# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1f _audit_creation_date 2013-03-05T14:13:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H8 N4' _chemical_formula_sum 'C11 H8 N4' _chemical_formula_weight 196.21 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.2914(14) _cell_length_b 3.7335(4) _cell_length_c 21.924(3) _cell_angle_alpha 90 _cell_angle_beta 96.597(7) _cell_angle_gamma 90 _cell_volume 918.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 215 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 22.94 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.42 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.820 _exptl_absorpt_correction_T_max 0.997 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_unetI/netI 0.08 _diffrn_reflns_number 5968 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 27.43 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 2081 _reflns_number_gt 1241 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 2012), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0597P)^2^+0.0000P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.021(4) _refine_ls_number_reflns 2081 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1134 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.02 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.237 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.058 _iucr_refine_instructions_details ; .res file for SHELXL : EN1147e.res ................................................................. TITL import in P 21/c CELL 0.71073 11.2914 3.7335 21.9240 90.000 96.597 90.000 ZERR 4.00 0.0014 0.0004 0.0030 0.000 0.007 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N UNIT 44 32 16 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.059700 EXTI 0.021194 FVAR 0.95145 C1 1 0.833502 0.010455 0.724364 11.00000 0.01960 0.02523 = 0.02915 -0.00182 0.00415 0.00046 AFIX 43 H1 2 0.916356 -0.028407 0.735347 11.00000 -1.20000 AFIX 0 C2 1 0.781450 -0.044419 0.664749 11.00000 0.02908 0.03213 = 0.02421 -0.00068 0.00634 -0.00069 AFIX 43 H2 2 0.828112 -0.119042 0.633654 11.00000 -1.20000 AFIX 0 C3 1 0.659894 0.011786 0.651399 11.00000 0.03038 0.02924 = 0.02232 0.00110 0.00304 -0.00174 AFIX 43 H3 2 0.624770 -0.031758 0.610594 11.00000 -1.20000 AFIX 0 N4 3 0.588604 0.124139 0.692634 11.00000 0.02517 0.03128 = 0.02268 0.00262 0.00192 0.00237 C5 1 0.640133 0.182320 0.750080 11.00000 0.02130 0.02646 = 0.02304 -0.00023 0.00411 0.00133 AFIX 43 H5 2 0.592240 0.266659 0.779972 11.00000 -1.20000 AFIX 0 C6 1 0.761014 0.123775 0.767491 11.00000 0.02026 0.02291 = 0.02219 0.00123 0.00268 -0.00207 N7 3 0.809330 0.186452 0.829430 11.00000 0.01828 0.02815 = 0.02172 -0.00155 0.00186 -0.00115 N8 3 0.921962 0.328957 0.841734 11.00000 0.02038 0.03496 = 0.03153 -0.00275 -0.00037 -0.00590 N9 3 0.949047 0.350520 0.901031 11.00000 0.02640 0.03126 = 0.02845 -0.00203 -0.00182 -0.00219 C10 1 0.853586 0.219882 0.929107 11.00000 0.02104 0.02354 = 0.02718 -0.00202 0.00070 -0.00078 C11 1 0.840302 0.184969 0.991394 11.00000 0.03081 0.02262 = 0.02783 -0.00163 -0.00306 0.00380 AFIX 43 H11 2 0.900784 0.259639 1.022512 11.00000 -1.20000 AFIX 0 C12 1 0.734838 0.036480 1.005409 11.00000 0.03843 0.02664 = 0.02233 0.00053 0.00404 0.00194 AFIX 43 H12 2 0.722367 0.007979 1.047255 11.00000 -1.20000 AFIX 0 C13 1 0.645211 -0.073893 0.959222 11.00000 0.02767 0.02663 = 0.02856 0.00008 0.00677 0.00028 AFIX 43 H13 2 0.574017 -0.174862 0.970987 11.00000 -1.20000 AFIX 0 C14 1 0.656948 -0.040878 0.897629 11.00000 0.02303 0.02682 = 0.02487 -0.00082 0.00400 -0.00061 AFIX 43 H14 2 0.596453 -0.117614 0.866683 11.00000 -1.20000 AFIX 0 C15 1 0.763500 0.112696 0.883453 11.00000 0.02069 0.02264 = 0.02004 -0.00199 0.00244 0.00198 HKLF 4 REM import in P 21/c REM R1 = 0.0533 for 1241 Fo > 4sig(Fo) and 0.0999 for all 2081 data REM 137 parameters refined using 0 restraints END WGHT 0.0516 0.0000 REM Highest difference peak 0.24, deepest hole -0.21, 1-sigma level 0.06 Q1 1 0.8018 0.1448 0.9116 11.00000 0.05 0.24 Q2 1 0.7950 0.3232 1.0719 11.00000 0.05 0.23 Q3 1 0.7068 0.1768 0.7589 11.00000 0.05 0.23 Q4 1 1.0107 0.2571 0.9525 11.00000 0.05 0.21 Q5 1 0.5812 -0.1028 0.7772 11.00000 0.05 0.20 Q6 1 0.8251 -0.0773 0.5636 11.00000 0.05 0.20 Q7 1 0.4323 -0.1717 0.9793 11.00000 0.05 0.19 Q8 1 0.7219 -0.3699 0.9608 11.00000 0.05 0.19 Q9 1 0.7824 0.1228 0.7966 11.00000 0.05 0.19 Q10 1 0.6803 -0.1879 0.9979 11.00000 0.05 0.19 Q11 1 0.7639 -0.2340 0.9100 11.00000 0.05 0.19 Q12 1 0.5860 0.3841 0.7725 11.00000 0.05 0.19 Q13 1 0.8628 -0.0437 0.6103 11.00000 0.05 0.18 Q14 1 0.8749 0.1250 1.0621 11.00000 0.05 0.18 Q15 1 1.0569 0.2994 0.9135 11.00000 0.05 0.18 Q16 1 0.8617 0.0910 0.9543 11.00000 0.05 0.18 Q17 1 0.6995 0.1321 0.8881 11.00000 0.05 0.17 Q18 1 0.5158 -0.2639 0.9719 11.00000 0.05 0.17 Q19 1 1.0202 0.4736 0.9385 11.00000 0.05 0.17 Q20 1 0.7067 -0.2629 0.7746 11.00000 0.05 0.17 ; #----------------------------------------------------------------------------# # 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' 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 0.83350(18) 0.0105(6) 0.72436(10) 0.0246(5) Uani 1 1 d . . . H1 H 0.9164 -0.0284 0.7353 0.029 Uiso 1 1 calc R . . C2 C 0.78145(18) -0.0444(6) 0.66475(10) 0.0282(6) Uani 1 1 d . . . H2 H 0.8281 -0.119 0.6337 0.034 Uiso 1 1 calc R . . C3 C 0.65989(18) 0.0118(6) 0.65140(10) 0.0273(6) Uani 1 1 d . . . H3 H 0.6248 -0.0318 0.6106 0.033 Uiso 1 1 calc R . . N4 N 0.58860(14) 0.1241(5) 0.69263(8) 0.0264(5) Uani 1 1 d . . . C5 C 0.64013(17) 0.1823(6) 0.75008(9) 0.0235(5) Uani 1 1 d . . . H5 H 0.5922 0.2667 0.78 0.028 Uiso 1 1 calc R . . C6 C 0.76101(17) 0.1238(6) 0.76749(9) 0.0218(5) Uani 1 1 d . . . N7 N 0.80933(14) 0.1865(5) 0.82943(8) 0.0227(5) Uani 1 1 d . . . N8 N 0.92196(14) 0.3290(5) 0.84173(8) 0.0292(5) Uani 1 1 d . . . N9 N 0.94905(15) 0.3505(5) 0.90103(8) 0.0291(5) Uani 1 1 d . . . C10 C 0.85359(17) 0.2199(6) 0.92911(10) 0.0241(5) Uani 1 1 d . . . C11 C 0.84030(19) 0.1850(6) 0.99139(10) 0.0276(6) Uani 1 1 d . . . H11 H 0.9008 0.2596 1.0225 0.033 Uiso 1 1 calc R . . C12 C 0.73484(19) 0.0365(6) 1.00541(10) 0.0291(6) Uani 1 1 d . . . H12 H 0.7224 0.008 1.0473 0.035 Uiso 1 1 calc R . . C13 C 0.64521(19) -0.0739(6) 0.95922(10) 0.0273(6) Uani 1 1 d . . . H13 H 0.574 -0.1749 0.971 0.033 Uiso 1 1 calc R . . C14 C 0.65695(17) -0.0409(6) 0.89763(10) 0.0248(5) Uani 1 1 d . . . H14 H 0.5965 -0.1176 0.8667 0.03 Uiso 1 1 calc R . . C15 C 0.76350(17) 0.1127(6) 0.88345(9) 0.0211(5) 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 0.0196(10) 0.0252(14) 0.0291(13) -0.0018(10) 0.0042(9) 0.0005(9) C2 0.0291(12) 0.0321(15) 0.0242(13) -0.0007(10) 0.0063(9) -0.0007(10) C3 0.0304(12) 0.0292(15) 0.0223(12) 0.0011(10) 0.0030(9) -0.0017(10) N4 0.0252(10) 0.0313(12) 0.0227(10) 0.0026(9) 0.0019(7) 0.0024(8) C5 0.0213(11) 0.0265(14) 0.0230(12) -0.0002(10) 0.0041(8) 0.0013(9) C6 0.0203(10) 0.0229(13) 0.0222(12) 0.0012(9) 0.0027(8) -0.0021(9) N7 0.0183(9) 0.0281(12) 0.0217(10) -0.0016(8) 0.0019(7) -0.0012(8) N8 0.0204(9) 0.0350(13) 0.0315(12) -0.0027(9) -0.0004(8) -0.0059(8) N9 0.0264(10) 0.0313(12) 0.0285(11) -0.0020(9) -0.0018(8) -0.0022(9) C10 0.0210(10) 0.0235(13) 0.0272(13) -0.0020(10) 0.0007(9) -0.0008(9) C11 0.0308(12) 0.0226(14) 0.0278(13) -0.0016(10) -0.0031(9) 0.0038(10) C12 0.0384(13) 0.0266(15) 0.0223(12) 0.0005(10) 0.0040(9) 0.0019(11) C13 0.0277(12) 0.0266(14) 0.0286(13) 0.0001(10) 0.0068(9) 0.0003(10) C14 0.0230(11) 0.0268(14) 0.0249(12) -0.0008(10) 0.0040(9) -0.0006(10) C15 0.0207(10) 0.0226(13) 0.0200(12) -0.0020(9) 0.0024(8) 0.0020(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.385(3) . ? C1 C6 1.386(3) . ? C1 H1 0.95 . ? C2 C3 1.386(3) . ? C2 H2 0.95 . ? C3 N4 1.345(3) . ? C3 H3 0.95 . ? N4 C5 1.343(2) . ? C5 C6 1.392(3) . ? C5 H5 0.95 . ? C6 N7 1.423(3) . ? N7 C15 1.374(3) . ? N7 N8 1.376(2) . ? N8 N9 1.303(2) . ? N9 C10 1.390(3) . ? C10 C11 1.397(3) . ? C10 C15 1.401(3) . ? C11 C12 1.380(3) . ? C11 H11 0.95 . ? C12 C13 1.409(3) . ? C12 H12 0.95 . ? C13 C14 1.377(3) . ? C13 H13 0.95 . ? C14 C15 1.400(3) . ? C14 H14 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 C2 C1 C6 117.97(19) . . ? C2 C1 H1 121 . . ? C6 C1 H1 121 . . ? C1 C2 C3 118.6(2) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? N4 C3 C2 124.1(2) . . ? N4 C3 H3 118 . . ? C2 C3 H3 118 . . ? C5 N4 C3 116.91(18) . . ? N4 C5 C6 122.5(2) . . ? N4 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C1 C6 C5 119.89(19) . . ? C1 C6 N7 120.62(18) . . ? C5 C6 N7 119.48(19) . . ? C15 N7 N8 109.85(16) . . ? C15 N7 C6 130.43(17) . . ? N8 N7 C6 119.65(17) . . ? N9 N8 N7 108.97(17) . . ? N8 N9 C10 108.37(16) . . ? N9 C10 C11 129.91(19) . . ? N9 C10 C15 108.68(19) . . ? C11 C10 C15 121.4(2) . . ? C12 C11 C10 116.59(19) . . ? C12 C11 H11 121.7 . . ? C10 C11 H11 121.7 . . ? C11 C12 C13 121.6(2) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C14 C13 C12 122.4(2) . . ? C14 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C13 C14 C15 115.87(19) . . ? C13 C14 H14 122.1 . . ? C15 C14 H14 122.1 . . ? N7 C15 C14 133.80(18) . . ? N7 C15 C10 104.14(18) . . ? C14 C15 C10 122.0(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 C6 C1 C2 C3 -0.8(3) . . . . ? C1 C2 C3 N4 1.4(3) . . . . ? C2 C3 N4 C5 -0.3(3) . . . . ? C3 N4 C5 C6 -1.3(3) . . . . ? C2 C1 C6 C5 -0.7(3) . . . . ? C2 C1 C6 N7 -179.7(2) . . . . ? N4 C5 C6 C1 1.8(3) . . . . ? N4 C5 C6 N7 -179.1(2) . . . . ? C1 C6 N7 C15 -140.7(2) . . . . ? C5 C6 N7 C15 40.2(3) . . . . ? C1 C6 N7 N8 36.0(3) . . . . ? C5 C6 N7 N8 -143.1(2) . . . . ? C15 N7 N8 N9 -0.4(2) . . . . ? C6 N7 N8 N9 -177.72(18) . . . . ? N7 N8 N9 C10 0.2(2) . . . . ? N8 N9 C10 C11 179.4(2) . . . . ? N8 N9 C10 C15 0.1(3) . . . . ? N9 C10 C11 C12 -178.6(2) . . . . ? C15 C10 C11 C12 0.7(3) . . . . ? C10 C11 C12 C13 0.0(3) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? C12 C13 C14 C15 -0.5(3) . . . . ? N8 N7 C15 C14 -177.7(2) . . . . ? C6 N7 C15 C14 -0.7(4) . . . . ? N8 N7 C15 C10 0.4(2) . . . . ? C6 N7 C15 C10 177.4(2) . . . . ? C13 C14 C15 N7 179.0(2) . . . . ? C13 C14 C15 C10 1.2(3) . . . . ? N9 C10 C15 N7 -0.3(2) . . . . ? C11 C10 C15 N7 -179.7(2) . . . . ? N9 C10 C15 C14 178.1(2) . . . . ? C11 C10 C15 C14 -1.3(3) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962368' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2g _audit_creation_date 2012-10-09T18:43:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H8 N2 S' _chemical_formula_sum 'C11 H8 N2 S' _chemical_formula_weight 200.25 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.4535(5) _cell_length_b 7.2728(5) _cell_length_c 10.4085(6) _cell_angle_alpha 90 _cell_angle_beta 105.814(3) _cell_angle_gamma 90 _cell_volume 470.03(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1087 _cell_measurement_theta_min 3.28 _cell_measurement_theta_max 25.27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description board _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.847 _exptl_absorpt_correction_T_max 0.982 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_unetI/netI 0.055 _diffrn_reflns_number 3017 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 1885 _reflns_number_gt 1683 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0342P)^2^+0.1159P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 1885 _refine_ls_number_parameters 127 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.0893 _refine_ls_wR_factor_gt 0.0857 _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_restrained_S_all 1.03 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(10) _refine_diff_density_max 0.264 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.051 _iucr_refine_instructions_details ; .res file for SHELXL : job.res ................................................................. TITL import in P 21 CELL 0.71073 6.4535 7.2728 10.4085 90.000 105.814 90.000 ZERR 2.00 0.0005 0.0005 0.0006 0.000 0.003 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N S UNIT 22 16 4 2 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.034200 0.115900 FVAR 1.67393 S1 4 0.941598 0.513118 0.423628 11.00000 0.03086 0.03307 = 0.03016 -0.00739 0.00903 0.00227 C1 1 1.209638 0.506582 0.511720 11.00000 0.03923 0.03511 = 0.02038 0.00023 -0.00067 -0.00933 AFIX 43 H1 2 1.267144 0.565921 0.595156 11.00000 -1.20000 AFIX 0 C2 1 1.327360 0.407853 0.448564 11.00000 0.02268 0.03649 = 0.02612 0.00521 -0.00126 -0.00474 AFIX 43 H2 2 1.478730 0.392459 0.481926 11.00000 -1.20000 AFIX 0 C3 1 1.203960 0.328276 0.326747 11.00000 0.02010 0.02917 = 0.02220 0.00022 0.00456 0.00306 AFIX 43 H3 2 1.262030 0.252396 0.270838 11.00000 -1.20000 AFIX 0 C4 1 0.993148 0.374497 0.300659 11.00000 0.02394 0.02167 = 0.02001 -0.00193 0.00553 -0.00453 N5 3 0.827456 0.329327 0.186578 11.00000 0.01882 0.02427 = 0.02381 -0.00141 0.00491 -0.00308 C6 1 0.833653 0.333853 0.054785 11.00000 0.01868 0.01778 = 0.02311 -0.00197 0.00165 0.00434 C7 1 0.994023 0.396479 -0.001952 11.00000 0.02453 0.02019 = 0.02627 0.00351 0.00449 0.00105 AFIX 43 H7 2 1.125311 0.447207 0.050891 11.00000 -1.20000 AFIX 0 C8 1 0.951258 0.380605 -0.137903 11.00000 0.03794 0.02748 = 0.02919 0.00419 0.01021 0.00397 AFIX 43 H8 2 1.056436 0.420859 -0.180153 11.00000 -1.20000 AFIX 0 C9 1 0.756334 0.306509 -0.217061 11.00000 0.04649 0.03045 = 0.02059 -0.00193 0.00051 0.01008 AFIX 43 H9 2 0.733726 0.296615 -0.310885 11.00000 -1.20000 AFIX 0 C10 1 0.599241 0.248637 -0.160836 11.00000 0.02911 0.02776 = 0.03075 -0.00702 -0.00869 0.00662 AFIX 43 H10 2 0.467258 0.200598 -0.214831 11.00000 -1.20000 AFIX 0 C11 1 0.636978 0.261658 -0.021145 11.00000 0.02350 0.01652 = 0.03027 -0.00122 -0.00060 0.00320 C12 1 0.523106 0.217927 0.074310 11.00000 0.01237 0.02488 = 0.04255 -0.00104 0.00104 0.00045 AFIX 43 H12 2 0.382661 0.166159 0.052126 11.00000 -1.20000 AFIX 0 N13 3 0.635928 0.257878 0.197654 11.00000 0.01615 0.02853 = 0.03543 -0.00319 0.00703 -0.00193 HKLF 4 REM import in P 21 REM R1 = 0.0414 for 1683 Fo > 4sig(Fo) and 0.0481 for all 1885 data REM 127 parameters refined using 1 restraints END WGHT 0.0329 0.1268 REM Highest difference peak 0.264, deepest hole -0.241, 1-sigma level 0.051 Q1 1 1.0955 0.5083 0.4758 11.00000 0.05 0.26 Q2 1 0.8548 0.5139 0.5074 11.00000 0.05 0.20 Q3 1 0.5473 0.3202 0.0228 11.00000 0.05 0.19 Q4 1 0.8015 0.2737 -0.3179 11.00000 0.05 0.18 Q5 1 0.9500 0.4689 0.3418 11.00000 0.05 0.17 Q6 1 1.1360 0.5332 0.6078 11.00000 0.05 0.17 Q7 1 1.2374 0.4212 0.4827 11.00000 0.05 0.17 Q8 1 0.6347 0.3786 -0.2125 11.00000 0.05 0.16 Q9 1 0.8237 0.4348 0.2474 11.00000 0.05 0.16 Q10 1 0.9738 0.1628 -0.1262 11.00000 0.05 0.16 Q11 1 1.5757 0.2022 0.4950 11.00000 0.05 0.16 Q12 1 0.9847 0.6268 0.3740 11.00000 0.05 0.16 Q13 1 0.7982 0.4913 0.4221 11.00000 0.05 0.16 Q14 1 0.9475 0.5997 0.0147 11.00000 0.05 0.16 Q15 1 0.9291 0.3856 0.4782 11.00000 0.05 0.15 Q16 1 1.2527 0.4363 0.3569 11.00000 0.05 0.15 Q17 1 1.1673 0.5270 0.2002 11.00000 0.05 0.15 Q18 1 1.1303 0.3835 0.5858 11.00000 0.05 0.15 Q19 1 1.2680 0.4186 0.6713 11.00000 0.05 0.15 Q20 1 0.8210 0.3501 0.1332 11.00000 0.05 0.15 ; #----------------------------------------------------------------------------# # 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' S S 0.1246 0.1234 '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 S1 S 0.94160(11) 0.51312(11) 0.42363(6) 0.03122(19) Uani 1 1 d . . . C1 C 1.2096(4) 0.5066(5) 0.5117(2) 0.0333(6) Uani 1 1 d . . . H1 H 1.2671 0.5659 0.5952 0.04 Uiso 1 1 calc R . . C2 C 1.3274(4) 0.4079(4) 0.4486(3) 0.0300(6) Uani 1 1 d . . . H2 H 1.4787 0.3925 0.4819 0.036 Uiso 1 1 calc R . . C3 C 1.2040(4) 0.3283(4) 0.3267(2) 0.0241(6) Uani 1 1 d . . . H3 H 1.262 0.2524 0.2708 0.029 Uiso 1 1 calc R . . C4 C 0.9931(4) 0.3745(4) 0.3007(2) 0.0220(6) Uani 1 1 d . . . N5 N 0.8275(3) 0.3293(3) 0.1866(2) 0.0225(5) Uani 1 1 d . . . C6 C 0.8337(4) 0.3339(4) 0.0548(2) 0.0206(5) Uani 1 1 d . . . C7 C 0.9940(4) 0.3965(4) -0.0020(3) 0.0241(6) Uani 1 1 d . . . H7 H 1.1253 0.4472 0.0509 0.029 Uiso 1 1 calc R . . C8 C 0.9513(5) 0.3806(4) -0.1379(3) 0.0313(7) Uani 1 1 d . . . H8 H 1.0564 0.4209 -0.1802 0.038 Uiso 1 1 calc R . . C9 C 0.7563(5) 0.3065(4) -0.2171(3) 0.0342(7) Uani 1 1 d . . . H9 H 0.7337 0.2966 -0.3109 0.041 Uiso 1 1 calc R . . C10 C 0.5992(5) 0.2486(4) -0.1608(3) 0.0325(7) Uani 1 1 d . . . H10 H 0.4673 0.2006 -0.2148 0.039 Uiso 1 1 calc R . . C11 C 0.6370(4) 0.2617(4) -0.0211(3) 0.0250(6) Uani 1 1 d . . . C12 C 0.5231(4) 0.2179(4) 0.0743(3) 0.0279(6) Uani 1 1 d . . . H12 H 0.3827 0.1662 0.0521 0.033 Uiso 1 1 calc R . . N13 N 0.6359(3) 0.2579(3) 0.1977(2) 0.0267(5) 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 S1 0.0309(4) 0.0331(4) 0.0302(3) -0.0074(3) 0.0090(3) 0.0023(3) C1 0.0392(16) 0.0351(17) 0.0204(12) 0.0002(15) -0.0007(10) -0.0093(17) C2 0.0227(14) 0.0365(18) 0.0261(13) 0.0052(13) -0.0013(11) -0.0047(12) C3 0.0201(13) 0.0292(15) 0.0222(12) 0.0002(12) 0.0046(10) 0.0031(11) C4 0.0239(13) 0.0217(15) 0.0200(12) -0.0019(10) 0.0055(10) -0.0045(11) N5 0.0188(11) 0.0243(12) 0.0238(10) -0.0014(10) 0.0049(8) -0.0031(9) C6 0.0187(12) 0.0178(13) 0.0231(12) -0.0020(11) 0.0017(9) 0.0043(10) C7 0.0245(13) 0.0202(14) 0.0263(13) 0.0035(11) 0.0045(11) 0.0011(11) C8 0.0379(17) 0.0275(17) 0.0292(14) 0.0042(13) 0.0102(12) 0.0040(13) C9 0.0465(19) 0.0304(18) 0.0206(13) -0.0019(12) 0.0005(13) 0.0101(14) C10 0.0291(15) 0.0278(17) 0.0307(15) -0.0070(12) -0.0087(11) 0.0066(12) C11 0.0235(14) 0.0165(13) 0.0303(14) -0.0012(11) -0.0006(11) 0.0032(11) C12 0.0124(12) 0.0249(16) 0.0426(16) -0.0010(12) 0.0010(11) 0.0005(10) N13 0.0161(11) 0.0285(13) 0.0354(13) -0.0032(10) 0.0070(9) -0.0019(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.724(3) . ? S1 C4 1.731(3) . ? C1 C2 1.341(4) . ? C1 H1 0.95 . ? C2 C3 1.424(4) . ? C2 H2 0.95 . ? C3 C4 1.355(4) . ? C3 H3 0.95 . ? C4 N5 1.403(3) . ? N5 N13 1.374(3) . ? N5 C6 1.384(3) . ? C6 C7 1.400(4) . ? C6 C11 1.402(4) . ? C7 C8 1.371(4) . ? C7 H7 0.95 . ? C8 C9 1.410(4) . ? C8 H8 0.95 . ? C9 C10 1.368(4) . ? C9 H9 0.95 . ? C10 C11 1.410(4) . ? C10 H10 0.95 . ? C11 C12 1.423(4) . ? C12 N13 1.324(4) . ? 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 C1 S1 C4 90.58(14) . . ? C2 C1 S1 112.0(2) . . ? C2 C1 H1 124 . . ? S1 C1 H1 124 . . ? C1 C2 C3 113.6(2) . . ? C1 C2 H2 123.2 . . ? C3 C2 H2 123.2 . . ? C4 C3 C2 111.4(2) . . ? C4 C3 H3 124.3 . . ? C2 C3 H3 124.3 . . ? C3 C4 N5 127.1(2) . . ? C3 C4 S1 112.40(19) . . ? N5 C4 S1 120.41(19) . . ? N13 N5 C6 111.2(2) . . ? N13 N5 C4 120.9(2) . . ? C6 N5 C4 127.7(2) . . ? N5 C6 C7 130.6(2) . . ? N5 C6 C11 106.5(2) . . ? C7 C6 C11 122.9(2) . . ? C8 C7 C6 116.4(3) . . ? C8 C7 H7 121.8 . . ? C6 C7 H7 121.8 . . ? C7 C8 C9 122.2(3) . . ? C7 C8 H8 118.9 . . ? C9 C8 H8 118.9 . . ? C10 C9 C8 121.0(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 118.7(3) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C6 C11 C10 118.8(2) . . ? C6 C11 C12 104.5(2) . . ? C10 C11 C12 136.7(3) . . ? N13 C12 C11 112.1(2) . . ? N13 C12 H12 124 . . ? C11 C12 H12 124 . . ? C12 N13 N5 105.7(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 C4 S1 C1 C2 1.1(3) . . . . ? S1 C1 C2 C3 -1.6(4) . . . . ? C1 C2 C3 C4 1.3(4) . . . . ? C2 C3 C4 N5 176.3(2) . . . . ? C2 C3 C4 S1 -0.4(3) . . . . ? C1 S1 C4 C3 -0.4(2) . . . . ? C1 S1 C4 N5 -177.4(2) . . . . ? C3 C4 N5 N13 131.8(3) . . . . ? S1 C4 N5 N13 -51.6(3) . . . . ? C3 C4 N5 C6 -42.7(4) . . . . ? S1 C4 N5 C6 133.9(2) . . . . ? N13 N5 C6 C7 179.3(3) . . . . ? C4 N5 C6 C7 -5.7(5) . . . . ? N13 N5 C6 C11 -0.1(3) . . . . ? C4 N5 C6 C11 174.9(2) . . . . ? N5 C6 C7 C8 179.5(3) . . . . ? C11 C6 C7 C8 -1.2(4) . . . . ? C6 C7 C8 C9 0.4(4) . . . . ? C7 C8 C9 C10 0.7(5) . . . . ? C8 C9 C10 C11 -1.0(5) . . . . ? N5 C6 C11 C10 -179.6(2) . . . . ? C7 C6 C11 C10 1.0(4) . . . . ? N5 C6 C11 C12 0.1(3) . . . . ? C7 C6 C11 C12 -179.3(3) . . . . ? C9 C10 C11 C6 0.2(4) . . . . ? C9 C10 C11 C12 -179.4(3) . . . . ? C6 C11 C12 N13 -0.1(3) . . . . ? C10 C11 C12 N13 179.5(3) . . . . ? C11 C12 N13 N5 0.1(3) . . . . ? C6 N5 N13 C12 0.0(3) . . . . ? C4 N5 N13 C12 -175.4(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962369' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3b _audit_creation_date 2012-05-23T15:26:26-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H8 I N3' _chemical_formula_sum 'C12 H8 I N3' _chemical_formula_weight 321.11 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.00450(10) _cell_length_b 15.6507(3) _cell_length_c 9.0232(2) _cell_angle_alpha 90 _cell_angle_beta 100.4390(10) _cell_angle_gamma 90 _cell_volume 1111.68(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4753 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 27.45 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_diffrn 1.919 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.854 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.611 _exptl_absorpt_correction_T_max 0.731 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_unetI/netI 0.0291 _diffrn_reflns_number 10038 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 2544 _reflns_number_gt 2303 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0189P)^2^+0.8137P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 2544 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0247 _refine_ls_R_factor_gt 0.0215 _refine_ls_wR_factor_ref 0.0522 _refine_ls_wR_factor_gt 0.0507 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.588 _refine_diff_density_min -0.649 _refine_diff_density_rms 0.08 _iucr_refine_instructions_details ; .res file for SHELXL : job.res ................................................................. TITL import in P 21/c CELL 0.71073 8.0045 15.6507 9.0232 90.000 100.439 90.000 ZERR 4.00 0.0001 0.0003 0.0002 0.000 0.001 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N I UNIT 48 32 12 4 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.018900 0.813700 FVAR 0.37415 I1 4 -0.038694 -0.235654 -0.125038 11.00000 0.02647 0.02600 = 0.03071 -0.00854 0.00425 -0.00382 C1 1 -0.026810 -0.140830 0.039215 11.00000 0.02184 0.01920 = 0.01879 0.00335 0.00234 -0.00068 C2 1 -0.168695 -0.114467 0.092614 11.00000 0.01584 0.02437 = 0.02291 0.00642 0.00286 -0.00200 AFIX 43 H2 2 -0.274470 -0.141984 0.058550 11.00000 -1.20000 AFIX 0 C3 1 -0.158761 -0.046734 0.197842 11.00000 0.01740 0.02476 = 0.02278 0.00661 0.00769 0.00393 AFIX 43 H3 2 -0.259182 -0.029624 0.231988 11.00000 -1.20000 AFIX 0 C4 1 -0.009285 -0.004714 0.252591 11.00000 0.01980 0.02031 = 0.01993 0.00252 0.00599 0.00354 AFIX 43 H4 2 -0.004032 0.040834 0.322877 11.00000 -1.20000 AFIX 0 C5 1 0.135056 -0.033032 0.198595 11.00000 0.01485 0.01743 = 0.01658 0.00306 0.00293 0.00073 C6 1 0.127109 -0.099439 0.093778 11.00000 0.01747 0.02005 = 0.01679 0.00292 0.00473 0.00219 N7 3 0.285533 -0.110601 0.056993 11.00000 0.01811 0.02084 = 0.02185 0.00077 0.00450 0.00176 N8 3 0.387983 -0.055011 0.132795 11.00000 0.01868 0.02215 = 0.02134 -0.00132 0.00637 0.00292 N9 3 0.300761 -0.007013 0.219634 11.00000 0.01454 0.01978 = 0.01988 -0.00062 0.00631 0.00151 C10 1 0.384771 0.060342 0.309364 11.00000 0.01458 0.01971 = 0.01934 0.00193 0.00172 0.00315 C11 1 0.346340 0.076663 0.450818 11.00000 0.01795 0.02417 = 0.02155 0.00208 0.00625 0.00000 AFIX 43 H11 2 0.264270 0.042907 0.487929 11.00000 -1.20000 AFIX 0 C12 1 0.428414 0.142369 0.537083 11.00000 0.02545 0.02697 = 0.01975 -0.00163 0.00448 0.00370 AFIX 43 H12 2 0.401157 0.154442 0.633105 11.00000 -1.20000 AFIX 0 C13 1 0.550410 0.190794 0.484183 11.00000 0.02790 0.02511 = 0.02799 -0.00367 0.00149 -0.00426 AFIX 43 H13 2 0.606106 0.236139 0.543512 11.00000 -1.20000 AFIX 0 C14 1 0.590965 0.172652 0.343590 11.00000 0.02544 0.02832 = 0.02929 0.00101 0.00709 -0.00902 AFIX 43 H14 2 0.676664 0.204774 0.308472 11.00000 -1.20000 AFIX 0 C15 1 0.506965 0.108005 0.254710 11.00000 0.02006 0.02519 = 0.02038 0.00218 0.00643 0.00119 AFIX 43 H15 2 0.532582 0.096479 0.157904 11.00000 -1.20000 HKLF 4 REM import in P 21/c REM R1 = 0.0215 for 2303 Fo > 4sig(Fo) and 0.0247 for all 2544 data REM 145 parameters refined using 0 restraints END WGHT 0.0175 0.8364 REM Highest difference peak 0.59, deepest hole -0.65, 1-sigma level 0.08 Q1 1 -0.0242 -0.2725 -0.0657 11.00000 0.05 0.59 Q2 1 -0.0829 -0.0344 0.2390 11.00000 0.05 0.36 Q3 1 0.3980 0.0647 0.3875 11.00000 0.05 0.35 Q4 1 0.2030 -0.1017 0.0527 11.00000 0.05 0.32 Q5 1 0.0923 -0.0253 0.2586 11.00000 0.05 0.32 Q6 1 0.2203 -0.0167 0.2229 11.00000 0.05 0.32 Q7 1 0.2732 -0.1385 -0.0242 11.00000 0.05 0.31 Q8 1 -0.0967 -0.1359 0.0862 11.00000 0.05 0.31 Q9 1 0.0533 -0.1273 0.0876 11.00000 0.05 0.30 Q10 1 -0.0369 -0.1955 -0.0453 11.00000 0.05 0.30 Q11 1 0.4190 0.0902 0.2685 11.00000 0.05 0.30 Q12 1 0.4744 0.1677 0.4894 11.00000 0.05 0.28 Q13 1 -0.1550 -0.0908 0.1650 11.00000 0.05 0.28 Q14 1 0.3433 -0.0290 0.1736 11.00000 0.05 0.27 Q15 1 0.1172 -0.1891 0.1631 11.00000 0.05 0.27 Q16 1 0.3588 0.0842 0.3636 11.00000 0.05 0.27 Q17 1 0.5712 0.1694 0.4276 11.00000 0.05 0.27 Q18 1 0.2393 -0.1962 0.1229 11.00000 0.05 0.26 Q19 1 -0.0010 -0.2362 0.1668 11.00000 0.05 0.26 Q20 1 -0.2265 -0.1310 0.0849 11.00000 0.05 0.26 ; #----------------------------------------------------------------------------# # 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' 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 -0.03869(2) -0.235654(11) -0.125038(18) 0.02784(7) Uani 1 1 d . . . C1 C -0.0268(3) -0.14083(15) 0.0392(2) 0.0201(5) Uani 1 1 d . . . C2 C -0.1687(3) -0.11447(15) 0.0926(2) 0.0211(5) Uani 1 1 d . . . H2 H -0.2745 -0.142 0.0585 0.025 Uiso 1 1 calc R . . C3 C -0.1588(3) -0.04673(15) 0.1978(2) 0.0211(5) Uani 1 1 d . . . H3 H -0.2592 -0.0296 0.232 0.025 Uiso 1 1 calc R . . C4 C -0.0093(3) -0.00471(14) 0.2526(2) 0.0197(5) Uani 1 1 d . . . H4 H -0.004 0.0408 0.3229 0.024 Uiso 1 1 calc R . . C5 C 0.1351(3) -0.03303(14) 0.1986(2) 0.0163(4) Uani 1 1 d . . . C6 C 0.1271(3) -0.09944(14) 0.0938(2) 0.0179(4) Uani 1 1 d . . . N7 N 0.2855(2) -0.11060(12) 0.0570(2) 0.0202(4) Uani 1 1 d . . . N8 N 0.3880(2) -0.05501(12) 0.1328(2) 0.0204(4) Uani 1 1 d . . . N9 N 0.3008(2) -0.00701(12) 0.2196(2) 0.0177(4) Uani 1 1 d . . . C10 C 0.3848(3) 0.06034(14) 0.3094(2) 0.0180(4) Uani 1 1 d . . . C11 C 0.3463(3) 0.07666(15) 0.4508(2) 0.0209(5) Uani 1 1 d . . . H11 H 0.2643 0.0429 0.4879 0.025 Uiso 1 1 calc R . . C12 C 0.4284(3) 0.14237(16) 0.5371(2) 0.0240(5) Uani 1 1 d . . . H12 H 0.4012 0.1544 0.6331 0.029 Uiso 1 1 calc R . . C13 C 0.5504(3) 0.19079(16) 0.4842(3) 0.0274(5) Uani 1 1 d . . . H13 H 0.6061 0.2361 0.5435 0.033 Uiso 1 1 calc R . . C14 C 0.5910(3) 0.17265(16) 0.3436(3) 0.0274(5) Uani 1 1 d . . . H14 H 0.6767 0.2048 0.3085 0.033 Uiso 1 1 calc R . . C15 C 0.5070(3) 0.10801(15) 0.2547(2) 0.0215(5) Uani 1 1 d . . . H15 H 0.5326 0.0965 0.1579 0.026 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 I1 0.02647(11) 0.02600(10) 0.03071(10) -0.00854(6) 0.00425(7) -0.00382(6) C1 0.0218(12) 0.0192(11) 0.0188(10) 0.0034(8) 0.0023(8) -0.0007(9) C2 0.0158(11) 0.0244(12) 0.0229(10) 0.0064(9) 0.0029(8) -0.0020(9) C3 0.0174(11) 0.0248(12) 0.0228(11) 0.0066(9) 0.0077(8) 0.0039(9) C4 0.0198(11) 0.0203(12) 0.0199(10) 0.0025(9) 0.0060(9) 0.0035(9) C5 0.0148(10) 0.0174(11) 0.0166(10) 0.0031(8) 0.0029(8) 0.0007(8) C6 0.0175(11) 0.0201(11) 0.0168(10) 0.0029(8) 0.0047(8) 0.0022(9) N7 0.0181(9) 0.0208(10) 0.0218(9) 0.0008(7) 0.0045(7) 0.0018(8) N8 0.0187(10) 0.0222(10) 0.0213(9) -0.0013(8) 0.0064(7) 0.0029(8) N9 0.0145(9) 0.0198(10) 0.0199(9) -0.0006(7) 0.0063(7) 0.0015(7) C10 0.0146(10) 0.0197(11) 0.0193(10) 0.0019(8) 0.0017(8) 0.0032(8) C11 0.0180(11) 0.0242(12) 0.0216(11) 0.0021(9) 0.0063(8) 0.0000(9) C12 0.0254(12) 0.0270(13) 0.0197(10) -0.0016(9) 0.0045(9) 0.0037(10) C13 0.0279(13) 0.0251(13) 0.0280(12) -0.0037(10) 0.0015(10) -0.0043(10) C14 0.0254(13) 0.0283(13) 0.0293(12) 0.0010(10) 0.0071(10) -0.0090(10) C15 0.0201(11) 0.0252(12) 0.0204(10) 0.0022(9) 0.0064(8) 0.0012(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.087(2) . ? C1 C2 1.375(3) . ? C1 C6 1.400(3) . ? C2 C3 1.416(3) . ? C2 H2 0.95 . ? C3 C4 1.376(3) . ? C3 H3 0.95 . ? C4 C5 1.405(3) . ? C4 H4 0.95 . ? C5 N9 1.367(3) . ? C5 C6 1.399(3) . ? C6 N7 1.379(3) . ? N7 N8 1.302(3) . ? N8 N9 1.365(2) . ? N9 C10 1.422(3) . ? C10 C15 1.390(3) . ? C10 C11 1.390(3) . ? C11 C12 1.382(3) . ? C11 H11 0.95 . ? C12 C13 1.387(3) . ? C12 H12 0.95 . ? C13 C14 1.394(3) . ? C13 H13 0.95 . ? C14 C15 1.387(3) . ? C14 H14 0.95 . ? C15 H15 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 C2 C1 C6 117.9(2) . . ? C2 C1 I1 121.86(17) . . ? C6 C1 I1 120.17(16) . . ? C1 C2 C3 120.7(2) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 122.6(2) . . ? C4 C3 H3 118.7 . . ? C2 C3 H3 118.7 . . ? C3 C4 C5 116.2(2) . . ? C3 C4 H4 121.9 . . ? C5 C4 H4 121.9 . . ? N9 C5 C6 103.84(18) . . ? N9 C5 C4 134.1(2) . . ? C6 C5 C4 122.0(2) . . ? N7 C6 C1 130.2(2) . . ? N7 C6 C5 109.01(19) . . ? C1 C6 C5 120.7(2) . . ? N8 N7 C6 107.95(18) . . ? N7 N8 N9 109.29(17) . . ? N8 N9 C5 109.91(17) . . ? N8 N9 C10 119.77(17) . . ? C5 N9 C10 130.29(18) . . ? C15 C10 C11 121.0(2) . . ? C15 C10 N9 119.12(19) . . ? C11 C10 N9 119.9(2) . . ? C12 C11 C10 119.5(2) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C14 119.7(2) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 120.4(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C10 119.0(2) . . ? C14 C15 H15 120.5 . . ? C10 C15 H15 120.5 . . ? 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 0.9(3) . . . . ? I1 C1 C2 C3 -176.45(16) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 N9 177.0(2) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C2 C1 C6 N7 -177.7(2) . . . . ? I1 C1 C6 N7 -0.3(3) . . . . ? C2 C1 C6 C5 -0.4(3) . . . . ? I1 C1 C6 C5 176.97(15) . . . . ? N9 C5 C6 N7 0.1(2) . . . . ? C4 C5 C6 N7 177.38(19) . . . . ? N9 C5 C6 C1 -177.67(19) . . . . ? C4 C5 C6 C1 -0.4(3) . . . . ? C1 C6 N7 N8 177.4(2) . . . . ? C5 C6 N7 N8 -0.1(2) . . . . ? C6 N7 N8 N9 0.1(2) . . . . ? N7 N8 N9 C5 0.0(2) . . . . ? N7 N8 N9 C10 -177.90(18) . . . . ? C6 C5 N9 N8 -0.1(2) . . . . ? C4 C5 N9 N8 -176.8(2) . . . . ? C6 C5 N9 C10 177.5(2) . . . . ? C4 C5 N9 C10 0.8(4) . . . . ? N8 N9 C10 C15 35.7(3) . . . . ? C5 N9 C10 C15 -141.7(2) . . . . ? N8 N9 C10 C11 -143.1(2) . . . . ? C5 N9 C10 C11 39.4(3) . . . . ? C15 C10 C11 C12 1.3(3) . . . . ? N9 C10 C11 C12 -179.9(2) . . . . ? C10 C11 C12 C13 -1.1(3) . . . . ? C11 C12 C13 C14 -0.4(4) . . . . ? C12 C13 C14 C15 1.7(4) . . . . ? C13 C14 C15 C10 -1.5(4) . . . . ? C11 C10 C15 C14 0.0(3) . . . . ? N9 C10 C15 C14 -178.8(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962370' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3b' _audit_creation_date 2012-05-23T16:23:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H8 I N3' _chemical_formula_sum 'C12 H8 I N3' _chemical_formula_weight 321.11 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.9051(6) _cell_length_b 7.5720(5) _cell_length_c 14.9735(9) _cell_angle_alpha 90 _cell_angle_beta 100.491(3) _cell_angle_gamma 90 _cell_volume 1104.26(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4619 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 27.37 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.932 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.873 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.488 _exptl_absorpt_correction_T_max 0.669 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_unetI/netI 0.0306 _diffrn_reflns_number 8834 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 2504 _reflns_number_gt 2241 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0334P)^2^+0.7735P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 2504 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0649 _refine_ls_wR_factor_gt 0.0627 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.826 _refine_diff_density_min -0.99 _refine_diff_density_rms 0.096 _iucr_refine_instructions_details ; .res file for SHELXL : job.res ................................................................. TITL import in P 21/n CELL 0.71073 9.9051 7.5720 14.9735 90.000 100.491 90.000 ZERR 4.00 0.0006 0.0005 0.0009 0.000 0.003 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N I UNIT 48 32 12 4 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.033400 0.773500 FVAR 0.36028 I1 4 0.011626 0.200920 0.601471 11.00000 0.02125 0.03887 = 0.02218 -0.00601 -0.00060 0.00510 C1 1 0.204802 0.199905 0.685785 11.00000 0.01790 0.01574 = 0.01782 -0.00110 0.00169 0.00119 C2 1 0.213619 0.227975 0.778695 11.00000 0.02229 0.02055 = 0.02080 -0.00207 0.00831 0.00023 AFIX 43 H2 2 0.132855 0.250093 0.802739 11.00000 -1.20000 AFIX 0 C3 1 0.340183 0.223558 0.835798 11.00000 0.02908 0.02240 = 0.01713 -0.00326 0.00492 -0.00135 AFIX 43 H3 2 0.345731 0.243106 0.899033 11.00000 -1.20000 AFIX 0 C4 1 0.459418 0.190855 0.801791 11.00000 0.01951 0.02500 = 0.02392 0.00063 0.00096 -0.00183 AFIX 43 H4 2 0.545750 0.187044 0.841656 11.00000 -1.20000 AFIX 0 C5 1 0.451618 0.163804 0.709265 11.00000 0.01828 0.01940 = 0.02485 0.00148 0.00780 0.00132 AFIX 43 H5 2 0.532651 0.142678 0.685364 11.00000 -1.20000 AFIX 0 C6 1 0.323820 0.167866 0.651564 11.00000 0.02514 0.01032 = 0.01768 -0.00104 0.00870 0.00008 N7 3 0.320040 0.139527 0.556279 11.00000 0.02372 0.01146 = 0.01822 -0.00095 0.00697 0.00160 N8 3 0.326316 -0.027181 0.522240 11.00000 0.02747 0.01170 = 0.02198 -0.00168 0.00794 0.00032 N9 3 0.334188 -0.015429 0.436139 11.00000 0.02384 0.01493 = 0.02216 -0.00232 0.00902 -0.00065 C10 1 0.334420 0.161084 0.413237 11.00000 0.01535 0.01506 = 0.01866 -0.00156 0.00345 0.00016 C11 1 0.324611 0.262730 0.490000 11.00000 0.01807 0.01528 = 0.01744 0.00110 0.00430 0.00222 C12 1 0.322362 0.447429 0.488882 11.00000 0.02563 0.01426 = 0.02332 -0.00470 0.00619 0.00235 AFIX 43 H12 2 0.314110 0.514553 0.541221 11.00000 -1.20000 AFIX 0 C13 1 0.332832 0.526686 0.407268 11.00000 0.02653 0.01430 = 0.03173 0.00260 0.00621 0.00257 AFIX 43 H13 2 0.331265 0.651887 0.403119 11.00000 -1.20000 AFIX 0 C14 1 0.345844 0.425653 0.329669 11.00000 0.02287 0.02253 = 0.02212 0.00661 0.00475 0.00121 AFIX 43 H14 2 0.354739 0.485199 0.275197 11.00000 -1.20000 AFIX 0 C15 1 0.345999 0.244282 0.330733 11.00000 0.02136 0.02044 = 0.01801 -0.00142 0.00493 -0.00013 AFIX 43 H15 2 0.353588 0.177701 0.278100 11.00000 -1.20000 HKLF 4 REM import in P 21/n REM R1 = 0.0257 for 2241 Fo > 4sig(Fo) and 0.0299 for all 2504 data REM 145 parameters refined using 0 restraints END WGHT 0.0326 0.8035 REM Highest difference peak 0.83, deepest hole -0.99, 1-sigma level 0.10 Q1 1 0.0943 0.1989 0.6403 11.00000 0.05 0.83 Q2 1 -0.0652 0.2028 0.5626 11.00000 0.05 0.75 Q3 1 0.0458 0.2784 0.5799 11.00000 0.05 0.65 Q4 1 0.0634 0.2065 0.5614 11.00000 0.05 0.60 Q5 1 -0.0626 0.2079 0.6447 11.00000 0.05 0.45 Q6 1 0.3870 0.1815 0.6784 11.00000 0.05 0.39 Q7 1 0.2760 0.1926 0.6750 11.00000 0.05 0.38 Q8 1 0.3485 0.1960 0.3772 11.00000 0.05 0.33 Q9 1 0.1559 0.1595 0.5534 11.00000 0.05 0.32 Q10 1 0.2187 0.1987 0.7311 11.00000 0.05 0.31 Q11 1 0.3237 0.2109 0.6447 11.00000 0.05 0.31 Q12 1 0.2792 0.2128 0.7979 11.00000 0.05 0.31 Q13 1 0.3449 0.2164 0.4532 11.00000 0.05 0.30 Q14 1 0.3873 0.2412 0.7994 11.00000 0.05 0.28 Q15 1 0.3976 0.1746 0.8142 11.00000 0.05 0.26 Q16 1 0.0911 0.3607 0.5354 11.00000 0.05 0.25 Q17 1 0.3762 0.2002 1.0048 11.00000 0.05 0.25 Q18 1 0.3517 0.4615 0.3754 11.00000 0.05 0.24 Q19 1 0.3674 -0.0593 0.3986 11.00000 0.05 0.24 Q20 1 0.4614 0.1923 0.7552 11.00000 0.05 0.24 ; #----------------------------------------------------------------------------# # 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' 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 0.011626(17) 0.20092(3) 0.601471(11) 0.02800(8) Uani 1 1 d . . . C1 C 0.2048(3) 0.1999(3) 0.68579(17) 0.0173(5) Uani 1 1 d . . . C2 C 0.2136(3) 0.2280(4) 0.77870(18) 0.0207(5) Uani 1 1 d . . . H2 H 0.1329 0.2501 0.8027 0.025 Uiso 1 1 calc R . . C3 C 0.3402(3) 0.2236(4) 0.83580(18) 0.0228(6) Uani 1 1 d . . . H3 H 0.3457 0.2431 0.899 0.027 Uiso 1 1 calc R . . C4 C 0.4594(3) 0.1909(4) 0.80179(19) 0.0232(6) Uani 1 1 d . . . H4 H 0.5458 0.187 0.8417 0.028 Uiso 1 1 calc R . . C5 C 0.4516(3) 0.1638(4) 0.70926(18) 0.0204(5) Uani 1 1 d . . . H5 H 0.5327 0.1427 0.6854 0.024 Uiso 1 1 calc R . . C6 C 0.3238(3) 0.1679(3) 0.65156(17) 0.0171(5) Uani 1 1 d . . . N7 N 0.3200(2) 0.1395(3) 0.55628(14) 0.0174(4) Uani 1 1 d . . . N8 N 0.3263(2) -0.0272(3) 0.52224(15) 0.0200(5) Uani 1 1 d . . . N9 N 0.3342(2) -0.0154(3) 0.43614(14) 0.0197(4) Uani 1 1 d . . . C10 C 0.3344(3) 0.1611(3) 0.41324(17) 0.0163(5) Uani 1 1 d . . . C11 C 0.3246(3) 0.2627(4) 0.49000(17) 0.0168(5) Uani 1 1 d . . . C12 C 0.3224(3) 0.4474(3) 0.48888(18) 0.0208(5) Uani 1 1 d . . . H12 H 0.3141 0.5146 0.5412 0.025 Uiso 1 1 calc R . . C13 C 0.3328(3) 0.5267(4) 0.40727(19) 0.0241(6) Uani 1 1 d . . . H13 H 0.3313 0.6519 0.4031 0.029 Uiso 1 1 calc R . . C14 C 0.3458(3) 0.4257(4) 0.32967(18) 0.0224(5) Uani 1 1 d . . . H14 H 0.3547 0.4852 0.2752 0.027 Uiso 1 1 calc R . . C15 C 0.3460(3) 0.2443(4) 0.33073(18) 0.0198(5) Uani 1 1 d . . . H15 H 0.3536 0.1777 0.2781 0.024 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 I1 0.02125(12) 0.03887(14) 0.02218(11) -0.00601(7) -0.00060(7) 0.00510(8) C1 0.0179(12) 0.0157(12) 0.0178(12) -0.0011(9) 0.0017(9) 0.0012(10) C2 0.0223(13) 0.0205(13) 0.0208(13) -0.0021(10) 0.0083(10) 0.0002(11) C3 0.0291(15) 0.0224(14) 0.0171(12) -0.0033(10) 0.0049(10) -0.0013(12) C4 0.0195(13) 0.0250(14) 0.0239(13) 0.0006(11) 0.0010(10) -0.0018(11) C5 0.0183(12) 0.0194(13) 0.0249(13) 0.0015(10) 0.0078(10) 0.0013(10) C6 0.0251(13) 0.0103(11) 0.0177(12) -0.0010(9) 0.0087(10) 0.0001(10) N7 0.0237(11) 0.0115(10) 0.0182(10) -0.0010(8) 0.0070(8) 0.0016(9) N8 0.0275(11) 0.0117(10) 0.0220(10) -0.0017(8) 0.0079(9) 0.0003(9) N9 0.0238(11) 0.0149(11) 0.0222(10) -0.0023(9) 0.0090(9) -0.0007(9) C10 0.0153(12) 0.0151(12) 0.0187(12) -0.0016(9) 0.0035(9) 0.0002(10) C11 0.0181(12) 0.0153(12) 0.0174(12) 0.0011(10) 0.0043(9) 0.0022(10) C12 0.0256(13) 0.0143(13) 0.0233(13) -0.0047(10) 0.0062(10) 0.0023(10) C13 0.0265(14) 0.0143(13) 0.0317(14) 0.0026(11) 0.0062(11) 0.0026(11) C14 0.0229(13) 0.0225(14) 0.0221(12) 0.0066(11) 0.0048(10) 0.0012(11) C15 0.0214(13) 0.0204(13) 0.0180(12) -0.0014(10) 0.0049(10) -0.0001(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.092(3) . ? C1 C6 1.390(4) . ? C1 C2 1.394(4) . ? C2 C3 1.383(4) . ? C2 H2 0.95 . ? C3 C4 1.391(4) . ? C3 H3 0.95 . ? C4 C5 1.389(4) . ? C4 H4 0.95 . ? C5 C6 1.397(4) . ? C5 H5 0.95 . ? C6 N7 1.437(3) . ? N7 N8 1.367(3) . ? N7 C11 1.369(3) . ? N8 N9 1.309(3) . ? N9 C10 1.380(3) . ? C10 C11 1.401(3) . ? C10 C15 1.410(4) . ? C11 C12 1.399(4) . ? C12 C13 1.382(4) . ? C12 H12 0.95 . ? C13 C14 1.417(4) . ? C13 H13 0.95 . ? C14 C15 1.373(4) . ? C14 H14 0.95 . ? C15 H15 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 C6 C1 C2 119.4(2) . . ? C6 C1 I1 121.49(19) . . ? C2 C1 I1 119.1(2) . . ? C3 C2 C1 119.9(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.8(2) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 119.7(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 119.6(2) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C1 C6 C5 120.7(2) . . ? C1 C6 N7 121.5(2) . . ? C5 C6 N7 117.9(2) . . ? N8 N7 C11 110.4(2) . . ? N8 N7 C6 120.9(2) . . ? C11 N7 C6 128.3(2) . . ? N9 N8 N7 108.6(2) . . ? N8 N9 C10 108.3(2) . . ? N9 C10 C11 108.9(2) . . ? N9 C10 C15 130.9(2) . . ? C11 C10 C15 120.1(2) . . ? N7 C11 C12 133.4(2) . . ? N7 C11 C10 103.7(2) . . ? C12 C11 C10 122.9(2) . . ? C13 C12 C11 116.2(2) . . ? C13 C12 H12 121.9 . . ? C11 C12 H12 121.9 . . ? C12 C13 C14 121.6(3) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C15 C14 C13 122.0(2) . . ? C15 C14 H14 119 . . ? C13 C14 H14 119 . . ? C14 C15 C10 117.2(2) . . ? C14 C15 H15 121.4 . . ? C10 C15 H15 121.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.1(4) . . . . ? I1 C1 C2 C3 178.5(2) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? C3 C4 C5 C6 -0.7(4) . . . . ? C2 C1 C6 C5 -0.1(4) . . . . ? I1 C1 C6 C5 -178.55(19) . . . . ? C2 C1 C6 N7 -179.5(2) . . . . ? I1 C1 C6 N7 2.0(3) . . . . ? C4 C5 C6 C1 0.5(4) . . . . ? C4 C5 C6 N7 179.9(2) . . . . ? C1 C6 N7 N8 -100.2(3) . . . . ? C5 C6 N7 N8 80.3(3) . . . . ? C1 C6 N7 C11 87.2(3) . . . . ? C5 C6 N7 C11 -92.3(3) . . . . ? C11 N7 N8 N9 -0.3(3) . . . . ? C6 N7 N8 N9 -174.1(2) . . . . ? N7 N8 N9 C10 0.6(3) . . . . ? N8 N9 C10 C11 -0.7(3) . . . . ? N8 N9 C10 C15 177.5(3) . . . . ? N8 N7 C11 C12 -179.6(3) . . . . ? C6 N7 C11 C12 -6.4(5) . . . . ? N8 N7 C11 C10 -0.1(3) . . . . ? C6 N7 C11 C10 173.1(2) . . . . ? N9 C10 C11 N7 0.5(3) . . . . ? C15 C10 C11 N7 -177.9(2) . . . . ? N9 C10 C11 C12 180.0(2) . . . . ? C15 C10 C11 C12 1.6(4) . . . . ? N7 C11 C12 C13 178.3(3) . . . . ? C10 C11 C12 C13 -1.1(4) . . . . ? C11 C12 C13 C14 -0.3(4) . . . . ? C12 C13 C14 C15 1.3(4) . . . . ? C13 C14 C15 C10 -0.8(4) . . . . ? N9 C10 C15 C14 -178.6(3) . . . . ? C11 C10 C15 C14 -0.6(4) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962371' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3e _audit_creation_date 2013-01-22T15:48:43-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H10 I N3 O' _chemical_formula_sum 'C13 H10 I N3 O' _chemical_formula_weight 351.14 _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 12.1661(7) _cell_length_b 7.2750(4) _cell_length_c 14.9877(8) _cell_angle_alpha 90 _cell_angle_beta 111.5170(17) _cell_angle_gamma 90 _cell_volume 1234.09(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4709 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 27.43 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.89 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.586 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.512 _exptl_absorpt_correction_T_max 0.696 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_unetI/netI 0.0289 _diffrn_reflns_number 9552 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 2827 _reflns_number_gt 2515 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0321P)^2^+0.5693P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 2827 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0653 _refine_ls_wR_factor_gt 0.0629 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.845 _refine_diff_density_min -0.45 _refine_diff_density_rms 0.088 _iucr_refine_instructions_details ; .res file for SHELXL : job.res ................................................................. TITL import in P 21/a CELL 0.71073 12.1661 7.2750 14.9877 90.0000 111.5170 90.0000 ZERR 4 0.0007 0.0004 0.0008 0.0000 0.0017 0.0000 LATT 1 SYMM 1/2 - X, 1/2 + Y, - Z SFAC C H N O I UNIT 52 40 12 4 4 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.032100 0.569300 FVAR 0.54705 C1 1 0.161489 0.093018 0.685647 11.00000 0.02033 0.01675 = 0.02175 0.00094 0.01064 0.00013 C2 1 0.042403 0.057291 0.661514 11.00000 0.01635 0.02629 = 0.02064 -0.00101 0.00313 0.00041 AFIX 43 H2 2 -0.006851 0.042583 0.596024 11.00000 -1.20000 AFIX 0 C3 1 -0.006400 0.042551 0.732663 11.00000 0.01346 0.02578 = 0.02691 0.00019 0.00676 -0.00095 AFIX 43 H3 2 -0.088337 0.016536 0.713712 11.00000 -1.20000 AFIX 0 C4 1 0.059456 0.064203 0.829020 11.00000 0.01319 0.02017 = 0.02448 -0.00004 0.00794 -0.00138 AFIX 43 H4 2 0.025578 0.052466 0.876647 11.00000 -1.20000 AFIX 0 C5 1 0.179393 0.104573 0.852307 11.00000 0.01402 0.01154 = 0.02303 -0.00022 0.00659 0.00097 C6 1 0.230456 0.118012 0.782684 11.00000 0.01164 0.01695 = 0.02703 -0.00198 0.00721 0.00049 N7 3 0.348748 0.154641 0.827015 11.00000 0.01470 0.02594 = 0.02549 -0.00089 0.00784 -0.00348 N8 3 0.373055 0.165581 0.918675 11.00000 0.01111 0.02901 = 0.02612 -0.00021 0.00912 -0.00383 N9 3 0.271797 0.136231 0.937071 11.00000 0.01085 0.01961 = 0.02146 -0.00068 0.00647 -0.00060 C10 1 0.278056 0.130983 1.034157 11.00000 0.01660 0.01335 = 0.01997 -0.00100 0.00518 -0.00217 C11 1 0.183082 0.188209 1.057899 11.00000 0.01355 0.01789 = 0.02341 0.00061 0.00590 0.00107 AFIX 43 H11 2 0.112091 0.229555 1.009544 11.00000 -1.20000 AFIX 0 C12 1 0.193563 0.183999 1.152713 11.00000 0.01577 0.01871 = 0.02596 -0.00014 0.00956 -0.00170 AFIX 43 H12 2 0.128998 0.221420 1.169692 11.00000 -1.20000 AFIX 0 C13 1 0.298825 0.124886 1.224196 11.00000 0.02133 0.01757 = 0.02047 0.00043 0.00943 -0.00496 C14 1 0.392324 0.066674 1.200228 11.00000 0.01543 0.02093 = 0.02248 0.00011 0.00279 0.00079 AFIX 43 H14 2 0.463231 0.024881 1.248523 11.00000 -1.20000 AFIX 0 C15 1 0.381773 0.069766 1.104753 11.00000 0.01249 0.01968 = 0.02425 -0.00356 0.00544 0.00038 AFIX 43 H15 2 0.445762 0.029844 1.087650 11.00000 -1.20000 AFIX 0 O16 4 0.298561 0.128452 1.315537 11.00000 0.02257 0.03869 = 0.02081 0.00234 0.00814 0.00041 C17 1 0.408067 0.089004 1.391961 11.00000 0.03034 0.03932 = 0.01994 0.00394 0.00405 0.00044 AFIX 137 H17A 2 0.430612 -0.038795 1.386952 11.00000 -1.50000 H17B 2 0.398944 0.107365 1.453654 11.00000 -1.50000 H17C 2 0.469601 0.171442 1.387589 11.00000 -1.50000 AFIX 0 I1 5 0.238570 0.106253 0.582252 11.00000 0.02681 0.05206 = 0.02382 -0.00487 0.01394 -0.00681 HKLF 4 REM import in P 21/a REM R1 = 0.0281 for 2515 Fo > 4sig(Fo) and 0.0336 for all 2827 data REM 164 parameters refined using 0 restraints END WGHT 0.0304 0.5967 REM Highest difference peak 0.85, deepest hole -0.45, 1-sigma level 0.09 Q1 1 0.2316 -0.0205 0.5839 11.00000 0.05 0.85 Q2 1 0.2846 0.0962 0.6380 11.00000 0.05 0.58 Q3 1 0.2027 0.1056 0.5182 11.00000 0.05 0.56 Q4 1 0.2223 0.2325 0.5995 11.00000 0.05 0.53 Q5 1 0.2589 0.2328 0.5554 11.00000 0.05 0.45 Q6 1 0.3383 0.1457 1.0755 11.00000 0.05 0.41 Q7 1 0.1854 0.0999 0.7386 11.00000 0.05 0.37 Q8 1 0.2968 -0.0039 1.2819 11.00000 0.05 0.33 Q9 1 0.4067 0.1271 1.1660 11.00000 0.05 0.33 Q10 1 0.0336 0.0251 0.7847 11.00000 0.05 0.33 Q11 1 0.3794 0.0226 1.1565 11.00000 0.05 0.32 Q12 1 0.1001 0.0580 0.6829 11.00000 0.05 0.32 Q13 1 0.2445 0.1349 1.1889 11.00000 0.05 0.32 Q14 1 0.3558 0.1120 1.3507 11.00000 0.05 0.31 Q15 1 0.2786 0.1396 0.9923 11.00000 0.05 0.29 Q16 1 0.0248 0.0536 0.6983 11.00000 0.05 0.29 Q17 1 0.2068 0.0991 0.9059 11.00000 0.05 0.29 Q18 1 0.1184 0.1056 0.8441 11.00000 0.05 0.28 Q19 1 0.1927 0.1421 0.8123 11.00000 0.05 0.28 Q20 1 0.1979 0.2172 1.1103 11.00000 0.05 0.28 ; #----------------------------------------------------------------------------# # 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 C1 C 0.1615(2) 0.0930(3) 0.68565(18) 0.0188(5) Uani 1 1 d . . . C2 C 0.0424(2) 0.0573(4) 0.66151(18) 0.0221(5) Uani 1 1 d . . . H2 H -0.0069 0.0426 0.596 0.027 Uiso 1 1 calc R . . C3 C -0.0064(2) 0.0426(4) 0.73266(18) 0.0222(5) Uani 1 1 d . . . H3 H -0.0883 0.0165 0.7137 0.027 Uiso 1 1 calc R . . C4 C 0.0595(2) 0.0642(3) 0.82902(18) 0.0190(5) Uani 1 1 d . . . H4 H 0.0256 0.0525 0.8766 0.023 Uiso 1 1 calc R . . C5 C 0.1794(2) 0.1046(3) 0.85231(18) 0.0163(5) Uani 1 1 d . . . C6 C 0.2305(2) 0.1180(3) 0.78268(18) 0.0185(5) Uani 1 1 d . . . N7 N 0.34875(17) 0.1546(3) 0.82701(15) 0.0219(5) Uani 1 1 d . . . N8 N 0.37306(16) 0.1656(3) 0.91867(15) 0.0214(4) Uani 1 1 d . . . N9 N 0.27180(16) 0.1362(3) 0.93707(14) 0.0172(4) Uani 1 1 d . . . C10 C 0.2781(2) 0.1310(3) 1.03416(17) 0.0171(5) Uani 1 1 d . . . C11 C 0.1831(2) 0.1882(3) 1.05790(17) 0.0185(5) Uani 1 1 d . . . H11 H 0.1121 0.2296 1.0095 0.022 Uiso 1 1 calc R . . C12 C 0.1936(2) 0.1840(3) 1.15271(17) 0.0196(5) Uani 1 1 d . . . H12 H 0.129 0.2214 1.1697 0.024 Uiso 1 1 calc R . . C13 C 0.2988(2) 0.1249(3) 1.22420(18) 0.0193(5) Uani 1 1 d . . . C14 C 0.3923(2) 0.0667(3) 1.20023(18) 0.0208(5) Uani 1 1 d . . . H14 H 0.4632 0.0249 1.2485 0.025 Uiso 1 1 calc R . . C15 C 0.3818(2) 0.0698(3) 1.10475(17) 0.0192(5) Uani 1 1 d . . . H15 H 0.4458 0.0298 1.0877 0.023 Uiso 1 1 calc R . . O16 O 0.29856(16) 0.1285(3) 1.31554(13) 0.0273(4) Uani 1 1 d . . . C17 C 0.4081(2) 0.0890(4) 1.39196(19) 0.0313(6) Uani 1 1 d . . . H17A H 0.4306 -0.0388 1.387 0.047 Uiso 1 1 calc R . . H17B H 0.3989 0.1074 1.4537 0.047 Uiso 1 1 calc R . . H17C H 0.4696 0.1714 1.3876 0.047 Uiso 1 1 calc R . . I1 I 0.238570(15) 0.10625(3) 0.582252(12) 0.03291(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 0.0203(12) 0.0168(12) 0.0217(12) 0.0009(10) 0.0106(10) 0.0001(9) C2 0.0163(12) 0.0263(14) 0.0206(12) -0.0010(10) 0.0031(9) 0.0004(10) C3 0.0135(11) 0.0258(13) 0.0269(13) 0.0002(11) 0.0068(10) -0.0009(10) C4 0.0132(11) 0.0202(13) 0.0245(12) 0.0000(10) 0.0079(9) -0.0014(9) C5 0.0140(11) 0.0115(11) 0.0230(12) -0.0002(9) 0.0066(9) 0.0010(9) C6 0.0116(10) 0.0170(12) 0.0270(12) -0.0020(10) 0.0072(9) 0.0005(9) N7 0.0147(10) 0.0259(11) 0.0255(11) -0.0009(9) 0.0078(8) -0.0035(8) N8 0.0111(9) 0.0290(11) 0.0261(11) -0.0002(9) 0.0091(8) -0.0038(8) N9 0.0108(9) 0.0196(11) 0.0215(10) -0.0007(8) 0.0065(8) -0.0006(7) C10 0.0166(11) 0.0133(12) 0.0200(11) -0.0010(9) 0.0052(9) -0.0022(9) C11 0.0136(11) 0.0179(12) 0.0234(12) 0.0006(10) 0.0059(9) 0.0011(9) C12 0.0158(11) 0.0187(12) 0.0260(12) -0.0001(10) 0.0096(9) -0.0017(10) C13 0.0213(12) 0.0176(13) 0.0205(11) 0.0004(9) 0.0094(10) -0.0050(9) C14 0.0154(11) 0.0209(13) 0.0225(12) 0.0001(10) 0.0028(9) 0.0008(9) C15 0.0125(11) 0.0197(13) 0.0243(12) -0.0036(10) 0.0054(9) 0.0004(9) O16 0.0226(9) 0.0387(12) 0.0208(9) 0.0023(8) 0.0081(7) 0.0004(8) C17 0.0303(14) 0.0393(17) 0.0199(13) 0.0039(11) 0.0040(11) 0.0004(12) I1 0.02681(11) 0.05206(15) 0.02382(11) -0.00487(8) 0.01394(8) -0.00681(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.383(3) . ? C1 C6 1.399(3) . ? C1 I1 2.087(3) . ? C2 C3 1.402(3) . ? C2 H2 0.95 . ? C3 C4 1.380(3) . ? C3 H3 0.95 . ? C4 C5 1.401(3) . ? C4 H4 0.95 . ? C5 N9 1.372(3) . ? C5 C6 1.400(4) . ? C6 N7 1.372(3) . ? N7 N8 1.297(3) . ? N8 N9 1.374(3) . ? N9 C10 1.429(3) . ? C10 C15 1.389(3) . ? C10 C11 1.392(3) . ? C11 C12 1.380(3) . ? C11 H11 0.95 . ? C12 C13 1.402(3) . ? C12 H12 0.95 . ? C13 O16 1.370(3) . ? C13 C14 1.379(4) . ? C14 C15 1.389(4) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? O16 C17 1.432(3) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 117.9(2) . . ? C2 C1 I1 121.82(18) . . ? C6 C1 I1 120.29(18) . . ? C1 C2 C3 120.7(2) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 122.8(2) . . ? C4 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? C3 C4 C5 115.9(2) . . ? C3 C4 H4 122.1 . . ? C5 C4 H4 122.1 . . ? N9 C5 C6 104.0(2) . . ? N9 C5 C4 133.7(2) . . ? C6 C5 C4 122.4(2) . . ? N7 C6 C5 109.0(2) . . ? N7 C6 C1 130.6(2) . . ? C5 C6 C1 120.3(2) . . ? N8 N7 C6 108.4(2) . . ? N7 N8 N9 109.27(18) . . ? C5 N9 N8 109.3(2) . . ? C5 N9 C10 131.1(2) . . ? N8 N9 C10 119.43(19) . . ? C15 C10 C11 120.6(2) . . ? C15 C10 N9 118.6(2) . . ? C11 C10 N9 120.9(2) . . ? C12 C11 C10 119.0(2) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 120.5(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? O16 C13 C14 124.8(2) . . ? O16 C13 C12 114.9(2) . . ? C14 C13 C12 120.3(2) . . ? C13 C14 C15 119.3(2) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C10 120.3(2) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? C13 O16 C17 116.9(2) . . ? O16 C17 H17A 109.5 . . ? O16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 C6 C1 C2 C3 -1.5(4) . . . . ? I1 C1 C2 C3 177.68(19) . . . . ? C1 C2 C3 C4 0.7(4) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C3 C4 C5 N9 179.6(2) . . . . ? C3 C4 C5 C6 -1.5(3) . . . . ? N9 C5 C6 N7 0.5(3) . . . . ? C4 C5 C6 N7 -178.7(2) . . . . ? N9 C5 C6 C1 179.9(2) . . . . ? C4 C5 C6 C1 0.7(4) . . . . ? C2 C1 C6 N7 -180.0(2) . . . . ? I1 C1 C6 N7 0.9(4) . . . . ? C2 C1 C6 C5 0.8(3) . . . . ? I1 C1 C6 C5 -178.39(17) . . . . ? C5 C6 N7 N8 -0.4(3) . . . . ? C1 C6 N7 N8 -179.7(2) . . . . ? C6 N7 N8 N9 0.1(3) . . . . ? C6 C5 N9 N8 -0.5(2) . . . . ? C4 C5 N9 N8 178.6(3) . . . . ? C6 C5 N9 C10 -176.0(2) . . . . ? C4 C5 N9 C10 3.1(4) . . . . ? N7 N8 N9 C5 0.2(3) . . . . ? N7 N8 N9 C10 176.4(2) . . . . ? C5 N9 C10 C15 145.2(2) . . . . ? N8 N9 C10 C15 -29.9(3) . . . . ? C5 N9 C10 C11 -35.6(4) . . . . ? N8 N9 C10 C11 149.2(2) . . . . ? C15 C10 C11 C12 0.3(4) . . . . ? N9 C10 C11 C12 -178.9(2) . . . . ? C10 C11 C12 C13 0.7(4) . . . . ? C11 C12 C13 O16 179.5(2) . . . . ? C11 C12 C13 C14 -1.3(4) . . . . ? O16 C13 C14 C15 -179.9(2) . . . . ? C12 C13 C14 C15 0.9(4) . . . . ? C13 C14 C15 C10 0.0(4) . . . . ? C11 C10 C15 C14 -0.6(4) . . . . ? N9 C10 C15 C14 178.5(2) . . . . ? C14 C13 O16 C17 7.6(4) . . . . ? C12 C13 O16 C17 -173.3(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962372' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3g _audit_creation_date 2013-01-24T10:36:54-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H6 I N3 S' _chemical_formula_sum 'C10 H6 I N3 S' _chemical_formula_weight 327.14 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.6989(10) _cell_length_b 8.5117(12) _cell_length_c 19.409(3) _cell_angle_alpha 90 _cell_angle_beta 96.629(5) _cell_angle_gamma 90 _cell_volume 1099.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4060 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 27.33 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.977 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.621 _exptl_absorpt_correction_T_max 0.807 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0586 _diffrn_reflns_av_unetI/netI 0.061 _diffrn_reflns_number 8112 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 2509 _reflns_number_gt 1970 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0342P)^2^+0.7091P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 2509 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.988 _refine_diff_density_min -0.729 _refine_diff_density_rms 0.137 _iucr_refine_instructions_details ; .res file for SHELXL : job2.res ................................................................. TITL import in P 21/c CELL 0.71073 6.6989 8.5117 19.4090 90.000 96.629 90.000 ZERR 4.00 0.0010 0.0012 0.0030 0.000 0.005 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N S I UNIT 40 24 12 4 4 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.034200 0.709100 FVAR 0.35698 C1 1 0.289461 -0.422973 -0.092389 11.00000 0.03628 0.02844 = 0.02873 -0.00457 -0.00500 0.00204 AFIX 43 H1 2 0.156476 -0.458615 -0.106219 11.00000 -1.20000 AFIX 0 C2 1 0.445987 -0.462496 -0.128190 11.00000 0.05951 0.02958 = 0.03130 -0.00742 -0.00206 0.01316 AFIX 43 H2 2 0.421175 -0.529830 -0.167276 11.00000 -1.20000 AFIX 0 C3 1 0.643186 -0.407098 -0.109321 11.00000 0.03857 0.03610 = 0.02926 -0.00230 0.01166 0.00932 AFIX 43 H3 2 0.745215 -0.435748 -0.137104 11.00000 -1.20000 AFIX 0 C4 1 0.694436 -0.311565 -0.051264 11.00000 0.03546 0.03325 = 0.02860 0.00081 0.00831 0.00806 AFIX 43 H4 2 0.827754 -0.276247 -0.037780 11.00000 -1.20000 AFIX 0 C5 1 0.530629 -0.271731 -0.014137 11.00000 0.02973 0.02098 = 0.02182 0.00010 0.00350 0.00755 C6 1 0.336313 -0.325966 -0.033536 11.00000 0.03535 0.02321 = 0.02406 0.00169 0.00017 0.00455 N7 3 0.210504 -0.267969 0.012829 11.00000 0.02675 0.02819 = 0.03148 -0.00113 0.00168 0.00127 N8 3 0.318524 -0.181452 0.059082 11.00000 0.02440 0.03288 = 0.02858 -0.00472 0.00651 0.00743 N9 3 0.514926 -0.182170 0.044647 11.00000 0.02394 0.02256 = 0.02366 -0.00200 0.00457 0.00313 C10 1 0.658578 -0.094968 0.087421 11.00000 0.03083 0.02062 = 0.01969 0.00063 0.00589 0.00630 C11 1 0.855101 -0.068990 0.079593 11.00000 0.02762 0.03313 = 0.02573 0.00106 0.00827 0.00185 AFIX 43 H11 2 0.919830 -0.110146 0.042454 11.00000 -1.20000 AFIX 0 C12 1 0.952345 0.026602 0.133238 11.00000 0.02666 0.02618 = 0.03060 0.00456 0.00545 -0.00419 AFIX 43 H12 2 1.090068 0.055441 0.136198 11.00000 -1.20000 AFIX 0 C13 1 0.826204 0.073051 0.180461 11.00000 0.02865 0.02921 = 0.02367 0.00279 -0.00384 -0.00424 I1 5 0.900392 0.213030 0.266515 11.00000 0.04785 0.03110 = 0.02749 -0.00346 -0.00480 -0.00371 S1 4 0.587948 -0.004345 0.161043 11.00000 0.02770 0.03204 = 0.02560 -0.00521 0.00615 -0.00077 HKLF 4 REM import in P 21/c REM R1 = 0.0392 for 1970 Fo > 4sig(Fo) and 0.0492 for all 2509 data REM 136 parameters refined using 0 restraints END WGHT 0.0285 0.5108 REM Highest difference peak 0.99, deepest hole -0.73, 1-sigma level 0.14 Q1 1 0.7481 0.2753 0.2730 11.00000 0.05 0.99 Q2 1 0.1170 -0.5169 -0.1240 11.00000 0.05 0.90 Q3 1 0.7982 0.2808 0.2443 11.00000 0.05 0.87 Q4 1 0.8656 0.1536 0.2163 11.00000 0.05 0.67 Q5 1 0.9309 0.2357 0.2797 11.00000 0.05 0.66 Q6 1 0.9430 0.1559 0.3162 11.00000 0.05 0.65 Q7 1 1.0239 0.2750 0.3038 11.00000 0.05 0.59 Q8 1 1.1305 0.1297 0.2995 11.00000 0.05 0.57 Q9 1 0.9462 0.1636 0.2408 11.00000 0.05 0.53 Q10 1 0.7865 0.1574 0.2715 11.00000 0.05 0.52 Q11 1 1.0746 0.1630 0.2799 11.00000 0.05 0.50 Q12 1 0.0357 -0.4519 -0.1893 11.00000 0.05 0.49 Q13 1 0.7391 0.0002 0.2185 11.00000 0.05 0.48 Q14 1 0.5278 0.1190 0.1330 11.00000 0.05 0.46 Q15 1 0.7393 0.3191 0.3277 11.00000 0.05 0.45 Q16 1 1.1027 0.1249 0.1726 11.00000 0.05 0.44 Q17 1 0.3086 -0.0724 0.0692 11.00000 0.05 0.42 Q18 1 0.8333 -0.1562 0.2181 11.00000 0.05 0.42 Q19 1 0.5235 -0.4659 -0.0305 11.00000 0.05 0.42 Q20 1 1.0003 0.0121 0.1693 11.00000 0.05 0.40 ; #----------------------------------------------------------------------------# # 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' S S 0.1246 0.1234 '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 C1 C 0.2895(8) -0.4230(6) -0.0924(3) 0.0318(12) Uani 1 1 d . . . H1 H 0.1565 -0.4586 -0.1062 0.038 Uiso 1 1 calc R . . C2 C 0.4460(9) -0.4625(7) -0.1282(3) 0.0407(14) Uani 1 1 d . . . H2 H 0.4212 -0.5298 -0.1673 0.049 Uiso 1 1 calc R . . C3 C 0.6432(8) -0.4071(6) -0.1093(3) 0.0340(12) Uani 1 1 d . . . H3 H 0.7452 -0.4357 -0.1371 0.041 Uiso 1 1 calc R . . C4 C 0.6944(8) -0.3116(6) -0.0513(3) 0.0321(12) Uani 1 1 d . . . H4 H 0.8278 -0.2762 -0.0378 0.038 Uiso 1 1 calc R . . C5 C 0.5306(8) -0.2717(5) -0.0141(2) 0.0241(10) Uani 1 1 d . . . C6 C 0.3363(8) -0.3260(6) -0.0335(3) 0.0278(11) Uani 1 1 d . . . N7 N 0.2105(6) -0.2680(5) 0.0128(2) 0.0289(9) Uani 1 1 d . . . N8 N 0.3185(6) -0.1815(5) 0.0591(2) 0.0284(9) Uani 1 1 d . . . N9 N 0.5149(6) -0.1822(5) 0.0446(2) 0.0232(9) Uani 1 1 d . . . C10 C 0.6586(7) -0.0950(6) 0.0874(2) 0.0235(10) Uani 1 1 d . . . C11 C 0.8551(7) -0.0690(6) 0.0796(3) 0.0284(11) Uani 1 1 d . . . H11 H 0.9198 -0.1101 0.0425 0.034 Uiso 1 1 calc R . . C12 C 0.9523(8) 0.0266(6) 0.1332(3) 0.0276(11) Uani 1 1 d . . . H12 H 1.0901 0.0554 0.1362 0.033 Uiso 1 1 calc R . . C13 C 0.8262(7) 0.0731(6) 0.1805(2) 0.0277(11) Uani 1 1 d . . . I1 I 0.90039(5) 0.21303(4) 0.266515(17) 0.03619(15) Uani 1 1 d . . . S1 S 0.58795(19) -0.00434(15) 0.16104(6) 0.0282(3) 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 0.036(3) 0.028(3) 0.029(3) -0.005(2) -0.005(2) 0.002(2) C2 0.060(4) 0.030(3) 0.031(3) -0.007(2) -0.002(3) 0.013(3) C3 0.039(3) 0.036(3) 0.029(3) -0.002(2) 0.012(2) 0.009(3) C4 0.035(3) 0.033(3) 0.029(3) 0.001(2) 0.008(2) 0.008(2) C5 0.030(3) 0.021(2) 0.022(2) 0.000(2) 0.0035(19) 0.008(2) C6 0.035(3) 0.023(3) 0.024(3) 0.002(2) 0.000(2) 0.005(2) N7 0.027(2) 0.028(2) 0.031(2) -0.0011(19) 0.0017(18) 0.0013(18) N8 0.024(2) 0.033(2) 0.029(2) -0.0047(19) 0.0065(18) 0.0074(18) N9 0.024(2) 0.023(2) 0.024(2) -0.0020(16) 0.0046(16) 0.0031(17) C10 0.031(3) 0.021(2) 0.020(2) 0.0006(19) 0.0059(19) 0.006(2) C11 0.028(3) 0.033(3) 0.026(3) 0.001(2) 0.008(2) 0.002(2) C12 0.027(3) 0.026(3) 0.031(3) 0.005(2) 0.005(2) -0.004(2) C13 0.029(3) 0.029(3) 0.024(2) 0.003(2) -0.004(2) -0.004(2) I1 0.0479(3) 0.0311(2) 0.0275(2) -0.00346(14) -0.00480(16) -0.00371(16) S1 0.0277(7) 0.0320(7) 0.0256(7) -0.0052(5) 0.0061(5) -0.0008(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.365(8) . ? C1 C6 1.415(7) . ? C1 H1 0.95 . ? C2 C3 1.411(8) . ? C2 H2 0.95 . ? C3 C4 1.400(7) . ? C3 H3 0.95 . ? C4 C5 1.422(7) . ? C4 H4 0.95 . ? C5 N9 1.386(6) . ? C5 C6 1.391(7) . ? C6 N7 1.392(6) . ? N7 N8 1.312(6) . ? N8 N9 1.376(6) . ? N9 C10 1.408(6) . ? C10 C11 1.361(7) . ? C10 S1 1.737(5) . ? C11 C12 1.419(7) . ? C11 H11 0.95 . ? C12 C13 1.374(7) . ? C12 H12 0.95 . ? C13 S1 1.728(5) . ? C13 I1 2.065(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 C2 C1 C6 116.3(5) . . ? C2 C1 H1 121.9 . . ? C6 C1 H1 121.9 . . ? C1 C2 C3 122.5(5) . . ? C1 C2 H2 118.8 . . ? C3 C2 H2 118.8 . . ? C4 C3 C2 122.6(5) . . ? C4 C3 H3 118.7 . . ? C2 C3 H3 118.7 . . ? C3 C4 C5 114.5(5) . . ? C3 C4 H4 122.8 . . ? C5 C4 H4 122.8 . . ? N9 C5 C6 104.3(4) . . ? N9 C5 C4 133.2(5) . . ? C6 C5 C4 122.4(5) . . ? C5 C6 N7 108.9(4) . . ? C5 C6 C1 121.7(5) . . ? N7 C6 C1 129.4(5) . . ? N8 N7 C6 108.3(4) . . ? N7 N8 N9 108.8(4) . . ? N8 N9 C5 109.6(4) . . ? N8 N9 C10 118.8(4) . . ? C5 N9 C10 131.6(4) . . ? C11 C10 N9 128.6(4) . . ? C11 C10 S1 112.3(4) . . ? N9 C10 S1 119.1(3) . . ? C10 C11 C12 112.3(4) . . ? C10 C11 H11 123.9 . . ? C12 C11 H11 123.9 . . ? C13 C12 C11 112.9(5) . . ? C13 C12 H12 123.6 . . ? C11 C12 H12 123.6 . . ? C12 C13 S1 111.6(4) . . ? C12 C13 I1 126.6(4) . . ? S1 C13 I1 121.8(3) . . ? C13 S1 C10 90.9(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 C6 C1 C2 C3 -1.7(8) . . . . ? C1 C2 C3 C4 2.1(9) . . . . ? C2 C3 C4 C5 -1.6(8) . . . . ? C3 C4 C5 N9 -179.9(5) . . . . ? C3 C4 C5 C6 1.1(7) . . . . ? N9 C5 C6 N7 0.4(5) . . . . ? C4 C5 C6 N7 179.7(5) . . . . ? N9 C5 C6 C1 179.9(5) . . . . ? C4 C5 C6 C1 -0.9(8) . . . . ? C2 C1 C6 C5 1.1(8) . . . . ? C2 C1 C6 N7 -179.5(5) . . . . ? C5 C6 N7 N8 0.1(6) . . . . ? C1 C6 N7 N8 -179.3(5) . . . . ? C6 N7 N8 N9 -0.6(5) . . . . ? N7 N8 N9 C5 0.9(5) . . . . ? N7 N8 N9 C10 179.3(4) . . . . ? C6 C5 N9 N8 -0.8(5) . . . . ? C4 C5 N9 N8 -179.9(5) . . . . ? C6 C5 N9 C10 -178.9(5) . . . . ? C4 C5 N9 C10 1.9(9) . . . . ? N8 N9 C10 C11 -174.2(5) . . . . ? C5 N9 C10 C11 3.8(8) . . . . ? N8 N9 C10 S1 5.7(6) . . . . ? C5 N9 C10 S1 -176.3(4) . . . . ? N9 C10 C11 C12 179.4(5) . . . . ? S1 C10 C11 C12 -0.5(6) . . . . ? C10 C11 C12 C13 -0.8(6) . . . . ? C11 C12 C13 S1 1.6(6) . . . . ? C11 C12 C13 I1 -179.7(4) . . . . ? C12 C13 S1 C10 -1.6(4) . . . . ? I1 C13 S1 C10 179.7(3) . . . . ? C11 C10 S1 C13 1.2(4) . . . . ? N9 C10 S1 C13 -178.7(4) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962373' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4b _audit_creation_date 2012-05-23T17:20:27-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H7 I2 N3' _chemical_formula_sum 'C12 H7 I2 N3' _chemical_formula_weight 447.01 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.4884(2) _cell_length_b 12.4932(5) _cell_length_c 22.1910(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1244.35(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3498 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.37 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 2.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.034 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.440 _exptl_absorpt_correction_T_max 0.739 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_unetI/netI 0.0537 _diffrn_reflns_number 6622 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.2 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 2732 _reflns_number_gt 2611 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0349P)^2^+0.2172P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 2732 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.033 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_gt 0.0747 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _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 -0.02(4) _refine_diff_density_max 0.798 _refine_diff_density_min -1.083 _refine_diff_density_rms 0.168 _iucr_refine_instructions_details ; .res file for SHELXL : job.res ................................................................. TITL import in P 21 21 21 CELL 0.71073 4.4884 12.4932 22.1910 90.000 90.000 90.000 ZERR 4.00 0.0002 0.0005 0.0010 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N I UNIT 48 28 12 8 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.034900 0.217200 FVAR 0.30799 I1 4 0.777700 0.158984 0.152325 11.00000 0.01993 0.01635 = 0.02116 -0.00221 -0.00198 0.00091 C1 1 0.552432 0.298961 0.127138 11.00000 0.01740 0.01548 = 0.02250 0.00121 0.00077 -0.00226 C2 1 0.432277 0.303979 0.069466 11.00000 0.02479 0.02109 = 0.02327 -0.00629 0.00029 -0.00280 AFIX 43 H2 2 0.447983 0.244173 0.043218 11.00000 -1.20000 AFIX 0 C3 1 0.288768 0.396781 0.050170 11.00000 0.02689 0.02418 = 0.01628 0.00051 -0.00296 -0.00221 AFIX 43 H3 2 0.209154 0.400022 0.010546 11.00000 -1.20000 AFIX 0 C4 1 0.260843 0.484061 0.087911 11.00000 0.02614 0.02387 = 0.02027 0.00757 0.00162 0.00375 AFIX 43 H4 2 0.164503 0.547248 0.074217 11.00000 -1.20000 AFIX 0 C5 1 0.374065 0.478852 0.145768 11.00000 0.02361 0.01454 = 0.02322 -0.00303 0.00042 0.00323 AFIX 43 H5 2 0.351206 0.538175 0.172148 11.00000 -1.20000 AFIX 0 C6 1 0.520506 0.387888 0.165584 11.00000 0.01385 0.01656 = 0.01984 0.00207 0.00023 -0.00325 N7 3 0.630715 0.387413 0.225700 11.00000 0.02020 0.01580 = 0.01307 -0.00119 -0.00128 -0.00172 N8 3 0.818087 0.468740 0.244283 11.00000 0.02018 0.01049 = 0.01966 -0.00311 0.00043 -0.00779 N9 3 0.846880 0.464778 0.302398 11.00000 0.02244 0.01338 = 0.01385 -0.00199 -0.00071 -0.00258 C10 1 0.669470 0.383247 0.323506 11.00000 0.01665 0.00837 = 0.01918 -0.00082 0.00011 0.00406 C11 1 0.527465 0.334256 0.275276 11.00000 0.01717 0.01332 = 0.01305 -0.00072 0.00239 0.00370 C12 1 0.329744 0.248289 0.282223 11.00000 0.01658 0.01764 = 0.01607 -0.00099 -0.00245 -0.00103 AFIX 43 H12 2 0.236494 0.214474 0.248838 11.00000 -1.20000 AFIX 0 C13 1 0.279936 0.216241 0.340597 11.00000 0.02216 0.01578 = 0.02784 0.00603 -0.00046 -0.00306 AFIX 43 H13 2 0.147155 0.158400 0.347742 11.00000 -1.20000 AFIX 0 C14 1 0.418013 0.265798 0.390143 11.00000 0.02549 0.02224 = 0.01787 0.00394 0.00430 0.00363 AFIX 43 H14 2 0.376649 0.240506 0.429639 11.00000 -1.20000 AFIX 0 C15 1 0.611577 0.350051 0.382705 11.00000 0.01978 0.01790 = 0.01474 -0.00522 -0.00126 0.00638 I2 4 0.802981 0.428579 0.456006 11.00000 0.02712 0.02858 = 0.01382 -0.00332 -0.00094 0.00168 HKLF 4 REM import in P 21 21 21 REM R1 = 0.0314 for 2611 Fo > 4sig(Fo) and 0.0330 for all 2732 data REM 154 parameters refined using 0 restraints END WGHT 0.0340 0.0000 REM Highest difference peak 0.80, deepest hole -1.08, 1-sigma level 0.17 Q1 1 0.1609 0.5716 0.0336 11.00000 0.05 0.80 Q2 1 0.3142 0.1589 0.2322 11.00000 0.05 0.79 Q3 1 0.2521 0.1602 0.0727 11.00000 0.05 0.75 Q4 1 -0.1344 0.5177 0.0407 11.00000 0.05 0.71 Q5 1 0.1394 0.3259 0.4568 11.00000 0.05 0.71 Q6 1 1.1139 0.4340 0.4556 11.00000 0.05 0.67 Q7 1 0.1964 0.4778 -0.0430 11.00000 0.05 0.66 Q8 1 0.7625 0.1568 0.1148 11.00000 0.05 0.66 Q9 1 0.9952 0.1548 0.1020 11.00000 0.05 0.65 Q10 1 0.5425 0.3159 0.4565 11.00000 0.05 0.62 Q11 1 0.5740 0.3837 -0.0480 11.00000 0.05 0.61 Q12 1 0.3680 0.5763 0.0221 11.00000 0.05 0.61 Q13 1 0.2736 0.4374 0.3784 11.00000 0.05 0.61 Q14 1 0.7951 0.4357 0.4911 11.00000 0.05 0.60 Q15 1 0.4421 0.4369 0.3852 11.00000 0.05 0.59 Q16 1 1.0360 0.4208 0.4043 11.00000 0.05 0.58 Q17 1 0.0444 0.1600 0.2103 11.00000 0.05 0.58 Q18 1 0.3832 0.1594 0.0804 11.00000 0.05 0.58 Q19 1 0.4914 0.2621 0.1527 11.00000 0.05 0.58 Q20 1 0.9745 0.5439 0.3469 11.00000 0.05 0.58 ; #----------------------------------------------------------------------------# # 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' 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 0.77770(8) 0.15898(3) 0.152325(16) 0.01915(10) Uani 1 1 d . . . C1 C 0.5524(13) 0.2990(5) 0.1271(3) 0.0185(12) Uani 1 1 d . . . C2 C 0.4323(14) 0.3040(5) 0.0695(3) 0.0230(13) Uani 1 1 d . . . H2 H 0.448 0.2442 0.0432 0.028 Uiso 1 1 calc R . . C3 C 0.2888(14) 0.3968(5) 0.0502(2) 0.0224(12) Uani 1 1 d . . . H3 H 0.2092 0.4 0.0105 0.027 Uiso 1 1 calc R . . C4 C 0.2608(15) 0.4841(5) 0.0879(2) 0.0234(12) Uani 1 1 d . . . H4 H 0.1645 0.5472 0.0742 0.028 Uiso 1 1 calc R . . C5 C 0.3741(13) 0.4789(5) 0.1458(3) 0.0205(12) Uani 1 1 d . . . H5 H 0.3512 0.5382 0.1721 0.025 Uiso 1 1 calc R . . C6 C 0.5205(12) 0.3879(4) 0.1656(2) 0.0167(11) Uani 1 1 d . . . N7 N 0.6307(10) 0.3874(4) 0.22570(19) 0.0164(10) Uani 1 1 d . . . N8 N 0.8181(11) 0.4687(3) 0.2443(2) 0.0168(9) Uani 1 1 d . . . N9 N 0.8469(11) 0.4648(4) 0.30240(19) 0.0166(10) Uani 1 1 d . . . C10 C 0.6695(12) 0.3832(4) 0.3235(2) 0.0147(11) Uani 1 1 d . . . C11 C 0.5275(12) 0.3343(4) 0.2753(2) 0.0145(10) Uani 1 1 d . . . C12 C 0.3297(12) 0.2483(4) 0.2822(2) 0.0168(11) Uani 1 1 d . . . H12 H 0.2365 0.2145 0.2488 0.02 Uiso 1 1 calc R . . C13 C 0.2799(14) 0.2162(4) 0.3406(2) 0.0219(12) Uani 1 1 d . . . H13 H 0.1472 0.1584 0.3477 0.026 Uiso 1 1 calc R . . C14 C 0.4180(14) 0.2658(5) 0.3901(3) 0.0219(13) Uani 1 1 d . . . H14 H 0.3766 0.2405 0.4296 0.026 Uiso 1 1 calc R . . C15 C 0.6116(12) 0.3501(5) 0.3827(2) 0.0175(11) Uani 1 1 d . . . I2 I 0.80298(9) 0.42858(3) 0.456006(15) 0.02317(11) 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 I1 0.01993(18) 0.01635(18) 0.02116(17) -0.00221(14) -0.00198(15) 0.00091(14) C1 0.017(3) 0.015(3) 0.022(3) 0.001(3) 0.001(2) -0.002(2) C2 0.025(3) 0.021(3) 0.023(3) -0.006(3) 0.000(3) -0.003(2) C3 0.027(3) 0.024(3) 0.016(2) 0.001(2) -0.003(3) -0.002(3) C4 0.026(3) 0.024(3) 0.020(2) 0.008(2) 0.002(3) 0.004(3) C5 0.024(3) 0.015(3) 0.023(3) -0.003(3) 0.000(2) 0.003(2) C6 0.014(2) 0.017(3) 0.020(3) 0.002(2) 0.000(2) -0.003(2) N7 0.020(2) 0.016(2) 0.013(2) -0.0012(19) -0.0013(18) -0.0017(18) N8 0.020(2) 0.010(2) 0.020(2) -0.0031(18) 0.000(2) -0.0078(19) N9 0.022(3) 0.013(2) 0.014(2) -0.0020(18) -0.0007(19) -0.0026(18) C10 0.017(3) 0.008(2) 0.019(2) -0.001(2) 0.000(2) 0.004(2) C11 0.017(2) 0.013(3) 0.013(2) -0.001(2) 0.0024(19) 0.004(2) C12 0.017(3) 0.018(3) 0.016(2) -0.001(2) -0.002(2) -0.001(2) C13 0.022(3) 0.016(3) 0.028(3) 0.006(2) 0.000(3) -0.003(2) C14 0.025(3) 0.022(3) 0.018(3) 0.004(3) 0.004(2) 0.004(3) C15 0.020(3) 0.018(3) 0.015(2) -0.005(2) -0.001(2) 0.006(2) I2 0.0271(2) 0.0286(2) 0.01382(16) -0.00332(16) -0.00094(15) 0.00168(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.096(6) . ? C1 C2 1.390(9) . ? C1 C6 1.408(8) . ? C2 C3 1.394(9) . ? C2 H2 0.95 . ? C3 C4 1.381(8) . ? C3 H3 0.95 . ? C4 C5 1.382(7) . ? C4 H4 0.95 . ? C5 C6 1.385(8) . ? C5 H5 0.95 . ? C6 N7 1.423(7) . ? N7 C11 1.366(7) . ? N7 N8 1.382(6) . ? N8 N9 1.297(6) . ? N9 C10 1.375(7) . ? C10 C11 1.388(7) . ? C10 C15 1.402(7) . ? C11 C12 1.402(8) . ? C12 C13 1.374(8) . ? C12 H12 0.95 . ? C13 C14 1.406(8) . ? C13 H13 0.95 . ? C14 C15 1.375(9) . ? C14 H14 0.95 . ? C15 I2 2.085(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 C2 C1 C6 118.9(6) . . ? C2 C1 I1 118.1(5) . . ? C6 C1 I1 123.1(4) . . ? C1 C2 C3 120.0(6) . . ? C1 C2 H2 120 . . ? C3 C2 H2 120 . . ? C4 C3 C2 120.8(5) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.5(6) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 120.5(6) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 120.2(5) . . ? C5 C6 N7 117.8(5) . . ? C1 C6 N7 122.0(5) . . ? C11 N7 N8 108.9(4) . . ? C11 N7 C6 129.7(5) . . ? N8 N7 C6 119.2(4) . . ? N9 N8 N7 109.2(4) . . ? N8 N9 C10 108.0(4) . . ? N9 C10 C11 109.3(5) . . ? N9 C10 C15 130.2(5) . . ? C11 C10 C15 120.5(5) . . ? N7 C11 C10 104.5(5) . . ? N7 C11 C12 132.5(5) . . ? C10 C11 C12 122.9(5) . . ? C13 C12 C11 115.5(5) . . ? C13 C12 H12 122.3 . . ? C11 C12 H12 122.3 . . ? C12 C13 C14 122.5(5) . . ? C12 C13 H13 118.8 . . ? C14 C13 H13 118.8 . . ? C15 C14 C13 121.5(5) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C10 117.1(5) . . ? C14 C15 I2 121.8(4) . . ? C10 C15 I2 121.0(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.3(9) . . . . ? I1 C1 C2 C3 -178.0(4) . . . . ? C1 C2 C3 C4 -0.7(9) . . . . ? C2 C3 C4 C5 -0.7(10) . . . . ? C3 C4 C5 C6 1.4(9) . . . . ? C4 C5 C6 C1 -0.8(9) . . . . ? C4 C5 C6 N7 -179.7(5) . . . . ? C2 C1 C6 C5 -0.6(9) . . . . ? I1 C1 C6 C5 178.7(4) . . . . ? C2 C1 C6 N7 178.3(5) . . . . ? I1 C1 C6 N7 -2.4(7) . . . . ? C5 C6 N7 C11 106.7(7) . . . . ? C1 C6 N7 C11 -72.2(8) . . . . ? C5 C6 N7 N8 -54.6(7) . . . . ? C1 C6 N7 N8 126.5(6) . . . . ? C11 N7 N8 N9 3.2(6) . . . . ? C6 N7 N8 N9 168.1(5) . . . . ? N7 N8 N9 C10 -2.3(6) . . . . ? N8 N9 C10 C11 0.7(6) . . . . ? N8 N9 C10 C15 -176.6(6) . . . . ? N8 N7 C11 C10 -2.6(6) . . . . ? C6 N7 C11 C10 -165.4(5) . . . . ? N8 N7 C11 C12 178.5(6) . . . . ? C6 N7 C11 C12 15.7(10) . . . . ? N9 C10 C11 N7 1.2(6) . . . . ? C15 C10 C11 N7 178.8(5) . . . . ? N9 C10 C11 C12 -179.7(5) . . . . ? C15 C10 C11 C12 -2.2(8) . . . . ? N7 C11 C12 C13 179.9(6) . . . . ? C10 C11 C12 C13 1.2(8) . . . . ? C11 C12 C13 C14 -0.2(8) . . . . ? C12 C13 C14 C15 0.2(9) . . . . ? C13 C14 C15 C10 -1.1(9) . . . . ? C13 C14 C15 I2 177.2(4) . . . . ? N9 C10 C15 C14 179.0(5) . . . . ? C11 C10 C15 C14 2.0(8) . . . . ? N9 C10 C15 I2 0.7(8) . . . . ? C11 C10 C15 I2 -176.3(4) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962374' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4c _audit_creation_date 2012-10-12T15:36:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H6 Cl I2 N3' _chemical_formula_sum 'C12 H6 Cl I2 N3' _chemical_formula_weight 481.45 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c 21' _symmetry_space_group_name_Hall 'P 2c -2b' _symmetry_Int_Tables_number 29 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y+1/2, z' 'x, -y+1/2, z+1/2' _cell_length_a 4.0838(4) _cell_length_b 14.2493(13) _cell_length_c 23.294(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1355.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1920 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 26.94 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description stick _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 2.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.821 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.517 _exptl_absorpt_correction_T_max 0.865 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_unetI/netI 0.0808 _diffrn_reflns_number 5877 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _reflns_number_total 2941 _reflns_number_gt 2555 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0122P)^2^+0.5514P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 2941 _refine_ls_number_parameters 163 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.0844 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.002 _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 0.00(5) _refine_diff_density_max 0.9 _refine_diff_density_min -0.753 _refine_diff_density_rms 0.161 _iucr_refine_instructions_details ; .res file for SHELXL : job.res ................................................................. TITL import in P b c 21 CELL 0.71073 4.0838 14.2493 23.2940 90.000 90.000 90.000 ZERR 4.00 0.0004 0.0013 0.0020 0.000 0.000 0.000 LATT -1 SYMM - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, Z SYMM X, 1/2 - Y, 1/2 + Z SFAC C H N CL I UNIT 48.00 24.00 12.00 4.00 8.00 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.012200 0.551400 FVAR 0.27536 C1 1 0.857750 0.980522 0.863652 11.00000 0.00752 0.01833 = 0.02582 0.00241 -0.00400 0.00456 C2 1 0.717415 0.923453 0.823228 11.00000 0.01989 0.02834 = 0.01987 0.00349 -0.00161 0.00546 AFIX 43 H2 2 0.727152 0.939228 0.783639 11.00000 -1.20000 AFIX 0 C3 1 0.557608 0.840532 0.841542 11.00000 0.02279 0.01954 = 0.03444 -0.00124 -0.00769 0.00583 AFIX 43 H3 2 0.449704 0.803550 0.813370 11.00000 -1.20000 AFIX 0 C4 1 0.548898 0.810578 0.896784 11.00000 0.01692 0.01923 = 0.02603 -0.00969 -0.00292 -0.00210 AFIX 43 H4 2 0.441652 0.754176 0.907710 11.00000 -1.20000 AFIX 0 C5 1 0.706433 0.867531 0.936211 11.00000 0.01739 0.01835 = 0.02252 -0.00774 -0.00155 0.00395 C6 1 0.854729 0.951927 0.920909 11.00000 0.01266 0.01907 = 0.02273 -0.00253 -0.00962 0.00212 N7 3 0.983403 0.995059 0.969061 11.00000 0.02644 0.01943 = 0.01829 -0.00103 -0.00574 -0.00403 N8 3 0.920352 0.941072 1.013214 11.00000 0.02394 0.02306 = 0.02729 -0.00680 -0.00675 0.00194 N9 3 0.749686 0.863668 0.994869 11.00000 0.02997 0.01689 = 0.01620 -0.00549 -0.00039 0.00063 C10 1 0.640776 0.794391 1.034090 11.00000 0.02775 0.02583 = 0.02166 -0.00306 -0.00250 -0.00226 C11 1 0.689107 0.699548 1.023017 11.00000 0.02910 0.02805 = 0.02360 0.00112 0.00505 0.00355 AFIX 43 H11 2 0.793625 0.679761 0.988652 11.00000 -1.20000 AFIX 0 C12 1 0.581957 0.634231 1.063060 11.00000 0.03160 0.01946 = 0.03348 0.00030 -0.00131 0.00494 AFIX 43 H12 2 0.606453 0.569091 1.055509 11.00000 -1.20000 AFIX 0 C13 1 0.440857 0.663276 1.113487 11.00000 0.03086 0.02642 = 0.02667 -0.00184 0.00054 0.00228 C14 1 0.397883 0.755869 1.124691 11.00000 0.01880 0.03429 = 0.01309 -0.00512 -0.00318 0.00157 C15 1 0.500457 0.824493 1.085032 11.00000 0.02431 0.02121 = 0.02998 0.00150 -0.00492 0.00326 AFIX 43 H15 2 0.474216 0.889452 1.092975 11.00000 -1.20000 AFIX 0 CL1 4 0.314793 0.576631 1.161574 11.00000 0.05523 0.03044 = 0.03253 0.00950 0.00759 -0.00441 I1 5 1.080247 1.108454 0.843072 11.00000 0.02265 0.02669 = 0.03323 0.00840 -0.00243 -0.00034 I2 5 0.192931 0.807077 1.201386 11.00000 0.02892 0.04089 = 0.02043 -0.00122 0.00187 0.00607 HKLF 4 REM import in P b c 21 REM R1 = 0.0429 for 2555 Fo > 4sig(Fo) and 0.0529 for all 2941 data REM 163 parameters refined using 1 restraints END WGHT 0.0076 0.8525 REM Highest difference peak 0.90, deepest hole -0.75, 1-sigma level 0.16 Q1 1 0.9333 1.1043 0.8140 11.00000 0.05 0.90 Q2 1 0.8479 1.1076 0.8661 11.00000 0.05 0.79 Q3 1 1.0673 1.0728 0.8168 11.00000 0.05 0.79 Q4 1 -0.0411 0.8001 1.2273 11.00000 0.05 0.69 Q5 1 0.3667 0.8020 1.2338 11.00000 0.05 0.69 Q6 1 1.2828 1.1089 0.8090 11.00000 0.05 0.66 Q7 1 1.2411 1.0378 0.8371 11.00000 0.05 0.65 Q8 1 1.0939 1.1779 0.8784 11.00000 0.05 0.64 Q9 1 0.0588 0.7413 1.2094 11.00000 0.05 0.64 Q10 1 -0.0616 0.8038 1.1805 11.00000 0.05 0.64 Q11 1 -0.1106 0.7996 1.2031 11.00000 0.05 0.64 Q12 1 0.3971 0.7873 1.1694 11.00000 0.05 0.62 Q13 1 0.2746 0.7178 1.2397 11.00000 0.05 0.59 Q14 1 0.8803 1.0394 0.8413 11.00000 0.05 0.59 Q15 1 1.0243 1.1851 0.8065 11.00000 0.05 0.58 Q16 1 0.1555 0.7504 1.2392 11.00000 0.05 0.58 Q17 1 1.2533 1.1071 0.8812 11.00000 0.05 0.56 Q18 1 0.5645 1.0668 0.8452 11.00000 0.05 0.54 Q19 1 0.6763 0.8360 1.2022 11.00000 0.05 0.52 Q20 1 0.3824 0.8393 0.8440 11.00000 0.05 0.51 ; #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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 C1 C 0.8577(17) 0.9805(5) 0.8637(3) 0.0172(17) Uani 1 1 d . . . C2 C 0.7174(19) 0.9235(6) 0.8232(4) 0.0227(17) Uani 1 1 d . . . H2 H 0.7272 0.9392 0.7836 0.027 Uiso 1 1 calc R . . C3 C 0.558(2) 0.8405(5) 0.8415(5) 0.0256(16) Uani 1 1 d . . . H3 H 0.4497 0.8036 0.8134 0.031 Uiso 1 1 calc R . . C4 C 0.549(2) 0.8106(6) 0.8968(4) 0.0207(18) Uani 1 1 d . . . H4 H 0.4417 0.7542 0.9077 0.025 Uiso 1 1 calc R . . C5 C 0.706(2) 0.8675(6) 0.9362(4) 0.0194(17) Uani 1 1 d . . . C6 C 0.8547(18) 0.9519(6) 0.9209(3) 0.0182(17) Uani 1 1 d . . . N7 N 0.9834(16) 0.9951(5) 0.9691(3) 0.0214(15) Uani 1 1 d . . . N8 N 0.9204(16) 0.9411(5) 1.0132(3) 0.0248(16) Uani 1 1 d . . . N9 N 0.7497(17) 0.8637(5) 0.9949(3) 0.0210(15) Uani 1 1 d . . . C10 C 0.641(2) 0.7944(6) 1.0341(4) 0.0251(19) Uani 1 1 d . . . C11 C 0.689(2) 0.6995(6) 1.0230(4) 0.027(2) Uani 1 1 d . . . H11 H 0.7936 0.6798 0.9887 0.032 Uiso 1 1 calc R . . C12 C 0.582(2) 0.6342(6) 1.0631(4) 0.028(2) Uani 1 1 d . . . H12 H 0.6065 0.5691 1.0555 0.034 Uiso 1 1 calc R . . C13 C 0.441(2) 0.6633(7) 1.1135(4) 0.028(2) Uani 1 1 d . . . C14 C 0.3979(19) 0.7559(7) 1.1247(3) 0.0221(18) Uani 1 1 d . . . C15 C 0.500(2) 0.8245(7) 1.0850(4) 0.0252(19) Uani 1 1 d . . . H15 H 0.4742 0.8895 1.093 0.03 Uiso 1 1 calc R . . Cl1 Cl 0.3148(7) 0.57663(18) 1.16157(10) 0.0394(6) Uani 1 1 d . . . I1 I 1.08025(13) 1.10845(4) 0.84307(2) 0.02753(13) Uani 1 1 d . . . I2 I 0.19293(13) 0.80708(4) 1.20139(3) 0.03008(14) 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 0.008(4) 0.018(4) 0.026(4) 0.002(3) -0.004(3) 0.005(3) C2 0.020(4) 0.028(4) 0.020(4) 0.003(3) -0.002(3) 0.005(4) C3 0.023(4) 0.020(4) 0.034(4) -0.001(5) -0.008(4) 0.006(4) C4 0.017(4) 0.019(4) 0.026(4) -0.010(3) -0.003(3) -0.002(4) C5 0.017(4) 0.018(4) 0.023(4) -0.008(3) -0.002(3) 0.004(3) C6 0.013(4) 0.019(4) 0.023(4) -0.003(3) -0.010(3) 0.002(3) N7 0.026(4) 0.019(3) 0.018(3) -0.001(3) -0.006(3) -0.004(3) N8 0.024(4) 0.023(4) 0.027(4) -0.007(3) -0.007(3) 0.002(3) N9 0.030(4) 0.017(3) 0.016(3) -0.005(3) 0.000(3) 0.001(3) C10 0.028(5) 0.026(4) 0.022(4) -0.003(4) -0.003(3) -0.002(4) C11 0.029(5) 0.028(5) 0.024(4) 0.001(4) 0.005(4) 0.004(4) C12 0.032(5) 0.019(4) 0.033(5) 0.000(4) -0.001(4) 0.005(4) C13 0.031(5) 0.026(5) 0.027(5) -0.002(4) 0.001(4) 0.002(4) C14 0.019(4) 0.034(5) 0.013(4) -0.005(3) -0.003(3) 0.002(4) C15 0.024(5) 0.021(4) 0.030(5) 0.002(4) -0.005(3) 0.003(4) Cl1 0.0552(16) 0.0304(13) 0.0325(13) 0.0095(10) 0.0076(11) -0.0044(12) I1 0.0226(3) 0.0267(2) 0.0332(3) 0.0084(3) -0.0024(3) -0.0003(2) I2 0.0289(3) 0.0409(3) 0.0204(2) -0.0012(3) 0.0019(3) 0.0061(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.370(11) . ? C1 C6 1.395(11) . ? C1 I1 2.093(8) . ? C2 C3 1.416(12) . ? C2 H2 0.95 . ? C3 C4 1.356(14) . ? C3 H3 0.95 . ? C4 C5 1.384(11) . ? C4 H4 0.95 . ? C5 N9 1.379(10) . ? C5 C6 1.393(12) . ? C6 N7 1.383(10) . ? N7 N8 1.310(10) . ? N8 N9 1.373(10) . ? N9 C10 1.417(11) . ? C10 C15 1.386(12) . ? C10 C11 1.390(12) . ? C11 C12 1.388(12) . ? C11 H11 0.95 . ? C12 C13 1.372(13) . ? C12 H12 0.95 . ? C13 C14 1.356(13) . ? C13 Cl1 1.745(10) . ? C14 C15 1.409(13) . ? C14 I2 2.103(8) . ? C15 H15 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 C2 C1 C6 118.7(8) . . ? C2 C1 I1 122.8(6) . . ? C6 C1 I1 118.5(6) . . ? C1 C2 C3 118.8(8) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 124.1(9) . . ? C4 C3 H3 117.9 . . ? C2 C3 H3 117.9 . . ? C3 C4 C5 115.6(8) . . ? C3 C4 H4 122.2 . . ? C5 C4 H4 122.2 . . ? N9 C5 C4 133.9(8) . . ? N9 C5 C6 103.4(7) . . ? C4 C5 C6 122.6(8) . . ? N7 C6 C1 130.0(8) . . ? N7 C6 C5 110.0(7) . . ? C1 C6 C5 120.1(7) . . ? N8 N7 C6 107.5(6) . . ? N7 N8 N9 109.1(6) . . ? N8 N9 C5 110.0(7) . . ? N8 N9 C10 121.2(7) . . ? C5 N9 C10 128.8(7) . . ? C15 C10 C11 121.2(8) . . ? C15 C10 N9 117.8(8) . . ? C11 C10 N9 120.9(8) . . ? C12 C11 C10 118.8(8) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C13 C12 C11 120.3(9) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 120.8(9) . . ? C14 C13 Cl1 121.8(7) . . ? C12 C13 Cl1 117.4(8) . . ? C13 C14 C15 120.7(8) . . ? C13 C14 I2 123.5(7) . . ? C15 C14 I2 115.7(7) . . ? C10 C15 C14 118.0(9) . . ? C10 C15 H15 121 . . ? C14 C15 H15 121 . . ? 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 3.8(11) . . . . ? I1 C1 C2 C3 -176.7(5) . . . . ? C1 C2 C3 C4 -3.8(12) . . . . ? C2 C3 C4 C5 0.7(12) . . . . ? C3 C4 C5 N9 178.8(9) . . . . ? C3 C4 C5 C6 2.2(12) . . . . ? C2 C1 C6 N7 178.6(8) . . . . ? I1 C1 C6 N7 -0.9(12) . . . . ? C2 C1 C6 C5 -1.0(12) . . . . ? I1 C1 C6 C5 179.5(6) . . . . ? N9 C5 C6 N7 0.7(9) . . . . ? C4 C5 C6 N7 178.2(7) . . . . ? N9 C5 C6 C1 -179.6(7) . . . . ? C4 C5 C6 C1 -2.1(12) . . . . ? C1 C6 N7 N8 -179.7(8) . . . . ? C5 C6 N7 N8 -0.1(9) . . . . ? C6 N7 N8 N9 -0.6(8) . . . . ? N7 N8 N9 C5 1.1(9) . . . . ? N7 N8 N9 C10 -178.2(7) . . . . ? C4 C5 N9 N8 -178.1(9) . . . . ? C6 C5 N9 N8 -1.1(9) . . . . ? C4 C5 N9 C10 1.1(16) . . . . ? C6 C5 N9 C10 178.1(8) . . . . ? N8 N9 C10 C15 43.7(11) . . . . ? C5 N9 C10 C15 -135.4(9) . . . . ? N8 N9 C10 C11 -133.0(8) . . . . ? C5 N9 C10 C11 47.9(13) . . . . ? C15 C10 C11 C12 2.6(13) . . . . ? N9 C10 C11 C12 179.2(8) . . . . ? C10 C11 C12 C13 -2.2(14) . . . . ? C11 C12 C13 C14 1.2(14) . . . . ? C11 C12 C13 Cl1 -179.7(7) . . . . ? C12 C13 C14 C15 -0.7(13) . . . . ? Cl1 C13 C14 C15 -179.7(7) . . . . ? C12 C13 C14 I2 -178.7(7) . . . . ? Cl1 C13 C14 I2 2.3(11) . . . . ? C11 C10 C15 C14 -2.0(13) . . . . ? N9 C10 C15 C14 -178.7(7) . . . . ? C13 C14 C15 C10 1.1(13) . . . . ? I2 C14 C15 C10 179.2(6) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962375' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4c' _audit_creation_date 2012-10-10T09:21:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H6 Cl I2 N3' _chemical_formula_sum 'C12 H6 Cl I2 N3' _chemical_formula_weight 481.45 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1169(3) _cell_length_b 8.2892(3) _cell_length_c 12.3378(5) _cell_angle_alpha 77.399(2) _cell_angle_beta 74.075(2) _cell_angle_gamma 73.384(2) _cell_volume 662.94(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1918 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 24.39 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description stick _exptl_crystal_colour colourless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 2.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.929 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.763 _exptl_absorpt_correction_T_max 0.906 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_unetI/netI 0.0685 _diffrn_reflns_number 8433 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 2987 _reflns_number_gt 2162 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0247P)^2^+2.3625P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 2987 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0789 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.182 _refine_diff_density_min -1.252 _refine_diff_density_rms 0.209 _iucr_refine_instructions_details ; .res file for SHELXL : job.res ................................................................. TITL import in P -1 CELL 0.71073 7.1169 8.2892 12.3378 77.399 74.075 73.384 ZERR 2.00 0.0003 0.0003 0.0005 0.002 0.002 0.002 LATT 1 SFAC C H N CL I UNIT 24 12 6 2 4 MERG 2 FMAP 2 PLAN 20 htab ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.024700 2.362500 FVAR 0.36545 I1 5 0.722910 -0.022535 0.340713 11.00000 0.03193 0.01894 = 0.02495 -0.00299 -0.00571 -0.00872 I2 5 0.265768 0.367138 0.232539 11.00000 0.02211 0.03111 = 0.02617 -0.01145 -0.00397 -0.00743 CL1 4 0.718171 0.083087 -0.167775 11.00000 0.04455 0.03244 = 0.01760 -0.00765 -0.00292 -0.01735 C1 1 0.741472 0.196365 0.392630 11.00000 0.02100 0.02208 = 0.02035 -0.00417 -0.00527 -0.00856 C2 1 0.763955 0.188542 0.500874 11.00000 0.02926 0.01877 = 0.02244 0.00138 -0.00725 -0.00537 AFIX 43 H2 2 0.770148 0.083372 0.551032 11.00000 -1.20000 AFIX 0 C3 1 0.778147 0.331088 0.540082 11.00000 0.03761 0.02694 = 0.01894 -0.00244 -0.01158 -0.01659 AFIX 43 H3 2 0.797454 0.318766 0.614928 11.00000 -1.20000 AFIX 0 C4 1 0.764717 0.487085 0.472647 11.00000 0.02519 0.02236 = 0.01780 -0.00467 -0.00905 -0.00739 AFIX 43 H4 2 0.768881 0.584301 0.500043 11.00000 -1.20000 AFIX 0 C5 1 0.744623 0.496694 0.361775 11.00000 0.01868 0.01188 = 0.01859 -0.00045 -0.00210 -0.00745 C6 1 0.733437 0.355177 0.321711 11.00000 0.01275 0.01714 = 0.01744 -0.00432 -0.00298 -0.00430 N7 3 0.716730 0.415526 0.210570 11.00000 0.02847 0.01629 = 0.01209 -0.00098 -0.00688 -0.01077 N8 3 0.720346 0.586460 0.185392 11.00000 0.02601 0.01530 = 0.02512 0.00148 -0.01100 -0.00754 N9 3 0.734786 0.634522 0.275058 11.00000 0.02349 0.01925 = 0.02941 -0.00566 -0.00738 -0.01036 C10 1 0.715286 0.333282 0.122026 11.00000 0.02114 0.01527 = 0.01154 0.00050 -0.00513 -0.00382 C11 1 0.537397 0.302217 0.111374 11.00000 0.02406 0.01777 = 0.01834 -0.00119 -0.00440 -0.00799 C12 1 0.538941 0.226187 0.022201 11.00000 0.03008 0.02402 = 0.01503 -0.00046 -0.00659 -0.01120 AFIX 43 H12 2 0.418880 0.205890 0.014354 11.00000 -1.20000 AFIX 0 C13 1 0.717883 0.180283 -0.055220 11.00000 0.04427 0.01484 = 0.00754 0.00089 -0.00843 -0.01075 C14 1 0.893963 0.209858 -0.047509 11.00000 0.02825 0.02807 = 0.02341 -0.00719 -0.00129 -0.00707 AFIX 43 H14 2 1.015555 0.177402 -0.102227 11.00000 -1.20000 AFIX 0 C15 1 0.890212 0.288118 0.041905 11.00000 0.02419 0.02155 = 0.01973 0.00460 -0.00657 -0.00806 AFIX 43 H15 2 1.010268 0.310783 0.047801 11.00000 -1.20000 HKLF 4 REM import in P -1 REM R1 = 0.0416 for 2162 Fo > 4sig(Fo) and 0.0695 for all 2987 data REM 163 parameters refined using 0 restraints END WGHT 0.0243 2.4055 REM Highest difference peak 1.18, deepest hole -1.25, 1-sigma level 0.21 Q1 1 0.7738 0.7602 0.4618 11.00000 0.05 1.18 Q2 1 0.2043 0.3919 0.2448 11.00000 0.05 0.97 Q3 1 0.7605 0.6389 0.5918 11.00000 0.05 0.82 Q4 1 0.0620 0.4805 0.2246 11.00000 0.05 0.82 Q5 1 0.7811 0.4728 0.4110 11.00000 0.05 0.80 Q6 1 0.2977 0.2902 0.2734 11.00000 0.05 0.79 Q7 1 0.3027 0.3850 0.1847 11.00000 0.05 0.75 Q8 1 0.9135 -0.0860 0.2720 11.00000 0.05 0.73 Q9 1 0.3134 0.4004 0.2521 11.00000 0.05 0.71 Q10 1 0.6998 0.1228 0.3586 11.00000 0.05 0.71 Q11 1 0.8389 0.3143 -0.0498 11.00000 0.05 0.70 Q12 1 0.2705 0.4096 0.2788 11.00000 0.05 0.70 Q13 1 0.8001 0.1996 -0.0445 11.00000 0.05 0.69 Q14 1 0.3679 0.3102 0.3364 11.00000 0.05 0.69 Q15 1 1.0554 0.2186 0.3751 11.00000 0.05 0.68 Q16 1 0.5386 0.0832 0.3416 11.00000 0.05 0.67 Q17 1 0.7611 -0.0842 -0.1640 11.00000 0.05 0.66 Q18 1 0.9464 0.2479 -0.0959 11.00000 0.05 0.64 Q19 1 0.7657 0.2271 0.5368 11.00000 0.05 0.64 Q20 1 0.2109 0.5311 0.2395 11.00000 0.05 0.63 ; #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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 0.72291(7) -0.02254(6) 0.34071(4) 0.02492(15) Uani 1 1 d . . . I2 I 0.26577(7) 0.36714(6) 0.23254(4) 0.02541(15) Uani 1 1 d . . . Cl1 Cl 0.7182(3) 0.0831(2) -0.16777(16) 0.0300(4) Uani 1 1 d . . . C1 C 0.7415(10) 0.1964(8) 0.3926(6) 0.0201(15) Uani 1 1 d . . . C2 C 0.7640(10) 0.1885(9) 0.5009(6) 0.0240(16) Uani 1 1 d . . . H2 H 0.7701 0.0834 0.551 0.029 Uiso 1 1 calc R . . C3 C 0.7781(11) 0.3311(9) 0.5401(6) 0.0250(17) Uani 1 1 d . . . H3 H 0.7975 0.3188 0.6149 0.03 Uiso 1 1 calc R . . C4 C 0.7647(10) 0.4871(9) 0.4726(6) 0.0203(15) Uani 1 1 d . . . H4 H 0.7689 0.5843 0.5 0.024 Uiso 1 1 calc R . . C5 C 0.7446(10) 0.4967(8) 0.3618(6) 0.0163(14) Uani 1 1 d . . . C6 C 0.7334(9) 0.3552(8) 0.3217(6) 0.0154(14) Uani 1 1 d . . . N7 N 0.7167(8) 0.4155(7) 0.2106(5) 0.0175(12) Uani 1 1 d . . . N8 N 0.7203(8) 0.5865(7) 0.1854(5) 0.0213(13) Uani 1 1 d . . . N9 N 0.7348(8) 0.6345(7) 0.2751(5) 0.0223(13) Uani 1 1 d . . . C10 C 0.7153(10) 0.3333(8) 0.1220(6) 0.0162(14) Uani 1 1 d . . . C11 C 0.5374(10) 0.3022(8) 0.1114(6) 0.0198(15) Uani 1 1 d . . . C12 C 0.5389(11) 0.2262(8) 0.0222(6) 0.0221(16) Uani 1 1 d . . . H12 H 0.4189 0.2059 0.0144 0.027 Uiso 1 1 calc R . . C13 C 0.7179(11) 0.1803(8) -0.0552(6) 0.0213(16) Uani 1 1 d . . . C14 C 0.8940(11) 0.2099(9) -0.0475(7) 0.0269(17) Uani 1 1 d . . . H14 H 1.0156 0.1774 -0.1022 0.032 Uiso 1 1 calc R . . C15 C 0.8902(11) 0.2881(8) 0.0419(6) 0.0222(16) Uani 1 1 d . . . H15 H 1.0103 0.3108 0.0478 0.027 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 I1 0.0319(3) 0.0189(2) 0.0249(3) -0.0030(2) -0.0057(2) -0.0087(2) I2 0.0221(3) 0.0311(3) 0.0262(3) -0.0115(2) -0.0040(2) -0.0074(2) Cl1 0.0445(12) 0.0324(10) 0.0176(10) -0.0076(8) -0.0029(8) -0.0174(9) C1 0.021(4) 0.022(4) 0.020(4) -0.004(3) -0.005(3) -0.009(3) C2 0.029(4) 0.019(3) 0.022(4) 0.001(3) -0.007(3) -0.005(3) C3 0.038(5) 0.027(4) 0.019(4) -0.002(3) -0.012(3) -0.017(3) C4 0.025(4) 0.022(3) 0.018(4) -0.005(3) -0.009(3) -0.007(3) C5 0.019(4) 0.012(3) 0.019(4) 0.000(3) -0.002(3) -0.007(3) C6 0.013(3) 0.017(3) 0.017(4) -0.004(3) -0.003(3) -0.004(3) N7 0.028(3) 0.016(3) 0.012(3) -0.001(2) -0.007(2) -0.011(2) N8 0.026(3) 0.015(3) 0.025(4) 0.001(3) -0.011(3) -0.008(2) N9 0.023(3) 0.019(3) 0.029(4) -0.006(3) -0.007(3) -0.010(2) C10 0.021(4) 0.015(3) 0.012(4) 0.001(3) -0.005(3) -0.004(3) C11 0.024(4) 0.018(3) 0.018(4) -0.001(3) -0.004(3) -0.008(3) C12 0.030(4) 0.024(4) 0.015(4) 0.000(3) -0.007(3) -0.011(3) C13 0.044(5) 0.015(3) 0.008(3) 0.001(3) -0.008(3) -0.011(3) C14 0.028(4) 0.028(4) 0.023(4) -0.007(3) -0.001(3) -0.007(3) C15 0.024(4) 0.022(3) 0.020(4) 0.005(3) -0.007(3) -0.008(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.100(7) . ? I2 C11 2.105(7) . ? Cl1 C13 1.750(7) . ? C1 C2 1.374(10) . ? C1 C6 1.408(9) . ? C2 C3 1.409(9) . ? C2 H2 0.95 . ? C3 C4 1.370(9) . ? C3 H3 0.95 . ? C4 C5 1.397(9) . ? C4 H4 0.95 . ? C5 N9 1.385(8) . ? C5 C6 1.398(9) . ? C6 N7 1.379(8) . ? N7 N8 1.389(7) . ? N7 C10 1.412(8) . ? N8 N9 1.293(8) . ? C10 C15 1.374(9) . ? C10 C11 1.407(9) . ? C11 C12 1.378(9) . ? C12 C13 1.376(10) . ? C12 H12 0.95 . ? C13 C14 1.375(10) . ? C14 C15 1.387(10) . ? C14 H14 0.95 . ? C15 H15 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 C2 C1 C6 116.6(6) . . ? C2 C1 I1 119.8(5) . . ? C6 C1 I1 123.6(5) . . ? C1 C2 C3 122.3(6) . . ? C1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C4 C3 C2 121.5(7) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 117.0(6) . . ? C3 C4 H4 121.5 . . ? C5 C4 H4 121.5 . . ? N9 C5 C4 129.3(6) . . ? N9 C5 C6 108.8(6) . . ? C4 C5 C6 121.9(6) . . ? N7 C6 C5 104.2(5) . . ? N7 C6 C1 135.0(6) . . ? C5 C6 C1 120.8(6) . . ? C6 N7 N8 109.2(5) . . ? C6 N7 C10 132.1(5) . . ? N8 N7 C10 118.5(5) . . ? N9 N8 N7 108.9(5) . . ? N8 N9 C5 108.9(5) . . ? C15 C10 C11 119.1(6) . . ? C15 C10 N7 119.2(6) . . ? C11 C10 N7 121.6(6) . . ? C12 C11 C10 120.4(6) . . ? C12 C11 I2 118.9(5) . . ? C10 C11 I2 120.7(5) . . ? C13 C12 C11 118.7(7) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C14 C13 C12 122.3(7) . . ? C14 C13 Cl1 119.5(6) . . ? C12 C13 Cl1 118.2(6) . . ? C13 C14 C15 118.6(7) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? C10 C15 C14 120.9(7) . . ? C10 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? 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 0.1(10) . . . . ? I1 C1 C2 C3 179.7(5) . . . . ? C1 C2 C3 C4 1.8(11) . . . . ? C2 C3 C4 C5 -2.5(10) . . . . ? C3 C4 C5 N9 -177.6(7) . . . . ? C3 C4 C5 C6 1.6(10) . . . . ? N9 C5 C6 N7 -0.1(7) . . . . ? C4 C5 C6 N7 -179.4(6) . . . . ? N9 C5 C6 C1 179.5(6) . . . . ? C4 C5 C6 C1 0.2(10) . . . . ? C2 C1 C6 N7 178.5(7) . . . . ? I1 C1 C6 N7 -1.1(11) . . . . ? C2 C1 C6 C5 -1.0(10) . . . . ? I1 C1 C6 C5 179.4(5) . . . . ? C5 C6 N7 N8 0.7(7) . . . . ? C1 C6 N7 N8 -178.9(7) . . . . ? C5 C6 N7 C10 174.4(6) . . . . ? C1 C6 N7 C10 -5.2(12) . . . . ? C6 N7 N8 N9 -1.1(7) . . . . ? C10 N7 N8 N9 -175.7(5) . . . . ? N7 N8 N9 C5 1.0(7) . . . . ? C4 C5 N9 N8 178.7(7) . . . . ? C6 C5 N9 N8 -0.6(7) . . . . ? C6 N7 C10 C15 -97.5(8) . . . . ? N8 N7 C10 C15 75.7(7) . . . . ? C6 N7 C10 C11 85.0(9) . . . . ? N8 N7 C10 C11 -101.8(7) . . . . ? C15 C10 C11 C12 0.5(9) . . . . ? N7 C10 C11 C12 178.1(6) . . . . ? C15 C10 C11 I2 179.5(5) . . . . ? N7 C10 C11 I2 -2.9(8) . . . . ? C10 C11 C12 C13 0.5(9) . . . . ? I2 C11 C12 C13 -178.5(5) . . . . ? C11 C12 C13 C14 -0.9(10) . . . . ? C11 C12 C13 Cl1 179.8(5) . . . . ? C12 C13 C14 C15 0.3(10) . . . . ? Cl1 C13 C14 C15 179.6(5) . . . . ? C11 C10 C15 C14 -1.2(9) . . . . ? N7 C10 C15 C14 -178.8(6) . . . . ? C13 C14 C15 C10 0.8(10) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962376' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4d _audit_creation_date 2012-07-12T18:20:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H6 F3 I2 N3' _chemical_formula_sum 'C13 H6 F3 I2 N3' _chemical_formula_weight 515.01 _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 13.300(3) _cell_length_b 5.2093(11) _cell_length_c 21.672(6) _cell_angle_alpha 90 _cell_angle_beta 95.208(8) _cell_angle_gamma 90 _cell_volume 1495.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 4443 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 27.36 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 2.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.431 _exptl_absorpt_correction_T_max 0.683 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 250(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_unetI/netI 0.04 _diffrn_reflns_number 12388 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3424 _reflns_number_gt 2806 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0258P)^2^+2.0859P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 3424 _refine_ls_number_parameters 209 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_gt 0.0706 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.034 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.58 _refine_diff_density_min -1.012 _refine_diff_density_rms 0.11 _iucr_refine_instructions_details ; .res file for SHELXL : EN1164b.res ................................................................. TITL import in P 21/a CELL 0.71073 13.3000 5.2093 21.6720 90.000 95.208 90.000 ZERR 4.00 0.0030 0.0011 0.0060 0.000 0.008 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, - Z SFAC C H N F I UNIT 52 24 12 12 8 MERG 2 SUMP 1 0.0001 1 2 1 3 1 4 1 5 EADP F14A F14B F15A F15B F16A F16B F14C F14D F15C F15D F16C F16D FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.025800 2.085900 FVAR 0.32422 0.31907 0.20324 0.18116 0.29653 I1 5 -0.216904 -0.223050 0.931269 11.00000 0.05590 0.05244 = 0.06206 0.01470 0.02532 0.00645 I2 5 0.175433 -0.017299 0.745578 11.00000 0.03085 0.03290 = 0.04417 0.00435 0.00238 0.00264 C1 1 -0.111122 0.059746 0.832569 11.00000 0.03299 0.02734 = 0.03629 0.00082 0.00488 0.00356 C2 1 -0.116926 0.035373 0.896295 11.00000 0.04080 0.03157 = 0.04242 0.00199 0.00900 0.00766 C3 1 -0.054301 0.185545 0.934224 11.00000 0.05617 0.05299 = 0.03242 -0.00240 0.00410 0.00632 AFIX 43 H3 2 -0.057305 0.176380 0.977798 11.00000 -1.20000 AFIX 0 C4 1 0.015203 0.355090 0.909694 11.00000 0.05384 0.05741 = 0.04086 -0.01856 -0.00468 -0.00809 AFIX 43 H4 2 0.059015 0.453247 0.937588 11.00000 -1.20000 AFIX 0 C5 1 0.021663 0.382781 0.848045 11.00000 0.04445 0.04605 = 0.04456 -0.00957 0.00173 -0.00811 AFIX 43 H5 2 0.067204 0.500570 0.832001 11.00000 -1.20000 AFIX 0 C6 1 -0.042481 0.228188 0.809508 11.00000 0.02779 0.03297 = 0.03596 -0.00242 0.00195 0.00125 C7 1 -0.006545 0.319302 0.699462 11.00000 0.03092 0.03167 = 0.03065 -0.00331 0.00057 -0.00475 C8 1 0.093829 0.259619 0.691882 11.00000 0.02653 0.02923 = 0.03232 -0.00306 0.00033 0.00067 C9 1 0.141052 0.380948 0.645601 11.00000 0.02712 0.03807 = 0.04139 -0.00424 0.00670 0.00104 AFIX 43 H9 2 0.209603 0.343588 0.640166 11.00000 -1.20000 AFIX 0 C10 1 0.088110 0.557663 0.607030 11.00000 0.04255 0.03976 = 0.02909 -0.00368 0.00155 -0.00448 C11 1 -0.011056 0.614233 0.614903 11.00000 0.04352 0.04518 = 0.03215 0.00558 -0.00363 0.00657 AFIX 43 H11 2 -0.046740 0.735471 0.588489 11.00000 -1.20000 AFIX 0 C12 1 -0.058581 0.495273 0.661025 11.00000 0.02741 0.04695 = 0.04048 -0.00255 0.00385 0.00468 AFIX 43 H12 2 -0.127026 0.534172 0.666394 11.00000 -1.20000 AFIX 0 C13 1 0.141971 0.683355 0.557424 11.00000 0.05161 0.05441 = 0.04325 0.00161 0.00551 0.00735 N1 3 -0.163508 -0.065322 0.783657 11.00000 0.03576 0.03256 = 0.04222 -0.00296 0.00289 -0.00378 N2 3 -0.130458 0.019345 0.732440 11.00000 0.02876 0.03386 = 0.04091 -0.00506 0.00172 -0.00371 N3 3 -0.057155 0.198004 0.746809 11.00000 0.02603 0.03087 = 0.03568 -0.00533 0.00316 -0.00345 PART 1 F14A 4 0.219812 0.843553 0.584622 21.00000 0.06776 0.05835 = 0.04125 -0.00397 0.01344 -0.01149 F15A 4 0.083346 0.834181 0.519458 21.00000 0.06776 0.05835 = 0.04125 -0.00397 0.01344 -0.01149 F16A 4 0.183812 0.530785 0.520991 21.00000 0.06776 0.05835 = 0.04125 -0.00397 0.01344 -0.01149 PART 2 F14B 4 0.119890 0.604590 0.501260 31.00000 0.06776 0.05835 = 0.04125 -0.00397 0.01344 -0.01149 F15B 4 0.245093 0.657732 0.564479 31.00000 0.06776 0.05835 = 0.04125 -0.00397 0.01344 -0.01149 F16B 4 0.127827 0.933933 0.552672 31.00000 0.06776 0.05835 = 0.04125 -0.00397 0.01344 -0.01149 PART 3 F14C 4 0.230847 0.544859 0.543747 41.00000 0.06776 0.05835 = 0.04125 -0.00397 0.01344 -0.01149 F15C 4 0.078107 0.717731 0.504409 41.00000 0.06776 0.05835 = 0.04125 -0.00397 0.01344 -0.01149 F16C 4 0.179253 0.910484 0.572014 41.00000 0.06776 0.05835 = 0.04125 -0.00397 0.01344 -0.01149 PART 4 F14D 4 0.090749 0.907577 0.538164 51.00000 0.06776 0.05835 = 0.04125 -0.00397 0.01344 -0.01149 F15D 4 0.230178 0.762076 0.576421 51.00000 0.06776 0.05835 = 0.04125 -0.00397 0.01344 -0.01149 F16D 4 0.146703 0.513788 0.510651 51.00000 0.06776 0.05835 = 0.04125 -0.00397 0.01344 -0.01149 HKLF 4 REM import in P 21/a REM R1 = 0.0327 for 2806 Fo > 4sig(Fo) and 0.0436 for all 3424 data REM 209 parameters refined using 1 restraints END WGHT 0.0252 2.0361 REM Highest difference peak 0.580, deepest hole -1.012, 1-sigma level 0.110 Q1 1 0.0434 0.7586 0.5193 11.00000 0.05 0.58 Q2 1 0.1470 0.0387 0.7731 11.00000 0.05 0.58 Q3 1 0.1797 0.4233 0.5281 11.00000 0.05 0.53 Q4 1 0.0813 0.5559 0.5052 11.00000 0.05 0.45 Q5 1 0.1142 0.7596 0.4982 11.00000 0.05 0.45 Q6 1 0.1653 -0.2062 0.7440 11.00000 0.05 0.44 Q7 1 -0.2627 -0.3280 0.9025 11.00000 0.05 0.43 Q8 1 0.1668 0.6335 0.5066 11.00000 0.05 0.43 Q9 1 0.0590 0.9591 0.5587 11.00000 0.05 0.38 Q10 1 0.1625 -0.0091 0.7194 11.00000 0.05 0.38 Q11 1 -0.2590 -0.2872 0.8486 11.00000 0.05 0.38 Q12 1 0.2369 0.2347 0.8052 11.00000 0.05 0.37 Q13 1 0.0828 0.7478 0.9330 11.00000 0.05 0.37 Q14 1 0.0064 0.2545 0.8340 11.00000 0.05 0.37 Q15 1 -0.0620 0.1239 0.8272 11.00000 0.05 0.37 Q16 1 -0.2153 -0.0553 0.9277 11.00000 0.05 0.36 Q17 1 -0.1192 -0.0110 0.8160 11.00000 0.05 0.36 Q18 1 0.0460 0.4693 0.9945 11.00000 0.05 0.35 Q19 1 -0.0568 0.3483 0.8259 11.00000 0.05 0.35 Q20 1 0.2451 0.7284 0.5938 11.00000 0.05 0.34 ; #----------------------------------------------------------------------------# # 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' F F 0.0171 0.0103 '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 -0.21690(3) -0.22305(7) 0.931269(17) 0.05558(12) Uani 1 1 d . . . I2 I 0.175433(19) -0.01730(5) 0.745578(13) 0.03604(10) Uani 1 1 d . . . C1 C -0.1111(3) 0.0597(8) 0.83257(19) 0.0321(9) Uani 1 1 d . . . C2 C -0.1169(3) 0.0354(8) 0.8963(2) 0.0379(10) Uani 1 1 d . . . C3 C -0.0543(4) 0.1855(9) 0.9342(2) 0.0472(12) Uani 1 1 d . . . H3 H -0.0573 0.1764 0.9778 0.057 Uiso 1 1 calc R . . C4 C 0.0152(4) 0.3551(10) 0.9097(2) 0.0513(12) Uani 1 1 d . . . H4 H 0.059 0.4532 0.9376 0.062 Uiso 1 1 calc R . . C5 C 0.0217(4) 0.3828(9) 0.8480(2) 0.0452(11) Uani 1 1 d . . . H5 H 0.0672 0.5006 0.832 0.054 Uiso 1 1 calc R . . C6 C -0.0425(3) 0.2282(8) 0.80951(19) 0.0323(9) Uani 1 1 d . . . C7 C -0.0065(3) 0.3193(8) 0.69946(19) 0.0312(9) Uani 1 1 d . . . C8 C 0.0938(3) 0.2596(7) 0.69188(19) 0.0295(8) Uani 1 1 d . . . C9 C 0.1411(3) 0.3809(8) 0.6456(2) 0.0353(9) Uani 1 1 d . . . H9 H 0.2096 0.3436 0.6402 0.042 Uiso 1 1 calc R . . C10 C 0.0881(3) 0.5577(9) 0.60703(19) 0.0372(10) Uani 1 1 d . . . C11 C -0.0111(3) 0.6142(9) 0.6149(2) 0.0407(10) Uani 1 1 d . . . H11 H -0.0467 0.7355 0.5885 0.049 Uiso 1 1 calc R . . C12 C -0.0586(3) 0.4953(8) 0.6610(2) 0.0382(10) Uani 1 1 d . . . H12 H -0.127 0.5342 0.6664 0.046 Uiso 1 1 calc R . . C13 C 0.1420(4) 0.6834(10) 0.5574(2) 0.0497(12) Uani 1 1 d . . . N1 N -0.1635(3) -0.0653(7) 0.78366(17) 0.0369(8) Uani 1 1 d . . . N2 N -0.1305(2) 0.0193(6) 0.73244(17) 0.0346(8) Uani 1 1 d . . . N3 N -0.0572(2) 0.1980(6) 0.74681(16) 0.0308(7) Uani 1 1 d . . . F14A F 0.2198(15) 0.844(3) 0.5846(7) 0.0553(10) Uani 0.319(4) 1 d P A 1 F15A F 0.0833(10) 0.834(4) 0.5195(7) 0.0553(10) Uani 0.319(4) 1 d P A 1 F16A F 0.1838(15) 0.531(3) 0.5210(7) 0.0553(10) Uani 0.319(4) 1 d P A 1 F14B F 0.120(2) 0.605(6) 0.5013(9) 0.0553(10) Uani 0.203(10) 1 d P A 2 F15B F 0.2451(15) 0.658(6) 0.5645(10) 0.0553(10) Uani 0.203(10) 1 d P A 2 F16B F 0.128(3) 0.934(4) 0.5527(11) 0.0553(10) Uani 0.203(10) 1 d P A 2 F14C F 0.231(2) 0.545(4) 0.5437(12) 0.0553(10) Uani 0.181(8) 1 d P A 3 F15C F 0.0781(17) 0.718(6) 0.5044(9) 0.0553(10) Uani 0.181(8) 1 d P A 3 F16C F 0.179(2) 0.910(5) 0.5720(11) 0.0553(10) Uani 0.181(8) 1 d P A 3 F14D F 0.0907(15) 0.908(3) 0.5382(8) 0.0553(10) Uani 0.297(13) 1 d P A 4 F15D F 0.2302(13) 0.762(4) 0.5764(8) 0.0553(10) Uani 0.297(13) 1 d P A 4 F16D F 0.1467(13) 0.514(4) 0.5107(7) 0.0553(10) Uani 0.297(13) 1 d P A 4 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 0.0559(2) 0.0524(2) 0.0621(2) 0.01470(16) 0.02532(17) 0.00645(16) I2 0.03085(15) 0.03290(17) 0.04417(17) 0.00435(12) 0.00238(11) 0.00264(12) C1 0.033(2) 0.027(2) 0.036(2) 0.0008(17) 0.0049(17) 0.0036(18) C2 0.041(2) 0.032(2) 0.042(3) 0.0020(19) 0.0090(19) 0.0077(19) C3 0.056(3) 0.053(3) 0.032(2) -0.002(2) 0.004(2) 0.006(3) C4 0.054(3) 0.057(3) 0.041(3) -0.019(2) -0.005(2) -0.008(3) C5 0.044(3) 0.046(3) 0.045(3) -0.010(2) 0.002(2) -0.008(2) C6 0.0278(19) 0.033(2) 0.036(2) -0.0024(18) 0.0020(16) 0.0013(17) C7 0.031(2) 0.032(2) 0.031(2) -0.0033(17) 0.0006(16) -0.0048(18) C8 0.0265(19) 0.029(2) 0.032(2) -0.0031(17) 0.0003(15) 0.0007(17) C9 0.027(2) 0.038(2) 0.041(2) -0.0042(19) 0.0067(17) 0.0010(19) C10 0.043(2) 0.040(2) 0.029(2) -0.0037(18) 0.0016(18) -0.004(2) C11 0.044(2) 0.045(3) 0.032(2) 0.006(2) -0.0036(19) 0.007(2) C12 0.027(2) 0.047(3) 0.040(2) -0.003(2) 0.0039(17) 0.0047(19) C13 0.052(3) 0.054(3) 0.043(3) 0.002(2) 0.006(2) 0.007(3) N1 0.0358(19) 0.0326(19) 0.042(2) -0.0030(16) 0.0029(16) -0.0038(16) N2 0.0288(17) 0.034(2) 0.041(2) -0.0051(16) 0.0017(15) -0.0037(15) N3 0.0260(16) 0.0309(18) 0.0357(19) -0.0053(15) 0.0032(14) -0.0035(15) F14A 0.068(3) 0.058(3) 0.041(3) -0.004(2) 0.013(2) -0.011(3) F15A 0.068(3) 0.058(3) 0.041(3) -0.004(2) 0.013(2) -0.011(3) F16A 0.068(3) 0.058(3) 0.041(3) -0.004(2) 0.013(2) -0.011(3) F14B 0.068(3) 0.058(3) 0.041(3) -0.004(2) 0.013(2) -0.011(3) F15B 0.068(3) 0.058(3) 0.041(3) -0.004(2) 0.013(2) -0.011(3) F16B 0.068(3) 0.058(3) 0.041(3) -0.004(2) 0.013(2) -0.011(3) F14C 0.068(3) 0.058(3) 0.041(3) -0.004(2) 0.013(2) -0.011(3) F15C 0.068(3) 0.058(3) 0.041(3) -0.004(2) 0.013(2) -0.011(3) F16C 0.068(3) 0.058(3) 0.041(3) -0.004(2) 0.013(2) -0.011(3) F14D 0.068(3) 0.058(3) 0.041(3) -0.004(2) 0.013(2) -0.011(3) F15D 0.068(3) 0.058(3) 0.041(3) -0.004(2) 0.013(2) -0.011(3) F16D 0.068(3) 0.058(3) 0.041(3) -0.004(2) 0.013(2) -0.011(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C2 2.083(4) . ? I2 C8 2.094(4) . ? C1 N1 1.378(5) . ? C1 C6 1.391(6) . ? C1 C2 1.396(6) . ? C2 C3 1.363(7) . ? C3 C4 1.416(7) . ? C3 H3 0.95 . ? C4 C5 1.354(7) . ? C4 H4 0.95 . ? C5 C6 1.394(6) . ? C5 H5 0.95 . ? C6 N3 1.364(5) . ? C7 C12 1.381(6) . ? C7 C8 1.395(5) . ? C7 N3 1.425(5) . ? C8 C9 1.384(6) . ? C9 C10 1.391(6) . ? C9 H9 0.95 . ? C10 C11 1.377(6) . ? C10 C13 1.496(7) . ? C11 C12 1.377(6) . ? C11 H11 0.95 . ? C12 H12 0.95 . ? C13 F15D 1.275(18) . ? C13 F16A 1.282(14) . ? C13 F14B 1.293(19) . ? C13 F16C 1.31(2) . ? C13 F16B 1.32(2) . ? C13 F15A 1.336(14) . ? C13 F16D 1.350(17) . ? C13 F15B 1.37(2) . ? C13 F15C 1.38(2) . ? C13 F14D 1.397(18) . ? C13 F14A 1.416(17) . ? C13 F14C 1.44(2) . ? N1 N2 1.307(5) . ? N2 N3 1.363(4) . ? 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 C1 C6 108.9(4) . . ? N1 C1 C2 130.4(4) . . ? C6 C1 C2 120.6(4) . . ? C3 C2 C1 117.3(4) . . ? C3 C2 I1 121.8(3) . . ? C1 C2 I1 120.9(3) . . ? C2 C3 C4 121.0(4) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 122.6(4) . . ? C5 C4 H4 118.7 . . ? C3 C4 H4 118.7 . . ? C4 C5 C6 116.1(4) . . ? C4 C5 H5 122 . . ? C6 C5 H5 122 . . ? N3 C6 C1 104.2(3) . . ? N3 C6 C5 133.4(4) . . ? C1 C6 C5 122.3(4) . . ? C12 C7 C8 120.6(4) . . ? C12 C7 N3 119.0(4) . . ? C8 C7 N3 120.4(4) . . ? C9 C8 C7 119.1(4) . . ? C9 C8 I2 118.1(3) . . ? C7 C8 I2 122.8(3) . . ? C8 C9 C10 120.0(4) . . ? C8 C9 H9 120 . . ? C10 C9 H9 120 . . ? C11 C10 C9 120.4(4) . . ? C11 C10 C13 121.5(4) . . ? C9 C10 C13 118.2(4) . . ? C10 C11 C12 120.1(4) . . ? C10 C11 H11 120 . . ? C12 C11 H11 120 . . ? C11 C12 C7 119.9(4) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? F15D C13 F16A 87.7(11) . . ? F15D C13 F14B 122.0(11) . . ? F16A C13 F14B 45.4(17) . . ? F15D C13 F16C 46.8(13) . . ? F16A C13 F16C 122.2(11) . . ? F14B C13 F16C 124.2(14) . . ? F15D C13 F16B 80.1(13) . . ? F16A C13 F16B 129.1(11) . . ? F14B C13 F16B 102.8(13) . . ? F15D C13 F15A 118.6(11) . . ? F16A C13 F15A 104.3(9) . . ? F14B C13 F15A 62.4(17) . . ? F16C C13 F15A 78.7(13) . . ? F16B C13 F15A 45.6(15) . . ? F15D C13 F16D 110.4(10) . . ? F16C C13 F16D 136.8(12) . . ? F16B C13 F16D 127.1(11) . . ? F15A C13 F16D 89.2(11) . . ? F16A C13 F15B 61.5(15) . . ? F14B C13 F15B 102.3(13) . . ? F16C C13 F15B 73.1(15) . . ? F16B C13 F15B 103.8(13) . . ? F15A C13 F15B 130.3(10) . . ? F16D C13 F15B 84.6(13) . . ? F15D C13 F15C 135.0(12) . . ? F16A C13 F15C 80.6(13) . . ? F16C C13 F15C 106.0(14) . . ? F16B C13 F15C 74.6(15) . . ? F16D C13 F15C 61.7(13) . . ? F15B C13 F15C 129.8(12) . . ? F15D C13 F14D 103.7(9) . . ? F16A C13 F14D 124.2(9) . . ? F14B C13 F14D 85.5(14) . . ? F16C C13 F14D 58.7(14) . . ? F16D C13 F14D 112.2(9) . . ? F15B C13 F14D 124.7(11) . . ? F15C C13 F14D 52.8(12) . . ? F16A C13 F14A 106.3(9) . . ? F14B C13 F14A 132.4(11) . . ? F16B C13 F14A 62.9(16) . . ? F15A C13 F14A 105.9(8) . . ? F16D C13 F14A 128.0(9) . . ? F15B C13 F14A 47.6(16) . . ? F15C C13 F14A 130.0(10) . . ? F14D C13 F14A 87.1(10) . . ? F15D C13 F14C 58.6(12) . . ? F14B C13 F14C 76.6(16) . . ? F16C C13 F14C 101.7(14) . . ? F16B C13 F14C 126.4(14) . . ? F15A C13 F14C 127.8(10) . . ? F16D C13 F14C 54.7(12) . . ? F15C C13 F14C 110.5(13) . . ? F14D C13 F14C 138.2(10) . . ? F14A C13 F14C 78.3(12) . . ? N2 N1 C1 107.9(3) . . ? N1 N2 N3 109.0(3) . . ? N2 N3 C6 109.9(3) . . ? N2 N3 C7 120.9(3) . . ? C6 N3 C7 129.2(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 179.6(4) . . . . ? C6 C1 C2 C3 1.1(6) . . . . ? N1 C1 C2 I1 0.0(6) . . . . ? C6 C1 C2 I1 -178.4(3) . . . . ? C1 C2 C3 C4 -1.3(7) . . . . ? I1 C2 C3 C4 178.2(4) . . . . ? C2 C3 C4 C5 1.8(8) . . . . ? C3 C4 C5 C6 -1.8(7) . . . . ? N1 C1 C6 N3 0.4(4) . . . . ? C2 C1 C6 N3 179.1(4) . . . . ? N1 C1 C6 C5 179.9(4) . . . . ? C2 C1 C6 C5 -1.3(6) . . . . ? C4 C5 C6 N3 -179.0(5) . . . . ? C4 C5 C6 C1 1.6(7) . . . . ? C12 C7 C8 C9 0.6(6) . . . . ? N3 C7 C8 C9 -179.8(4) . . . . ? C12 C7 C8 I2 -177.1(3) . . . . ? N3 C7 C8 I2 2.5(5) . . . . ? C7 C8 C9 C10 -0.7(6) . . . . ? I2 C8 C9 C10 177.1(3) . . . . ? C8 C9 C10 C11 0.5(7) . . . . ? C8 C9 C10 C13 -179.7(4) . . . . ? C9 C10 C11 C12 -0.2(7) . . . . ? C13 C10 C11 C12 -180.0(4) . . . . ? C10 C11 C12 C7 0.1(7) . . . . ? C8 C7 C12 C11 -0.3(6) . . . . ? N3 C7 C12 C11 -179.9(4) . . . . ? C6 C1 N1 N2 -0.3(4) . . . . ? C2 C1 N1 N2 -178.9(4) . . . . ? C1 N1 N2 N3 0.0(4) . . . . ? N1 N2 N3 C6 0.2(4) . . . . ? N1 N2 N3 C7 178.9(3) . . . . ? C1 C6 N3 N2 -0.4(4) . . . . ? C5 C6 N3 N2 -179.9(4) . . . . ? C1 C6 N3 C7 -178.9(4) . . . . ? C5 C6 N3 C7 1.6(7) . . . . ? C12 C7 N3 N2 71.2(5) . . . . ? C8 C7 N3 N2 -108.4(4) . . . . ? C12 C7 N3 C6 -110.4(5) . . . . ? C8 C7 N3 C6 70.0(6) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962377' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4e _audit_creation_date 2012-09-10T11:23:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H9 I2 N3 O' _chemical_formula_sum 'C13 H9 I2 N3 O' _chemical_formula_weight 477.03 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2536(4) _cell_length_b 15.6664(7) _cell_length_c 11.6615(5) _cell_angle_alpha 90 _cell_angle_beta 108.822(2) _cell_angle_gamma 90 _cell_volume 1427.25(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5329 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 27.48 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 2.22 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.402 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.194 _exptl_absorpt_correction_T_max 0.292 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_unetI/netI 0.0331 _diffrn_reflns_number 12392 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 3270 _reflns_number_gt 2889 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0242P)^2^+4.9155P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 3270 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0808 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.641 _refine_diff_density_min -0.86 _refine_diff_density_rms 0.129 _iucr_refine_instructions_details ; .res file for SHELXL : job.res ................................................................. TITL import in P 21/c CELL 0.71073 8.2536 15.6664 11.6615 90.000 108.822 90.000 ZERR 4.00 0.0004 0.0007 0.0005 0.000 0.002 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N I O UNIT 52.00 36.00 12.00 8.00 4.00 MERG 2 FMAP 2 PLAN 20 ACTA HTAB 2.00000 BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.024200 4.915501 FVAR 0.32638 I1 4 -0.173326 0.194487 -0.236537 11.00000 0.04403 0.03606 = 0.02558 0.00107 0.00403 0.00398 C1 1 -0.079378 0.145054 -0.061618 11.00000 0.02907 0.01697 = 0.02393 -0.00087 0.00655 -0.00095 C2 1 -0.183341 0.128632 0.007189 11.00000 0.02319 0.02034 = 0.03082 -0.00835 0.00545 -0.00308 AFIX 43 H2 2 -0.301422 0.142813 -0.023775 11.00000 -1.20000 AFIX 0 C3 1 -0.117722 0.091093 0.122957 11.00000 0.02652 0.02321 = 0.03394 -0.00378 0.01608 -0.00901 AFIX 43 H3 2 -0.194336 0.078959 0.166589 11.00000 -1.20000 AFIX 0 C4 1 0.053835 0.071208 0.175596 11.00000 0.02387 0.02099 = 0.02673 -0.00126 0.01140 -0.00529 AFIX 43 H4 2 0.097418 0.045718 0.253455 11.00000 -1.20000 AFIX 0 C5 1 0.158297 0.091343 0.105913 11.00000 0.02393 0.01249 = 0.02430 -0.00641 0.00952 -0.00289 C6 1 0.096814 0.127190 -0.009046 11.00000 0.02705 0.01420 = 0.02232 -0.00357 0.00898 -0.00256 N7 3 0.231446 0.137683 -0.053826 11.00000 0.03088 0.02303 = 0.02374 0.00252 0.01398 -0.00291 N8 3 0.370332 0.111952 0.029481 11.00000 0.02875 0.02576 = 0.02552 0.00373 0.01544 0.00087 N9 3 0.330030 0.083590 0.127208 11.00000 0.01980 0.01963 = 0.02136 0.00092 0.01002 -0.00203 C10 1 0.461123 0.049142 0.228295 11.00000 0.01802 0.01981 = 0.02089 -0.00071 0.00583 -0.00484 C11 1 0.547821 -0.023977 0.210945 11.00000 0.02377 0.02260 = 0.02400 -0.00436 0.00930 -0.00301 AFIX 43 H11 2 0.516728 -0.049680 0.133062 11.00000 -1.20000 AFIX 0 C12 1 0.677182 -0.059169 0.304769 11.00000 0.02177 0.01827 = 0.03293 -0.00508 0.01301 -0.00176 AFIX 43 H12 2 0.736886 -0.108053 0.291496 11.00000 -1.20000 AFIX 0 C13 1 0.720042 -0.022516 0.419590 11.00000 0.02373 0.02100 = 0.02509 0.00435 0.01236 -0.00388 C14 1 0.634192 0.051155 0.437816 11.00000 0.02333 0.02476 = 0.01976 -0.00543 0.00918 -0.00478 AFIX 43 H14 2 0.663121 0.075810 0.516281 11.00000 -1.20000 AFIX 0 C15 1 0.507882 0.087938 0.342190 11.00000 0.02034 0.01661 = 0.02851 -0.00364 0.01481 -0.00366 I2 4 0.399396 0.202883 0.372421 11.00000 0.02713 0.01951 = 0.03208 -0.00641 0.01327 -0.00115 O16 5 0.844237 -0.051983 0.518514 11.00000 0.02789 0.03042 = 0.02889 0.00178 0.00972 0.00401 C17 1 0.939558 -0.124963 0.501722 11.00000 0.03294 0.03111 = 0.03589 0.00663 0.01033 0.01000 AFIX 137 H17A 2 0.861979 -0.173627 0.474671 11.00000 -1.50000 H17B 2 1.027706 -0.139128 0.578533 11.00000 -1.50000 H17C 2 0.994011 -0.111918 0.440505 11.00000 -1.50000 HKLF 4 REM import in P 21/c REM R1 = 0.0348 for 2889 Fo > 4sig(Fo) and 0.0419 for all 3270 data REM 173 parameters refined using 0 restraints END WGHT 0.0242 4.9149 REM Highest difference peak 1.64, deepest hole -0.86, 1-sigma level 0.13 Q1 1 0.6690 0.1293 0.5710 11.00000 0.05 1.64 Q2 1 -0.1408 0.2331 -0.1822 11.00000 0.05 1.46 Q3 1 -0.2697 0.2093 -0.2728 11.00000 0.05 1.13 Q4 1 0.8291 -0.0809 0.4178 11.00000 0.05 0.55 Q5 1 -0.0982 0.2064 -0.2644 11.00000 0.05 0.54 Q6 1 0.6461 -0.0268 0.2519 11.00000 0.05 0.48 Q7 1 0.4957 0.1928 0.4319 11.00000 0.05 0.48 Q8 1 0.4911 0.0658 0.2885 11.00000 0.05 0.45 Q9 1 0.7515 0.0676 0.6009 11.00000 0.05 0.44 Q10 1 0.8328 -0.2011 0.4209 11.00000 0.05 0.44 Q11 1 0.7788 -0.1180 0.3760 11.00000 0.05 0.43 Q12 1 0.3072 0.1944 0.0390 11.00000 0.05 0.42 Q13 1 0.6958 -0.0371 0.3474 11.00000 0.05 0.42 Q14 1 0.5948 0.0791 0.3797 11.00000 0.05 0.41 Q15 1 0.2234 0.1716 -0.0960 11.00000 0.05 0.40 Q16 1 0.1177 0.1171 0.0644 11.00000 0.05 0.40 Q17 1 0.4036 0.0751 0.1736 11.00000 0.05 0.40 Q18 1 0.5276 0.0129 0.2263 11.00000 0.05 0.39 Q19 1 -0.1363 0.1112 0.0597 11.00000 0.05 0.39 Q20 1 0.1482 0.1353 -0.0563 11.00000 0.05 0.38 ; #----------------------------------------------------------------------------# # 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' I I -0.4742 1.8119 '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' 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 -0.17333(5) 0.19449(2) -0.23654(3) 0.03695(11) Uani 1 1 d . . . C1 C -0.0794(6) 0.1451(3) -0.0616(4) 0.0238(10) Uani 1 1 d . . . C2 C -0.1833(6) 0.1286(3) 0.0072(4) 0.0256(10) Uani 1 1 d . . . H2 H -0.3014 0.1428 -0.0238 0.031 Uiso 1 1 calc R . . C3 C -0.1177(6) 0.0911(3) 0.1230(4) 0.0264(10) Uani 1 1 d . . . H3 H -0.1943 0.079 0.1666 0.032 Uiso 1 1 calc R . . C4 C 0.0538(6) 0.0712(3) 0.1756(4) 0.0231(9) Uani 1 1 d . . . H4 H 0.0974 0.0457 0.2535 0.028 Uiso 1 1 calc R . . C5 C 0.1583(5) 0.0913(3) 0.1059(4) 0.0198(9) Uani 1 1 d . . . C6 C 0.0968(6) 0.1272(3) -0.0090(4) 0.0209(9) Uani 1 1 d . . . N7 N 0.2314(5) 0.1377(2) -0.0538(4) 0.0246(8) Uani 1 1 d . . . N8 N 0.3703(5) 0.1120(2) 0.0295(4) 0.0251(8) Uani 1 1 d . . . N9 N 0.3300(4) 0.0836(2) 0.1272(3) 0.0194(7) Uani 1 1 d . . . C10 C 0.4611(5) 0.0491(3) 0.2283(4) 0.0197(9) Uani 1 1 d . . . C11 C 0.5478(6) -0.0240(3) 0.2109(4) 0.0231(9) Uani 1 1 d . . . H11 H 0.5167 -0.0497 0.1331 0.028 Uiso 1 1 calc R . . C12 C 0.6772(6) -0.0592(3) 0.3048(4) 0.0233(9) Uani 1 1 d . . . H12 H 0.7369 -0.1081 0.2915 0.028 Uiso 1 1 calc R . . C13 C 0.7200(6) -0.0225(3) 0.4196(4) 0.0222(9) Uani 1 1 d . . . C14 C 0.6342(5) 0.0512(3) 0.4378(4) 0.0221(9) Uani 1 1 d . . . H14 H 0.6631 0.0758 0.5163 0.026 Uiso 1 1 calc R . . C15 C 0.5079(5) 0.0879(3) 0.3422(4) 0.0202(9) Uani 1 1 d . . . I2 I 0.39940(4) 0.202883(18) 0.37242(3) 0.02535(10) Uani 1 1 d . . . O16 O 0.8442(4) -0.0520(2) 0.5185(3) 0.0289(7) Uani 1 1 d . . . C17 C 0.9396(7) -0.1250(3) 0.5017(5) 0.0335(12) Uani 1 1 d . . . H17A H 0.862 -0.1736 0.4747 0.05 Uiso 1 1 calc R . . H17B H 1.0277 -0.1391 0.5785 0.05 Uiso 1 1 calc R . . H17C H 0.994 -0.1119 0.4405 0.05 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 I1 0.0440(2) 0.0361(2) 0.02558(19) 0.00107(15) 0.00403(15) 0.00398(15) C1 0.029(2) 0.017(2) 0.024(2) -0.0009(19) 0.0065(19) -0.0010(17) C2 0.023(2) 0.020(2) 0.031(3) -0.008(2) 0.0054(19) -0.0031(18) C3 0.027(2) 0.023(2) 0.034(3) -0.004(2) 0.016(2) -0.0090(19) C4 0.024(2) 0.021(2) 0.027(2) -0.0013(19) 0.0114(19) -0.0053(17) C5 0.024(2) 0.0125(19) 0.024(2) -0.0064(18) 0.0095(18) -0.0029(16) C6 0.027(2) 0.0142(19) 0.022(2) -0.0036(18) 0.0090(19) -0.0026(17) N7 0.031(2) 0.023(2) 0.024(2) 0.0025(17) 0.0140(17) -0.0029(16) N8 0.029(2) 0.026(2) 0.026(2) 0.0037(17) 0.0154(17) 0.0009(16) N9 0.0198(17) 0.0196(18) 0.0214(19) 0.0009(16) 0.0100(15) -0.0020(14) C10 0.018(2) 0.020(2) 0.021(2) -0.0007(18) 0.0058(17) -0.0048(16) C11 0.024(2) 0.023(2) 0.024(2) -0.0044(19) 0.0093(19) -0.0030(18) C12 0.022(2) 0.018(2) 0.033(3) -0.005(2) 0.0130(19) -0.0018(17) C13 0.024(2) 0.021(2) 0.025(2) 0.0043(19) 0.0124(19) -0.0039(17) C14 0.023(2) 0.025(2) 0.020(2) -0.0054(19) 0.0092(18) -0.0048(18) C15 0.020(2) 0.017(2) 0.029(2) -0.0036(19) 0.0148(18) -0.0037(16) I2 0.02713(16) 0.01951(15) 0.03208(19) -0.00641(13) 0.01327(13) -0.00115(11) O16 0.0279(17) 0.0304(18) 0.0289(19) 0.0018(15) 0.0097(15) 0.0040(14) C17 0.033(3) 0.031(3) 0.036(3) 0.007(2) 0.010(2) 0.010(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.084(5) . ? C1 C2 1.375(6) . ? C1 C6 1.412(6) . ? C2 C3 1.411(7) . ? C2 H2 0.95 . ? C3 C4 1.385(6) . ? C3 H3 0.95 . ? C4 C5 1.398(6) . ? C4 H4 0.95 . ? C5 N9 1.363(5) . ? C5 C6 1.390(6) . ? C6 N7 1.382(6) . ? N7 N8 1.305(5) . ? N8 N9 1.361(5) . ? N9 C10 1.424(6) . ? C10 C15 1.397(6) . ? C10 C11 1.399(6) . ? C11 C12 1.374(6) . ? C11 H11 0.95 . ? C12 C13 1.394(6) . ? C12 H12 0.95 . ? C13 O16 1.353(6) . ? C13 C14 1.406(6) . ? C14 C15 1.383(6) . ? C14 H14 0.95 . ? C15 I2 2.091(4) . ? O16 C17 1.437(6) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 117.3(4) . . ? C2 C1 I1 122.4(4) . . ? C6 C1 I1 120.3(3) . . ? C1 C2 C3 121.2(4) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 122.7(4) . . ? C4 C3 H3 118.7 . . ? C2 C3 H3 118.7 . . ? C3 C4 C5 115.2(4) . . ? C3 C4 H4 122.4 . . ? C5 C4 H4 122.4 . . ? N9 C5 C6 104.3(4) . . ? N9 C5 C4 132.4(4) . . ? C6 C5 C4 123.4(4) . . ? N7 C6 C5 109.0(4) . . ? N7 C6 C1 130.8(4) . . ? C5 C6 C1 120.2(4) . . ? N8 N7 C6 107.6(4) . . ? N7 N8 N9 109.3(3) . . ? N8 N9 C5 109.8(4) . . ? N8 N9 C10 119.4(3) . . ? C5 N9 C10 130.7(4) . . ? C15 C10 C11 119.8(4) . . ? C15 C10 N9 121.7(4) . . ? C11 C10 N9 118.5(4) . . ? C12 C11 C10 121.0(4) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 119.4(4) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? O16 C13 C12 124.5(4) . . ? O16 C13 C14 115.5(4) . . ? C12 C13 C14 120.0(4) . . ? C15 C14 C13 120.4(4) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C10 119.4(4) . . ? C14 C15 I2 118.4(3) . . ? C10 C15 I2 122.2(3) . . ? C13 O16 C17 116.9(4) . . ? O16 C17 H17A 109.5 . . ? O16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 C6 C1 C2 C3 -3.4(7) . . . . ? I1 C1 C2 C3 176.7(3) . . . . ? C1 C2 C3 C4 2.1(7) . . . . ? C2 C3 C4 C5 0.3(7) . . . . ? C3 C4 C5 N9 178.2(4) . . . . ? C3 C4 C5 C6 -1.2(6) . . . . ? N9 C5 C6 N7 1.5(5) . . . . ? C4 C5 C6 N7 -178.9(4) . . . . ? N9 C5 C6 C1 -179.7(4) . . . . ? C4 C5 C6 C1 -0.1(7) . . . . ? C2 C1 C6 N7 -179.0(4) . . . . ? I1 C1 C6 N7 0.8(7) . . . . ? C2 C1 C6 C5 2.4(6) . . . . ? I1 C1 C6 C5 -177.7(3) . . . . ? C5 C6 N7 N8 -1.5(5) . . . . ? C1 C6 N7 N8 179.8(4) . . . . ? C6 N7 N8 N9 0.9(5) . . . . ? N7 N8 N9 C5 0.0(5) . . . . ? N7 N8 N9 C10 177.6(4) . . . . ? C6 C5 N9 N8 -0.9(5) . . . . ? C4 C5 N9 N8 179.5(4) . . . . ? C6 C5 N9 C10 -178.2(4) . . . . ? C4 C5 N9 C10 2.3(8) . . . . ? N8 N9 C10 C15 116.4(5) . . . . ? C5 N9 C10 C15 -66.6(6) . . . . ? N8 N9 C10 C11 -61.7(5) . . . . ? C5 N9 C10 C11 115.3(5) . . . . ? C15 C10 C11 C12 0.9(6) . . . . ? N9 C10 C11 C12 179.0(4) . . . . ? C10 C11 C12 C13 1.4(6) . . . . ? C11 C12 C13 O16 179.6(4) . . . . ? C11 C12 C13 C14 -1.7(6) . . . . ? O16 C13 C14 C15 178.4(4) . . . . ? C12 C13 C14 C15 -0.4(6) . . . . ? C13 C14 C15 C10 2.7(6) . . . . ? C13 C14 C15 I2 -175.1(3) . . . . ? C11 C10 C15 C14 -3.0(6) . . . . ? N9 C10 C15 C14 179.0(4) . . . . ? C11 C10 C15 I2 174.7(3) . . . . ? N9 C10 C15 I2 -3.3(5) . . . . ? C12 C13 O16 C17 1.4(6) . . . . ? C14 C13 O16 C17 -177.3(4) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962378' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4e' _audit_creation_date 2012-09-11T11:45:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H9 I2 N3 O' _chemical_formula_sum 'C13 H9 I2 N3 O' _chemical_formula_weight 477.03 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.2004(2) _cell_length_b 20.7217(14) _cell_length_c 15.9102(11) _cell_angle_alpha 90 _cell_angle_beta 97.125(3) _cell_angle_gamma 90 _cell_volume 1374.12(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5300 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.42 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description stick _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_diffrn 2.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.572 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.445 _exptl_absorpt_correction_T_max 0.605 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_unetI/netI 0.0427 _diffrn_reflns_number 11350 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 3121 _reflns_number_gt 2789 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0512P)^2^+2.5306P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 3121 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.108 _refine_ls_goodness_of_fit_ref 1.217 _refine_ls_restrained_S_all 1.217 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.524 _refine_diff_density_min -0.905 _refine_diff_density_rms 0.198 _iucr_refine_instructions_details ; .res file for SHELXL : job.res ................................................................. TITL import in P 21/n CELL 0.71073 4.2004 20.7217 15.9102 90.000 97.125 90.000 ZERR 4.00 0.0002 0.0014 0.0011 0.000 0.003 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O I UNIT 52.00 36.00 12.00 4.00 8.00 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.051200 2.530600 FVAR 0.31558 C1 1 0.620225 0.086181 0.231096 11.00000 0.01884 0.01466 = 0.02183 0.00308 0.00635 -0.00223 C2 1 0.677887 0.144357 0.275279 11.00000 0.02765 0.01846 = 0.01862 -0.00307 0.00388 -0.00244 AFIX 43 H2 2 0.582538 0.183697 0.254376 11.00000 -1.20000 AFIX 0 C3 1 0.880177 0.141815 0.350765 11.00000 0.03318 0.02094 = 0.02275 0.00089 0.00171 -0.00622 AFIX 43 H3 2 0.921480 0.180427 0.382437 11.00000 -1.20000 AFIX 0 C4 1 1.029176 0.083471 0.382900 11.00000 0.03006 0.02752 = 0.01921 0.00280 -0.00038 -0.00418 AFIX 43 H4 2 1.169807 0.083982 0.434490 11.00000 -1.20000 AFIX 0 C5 1 0.970297 0.026861 0.339727 11.00000 0.02042 0.02064 = 0.01879 0.00576 0.00444 -0.00227 C6 1 0.765342 0.027964 0.261891 11.00000 0.02072 0.01663 = 0.01561 0.00233 0.00124 0.00282 N7 3 0.671482 -0.021004 0.206115 11.00000 0.03322 0.01715 = 0.01908 -0.00086 0.00791 0.00125 N8 3 0.482179 0.003082 0.143710 11.00000 0.03499 0.01580 = 0.02131 -0.00061 0.00493 0.00293 N9 3 0.445073 0.068253 0.156439 11.00000 0.02279 0.01667 = 0.01281 -0.00154 0.00177 0.00204 C10 1 0.262920 0.104859 0.091381 11.00000 0.01680 0.01929 = 0.01779 0.00165 0.00262 -0.00054 C11 1 0.126718 0.163232 0.110562 11.00000 0.02094 0.01858 = 0.01620 -0.00437 0.00132 -0.00356 AFIX 43 H11 2 0.148200 0.178607 0.167235 11.00000 -1.20000 AFIX 0 C12 1 -0.041095 0.198738 0.045761 11.00000 0.01529 0.01543 = 0.01883 -0.00264 -0.00072 -0.00140 C13 1 -0.086779 0.175943 -0.037557 11.00000 0.01939 0.01974 = 0.01430 0.00148 -0.00121 -0.00138 C14 1 0.043696 0.116583 -0.055428 11.00000 0.03010 0.02214 = 0.01892 -0.00382 -0.00297 0.00043 AFIX 43 H14 2 0.010813 0.099750 -0.111372 11.00000 -1.20000 AFIX 0 C15 1 0.222904 0.081827 0.008957 11.00000 0.02812 0.02232 = 0.01990 -0.00531 0.00036 0.00216 AFIX 43 H15 2 0.318408 0.042019 -0.003769 11.00000 -1.20000 AFIX 0 O16 4 -0.257365 0.213872 -0.097388 11.00000 0.03710 0.02298 = 0.01489 -0.00187 -0.01037 0.00691 C17 1 -0.311708 0.189099 -0.181949 11.00000 0.04344 0.03412 = 0.01719 -0.00236 -0.00858 0.00536 AFIX 137 H17A 2 -0.105370 0.182421 -0.203415 11.00000 -1.50000 H17B 2 -0.440479 0.219995 -0.218366 11.00000 -1.50000 H17C 2 -0.426475 0.147923 -0.181952 11.00000 -1.50000 AFIX 0 I1 5 1.187116 -0.059752 0.383163 11.00000 0.02183 0.02508 = 0.02665 0.00981 0.00232 0.00122 I2 5 -0.234363 0.288583 0.075142 11.00000 0.02231 0.01709 = 0.02193 -0.00333 -0.00053 0.00301 HKLF 4 REM import in P 21/n REM R1 = 0.0356 for 2789 Fo > 4sig(Fo) and 0.0403 for all 3121 data REM 173 parameters refined using 0 restraints END WGHT 0.0533 2.9256 REM Highest difference peak 1.52, deepest hole -0.90, 1-sigma level 0.20 Q1 1 -0.2163 0.2447 0.0777 11.00000 0.05 1.52 Q2 1 -0.2147 0.3341 0.0794 11.00000 0.05 1.45 Q3 1 1.1784 -0.0139 0.3823 11.00000 0.05 1.44 Q4 1 1.1851 -0.1083 0.3820 11.00000 0.05 1.28 Q5 1 -0.5540 0.2859 0.0433 11.00000 0.05 1.24 Q6 1 0.8447 -0.0560 0.3537 11.00000 0.05 1.08 Q7 1 1.5132 -0.0555 0.4166 11.00000 0.05 1.06 Q8 1 0.0960 0.2868 0.1097 11.00000 0.05 0.89 Q9 1 0.9020 -0.0922 0.3554 11.00000 0.05 0.83 Q10 1 0.4873 0.0678 0.2198 11.00000 0.05 0.65 Q11 1 1.2821 -0.1459 0.3820 11.00000 0.05 0.63 Q12 1 0.1318 0.2731 0.0171 11.00000 0.05 0.63 Q13 1 -0.1153 0.1404 -0.2609 11.00000 0.05 0.63 Q14 1 0.9113 0.1588 0.2813 11.00000 0.05 0.62 Q15 1 0.5722 0.1196 0.2215 11.00000 0.05 0.60 Q16 1 -0.5656 0.2860 -0.2212 11.00000 0.05 0.59 Q17 1 0.6131 0.1791 0.2241 11.00000 0.05 0.58 Q18 1 1.2507 0.1262 0.4769 11.00000 0.05 0.58 Q19 1 0.8614 0.0236 0.3017 11.00000 0.05 0.57 Q20 1 1.5344 0.1012 0.4785 11.00000 0.05 0.57 ; #----------------------------------------------------------------------------# # 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 C1 C 0.6202(13) 0.0862(3) 0.2311(3) 0.0181(10) Uani 1 1 d . . . C2 C 0.6779(14) 0.1444(3) 0.2753(3) 0.0215(11) Uani 1 1 d . . . H2 H 0.5825 0.1837 0.2544 0.026 Uiso 1 1 calc R . . C3 C 0.8802(15) 0.1418(3) 0.3508(4) 0.0258(12) Uani 1 1 d . . . H3 H 0.9215 0.1804 0.3824 0.031 Uiso 1 1 calc R . . C4 C 1.0292(15) 0.0835(3) 0.3829(4) 0.0259(12) Uani 1 1 d . . . H4 H 1.1698 0.084 0.4345 0.031 Uiso 1 1 calc R . . C5 C 0.9703(13) 0.0269(3) 0.3397(3) 0.0198(11) Uani 1 1 d . . . C6 C 0.7653(13) 0.0280(3) 0.2619(3) 0.0177(10) Uani 1 1 d . . . N7 N 0.6715(12) -0.0210(2) 0.2061(3) 0.0228(10) Uani 1 1 d . . . N8 N 0.4822(13) 0.0031(2) 0.1437(3) 0.0239(10) Uani 1 1 d . . . N9 N 0.4451(11) 0.0683(2) 0.1564(3) 0.0175(9) Uani 1 1 d . . . C10 C 0.2629(13) 0.1049(3) 0.0914(3) 0.0179(10) Uani 1 1 d . . . C11 C 0.1267(13) 0.1632(3) 0.1106(3) 0.0187(11) Uani 1 1 d . . . H11 H 0.1482 0.1786 0.1672 0.022 Uiso 1 1 calc R . . C12 C -0.0411(13) 0.1987(2) 0.0458(3) 0.0168(10) Uani 1 1 d . . . C13 C -0.0868(13) 0.1759(3) -0.0376(3) 0.0181(10) Uani 1 1 d . . . C14 C 0.0437(15) 0.1166(3) -0.0554(4) 0.0242(12) Uani 1 1 d . . . H14 H 0.0108 0.0998 -0.1114 0.029 Uiso 1 1 calc R . . C15 C 0.2229(14) 0.0818(3) 0.0090(4) 0.0237(12) Uani 1 1 d . . . H15 H 0.3184 0.042 -0.0038 0.028 Uiso 1 1 calc R . . O16 O -0.2574(11) 0.21387(19) -0.0974(3) 0.0261(9) Uani 1 1 d . . . C17 C -0.3117(17) 0.1891(3) -0.1819(4) 0.0326(14) Uani 1 1 d . . . H17A H -0.1054 0.1824 -0.2034 0.049 Uiso 1 1 calc R . . H17B H -0.4405 0.22 -0.2184 0.049 Uiso 1 1 calc R . . H17C H -0.4265 0.1479 -0.182 0.049 Uiso 1 1 calc R . . I1 I 1.18712(9) -0.059752(18) 0.38316(2) 0.02458(13) Uani 1 1 d . . . I2 I -0.23436(9) 0.288583(16) 0.07514(2) 0.02072(13) 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 0.019(3) 0.015(3) 0.022(3) 0.003(2) 0.006(2) -0.0022(19) C2 0.028(3) 0.018(3) 0.019(3) -0.003(2) 0.004(2) -0.002(2) C3 0.033(3) 0.021(3) 0.023(3) 0.001(2) 0.002(2) -0.006(2) C4 0.030(3) 0.028(3) 0.019(3) 0.003(2) 0.000(2) -0.004(2) C5 0.020(3) 0.021(3) 0.019(3) 0.006(2) 0.004(2) -0.002(2) C6 0.021(3) 0.017(3) 0.016(2) 0.002(2) 0.001(2) 0.0028(19) N7 0.033(3) 0.017(2) 0.019(2) -0.0009(18) 0.008(2) 0.0013(18) N8 0.035(3) 0.016(2) 0.021(2) -0.0006(18) 0.005(2) 0.0029(19) N9 0.023(2) 0.017(2) 0.013(2) -0.0015(17) 0.0018(18) 0.0020(17) C10 0.017(3) 0.019(3) 0.018(2) 0.002(2) 0.003(2) -0.0005(19) C11 0.021(3) 0.019(3) 0.016(2) -0.004(2) 0.001(2) -0.004(2) C12 0.015(3) 0.015(2) 0.019(3) -0.003(2) -0.001(2) -0.0014(18) C13 0.019(3) 0.020(3) 0.014(2) 0.001(2) -0.001(2) -0.0014(19) C14 0.030(3) 0.022(3) 0.019(3) -0.004(2) -0.003(2) 0.000(2) C15 0.028(3) 0.022(3) 0.020(3) -0.005(2) 0.000(2) 0.002(2) O16 0.037(3) 0.023(2) 0.0149(19) -0.0019(15) -0.0104(17) 0.0069(17) C17 0.043(4) 0.034(4) 0.017(3) -0.002(2) -0.009(3) 0.005(3) I1 0.0218(2) 0.0251(2) 0.0267(2) 0.00981(14) 0.00232(15) 0.00122(13) I2 0.0223(2) 0.0171(2) 0.0219(2) -0.00333(13) -0.00053(15) 0.00301(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N9 1.369(7) . ? C1 C2 1.401(7) . ? C1 C6 1.412(7) . ? C2 C3 1.383(8) . ? C2 H2 0.95 . ? C3 C4 1.427(8) . ? C3 H3 0.95 . ? C4 C5 1.366(8) . ? C4 H4 0.95 . ? C5 C6 1.418(7) . ? C5 I1 2.091(5) . ? C6 N7 1.373(7) . ? N7 N8 1.293(7) . ? N8 N9 1.377(6) . ? N9 C10 1.427(7) . ? C10 C15 1.386(8) . ? C10 C11 1.388(7) . ? C11 C12 1.386(7) . ? C11 H11 0.95 . ? C12 C13 1.398(7) . ? C12 I2 2.107(5) . ? C13 O16 1.367(6) . ? C13 C14 1.390(8) . ? C14 C15 1.394(8) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? O16 C17 1.432(7) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? 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 N9 C1 C2 135.2(5) . . ? N9 C1 C6 103.4(4) . . ? C2 C1 C6 121.4(5) . . ? C3 C2 C1 116.9(5) . . ? C3 C2 H2 121.6 . . ? C1 C2 H2 121.6 . . ? C2 C3 C4 122.6(5) . . ? C2 C3 H3 118.7 . . ? C4 C3 H3 118.7 . . ? C5 C4 C3 120.2(5) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 118.5(5) . . ? C4 C5 I1 121.8(4) . . ? C6 C5 I1 119.7(4) . . ? N7 C6 C1 109.3(5) . . ? N7 C6 C5 130.3(5) . . ? C1 C6 C5 120.4(5) . . ? N8 N7 C6 108.1(4) . . ? N7 N8 N9 109.6(4) . . ? C1 N9 N8 109.6(4) . . ? C1 N9 C10 131.9(5) . . ? N8 N9 C10 118.4(4) . . ? C15 C10 C11 120.2(5) . . ? C15 C10 N9 119.6(5) . . ? C11 C10 N9 120.2(5) . . ? C12 C11 C10 119.0(5) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 121.6(5) . . ? C11 C12 I2 118.6(4) . . ? C13 C12 I2 119.8(4) . . ? O16 C13 C14 123.5(5) . . ? O16 C13 C12 117.7(5) . . ? C14 C13 C12 118.8(5) . . ? C13 C14 C15 119.8(5) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C10 C15 C14 120.6(5) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C13 O16 C17 117.2(4) . . ? O16 C17 H17A 109.5 . . ? O16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 N9 C1 C2 C3 -179.1(6) . . . . ? C6 C1 C2 C3 -0.7(8) . . . . ? C1 C2 C3 C4 0.8(9) . . . . ? C2 C3 C4 C5 -1.2(9) . . . . ? C3 C4 C5 C6 1.5(8) . . . . ? C3 C4 C5 I1 179.2(4) . . . . ? N9 C1 C6 N7 -0.4(6) . . . . ? C2 C1 C6 N7 -179.2(5) . . . . ? N9 C1 C6 C5 179.9(5) . . . . ? C2 C1 C6 C5 1.1(8) . . . . ? C4 C5 C6 N7 178.9(6) . . . . ? I1 C5 C6 N7 1.2(8) . . . . ? C4 C5 C6 C1 -1.5(8) . . . . ? I1 C5 C6 C1 -179.2(4) . . . . ? C1 C6 N7 N8 0.3(6) . . . . ? C5 C6 N7 N8 180.0(6) . . . . ? C6 N7 N8 N9 -0.1(6) . . . . ? C2 C1 N9 N8 178.9(6) . . . . ? C6 C1 N9 N8 0.3(6) . . . . ? C2 C1 N9 C10 4.1(10) . . . . ? C6 C1 N9 C10 -174.5(5) . . . . ? N7 N8 N9 C1 -0.1(6) . . . . ? N7 N8 N9 C10 175.5(5) . . . . ? C1 N9 C10 C15 152.4(6) . . . . ? N8 N9 C10 C15 -22.1(8) . . . . ? C1 N9 C10 C11 -27.6(9) . . . . ? N8 N9 C10 C11 158.0(5) . . . . ? C15 C10 C11 C12 -1.8(8) . . . . ? N9 C10 C11 C12 178.1(5) . . . . ? C10 C11 C12 C13 2.6(8) . . . . ? C10 C11 C12 I2 -178.1(4) . . . . ? C11 C12 C13 O16 179.5(5) . . . . ? I2 C12 C13 O16 0.2(7) . . . . ? C11 C12 C13 C14 -0.9(8) . . . . ? I2 C12 C13 C14 179.9(4) . . . . ? O16 C13 C14 C15 178.1(6) . . . . ? C12 C13 C14 C15 -1.6(9) . . . . ? C11 C10 C15 C14 -0.5(9) . . . . ? N9 C10 C15 C14 179.5(5) . . . . ? C13 C14 C15 C10 2.3(9) . . . . ? C14 C13 O16 C17 2.4(9) . . . . ? C12 C13 O16 C17 -178.0(5) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962379' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4g _audit_creation_date 2013-09-19T17:26:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H5 I2 N3 S1' _chemical_formula_sum 'C10 H5 I2 N3 S1' _chemical_formula_weight 453.04 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c 21' _symmetry_space_group_name_Hall 'P 2c -2b' _symmetry_Int_Tables_number 29 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y+1/2, z' 'x, -y+1/2, z+1/2' _cell_length_a 4.10400(10) _cell_length_b 22.5488(7) _cell_length_c 25.9538(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2401.77(13) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7116 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.41 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 2.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.386 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.401 _exptl_absorpt_correction_T_max 0.764 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_unetI/netI 0.0574 _diffrn_reflns_number 14499 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _reflns_number_total 5344 _reflns_number_gt 5098 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 2012), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^ > 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^)+(0.0456P)^2^+9.1219P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 5344 _refine_ls_number_parameters 217 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.001 _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 0.06(4) _refine_diff_density_max 2.406 _refine_diff_density_min -0.974 _refine_diff_density_rms 0.215 #----------------------------------------------------------------------------# # 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' S S 0.1246 0.1234 '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 0.54559(14) 0.07297(3) 0.34338(2) 0.02659(15) Uani 1 1 d . . . I2 I -0.15828(14) 0.03179(3) 0.74651(3) 0.02289(14) Uani 1 1 d . . . S1 S 0.3430(5) 0.04262(9) 0.46319(9) 0.0191(5) Uani 1 1 d . . . C1 C 0.349(2) 0.0945(4) 0.4145(4) 0.0215(11) Uani 1 1 d . . . C2 C 0.225(2) 0.1473(4) 0.4288(4) 0.0215(11) Uani 1 1 d . . . H2 H 0.2176 0.1812 0.4071 0.026 Uiso 1 1 calc R . . C3 C 0.103(2) 0.1461(4) 0.4812(4) 0.0215(11) Uani 1 1 d . . . H3 H 0.0003 0.1787 0.4978 0.026 Uiso 1 1 calc R . . C4 C 0.155(2) 0.0932(4) 0.5034(3) 0.0165(17) Uani 1 1 d . . . N5 N 0.0718(18) 0.0776(3) 0.5542(3) 0.0139(14) Uani 1 1 d . . . N6 N -0.085(2) 0.0257(3) 0.5643(3) 0.0231(17) Uani 1 1 d . . . N7 N -0.1283(18) 0.0213(3) 0.6141(3) 0.0181(16) Uani 1 1 d . . . C8 C 0.006(2) 0.0710(4) 0.6375(4) 0.0173(7) Uani 1 1 d . . . C9 C 0.026(2) 0.0878(4) 0.6894(4) 0.0173(7) Uani 1 1 d . . . C10 C 0.176(2) 0.1407(3) 0.6996(4) 0.0173(7) Uani 1 1 d . . . H10 H 0.19 0.1536 0.7343 0.021 Uiso 1 1 calc R . . C11 C 0.309(2) 0.1763(4) 0.6612(3) 0.0173(7) Uani 1 1 d . . . H11 H 0.4118 0.2124 0.6706 0.021 Uiso 1 1 calc R . . C12 C 0.295(2) 0.1605(4) 0.6102(3) 0.0173(7) Uani 1 1 d . . . H12 H 0.3873 0.1845 0.5839 0.021 Uiso 1 1 calc R . . C13 C 0.137(2) 0.1074(4) 0.5993(4) 0.0173(7) Uani 1 1 d . . . I3 I 0.98190(14) 0.16288(3) 0.22618(2) 0.02276(14) Uani 1 1 d . . . I4 I 0.59234(13) 0.22999(2) -0.18054(2) 0.02041(13) Uani 1 1 d . . . S2 S 0.8421(5) 0.19752(9) 0.10567(9) 0.0173(4) Uani 1 1 d . . . C21 C 0.795(2) 0.1459(4) 0.1536(3) 0.0169(9) Uani 1 1 d . . . C22 C 0.628(2) 0.0954(4) 0.1374(4) 0.0169(9) Uani 1 1 d . . . H22 H 0.5745 0.0628 0.1591 0.02 Uiso 1 1 calc R . . C23 C 0.547(2) 0.0991(4) 0.0847(4) 0.0169(9) Uani 1 1 d . . . H23 H 0.4371 0.0686 0.0665 0.02 Uiso 1 1 calc R . . C24 C 0.645(2) 0.1512(4) 0.0624(4) 0.0169(9) Uani 1 1 d . . . N25 N 0.6093(17) 0.1703(3) 0.0116(3) 0.0147(14) Uani 1 1 d . . . N26 N 0.771(2) 0.2217(3) -0.0022(3) 0.0250(18) Uani 1 1 d . . . N27 N 0.7323(19) 0.2304(3) -0.0515(3) 0.0215(17) Uani 1 1 d . . . C28 C 0.542(2) 0.1842(3) -0.0705(4) 0.0144(17) Uani 1 1 d . . . C29 C 0.4465(19) 0.1732(3) -0.1212(4) 0.0129(16) Uani 1 1 d . . . C30 C 0.261(2) 0.1232(3) -0.1298(4) 0.0178(10) Uani 1 1 d . . . H30 H 0.1916 0.1141 -0.1638 0.021 Uiso 1 1 calc R . . C31 C 0.172(2) 0.0853(4) -0.0888(4) 0.0178(10) Uani 1 1 d . . . H31 H 0.0425 0.0514 -0.0961 0.021 Uiso 1 1 calc R . . C32 C 0.265(2) 0.0956(4) -0.0388(4) 0.0178(10) Uani 1 1 d . . . H32 H 0.2039 0.0699 -0.0114 0.021 Uiso 1 1 calc R . . C33 C 0.456(2) 0.1464(4) -0.0306(4) 0.0157(17) 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 I1 0.0187(3) 0.0448(4) 0.0163(3) -0.0085(3) 0.0031(3) -0.0043(2) I2 0.0196(3) 0.0307(3) 0.0183(3) 0.0081(3) 0.0001(2) -0.0057(2) S1 0.0248(12) 0.0132(9) 0.0193(12) -0.0033(9) 0.0003(9) 0.0045(8) C1 0.026(3) 0.018(2) 0.020(3) -0.003(2) 0.005(2) 0.005(2) C2 0.026(3) 0.018(2) 0.020(3) -0.003(2) 0.005(2) 0.005(2) C3 0.026(3) 0.018(2) 0.020(3) -0.003(2) 0.005(2) 0.005(2) C4 0.021(4) 0.017(4) 0.011(4) -0.004(3) 0.007(3) -0.004(3) N5 0.022(4) 0.011(3) 0.009(4) 0.004(3) -0.007(3) -0.002(3) N6 0.036(5) 0.015(3) 0.018(4) -0.003(3) -0.006(3) -0.005(3) N7 0.023(4) 0.015(3) 0.016(4) 0.000(3) -0.005(3) -0.005(3) C8 0.0222(19) 0.0133(16) 0.0164(19) 0.0010(14) -0.0017(14) -0.0007(13) C9 0.0222(19) 0.0133(16) 0.0164(19) 0.0010(14) -0.0017(14) -0.0007(13) C10 0.0222(19) 0.0133(16) 0.0164(19) 0.0010(14) -0.0017(14) -0.0007(13) C11 0.0222(19) 0.0133(16) 0.0164(19) 0.0010(14) -0.0017(14) -0.0007(13) C12 0.0222(19) 0.0133(16) 0.0164(19) 0.0010(14) -0.0017(14) -0.0007(13) C13 0.0222(19) 0.0133(16) 0.0164(19) 0.0010(14) -0.0017(14) -0.0007(13) I3 0.0183(3) 0.0372(3) 0.0128(3) -0.0046(3) -0.0011(2) 0.0011(2) I4 0.0183(3) 0.0261(3) 0.0168(3) 0.0066(2) -0.0005(2) -0.0036(2) S2 0.0182(11) 0.0149(10) 0.0188(11) -0.0003(8) -0.0011(9) -0.0036(8) C21 0.018(2) 0.0181(19) 0.014(2) -0.0002(18) -0.0008(16) -0.0027(16) C22 0.018(2) 0.0181(19) 0.014(2) -0.0002(18) -0.0008(16) -0.0027(16) C23 0.018(2) 0.0181(19) 0.014(2) -0.0002(18) -0.0008(16) -0.0027(16) C24 0.018(2) 0.0181(19) 0.014(2) -0.0002(18) -0.0008(16) -0.0027(16) N25 0.016(4) 0.012(3) 0.016(4) 0.001(3) 0.000(3) -0.005(2) N26 0.035(5) 0.016(3) 0.024(4) -0.003(3) -0.003(4) -0.010(3) N27 0.023(4) 0.015(3) 0.027(4) 0.003(3) -0.006(3) -0.005(3) C28 0.015(4) 0.006(3) 0.022(5) -0.001(3) -0.006(3) 0.002(3) C29 0.011(4) 0.014(3) 0.013(4) 0.004(3) 0.003(3) 0.001(3) C30 0.022(3) 0.012(2) 0.019(3) -0.003(2) -0.003(2) -0.0030(18) C31 0.022(3) 0.012(2) 0.019(3) -0.003(2) -0.003(2) -0.0030(18) C32 0.022(3) 0.012(2) 0.019(3) -0.003(2) -0.003(2) -0.0030(18) C33 0.012(4) 0.015(4) 0.020(5) 0.001(4) 0.001(3) -0.001(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.072(9) . ? I2 C9 2.088(9) . ? S1 C1 1.721(10) . ? S1 C4 1.728(9) . ? C1 C2 1.347(12) . ? C2 C3 1.450(13) . ? C2 H2 0.95 . ? C3 C4 1.341(12) . ? C3 H3 0.95 . ? C4 N5 1.408(11) . ? N5 N6 1.362(10) . ? N5 C13 1.374(11) . ? N6 N7 1.310(11) . ? N7 C8 1.389(11) . ? C8 C13 1.395(12) . ? C8 C9 1.401(13) . ? C9 C10 1.368(11) . ? C10 C11 1.390(12) . ? C10 H10 0.95 . ? C11 C12 1.373(12) . ? C11 H11 0.95 . ? C12 C13 1.390(11) . ? C12 H12 0.95 . ? I3 C21 2.070(9) . ? I4 C29 2.090(8) . ? S2 C21 1.713(9) . ? S2 C24 1.733(9) . ? C21 C22 1.396(12) . ? C22 C23 1.410(13) . ? C22 H22 0.95 . ? C23 C24 1.368(12) . ? C23 H23 0.95 . ? C24 N25 1.396(11) . ? N25 C33 1.374(11) . ? N25 N26 1.382(10) . ? N26 N27 1.305(11) . ? N27 C28 1.390(10) . ? C28 C33 1.387(12) . ? C28 C29 1.398(13) . ? C29 C30 1.378(11) . ? C30 C31 1.413(12) . ? C30 H30 0.95 . ? C31 C32 1.372(13) . ? C31 H31 0.95 . ? C32 C33 1.404(11) . ? C32 H32 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 C1 S1 C4 90.1(4) . . ? C2 C1 S1 113.2(7) . . ? C2 C1 I1 126.7(7) . . ? S1 C1 I1 120.1(5) . . ? C1 C2 C3 111.8(8) . . ? C1 C2 H2 124.1 . . ? C3 C2 H2 124.1 . . ? C4 C3 C2 111.4(8) . . ? C4 C3 H3 124.3 . . ? C2 C3 H3 124.3 . . ? C3 C4 N5 125.9(8) . . ? C3 C4 S1 113.5(7) . . ? N5 C4 S1 120.6(6) . . ? N6 N5 C13 110.4(7) . . ? N6 N5 C4 120.6(7) . . ? C13 N5 C4 128.9(7) . . ? N7 N6 N5 108.6(7) . . ? N6 N7 C8 108.4(7) . . ? N7 C8 C13 108.5(8) . . ? N7 C8 C9 131.3(8) . . ? C13 C8 C9 120.2(8) . . ? C10 C9 C8 116.5(8) . . ? C10 C9 I2 123.6(7) . . ? C8 C9 I2 119.9(6) . . ? C9 C10 C11 122.9(9) . . ? C9 C10 H10 118.6 . . ? C11 C10 H10 118.6 . . ? C12 C11 C10 121.6(8) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C13 116.1(8) . . ? C11 C12 H12 122 . . ? C13 C12 H12 122 . . ? N5 C13 C12 133.2(8) . . ? N5 C13 C8 104.1(7) . . ? C12 C13 C8 122.7(9) . . ? C21 S2 C24 90.4(4) . . ? C22 C21 S2 113.1(7) . . ? C22 C21 I3 127.3(6) . . ? S2 C21 I3 119.6(4) . . ? C21 C22 C23 110.9(8) . . ? C21 C22 H22 124.6 . . ? C23 C22 H22 124.6 . . ? C24 C23 C22 113.2(8) . . ? C24 C23 H23 123.4 . . ? C22 C23 H23 123.4 . . ? C23 C24 N25 129.3(8) . . ? C23 C24 S2 112.4(7) . . ? N25 C24 S2 118.3(6) . . ? C33 N25 N26 110.1(7) . . ? C33 N25 C24 132.8(7) . . ? N26 N25 C24 117.0(7) . . ? N27 N26 N25 108.7(7) . . ? N26 N27 C28 107.7(7) . . ? C33 C28 N27 109.8(8) . . ? C33 C28 C29 121.4(7) . . ? N27 C28 C29 128.7(8) . . ? C30 C29 C28 117.0(8) . . ? C30 C29 I4 122.8(7) . . ? C28 C29 I4 120.2(6) . . ? C29 C30 C31 121.0(8) . . ? C29 C30 H30 119.5 . . ? C31 C30 H30 119.5 . . ? C32 C31 C30 122.6(8) . . ? C32 C31 H31 118.7 . . ? C30 C31 H31 118.7 . . ? C31 C32 C33 115.8(8) . . ? C31 C32 H32 122.1 . . ? C33 C32 H32 122.1 . . ? N25 C33 C28 103.7(7) . . ? N25 C33 C32 134.2(8) . . ? C28 C33 C32 122.1(8) . . ? 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 C4 S1 C1 C2 1.7(8) . . . . ? C4 S1 C1 I1 -179.6(6) . . . . ? S1 C1 C2 C3 -2.5(11) . . . . ? I1 C1 C2 C3 179.0(7) . . . . ? C1 C2 C3 C4 2.2(12) . . . . ? C2 C3 C4 N5 179.0(8) . . . . ? C2 C3 C4 S1 -0.9(11) . . . . ? C1 S1 C4 C3 -0.4(8) . . . . ? C1 S1 C4 N5 179.7(7) . . . . ? C3 C4 N5 N6 132.7(10) . . . . ? S1 C4 N5 N6 -47.5(11) . . . . ? C3 C4 N5 C13 -49.9(14) . . . . ? S1 C4 N5 C13 129.9(8) . . . . ? C13 N5 N6 N7 0.9(10) . . . . ? C4 N5 N6 N7 178.7(8) . . . . ? N5 N6 N7 C8 -0.5(10) . . . . ? N6 N7 C8 C13 0.0(10) . . . . ? N6 N7 C8 C9 -179.9(9) . . . . ? N7 C8 C9 C10 -179.8(9) . . . . ? C13 C8 C9 C10 0.3(13) . . . . ? N7 C8 C9 I2 1.8(13) . . . . ? C13 C8 C9 I2 -178.1(6) . . . . ? C8 C9 C10 C11 -1.0(13) . . . . ? I2 C9 C10 C11 177.3(7) . . . . ? C9 C10 C11 C12 0.5(14) . . . . ? C10 C11 C12 C13 0.7(13) . . . . ? N6 N5 C13 C12 178.5(9) . . . . ? C4 N5 C13 C12 0.8(16) . . . . ? N6 N5 C13 C8 -0.8(9) . . . . ? C4 N5 C13 C8 -178.4(9) . . . . ? C11 C12 C13 N5 179.3(9) . . . . ? C11 C12 C13 C8 -1.5(13) . . . . ? N7 C8 C13 N5 0.5(9) . . . . ? C9 C8 C13 N5 -179.6(8) . . . . ? N7 C8 C13 C12 -178.9(8) . . . . ? C9 C8 C13 C12 1.0(14) . . . . ? C24 S2 C21 C22 -1.4(7) . . . . ? C24 S2 C21 I3 178.6(5) . . . . ? S2 C21 C22 C23 1.8(10) . . . . ? I3 C21 C22 C23 -178.2(6) . . . . ? C21 C22 C23 C24 -1.4(11) . . . . ? C22 C23 C24 N25 179.8(9) . . . . ? C22 C23 C24 S2 0.4(10) . . . . ? C21 S2 C24 C23 0.6(7) . . . . ? C21 S2 C24 N25 -178.9(7) . . . . ? C23 C24 N25 C33 4.1(16) . . . . ? S2 C24 N25 C33 -176.5(7) . . . . ? C23 C24 N25 N26 -171.2(9) . . . . ? S2 C24 N25 N26 8.2(11) . . . . ? C33 N25 N26 N27 -1.2(10) . . . . ? C24 N25 N26 N27 175.1(8) . . . . ? N25 N26 N27 C28 -0.1(10) . . . . ? N26 N27 C28 C33 1.4(10) . . . . ? N26 N27 C28 C29 -177.3(8) . . . . ? C33 C28 C29 C30 0.4(12) . . . . ? N27 C28 C29 C30 178.9(8) . . . . ? C33 C28 C29 I4 -178.3(6) . . . . ? N27 C28 C29 I4 0.2(12) . . . . ? C28 C29 C30 C31 0.2(12) . . . . ? I4 C29 C30 C31 178.9(6) . . . . ? C29 C30 C31 C32 -0.4(14) . . . . ? C30 C31 C32 C33 -0.1(13) . . . . ? N26 N25 C33 C28 1.9(9) . . . . ? C24 N25 C33 C28 -173.6(9) . . . . ? N26 N25 C33 C32 179.3(9) . . . . ? C24 N25 C33 C32 3.7(17) . . . . ? N27 C28 C33 N25 -2.0(9) . . . . ? C29 C28 C33 N25 176.8(7) . . . . ? N27 C28 C33 C32 -179.7(8) . . . . ? C29 C28 C33 C32 -1.0(13) . . . . ? C31 C32 C33 N25 -176.2(9) . . . . ? C31 C32 C33 C28 0.8(13) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962380'