# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FO _publ_contact_author_email floris.chevallier@univ-rennes1.fr loop_ _publ_author_name 'Thomas Blin' 'Elisabeth Nagaradja' 'Frederic Lassagne' 'Thierry Roisnel' 'Yury S. Halauko' 'Vadim E. Matulis' 'Oleg A. Ivashkevich' 'Floris Chevallier' 'Florence Mongin' _publ_contact_author_name 'Floris Chevallier' data_job_d _database_code_depnum_ccdc_archive 'CCDC 864272' #TrackingRef 'd.cif' _audit_creation_date 2011-09-01T14:51:38-00:00 _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 'C9 H7 I2 N3 O' _chemical_formula_sum 'C9 H7 I2 N3 O' _chemical_formula_weight 426.98 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c 21 n' _symmetry_space_group_name_Hall 'P -2n -2ac' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x+1/2, y, z+1/2' 'x+1/2, y+1/2, -z+1/2' _cell_length_a 4.1304(2) _cell_length_b 12.9948(5) _cell_length_c 21.5358(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1155.91(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3199 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.45 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 2.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.419 _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 0.392 _exptl_absorpt_correction_T_max 0.614 #----------------------------------------------------------------------------# # 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 0.027 _diffrn_reflns_av_unetI/netI 0.0388 _diffrn_reflns_number 4879 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 2314 _reflns_number_gt 2273 _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^)+(0.0153P)^2^+0.6044P] 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 2314 _refine_ls_number_parameters 137 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0502 _refine_ls_wR_factor_gt 0.0498 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.04(3) _refine_diff_density_max 0.58 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.109 #----------------------------------------------------------------------------# # 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 -0.1046(10) 0.0950(5) 0.21453(19) 0.0187(8) Uani 1 1 d . . . C2 C -0.0515(16) -0.0019(5) 0.2384(2) 0.0305(14) Uani 1 1 d . . . H2 H -0.0869 -0.0221 0.2802 0.037 Uiso 1 1 calc R . . N3 N 0.0585(12) -0.0631(3) 0.1928(2) 0.0285(11) Uani 1 1 d . . . N4 N 0.0658(9) -0.0006(3) 0.14375(19) 0.0176(9) Uani 1 1 d . . . N5 N -0.0313(9) 0.0974(4) 0.15450(16) 0.0186(8) Uani 1 1 d . . . C6 C 0.1791(12) -0.0329(4) 0.0838(2) 0.0168(9) Uani 1 1 d . . . C7 C 0.1089(12) 0.0292(4) 0.0329(2) 0.0187(10) Uani 1 1 d . . . H7 H -0.0111 0.0911 0.0377 0.022 Uiso 1 1 calc R . . C8 C 0.2186(11) -0.0016(4) -0.0250(2) 0.0166(10) Uani 1 1 d . . . C9 C 0.3970(12) -0.0917(4) -0.0322(2) 0.0200(11) Uani 1 1 d . . . C10 C 0.4580(13) -0.1532(4) 0.0193(2) 0.0210(11) Uani 1 1 d . . . H10 H 0.5729 -0.216 0.0145 0.025 Uiso 1 1 calc R . . C11 C 0.3510(13) -0.1229(4) 0.0780(2) 0.0213(11) Uani 1 1 d . . . H11 H 0.3964 -0.164 0.1134 0.026 Uiso 1 1 calc R . . O12 O 0.4928(9) -0.1151(3) -0.09118(15) 0.0233(8) Uani 1 1 d . . . C13 C 0.6739(15) -0.2084(5) -0.0998(3) 0.0276(13) Uani 1 1 d . . . H13A H 0.8703 -0.2062 -0.0743 0.041 Uiso 1 1 calc R . . H13B H 0.7339 -0.2153 -0.1436 0.041 Uiso 1 1 calc R . . H13C H 0.5411 -0.2674 -0.0874 0.041 Uiso 1 1 calc R . . I1 I -0.25664(8) 0.22870(3) 0.258362(12) 0.01886(8) Uani 1 1 d . . . I2 I 0.10601(7) 0.09051(3) -0.102028(12) 0.02184(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 0.021(2) 0.0155(19) 0.0199(19) -0.005(3) 0.0008(18) -0.001(3) C2 0.050(4) 0.024(3) 0.017(3) 0.002(2) 0.000(3) 0.009(3) N3 0.047(3) 0.019(2) 0.020(2) 0.0037(17) 0.004(2) 0.010(2) N4 0.022(2) 0.0109(18) 0.020(2) 0.0004(16) 0.0021(17) 0.0033(17) N5 0.0228(19) 0.0128(17) 0.0202(16) 0.000(2) 0.0025(15) 0.002(2) C6 0.018(2) 0.015(2) 0.018(2) -0.0033(19) 0.002(2) -0.002(2) C7 0.017(2) 0.013(2) 0.026(3) -0.0043(19) -0.001(2) -0.001(2) C8 0.013(2) 0.017(2) 0.019(2) 0.002(2) 0.0005(19) -0.002(2) C9 0.021(3) 0.018(2) 0.021(2) -0.0034(19) 0.003(2) -0.003(2) C10 0.024(3) 0.013(2) 0.027(3) -0.001(2) 0.002(2) 0.000(2) C11 0.025(3) 0.016(2) 0.023(3) 0.003(2) -0.002(2) 0.002(2) O12 0.0289(19) 0.0214(19) 0.0197(17) -0.0046(14) 0.0048(16) 0.0055(17) C13 0.029(3) 0.026(3) 0.027(3) -0.008(2) 0.003(2) 0.007(3) I1 0.02352(16) 0.01588(13) 0.01720(13) -0.00121(16) 0.00264(12) 0.00471(13) I2 0.02282(16) 0.02271(14) 0.02000(13) 0.00366(16) -0.00111(12) 0.00266(19) #----------------------------------------------------------------------------# # 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 N5 1.328(5) . ? C1 C2 1.378(9) . ? C1 I1 2.075(6) . ? C2 N3 1.342(7) . ? C2 H2 0.95 . ? N3 N4 1.333(6) . ? N4 N5 1.355(6) . ? N4 C6 1.436(6) . ? C6 C11 1.373(7) . ? C6 C7 1.393(7) . ? C7 C8 1.385(7) . ? C7 H7 0.95 . ? C8 C9 1.392(7) . ? C8 I2 2.098(5) . ? C9 O12 1.365(6) . ? C9 C10 1.389(7) . ? C10 C11 1.396(7) . ? C10 H10 0.95 . ? C11 H11 0.95 . ? O12 C13 1.437(7) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 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 N5 C1 C2 110.4(5) . . ? N5 C1 I1 119.5(5) . . ? C2 C1 I1 130.1(4) . . ? N3 C2 C1 108.8(5) . . ? N3 C2 H2 125.6 . . ? C1 C2 H2 125.6 . . ? N4 N3 C2 103.1(4) . . ? N3 N4 N5 115.5(4) . . ? N3 N4 C6 122.8(4) . . ? N5 N4 C6 121.7(4) . . ? C1 N5 N4 102.2(4) . . ? C11 C6 C7 121.9(5) . . ? C11 C6 N4 120.0(5) . . ? C7 C6 N4 118.1(4) . . ? C8 C7 C6 118.2(5) . . ? C8 C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? C7 C8 C9 121.1(5) . . ? C7 C8 I2 118.3(4) . . ? C9 C8 I2 120.6(4) . . ? O12 C9 C10 124.2(5) . . ? O12 C9 C8 116.4(4) . . ? C10 C9 C8 119.3(5) . . ? C9 C10 C11 120.2(5) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C6 C11 C10 119.1(5) . . ? C6 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C9 O12 C13 117.4(4) . . ? O12 C13 H13A 109.5 . . ? O12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 N5 C1 C2 N3 0.1(7) . . . . ? I1 C1 C2 N3 -177.5(4) . . . . ? C1 C2 N3 N4 -0.1(7) . . . . ? C2 N3 N4 N5 0.2(6) . . . . ? C2 N3 N4 C6 178.1(5) . . . . ? C2 C1 N5 N4 0.1(5) . . . . ? I1 C1 N5 N4 177.9(3) . . . . ? N3 N4 N5 C1 -0.2(5) . . . . ? C6 N4 N5 C1 -178.1(4) . . . . ? N3 N4 C6 C11 -14.4(7) . . . . ? N5 N4 C6 C11 163.3(4) . . . . ? N3 N4 C6 C7 165.5(5) . . . . ? N5 N4 C6 C7 -16.8(7) . . . . ? C11 C6 C7 C8 -0.3(7) . . . . ? N4 C6 C7 C8 179.8(4) . . . . ? C6 C7 C8 C9 -0.6(7) . . . . ? C6 C7 C8 I2 178.9(4) . . . . ? C7 C8 C9 O12 179.9(4) . . . . ? I2 C8 C9 O12 0.4(6) . . . . ? C7 C8 C9 C10 1.8(7) . . . . ? I2 C8 C9 C10 -177.7(4) . . . . ? O12 C9 C10 C11 179.9(5) . . . . ? C8 C9 C10 C11 -2.2(8) . . . . ? C7 C6 C11 C10 -0.1(8) . . . . ? N4 C6 C11 C10 179.8(5) . . . . ? C9 C10 C11 C6 1.4(8) . . . . ? C10 C9 O12 C13 -1.3(7) . . . . ? C8 C9 O12 C13 -179.3(5) . . . . ? # Attachment 'e.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-09-01 at 14:20:39 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : d:\progs\wingx\files\archive.dat # CIF files read : job struct data_job_e _database_code_depnum_ccdc_archive 'CCDC 864273' #TrackingRef 'e.cif' _audit_creation_date 2011-09-01T14:20:39-00:00 _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 'C8 H4 Cl I2 N3' _chemical_formula_sum 'C8 H4 Cl I2 N3' _chemical_formula_weight 431.39 _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 c n' _symmetry_space_group_name_Hall 'P -2n 2a' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, -z' 'x, -y+1/2, z+1/2' 'x+1/2, y+1/2, -z+1/2' _cell_length_a 7.8011(19) _cell_length_b 9.106(2) _cell_length_c 15.558(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1105.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9872 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 27.5 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.17 _exptl_crystal_density_diffrn 2.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.896 _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 0.228 _exptl_absorpt_correction_T_max 0.367 #----------------------------------------------------------------------------# # 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 0.0403 _diffrn_reflns_av_unetI/netI 0.0252 _diffrn_reflns_number 16947 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2515 _reflns_number_gt 2480 _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^)+(0.0094P)^2^+1.5192P] 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 2515 _refine_ls_number_parameters 127 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0182 _refine_ls_R_factor_gt 0.0178 _refine_ls_wR_factor_ref 0.0388 _refine_ls_wR_factor_gt 0.0386 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.03 _refine_ls_shift/su_mean 0.004 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_diff_density_max 0.352 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.086 #----------------------------------------------------------------------------# # 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 0.66107(3) 1.04033(2) 0.574113(16) 0.02221(6) Uani 1 1 d . . . I2 I 0.41614(3) 0.44871(2) 0.683937(14) 0.01914(6) Uani 1 1 d . . . C1 C 0.4574(4) 0.9294(4) 0.6275(2) 0.0163(7) Uani 1 1 d . . . C2 C 0.3619(5) 0.9687(4) 0.6995(2) 0.0194(8) Uani 1 1 d . . . H2 H 0.3828 1.0515 0.7351 0.023 Uiso 1 1 calc R . . N3 N 0.2354(4) 0.8706(3) 0.7105(2) 0.0212(7) Uani 1 1 d . . . N4 N 0.2616(4) 0.7748(3) 0.64648(19) 0.0171(6) Uani 1 1 d . . . N5 N 0.3928(4) 0.8061(3) 0.59386(19) 0.0185(6) Uani 1 1 d . . . C6 C 0.1380(4) 0.6637(4) 0.6265(2) 0.0150(7) Uani 1 1 d . . . C7 C 0.1812(5) 0.5157(4) 0.6334(2) 0.0150(6) Uani 1 1 d . . . C8 C 0.0541(5) 0.4135(4) 0.6089(2) 0.0170(7) Uani 1 1 d . . . C9 C -0.1068(6) 0.4580(4) 0.5812(2) 0.0218(8) Uani 1 1 d . . . H9 H -0.1897 0.3869 0.5648 0.026 Uiso 1 1 calc R . . C10 C -0.1467(5) 0.6066(4) 0.5774(2) 0.0212(8) Uani 1 1 d . . . H10 H -0.2579 0.6358 0.5594 0.025 Uiso 1 1 calc R . . C11 C -0.0304(4) 0.7102(3) 0.5988(2) 0.0130(7) Uani 1 1 d . . . H11 H -0.0586 0.8115 0.5956 0.016 Uiso 1 1 calc R . . Cl1 Cl 0.09237(13) 0.22765(10) 0.61767(7) 0.0296(2) 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 0.01658(11) 0.01878(10) 0.03126(13) 0.00441(9) 0.00294(11) -0.00371(10) I2 0.01460(10) 0.01924(10) 0.02357(12) 0.00112(8) -0.00250(10) 0.00138(11) C1 0.0159(19) 0.0137(15) 0.0194(18) 0.0060(13) -0.0013(13) 0.0000(12) C2 0.0213(19) 0.0156(16) 0.0212(19) -0.0005(14) 0.0046(15) -0.0001(13) N3 0.0219(15) 0.0222(16) 0.0197(16) -0.0033(13) 0.0049(13) -0.0046(13) N4 0.0187(15) 0.0144(14) 0.0181(15) 0.0008(12) 0.0047(12) -0.0009(11) N5 0.0155(15) 0.0200(14) 0.0201(14) 0.0016(11) 0.0043(13) -0.0001(12) C6 0.0119(18) 0.0181(15) 0.0151(16) 0.0004(12) 0.0013(14) -0.0029(13) C7 0.0115(16) 0.0192(15) 0.0144(15) 0.0026(12) 0.0048(14) -0.0005(14) C8 0.0185(18) 0.0155(15) 0.0171(18) 0.0006(14) 0.0005(14) -0.0008(14) C9 0.022(2) 0.0251(19) 0.0182(17) -0.0008(13) -0.0035(17) -0.0053(16) C10 0.0166(17) 0.030(2) 0.0169(19) 0.0065(15) -0.0036(14) 0.0036(15) C11 0.0185(17) 0.0094(15) 0.0110(16) 0.0044(12) 0.0068(13) -0.0017(12) Cl1 0.0287(5) 0.0154(4) 0.0446(6) -0.0006(4) -0.0077(5) -0.0030(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 2.058(3) . ? I2 C7 2.086(4) . ? C1 N5 1.338(4) . ? C1 C2 1.392(5) . ? C2 N3 1.341(5) . ? C2 H2 0.95 . ? N3 N4 1.340(4) . ? N4 N5 1.341(4) . ? N4 C6 1.432(4) . ? C6 C7 1.393(4) . ? C6 C11 1.446(5) . ? C7 C8 1.412(5) . ? C8 C9 1.388(6) . ? C8 Cl1 1.724(4) . ? C9 C10 1.390(5) . ? C9 H9 0.95 . ? C10 C11 1.351(5) . ? C10 H10 0.95 . ? C11 H11 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 N5 C1 C2 109.2(3) . . ? N5 C1 I1 123.0(3) . . ? C2 C1 I1 127.7(3) . . ? N3 C2 C1 109.0(3) . . ? N3 C2 H2 125.5 . . ? C1 C2 H2 125.5 . . ? N4 N3 C2 103.1(3) . . ? N5 N4 N3 115.6(3) . . ? N5 N4 C6 122.1(3) . . ? N3 N4 C6 121.3(3) . . ? C1 N5 N4 103.1(3) . . ? C7 C6 N4 120.2(3) . . ? C7 C6 C11 121.8(3) . . ? N4 C6 C11 118.0(3) . . ? C6 C7 C8 116.6(3) . . ? C6 C7 I2 121.6(3) . . ? C8 C7 I2 121.7(2) . . ? C9 C8 C7 121.7(3) . . ? C9 C8 Cl1 117.9(3) . . ? C7 C8 Cl1 120.3(3) . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120 . . ? C8 C9 H9 120 . . ? C11 C10 C9 121.3(3) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C6 118.6(3) . . ? C10 C11 H11 120.7 . . ? C6 C11 H11 120.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 C1 C2 N3 -0.7(4) . . . . ? I1 C1 C2 N3 177.0(3) . . . . ? C1 C2 N3 N4 1.4(4) . . . . ? C2 N3 N4 N5 -1.7(4) . . . . ? C2 N3 N4 C6 -170.1(3) . . . . ? C2 C1 N5 N4 -0.3(4) . . . . ? I1 C1 N5 N4 -178.1(2) . . . . ? N3 N4 N5 C1 1.2(4) . . . . ? C6 N4 N5 C1 169.6(3) . . . . ? N5 N4 C6 C7 74.1(4) . . . . ? N3 N4 C6 C7 -118.2(4) . . . . ? N5 N4 C6 C11 -105.4(4) . . . . ? N3 N4 C6 C11 62.3(4) . . . . ? N4 C6 C7 C8 -177.4(3) . . . . ? C11 C6 C7 C8 2.1(5) . . . . ? N4 C6 C7 I2 6.2(4) . . . . ? C11 C6 C7 I2 -174.4(2) . . . . ? C6 C7 C8 C9 -1.3(5) . . . . ? I2 C7 C8 C9 175.2(3) . . . . ? C6 C7 C8 Cl1 -178.2(2) . . . . ? I2 C7 C8 Cl1 -1.8(4) . . . . ? C7 C8 C9 C10 -0.4(5) . . . . ? Cl1 C8 C9 C10 176.7(3) . . . . ? C8 C9 C10 C11 1.3(6) . . . . ? C9 C10 C11 C6 -0.4(5) . . . . ? C7 C6 C11 C10 -1.3(5) . . . . ? N4 C6 C11 C10 178.2(3) . . . . ? # Attachment 'web_deposit_cif_file_0_FlorisChevallier_1327423415.TB018F_150K_2a.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-09-21 at 08:45:39 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : d:\progs\wingx\files\archive.dat # CIF files read : job struct data_job_F_150K_2a _database_code_depnum_ccdc_archive 'CCDC 864274' #TrackingRef 'web_deposit_cif_file_0_FlorisChevallier_1327423415.TB018F_150K_2a.cif' _audit_creation_date 2011-09-21T08:45:39-00:00 _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 'C8 H6 I N3' _chemical_formula_sum 'C8 H6 I N3' _chemical_formula_weight 271.06 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c 21 n' _symmetry_space_group_name_Hall 'P -2n -2ac' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x+1/2, y, z+1/2' 'x+1/2, y+1/2, -z+1/2' _cell_length_a 4.3176(3) _cell_length_b 13.3505(10) _cell_length_c 15.2661(12) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 879.97(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5825 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 27.46 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description stick _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 2.046 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.584 _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 0.773 _exptl_absorpt_correction_T_max 0.898 #----------------------------------------------------------------------------# # 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 0.0345 _diffrn_reflns_av_unetI/netI 0.0235 _diffrn_reflns_number 12103 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.06 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 1992 _reflns_number_gt 1792 _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^)+(0.0157P)^2^+0.3755P] 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 1992 _refine_ls_number_parameters 109 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0228 _refine_ls_R_factor_gt 0.0183 _refine_ls_wR_factor_ref 0.0419 _refine_ls_wR_factor_gt 0.0398 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_diff_density_max 0.539 _refine_diff_density_min -0.768 _refine_diff_density_rms 0.072 #----------------------------------------------------------------------------# # 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 C1 C 0.1490(7) 0.5171(2) 0.46062(19) 0.0200(6) Uani 1 1 d . . . C2 C 0.0869(8) 0.4175(3) 0.4832(2) 0.0240(6) Uani 1 1 d . . . H2 H -0.0423 0.396 0.53 0.029 Uiso 1 1 calc R . . N3 N 0.2387(6) 0.35817(18) 0.42845(17) 0.0227(5) Uani 1 1 d . . . N4 N 0.3850(6) 0.42086(19) 0.37510(17) 0.0186(5) Uani 1 1 d . . . N5 N 0.3396(5) 0.51903(17) 0.39220(16) 0.0204(5) Uani 1 1 d . . . C6 C 0.5773(8) 0.3888(2) 0.3044(2) 0.0199(7) Uani 1 1 d . . . C7 C 0.5998(7) 0.2866(2) 0.2869(2) 0.0261(7) Uani 1 1 d . . . H7 H 0.4934 0.2392 0.3222 0.031 Uiso 1 1 calc R . . C8 C 0.7805(7) 0.2556(3) 0.2170(2) 0.0296(7) Uani 1 1 d . . . H8 H 0.7975 0.1862 0.2043 0.036 Uiso 1 1 calc R . . C9 C 0.9355(8) 0.3238(3) 0.1658(2) 0.0345(8) Uani 1 1 d . . . H9 H 1.0577 0.3015 0.1179 0.041 Uiso 1 1 calc R . . C10 C 0.9133(9) 0.4259(3) 0.1842(2) 0.0323(8) Uani 1 1 d . . . H10 H 1.0218 0.4731 0.1491 0.039 Uiso 1 1 calc R . . C11 C 0.7327(6) 0.4586(2) 0.25377(19) 0.0239(6) Uani 1 1 d . . . H11 H 0.7159 0.528 0.2665 0.029 Uiso 1 1 calc R . . I1 I -0.01365(3) 0.64652(5) 0.519095(10) 0.02283(6) 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 0.0221(14) 0.0142(14) 0.0236(16) -0.0026(12) -0.0026(12) 0.0020(12) C2 0.0294(15) 0.0192(16) 0.0233(17) 0.0022(13) 0.0048(12) -0.0009(13) N3 0.0286(14) 0.0155(12) 0.0240(14) 0.0017(11) 0.0032(11) -0.0009(11) N4 0.0204(12) 0.0130(11) 0.0225(14) -0.0029(11) -0.0001(11) 0.0026(11) N5 0.0253(13) 0.0100(11) 0.0259(14) -0.0005(10) -0.0011(11) 0.0007(10) C6 0.0219(15) 0.0207(18) 0.0171(16) -0.0041(12) -0.0038(14) 0.0038(12) C7 0.0295(15) 0.0193(15) 0.0294(17) -0.0032(15) -0.0041(14) 0.0039(14) C8 0.0350(17) 0.0264(17) 0.0276(18) -0.0103(14) -0.0055(14) 0.0118(14) C9 0.0309(18) 0.044(2) 0.028(2) -0.0104(18) -0.0023(15) 0.0150(17) C10 0.0273(16) 0.044(2) 0.0253(19) 0.0056(17) 0.0009(15) 0.0019(18) C11 0.0237(14) 0.0236(17) 0.0244(16) -0.0011(14) -0.0008(13) 0.0026(13) I1 0.02532(9) 0.01543(9) 0.02774(10) -0.00407(17) 0.00295(7) 0.00157(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N5 1.330(4) . ? C1 C2 1.400(4) . ? C1 I1 2.068(3) . ? C2 N3 1.325(4) . ? C2 H2 0.95 . ? N3 N4 1.328(4) . ? N4 N5 1.351(3) . ? N4 C6 1.427(4) . ? C6 C11 1.383(4) . ? C6 C7 1.394(4) . ? C7 C8 1.385(4) . ? C7 H7 0.95 . ? C8 C9 1.374(5) . ? C8 H8 0.95 . ? C9 C10 1.394(6) . ? C9 H9 0.95 . ? C10 C11 1.388(4) . ? C10 H10 0.95 . ? C11 H11 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 N5 C1 C2 109.3(3) . . ? N5 C1 I1 122.2(2) . . ? C2 C1 I1 128.5(2) . . ? N3 C2 C1 108.5(3) . . ? N3 C2 H2 125.8 . . ? C1 C2 H2 125.8 . . ? C2 N3 N4 104.2(2) . . ? N3 N4 N5 115.1(2) . . ? N3 N4 C6 123.5(2) . . ? N5 N4 C6 121.4(3) . . ? C1 N5 N4 102.9(2) . . ? C11 C6 C7 121.2(3) . . ? C11 C6 N4 120.2(3) . . ? C7 C6 N4 118.6(3) . . ? C8 C7 C6 118.6(3) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C9 C8 C7 120.9(3) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 120.0(3) . . ? C8 C9 H9 120 . . ? C10 C9 H9 120 . . ? C11 C10 C9 120.0(4) . . ? C11 C10 H10 120 . . ? C9 C10 H10 120 . . ? C6 C11 C10 119.3(3) . . ? C6 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? 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 N5 C1 C2 N3 -0.2(4) . . . . ? I1 C1 C2 N3 180.0(2) . . . . ? C1 C2 N3 N4 -0.1(3) . . . . ? C2 N3 N4 N5 0.5(3) . . . . ? C2 N3 N4 C6 -179.5(3) . . . . ? C2 C1 N5 N4 0.5(3) . . . . ? I1 C1 N5 N4 -179.7(2) . . . . ? N3 N4 N5 C1 -0.6(3) . . . . ? C6 N4 N5 C1 179.4(3) . . . . ? N3 N4 C6 C11 -177.3(3) . . . . ? N5 N4 C6 C11 2.7(4) . . . . ? N3 N4 C6 C7 3.8(4) . . . . ? N5 N4 C6 C7 -176.2(3) . . . . ? C11 C6 C7 C8 -0.4(5) . . . . ? N4 C6 C7 C8 178.5(3) . . . . ? C6 C7 C8 C9 0.1(5) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C8 C9 C10 C11 -0.5(5) . . . . ? C7 C6 C11 C10 0.2(5) . . . . ? N4 C6 C11 C10 -178.7(3) . . . . ? C9 C10 C11 C6 0.3(5) . . . . ? # Attachment 'web_deposit_cif_file_1_FlorisChevallier_1327423415.TB50F1_150K_2e.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-09-20 at 11:46:09 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : d:\progs\wingx\files\archive.dat # CIF files read : job struct data_job_2e _database_code_depnum_ccdc_archive 'CCDC 864275' #TrackingRef 'web_deposit_cif_file_1_FlorisChevallier_1327423415.TB50F1_150K_2e.cif' _audit_creation_date 2011-09-20T11:46:09-00:00 _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 'C8 H5 Cl I N3' _chemical_formula_sum 'C8 H5 Cl I N3' _chemical_formula_weight 305.5 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c 21 n' _symmetry_space_group_name_Hall 'P -2n -2ac' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x+1/2, y, z+1/2' 'x+1/2, y+1/2, -z+1/2' _cell_length_a 4.2056(5) _cell_length_b 13.2551(18) _cell_length_c 17.169(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 957.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7281 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.54 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 2.12 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.578 _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 0.463 _exptl_absorpt_correction_T_max 0.651 #----------------------------------------------------------------------------# # 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 0.0469 _diffrn_reflns_av_unetI/netI 0.0303 _diffrn_reflns_number 13299 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.88 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2164 _reflns_number_gt 2059 _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^)+(0.0088P)^2^+0.2264P] 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 2164 _refine_ls_number_parameters 118 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0196 _refine_ls_R_factor_gt 0.0183 _refine_ls_wR_factor_ref 0.0424 _refine_ls_wR_factor_gt 0.0418 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.006 _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 0.00(2) _refine_diff_density_max 0.268 _refine_diff_density_min -0.43 _refine_diff_density_rms 0.084 #----------------------------------------------------------------------------# # 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 -0.02587(3) 0.12622(7) 0.497295(8) 0.02352(6) Uani 1 1 d . . . C1 C 0.1181(6) 0.26219(17) 0.45004(13) 0.0216(5) Uani 1 1 d . . . C2 C 0.0481(6) 0.3574(2) 0.47605(18) 0.0251(6) Uani 1 1 d . . . H2 H -0.0845 0.3726 0.5193 0.03 Uiso 1 1 calc R . . N3 N 0.1940(5) 0.42507(16) 0.43162(11) 0.0257(4) Uani 1 1 d . . . N4 N 0.3465(5) 0.36787(15) 0.37967(11) 0.0207(4) Uani 1 1 d . . . N5 N 0.3072(5) 0.26811(15) 0.38858(10) 0.0217(4) Uani 1 1 d . . . C6 C 0.5291(5) 0.4085(2) 0.31771(17) 0.0236(6) Uani 1 1 d . . . C7 C 0.5438(6) 0.5130(2) 0.30775(19) 0.0300(7) Uani 1 1 d . . . H7 H 0.4398 0.5573 0.343 0.036 Uiso 1 1 calc R . . C8 C 0.7146(6) 0.5501(2) 0.24486(15) 0.0377(7) Uani 1 1 d . . . H8 H 0.7275 0.6209 0.2372 0.045 Uiso 1 1 calc R . . C9 C 0.8655(7) 0.4870(2) 0.19344(17) 0.0356(7) Uani 1 1 d . . . H9 H 0.9777 0.5134 0.1499 0.043 Uiso 1 1 calc R . . C10 C 0.8507(7) 0.3847(2) 0.20626(16) 0.0306(7) Uani 1 1 d . . . C11 C 0.6841(6) 0.3430(2) 0.26791(14) 0.0249(5) Uani 1 1 d . . . H11 H 0.6765 0.2721 0.2757 0.03 Uiso 1 1 calc R . . Cl2 Cl 1.04071(15) 0.30137(9) 0.14260(4) 0.04317(19) 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 0.02363(9) 0.01792(10) 0.02903(10) 0.00220(10) 0.00295(5) -0.0015(2) C1 0.0201(12) 0.0198(13) 0.0249(12) 0.0027(10) -0.0034(9) -0.0023(9) C2 0.0293(15) 0.0205(14) 0.0254(13) 0.0003(11) 0.0034(11) 0.0023(11) N3 0.0294(11) 0.0198(10) 0.0279(11) -0.0004(9) 0.0020(9) 0.0003(9) N4 0.0230(11) 0.0192(11) 0.0199(10) 0.0010(8) -0.0020(8) -0.0010(8) N5 0.0231(11) 0.0184(11) 0.0237(10) 0.0018(8) -0.0003(8) 0.0004(8) C6 0.0206(14) 0.0270(16) 0.0232(14) 0.0054(11) -0.0040(10) -0.0027(10) C7 0.0312(15) 0.0236(16) 0.0353(17) 0.0080(13) -0.0041(12) -0.0032(11) C8 0.0354(16) 0.0333(18) 0.0444(17) 0.0150(12) -0.0075(14) -0.0087(12) C9 0.0309(16) 0.047(2) 0.0287(15) 0.0111(12) -0.0037(12) -0.0110(13) C10 0.0233(14) 0.048(2) 0.0204(13) 0.0002(11) -0.0043(11) -0.0053(12) C11 0.0215(12) 0.0279(14) 0.0253(12) 0.0009(10) -0.0046(10) -0.0049(11) Cl2 0.0380(4) 0.0633(5) 0.0282(4) -0.0097(4) 0.0060(3) -0.0093(4) #----------------------------------------------------------------------------# # 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 2.067(3) . ? C1 N5 1.324(3) . ? C1 C2 1.371(4) . ? C2 N3 1.328(4) . ? C2 H2 0.95 . ? N3 N4 1.335(3) . ? N4 N5 1.341(2) . ? N4 C6 1.418(3) . ? C6 C11 1.382(4) . ? C6 C7 1.396(4) . ? C7 C8 1.387(4) . ? C7 H7 0.95 . ? C8 C9 1.372(4) . ? C8 H8 0.95 . ? C9 C10 1.375(4) . ? C9 H9 0.95 . ? C10 C11 1.384(4) . ? C10 Cl2 1.747(3) . ? C11 H11 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 N5 C1 C2 109.5(2) . . ? N5 C1 I1 122.72(17) . . ? C2 C1 I1 127.73(19) . . ? N3 C2 C1 109.6(2) . . ? N3 C2 H2 125.2 . . ? C1 C2 H2 125.2 . . ? C2 N3 N4 102.8(2) . . ? N3 N4 N5 115.1(2) . . ? N3 N4 C6 123.1(2) . . ? N5 N4 C6 121.8(2) . . ? C1 N5 N4 102.91(18) . . ? C11 C6 C7 121.8(3) . . ? C11 C6 N4 118.7(2) . . ? C7 C6 N4 119.5(3) . . ? C8 C7 C6 118.0(3) . . ? C8 C7 H7 121 . . ? C6 C7 H7 121 . . ? C9 C8 C7 121.6(3) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 118.5(3) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C9 C10 C11 122.6(3) . . ? C9 C10 Cl2 120.1(2) . . ? C11 C10 Cl2 117.2(2) . . ? C6 C11 C10 117.4(3) . . ? C6 C11 H11 121.3 . . ? C10 C11 H11 121.3 . . ? 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 N5 C1 C2 N3 -0.4(3) . . . . ? I1 C1 C2 N3 177.82(17) . . . . ? C1 C2 N3 N4 0.4(3) . . . . ? C2 N3 N4 N5 -0.2(3) . . . . ? C2 N3 N4 C6 177.8(2) . . . . ? C2 C1 N5 N4 0.2(3) . . . . ? I1 C1 N5 N4 -178.09(16) . . . . ? N3 N4 N5 C1 0.0(3) . . . . ? C6 N4 N5 C1 -178.0(2) . . . . ? N3 N4 C6 C11 178.6(2) . . . . ? N5 N4 C6 C11 -3.5(3) . . . . ? N3 N4 C6 C7 -2.5(4) . . . . ? N5 N4 C6 C7 175.4(2) . . . . ? C11 C6 C7 C8 1.3(4) . . . . ? N4 C6 C7 C8 -177.6(2) . . . . ? C6 C7 C8 C9 0.1(4) . . . . ? C7 C8 C9 C10 -1.4(4) . . . . ? C8 C9 C10 C11 1.4(4) . . . . ? C8 C9 C10 Cl2 -179.7(2) . . . . ? C7 C6 C11 C10 -1.3(4) . . . . ? N4 C6 C11 C10 177.6(2) . . . . ? C9 C10 C11 C6 -0.1(4) . . . . ? Cl2 C10 C11 C6 -179.00(18) . . . . ? # Attachment 'web_deposit_cif_file_2_FlorisChevallier_1327423415.TB038F2_150K_3b.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-08-30 at 17:08:07 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : d:\progs\wingx\files\archive.dat # CIF files read : job struct data_job_3b _database_code_depnum_ccdc_archive 'CCDC 864276' #TrackingRef 'web_deposit_cif_file_2_FlorisChevallier_1327423415.TB038F2_150K_3b.cif' _audit_creation_date 2011-08-30T17:08:07-00:00 _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 'C9 H7 I2 N3' _chemical_formula_sum 'C9 H7 I2 N3' _chemical_formula_weight 410.98 _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 10.3473(15) _cell_length_b 7.1028(8) _cell_length_c 15.555(2) _cell_angle_alpha 90 _cell_angle_beta 104.138(6) _cell_angle_gamma 90 _cell_volume 1108.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4965 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 27.46 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 2.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.638 _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 0.211 _exptl_absorpt_correction_T_max 0.362 #----------------------------------------------------------------------------# # 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 0.0407 _diffrn_reflns_av_unetI/netI 0.0362 _diffrn_reflns_number 8769 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 2544 _reflns_number_gt 2320 _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^)+(0.0227P)^2^+0.2687P] 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 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0282 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0603 _refine_ls_wR_factor_gt 0.0588 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.66 _refine_diff_density_min -1.228 _refine_diff_density_rms 0.206 #----------------------------------------------------------------------------# # 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 C1 C 0.6385(3) 0.3828(4) 0.3456(2) 0.0179(6) Uani 1 1 d . . . C2 C 0.5594(3) 0.4106(5) 0.4053(2) 0.0222(7) Uani 1 1 d . . . H2 H 0.4708 0.4577 0.3912 0.027 Uiso 1 1 calc R . . N3 N 0.6297(3) 0.3597(4) 0.48545(19) 0.0226(6) Uani 1 1 d . . . N4 N 0.7464(3) 0.3051(4) 0.47207(17) 0.0173(5) Uani 1 1 d . . . N5 N 0.7569(3) 0.3156(4) 0.38828(17) 0.0194(6) Uani 1 1 d . . . C6 C 0.8541(3) 0.2379(5) 0.5419(2) 0.0174(6) Uani 1 1 d . . . C7 C 0.9496(3) 0.3672(5) 0.5849(2) 0.0229(7) Uani 1 1 d . . . H7 H 0.9418 0.4966 0.569 0.027 Uiso 1 1 calc R . . C8 C 1.0561(3) 0.3045(5) 0.6509(2) 0.0241(7) Uani 1 1 d . . . H8 H 1.1212 0.3925 0.6803 0.029 Uiso 1 1 calc R . . C9 C 1.0701(3) 0.1177(5) 0.6752(2) 0.0211(7) Uani 1 1 d . . . C10 C 0.9727(3) -0.0112(5) 0.6320(2) 0.0199(6) Uani 1 1 d . . . H10 H 0.9808 -0.1406 0.6478 0.024 Uiso 1 1 calc R . . C11 C 0.8644(3) 0.0501(4) 0.5661(2) 0.0179(6) Uani 1 1 d . . . C12 C 1.1899(4) 0.0501(6) 0.7448(2) 0.0284(8) Uani 1 1 d . . . H12A H 1.2678 0.046 0.7195 0.043 Uiso 1 1 calc R . . H12B H 1.1723 -0.0762 0.7646 0.043 Uiso 1 1 calc R . . H12C H 1.2073 0.1367 0.7954 0.043 Uiso 1 1 calc R . . I1 I 0.59352(2) 0.43062(4) 0.210779(14) 0.02701(8) Uani 1 1 d . . . I2 I 0.71898(2) -0.14388(3) 0.503989(14) 0.02405(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 0.0160(15) 0.0167(16) 0.0196(16) 0.0024(13) 0.0013(12) 0.0001(12) C2 0.0171(16) 0.0262(18) 0.0231(17) -0.0002(14) 0.0047(14) 0.0030(13) N3 0.0194(14) 0.0271(16) 0.0218(14) 0.0010(12) 0.0062(12) 0.0042(12) N4 0.0170(12) 0.0200(14) 0.0148(12) 0.0012(11) 0.0038(10) 0.0024(11) N5 0.0193(13) 0.0221(15) 0.0173(13) 0.0022(11) 0.0056(11) 0.0020(11) C6 0.0151(14) 0.0226(17) 0.0147(14) 0.0002(12) 0.0041(12) 0.0048(12) C7 0.0243(17) 0.0219(18) 0.0222(17) -0.0002(13) 0.0052(14) -0.0016(14) C8 0.0196(16) 0.0289(19) 0.0214(17) -0.0034(15) 0.0005(14) -0.0057(14) C9 0.0155(15) 0.032(2) 0.0154(15) 0.0000(14) 0.0033(13) 0.0024(13) C10 0.0213(15) 0.0216(17) 0.0164(15) 0.0021(13) 0.0040(13) 0.0017(13) C11 0.0172(15) 0.0208(18) 0.0158(15) -0.0028(12) 0.0041(12) -0.0032(12) C12 0.0213(17) 0.040(2) 0.0221(17) 0.0023(15) 0.0011(14) 0.0040(15) I1 0.02458(13) 0.03609(16) 0.01716(12) 0.00514(9) -0.00105(9) 0.00371(9) I2 0.02519(13) 0.02202(14) 0.02147(13) -0.00010(8) -0.00099(9) -0.00475(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 N5 1.331(4) . ? C1 C2 1.394(4) . ? C1 I1 2.062(3) . ? C2 N3 1.331(4) . ? C2 H2 0.95 . ? N3 N4 1.332(4) . ? N4 N5 1.336(4) . ? N4 C6 1.435(4) . ? C6 C11 1.383(5) . ? C6 C7 1.395(5) . ? C7 C8 1.384(5) . ? C7 H7 0.95 . ? C8 C9 1.378(5) . ? C8 H8 0.95 . ? C9 C10 1.405(5) . ? C9 C12 1.511(5) . ? C10 C11 1.391(4) . ? C10 H10 0.95 . ? C11 I2 2.094(3) . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 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 N5 C1 C2 109.7(3) . . ? N5 C1 I1 121.2(2) . . ? C2 C1 I1 129.1(2) . . ? N3 C2 C1 108.1(3) . . ? N3 C2 H2 126 . . ? C1 C2 H2 126 . . ? C2 N3 N4 104.0(3) . . ? N3 N4 N5 115.4(3) . . ? N3 N4 C6 123.0(3) . . ? N5 N4 C6 121.6(2) . . ? C1 N5 N4 102.9(3) . . ? C11 C6 C7 120.4(3) . . ? C11 C6 N4 121.4(3) . . ? C7 C6 N4 118.2(3) . . ? C8 C7 C6 119.1(3) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C9 C8 C7 121.6(3) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 118.8(3) . . ? C8 C9 C12 121.0(3) . . ? C10 C9 C12 120.2(3) . . ? C11 C10 C9 120.2(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C6 C11 C10 119.8(3) . . ? C6 C11 I2 120.7(2) . . ? C10 C11 I2 119.5(2) . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 N5 C1 C2 N3 -0.1(4) . . . . ? I1 C1 C2 N3 179.7(2) . . . . ? C1 C2 N3 N4 0.3(4) . . . . ? C2 N3 N4 N5 -0.5(4) . . . . ? C2 N3 N4 C6 -180.0(3) . . . . ? C2 C1 N5 N4 -0.1(4) . . . . ? I1 C1 N5 N4 180.0(2) . . . . ? N3 N4 N5 C1 0.4(4) . . . . ? C6 N4 N5 C1 179.9(3) . . . . ? N3 N4 C6 C11 87.4(4) . . . . ? N5 N4 C6 C11 -92.1(4) . . . . ? N3 N4 C6 C7 -93.1(4) . . . . ? N5 N4 C6 C7 87.4(4) . . . . ? C11 C6 C7 C8 1.1(5) . . . . ? N4 C6 C7 C8 -178.5(3) . . . . ? C6 C7 C8 C9 0.1(5) . . . . ? C7 C8 C9 C10 -0.6(5) . . . . ? C7 C8 C9 C12 177.4(3) . . . . ? C8 C9 C10 C11 -0.1(5) . . . . ? C12 C9 C10 C11 -178.1(3) . . . . ? C7 C6 C11 C10 -1.7(5) . . . . ? N4 C6 C11 C10 177.8(3) . . . . ? C7 C6 C11 I2 178.5(2) . . . . ? N4 C6 C11 I2 -2.0(4) . . . . ? C9 C10 C11 C6 1.2(5) . . . . ? C9 C10 C11 I2 -179.0(2) . . . . ? # Attachment 'web_deposit_cif_file_3_FlorisChevallier_1327423415.TB034_F3_150K_3d.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-10-28 at 17:04:34 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : d:\progs\wingx\files\archive.dat # CIF files read : job struct data_job_3d _database_code_depnum_ccdc_archive 'CCDC 864277' #TrackingRef 'web_deposit_cif_file_3_FlorisChevallier_1327423415.TB034_F3_150K_3d.cif' _audit_creation_date 2011-10-28T17:04:34-00:00 _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 '2(C9 H7 I2 N3 O)' _chemical_formula_sum 'C18 H14 I4 N6 O2' _chemical_formula_weight 853.95 _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 7.7817(6) _cell_length_b 10.5301(8) _cell_length_c 14.2726(11) _cell_angle_alpha 79.833(4) _cell_angle_beta 89.092(4) _cell_angle_gamma 80.124(4) _cell_volume 1133.98(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5667 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.37 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description stick _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 2.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.524 _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 0.590 _exptl_absorpt_correction_T_max 0.847 #----------------------------------------------------------------------------# # 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 0.0414 _diffrn_reflns_av_unetI/netI 0.0473 _diffrn_reflns_number 14983 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 5165 _reflns_number_gt 4179 _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^)+(0.0534P)^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 none _refine_ls_number_reflns 5165 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.049 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.02 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 2.739 _refine_diff_density_min -1.154 _refine_diff_density_rms 0.221 #----------------------------------------------------------------------------# # 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 0.57851(5) -0.35818(3) 0.91725(3) 0.02643(11) Uani 1 1 d . . . I2 I 0.29414(5) 0.30501(3) 0.81299(2) 0.02429(11) Uani 1 1 d . . . C1 C 0.5784(6) -0.1613(5) 0.8698(4) 0.0192(11) Uani 1 1 d . . . C2 C 0.6318(7) -0.0714(5) 0.9170(4) 0.0249(12) Uani 1 1 d . . . H2 H 0.6763 -0.0893 0.9804 0.03 Uiso 1 1 calc R . . N3 N 0.6111(6) 0.0455(4) 0.8594(3) 0.0259(10) Uani 1 1 d . . . N4 N 0.5432(6) 0.0215(4) 0.7798(3) 0.0208(9) Uani 1 1 d . . . N5 N 0.5232(6) -0.1027(4) 0.7821(3) 0.0221(10) Uani 1 1 d . . . C6 C 0.5087(7) 0.1157(5) 0.6942(4) 0.0211(11) Uani 1 1 d . . . C7 C 0.5750(7) 0.0784(5) 0.6104(4) 0.0212(11) Uani 1 1 d . . . H7 H 0.6424 -0.0064 0.6124 0.025 Uiso 1 1 calc R . . C8 C 0.5447(7) 0.1622(5) 0.5244(4) 0.0225(11) Uani 1 1 d . . . H8 H 0.591 0.1363 0.4673 0.027 Uiso 1 1 calc R . . C9 C 0.4446(7) 0.2860(5) 0.5227(4) 0.0181(10) Uani 1 1 d . . . C10 C 0.3770(7) 0.3259(5) 0.6046(4) 0.0196(11) Uani 1 1 d . . . H10 H 0.3104 0.411 0.6018 0.024 Uiso 1 1 calc R . . C11 C 0.4073(6) 0.2397(5) 0.6924(3) 0.0170(10) Uani 1 1 d . . . O12 O 0.4065(5) 0.3784(4) 0.4417(3) 0.0255(8) Uani 1 1 d . . . C13 C 0.5057(8) 0.3581(6) 0.3583(4) 0.0296(13) Uani 1 1 d . . . H13A H 0.6302 0.337 0.3749 0.044 Uiso 1 1 calc R . . H13B H 0.4835 0.4379 0.31 0.044 Uiso 1 1 calc R . . H13C H 0.4709 0.2854 0.3329 0.044 Uiso 1 1 calc R . . I11 I -0.12151(5) 0.35854(3) 0.58349(2) 0.02288(10) Uani 1 1 d . . . I12 I -0.04734(5) -0.30443(3) 0.69079(2) 0.02387(11) Uani 1 1 d . . . C21 C -0.0059(7) 0.1657(5) 0.6267(4) 0.0183(10) Uani 1 1 d . . . C22 C 0.0970(7) 0.0789(5) 0.5782(4) 0.0243(12) Uani 1 1 d . . . H22 H 0.1319 0.0984 0.5139 0.029 Uiso 1 1 calc R . . N23 N 0.1395(6) -0.0366(4) 0.6357(3) 0.0233(10) Uani 1 1 d . . . N24 N 0.0591(6) -0.0164(4) 0.7173(3) 0.0198(9) Uani 1 1 d . . . N25 N -0.0299(6) 0.1044(4) 0.7156(3) 0.0200(9) Uani 1 1 d . . . C26 C 0.0753(7) -0.1098(5) 0.8031(4) 0.0192(11) Uani 1 1 d . . . C27 C 0.1214(7) -0.0697(5) 0.8845(4) 0.0193(11) Uani 1 1 d . . . H27 H 0.1446 0.0167 0.8806 0.023 Uiso 1 1 calc R . . C28 C 0.1349(7) -0.1533(5) 0.9724(4) 0.0227(11) Uani 1 1 d . . . H28 H 0.1687 -0.1254 1.0281 0.027 Uiso 1 1 calc R . . C29 C 0.0979(7) -0.2780(5) 0.9764(3) 0.0184(11) Uani 1 1 d . . . C30 C 0.0497(7) -0.3224(5) 0.8976(4) 0.0195(11) Uani 1 1 d . . . H30 H 0.0252 -0.4087 0.9027 0.023 Uiso 1 1 calc R . . C31 C 0.0370(7) -0.2363(5) 0.8082(3) 0.0186(10) Uani 1 1 d . . . O32 O 0.1058(5) -0.3686(3) 1.0594(3) 0.0227(8) Uani 1 1 d . . . C33 C 0.1822(7) -0.3371(5) 1.1415(4) 0.0236(12) Uani 1 1 d . . . H33A H 0.296 -0.3123 1.125 0.035 Uiso 1 1 calc R . . H33B H 0.1971 -0.4136 1.1928 0.035 Uiso 1 1 calc R . . H33C H 0.1055 -0.264 1.1627 0.035 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 0.0381(2) 0.01656(18) 0.0219(2) 0.00155(14) 0.00552(15) -0.00265(15) I2 0.0314(2) 0.02277(19) 0.01728(19) -0.00388(14) 0.00393(14) -0.00070(15) C1 0.019(3) 0.014(2) 0.020(3) 0.004(2) 0.000(2) 0.003(2) C2 0.034(3) 0.018(3) 0.021(3) 0.000(2) -0.007(2) -0.004(2) N3 0.040(3) 0.020(2) 0.018(2) -0.0023(18) -0.006(2) -0.004(2) N4 0.026(2) 0.016(2) 0.020(2) -0.0029(17) 0.0001(19) -0.0024(18) N5 0.029(2) 0.017(2) 0.021(2) -0.0034(17) 0.0027(19) -0.0046(18) C6 0.019(3) 0.021(3) 0.024(3) -0.003(2) -0.001(2) -0.004(2) C7 0.027(3) 0.017(3) 0.019(3) -0.005(2) 0.003(2) 0.000(2) C8 0.025(3) 0.023(3) 0.019(3) -0.004(2) 0.001(2) -0.003(2) C9 0.017(3) 0.023(3) 0.016(3) -0.004(2) 0.0004(19) -0.007(2) C10 0.023(3) 0.019(3) 0.017(3) -0.010(2) -0.004(2) 0.002(2) C11 0.021(3) 0.016(2) 0.015(2) -0.0016(19) 0.006(2) -0.005(2) O12 0.035(2) 0.023(2) 0.0131(18) 0.0028(15) 0.0022(16) 0.0010(17) C13 0.035(3) 0.029(3) 0.021(3) 0.003(2) 0.001(2) -0.005(3) I11 0.0327(2) 0.01647(18) 0.01795(19) 0.00139(13) -0.00403(14) -0.00403(14) I12 0.0352(2) 0.02257(19) 0.01539(18) -0.00358(13) -0.00189(14) -0.00883(15) C21 0.024(3) 0.014(2) 0.016(3) 0.0022(19) -0.002(2) -0.005(2) C22 0.029(3) 0.026(3) 0.016(3) 0.000(2) 0.002(2) -0.006(2) N23 0.031(3) 0.022(2) 0.015(2) -0.0022(18) 0.0035(19) -0.0016(19) N24 0.026(2) 0.018(2) 0.013(2) 0.0003(17) 0.0032(18) -0.0005(18) N25 0.028(2) 0.015(2) 0.017(2) -0.0022(16) 0.0017(18) -0.0023(18) C26 0.020(3) 0.018(3) 0.019(3) -0.002(2) 0.003(2) 0.000(2) C27 0.028(3) 0.013(2) 0.018(3) -0.0032(19) 0.000(2) -0.006(2) C28 0.030(3) 0.023(3) 0.013(3) -0.001(2) -0.006(2) -0.002(2) C29 0.022(3) 0.019(3) 0.012(2) 0.0036(19) 0.002(2) -0.003(2) C30 0.026(3) 0.020(3) 0.016(3) -0.011(2) 0.005(2) -0.006(2) C31 0.026(3) 0.017(2) 0.013(2) -0.0052(19) 0.000(2) -0.004(2) O32 0.035(2) 0.0164(18) 0.0149(18) 0.0024(14) -0.0029(16) -0.0055(16) C33 0.028(3) 0.023(3) 0.019(3) -0.002(2) -0.006(2) -0.001(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 2.064(5) . ? I2 C11 2.091(5) . ? C1 N5 1.337(6) . ? C1 C2 1.375(7) . ? C2 N3 1.340(7) . ? C2 H2 0.95 . ? N3 N4 1.342(6) . ? N4 N5 1.338(6) . ? N4 C6 1.428(6) . ? C6 C7 1.388(7) . ? C6 C11 1.402(7) . ? C7 C8 1.378(7) . ? C7 H7 0.95 . ? C8 C9 1.395(7) . ? C8 H8 0.95 . ? C9 O12 1.373(6) . ? C9 C10 1.377(7) . ? C10 C11 1.409(7) . ? C10 H10 0.95 . ? O12 C13 1.436(7) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? I11 C21 2.064(5) . ? I12 C31 2.091(5) . ? C21 N25 1.343(6) . ? C21 C22 1.383(8) . ? C22 N23 1.334(7) . ? C22 H22 0.95 . ? N23 N24 1.346(6) . ? N24 N25 1.336(6) . ? N24 C26 1.422(6) . ? C26 C27 1.376(7) . ? C26 C31 1.403(7) . ? C27 C28 1.394(7) . ? C27 H27 0.95 . ? C28 C29 1.384(7) . ? C28 H28 0.95 . ? C29 C30 1.372(7) . ? C29 O32 1.379(6) . ? C30 C31 1.423(7) . ? C30 H30 0.95 . ? O32 C33 1.436(6) . ? C33 H33A 0.98 . ? C33 H33B 0.98 . ? C33 H33C 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 N5 C1 C2 109.4(4) . . ? N5 C1 I1 121.6(4) . . ? C2 C1 I1 128.9(4) . . ? N3 C2 C1 109.3(5) . . ? N3 C2 H2 125.4 . . ? C1 C2 H2 125.4 . . ? N4 N3 C2 103.0(4) . . ? N5 N4 N3 115.1(4) . . ? N5 N4 C6 120.6(4) . . ? N3 N4 C6 124.0(4) . . ? N4 N5 C1 103.1(4) . . ? C7 C6 C11 120.2(5) . . ? C7 C6 N4 117.3(5) . . ? C11 C6 N4 122.4(5) . . ? C6 C7 C8 121.1(5) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C7 C8 C9 118.7(5) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? O12 C9 C10 114.2(4) . . ? O12 C9 C8 124.1(5) . . ? C10 C9 C8 121.6(5) . . ? C9 C10 C11 119.6(5) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C6 C11 C10 118.8(5) . . ? C6 C11 I2 123.8(4) . . ? C10 C11 I2 117.4(4) . . ? C9 O12 C13 117.5(4) . . ? O12 C13 H13A 109.5 . . ? O12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N25 C21 C22 109.0(4) . . ? N25 C21 I11 119.9(4) . . ? C22 C21 I11 131.1(4) . . ? N23 C22 C21 109.4(5) . . ? N23 C22 H22 125.3 . . ? C21 C22 H22 125.3 . . ? C22 N23 N24 103.3(4) . . ? N25 N24 N23 115.0(4) . . ? N25 N24 C26 120.3(4) . . ? N23 N24 C26 124.4(4) . . ? N24 N25 C21 103.3(4) . . ? C27 C26 C31 119.9(5) . . ? C27 C26 N24 117.3(4) . . ? C31 C26 N24 122.7(5) . . ? C26 C27 C28 121.4(5) . . ? C26 C27 H27 119.3 . . ? C28 C27 H27 119.3 . . ? C29 C28 C27 118.2(5) . . ? C29 C28 H28 120.9 . . ? C27 C28 H28 120.9 . . ? C30 C29 O32 114.0(4) . . ? C30 C29 C28 122.8(5) . . ? O32 C29 C28 123.3(5) . . ? C29 C30 C31 118.5(5) . . ? C29 C30 H30 120.7 . . ? C31 C30 H30 120.7 . . ? C26 C31 C30 119.3(5) . . ? C26 C31 I12 123.2(4) . . ? C30 C31 I12 117.5(4) . . ? C29 O32 C33 117.0(4) . . ? O32 C33 H33A 109.5 . . ? O32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 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 N5 C1 C2 N3 -0.1(7) . . . . ? I1 C1 C2 N3 179.3(4) . . . . ? C1 C2 N3 N4 0.9(6) . . . . ? C2 N3 N4 N5 -1.5(6) . . . . ? C2 N3 N4 C6 -175.6(5) . . . . ? N3 N4 N5 C1 1.4(6) . . . . ? C6 N4 N5 C1 175.7(5) . . . . ? C2 C1 N5 N4 -0.7(6) . . . . ? I1 C1 N5 N4 179.8(3) . . . . ? N5 N4 C6 C7 -45.3(7) . . . . ? N3 N4 C6 C7 128.5(6) . . . . ? N5 N4 C6 C11 132.4(5) . . . . ? N3 N4 C6 C11 -53.8(7) . . . . ? C11 C6 C7 C8 0.8(8) . . . . ? N4 C6 C7 C8 178.6(5) . . . . ? C6 C7 C8 C9 -0.4(8) . . . . ? C7 C8 C9 O12 179.5(5) . . . . ? C7 C8 C9 C10 0.3(8) . . . . ? O12 C9 C10 C11 180.0(5) . . . . ? C8 C9 C10 C11 -0.7(8) . . . . ? C7 C6 C11 C10 -1.2(8) . . . . ? N4 C6 C11 C10 -178.9(5) . . . . ? C7 C6 C11 I2 178.1(4) . . . . ? N4 C6 C11 I2 0.4(7) . . . . ? C9 C10 C11 C6 1.2(7) . . . . ? C9 C10 C11 I2 -178.2(4) . . . . ? C10 C9 O12 C13 165.0(5) . . . . ? C8 C9 O12 C13 -14.2(7) . . . . ? N25 C21 C22 N23 -0.5(6) . . . . ? I11 C21 C22 N23 -179.0(4) . . . . ? C21 C22 N23 N24 0.7(6) . . . . ? C22 N23 N24 N25 -0.6(6) . . . . ? C22 N23 N24 C26 -175.7(5) . . . . ? N23 N24 N25 C21 0.3(6) . . . . ? C26 N24 N25 C21 175.6(4) . . . . ? C22 C21 N25 N24 0.1(6) . . . . ? I11 C21 N25 N24 178.8(3) . . . . ? N25 N24 C26 C27 -47.1(7) . . . . ? N23 N24 C26 C27 127.7(6) . . . . ? N25 N24 C26 C31 129.3(5) . . . . ? N23 N24 C26 C31 -55.9(7) . . . . ? C31 C26 C27 C28 1.4(8) . . . . ? N24 C26 C27 C28 177.9(5) . . . . ? C26 C27 C28 C29 -1.0(8) . . . . ? C27 C28 C29 C30 0.3(8) . . . . ? C27 C28 C29 O32 -179.6(5) . . . . ? O32 C29 C30 C31 179.8(4) . . . . ? C28 C29 C30 C31 -0.1(8) . . . . ? C27 C26 C31 C30 -1.1(8) . . . . ? N24 C26 C31 C30 -177.4(5) . . . . ? C27 C26 C31 I12 176.6(4) . . . . ? N24 C26 C31 I12 0.3(7) . . . . ? C29 C30 C31 C26 0.5(8) . . . . ? C29 C30 C31 I12 -177.4(4) . . . . ? C30 C29 O32 C33 170.2(5) . . . . ? C28 C29 O32 C33 -9.9(7) . . . . ? # Attachment 'web_deposit_cif_file_5_FlorisChevallier_1327423415.TB050F2_150K_3e.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-09-01 at 12:31:27 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : d:\progs\wingx\files\archive.dat # CIF files read : job struct data_job_3e _database_code_depnum_ccdc_archive 'CCDC 864278' #TrackingRef 'web_deposit_cif_file_5_FlorisChevallier_1327423415.TB050F2_150K_3e.cif' _audit_creation_date 2011-09-01T12:31:27-00:00 _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 'C8 H4 Cl I2 N3' _chemical_formula_sum 'C8 H4 Cl I2 N3' _chemical_formula_weight 431.39 _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 10.8653(4) _cell_length_b 7.7070(2) _cell_length_c 13.2464(5) _cell_angle_alpha 90 _cell_angle_beta 93.5294(18) _cell_angle_gamma 90 _cell_volume 1107.13(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6309 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 27.47 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_diffrn 2.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.886 _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 0.275 _exptl_absorpt_correction_T_max 0.368 #----------------------------------------------------------------------------# # 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 0.0272 _diffrn_reflns_av_unetI/netI 0.0241 _diffrn_reflns_number 9490 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 2508 _reflns_number_gt 2368 _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^)+(0.0265P)^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 none _refine_ls_number_reflns 2508 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0243 _refine_ls_R_factor_gt 0.0224 _refine_ls_wR_factor_ref 0.0567 _refine_ls_wR_factor_gt 0.056 _refine_ls_goodness_of_fit_ref 1.277 _refine_ls_restrained_S_all 1.277 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.508 _refine_diff_density_min -1.423 _refine_diff_density_rms 0.189 #----------------------------------------------------------------------------# # 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 0.0963(3) 0.4301(4) 0.7666(2) 0.0165(6) Uani 1 1 d . . . C2 C 0.0828(3) 0.3970(4) 0.8686(2) 0.0217(7) Uani 1 1 d . . . H2 H 0.0138 0.3429 0.896 0.026 Uiso 1 1 calc R . . N3 N 0.1834(2) 0.4542(3) 0.92149(19) 0.0211(6) Uani 1 1 d . . . N4 N 0.2509(2) 0.5247(3) 0.85066(18) 0.0162(5) Uani 1 1 d . . . N5 N 0.2020(2) 0.5104(3) 0.75481(18) 0.0162(5) Uani 1 1 d . . . C6 C 0.3725(3) 0.5897(4) 0.8693(2) 0.0146(6) Uani 1 1 d . . . C7 C 0.4581(3) 0.5478(4) 0.8003(2) 0.0172(6) Uani 1 1 d . . . H7 H 0.4351 0.4765 0.7437 0.021 Uiso 1 1 calc R . . C8 C 0.5770(3) 0.6099(4) 0.8138(2) 0.0168(6) Uani 1 1 d . . . C9 C 0.6147(3) 0.7086(4) 0.8977(2) 0.0195(6) Uani 1 1 d . . . H9 H 0.6978 0.7463 0.9079 0.023 Uiso 1 1 calc R . . C10 C 0.5286(3) 0.7505(4) 0.9658(2) 0.0178(6) Uani 1 1 d . . . H10 H 0.5531 0.8192 1.023 0.021 Uiso 1 1 calc R . . C11 C 0.4065(3) 0.6949(4) 0.9531(2) 0.0148(6) Uani 1 1 d . . . Cl1 Cl 0.68233(7) 0.56187(11) 0.72385(6) 0.02634(17) Uani 1 1 d . . . I1 I -0.022551(18) 0.37983(3) 0.641018(15) 0.02157(8) Uani 1 1 d . . . I2 I 0.286260(18) 0.79038(2) 1.057932(14) 0.01909(7) 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 0.0183(14) 0.0130(13) 0.0179(14) -0.0023(11) -0.0020(12) -0.0017(11) C2 0.0242(16) 0.0179(15) 0.0229(16) 0.0008(12) 0.0008(13) -0.0081(12) N3 0.0211(13) 0.0231(13) 0.0192(13) 0.0027(11) 0.0017(11) -0.0049(11) N4 0.0188(12) 0.0161(12) 0.0138(11) 0.0002(10) 0.0013(10) -0.0017(10) N5 0.0179(12) 0.0185(12) 0.0121(11) -0.0006(10) -0.0004(10) -0.0013(10) C6 0.0151(14) 0.0150(13) 0.0133(13) 0.0015(11) -0.0024(11) 0.0001(10) C7 0.0221(15) 0.0148(14) 0.0146(14) -0.0011(11) -0.0007(12) 0.0025(11) C8 0.0187(15) 0.0190(15) 0.0131(14) 0.0036(11) 0.0039(11) 0.0034(11) C9 0.0162(14) 0.0188(15) 0.0229(16) 0.0035(12) -0.0030(12) 0.0001(11) C10 0.0207(15) 0.0193(14) 0.0128(14) -0.0011(11) -0.0045(12) -0.0012(12) C11 0.0181(14) 0.0150(14) 0.0113(13) 0.0010(11) 0.0005(11) 0.0023(11) Cl1 0.0230(4) 0.0323(4) 0.0246(4) -0.0016(3) 0.0087(3) 0.0005(3) I1 0.01939(12) 0.02461(13) 0.02024(12) -0.00332(8) -0.00258(8) -0.00532(8) I2 0.02047(12) 0.02069(12) 0.01619(11) -0.00251(7) 0.00183(8) 0.00216(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N5 1.322(4) . ? C1 C2 1.392(4) . ? C1 I1 2.078(3) . ? C2 N3 1.336(4) . ? C2 H2 0.95 . ? N3 N4 1.341(4) . ? N4 N5 1.351(3) . ? N4 C6 1.420(4) . ? C6 C7 1.382(4) . ? C6 C11 1.406(4) . ? C7 C8 1.379(4) . ? C7 H7 0.95 . ? C8 C9 1.387(4) . ? C8 Cl1 1.743(3) . ? C9 C10 1.377(5) . ? C9 H9 0.95 . ? C10 C11 1.395(4) . ? C10 H10 0.95 . ? C11 I2 2.098(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 C1 C2 110.1(2) . . ? N5 C1 I1 119.6(2) . . ? C2 C1 I1 130.2(2) . . ? N3 C2 C1 108.5(3) . . ? N3 C2 H2 125.7 . . ? C1 C2 H2 125.7 . . ? C2 N3 N4 103.4(2) . . ? N3 N4 N5 115.1(2) . . ? N3 N4 C6 124.4(2) . . ? N5 N4 C6 120.0(2) . . ? C1 N5 N4 102.8(2) . . ? C7 C6 C11 120.1(3) . . ? C7 C6 N4 117.4(2) . . ? C11 C6 N4 122.5(3) . . ? C8 C7 C6 119.8(3) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 121.5(3) . . ? C7 C8 Cl1 119.1(2) . . ? C9 C8 Cl1 119.4(2) . . ? C10 C9 C8 118.3(3) . . ? C10 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? C9 C10 C11 121.9(3) . . ? C9 C10 H10 119 . . ? C11 C10 H10 119 . . ? C10 C11 C6 118.3(3) . . ? C10 C11 I2 116.1(2) . . ? C6 C11 I2 125.5(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 C1 C2 N3 -1.5(4) . . . . ? I1 C1 C2 N3 -179.3(2) . . . . ? C1 C2 N3 N4 2.2(3) . . . . ? C2 N3 N4 N5 -2.4(3) . . . . ? C2 N3 N4 C6 -174.1(3) . . . . ? C2 C1 N5 N4 0.0(3) . . . . ? I1 C1 N5 N4 178.13(18) . . . . ? N3 N4 N5 C1 1.5(3) . . . . ? C6 N4 N5 C1 173.6(3) . . . . ? N3 N4 C6 C7 136.1(3) . . . . ? N5 N4 C6 C7 -35.2(4) . . . . ? N3 N4 C6 C11 -44.9(4) . . . . ? N5 N4 C6 C11 143.8(3) . . . . ? C11 C6 C7 C8 -0.1(4) . . . . ? N4 C6 C7 C8 178.9(3) . . . . ? C6 C7 C8 C9 2.6(4) . . . . ? C6 C7 C8 Cl1 -177.9(2) . . . . ? C7 C8 C9 C10 -2.9(4) . . . . ? Cl1 C8 C9 C10 177.6(2) . . . . ? C8 C9 C10 C11 0.8(4) . . . . ? C9 C10 C11 C6 1.6(4) . . . . ? C9 C10 C11 I2 -174.8(2) . . . . ? C7 C6 C11 C10 -1.9(4) . . . . ? N4 C6 C11 C10 179.1(3) . . . . ? C7 C6 C11 I2 174.1(2) . . . . ? N4 C6 C11 I2 -4.9(4) . . . . ? # Attachment 'web_deposit_cif_file_7_FlorisChevallier_1327423415.TB046F2_150K_4b.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-08-30 at 17:54:12 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : d:\progs\wingx\files\archive.dat # CIF files read : job struct data_job_4b _database_code_depnum_ccdc_archive 'CCDC 864279' #TrackingRef 'web_deposit_cif_file_7_FlorisChevallier_1327423415.TB046F2_150K_4b.cif' _audit_creation_date 2011-08-30T17:54:12-00:00 _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 'C9 H8 I N3' _chemical_formula_sum 'C9 H8 I N3' _chemical_formula_weight 285.08 _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 7.993(2) _cell_length_b 14.366(4) _cell_length_c 8.736(2) _cell_angle_alpha 90 _cell_angle_beta 94.686(13) _cell_angle_gamma 90 _cell_volume 999.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4897 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 27.34 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.38 _exptl_crystal_density_diffrn 1.894 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.160 _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 0.173 _exptl_absorpt_correction_T_max 0.301 #----------------------------------------------------------------------------# # 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 0.0368 _diffrn_reflns_av_unetI/netI 0.034 _diffrn_reflns_number 7639 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _reflns_number_total 2254 _reflns_number_gt 2096 _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^+4.0708P] 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 2254 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.088 _refine_diff_density_min -0.869 _refine_diff_density_rms 0.125 #----------------------------------------------------------------------------# # 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 0.82373(3) 0.28777(2) 0.60193(3) 0.02347(11) Uani 1 1 d . . . C1 C 0.8937(5) 0.3941(3) 1.0620(5) 0.0250(9) Uani 1 1 d . . . H1 H 1.0002 0.4139 1.1064 0.03 Uiso 1 1 calc R . . C2 C 0.7878(6) 0.3313(3) 1.1276(5) 0.0264(9) Uani 1 1 d . . . H2 H 0.8111 0.3007 1.2234 0.032 Uiso 1 1 calc R . . N3 N 0.6488(5) 0.3208(3) 1.0347(4) 0.0251(8) Uani 1 1 d . . . N4 N 0.6755(4) 0.3760(2) 0.9164(4) 0.0199(7) Uani 1 1 d . . . N5 N 0.8217(5) 0.4220(3) 0.9270(4) 0.0274(8) Uani 1 1 d . . . C6 C 0.5564(5) 0.3848(3) 0.7851(5) 0.0198(8) Uani 1 1 d . . . C7 C 0.3985(5) 0.4228(3) 0.8072(5) 0.0259(9) Uani 1 1 d . . . H7 H 0.3722 0.441 0.907 0.031 Uiso 1 1 calc R . . C8 C 0.2817(5) 0.4336(3) 0.6831(5) 0.0264(9) Uani 1 1 d . . . H8 H 0.1743 0.4588 0.6978 0.032 Uiso 1 1 calc R . . C9 C 0.3208(5) 0.4075(3) 0.5356(5) 0.0225(8) Uani 1 1 d . . . C10 C 0.4790(5) 0.3693(3) 0.5158(5) 0.0222(8) Uani 1 1 d . . . H10 H 0.506 0.352 0.4158 0.027 Uiso 1 1 calc R . . C11 C 0.5967(5) 0.3564(3) 0.6394(4) 0.0194(8) Uani 1 1 d . . . C12 C 0.1936(5) 0.4192(3) 0.3989(5) 0.0270(9) Uani 1 1 d . . . H12A H 0.2521 0.4315 0.3068 0.041 Uiso 1 1 calc R . . H12B H 0.1191 0.4715 0.4174 0.041 Uiso 1 1 calc R . . H12C H 0.1271 0.3621 0.3841 0.041 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 0.01629(15) 0.03493(17) 0.01896(15) 0.00133(11) 0.00011(10) 0.00414(11) C1 0.019(2) 0.034(2) 0.021(2) -0.0002(18) -0.0056(16) -0.0015(18) C2 0.028(2) 0.030(2) 0.019(2) 0.0026(18) -0.0048(17) 0.0019(18) N3 0.0216(18) 0.0328(19) 0.0201(17) 0.0053(15) -0.0025(14) -0.0041(15) N4 0.0174(16) 0.0251(17) 0.0165(16) 0.0008(14) -0.0028(13) -0.0038(14) N5 0.0212(18) 0.038(2) 0.0214(18) 0.0024(16) -0.0064(14) -0.0073(16) C6 0.0165(18) 0.024(2) 0.0177(18) 0.0011(16) -0.0048(15) -0.0028(16) C7 0.022(2) 0.033(2) 0.022(2) -0.0048(18) -0.0001(17) 0.0023(18) C8 0.019(2) 0.031(2) 0.028(2) -0.0051(19) -0.0020(17) 0.0036(17) C9 0.021(2) 0.0222(19) 0.023(2) 0.0006(17) -0.0052(16) -0.0017(16) C10 0.023(2) 0.027(2) 0.0155(18) 0.0006(16) -0.0022(16) -0.0013(17) C11 0.0123(17) 0.0255(19) 0.0201(19) -0.0007(16) -0.0008(15) -0.0017(15) C12 0.023(2) 0.031(2) 0.025(2) 0.0021(19) -0.0109(18) 0.0034(18) #----------------------------------------------------------------------------# # 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 C11 2.114(4) . ? C1 N5 1.331(6) . ? C1 C2 1.393(6) . ? C1 H1 0.95 . ? C2 N3 1.330(6) . ? C2 H2 0.95 . ? N3 N4 1.334(5) . ? N4 N5 1.339(5) . ? N4 C6 1.435(5) . ? C6 C11 1.399(5) . ? C6 C7 1.403(6) . ? C7 C8 1.381(6) . ? C7 H7 0.95 . ? C8 C9 1.402(6) . ? C8 H8 0.95 . ? C9 C10 1.402(6) . ? C9 C12 1.513(6) . ? C10 C11 1.386(6) . ? C10 H10 0.95 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 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 N5 C1 C2 109.1(4) . . ? N5 C1 H1 125.5 . . ? C2 C1 H1 125.5 . . ? N3 C2 C1 109.1(4) . . ? N3 C2 H2 125.4 . . ? C1 C2 H2 125.4 . . ? C2 N3 N4 103.1(3) . . ? N3 N4 N5 115.7(3) . . ? N3 N4 C6 122.3(3) . . ? N5 N4 C6 122.0(3) . . ? C1 N5 N4 103.0(3) . . ? C11 C6 C7 121.0(4) . . ? C11 C6 N4 121.0(4) . . ? C7 C6 N4 118.0(4) . . ? C8 C7 C6 119.6(4) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 120.3(4) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 119.2(4) . . ? C10 C9 C12 120.1(4) . . ? C8 C9 C12 120.7(4) . . ? C11 C10 C9 121.3(4) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C6 118.5(4) . . ? C10 C11 I1 118.6(3) . . ? C6 C11 I1 122.8(3) . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 N5 C1 C2 N3 -0.8(6) . . . . ? C1 C2 N3 N4 0.8(5) . . . . ? C2 N3 N4 N5 -0.5(5) . . . . ? C2 N3 N4 C6 178.7(4) . . . . ? C2 C1 N5 N4 0.5(5) . . . . ? N3 N4 N5 C1 0.0(5) . . . . ? C6 N4 N5 C1 -179.2(4) . . . . ? N3 N4 C6 C11 -116.2(4) . . . . ? N5 N4 C6 C11 63.0(6) . . . . ? N3 N4 C6 C7 63.9(5) . . . . ? N5 N4 C6 C7 -117.0(4) . . . . ? C11 C6 C7 C8 -0.9(7) . . . . ? N4 C6 C7 C8 179.1(4) . . . . ? C6 C7 C8 C9 -0.6(7) . . . . ? C7 C8 C9 C10 0.8(7) . . . . ? C7 C8 C9 C12 -179.9(4) . . . . ? C8 C9 C10 C11 0.5(6) . . . . ? C12 C9 C10 C11 -178.9(4) . . . . ? C9 C10 C11 C6 -1.8(6) . . . . ? C9 C10 C11 I1 174.8(3) . . . . ? C7 C6 C11 C10 2.0(6) . . . . ? N4 C6 C11 C10 -177.9(4) . . . . ? C7 C6 C11 I1 -174.4(3) . . . . ? N4 C6 C11 I1 5.7(5) . . . . ?