# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _audit_creation_method 'SHELXL-97 with enCIFer 1.2' _publ_contact_author_name 'Kari Rissanen' _publ_contact_author_email kari.t.rissanen@jyu.fi _publ_contact_author_address ; Prof. Kari Rissanen Department of Chemistry, Nanoscience Center P.O. BOX 35 40014 University of Jyv\"askyl\"a, Finland ; _publ_section_title ; Interaction Between Amines and N-Haloimides: a New Motif for Unprecedentedly Short Br[?][?][?]N and I[?][?][?]N Halogen Bonds ; loop_ _publ_author_name _publ_author_address 'Kari Raatikainen' ; Department of Chemistry Nanoscience Center P.O. Box 35 FIN-00014 University of Jyv\"askyl\"a Finland ; 'Kari Rissanen' ; Department of Chemistry Nanoscience Center P.O. Box 35 FIN-00014 University of Jyv\"askyl\"a Finland ; data_DABCO-NBS _database_code_depnum_ccdc_archive 'CCDC 821711' _audit_creation_date 2011-01-27T16:22:29-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H12 N2, 2(C4 H4 Br N O2), 2(C H Cl3)' _chemical_formula_sum 'C16 H22 Br2 Cl6 N4 O4' _chemical_formula_weight 706.9 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 18.0736(5) _cell_length_b 6.1490(2) _cell_length_c 23.5057(6) _cell_angle_alpha 90 _cell_angle_beta 97.3440(10) _cell_angle_gamma 90 _cell_volume 2590.87(13) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5088 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.812 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.779 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.4936 _exptl_absorpt_correction_T_max 0.7457 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.382021E-1 _diffrn_orient_matrix_ub_12 0.327964E-1 _diffrn_orient_matrix_ub_13 -0.260372E-1 _diffrn_orient_matrix_ub_21 0.400507E-1 _diffrn_orient_matrix_ub_22 -0.571965E-1 _diffrn_orient_matrix_ub_23 0.294942E-1 _diffrn_orient_matrix_ub_31 -0.69813E-2 _diffrn_orient_matrix_ub_32 -0.148664 _diffrn_orient_matrix_ub_33 -0.170915E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_unetI/netI 0.0469 _diffrn_reflns_number 19738 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 20 _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 0.87 _diffrn_reflns_theta_max 28.45 _diffrn_reflns_theta_full 28.45 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 6499 _reflns_number_gt 5179 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0139P)^2^+3.2193P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6499 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0728 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.471 _refine_diff_density_min -0.713 _refine_diff_density_rms 0.087 #----------------------------------------------------------------------------# # 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' Br Br -0.2901 2.4595 '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.184454(14) 0.76391(4) 0.871261(10) 0.01997(7) Uani 1 1 d . . . N2 N 0.16145(11) 0.9367(3) 0.93556(8) 0.0187(4) Uani 1 1 d . . . C3 C 0.20026(14) 1.1237(4) 0.95441(10) 0.0183(5) Uani 1 1 d . . . O4 O 0.25463(10) 1.1932(3) 0.93503(7) 0.0246(4) Uani 1 1 d . . . C5 C 0.16246(14) 1.2200(4) 1.00214(11) 0.0219(5) Uani 1 1 d . . . H5A H 0.1398 1.3623 0.9905 0.026 Uiso 1 1 calc R . . H5B H 0.1987 1.2407 1.037 0.026 Uiso 1 1 calc R . . C6 C 0.10261(15) 1.0568(4) 1.01320(11) 0.0235(5) Uani 1 1 d . . . H6A H 0.1137 0.9927 1.052 0.028 Uiso 1 1 calc R . . H6B H 0.053 1.1271 1.0098 0.028 Uiso 1 1 calc R . . C7 C 0.10480(14) 0.8849(4) 0.96763(10) 0.0198(5) Uani 1 1 d . . . O8 O 0.06421(11) 0.7265(3) 0.95925(8) 0.0280(4) Uani 1 1 d . . . Br9 Br 0.311203(14) 0.19513(4) 0.631136(10) 0.02116(7) Uani 1 1 d . . . N10 N 0.33686(12) 0.0309(3) 0.56630(8) 0.0192(4) Uani 1 1 d . . . C11 C 0.39227(14) 0.0902(4) 0.53390(10) 0.0209(5) Uani 1 1 d . . . O12 O 0.43068(11) 0.2523(3) 0.54203(8) 0.0284(4) Uani 1 1 d . . . C13 C 0.39583(15) -0.0788(4) 0.48770(10) 0.0229(5) Uani 1 1 d . . . H13A H 0.4461 -0.1448 0.4906 0.028 Uiso 1 1 calc R . . H13B H 0.3837 -0.0137 0.4491 0.028 Uiso 1 1 calc R . . C14 C 0.33767(15) -0.2481(4) 0.49875(11) 0.0235(5) Uani 1 1 d . . . H14A H 0.3007 -0.268 0.4642 0.028 Uiso 1 1 calc R . . H14B H 0.3617 -0.3898 0.5091 0.028 Uiso 1 1 calc R . . C15 C 0.30056(14) -0.1601(4) 0.54783(10) 0.0206(5) Uani 1 1 d . . . O16 O 0.24846(11) -0.2379(3) 0.56857(8) 0.0286(4) Uani 1 1 d . . . N17 N 0.27134(12) 0.3825(3) 0.70871(8) 0.0202(4) Uani 1 1 d . . . C18 C 0.25062(19) 0.2186(4) 0.74925(12) 0.0319(7) Uani 1 1 d . . . H18A H 0.2955 0.1353 0.765 0.038 Uiso 1 1 calc R . . H18B H 0.2143 0.1156 0.7289 0.038 Uiso 1 1 calc R . . C19 C 0.21586(17) 0.3272(4) 0.79890(11) 0.0264(6) Uani 1 1 d . . . H19A H 0.163 0.2827 0.7976 0.032 Uiso 1 1 calc R . . H19B H 0.243 0.2805 0.8362 0.032 Uiso 1 1 calc R . . N20 N 0.22073(12) 0.5659(3) 0.79317(8) 0.0187(4) Uani 1 1 d . . . C21 C 0.17601(15) 0.6301(4) 0.73885(10) 0.0224(5) Uani 1 1 d . . . H21A H 0.1795 0.7893 0.7336 0.027 Uiso 1 1 calc R . . H21B H 0.123 0.5927 0.7402 0.027 Uiso 1 1 calc R . . C22 C 0.20463(16) 0.5115(5) 0.68781(11) 0.0270(6) Uani 1 1 d . . . H22A H 0.1651 0.4147 0.6689 0.032 Uiso 1 1 calc R . . H22B H 0.2172 0.6193 0.6593 0.032 Uiso 1 1 calc R . . C23 C 0.32871(16) 0.5258(5) 0.73861(13) 0.0346(7) Uani 1 1 d . . . H23A H 0.3406 0.6437 0.7126 0.041 Uiso 1 1 calc R . . H23B H 0.3749 0.4418 0.7504 0.041 Uiso 1 1 calc R . . C24 C 0.29972(14) 0.6240(5) 0.79200(11) 0.0252(6) Uani 1 1 d . . . H24A H 0.33 0.5688 0.8271 0.03 Uiso 1 1 calc R . . H24B H 0.3049 0.7842 0.7914 0.03 Uiso 1 1 calc R . . C25 C 0.98131(15) 0.4518(4) 0.86120(11) 0.0254(6) Uani 1 1 d . . . H25 H 1.0163 0.5356 0.8895 0.031 Uiso 1 1 calc R . . Cl26 Cl 0.97447(4) 0.58401(12) 0.79396(3) 0.03496(17) Uani 1 1 d . . . Cl27 Cl 1.01696(5) 0.18653(13) 0.85509(3) 0.03996(19) Uani 1 1 d . . . Cl28 Cl 0.89368(4) 0.43918(12) 0.88598(3) 0.02932(15) Uani 1 1 d . . . C29 C 0.51791(15) 0.5225(4) 0.63867(11) 0.0247(5) Uani 1 1 d . . . H29 H 0.4834 0.4387 0.61 0.03 Uiso 1 1 calc R . . Cl30 Cl 0.52709(4) 0.38366(13) 0.70484(3) 0.03734(18) Uani 1 1 d . . . Cl31 Cl 0.60498(4) 0.54661(12) 0.61337(3) 0.03083(16) Uani 1 1 d . . . Cl32 Cl 0.47960(5) 0.78386(13) 0.64707(3) 0.03918(18) 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 Br1 0.01933(13) 0.02496(13) 0.01574(12) -0.00452(9) 0.00272(9) 0.00276(10) N2 0.0179(11) 0.0229(11) 0.0160(9) -0.0037(8) 0.0046(8) 0.0017(8) C3 0.0197(12) 0.0214(12) 0.0137(10) 0.0016(9) 0.0022(9) 0.0023(10) O4 0.0226(10) 0.0322(10) 0.0201(9) 0.0007(7) 0.0073(7) -0.0027(8) C5 0.0211(13) 0.0258(13) 0.0195(12) -0.0063(10) 0.0047(10) -0.0013(10) C6 0.0218(13) 0.0290(14) 0.0216(12) -0.0073(10) 0.0098(10) -0.0026(10) C7 0.0151(12) 0.0258(13) 0.0190(11) -0.0022(10) 0.0041(9) 0.0023(10) O8 0.0263(10) 0.0273(10) 0.0312(10) -0.0079(8) 0.0073(8) -0.0063(8) Br9 0.02071(13) 0.02694(14) 0.01610(12) -0.00492(9) 0.00343(9) 0.00439(10) N10 0.0185(11) 0.0242(11) 0.0156(9) -0.0063(8) 0.0048(8) 0.0028(8) C11 0.0174(12) 0.0273(14) 0.0182(11) -0.0054(10) 0.0034(10) 0.0027(10) O12 0.0251(10) 0.0269(10) 0.0341(11) -0.0104(8) 0.0072(8) -0.0060(8) C13 0.0225(13) 0.0280(14) 0.0195(12) -0.0079(10) 0.0073(10) -0.0019(10) C14 0.0239(14) 0.0265(13) 0.0214(12) -0.0066(10) 0.0072(11) -0.0020(11) C15 0.0202(13) 0.0247(13) 0.0172(11) 0.0001(10) 0.0037(10) 0.0028(10) O16 0.0268(10) 0.0319(10) 0.0295(10) -0.0003(8) 0.0124(8) -0.0046(8) N17 0.0231(11) 0.0212(11) 0.0172(10) -0.0018(8) 0.0056(8) 0.0029(9) C18 0.053(2) 0.0182(13) 0.0257(14) 0.0005(10) 0.0110(13) 0.0047(12) C19 0.0374(16) 0.0242(13) 0.0191(12) 0.0041(10) 0.0095(11) -0.0015(11) N20 0.0202(11) 0.0221(11) 0.0142(9) -0.0023(8) 0.0043(8) 0.0020(8) C21 0.0217(13) 0.0251(13) 0.0204(12) -0.0009(10) 0.0029(10) 0.0057(10) C22 0.0283(15) 0.0345(15) 0.0185(12) 0.0029(11) 0.0050(11) 0.0101(12) C23 0.0238(15) 0.0462(18) 0.0356(15) -0.0175(13) 0.0112(12) -0.0070(13) C24 0.0193(13) 0.0308(14) 0.0261(13) -0.0101(11) 0.0048(10) -0.0021(11) C25 0.0217(14) 0.0312(14) 0.0230(12) -0.0009(11) 0.0015(11) -0.0004(11) Cl26 0.0322(4) 0.0422(4) 0.0329(4) 0.0130(3) 0.0134(3) 0.0055(3) Cl27 0.0441(5) 0.0400(4) 0.0371(4) 0.0058(3) 0.0105(3) 0.0192(3) Cl28 0.0263(4) 0.0376(4) 0.0259(3) 0.0037(3) 0.0106(3) 0.0037(3) C29 0.0215(14) 0.0283(14) 0.0244(13) -0.0024(11) 0.0032(11) -0.0014(11) Cl30 0.0317(4) 0.0447(4) 0.0376(4) 0.0164(3) 0.0117(3) 0.0051(3) Cl31 0.0301(4) 0.0380(4) 0.0264(3) -0.0040(3) 0.0115(3) -0.0014(3) Cl32 0.0420(5) 0.0389(4) 0.0368(4) 0.0036(3) 0.0056(3) 0.0159(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Br1 N2 1.9356(19) . ? Br1 N20 2.3643(19) . ? N2 C7 1.384(3) . ? N2 C3 1.390(3) . ? C3 O4 1.213(3) . ? C3 C5 1.507(3) . ? C5 C6 1.522(4) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.509(3) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 O8 1.220(3) . ? Br9 N10 1.9335(19) . ? Br9 N17 2.347(2) . ? N10 C11 1.382(3) . ? N10 C15 1.387(3) . ? C11 O12 1.215(3) . ? C11 C13 1.511(3) . ? C13 C14 1.525(4) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.507(3) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 O16 1.213(3) . ? N17 C18 1.468(3) . ? N17 C23 1.469(3) . ? N17 C22 1.474(3) . ? C18 C19 1.546(4) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? C19 N20 1.477(3) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? N20 C21 1.475(3) . ? N20 C24 1.476(3) . ? C21 C22 1.548(3) . ? C21 H21A 0.99 . ? C21 H21B 0.99 . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? C23 C24 1.543(3) . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C25 Cl28 1.758(3) . ? C25 Cl27 1.766(3) . ? C25 Cl26 1.768(3) . ? C25 H25 1 . ? C29 Cl31 1.758(3) . ? C29 Cl30 1.763(3) . ? C29 Cl32 1.771(3) . ? C29 H29 1 . ? 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 N2 Br1 N20 175.95(8) . . ? C7 N2 C3 113.3(2) . . ? C7 N2 Br1 123.14(17) . . ? C3 N2 Br1 123.58(16) . . ? O4 C3 N2 124.9(2) . . ? O4 C3 C5 127.4(2) . . ? N2 C3 C5 107.7(2) . . ? C3 C5 C6 105.5(2) . . ? C3 C5 H5A 110.6 . . ? C6 C5 H5A 110.6 . . ? C3 C5 H5B 110.6 . . ? C6 C5 H5B 110.6 . . ? H5A C5 H5B 108.8 . . ? C7 C6 C5 104.89(19) . . ? C7 C6 H6A 110.8 . . ? C5 C6 H6A 110.8 . . ? C7 C6 H6B 110.8 . . ? C5 C6 H6B 110.8 . . ? H6A C6 H6B 108.8 . . ? O8 C7 N2 124.6(2) . . ? O8 C7 C6 127.2(2) . . ? N2 C7 C6 108.3(2) . . ? N10 Br9 N17 175.78(8) . . ? C11 N10 C15 113.5(2) . . ? C11 N10 Br9 124.05(17) . . ? C15 N10 Br9 122.50(16) . . ? O12 C11 N10 124.7(2) . . ? O12 C11 C13 127.0(2) . . ? N10 C11 C13 108.3(2) . . ? C11 C13 C14 104.7(2) . . ? C11 C13 H13A 110.8 . . ? C14 C13 H13A 110.8 . . ? C11 C13 H13B 110.8 . . ? C14 C13 H13B 110.8 . . ? H13A C13 H13B 108.9 . . ? C15 C14 C13 105.6(2) . . ? C15 C14 H14A 110.6 . . ? C13 C14 H14A 110.6 . . ? C15 C14 H14B 110.6 . . ? C13 C14 H14B 110.6 . . ? H14A C14 H14B 108.7 . . ? O16 C15 N10 124.7(2) . . ? O16 C15 C14 127.6(2) . . ? N10 C15 C14 107.7(2) . . ? C18 N17 C23 108.9(2) . . ? C18 N17 C22 108.7(2) . . ? C23 N17 C22 109.5(2) . . ? C18 N17 Br9 107.24(15) . . ? C23 N17 Br9 113.46(15) . . ? C22 N17 Br9 108.94(14) . . ? N17 C18 C19 110.8(2) . . ? N17 C18 H18A 109.5 . . ? C19 C18 H18A 109.5 . . ? N17 C18 H18B 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? N20 C19 C18 109.0(2) . . ? N20 C19 H19A 109.9 . . ? C18 C19 H19A 109.9 . . ? N20 C19 H19B 109.9 . . ? C18 C19 H19B 109.9 . . ? H19A C19 H19B 108.3 . . ? C21 N20 C24 110.1(2) . . ? C21 N20 C19 108.2(2) . . ? C24 N20 C19 108.1(2) . . ? C21 N20 Br1 111.01(14) . . ? C24 N20 Br1 104.75(14) . . ? C19 N20 Br1 114.54(15) . . ? N20 C21 C22 110.1(2) . . ? N20 C21 H21A 109.6 . . ? C22 C21 H21A 109.6 . . ? N20 C21 H21B 109.6 . . ? C22 C21 H21B 109.6 . . ? H21A C21 H21B 108.1 . . ? N17 C22 C21 109.6(2) . . ? N17 C22 H22A 109.8 . . ? C21 C22 H22A 109.8 . . ? N17 C22 H22B 109.8 . . ? C21 C22 H22B 109.8 . . ? H22A C22 H22B 108.2 . . ? N17 C23 C24 109.4(2) . . ? N17 C23 H23A 109.8 . . ? C24 C23 H23A 109.8 . . ? N17 C23 H23B 109.8 . . ? C24 C23 H23B 109.8 . . ? H23A C23 H23B 108.2 . . ? N20 C24 C23 110.5(2) . . ? N20 C24 H24A 109.6 . . ? C23 C24 H24A 109.6 . . ? N20 C24 H24B 109.6 . . ? C23 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? Cl28 C25 Cl27 109.86(15) . . ? Cl28 C25 Cl26 110.70(15) . . ? Cl27 C25 Cl26 109.67(14) . . ? Cl28 C25 H25 108.9 . . ? Cl27 C25 H25 108.9 . . ? Cl26 C25 H25 108.9 . . ? Cl31 C29 Cl30 110.59(15) . . ? Cl31 C29 Cl32 109.94(15) . . ? Cl30 C29 Cl32 109.58(14) . . ? Cl31 C29 H29 108.9 . . ? Cl30 C29 H29 108.9 . . ? Cl32 C29 H29 108.9 . . ? 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 N20 Br1 N2 C7 -164.0(10) . . . . ? N20 Br1 N2 C3 15.6(12) . . . . ? C7 N2 C3 O4 175.6(2) . . . . ? Br1 N2 C3 O4 -4.0(3) . . . . ? C7 N2 C3 C5 -4.5(3) . . . . ? Br1 N2 C3 C5 175.93(16) . . . . ? O4 C3 C5 C6 -174.3(2) . . . . ? N2 C3 C5 C6 5.7(3) . . . . ? C3 C5 C6 C7 -4.8(3) . . . . ? C3 N2 C7 O8 -179.1(2) . . . . ? Br1 N2 C7 O8 0.5(4) . . . . ? C3 N2 C7 C6 1.2(3) . . . . ? Br1 N2 C7 C6 -179.14(16) . . . . ? C5 C6 C7 O8 -177.2(3) . . . . ? C5 C6 C7 N2 2.4(3) . . . . ? N17 Br9 N10 C11 156.5(10) . . . . ? N17 Br9 N10 C15 -23.4(12) . . . . ? C15 N10 C11 O12 179.3(2) . . . . ? Br9 N10 C11 O12 -0.6(4) . . . . ? C15 N10 C11 C13 -0.5(3) . . . . ? Br9 N10 C11 C13 179.60(16) . . . . ? O12 C11 C13 C14 178.1(3) . . . . ? N10 C11 C13 C14 -2.1(3) . . . . ? C11 C13 C14 C15 3.7(3) . . . . ? C11 N10 C15 O16 -177.2(2) . . . . ? Br9 N10 C15 O16 2.7(4) . . . . ? C11 N10 C15 C14 3.0(3) . . . . ? Br9 N10 C15 C14 -177.14(16) . . . . ? C13 C14 C15 O16 176.0(3) . . . . ? C13 C14 C15 N10 -4.1(3) . . . . ? N10 Br9 N17 C18 59.4(11) . . . . ? N10 Br9 N17 C23 18E1(10) . . . . ? N10 Br9 N17 C22 -58.0(11) . . . . ? C23 N17 C18 C19 62.7(3) . . . . ? C22 N17 C18 C19 -56.5(3) . . . . ? Br9 N17 C18 C19 -174.12(19) . . . . ? N17 C18 C19 N20 -5.3(3) . . . . ? C18 C19 N20 C21 62.9(3) . . . . ? C18 C19 N20 C24 -56.3(3) . . . . ? C18 C19 N20 Br1 -172.68(18) . . . . ? N2 Br1 N20 C21 -110.2(11) . . . . ? N2 Br1 N20 C24 8.6(12) . . . . ? N2 Br1 N20 C19 126.9(11) . . . . ? C24 N20 C21 C22 60.2(3) . . . . ? C19 N20 C21 C22 -57.8(3) . . . . ? Br1 N20 C21 C22 175.70(17) . . . . ? C18 N17 C22 C21 61.5(3) . . . . ? C23 N17 C22 C21 -57.3(3) . . . . ? Br9 N17 C22 C21 178.08(17) . . . . ? N20 C21 C22 N17 -4.0(3) . . . . ? C18 N17 C23 C24 -55.3(3) . . . . ? C22 N17 C23 C24 63.4(3) . . . . ? Br9 N17 C23 C24 -174.68(18) . . . . ? C21 N20 C24 C23 -54.2(3) . . . . ? C19 N20 C24 C23 63.8(3) . . . . ? Br1 N20 C24 C23 -173.7(2) . . . . ? N17 C23 C24 N20 -6.6(3) . . . . ? data_HMTA-NBS _database_code_depnum_ccdc_archive 'CCDC 821712' _audit_creation_date 2009-11-02T17:55:27-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H12 N4, 2(C4 H4 Br N O2)' _chemical_formula_sum 'C14 H20 Br2 N6 O4' _chemical_formula_weight 496.18 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P n' _symmetry_space_group_name_Hall 'P -2yac' _symmetry_Int_Tables_number 7 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 6.7065(2) _cell_length_b 18.5969(6) _cell_length_c 7.1006(2) _cell_angle_alpha 90 _cell_angle_beta 99.500(2) _cell_angle_gamma 90 _cell_volume 873.44(5) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 1807 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.7 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.887 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.676 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.4643 _exptl_absorpt_correction_T_max 0.7457 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.479157E-1 _diffrn_orient_matrix_ub_12 -0.43735E-2 _diffrn_orient_matrix_ub_13 -0.125611 _diffrn_orient_matrix_ub_21 -0.142125 _diffrn_orient_matrix_ub_22 -0.8545E-2 _diffrn_orient_matrix_ub_23 -0.646343E-1 _diffrn_orient_matrix_ub_31 -0.189931E-1 _diffrn_orient_matrix_ub_32 0.529087E-1 _diffrn_orient_matrix_ub_33 -0.208219E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_unetI/netI 0.0426 _diffrn_reflns_number 5612 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 28.51 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.971 _reflns_number_total 3177 _reflns_number_gt 3031 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0411P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3177 _refine_ls_number_parameters 235 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.03 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0689 _refine_ls_wR_factor_gt 0.068 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.009(9) _refine_diff_density_max 0.563 _refine_diff_density_min -0.522 _refine_diff_density_rms 0.089 #----------------------------------------------------------------------------# # 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' Br Br -0.2901 2.4595 '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.86597(5) 0.33833(2) 1.47820(4) 0.01626(9) Uani 1 1 d . . . N2 N 1.0507(5) 0.39888(18) 1.6415(4) 0.0159(7) Uani 1 1 d . . . C3 C 1.0151(6) 0.4225(2) 1.8182(5) 0.0175(8) Uani 1 1 d . . . O4 O 0.8708(5) 0.40425(18) 1.8882(4) 0.0288(7) Uani 1 1 d . . . C5 C 1.1823(6) 0.4728(2) 1.8970(5) 0.0185(8) Uani 1 1 d . . . H5A H 1.2498 0.4564 2.0244 0.022 Uiso 1 1 calc R . . H5B H 1.1292 0.5219 1.909 0.022 Uiso 1 1 calc R . . C6 C 1.3314(6) 0.4717(2) 1.7535(6) 0.0193(8) Uani 1 1 d . . . H6A H 1.3514 0.5206 1.7051 0.023 Uiso 1 1 calc R . . H6B H 1.4641 0.452 1.8133 0.023 Uiso 1 1 calc R . . C7 C 1.2314(6) 0.4233(2) 1.5945(6) 0.0199(8) Uani 1 1 d . . . O8 O 1.2944(5) 0.40709(19) 1.4502(5) 0.0336(8) Uani 1 1 d . . . Br9 Br 0.75245(5) 0.13545(2) 0.73807(4) 0.01621(9) Uani 1 1 d . . . N10 N 0.8703(5) 0.08918(18) 0.5402(4) 0.0151(6) Uani 1 1 d . . . C11 C 1.0596(6) 0.1068(2) 0.4989(5) 0.0162(7) Uani 1 1 d . . . O12 O 1.1748(5) 0.14924(17) 0.5910(4) 0.0256(7) Uani 1 1 d . . . C13 C 1.0880(6) 0.0665(2) 0.3219(5) 0.0182(8) Uani 1 1 d . . . H13A H 1.205 0.0335 0.3492 0.022 Uiso 1 1 calc R . . H13B H 1.1113 0.1003 0.22 0.022 Uiso 1 1 calc R . . C14 C 0.8928(6) 0.0244(2) 0.2617(5) 0.0174(8) Uani 1 1 d . . . H14A H 0.8258 0.0393 0.1328 0.021 Uiso 1 1 calc R . . H14B H 0.9203 -0.0279 0.2605 0.021 Uiso 1 1 calc R . . C15 C 0.7626(6) 0.0424(2) 0.4093(5) 0.0177(8) Uani 1 1 d . . . O16 O 0.5907(5) 0.02181(18) 0.4134(4) 0.0268(7) Uani 1 1 d . . . N17 N 0.3070(5) 0.21004(18) 1.1422(4) 0.0158(6) Uani 1 1 d . . . C18 C 0.2290(5) 0.2721(2) 1.0249(5) 0.0169(8) Uani 1 1 d . . . H18A H 0.1312 0.255 0.9141 0.02 Uiso 1 1 calc R . . H18B H 0.1556 0.3042 1.1013 0.02 Uiso 1 1 calc R . . N19 N 0.3886(5) 0.31315(18) 0.9559(4) 0.0158(6) Uani 1 1 d . . . C20 C 0.4955(6) 0.2647(2) 0.8437(5) 0.0161(8) Uani 1 1 d . . . H20A H 0.6051 0.2915 0.7969 0.019 Uiso 1 1 calc R . . H20B H 0.4004 0.2474 0.7313 0.019 Uiso 1 1 calc R . . N21 N 0.5838(5) 0.20158(17) 0.9585(4) 0.0160(7) Uani 1 1 d . . . C22 C 0.4144(6) 0.1627(2) 1.0273(5) 0.0161(8) Uani 1 1 d . . . H22A H 0.3186 0.1447 0.9163 0.019 Uiso 1 1 calc R . . H22B H 0.469 0.1208 1.1052 0.019 Uiso 1 1 calc R . . N23 N 0.6195(5) 0.27634(18) 1.2441(4) 0.0154(6) Uani 1 1 d . . . C24 C 0.5317(6) 0.3375(2) 1.1223(5) 0.0158(7) Uani 1 1 d . . . H24A H 0.4614 0.3704 1.1994 0.019 Uiso 1 1 calc R . . H24B H 0.6422 0.3648 1.0783 0.019 Uiso 1 1 calc R . . C25 C 0.4499(6) 0.2365(2) 1.3071(5) 0.0172(8) Uani 1 1 d . . . H25A H 0.5043 0.1953 1.3879 0.021 Uiso 1 1 calc R . . H25B H 0.3782 0.2686 1.3849 0.021 Uiso 1 1 calc R . . C26 C 0.7225(6) 0.2282(2) 1.1263(5) 0.0192(8) Uani 1 1 d . . . H26A H 0.8353 0.2545 1.0833 0.023 Uiso 1 1 calc R . . H26B H 0.7802 0.1869 1.2046 0.023 Uiso 1 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 Br1 0.01664(17) 0.0162(2) 0.01614(16) -0.00086(15) 0.00338(13) -0.00106(15) N2 0.0165(16) 0.0188(18) 0.0126(13) -0.0040(13) 0.0027(12) -0.0037(13) C3 0.023(2) 0.016(2) 0.0145(16) 0.0005(15) 0.0054(15) -0.0024(16) O4 0.0267(16) 0.037(2) 0.0252(15) -0.0092(14) 0.0128(12) -0.0146(14) C5 0.021(2) 0.016(2) 0.0179(17) -0.0036(16) 0.0020(15) -0.0014(16) C6 0.0150(17) 0.019(2) 0.0240(18) -0.0009(17) 0.0041(15) -0.0037(15) C7 0.0153(18) 0.020(2) 0.0259(19) -0.0008(17) 0.0073(15) -0.0009(16) O8 0.0294(17) 0.040(2) 0.0365(17) -0.0153(16) 0.0211(14) -0.0101(15) Br9 0.01790(18) 0.0170(2) 0.01423(15) -0.00151(15) 0.00424(13) -0.00104(15) N10 0.0140(15) 0.0166(16) 0.0149(13) -0.0023(13) 0.0030(12) 0.0014(13) C11 0.0162(17) 0.0163(19) 0.0163(16) 0.0044(15) 0.0037(14) 0.0032(15) O12 0.0191(15) 0.0325(18) 0.0249(14) -0.0071(13) 0.0028(12) -0.0082(13) C13 0.0152(18) 0.023(2) 0.0177(17) 0.0015(17) 0.0052(14) -0.0002(16) C14 0.0197(19) 0.018(2) 0.0156(16) -0.0052(15) 0.0044(15) 0.0000(15) C15 0.0159(19) 0.020(2) 0.0185(17) 0.0025(16) 0.0067(15) 0.0001(15) O16 0.0201(16) 0.0321(19) 0.0304(16) -0.0053(14) 0.0108(13) -0.0080(13) N17 0.0148(15) 0.0177(17) 0.0144(13) -0.0015(13) 0.0014(12) -0.0030(13) C18 0.0122(18) 0.020(2) 0.0186(17) 0.0016(16) 0.0030(14) 0.0005(16) N19 0.0154(15) 0.0169(16) 0.0153(14) -0.0050(13) 0.0025(12) -0.0049(14) C20 0.0150(19) 0.019(2) 0.0144(16) -0.0011(15) 0.0035(14) -0.0007(15) N21 0.0164(16) 0.0166(17) 0.0158(14) -0.0031(13) 0.0047(12) -0.0012(13) C22 0.0186(19) 0.0134(19) 0.0159(17) -0.0005(15) 0.0016(14) -0.0039(14) N23 0.0142(14) 0.0163(17) 0.0144(13) 0.0001(13) -0.0014(11) -0.0018(13) C24 0.0181(19) 0.0130(19) 0.0160(16) -0.0017(15) 0.0021(14) -0.0044(15) C25 0.0203(18) 0.019(2) 0.0127(15) -0.0002(15) 0.0038(14) -0.0058(16) C26 0.0147(18) 0.023(2) 0.0191(17) -0.0029(16) 0.0014(14) -0.0009(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Br1 N2 1.917(3) . ? N2 C7 1.386(5) . ? N2 C3 1.386(5) . ? C3 O4 1.207(5) . ? C3 C5 1.496(5) . ? C5 C6 1.541(6) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.512(6) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 O8 1.210(5) . ? Br9 N10 1.925(3) . ? N10 C15 1.386(5) . ? N10 C11 1.389(5) . ? C11 O12 1.217(5) . ? C11 C13 1.502(5) . ? C13 C14 1.525(5) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.509(5) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 O16 1.219(5) . ? N17 C22 1.467(5) . ? N17 C18 1.468(5) . ? N17 C25 1.470(5) . ? C18 N19 1.464(5) . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? N19 C24 1.466(5) . ? N19 C20 1.466(5) . ? C20 N21 1.494(5) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? N21 C26 1.471(5) . ? N21 C22 1.495(5) . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? N23 C26 1.472(5) . ? N23 C25 1.487(5) . ? N23 C24 1.491(5) . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C25 H25A 0.99 . ? C25 H25B 0.99 . ? C26 H26A 0.99 . ? C26 H26B 0.99 . ? 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 N2 C3 113.7(3) . . ? C7 N2 Br1 123.4(3) . . ? C3 N2 Br1 122.9(3) . . ? O4 C3 N2 123.6(4) . . ? O4 C3 C5 128.6(4) . . ? N2 C3 C5 107.8(3) . . ? C3 C5 C6 105.8(3) . . ? C3 C5 H5A 110.6 . . ? C6 C5 H5A 110.6 . . ? C3 C5 H5B 110.6 . . ? C6 C5 H5B 110.6 . . ? H5A C5 H5B 108.7 . . ? C7 C6 C5 104.2(3) . . ? C7 C6 H6A 110.9 . . ? C5 C6 H6A 110.9 . . ? C7 C6 H6B 110.9 . . ? C5 C6 H6B 110.9 . . ? H6A C6 H6B 108.9 . . ? O8 C7 N2 124.4(4) . . ? O8 C7 C6 127.4(4) . . ? N2 C7 C6 108.2(3) . . ? C15 N10 C11 113.6(3) . . ? C15 N10 Br9 122.6(2) . . ? C11 N10 Br9 123.2(3) . . ? O12 C11 N10 124.1(3) . . ? O12 C11 C13 128.0(3) . . ? N10 C11 C13 107.8(3) . . ? C11 C13 C14 105.6(3) . . ? C11 C13 H13A 110.6 . . ? C14 C13 H13A 110.6 . . ? C11 C13 H13B 110.6 . . ? C14 C13 H13B 110.6 . . ? H13A C13 H13B 108.8 . . ? C15 C14 C13 105.1(3) . . ? C15 C14 H14A 110.7 . . ? C13 C14 H14A 110.7 . . ? C15 C14 H14B 110.7 . . ? C13 C14 H14B 110.7 . . ? H14A C14 H14B 108.8 . . ? O16 C15 N10 124.8(4) . . ? O16 C15 C14 127.2(4) . . ? N10 C15 C14 107.9(3) . . ? C22 N17 C18 108.5(3) . . ? C22 N17 C25 109.1(3) . . ? C18 N17 C25 108.3(3) . . ? N19 C18 N17 112.8(3) . . ? N19 C18 H18A 109 . . ? N17 C18 H18A 109 . . ? N19 C18 H18B 109 . . ? N17 C18 H18B 109 . . ? H18A C18 H18B 107.8 . . ? C18 N19 C24 108.0(3) . . ? C18 N19 C20 108.2(3) . . ? C24 N19 C20 108.3(3) . . ? N19 C20 N21 111.8(3) . . ? N19 C20 H20A 109.2 . . ? N21 C20 H20A 109.2 . . ? N19 C20 H20B 109.2 . . ? N21 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? C26 N21 C20 108.5(3) . . ? C26 N21 C22 108.1(3) . . ? C20 N21 C22 107.7(3) . . ? N17 C22 N21 111.2(3) . . ? N17 C22 H22A 109.4 . . ? N21 C22 H22A 109.4 . . ? N17 C22 H22B 109.4 . . ? N21 C22 H22B 109.4 . . ? H22A C22 H22B 108 . . ? C26 N23 C25 108.7(3) . . ? C26 N23 C24 108.1(3) . . ? C25 N23 C24 107.9(3) . . ? N19 C24 N23 112.0(3) . . ? N19 C24 H24A 109.2 . . ? N23 C24 H24A 109.2 . . ? N19 C24 H24B 109.2 . . ? N23 C24 H24B 109.2 . . ? H24A C24 H24B 107.9 . . ? N17 C25 N23 111.0(3) . . ? N17 C25 H25A 109.4 . . ? N23 C25 H25A 109.4 . . ? N17 C25 H25B 109.4 . . ? N23 C25 H25B 109.4 . . ? H25A C25 H25B 108 . . ? N21 C26 N23 111.8(3) . . ? N21 C26 H26A 109.2 . . ? N23 C26 H26A 109.2 . . ? N21 C26 H26B 109.2 . . ? N23 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? 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 N2 C3 O4 -176.3(4) . . . . ? Br1 N2 C3 O4 3.8(6) . . . . ? C7 N2 C3 C5 4.2(5) . . . . ? Br1 N2 C3 C5 -175.7(3) . . . . ? O4 C3 C5 C6 176.1(4) . . . . ? N2 C3 C5 C6 -4.4(4) . . . . ? C3 C5 C6 C7 3.2(4) . . . . ? C3 N2 C7 O8 177.4(4) . . . . ? Br1 N2 C7 O8 -2.7(6) . . . . ? C3 N2 C7 C6 -2.1(5) . . . . ? Br1 N2 C7 C6 177.8(3) . . . . ? C5 C6 C7 O8 179.7(4) . . . . ? C5 C6 C7 N2 -0.9(4) . . . . ? C15 N10 C11 O12 176.9(4) . . . . ? Br9 N10 C11 O12 5.3(5) . . . . ? C15 N10 C11 C13 -1.3(4) . . . . ? Br9 N10 C11 C13 -172.9(3) . . . . ? O12 C11 C13 C14 -177.0(4) . . . . ? N10 C11 C13 C14 1.1(4) . . . . ? C11 C13 C14 C15 -0.5(4) . . . . ? C11 N10 C15 O16 -177.3(4) . . . . ? Br9 N10 C15 O16 -5.6(6) . . . . ? C11 N10 C15 C14 1.0(4) . . . . ? Br9 N10 C15 C14 172.7(3) . . . . ? C13 C14 C15 O16 177.9(4) . . . . ? C13 C14 C15 N10 -0.3(4) . . . . ? C22 N17 C18 N19 -59.0(4) . . . . ? C25 N17 C18 N19 59.4(4) . . . . ? N17 C18 N19 C24 -58.5(4) . . . . ? N17 C18 N19 C20 58.6(4) . . . . ? C18 N19 C20 N21 -58.4(4) . . . . ? C24 N19 C20 N21 58.5(4) . . . . ? N19 C20 N21 C26 -58.1(4) . . . . ? N19 C20 N21 C22 58.7(4) . . . . ? C18 N17 C22 N21 58.5(4) . . . . ? C25 N17 C22 N21 -59.3(4) . . . . ? C26 N21 C22 N17 58.6(4) . . . . ? C20 N21 C22 N17 -58.5(4) . . . . ? C18 N19 C24 N23 58.0(4) . . . . ? C20 N19 C24 N23 -59.0(4) . . . . ? C26 N23 C24 N19 58.7(4) . . . . ? C25 N23 C24 N19 -58.7(4) . . . . ? C22 N17 C25 N23 58.9(4) . . . . ? C18 N17 C25 N23 -59.0(4) . . . . ? C26 N23 C25 N17 -58.2(4) . . . . ? C24 N23 C25 N17 58.8(4) . . . . ? C20 N21 C26 N23 58.0(4) . . . . ? C22 N21 C26 N23 -58.5(4) . . . . ? C25 N23 C26 N21 58.7(4) . . . . ? C24 N23 C26 N21 -58.2(4) . . . . ? data_HMTA-NIS _database_code_depnum_ccdc_archive 'CCDC 821713' _audit_creation_date 2011-01-27T15:36:59-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H12 N4, 4(C4 H4 I N O2)' _chemical_formula_sum 'C22 H28 I4 N8 O8' _chemical_formula_weight 1040.12 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I -4 c 2' _symmetry_space_group_name_Hall 'I -4 -2c' _symmetry_Int_Tables_number 120 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, -x, -z+1/2' 'y, x, -z+1/2' '-x, y, z+1/2' 'x, -y, z+1/2' '-y, x, -z' 'y, -x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-y+1/2, -x+1/2, -z+1' 'y+1/2, x+1/2, -z+1' '-x+1/2, y+1/2, z+1' 'x+1/2, -y+1/2, z+1' '-y+1/2, x+1/2, -z+1/2' 'y+1/2, -x+1/2, -z+1/2' _cell_length_a 16.8164(7) _cell_length_b 16.8164(7) _cell_length_c 14.3925(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4070.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2234 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.697 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.5528 _exptl_absorpt_correction_T_max 0.7457 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.138563E-1 _diffrn_orient_matrix_ub_12 0.577713E-1 _diffrn_orient_matrix_ub_13 0.30145E-2 _diffrn_orient_matrix_ub_21 -0.42028E-1 _diffrn_orient_matrix_ub_22 -0.82379E-2 _diffrn_orient_matrix_ub_23 -0.482028E-1 _diffrn_orient_matrix_ub_31 -0.397219E-1 _diffrn_orient_matrix_ub_32 -0.114363E-1 _diffrn_orient_matrix_ub_33 0.499496E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0533 _diffrn_reflns_av_unetI/netI 0.0455 _diffrn_reflns_number 12879 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 2295 _reflns_number_gt 1974 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0366P)^2^+72.0800P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2295 _refine_ls_number_parameters 97 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1228 _refine_ls_goodness_of_fit_ref 1.197 _refine_ls_restrained_S_all 1.197 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.14(8) _refine_diff_density_max 0.934 _refine_diff_density_min -1.485 _refine_diff_density_rms 0.205 #----------------------------------------------------------------------------# # 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' I I -0.4742 1.8119 '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.80950(3) 0.02025(4) 0.17022(6) 0.03214(18) Uani 1 1 d . . . N1 N 0.7182(5) 0.0321(5) 0.2709(6) 0.0267(19) Uani 1 1 d . . . C2 C 0.7273(6) -0.0001(7) 0.3592(8) 0.034(3) Uani 1 1 d . . . O3 O 0.7861(5) -0.0390(5) 0.3831(6) 0.046(2) Uani 1 1 d . . . C4 C 0.6591(8) 0.0269(9) 0.4146(9) 0.049(3) Uani 1 1 d . . . H4A H 0.6776 0.0613 0.4661 0.059 Uiso 1 1 calc R . . H4B H 0.6311 -0.0194 0.4415 0.059 Uiso 1 1 calc R . . C5 C 0.6051(7) 0.0717(8) 0.3536(7) 0.045(3) Uani 1 1 d . . . H5A H 0.5979 0.1267 0.3765 0.054 Uiso 1 1 calc R . . H5B H 0.5525 0.0455 0.35 0.054 Uiso 1 1 calc R . . C6 C 0.6468(6) 0.0713(6) 0.2577(9) 0.033(3) Uani 1 1 d . . . O7 O 0.6259(4) 0.1010(5) 0.1877(5) 0.041(2) Uani 1 1 d . . . N8 N 0.9275(4) 0.0099(5) 0.0596(6) 0.0256(19) Uani 1 1 d . . . C9 C 0.9378(5) 0.0795(5) 0.0010(7) 0.025(2) Uani 1 1 d . . . H9A H 0.9428 0.1273 0.0407 0.031 Uiso 1 1 calc R . . H9B H 0.8901 0.0862 -0.0385 0.031 Uiso 1 1 calc R . . C10 C 1 0 0.1146(8) 0.019(3) Uani 1 2 d S . . H10A H 0.9936 -0.0471 0.1553 0.023 Uiso 0.5 1 calc PR . . H10B H 1.0064 0.0471 0.1553 0.023 Uiso 0.5 1 calc PR . . 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 I1 0.0223(3) 0.0289(3) 0.0451(3) -0.0037(3) -0.0001(4) 0.0013(2) N1 0.013(3) 0.020(4) 0.048(5) -0.005(4) 0.001(4) -0.008(3) C2 0.021(5) 0.033(6) 0.048(7) -0.012(5) -0.001(4) -0.009(4) O3 0.025(4) 0.063(6) 0.049(5) -0.004(4) -0.009(3) 0.004(3) C4 0.043(6) 0.052(9) 0.051(8) -0.003(6) -0.018(7) 0.013(6) C5 0.045(7) 0.062(8) 0.027(6) -0.015(5) 0.002(5) -0.003(6) C6 0.024(5) 0.015(5) 0.060(8) -0.014(5) 0.000(5) 0.005(4) O7 0.042(4) 0.044(4) 0.036(5) 0.009(4) 0.003(4) -0.003(4) N8 0.011(3) 0.021(4) 0.045(6) -0.001(4) -0.005(3) 0.002(3) C9 0.022(4) 0.018(4) 0.037(5) -0.003(4) 0.001(4) 0.007(3) C10 0.016(6) 0.031(7) 0.010(6) 0 0 0.004(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 I1 N1 2.121(9) . ? I1 N8 2.549(8) . ? N1 C6 1.384(13) . ? N1 C2 1.389(15) . ? C2 O3 1.234(13) . ? C2 C4 1.468(16) . ? C4 C5 1.470(17) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.548(16) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 O7 1.179(14) . ? N8 C9 1.452(12) . ? N8 C10 1.464(10) . ? N8 C9 1.500(13) 7_645 ? C9 N8 1.500(13) 8_665 ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 N8 1.464(10) 2_755 ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? 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 N1 I1 N8 175.2(3) . . ? C6 N1 C2 114.0(9) . . ? C6 N1 I1 125.4(8) . . ? C2 N1 I1 120.6(6) . . ? O3 C2 N1 123.4(10) . . ? O3 C2 C4 129.6(11) . . ? N1 C2 C4 106.9(9) . . ? C2 C4 C5 108.5(10) . . ? C2 C4 H4A 110 . . ? C5 C4 H4A 110 . . ? C2 C4 H4B 110 . . ? C5 C4 H4B 110 . . ? H4A C4 H4B 108.4 . . ? C4 C5 C6 104.5(10) . . ? C4 C5 H5A 110.9 . . ? C6 C5 H5A 110.9 . . ? C4 C5 H5B 110.9 . . ? C6 C5 H5B 110.9 . . ? H5A C5 H5B 108.9 . . ? O7 C6 N1 125.4(11) . . ? O7 C6 C5 128.7(9) . . ? N1 C6 C5 105.8(10) . . ? C9 N8 C10 107.8(6) . . ? C9 N8 C9 108.8(6) . 7_645 ? C10 N8 C9 106.7(6) . 7_645 ? C9 N8 I1 113.6(5) . . ? C10 N8 I1 108.6(6) . . ? C9 N8 I1 111.0(5) 7_645 . ? N8 C9 N8 111.9(8) . 8_665 ? N8 C9 H9A 109.2 . . ? N8 C9 H9A 109.2 8_665 . ? N8 C9 H9B 109.2 . . ? N8 C9 H9B 109.2 8_665 . ? H9A C9 H9B 107.9 . . ? N8 C10 N8 114.5(10) . 2_755 ? N8 C10 H10A 108.6 . . ? N8 C10 H10A 108.6 2_755 . ? N8 C10 H10B 108.6 . . ? N8 C10 H10B 108.6 2_755 . ? H10A C10 H10B 107.6 . . ? 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 N8 I1 N1 C6 131(3) . . . . ? N8 I1 N1 C2 -48(4) . . . . ? C6 N1 C2 O3 177.9(9) . . . . ? I1 N1 C2 O3 -2.7(13) . . . . ? C6 N1 C2 C4 -6.3(12) . . . . ? I1 N1 C2 C4 173.0(8) . . . . ? O3 C2 C4 C5 179.7(11) . . . . ? N1 C2 C4 C5 4.4(14) . . . . ? C2 C4 C5 C6 -1.2(14) . . . . ? C2 N1 C6 O7 -177.9(10) . . . . ? I1 N1 C6 O7 2.8(14) . . . . ? C2 N1 C6 C5 5.5(11) . . . . ? I1 N1 C6 C5 -173.8(7) . . . . ? C4 C5 C6 O7 -178.9(11) . . . . ? C4 C5 C6 N1 -2.4(12) . . . . ? N1 I1 N8 C9 -96(3) . . . . ? N1 I1 N8 C10 24(4) . . . . ? N1 I1 N8 C9 141(3) . . . 7_645 ? C10 N8 C9 N8 56.9(9) . . . 8_665 ? C9 N8 C9 N8 -58.5(7) 7_645 . . 8_665 ? I1 N8 C9 N8 177.3(6) . . . 8_665 ? C9 N8 C10 N8 -58.8(6) . . . 2_755 ? C9 N8 C10 N8 58.0(6) 7_645 . . 2_755 ? I1 N8 C10 N8 177.7(5) . . . 2_755 ? data_TRZ-NIS _database_code_depnum_ccdc_archive 'CCDC 821714' _audit_creation_date 2009-11-20T13:44:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C4 H4 I N O2), C3 H3 N3' _chemical_formula_sum 'C11 H11 I2 N5 O4' _chemical_formula_weight 531.05 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 30.8657(8) _cell_length_b 6.10710(10) _cell_length_c 8.2339(2) _cell_angle_alpha 90 _cell_angle_beta 95.363(2) _cell_angle_gamma 90 _cell_volume 1545.30(6) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2022 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 2.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.519 _exptl_absorpt_correction_T_max 0.7456 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.55018E-2 _diffrn_orient_matrix_ub_12 0.825636E-1 _diffrn_orient_matrix_ub_13 -0.104778 _diffrn_orient_matrix_ub_21 -0.293555E-1 _diffrn_orient_matrix_ub_22 0.437071E-1 _diffrn_orient_matrix_ub_23 0.308907E-1 _diffrn_orient_matrix_ub_31 0.129186E-1 _diffrn_orient_matrix_ub_32 0.13448 _diffrn_orient_matrix_ub_33 0.542882E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_unetI/netI 0.0213 _diffrn_reflns_number 9304 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.4 _diffrn_reflns_theta_max 27.86 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.958 _reflns_number_total 1771 _reflns_number_gt 1652 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0129P)^2^+3.5326P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1771 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0207 _refine_ls_R_factor_gt 0.0188 _refine_ls_wR_factor_ref 0.0447 _refine_ls_wR_factor_gt 0.0437 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.159 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.412 _refine_diff_density_min -1.005 _refine_diff_density_rms 0.123 #----------------------------------------------------------------------------# # 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' I I -0.4742 1.8119 '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.905615(4) 0.49260(2) 0.016047(16) 0.01448(7) Uani 1 1 d . . . N2 N 0.85501(6) 0.6838(3) -0.0910(2) 0.0153(4) Uani 1 1 d . . . C3 C 0.86241(7) 0.8797(3) -0.1699(3) 0.0165(4) Uani 1 1 d . . . O4 O 0.89799(6) 0.9613(3) -0.1749(2) 0.0231(4) Uani 1 1 d . . . C5 C 0.81913(9) 0.9664(4) -0.2431(3) 0.0231(5) Uani 1 1 d . . . H5A H 0.8181 0.9708 -0.3636 0.028 Uiso 1 1 calc R . . H5B H 0.814 1.1159 -0.2025 0.028 Uiso 1 1 calc R . . C6 C 0.78536(7) 0.8073(4) -0.1888(3) 0.0200(5) Uani 1 1 d . . . H6A H 0.7659 0.8813 -0.1171 0.024 Uiso 1 1 calc R . . H6B H 0.7675 0.7459 -0.2842 0.024 Uiso 1 1 calc R . . C7 C 0.81143(7) 0.6293(4) -0.0971(3) 0.0166(4) Uani 1 1 d . . . O8 O 0.79748(6) 0.4653(3) -0.0360(2) 0.0239(4) Uani 1 1 d . . . N9 N 1 -0.0664(5) 0.25 0.0183(6) Uani 1 2 d S . . C10 C 0.97106(8) 0.0523(4) 0.1561(3) 0.0173(4) Uani 1 1 d . . . H10 H 0.9498 -0.0248 0.0872 0.021 Uiso 1 1 calc R . . N11 N 0.96978(6) 0.2705(3) 0.1519(2) 0.0168(4) Uani 1 1 d . . . C12 C 1 0.3729(5) 0.25 0.0165(6) Uani 1 2 d S . . H12 H 1 0.5284 0.25 0.02 Uiso 1 2 calc SR . . 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 I1 0.01282(11) 0.01508(9) 0.01523(9) 0.00088(5) -0.00042(6) 0.00045(5) N2 0.0120(9) 0.0151(8) 0.0184(9) 0.0016(7) 0.0001(7) 0.0011(7) C3 0.0185(12) 0.0140(10) 0.0171(10) -0.0022(8) 0.0022(8) 0.0005(9) O4 0.0196(9) 0.0188(8) 0.0315(9) 0.0005(7) 0.0057(8) -0.0036(7) C5 0.0216(14) 0.0206(11) 0.0266(13) 0.0061(9) -0.0004(10) 0.0039(10) C6 0.0163(12) 0.0213(11) 0.0218(11) 0.0010(9) -0.0020(9) 0.0022(9) C7 0.0143(11) 0.0181(10) 0.0174(10) -0.0023(8) 0.0013(8) 0.0004(9) O8 0.0182(9) 0.0212(8) 0.0325(10) 0.0049(7) 0.0032(7) -0.0023(7) N9 0.0138(14) 0.0143(12) 0.0270(15) 0 0.0030(11) 0 C10 0.0132(11) 0.0185(10) 0.0200(11) -0.0017(9) 0.0016(9) -0.0009(9) N11 0.0141(10) 0.0170(9) 0.0189(9) 0.0002(7) -0.0002(7) 0.0004(7) C12 0.0153(16) 0.0142(14) 0.0203(15) 0 0.0027(12) 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 I1 N2 2.0790(18) . ? N2 C7 1.382(3) . ? N2 C3 1.390(3) . ? C3 O4 1.210(3) . ? C3 C5 1.509(3) . ? C5 C6 1.522(3) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.512(3) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 O8 1.217(3) . ? N9 C10 1.339(3) . ? N9 C10 1.339(3) 2_755 ? C10 N11 1.333(3) . ? C10 H10 0.95 . ? N11 C12 1.331(2) . ? C12 N11 1.331(2) 2_755 ? C12 H12 0.95 . ? 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 N2 C3 113.08(18) . . ? C7 N2 I1 124.77(14) . . ? C3 N2 I1 122.11(15) . . ? O4 C3 N2 124.0(2) . . ? O4 C3 C5 127.9(2) . . ? N2 C3 C5 108.10(19) . . ? C3 C5 C6 105.29(18) . . ? C3 C5 H5A 110.7 . . ? C6 C5 H5A 110.7 . . ? C3 C5 H5B 110.7 . . ? C6 C5 H5B 110.7 . . ? H5A C5 H5B 108.8 . . ? C7 C6 C5 104.98(19) . . ? C7 C6 H6A 110.8 . . ? C5 C6 H6A 110.8 . . ? C7 C6 H6B 110.8 . . ? C5 C6 H6B 110.8 . . ? H6A C6 H6B 108.8 . . ? O8 C7 N2 124.3(2) . . ? O8 C7 C6 127.3(2) . . ? N2 C7 C6 108.40(18) . . ? C10 N9 C10 114.4(3) . 2_755 ? N11 C10 N9 124.9(2) . . ? N11 C10 H10 117.5 . . ? N9 C10 H10 117.5 . . ? C12 N11 C10 115.9(2) . . ? N11 C12 N11 124.0(3) . 2_755 ? N11 C12 H12 118 . . ? N11 C12 H12 118 2_755 . ? 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 N2 C3 O4 177.6(2) . . . . ? I1 N2 C3 O4 -4.5(3) . . . . ? C7 N2 C3 C5 -1.9(3) . . . . ? I1 N2 C3 C5 175.98(15) . . . . ? O4 C3 C5 C6 -175.9(2) . . . . ? N2 C3 C5 C6 3.6(2) . . . . ? C3 C5 C6 C7 -3.8(2) . . . . ? C3 N2 C7 O8 -179.9(2) . . . . ? I1 N2 C7 O8 2.3(3) . . . . ? C3 N2 C7 C6 -0.6(2) . . . . ? I1 N2 C7 C6 -178.45(14) . . . . ? C5 C6 C7 O8 -177.9(2) . . . . ? C5 C6 C7 N2 2.8(2) . . . . ? C10 N9 C10 N11 0.02(16) 2_755 . . . ? N9 C10 N11 C12 0.0(3) . . . . ? C10 N11 C12 N11 0.01(14) . . . 2_755 ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF