3669 0.4013 0.0278 0.068 Uiso 1 calc R . . O2 O 0.30178(17) 0.34155(16) 0.61667(14) 0.0624(4) Uani 1 d . . . C3 C 0.38322(19) 0.40611(18) 0.40422(17) 0.0430(4) Uani 1 d . . . C4 C 0.3569(3) 0.2049(2) -0.0580(3) 0.0694(6) Uani 1 d . . . H4A H 0.4718 0.1896 -0.0266 0.104 Uiso 1 calc R . . H4B H 0.3136 0.1633 -0.1553 0.104 Uiso 1 calc R . . H4C H 0.3079 0.1586 0.0114 0.104 Uiso 1 calc R . . C5 C 0.1494(3) 0.4013(3) -0.1093(3) 0.0756(6) Uani 1 d . . . H5A H 0.1376 0.506 -0.1097 0.113 Uiso 1 calc R . . H5C H 0.0966 0.359 -0.0406 0.113 Uiso 1 calc R . . H5B H 0.1012 0.3637 -0.2075 0.113 Uiso 1 calc R . . 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 0.0738(4) 0.0962(5) 0.0447(3) -0.0214(2) 0.0240(2) -0.0408(3) O1 0.0578(7) 0.0647(7) 0.0314(6) -0.0054(5) 0.0191(5) -0.0129(5) C2 0.0451(8) 0.0477(8) 0.0353(8) -0.0012(6) 0.0175(6) -0.0029(6) C1 0.0440(8) 0.0456(8) 0.0309(7) -0.0013(6) 0.0147(6) 0.0011(6) N1 0.0654(9) 0.0757(10) 0.0347(7) -0.0089(7) 0.0214(6) -0.0301(8) O2 0.0724(8) 0.0803(9) 0.0416(7) -0.0071(6) 0.0274(6) -0.0315(7) C3 0.0457(8) 0.0513(8) 0.0339(8) -0.0064(6) 0.0143(6) -0.0078(6) C4 0.0807(14) 0.0805(14) 0.0543(12) -0.0051(10) 0.0306(10) -0.0166(11) C5 0.0720(13) 0.1024(17) 0.0574(12) 0.0031(12) 0.0262(10) -0.0088(12) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C3 1.7340(16) . ? O1 C1 1.2561(18) . ? C2 O2 1.2320(19) . ? C2 C3 1.417(2) . ? C2 C1 1.540(2) . ? C1 C3 1.384(2) 3_666 ? N1 C4 1.469(3) . ? N1 C5 1.474(3) . ? N1 H1A 0.9 . ? N1 H1B 0.9 . ? C3 C1 1.384(2) 3_666 ? C4 H4A 0.96 . ? C4 H4B 0.96 . ? C4 H4C 0.96 . ? C5 H5A 0.96 . ? C5 H5C 0.96 . ? C5 H5B 0.96 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C2 C3 124.58(15) . . ? O2 C2 C1 117.02(13) . . ? C3 C2 C1 118.40(13) . . ? O1 C1 C3 125.93(14) . 3_666 ? O1 C1 C2 116.09(13) . . ? C3 C1 C2 117.97(13) 3_666 . ? C4 N1 C5 114.78(17) . . ? C4 N1 H1A 108.6 . . ? C5 N1 H1A 108.6 . . ? C4 N1 H1B 108.6 . . ? C5 N1 H1B 108.6 . . ? H1A N1 H1B 107.5 . . ? C1 C3 C2 123.57(14) 3_666 . ? C1 C3 Cl1 119.18(11) 3_666 . ? C2 C3 Cl1 117.18(12) . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? H5C C5 H5B 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C2 C1 O1 -2.7(2) . . . . ? C3 C2 C1 O1 176.67(15) . . . . ? O2 C2 C1 C3 177.89(16) . . . 3_666 ? C3 C2 C1 C3 -2.7(2) . . . 3_666 ? O2 C2 C3 C1 -177.78(17) . . . 3_666 ? C1 C2 C3 C1 2.8(3) . . . 3_666 ? O2 C2 C3 Cl1 -0.7(2) . . . . ? C1 C2 C3 Cl1 179.88(11) . . . . ? # Attachment '2-MePy-HCA-monoclinic1.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-02-11 at 12:43:05 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : f:\programs\wingx\files\cifdoc.dat # CIF files read : 2-mepy-11 2-mepy-11-teh struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_2-MePy-HCA-monoclinic _database_code_depnum_ccdc_archive 'CCDC 729423' _audit_creation_date 2008-02-11T12:43:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C6 H8 N, C6 H Cl2 O4' _chemical_formula_sum 'C12 H9 Cl2 N1 O4' _chemical_formula_weight 302.11 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 7.1312(1) _cell_length_b 11.8937(1) _cell_length_c 15.3644(2) _cell_angle_alpha 90 _cell_angle_beta 103.206(1) _cell_angle_gamma 90 _cell_volume 1268.69(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8012 _cell_measurement_theta_min 2.9483 _cell_measurement_theta_max 75.9707 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description rod _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 4.715 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4482 _exptl_absorpt_correction_T_max 0.6900 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_measurement_device_type 'Oxford Xcalibur Nova' _diffrn_measurement_method ; CCD detector ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4323 _diffrn_reflns_number 12298 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.75 _diffrn_reflns_theta_max 76.27 _diffrn_reflns_theta_full 76.27 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measured_fraction_theta_full 0.981 _reflns_number_total 2607 _reflns_number_gt 2392 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0670P)^2^+0.1892P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 2607 _refine_ls_number_parameters 198 _refine_ls_number_restraints 7 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.1005 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.284 _refine_ls_shift/su_max 0.01 _refine_diff_density_max 0.293 _refine_diff_density_min -0.317 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly H8 H -0.751(4) 1.339(2) 0.2773(18) 0.063(7) Uiso 1 d . . . H9 H -0.868(4) 1.479(2) 0.1717(19) 0.063(7) Uiso 1 d . . . H11 H -0.481(4) 1.388(2) 0.039(2) 0.068(8) Uiso 1 d . . . H1 H -0.374(4) 1.263(2) 0.1408(16) 0.053(6) Uiso 1 d . . . H10 H -0.723(4) 1.504(3) 0.051(2) 0.074(8) Uiso 1 d . . . H2 H 0.414(4) 1.087(2) -0.043(2) 0.092(11) Uiso 1 d D . . Cl2 Cl 0.12585(7) 0.97002(4) 0.20582(3) 0.05208(18) Uani 1 d . . . Cl1 Cl 0.06130(8) 1.31994(5) -0.11009(3) 0.0597(2) Uani 1 d . . . O1 O 0.3614(2) 0.98907(13) 0.06928(10) 0.0570(4) Uani 1 d . . . O3 O -0.1878(2) 1.30192(13) 0.02079(11) 0.0626(4) Uani 1 d . . . O2 O 0.3421(2) 1.14049(14) -0.05922(10) 0.0561(4) Uani 1 d D . . O4 O -0.1690(2) 1.15333(14) 0.15379(11) 0.0579(4) Uani 1 d . . . N1 N -0.4688(2) 1.30119(13) 0.14565(10) 0.0414(3) Uani 1 d . . . C4 C -0.0632(2) 1.23053(15) 0.03022(12) 0.0419(4) Uani 1 d . . . C2 C 0.2129(2) 1.14488(15) -0.01035(11) 0.0393(4) Uani 1 d . . . C6 C 0.0997(2) 1.06557(14) 0.11883(11) 0.0377(4) Uani 1 d . . . C3 C 0.0741(3) 1.22339(15) -0.02544(12) 0.0413(4) Uani 1 d . . . C1 C 0.2303(2) 1.05883(14) 0.06320(11) 0.0380(4) Uani 1 d . . . C5 C -0.0480(2) 1.14460(15) 0.10719(11) 0.0399(4) Uani 1 d . . . C7 C -0.5465(3) 1.28268(16) 0.21594(12) 0.0424(4) Uani 1 d . . . C8 C -0.6994(3) 1.34920(19) 0.22514(14) 0.0512(5) Uani 1 d . . . C10 C -0.6835(3) 1.44864(18) 0.09290(16) 0.0548(5) Uani 1 d . . . C11 C -0.5338(3) 1.38117(18) 0.08493(15) 0.0523(5) Uani 1 d . . . C12 C -0.4654(4) 1.1915(2) 0.27952(17) 0.0678(7) Uani 1 d D . . H12A H -0.394(3) 1.1355(12) 0.2487(6) 0.102 Uiso 1 calc RD . . H12B H -0.5742(11) 1.1513(13) 0.2998(12) 0.102 Uiso 1 calc RD . . H12C H -0.372(3) 1.2250(5) 0.3336(9) 0.102 Uiso 1 calc RD . . C9 C -0.7671(3) 1.43158(17) 0.16433(15) 0.0533(5) Uani 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 Cl2 0.0536(3) 0.0565(3) 0.0524(3) 0.01672(19) 0.0251(2) 0.01190(19) Cl1 0.0645(3) 0.0601(3) 0.0614(3) 0.0253(2) 0.0288(2) 0.0269(2) O1 0.0533(8) 0.0639(9) 0.0631(9) 0.0206(7) 0.0327(7) 0.0307(7) O3 0.0568(9) 0.0625(9) 0.0774(10) 0.0185(7) 0.0340(8) 0.0313(7) O2 0.0564(8) 0.0645(9) 0.0580(8) 0.0239(7) 0.0349(6) 0.0306(7) O4 0.0529(8) 0.0661(9) 0.0658(9) 0.0135(7) 0.0367(7) 0.0211(7) N1 0.0355(7) 0.0428(7) 0.0498(8) 0.0013(6) 0.0178(6) 0.0075(6) C4 0.0374(9) 0.0424(9) 0.0486(9) 0.0008(7) 0.0155(7) 0.0103(7) C2 0.0379(9) 0.0436(8) 0.0398(8) 0.0038(7) 0.0163(6) 0.0093(7) C6 0.0369(8) 0.0394(8) 0.0392(8) 0.0030(6) 0.0139(6) 0.0046(6) C3 0.0412(9) 0.0425(9) 0.0430(8) 0.0068(7) 0.0155(7) 0.0102(7) C1 0.0356(8) 0.0401(8) 0.0404(8) 0.0028(6) 0.0129(6) 0.0097(6) C5 0.0362(8) 0.0430(8) 0.0441(8) -0.0008(7) 0.0170(7) 0.0062(6) C7 0.0386(8) 0.0471(9) 0.0432(8) 0.0014(7) 0.0127(7) 0.0022(7) C8 0.0518(11) 0.0577(11) 0.0512(10) 0.0014(8) 0.0268(9) 0.0093(9) C10 0.0557(11) 0.0456(10) 0.0699(13) 0.0163(9) 0.0285(10) 0.0134(9) C11 0.0511(11) 0.0545(11) 0.0600(11) 0.0130(9) 0.0308(9) 0.0112(9) C12 0.0579(13) 0.0871(17) 0.0622(13) 0.0289(12) 0.0215(10) 0.0231(12) C9 0.0515(11) 0.0462(10) 0.0698(13) 0.0009(9) 0.0296(9) 0.0132(8) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl2 C6 1.7317(17) . ? Cl1 C3 1.7216(17) . ? O1 C1 1.237(2) . ? O3 C4 1.213(2) . ? O2 C2 1.316(2) . ? O2 H2 0.82(2) . ? O4 C5 1.245(2) . ? N1 C11 1.339(2) . ? N1 C7 1.340(2) . ? N1 H1 0.84(3) . ? C4 C3 1.442(2) . ? C4 C5 1.548(2) . ? C2 C3 1.342(2) . ? C2 C1 1.509(2) . ? C6 C5 1.392(2) . ? C6 C1 1.403(2) . ? C7 C8 1.380(3) . ? C7 C12 1.486(3) . ? C8 C9 1.364(3) . ? C8 H8 0.96(3) . ? C10 C11 1.363(3) . ? C10 C9 1.378(3) . ? C10 H10 0.92(3) . ? C11 H11 0.88(3) . ? C12 H12A 1.0187 . ? C12 H12B 1.0187 . ? C12 H12C 1.0187 . ? C9 H9 0.94(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 H2 109(3) . . ? C11 N1 C7 122.50(16) . . ? C11 N1 H1 119.1(17) . . ? C7 N1 H1 118.4(17) . . ? O3 C4 C3 123.24(17) . . ? O3 C4 C5 118.35(15) . . ? C3 C4 C5 118.39(14) . . ? O2 C2 C3 120.93(16) . . ? O2 C2 C1 116.86(14) . . ? C3 C2 C1 122.21(15) . . ? C5 C6 C1 123.25(15) . . ? C5 C6 Cl2 119.15(13) . . ? C1 C6 Cl2 117.60(12) . . ? C2 C3 C4 120.83(16) . . ? C2 C3 Cl1 120.29(13) . . ? C4 C3 Cl1 118.86(13) . . ? O1 C1 C6 125.98(16) . . ? O1 C1 C2 116.31(15) . . ? C6 C1 C2 117.70(14) . . ? O4 C5 C6 125.85(17) . . ? O4 C5 C4 116.57(15) . . ? C6 C5 C4 117.57(14) . . ? N1 C7 C8 118.05(17) . . ? N1 C7 C12 118.63(17) . . ? C8 C7 C12 123.32(18) . . ? C9 C8 C7 120.40(18) . . ? C9 C8 H8 121.5(16) . . ? C7 C8 H8 118.0(16) . . ? C11 C10 C9 118.35(19) . . ? C11 C10 H10 119(2) . . ? C9 C10 H10 123(2) . . ? N1 C11 C10 120.62(18) . . ? N1 C11 H11 119.0(19) . . ? C10 C11 H11 120.4(19) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C9 C10 120.09(18) . . ? C8 C9 H9 120.6(18) . . ? C10 C9 H9 119.3(18) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C2 C3 C4 -177.79(18) . . . . ? C1 C2 C3 C4 1.5(3) . . . . ? O2 C2 C3 Cl1 0.4(3) . . . . ? C1 C2 C3 Cl1 179.77(13) . . . . ? O3 C4 C3 C2 177.9(2) . . . . ? C5 C4 C3 C2 -0.6(3) . . . . ? O3 C4 C3 Cl1 -0.4(3) . . . . ? C5 C4 C3 Cl1 -178.90(13) . . . . ? C5 C6 C1 O1 -178.39(19) . . . . ? Cl2 C6 C1 O1 1.5(3) . . . . ? C5 C6 C1 C2 2.5(3) . . . . ? Cl2 C6 C1 C2 -177.60(13) . . . . ? O2 C2 C1 O1 -2.3(3) . . . . ? C3 C2 C1 O1 178.36(19) . . . . ? O2 C2 C1 C6 176.94(17) . . . . ? C3 C2 C1 C6 -2.4(3) . . . . ? C1 C6 C5 O4 179.04(19) . . . . ? Cl2 C6 C5 O4 -0.9(3) . . . . ? C1 C6 C5 C4 -1.6(3) . . . . ? Cl2 C6 C5 C4 178.42(12) . . . . ? O3 C4 C5 O4 1.4(3) . . . . ? C3 C4 C5 O4 -179.98(18) . . . . ? O3 C4 C5 C6 -177.95(18) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C11 N1 C7 C8 0.1(3) . . . . ? C11 N1 C7 C12 179.6(2) . . . . ? N1 C7 C8 C9 -0.4(3) . . . . ? C12 C7 C8 C9 -180.0(2) . . . . ? C7 N1 C11 C10 0.5(3) . . . . ? C9 C10 C11 N1 -0.7(4) . . . . ? C7 C8 C9 C10 0.3(4) . . . . ? C11 C10 C9 C8 0.3(4) . . . . ? # Attachment '2-MePy-HCA-triclinic1.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-02-11 at 11:31:11 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : f:\programs\wingx\files\cifdoc.dat # CIF files read : 2-mepy-1 2-mepy-1-teh struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_2-MePy-HCA-triclinic _database_code_depnum_ccdc_archive 'CCDC 729424' _audit_creation_date 2008-02-11T11:31:11-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C6 H8 N, C6 H Cl2 O4' _chemical_formula_sum 'C12 H9 Cl2 N1 O4' _chemical_formula_weight 302.11 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5343(3) _cell_length_b 9.1981(4) _cell_length_c 9.7929(5) _cell_angle_alpha 101.951(4) _cell_angle_beta 103.166(4) _cell_angle_gamma 98.562(4) _cell_volume 632.66(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4480 _cell_measurement_theta_min 4.7735 _cell_measurement_theta_max 76.1861 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 4.727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5063 _exptl_absorpt_correction_T_max 0.6500 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.54179 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_measurement_device_type 'Oxford Xcalibur Nova' _diffrn_measurement_method ; CCD detector ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4323 _diffrn_radiation_probe x-ray _diffrn_reflns_number 6799 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.79 _diffrn_reflns_theta_max 75 _diffrn_reflns_theta_full 75 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measured_fraction_theta_full 0.979 _reflns_number_total 2550 _reflns_number_gt 2296 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0581P)^2^+0.1559P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 2550 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.1055 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.283 _refine_diff_density_min -0.436 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 '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' Cl Cl 0.364 0.702 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.031 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.049 0.032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly N1 N 0.1136(2) 0.54049(16) 0.23417(16) 0.0449(3) Uani 1 d . . . C7 C 0.1471(2) 0.43550(18) 0.13171(18) 0.0439(4) Uani 1 d . . . C12 C 0.2967(3) 0.4805(3) 0.0636(2) 0.0577(5) Uani 1 d . . . C8 C 0.0397(3) 0.2903(2) 0.0966(2) 0.0551(5) Uani 1 d . . . C11 C -0.0145(3) 0.5110(2) 0.3053(2) 0.0574(5) Uani 1 d . . . C10 C -0.1199(3) 0.3678(3) 0.2740(3) 0.0643(5) Uani 1 d . . . C9 C -0.0928(3) 0.2573(2) 0.1682(3) 0.0645(6) Uani 1 d . . . H9 H -0.168(4) 0.160(3) 0.139(3) 0.079(8) Uiso 1 d . . . H11 H -0.030(3) 0.593(3) 0.374(3) 0.065(7) Uiso 1 d . . . H8 H 0.062(4) 0.217(4) 0.020(3) 0.084(8) Uiso 1 d . . . H10 H -0.221(4) 0.346(3) 0.319(3) 0.079(8) Uiso 1 d . . . H12C H 0.408(5) 0.463(4) 0.119(4) 0.093(9) Uiso 1 d . . . H12A H 0.320(5) 0.580(4) 0.070(3) 0.098(10) Uiso 1 d . . . H12B H 0.281(4) 0.421(4) -0.029(4) 0.088(9) Uiso 1 d . . . H1 H 0.173(3) 0.635(3) 0.258(3) 0.059(6) Uiso 1 d . . . H2 H 0.424(4) 0.429(4) 0.586(3) 0.090(10) Uiso 1 d . . . Cl2 Cl 0.40292(7) 0.08925(5) 0.12337(5) 0.05396(16) Uani 1 d . . . Cl1 Cl 0.22438(8) 0.10690(6) 0.72835(5) 0.06218(17) Uani 1 d . . . O1 O 0.4535(2) 0.35509(13) 0.37385(14) 0.0524(3) Uani 1 d . . . C2 C 0.3428(2) 0.22934(17) 0.53161(18) 0.0408(3) Uani 1 d . . . O4 O 0.2561(2) -0.17541(13) 0.22886(15) 0.0564(3) Uani 1 d . . . O2 O 0.3758(2) 0.36458(14) 0.62324(14) 0.0545(3) Uani 1 d . . . O3 O 0.1889(2) -0.16472(14) 0.48822(16) 0.0613(4) Uani 1 d . . . C4 C 0.2432(2) -0.04485(18) 0.46248(19) 0.0432(4) Uani 1 d . . . C5 C 0.2847(2) -0.04807(17) 0.31460(19) 0.0419(3) Uani 1 d . . . C1 C 0.3880(2) 0.22938(16) 0.38939(17) 0.0391(3) Uani 1 d . . . C3 C 0.2733(2) 0.10136(19) 0.56466(18) 0.0428(4) Uani 1 d . . . C6 C 0.3527(2) 0.08961(17) 0.28703(18) 0.0409(3) Uani 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 N1 0.0512(8) 0.0302(6) 0.0473(7) 0.0058(6) 0.0120(6) -0.0026(6) C7 0.0459(8) 0.0373(8) 0.0442(8) 0.0089(6) 0.0058(7) 0.0070(6) C12 0.0586(11) 0.0580(12) 0.0550(11) 0.0091(9) 0.0189(9) 0.0089(9) C8 0.0588(10) 0.0348(8) 0.0608(11) 0.0009(8) 0.0064(8) 0.0061(7) C11 0.0657(11) 0.0455(10) 0.0561(11) 0.0043(8) 0.0240(9) -0.0034(8) C10 0.0653(12) 0.0563(11) 0.0674(12) 0.0174(10) 0.0220(10) -0.0093(9) C9 0.0636(12) 0.0357(9) 0.0826(14) 0.0147(9) 0.0082(10) -0.0076(8) Cl2 0.0683(3) 0.0418(2) 0.0519(3) 0.00291(18) 0.0280(2) 0.00541(19) Cl1 0.0858(4) 0.0556(3) 0.0476(3) 0.0175(2) 0.0237(2) 0.0065(2) O1 0.0755(8) 0.0275(5) 0.0510(7) 0.0050(5) 0.0221(6) -0.0011(5) C2 0.0455(8) 0.0306(7) 0.0419(8) 0.0050(6) 0.0083(6) 0.0050(6) O4 0.0715(8) 0.0287(6) 0.0629(8) -0.0012(5) 0.0246(7) -0.0016(5) O2 0.0832(9) 0.0306(6) 0.0464(7) 0.0025(5) 0.0232(6) 0.0025(6) O3 0.0792(9) 0.0359(6) 0.0596(8) 0.0156(6) 0.0095(7) -0.0070(6) C4 0.0426(8) 0.0319(7) 0.0488(9) 0.0100(6) 0.0048(7) 0.0004(6) C5 0.0404(8) 0.0280(7) 0.0514(9) 0.0037(6) 0.0092(6) 0.0024(6) C1 0.0433(8) 0.0276(7) 0.0435(8) 0.0060(6) 0.0108(6) 0.0038(6) C3 0.0481(8) 0.0371(8) 0.0409(8) 0.0098(6) 0.0101(6) 0.0040(6) C6 0.0454(8) 0.0305(7) 0.0441(8) 0.0040(6) 0.0141(6) 0.0037(6) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.338(2) . ? N1 C11 1.341(2) . ? N1 H1 0.88(3) . ? C7 C8 1.385(2) . ? C7 C12 1.485(3) . ? C12 H12C 0.95(3) . ? C12 H12A 0.90(4) . ? C12 H12B 0.92(3) . ? C8 C9 1.378(3) . ? C8 H8 0.97(3) . ? C11 C10 1.368(3) . ? C11 H11 0.94(3) . ? C10 C9 1.367(3) . ? C10 H10 0.98(3) . ? C9 H9 0.94(3) . ? Cl2 C6 1.7279(17) . ? Cl1 C3 1.7174(17) . ? O1 C1 1.2413(19) . ? C2 O2 1.326(2) . ? C2 C3 1.348(2) . ? C2 C1 1.507(2) . ? O4 C5 1.248(2) . ? O2 H2 0.84(3) . ? O3 C4 1.214(2) . ? C4 C3 1.453(2) . ? C4 C5 1.545(2) . ? C5 C6 1.397(2) . ? C1 C6 1.404(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C11 123.38(15) . . ? C7 N1 H1 121.7(15) . . ? C11 N1 H1 114.9(15) . . ? N1 C7 C8 117.43(17) . . ? N1 C7 C12 118.54(16) . . ? C8 C7 C12 124.03(18) . . ? C7 C12 H12C 107.0(19) . . ? C7 C12 H12A 112(2) . . ? H12C C12 H12A 105(3) . . ? C7 C12 H12B 114.0(18) . . ? H12C C12 H12B 105(3) . . ? H12A C12 H12B 113(3) . . ? C9 C8 C7 120.22(19) . . ? C9 C8 H8 123.1(17) . . ? C7 C8 H8 116.7(17) . . ? N1 C11 C10 120.10(19) . . ? N1 C11 H11 117.0(15) . . ? C10 C11 H11 122.9(15) . . ? C9 C10 C11 118.6(2) . . ? C9 C10 H10 119.7(17) . . ? C11 C10 H10 121.5(17) . . ? C10 C9 C8 120.24(18) . . ? C10 C9 H9 121.2(17) . . ? C8 C9 H9 118.4(17) . . ? O2 C2 C3 121.71(16) . . ? O2 C2 C1 115.49(14) . . ? C3 C2 C1 122.81(14) . . ? C2 O2 H2 108(2) . . ? O3 C4 C3 123.19(17) . . ? O3 C4 C5 118.43(15) . . ? C3 C4 C5 118.38(14) . . ? O4 C5 C6 124.89(17) . . ? O4 C5 C4 116.79(15) . . ? C6 C5 C4 118.32(14) . . ? O1 C1 C6 125.89(15) . . ? O1 C1 C2 116.12(13) . . ? C6 C1 C2 117.99(14) . . ? C2 C3 C4 119.94(16) . . ? C2 C3 Cl1 121.15(13) . . ? C4 C3 Cl1 118.89(13) . . ? C5 C6 C1 122.49(15) . . ? C5 C6 Cl2 119.32(12) . . ? C1 C6 Cl2 118.15(12) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 C7 C8 1.5(3) . . . . ? C11 N1 C7 C12 -178.08(19) . . . . ? N1 C7 C8 C9 -1.4(3) . . . . ? C12 C7 C8 C9 178.1(2) . . . . ? C7 N1 C11 C10 -0.4(3) . . . . ? N1 C11 C10 C9 -0.7(4) . . . . ? C11 C10 C9 C8 0.7(4) . . . . ? C7 C8 C9 C10 0.4(3) . . . . ? O3 C4 C5 O4 1.2(2) . . . . ? C3 C4 C5 O4 -179.49(16) . . . . ? O3 C4 C5 C6 -178.03(16) . . . . ? C3 C4 C5 C6 1.3(2) . . . . ? O2 C2 C1 O1 1.0(2) . . . . ? C3 C2 C1 O1 -179.08(16) . . . . ? O2 C2 C1 C6 -178.87(15) . . . . ? C3 C2 C1 C6 1.0(2) . . . . ? O2 C2 C3 C4 -178.61(16) . . . . ? C1 C2 C3 C4 1.5(3) . . . . ? O2 C2 C3 Cl1 -0.2(2) . . . . ? C1 C2 C3 Cl1 179.88(12) . . . . ? O3 C4 C3 C2 176.66(17) . . . . ? C5 C4 C3 C2 -2.6(2) . . . . ? O3 C4 C3 Cl1 -1.8(2) . . . . ? C5 C4 C3 Cl1 178.99(12) . . . . ? O4 C5 C6 C1 -177.90(17) . . . . ? C4 C5 C6 C1 1.3(2) . . . . ? O4 C5 C6 Cl2 0.1(2) . . . . ? C4 C5 C6 Cl2 179.24(12) . . . . ? O1 C1 C6 C5 177.70(16) . . . . ? C2 C1 C6 C5 -2.4(2) . . . . ? O1 C1 C6 Cl2 -0.3(2) . . . . ? C2 C1 C6 Cl2 179.60(11) . . . . ? # Attachment '2-MePyClxH2CA1.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-04-22 at 13:54:10 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : f:\programs\wingx\files\cifdoc.dat # CIF files read : pbf122 dreduc psi_scan struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_2-MePyClxH2CA _database_code_depnum_ccdc_archive 'CCDC 729425' _audit_creation_date 2008-04-22T13:54:10-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C9 H9 Cl2 N1 O2' _chemical_formula_sum 'C9 H9 Cl2 N1 O2' _chemical_formula_weight 234.08 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' 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' _cell_length_a 7.6088(8) _cell_length_b 10.3187(6) _cell_length_c 13.2129(10) _cell_angle_alpha 90 _cell_angle_beta 97.033(8) _cell_angle_gamma 90 _cell_volume 1029.58(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.3 _cell_measurement_theta_max 18.9 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour 'dark yellow' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.51 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 5.469 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.2740 _exptl_absorpt_correction_T_max 0.3733 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 10 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 -2 0 -1 -2 -3 0 3 -2 _diffrn_reflns_number 2126 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.46 _diffrn_reflns_theta_max 71.62 _diffrn_reflns_theta_full 71.62 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measured_fraction_theta_full 0.978 _reflns_number_total 1974 _reflns_number_gt 1733 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0888P)^2^+0.3323P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0071(11) _refine_ls_number_reflns 1974 _refine_ls_number_parameters 164 _refine_ls_number_restraints 7 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1328 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.555 _refine_diff_density_min -0.482 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Cl2 Cl 0.14508(7) 0.94422(6) 0.13932(4) 0.0422(2) Uani 1 d . . . Cl1 Cl 0.00330(9) 0.26244(6) 0.65081(5) 0.0477(3) Uani 1 d . . . O2 O 0.2746(3) 0.4702(2) 0.65655(15) 0.0464(5) Uani 1 d . . . O1 O 0.2417(2) 0.68425(17) 0.53911(16) 0.0482(5) Uani 1 d . . . C2 C 0.1403(3) 0.4801(2) 0.58258(19) 0.0356(5) Uani 1 d . . . N1 N 0.3703(3) 0.2137(2) 0.50657(16) 0.0374(5) Uani 1 d . . . C4 C 0.2624(3) 0.1160(2) 0.47094(18) 0.0373(5) Uani 1 d . . . C1 C 0.1337(3) 0.5985(2) 0.51554(18) 0.0352(5) Uani 1 d . . . C8 C 0.4762(4) 0.2106(3) 0.5963(2) 0.0420(6) Uani 1 d . . . C7 C 0.4783(4) 0.1024(3) 0.6564(2) 0.0501(7) Uani 1 d D . . C3 C 0.0076(3) 0.3924(2) 0.56929(18) 0.0359(5) Uani 1 d . . . C5 C 0.2646(4) 0.0054(2) 0.5303(2) 0.0450(6) Uani 1 d . . . C6 C 0.3716(4) -0.0006(3) 0.6226(2) 0.0499(7) Uani 1 d . . . C9 C 0.1503(4) 0.1325(3) 0.3709(2) 0.0543(7) Uani 1 d D . . H7 H 0.560(4) 0.093(3) 0.7150(19) 0.063(10) Uiso 1 d D . . H2 H 0.362(5) 0.518(5) 0.653(3) 0.079(12) Uiso 1 d . . . H5 H 0.186(5) -0.059(4) 0.501(3) 0.074(11) Uiso 1 d . . . H6 H 0.373(4) -0.078(4) 0.659(3) 0.061(9) Uiso 1 d . . . H8 H 0.554(4) 0.276(3) 0.614(3) 0.056(9) Uiso 1 d . . . H1 H 0.373(4) 0.281(3) 0.471(3) 0.048(8) Uiso 1 d . . . H9B H 0.045(4) 0.183(4) 0.362(3) 0.098(15) Uiso 1 d D . . H9C H 0.120(6) 0.046(2) 0.347(4) 0.14(2) Uiso 1 d D . . H9A H 0.216(5) 0.162(4) 0.317(3) 0.119(17) Uiso 1 d 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 Cl2 0.0412(4) 0.0401(4) 0.0446(4) -0.0090(2) 0.0019(3) 0.0036(2) Cl1 0.0558(4) 0.0344(4) 0.0540(4) 0.0108(2) 0.0114(3) -0.0062(2) O2 0.0421(10) 0.0470(10) 0.0499(11) 0.0078(8) 0.0049(8) -0.0090(8) O1 0.0476(10) 0.0316(9) 0.0659(12) -0.0011(8) 0.0089(9) -0.0096(8) C2 0.0349(12) 0.0310(11) 0.0430(12) -0.0007(9) 0.0135(9) 0.0007(9) N1 0.0461(11) 0.0287(10) 0.0393(11) 0.0010(8) 0.0129(9) 0.0000(8) C4 0.0429(12) 0.0318(12) 0.0389(12) -0.0055(9) 0.0115(10) -0.0018(10) C1 0.0355(11) 0.0255(10) 0.0477(13) -0.0026(9) 0.0175(10) -0.0014(9) C8 0.0413(13) 0.0419(14) 0.0431(14) -0.0072(11) 0.0070(11) -0.0018(11) C7 0.0551(16) 0.0589(17) 0.0365(13) 0.0014(12) 0.0058(11) 0.0121(14) C3 0.0394(12) 0.0265(10) 0.0444(13) 0.0032(9) 0.0162(10) -0.0004(9) C5 0.0552(15) 0.0303(12) 0.0525(15) -0.0021(10) 0.0192(12) -0.0042(11) C6 0.0625(17) 0.0392(14) 0.0513(15) 0.0112(12) 0.0209(13) 0.0090(12) C9 0.0617(18) 0.0544(17) 0.0457(15) -0.0054(13) 0.0019(13) -0.0028(14) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C3 1.723(2) . ? O2 C2 1.329(3) . ? O2 H2 0.83(4) . ? O1 C1 1.222(3) . ? C2 C3 1.351(3) . ? C2 C1 1.506(3) . ? N1 C4 1.348(3) . ? N1 C8 1.350(3) . ? N1 H1 0.84(4) . ? C4 C5 1.384(4) . ? C4 C9 1.493(4) . ? C1 C3 1.458(3) 3_566 ? C8 C7 1.369(4) . ? C8 H8 0.90(3) . ? C7 C6 1.378(4) . ? C7 H7 0.936(18) . ? C3 C1 1.458(3) 3_566 ? C5 C6 1.382(4) . ? C5 H5 0.95(4) . ? C6 H6 0.93(4) . ? C9 H9B 0.953(18) . ? C9 H9C 0.966(19) . ? C9 H9A 0.970(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 H2 118(3) . . ? O2 C2 C3 122.6(2) . . ? O2 C2 C1 117.6(2) . . ? C3 C2 C1 119.7(2) . . ? C4 N1 C8 124.1(2) . . ? C4 N1 H1 118(2) . . ? C8 N1 H1 118(2) . . ? N1 C4 C5 117.0(2) . . ? N1 C4 C9 118.8(2) . . ? C5 C4 C9 124.2(2) . . ? O1 C1 C3 124.0(2) . 3_566 ? O1 C1 C2 117.7(2) . . ? C3 C1 C2 118.2(2) 3_566 . ? N1 C8 C7 119.5(3) . . ? N1 C8 H8 120(2) . . ? C7 C8 H8 120(2) . . ? C8 C7 C6 118.4(3) . . ? C8 C7 H7 121(2) . . ? C6 C7 H7 120(2) . . ? C2 C3 C1 121.7(2) . 3_566 ? C2 C3 Cl1 120.7(2) . . ? C1 C3 Cl1 117.51(17) 3_566 . ? C6 C5 C4 120.1(3) . . ? C6 C5 H5 127(2) . . ? C4 C5 H5 113(2) . . ? C7 C6 C5 120.8(3) . . ? C7 C6 H6 122(2) . . ? C5 C6 H6 118(2) . . ? C4 C9 H9B 124(3) . . ? C4 C9 H9C 106(3) . . ? H9B C9 H9C 107(3) . . ? C4 C9 H9A 113(3) . . ? H9B C9 H9A 104(3) . . ? H9C C9 H9A 100(3) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C4 C5 -1.2(3) . . . . ? C8 N1 C4 C9 179.3(2) . . . . ? O2 C2 C1 O1 -7.1(3) . . . . ? C3 C2 C1 O1 169.6(2) . . . . ? O2 C2 C1 C3 176.8(2) . . . 3_566 ? C3 C2 C1 C3 -6.5(3) . . . 3_566 ? C4 N1 C8 C7 0.5(4) . . . . ? N1 C8 C7 C6 0.2(4) . . . . ? O2 C2 C3 C1 -176.7(2) . . . 3_566 ? C1 C2 C3 C1 6.8(4) . . . 3_566 ? O2 C2 C3 Cl1 1.4(3) . . . . ? C1 C2 C3 Cl1 -175.16(16) . . . . ? N1 C4 C5 C6 1.2(4) . . . . ? C9 C4 C5 C6 -179.3(3) . . . . ? C8 C7 C6 C5 -0.2(4) . . . . ? C4 C5 C6 C7 -0.5(4) . . . . ? # Attachment '2-MePyClxH2CAxH2O1.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-02-29 at 12:44:40 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : f:\programs\wingx\files\cifdoc.dat # CIF files read : 2-mepy-12 2-mepy-12-teh #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_2-MePyClxH2CAxH2O _database_code_depnum_ccdc_archive 'CCDC 729426' _audit_creation_date 2008-02-29T12:44:40-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_sum 'C9 H11 Cl2 N O3' _chemical_formula_moiety 'C9 H11 Cl2 N O3' _chemical_formula_weight 252.09 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' 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' _cell_length_a 4.21400(10) _cell_length_b 19.9252(4) _cell_length_c 13.3364(3) _cell_angle_alpha 90 _cell_angle_beta 98.591(2) _cell_angle_gamma 90 _cell_volume 1107.22(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7501 _cell_measurement_theta_min 3.342 _cell_measurement_theta_max 75.8228 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 5.195 _exptl_absorpt_correction_T_min 0.65595 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_measurement_device_type 'Oxford Xcalibur Nova' _diffrn_measurement_method ; CCD detector ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4323 _diffrn_reflns_number 10559 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.02 _diffrn_reflns_theta_max 76.12 _diffrn_reflns_theta_full 76.12 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measured_fraction_theta_full 0.982 _reflns_number_total 2283 _reflns_number_gt 2185 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0409P)^2^+0.5509P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 2283 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0736 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.343 _refine_diff_density_min -0.225 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly O3 O -0.1160(3) -0.06930(5) 0.68920(8) 0.0242(2) Uani 1 d . . . H6 H 1.286(5) 0.2764(10) 1.3023(15) 0.032(5) Uiso 1 d . . . H8 H 0.629(4) 0.2236(9) 1.0654(13) 0.024(4) Uiso 1 d . . . H5 H 1.187(4) 0.3888(9) 1.2547(14) 0.022(4) Uiso 1 d . . . H1 H 0.562(5) 0.3289(10) 1.0306(16) 0.030(5) Uiso 1 d . . . H7 H 1.002(5) 0.1918(12) 1.2059(16) 0.038(5) Uiso 1 d . . . H2 H 0.015(6) -0.0200(13) 0.7895(19) 0.053(7) Uiso 1 d . . . H9B H 0.929(6) 0.4718(12) 1.1308(18) 0.047(6) Uiso 1 d . . . H9A H 0.584(7) 0.4534(13) 1.1042(19) 0.057(7) Uiso 1 d . . . H9C H 0.817(6) 0.4429(14) 1.028(2) 0.061(7) Uiso 1 d . . . H3A H -0.285(6) -0.0926(12) 0.6780(16) 0.042(6) Uiso 1 d . . . H3B H 0.020(6) -0.0962(12) 0.6660(17) 0.046(6) Uiso 1 d . . . Cl1 Cl 0.13979(8) 0.137927(16) 0.95547(2) 0.02553(11) Uani 1 d . . . O2 O 0.0458(2) 0.01484(5) 0.82968(7) 0.0238(2) Uani 1 d . . . O1 O 0.6054(3) 0.09922(5) 1.13354(8) 0.0267(2) Uani 1 d . . . C2 C 0.3298(3) 0.06168(7) 0.97696(10) 0.0197(3) Uani 1 d . . . C1 C 0.5561(3) 0.05515(7) 1.07022(10) 0.0194(3) Uani 1 d . . . C3 C 0.2638(3) 0.01029(7) 0.91129(10) 0.0189(3) Uani 1 d . . . Cl2 Cl 0.16459(8) 0.332767(17) 0.90145(2) 0.02382(11) Uani 1 d . . . N1 N 0.7027(3) 0.31948(6) 1.08125(9) 0.0196(2) Uani 1 d . . . C6 C 1.1327(4) 0.28761(8) 1.24552(11) 0.0256(3) Uani 1 d . . . C4 C 0.8607(3) 0.37012(7) 1.13337(10) 0.0200(3) Uani 1 d . . . C5 C 1.0794(4) 0.35423(7) 1.21809(11) 0.0234(3) Uani 1 d . . . C9 C 0.7889(4) 0.43964(7) 1.09490(12) 0.0267(3) Uani 1 d . . . C8 C 0.7496(4) 0.25457(7) 1.10614(11) 0.0226(3) Uani 1 d . . . C7 C 0.9680(4) 0.23705(7) 1.18844(11) 0.0253(3) Uani 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 O3 0.0245(5) 0.0233(5) 0.0231(5) -0.0056(4) -0.0019(4) -0.0018(4) Cl1 0.0317(2) 0.01873(18) 0.02316(18) -0.00301(11) -0.00559(14) 0.00574(12) O2 0.0292(5) 0.0201(5) 0.0193(5) -0.0031(4) -0.0060(4) 0.0019(4) O1 0.0355(6) 0.0199(5) 0.0216(5) -0.0045(4) -0.0061(4) 0.0012(4) C2 0.0224(7) 0.0163(6) 0.0195(6) 0.0013(5) 0.0003(5) 0.0007(5) C1 0.0221(7) 0.0172(6) 0.0184(6) -0.0001(5) 0.0015(5) -0.0027(5) C3 0.0205(6) 0.0194(6) 0.0162(6) 0.0014(5) 0.0011(5) -0.0012(5) Cl2 0.02070(18) 0.0298(2) 0.01988(18) 0.00280(12) -0.00051(13) 0.00117(12) N1 0.0202(6) 0.0220(6) 0.0159(5) 0.0001(4) 0.0005(5) -0.0003(4) C6 0.0288(7) 0.0271(7) 0.0192(7) 0.0022(5) -0.0024(6) 0.0022(6) C4 0.0218(7) 0.0206(6) 0.0182(6) -0.0010(5) 0.0050(5) -0.0003(5) C5 0.0263(7) 0.0223(7) 0.0206(7) -0.0036(5) 0.0001(6) -0.0028(6) C9 0.0338(8) 0.0200(7) 0.0254(8) 0.0007(6) 0.0017(6) 0.0021(6) C8 0.0263(7) 0.0196(6) 0.0219(6) -0.0018(5) 0.0032(5) -0.0046(5) C7 0.0321(8) 0.0198(7) 0.0236(7) 0.0031(6) 0.0028(6) 0.0005(6) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 H3A 0.85(2) . ? O3 H3B 0.87(3) . ? Cl1 C2 1.7211(14) . ? O2 C3 1.3182(16) . ? O2 H2 0.87(3) . ? O1 C1 1.2145(17) . ? C2 C3 1.3492(19) . ? C2 C1 1.4558(18) . ? C1 C3 1.5102(18) 3_657 ? C3 C1 1.5102(18) 3_657 ? N1 C8 1.3426(19) . ? N1 C4 1.3439(19) . ? N1 H1 0.85(2) . ? C6 C7 1.385(2) . ? C6 C5 1.386(2) . ? C6 H6 0.94(2) . ? C4 C5 1.384(2) . ? C4 C9 1.492(2) . ? C5 H5 0.925(19) . ? C9 H9B 0.95(3) . ? C9 H9A 0.93(3) . ? C9 H9C 0.92(3) . ? C8 C7 1.368(2) . ? C8 H8 0.923(19) . ? C7 H7 0.94(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H3A O3 H3B 100(2) . . ? C3 O2 H2 118.3(16) . . ? C3 C2 C1 122.13(12) . . ? C3 C2 Cl1 121.08(11) . . ? C1 C2 Cl1 116.77(10) . . ? O1 C1 C2 123.46(13) . . ? O1 C1 C3 118.76(12) . 3_657 ? C2 C1 C3 117.77(12) . 3_657 ? O2 C3 C2 122.30(12) . . ? O2 C3 C1 117.73(12) . 3_657 ? C2 C3 C1 119.96(12) . 3_657 ? C8 N1 C4 123.51(13) . . ? C8 N1 H1 117.9(13) . . ? C4 N1 H1 118.5(13) . . ? C7 C6 C5 120.21(14) . . ? C7 C6 H6 119.6(12) . . ? C5 C6 H6 120.2(12) . . ? N1 C4 C5 117.94(13) . . ? N1 C4 C9 117.37(13) . . ? C5 C4 C9 124.69(13) . . ? C4 C5 C6 119.77(13) . . ? C4 C5 H5 118.4(11) . . ? C6 C5 H5 121.8(11) . . ? C4 C9 H9B 112.0(14) . . ? C4 C9 H9A 111.8(16) . . ? H9B C9 H9A 105(2) . . ? C4 C9 H9C 110.4(17) . . ? H9B C9 H9C 106(2) . . ? H9A C9 H9C 111(2) . . ? N1 C8 C7 120.06(13) . . ? N1 C8 H8 116.8(11) . . ? C7 C8 H8 123.1(11) . . ? C8 C7 C6 118.50(14) . . ? C8 C7 H7 120.2(13) . . ? C6 C7 H7 121.3(13) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C2 C1 O1 -175.36(14) . . . . ? Cl1 C2 C1 O1 2.94(19) . . . . ? C3 C2 C1 C3 4.2(2) . . . 3_657 ? Cl1 C2 C1 C3 -177.50(10) . . . 3_657 ? C1 C2 C3 O2 176.10(12) . . . . ? Cl1 C2 C3 O2 -2.1(2) . . . . ? C1 C2 C3 C1 -4.3(2) . . . 3_657 ? Cl1 C2 C3 C1 177.48(10) . . . 3_657 ? C8 N1 C4 C5 -1.1(2) . . . . ? C8 N1 C4 C9 178.42(14) . . . . ? N1 C4 C5 C6 1.0(2) . . . . ? C9 C4 C5 C6 -178.41(15) . . . . ? C7 C6 C5 C4 0.0(2) . . . . ? C4 N1 C8 C7 0.0(2) . . . . ? N1 C8 C7 C6 1.1(2) . . . . ? C5 C6 C7 C8 -1.1(2) . . . . ? # Attachment '2-MePyNaHCAxH2O1.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-02-29 at 12:16:52 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : f:\programs\wingx\files\cifdoc.dat # CIF files read : 2-mepy-6 2-mepy-6-tehn struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_2-MePyNaHCAxH2O _database_code_depnum_ccdc_archive 'CCDC 729427' _audit_creation_date 2008-02-29T12:16:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C6 H2 Cl2 Na O5, C6 H8 N' _chemical_formula_sum 'C12 H10 Cl2 N1 Na1 O5' _chemical_formula_weight 342.11 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.9601(2) _cell_length_b 8.4990(4) _cell_length_c 16.4150(7) _cell_angle_alpha 88.135(4) _cell_angle_beta 84.817(3) _cell_angle_gamma 88.068(4) _cell_volume 688.47(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4996 _cell_measurement_theta_min 2.6995 _cell_measurement_theta_max 75.8539 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.65 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 4.764 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5990 _exptl_absorpt_correction_T_max 0.7500 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_measurement_device_type 'Oxford Xcalibur Nova' _diffrn_measurement_method ; CCD detector ; _diffrn_radiation_monochromator graphite _diffrn_reflns_number 7053 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.7 _diffrn_reflns_theta_max 75.8 _diffrn_reflns_theta_full 75.8 _diffrn_measured_fraction_theta_max 0.96 _diffrn_measured_fraction_theta_full 0.96 _reflns_number_total 2759 _reflns_number_gt 2535 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0543P)^2^+0.1545P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 2759 _refine_ls_number_parameters 230 _refine_ls_number_restraints 3 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0907 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.1 _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.259 _refine_diff_density_min -0.223 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Cl2 Cl 0.02871(7) 0.25813(4) 0.98421(2) 0.04052(13) Uani 1 d . . . Cl1 Cl 0.91576(9) -0.29022(5) 0.47735(3) 0.05221(15) Uani 1 d . . . Na1 Na 0.69984(14) 0.03666(8) 0.74509(4) 0.04262(18) Uani 1 d . . . O3 O 0.2115(2) 0.10147(14) 1.13611(7) 0.0427(3) Uani 1 d . . . O2 O 0.7872(3) -0.09683(15) 0.62467(7) 0.0466(3) Uani 1 d . . . O1 O 0.4302(3) 0.14197(15) 0.64578(7) 0.0446(3) Uani 1 d . . . O5 O 1.0155(2) 0.24297(16) 0.75363(7) 0.0447(3) Uani 1 d D . . O4 O 0.4008(2) 0.12130(15) 0.85083(7) 0.0427(3) Uani 1 d . . . N1 N 0.3832(3) 0.52463(17) 1.25893(9) 0.0425(3) Uani 1 d . . . C2 C 0.6603(3) -0.05740(18) 0.56530(9) 0.0340(3) Uani 1 d . . . C5 C 0.2895(3) 0.11830(17) 0.99282(9) 0.0319(3) Uani 1 d . . . C4 C 0.3368(3) 0.05866(17) 1.07158(9) 0.0317(3) Uani 1 d . . . C6 C 0.4358(3) 0.06933(17) 0.92160(9) 0.0315(3) Uani 1 d . . . C1 C 0.4540(3) 0.08199(18) 0.57678(9) 0.0339(3) Uani 1 d . . . C3 C 0.6881(3) -0.13085(19) 0.48929(9) 0.0365(3) Uani 1 d . . . C7 C 0.5079(3) 0.44584(19) 1.19671(10) 0.0398(3) Uani 1 d . . . C11 C 0.4420(5) 0.5027(3) 1.33693(12) 0.0551(5) Uani 1 d . . . C8 C 0.7065(4) 0.3358(2) 1.21364(14) 0.0547(5) Uani 1 d . . . C10 C 0.6372(5) 0.3955(3) 1.35506(15) 0.0651(6) Uani 1 d . . . C12 C 0.4246(6) 0.4834(3) 1.11341(14) 0.0600(5) Uani 1 d . . . C9 C 0.7703(5) 0.3119(3) 1.29279(17) 0.0663(6) Uani 1 d . . . H5A H 1.130(4) 0.226(3) 0.7087(11) 0.062(7) Uiso 1 d D . . H5B H 1.105(5) 0.221(3) 0.7987(12) 0.068(7) Uiso 1 d D . . H1 H 0.248(6) 0.593(3) 1.2477(16) 0.066(7) Uiso 1 d . . . H3 H 0.795(6) 0.283(3) 1.1724(17) 0.070(7) Uiso 1 d . . . H11 H 0.337(6) 0.566(3) 1.3761(18) 0.078(8) Uiso 1 d . . . H9 H 0.909(7) 0.236(4) 1.305(2) 0.093(9) Uiso 1 d . . . H12A H 0.256(9) 0.452(5) 1.107(2) 0.125(14) Uiso 1 d . . . H10 H 0.665(7) 0.385(4) 1.410(2) 0.092(9) Uiso 1 d . . . H12C H 0.532(9) 0.431(5) 1.074(3) 0.124(14) Uiso 1 d . . . H12B H 0.461(7) 0.586(5) 1.098(2) 0.107(11) Uiso 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 Cl2 0.0376(2) 0.0435(2) 0.0399(2) 0.00008(15) -0.00736(15) 0.01625(15) Cl1 0.0588(3) 0.0573(3) 0.0402(2) -0.01060(18) -0.01194(18) 0.0327(2) Na1 0.0509(4) 0.0509(4) 0.0257(3) -0.0030(2) -0.0064(3) 0.0145(3) O3 0.0494(6) 0.0491(6) 0.0276(5) -0.0005(4) -0.0005(5) 0.0179(5) O2 0.0550(7) 0.0553(7) 0.0301(5) -0.0060(5) -0.0152(5) 0.0238(6) O1 0.0503(6) 0.0565(7) 0.0267(5) -0.0097(5) -0.0077(5) 0.0209(5) O5 0.0399(6) 0.0587(7) 0.0344(6) 0.0004(5) -0.0050(5) 0.0188(5) O4 0.0449(6) 0.0557(7) 0.0265(5) 0.0029(4) -0.0059(4) 0.0184(5) N1 0.0394(7) 0.0410(7) 0.0467(8) -0.0012(6) -0.0050(6) 0.0101(6) C2 0.0354(7) 0.0400(7) 0.0263(7) -0.0006(5) -0.0046(5) 0.0087(6) C5 0.0311(7) 0.0346(7) 0.0299(7) 0.0007(5) -0.0068(5) 0.0090(5) C4 0.0324(7) 0.0348(7) 0.0280(7) -0.0012(5) -0.0049(5) 0.0045(5) C6 0.0306(7) 0.0358(7) 0.0284(7) 0.0000(5) -0.0072(5) 0.0043(5) C1 0.0352(7) 0.0395(8) 0.0265(7) -0.0025(5) -0.0035(6) 0.0091(6) C3 0.0384(8) 0.0413(8) 0.0289(7) -0.0038(6) -0.0044(6) 0.0160(6) C7 0.0392(8) 0.0391(8) 0.0411(8) -0.0011(6) -0.0053(6) 0.0026(6) C11 0.0658(12) 0.0573(11) 0.0418(9) -0.0053(8) -0.0026(9) 0.0014(9) C8 0.0474(10) 0.0494(10) 0.0658(13) -0.0042(9) -0.0022(9) 0.0150(8) C10 0.0786(15) 0.0681(13) 0.0518(11) 0.0127(10) -0.0277(11) -0.0073(11) C12 0.0759(14) 0.0603(12) 0.0454(10) 0.0027(9) -0.0166(10) -0.0028(11) C9 0.0553(11) 0.0572(12) 0.0879(17) 0.0127(11) -0.0258(11) 0.0149(9) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl2 C5 1.7388(14) . ? Cl1 C3 1.7385(15) . ? Na1 O4 2.2966(13) . ? Na1 O2 2.3108(13) . ? Na1 O3 2.3121(12) 2_657 ? Na1 O1 2.3378(13) . ? Na1 O5 2.4054(16) . ? Na1 C4 3.0818(15) 2_657 ? Na1 C6 3.0869(16) . ? Na1 C2 3.1075(16) . ? Na1 C1 3.1267(15) . ? O3 C4 1.2375(19) . ? O3 Na1 2.3121(12) 2_657 ? O2 C2 1.2384(19) . ? O1 C1 1.2514(18) . ? O5 H5A 0.903(16) . ? O5 H5B 0.908(16) . ? O4 C6 1.2540(18) . ? N1 C7 1.333(2) . ? N1 C11 1.344(2) . ? N1 H1 0.90(3) . ? C2 C3 1.407(2) . ? C2 C1 1.544(2) . ? C5 C6 1.387(2) . ? C5 C4 1.410(2) . ? C4 C6 1.549(2) 2_657 ? C4 Na1 3.0818(15) 2_657 ? C6 C4 1.549(2) 2_657 ? C1 C3 1.391(2) 2_656 ? C3 C1 1.391(2) 2_656 ? C7 C8 1.376(3) . ? C7 C12 1.486(3) . ? C11 C10 1.353(3) . ? C11 H11 0.96(3) . ? C8 C9 1.372(3) . ? C8 H3 0.90(3) . ? C10 C9 1.371(4) . ? C10 H10 0.92(3) . ? C12 H12A 0.90(4) . ? C12 H12C 0.91(5) . ? C12 H12B 0.92(4) . ? C9 H9 0.96(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Na1 O2 150.08(6) . . ? O4 Na1 O3 70.82(4) . 2_657 ? O2 Na1 O3 116.27(5) . 2_657 ? O4 Na1 O1 92.76(5) . . ? O2 Na1 O1 69.75(4) . . ? O3 Na1 O1 155.88(6) 2_657 . ? O4 Na1 O5 95.59(5) . . ? O2 Na1 O5 111.25(5) . . ? O3 Na1 O5 97.70(5) 2_657 . ? O1 Na1 O5 101.50(5) . . ? O4 Na1 C4 50.11(4) . 2_657 ? O2 Na1 C4 134.84(5) . 2_657 ? O3 Na1 C4 20.92(4) 2_657 2_657 ? O1 Na1 C4 140.55(5) . 2_657 ? O5 Na1 C4 95.77(4) . 2_657 ? O4 Na1 C6 21.07(4) . . ? O2 Na1 C6 152.60(5) . . ? O3 Na1 C6 49.92(4) 2_657 . ? O1 Na1 C6 113.37(4) . . ? O5 Na1 C6 95.10(4) . . ? C4 Na1 C6 29.09(4) 2_657 . ? O4 Na1 C2 135.86(5) . . ? O2 Na1 C2 20.38(4) . . ? O3 Na1 C2 134.07(5) 2_657 . ? O1 Na1 C2 49.38(4) . . ? O5 Na1 C2 111.73(5) . . ? C4 Na1 C2 148.82(5) 2_657 . ? C6 Na1 C2 149.76(5) . . ? O4 Na1 C1 111.42(4) . . ? O2 Na1 C1 49.05(4) . . ? O3 Na1 C1 154.36(5) 2_657 . ? O1 Na1 C1 20.70(4) . . ? O5 Na1 C1 107.28(5) . . ? C4 Na1 C1 152.53(5) 2_657 . ? C6 Na1 C1 130.83(4) . . ? C2 Na1 C1 28.68(4) . . ? C4 O3 Na1 117.25(10) . 2_657 ? C2 O2 Na1 119.09(10) . . ? C1 O1 Na1 117.97(10) . . ? Na1 O5 H5A 101.0(16) . . ? Na1 O5 H5B 107.1(17) . . ? H5A O5 H5B 109(2) . . ? C6 O4 Na1 117.75(10) . . ? C7 N1 C11 123.53(16) . . ? C7 N1 H1 117.4(17) . . ? C11 N1 H1 119.0(17) . . ? O2 C2 C3 125.03(14) . . ? O2 C2 C1 116.87(13) . . ? C3 C2 C1 118.10(13) . . ? O2 C2 Na1 40.53(8) . . ? C3 C2 Na1 165.50(11) . . ? C1 C2 Na1 76.35(8) . . ? C6 C5 C4 123.66(13) . . ? C6 C5 Cl2 118.12(11) . . ? C4 C5 Cl2 118.21(11) . . ? O3 C4 C5 124.98(14) . . ? O3 C4 C6 117.19(13) . 2_657 ? C5 C4 C6 117.82(13) . 2_657 ? O3 C4 Na1 41.83(7) . 2_657 ? C5 C4 Na1 165.91(11) . 2_657 ? C6 C4 Na1 75.64(8) 2_657 2_657 ? O4 C6 C5 125.18(14) . . ? O4 C6 C4 116.30(13) . 2_657 ? C5 C6 C4 118.52(12) . 2_657 ? O4 C6 Na1 41.18(7) . . ? C5 C6 Na1 165.68(11) . . ? C4 C6 Na1 75.27(8) 2_657 . ? O1 C1 C3 125.49(14) . 2_656 ? O1 C1 C2 116.30(13) . . ? C3 C1 C2 118.21(13) 2_656 . ? O1 C1 Na1 41.33(7) . . ? C3 C1 Na1 166.81(11) 2_656 . ? C2 C1 Na1 74.97(8) . . ? C1 C3 C2 123.66(14) 2_656 . ? C1 C3 Cl1 118.42(12) 2_656 . ? C2 C3 Cl1 117.91(11) . . ? N1 C7 C8 117.97(17) . . ? N1 C7 C12 117.80(17) . . ? C8 C7 C12 124.23(19) . . ? N1 C11 C10 119.6(2) . . ? N1 C11 H11 115.6(17) . . ? C10 C11 H11 124.8(17) . . ? C9 C8 C7 119.5(2) . . ? C9 C8 H3 121.3(17) . . ? C7 C8 H3 119.2(18) . . ? C11 C10 C9 118.7(2) . . ? C11 C10 H10 115(2) . . ? C9 C10 H10 126(2) . . ? C7 C12 H12A 113(2) . . ? C7 C12 H12C 112(3) . . ? H12A C12 H12C 104(3) . . ? C7 C12 H12B 111(2) . . ? H12A C12 H12B 116(3) . . ? H12C C12 H12B 100(3) . . ? C10 C9 C8 120.75(19) . . ? C10 C9 H9 120(2) . . ? C8 C9 H9 120(2) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Na1 O2 C2 56.88(18) . . . . ? O3 Na1 O2 C2 153.97(12) 2_657 . . . ? O1 Na1 O2 C2 -0.56(12) . . . . ? O5 Na1 O2 C2 -95.41(13) . . . . ? C4 Na1 O2 C2 141.99(12) 2_657 . . . ? C6 Na1 O2 C2 101.41(15) . . . . ? C1 Na1 O2 C2 -0.55(11) . . . . ? O4 Na1 O1 C1 -155.11(12) . . . . ? O2 Na1 O1 C1 0.01(12) . . . . ? O3 Na1 O1 C1 -109.30(16) 2_657 . . . ? O5 Na1 O1 C1 108.62(12) . . . . ? C4 Na1 O1 C1 -137.26(11) 2_657 . . . ? C6 Na1 O1 C1 -150.62(12) . . . . ? C2 Na1 O1 C1 -0.25(11) . . . . ? O2 Na1 O4 C6 116.14(13) . . . . ? O3 Na1 O4 C6 6.55(11) 2_657 . . . ? O1 Na1 O4 C6 168.48(12) . . . . ? O5 Na1 O4 C6 -89.68(12) . . . . ? C4 Na1 O4 C6 3.18(10) 2_657 . . . ? C2 Na1 O4 C6 140.89(11) . . . . ? C1 Na1 O4 C6 159.28(11) . . . . ? Na1 O2 C2 C3 -178.28(13) . . . . ? Na1 O2 C2 C1 0.95(19) . . . . ? O4 Na1 C2 O2 -143.15(13) . . . . ? O3 Na1 C2 O2 -33.21(15) 2_657 . . . ? O1 Na1 C2 O2 179.31(15) . . . . ? O5 Na1 C2 O2 92.71(13) . . . . ? C4 Na1 C2 O2 -57.50(16) 2_657 . . . ? C6 Na1 C2 O2 -116.38(14) . . . . ? C1 Na1 C2 O2 179.13(18) . . . . ? O4 Na1 C2 C3 -137.5(4) . . . . ? O2 Na1 C2 C3 5.6(4) . . . . ? O3 Na1 C2 C3 -27.6(5) 2_657 . . . ? O1 Na1 C2 C3 -175.1(5) . . . . ? O5 Na1 C2 C3 98.3(5) . . . . ? C4 Na1 C2 C3 -51.9(5) 2_657 . . . ? C6 Na1 C2 C3 -110.8(5) . . . . ? C1 Na1 C2 C3 -175.2(5) . . . . ? O4 Na1 C2 C1 37.73(11) . . . . ? O2 Na1 C2 C1 -179.13(18) . . . . ? O3 Na1 C2 C1 147.66(9) 2_657 . . . ? O1 Na1 C2 C1 0.18(8) . . . . ? O5 Na1 C2 C1 -86.42(9) . . . . ? C4 Na1 C2 C1 123.37(10) 2_657 . . . ? C6 Na1 C2 C1 64.49(12) . . . . ? Na1 O3 C4 C5 173.30(12) 2_657 . . . ? Na1 O3 C4 C6 -7.19(18) 2_657 . . 2_657 ? C6 C5 C4 O3 179.14(15) . . . . ? Cl2 C5 C4 O3 -2.2(2) . . . . ? C6 C5 C4 C6 -0.4(2) . . . 2_657 ? Cl2 C5 C4 C6 178.29(10) . . . 2_657 ? C6 C5 C4 Na1 -162.2(4) . . . 2_657 ? Cl2 C5 C4 Na1 16.4(5) . . . 2_657 ? Na1 O4 C6 C5 174.09(12) . . . . ? Na1 O4 C6 C4 -5.41(17) . . . 2_657 ? C4 C5 C6 O4 -179.13(15) . . . . ? Cl2 C5 C6 O4 2.2(2) . . . . ? C4 C5 C6 C4 0.4(2) . . . 2_657 ? Cl2 C5 C6 C4 -178.29(10) . . . 2_657 ? C4 C5 C6 Na1 -163.2(3) . . . . ? Cl2 C5 C6 Na1 18.1(5) . . . . ? O2 Na1 C6 O4 -103.39(15) . . . . ? O3 Na1 C6 O4 -171.91(14) 2_657 . . . ? O1 Na1 C6 O4 -12.56(13) . . . . ? O5 Na1 C6 O4 92.31(12) . . . . ? C4 Na1 C6 O4 -174.98(16) 2_657 . . . ? C2 Na1 C6 O4 -60.72(15) . . . . ? C1 Na1 C6 O4 -25.81(14) . . . . ? O4 Na1 C6 C5 -19.9(4) . . . . ? O2 Na1 C6 C5 -123.3(4) . . . . ? O3 Na1 C6 C5 168.2(4) 2_657 . . . ? O1 Na1 C6 C5 -32.4(4) . . . . ? O5 Na1 C6 C5 72.4(4) . . . . ? C4 Na1 C6 C5 165.1(5) 2_657 . . . ? C2 Na1 C6 C5 -80.6(4) . . . . ? C1 Na1 C6 C5 -45.7(4) . . . . ? O4 Na1 C6 C4 174.98(16) . . . 2_657 ? O2 Na1 C6 C4 71.59(13) . . . 2_657 ? O3 Na1 C6 C4 3.08(8) 2_657 . . 2_657 ? O1 Na1 C6 C4 162.43(8) . . . 2_657 ? O5 Na1 C6 C4 -92.70(8) . . . 2_657 ? C2 Na1 C6 C4 114.26(10) . . . 2_657 ? C1 Na1 C6 C4 149.18(8) . . . 2_657 ? Na1 O1 C1 C3 -179.36(13) . . . 2_656 ? Na1 O1 C1 C2 0.42(18) . . . . ? O2 C2 C1 O1 -0.9(2) . . . . ? C3 C2 C1 O1 178.36(15) . . . . ? Na1 C2 C1 O1 -0.29(13) . . . . ? O2 C2 C1 C3 178.88(15) . . . 2_656 ? C3 C2 C1 C3 -1.8(2) . . . 2_656 ? Na1 C2 C1 C3 179.51(14) . . . 2_656 ? O2 C2 C1 Na1 -0.63(13) . . . . ? C3 C2 C1 Na1 178.65(15) . . . . ? O4 Na1 C1 O1 26.85(13) . . . . ? O2 Na1 C1 O1 -179.99(15) . . . . ? O3 Na1 C1 O1 116.96(15) 2_657 . . . ? O5 Na1 C1 O1 -76.54(13) . . . . ? C4 Na1 C1 O1 69.22(16) 2_657 . . . ? C6 Na1 C1 O1 36.53(14) . . . . ? C2 Na1 C1 O1 179.61(17) . . . . ? O4 Na1 C1 C3 29.1(5) . . . 2_656 ? O2 Na1 C1 C3 -177.7(5) . . . 2_656 ? O3 Na1 C1 C3 119.2(5) 2_657 . . 2_656 ? O1 Na1 C1 C3 2.3(5) . . . 2_656 ? O5 Na1 C1 C3 -74.3(5) . . . 2_656 ? C4 Na1 C1 C3 71.5(5) 2_657 . . 2_656 ? C6 Na1 C1 C3 38.8(5) . . . 2_656 ? C2 Na1 C1 C3 -178.1(6) . . . 2_656 ? O4 Na1 C1 C2 -152.76(9) . . . . ? O2 Na1 C1 C2 0.40(8) . . . . ? O3 Na1 C1 C2 -62.64(14) 2_657 . . . ? O1 Na1 C1 C2 -179.61(17) . . . . ? O5 Na1 C1 C2 103.85(9) . . . . ? C4 Na1 C1 C2 -110.39(11) 2_657 . . . ? C6 Na1 C1 C2 -143.08(8) . . . . ? O2 C2 C3 C1 -178.83(16) . . . 2_656 ? C1 C2 C3 C1 1.9(3) . . . 2_656 ? Na1 C2 C3 C1 176.7(4) . . . 2_656 ? O2 C2 C3 Cl1 0.5(2) . . . . ? C1 C2 C3 Cl1 -178.75(11) . . . . ? Na1 C2 C3 Cl1 -4.0(5) . . . . ? C11 N1 C7 C8 0.3(3) . . . . ? C11 N1 C7 C12 -179.29(19) . . . . ? C7 N1 C11 C10 -0.1(3) . . . . ? N1 C7 C8 C9 -0.5(3) . . . . ? C12 C7 C8 C9 179.1(2) . . . . ? N1 C11 C10 C9 0.1(3) . . . . ? C11 C10 C9 C8 -0.3(4) . . . . ? C7 C8 C9 C10 0.5(3) . . . . ? # Attachment 'Me2NH2HCA-monoclinic1.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-04-22 at 15:32:32 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : f:\programs\wingx\files\cifdoc.dat # CIF files read : inozin-ca-4 inozin-ca-4-tehn struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_Me2NH2HCA-monoclinic _database_code_depnum_ccdc_archive 'CCDC 729428' _audit_creation_date 2008-04-22T15:32:32-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C6 H Cl2 O4, C2 H8 N' _chemical_formula_sum 'C8 H9 Cl2 N O4' _chemical_formula_weight 254.06 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' 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' _cell_length_a 9.575(5) _cell_length_b 28.271(5) _cell_length_c 15.831(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 99.420(5) _cell_angle_gamma 90.000(5) _cell_volume 4228(3) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13508 _cell_measurement_theta_min 2.8271 _cell_measurement_theta_max 76.0698 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description rod _exptl_crystal_colour red _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 5.523 _exptl_absorpt_correction_T_min 0.4389 _exptl_absorpt_correction_T_max 0.6800 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_measurement_device_type 'Oxford Xcalibur Nova' _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_measurement_method ; CCD detector ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4323 _diffrn_reflns_number 25512 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 76 _diffrn_reflns_theta_full 76 _diffrn_measured_fraction_theta_max 0.974 _diffrn_measured_fraction_theta_full 0.974 _reflns_number_total 8623 _reflns_number_gt 7124 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0682P)^2^+1.0955P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8623 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1194 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.441 _refine_diff_density_min -0.286 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Cl8 Cl 0.52928(5) 0.43132(2) 0.02271(3) 0.04839(13) Uani 1 d . . . Cl6 Cl 0.01934(5) 0.31850(2) 0.08084(3) 0.05019(14) Uani 1 d . . . Cl2 Cl 0.60428(5) 0.06288(2) 0.99425(3) 0.05069(14) Uani 1 d . . . Cl1 Cl 1.25766(5) 0.07123(3) 0.97292(3) 0.06177(18) Uani 1 d . . . Cl3 Cl 0.29280(6) 0.17923(3) 0.12954(3) 0.06398(18) Uani 1 d . . . Cl4 Cl 0.94429(5) 0.17630(2) 0.10192(3) 0.05104(14) Uani 1 d . . . Cl5 Cl 0.67429(6) 0.30630(3) 0.06496(4) 0.06461(18) Uani 1 d . . . Cl7 Cl -0.12886(5) 0.43983(2) 0.03129(3) 0.05675(16) Uani 1 d . . . O9 O 0.16922(15) 0.32794(6) -0.07110(8) 0.0491(3) Uani 1 d . . . O16 O 0.29243(15) 0.43641(5) -0.12849(8) 0.0465(3) Uani 1 d . . . O10 O 0.44024(16) 0.32227(6) -0.07855(9) 0.0517(4) Uani 1 d . . . H10 H 0.3698 0.3262 -0.1149 0.078 Uiso 1 calc R . . O12 O 0.25702(16) 0.31034(6) 0.22824(8) 0.0511(4) Uani 1 d . . . O1 O 0.74512(16) 0.07514(7) 0.84029(9) 0.0601(4) Uani 1 d . . . C24 C 0.34857(18) 0.43241(6) 0.02195(11) 0.0344(4) Uani 1 d . . . C13 C 0.2457(2) 0.32080(7) -0.00109(11) 0.0375(4) Uani 1 d . . . O13 O 0.37596(14) 0.42052(5) 0.17080(8) 0.0435(3) Uani 1 d . . . O8 O 0.69936(15) 0.18543(6) -0.04190(8) 0.0494(3) Uani 1 d . . . C19 C 0.30075(18) 0.42753(6) 0.10050(10) 0.0333(3) Uani 1 d . . . C3 C 1.08015(19) 0.06833(7) 0.97780(11) 0.0411(4) Uani 1 d . . . C5 C 0.87910(19) 0.06088(7) 1.06618(11) 0.0360(4) Uani 1 d . . . C9 C 0.4690(2) 0.17636(7) 0.12159(12) 0.0425(4) Uani 1 d . . . O15 O 0.01658(16) 0.44292(6) -0.12111(9) 0.0551(4) Uani 1 d . . . C14 C 0.4017(2) 0.31759(7) -0.00237(11) 0.0404(4) Uani 1 d . . . C10 C 0.5108(2) 0.18378(7) 0.03833(11) 0.0404(4) Uani 1 d . . . O7 O 0.42638(16) 0.19214(7) -0.02594(9) 0.0572(4) Uani 1 d . . . O4 O 0.84757(15) 0.05757(5) 1.13984(8) 0.0455(3) Uani 1 d . . . C20 C 0.14367(19) 0.43105(7) 0.10105(11) 0.0360(4) Uani 1 d . . . C12 C 0.76533(19) 0.17555(7) 0.10719(11) 0.0378(4) Uani 1 d . . . O5 O 0.80498(15) 0.16167(6) 0.25625(8) 0.0518(4) Uani 1 d . . . O6 O 0.53191(16) 0.15888(7) 0.26664(9) 0.0585(4) Uani 1 d . . . H6 H 0.6034 0.1544 0.302 0.088 Uiso 1 calc R . . O2 O 1.02016(16) 0.07915(7) 0.83073(9) 0.0629(5) Uani 1 d . . . H2 H 0.9492 0.0809 0.7941 0.094 Uiso 1 calc R . . C1 C 0.8256(2) 0.07034(7) 0.90946(11) 0.0410(4) Uani 1 d . . . C7 C 0.7240(2) 0.16800(7) 0.18704(11) 0.0392(4) Uani 1 d . . . O3 O 1.12270(15) 0.05741(7) 1.12635(9) 0.0565(4) Uani 1 d . . . O14 O 0.10427(14) 0.42842(6) 0.17744(8) 0.0484(3) Uani 1 d . . . H14 H 0.1745 0.4253 0.2143 0.073 Uiso 1 calc R . . C11 C 0.6687(2) 0.18128(7) 0.03149(11) 0.0388(4) Uani 1 d . . . O11 O 0.53165(17) 0.29969(8) 0.21833(10) 0.0675(5) Uani 1 d . . . C6 C 0.78380(19) 0.06413(7) 0.98960(11) 0.0387(4) Uani 1 d . . . C8 C 0.5681(2) 0.16774(7) 0.19086(11) 0.0409(4) Uani 1 d . . . C22 C 0.09680(19) 0.43853(7) -0.05383(11) 0.0378(4) Uani 1 d . . . C18 C 0.1989(2) 0.31593(7) 0.07817(11) 0.0382(4) Uani 1 d . . . C23 C 0.2575(2) 0.43569(6) -0.05636(11) 0.0354(4) Uani 1 d . . . C2 C 0.9825(2) 0.07244(8) 0.90635(11) 0.0427(4) Uani 1 d . . . C16 C 0.4509(2) 0.30679(8) 0.15177(12) 0.0444(4) Uani 1 d . . . C21 C 0.0499(2) 0.43627(7) 0.02858(11) 0.0396(4) Uani 1 d . . . C15 C 0.4964(2) 0.31057(8) 0.06923(12) 0.0438(4) Uani 1 d . . . C4 C 1.0379(2) 0.06184(7) 1.06072(11) 0.0389(4) Uani 1 d . . . C17 C 0.2916(2) 0.31131(7) 0.15547(11) 0.0400(4) Uani 1 d . . . N1 N 0.92709(19) 0.21349(7) 0.88264(10) 0.0512(4) Uani 1 d . . . H1B H 0.9093 0.1996 0.8309 0.061 Uiso 1 calc R . . H1A H 0.8791 0.1974 0.9177 0.061 Uiso 1 calc R . . N2 N 0.50589(18) 0.18392(6) 0.80078(10) 0.0462(4) Uani 1 d . . . H2A H 0.573 0.1809 0.7674 0.055 Uiso 1 calc R . . H2B H 0.5497 0.185 0.8556 0.055 Uiso 1 calc R . . N3 N 0.11839(18) 0.46829(7) 0.71936(10) 0.0480(4) Uani 1 d . . . H3A H 0.137 0.4523 0.7691 0.058 Uiso 1 calc R . . H3B H 0.169 0.4548 0.6826 0.058 Uiso 1 calc R . . C29 C -0.0338(3) 0.46345(12) 0.68456(15) 0.0687(7) Uani 1 d . . . H29C H -0.0572 0.4306 0.6766 0.103 Uiso 1 calc R . . H29A H -0.0543 0.4796 0.6306 0.103 Uiso 1 calc R . . H29B H -0.0888 0.4771 0.7239 0.103 Uiso 1 calc R . . C31 C 0.3977(3) 0.53031(9) 0.18317(14) 0.0585(6) Uani 1 d . . . H31B H 0.4702 0.5066 0.1937 0.088 Uiso 1 calc R . . H31A H 0.3548 0.5294 0.124 0.088 Uiso 1 calc R . . H31C H 0.327 0.5243 0.2184 0.088 Uiso 1 calc R . . C30 C 0.1651(3) 0.51751(10) 0.73426(18) 0.0712(7) Uani 1 d . . . H30C H 0.2645 0.5181 0.7569 0.107 Uiso 1 calc R . . H30A H 0.1133 0.532 0.7744 0.107 Uiso 1 calc R . . H30B H 0.1482 0.5346 0.6812 0.107 Uiso 1 calc R . . C27 C 0.4140(3) 0.14198(9) 0.78926(17) 0.0643(6) Uani 1 d . . . H27B H 0.47 0.1141 0.8041 0.096 Uiso 1 calc R . . H27A H 0.3688 0.14 0.7306 0.096 Uiso 1 calc R . . H27C H 0.3433 0.1444 0.8256 0.096 Uiso 1 calc R . . C28 C 0.4308(3) 0.22887(9) 0.78002(15) 0.0650(6) Uani 1 d . . . H58A H 0.4971 0.2546 0.7891 0.098 Uiso 1 calc R . . H58B H 0.3604 0.2329 0.8162 0.098 Uiso 1 calc R . . H58C H 0.3859 0.2285 0.7212 0.098 Uiso 1 calc R . . C25 C 1.0798(3) 0.20958(11) 0.91572(16) 0.0688(7) Uani 1 d . . . H25A H 1.1068 0.1768 0.9187 0.103 Uiso 1 calc R . . H25B H 1.0996 0.2233 0.9718 0.103 Uiso 1 calc R . . H25C H 1.1323 0.226 0.8781 0.103 Uiso 1 calc R . . C32 C 0.3571(2) 0.61618(9) 0.18960(16) 0.0597(6) Uani 1 d . . . H32B H 0.4044 0.6457 0.2041 0.09 Uiso 1 calc R . . H32C H 0.2858 0.6115 0.225 0.09 Uiso 1 calc R . . H32A H 0.3135 0.6167 0.1305 0.09 Uiso 1 calc R . . C26 C 0.8735(3) 0.26229(10) 0.87464(18) 0.0721(7) Uani 1 d . . . H26B H 0.7739 0.2619 0.8526 0.108 Uiso 1 calc R . . H26C H 0.9223 0.2796 0.8362 0.108 Uiso 1 calc R . . H26A H 0.8892 0.2772 0.9299 0.108 Uiso 1 calc R . . N4 N 0.46061(17) 0.57728(6) 0.20375(10) 0.0430(4) Uani 1 d . . . H4B H 0.5282 0.5823 0.1714 0.052 Uiso 1 calc R . . H4A H 0.5025 0.5775 0.259 0.052 Uiso 1 calc R . . 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 Cl8 0.0303(2) 0.0756(3) 0.0407(2) 0.0019(2) 0.00995(18) -0.0019(2) Cl6 0.0371(3) 0.0779(3) 0.0363(2) -0.0004(2) 0.00824(19) -0.0083(2) Cl2 0.0306(2) 0.0849(4) 0.0371(2) -0.0025(2) 0.00721(18) -0.0070(2) Cl1 0.0305(2) 0.1209(5) 0.0349(2) 0.0006(3) 0.00822(19) 0.0000(3) Cl3 0.0362(3) 0.1168(5) 0.0401(3) 0.0055(3) 0.0097(2) 0.0044(3) Cl4 0.0356(2) 0.0774(3) 0.0406(3) 0.0006(2) 0.00777(19) -0.0047(2) Cl5 0.0401(3) 0.1074(5) 0.0479(3) 0.0046(3) 0.0117(2) 0.0141(3) Cl7 0.0298(2) 0.1000(4) 0.0409(3) 0.0037(3) 0.00687(19) 0.0044(2) O9 0.0479(8) 0.0733(9) 0.0243(6) 0.0013(6) 0.0009(5) -0.0133(7) O16 0.0436(8) 0.0720(9) 0.0258(6) 0.0056(6) 0.0110(5) 0.0055(6) O10 0.0444(8) 0.0846(11) 0.0278(6) -0.0011(6) 0.0104(6) -0.0024(7) O12 0.0465(8) 0.0813(10) 0.0270(6) 0.0074(6) 0.0099(6) 0.0074(7) O1 0.0408(8) 0.1137(14) 0.0243(6) 0.0035(7) 0.0006(6) -0.0007(8) C24 0.0293(8) 0.0460(9) 0.0285(8) -0.0004(7) 0.0063(6) -0.0012(7) C13 0.0405(10) 0.0445(9) 0.0269(8) -0.0025(7) 0.0040(7) -0.0060(7) O13 0.0387(7) 0.0670(9) 0.0236(6) -0.0001(5) 0.0013(5) -0.0003(6) O8 0.0434(8) 0.0782(10) 0.0274(6) 0.0059(6) 0.0086(6) -0.0068(7) C19 0.0331(8) 0.0413(9) 0.0252(8) -0.0023(6) 0.0034(6) -0.0009(7) C3 0.0308(9) 0.0654(12) 0.0276(8) -0.0012(8) 0.0064(7) -0.0017(8) C5 0.0367(9) 0.0471(10) 0.0250(8) 0.0005(7) 0.0072(7) -0.0027(7) C9 0.0367(10) 0.0615(12) 0.0300(9) 0.0001(8) 0.0076(7) -0.0012(8) O15 0.0429(8) 0.0930(12) 0.0277(7) 0.0068(7) 0.0010(6) 0.0031(7) C14 0.0444(10) 0.0493(10) 0.0284(8) -0.0022(7) 0.0090(7) -0.0033(8) C10 0.0408(10) 0.0528(10) 0.0270(8) 0.0021(7) 0.0043(7) -0.0012(8) O7 0.0458(8) 0.0953(12) 0.0293(7) 0.0100(7) 0.0025(6) 0.0045(8) O4 0.0406(7) 0.0730(9) 0.0240(6) 0.0035(6) 0.0087(5) -0.0068(6) C20 0.0339(9) 0.0504(10) 0.0249(8) -0.0006(7) 0.0082(7) -0.0011(7) C12 0.0339(9) 0.0501(10) 0.0296(8) 0.0010(7) 0.0061(7) -0.0021(7) O5 0.0464(8) 0.0821(10) 0.0256(6) 0.0032(6) 0.0018(6) 0.0051(7) O6 0.0463(8) 0.1044(13) 0.0257(6) 0.0070(7) 0.0089(6) 0.0015(8) O2 0.0391(8) 0.1278(15) 0.0224(6) 0.0055(8) 0.0064(5) -0.0054(8) C1 0.0354(9) 0.0614(11) 0.0251(8) -0.0014(7) 0.0021(7) -0.0015(8) C7 0.0431(10) 0.0469(10) 0.0268(8) -0.0006(7) 0.0036(7) 0.0004(8) O3 0.0401(8) 0.1024(12) 0.0259(6) 0.0059(7) 0.0016(6) 0.0051(8) O14 0.0339(7) 0.0877(11) 0.0249(6) 0.0013(6) 0.0084(5) 0.0018(7) C11 0.0438(10) 0.0463(10) 0.0269(8) 0.0018(7) 0.0071(7) -0.0036(8) O11 0.0484(9) 0.1196(15) 0.0333(8) 0.0138(8) 0.0027(7) 0.0144(9) C6 0.0316(9) 0.0567(11) 0.0277(8) -0.0003(7) 0.0050(7) -0.0041(7) C8 0.0431(10) 0.0557(11) 0.0251(8) 0.0014(7) 0.0086(7) -0.0008(8) C22 0.0348(9) 0.0517(10) 0.0264(8) 0.0014(7) 0.0030(7) 0.0006(7) C18 0.0375(9) 0.0491(10) 0.0281(8) -0.0005(7) 0.0058(7) -0.0043(7) C23 0.0385(9) 0.0435(9) 0.0250(8) 0.0018(6) 0.0080(7) 0.0007(7) C2 0.0392(10) 0.0652(12) 0.0244(8) 0.0007(7) 0.0072(7) -0.0016(8) C16 0.0426(10) 0.0584(11) 0.0316(9) 0.0043(8) 0.0041(8) 0.0061(9) C21 0.0312(9) 0.0591(11) 0.0294(8) 0.0011(7) 0.0070(7) 0.0022(8) C15 0.0365(10) 0.0603(12) 0.0356(9) 0.0010(8) 0.0091(8) 0.0062(8) C4 0.0367(9) 0.0543(11) 0.0249(8) 0.0006(7) 0.0026(7) 0.0001(8) C17 0.0438(10) 0.0494(10) 0.0274(8) 0.0018(7) 0.0073(7) 0.0013(8) N1 0.0506(10) 0.0744(12) 0.0295(8) -0.0050(7) 0.0090(7) -0.0193(9) N2 0.0460(9) 0.0661(11) 0.0271(7) 0.0014(7) 0.0080(7) 0.0023(8) N3 0.0508(10) 0.0670(11) 0.0282(7) 0.0080(7) 0.0124(7) 0.0192(8) C29 0.0511(13) 0.112(2) 0.0418(12) 0.0062(12) 0.0040(10) 0.0196(14) C31 0.0707(15) 0.0649(14) 0.0411(11) -0.0067(10) 0.0129(10) -0.0147(11) C30 0.089(2) 0.0658(15) 0.0656(16) 0.0071(12) 0.0319(14) 0.0094(14) C27 0.0728(16) 0.0669(15) 0.0563(14) -0.0042(11) 0.0194(12) -0.0082(12) C28 0.0856(18) 0.0640(14) 0.0466(12) 0.0026(10) 0.0145(12) 0.0124(13) C25 0.0528(13) 0.105(2) 0.0474(13) -0.0004(13) 0.0059(10) -0.0156(13) C32 0.0515(13) 0.0747(15) 0.0542(13) -0.0031(11) 0.0123(10) 0.0036(11) C26 0.0723(17) 0.0770(17) 0.0636(15) -0.0035(13) 0.0013(13) -0.0190(14) N4 0.0393(8) 0.0637(10) 0.0267(7) -0.0017(7) 0.0072(6) -0.0059(7) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl8 C24 1.729(2) . ? Cl6 C18 1.729(2) . ? Cl2 C6 1.733(2) . ? Cl1 C3 1.716(2) . ? Cl3 C9 1.714(2) . ? Cl4 C12 1.729(2) . ? Cl5 C15 1.720(2) . ? Cl7 C21 1.722(2) . ? O9 C13 1.241(2) . ? O16 C23 1.241(2) . ? O10 C14 1.324(2) . ? O10 H10 0.82 . ? O12 C17 1.250(2) . ? O1 C1 1.239(2) . ? C24 C23 1.397(2) . ? C24 C19 1.401(2) . ? C13 C18 1.406(3) . ? C13 C14 1.501(3) . ? O13 C19 1.239(2) . ? O8 C11 1.249(2) . ? C19 C20 1.509(3) . ? C3 C2 1.349(3) . ? C3 C4 1.447(2) . ? C5 O4 1.255(2) . ? C5 C6 1.396(3) . ? C5 C4 1.537(3) . ? C9 C8 1.350(3) . ? C9 C10 1.454(3) . ? O15 C22 1.213(2) . ? C14 C15 1.345(3) . ? C10 O7 1.215(2) . ? C10 C11 1.535(3) . ? C20 O14 1.326(2) . ? C20 C21 1.344(3) . ? C12 C11 1.398(3) . ? C12 C7 1.401(3) . ? O5 C7 1.247(2) . ? O6 C8 1.326(2) . ? O6 H6 0.82 . ? O2 C2 1.319(2) . ? O2 H2 0.82 . ? C1 C6 1.403(3) . ? C1 C2 1.512(3) . ? C7 C8 1.504(3) . ? O3 C4 1.216(2) . ? O14 H14 0.82 . ? O11 C16 1.217(2) . ? C22 C21 1.449(2) . ? C22 C23 1.548(3) . ? C18 C17 1.395(3) . ? C16 C15 1.447(3) . ? C16 C17 1.542(3) . ? N1 C26 1.470(4) . ? N1 C25 1.474(3) . ? N1 H1B 0.9 . ? N1 H1A 0.9 . ? N2 C27 1.470(3) . ? N2 C28 1.471(3) . ? N2 H2A 0.9 . ? N2 H2B 0.9 . ? N3 C30 1.469(3) . ? N3 C29 1.478(3) . ? N3 H3A 0.9 . ? N3 H3B 0.9 . ? C29 H29C 0.96 . ? C29 H29A 0.96 . ? C29 H29B 0.96 . ? C31 N4 1.472(3) . ? C31 H31B 0.96 . ? C31 H31A 0.96 . ? C31 H31C 0.96 . ? C30 H30C 0.96 . ? C30 H30A 0.96 . ? C30 H30B 0.96 . ? C27 H27B 0.96 . ? C27 H27A 0.96 . ? C27 H27C 0.96 . ? C28 H58A 0.96 . ? C28 H58B 0.96 . ? C28 H58C 0.96 . ? C25 H25A 0.96 . ? C25 H25B 0.96 . ? C25 H25C 0.96 . ? C32 N4 1.473(3) . ? C32 H32B 0.96 . ? C32 H32C 0.96 . ? C32 H32A 0.96 . ? C26 H26B 0.96 . ? C26 H26C 0.96 . ? C26 H26A 0.96 . ? N4 H4B 0.9 . ? N4 H4A 0.9 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O10 H10 109.5 . . ? C23 C24 C19 123.18(16) . . ? C23 C24 Cl8 119.07(14) . . ? C19 C24 Cl8 117.67(13) . . ? O9 C13 C18 125.86(18) . . ? O9 C13 C14 116.17(16) . . ? C18 C13 C14 117.97(16) . . ? O13 C19 C24 125.95(17) . . ? O13 C19 C20 116.04(15) . . ? C24 C19 C20 118.01(15) . . ? C2 C3 C4 120.87(17) . . ? C2 C3 Cl1 120.90(15) . . ? C4 C3 Cl1 118.22(14) . . ? O4 C5 C6 126.11(18) . . ? O4 C5 C4 116.37(15) . . ? C6 C5 C4 117.52(15) . . ? C8 C9 C10 120.05(18) . . ? C8 C9 Cl3 121.25(15) . . ? C10 C9 Cl3 118.71(14) . . ? O10 C14 C15 122.18(19) . . ? O10 C14 C13 115.63(16) . . ? C15 C14 C13 122.19(17) . . ? O7 C10 C9 122.87(19) . . ? O7 C10 C11 118.57(17) . . ? C9 C10 C11 118.56(16) . . ? O14 C20 C21 122.29(17) . . ? O14 C20 C19 115.72(15) . . ? C21 C20 C19 121.99(16) . . ? C11 C12 C7 123.10(17) . . ? C11 C12 Cl4 118.61(14) . . ? C7 C12 Cl4 118.27(14) . . ? C8 O6 H6 109.5 . . ? C2 O2 H2 109.5 . . ? O1 C1 C6 125.77(18) . . ? O1 C1 C2 116.40(17) . . ? C6 C1 C2 117.82(16) . . ? O5 C7 C12 126.00(19) . . ? O5 C7 C8 116.25(16) . . ? C12 C7 C8 117.75(16) . . ? C20 O14 H14 109.5 . . ? O8 C11 C12 125.80(19) . . ? O8 C11 C10 116.42(16) . . ? C12 C11 C10 117.76(16) . . ? C5 C6 C1 123.43(17) . . ? C5 C6 Cl2 118.28(14) . . ? C1 C6 Cl2 118.24(14) . . ? O6 C8 C9 121.04(18) . . ? O6 C8 C7 116.46(16) . . ? C9 C8 C7 122.50(17) . . ? O15 C22 C21 123.35(18) . . ? O15 C22 C23 118.15(16) . . ? C21 C22 C23 118.50(15) . . ? C17 C18 C13 122.86(18) . . ? C17 C18 Cl6 118.34(14) . . ? C13 C18 Cl6 118.73(14) . . ? O16 C23 C24 126.47(18) . . ? O16 C23 C22 116.20(15) . . ? C24 C23 C22 117.33(15) . . ? O2 C2 C3 121.22(18) . . ? O2 C2 C1 117.11(16) . . ? C3 C2 C1 121.66(16) . . ? O11 C16 C15 123.4(2) . . ? O11 C16 C17 118.24(18) . . ? C15 C16 C17 118.31(16) . . ? C20 C21 C22 120.71(17) . . ? C20 C21 Cl7 120.87(14) . . ? C22 C21 Cl7 118.41(14) . . ? C14 C15 C16 120.71(18) . . ? C14 C15 Cl5 120.82(15) . . ? C16 C15 Cl5 118.47(15) . . ? O3 C4 C3 122.78(18) . . ? O3 C4 C5 118.59(16) . . ? C3 C4 C5 118.63(15) . . ? O12 C17 C18 125.77(19) . . ? O12 C17 C16 116.49(16) . . ? C18 C17 C16 117.74(16) . . ? C26 N1 C25 114.4(2) . . ? C26 N1 H1B 108.7 . . ? C25 N1 H1B 108.7 . . ? C26 N1 H1A 108.7 . . ? C25 N1 H1A 108.7 . . ? H1B N1 H1A 107.6 . . ? C27 N2 C28 114.1(2) . . ? C27 N2 H2A 108.7 . . ? C28 N2 H2A 108.7 . . ? C27 N2 H2B 108.7 . . ? C28 N2 H2B 108.7 . . ? H2A N2 H2B 107.6 . . ? C30 N3 C29 113.8(2) . . ? C30 N3 H3A 108.8 . . ? C29 N3 H3A 108.8 . . ? C30 N3 H3B 108.8 . . ? C29 N3 H3B 108.8 . . ? H3A N3 H3B 107.7 . . ? N3 C29 H29C 109.5 . . ? N3 C29 H29A 109.5 . . ? H29C C29 H29A 109.5 . . ? N3 C29 H29B 109.5 . . ? H29C C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N4 C31 H31B 109.5 . . ? N4 C31 H31A 109.5 . . ? H31B C31 H31A 109.5 . . ? N4 C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? N3 C30 H30C 109.5 . . ? N3 C30 H30A 109.5 . . ? H30C C30 H30A 109.5 . . ? N3 C30 H30B 109.5 . . ? H30C C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N2 C27 H27B 109.5 . . ? N2 C27 H27A 109.5 . . ? H27B C27 H27A 109.5 . . ? N2 C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? N2 C28 H58A 109.5 . . ? N2 C28 H58B 109.5 . . ? H58A C28 H58B 109.5 . . ? N2 C28 H58C 109.5 . . ? H58A C28 H58C 109.5 . . ? H58B C28 H58C 109.5 . . ? N1 C25 H25A 109.5 . . ? N1 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N4 C32 H32B 109.5 . . ? N4 C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N4 C32 H32A 109.5 . . ? H32B C32 H32A 109.5 . . ? H32C C32 H32A 109.5 . . ? N1 C26 H26B 109.5 . . ? N1 C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N1 C26 H26A 109.5 . . ? H26B C26 H26A 109.5 . . ? H26C C26 H26A 109.5 . . ? C31 N4 C32 113.51(18) . . ? C31 N4 H4B 108.9 . . ? C32 N4 H4B 108.9 . . ? C31 N4 H4A 108.9 . . ? C32 N4 H4A 108.9 . . ? H4B N4 H4A 107.7 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C23 C24 C19 O13 173.57(18) . . . . ? Cl8 C24 C19 O13 -3.1(3) . . . . ? C23 C24 C19 C20 -6.5(3) . . . . ? Cl8 C24 C19 C20 176.80(13) . . . . ? O9 C13 C14 O10 -0.7(3) . . . . ? C18 C13 C14 O10 179.82(17) . . . . ? O9 C13 C14 C15 179.12(19) . . . . ? C18 C13 C14 C15 -0.4(3) . . . . ? C8 C9 C10 O7 -179.2(2) . . . . ? Cl3 C9 C10 O7 0.3(3) . . . . ? C8 C9 C10 C11 0.3(3) . . . . ? Cl3 C9 C10 C11 179.89(14) . . . . ? O13 C19 C20 O14 3.0(2) . . . . ? C24 C19 C20 O14 -176.95(16) . . . . ? O13 C19 C20 C21 -176.67(18) . . . . ? C24 C19 C20 C21 3.4(3) . . . . ? C11 C12 C7 O5 178.4(2) . . . . ? Cl4 C12 C7 O5 0.1(3) . . . . ? C11 C12 C7 C8 -2.1(3) . . . . ? Cl4 C12 C7 C8 179.61(14) . . . . ? C7 C12 C11 O8 -175.7(2) . . . . ? Cl4 C12 C11 O8 2.6(3) . . . . ? C7 C12 C11 C10 5.6(3) . . . . ? Cl4 C12 C11 C10 -176.05(14) . . . . ? O7 C10 C11 O8 -4.0(3) . . . . ? C9 C10 C11 O8 176.43(18) . . . . ? O7 C10 C11 C12 174.78(19) . . . . ? C9 C10 C11 C12 -4.8(3) . . . . ? O4 C5 C6 C1 176.4(2) . . . . ? C4 C5 C6 C1 -3.0(3) . . . . ? O4 C5 C6 Cl2 -0.8(3) . . . . ? C4 C5 C6 Cl2 179.76(14) . . . . ? O1 C1 C6 C5 -177.2(2) . . . . ? C2 C1 C6 C5 1.5(3) . . . . ? O1 C1 C6 Cl2 0.1(3) . . . . ? C2 C1 C6 Cl2 178.71(15) . . . . ? C10 C9 C8 O6 -177.09(19) . . . . ? Cl3 C9 C8 O6 3.4(3) . . . . ? C10 C9 C8 C7 3.4(3) . . . . ? Cl3 C9 C8 C7 -176.11(15) . . . . ? O5 C7 C8 O6 -2.7(3) . . . . ? C12 C7 C8 O6 177.72(18) . . . . ? O5 C7 C8 C9 176.8(2) . . . . ? C12 C7 C8 C9 -2.8(3) . . . . ? O9 C13 C18 C17 -175.28(19) . . . . ? C14 C13 C18 C17 4.2(3) . . . . ? O9 C13 C18 Cl6 1.6(3) . . . . ? C14 C13 C18 Cl6 -178.89(14) . . . . ? C19 C24 C23 O16 -174.09(19) . . . . ? Cl8 C24 C23 O16 2.6(3) . . . . ? C19 C24 C23 C22 5.7(3) . . . . ? Cl8 C24 C23 C22 -177.67(13) . . . . ? O15 C22 C23 O16 -2.5(3) . . . . ? C21 C22 C23 O16 178.03(18) . . . . ? O15 C22 C23 C24 177.68(18) . . . . ? C21 C22 C23 C24 -1.7(3) . . . . ? C4 C3 C2 O2 178.8(2) . . . . ? Cl1 C3 C2 O2 -0.5(3) . . . . ? C4 C3 C2 C1 -0.2(3) . . . . ? Cl1 C3 C2 C1 -179.54(16) . . . . ? O1 C1 C2 O2 0.0(3) . . . . ? C6 C1 C2 O2 -178.79(19) . . . . ? O1 C1 C2 C3 179.0(2) . . . . ? C6 C1 C2 C3 0.3(3) . . . . ? O14 C20 C21 C22 -179.37(18) . . . . ? C19 C20 C21 C22 0.3(3) . . . . ? O14 C20 C21 Cl7 0.0(3) . . . . ? C19 C20 C21 Cl7 179.61(14) . . . . ? O15 C22 C21 C20 179.5(2) . . . . ? C23 C22 C21 C20 -1.1(3) . . . . ? O15 C22 C21 Cl7 0.2(3) . . . . ? C23 C22 C21 Cl7 179.58(14) . . . . ? O10 C14 C15 C16 178.43(19) . . . . ? C13 C14 C15 C16 -1.3(3) . . . . ? O10 C14 C15 Cl5 -1.1(3) . . . . ? C13 C14 C15 Cl5 179.13(15) . . . . ? O11 C16 C15 C14 178.8(2) . . . . ? C17 C16 C15 C14 -0.4(3) . . . . ? O11 C16 C15 Cl5 -1.7(3) . . . . ? C17 C16 C15 Cl5 179.19(15) . . . . ? C2 C3 C4 O3 179.1(2) . . . . ? Cl1 C3 C4 O3 -1.6(3) . . . . ? C2 C3 C4 C5 -1.4(3) . . . . ? Cl1 C3 C4 C5 177.97(14) . . . . ? O4 C5 C4 O3 3.0(3) . . . . ? C6 C5 C4 O3 -177.49(19) . . . . ? O4 C5 C4 C3 -176.52(18) . . . . ? C6 C5 C4 C3 2.9(3) . . . . ? C13 C18 C17 O12 174.4(2) . . . . ? Cl6 C18 C17 O12 -2.5(3) . . . . ? C13 C18 C17 C16 -5.8(3) . . . . ? Cl6 C18 C17 C16 177.28(14) . . . . ? O11 C16 C17 O12 4.4(3) . . . . ? C15 C16 C17 O12 -176.38(19) . . . . ? O11 C16 C17 C18 -175.3(2) . . . . ? C15 C16 C17 C18 3.8(3) . . . . ? # Attachment 'Me2NH2HCA-triclinic1.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-02-29 at 12:25:52 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : f:\programs\wingx\files\cifdoc.dat # CIF files read : inozin-ca-1 inozin-ca-1-teh struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_Me2NH2HCA-triclinic _database_code_depnum_ccdc_archive 'CCDC 729429' _audit_creation_date 2008-02-29T12:25:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C6 H Cl2 O4, C2 H8 N' _chemical_formula_sum 'C8 H9 Cl2 N O4' _chemical_formula_weight 254.07 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7169(4) _cell_length_b 8.7529(4) _cell_length_c 15.8026(6) _cell_angle_alpha 85.440(3) _cell_angle_beta 75.118(4) _cell_angle_gamma 66.352(4) _cell_volume 1067.04(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5647 _cell_measurement_theta_min 2.8889 _cell_measurement_theta_max 75.915 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 5.471 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4660 _exptl_absorpt_correction_T_max 0.7200 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.54179 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Oxford Xcalibur Nova' _diffrn_measurement_method ; CCD detector ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4323 _diffrn_reflns_number 11555 _diffrn_reflns_av_R_equivalents 0.029 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 75 _diffrn_reflns_theta_full 75 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measured_fraction_theta_full 0.979 _reflns_number_total 4280 _reflns_number_gt 3612 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.1168P)^2^+0.5058P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4280 _refine_ls_number_parameters 271 _refine_ls_number_restraints 2 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.1869 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 2.625 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.821 _refine_diff_density_min -0.309 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 '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' Cl Cl 0.148 0.159 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.011 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Cl1 Cl 0.3988(3) 0.8789(3) 0.44365(13) 0.0713(8) Uani 1 d . . . Cl2 Cl 1.0486(3) 0.2222(2) 0.46675(13) 0.0583(7) Uani 1 d . . . O4 O 0.7916(8) 0.4517(6) 0.6146(3) 0.0497(13) Uani 1 d . . . O3 O 0.5102(8) 0.7204(8) 0.6010(3) 0.0615(17) Uani 1 d D . . C5 C 0.7668(10) 0.4887(9) 0.5402(4) 0.0412(15) Uani 1 d . . . C2 C 0.6830(10) 0.6125(9) 0.3759(5) 0.0472(17) Uani 1 d . . . C6 C 0.8700(10) 0.4017(9) 0.4618(5) 0.0447(16) Uani 1 d . . . C1 C 0.8375(10) 0.4552(9) 0.3793(4) 0.0454(16) Uani 1 d D . . C4 C 0.6053(9) 0.6464(9) 0.5346(4) 0.0423(15) Uani 1 d . . . C3 C 0.5748(10) 0.6997(9) 0.4491(5) 0.0474(17) Uani 1 d . . . Cl4 Cl 0.3751(2) 0.3524(2) 0.00708(12) 0.0479(6) Uani 1 d . . . Cl3 Cl -0.2643(3) 1.0259(2) -0.00852(13) 0.0581(7) Uani 1 d . . . O5 O 0.1978(6) 0.4826(6) -0.1375(3) 0.0424(11) Uani 1 d . . . O8 O 0.1486(7) 0.6012(6) 0.1552(3) 0.0475(12) Uani 1 d . . . C10 C -0.0427(9) 0.7996(8) 0.0786(4) 0.0397(14) Uani 1 d . . . C8 C -0.0129(8) 0.7351(8) -0.0726(4) 0.0367(13) Uani 1 d . . . C7 C 0.1378(8) 0.5716(8) -0.0705(4) 0.0334(13) Uani 1 d . . . C12 C 0.1963(8) 0.5346(8) 0.0067(4) 0.0341(13) Uani 1 d . . . C11 C 0.1124(9) 0.6332(8) 0.0830(4) 0.0361(13) Uani 1 d . . . C9 C -0.0936(9) 0.8402(8) -0.0034(5) 0.0400(14) Uani 1 d . . . N1 N 0.9702(9) 0.1723(8) 0.7018(4) 0.0504(16) Uani 1 d . . . H1A H 0.9803 0.2211 0.747 0.061 Uiso 1 calc R . . H1B H 0.948 0.2487 0.6602 0.061 Uiso 1 calc R . . C13 C 1.1363(15) 0.0329(12) 0.6662(7) 0.079(3) Uani 1 d . . . H13A H 1.226 0.0743 0.6479 0.119 Uiso 1 calc R . . H13B H 1.1281 -0.0183 0.617 0.119 Uiso 1 calc R . . H13C H 1.163 -0.0481 0.7107 0.119 Uiso 1 calc R . . C14 C 0.8223(16) 0.1227(13) 0.7322(7) 0.076(3) Uani 1 d . . . H14A H 0.7192 0.2193 0.7544 0.114 Uiso 1 calc R . . H14B H 0.8432 0.0434 0.7779 0.114 Uiso 1 calc R . . H14C H 0.8084 0.0731 0.6842 0.114 Uiso 1 calc R . . N2 N 0.6243(7) 0.6646(8) 0.7676(4) 0.0422(13) Uani 1 d . . . H2A H 0.6676 0.6209 0.7127 0.051 Uiso 1 calc R . . H2B H 0.7006 0.6061 0.7991 0.051 Uiso 1 calc R . . C15 C 0.4614(11) 0.6442(13) 0.8052(6) 0.061(2) Uani 1 d . . . H15A H 0.4823 0.5279 0.8053 0.092 Uiso 1 calc R . . H15B H 0.3803 0.7029 0.7708 0.092 Uiso 1 calc R . . H15C H 0.4151 0.6887 0.8642 0.092 Uiso 1 calc R . . C16 C 0.6078(12) 0.8384(11) 0.7649(6) 0.061(2) Uani 1 d . . . H16A H 0.7188 0.842 0.7396 0.092 Uiso 1 calc R . . H16B H 0.5647 0.8855 0.8233 0.092 Uiso 1 calc R . . H16C H 0.529 0.9014 0.73 0.092 Uiso 1 calc R . . O6 O -0.0586(7) 0.7669(7) -0.1477(3) 0.0500(13) Uani 1 d . . . H6 H 0.0046 0.6897 -0.1828 0.075 Uiso 1 calc R . . O7 O -0.1133(8) 0.8895(7) 0.1437(4) 0.0578(15) Uani 1 d . . . O1 O 0.9296(9) 0.3825(8) 0.3089(3) 0.0667(19) Uani 1 d . . . O2 O 0.6584(9) 0.6617(8) 0.2990(4) 0.0677(19) Uani 1 d . . . H2 H 0.6114 0.6093 0.2824 0.102 Uiso 1 calc RD . . 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 0.0685(14) 0.0629(13) 0.0403(11) -0.0076(9) -0.0235(9) 0.0245(11) Cl2 0.0627(12) 0.0430(10) 0.0416(10) -0.0046(7) -0.0193(8) 0.0119(8) O4 0.064(3) 0.043(3) 0.027(2) 0.0028(19) -0.015(2) -0.003(2) O3 0.061(3) 0.063(3) 0.029(3) -0.005(2) -0.012(2) 0.008(3) C5 0.051(4) 0.037(3) 0.027(3) 0.004(2) -0.014(3) -0.008(3) C2 0.054(4) 0.045(4) 0.029(3) -0.004(3) -0.014(3) -0.003(3) C6 0.051(4) 0.034(3) 0.033(3) -0.001(3) -0.014(3) 0.002(3) C1 0.052(4) 0.042(4) 0.028(3) -0.005(3) -0.011(3) -0.003(3) C4 0.047(4) 0.041(3) 0.027(3) -0.001(3) -0.010(3) -0.005(3) C3 0.051(4) 0.042(4) 0.032(4) -0.002(3) -0.015(3) 0.003(3) Cl4 0.0421(9) 0.0430(10) 0.0436(10) -0.0018(7) -0.0181(7) 0.0036(7) Cl3 0.0585(12) 0.0431(10) 0.0489(11) -0.0063(8) -0.0230(9) 0.0113(8) O5 0.045(2) 0.045(3) 0.026(2) -0.0042(18) -0.0085(18) -0.005(2) O8 0.056(3) 0.045(3) 0.032(2) -0.003(2) -0.022(2) -0.003(2) C10 0.042(3) 0.039(3) 0.032(3) -0.004(3) -0.011(3) -0.008(3) C8 0.041(3) 0.039(3) 0.027(3) 0.002(2) -0.013(2) -0.010(3) C7 0.034(3) 0.035(3) 0.028(3) 0.002(2) -0.009(2) -0.010(2) C12 0.033(3) 0.033(3) 0.030(3) 0.001(2) -0.012(2) -0.005(2) C11 0.043(3) 0.036(3) 0.028(3) 0.001(2) -0.014(2) -0.011(3) C9 0.040(3) 0.033(3) 0.036(3) -0.001(2) -0.014(3) 0.000(3) N1 0.074(4) 0.038(3) 0.034(3) -0.001(2) -0.025(3) -0.009(3) C13 0.093(7) 0.057(5) 0.050(5) -0.007(4) -0.024(5) 0.014(5) C14 0.105(8) 0.067(6) 0.074(7) 0.018(5) -0.046(6) -0.041(6) N2 0.041(3) 0.049(3) 0.028(3) 0.000(2) -0.013(2) -0.007(2) C15 0.058(5) 0.086(6) 0.044(4) 0.004(4) -0.014(4) -0.032(4) C16 0.070(5) 0.058(5) 0.057(5) 0.009(4) -0.024(4) -0.023(4) O6 0.056(3) 0.045(3) 0.032(2) -0.002(2) -0.020(2) 0.003(2) O7 0.065(3) 0.052(3) 0.037(3) -0.013(2) -0.019(2) 0.003(3) O1 0.073(4) 0.065(4) 0.027(3) -0.011(2) -0.013(2) 0.011(3) O2 0.081(4) 0.060(3) 0.029(3) -0.004(2) -0.023(3) 0.013(3) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C3 1.714(7) . ? Cl2 C6 1.725(7) . ? O4 C5 1.244(8) . ? O3 C4 1.200(9) . ? C5 C6 1.397(10) . ? C5 C4 1.543(9) . ? C2 O2 1.298(9) . ? C2 C3 1.346(10) . ? C2 C1 1.501(10) . ? C6 C1 1.409(10) . ? C1 O1 1.237(9) . ? C4 C3 1.449(10) . ? Cl4 C12 1.726(6) . ? Cl3 C9 1.721(7) . ? O5 C7 1.234(8) . ? O8 C11 1.243(8) . ? C10 O7 1.213(9) . ? C10 C9 1.448(9) . ? C10 C11 1.551(9) . ? C8 O6 1.320(8) . ? C8 C9 1.336(9) . ? C8 C7 1.511(9) . ? C7 C12 1.406(9) . ? C12 C11 1.392(9) . ? N1 C14 1.476(14) . ? N1 C13 1.475(11) . ? N1 H1A 0.9 . ? N1 H1B 0.9 . ? C13 H13A 0.96 . ? C13 H13B 0.96 . ? C13 H13C 0.96 . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? N2 C15 1.468(10) . ? N2 C16 1.468(11) . ? N2 H2A 0.9 . ? N2 H2B 0.9 . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? O6 H6 0.82 . ? O2 H2 0.82 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 C5 C6 126.5(7) . . ? O4 C5 C4 116.4(6) . . ? C6 C5 C4 117.1(6) . . ? O2 C2 C3 121.3(7) . . ? O2 C2 C1 117.0(6) . . ? C3 C2 C1 121.7(6) . . ? C5 C6 C1 123.3(6) . . ? C5 C6 Cl2 118.0(5) . . ? C1 C6 Cl2 118.7(5) . . ? O1 C1 C6 124.4(7) . . ? O1 C1 C2 117.4(6) . . ? C6 C1 C2 118.1(6) . . ? O3 C4 C3 122.5(7) . . ? O3 C4 C5 118.8(6) . . ? C3 C4 C5 118.6(6) . . ? C2 C3 C4 121.0(7) . . ? C2 C3 Cl1 120.9(6) . . ? C4 C3 Cl1 118.0(5) . . ? O7 C10 C9 123.6(6) . . ? O7 C10 C11 118.2(6) . . ? C9 C10 C11 118.2(5) . . ? O6 C8 C9 122.5(6) . . ? O6 C8 C7 115.4(5) . . ? C9 C8 C7 122.2(6) . . ? O5 C7 C12 126.2(6) . . ? O5 C7 C8 116.1(5) . . ? C12 C7 C8 117.7(5) . . ? C11 C12 C7 123.1(6) . . ? C11 C12 Cl4 119.2(5) . . ? C7 C12 Cl4 117.6(5) . . ? O8 C11 C12 126.5(6) . . ? O8 C11 C10 116.0(6) . . ? C12 C11 C10 117.5(5) . . ? C8 C9 C10 121.0(6) . . ? C8 C9 Cl3 120.8(5) . . ? C10 C9 Cl3 118.2(5) . . ? C14 N1 C13 114.2(8) . . ? C14 N1 H1A 108.7 . . ? C13 N1 H1A 108.7 . . ? C14 N1 H1B 108.7 . . ? C13 N1 H1B 108.7 . . ? H1A N1 H1B 107.6 . . ? N1 C13 H13A 109.5 . . ? N1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C15 N2 C16 114.2(7) . . ? C15 N2 H2A 108.7 . . ? C16 N2 H2A 108.7 . . ? C15 N2 H2B 108.7 . . ? C16 N2 H2B 108.7 . . ? H2A N2 H2B 107.6 . . ? N2 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 C16 H16A 109.5 . . ? N2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C8 O6 H6 109.5 . . ? C2 O2 H2 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 C5 C6 C1 -177.3(8) . . . . ? C4 C5 C6 C1 2.9(12) . . . . ? O4 C5 C6 Cl2 1.3(12) . . . . ? C4 C5 C6 Cl2 -178.5(6) . . . . ? C5 C6 C1 O1 178.0(8) . . . . ? Cl2 C6 C1 O1 -0.5(12) . . . . ? C5 C6 C1 C2 -0.7(12) . . . . ? Cl2 C6 C1 C2 -179.3(6) . . . . ? O2 C2 C1 O1 -0.7(13) . . . . ? C3 C2 C1 O1 179.7(8) . . . . ? O2 C2 C1 C6 178.2(8) . . . . ? C3 C2 C1 C6 -1.5(13) . . . . ? O4 C5 C4 O3 -2.7(11) . . . . ? C6 C5 C4 O3 177.1(8) . . . . ? O4 C5 C4 C3 177.1(7) . . . . ? C6 C5 C4 C3 -3.1(11) . . . . ? O2 C2 C3 C4 -178.4(8) . . . . ? C1 C2 C3 C4 1.2(13) . . . . ? O2 C2 C3 Cl1 0.5(13) . . . . ? C1 C2 C3 Cl1 -179.9(6) . . . . ? O3 C4 C3 C2 -179.2(9) . . . . ? C5 C4 C3 C2 1.1(12) . . . . ? O3 C4 C3 Cl1 1.8(12) . . . . ? C5 C4 C3 Cl1 -177.9(6) . . . . ? O6 C8 C7 O5 -2.6(9) . . . . ? C9 C8 C7 O5 177.6(7) . . . . ? O6 C8 C7 C12 177.5(6) . . . . ? C9 C8 C7 C12 -2.3(10) . . . . ? O5 C7 C12 C11 -173.7(7) . . . . ? C8 C7 C12 C11 6.2(9) . . . . ? O5 C7 C12 Cl4 3.2(9) . . . . ? C8 C7 C12 Cl4 -176.9(5) . . . . ? C7 C12 C11 O8 173.8(7) . . . . ? Cl4 C12 C11 O8 -3.0(10) . . . . ? C7 C12 C11 C10 -5.8(10) . . . . ? Cl4 C12 C11 C10 177.4(5) . . . . ? O7 C10 C11 O8 2.9(10) . . . . ? C9 C10 C11 O8 -178.1(6) . . . . ? O7 C10 C11 C12 -177.5(7) . . . . ? C9 C10 C11 C12 1.6(10) . . . . ? O6 C8 C9 C10 178.5(7) . . . . ? C7 C8 C9 C10 -1.7(11) . . . . ? O6 C8 C9 Cl3 -0.1(10) . . . . ? C7 C8 C9 Cl3 179.7(5) . . . . ? O7 C10 C9 C8 -179.0(8) . . . . ? C11 C10 C9 C8 2.0(10) . . . . ? O7 C10 C9 Cl3 -0.3(11) . . . . ? C11 C10 C9 Cl3 -179.3(5) . . . . ? # Attachment 'TrpHCAxH2O1.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-04-17 at 10:03:12 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : f:\programs\wingx\files\cifdoc.dat # CIF files read : trp-ca-1 trp-ca-1-teh #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_TrpHCAxH2O _database_code_depnum_ccdc_archive 'CCDC 729430' _audit_creation_date 2008-04-17T10:03:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_sum 'C17 H16 Cl2 N2 O7' _chemical_formula_moiety 'C11 H13 N2 O2, C6 H Cl2 O4, H2 O' _chemical_formula_weight 431.23 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.1988(5) _cell_length_b 8.9661(3) _cell_length_c 30.9737(9) _cell_angle_alpha 90 _cell_angle_beta 95.401(3) _cell_angle_gamma 90 _cell_volume 3649.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3503 _cell_measurement_theta_min 2.8626 _cell_measurement_theta_max 75.9777 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.57 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1776 _exptl_absorpt_coefficient_mu 3.616 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5244 _exptl_absorpt_correction_T_max 0.8100 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_measurement_device_type 'Oxford Xcalibur Nova' _diffrn_measurement_method ; CCD detector ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4323 _diffrn_radiation_probe x-ray _diffrn_reflns_number 11339 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 76.09 _diffrn_reflns_theta_full 76.09 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measured_fraction_theta_full 0.972 _reflns_number_total 3703 _reflns_number_gt 2813 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0890P)^2^+3.0970P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 3703 _refine_ls_number_parameters 317 _refine_ls_number_restraints 21 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1567 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.54 _refine_diff_density_min -0.269 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 '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' O O 0.049 0.032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.333 0.557 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.364 0.702 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.031 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Cl1 Cl 0.36401(7) 0.21512(10) 0.24952(2) 0.0568(2) Uani 1 d . . . Cl2 Cl 0.50520(7) 0.50496(9) 0.43177(2) 0.0532(2) Uani 1 d . . . O3 O 0.44980(18) 0.0639(2) 0.33070(7) 0.0495(5) Uani 1 d . . . O4 O 0.52018(18) 0.1827(2) 0.40581(7) 0.0484(5) Uani 1 d . . . O1 O 0.4201(2) 0.6529(3) 0.34931(8) 0.0582(6) Uani 1 d . . . O2 O 0.3729(2) 0.5371(3) 0.27234(8) 0.0624(7) Uani 1 d D . . C3 C 0.4071(2) 0.2961(4) 0.29843(9) 0.0428(6) Uani 1 d . . . N1 N 0.4745(2) -0.1247(3) 0.41051(8) 0.0441(6) Uani 1 d D . . C4 C 0.4450(2) 0.1992(3) 0.33365(9) 0.0394(6) Uani 1 d . . . C5 C 0.4831(2) 0.2712(3) 0.37747(9) 0.0389(6) Uani 1 d . . . O5 O 0.54021(19) -0.1977(3) 0.49127(7) 0.0570(6) Uani 1 d . . . O6 O 0.38770(19) -0.1800(3) 0.51599(7) 0.0613(7) Uani 1 d D . . C2 C 0.4046(2) 0.4446(4) 0.30364(10) 0.0451(7) Uani 1 d . . . C1 C 0.4340(2) 0.5157(4) 0.34756(9) 0.0433(6) Uani 1 d . . . N2 N 0.1928(2) 0.0369(4) 0.32685(10) 0.0647(8) Uani 1 d D . . C6 C 0.4723(2) 0.4242(3) 0.38180(9) 0.0422(6) Uani 1 d . . . C7 C 0.4517(2) -0.1690(3) 0.48610(9) 0.0431(7) Uani 1 d . . . C9 C 0.2963(3) -0.1348(5) 0.42956(11) 0.0571(9) Uani 1 d D . . C17 C 0.2000(3) 0.1647(5) 0.35127(11) 0.0559(9) Uani 1 d . . . C10 C 0.2550(2) -0.0363(5) 0.39263(11) 0.0553(8) Uani 1 d . . . C8 C 0.4051(3) -0.0957(4) 0.44434(10) 0.0489(7) Uani 1 d D . . C11 C 0.2274(3) -0.0819(5) 0.35162(12) 0.0605(9) Uani 1 d D . . C16 C 0.1754(3) 0.3125(6) 0.34040(15) 0.0699(11) Uani 1 d D . . C12 C 0.2389(2) 0.1236(5) 0.39346(11) 0.0541(8) Uani 1 d . . . C14 C 0.2303(3) 0.3763(6) 0.41466(17) 0.0748(12) Uani 1 d D . . C15 C 0.1926(3) 0.4176(6) 0.37248(19) 0.0789(13) Uani 1 d D . . C13 C 0.2528(3) 0.2323(5) 0.42554(13) 0.0637(10) Uani 1 d D . . O7 O 0.4012(5) 0.8344(4) 0.26952(11) 0.1101(16) Uani 1 d D . . H13 H 0.275(3) 0.208(5) 0.4548(7) 0.061(11) Uiso 1 d D . . H6 H 0.421(3) -0.200(4) 0.5393(8) 0.053(10) Uiso 1 d D . . H16 H 0.148(3) 0.330(5) 0.3123(8) 0.081(14) Uiso 1 d D . . H14 H 0.236(4) 0.448(5) 0.4364(13) 0.087(15) Uiso 1 d D . . H15 H 0.176(4) 0.515(3) 0.3645(16) 0.083(14) Uiso 1 d D . . H2A H 0.180(4) 0.025(7) 0.2999(7) 0.11(2) Uiso 1 d D . . H2 H 0.383(4) 0.624(3) 0.2802(15) 0.077(15) Uiso 1 d D . . H11 H 0.235(3) -0.177(3) 0.3397(14) 0.075(14) Uiso 1 d D . . H1A H 0.458(3) -0.204(3) 0.3944(11) 0.062(11) Uiso 1 d D . . H9A H 0.292(3) -0.242(2) 0.4233(13) 0.074(13) Uiso 1 d D . . H1C H 0.474(3) -0.045(3) 0.3937(12) 0.074(13) Uiso 1 d D . . H9B H 0.258(3) -0.114(4) 0.4543(9) 0.063(11) Uiso 1 d D . . H1B H 0.533(2) -0.135(5) 0.4261(12) 0.077(14) Uiso 1 d D . . H8 H 0.405(3) 0.013(2) 0.4495(14) 0.073(13) Uiso 1 d D . . H7A H 0.409(6) 0.919(6) 0.288(2) 0.16(3) Uiso 1 d D . . H7B H 0.468(4) 0.812(11) 0.262(5) 0.33(9) Uiso 1 d 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 0.0749(5) 0.0530(5) 0.0396(4) -0.0019(3) -0.0103(3) -0.0014(4) Cl2 0.0728(5) 0.0425(4) 0.0423(4) -0.0043(3) -0.0041(3) -0.0002(4) O3 0.0676(14) 0.0363(12) 0.0435(11) -0.0012(9) -0.0003(10) 0.0015(10) O4 0.0656(13) 0.0384(11) 0.0392(10) 0.0027(8) -0.0055(9) 0.0017(10) O1 0.0857(17) 0.0351(12) 0.0515(12) -0.0003(10) -0.0063(12) 0.0107(12) O2 0.098(2) 0.0409(13) 0.0445(12) 0.0048(10) -0.0138(12) 0.0116(13) C3 0.0487(16) 0.0435(16) 0.0354(13) -0.0001(11) -0.0005(11) 0.0012(13) N1 0.0560(15) 0.0364(14) 0.0392(12) 0.0027(11) 0.0006(11) 0.0006(12) C4 0.0428(14) 0.0366(15) 0.0387(13) 0.0011(11) 0.0035(11) 0.0023(12) C5 0.0412(14) 0.0387(15) 0.0368(13) 0.0039(11) 0.0039(11) -0.0007(12) O5 0.0558(13) 0.0662(16) 0.0472(12) 0.0025(11) -0.0041(10) 0.0060(12) O6 0.0570(14) 0.0871(19) 0.0389(11) 0.0095(12) -0.0004(10) 0.0019(13) C2 0.0507(17) 0.0411(16) 0.0428(15) 0.0072(12) 0.0010(12) 0.0057(13) C1 0.0484(15) 0.0395(16) 0.0422(15) 0.0019(12) 0.0046(12) 0.0032(13) N2 0.0634(18) 0.085(2) 0.0435(15) 0.0040(16) -0.0053(13) 0.0019(17) C6 0.0465(15) 0.0409(16) 0.0387(14) -0.0019(12) 0.0013(11) 0.0004(13) C7 0.0491(17) 0.0407(16) 0.0386(14) -0.0024(12) -0.0002(12) -0.0032(13) C9 0.0554(19) 0.068(2) 0.0468(17) 0.0094(16) 0.0012(14) -0.0069(18) C17 0.0423(16) 0.077(2) 0.0481(17) 0.0113(17) 0.0046(13) 0.0069(16) C10 0.0420(16) 0.074(2) 0.0502(17) 0.0104(16) 0.0030(13) -0.0003(16) C8 0.0541(17) 0.0523(19) 0.0401(15) 0.0015(13) 0.0026(13) 0.0023(15) C11 0.0551(19) 0.071(3) 0.0550(19) 0.0058(18) 0.0013(15) -0.0012(19) C16 0.053(2) 0.086(3) 0.071(2) 0.022(2) 0.0093(17) 0.014(2) C12 0.0392(15) 0.078(3) 0.0452(16) 0.0028(16) 0.0020(12) 0.0019(16) C14 0.055(2) 0.082(3) 0.089(3) -0.017(3) 0.015(2) 0.002(2) C15 0.054(2) 0.068(3) 0.119(4) 0.014(3) 0.029(2) 0.013(2) C13 0.0491(18) 0.082(3) 0.060(2) -0.007(2) 0.0061(15) 0.0036(19) O7 0.205(5) 0.0602(19) 0.0590(18) 0.0036(15) -0.018(2) -0.041(3) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C3 1.727(3) . ? Cl2 C6 1.727(3) . ? O3 C4 1.219(4) . ? O4 C5 1.249(3) . ? O1 C1 1.246(4) . ? O2 C2 1.314(4) . ? O2 H2 0.826(19) . ? C3 C2 1.342(5) . ? C3 C4 1.447(4) . ? N1 C8 1.478(4) . ? N1 H1A 0.881(18) . ? N1 H1C 0.885(18) . ? N1 H1B 0.872(18) . ? C4 C5 1.544(4) . ? C5 C6 1.387(4) . ? O5 C7 1.192(4) . ? O6 C7 1.315(4) . ? O6 H6 0.828(19) . ? C2 C1 1.519(4) . ? C1 C6 1.397(4) . ? N2 C11 1.366(5) . ? N2 C17 1.371(6) . ? N2 H2A 0.84(2) . ? C7 C8 1.527(4) . ? C9 C10 1.506(5) . ? C9 C8 1.508(5) . ? C9 H9A 0.976(19) . ? C9 H9B 0.973(18) . ? C17 C16 1.398(6) . ? C17 C12 1.407(5) . ? C10 C11 1.351(5) . ? C10 C12 1.450(6) . ? C8 H8 0.988(19) . ? C11 H11 0.937(19) . ? C16 C15 1.373(7) . ? C16 H16 0.925(19) . ? C12 C13 1.392(6) . ? C14 C13 1.360(7) . ? C14 C15 1.404(7) . ? C14 H14 0.93(2) . ? C15 H15 0.929(19) . ? C13 H13 0.951(19) . ? O7 H7A 0.94(2) . ? O7 H7B 0.95(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 H2 110(3) . . ? C2 C3 C4 121.1(3) . . ? C2 C3 Cl1 120.9(2) . . ? C4 C3 Cl1 118.1(2) . . ? C8 N1 H1A 114(3) . . ? C8 N1 H1C 108(3) . . ? H1A N1 H1C 109(3) . . ? C8 N1 H1B 101(3) . . ? H1A N1 H1B 113(3) . . ? H1C N1 H1B 112(3) . . ? O3 C4 C3 123.9(3) . . ? O3 C4 C5 117.9(2) . . ? C3 C4 C5 118.2(3) . . ? O4 C5 C6 126.7(3) . . ? O4 C5 C4 115.2(3) . . ? C6 C5 C4 118.1(2) . . ? C7 O6 H6 108(3) . . ? O2 C2 C3 123.2(3) . . ? O2 C2 C1 115.6(3) . . ? C3 C2 C1 121.1(3) . . ? O1 C1 C6 126.2(3) . . ? O1 C1 C2 115.3(3) . . ? C6 C1 C2 118.5(3) . . ? C11 N2 C17 109.8(3) . . ? C11 N2 H2A 119(4) . . ? C17 N2 H2A 131(4) . . ? C5 C6 C1 122.7(3) . . ? C5 C6 Cl2 118.8(2) . . ? C1 C6 Cl2 118.5(2) . . ? O5 C7 O6 125.2(3) . . ? O5 C7 C8 121.2(3) . . ? O6 C7 C8 113.2(3) . . ? C10 C9 C8 111.1(3) . . ? C10 C9 H9A 115(3) . . ? C8 C9 H9A 109(3) . . ? C10 C9 H9B 108(2) . . ? C8 C9 H9B 105(2) . . ? H9A C9 H9B 109(3) . . ? N2 C17 C16 131.0(4) . . ? N2 C17 C12 107.1(3) . . ? C16 C17 C12 121.9(4) . . ? C11 C10 C12 106.8(3) . . ? C11 C10 C9 125.7(4) . . ? C12 C10 C9 127.5(3) . . ? N1 C8 C9 112.3(3) . . ? N1 C8 C7 107.3(3) . . ? C9 C8 C7 117.0(3) . . ? N1 C8 H8 107(3) . . ? C9 C8 H8 105(3) . . ? C7 C8 H8 107(3) . . ? C10 C11 N2 109.8(4) . . ? C10 C11 H11 128(3) . . ? N2 C11 H11 122(3) . . ? C15 C16 C17 117.2(4) . . ? C15 C16 H16 126(3) . . ? C17 C16 H16 117(3) . . ? C13 C12 C17 119.4(4) . . ? C13 C12 C10 134.1(3) . . ? C17 C12 C10 106.5(3) . . ? C13 C14 C15 122.1(4) . . ? C13 C14 H14 119(3) . . ? C15 C14 H14 119(3) . . ? C16 C15 C14 120.8(4) . . ? C16 C15 H15 116(3) . . ? C14 C15 H15 123(3) . . ? C14 C13 C12 118.5(4) . . ? C14 C13 H13 119(3) . . ? C12 C13 H13 122(3) . . ? H7A O7 H7B 105(4) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C3 C4 O3 -179.4(3) . . . . ? Cl1 C3 C4 O3 1.1(4) . . . . ? C2 C3 C4 C5 -0.3(4) . . . . ? Cl1 C3 C4 C5 -179.7(2) . . . . ? O3 C4 C5 O4 3.1(4) . . . . ? C3 C4 C5 O4 -176.1(3) . . . . ? O3 C4 C5 C6 -176.3(3) . . . . ? C3 C4 C5 C6 4.5(4) . . . . ? C4 C3 C2 O2 178.4(3) . . . . ? Cl1 C3 C2 O2 -2.1(5) . . . . ? C4 C3 C2 C1 -4.6(5) . . . . ? Cl1 C3 C2 C1 174.8(2) . . . . ? O2 C2 C1 O1 3.3(4) . . . . ? C3 C2 C1 O1 -173.9(3) . . . . ? O2 C2 C1 C6 -177.4(3) . . . . ? C3 C2 C1 C6 5.5(5) . . . . ? O4 C5 C6 C1 177.0(3) . . . . ? C4 C5 C6 C1 -3.7(4) . . . . ? O4 C5 C6 Cl2 -4.3(4) . . . . ? C4 C5 C6 Cl2 175.0(2) . . . . ? O1 C1 C6 C5 178.3(3) . . . . ? C2 C1 C6 C5 -1.0(5) . . . . ? O1 C1 C6 Cl2 -0.4(5) . . . . ? C2 C1 C6 Cl2 -179.7(2) . . . . ? C11 N2 C17 C16 179.2(4) . . . . ? C11 N2 C17 C12 -1.3(4) . . . . ? C8 C9 C10 C11 114.2(4) . . . . ? C8 C9 C10 C12 -64.5(5) . . . . ? C10 C9 C8 N1 -64.7(4) . . . . ? C10 C9 C8 C7 170.6(3) . . . . ? O5 C7 C8 N1 21.2(4) . . . . ? O6 C7 C8 N1 -165.9(3) . . . . ? O5 C7 C8 C9 148.4(3) . . . . ? O6 C7 C8 C9 -38.7(4) . . . . ? C12 C10 C11 N2 -1.5(4) . . . . ? C9 C10 C11 N2 179.6(3) . . . . ? C17 N2 C11 C10 1.8(4) . . . . ? N2 C17 C16 C15 -179.3(4) . . . . ? C12 C17 C16 C15 1.2(6) . . . . ? N2 C17 C12 C13 -179.1(3) . . . . ? C16 C17 C12 C13 0.5(5) . . . . ? N2 C17 C12 C10 0.3(4) . . . . ? C16 C17 C12 C10 179.9(3) . . . . ? C11 C10 C12 C13 180.0(4) . . . . ? C9 C10 C12 C13 -1.1(6) . . . . ? C11 C10 C12 C17 0.7(4) . . . . ? C9 C10 C12 C17 179.6(3) . . . . ? C17 C16 C15 C14 -1.9(6) . . . . ? C13 C14 C15 C16 0.9(7) . . . . ? C15 C14 C13 C12 0.9(6) . . . . ? C17 C12 C13 C14 -1.5(5) . . . . ? C10 C12 C13 C14 179.3(4) . . . . ? # Attachment 'pyr-CA1.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-01-09 at 13:49:37 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx\files\cifdoc.dat # CIF files read : pirimidin-ca-1 pirimidin-ca-1-teh struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_pyr-ca- _database_code_depnum_ccdc_archive 'CCDC 729431' _audit_creation_date 2009-01-09T13:49:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C9 H20 Cl1 N3 O7' _chemical_formula_sum 'C9 H20 Cl1 N3 O7' _chemical_formula_weight 317.72 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.417(4) _cell_length_b 6.7259(2) _cell_length_c 25.341(4) _cell_angle_alpha 90 _cell_angle_beta 145.35(3) _cell_angle_gamma 90 _cell_volume 2947(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8636 _cell_measurement_theta_min 3.0592 _cell_measurement_theta_max 75.9198 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description rod _exptl_crystal_colour purple _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 2.636 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.69319 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.11 (release 31-10-2007 CrysAlis171 .NET) (compiled Oct 31 2007,17:16:07) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_measurement_device_type 'Oxford Xcalibur Nova' _diffrn_measurement_method ; CCD detector ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4323 _diffrn_radiation_probe x-ray _diffrn_reflns_number 13348 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 76.29 _diffrn_reflns_theta_full 76.29 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measured_fraction_theta_full 0.987 _reflns_number_total 3054 _reflns_number_gt 2789 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0699P)^2^+1.0203P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3054 _refine_ls_number_parameters 233 _refine_ls_number_restraints 15 _refine_ls_R_factor_gt 0.036 _refine_ls_wR_factor_ref 0.109 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0 _refine_diff_density_max 0.375 _refine_diff_density_min -0.184 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly C9 C 0.27482(10) 0.0942(3) 0.38408(14) 0.0556(4) Uani 1 d . . . H9A H 0.2645 0.1031 0.3368 0.083 Uiso 0.5 calc PR . . H9B H 0.2988 -0.0312 0.4154 0.083 Uiso 0.5 calc PR . . H9C H 0.3088 0.2002 0.4279 0.083 Uiso 0.5 calc PR . . H9D H 0.3169 0.0783 0.45 0.083 Uiso 0.5 calc PR . . H9E H 0.2826 0.2126 0.3713 0.083 Uiso 0.5 calc PR . . H9F H 0.2726 -0.0188 0.3588 0.083 Uiso 0.5 calc PR . . H3C H 0.2430(16) 0.404(4) 0.8390(16) 0.089(9) Uiso 1 d D . . H7A H 0.1173(18) -0.069(3) 0.115(2) 0.113(11) Uiso 1 d D . . H1 H 0.1369(12) 0.124(3) 0.2133(15) 0.053(5) Uiso 1 d . . . H5A H 0.0602(14) 0.661(3) 0.4712(16) 0.072(7) Uiso 1 d D . . H3D H 0.2738(16) 0.418(6) 0.813(3) 0.147(15) Uiso 1 d D . . H5B H 0.0039(12) 0.654(5) 0.464(2) 0.117(12) Uiso 1 d D . . H7B H 0.1066(17) 0.148(4) 0.0870(18) 0.111(11) Uiso 1 d D . . H3A H 0.0627(15) 0.127(3) 0.3452(17) 0.062(6) Uiso 1 d . . . H3B H 0.1450(14) 0.084(3) 0.4333(17) 0.059(6) Uiso 1 d . . . H6A H 0.2344(12) 0.619(3) 0.4241(18) 0.080(8) Uiso 1 d D . . H6B H 0.3125(13) 0.690(3) 0.4905(16) 0.089(8) Uiso 1 d D . . H4B H 0.0901(18) 0.431(4) 0.574(2) 0.111(11) Uiso 1 d D . . H4A H 0.137(2) 0.370(6) 0.6690(14) 0.18(2) Uiso 1 d D . . Cl1 Cl 0.088215(18) 0.64357(5) 0.22812(2) 0.03999(14) Uani 1 d . . . O2 O 0.15593(6) 0.63125(17) 0.40243(7) 0.0443(3) Uani 1 d . . . N1 N 0.13507(7) 0.13341(18) 0.24682(9) 0.0388(3) Uani 1 d . . . O1 O 0.08196(6) 0.66362(19) 0.42171(7) 0.0474(3) Uani 1 d . . . O5 O 0.05443(7) 0.66220(19) 0.50071(8) 0.0498(3) Uani 1 d D . . N2 N 0.05595(7) 0.14708(17) 0.24306(8) 0.0372(3) Uani 1 d . . . C2 C 0.08410(8) 0.63885(19) 0.33011(9) 0.0322(3) Uani 1 d . . . C1 C 0.04108(8) 0.64997(19) 0.34079(9) 0.0328(3) Uani 1 d . . . O6 O 0.27734(7) 0.6000(2) 0.44541(8) 0.0504(3) Uani 1 d D . . N3 N 0.10850(9) 0.1208(2) 0.37724(10) 0.0457(3) Uani 1 d . . . C3 C 0.03944(7) 0.64268(19) 0.23968(9) 0.0323(3) Uani 1 d . . . C5 C 0.11999(8) 0.1239(2) 0.33693(10) 0.0368(3) Uani 1 d . . . C6 C 0.19440(9) 0.1038(2) 0.38770(11) 0.0423(3) Uani 1 d . . . H6 H 0.2379 0.0864 0.4517 0.051 Uiso 1 calc R . . C4 C 0.06561(9) 0.1488(2) 0.20138(10) 0.0375(3) Uani 1 d . . . C7 C 0.20069(9) 0.1106(2) 0.34071(11) 0.0401(3) Uani 1 d . . . C8 C -0.00385(10) 0.1674(3) 0.09797(11) 0.0524(4) Uani 1 d . . . H8A H 0.0121 0.1662 0.0775 0.079 Uiso 1 calc R . . H8B H -0.03 0.29 0.0796 0.079 Uiso 1 calc R . . H8C H -0.0382 0.0579 0.0704 0.079 Uiso 1 calc R . . O4 O 0.09640(7) 0.3404(2) 0.60660(9) 0.0546(3) Uani 1 d D . . O3 O 0.23058(9) 0.4268(3) 0.79166(10) 0.0826(5) Uani 1 d D . . O7 O 0.13596(7) 0.0614(2) 0.13768(9) 0.0535(3) Uani 1 d 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 C9 0.0417(8) 0.0691(11) 0.0562(10) 0.0095(8) 0.0403(8) 0.0064(7) Cl1 0.0348(2) 0.0562(2) 0.0368(2) -0.00211(13) 0.03100(18) -0.00124(12) O2 0.0268(5) 0.0684(7) 0.0295(5) 0.0021(4) 0.0216(4) 0.0010(4) N1 0.0394(6) 0.0440(6) 0.0389(6) 0.0052(5) 0.0334(6) 0.0038(5) O1 0.0333(5) 0.0797(8) 0.0275(5) -0.0009(5) 0.0247(5) -0.0025(5) O5 0.0475(6) 0.0684(7) 0.0404(6) -0.0033(5) 0.0375(6) -0.0041(5) N2 0.0346(6) 0.0400(6) 0.0349(6) 0.0033(4) 0.0281(5) 0.0029(4) C2 0.0287(6) 0.0360(6) 0.0298(6) -0.0003(4) 0.0236(6) -0.0007(4) C1 0.0308(6) 0.0389(7) 0.0282(6) 0.0005(5) 0.0241(6) -0.0012(5) O6 0.0368(5) 0.0692(7) 0.0365(5) -0.0041(5) 0.0285(5) -0.0039(5) N3 0.0418(7) 0.0608(8) 0.0383(7) 0.0031(6) 0.0337(7) 0.0025(6) C3 0.0297(6) 0.0394(7) 0.0314(7) -0.0010(5) 0.0258(6) -0.0011(5) C5 0.0385(7) 0.0366(7) 0.0359(7) 0.0011(5) 0.0307(6) 0.0004(5) C6 0.0354(7) 0.0497(8) 0.0344(7) 0.0015(6) 0.0273(6) 0.0004(6) C4 0.0375(7) 0.0395(7) 0.0363(7) 0.0014(5) 0.0305(7) 0.0007(5) C7 0.0361(7) 0.0402(7) 0.0403(7) 0.0029(5) 0.0307(6) 0.0010(5) C8 0.0439(8) 0.0696(11) 0.0360(8) 0.0077(7) 0.0314(7) 0.0070(7) O4 0.0497(7) 0.0701(8) 0.0449(6) 0.0020(5) 0.0390(6) -0.0003(5) O3 0.0543(8) 0.1479(16) 0.0531(8) -0.0101(9) 0.0457(7) -0.0109(9) O7 0.0535(7) 0.0668(8) 0.0485(6) 0.0041(6) 0.0436(6) 0.0026(6) #------------------ MOLECULAR GEOMETRY --------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C9 C7 1.492(2) . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? C9 H9D 0.96 . ? C9 H9E 0.96 . ? C9 H9F 0.96 . ? Cl1 C3 1.7325(14) . ? O2 C2 1.244(2) . ? N1 C4 1.341(2) . ? N1 C7 1.362(2) . ? N1 H1 0.90(2) . ? O1 C1 1.2506(18) . ? O5 H5A 0.899(16) . ? O5 H5B 0.933(17) . ? N2 C4 1.3085(19) . ? N2 C5 1.361(2) . ? C2 C3 1.406(2) . ? C2 C1 1.5407(19) . ? C1 C3 1.394(2) 2 ? O6 H6A 0.924(16) . ? O6 H6B 0.896(17) . ? N3 C5 1.324(2) . ? N3 H3A 0.86(3) . ? N3 H3B 0.85(2) . ? C3 C1 1.394(2) 2 ? C5 C6 1.416(2) . ? C6 C7 1.353(2) . ? C6 H6 0.93 . ? C4 C8 1.496(2) . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C8 H8C 0.96 . ? O4 H4B 0.908(17) . ? O4 H4A 0.924(19) . ? O3 H3C 0.928(17) . ? O3 H3D 0.92(8) . ? O7 H7A 0.938(17) . ? O7 H7B 0.946(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C9 H9D 109.5 . . ? H9A C9 H9D 141.1 . . ? H9B C9 H9D 56.3 . . ? H9C C9 H9D 56.3 . . ? C7 C9 H9E 109.5 . . ? H9A C9 H9E 56.3 . . ? H9B C9 H9E 141.1 . . ? H9C C9 H9E 56.3 . . ? H9D C9 H9E 109.5 . . ? C7 C9 H9F 109.5 . . ? H9A C9 H9F 56.3 . . ? H9B C9 H9F 56.3 . . ? H9C C9 H9F 141.1 . . ? H9D C9 H9F 109.5 . . ? H9E C9 H9F 109.5 . . ? C4 N1 C7 121.21(14) . . ? C4 N1 H1 118.3(14) . . ? C7 N1 H1 120.1(14) . . ? H5A O5 H5B 117(2) . . ? C4 N2 C5 117.56(13) . . ? O2 C2 C3 124.97(14) . . ? O2 C2 C1 117.35(12) . . ? C3 C2 C1 117.66(12) . . ? O1 C1 C3 125.56(14) . 2 ? O1 C1 C2 116.69(12) . . ? C3 C1 C2 117.74(12) 2 . ? H6A O6 H6B 107(2) . . ? C5 N3 H3A 121.4(16) . . ? C5 N3 H3B 119.0(15) . . ? H3A N3 H3B 118(2) . . ? C1 C3 C2 124.34(13) 2 . ? C1 C3 Cl1 118.11(11) 2 . ? C2 C3 Cl1 117.53(11) . . ? N3 C5 N2 116.32(14) . . ? N3 C5 C6 122.45(15) . . ? N2 C5 C6 121.23(14) . . ? C7 C6 C5 118.34(15) . . ? C7 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? N2 C4 N1 123.21(14) . . ? N2 C4 C8 118.91(14) . . ? N1 C4 C8 117.88(15) . . ? C6 C7 N1 118.44(14) . . ? C6 C7 C9 124.83(16) . . ? N1 C7 C9 116.73(15) . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? H4B O4 H4A 114(3) . . ? H3C O3 H3D 112(3) . . ? H7A O7 H7B 109(2) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C2 C1 O1 4.53(19) . . . . ? C3 C2 C1 O1 -174.04(12) . . . . ? O2 C2 C1 C3 -175.04(12) . . . 2 ? C3 C2 C1 C3 6.40(16) . . . 2 ? O2 C2 C3 C1 179.58(14) . . . 2 ? C1 C2 C3 C1 -1.97(17) . . . 2 ? O2 C2 C3 Cl1 -1.82(18) . . . . ? C1 C2 C3 Cl1 176.63(9) . . . . ? C4 N2 C5 N3 -179.37(13) . . . . ? C4 N2 C5 C6 0.5(2) . . . . ? N3 C5 C6 C7 -179.39(14) . . . . ? N2 C5 C6 C7 0.8(2) . . . . ? C5 N2 C4 N1 -1.6(2) . . . . ? C5 N2 C4 C8 178.03(13) . . . . ? C7 N1 C4 N2 1.4(2) . . . . ? C7 N1 C4 C8 -178.21(14) . . . . ? C5 C6 C7 N1 -1.0(2) . . . . ? C5 C6 C7 C9 179.27(15) . . . . ? C4 N1 C7 C6 0.0(2) . . . . ? C4 N1 C7 C9 179.75(14) . . . . ?