# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm #=============================================================================== # 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY) _journal_coden_Cambridge 1350 #TrackingRef 'L-AAfinalNEW.cif' #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'Aug 24 23:59:22 2010' _audit_creation_method 'PLATON option' _audit_update_record ; ; #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name 'Prof.T.N.Guru Row' _publ_contact_author_address ; Solid State and Structural Chemistry Unit Indian Institute of Science Bangalore, 560 012 India ; _publ_contact_author_email ssctng@sscu.iisc.ernet.in _publ_contact_author_fax '(91) 80 2360 1310' _publ_contact_author_phone '(91) 80 2293 2796' _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for publication in CrystEngComm as a new-style paper. All required files have been provided. The manuscript has passed the checkcif tests and generates an acceptable printcif output. Yours sincerely T. N. Guru Row. ; _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; ; _publ_section_title_footnote ; ; # The loop structure below should contain the names and adresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Archi Dasgupta ' ; Solid State and Structural Chemistry Unit Indian Institute of Science Bangalore 560 012, Karnataka India ; 'T.N.Guru Row' ; Solid State and Structural Chemistry Unit Indian Institute of Science Bangalore 560 012, Karnataka India ; #=============================================================================== # 4. TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; # Insert blank lines between paragraphs _publ_section_comment ; ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ; _publ_section_references ; Farrugia, L. J. (1999). J. Appl. Cryst.32, 837--838. Sheldrick, G.M. (1997). SHELXL97. University of G\"ottingen, Germany. Spek, A.L. (2003). J. Appl. Cryst.36, 7--13. Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England. ; _publ_section_acknowledgements ; We thank the Department of Science and Technology, India, for use of the CCD facility setup under the IRHPA-DST program at IISc. ; _publ_section_figure_captions ; Fig. 1. View of the molecular structure of (I) showing the atom labelling scheme. Displacement ellipsoids are showed at the 50% probability level. H atoms are shown as small spheres of arbitrary radii. ; #===END # Attachment 'acetamidofinalNEW.cif' # CIF-file generated for acetamido in P -1 #============================================================================== #=============================================================================== data_acetamido _database_code_depnum_ccdc_archive 'CCDC 791931' #TrackingRef 'acetamidofinalNEW.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H7 Cl2 N5, C2 H5 N O' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C11 H12 Cl2 N6 O' _chemical_formula_iupac ? _chemical_formula_weight 315.17 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 7.7752(3) _cell_length_b 9.6284(4) _cell_length_c 10.4511(3) _cell_angle_alpha 106.390(3) _cell_angle_beta 107.730(3) _cell_angle_gamma 101.093(3) _cell_volume 680.98(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14019 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.482 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_absorpt_correction_T_min 0.8690 _exptl_absorpt_correction_T_max 0.9098 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method 'f\w scans' _diffrn_reflns_number 14019 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0107 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2400 # number of observed reflections (> n sig(I)) _reflns_number_gt 2163 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+0.9261P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2400 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1628 _refine_ls_wR_factor_gt 0.1590 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 1.894 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 1.332 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.069 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6271(4) 0.3708(3) 0.1223(3) 0.0345(6) Uani 1 1 d . . . C2 C 0.6221(4) 0.4966(4) 0.2272(3) 0.0395(7) Uani 1 1 d . . . C3 C 0.7134(4) 0.6405(4) 0.2428(3) 0.0426(8) Uani 1 1 d . . . H3 H 0.7144 0.7239 0.3148 0.051 Uiso 1 1 calc R . . C4 C 0.8036(4) 0.6622(4) 0.1525(4) 0.0440(8) Uani 1 1 d . . . H4 H 0.8619 0.7609 0.1632 0.053 Uiso 1 1 calc R . . C5 C 0.8106(4) 0.5403(3) 0.0448(4) 0.0374(7) Uani 1 1 d . . . H5 H 0.8700 0.5564 -0.0169 0.045 Uiso 1 1 calc R . . C6 C 0.7232(4) 0.3907(3) 0.0337(3) 0.0305(6) Uani 1 1 d . . . C7 C 0.7288(4) 0.2587(3) -0.0800(3) 0.0287(6) Uani 1 1 d . . . C8 C 0.8314(4) 0.1550(3) -0.0498(3) 0.0263(6) Uani 1 1 d . . . C9 C 0.7142(4) 0.0236(3) -0.2911(3) 0.0270(6) Uani 1 1 d . . . C10 C 0.0955(5) 0.7374(4) 0.5719(3) 0.0431(7) Uani 1 1 d . . . C11 C 0.1655(6) 0.9079(4) 0.6257(5) 0.0591(10) Uani 1 1 d . . . H11A H 0.0594 0.9466 0.6050 0.089 Uiso 1 1 calc R . . H11B H 0.2459 0.9390 0.5785 0.089 Uiso 1 1 calc R . . H11C H 0.2360 0.9471 0.7280 0.089 Uiso 1 1 calc R . . Cl1 Cl 0.50274(14) 0.18947(10) 0.09659(10) 0.0533(3) Uani 1 1 d . . . Cl2 Cl 0.49505(16) 0.47231(12) 0.33299(11) 0.0623(3) Uani 1 1 d . . . H6A H 0.228(7) 0.711(5) 0.444(5) 0.065(13) Uiso 1 1 d . . . H6B H 0.130(7) 0.580(6) 0.449(5) 0.061(15) Uiso 1 1 d . . . N1 N 0.9438(4) 0.1773(3) 0.0841(2) 0.0376(6) Uani 1 1 d . . . H1A H 1.0075 0.1157 0.0989 0.045 Uiso 1 1 calc R . . H1B H 0.9526 0.2534 0.1555 0.045 Uiso 1 1 calc R . . N2 N 0.8212(3) 0.0361(2) -0.1578(2) 0.0270(5) Uani 1 1 d . . . N3 N 0.6846(4) -0.1020(3) -0.4028(2) 0.0392(6) Uani 1 1 d . . . H3A H 0.6186 -0.1119 -0.4892 0.047 Uiso 1 1 calc R . . H3B H 0.7318 -0.1724 -0.3877 0.047 Uiso 1 1 calc R . . N4 N 0.6354(4) 0.1274(3) -0.3247(2) 0.0358(6) Uani 1 1 d . . . N5 N 0.6445(4) 0.2461(3) -0.2138(3) 0.0353(6) Uani 1 1 d . . . N6 N 0.1535(5) 0.6614(5) 0.4760(4) 0.0529(8) Uani 1 1 d . . . O1 O -0.0139(4) 0.6738(3) 0.6172(3) 0.0645(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0384(15) 0.0356(15) 0.0359(15) 0.0168(12) 0.0155(13) 0.0171(12) C2 0.0431(16) 0.0486(18) 0.0329(15) 0.0147(13) 0.0144(13) 0.0275(14) C3 0.0389(16) 0.0485(19) 0.0377(16) 0.0082(14) 0.0109(13) 0.0244(14) C4 0.0368(16) 0.0308(16) 0.058(2) 0.0084(14) 0.0165(15) 0.0114(12) C5 0.0259(13) 0.0249(14) 0.0513(18) 0.0033(12) 0.0095(12) 0.0100(11) C6 0.0290(13) 0.0349(15) 0.0302(14) 0.0139(12) 0.0095(11) 0.0155(11) C7 0.0290(13) 0.0314(14) 0.0265(13) 0.0096(11) 0.0103(11) 0.0130(11) C8 0.0289(13) 0.0260(13) 0.0238(12) 0.0093(10) 0.0100(10) 0.0080(10) C9 0.0276(13) 0.0301(13) 0.0229(12) 0.0090(11) 0.0100(10) 0.0085(11) C10 0.0440(17) 0.0479(18) 0.0301(15) 0.0141(14) 0.0087(13) 0.0069(14) C11 0.063(2) 0.052(2) 0.068(2) 0.0297(19) 0.027(2) 0.0163(18) Cl1 0.0667(6) 0.0413(5) 0.0694(6) 0.0275(4) 0.0417(5) 0.0174(4) Cl2 0.0902(7) 0.0782(7) 0.0592(6) 0.0385(5) 0.0544(6) 0.0507(6) N1 0.0519(15) 0.0389(13) 0.0215(11) 0.0071(10) 0.0084(10) 0.0278(12) N2 0.0334(12) 0.0253(11) 0.0232(11) 0.0088(9) 0.0097(9) 0.0128(9) N3 0.0524(15) 0.0367(14) 0.0224(12) 0.0050(10) 0.0072(11) 0.0202(12) N4 0.0430(14) 0.0403(14) 0.0232(11) 0.0090(10) 0.0085(10) 0.0216(11) N5 0.0404(13) 0.0403(14) 0.0287(12) 0.0125(11) 0.0114(10) 0.0226(11) N6 0.0572(19) 0.056(2) 0.0486(18) 0.0216(17) 0.0248(15) 0.0131(17) O1 0.0846(19) 0.0517(15) 0.0410(14) 0.0008(11) 0.0361(14) -0.0100(13) _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 C1 C6 1.386(4) . ? C1 C2 1.402(4) . ? C1 Cl1 1.727(3) . ? C2 C3 1.369(5) . ? C2 Cl2 1.724(3) . ? C3 C4 1.372(5) . ? C3 H3 0.9300 . ? C4 C5 1.401(4) . ? C4 H4 0.9300 . ? C5 C6 1.425(4) . ? C5 H5 0.9300 . ? C6 C7 1.494(4) . ? C7 N5 1.310(4) . ? C7 C8 1.437(4) . ? C8 N2 1.331(3) . ? C8 N1 1.334(3) . ? C9 N4 1.342(4) . ? C9 N2 1.345(3) . ? C9 N3 1.345(4) . ? C10 O1 1.238(4) . ? C10 N6 1.316(5) . ? C10 C11 1.502(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? N4 N5 1.350(3) . ? N6 H6A 0.88(5) . ? N6 H6B 0.72(5) . ? 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 C6 C1 C2 120.5(3) . . ? C6 C1 Cl1 119.4(2) . . ? C2 C1 Cl1 119.9(2) . . ? C3 C2 C1 119.8(3) . . ? C3 C2 Cl2 119.5(2) . . ? C1 C2 Cl2 120.6(3) . . ? C2 C3 C4 120.3(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 122.1(3) . . ? C3 C4 H4 119.0 . . ? C5 C4 H4 119.0 . . ? C4 C5 C6 117.4(3) . . ? C4 C5 H5 121.3 . . ? C6 C5 H5 121.3 . . ? C1 C6 C5 119.8(3) . . ? C1 C6 C7 121.6(3) . . ? C5 C6 C7 118.5(3) . . ? N5 C7 C8 119.7(2) . . ? N5 C7 C6 116.3(2) . . ? C8 C7 C6 123.9(2) . . ? N2 C8 N1 118.4(2) . . ? N2 C8 C7 119.8(2) . . ? N1 C8 C7 121.8(2) . . ? N4 C9 N2 125.8(2) . . ? N4 C9 N3 116.0(2) . . ? N2 C9 N3 118.2(2) . . ? O1 C10 N6 122.6(4) . . ? O1 C10 C11 119.8(3) . . ? N6 C10 C11 117.6(3) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 N1 H1A 120.0 . . ? C8 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C8 N2 C9 115.9(2) . . ? C9 N3 H3A 120.0 . . ? C9 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C9 N4 N5 117.0(2) . . ? C7 N5 N4 120.9(2) . . ? C10 N6 H6A 120(3) . . ? C10 N6 H6B 123(4) . . ? H6A N6 H6B 117(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 C6 C1 C2 C3 -0.3(4) . . . . ? Cl1 C1 C2 C3 -176.9(2) . . . . ? C6 C1 C2 Cl2 177.5(2) . . . . ? Cl1 C1 C2 Cl2 0.9(4) . . . . ? C1 C2 C3 C4 2.6(5) . . . . ? Cl2 C2 C3 C4 -175.3(2) . . . . ? C2 C3 C4 C5 -1.7(5) . . . . ? C3 C4 C5 C6 -1.3(5) . . . . ? C2 C1 C6 C5 -2.7(4) . . . . ? Cl1 C1 C6 C5 173.9(2) . . . . ? C2 C1 C6 C7 -179.3(2) . . . . ? Cl1 C1 C6 C7 -2.6(4) . . . . ? C4 C5 C6 C1 3.5(4) . . . . ? C4 C5 C6 C7 -179.9(3) . . . . ? C1 C6 C7 N5 114.8(3) . . . . ? C5 C6 C7 N5 -61.8(3) . . . . ? C1 C6 C7 C8 -70.0(4) . . . . ? C5 C6 C7 C8 113.5(3) . . . . ? N5 C7 C8 N2 -8.0(4) . . . . ? C6 C7 C8 N2 176.8(2) . . . . ? N5 C7 C8 N1 169.2(3) . . . . ? C6 C7 C8 N1 -5.9(4) . . . . ? N1 C8 N2 C9 -176.4(2) . . . . ? C7 C8 N2 C9 0.9(4) . . . . ? N4 C9 N2 C8 7.6(4) . . . . ? N3 C9 N2 C8 -173.8(2) . . . . ? N2 C9 N4 N5 -8.6(4) . . . . ? N3 C9 N4 N5 172.7(3) . . . . ? C8 C7 N5 N4 7.1(4) . . . . ? C6 C7 N5 N4 -177.4(2) . . . . ? C9 N4 N5 C7 0.7(4) . . . . ? #===END #=============================================================================== data_ltghba _database_code_depnum_ccdc_archive 'CCDC 819591' #TrackingRef 'FINALltghba.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 Cl2 N5, C7 H5 O3' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C16 H13 Cl2 N5 O3' _chemical_formula_iupac ? _chemical_formula_weight 394.21 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 15.5808(10) _cell_length_b 9.6890(6) _cell_length_c 11.1057(7) _cell_angle_alpha 90 _cell_angle_beta 91.312(3) _cell_angle_gamma 90 _cell_volume 1676.10(18) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 9221 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.5 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.416 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_absorpt_correction_T_min 0.8853 _exptl_absorpt_correction_T_max 0.9214 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method 'f\w scans' _diffrn_reflns_number 9221 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measured_fraction_theta_full 0.985 _diffrn_reflns_reduction_process ; ; _reflns_number_total 3075 # number of observed reflections (> n sig(I)) _reflns_number_gt 2539 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0413P)^2^+1.1953P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3075 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0913 _refine_ls_wR_factor_gt 0.0872 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.281 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.055 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.39944(3) 0.48763(6) 0.58325(5) 0.02368(15) Uani 1 1 d . . . Cl2 Cl 0.20042(4) 0.43949(7) 0.61033(5) 0.03209(17) Uani 1 1 d . . . N2 N 0.55977(10) 0.86315(18) 0.58257(15) 0.0169(4) Uani 1 1 d . . . N1 N 0.41485(10) 0.90277(19) 0.57683(16) 0.0191(4) Uani 1 1 d . . . H1A H 0.4217 0.9633 0.5213 0.023 Uiso 1 1 calc R . . H1B H 0.3643 0.8856 0.6025 0.023 Uiso 1 1 calc R . . N4 N 0.61410(11) 0.70443(19) 0.72563(16) 0.0186(4) Uani 1 1 d . . . N3 N 0.70391(10) 0.81235(19) 0.59487(16) 0.0194(4) Uani 1 1 d . . . H3A H 0.7130 0.8694 0.5372 0.023 Uiso 1 1 calc R . . H3B H 0.7461 0.7676 0.6274 0.023 Uiso 1 1 calc R . . C1 C 0.34044(13) 0.5878(2) 0.68059(19) 0.0182(5) Uani 1 1 d . . . C7 C 0.47032(12) 0.7322(2) 0.71527(18) 0.0165(4) Uani 1 1 d . . . C8 C 0.48180(12) 0.8363(2) 0.62259(18) 0.0166(4) Uani 1 1 d . . . C2 C 0.25268(13) 0.5656(2) 0.69253(19) 0.0207(5) Uani 1 1 d . . . C6 C 0.38118(13) 0.6934(2) 0.74550(19) 0.0178(5) Uani 1 1 d . . . N5 N 0.53539(10) 0.67037(19) 0.76558(16) 0.0194(4) Uani 1 1 d . . . C4 C 0.24677(14) 0.7505(2) 0.8354(2) 0.0233(5) Uani 1 1 d . . . H4 H 0.2154 0.8041 0.8881 0.028 Uiso 1 1 calc R . . C9 C 0.62559(12) 0.7935(2) 0.63323(18) 0.0165(4) Uani 1 1 d . . . C5 C 0.33369(13) 0.7741(2) 0.82376(19) 0.0205(5) Uani 1 1 d . . . H5 H 0.3605 0.8439 0.8681 0.025 Uiso 1 1 calc R . . C3 C 0.20624(13) 0.6478(2) 0.7692(2) 0.0226(5) Uani 1 1 d . . . H3 H 0.1475 0.6340 0.7762 0.027 Uiso 1 1 calc R . . O1 O 0.26307(8) 0.43259(16) 0.14875(13) 0.0191(3) Uani 1 1 d . . . O3 O -0.06705(10) 0.79539(19) 0.04053(14) 0.0303(4) Uani 1 1 d . . . H3O H -0.0994 0.8174 0.0945 0.045 Uiso 1 1 calc R . . O2 O 0.18481(9) 0.37333(17) 0.30619(13) 0.0235(4) Uani 1 1 d . . . C16 C 0.19380(13) 0.4381(2) 0.20881(19) 0.0194(5) Uani 1 1 d . . . C12 C -0.00790(13) 0.6551(2) 0.20059(19) 0.0215(5) Uani 1 1 d . . . H12 H -0.0514 0.6802 0.2521 0.026 Uiso 1 1 calc R . . C10 C 0.12258(13) 0.5281(2) 0.16466(19) 0.0195(5) Uani 1 1 d . . . C14 C 0.05802(14) 0.6684(3) 0.0080(2) 0.0284(6) Uani 1 1 d . . . H14 H 0.0581 0.7013 -0.0707 0.034 Uiso 1 1 calc R . . C11 C 0.05589(13) 0.5650(2) 0.2396(2) 0.0202(5) Uani 1 1 d . . . H11 H 0.0542 0.5286 0.3170 0.024 Uiso 1 1 calc R . . C15 C 0.12224(14) 0.5807(3) 0.0481(2) 0.0253(5) Uani 1 1 d . . . H15 H 0.1659 0.5563 -0.0035 0.030 Uiso 1 1 calc R . . C13 C -0.00679(13) 0.7078(2) 0.0846(2) 0.0221(5) Uani 1 1 d . . . H4A H 0.6572(18) 0.660(3) 0.765(2) 0.043(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0222(3) 0.0236(3) 0.0256(3) -0.0032(2) 0.0079(2) -0.0008(2) Cl2 0.0257(3) 0.0391(4) 0.0318(3) -0.0089(3) 0.0059(2) -0.0151(3) N2 0.0137(8) 0.0179(10) 0.0191(9) 0.0003(8) 0.0020(7) -0.0002(7) N1 0.0118(8) 0.0206(10) 0.0249(10) 0.0072(8) 0.0014(7) -0.0010(7) N4 0.0122(9) 0.0234(11) 0.0203(10) 0.0034(8) 0.0015(7) 0.0008(7) N3 0.0134(8) 0.0220(11) 0.0228(10) 0.0046(8) 0.0015(7) 0.0026(7) C1 0.0189(10) 0.0192(12) 0.0166(11) 0.0046(9) 0.0038(8) 0.0015(9) C7 0.0150(10) 0.0166(12) 0.0181(11) -0.0012(9) 0.0019(8) -0.0001(8) C8 0.0156(10) 0.0167(11) 0.0174(11) -0.0026(9) 0.0018(8) -0.0029(8) C2 0.0199(11) 0.0227(13) 0.0196(11) 0.0034(9) 0.0019(9) -0.0050(9) C6 0.0156(10) 0.0194(12) 0.0185(11) 0.0052(9) 0.0009(8) -0.0018(8) N5 0.0138(9) 0.0232(11) 0.0214(10) 0.0012(8) 0.0028(7) -0.0007(7) C4 0.0218(11) 0.0271(14) 0.0211(12) 0.0019(10) 0.0072(9) 0.0031(10) C9 0.0147(10) 0.0175(12) 0.0171(11) -0.0030(9) 0.0011(8) -0.0022(8) C5 0.0219(11) 0.0210(12) 0.0187(11) 0.0019(9) 0.0024(9) -0.0023(9) C3 0.0142(10) 0.0298(14) 0.0241(12) 0.0047(10) 0.0051(9) -0.0014(9) O1 0.0094(7) 0.0257(9) 0.0223(8) -0.0010(7) 0.0040(6) 0.0023(6) O3 0.0215(8) 0.0436(11) 0.0262(9) 0.0035(8) 0.0059(7) 0.0134(7) O2 0.0156(7) 0.0312(9) 0.0239(8) 0.0058(7) 0.0053(6) 0.0023(6) C16 0.0143(10) 0.0233(12) 0.0207(12) -0.0043(9) 0.0016(8) -0.0030(9) C12 0.0132(10) 0.0272(13) 0.0242(12) -0.0040(10) 0.0065(9) -0.0002(9) C10 0.0122(10) 0.0234(13) 0.0229(11) -0.0007(9) 0.0025(8) -0.0020(8) C14 0.0235(12) 0.0401(15) 0.0220(12) 0.0082(11) 0.0070(9) 0.0078(10) C11 0.0164(10) 0.0244(13) 0.0199(11) 0.0015(9) 0.0026(8) -0.0009(9) C15 0.0163(11) 0.0348(15) 0.0251(12) 0.0029(10) 0.0081(9) 0.0064(10) C13 0.0142(10) 0.0269(13) 0.0251(12) 0.0016(10) 0.0011(8) 0.0069(9) _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 C1 1.732(2) . ? Cl2 C2 1.719(2) . ? N2 C8 1.329(3) . ? N2 C9 1.340(3) . ? N1 C8 1.318(3) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N4 N5 1.355(2) . ? N4 C9 1.356(3) . ? N4 H4A 0.90(3) . ? N3 C9 1.314(3) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? C1 C2 1.393(3) . ? C1 C6 1.396(3) . ? C7 N5 1.293(3) . ? C7 C8 1.455(3) . ? C7 C6 1.485(3) . ? C2 C3 1.382(3) . ? C6 C5 1.394(3) . ? C4 C3 1.381(3) . ? C4 C5 1.382(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C3 H3 0.9300 . ? O1 C16 1.283(2) . ? O3 C13 1.349(3) . ? O3 H3O 0.8200 . ? O2 C16 1.261(3) . ? C16 C10 1.486(3) . ? C12 C11 1.385(3) . ? C12 C13 1.387(3) . ? C12 H12 0.9300 . ? C10 C15 1.391(3) . ? C10 C11 1.393(3) . ? C14 C15 1.379(3) . ? C14 C13 1.389(3) . ? C14 H14 0.9300 . ? C11 H11 0.9300 . ? C15 H15 0.9300 . ? 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 N2 C9 117.23(18) . . ? C8 N1 H1A 120.0 . . ? C8 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? N5 N4 C9 122.63(18) . . ? N5 N4 H4A 113.1(18) . . ? C9 N4 H4A 124.2(18) . . ? C9 N3 H3A 120.0 . . ? C9 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C2 C1 C6 120.0(2) . . ? C2 C1 Cl1 120.60(17) . . ? C6 C1 Cl1 119.43(16) . . ? N5 C7 C8 121.25(18) . . ? N5 C7 C6 120.88(19) . . ? C8 C7 C6 117.79(17) . . ? N1 C8 N2 119.79(19) . . ? N1 C8 C7 120.17(18) . . ? N2 C8 C7 120.03(18) . . ? C3 C2 C1 119.9(2) . . ? C3 C2 Cl2 119.24(16) . . ? C1 C2 Cl2 120.84(17) . . ? C5 C6 C1 119.46(19) . . ? C5 C6 C7 120.75(19) . . ? C1 C6 C7 119.04(19) . . ? C7 N5 N4 116.89(18) . . ? C3 C4 C5 120.4(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N3 C9 N2 120.08(19) . . ? N3 C9 N4 118.24(18) . . ? N2 C9 N4 121.67(18) . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C3 C2 120.24(19) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C13 O3 H3O 109.5 . . ? O2 C16 O1 122.5(2) . . ? O2 C16 C10 118.58(18) . . ? O1 C16 C10 118.92(19) . . ? C11 C12 C13 119.93(19) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C15 C10 C11 118.4(2) . . ? C15 C10 C16 120.59(19) . . ? C11 C10 C16 121.00(19) . . ? C15 C14 C13 120.3(2) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C12 C11 C10 121.0(2) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C14 C15 C10 120.9(2) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? O3 C13 C12 123.04(19) . . ? O3 C13 C14 117.4(2) . . ? C12 C13 C14 119.5(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 C9 N2 C8 N1 179.31(19) . . . . ? C9 N2 C8 C7 -1.7(3) . . . . ? N5 C7 C8 N1 -176.65(19) . . . . ? C6 C7 C8 N1 6.7(3) . . . . ? N5 C7 C8 N2 4.3(3) . . . . ? C6 C7 C8 N2 -172.29(19) . . . . ? C6 C1 C2 C3 -0.4(3) . . . . ? Cl1 C1 C2 C3 -178.98(17) . . . . ? C6 C1 C2 Cl2 178.11(16) . . . . ? Cl1 C1 C2 Cl2 -0.5(3) . . . . ? C2 C1 C6 C5 1.3(3) . . . . ? Cl1 C1 C6 C5 179.92(16) . . . . ? C2 C1 C6 C7 -168.86(19) . . . . ? Cl1 C1 C6 C7 9.8(3) . . . . ? N5 C7 C6 C5 101.7(2) . . . . ? C8 C7 C6 C5 -81.6(3) . . . . ? N5 C7 C6 C1 -88.2(3) . . . . ? C8 C7 C6 C1 88.4(2) . . . . ? C8 C7 N5 N4 -1.7(3) . . . . ? C6 C7 N5 N4 174.79(18) . . . . ? C9 N4 N5 C7 -3.3(3) . . . . ? C8 N2 C9 N3 177.84(19) . . . . ? C8 N2 C9 N4 -3.3(3) . . . . ? N5 N4 C9 N3 -174.98(19) . . . . ? N5 N4 C9 N2 6.1(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C1 C6 C5 C4 -0.9(3) . . . . ? C7 C6 C5 C4 169.1(2) . . . . ? C5 C4 C3 C2 1.4(3) . . . . ? C1 C2 C3 C4 -1.0(3) . . . . ? Cl2 C2 C3 C4 -179.50(17) . . . . ? O2 C16 C10 C15 -167.8(2) . . . . ? O1 C16 C10 C15 14.5(3) . . . . ? O2 C16 C10 C11 14.0(3) . . . . ? O1 C16 C10 C11 -163.8(2) . . . . ? C13 C12 C11 C10 1.2(3) . . . . ? C15 C10 C11 C12 -1.9(3) . . . . ? C16 C10 C11 C12 176.4(2) . . . . ? C13 C14 C15 C10 1.2(4) . . . . ? C11 C10 C15 C14 0.7(3) . . . . ? C16 C10 C15 C14 -177.6(2) . . . . ? C11 C12 C13 O3 179.7(2) . . . . ? C11 C12 C13 C14 0.7(3) . . . . ? C15 C14 C13 O3 179.1(2) . . . . ? C15 C14 C13 C12 -1.9(4) . . . . ? #=============================================================================== data_ltgaa _database_code_depnum_ccdc_archive 'CCDC 819592' #TrackingRef 'Finalltgaa.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 Cl2 N5, 2(C2 H4 O2), C2 H3 O2' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C15 H19 Cl2 N5 O6' _chemical_formula_iupac ? _chemical_formula_weight 436.25 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 7.0795(3) _cell_length_b 17.7124(7) _cell_length_c 15.9227(7) _cell_angle_alpha 90 _cell_angle_beta 94.618(2) _cell_angle_gamma 90 _cell_volume 1990.14(14) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 11400 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 25.0 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.368 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_absorpt_correction_T_min 0.8975 _exptl_absorpt_correction_T_max 0.9299 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method 'f\w scans' _diffrn_reflns_number 11400 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3498 # number of observed reflections (> n sig(I)) _reflns_number_gt 2969 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+0.5395P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3498 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0775 _refine_ls_wR_factor_gt 0.0747 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.229 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.046 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl2 Cl 0.78734(6) 0.48867(2) 0.55262(3) 0.02815(13) Uani 1 1 d . . . Cl1 Cl 0.91211(6) 0.32985(2) 0.49113(3) 0.02288(12) Uani 1 1 d . . . O1 O 0.50015(16) 0.10556(7) 0.80275(8) 0.0236(3) Uani 1 1 d . . . O2 O 0.26410(16) 0.12753(7) 0.70563(8) 0.0254(3) Uani 1 1 d . . . O3 O 0.92716(17) 0.35329(7) 0.85409(7) 0.0231(3) Uani 1 1 d . . . O4 O 0.95946(16) 0.31887(6) 0.72120(7) 0.0206(3) Uani 1 1 d . . . O5 O 0.23098(15) 0.43113(7) 0.85595(7) 0.0226(3) Uani 1 1 d . . . O6 O 0.40441(16) 0.52537(7) 0.81661(8) 0.0256(3) Uani 1 1 d . . . N5 N 0.52212(18) 0.16609(8) 0.47728(9) 0.0169(3) Uani 1 1 d . . . N4 N 0.56018(19) 0.09576(8) 0.45126(9) 0.0178(3) Uani 1 1 d . . . N2 N 0.85493(18) 0.08915(7) 0.52962(8) 0.0153(3) Uani 1 1 d . . . N1 N 0.93391(18) 0.18642(8) 0.62041(9) 0.0174(3) Uani 1 1 d . . . H1A H 1.0320 0.1614 0.6399 0.021 Uiso 1 1 calc R . . H1B H 0.9114 0.2303 0.6404 0.021 Uiso 1 1 calc R . . N3 N 0.75408(19) -0.00646(8) 0.43800(9) 0.0195(3) Uani 1 1 d . . . H3A H 0.8567 -0.0311 0.4516 0.023 Uiso 1 1 calc R . . H3B H 0.6702 -0.0250 0.4016 0.023 Uiso 1 1 calc R . . C3 C 0.4864(2) 0.41786(10) 0.60957(11) 0.0234(4) Uani 1 1 d . . . H3 H 0.4504 0.4652 0.6280 0.028 Uiso 1 1 calc R . . C4 C 0.3748(2) 0.35548(10) 0.62146(12) 0.0244(4) Uani 1 1 d . . . H4 H 0.2621 0.3609 0.6471 0.029 Uiso 1 1 calc R . . C5 C 0.4298(2) 0.28485(10) 0.59541(11) 0.0198(4) Uani 1 1 d . . . H5 H 0.3536 0.2432 0.6037 0.024 Uiso 1 1 calc R . . C6 C 0.5986(2) 0.27542(9) 0.55669(10) 0.0150(3) Uani 1 1 d . . . C7 C 0.6486(2) 0.19861(9) 0.52850(10) 0.0149(3) Uani 1 1 d . . . C9 C 0.7253(2) 0.05976(9) 0.47288(10) 0.0162(3) Uani 1 1 d . . . C10 C 0.8734(2) 0.31699(9) 0.78452(11) 0.0183(4) Uani 1 1 d . . . C2 C 0.6527(2) 0.40958(10) 0.56993(11) 0.0199(4) Uani 1 1 d . . . C8 C 0.8182(2) 0.15740(9) 0.55997(10) 0.0144(3) Uani 1 1 d . . . C1 C 0.7083(2) 0.33900(10) 0.54337(10) 0.0172(4) Uani 1 1 d . . . C12 C 0.3370(2) 0.13621(9) 0.77718(12) 0.0204(4) Uani 1 1 d . . . C13 C 0.2504(3) 0.18227(11) 0.84239(13) 0.0310(5) Uani 1 1 d . . . H13A H 0.2764 0.2347 0.8335 0.046 Uiso 1 1 calc R . . H13B H 0.3033 0.1674 0.8973 0.046 Uiso 1 1 calc R . . H13C H 0.1159 0.1743 0.8383 0.046 Uiso 1 1 calc R . . C11 C 0.6961(3) 0.27243(12) 0.79139(12) 0.0305(5) Uani 1 1 d . . . H11A H 0.5905 0.3063 0.7931 0.046 Uiso 1 1 calc R . . H11B H 0.7080 0.2427 0.8420 0.046 Uiso 1 1 calc R . . H11C H 0.6758 0.2397 0.7435 0.046 Uiso 1 1 calc R . . C14 C 0.2543(2) 0.48681(10) 0.80884(11) 0.0192(4) Uani 1 1 d . . . C15 C 0.0992(2) 0.50765(10) 0.74301(11) 0.0234(4) Uani 1 1 d . . . H15A H 0.0573 0.4633 0.7123 0.035 Uiso 1 1 calc R . . H15B H 0.1463 0.5438 0.7049 0.035 Uiso 1 1 calc R . . H15C H -0.0051 0.5292 0.7697 0.035 Uiso 1 1 calc R . . H3O H 1.029(4) 0.3798(15) 0.8464(16) 0.064(8) Uiso 1 1 d . . . H4A H 0.469(3) 0.0783(12) 0.4148(14) 0.041(6) Uiso 1 1 d . . . H1O H 0.546(4) 0.0743(16) 0.7528(19) 0.079(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl2 0.0341(2) 0.0166(2) 0.0326(3) 0.00288(19) -0.0044(2) -0.00431(18) Cl1 0.0205(2) 0.0245(2) 0.0245(2) 0.00134(18) 0.00675(17) -0.00242(17) O1 0.0201(6) 0.0243(7) 0.0254(7) -0.0012(6) -0.0043(5) 0.0021(5) O2 0.0215(6) 0.0285(7) 0.0252(7) 0.0033(6) -0.0047(5) 0.0029(5) O3 0.0233(6) 0.0286(7) 0.0175(7) -0.0077(6) 0.0027(5) -0.0063(6) O4 0.0251(6) 0.0198(6) 0.0172(6) -0.0034(5) 0.0041(5) -0.0025(5) O5 0.0215(6) 0.0225(7) 0.0226(7) 0.0027(6) -0.0051(5) -0.0007(5) O6 0.0193(6) 0.0322(7) 0.0245(7) 0.0059(6) -0.0034(5) -0.0042(5) N5 0.0179(7) 0.0167(8) 0.0163(7) -0.0011(6) 0.0017(6) -0.0014(6) N4 0.0177(7) 0.0170(8) 0.0180(8) -0.0035(6) -0.0021(6) -0.0018(6) N2 0.0180(6) 0.0146(7) 0.0132(7) -0.0010(6) 0.0014(6) -0.0018(6) N1 0.0184(7) 0.0152(7) 0.0179(7) -0.0037(6) -0.0028(6) 0.0037(6) N3 0.0222(7) 0.0164(8) 0.0192(8) -0.0037(6) -0.0027(6) -0.0006(6) C3 0.0259(9) 0.0194(9) 0.0241(10) -0.0043(8) -0.0034(8) 0.0072(7) C4 0.0191(8) 0.0280(10) 0.0263(10) -0.0025(8) 0.0024(7) 0.0056(8) C5 0.0175(8) 0.0215(9) 0.0201(9) 0.0007(8) 0.0006(7) -0.0004(7) C6 0.0161(7) 0.0169(9) 0.0115(8) 0.0008(7) -0.0025(6) 0.0021(7) C7 0.0151(8) 0.0182(9) 0.0118(8) 0.0017(7) 0.0031(6) -0.0009(7) C9 0.0202(8) 0.0166(9) 0.0121(8) 0.0021(7) 0.0030(7) -0.0013(7) C10 0.0209(8) 0.0167(9) 0.0168(9) -0.0012(7) -0.0019(7) 0.0006(7) C2 0.0239(8) 0.0166(9) 0.0178(9) 0.0021(7) -0.0065(7) -0.0005(7) C8 0.0155(7) 0.0163(9) 0.0119(8) 0.0007(7) 0.0031(6) -0.0007(6) C1 0.0157(7) 0.0216(9) 0.0140(8) 0.0009(7) -0.0012(6) 0.0017(7) C12 0.0172(8) 0.0148(9) 0.0293(11) 0.0044(8) 0.0015(7) -0.0047(7) C13 0.0253(9) 0.0294(11) 0.0385(12) -0.0045(9) 0.0044(9) 0.0011(8) C11 0.0322(10) 0.0402(12) 0.0192(10) -0.0026(9) 0.0018(8) -0.0138(9) C14 0.0190(8) 0.0199(9) 0.0185(9) -0.0042(8) 0.0003(7) 0.0029(7) C15 0.0218(9) 0.0224(10) 0.0252(10) 0.0007(8) -0.0036(7) 0.0018(7) _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 C2 1.7289(17) . ? Cl1 C1 1.7299(16) . ? O1 C12 1.311(2) . ? O1 H1O 1.04(3) . ? O2 C12 1.222(2) . ? O3 C10 1.311(2) . ? O3 H3O 0.87(3) . ? O4 C10 1.220(2) . ? O5 C14 1.258(2) . ? O6 C14 1.261(2) . ? N5 C7 1.296(2) . ? N5 N4 1.3468(19) . ? N4 C9 1.351(2) . ? N4 H4A 0.89(2) . ? N2 C8 1.335(2) . ? N2 C9 1.340(2) . ? N1 C8 1.317(2) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N3 C9 1.321(2) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? C3 C4 1.380(3) . ? C3 C2 1.388(2) . ? C3 H3 0.9300 . ? C4 C5 1.384(2) . ? C4 H4 0.9300 . ? C5 C6 1.398(2) . ? C5 H5 0.9300 . ? C6 C1 1.394(2) . ? C6 C7 1.484(2) . ? C7 C8 1.459(2) . ? C10 C11 1.495(2) . ? C2 C1 1.387(2) . ? C12 C13 1.491(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C14 C15 1.501(2) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? 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 C12 O1 H1O 107.6(15) . . ? C10 O3 H3O 109.3(17) . . ? C7 N5 N4 117.35(14) . . ? N5 N4 C9 123.26(14) . . ? N5 N4 H4A 111.8(14) . . ? C9 N4 H4A 124.7(14) . . ? C8 N2 C9 116.92(14) . . ? C8 N1 H1A 120.0 . . ? C8 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C9 N3 H3A 120.0 . . ? C9 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C4 C3 C2 119.58(16) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.32(16) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 120.74(16) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 118.51(15) . . ? C1 C6 C7 123.02(14) . . ? C5 C6 C7 118.42(14) . . ? N5 C7 C8 120.08(15) . . ? N5 C7 C6 115.35(14) . . ? C8 C7 C6 124.36(14) . . ? N3 C9 N2 120.53(15) . . ? N3 C9 N4 118.14(15) . . ? N2 C9 N4 121.32(15) . . ? O4 C10 O3 123.72(15) . . ? O4 C10 C11 123.60(15) . . ? O3 C10 C11 112.68(15) . . ? C1 C2 C3 120.40(16) . . ? C1 C2 Cl2 120.53(13) . . ? C3 C2 Cl2 119.05(13) . . ? N1 C8 N2 119.34(14) . . ? N1 C8 C7 120.13(14) . . ? N2 C8 C7 120.50(14) . . ? C2 C1 C6 120.42(15) . . ? C2 C1 Cl1 119.95(13) . . ? C6 C1 Cl1 119.61(13) . . ? O2 C12 O1 122.21(16) . . ? O2 C12 C13 123.48(16) . . ? O1 C12 C13 114.31(16) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O5 C14 O6 121.06(15) . . ? O5 C14 C15 119.04(15) . . ? O6 C14 C15 119.90(16) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 C7 N5 N4 C9 -3.1(2) . . . . ? C2 C3 C4 C5 1.1(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C4 C5 C6 C1 -1.3(2) . . . . ? C4 C5 C6 C7 -178.81(15) . . . . ? N4 N5 C7 C8 -3.9(2) . . . . ? N4 N5 C7 C6 -178.85(13) . . . . ? C1 C6 C7 N5 -121.42(17) . . . . ? C5 C6 C7 N5 56.0(2) . . . . ? C1 C6 C7 C8 63.9(2) . . . . ? C5 C6 C7 C8 -118.71(17) . . . . ? C8 N2 C9 N3 177.89(14) . . . . ? C8 N2 C9 N4 -3.8(2) . . . . ? N5 N4 C9 N3 -174.26(15) . . . . ? N5 N4 C9 N2 7.3(2) . . . . ? C4 C3 C2 C1 -0.9(3) . . . . ? C4 C3 C2 Cl2 178.07(13) . . . . ? C9 N2 C8 N1 174.99(14) . . . . ? C9 N2 C8 C7 -3.1(2) . . . . ? N5 C7 C8 N1 -170.86(15) . . . . ? C6 C7 C8 N1 3.6(2) . . . . ? N5 C7 C8 N2 7.2(2) . . . . ? C6 C7 C8 N2 -178.30(14) . . . . ? C3 C2 C1 C6 -0.5(3) . . . . ? Cl2 C2 C1 C6 -179.39(12) . . . . ? C3 C2 C1 Cl1 178.00(13) . . . . ? Cl2 C2 C1 Cl1 -0.9(2) . . . . ? C5 C6 C1 C2 1.5(2) . . . . ? C7 C6 C1 C2 178.92(15) . . . . ? C5 C6 C1 Cl1 -176.94(12) . . . . ? C7 C6 C1 Cl1 0.5(2) . . . . ? #===END