# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_2N2Cl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? 4-(2-Chlorophenyl)-1-(2-nitrophenyl)-1H-1,2,3-triazole ; _chemical_name_common ? _chemical_melting_point 168-169 _chemical_formula_moiety 'C14 H9 Cl1 N4 O2' _chemical_formula_sum 'C14 H9 Cl1 N4 O2' _chemical_formula_weight 300.70 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.340(3) _cell_length_b 7.8967(15) _cell_length_c 14.187(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.414(3) _cell_angle_gamma 90.00 _cell_volume 1359.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2953 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 22.10 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.291 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9415 _exptl_absorpt_correction_T_max 0.9799 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12671 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2399 _reflns_number_gt 1878 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0402P)^2^+0.3141P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2399 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.21515(5) 1.01298(6) 0.57122(4) 0.0806(2) Uani 1 1 d . . . O1 O 0.31218(15) 0.8057(2) 0.17141(13) 0.1001(6) Uani 1 1 d . . . O2 O 0.43385(16) 0.8125(2) 0.08144(12) 0.1055(6) Uani 1 1 d . . . N1 N 0.41088(13) 0.96320(19) 0.34156(11) 0.0592(4) Uani 1 1 d . . . N2 N 0.44999(16) 0.7354(2) 0.42091(14) 0.0845(6) Uani 1 1 d . . . N3 N 0.47913(16) 0.8282(3) 0.35339(14) 0.0874(6) Uani 1 1 d . . . N4 N 0.38708(15) 0.8744(2) 0.14144(13) 0.0732(5) Uani 1 1 d . . . C1 C 0.33950(17) 0.9553(2) 0.40197(13) 0.0566(5) Uani 1 1 d . . . C2 C 0.36317(15) 0.8088(2) 0.45259(12) 0.0564(4) Uani 1 1 d . . . C3 C 0.31342(15) 0.7217(2) 0.52604(12) 0.0546(4) Uani 1 1 d . . . C4 C 0.33372(18) 0.5487(2) 0.54080(15) 0.0648(5) Uani 1 1 d . . . C5 C 0.2888(2) 0.4591(3) 0.60766(17) 0.0754(6) Uani 1 1 d . . . C6 C 0.2220(2) 0.5374(3) 0.66129(17) 0.0746(6) Uani 1 1 d . . . C7 C 0.20128(19) 0.7077(3) 0.64969(15) 0.0687(5) Uani 1 1 d . . . C8 C 0.24656(16) 0.7986(2) 0.58284(12) 0.0588(5) Uani 1 1 d . . . C9 C 0.42256(14) 1.0883(2) 0.27211(13) 0.0559(4) Uani 1 1 d . . . C10 C 0.44405(17) 1.2536(3) 0.30029(16) 0.0684(5) Uani 1 1 d . . . C11 C 0.46137(19) 1.3739(3) 0.2340(2) 0.0807(7) Uani 1 1 d . . . C12 C 0.46189(19) 1.3282(3) 0.1408(2) 0.0809(7) Uani 1 1 d . . . C13 C 0.44104(17) 1.1640(3) 0.11170(17) 0.0727(6) Uani 1 1 d . . . C14 C 0.41931(15) 1.0452(2) 0.17672(13) 0.0583(5) Uani 1 1 d . . . H1 H 0.2876(16) 1.036(3) 0.4018(13) 0.065(6) Uiso 1 1 d . . . H4 H 0.3777(18) 0.495(2) 0.5013(15) 0.075(6) Uiso 1 1 d . . . H5 H 0.3059(18) 0.348(3) 0.6152(15) 0.091(7) Uiso 1 1 d . . . H6 H 0.1916(19) 0.477(3) 0.7054(16) 0.084(7) Uiso 1 1 d . . . H7 H 0.1561(17) 0.761(3) 0.6833(15) 0.080(7) Uiso 1 1 d . . . H10 H 0.4505(17) 1.281(3) 0.3658(16) 0.082(7) Uiso 1 1 d . . . H11 H 0.476(2) 1.488(3) 0.2553(17) 0.094(7) Uiso 1 1 d . . . H12 H 0.4752(19) 1.408(3) 0.0960(16) 0.091(7) Uiso 1 1 d . . . H13 H 0.4397(16) 1.131(3) 0.0521(15) 0.072(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1109(5) 0.0549(3) 0.0835(4) -0.0015(2) 0.0371(3) 0.0139(3) O1 0.1059(13) 0.0865(11) 0.1140(13) -0.0212(10) 0.0361(11) -0.0354(10) O2 0.1184(14) 0.1076(14) 0.0974(12) -0.0350(11) 0.0380(11) -0.0030(11) N1 0.0614(9) 0.0570(9) 0.0602(9) 0.0070(7) 0.0136(8) 0.0099(7) N2 0.0921(13) 0.0776(12) 0.0916(13) 0.0285(10) 0.0372(10) 0.0340(10) N3 0.0914(13) 0.0852(13) 0.0941(13) 0.0279(11) 0.0398(11) 0.0364(10) N4 0.0745(11) 0.0752(12) 0.0692(11) -0.0079(9) 0.0109(9) -0.0050(10) C1 0.0607(11) 0.0525(11) 0.0573(11) 0.0028(8) 0.0122(9) 0.0100(9) C2 0.0606(11) 0.0520(10) 0.0558(10) 0.0013(8) 0.0082(8) 0.0092(8) C3 0.0593(10) 0.0486(10) 0.0527(10) 0.0014(8) 0.0019(8) 0.0008(8) C4 0.0731(13) 0.0491(11) 0.0700(13) 0.0006(9) 0.0075(11) 0.0040(9) C5 0.0885(16) 0.0512(12) 0.0810(15) 0.0104(11) 0.0007(12) -0.0041(11) C6 0.0836(15) 0.0700(14) 0.0677(13) 0.0135(12) 0.0072(12) -0.0153(12) C7 0.0755(14) 0.0738(14) 0.0567(11) -0.0005(10) 0.0120(10) -0.0057(11) C8 0.0695(12) 0.0513(10) 0.0530(10) -0.0020(8) 0.0043(9) 0.0000(9) C9 0.0502(10) 0.0594(11) 0.0575(11) 0.0049(9) 0.0079(8) 0.0010(8) C10 0.0694(13) 0.0664(13) 0.0664(13) -0.0027(11) 0.0040(10) -0.0039(10) C11 0.0741(14) 0.0626(14) 0.1010(19) 0.0077(13) 0.0039(13) -0.0132(11) C12 0.0702(14) 0.0823(16) 0.0897(17) 0.0296(14) 0.0133(12) -0.0096(12) C13 0.0659(13) 0.0903(17) 0.0627(13) 0.0097(12) 0.0137(10) -0.0015(11) C14 0.0510(10) 0.0638(11) 0.0592(11) 0.0027(9) 0.0077(8) -0.0028(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C8 1.7379(19) . ? O1 N4 1.213(2) . ? O2 N4 1.214(2) . ? N1 C1 1.337(2) . ? N1 N3 1.350(2) . ? N1 C9 1.421(2) . ? N2 N3 1.307(2) . ? N2 C2 1.363(2) . ? N4 C14 1.469(3) . ? C1 C2 1.365(3) . ? C1 H1 0.90(2) . ? C2 C3 1.472(2) . ? C3 C8 1.392(2) . ? C3 C4 1.398(3) . ? C4 C5 1.377(3) . ? C4 H4 0.95(2) . ? C5 C6 1.366(3) . ? C5 H5 0.91(2) . ? C6 C7 1.373(3) . ? C6 H6 0.92(2) . ? C7 C8 1.385(3) . ? C7 H7 0.90(2) . ? C9 C10 1.376(3) . ? C9 C14 1.389(3) . ? C10 C11 1.380(3) . ? C10 H10 0.94(2) . ? C11 C12 1.372(3) . ? C11 H11 0.96(2) . ? C12 C13 1.371(3) . ? C12 H12 0.93(2) . ? C13 C14 1.376(3) . ? C13 H13 0.88(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N3 110.61(15) . . ? C1 N1 C9 129.66(15) . . ? N3 N1 C9 119.74(15) . . ? N3 N2 C2 109.90(16) . . ? N2 N3 N1 106.59(15) . . ? O1 N4 O2 123.7(2) . . ? O1 N4 C14 117.88(17) . . ? O2 N4 C14 118.36(19) . . ? N1 C1 C2 105.88(17) . . ? N1 C1 H1 121.0(12) . . ? C2 C1 H1 133.1(13) . . ? N2 C2 C1 107.02(16) . . ? N2 C2 C3 119.23(16) . . ? C1 C2 C3 133.72(17) . . ? C8 C3 C4 116.64(18) . . ? C8 C3 C2 124.93(16) . . ? C4 C3 C2 118.43(17) . . ? C5 C4 C3 121.4(2) . . ? C5 C4 H4 121.6(12) . . ? C3 C4 H4 116.9(12) . . ? C6 C5 C4 120.6(2) . . ? C6 C5 H5 121.7(14) . . ? C4 C5 H5 117.7(14) . . ? C5 C6 C7 119.6(2) . . ? C5 C6 H6 120.2(14) . . ? C7 C6 H6 120.1(14) . . ? C6 C7 C8 120.0(2) . . ? C6 C7 H7 120.7(14) . . ? C8 C7 H7 119.2(14) . . ? C7 C8 C3 121.65(18) . . ? C7 C8 Cl1 117.33(16) . . ? C3 C8 Cl1 121.01(14) . . ? C10 C9 C14 119.04(18) . . ? C10 C9 N1 119.74(17) . . ? C14 C9 N1 121.10(17) . . ? C9 C10 C11 120.0(2) . . ? C9 C10 H10 118.7(13) . . ? C11 C10 H10 121.2(13) . . ? C12 C11 C10 120.3(2) . . ? C12 C11 H11 121.2(15) . . ? C10 C11 H11 118.5(15) . . ? C13 C12 C11 120.4(2) . . ? C13 C12 H12 118.9(14) . . ? C11 C12 H12 120.7(14) . . ? C12 C13 C14 119.5(2) . . ? C12 C13 H13 122.8(14) . . ? C14 C13 H13 117.8(14) . . ? C13 C14 C9 120.8(2) . . ? C13 C14 N4 118.14(19) . . ? C9 C14 N4 121.04(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N2 N3 N1 0.3(3) . . . . ? C1 N1 N3 N2 0.3(2) . . . . ? C9 N1 N3 N2 179.98(18) . . . . ? N3 N1 C1 C2 -0.8(2) . . . . ? C9 N1 C1 C2 179.60(17) . . . . ? N3 N2 C2 C1 -0.8(3) . . . . ? N3 N2 C2 C3 177.32(18) . . . . ? N1 C1 C2 N2 0.9(2) . . . . ? N1 C1 C2 C3 -176.77(19) . . . . ? N2 C2 C3 C8 161.72(19) . . . . ? C1 C2 C3 C8 -20.8(3) . . . . ? N2 C2 C3 C4 -18.4(3) . . . . ? C1 C2 C3 C4 159.1(2) . . . . ? C8 C3 C4 C5 0.6(3) . . . . ? C2 C3 C4 C5 -179.31(18) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C4 C5 C6 C7 -1.2(3) . . . . ? C5 C6 C7 C8 1.0(3) . . . . ? C6 C7 C8 C3 0.1(3) . . . . ? C6 C7 C8 Cl1 179.21(17) . . . . ? C4 C3 C8 C7 -0.8(3) . . . . ? C2 C3 C8 C7 179.04(17) . . . . ? C4 C3 C8 Cl1 -179.95(14) . . . . ? C2 C3 C8 Cl1 -0.1(3) . . . . ? C1 N1 C9 C10 59.0(3) . . . . ? N3 N1 C9 C10 -120.6(2) . . . . ? C1 N1 C9 C14 -124.9(2) . . . . ? N3 N1 C9 C14 55.5(3) . . . . ? C14 C9 C10 C11 0.4(3) . . . . ? N1 C9 C10 C11 176.51(18) . . . . ? C9 C10 C11 C12 -2.8(3) . . . . ? C10 C11 C12 C13 2.5(4) . . . . ? C11 C12 C13 C14 0.1(3) . . . . ? C12 C13 C14 C9 -2.5(3) . . . . ? C12 C13 C14 N4 174.35(19) . . . . ? C10 C9 C14 C13 2.3(3) . . . . ? N1 C9 C14 C13 -173.79(17) . . . . ? C10 C9 C14 N4 -174.51(17) . . . . ? N1 C9 C14 N4 9.4(3) . . . . ? O1 N4 C14 C13 -137.3(2) . . . . ? O2 N4 C14 C13 40.0(3) . . . . ? O1 N4 C14 C9 39.6(3) . . . . ? O2 N4 C14 C9 -143.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 O1 0.90(2) 2.58(2) 3.397(3) 150.4(16) 2 C13 H13 O2 0.88(2) 2.70(2) 3.385(3) 135.1(17) 3_675 C5 H5 Cl1 0.91(2) 2.89(2) 3.652(2) 142.0(18) 1_545 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.185 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.031 _database_code_depnum_ccdc_archive 'CCDC 731506' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '2N3Cl.cif' data_2N3Cl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? 4-(3-Chlorophenyl)-1-(2-nitrophenyl)-1H-1,2,3-triazole ; _chemical_name_common ? _chemical_melting_point 129 _chemical_formula_moiety 'C14 H9 Cl N4 O2' _chemical_formula_sum 'C14 H9 Cl N4 O2' _chemical_formula_weight 300.70 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Monoclinic' _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.705(18) _cell_length_b 7.191(18) _cell_length_c 12.34(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.39(7) _cell_angle_gamma 90.00 _cell_volume 683(3) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1683 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 25.06 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.289 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9106 _exptl_absorpt_correction_T_max 0.9717 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3964 _diffrn_reflns_av_R_equivalents 0.0991 _diffrn_reflns_av_sigmaI/netI 0.1127 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2311 _reflns_number_gt 1804 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0794P)^2^+0.0243P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.009(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.23(16) _refine_ls_number_reflns 2311 _refine_ls_number_parameters 191 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0845 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.1845 _refine_ls_wR_factor_gt 0.1752 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.3619(2) 0.3827(3) 1.14581(14) 0.0963(7) Uani 1 1 d . . . O1 O 0.8646(4) 0.7858(6) 0.6266(3) 0.0673(11) Uani 1 1 d . . . O2 O 0.8748(5) 0.6482(8) 0.4716(3) 0.0868(15) Uani 1 1 d . . . N1 N 1.0390(4) 0.5113(6) 0.7608(2) 0.0476(10) Uani 1 1 d . . . N2 N 0.8917(5) 0.4245(7) 0.7300(3) 0.0560(11) Uani 1 1 d . . . N3 N 0.7985(5) 0.4048(6) 0.8168(3) 0.0547(11) Uani 1 1 d . . . N4 N 0.9411(5) 0.6922(6) 0.5603(3) 0.0546(11) Uani 1 1 d . . . C1 C 1.0411(6) 0.5513(7) 0.8686(3) 0.0480(11) Uani 1 1 d . . . H1 H 1.1274 0.6121 0.9099 0.058 Uiso 1 1 calc R . . C2 C 0.8881(5) 0.4821(6) 0.9023(3) 0.0428(10) Uani 1 1 d . . . C3 C 0.8151(5) 0.4870(7) 1.0126(3) 0.0446(11) Uani 1 1 d . . . C4 C 0.9184(6) 0.5394(7) 1.1022(3) 0.0546(13) Uani 1 1 d . . . H4 H 1.0337 0.5725 1.0938 0.065 Uiso 1 1 calc R . . C5 C 0.8496(8) 0.5423(8) 1.2048(4) 0.0660(15) Uani 1 1 d . . . H5 H 0.9200 0.5755 1.2647 0.079 Uiso 1 1 calc R . . C6 C 0.6795(8) 0.4968(8) 1.2182(4) 0.0657(15) Uani 1 1 d . . . H6 H 0.6335 0.5011 1.2867 0.079 Uiso 1 1 calc R . . C7 C 0.5768(7) 0.4447(8) 1.1292(4) 0.0634(15) Uani 1 1 d . . . C8 C 0.6440(6) 0.4385(8) 1.0258(4) 0.0562(13) Uani 1 1 d . . . H8 H 0.5739 0.4021 0.9664 0.067 Uiso 1 1 calc R . . C9 C 1.1683(5) 0.5536(7) 0.6837(3) 0.0466(11) Uani 1 1 d . . . C10 C 1.3385(6) 0.5137(8) 0.7052(4) 0.0558(13) Uani 1 1 d . . . H10 H 1.3721 0.4594 0.7712 0.067 Uiso 1 1 calc R . . C11 C 1.4630(6) 0.5526(10) 0.6307(4) 0.0677(16) Uani 1 1 d . . . H11 H 1.5794 0.5263 0.6467 0.081 Uiso 1 1 calc R . . C12 C 1.4117(7) 0.6316(9) 0.5315(4) 0.0633(15) Uani 1 1 d . . . H12 H 1.4946 0.6589 0.4812 0.076 Uiso 1 1 calc R . . C13 C 1.2414(7) 0.6692(8) 0.5075(4) 0.0577(14) Uani 1 1 d . . . H13 H 1.2075 0.7185 0.4402 0.069 Uiso 1 1 calc R . . C14 C 1.1178(6) 0.6334(7) 0.5842(3) 0.0479(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0704(10) 0.1230(16) 0.0973(12) 0.0041(11) 0.0254(8) -0.0156(10) O1 0.053(2) 0.083(3) 0.066(2) -0.001(2) 0.0077(17) 0.019(2) O2 0.064(2) 0.149(4) 0.046(2) 0.001(2) -0.0122(18) 0.003(3) N1 0.049(2) 0.059(3) 0.0339(17) -0.0013(18) -0.0093(15) -0.0041(19) N2 0.051(2) 0.081(3) 0.0349(18) 0.000(2) -0.0043(15) -0.008(2) N3 0.054(2) 0.067(3) 0.0422(19) 0.001(2) -0.0077(16) -0.014(2) N4 0.051(2) 0.070(3) 0.043(2) 0.015(2) -0.0053(18) 0.000(2) C1 0.056(3) 0.050(3) 0.036(2) 0.001(2) -0.0117(18) -0.007(2) C2 0.044(2) 0.047(3) 0.037(2) 0.008(2) -0.0036(17) -0.001(2) C3 0.051(2) 0.046(3) 0.037(2) 0.006(2) 0.0014(17) 0.007(2) C4 0.063(3) 0.058(3) 0.042(2) 0.001(2) -0.002(2) -0.005(3) C5 0.084(4) 0.073(4) 0.040(2) -0.006(3) -0.005(2) -0.012(3) C6 0.094(4) 0.064(3) 0.040(2) -0.001(2) 0.016(2) 0.000(3) C7 0.060(3) 0.076(4) 0.054(3) 0.004(3) 0.010(2) 0.004(3) C8 0.058(3) 0.064(4) 0.047(2) 0.002(2) -0.0026(19) -0.002(2) C9 0.043(2) 0.058(3) 0.039(2) 0.000(2) 0.0002(17) -0.002(2) C10 0.052(3) 0.066(4) 0.049(2) 0.000(2) -0.0074(19) 0.004(3) C11 0.038(2) 0.093(4) 0.071(3) -0.007(3) 0.000(2) 0.016(3) C12 0.052(3) 0.079(4) 0.060(3) -0.004(3) 0.011(2) 0.002(3) C13 0.058(3) 0.076(4) 0.040(2) 0.005(2) 0.007(2) -0.005(3) C14 0.047(3) 0.054(3) 0.042(2) -0.005(2) -0.001(2) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C7 1.736(7) . ? O1 N4 1.229(6) . ? O2 N4 1.230(6) . ? N1 N2 1.337(6) . ? N1 C1 1.361(6) . ? N1 C9 1.439(6) . ? N2 N3 1.321(5) . ? N3 C2 1.356(6) . ? N4 C14 1.444(7) . ? C1 C2 1.361(6) . ? C1 H1 0.9300 . ? C2 C3 1.496(6) . ? C3 C8 1.380(7) . ? C3 C4 1.388(7) . ? C4 C5 1.393(7) . ? C4 H4 0.9300 . ? C5 C6 1.368(8) . ? C5 H5 0.9300 . ? C6 C7 1.379(8) . ? C6 H6 0.9300 . ? C7 C8 1.398(7) . ? C8 H8 0.9300 . ? C9 C10 1.358(7) . ? C9 C14 1.396(7) . ? C10 C11 1.385(8) . ? C10 H10 0.9300 . ? C11 C12 1.392(8) . ? C11 H11 0.9300 . ? C12 C13 1.361(8) . ? C12 H12 0.9300 . ? C13 C14 1.394(7) . ? C13 H13 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C1 110.6(4) . . ? N2 N1 C9 120.9(4) . . ? C1 N1 C9 128.5(4) . . ? N3 N2 N1 107.7(3) . . ? N2 N3 C2 108.1(4) . . ? O1 N4 O2 122.7(4) . . ? O1 N4 C14 119.9(4) . . ? O2 N4 C14 117.3(4) . . ? C2 C1 N1 104.3(4) . . ? C2 C1 H1 127.9 . . ? N1 C1 H1 127.9 . . ? N3 C2 C1 109.4(4) . . ? N3 C2 C3 121.4(4) . . ? C1 C2 C3 129.2(4) . . ? C8 C3 C4 119.6(4) . . ? C8 C3 C2 119.9(4) . . ? C4 C3 C2 120.5(4) . . ? C3 C4 C5 120.1(5) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.6(5) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.3(4) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C6 C7 C8 121.0(5) . . ? C6 C7 Cl1 119.6(4) . . ? C8 C7 Cl1 119.4(4) . . ? C3 C8 C7 119.4(4) . . ? C3 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C10 C9 C14 119.4(4) . . ? C10 C9 N1 121.0(4) . . ? C14 C9 N1 119.6(4) . . ? C9 C10 C11 121.1(5) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C10 C11 C12 119.2(5) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C13 C12 C11 120.5(5) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.7(5) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C9 120.0(5) . . ? C13 C14 N4 118.2(4) . . ? C9 C14 N4 121.7(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 C1 N1 N2 N3 -0.9(6) . . . . ? C9 N1 N2 N3 -179.8(4) . . . . ? N1 N2 N3 C2 0.7(5) . . . . ? N2 N1 C1 C2 0.7(5) . . . . ? C9 N1 C1 C2 179.6(5) . . . . ? N2 N3 C2 C1 -0.2(5) . . . . ? N2 N3 C2 C3 178.4(4) . . . . ? N1 C1 C2 N3 -0.3(5) . . . . ? N1 C1 C2 C3 -178.8(4) . . . . ? N3 C2 C3 C8 -10.0(7) . . . . ? C1 C2 C3 C8 168.3(5) . . . . ? N3 C2 C3 C4 169.8(4) . . . . ? C1 C2 C3 C4 -12.0(7) . . . . ? C8 C3 C4 C5 0.2(7) . . . . ? C2 C3 C4 C5 -179.5(5) . . . . ? C3 C4 C5 C6 -1.1(8) . . . . ? C4 C5 C6 C7 1.1(9) . . . . ? C5 C6 C7 C8 -0.3(9) . . . . ? C5 C6 C7 Cl1 178.8(5) . . . . ? C4 C3 C8 C7 0.6(8) . . . . ? C2 C3 C8 C7 -179.6(5) . . . . ? C6 C7 C8 C3 -0.6(9) . . . . ? Cl1 C7 C8 C3 -179.7(4) . . . . ? N2 N1 C9 C10 -132.2(5) . . . . ? C1 N1 C9 C10 49.1(8) . . . . ? N2 N1 C9 C14 46.5(7) . . . . ? C1 N1 C9 C14 -132.2(5) . . . . ? C14 C9 C10 C11 0.7(8) . . . . ? N1 C9 C10 C11 179.4(5) . . . . ? C9 C10 C11 C12 -0.9(9) . . . . ? C10 C11 C12 C13 -0.4(9) . . . . ? C11 C12 C13 C14 1.9(8) . . . . ? C12 C13 C14 C9 -2.1(8) . . . . ? C12 C13 C14 N4 173.9(5) . . . . ? C10 C9 C14 C13 0.8(7) . . . . ? N1 C9 C14 C13 -177.9(5) . . . . ? C10 C9 C14 N4 -175.0(5) . . . . ? N1 C9 C14 N4 6.3(7) . . . . ? O1 N4 C14 C13 -128.5(5) . . . . ? O2 N4 C14 C13 49.9(7) . . . . ? O1 N4 C14 C9 47.5(7) . . . . ? O2 N4 C14 C9 -134.1(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C13 H13 N2 0.93 2.66 3.573(9) 168.3 2_756 C11 H11 N2 0.93 2.68 3.596(9) 168.6 1_655 C5 H5 O2 0.93 2.64 3.379(10) 136.3 1_556 C4 H4 Cl1 0.93 2.92 3.617(9) 132.7 1_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.240 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 731507' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '2N4Cl.cif' data_2N4Cl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? 4-(4-Chlorophenyl)-1-(2-nitrophenyl)-1H-1,2,3-triazole ; _chemical_name_common ? _chemical_melting_point 136-138 _chemical_formula_moiety 'C14 H9 Cl N4 O2' _chemical_formula_sum 'C14 H9 Cl N4 O2' _chemical_formula_weight 300.70 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.8467(15) _cell_length_b 14.129(2) _cell_length_c 26.790(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4105.5(10) _cell_formula_units_Z 12 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3760 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 19.25 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1848 _exptl_absorpt_coefficient_mu 0.289 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8573 _exptl_absorpt_correction_T_max 0.9580 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27374 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 25.99 _reflns_number_total 7975 _reflns_number_gt 5193 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0318P)^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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(5) _refine_ls_number_reflns 7975 _refine_ls_number_parameters 568 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.0883 _refine_ls_wR_factor_gt 0.0761 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Cl1A Cl 0.28069(9) 1.01175(5) 0.07196(3) 0.0847(3) Uani 1 1 d . . . O1A O 0.2313(2) 0.37282(15) 0.08497(8) 0.0913(8) Uani 1 1 d . . . O2A O 0.2558(3) 0.22366(15) 0.08192(9) 0.1000(9) Uani 1 1 d . . . N1A N 0.2410(2) 0.45947(15) -0.00481(9) 0.0586(6) Uani 1 1 d . . . N2A N 0.3642(3) 0.46266(16) 0.00194(11) 0.0761(8) Uani 1 1 d . . . N3A N 0.3916(2) 0.54951(17) 0.01635(10) 0.0709(7) Uani 1 1 d . . . N4A N 0.2257(2) 0.29783(17) 0.06307(10) 0.0634(7) Uani 1 1 d . . . C1A C 0.1913(3) 0.54440(18) 0.00495(10) 0.0544(7) Uani 1 1 d . . . H1A H 0.1084 0.5608 0.0028 0.065 Uiso 1 1 calc R . . C2A C 0.2859(3) 0.60172(18) 0.01851(10) 0.0521(7) Uani 1 1 d . . . C3A C 0.2848(3) 0.70190(18) 0.03298(9) 0.0485(7) Uani 1 1 d . . . C4A C 0.3890(3) 0.74532(18) 0.05261(10) 0.0557(8) Uani 1 1 d . . . H4A H 0.4605 0.7102 0.0575 0.067 Uiso 1 1 calc R . . C5A C 0.3870(3) 0.8399(2) 0.06478(10) 0.0576(8) Uani 1 1 d . . . H5A H 0.4575 0.8687 0.0774 0.069 Uiso 1 1 calc R . . C6A C 0.2821(3) 0.89140(17) 0.05835(10) 0.0532(7) Uani 1 1 d . . . C7A C 0.1762(3) 0.8498(2) 0.04053(10) 0.0600(8) Uani 1 1 d . . . H7A H 0.1043 0.8850 0.0368 0.072 Uiso 1 1 calc R . . C8A C 0.1783(3) 0.75505(19) 0.02826(10) 0.0570(8) Uani 1 1 d . . . H8A H 0.1068 0.7263 0.0166 0.068 Uiso 1 1 calc R . . C9A C 0.1789(3) 0.37457(19) -0.01852(11) 0.0567(8) Uani 1 1 d . . . C10A C 0.1201(3) 0.3714(2) -0.06371(12) 0.0720(9) Uani 1 1 d . . . H10A H 0.1209 0.4242 -0.0845 0.086 Uiso 1 1 calc R . . C11A C 0.0597(3) 0.2904(2) -0.07855(12) 0.0808(10) Uani 1 1 d . . . H11A H 0.0208 0.2884 -0.1095 0.097 Uiso 1 1 calc R . . C12A C 0.0567(3) 0.2127(2) -0.04775(13) 0.0720(9) Uani 1 1 d . . . H12A H 0.0151 0.1585 -0.0579 0.086 Uiso 1 1 calc R . . C13A C 0.1143(3) 0.21443(19) -0.00238(12) 0.0650(9) Uani 1 1 d . . . H13A H 0.1128 0.1616 0.0183 0.078 Uiso 1 1 calc R . . C14A C 0.1748(3) 0.29577(19) 0.01229(10) 0.0543(7) Uani 1 1 d . . . Cl1B Cl 0.89978(9) 0.35422(5) 0.06612(4) 0.0915(3) Uani 1 1 d . . . O1B O 0.6730(2) 0.92653(17) 0.21959(8) 0.0863(7) Uani 1 1 d . . . O2B O 0.5604(3) 1.04743(19) 0.20060(10) 0.1052(9) Uani 1 1 d . . . N1B N 0.8091(2) 0.91057(14) 0.12806(8) 0.0503(6) Uani 1 1 d . . . N2B N 0.6928(2) 0.89124(15) 0.11263(8) 0.0579(6) Uani 1 1 d . . . N3B N 0.6909(2) 0.80228(16) 0.09938(8) 0.0543(6) Uani 1 1 d . . . N4B N 0.6581(3) 1.0036(2) 0.20101(10) 0.0690(7) Uani 1 1 d . . . C1B C 0.8801(3) 0.83285(18) 0.12452(9) 0.0533(7) Uani 1 1 d . . . H1B H 0.9631 0.8276 0.1328 0.064 Uiso 1 1 calc R . . C2B C 0.8056(3) 0.76329(17) 0.10633(9) 0.0457(7) Uani 1 1 d . . . C3B C 0.8301(3) 0.66330(18) 0.09601(9) 0.0489(7) Uani 1 1 d . . . C4B C 0.7369(3) 0.60447(19) 0.07921(10) 0.0586(8) Uani 1 1 d . . . H4B H 0.6582 0.6289 0.0743 0.070 Uiso 1 1 calc R . . C5B C 0.7594(3) 0.51001(19) 0.06970(11) 0.0650(9) Uani 1 1 d . . . H5B H 0.6962 0.4712 0.0581 0.078 Uiso 1 1 calc R . . C6B C 0.8740(3) 0.47372(18) 0.07726(11) 0.0594(8) Uani 1 1 d . . . C7B C 0.9683(3) 0.5293(2) 0.09438(10) 0.0632(8) Uani 1 1 d . . . H7B H 1.0459 0.5035 0.1002 0.076 Uiso 1 1 calc R . . C8B C 0.9463(3) 0.62557(19) 0.10293(10) 0.0577(8) Uani 1 1 d . . . H8B H 1.0105 0.6645 0.1134 0.069 Uiso 1 1 calc R . . C9B C 0.8392(3) 1.00346(19) 0.14426(10) 0.0503(7) Uani 1 1 d . . . C10B C 0.9398(3) 1.0488(2) 0.12524(11) 0.0629(8) Uani 1 1 d . . . H10B H 0.9918 1.0173 0.1032 0.075 Uiso 1 1 calc R . . C11B C 0.9648(3) 1.1415(2) 0.13852(12) 0.0728(9) Uani 1 1 d . . . H11B H 1.0350 1.1714 0.1262 0.087 Uiso 1 1 calc R . . C12B C 0.8870(4) 1.1894(2) 0.16964(13) 0.0778(10) Uani 1 1 d . . . H12B H 0.9029 1.2523 0.1776 0.093 Uiso 1 1 calc R . . C13B C 0.7850(3) 1.1451(2) 0.18937(11) 0.0685(9) Uani 1 1 d . . . H13B H 0.7313 1.1775 0.2104 0.082 Uiso 1 1 calc R . . C14B C 0.7640(3) 1.05104(19) 0.17722(11) 0.0555(7) Uani 1 1 d . . . Cl1C Cl 0.44099(10) -0.06550(6) 0.33134(3) 0.0977(3) Uani 1 1 d . . . O1C O 0.9009(3) 0.42231(16) 0.20292(9) 0.0917(8) Uani 1 1 d . . . O2C O 1.0678(3) 0.50190(18) 0.21616(10) 0.1020(9) Uani 1 1 d . . . N1C N 0.7771(2) 0.44200(15) 0.29485(8) 0.0562(6) Uani 1 1 d . . . N2C N 0.8764(2) 0.39060(18) 0.30941(10) 0.0687(7) Uani 1 1 d . . . N3C N 0.8370(2) 0.30486(17) 0.31887(9) 0.0637(7) Uani 1 1 d . . . N4C N 0.9572(3) 0.4895(2) 0.22033(10) 0.0721(8) Uani 1 1 d . . . C1C C 0.6757(3) 0.38766(19) 0.29486(10) 0.0549(7) Uani 1 1 d . . . H1C H 0.5961 0.4058 0.2862 0.066 Uiso 1 1 calc R . . C2C C 0.7135(3) 0.3007(2) 0.31013(10) 0.0507(7) Uani 1 1 d . . . C3C C 0.6446(3) 0.2120(2) 0.31665(9) 0.0509(7) Uani 1 1 d . . . C4C C 0.7058(3) 0.1287(2) 0.32887(11) 0.0641(8) Uani 1 1 d . . . H4C H 0.7906 0.1300 0.3338 0.077 Uiso 1 1 calc R . . C5C C 0.6434(4) 0.0443(2) 0.33376(11) 0.0711(9) Uani 1 1 d . . . H5C H 0.6860 -0.0108 0.3417 0.085 Uiso 1 1 calc R . . C6C C 0.5181(3) 0.0419(2) 0.32686(10) 0.0635(8) Uani 1 1 d . . . C7C C 0.4546(3) 0.1228(2) 0.31527(10) 0.0689(9) Uani 1 1 d . . . H7C H 0.3697 0.1210 0.3107 0.083 Uiso 1 1 calc R . . C8C C 0.5182(3) 0.2073(2) 0.31037(10) 0.0638(8) Uani 1 1 d . . . H8C H 0.4749 0.2621 0.3027 0.077 Uiso 1 1 calc R . . C9C C 0.7944(3) 0.53843(19) 0.28040(11) 0.0560(8) Uani 1 1 d . . . C10C C 0.7255(3) 0.6089(2) 0.30216(11) 0.0670(9) Uani 1 1 d . . . H10C H 0.6654 0.5936 0.3256 0.080 Uiso 1 1 calc R . . C11C C 0.7455(4) 0.7026(2) 0.28917(13) 0.0812(11) Uani 1 1 d . . . H11C H 0.6962 0.7498 0.3027 0.097 Uiso 1 1 calc R . . C12C C 0.8384(4) 0.7261(2) 0.25620(13) 0.0765(10) Uani 1 1 d . . . H12C H 0.8528 0.7893 0.2484 0.092 Uiso 1 1 calc R . . C13C C 0.9097(3) 0.6562(2) 0.23488(11) 0.0696(9) Uani 1 1 d . . . H13C H 0.9735 0.6717 0.2131 0.083 Uiso 1 1 calc R . . C14C C 0.8850(3) 0.5629(2) 0.24636(11) 0.0587(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 Cl1A 0.1028(8) 0.0527(4) 0.0985(7) -0.0148(4) -0.0102(6) 0.0016(5) O1A 0.129(2) 0.0610(13) 0.0837(16) -0.0133(12) -0.0189(15) 0.0034(15) O2A 0.145(3) 0.0555(13) 0.0995(18) 0.0207(13) -0.0215(17) 0.0083(15) N1A 0.0536(18) 0.0451(14) 0.0771(17) 0.0040(12) 0.0042(14) -0.0049(13) N2A 0.058(2) 0.0488(15) 0.121(2) -0.0015(15) 0.0073(17) 0.0002(14) N3A 0.0530(17) 0.0484(14) 0.111(2) 0.0016(14) 0.0014(15) 0.0013(14) N4A 0.0705(19) 0.0478(14) 0.0718(18) 0.0062(14) 0.0059(14) -0.0002(14) C1A 0.056(2) 0.0415(15) 0.0655(18) 0.0031(14) 0.0040(16) 0.0043(16) C2A 0.050(2) 0.0461(16) 0.0598(18) 0.0090(13) 0.0008(15) 0.0018(16) C3A 0.049(2) 0.0482(15) 0.0485(16) 0.0101(13) 0.0015(15) -0.0013(15) C4A 0.0446(19) 0.0519(17) 0.0705(19) 0.0078(15) -0.0011(16) 0.0040(15) C5A 0.0498(19) 0.0583(18) 0.0649(18) 0.0030(15) -0.0089(16) -0.0105(16) C6A 0.064(2) 0.0429(15) 0.0525(17) -0.0015(13) -0.0030(16) 0.0016(16) C7A 0.055(2) 0.0562(18) 0.0693(19) -0.0054(16) -0.0070(17) 0.0132(17) C8A 0.0445(19) 0.0534(17) 0.073(2) 0.0014(15) -0.0093(16) 0.0002(15) C9A 0.059(2) 0.0457(16) 0.065(2) 0.0050(15) 0.0107(16) 0.0007(15) C10A 0.079(3) 0.066(2) 0.071(2) 0.0064(18) 0.004(2) -0.0087(19) C11A 0.087(3) 0.082(2) 0.073(2) -0.005(2) -0.005(2) -0.011(2) C12A 0.071(2) 0.0542(19) 0.091(3) -0.0130(19) 0.008(2) -0.0042(18) C13A 0.075(2) 0.0404(16) 0.080(2) -0.0008(16) 0.011(2) 0.0015(16) C14A 0.058(2) 0.0468(16) 0.0586(19) -0.0024(15) 0.0073(15) 0.0030(15) Cl1B 0.0988(7) 0.0520(4) 0.1237(7) -0.0132(5) 0.0051(6) 0.0172(5) O1B 0.101(2) 0.0715(15) 0.0863(16) 0.0070(13) 0.0154(14) -0.0183(15) O2B 0.0658(18) 0.107(2) 0.143(2) -0.0233(17) 0.0188(17) 0.0090(16) N1B 0.0471(16) 0.0417(13) 0.0621(15) -0.0050(11) -0.0079(13) -0.0008(12) N2B 0.0515(17) 0.0501(14) 0.0721(16) -0.0086(12) -0.0134(13) 0.0011(13) N3B 0.0521(17) 0.0462(13) 0.0646(15) -0.0067(12) -0.0079(12) 0.0007(13) N4B 0.068(2) 0.0704(19) 0.0686(17) -0.0128(16) 0.0068(16) -0.0080(18) C1B 0.0471(19) 0.0522(17) 0.0605(18) -0.0008(14) -0.0062(15) 0.0086(16) C2B 0.0430(19) 0.0426(15) 0.0515(16) -0.0026(12) -0.0039(14) 0.0026(14) C3B 0.0501(19) 0.0494(16) 0.0472(16) -0.0005(13) 0.0015(14) 0.0048(15) C4B 0.050(2) 0.0537(17) 0.072(2) -0.0104(15) -0.0066(16) 0.0052(15) C5B 0.066(2) 0.0528(17) 0.076(2) -0.0124(16) -0.0037(18) -0.0034(16) C6B 0.071(2) 0.0451(16) 0.0620(19) -0.0018(14) 0.0054(18) 0.0073(17) C7B 0.061(2) 0.064(2) 0.0640(19) 0.0019(16) 0.0039(16) 0.0188(18) C8B 0.055(2) 0.0546(18) 0.0631(19) 0.0001(14) -0.0006(15) 0.0033(16) C9B 0.0512(19) 0.0442(15) 0.0556(17) 0.0006(14) -0.0044(15) 0.0015(15) C10B 0.064(2) 0.0571(18) 0.067(2) 0.0004(16) 0.0053(17) -0.0021(17) C11B 0.070(2) 0.061(2) 0.086(2) 0.0149(19) -0.008(2) -0.0168(19) C12B 0.103(3) 0.0473(18) 0.083(2) -0.0022(18) -0.012(2) -0.016(2) C13B 0.087(3) 0.0532(18) 0.065(2) -0.0091(15) -0.0044(19) 0.0078(19) C14B 0.062(2) 0.0461(16) 0.0588(18) -0.0024(14) -0.0076(16) -0.0012(16) Cl1C 0.1181(9) 0.0822(6) 0.0929(6) 0.0081(5) 0.0044(6) -0.0355(6) O1C 0.109(2) 0.0713(15) 0.0948(17) -0.0210(13) 0.0082(15) -0.0087(15) O2C 0.074(2) 0.1012(19) 0.131(2) -0.0027(16) 0.0238(18) 0.0006(17) N1C 0.0561(17) 0.0504(14) 0.0619(15) 0.0054(12) -0.0075(13) 0.0089(14) N2C 0.0577(18) 0.0574(16) 0.0911(19) 0.0102(14) -0.0175(15) 0.0034(14) N3C 0.0547(19) 0.0553(15) 0.0812(18) 0.0109(13) -0.0087(14) 0.0036(14) N4C 0.083(2) 0.0628(18) 0.0703(18) 0.0003(15) 0.0070(17) 0.0023(18) C1C 0.0430(19) 0.0574(18) 0.0642(18) 0.0044(15) -0.0040(15) 0.0028(16) C2C 0.049(2) 0.0539(17) 0.0489(16) -0.0005(14) -0.0027(14) 0.0062(16) C3C 0.054(2) 0.0545(18) 0.0445(16) -0.0010(13) 0.0005(14) 0.0019(15) C4C 0.056(2) 0.0569(19) 0.079(2) 0.0080(16) -0.0027(18) 0.0035(17) C5C 0.082(3) 0.056(2) 0.075(2) 0.0099(17) -0.0019(19) 0.0056(19) C6C 0.075(3) 0.065(2) 0.0506(17) 0.0042(16) 0.0034(17) -0.0153(19) C7C 0.053(2) 0.082(2) 0.072(2) 0.0068(18) -0.0044(17) -0.0078(19) C8C 0.061(2) 0.064(2) 0.066(2) 0.0050(17) 0.0040(17) 0.0061(18) C9C 0.058(2) 0.0498(17) 0.0599(18) 0.0027(14) -0.0098(17) -0.0005(16) C10C 0.070(2) 0.0616(19) 0.069(2) 0.0010(17) 0.0009(18) 0.0066(18) C11C 0.104(3) 0.055(2) 0.085(3) -0.0034(19) -0.010(2) 0.020(2) C12C 0.101(3) 0.0502(19) 0.078(2) 0.0055(18) -0.016(2) -0.001(2) C13C 0.077(3) 0.065(2) 0.068(2) 0.0067(17) -0.0083(18) -0.006(2) C14C 0.066(2) 0.0537(18) 0.0563(18) 0.0003(15) -0.0081(17) 0.0012(18) _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 Cl1A C6A 1.739(3) . ? O1A N4A 1.213(3) . ? O2A N4A 1.208(3) . ? N1A C1A 1.341(3) . ? N1A N2A 1.349(3) . ? N1A C9A 1.424(3) . ? N2A N3A 1.320(3) . ? N3A C2A 1.364(3) . ? N4A C14A 1.469(4) . ? C1A C2A 1.357(4) . ? C1A H1A 0.9300 . ? C2A C3A 1.468(3) . ? C3A C8A 1.384(4) . ? C3A C4A 1.389(4) . ? C4A C5A 1.375(3) . ? C4A H4A 0.9300 . ? C5A C6A 1.361(4) . ? C5A H5A 0.9300 . ? C6A C7A 1.377(4) . ? C7A C8A 1.378(3) . ? C7A H7A 0.9300 . ? C8A H8A 0.9300 . ? C9A C10A 1.369(4) . ? C9A C14A 1.387(4) . ? C10A C11A 1.377(4) . ? C10A H10A 0.9300 . ? C11A C12A 1.374(4) . ? C11A H11A 0.9300 . ? C12A C13A 1.367(4) . ? C12A H12A 0.9300 . ? C13A C14A 1.380(4) . ? C13A H13A 0.9300 . ? Cl1B C6B 1.737(3) . ? O1B N4B 1.207(3) . ? O2B N4B 1.228(3) . ? N1B C1B 1.345(3) . ? N1B N2B 1.356(3) . ? N1B C9B 1.420(3) . ? N2B N3B 1.306(3) . ? N3B C2B 1.373(3) . ? N4B C14B 1.475(4) . ? C1B C2B 1.363(3) . ? C1B H1B 0.9300 . ? C2B C3B 1.464(3) . ? C3B C8B 1.381(4) . ? C3B C4B 1.384(4) . ? C4B C5B 1.380(3) . ? C4B H4B 0.9300 . ? C5B C6B 1.360(4) . ? C5B H5B 0.9300 . ? C6B C7B 1.369(4) . ? C7B C8B 1.400(4) . ? C7B H7B 0.9300 . ? C8B H8B 0.9300 . ? C9B C10B 1.363(4) . ? C9B C14B 1.377(4) . ? C10B C11B 1.385(4) . ? C10B H10B 0.9300 . ? C11B C12B 1.366(4) . ? C11B H11B 0.9300 . ? C12B C13B 1.377(4) . ? C12B H12B 0.9300 . ? C13B C14B 1.387(4) . ? C13B H13B 0.9300 . ? Cl1C C6C 1.737(3) . ? O1C N4C 1.222(3) . ? O2C N4C 1.217(3) . ? N1C C1C 1.341(3) . ? N1C N2C 1.357(3) . ? N1C C9C 1.429(3) . ? N2C N3C 1.309(3) . ? N3C C2C 1.361(4) . ? N4C C14C 1.475(4) . ? C1C C2C 1.358(4) . ? C1C H1C 0.9300 . ? C2C C3C 1.470(4) . ? C3C C8C 1.383(4) . ? C3C C4C 1.390(4) . ? C4C C5C 1.377(4) . ? C4C H4C 0.9300 . ? C5C C6C 1.373(4) . ? C5C H5C 0.9300 . ? C6C C7C 1.370(4) . ? C7C C8C 1.384(4) . ? C7C H7C 0.9300 . ? C8C H8C 0.9300 . ? C9C C10C 1.374(4) . ? C9C C14C 1.384(4) . ? C10C C11C 1.386(4) . ? C10C H10C 0.9300 . ? C11C C12C 1.380(5) . ? C11C H11C 0.9300 . ? C12C C13C 1.378(4) . ? C12C H12C 0.9300 . ? C13C C14C 1.380(4) . ? C13C H13C 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1A N1A N2A 110.0(2) . . ? C1A N1A C9A 127.9(3) . . ? N2A N1A C9A 122.1(2) . . ? N3A N2A N1A 107.1(2) . . ? N2A N3A C2A 109.0(2) . . ? O2A N4A O1A 122.8(3) . . ? O2A N4A C14A 118.2(3) . . ? O1A N4A C14A 119.0(2) . . ? N1A C1A C2A 106.4(3) . . ? N1A C1A H1A 126.8 . . ? C2A C1A H1A 126.8 . . ? C1A C2A N3A 107.5(2) . . ? C1A C2A C3A 129.8(3) . . ? N3A C2A C3A 122.6(3) . . ? C8A C3A C4A 118.3(2) . . ? C8A C3A C2A 120.4(3) . . ? C4A C3A C2A 121.3(3) . . ? C5A C4A C3A 120.4(3) . . ? C5A C4A H4A 119.8 . . ? C3A C4A H4A 119.8 . . ? C6A C5A C4A 120.2(3) . . ? C6A C5A H5A 119.9 . . ? C4A C5A H5A 119.9 . . ? C5A C6A C7A 120.9(2) . . ? C5A C6A Cl1A 120.3(2) . . ? C7A C6A Cl1A 118.9(2) . . ? C6A C7A C8A 118.9(3) . . ? C6A C7A H7A 120.5 . . ? C8A C7A H7A 120.5 . . ? C7A C8A C3A 121.3(3) . . ? C7A C8A H8A 119.4 . . ? C3A C8A H8A 119.4 . . ? C10A C9A C14A 119.0(3) . . ? C10A C9A N1A 118.4(3) . . ? C14A C9A N1A 122.5(3) . . ? C9A C10A C11A 120.3(3) . . ? C9A C10A H10A 119.9 . . ? C11A C10A H10A 119.9 . . ? C12A C11A C10A 120.1(3) . . ? C12A C11A H11A 119.9 . . ? C10A C11A H11A 119.9 . . ? C13A C12A C11A 120.6(3) . . ? C13A C12A H12A 119.7 . . ? C11A C12A H12A 119.7 . . ? C12A C13A C14A 119.0(3) . . ? C12A C13A H13A 120.5 . . ? C14A C13A H13A 120.5 . . ? C13A C14A C9A 120.9(3) . . ? C13A C14A N4A 117.3(3) . . ? C9A C14A N4A 121.6(3) . . ? C1B N1B N2B 110.3(2) . . ? C1B N1B C9B 130.1(2) . . ? N2B N1B C9B 119.6(2) . . ? N3B N2B N1B 106.9(2) . . ? N2B N3B C2B 109.6(2) . . ? O1B N4B O2B 125.0(3) . . ? O1B N4B C14B 118.9(3) . . ? O2B N4B C14B 116.0(3) . . ? N1B C1B C2B 105.9(2) . . ? N1B C1B H1B 127.0 . . ? C2B C1B H1B 127.0 . . ? C1B C2B N3B 107.3(2) . . ? C1B C2B C3B 130.9(3) . . ? N3B C2B C3B 121.8(2) . . ? C8B C3B C4B 118.6(2) . . ? C8B C3B C2B 120.9(3) . . ? C4B C3B C2B 120.5(3) . . ? C5B C4B C3B 120.8(3) . . ? C5B C4B H4B 119.6 . . ? C3B C4B H4B 119.6 . . ? C6B C5B C4B 119.9(3) . . ? C6B C5B H5B 120.1 . . ? C4B C5B H5B 120.1 . . ? C5B C6B C7B 121.1(3) . . ? C5B C6B Cl1B 119.2(3) . . ? C7B C6B Cl1B 119.6(3) . . ? C6B C7B C8B 119.0(3) . . ? C6B C7B H7B 120.5 . . ? C8B C7B H7B 120.5 . . ? C3B C8B C7B 120.6(3) . . ? C3B C8B H8B 119.7 . . ? C7B C8B H8B 119.7 . . ? C10B C9B C14B 119.0(3) . . ? C10B C9B N1B 120.3(3) . . ? C14B C9B N1B 120.7(3) . . ? C9B C10B C11B 120.4(3) . . ? C9B C10B H10B 119.8 . . ? C11B C10B H10B 119.8 . . ? C12B C11B C10B 120.3(3) . . ? C12B C11B H11B 119.9 . . ? C10B C11B H11B 119.9 . . ? C11B C12B C13B 120.4(3) . . ? C11B C12B H12B 119.8 . . ? C13B C12B H12B 119.8 . . ? C12B C13B C14B 118.5(3) . . ? C12B C13B H13B 120.7 . . ? C14B C13B H13B 120.7 . . ? C9B C14B C13B 121.4(3) . . ? C9B C14B N4B 121.1(3) . . ? C13B C14B N4B 117.5(3) . . ? C1C N1C N2C 110.2(2) . . ? C1C N1C C9C 130.8(3) . . ? N2C N1C C9C 119.0(3) . . ? N3C N2C N1C 107.0(2) . . ? N2C N3C C2C 109.1(2) . . ? O2C N4C O1C 124.7(3) . . ? O2C N4C C14C 117.8(3) . . ? O1C N4C C14C 117.4(3) . . ? N1C C1C C2C 105.7(3) . . ? N1C C1C H1C 127.2 . . ? C2C C1C H1C 127.2 . . ? C1C C2C N3C 108.0(3) . . ? C1C C2C C3C 130.8(3) . . ? N3C C2C C3C 121.1(3) . . ? C8C C3C C4C 117.5(3) . . ? C8C C3C C2C 122.1(3) . . ? C4C C3C C2C 120.5(3) . . ? C5C C4C C3C 121.4(3) . . ? C5C C4C H4C 119.3 . . ? C3C C4C H4C 119.3 . . ? C6C C5C C4C 119.7(3) . . ? C6C C5C H5C 120.2 . . ? C4C C5C H5C 120.2 . . ? C7C C6C C5C 120.5(3) . . ? C7C C6C Cl1C 120.2(3) . . ? C5C C6C Cl1C 119.3(3) . . ? C6C C7C C8C 119.4(3) . . ? C6C C7C H7C 120.3 . . ? C8C C7C H7C 120.3 . . ? C3C C8C C7C 121.6(3) . . ? C3C C8C H8C 119.2 . . ? C7C C8C H8C 119.2 . . ? C10C C9C C14C 119.0(3) . . ? C10C C9C N1C 120.3(3) . . ? C14C C9C N1C 120.7(3) . . ? C9C C10C C11C 120.0(3) . . ? C9C C10C H10C 120.0 . . ? C11C C10C H10C 120.0 . . ? C12C C11C C10C 120.4(3) . . ? C12C C11C H11C 119.8 . . ? C10C C11C H11C 119.8 . . ? C13C C12C C11C 120.1(3) . . ? C13C C12C H12C 119.9 . . ? C11C C12C H12C 119.9 . . ? C12C C13C C14C 118.9(3) . . ? C12C C13C H13C 120.6 . . ? C14C C13C H13C 120.6 . . ? C13C C14C C9C 121.6(3) . . ? C13C C14C N4C 117.6(3) . . ? C9C C14C N4C 120.8(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 C1A N1A N2A N3A 0.5(3) . . . . ? C9A N1A N2A N3A -177.4(2) . . . . ? N1A N2A N3A C2A -0.3(3) . . . . ? N2A N1A C1A C2A -0.5(3) . . . . ? C9A N1A C1A C2A 177.2(3) . . . . ? N1A C1A C2A N3A 0.3(3) . . . . ? N1A C1A C2A C3A 179.8(3) . . . . ? N2A N3A C2A C1A 0.0(3) . . . . ? N2A N3A C2A C3A -179.5(2) . . . . ? C1A C2A C3A C8A -8.0(4) . . . . ? N3A C2A C3A C8A 171.4(3) . . . . ? C1A C2A C3A C4A 170.6(3) . . . . ? N3A C2A C3A C4A -9.9(4) . . . . ? C8A C3A C4A C5A -2.9(4) . . . . ? C2A C3A C4A C5A 178.4(2) . . . . ? C3A C4A C5A C6A 1.0(4) . . . . ? C4A C5A C6A C7A 1.2(4) . . . . ? C4A C5A C6A Cl1A -178.1(2) . . . . ? C5A C6A C7A C8A -1.3(4) . . . . ? Cl1A C6A C7A C8A 178.0(2) . . . . ? C6A C7A C8A C3A -0.8(4) . . . . ? C4A C3A C8A C7A 2.8(4) . . . . ? C2A C3A C8A C7A -178.4(3) . . . . ? C1A N1A C9A C10A 66.4(4) . . . . ? N2A N1A C9A C10A -116.1(3) . . . . ? C1A N1A C9A C14A -112.9(3) . . . . ? N2A N1A C9A C14A 64.5(4) . . . . ? C14A C9A C10A C11A -1.1(5) . . . . ? N1A C9A C10A C11A 179.5(3) . . . . ? C9A C10A C11A C12A 0.9(5) . . . . ? C10A C11A C12A C13A -0.6(5) . . . . ? C11A C12A C13A C14A 0.6(5) . . . . ? C12A C13A C14A C9A -0.8(4) . . . . ? C12A C13A C14A N4A 174.5(3) . . . . ? C10A C9A C14A C13A 1.1(4) . . . . ? N1A C9A C14A C13A -179.6(3) . . . . ? C10A C9A C14A N4A -174.1(3) . . . . ? N1A C9A C14A N4A 5.3(4) . . . . ? O2A N4A C14A C13A 28.1(4) . . . . ? O1A N4A C14A C13A -149.1(3) . . . . ? O2A N4A C14A C9A -156.6(3) . . . . ? O1A N4A C14A C9A 26.2(4) . . . . ? C1B N1B N2B N3B -0.2(3) . . . . ? C9B N1B N2B N3B 179.2(2) . . . . ? N1B N2B N3B C2B 0.3(3) . . . . ? N2B N1B C1B C2B 0.0(3) . . . . ? C9B N1B C1B C2B -179.3(3) . . . . ? N1B C1B C2B N3B 0.1(3) . . . . ? N1B C1B C2B C3B -178.1(3) . . . . ? N2B N3B C2B C1B -0.3(3) . . . . ? N2B N3B C2B C3B 178.1(2) . . . . ? C1B C2B C3B C8B -2.4(5) . . . . ? N3B C2B C3B C8B 179.6(2) . . . . ? C1B C2B C3B C4B 177.4(3) . . . . ? N3B C2B C3B C4B -0.6(4) . . . . ? C8B C3B C4B C5B 0.2(4) . . . . ? C2B C3B C4B C5B -179.6(3) . . . . ? C3B C4B C5B C6B 0.6(5) . . . . ? C4B C5B C6B C7B 0.2(5) . . . . ? C4B C5B C6B Cl1B 178.9(2) . . . . ? C5B C6B C7B C8B -1.6(5) . . . . ? Cl1B C6B C7B C8B 179.7(2) . . . . ? C4B C3B C8B C7B -1.7(4) . . . . ? C2B C3B C8B C7B 178.1(2) . . . . ? C6B C7B C8B C3B 2.4(4) . . . . ? C1B N1B C9B C10B 49.9(4) . . . . ? N2B N1B C9B C10B -129.4(3) . . . . ? C1B N1B C9B C14B -133.7(3) . . . . ? N2B N1B C9B C14B 47.1(4) . . . . ? C14B C9B C10B C11B -0.7(4) . . . . ? N1B C9B C10B C11B 175.8(2) . . . . ? C9B C10B C11B C12B -2.0(5) . . . . ? C10B C11B C12B C13B 2.1(5) . . . . ? C11B C12B C13B C14B 0.5(5) . . . . ? C10B C9B C14B C13B 3.3(4) . . . . ? N1B C9B C14B C13B -173.2(3) . . . . ? C10B C9B C14B N4B -176.6(3) . . . . ? N1B C9B C14B N4B 7.0(4) . . . . ? C12B C13B C14B C9B -3.2(5) . . . . ? C12B C13B C14B N4B 176.7(3) . . . . ? O1B N4B C14B C9B 47.7(4) . . . . ? O2B N4B C14B C9B -133.1(3) . . . . ? O1B N4B C14B C13B -132.2(3) . . . . ? O2B N4B C14B C13B 47.1(4) . . . . ? C1C N1C N2C N3C -0.6(3) . . . . ? C9C N1C N2C N3C -177.8(2) . . . . ? N1C N2C N3C C2C 0.5(3) . . . . ? N2C N1C C1C C2C 0.4(3) . . . . ? C9C N1C C1C C2C 177.3(3) . . . . ? N1C C1C C2C N3C -0.1(3) . . . . ? N1C C1C C2C C3C -178.9(3) . . . . ? N2C N3C C2C C1C -0.3(3) . . . . ? N2C N3C C2C C3C 178.7(2) . . . . ? C1C C2C C3C C8C -4.6(5) . . . . ? N3C C2C C3C C8C 176.7(3) . . . . ? C1C C2C C3C C4C 174.5(3) . . . . ? N3C C2C C3C C4C -4.1(4) . . . . ? C8C C3C C4C C5C 1.0(4) . . . . ? C2C C3C C4C C5C -178.1(3) . . . . ? C3C C4C C5C C6C -0.5(5) . . . . ? C4C C5C C6C C7C -0.1(5) . . . . ? C4C C5C C6C Cl1C 178.1(2) . . . . ? C5C C6C C7C C8C 0.2(5) . . . . ? Cl1C C6C C7C C8C -178.0(2) . . . . ? C4C C3C C8C C7C -0.9(4) . . . . ? C2C C3C C8C C7C 178.2(2) . . . . ? C6C C7C C8C C3C 0.3(4) . . . . ? C1C N1C C9C C10C 56.5(4) . . . . ? N2C N1C C9C C10C -126.9(3) . . . . ? C1C N1C C9C C14C -127.0(3) . . . . ? N2C N1C C9C C14C 49.6(4) . . . . ? C14C C9C C10C C11C 1.3(5) . . . . ? N1C C9C C10C C11C 177.9(3) . . . . ? C9C C10C C11C C12C -3.1(5) . . . . ? C10C C11C C12C C13C 1.8(5) . . . . ? C11C C12C C13C C14C 1.2(5) . . . . ? C12C C13C C14C C9C -3.1(5) . . . . ? C12C C13C C14C N4C 175.9(3) . . . . ? C10C C9C C14C C13C 1.8(4) . . . . ? N1C C9C C14C C13C -174.8(3) . . . . ? C10C C9C C14C N4C -177.1(3) . . . . ? N1C C9C C14C N4C 6.3(4) . . . . ? O2C N4C C14C C13C 43.9(4) . . . . ? O1C N4C C14C C13C -133.5(3) . . . . ? O2C N4C C14C C9C -137.1(3) . . . . ? O1C N4C C14C C9C 45.5(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C10C H10C O2B 0.93 2.63 3.221(4) 122.0 3_645 C1C H1C O2B 0.93 2.65 3.416(4) 140.3 3_645 C5C H5C O1A 0.93 2.71 3.530(4) 146.8 3_645 C1B H1B N3C 0.93 2.55 3.445(4) 162.8 3_755 C1B H1B N2C 0.93 2.49 3.282(4) 142.7 3_755 C12B H12B O1C 0.93 2.50 3.413(4) 168.5 1_565 C5A H5A N2B 0.93 2.74 3.629(4) 160.4 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.155 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.032 _database_code_depnum_ccdc_archive 'CCDC 731508' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '3N2Cl.cif' data_3N2Cl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? 4-(2-Chlorophenyl)-1-(3-nitrophenyl)-1H-1,2,3-triazole ; _chemical_name_common ? _chemical_melting_point 149 _chemical_formula_moiety 'C14 H9 Cl N4 O2' _chemical_formula_sum 'C14 H9 Cl N4 O2' _chemical_formula_weight 300.70 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c 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 12.448(4) _cell_length_b 6.999(2) _cell_length_c 15.083(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.273(6) _cell_angle_gamma 90.00 _cell_volume 1308.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1745 _cell_measurement_theta_min 2.712 _cell_measurement_theta_max 27.017 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_type multi-scan' _exptl_absorpt_correction_T_min 0.9561 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9013 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2285 _reflns_number_gt 1826 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0310P)^2^+1.4691P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2285 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1069 _refine_ls_R_factor_gt 0.0844 _refine_ls_wR_factor_ref 0.1596 _refine_ls_wR_factor_gt 0.1507 _refine_ls_goodness_of_fit_ref 1.243 _refine_ls_restrained_S_all 1.243 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.67043(12) 0.23088(18) 0.38798(10) 0.0802(5) Uani 1 1 d . . . O1 O 1.2279(3) 0.5855(6) 0.8059(3) 0.0831(12) Uani 1 1 d . . . O2 O 1.3249(3) 0.3301(6) 0.8108(2) 0.0833(12) Uani 1 1 d . . . N1 N 0.9149(3) 0.4517(5) 0.5863(2) 0.0443(9) Uani 1 1 d . . . N2 N 0.9224(3) 0.6458(5) 0.5831(2) 0.0494(9) Uani 1 1 d . . . N3 N 0.8355(3) 0.7082(5) 0.5387(2) 0.0517(10) Uani 1 1 d . . . N4 N 1.2444(3) 0.4207(7) 0.7849(2) 0.0577(10) Uani 1 1 d . . . C1 C 0.8205(4) 0.3961(6) 0.5425(3) 0.0473(11) Uani 1 1 d . . . C2 C 0.7707(3) 0.5578(6) 0.5118(3) 0.0414(10) Uani 1 1 d . . . C3 C 0.6669(3) 0.5903(6) 0.4583(3) 0.0423(10) Uani 1 1 d . . . C4 C 0.6165(4) 0.7686(7) 0.4624(3) 0.0580(13) Uani 1 1 d . . . C5 C 0.5196(4) 0.8054(8) 0.4135(4) 0.0660(15) Uani 1 1 d . . . C6 C 0.4709(4) 0.6706(8) 0.3585(4) 0.0642(14) Uani 1 1 d . . . C7 C 0.5183(4) 0.4941(8) 0.3532(3) 0.0621(14) Uani 1 1 d . . . C8 C 0.6148(3) 0.4567(6) 0.4017(3) 0.0492(11) Uani 1 1 d . . . C9 C 1.0003(3) 0.3419(6) 0.6293(3) 0.0413(10) Uani 1 1 d . . . C10 C 1.0069(4) 0.1455(7) 0.6137(3) 0.0517(12) Uani 1 1 d . . . C11 C 1.0909(4) 0.0424(7) 0.6537(3) 0.0571(13) Uani 1 1 d . . . C12 C 1.1710(4) 0.1301(7) 0.7092(3) 0.0539(13) Uani 1 1 d . . . C13 C 1.1620(3) 0.3230(6) 0.7239(3) 0.0456(11) Uani 1 1 d . . . C14 C 1.0785(4) 0.4309(7) 0.6854(3) 0.0457(11) Uani 1 1 d . . . H1 H 0.805(3) 0.268(5) 0.540(2) 0.028(9) Uiso 1 1 d . . . H4 H 0.646(3) 0.858(6) 0.500(3) 0.056(14) Uiso 1 1 d . . . H5 H 0.495(3) 0.925(6) 0.416(2) 0.044(12) Uiso 1 1 d . . . H6 H 0.405(4) 0.700(8) 0.324(4) 0.099(19) Uiso 1 1 d . . . H7 H 0.486(3) 0.403(6) 0.313(3) 0.054(13) Uiso 1 1 d . . . H10 H 0.958(3) 0.086(6) 0.578(3) 0.054(14) Uiso 1 1 d . . . H11 H 1.098(3) -0.082(6) 0.644(3) 0.048(12) Uiso 1 1 d . . . H12 H 1.227(3) 0.069(6) 0.731(3) 0.050(13) Uiso 1 1 d . . . H14 H 1.072(3) 0.565(6) 0.702(3) 0.052(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0833(10) 0.0515(8) 0.0992(11) -0.0214(7) -0.0269(8) 0.0136(7) O1 0.064(2) 0.084(3) 0.098(3) -0.030(2) -0.012(2) -0.010(2) O2 0.052(2) 0.110(3) 0.083(3) 0.002(2) -0.0206(19) 0.009(2) N1 0.044(2) 0.039(2) 0.049(2) 0.0041(16) -0.0031(17) 0.0008(16) N2 0.046(2) 0.041(2) 0.059(2) -0.0003(17) -0.0027(18) 0.0008(17) N3 0.052(2) 0.042(2) 0.060(2) -0.0014(18) -0.0019(19) 0.0016(18) N4 0.042(2) 0.077(3) 0.053(2) 0.001(2) -0.0020(18) 0.000(2) C1 0.049(3) 0.040(3) 0.051(3) 0.000(2) -0.009(2) -0.006(2) C2 0.044(2) 0.042(2) 0.039(2) 0.0005(19) 0.0018(19) 0.002(2) C3 0.038(2) 0.045(2) 0.044(2) 0.006(2) -0.0001(19) 0.0030(19) C4 0.059(3) 0.049(3) 0.063(3) -0.006(3) -0.009(3) 0.011(2) C5 0.064(3) 0.055(3) 0.076(4) 0.005(3) -0.007(3) 0.024(3) C6 0.049(3) 0.070(4) 0.071(4) 0.008(3) -0.009(3) 0.010(3) C7 0.052(3) 0.066(3) 0.065(3) -0.003(3) -0.010(3) -0.006(3) C8 0.044(3) 0.045(3) 0.059(3) 0.001(2) 0.003(2) 0.003(2) C9 0.039(2) 0.047(2) 0.037(2) 0.0017(19) 0.0048(19) 0.001(2) C10 0.056(3) 0.045(3) 0.053(3) -0.004(2) 0.001(2) -0.001(2) C11 0.058(3) 0.043(3) 0.070(3) -0.004(3) 0.007(3) 0.008(2) C12 0.048(3) 0.058(3) 0.056(3) 0.006(2) 0.006(2) 0.014(3) C13 0.038(2) 0.051(3) 0.047(3) 0.002(2) 0.003(2) -0.003(2) C14 0.050(3) 0.043(3) 0.044(3) 0.000(2) 0.009(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C8 1.745(4) . ? O1 N4 1.218(5) . ? O2 N4 1.219(5) . ? N1 C1 1.351(5) . ? N1 N2 1.364(4) . ? N1 C9 1.419(5) . ? N2 N3 1.294(5) . ? N3 C2 1.365(5) . ? N4 C13 1.481(5) . ? C1 C2 1.352(6) . ? C1 H1 0.91(3) . ? C2 C3 1.477(5) . ? C3 C8 1.386(6) . ? C3 C4 1.400(6) . ? C4 C5 1.378(7) . ? C4 H4 0.89(4) . ? C5 C6 1.362(7) . ? C5 H5 0.89(4) . ? C6 C7 1.375(7) . ? C6 H6 0.95(5) . ? C7 C8 1.373(6) . ? C7 H7 0.94(4) . ? C9 C14 1.379(6) . ? C9 C10 1.398(6) . ? C10 C11 1.364(6) . ? C10 H10 0.87(4) . ? C11 C12 1.386(7) . ? C11 H11 0.89(4) . ? C12 C13 1.374(6) . ? C12 H12 0.85(4) . ? C13 C14 1.370(6) . ? C14 H14 0.97(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 109.2(3) . . ? C1 N1 C9 130.5(4) . . ? N2 N1 C9 120.3(3) . . ? N3 N2 N1 107.3(3) . . ? N2 N3 C2 109.7(3) . . ? O1 N4 O2 124.2(4) . . ? O1 N4 C13 118.4(4) . . ? O2 N4 C13 117.4(4) . . ? N1 C1 C2 106.1(4) . . ? N1 C1 H1 118(2) . . ? C2 C1 H1 135(2) . . ? C1 C2 N3 107.6(3) . . ? C1 C2 C3 131.9(4) . . ? N3 C2 C3 120.5(4) . . ? C8 C3 C4 116.3(4) . . ? C8 C3 C2 124.6(4) . . ? C4 C3 C2 119.1(4) . . ? C5 C4 C3 121.1(5) . . ? C5 C4 H4 119(3) . . ? C3 C4 H4 120(3) . . ? C6 C5 C4 121.0(5) . . ? C6 C5 H5 123(3) . . ? C4 C5 H5 116(3) . . ? C5 C6 C7 119.2(5) . . ? C5 C6 H6 120(3) . . ? C7 C6 H6 121(3) . . ? C8 C7 C6 120.0(5) . . ? C8 C7 H7 121(3) . . ? C6 C7 H7 119(3) . . ? C7 C8 C3 122.4(4) . . ? C7 C8 Cl1 116.5(4) . . ? C3 C8 Cl1 121.1(3) . . ? C14 C9 C10 119.9(4) . . ? C14 C9 N1 119.5(4) . . ? C10 C9 N1 120.6(4) . . ? C11 C10 C9 120.0(5) . . ? C11 C10 H10 118(3) . . ? C9 C10 H10 122(3) . . ? C10 C11 C12 120.9(5) . . ? C10 C11 H11 122(3) . . ? C12 C11 H11 117(3) . . ? C13 C12 C11 117.9(5) . . ? C13 C12 H12 120(3) . . ? C11 C12 H12 122(3) . . ? C14 C13 C12 122.9(4) . . ? C14 C13 N4 117.6(4) . . ? C12 C13 N4 119.5(4) . . ? C13 C14 C9 118.5(4) . . ? C13 C14 H14 120(2) . . ? C9 C14 H14 121(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 C1 N1 N2 N3 0.1(5) . . . . ? C9 N1 N2 N3 178.5(3) . . . . ? N1 N2 N3 C2 -0.5(5) . . . . ? N2 N1 C1 C2 0.4(5) . . . . ? C9 N1 C1 C2 -177.8(4) . . . . ? N1 C1 C2 N3 -0.7(5) . . . . ? N1 C1 C2 C3 178.9(4) . . . . ? N2 N3 C2 C1 0.8(5) . . . . ? N2 N3 C2 C3 -178.9(4) . . . . ? C1 C2 C3 C8 -24.1(8) . . . . ? N3 C2 C3 C8 155.5(4) . . . . ? C1 C2 C3 C4 157.1(5) . . . . ? N3 C2 C3 C4 -23.3(6) . . . . ? C8 C3 C4 C5 1.0(7) . . . . ? C2 C3 C4 C5 179.9(5) . . . . ? C3 C4 C5 C6 -1.2(9) . . . . ? C4 C5 C6 C7 1.2(9) . . . . ? C5 C6 C7 C8 -1.2(8) . . . . ? C6 C7 C8 C3 1.2(8) . . . . ? C6 C7 C8 Cl1 -178.2(4) . . . . ? C4 C3 C8 C7 -1.1(7) . . . . ? C2 C3 C8 C7 -179.9(4) . . . . ? C4 C3 C8 Cl1 178.3(4) . . . . ? C2 C3 C8 Cl1 -0.5(6) . . . . ? C1 N1 C9 C14 -166.5(4) . . . . ? N2 N1 C9 C14 15.5(6) . . . . ? C1 N1 C9 C10 14.8(7) . . . . ? N2 N1 C9 C10 -163.2(4) . . . . ? C14 C9 C10 C11 -0.3(7) . . . . ? N1 C9 C10 C11 178.4(4) . . . . ? C9 C10 C11 C12 -0.8(8) . . . . ? C10 C11 C12 C13 1.3(8) . . . . ? C11 C12 C13 C14 -0.7(7) . . . . ? C11 C12 C13 N4 178.2(4) . . . . ? O1 N4 C13 C14 8.2(6) . . . . ? O2 N4 C13 C14 -171.7(4) . . . . ? O1 N4 C13 C12 -170.8(5) . . . . ? O2 N4 C13 C12 9.3(6) . . . . ? C12 C13 C14 C9 -0.3(7) . . . . ? N4 C13 C14 C9 -179.2(4) . . . . ? C10 C9 C14 C13 0.8(6) . . . . ? N1 C9 C14 C13 -177.9(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 O1 0.91(3) 2.72(3) 3.252(6) 118(3) 2_746 C6 H6 O1 0.95(5) 2.66(6) 3.500(6) 147(4) 4_475 C7 H7 O2 0.94(4) 2.58(4) 3.328(6) 136(3) 4_465 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.214 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 731509' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '3N3Cl.cif' data_3N3Cl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? 4-(3-Chlorophenyl)-1-(3-nitrophenyl)-1H-1,2,3-triazole ; _chemical_name_common ? _chemical_melting_point 186 _chemical_formula_moiety 'C14 H9 Cl N4 O2' _chemical_formula_sum 'C14 H9 Cl N4 O2' _chemical_formula_weight 300.70 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.080(2) _cell_length_b 8.369(2) _cell_length_c 13.026(4) _cell_angle_alpha 102.628(4) _cell_angle_beta 94.538(5) _cell_angle_gamma 114.741(4) _cell_volume 671.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1697 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 24.12 _exptl_crystal_description NEEDLE _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9274 _exptl_absorpt_correction_T_max 0.9712 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6261 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2348 _reflns_number_gt 1794 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0918P)^2^+0.4181P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2348 _refine_ls_number_parameters 202 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1067 _refine_ls_R_factor_gt 0.0821 _refine_ls_wR_factor_ref 0.2050 _refine_ls_wR_factor_gt 0.1925 _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_restrained_S_all 1.167 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.4974(3) 0.7444(2) 0.02761(10) 0.0832(6) Uani 1 1 d . . . O1 O 0.8816(5) 0.2104(4) 0.6975(2) 0.0589(9) Uani 1 1 d . . . O2 O 0.9992(7) 0.3283(5) 0.8671(3) 0.0822(12) Uani 1 1 d . . . N1 N 0.7848(5) 0.6828(4) 0.5584(2) 0.0356(8) Uani 1 1 d . . . N2 N 0.7441(6) 0.5445(4) 0.4702(3) 0.0481(9) Uani 1 1 d . . . N3 N 0.6967(6) 0.5928(5) 0.3869(3) 0.0501(9) Uani 1 1 d . . . N4 N 0.9320(6) 0.3341(5) 0.7791(3) 0.0478(9) Uani 1 1 d . . . C1 C 0.7630(6) 0.8205(5) 0.5287(3) 0.0403(10) Uani 1 1 d . . . C2 C 0.7064(6) 0.7642(5) 0.4208(3) 0.0347(9) Uani 1 1 d . . . C3 C 0.6596(6) 0.8551(5) 0.3444(3) 0.0401(9) Uani 1 1 d . . . C4 C 0.6653(6) 1.0272(5) 0.3801(3) 0.0436(10) Uani 1 1 d . . . H4 H 0.7008 1.0861 0.4532 0.052 Uiso 1 1 calc R . . C5 C 0.6183(7) 1.1118(6) 0.3075(4) 0.0527(12) Uani 1 1 d . . . C6 C 0.5670(7) 1.0255(6) 0.1996(4) 0.0547(12) Uani 1 1 d . . . H6 H 0.5352 1.0805 0.1505 0.066 Uiso 1 1 calc R . . C7 C 0.5632(7) 0.8535(6) 0.1645(3) 0.0474(11) Uani 1 1 d . . . C8 C 0.6101(6) 0.7711(6) 0.2357(3) 0.0452(10) Uani 1 1 d . . . H8 H 0.6086 0.6576 0.2106 0.054 Uiso 1 1 calc R . . C9 C 0.8379(6) 0.6669(5) 0.6628(3) 0.0362(9) Uani 1 1 d . . . C10 C 0.8626(7) 0.7994(6) 0.7541(3) 0.0473(11) Uani 1 1 d . . . H10 H 0.8461 0.9019 0.7484 0.057 Uiso 1 1 calc R . . C11 C 0.9116(8) 0.7799(6) 0.8534(3) 0.0597(13) Uani 1 1 d . . . H11 H 0.9280 0.8699 0.9145 0.072 Uiso 1 1 calc R . . C12 C 0.9367(7) 0.6297(6) 0.8639(4) 0.0523(11) Uani 1 1 d D . . C13 C 0.9119(6) 0.5006(5) 0.7709(3) 0.0393(9) Uani 1 1 d . . . C14 C 0.8630(6) 0.5138(5) 0.6699(3) 0.0390(9) Uani 1 1 d . . . H14 H 0.8474 0.4239 0.6089 0.047 Uiso 1 1 calc R . . H1 H 0.784(5) 0.932(5) 0.583(3) 0.039(10) Uiso 1 1 d . . . H12 H 0.984(8) 0.639(7) 0.935(2) 0.084(17) Uiso 1 1 d D . . H5 H 0.616(7) 1.222(7) 0.337(4) 0.069(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1349(14) 0.0902(11) 0.0436(7) 0.0238(7) 0.0100(7) 0.0669(10) O1 0.086(2) 0.0401(17) 0.0556(19) 0.0122(15) 0.0105(16) 0.0337(17) O2 0.130(3) 0.093(3) 0.055(2) 0.0304(19) 0.005(2) 0.077(3) N1 0.0452(19) 0.0275(16) 0.0376(18) 0.0095(13) 0.0047(14) 0.0198(14) N2 0.075(3) 0.0371(19) 0.0372(19) 0.0061(15) 0.0023(17) 0.0335(18) N3 0.072(3) 0.042(2) 0.042(2) 0.0091(16) 0.0048(17) 0.0326(19) N4 0.057(2) 0.047(2) 0.053(2) 0.0223(18) 0.0113(17) 0.0302(18) C1 0.049(2) 0.025(2) 0.045(2) 0.0037(17) 0.0013(18) 0.0195(18) C2 0.036(2) 0.0248(19) 0.044(2) 0.0078(16) 0.0060(16) 0.0149(16) C3 0.035(2) 0.038(2) 0.049(2) 0.0144(18) 0.0100(17) 0.0159(18) C4 0.047(2) 0.034(2) 0.047(2) 0.0090(18) 0.0070(18) 0.0177(18) C5 0.055(3) 0.042(3) 0.068(3) 0.019(2) 0.013(2) 0.026(2) C6 0.062(3) 0.050(3) 0.070(3) 0.038(2) 0.017(2) 0.030(2) C7 0.053(3) 0.049(3) 0.047(2) 0.021(2) 0.0077(19) 0.026(2) C8 0.051(3) 0.041(2) 0.051(3) 0.019(2) 0.013(2) 0.023(2) C9 0.035(2) 0.034(2) 0.041(2) 0.0104(16) 0.0043(16) 0.0171(17) C10 0.068(3) 0.037(2) 0.045(2) 0.0079(18) 0.010(2) 0.034(2) C11 0.089(4) 0.052(3) 0.036(2) 0.001(2) 0.008(2) 0.035(3) C12 0.064(3) 0.058(3) 0.039(2) 0.011(2) 0.003(2) 0.032(2) C13 0.043(2) 0.032(2) 0.046(2) 0.0140(17) 0.0074(18) 0.0189(18) C14 0.047(2) 0.032(2) 0.038(2) 0.0069(16) 0.0059(17) 0.0182(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C7 1.740(4) . ? O1 N4 1.216(4) . ? O2 N4 1.224(4) . ? N1 N2 1.353(4) . ? N1 C1 1.355(5) . ? N1 C9 1.431(5) . ? N2 N3 1.305(5) . ? N3 C2 1.376(5) . ? N4 C13 1.484(5) . ? C1 C2 1.349(5) . ? C1 H1 0.98(4) . ? C2 C3 1.474(5) . ? C3 C8 1.379(6) . ? C3 C4 1.395(6) . ? C4 C5 1.396(6) . ? C4 H4 0.9300 . ? C5 C6 1.373(7) . ? C5 H5 0.93(5) . ? C6 C7 1.399(6) . ? C6 H6 0.9300 . ? C7 C8 1.367(6) . ? C8 H8 0.9300 . ? C9 C10 1.379(5) . ? C9 C14 1.387(5) . ? C10 C11 1.375(6) . ? C10 H10 0.9300 . ? C11 C12 1.374(7) . ? C11 H11 0.9300 . ? C12 C13 1.379(6) . ? C12 H12 0.94(2) . ? C13 C14 1.373(5) . ? C14 H14 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C1 109.5(3) . . ? N2 N1 C9 120.2(3) . . ? C1 N1 C9 130.3(3) . . ? N3 N2 N1 107.6(3) . . ? N2 N3 C2 109.0(3) . . ? O1 N4 O2 123.3(4) . . ? O1 N4 C13 118.0(3) . . ? O2 N4 C13 118.7(4) . . ? C2 C1 N1 106.2(3) . . ? C2 C1 H1 133(2) . . ? N1 C1 H1 121(2) . . ? C1 C2 N3 107.7(3) . . ? C1 C2 C3 130.8(3) . . ? N3 C2 C3 121.6(3) . . ? C8 C3 C4 118.8(4) . . ? C8 C3 C2 120.2(4) . . ? C4 C3 C2 121.0(4) . . ? C3 C4 C5 120.7(4) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 119.7(4) . . ? C6 C5 H5 124(3) . . ? C4 C5 H5 116(3) . . ? C5 C6 C7 119.1(4) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C8 C7 C6 121.1(4) . . ? C8 C7 Cl1 120.0(3) . . ? C6 C7 Cl1 118.9(3) . . ? C7 C8 C3 120.5(4) . . ? C7 C8 H8 119.8 . . ? C3 C8 H8 119.8 . . ? C10 C9 C14 120.7(4) . . ? C10 C9 N1 121.1(3) . . ? C14 C9 N1 118.2(3) . . ? C11 C10 C9 120.0(4) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C11 C10 121.2(4) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 117.2(4) . . ? C11 C12 H12 113(3) . . ? C13 C12 H12 129(3) . . ? C14 C13 C12 123.8(4) . . ? C14 C13 N4 117.4(3) . . ? C12 C13 N4 118.7(4) . . ? C13 C14 C9 117.2(4) . . ? C13 C14 H14 121.4 . . ? C9 C14 H14 121.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 N3 -0.3(4) . . . . ? C9 N1 N2 N3 178.8(3) . . . . ? N1 N2 N3 C2 0.0(5) . . . . ? N2 N1 C1 C2 0.5(4) . . . . ? C9 N1 C1 C2 -178.5(4) . . . . ? N1 C1 C2 N3 -0.5(4) . . . . ? N1 C1 C2 C3 179.5(4) . . . . ? N2 N3 C2 C1 0.3(5) . . . . ? N2 N3 C2 C3 -179.7(3) . . . . ? C1 C2 C3 C8 178.1(4) . . . . ? N3 C2 C3 C8 -1.8(6) . . . . ? C1 C2 C3 C4 -1.6(6) . . . . ? N3 C2 C3 C4 178.5(4) . . . . ? C8 C3 C4 C5 1.1(6) . . . . ? C2 C3 C4 C5 -179.2(4) . . . . ? C3 C4 C5 C6 -0.4(7) . . . . ? C4 C5 C6 C7 -0.1(7) . . . . ? C5 C6 C7 C8 -0.1(7) . . . . ? C5 C6 C7 Cl1 179.8(3) . . . . ? C6 C7 C8 C3 0.9(6) . . . . ? Cl1 C7 C8 C3 -179.1(3) . . . . ? C4 C3 C8 C7 -1.3(6) . . . . ? C2 C3 C8 C7 179.0(4) . . . . ? N2 N1 C9 C10 -174.5(4) . . . . ? C1 N1 C9 C10 4.4(6) . . . . ? N2 N1 C9 C14 5.2(5) . . . . ? C1 N1 C9 C14 -175.9(4) . . . . ? C14 C9 C10 C11 -0.3(6) . . . . ? N1 C9 C10 C11 179.4(4) . . . . ? C9 C10 C11 C12 0.0(7) . . . . ? C10 C11 C12 C13 0.4(7) . . . . ? C11 C12 C13 C14 -0.4(7) . . . . ? C11 C12 C13 N4 -178.3(4) . . . . ? O1 N4 C13 C14 -8.0(5) . . . . ? O2 N4 C13 C14 171.7(4) . . . . ? O1 N4 C13 C12 170.1(4) . . . . ? O2 N4 C13 C12 -10.3(6) . . . . ? C12 C13 C14 C9 0.1(6) . . . . ? N4 C13 C14 C9 178.0(3) . . . . ? C10 C9 C14 C13 0.3(6) . . . . ? N1 C9 C14 C13 -179.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C5 H5 N2 0.93(5) 2.60(5) 3.470(6) 157(4) 1_565 C12 H12 O2 0.94(2) 2.52(3) 3.418(6) 161(4) 2_767 C1 H1 O1 0.98(4) 2.26(4) 3.235(5) 171(3) 1_565 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.317 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 731510' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '3N4Cl.cif' data_3N4Cl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? 4-(3-Chlorophenyl)-1-(4-nitrophenyl)-1H-1,2,3-triazole ; _chemical_name_common ? _chemical_melting_point 223-224 _chemical_formula_moiety 'C14 H9 Cl N4 O2' _chemical_formula_sum 'C14 H9 Cl N4 O2' _chemical_formula_weight 300.70 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.550(5) _cell_length_b 5.256(3) _cell_length_c 29.749(18) _cell_angle_alpha 90.00 _cell_angle_beta 96.543(10) _cell_angle_gamma 90.00 _cell_volume 1328.1(14) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1212 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 22.59 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.298 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9108 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6072 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.0726 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2330 _reflns_number_gt 1548 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0545P)^2^+0.5779P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2330 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0649 _refine_ls_wR_factor_ref 0.1594 _refine_ls_wR_factor_gt 0.1399 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.08245(16) 0.6080(3) 0.19811(4) 0.1017(6) Uani 1 1 d . . . O1 O 0.0466(3) -0.0313(5) 0.55335(9) 0.0636(8) Uani 1 1 d . . . O2 O 0.1557(3) 0.0204(5) 0.62121(9) 0.0679(8) Uani 1 1 d . . . N1 N 0.2651(3) 0.6406(5) 0.46176(10) 0.0420(7) Uani 1 1 d . . . N2 N 0.3248(3) 0.8659(5) 0.44903(11) 0.0547(8) Uani 1 1 d . . . N3 N 0.2872(4) 0.8909(5) 0.40569(11) 0.0583(9) Uani 1 1 d . . . N4 N 0.1373(3) 0.0786(5) 0.58138(11) 0.0476(8) Uani 1 1 d . . . C1 C 0.1887(4) 0.5270(7) 0.42487(13) 0.0457(9) Uani 1 1 d . . . C2 C 0.2017(4) 0.6836(6) 0.38977(12) 0.0443(9) Uani 1 1 d . . . C3 C 0.1366(4) 0.6627(6) 0.34241(12) 0.0455(9) Uani 1 1 d . . . C4 C 0.1744(5) 0.8307(8) 0.31009(14) 0.0630(11) Uani 1 1 d . . . C5 C 0.1097(6) 0.8160(9) 0.26595(16) 0.0731(13) Uani 1 1 d . . . C6 C 0.0033(5) 0.6290(9) 0.25353(14) 0.0652(11) Uani 1 1 d . . . C7 C -0.0340(6) 0.4564(10) 0.28423(16) 0.0725(13) Uani 1 1 d . . . C8 C 0.0305(5) 0.4715(9) 0.32877(15) 0.0658(12) Uani 1 1 d . . . C9 C 0.2873(4) 0.5646(6) 0.50753(12) 0.0401(8) Uani 1 1 d . . . C10 C 0.3947(4) 0.6898(7) 0.53826(14) 0.0480(9) Uani 1 1 d . . . C11 C 0.4151(4) 0.6182(7) 0.58235(14) 0.0530(10) Uani 1 1 d . . . C12 C 0.3310(4) 0.4172(7) 0.59744(14) 0.0505(10) Uani 1 1 d . . . C13 C 0.2275(4) 0.2945(6) 0.56632(12) 0.0400(8) Uani 1 1 d . . . C14 C 0.2029(4) 0.3611(6) 0.52174(13) 0.0419(9) Uani 1 1 d . . . H1 H 0.139(4) 0.380(6) 0.4272(11) 0.049(10) Uiso 1 1 d . . . H4 H 0.241(5) 0.964(7) 0.3180(13) 0.067(12) Uiso 1 1 d . . . H5 H 0.137(5) 0.932(8) 0.2456(14) 0.080(14) Uiso 1 1 d . . . H7 H -0.100(5) 0.333(7) 0.2764(14) 0.072(13) Uiso 1 1 d . . . H8 H 0.012(5) 0.350(8) 0.3484(14) 0.075(14) Uiso 1 1 d . . . H10 H 0.448(4) 0.816(6) 0.5280(11) 0.041(9) Uiso 1 1 d . . . H11 H 0.485(5) 0.689(7) 0.6031(13) 0.075(13) Uiso 1 1 d . . . H12 H 0.347(3) 0.372(5) 0.6274(11) 0.035(9) Uiso 1 1 d . . . H14 H 0.132(4) 0.286(6) 0.5026(10) 0.036(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0972(10) 0.1442(13) 0.0585(8) -0.0066(8) -0.0135(7) 0.0164(9) O1 0.0640(17) 0.0584(16) 0.0658(18) -0.0035(14) -0.0039(14) -0.0258(13) O2 0.082(2) 0.0674(18) 0.0528(18) 0.0140(15) 0.0007(15) -0.0133(15) N1 0.0426(15) 0.0326(14) 0.0500(18) -0.0034(13) 0.0015(13) -0.0075(12) N2 0.063(2) 0.0366(16) 0.063(2) -0.0007(16) 0.0032(17) -0.0198(14) N3 0.073(2) 0.0432(17) 0.056(2) 0.0007(16) -0.0028(17) -0.0175(15) N4 0.0448(17) 0.0463(17) 0.051(2) 0.0003(16) 0.0044(15) -0.0022(14) C1 0.049(2) 0.0315(18) 0.054(2) -0.0053(18) -0.0014(18) -0.0073(16) C2 0.0426(19) 0.0333(18) 0.057(2) -0.0013(17) 0.0034(17) -0.0013(15) C3 0.049(2) 0.0391(19) 0.049(2) -0.0005(17) 0.0049(17) 0.0001(16) C4 0.078(3) 0.052(2) 0.057(3) 0.004(2) 0.002(2) -0.018(2) C5 0.090(3) 0.069(3) 0.058(3) 0.017(3) 0.001(3) -0.007(3) C6 0.063(3) 0.081(3) 0.050(2) -0.002(2) -0.001(2) 0.009(2) C7 0.073(3) 0.082(3) 0.061(3) -0.010(3) 0.003(2) -0.023(3) C8 0.079(3) 0.064(3) 0.054(3) 0.002(2) 0.005(2) -0.022(2) C9 0.0375(17) 0.0326(17) 0.049(2) -0.0057(16) 0.0009(16) -0.0016(15) C10 0.044(2) 0.043(2) 0.057(3) -0.0080(19) 0.0033(19) -0.0110(17) C11 0.042(2) 0.054(2) 0.060(3) -0.014(2) -0.0062(19) -0.0066(18) C12 0.050(2) 0.054(2) 0.046(2) -0.005(2) -0.0032(19) -0.0012(18) C13 0.0349(17) 0.0359(18) 0.049(2) -0.0057(16) 0.0027(16) -0.0052(14) C14 0.0386(18) 0.0372(18) 0.048(2) -0.0097(17) -0.0052(16) -0.0051(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C6 1.730(4) . ? O1 N4 1.217(3) . ? O2 N4 1.216(4) . ? N1 C1 1.351(4) . ? N1 N2 1.360(4) . ? N1 C9 1.411(4) . ? N2 N3 1.299(4) . ? N3 C2 1.366(4) . ? N4 C13 1.471(4) . ? C1 C2 1.344(5) . ? C1 H1 0.89(3) . ? C2 C3 1.459(5) . ? C3 C4 1.371(5) . ? C3 C8 1.383(5) . ? C4 C5 1.368(6) . ? C4 H4 0.92(4) . ? C5 C6 1.361(6) . ? C5 H5 0.91(4) . ? C6 C7 1.351(6) . ? C7 C8 1.378(6) . ? C7 H7 0.88(4) . ? C8 H8 0.89(4) . ? C9 C14 1.383(5) . ? C9 C10 1.386(4) . ? C10 C11 1.357(5) . ? C10 H10 0.88(3) . ? C11 C12 1.381(5) . ? C11 H11 0.89(4) . ? C12 C13 1.367(5) . ? C12 H12 0.92(3) . ? C13 C14 1.365(5) . ? C14 H14 0.88(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 108.7(3) . . ? C1 N1 C9 131.2(3) . . ? N2 N1 C9 120.1(3) . . ? N3 N2 N1 107.8(3) . . ? N2 N3 C2 109.0(3) . . ? O2 N4 O1 123.4(3) . . ? O2 N4 C13 118.4(3) . . ? O1 N4 C13 118.2(3) . . ? C2 C1 N1 106.6(3) . . ? C2 C1 H1 133(2) . . ? N1 C1 H1 121(2) . . ? C1 C2 N3 107.9(3) . . ? C1 C2 C3 130.4(3) . . ? N3 C2 C3 121.7(3) . . ? C4 C3 C8 117.5(4) . . ? C4 C3 C2 122.3(3) . . ? C8 C3 C2 120.2(3) . . ? C5 C4 C3 122.3(4) . . ? C5 C4 H4 118(2) . . ? C3 C4 H4 120(3) . . ? C6 C5 C4 119.1(4) . . ? C6 C5 H5 121(3) . . ? C4 C5 H5 120(3) . . ? C7 C6 C5 120.2(4) . . ? C7 C6 Cl1 119.6(4) . . ? C5 C6 Cl1 120.2(4) . . ? C6 C7 C8 120.8(4) . . ? C6 C7 H7 121(3) . . ? C8 C7 H7 118(3) . . ? C7 C8 C3 120.1(4) . . ? C7 C8 H8 121(3) . . ? C3 C8 H8 119(3) . . ? C14 C9 C10 119.7(3) . . ? C14 C9 N1 119.8(3) . . ? C10 C9 N1 120.5(3) . . ? C11 C10 C9 120.6(4) . . ? C11 C10 H10 122(2) . . ? C9 C10 H10 118(2) . . ? C10 C11 C12 120.8(4) . . ? C10 C11 H11 124(3) . . ? C12 C11 H11 115(3) . . ? C13 C12 C11 117.5(4) . . ? C13 C12 H12 123.2(19) . . ? C11 C12 H12 119.3(19) . . ? C14 C13 C12 123.6(3) . . ? C14 C13 N4 117.8(3) . . ? C12 C13 N4 118.7(3) . . ? C13 C14 C9 117.9(3) . . ? C13 C14 H14 122(2) . . ? C9 C14 H14 120(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 N3 -0.2(4) . . . . ? C9 N1 N2 N3 -179.5(3) . . . . ? N1 N2 N3 C2 0.4(4) . . . . ? N2 N1 C1 C2 -0.1(4) . . . . ? C9 N1 C1 C2 179.1(3) . . . . ? N1 C1 C2 N3 0.4(4) . . . . ? N1 C1 C2 C3 -177.1(3) . . . . ? N2 N3 C2 C1 -0.5(4) . . . . ? N2 N3 C2 C3 177.2(3) . . . . ? C1 C2 C3 C4 -173.8(4) . . . . ? N3 C2 C3 C4 9.0(5) . . . . ? C1 C2 C3 C8 7.4(6) . . . . ? N3 C2 C3 C8 -169.8(4) . . . . ? C8 C3 C4 C5 0.9(6) . . . . ? C2 C3 C4 C5 -177.9(4) . . . . ? C3 C4 C5 C6 0.3(7) . . . . ? C4 C5 C6 C7 -1.9(7) . . . . ? C4 C5 C6 Cl1 179.2(4) . . . . ? C5 C6 C7 C8 2.2(7) . . . . ? Cl1 C6 C7 C8 -178.8(4) . . . . ? C6 C7 C8 C3 -1.0(7) . . . . ? C4 C3 C8 C7 -0.6(6) . . . . ? C2 C3 C8 C7 178.3(4) . . . . ? C1 N1 C9 C14 -11.1(5) . . . . ? N2 N1 C9 C14 168.1(3) . . . . ? C1 N1 C9 C10 168.0(3) . . . . ? N2 N1 C9 C10 -12.9(5) . . . . ? C14 C9 C10 C11 -1.5(5) . . . . ? N1 C9 C10 C11 179.4(3) . . . . ? C9 C10 C11 C12 0.8(6) . . . . ? C10 C11 C12 C13 0.1(5) . . . . ? C11 C12 C13 C14 -0.4(5) . . . . ? C11 C12 C13 N4 179.5(3) . . . . ? O2 N4 C13 C14 -178.5(3) . . . . ? O1 N4 C13 C14 0.8(4) . . . . ? O2 N4 C13 C12 1.5(5) . . . . ? O1 N4 C13 C12 -179.2(3) . . . . ? C12 C13 C14 C9 -0.2(5) . . . . ? N4 C13 C14 C9 179.8(3) . . . . ? C10 C9 C14 C13 1.2(5) . . . . ? N1 C9 C14 C13 -179.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C10 H10 N2 0.88(3) 2.59(3) 3.338(5) 143(3) 3_676 C14 H14 O1 0.88(3) 2.51(3) 3.385(4) 173(3) 3_556 C8 H8 O2 0.89(4) 2.64(4) 3.460(5) 154(3) 3_556 C1 H1 O1 0.89(3) 2.53(3) 3.399(5) 165(3) 3_556 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.232 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 731511' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '4N2Cl.cif' data_4N2Cl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? 4-(4-Chlorophenyl)-1-(2-nitrophenyl)-1H-1,2,3-triazole ; _chemical_name_common ? _chemical_melting_point 214-216 _chemical_formula_moiety 'C14 H9 Cl N4 O2' _chemical_formula_sum 'C14 H9 Cl N4 O2' _chemical_formula_weight 300.70 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Triclinic' _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.013(4) _cell_length_b 7.312(4) _cell_length_c 13.309(7) _cell_angle_alpha 94.793(8) _cell_angle_beta 96.114(8) _cell_angle_gamma 107.261(8) _cell_volume 643.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2487 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 26.50 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.307 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9299 _exptl_absorpt_correction_T_max 0.9788 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5920 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2244 _reflns_number_gt 1792 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0822P)^2^+0.1040P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2244 _refine_ls_number_parameters 226 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1507 _refine_ls_wR_factor_gt 0.1434 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.12146(13) 0.16349(10) -0.07822(5) 0.0615(3) Uani 1 1 d . . . O1 O 0.2370(4) 0.0289(3) 0.64946(16) 0.0727(7) Uani 1 1 d . . . O2 O 0.2463(4) -0.2088(3) 0.54540(16) 0.0690(6) Uani 1 1 d . . . N1 N 0.2807(3) 0.4106(3) 0.24229(15) 0.0414(5) Uani 1 1 d . . . N2 N 0.3328(4) 0.6053(3) 0.25987(17) 0.0551(6) Uani 1 1 d . . . N3 N 0.3288(4) 0.6680(3) 0.17063(17) 0.0537(6) Uani 1 1 d . . . N4 N 0.2457(3) -0.0427(4) 0.56473(17) 0.0512(6) Uani 1 1 d . . . C1 C 0.2442(4) 0.3516(4) 0.14116(19) 0.0441(6) Uani 1 1 d D . . C2 C 0.2755(4) 0.5167(4) 0.09570(19) 0.0396(6) Uani 1 1 d . . . C3 C 0.2616(4) 0.5504(3) -0.01239(18) 0.0386(6) Uani 1 1 d . . . C4 C 0.3172(4) 0.7409(4) -0.0358(2) 0.0483(7) Uani 1 1 d . . . C5 C 0.3095(5) 0.7815(5) -0.1351(2) 0.0557(8) Uani 1 1 d . . . C6 C 0.2442(5) 0.6349(5) -0.2143(2) 0.0565(8) Uani 1 1 d . . . C7 C 0.1890(4) 0.4470(5) -0.1946(2) 0.0500(7) Uani 1 1 d . . . C8 C 0.1966(4) 0.4061(4) -0.09464(19) 0.0423(6) Uani 1 1 d . . . C9 C 0.2722(4) 0.2953(4) 0.32387(18) 0.0405(6) Uani 1 1 d . . . C10 C 0.2731(4) 0.1069(4) 0.3056(2) 0.0481(7) Uani 1 1 d . . . C11 C 0.2627(4) -0.0044(4) 0.3842(2) 0.0491(7) Uani 1 1 d . . . C12 C 0.2559(4) 0.0780(4) 0.48100(19) 0.0430(6) Uani 1 1 d . . . C13 C 0.2577(4) 0.2646(4) 0.5001(2) 0.0508(7) Uani 1 1 d . . . C14 C 0.2650(4) 0.3764(4) 0.4211(2) 0.0494(7) Uani 1 1 d . . . H1 H 0.202(5) 0.220(3) 0.115(2) 0.075(10) Uiso 1 1 d D . . H4 H 0.354(4) 0.843(4) 0.022(2) 0.056(8) Uiso 1 1 d . . . H5 H 0.349(4) 0.910(4) -0.145(2) 0.055(8) Uiso 1 1 d . . . H6 H 0.234(5) 0.655(4) -0.285(3) 0.069(9) Uiso 1 1 d . . . H7 H 0.148(5) 0.346(5) -0.243(3) 0.071(10) Uiso 1 1 d . . . H10 H 0.280(4) 0.052(4) 0.241(2) 0.046(7) Uiso 1 1 d . . . H11 H 0.267(4) -0.127(4) 0.376(2) 0.044(7) Uiso 1 1 d . . . H13 H 0.260(4) 0.327(4) 0.571(2) 0.060(8) Uiso 1 1 d . . . H14 H 0.267(4) 0.504(4) 0.435(2) 0.056(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0957(6) 0.0397(4) 0.0429(4) 0.0061(3) 0.0072(4) 0.0119(4) O1 0.1055(18) 0.0808(16) 0.0373(12) 0.0174(11) 0.0195(11) 0.0310(13) O2 0.1031(18) 0.0608(14) 0.0549(13) 0.0230(11) 0.0190(12) 0.0359(13) N1 0.0508(12) 0.0405(12) 0.0328(11) 0.0061(9) 0.0071(9) 0.0130(10) N2 0.0837(17) 0.0438(13) 0.0374(13) 0.0053(10) 0.0097(12) 0.0183(12) N3 0.0777(17) 0.0434(13) 0.0405(13) 0.0080(10) 0.0109(12) 0.0176(12) N4 0.0527(14) 0.0623(16) 0.0387(14) 0.0158(11) 0.0082(10) 0.0148(12) C1 0.0578(16) 0.0395(15) 0.0334(14) 0.0048(11) 0.0064(12) 0.0126(13) C2 0.0398(13) 0.0416(14) 0.0386(14) 0.0080(11) 0.0096(11) 0.0119(11) C3 0.0432(14) 0.0391(14) 0.0356(14) 0.0087(11) 0.0097(11) 0.0134(11) C4 0.0581(17) 0.0442(16) 0.0466(16) 0.0117(13) 0.0140(13) 0.0177(13) C5 0.0688(19) 0.0483(17) 0.0592(19) 0.0250(15) 0.0202(15) 0.0233(15) C6 0.0674(19) 0.067(2) 0.0450(18) 0.0245(15) 0.0164(14) 0.0276(15) C7 0.0616(18) 0.0546(18) 0.0348(15) 0.0059(13) 0.0085(13) 0.0190(14) C8 0.0471(14) 0.0431(15) 0.0394(14) 0.0096(11) 0.0108(11) 0.0152(12) C9 0.0411(14) 0.0440(14) 0.0345(14) 0.0087(11) 0.0062(10) 0.0089(11) C10 0.0675(18) 0.0474(16) 0.0311(14) 0.0033(12) 0.0103(12) 0.0197(13) C11 0.0630(18) 0.0457(16) 0.0404(15) 0.0095(12) 0.0084(13) 0.0177(14) C12 0.0428(14) 0.0484(15) 0.0364(14) 0.0117(12) 0.0061(11) 0.0099(12) C13 0.0650(18) 0.0553(18) 0.0307(14) 0.0042(12) 0.0112(12) 0.0149(14) C14 0.0667(18) 0.0434(16) 0.0381(15) 0.0033(12) 0.0112(13) 0.0162(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C8 1.734(3) . ? O1 N4 1.218(3) . ? O2 N4 1.222(3) . ? N1 C1 1.352(3) . ? N1 N2 1.353(3) . ? N1 C9 1.425(3) . ? N2 N3 1.309(3) . ? N3 C2 1.360(3) . ? N4 C12 1.473(3) . ? C1 C2 1.365(3) . ? C1 H1 0.941(18) . ? C2 C3 1.478(3) . ? C3 C8 1.391(4) . ? C3 C4 1.402(4) . ? C4 C5 1.377(4) . ? C4 H4 0.99(3) . ? C5 C6 1.374(4) . ? C5 H5 0.92(3) . ? C6 C7 1.368(4) . ? C6 H6 0.97(3) . ? C7 C8 1.387(4) . ? C7 H7 0.89(3) . ? C9 C10 1.381(4) . ? C9 C14 1.389(4) . ? C10 C11 1.373(4) . ? C10 H10 0.93(3) . ? C11 C12 1.388(4) . ? C11 H11 0.91(3) . ? C12 C13 1.362(4) . ? C13 C14 1.381(4) . ? C13 H13 1.01(3) . ? C14 H14 0.93(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 110.5(2) . . ? C1 N1 C9 128.1(2) . . ? N2 N1 C9 121.4(2) . . ? N3 N2 N1 106.6(2) . . ? N2 N3 C2 110.0(2) . . ? O1 N4 O2 123.7(2) . . ? O1 N4 C12 118.1(2) . . ? O2 N4 C12 118.3(2) . . ? N1 C1 C2 105.3(2) . . ? N1 C1 H1 122(2) . . ? C2 C1 H1 132(2) . . ? N3 C2 C1 107.7(2) . . ? N3 C2 C3 120.3(2) . . ? C1 C2 C3 132.0(2) . . ? C8 C3 C4 116.4(2) . . ? C8 C3 C2 124.9(2) . . ? C4 C3 C2 118.7(2) . . ? C5 C4 C3 121.4(3) . . ? C5 C4 H4 122.2(17) . . ? C3 C4 H4 116.3(17) . . ? C6 C5 C4 120.5(3) . . ? C6 C5 H5 122.4(18) . . ? C4 C5 H5 117.1(18) . . ? C7 C6 C5 119.9(3) . . ? C7 C6 H6 116.0(19) . . ? C5 C6 H6 124.2(19) . . ? C6 C7 C8 119.6(3) . . ? C6 C7 H7 124(2) . . ? C8 C7 H7 117(2) . . ? C7 C8 C3 122.2(3) . . ? C7 C8 Cl1 115.9(2) . . ? C3 C8 Cl1 121.87(19) . . ? C10 C9 C14 121.2(2) . . ? C10 C9 N1 119.9(2) . . ? C14 C9 N1 118.9(2) . . ? C11 C10 C9 119.7(3) . . ? C11 C10 H10 118.1(17) . . ? C9 C10 H10 122.2(17) . . ? C10 C11 C12 118.6(3) . . ? C10 C11 H11 122.6(17) . . ? C12 C11 H11 118.7(17) . . ? C13 C12 C11 122.1(2) . . ? C13 C12 N4 119.8(2) . . ? C11 C12 N4 118.1(2) . . ? C12 C13 C14 119.5(3) . . ? C12 C13 H13 122.3(16) . . ? C14 C13 H13 118.1(16) . . ? C13 C14 C9 118.8(3) . . ? C13 C14 H14 118.8(18) . . ? C9 C14 H14 122.3(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 N3 0.1(3) . . . . ? C9 N1 N2 N3 179.2(2) . . . . ? N1 N2 N3 C2 -0.2(3) . . . . ? N2 N1 C1 C2 0.0(3) . . . . ? C9 N1 C1 C2 -179.0(2) . . . . ? N2 N3 C2 C1 0.2(3) . . . . ? N2 N3 C2 C3 -179.6(2) . . . . ? N1 C1 C2 N3 -0.1(3) . . . . ? N1 C1 C2 C3 179.7(2) . . . . ? N3 C2 C3 C8 -175.8(2) . . . . ? C1 C2 C3 C8 4.4(5) . . . . ? N3 C2 C3 C4 4.2(4) . . . . ? C1 C2 C3 C4 -175.6(3) . . . . ? C8 C3 C4 C5 -0.7(4) . . . . ? C2 C3 C4 C5 179.3(3) . . . . ? C3 C4 C5 C6 0.8(5) . . . . ? C4 C5 C6 C7 -0.9(5) . . . . ? C5 C6 C7 C8 0.9(4) . . . . ? C6 C7 C8 C3 -0.8(4) . . . . ? C6 C7 C8 Cl1 179.5(2) . . . . ? C4 C3 C8 C7 0.7(4) . . . . ? C2 C3 C8 C7 -179.3(2) . . . . ? C4 C3 C8 Cl1 -179.64(19) . . . . ? C2 C3 C8 Cl1 0.4(4) . . . . ? C1 N1 C9 C10 16.6(4) . . . . ? N2 N1 C9 C10 -162.4(2) . . . . ? C1 N1 C9 C14 -164.0(3) . . . . ? N2 N1 C9 C14 17.0(4) . . . . ? C14 C9 C10 C11 1.3(4) . . . . ? N1 C9 C10 C11 -179.3(2) . . . . ? C9 C10 C11 C12 -1.4(4) . . . . ? C10 C11 C12 C13 0.5(4) . . . . ? C10 C11 C12 N4 -179.8(3) . . . . ? O1 N4 C12 C13 0.7(4) . . . . ? O2 N4 C12 C13 -179.3(2) . . . . ? O1 N4 C12 C11 -179.0(2) . . . . ? O2 N4 C12 C11 1.0(4) . . . . ? C11 C12 C13 C14 0.5(4) . . . . ? N4 C12 C13 C14 -179.3(2) . . . . ? C12 C13 C14 C9 -0.6(4) . . . . ? C10 C9 C14 C13 -0.3(4) . . . . ? N1 C9 C14 C13 -179.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C6 H6 O2 0.97(3) 2.54(3) 3.486(4) 166(3) 1_564 C14 H14 O2 0.93(3) 2.51(3) 3.377(4) 155(2) 1_565 C5 H5 Cl1 0.92(3) 2.93(3) 3.487(3) 120(2) 1_565 C11 H11 N2 0.91(3) 2.57(3) 3.367(4) 147(2) 1_545 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.221 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 731512' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '4N3Cl.cif' data_4N3Cl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? 4-(4-Chlorophenyl)-1-(3-nitrophenyl)-1H-1,2,3-triazole ; _chemical_name_common ? _chemical_melting_point 222-223 _chemical_formula_moiety 'C14 H9 Cl N4 O2' _chemical_formula_sum 'C14 H9 Cl N4 O2' _chemical_formula_weight 300.70 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.587(8) _cell_length_b 13.601(14) _cell_length_c 13.338(13) _cell_angle_alpha 90.00 _cell_angle_beta 91.266(17) _cell_angle_gamma 90.00 _cell_volume 1376(2) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1392 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 22.66 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.287 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9265 _exptl_absorpt_correction_T_max 0.9746 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6269 _diffrn_reflns_av_R_equivalents 0.0784 _diffrn_reflns_av_sigmaI/netI 0.0932 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2422 _reflns_number_gt 1560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.1288P)^2^+1.2889P] 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_extinction_coef ? _refine_ls_number_reflns 2422 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1394 _refine_ls_R_factor_gt 0.1000 _refine_ls_wR_factor_ref 0.2781 _refine_ls_wR_factor_gt 0.2470 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.8403(3) 0.10577(13) 0.04545(16) 0.1079(9) Uani 1 1 d . . . O1 O 0.4645(8) 1.0011(4) 0.1752(4) 0.116(2) Uani 1 1 d . . . O2 O 0.4165(6) 0.9010(3) 0.2977(4) 0.0877(14) Uani 1 1 d . . . N1 N 0.7308(5) 0.6073(3) -0.0169(3) 0.0443(10) Uani 1 1 d . . . N2 N 0.7978(6) 0.6244(4) -0.1092(3) 0.0640(13) Uani 1 1 d . . . N3 N 0.8483(6) 0.5395(4) -0.1444(3) 0.0667(13) Uani 1 1 d . . . N4 N 0.4689(7) 0.9196(4) 0.2144(4) 0.0748(15) Uani 1 1 d . . . C1 C 0.7393(6) 0.5106(4) 0.0036(3) 0.0461(12) Uani 1 1 d . . . H1 H 0.7020 0.4796 0.0616 0.055 Uiso 1 1 calc R . . C2 C 0.8133(6) 0.4669(4) -0.0772(4) 0.0476(12) Uani 1 1 d . . . C3 C 0.8567(6) 0.3641(4) -0.0969(4) 0.0517(13) Uani 1 1 d . . . C4 C 0.9226(7) 0.3360(5) -0.1900(4) 0.0678(16) Uani 1 1 d . . . H4 H 0.9418 0.3835 -0.2387 0.081 Uiso 1 1 calc R . . C5 C 0.9592(8) 0.2389(6) -0.2103(5) 0.0786(19) Uani 1 1 d . . . H5 H 1.0000 0.2218 -0.2731 0.094 Uiso 1 1 calc R . . C6 C 0.9368(8) 0.1672(5) -0.1398(5) 0.0773(19) Uani 1 1 d . . . H6 H 0.9635 0.1019 -0.1536 0.093 Uiso 1 1 calc R . . C7 C 0.8729(7) 0.1944(4) -0.0470(5) 0.0682(16) Uani 1 1 d . . . C8 C 0.8318(7) 0.2917(4) -0.0244(4) 0.0580(14) Uani 1 1 d . . . H8 H 0.7885 0.3081 0.0381 0.070 Uiso 1 1 calc R . . C9 C 0.6650(6) 0.6866(3) 0.0414(3) 0.0421(11) Uani 1 1 d . . . C10 C 0.6042(6) 0.6681(4) 0.1378(3) 0.0513(13) Uani 1 1 d . . . H10 H 0.6063 0.6047 0.1638 0.062 Uiso 1 1 calc R . . C11 C 0.5410(6) 0.7453(4) 0.1939(4) 0.0547(14) Uani 1 1 d . . . H11 H 0.4998 0.7342 0.2580 0.066 Uiso 1 1 calc R . . C12 C 0.5395(7) 0.8379(4) 0.1543(4) 0.0557(13) Uani 1 1 d . . . C13 C 0.5994(7) 0.8572(4) 0.0583(4) 0.0628(15) Uani 1 1 d . . . H13 H 0.5960 0.9207 0.0323 0.075 Uiso 1 1 calc R . . C14 C 0.6642(7) 0.7797(4) 0.0023(4) 0.0592(14) Uani 1 1 d . . . H14 H 0.7069 0.7909 -0.0615 0.071 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 Cl1 0.150(2) 0.0600(12) 0.1128(16) 0.0047(10) -0.0257(13) 0.0142(11) O1 0.179(6) 0.059(3) 0.112(4) -0.017(3) 0.026(4) 0.025(3) O2 0.098(3) 0.095(3) 0.071(3) -0.031(3) 0.019(2) 0.010(3) N1 0.042(2) 0.051(3) 0.039(2) 0.0027(19) 0.0011(16) -0.0039(19) N2 0.081(3) 0.063(3) 0.049(2) 0.004(2) 0.021(2) 0.002(3) N3 0.080(3) 0.069(3) 0.052(3) -0.004(2) 0.022(2) -0.004(3) N4 0.076(3) 0.064(4) 0.084(4) -0.027(3) -0.006(3) 0.014(3) C1 0.042(3) 0.050(3) 0.047(3) 0.006(2) 0.012(2) -0.004(2) C2 0.038(3) 0.051(3) 0.054(3) -0.005(3) 0.002(2) -0.001(2) C3 0.036(2) 0.064(4) 0.056(3) -0.012(3) 0.003(2) 0.003(2) C4 0.061(3) 0.081(4) 0.062(3) -0.026(3) 0.009(3) 0.001(3) C5 0.068(4) 0.091(5) 0.077(4) -0.041(4) 0.008(3) 0.014(4) C6 0.069(4) 0.062(4) 0.100(5) -0.035(4) -0.014(4) 0.024(3) C7 0.062(3) 0.060(4) 0.082(4) -0.007(3) -0.025(3) 0.011(3) C8 0.055(3) 0.057(4) 0.062(3) -0.011(3) -0.002(2) 0.005(3) C9 0.041(2) 0.045(3) 0.040(2) -0.003(2) -0.0015(19) -0.004(2) C10 0.049(3) 0.057(3) 0.048(3) 0.005(2) 0.003(2) -0.006(2) C11 0.052(3) 0.066(4) 0.046(3) -0.013(3) 0.008(2) 0.003(3) C12 0.055(3) 0.052(3) 0.060(3) -0.005(3) -0.006(2) 0.002(3) C13 0.072(4) 0.046(3) 0.070(4) 0.003(3) 0.001(3) 0.002(3) C14 0.063(3) 0.062(4) 0.053(3) 0.008(3) 0.007(2) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C7 1.746(7) . ? O1 N4 1.226(7) . ? O2 N4 1.215(7) . ? N1 C1 1.344(6) . ? N1 N2 1.363(5) . ? N1 C9 1.427(6) . ? N2 N3 1.308(6) . ? N3 C2 1.364(7) . ? N4 C12 1.478(7) . ? C1 C2 1.363(6) . ? C1 H1 0.9300 . ? C2 C3 1.461(7) . ? C3 C8 1.396(7) . ? C3 C4 1.402(7) . ? C4 C5 1.378(9) . ? C4 H4 0.9300 . ? C5 C6 1.368(9) . ? C5 H5 0.9300 . ? C6 C7 1.389(9) . ? C6 H6 0.9300 . ? C7 C8 1.394(8) . ? C8 H8 0.9300 . ? C9 C14 1.369(7) . ? C9 C10 1.398(6) . ? C10 C11 1.380(7) . ? C10 H10 0.9300 . ? C11 C12 1.366(7) . ? C11 H11 0.9300 . ? C12 C13 1.393(7) . ? C13 C14 1.389(8) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 109.5(4) . . ? C1 N1 C9 130.1(4) . . ? N2 N1 C9 120.4(4) . . ? N3 N2 N1 106.9(4) . . ? N2 N3 C2 109.9(4) . . ? O2 N4 O1 124.9(5) . . ? O2 N4 C12 118.0(6) . . ? O1 N4 C12 117.1(6) . . ? N1 C1 C2 106.5(4) . . ? N1 C1 H1 126.8 . . ? C2 C1 H1 126.8 . . ? C1 C2 N3 107.1(5) . . ? C1 C2 C3 131.1(5) . . ? N3 C2 C3 121.8(5) . . ? C8 C3 C4 118.5(5) . . ? C8 C3 C2 121.1(5) . . ? C4 C3 C2 120.4(5) . . ? C5 C4 C3 120.8(6) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 121.4(6) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 118.2(6) . . ? C5 C6 H6 120.9 . . ? C7 C6 H6 120.9 . . ? C6 C7 C8 122.0(6) . . ? C6 C7 Cl1 120.2(5) . . ? C8 C7 Cl1 117.8(5) . . ? C7 C8 C3 119.1(5) . . ? C7 C8 H8 120.5 . . ? C3 C8 H8 120.5 . . ? C14 C9 C10 121.1(5) . . ? C14 C9 N1 119.4(4) . . ? C10 C9 N1 119.5(4) . . ? C11 C10 C9 119.2(5) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C12 C11 C10 119.4(5) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 122.0(5) . . ? C11 C12 N4 118.9(5) . . ? C13 C12 N4 119.1(5) . . ? C14 C13 C12 118.5(5) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C9 C14 C13 119.8(5) . . ? C9 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? 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 C1 N1 N2 N3 -0.6(5) . . . . ? C9 N1 N2 N3 179.6(4) . . . . ? N1 N2 N3 C2 0.8(6) . . . . ? N2 N1 C1 C2 0.1(5) . . . . ? C9 N1 C1 C2 179.9(4) . . . . ? N1 C1 C2 N3 0.3(5) . . . . ? N1 C1 C2 C3 179.3(5) . . . . ? N2 N3 C2 C1 -0.7(6) . . . . ? N2 N3 C2 C3 -179.8(4) . . . . ? C1 C2 C3 C8 -3.6(8) . . . . ? N3 C2 C3 C8 175.3(5) . . . . ? C1 C2 C3 C4 175.7(5) . . . . ? N3 C2 C3 C4 -5.4(7) . . . . ? C8 C3 C4 C5 1.1(8) . . . . ? C2 C3 C4 C5 -178.2(5) . . . . ? C3 C4 C5 C6 -1.6(9) . . . . ? C4 C5 C6 C7 1.0(9) . . . . ? C5 C6 C7 C8 0.0(9) . . . . ? C5 C6 C7 Cl1 179.6(5) . . . . ? C6 C7 C8 C3 -0.4(8) . . . . ? Cl1 C7 C8 C3 180.0(4) . . . . ? C4 C3 C8 C7 -0.1(7) . . . . ? C2 C3 C8 C7 179.2(4) . . . . ? C1 N1 C9 C14 -177.5(5) . . . . ? N2 N1 C9 C14 2.3(6) . . . . ? C1 N1 C9 C10 3.1(7) . . . . ? N2 N1 C9 C10 -177.1(4) . . . . ? C14 C9 C10 C11 0.5(7) . . . . ? N1 C9 C10 C11 179.9(4) . . . . ? C9 C10 C11 C12 -0.1(7) . . . . ? C10 C11 C12 C13 0.3(8) . . . . ? C10 C11 C12 N4 179.0(4) . . . . ? O2 N4 C12 C11 0.9(7) . . . . ? O1 N4 C12 C11 -177.8(6) . . . . ? O2 N4 C12 C13 179.6(5) . . . . ? O1 N4 C12 C13 1.0(8) . . . . ? C11 C12 C13 C14 -0.8(8) . . . . ? N4 C12 C13 C14 -179.5(5) . . . . ? C10 C9 C14 C13 -1.0(7) . . . . ? N1 C9 C14 C13 179.6(4) . . . . ? C12 C13 C14 C9 1.1(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 O2 0.93 2.36 3.283(7) 175.1 2_645 C10 H10 O1 0.93 2.63 3.423(7) 143.0 2_645 C5 H5 N2 0.93 2.58 3.438(7) 152.9 2_744 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.290 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 731513' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '4N4Cl.cif' data_4N4Cl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? 4-(4-Chlorophenyl)-1-(4-nitrophenyl)-1H-1,2,3-triazole ; _chemical_name_common ? _chemical_melting_point 246-248 _chemical_formula_moiety 'C14 H9 Cl N4 O2' _chemical_formula_sum 'C14 H9 Cl N4 O2' _chemical_formula_weight 300.70 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.954(7) _cell_length_b 13.263(11) _cell_length_c 12.684(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.559(14) _cell_angle_gamma 90.00 _cell_volume 1334(2) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2992 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 26.87 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8376 _exptl_absorpt_correction_T_max 0.9681 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9661 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2607 _reflns_number_gt 2080 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0567P)^2^+0.4485P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2607 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.10793(9) 0.00091(5) 1.13793(6) 0.0670(3) Uani 1 1 d . . . O1 O 0.4440(3) 1.01858(14) 0.83047(16) 0.0773(6) Uani 1 1 d . . . O2 O 0.5247(2) 0.92052(14) 0.70804(14) 0.0665(5) Uani 1 1 d . . . N1 N 0.2434(2) 0.59477(13) 1.01064(13) 0.0404(4) Uani 1 1 d . . . N2 N 0.1647(2) 0.60608(14) 1.10100(14) 0.0493(5) Uani 1 1 d . . . N3 N 0.1333(2) 0.51579(14) 1.13564(14) 0.0496(5) Uani 1 1 d . . . N4 N 0.4604(2) 0.93524(16) 0.79166(17) 0.0548(5) Uani 1 1 d . . . C1 C 0.2607(3) 0.49610(16) 0.98853(18) 0.0433(5) Uani 1 1 d . . . C2 C 0.1910(2) 0.44506(15) 1.06794(16) 0.0409(5) Uani 1 1 d . . . C3 C 0.1716(2) 0.33626(16) 1.08514(16) 0.0417(5) Uani 1 1 d . . . C4 C 0.1099(3) 0.29965(18) 1.17809(19) 0.0491(5) Uani 1 1 d . . . C5 C 0.0896(3) 0.19753(18) 1.19455(19) 0.0498(6) Uani 1 1 d . . . C6 C 0.1324(3) 0.13007(16) 1.11711(18) 0.0467(5) Uani 1 1 d . . . C7 C 0.1939(3) 0.16388(17) 1.02434(18) 0.0495(5) Uani 1 1 d . . . C8 C 0.2125(3) 0.26639(17) 1.00914(18) 0.0470(5) Uani 1 1 d . . . C9 C 0.2968(2) 0.68122(15) 0.95445(16) 0.0384(5) Uani 1 1 d . . . C10 C 0.3651(3) 0.66843(18) 0.85802(17) 0.0472(5) Uani 1 1 d . . . C11 C 0.4182(3) 0.75159(17) 0.80426(19) 0.0482(5) Uani 1 1 d . . . C12 C 0.4012(3) 0.84614(17) 0.84785(17) 0.0447(5) Uani 1 1 d . . . C13 C 0.3332(3) 0.85963(17) 0.94350(19) 0.0517(6) Uani 1 1 d . . . C14 C 0.2805(3) 0.77664(17) 0.99754(19) 0.0489(5) Uani 1 1 d . . . H1 H 0.309(3) 0.4755(17) 0.9339(19) 0.051(7) Uiso 1 1 d . . . H4 H 0.085(3) 0.3480(17) 1.2309(17) 0.047(6) Uiso 1 1 d . . . H5 H 0.051(3) 0.1722(19) 1.256(2) 0.061(7) Uiso 1 1 d . . . H7 H 0.226(3) 0.1146(17) 0.9691(17) 0.049(6) Uiso 1 1 d . . . H8 H 0.256(3) 0.2875(17) 0.9459(18) 0.048(6) Uiso 1 1 d . . . H10 H 0.374(3) 0.6041(19) 0.8284(18) 0.056(7) Uiso 1 1 d . . . H11 H 0.462(3) 0.7447(17) 0.7406(18) 0.053(7) Uiso 1 1 d . . . H13 H 0.325(3) 0.9240(19) 0.9707(19) 0.060(7) Uiso 1 1 d . . . H14 H 0.238(3) 0.7852(16) 1.0595(17) 0.041(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0869(5) 0.0428(3) 0.0739(5) 0.0075(3) 0.0231(4) -0.0071(3) O1 0.1067(16) 0.0432(11) 0.0844(14) 0.0045(9) 0.0217(12) -0.0122(10) O2 0.0725(12) 0.0685(12) 0.0605(11) 0.0167(9) 0.0184(9) -0.0092(9) N1 0.0444(9) 0.0393(9) 0.0386(9) -0.0002(7) 0.0099(7) 0.0026(7) N2 0.0614(12) 0.0452(10) 0.0437(10) 0.0000(8) 0.0199(9) 0.0029(9) N3 0.0606(12) 0.0447(11) 0.0458(11) 0.0040(8) 0.0180(9) -0.0002(9) N4 0.0567(12) 0.0516(12) 0.0562(12) 0.0117(10) 0.0047(10) -0.0061(9) C1 0.0491(12) 0.0403(11) 0.0420(12) -0.0036(10) 0.0130(10) 0.0005(9) C2 0.0409(11) 0.0420(12) 0.0401(11) 0.0018(9) 0.0062(9) 0.0026(9) C3 0.0386(11) 0.0432(11) 0.0435(12) 0.0049(9) 0.0053(9) -0.0005(9) C4 0.0550(13) 0.0478(13) 0.0461(13) 0.0009(10) 0.0142(10) 0.0005(10) C5 0.0545(13) 0.0521(14) 0.0444(13) 0.0090(11) 0.0140(10) -0.0037(10) C6 0.0492(12) 0.0389(11) 0.0524(13) 0.0075(10) 0.0069(10) -0.0035(9) C7 0.0591(14) 0.0413(12) 0.0494(13) -0.0010(10) 0.0133(11) -0.0007(10) C8 0.0533(13) 0.0472(12) 0.0420(12) 0.0043(10) 0.0127(10) -0.0026(10) C9 0.0394(11) 0.0382(11) 0.0380(11) 0.0004(8) 0.0058(8) -0.0001(8) C10 0.0580(14) 0.0408(12) 0.0442(12) -0.0051(10) 0.0130(10) 0.0007(10) C11 0.0569(14) 0.0502(14) 0.0390(12) 0.0010(10) 0.0124(10) -0.0015(10) C12 0.0469(12) 0.0435(12) 0.0438(12) 0.0074(9) 0.0037(9) -0.0027(9) C13 0.0621(15) 0.0374(12) 0.0569(14) -0.0032(11) 0.0136(11) 0.0002(11) C14 0.0628(15) 0.0431(12) 0.0429(12) -0.0024(10) 0.0174(11) 0.0008(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C6 1.746(3) . ? O1 N4 1.221(3) . ? O2 N4 1.229(3) . ? N1 C1 1.348(3) . ? N1 N2 1.357(2) . ? N1 C9 1.432(3) . ? N2 N3 1.306(3) . ? N3 C2 1.375(3) . ? N4 C12 1.476(3) . ? C1 C2 1.367(3) . ? C1 H1 0.86(2) . ? C2 C3 1.469(3) . ? C3 C8 1.394(3) . ? C3 C4 1.399(3) . ? C4 C5 1.382(4) . ? C4 H4 0.96(2) . ? C5 C6 1.391(3) . ? C5 H5 0.92(3) . ? C6 C7 1.384(3) . ? C7 C8 1.383(3) . ? C7 H7 1.01(2) . ? C8 H8 0.94(2) . ? C9 C10 1.388(3) . ? C9 C14 1.389(3) . ? C10 C11 1.380(3) . ? C10 H10 0.94(2) . ? C11 C12 1.381(3) . ? C11 H11 0.91(2) . ? C12 C13 1.379(3) . ? C13 C14 1.379(3) . ? C13 H13 0.93(3) . ? C14 H14 0.89(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 110.16(17) . . ? C1 N1 C9 129.39(18) . . ? N2 N1 C9 120.44(17) . . ? N3 N2 N1 107.21(17) . . ? N2 N3 C2 109.47(18) . . ? O1 N4 O2 123.8(2) . . ? O1 N4 C12 118.8(2) . . ? O2 N4 C12 117.4(2) . . ? N1 C1 C2 105.9(2) . . ? N1 C1 H1 122.2(16) . . ? C2 C1 H1 131.9(16) . . ? C1 C2 N3 107.3(2) . . ? C1 C2 C3 130.5(2) . . ? N3 C2 C3 122.22(19) . . ? C8 C3 C4 117.9(2) . . ? C8 C3 C2 121.13(19) . . ? C4 C3 C2 120.9(2) . . ? C5 C4 C3 121.4(2) . . ? C5 C4 H4 121.1(14) . . ? C3 C4 H4 117.6(14) . . ? C4 C5 C6 119.1(2) . . ? C4 C5 H5 122.4(16) . . ? C6 C5 H5 118.5(16) . . ? C7 C6 C5 121.0(2) . . ? C7 C6 Cl1 119.83(18) . . ? C5 C6 Cl1 119.20(18) . . ? C8 C7 C6 119.1(2) . . ? C8 C7 H7 120.4(13) . . ? C6 C7 H7 120.5(13) . . ? C7 C8 C3 121.6(2) . . ? C7 C8 H8 117.5(14) . . ? C3 C8 H8 120.9(14) . . ? C10 C9 C14 120.89(19) . . ? C10 C9 N1 119.55(19) . . ? C14 C9 N1 119.56(19) . . ? C11 C10 C9 119.6(2) . . ? C11 C10 H10 119.6(14) . . ? C9 C10 H10 120.8(15) . . ? C10 C11 C12 119.0(2) . . ? C10 C11 H11 120.8(15) . . ? C12 C11 H11 120.2(15) . . ? C13 C12 C11 121.8(2) . . ? C13 C12 N4 118.9(2) . . ? C11 C12 N4 119.2(2) . . ? C12 C13 C14 119.3(2) . . ? C12 C13 H13 119.6(16) . . ? C14 C13 H13 121.1(16) . . ? C13 C14 C9 119.4(2) . . ? C13 C14 H14 119.4(14) . . ? C9 C14 H14 121.3(14) . . ? 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 C1 N1 N2 N3 0.2(2) . . . . ? C9 N1 N2 N3 -178.97(17) . . . . ? N1 N2 N3 C2 -0.2(2) . . . . ? N2 N1 C1 C2 -0.2(2) . . . . ? C9 N1 C1 C2 178.91(19) . . . . ? N1 C1 C2 N3 0.1(2) . . . . ? N1 C1 C2 C3 179.1(2) . . . . ? N2 N3 C2 C1 0.0(2) . . . . ? N2 N3 C2 C3 -179.11(18) . . . . ? C1 C2 C3 C8 -6.7(3) . . . . ? N3 C2 C3 C8 172.2(2) . . . . ? C1 C2 C3 C4 173.9(2) . . . . ? N3 C2 C3 C4 -7.2(3) . . . . ? C8 C3 C4 C5 -0.1(3) . . . . ? C2 C3 C4 C5 179.3(2) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C4 C5 C6 C7 -0.3(3) . . . . ? C4 C5 C6 Cl1 179.66(17) . . . . ? C5 C6 C7 C8 -0.1(3) . . . . ? Cl1 C6 C7 C8 -179.99(18) . . . . ? C6 C7 C8 C3 0.3(3) . . . . ? C4 C3 C8 C7 -0.2(3) . . . . ? C2 C3 C8 C7 -179.7(2) . . . . ? C1 N1 C9 C10 5.9(3) . . . . ? N2 N1 C9 C10 -175.04(19) . . . . ? C1 N1 C9 C14 -173.6(2) . . . . ? N2 N1 C9 C14 5.4(3) . . . . ? C14 C9 C10 C11 0.2(3) . . . . ? N1 C9 C10 C11 -179.36(19) . . . . ? C9 C10 C11 C12 -0.3(3) . . . . ? C10 C11 C12 C13 0.2(3) . . . . ? C10 C11 C12 N4 178.9(2) . . . . ? O1 N4 C12 C13 -1.6(3) . . . . ? O2 N4 C12 C13 178.1(2) . . . . ? O1 N4 C12 C11 179.6(2) . . . . ? O2 N4 C12 C11 -0.8(3) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? N4 C12 C13 C14 -178.8(2) . . . . ? C12 C13 C14 C9 -0.1(4) . . . . ? C10 C9 C14 C13 0.0(3) . . . . ? N1 C9 C14 C13 179.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 O2 0.86(2) 2.43(3) 3.288(3) 174(2) 2_646 C10 H10 O2 0.94(2) 2.62(3) 3.521(4) 162.1(18) 2_646 C5 H5 N2 0.92(3) 2.74(3) 3.622(4) 160.9(19) 2_547 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.307 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 731514' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_2n2i #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1354970842.Comb_cif_iodo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 I N4 O2' _chemical_formula_sum 'C14 H9 I N4 O2' _chemical_formula_weight 392.15 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.4744(14) _cell_length_b 11.366(3) _cell_length_c 11.235(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.816(4) _cell_angle_gamma 90.00 _cell_volume 697.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 3267 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.86 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.867 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 2.305 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5535 _exptl_absorpt_correction_T_max 0.8264 _exptl_absorpt_process_details "bruker's sadabs" _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3495 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2268 _reflns_number_gt 2237 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Ortep32, mercury 2.4' _computing_publication_material 'SHELXTL, Platon' _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^)+(0.0370P)^2^+0.1422P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 2268 _refine_ls_number_parameters 194 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0743 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.4096(8) 0.6604(4) 0.2489(4) 0.0325(9) Uani 1 1 d . . . C2 C 0.2500(8) 0.6208(4) 0.3288(4) 0.0317(9) Uani 1 1 d . . . C3 C 0.2998(8) 0.5749(3) 0.4496(4) 0.0300(9) Uani 1 1 d . . . C4 C 0.4887(9) 0.4961(5) 0.4732(4) 0.0338(10) Uani 1 1 d . . . H4 H 0.5872 0.4743 0.4103 0.041 Uiso 1 1 calc R . . C5 C 0.5393(10) 0.4480(4) 0.5840(5) 0.0441(11) Uani 1 1 d . . . H5 H 0.6735 0.3955 0.5976 0.053 Uiso 1 1 calc R . . C6 C 0.3930(10) 0.4764(5) 0.6767(4) 0.0448(11) Uani 1 1 d . . . H6 H 0.4206 0.4398 0.7524 0.054 Uiso 1 1 calc R . . C7 C 0.2090(10) 0.5575(5) 0.6580(4) 0.0412(11) Uani 1 1 d . . . H7 H 0.1120 0.5781 0.7219 0.049 Uiso 1 1 calc R . . C8 C 0.1621(8) 0.6100(4) 0.5473(4) 0.0306(9) Uani 1 1 d . . . C9 C 0.3361(9) 0.7289(5) 0.0374(3) 0.0339(11) Uani 1 1 d . . . C10 C 0.5154(10) 0.6680(5) -0.0196(4) 0.0401(10) Uani 1 1 d . . . H10 H 0.5951 0.6022 0.0179 0.048 Uiso 1 1 calc R . . C11 C 0.5770(11) 0.7044(5) -0.1324(5) 0.0474(13) Uani 1 1 d . . . H11 H 0.7038 0.6653 -0.1705 0.057 Uiso 1 1 calc R . . C12 C 0.4552(11) 0.7964(5) -0.1884(5) 0.0520(13) Uani 1 1 d . . . H12 H 0.4950 0.8194 -0.2661 0.062 Uiso 1 1 calc R . . C13 C 0.2755(10) 0.8553(5) -0.1327(4) 0.0474(12) Uani 1 1 d . . . H13 H 0.1898 0.9182 -0.1725 0.057 Uiso 1 1 calc R . . C14 C 0.2191(9) 0.8234(4) -0.0188(4) 0.0359(10) Uani 1 1 d . . . H1 H 0.583(9) 0.671(4) 0.253(3) 0.019(10) Uiso 1 1 d . . . I1 I -0.08942(4) 0.74813(4) 0.53400(2) 0.04251(12) Uani 1 1 d . . . N1 N 0.2668(7) 0.6865(4) 0.1506(3) 0.0365(8) Uani 1 1 d . . . N2 N 0.0301(7) 0.6637(4) 0.1660(4) 0.0467(10) Uani 1 1 d . . . N3 N 0.0194(7) 0.6242(5) 0.2736(3) 0.0448(10) Uani 1 1 d . . . N4 N 0.0381(9) 0.9000(4) 0.0444(4) 0.0527(12) Uani 1 1 d . . . O1 O 0.0999(10) 0.9225(5) 0.1442(4) 0.0795(15) Uani 1 1 d . . . O2 O -0.1321(10) 0.9330(5) -0.0155(6) 0.0872(16) 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 0.025(2) 0.039(2) 0.034(2) -0.0017(18) 0.0024(16) -0.0014(18) C2 0.025(2) 0.038(2) 0.032(2) -0.0076(17) 0.0051(16) -0.0032(18) C3 0.028(2) 0.030(2) 0.032(2) -0.0023(17) 0.0021(17) -0.0094(17) C4 0.027(2) 0.034(2) 0.041(3) -0.006(3) 0.007(2) -0.0018(17) C5 0.038(3) 0.032(2) 0.061(3) 0.004(2) 0.000(2) 0.003(2) C6 0.050(3) 0.042(2) 0.042(3) 0.006(2) -0.003(2) 0.005(2) C7 0.045(3) 0.045(3) 0.034(2) 0.003(2) 0.0100(19) 0.001(2) C8 0.030(2) 0.030(2) 0.033(2) 0.0009(16) 0.0061(17) -0.0017(17) C9 0.0288(19) 0.044(4) 0.0287(18) -0.0006(18) 0.0000(14) -0.005(2) C10 0.038(3) 0.043(3) 0.039(2) -0.001(2) 0.0051(19) 0.007(2) C11 0.047(3) 0.056(3) 0.041(3) -0.003(2) 0.014(2) 0.002(2) C12 0.064(4) 0.058(3) 0.036(3) 0.003(2) 0.014(2) 0.005(3) C13 0.055(3) 0.043(3) 0.043(3) 0.008(2) -0.005(2) 0.004(2) C14 0.035(2) 0.031(2) 0.040(2) -0.0083(18) -0.0019(18) 0.0008(18) I1 0.03881(18) 0.03991(17) 0.04989(18) 0.00296(16) 0.01098(11) 0.00714(15) N1 0.0266(19) 0.050(2) 0.0327(19) 0.0005(17) 0.0026(15) 0.0005(17) N2 0.025(2) 0.075(3) 0.040(2) 0.000(2) -0.0013(16) -0.006(2) N3 0.0233(19) 0.075(3) 0.037(2) 0.0023(19) 0.0047(15) -0.008(2) N4 0.058(3) 0.038(2) 0.060(3) 0.005(2) -0.017(2) -0.014(2) O1 0.079(3) 0.087(3) 0.073(3) -0.040(3) 0.005(3) 0.027(3) O2 0.067(3) 0.075(4) 0.120(4) 0.000(3) 0.009(3) 0.033(3) _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 N1 1.342(6) . ? C1 C2 1.370(6) . ? C1 H1 0.96(5) . ? C2 N3 1.369(6) . ? C2 C3 1.462(6) . ? C3 C4 1.381(7) . ? C3 C8 1.429(6) . ? C4 C5 1.371(8) . ? C4 H4 0.9500 . ? C5 C6 1.393(7) . ? C5 H5 0.9500 . ? C6 C7 1.371(8) . ? C6 H6 0.9500 . ? C7 C8 1.388(6) . ? C7 H7 0.9500 . ? C8 I1 2.088(4) . ? C9 C14 1.382(7) . ? C9 C10 1.392(7) . ? C9 N1 1.435(6) . ? C10 C11 1.396(7) . ? C10 H10 0.9500 . ? C11 C12 1.370(8) . ? C11 H11 0.9500 . ? C12 C13 1.375(8) . ? C12 H12 0.9500 . ? C13 C14 1.384(7) . ? C13 H13 0.9500 . ? C14 N4 1.529(7) . ? N1 N2 1.344(6) . ? N2 N3 1.295(6) . ? N4 O2 1.174(8) . ? N4 O1 1.178(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 104.5(4) . . ? N1 C1 H1 123(2) . . ? C2 C1 H1 133(2) . . ? N3 C2 C1 107.6(4) . . ? N3 C2 C3 122.6(4) . . ? C1 C2 C3 129.6(4) . . ? C4 C3 C8 117.4(4) . . ? C4 C3 C2 120.0(4) . . ? C8 C3 C2 122.6(4) . . ? C5 C4 C3 122.5(4) . . ? C5 C4 H4 118.8 . . ? C3 C4 H4 118.8 . . ? C4 C5 C6 119.6(5) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 119.7(5) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 121.1(5) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C7 C8 C3 119.6(4) . . ? C7 C8 I1 118.0(3) . . ? C3 C8 I1 122.2(3) . . ? C14 C9 C10 119.7(4) . . ? C14 C9 N1 121.7(4) . . ? C10 C9 N1 118.5(4) . . ? C9 C10 C11 119.4(5) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 120.2(5) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.3(5) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 120.2(5) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C9 C14 C13 120.1(4) . . ? C9 C14 N4 121.7(4) . . ? C13 C14 N4 118.1(4) . . ? C1 N1 N2 111.4(4) . . ? C1 N1 C9 129.0(4) . . ? N2 N1 C9 119.5(4) . . ? N3 N2 N1 106.9(4) . . ? N2 N3 C2 109.6(4) . . ? O2 N4 O1 130.0(6) . . ? O2 N4 C14 115.5(5) . . ? O1 N4 C14 114.3(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 N1 C1 C2 N3 0.5(5) . . . . ? N1 C1 C2 C3 177.1(4) . . . . ? N3 C2 C3 C4 132.4(5) . . . . ? C1 C2 C3 C4 -43.7(7) . . . . ? N3 C2 C3 C8 -48.7(6) . . . . ? C1 C2 C3 C8 135.2(5) . . . . ? C8 C3 C4 C5 2.8(7) . . . . ? C2 C3 C4 C5 -178.3(4) . . . . ? C3 C4 C5 C6 1.7(7) . . . . ? C4 C5 C6 C7 -3.9(8) . . . . ? C5 C6 C7 C8 1.5(8) . . . . ? C6 C7 C8 C3 3.1(7) . . . . ? C6 C7 C8 I1 -171.9(4) . . . . ? C4 C3 C8 C7 -5.1(6) . . . . ? C2 C3 C8 C7 176.0(4) . . . . ? C4 C3 C8 I1 169.7(3) . . . . ? C2 C3 C8 I1 -9.3(5) . . . . ? C14 C9 C10 C11 0.9(8) . . . . ? N1 C9 C10 C11 176.9(4) . . . . ? C9 C10 C11 C12 -2.6(8) . . . . ? C10 C11 C12 C13 1.6(8) . . . . ? C11 C12 C13 C14 1.0(8) . . . . ? C10 C9 C14 C13 1.7(7) . . . . ? N1 C9 C14 C13 -174.2(4) . . . . ? C10 C9 C14 N4 -174.3(4) . . . . ? N1 C9 C14 N4 9.7(6) . . . . ? C12 C13 C14 C9 -2.7(8) . . . . ? C12 C13 C14 N4 173.5(5) . . . . ? C2 C1 N1 N2 -0.7(5) . . . . ? C2 C1 N1 C9 -178.2(5) . . . . ? C14 C9 N1 C1 -132.2(5) . . . . ? C10 C9 N1 C1 51.9(7) . . . . ? C14 C9 N1 N2 50.5(6) . . . . ? C10 C9 N1 N2 -125.5(5) . . . . ? C1 N1 N2 N3 0.5(6) . . . . ? C9 N1 N2 N3 178.3(4) . . . . ? N1 N2 N3 C2 -0.2(6) . . . . ? C1 C2 N3 N2 -0.2(6) . . . . ? C3 C2 N3 N2 -177.1(4) . . . . ? C9 C14 N4 O2 -142.7(5) . . . . ? C13 C14 N4 O2 41.2(7) . . . . ? C9 C14 N4 O1 41.8(7) . . . . ? C13 C14 N4 O1 -134.3(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 N3 0.96(5) 2.44(5) 3.357(6) 160(3) 1_655 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.564 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.094 _database_code_depnum_ccdc_archive 'CCDC 914828' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #===END data_2n3i #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1354970842.Comb_cif_iodo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 I N4 O2' _chemical_formula_sum 'C14 H9 I N4 O2' _chemical_formula_weight 392.15 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.4462(15) _cell_length_b 7.2925(11) _cell_length_c 20.875(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.379(2) _cell_angle_gamma 90.00 _cell_volume 1429.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 4301 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 28.20 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.823 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 2.250 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4308 _exptl_absorpt_correction_T_max 0.8657 _exptl_absorpt_process_details "bruker's sadabs" _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6915 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2522 _reflns_number_gt 2308 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0456P)^2^+0.5044P] 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_extinction_coef ? _refine_ls_number_reflns 2522 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0828 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.5290(3) 0.7988(4) 0.26193(14) 0.0353(7) Uani 1 1 d . . . H1 H 0.5272 0.8988 0.2327 0.042 Uiso 1 1 calc R . . C2 C 0.4587(3) 0.6349(4) 0.25302(13) 0.0324(6) Uani 1 1 d . . . C3 C 0.3646(3) 0.5697(4) 0.19699(13) 0.0328(6) Uani 1 1 d . . . C4 C 0.3294(3) 0.3847(4) 0.18947(15) 0.0382(6) Uani 1 1 d . . . H4 H 0.3631 0.2998 0.2222 0.046 Uiso 1 1 calc R . . C5 C 0.2463(4) 0.3235(4) 0.13528(18) 0.0447(8) Uani 1 1 d . . . H5 H 0.2242 0.1968 0.1305 0.054 Uiso 1 1 calc R . . C6 C 0.1950(3) 0.4469(5) 0.08758(15) 0.0440(7) Uani 1 1 d . . . H6 H 0.1381 0.4050 0.0500 0.053 Uiso 1 1 calc R . . C7 C 0.2272(3) 0.6312(4) 0.09515(14) 0.0371(6) Uani 1 1 d . . . C8 C 0.3103(3) 0.6943(4) 0.14986(15) 0.0350(7) Uani 1 1 d . . . H8 H 0.3300 0.8215 0.1551 0.042 Uiso 1 1 calc R . . C9 C 0.6921(3) 0.9200(4) 0.35508(13) 0.0308(6) Uani 1 1 d . . . C10 C 0.6432(3) 1.0974(4) 0.36301(15) 0.0384(7) Uani 1 1 d . . . H10 H 0.5510 1.1323 0.3441 0.046 Uiso 1 1 calc R . . C11 C 0.7290(4) 1.2226(4) 0.39838(17) 0.0426(7) Uani 1 1 d . . . H11 H 0.6959 1.3445 0.4028 0.051 Uiso 1 1 calc R . . C12 C 0.8618(4) 1.1740(4) 0.42744(16) 0.0411(7) Uani 1 1 d . . . H12 H 0.9187 1.2604 0.4528 0.049 Uiso 1 1 calc R . . C13 C 0.9115(3) 0.9982(4) 0.41935(15) 0.0373(7) Uani 1 1 d . . . H13 H 1.0032 0.9632 0.4389 0.045 Uiso 1 1 calc R . . C14 C 0.8277(3) 0.8740(4) 0.38291(14) 0.0325(6) Uani 1 1 d . . . I1 I 0.14836(2) 0.81856(3) 0.023941(10) 0.05158(13) Uani 1 1 d . . . N1 N 0.6011(3) 0.7875(3) 0.32107(11) 0.0325(5) Uani 1 1 d . . . N2 N 0.5780(3) 0.6234(3) 0.34870(12) 0.0374(6) Uani 1 1 d . . . N3 N 0.4924(3) 0.5301(3) 0.30720(12) 0.0378(6) Uani 1 1 d . . . N4 N 0.8907(3) 0.6960(3) 0.37052(18) 0.0487(8) Uani 1 1 d . . . O1 O 0.8704(3) 0.6363(4) 0.31576(17) 0.0743(9) Uani 1 1 d . . . O2 O 0.9639(3) 0.6213(4) 0.41443(17) 0.0720(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 0.0406(16) 0.0362(16) 0.0277(15) 0.0052(11) -0.0026(13) -0.0050(12) C2 0.0312(14) 0.0367(14) 0.0286(15) 0.0023(12) 0.0011(11) -0.0007(12) C3 0.0312(14) 0.0388(15) 0.0281(14) -0.0032(12) 0.0016(11) -0.0019(12) C4 0.0364(15) 0.0399(16) 0.0380(16) 0.0004(13) 0.0023(13) -0.0040(13) C5 0.0379(17) 0.0436(18) 0.052(2) -0.0086(14) 0.0036(15) -0.0099(13) C6 0.0344(15) 0.058(2) 0.0383(17) -0.0141(15) -0.0023(13) -0.0075(14) C7 0.0294(14) 0.0505(17) 0.0303(15) -0.0016(13) -0.0016(12) 0.0025(13) C8 0.0368(16) 0.0366(16) 0.0305(15) -0.0034(11) -0.0009(12) -0.0003(11) C9 0.0330(14) 0.0327(15) 0.0261(14) 0.0017(11) 0.0005(11) -0.0039(11) C10 0.0391(16) 0.0345(16) 0.0402(17) 0.0065(13) -0.0025(13) 0.0049(13) C11 0.0509(19) 0.0282(15) 0.0482(19) -0.0022(13) 0.0030(15) 0.0032(13) C12 0.0493(19) 0.0350(16) 0.0383(18) -0.0046(12) 0.0012(15) -0.0063(13) C13 0.0341(15) 0.0382(16) 0.0387(17) 0.0001(13) 0.0000(12) -0.0028(12) C14 0.0317(14) 0.0302(13) 0.0360(16) -0.0014(12) 0.0055(12) 0.0006(11) I1 0.05116(18) 0.0665(2) 0.03382(17) 0.00392(9) -0.00968(11) 0.00668(9) N1 0.0373(13) 0.0299(12) 0.0289(13) 0.0033(9) -0.0029(10) -0.0040(9) N2 0.0456(14) 0.0317(12) 0.0324(13) 0.0044(11) -0.0068(11) -0.0039(11) N3 0.0441(14) 0.0329(12) 0.0342(13) 0.0032(10) -0.0053(11) -0.0035(11) N4 0.0338(14) 0.0347(15) 0.078(2) -0.0120(14) 0.0085(15) -0.0007(11) O1 0.0596(17) 0.0679(17) 0.098(2) -0.0452(17) 0.0188(16) 0.0040(14) O2 0.0505(15) 0.0423(13) 0.119(3) 0.0051(16) -0.0084(16) 0.0128(12) _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 N1 1.345(4) . ? C1 C2 1.370(4) . ? C1 H1 0.9500 . ? C2 N3 1.372(4) . ? C2 C3 1.468(4) . ? C3 C4 1.394(4) . ? C3 C8 1.395(4) . ? C4 C5 1.378(5) . ? C4 H4 0.9500 . ? C5 C6 1.389(5) . ? C5 H5 0.9500 . ? C6 C7 1.383(5) . ? C6 H6 0.9500 . ? C7 C8 1.390(4) . ? C7 I1 2.094(3) . ? C8 H8 0.9500 . ? C9 C14 1.388(4) . ? C9 C10 1.389(4) . ? C9 N1 1.428(4) . ? C10 C11 1.380(5) . ? C10 H10 0.9500 . ? C11 C12 1.378(5) . ? C11 H11 0.9500 . ? C12 C13 1.382(4) . ? C12 H12 0.9500 . ? C13 C14 1.375(4) . ? C13 H13 0.9500 . ? C14 N4 1.463(4) . ? N1 N2 1.357(3) . ? N2 N3 1.308(3) . ? N4 O2 1.214(4) . ? N4 O1 1.218(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 105.0(2) . . ? N1 C1 H1 127.5 . . ? C2 C1 H1 127.5 . . ? C1 C2 N3 108.0(3) . . ? C1 C2 C3 129.2(3) . . ? N3 C2 C3 122.7(3) . . ? C4 C3 C8 119.1(3) . . ? C4 C3 C2 121.3(3) . . ? C8 C3 C2 119.6(3) . . ? C5 C4 C3 120.9(3) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 119.5(3) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 120.8(3) . . ? C6 C7 I1 119.8(2) . . ? C8 C7 I1 119.4(2) . . ? C7 C8 C3 119.6(3) . . ? C7 C8 H8 120.2 . . ? C3 C8 H8 120.2 . . ? C14 C9 C10 118.6(3) . . ? C14 C9 N1 121.4(2) . . ? C10 C9 N1 120.0(3) . . ? C11 C10 C9 119.8(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 121.1(3) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 119.3(3) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 119.7(3) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C9 121.3(3) . . ? C13 C14 N4 117.5(3) . . ? C9 C14 N4 121.0(3) . . ? C1 N1 N2 110.8(2) . . ? C1 N1 C9 129.1(2) . . ? N2 N1 C9 120.1(2) . . ? N3 N2 N1 107.1(2) . . ? N2 N3 C2 109.0(2) . . ? O2 N4 O1 124.4(3) . . ? O2 N4 C14 118.3(3) . . ? O1 N4 C14 117.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N3 -0.5(3) . . . . ? N1 C1 C2 C3 -179.4(3) . . . . ? C1 C2 C3 C4 164.3(3) . . . . ? N3 C2 C3 C4 -14.5(4) . . . . ? C1 C2 C3 C8 -15.0(5) . . . . ? N3 C2 C3 C8 166.2(3) . . . . ? C8 C3 C4 C5 2.3(4) . . . . ? C2 C3 C4 C5 -177.0(3) . . . . ? C3 C4 C5 C6 -0.8(5) . . . . ? C4 C5 C6 C7 -0.4(5) . . . . ? C5 C6 C7 C8 0.0(5) . . . . ? C5 C6 C7 I1 -179.3(2) . . . . ? C6 C7 C8 C3 1.5(5) . . . . ? I1 C7 C8 C3 -179.1(2) . . . . ? C4 C3 C8 C7 -2.6(4) . . . . ? C2 C3 C8 C7 176.7(3) . . . . ? C14 C9 C10 C11 -0.5(4) . . . . ? N1 C9 C10 C11 177.1(3) . . . . ? C9 C10 C11 C12 -1.5(5) . . . . ? C10 C11 C12 C13 2.0(5) . . . . ? C11 C12 C13 C14 -0.5(5) . . . . ? C12 C13 C14 C9 -1.5(5) . . . . ? C12 C13 C14 N4 174.0(3) . . . . ? C10 C9 C14 C13 2.0(4) . . . . ? N1 C9 C14 C13 -175.5(3) . . . . ? C10 C9 C14 N4 -173.4(3) . . . . ? N1 C9 C14 N4 9.1(4) . . . . ? C2 C1 N1 N2 0.0(3) . . . . ? C2 C1 N1 C9 -179.8(3) . . . . ? C14 C9 N1 C1 -129.4(3) . . . . ? C10 C9 N1 C1 53.1(4) . . . . ? C14 C9 N1 N2 50.7(4) . . . . ? C10 C9 N1 N2 -126.8(3) . . . . ? C1 N1 N2 N3 0.4(3) . . . . ? C9 N1 N2 N3 -179.7(3) . . . . ? N1 N2 N3 C2 -0.8(3) . . . . ? C1 C2 N3 N2 0.8(3) . . . . ? C3 C2 N3 N2 179.8(3) . . . . ? C13 C14 N4 O2 41.5(4) . . . . ? C9 C14 N4 O2 -142.9(3) . . . . ? C13 C14 N4 O1 -135.6(3) . . . . ? C9 C14 N4 O1 39.9(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 O1 0.95 2.27 3.152(4) 153.1 2_655 C11 H11 N2 0.95 2.52 3.365(4) 147.6 1_565 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.682 _refine_diff_density_min -0.739 _refine_diff_density_rms 0.106 _database_code_depnum_ccdc_archive 'CCDC 914829' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #===END data_2n4i #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1354970842.Comb_cif_iodo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 I N4 O2' _chemical_formula_sum 'C14 H9 I N4 O2' _chemical_formula_weight 392.15 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 5.431(2) _cell_length_b 21.767(9) _cell_length_c 12.162(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.372(7) _cell_angle_gamma 90.00 _cell_volume 1409.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 5522 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 28.19 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.848 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 2.282 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3512 _exptl_absorpt_correction_T_max 0.5109 _exptl_absorpt_process_details "bruker's sadabs" _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6903 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2478 _reflns_number_gt 2319 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0359P)^2^+2.5220P] 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_extinction_coef ? _refine_ls_number_reflns 2478 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0952 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.6116(6) 0.63209(15) 0.7209(3) 0.0283(7) Uani 1 1 d . . . H1 H 0.7837 0.6381 0.7183 0.034 Uiso 1 1 calc R . . C2 C 0.4254(6) 0.61012(16) 0.6370(3) 0.0288(7) Uani 1 1 d . . . C3 C 0.4298(6) 0.59217(15) 0.5205(3) 0.0288(7) Uani 1 1 d . . . C4 C 0.2364(7) 0.55525(17) 0.4633(3) 0.0362(8) Uani 1 1 d . . . H4 H 0.1062 0.5423 0.5000 0.043 Uiso 1 1 calc R . . C5 C 0.2316(8) 0.53723(17) 0.3535(4) 0.0405(9) Uani 1 1 d . . . H5 H 0.1008 0.5114 0.3158 0.049 Uiso 1 1 calc R . . C6 C 0.4171(7) 0.55694(16) 0.2998(3) 0.0357(8) Uani 1 1 d . . . C7 C 0.6099(7) 0.59400(18) 0.3545(3) 0.0385(8) Uani 1 1 d . . . H7 H 0.7374 0.6076 0.3168 0.046 Uiso 1 1 calc R . . C8 C 0.6155(7) 0.61118(17) 0.4650(3) 0.0361(8) Uani 1 1 d . . . H8 H 0.7486 0.6363 0.5030 0.043 Uiso 1 1 calc R . . C9 C 0.5929(6) 0.66773(16) 0.9165(3) 0.0295(7) Uani 1 1 d . . . C10 C 0.8043(7) 0.64278(17) 0.9832(3) 0.0357(8) Uani 1 1 d . . . H10 H 0.8961 0.6115 0.9546 0.043 Uiso 1 1 calc R . . C11 C 0.8821(7) 0.66363(19) 1.0926(3) 0.0432(9) Uani 1 1 d . . . H11 H 1.0322 0.6479 1.1373 0.052 Uiso 1 1 calc R . . C12 C 0.7434(8) 0.70691(18) 1.1367(3) 0.0432(9) Uani 1 1 d . . . H12 H 0.7934 0.7193 1.2128 0.052 Uiso 1 1 calc R . . C13 C 0.5322(7) 0.73221(17) 1.0705(3) 0.0378(8) Uani 1 1 d . . . H13 H 0.4345 0.7616 1.1006 0.045 Uiso 1 1 calc R . . C14 C 0.4647(6) 0.71418(15) 0.9597(3) 0.0307(7) Uani 1 1 d . . . I1 I 0.40398(6) 0.529924(13) 0.13238(2) 0.05324(15) Uani 1 1 d . . . N1 N 0.4975(5) 0.64335(13) 0.8077(2) 0.0303(6) Uani 1 1 d . . . N2 N 0.2503(5) 0.62876(16) 0.7801(3) 0.0416(8) Uani 1 1 d . . . N3 N 0.2083(5) 0.60877(16) 0.6768(3) 0.0393(7) Uani 1 1 d . . . N4 N 0.2660(6) 0.75013(14) 0.8877(3) 0.0373(7) Uani 1 1 d . . . O1 O 0.2946(6) 0.76210(16) 0.7929(2) 0.0547(8) Uani 1 1 d . . . O2 O 0.0907(5) 0.76853(15) 0.9277(3) 0.0542(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 0.0235(15) 0.0323(17) 0.0298(17) -0.0011(14) 0.0071(13) 0.0010(13) C2 0.0274(16) 0.0293(17) 0.0309(18) -0.0027(13) 0.0084(13) 0.0005(13) C3 0.0288(16) 0.0274(16) 0.0304(17) -0.0012(13) 0.0063(13) 0.0036(13) C4 0.0381(19) 0.0360(19) 0.037(2) -0.0083(15) 0.0127(15) -0.0072(15) C5 0.044(2) 0.038(2) 0.040(2) -0.0110(16) 0.0090(17) -0.0056(16) C6 0.049(2) 0.0300(17) 0.0282(18) -0.0027(14) 0.0088(15) 0.0075(15) C7 0.041(2) 0.041(2) 0.036(2) 0.0011(16) 0.0150(16) -0.0006(15) C8 0.0331(18) 0.0406(19) 0.0342(19) -0.0035(16) 0.0060(14) -0.0029(15) C9 0.0274(16) 0.0337(17) 0.0269(17) -0.0035(14) 0.0041(13) -0.0070(13) C10 0.0334(18) 0.0345(18) 0.039(2) -0.0013(15) 0.0064(15) -0.0003(15) C11 0.040(2) 0.046(2) 0.038(2) 0.0028(18) -0.0053(16) -0.0030(17) C12 0.054(2) 0.044(2) 0.0281(18) -0.0039(16) -0.0012(16) -0.0067(18) C13 0.047(2) 0.0342(18) 0.0324(19) -0.0062(15) 0.0083(16) -0.0013(16) C14 0.0310(16) 0.0326(18) 0.0285(17) 0.0012(14) 0.0060(13) -0.0035(13) I1 0.0794(3) 0.0502(2) 0.03318(19) -0.00950(11) 0.01840(15) 0.00318(13) N1 0.0205(13) 0.0382(15) 0.0320(15) -0.0064(12) 0.0048(11) -0.0025(11) N2 0.0272(15) 0.061(2) 0.0380(17) -0.0177(15) 0.0093(13) -0.0080(14) N3 0.0276(15) 0.056(2) 0.0351(17) -0.0141(15) 0.0094(12) -0.0065(13) N4 0.0343(16) 0.0377(16) 0.0393(18) -0.0016(13) 0.0057(13) 0.0017(13) O1 0.0591(18) 0.069(2) 0.0353(16) 0.0149(14) 0.0084(13) 0.0144(15) O2 0.0460(16) 0.0596(18) 0.0589(19) 0.0019(15) 0.0148(14) 0.0176(14) _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 N1 1.348(4) . ? C1 C2 1.373(5) . ? C1 H1 0.9500 . ? C2 N3 1.360(4) . ? C2 C3 1.475(5) . ? C3 C8 1.383(5) . ? C3 C4 1.395(5) . ? C4 C5 1.387(6) . ? C4 H4 0.9500 . ? C5 C6 1.373(6) . ? C5 H5 0.9500 . ? C6 C7 1.384(5) . ? C6 I1 2.107(4) . ? C7 C8 1.390(5) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.380(5) . ? C9 C14 1.389(5) . ? C9 N1 1.425(4) . ? C10 C11 1.390(5) . ? C10 H10 0.9500 . ? C11 C12 1.379(6) . ? C11 H11 0.9500 . ? C12 C13 1.380(6) . ? C12 H12 0.9500 . ? C13 C14 1.381(5) . ? C13 H13 0.9500 . ? C14 N4 1.473(4) . ? N1 N2 1.355(4) . ? N2 N3 1.306(4) . ? N4 O2 1.219(4) . ? N4 O1 1.222(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 105.1(3) . . ? N1 C1 H1 127.5 . . ? C2 C1 H1 127.5 . . ? N3 C2 C1 107.8(3) . . ? N3 C2 C3 121.0(3) . . ? C1 C2 C3 131.1(3) . . ? C8 C3 C4 118.7(3) . . ? C8 C3 C2 122.7(3) . . ? C4 C3 C2 118.6(3) . . ? C5 C4 C3 120.8(4) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 119.6(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 120.6(3) . . ? C5 C6 I1 119.0(3) . . ? C7 C6 I1 120.4(3) . . ? C6 C7 C8 119.5(3) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C3 C8 C7 120.8(3) . . ? C3 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C10 C9 C14 119.0(3) . . ? C10 C9 N1 120.5(3) . . ? C14 C9 N1 120.3(3) . . ? C9 C10 C11 119.7(4) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C11 C10 120.6(3) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 120.0(4) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 119.1(4) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C13 C14 C9 121.3(3) . . ? C13 C14 N4 116.8(3) . . ? C9 C14 N4 121.6(3) . . ? C1 N1 N2 110.5(3) . . ? C1 N1 C9 131.0(3) . . ? N2 N1 C9 118.5(3) . . ? N3 N2 N1 107.0(3) . . ? N2 N3 C2 109.6(3) . . ? O2 N4 O1 124.1(3) . . ? O2 N4 C14 118.4(3) . . ? O1 N4 C14 117.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N3 -0.3(4) . . . . ? N1 C1 C2 C3 177.1(3) . . . . ? N3 C2 C3 C8 158.0(4) . . . . ? C1 C2 C3 C8 -19.2(6) . . . . ? N3 C2 C3 C4 -21.0(5) . . . . ? C1 C2 C3 C4 161.8(4) . . . . ? C8 C3 C4 C5 0.8(5) . . . . ? C2 C3 C4 C5 179.9(3) . . . . ? C3 C4 C5 C6 -1.2(6) . . . . ? C4 C5 C6 C7 0.7(6) . . . . ? C4 C5 C6 I1 -179.3(3) . . . . ? C5 C6 C7 C8 0.2(6) . . . . ? I1 C6 C7 C8 -179.8(3) . . . . ? C4 C3 C8 C7 0.1(5) . . . . ? C2 C3 C8 C7 -178.9(3) . . . . ? C6 C7 C8 C3 -0.6(6) . . . . ? C14 C9 C10 C11 1.2(5) . . . . ? N1 C9 C10 C11 -174.5(3) . . . . ? C9 C10 C11 C12 3.1(6) . . . . ? C10 C11 C12 C13 -3.3(6) . . . . ? C11 C12 C13 C14 -0.9(6) . . . . ? C12 C13 C14 C9 5.3(6) . . . . ? C12 C13 C14 N4 -169.5(3) . . . . ? C10 C9 C14 C13 -5.4(5) . . . . ? N1 C9 C14 C13 170.3(3) . . . . ? C10 C9 C14 N4 169.1(3) . . . . ? N1 C9 C14 N4 -15.2(5) . . . . ? C2 C1 N1 N2 0.4(4) . . . . ? C2 C1 N1 C9 -178.5(3) . . . . ? C10 C9 N1 C1 -51.9(5) . . . . ? C14 C9 N1 C1 132.5(4) . . . . ? C10 C9 N1 N2 129.3(4) . . . . ? C14 C9 N1 N2 -46.4(5) . . . . ? C1 N1 N2 N3 -0.3(4) . . . . ? C9 N1 N2 N3 178.8(3) . . . . ? N1 N2 N3 C2 0.1(4) . . . . ? C1 C2 N3 N2 0.1(4) . . . . ? C3 C2 N3 N2 -177.6(3) . . . . ? C13 C14 N4 O2 -38.0(5) . . . . ? C9 C14 N4 O2 147.3(4) . . . . ? C13 C14 N4 O1 138.6(4) . . . . ? C9 C14 N4 O1 -36.2(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 N3 0.95 2.54 3.425(4) 155.6 1_655 C1 H1 N2 0.95 2.51 3.402(5) 157.2 1_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.625 _refine_diff_density_min -1.320 _refine_diff_density_rms 0.109 _database_code_depnum_ccdc_archive 'CCDC 914830' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #===END data_3n2i #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1354970842.Comb_cif_iodo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 I N4 O2' _chemical_formula_sum 'C14 H9 I N4 O2' _chemical_formula_weight 392.15 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9450(14) _cell_length_b 15.147(2) _cell_length_c 10.2164(17) _cell_angle_alpha 90.00 _cell_angle_beta 92.321(3) _cell_angle_gamma 90.00 _cell_volume 1383.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 3921 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 28.25 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.883 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 2.325 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5288 _exptl_absorpt_correction_T_max 0.7427 _exptl_absorpt_process_details "bruker's sadabs" _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6877 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2431 _reflns_number_gt 2184 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0423P)^2^+1.0464P] 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_extinction_coef ? _refine_ls_number_reflns 2431 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0805 _refine_ls_wR_factor_gt 0.0781 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.7998(3) -0.00989(19) 0.5374(3) 0.0394(6) Uani 1 1 d . . . H1 H 0.8182 0.0359 0.4766 0.047 Uiso 1 1 calc R . . C2 C 0.8651(3) -0.02070(19) 0.6589(3) 0.0387(6) Uani 1 1 d . . . C3 C 0.9827(3) 0.0275(2) 0.7366(3) 0.0417(7) Uani 1 1 d . . . C4 C 1.0613(4) -0.0214(3) 0.8333(3) 0.0533(8) Uani 1 1 d . . . H4 H 1.0435 -0.0830 0.8401 0.064 Uiso 1 1 calc R . . C5 C 1.1645(4) 0.0183(3) 0.9191(4) 0.0663(10) Uani 1 1 d . . . H5 H 1.2162 -0.0161 0.9842 0.080 Uiso 1 1 calc R . . C6 C 1.1923(4) 0.1068(3) 0.9105(4) 0.0714(12) Uani 1 1 d . . . H6 H 1.2603 0.1343 0.9717 0.086 Uiso 1 1 calc R . . C7 C 1.1222(4) 0.1557(3) 0.8137(4) 0.0621(10) Uani 1 1 d . . . H7 H 1.1444 0.2168 0.8061 0.075 Uiso 1 1 calc R . . C8 C 1.0186(4) 0.1168(2) 0.7264(3) 0.0474(7) Uani 1 1 d . . . C9 C 0.6059(3) -0.10020(19) 0.4121(3) 0.0363(6) Uani 1 1 d . . . C10 C 0.5615(3) -0.03591(19) 0.3225(3) 0.0423(7) Uani 1 1 d . . . H10 H 0.5938 0.0234 0.3345 0.051 Uiso 1 1 calc R . . C11 C 0.4701(4) -0.0584(2) 0.2155(3) 0.0489(8) Uani 1 1 d . . . H11 H 0.4401 -0.0144 0.1537 0.059 Uiso 1 1 calc R . . C12 C 0.4218(4) -0.1445(2) 0.1977(3) 0.0467(7) Uani 1 1 d . . . H12 H 0.3591 -0.1605 0.1242 0.056 Uiso 1 1 calc R . . C13 C 0.4674(4) -0.20645(18) 0.2899(3) 0.0406(7) Uani 1 1 d . . . C14 C 0.5584(3) -0.18641(19) 0.3980(3) 0.0396(7) Uani 1 1 d . . . H14 H 0.5873 -0.2303 0.4604 0.048 Uiso 1 1 calc R . . I1 I 0.92825(3) 0.199026(14) 0.57733(3) 0.06373(13) Uani 1 1 d . . . N1 N 0.7028(3) -0.07822(15) 0.5216(2) 0.0366(5) Uani 1 1 d . . . N2 N 0.7063(3) -0.12896(17) 0.6307(2) 0.0461(6) Uani 1 1 d . . . N3 N 0.8051(3) -0.09451(17) 0.7132(2) 0.0468(6) Uani 1 1 d . . . N4 N 0.4154(3) -0.29794(17) 0.2748(3) 0.0497(7) Uani 1 1 d . . . O1 O 0.4456(3) -0.35042(15) 0.3627(2) 0.0655(7) Uani 1 1 d . . . O2 O 0.3448(3) -0.31738(16) 0.1743(3) 0.0695(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 0.0455(16) 0.0313(14) 0.0415(15) -0.0004(12) 0.0043(13) -0.0044(12) C2 0.0398(16) 0.0341(15) 0.0425(15) -0.0053(12) 0.0039(13) -0.0021(12) C3 0.0400(16) 0.0433(16) 0.0423(16) -0.0113(13) 0.0067(13) -0.0040(13) C4 0.0521(19) 0.060(2) 0.0473(18) -0.0040(15) -0.0020(15) -0.0038(16) C5 0.055(2) 0.090(3) 0.053(2) -0.0059(19) -0.0088(17) -0.009(2) C6 0.054(2) 0.093(3) 0.067(2) -0.033(2) -0.0002(19) -0.015(2) C7 0.054(2) 0.058(2) 0.076(2) -0.0293(19) 0.0131(19) -0.0142(18) C8 0.0459(17) 0.0437(17) 0.0531(18) -0.0118(14) 0.0095(14) -0.0020(14) C9 0.0378(15) 0.0318(14) 0.0392(15) -0.0044(11) 0.0017(12) 0.0017(12) C10 0.0489(17) 0.0291(14) 0.0486(17) 0.0009(12) -0.0014(14) 0.0004(12) C11 0.058(2) 0.0418(17) 0.0458(17) 0.0058(13) -0.0072(15) 0.0052(14) C12 0.0497(18) 0.0475(18) 0.0420(16) -0.0050(14) -0.0089(14) 0.0001(14) C13 0.0456(17) 0.0314(15) 0.0448(16) -0.0067(12) 0.0014(13) -0.0007(12) C14 0.0473(18) 0.0306(14) 0.0406(15) -0.0019(11) -0.0013(13) 0.0020(12) I1 0.0715(2) 0.03546(16) 0.0844(2) -0.00031(10) 0.00640(14) -0.00178(10) N1 0.0422(13) 0.0293(12) 0.0380(12) -0.0012(9) -0.0016(10) -0.0010(10) N2 0.0564(16) 0.0352(13) 0.0459(14) 0.0070(11) -0.0082(12) -0.0063(12) N3 0.0536(15) 0.0406(14) 0.0452(14) 0.0013(11) -0.0084(12) -0.0082(12) N4 0.0565(17) 0.0387(15) 0.0534(16) -0.0115(12) -0.0023(14) -0.0038(12) O1 0.101(2) 0.0367(13) 0.0584(14) -0.0012(11) -0.0072(14) -0.0124(13) O2 0.086(2) 0.0488(14) 0.0715(17) -0.0168(12) -0.0285(15) -0.0068(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.356(4) . ? C1 C2 1.360(4) . ? C1 H1 0.9500 . ? C2 N3 1.368(4) . ? C2 C3 1.484(4) . ? C3 C8 1.394(4) . ? C3 C4 1.401(5) . ? C4 C5 1.385(5) . ? C4 H4 0.9500 . ? C5 C6 1.368(6) . ? C5 H5 0.9500 . ? C6 C7 1.367(6) . ? C6 H6 0.9500 . ? C7 C8 1.391(5) . ? C7 H7 0.9500 . ? C8 I1 2.103(4) . ? C9 C14 1.379(4) . ? C9 C10 1.383(4) . ? C9 N1 1.427(4) . ? C10 C11 1.381(5) . ? C10 H10 0.9500 . ? C11 C12 1.385(5) . ? C11 H11 0.9500 . ? C12 C13 1.379(4) . ? C12 H12 0.9500 . ? C13 C14 1.380(4) . ? C13 N4 1.468(4) . ? C14 H14 0.9500 . ? N1 N2 1.353(3) . ? N2 N3 1.305(4) . ? N4 O2 1.220(4) . ? N4 O1 1.221(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 105.5(2) . . ? N1 C1 H1 127.3 . . ? C2 C1 H1 127.3 . . ? C1 C2 N3 107.9(3) . . ? C1 C2 C3 134.3(3) . . ? N3 C2 C3 117.8(3) . . ? C8 C3 C4 117.1(3) . . ? C8 C3 C2 126.7(3) . . ? C4 C3 C2 116.2(3) . . ? C5 C4 C3 121.3(4) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C6 C5 C4 120.2(4) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C7 C6 C5 119.9(4) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 120.6(4) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C8 C3 120.8(3) . . ? C7 C8 I1 116.1(3) . . ? C3 C8 I1 123.1(2) . . ? C14 C9 C10 121.3(3) . . ? C14 C9 N1 118.5(3) . . ? C10 C9 N1 120.2(3) . . ? C11 C10 C9 119.7(3) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.6(3) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 118.0(3) . . ? C13 C12 H12 121.0 . . ? C11 C12 H12 121.0 . . ? C12 C13 C14 123.1(3) . . ? C12 C13 N4 119.1(3) . . ? C14 C13 N4 117.8(3) . . ? C9 C14 C13 117.5(3) . . ? C9 C14 H14 121.3 . . ? C13 C14 H14 121.3 . . ? N2 N1 C1 110.0(2) . . ? N2 N1 C9 120.4(2) . . ? C1 N1 C9 129.6(2) . . ? N3 N2 N1 107.3(2) . . ? N2 N3 C2 109.4(2) . . ? O2 N4 O1 123.6(3) . . ? O2 N4 C13 117.8(3) . . ? O1 N4 C13 118.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N3 -0.5(3) . . . . ? N1 C1 C2 C3 178.0(3) . . . . ? C1 C2 C3 C8 27.2(5) . . . . ? N3 C2 C3 C8 -154.4(3) . . . . ? C1 C2 C3 C4 -155.3(3) . . . . ? N3 C2 C3 C4 23.1(4) . . . . ? C8 C3 C4 C5 3.3(5) . . . . ? C2 C3 C4 C5 -174.5(3) . . . . ? C3 C4 C5 C6 -0.3(6) . . . . ? C4 C5 C6 C7 -2.5(6) . . . . ? C5 C6 C7 C8 2.2(6) . . . . ? C6 C7 C8 C3 0.9(5) . . . . ? C6 C7 C8 I1 -177.1(3) . . . . ? C4 C3 C8 C7 -3.5(5) . . . . ? C2 C3 C8 C7 174.0(3) . . . . ? C4 C3 C8 I1 174.3(2) . . . . ? C2 C3 C8 I1 -8.2(4) . . . . ? C14 C9 C10 C11 -1.1(5) . . . . ? N1 C9 C10 C11 178.7(3) . . . . ? C9 C10 C11 C12 0.4(5) . . . . ? C10 C11 C12 C13 0.2(5) . . . . ? C11 C12 C13 C14 -0.1(5) . . . . ? C11 C12 C13 N4 178.8(3) . . . . ? C10 C9 C14 C13 1.2(4) . . . . ? N1 C9 C14 C13 -178.6(3) . . . . ? C12 C13 C14 C9 -0.6(5) . . . . ? N4 C13 C14 C9 -179.5(3) . . . . ? C2 C1 N1 N2 0.9(3) . . . . ? C2 C1 N1 C9 -179.2(3) . . . . ? C14 C9 N1 N2 -23.1(4) . . . . ? C10 C9 N1 N2 157.1(3) . . . . ? C14 C9 N1 C1 157.1(3) . . . . ? C10 C9 N1 C1 -22.7(4) . . . . ? C1 N1 N2 N3 -1.0(3) . . . . ? C9 N1 N2 N3 179.2(2) . . . . ? N1 N2 N3 C2 0.7(3) . . . . ? C1 C2 N3 N2 -0.1(3) . . . . ? C3 C2 N3 N2 -178.9(3) . . . . ? C12 C13 N4 O2 6.8(5) . . . . ? C14 C13 N4 O2 -174.3(3) . . . . ? C12 C13 N4 O1 -173.7(3) . . . . ? C14 C13 N4 O1 5.2(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C10 H10 O2 0.95 2.48 3.414(4) 169.4 2_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.570 _refine_diff_density_min -0.603 _refine_diff_density_rms 0.078 _database_code_depnum_ccdc_archive 'CCDC 914831' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #===END data_3n3i #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1354970842.Comb_cif_iodo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 I N4 O2' _chemical_formula_sum 'C14 H9 I N4 O2' _chemical_formula_weight 392.15 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 0.0000 0.0000 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.566(4) _cell_length_b 8.694(4) _cell_length_c 10.011(5) _cell_angle_alpha 85.508(7) _cell_angle_beta 71.441(7) _cell_angle_gamma 72.559(7) _cell_volume 674.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 3560 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.25 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.932 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 2.385 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7088 _exptl_absorpt_correction_T_max 0.9212 _exptl_absorpt_process_details "bruker's sadabs" _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6490 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2367 _reflns_number_gt 2237 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0409P)^2^+0.0659P] 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_extinction_coef ? _refine_ls_number_reflns 2367 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0781 _refine_ls_wR_factor_gt 0.0769 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 0.63197(3) 1.22359(3) -0.52521(2) 0.03789(12) Uani 1 1 d . . . O1 O -0.2594(4) 0.6954(4) 0.6678(3) 0.0493(7) Uani 1 1 d . . . O2 O -0.1143(4) 0.8674(4) 0.6094(3) 0.0475(7) Uani 1 1 d . . . N1 N 0.1365(3) 0.8195(3) 0.0823(3) 0.0277(6) Uani 1 1 d . . . N2 N 0.1818(4) 0.7702(4) -0.0533(3) 0.0390(8) Uani 1 1 d . . . N3 N 0.2631(4) 0.8671(4) -0.1319(3) 0.0396(8) Uani 1 1 d . . . N4 N -0.1647(4) 0.7613(4) 0.5813(3) 0.0337(7) Uani 1 1 d . . . C1 C 0.1911(4) 0.9485(4) 0.0889(4) 0.0302(8) Uani 1 1 d . . . H1 H 0.1767 1.0059 0.1709 0.036 Uiso 1 1 calc R . . C2 C 0.2713(4) 0.9786(4) -0.0477(4) 0.0294(7) Uani 1 1 d . . . C3 C 0.3539(4) 1.1054(4) -0.1054(4) 0.0285(7) Uani 1 1 d . . . C4 C 0.3451(5) 1.2282(4) -0.0196(4) 0.0346(8) Uani 1 1 d . . . H4 H 0.2880 1.2291 0.0788 0.042 Uiso 1 1 calc R . . C5 C 0.4199(5) 1.3495(4) -0.0778(4) 0.0376(9) Uani 1 1 d . . . H5 H 0.4125 1.4330 -0.0183 0.045 Uiso 1 1 calc R . . C6 C 0.5052(5) 1.3511(4) -0.2213(4) 0.0361(9) Uani 1 1 d . . . H6 H 0.5553 1.4347 -0.2603 0.043 Uiso 1 1 calc R . . C7 C 0.5151(4) 1.2282(4) -0.3055(4) 0.0302(8) Uani 1 1 d . . . C8 C 0.4404(4) 1.1055(4) -0.2500(4) 0.0298(7) Uani 1 1 d . . . H8 H 0.4482 1.0223 -0.3100 0.036 Uiso 1 1 calc R . . C9 C 0.0423(4) 0.7374(4) 0.1933(3) 0.0255(7) Uani 1 1 d . . . C10 C 0.0054(5) 0.6036(4) 0.1584(4) 0.0331(8) Uani 1 1 d . . . H10 H 0.0460 0.5667 0.0631 0.040 Uiso 1 1 calc R . . C11 C -0.0905(5) 0.5236(4) 0.2624(4) 0.0337(8) Uani 1 1 d . . . H11 H -0.1167 0.4329 0.2382 0.040 Uiso 1 1 calc R . . C12 C -0.1480(4) 0.5761(4) 0.4013(4) 0.0310(8) Uani 1 1 d . . . H12 H -0.2140 0.5228 0.4736 0.037 Uiso 1 1 calc R . . C13 C -0.1062(5) 0.7089(4) 0.4319(4) 0.0289(8) Uani 1 1 d . . . C14 C -0.0116(4) 0.7908(4) 0.3315(4) 0.0283(7) Uani 1 1 d . . . H14 H 0.0158 0.8807 0.3562 0.034 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 0.04115(18) 0.03924(18) 0.03203(18) 0.00313(11) -0.00349(12) -0.01888(12) O1 0.0527(17) 0.070(2) 0.0253(14) 0.0020(14) -0.0022(13) -0.0293(16) O2 0.0634(19) 0.0514(17) 0.0345(16) -0.0079(13) -0.0147(14) -0.0245(15) N1 0.0334(16) 0.0306(15) 0.0197(14) -0.0025(12) -0.0061(12) -0.0118(13) N2 0.058(2) 0.0390(17) 0.0215(16) -0.0033(13) -0.0011(14) -0.0269(16) N3 0.057(2) 0.0396(18) 0.0227(17) -0.0047(14) -0.0043(15) -0.0223(16) N4 0.0347(16) 0.0392(17) 0.0270(16) -0.0006(13) -0.0091(13) -0.0107(14) C1 0.037(2) 0.0328(19) 0.0241(18) -0.0024(14) -0.0071(15) -0.0176(16) C2 0.0286(18) 0.0319(18) 0.0289(19) -0.0003(14) -0.0091(15) -0.0101(15) C3 0.0304(18) 0.0287(17) 0.0280(19) 0.0004(14) -0.0113(15) -0.0086(14) C4 0.037(2) 0.040(2) 0.028(2) -0.0033(16) -0.0079(16) -0.0145(16) C5 0.043(2) 0.037(2) 0.037(2) -0.0094(16) -0.0121(18) -0.0153(17) C6 0.040(2) 0.033(2) 0.042(2) 0.0024(16) -0.0159(18) -0.0176(16) C7 0.0285(18) 0.0332(19) 0.0286(19) 0.0021(15) -0.0077(15) -0.0101(15) C8 0.0321(18) 0.0278(17) 0.0309(19) -0.0011(14) -0.0080(15) -0.0120(14) C9 0.0270(17) 0.0279(17) 0.0210(17) 0.0001(13) -0.0059(14) -0.0088(14) C10 0.039(2) 0.037(2) 0.0259(19) -0.0049(15) -0.0086(16) -0.0151(16) C11 0.038(2) 0.0297(18) 0.036(2) -0.0025(15) -0.0098(16) -0.0148(16) C12 0.0285(18) 0.0368(19) 0.0282(19) 0.0072(15) -0.0095(15) -0.0111(15) C13 0.0296(18) 0.0325(19) 0.0257(19) -0.0003(15) -0.0089(15) -0.0102(15) C14 0.0318(18) 0.0282(17) 0.0251(18) -0.0015(14) -0.0071(15) -0.0103(14) _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 C7 2.104(4) . ? O1 N4 1.221(4) . ? O2 N4 1.214(4) . ? N1 C1 1.352(4) . ? N1 N2 1.354(4) . ? N1 C9 1.431(4) . ? N2 N3 1.309(4) . ? N3 C2 1.364(4) . ? N4 C13 1.479(5) . ? C1 C2 1.365(5) . ? C1 H1 0.9500 . ? C2 C3 1.469(5) . ? C3 C4 1.391(5) . ? C3 C8 1.401(5) . ? C4 C5 1.390(5) . ? C4 H4 0.9500 . ? C5 C6 1.390(6) . ? C5 H5 0.9500 . ? C6 C7 1.379(5) . ? C6 H6 0.9500 . ? C7 C8 1.395(5) . ? C8 H8 0.9500 . ? C9 C14 1.382(5) . ? C9 C10 1.388(5) . ? C10 C11 1.389(5) . ? C10 H10 0.9500 . ? C11 C12 1.383(5) . ? C11 H11 0.9500 . ? C12 C13 1.389(5) . ? C12 H12 0.9500 . ? C13 C14 1.374(5) . ? C14 H14 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 110.2(3) . . ? C1 N1 C9 129.7(3) . . ? N2 N1 C9 120.1(3) . . ? N3 N2 N1 107.3(3) . . ? N2 N3 C2 109.2(3) . . ? O2 N4 O1 124.4(3) . . ? O2 N4 C13 117.3(3) . . ? O1 N4 C13 118.3(3) . . ? N1 C1 C2 105.2(3) . . ? N1 C1 H1 127.4 . . ? C2 C1 H1 127.4 . . ? C1 C2 N3 108.1(3) . . ? C1 C2 C3 129.7(3) . . ? N3 C2 C3 122.2(3) . . ? C4 C3 C8 119.0(3) . . ? C4 C3 C2 121.3(3) . . ? C8 C3 C2 119.6(3) . . ? C5 C4 C3 120.1(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 121.3(3) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C7 C6 C5 118.3(3) . . ? C7 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? C6 C7 C8 121.5(3) . . ? C6 C7 I1 121.6(3) . . ? C8 C7 I1 116.8(3) . . ? C7 C8 C3 119.7(3) . . ? C7 C8 H8 120.1 . . ? C3 C8 H8 120.1 . . ? C14 C9 C10 121.0(3) . . ? C14 C9 N1 120.7(3) . . ? C10 C9 N1 118.3(3) . . ? C9 C10 C11 120.1(3) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 118.0(3) . . ? C11 C12 H12 121.0 . . ? C13 C12 H12 121.0 . . ? C14 C13 C12 123.4(3) . . ? C14 C13 N4 119.1(3) . . ? C12 C13 N4 117.5(3) . . ? C13 C14 C9 117.4(3) . . ? C13 C14 H14 121.3 . . ? C9 C14 H14 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 C1 N1 N2 N3 -0.4(4) . . . . ? C9 N1 N2 N3 178.9(3) . . . . ? N1 N2 N3 C2 0.2(4) . . . . ? N2 N1 C1 C2 0.3(4) . . . . ? C9 N1 C1 C2 -178.9(3) . . . . ? N1 C1 C2 N3 -0.2(4) . . . . ? N1 C1 C2 C3 179.2(3) . . . . ? N2 N3 C2 C1 0.0(4) . . . . ? N2 N3 C2 C3 -179.5(3) . . . . ? C1 C2 C3 C4 -6.2(6) . . . . ? N3 C2 C3 C4 173.1(3) . . . . ? C1 C2 C3 C8 175.1(3) . . . . ? N3 C2 C3 C8 -5.6(5) . . . . ? C8 C3 C4 C5 0.7(5) . . . . ? C2 C3 C4 C5 -178.0(3) . . . . ? C3 C4 C5 C6 -0.3(6) . . . . ? C4 C5 C6 C7 -0.4(6) . . . . ? C5 C6 C7 C8 0.7(5) . . . . ? C5 C6 C7 I1 177.4(3) . . . . ? C6 C7 C8 C3 -0.4(5) . . . . ? I1 C7 C8 C3 -177.2(2) . . . . ? C4 C3 C8 C7 -0.3(5) . . . . ? C2 C3 C8 C7 178.3(3) . . . . ? C1 N1 C9 C14 2.1(5) . . . . ? N2 N1 C9 C14 -177.0(3) . . . . ? C1 N1 C9 C10 -178.3(3) . . . . ? N2 N1 C9 C10 2.5(5) . . . . ? C14 C9 C10 C11 1.6(5) . . . . ? N1 C9 C10 C11 -177.9(3) . . . . ? C9 C10 C11 C12 -0.7(5) . . . . ? C10 C11 C12 C13 -0.2(5) . . . . ? C11 C12 C13 C14 0.2(5) . . . . ? C11 C12 C13 N4 -178.5(3) . . . . ? O2 N4 C13 C14 -5.6(5) . . . . ? O1 N4 C13 C14 174.5(3) . . . . ? O2 N4 C13 C12 173.2(3) . . . . ? O1 N4 C13 C12 -6.7(5) . . . . ? C12 C13 C14 C9 0.6(5) . . . . ? N4 C13 C14 C9 179.4(3) . . . . ? C10 C9 C14 C13 -1.6(5) . . . . ? N1 C9 C14 C13 178.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 O2 0.95 2.37 3.314(4) 172.8 2_576 C4 H4 O1 0.95 2.59 3.437(5) 149.1 2_576 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.800 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 914832' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #===END data_3n4i #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1354970842.Comb_cif_iodo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 I N4 O2' _chemical_formula_sum 'C14 H9 I N4 O2' _chemical_formula_weight 392.15 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 0.0000 0.0000 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.587(4) _cell_length_b 8.310(4) _cell_length_c 12.755(6) _cell_angle_alpha 95.053(7) _cell_angle_beta 100.946(7) _cell_angle_gamma 116.761(7) _cell_volume 691.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 2833 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 23.18 _exptl_crystal_description 'thin plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.885 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 2.327 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5797 _exptl_absorpt_correction_T_max 0.9726 _exptl_absorpt_process_details "bruker's sadabs" _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6575 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2413 _reflns_number_gt 2204 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0542P)^2^+0.3497P] 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_extinction_coef ? _refine_ls_number_reflns 2413 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1014 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.63495(5) 1.30907(5) 0.90316(3) 0.04833(17) Uani 1 1 d . . . O1 O 0.0406(6) -0.3104(5) 0.2967(3) 0.0573(10) Uani 1 1 d . . . O2 O -0.1371(7) -0.3791(6) 0.1312(4) 0.0671(12) Uani 1 1 d . . . N1 N 0.1864(6) 0.3256(5) 0.4398(3) 0.0330(9) Uani 1 1 d . . . N2 N 0.2586(7) 0.2717(6) 0.5285(4) 0.0481(11) Uani 1 1 d . . . N3 N 0.3349(7) 0.4081(6) 0.6108(4) 0.0477(11) Uani 1 1 d . . . N4 N -0.0372(7) -0.2712(6) 0.2174(4) 0.0459(11) Uani 1 1 d . . . C1 C 0.2207(7) 0.5003(6) 0.4689(4) 0.0384(11) Uani 1 1 d . . . H1 H 0.1869 0.5714 0.4226 0.046 Uiso 1 1 calc R . . C2 C 0.3128(7) 0.5531(7) 0.5773(4) 0.0374(11) Uani 1 1 d . . . C3 C 0.3877(7) 0.7273(7) 0.6525(4) 0.0365(11) Uani 1 1 d . . . C4 C 0.4628(8) 0.7465(7) 0.7636(4) 0.0418(12) Uani 1 1 d . . . H4 H 0.4663 0.6453 0.7914 0.050 Uiso 1 1 calc R . . C5 C 0.5327(8) 0.9118(7) 0.8346(4) 0.0427(12) Uani 1 1 d . . . H5 H 0.5846 0.9236 0.9103 0.051 Uiso 1 1 calc R . . C6 C 0.5266(8) 1.0591(7) 0.7946(4) 0.0392(11) Uani 1 1 d . . . C7 C 0.4495(8) 1.0425(7) 0.6846(4) 0.0426(12) Uani 1 1 d . . . H7 H 0.4435 1.1432 0.6575 0.051 Uiso 1 1 calc R . . C8 C 0.3811(8) 0.8774(7) 0.6145(4) 0.0420(12) Uani 1 1 d . . . H8 H 0.3286 0.8661 0.5389 0.050 Uiso 1 1 calc R . . C9 C 0.1012(7) 0.2069(6) 0.3357(4) 0.0341(11) Uani 1 1 d . . . C10 C 0.0464(8) 0.2686(7) 0.2435(4) 0.0415(12) Uani 1 1 d . . . H10 H 0.0659 0.3906 0.2495 0.050 Uiso 1 1 calc R . . C11 C -0.0358(8) 0.1527(7) 0.1439(4) 0.0454(13) Uani 1 1 d . . . H11 H -0.0724 0.1959 0.0812 0.054 Uiso 1 1 calc R . . C12 C -0.0668(8) -0.0256(7) 0.1323(4) 0.0414(12) Uani 1 1 d . . . H12 H -0.1250 -0.1061 0.0631 0.050 Uiso 1 1 calc R . . C13 C -0.0089(7) -0.0824(7) 0.2267(4) 0.0387(11) Uani 1 1 d . . . C14 C 0.0732(7) 0.0278(7) 0.3284(4) 0.0360(11) Uani 1 1 d . . . H14 H 0.1094 -0.0157 0.3912 0.043 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 0.0524(3) 0.0399(2) 0.0488(3) 0.00584(16) 0.01088(17) 0.02012(18) O1 0.074(3) 0.045(2) 0.069(3) 0.020(2) 0.020(2) 0.040(2) O2 0.078(3) 0.048(2) 0.072(3) -0.005(2) 0.011(2) 0.033(2) N1 0.039(2) 0.033(2) 0.034(2) 0.0098(17) 0.0118(17) 0.0219(18) N2 0.070(3) 0.042(2) 0.046(3) 0.015(2) 0.013(2) 0.037(2) N3 0.065(3) 0.049(3) 0.041(2) 0.012(2) 0.010(2) 0.038(2) N4 0.047(3) 0.039(2) 0.060(3) 0.008(2) 0.018(2) 0.027(2) C1 0.039(3) 0.028(2) 0.049(3) 0.012(2) 0.007(2) 0.017(2) C2 0.039(3) 0.038(3) 0.045(3) 0.016(2) 0.016(2) 0.023(2) C3 0.036(3) 0.038(3) 0.039(3) 0.012(2) 0.011(2) 0.020(2) C4 0.043(3) 0.043(3) 0.046(3) 0.020(2) 0.010(2) 0.025(2) C5 0.041(3) 0.048(3) 0.040(3) 0.010(2) 0.008(2) 0.023(2) C6 0.043(3) 0.038(3) 0.037(3) 0.007(2) 0.015(2) 0.019(2) C7 0.049(3) 0.038(3) 0.047(3) 0.018(2) 0.011(2) 0.026(2) C8 0.049(3) 0.041(3) 0.041(3) 0.013(2) 0.010(2) 0.025(3) C9 0.030(2) 0.034(3) 0.043(3) 0.015(2) 0.014(2) 0.017(2) C10 0.045(3) 0.033(3) 0.051(3) 0.009(2) 0.007(2) 0.025(2) C11 0.052(3) 0.048(3) 0.044(3) 0.016(2) 0.007(2) 0.032(3) C12 0.041(3) 0.042(3) 0.039(3) 0.002(2) 0.009(2) 0.019(2) C13 0.037(3) 0.036(3) 0.055(3) 0.016(2) 0.020(2) 0.023(2) C14 0.044(3) 0.037(3) 0.038(3) 0.022(2) 0.019(2) 0.023(2) _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 C6 2.105(5) . ? O1 N4 1.217(6) . ? O2 N4 1.219(6) . ? N1 C1 1.357(6) . ? N1 N2 1.363(6) . ? N1 C9 1.422(6) . ? N2 N3 1.299(6) . ? N3 C2 1.382(6) . ? N4 C13 1.475(6) . ? C1 C2 1.358(7) . ? C1 H1 0.9500 . ? C2 C3 1.465(7) . ? C3 C4 1.389(7) . ? C3 C8 1.396(7) . ? C4 C5 1.389(7) . ? C4 H4 0.9500 . ? C5 C6 1.383(7) . ? C5 H5 0.9500 . ? C6 C7 1.382(7) . ? C7 C8 1.385(8) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.391(7) . ? C9 C14 1.397(7) . ? C10 C11 1.368(7) . ? C10 H10 0.9500 . ? C11 C12 1.381(7) . ? C11 H11 0.9500 . ? C12 C13 1.397(7) . ? C12 H12 0.9500 . ? C13 C14 1.372(7) . ? C14 H14 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 109.5(4) . . ? C1 N1 C9 130.0(4) . . ? N2 N1 C9 120.4(4) . . ? N3 N2 N1 107.4(4) . . ? N2 N3 C2 109.6(4) . . ? O1 N4 O2 123.7(5) . . ? O1 N4 C13 117.9(5) . . ? O2 N4 C13 118.4(5) . . ? N1 C1 C2 106.2(4) . . ? N1 C1 H1 126.9 . . ? C2 C1 H1 126.9 . . ? C1 C2 N3 107.2(4) . . ? C1 C2 C3 130.9(4) . . ? N3 C2 C3 121.9(4) . . ? C4 C3 C8 118.2(5) . . ? C4 C3 C2 121.1(4) . . ? C8 C3 C2 120.7(4) . . ? C3 C4 C5 120.8(5) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 119.8(5) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C7 C6 C5 120.5(5) . . ? C7 C6 I1 120.2(4) . . ? C5 C6 I1 119.3(4) . . ? C6 C7 C8 119.3(5) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C7 C8 C3 121.4(5) . . ? C7 C8 H8 119.3 . . ? C3 C8 H8 119.3 . . ? C10 C9 C14 121.0(5) . . ? C10 C9 N1 120.3(4) . . ? C14 C9 N1 118.7(4) . . ? C11 C10 C9 119.6(5) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 121.7(5) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C11 C12 C13 117.1(5) . . ? C11 C12 H12 121.5 . . ? C13 C12 H12 121.5 . . ? C14 C13 C12 123.6(5) . . ? C14 C13 N4 117.7(4) . . ? C12 C13 N4 118.7(5) . . ? C13 C14 C9 117.0(4) . . ? C13 C14 H14 121.5 . . ? C9 C14 H14 121.5 . . ? 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 C1 N1 N2 N3 0.2(6) . . . . ? C9 N1 N2 N3 177.3(4) . . . . ? N1 N2 N3 C2 0.4(6) . . . . ? N2 N1 C1 C2 -0.8(5) . . . . ? C9 N1 C1 C2 -177.4(5) . . . . ? N1 C1 C2 N3 1.0(6) . . . . ? N1 C1 C2 C3 179.0(5) . . . . ? N2 N3 C2 C1 -0.9(6) . . . . ? N2 N3 C2 C3 -179.1(4) . . . . ? C1 C2 C3 C4 174.5(5) . . . . ? N3 C2 C3 C4 -7.7(8) . . . . ? C1 C2 C3 C8 -4.0(8) . . . . ? N3 C2 C3 C8 173.8(5) . . . . ? C8 C3 C4 C5 -1.1(8) . . . . ? C2 C3 C4 C5 -179.7(5) . . . . ? C3 C4 C5 C6 0.4(8) . . . . ? C4 C5 C6 C7 0.6(8) . . . . ? C4 C5 C6 I1 -179.6(4) . . . . ? C5 C6 C7 C8 -1.0(8) . . . . ? I1 C6 C7 C8 179.3(4) . . . . ? C6 C7 C8 C3 0.2(8) . . . . ? C4 C3 C8 C7 0.8(8) . . . . ? C2 C3 C8 C7 179.4(5) . . . . ? C1 N1 C9 C10 2.8(7) . . . . ? N2 N1 C9 C10 -173.6(4) . . . . ? C1 N1 C9 C14 -177.0(5) . . . . ? N2 N1 C9 C14 6.7(7) . . . . ? C14 C9 C10 C11 -0.1(8) . . . . ? N1 C9 C10 C11 -179.9(5) . . . . ? C9 C10 C11 C12 0.2(8) . . . . ? C10 C11 C12 C13 -0.6(8) . . . . ? C11 C12 C13 C14 0.9(8) . . . . ? C11 C12 C13 N4 -179.3(4) . . . . ? O1 N4 C13 C14 -10.7(7) . . . . ? O2 N4 C13 C14 169.2(5) . . . . ? O1 N4 C13 C12 169.4(5) . . . . ? O2 N4 C13 C12 -10.7(7) . . . . ? C12 C13 C14 C9 -0.8(7) . . . . ? N4 C13 C14 C9 179.3(4) . . . . ? C10 C9 C14 C13 0.4(7) . . . . ? N1 C9 C14 C13 -179.8(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C7 H7 N2 0.95 2.57 3.428(7) 150.6 1_565 C1 H1 O1 0.95 2.31 3.251(6) 168.1 1_565 C10 H10 O1 0.95 2.60 3.526(6) 163.7 1_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.958 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.124 _database_code_depnum_ccdc_archive 'CCDC 914833' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #===END data_4n2i #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1354970842.Comb_cif_iodo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 I N4 O2' _chemical_formula_sum 'C14 H9 I N4 O2' _chemical_formula_weight 392.15 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1884(8) _cell_length_b 11.9850(13) _cell_length_c 16.2685(17) _cell_angle_alpha 90.00 _cell_angle_beta 96.660(2) _cell_angle_gamma 90.00 _cell_volume 1392.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 4280 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 27.71 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.871 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 2.310 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7261 _exptl_absorpt_correction_T_max 0.9795 _exptl_absorpt_process_details "bruker's sadabs" _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13158 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2457 _reflns_number_gt 2129 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0362P)^2^+0.5226P] 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_extinction_coef ? _refine_ls_number_reflns 2457 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0812 _refine_ls_wR_factor_gt 0.0776 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.2787(5) 0.4316(3) 0.9983(2) 0.0356(8) Uani 1 1 d . . . H1 H 0.3493 0.3914 1.0416 0.043 Uiso 1 1 calc R . . C2 C 0.1960(4) 0.3904(3) 0.9251(2) 0.0348(7) Uani 1 1 d . . . C3 C 0.1832(5) 0.2784(3) 0.8867(2) 0.0366(8) Uani 1 1 d . . . C4 C 0.1387(5) 0.2743(3) 0.8005(2) 0.0451(9) Uani 1 1 d . . . H4 H 0.1267 0.3421 0.7701 0.054 Uiso 1 1 calc R . . C5 C 0.1116(6) 0.1738(3) 0.7586(3) 0.0541(11) Uani 1 1 d . . . H5 H 0.0799 0.1734 0.7003 0.065 Uiso 1 1 calc R . . C6 C 0.1306(6) 0.0753(4) 0.8012(3) 0.0588(11) Uani 1 1 d . . . H6 H 0.1111 0.0065 0.7726 0.071 Uiso 1 1 calc R . . C7 C 0.1781(6) 0.0762(3) 0.8859(3) 0.0566(11) Uani 1 1 d . . . H7 H 0.1947 0.0078 0.9153 0.068 Uiso 1 1 calc R . . C8 C 0.2018(5) 0.1769(3) 0.9282(2) 0.0431(9) Uani 1 1 d . . . C9 C 0.2821(4) 0.6271(3) 1.0571(2) 0.0354(8) Uani 1 1 d . . . C10 C 0.3389(5) 0.5966(3) 1.1377(2) 0.0405(8) Uani 1 1 d . . . H10 H 0.3522 0.5199 1.1520 0.049 Uiso 1 1 calc R . . C11 C 0.3766(5) 0.6775(3) 1.1979(2) 0.0435(9) Uani 1 1 d . . . H11 H 0.4168 0.6575 1.2536 0.052 Uiso 1 1 calc R . . C12 C 0.3544(5) 0.7876(3) 1.1752(2) 0.0389(8) Uani 1 1 d . . . C13 C 0.2990(5) 0.8190(3) 1.0945(3) 0.0462(9) Uani 1 1 d . . . H13 H 0.2851 0.8957 1.0802 0.055 Uiso 1 1 calc R . . C14 C 0.2642(5) 0.7375(3) 1.0349(2) 0.0460(9) Uani 1 1 d . . . H14 H 0.2280 0.7575 0.9788 0.055 Uiso 1 1 calc R . . I1 I 0.26219(5) 0.16139(2) 1.057328(16) 0.06291(15) Uani 1 1 d . . . N1 N 0.2390(4) 0.5427(2) 0.99623(17) 0.0355(6) Uani 1 1 d . . . N2 N 0.1333(4) 0.5694(2) 0.92374(18) 0.0436(7) Uani 1 1 d . . . N3 N 0.1080(4) 0.4772(2) 0.88144(18) 0.0442(7) Uani 1 1 d . . . N4 N 0.3926(4) 0.8736(3) 1.2387(2) 0.0462(8) Uani 1 1 d . . . O1 O 0.3740(5) 0.9708(2) 1.21816(19) 0.0698(9) Uani 1 1 d . . . O2 O 0.4442(5) 0.8442(2) 1.30961(19) 0.0645(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0382(19) 0.0302(18) 0.0367(19) 0.0001(14) -0.0036(15) 0.0007(14) C2 0.0347(18) 0.0364(19) 0.0325(18) 0.0029(15) 0.0012(14) -0.0019(14) C3 0.0386(19) 0.0377(19) 0.0336(18) -0.0063(15) 0.0046(15) -0.0052(15) C4 0.054(2) 0.045(2) 0.036(2) -0.0025(16) 0.0037(17) -0.0070(18) C5 0.060(3) 0.062(3) 0.040(2) -0.0172(19) 0.0045(19) -0.009(2) C6 0.069(3) 0.050(3) 0.057(3) -0.022(2) 0.008(2) -0.008(2) C7 0.076(3) 0.037(2) 0.056(3) -0.0111(19) 0.005(2) -0.004(2) C8 0.054(2) 0.042(2) 0.0320(19) -0.0074(15) 0.0007(16) -0.0027(17) C9 0.0345(18) 0.0289(17) 0.042(2) -0.0019(14) 0.0017(15) -0.0032(14) C10 0.054(2) 0.0255(17) 0.040(2) 0.0029(15) -0.0039(16) -0.0006(16) C11 0.053(2) 0.036(2) 0.039(2) -0.0004(15) -0.0059(17) 0.0011(16) C12 0.0371(19) 0.0294(18) 0.048(2) -0.0051(15) -0.0042(16) -0.0025(15) C13 0.059(2) 0.0225(17) 0.055(2) 0.0064(16) -0.0042(19) 0.0008(16) C14 0.059(2) 0.0328(19) 0.042(2) 0.0080(16) -0.0089(18) -0.0008(17) I1 0.1072(3) 0.03734(18) 0.04068(19) 0.00277(10) -0.00622(15) -0.00253(14) N1 0.0402(16) 0.0287(15) 0.0366(16) 0.0005(12) 0.0006(13) 0.0000(12) N2 0.0558(19) 0.0358(16) 0.0362(17) 0.0041(13) -0.0070(14) 0.0025(14) N3 0.0563(19) 0.0382(17) 0.0354(16) 0.0011(13) -0.0062(14) -0.0010(14) N4 0.0509(19) 0.0351(17) 0.050(2) -0.0060(15) -0.0057(15) -0.0023(14) O1 0.103(2) 0.0307(15) 0.070(2) -0.0052(14) -0.0166(18) -0.0033(15) O2 0.089(2) 0.0493(18) 0.0503(18) -0.0116(13) -0.0134(16) 0.0000(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.361(5) . ? C1 N1 1.362(4) . ? C1 H1 0.9500 . ? C2 N3 1.372(4) . ? C2 C3 1.479(5) . ? C3 C8 1.390(5) . ? C3 C4 1.401(5) . ? C4 C5 1.386(5) . ? C4 H4 0.9500 . ? C5 C6 1.367(6) . ? C5 H5 0.9500 . ? C6 C7 1.380(6) . ? C6 H6 0.9500 . ? C7 C8 1.390(5) . ? C7 H7 0.9500 . ? C8 I1 2.104(4) . ? C9 C14 1.374(5) . ? C9 C10 1.377(5) . ? C9 N1 1.424(4) . ? C10 C11 1.382(5) . ? C10 H10 0.9500 . ? C11 C12 1.375(5) . ? C11 H11 0.9500 . ? C12 C13 1.379(5) . ? C12 N4 1.463(5) . ? C13 C14 1.379(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? N1 N2 1.365(4) . ? N2 N3 1.303(4) . ? N4 O1 1.215(4) . ? N4 O2 1.222(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 105.3(3) . . ? C2 C1 H1 127.3 . . ? N1 C1 H1 127.3 . . ? C1 C2 N3 107.8(3) . . ? C1 C2 C3 134.3(3) . . ? N3 C2 C3 117.9(3) . . ? C8 C3 C4 116.9(3) . . ? C8 C3 C2 126.2(3) . . ? C4 C3 C2 116.8(3) . . ? C5 C4 C3 121.7(4) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C6 C5 C4 120.1(4) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 119.8(4) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C6 C7 C8 120.2(4) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C3 121.3(4) . . ? C7 C8 I1 114.6(3) . . ? C3 C8 I1 124.0(3) . . ? C14 C9 C10 120.9(3) . . ? C14 C9 N1 119.7(3) . . ? C10 C9 N1 119.4(3) . . ? C9 C10 C11 120.0(3) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 118.5(3) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C11 C12 C13 121.9(3) . . ? C11 C12 N4 118.7(3) . . ? C13 C12 N4 119.4(3) . . ? C14 C13 C12 119.0(3) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C9 C14 C13 119.6(3) . . ? C9 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C1 N1 N2 110.2(3) . . ? C1 N1 C9 130.5(3) . . ? N2 N1 C9 119.3(3) . . ? N3 N2 N1 106.7(3) . . ? N2 N3 C2 110.0(3) . . ? O1 N4 O2 123.2(3) . . ? O1 N4 C12 118.4(3) . . ? O2 N4 C12 118.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N3 -0.4(4) . . . . ? N1 C1 C2 C3 179.8(4) . . . . ? C1 C2 C3 C8 23.8(6) . . . . ? N3 C2 C3 C8 -156.0(4) . . . . ? C1 C2 C3 C4 -159.7(4) . . . . ? N3 C2 C3 C4 20.6(5) . . . . ? C8 C3 C4 C5 0.9(6) . . . . ? C2 C3 C4 C5 -175.9(3) . . . . ? C3 C4 C5 C6 -0.9(6) . . . . ? C4 C5 C6 C7 -0.5(7) . . . . ? C5 C6 C7 C8 1.7(7) . . . . ? C6 C7 C8 C3 -1.6(6) . . . . ? C6 C7 C8 I1 177.4(3) . . . . ? C4 C3 C8 C7 0.3(6) . . . . ? C2 C3 C8 C7 176.8(4) . . . . ? C4 C3 C8 I1 -178.6(3) . . . . ? C2 C3 C8 I1 -2.1(5) . . . . ? C14 C9 C10 C11 0.8(5) . . . . ? N1 C9 C10 C11 -178.3(3) . . . . ? C9 C10 C11 C12 0.5(6) . . . . ? C10 C11 C12 C13 -1.0(6) . . . . ? C10 C11 C12 N4 179.5(3) . . . . ? C11 C12 C13 C14 0.2(6) . . . . ? N4 C12 C13 C14 179.7(3) . . . . ? C10 C9 C14 C13 -1.6(6) . . . . ? N1 C9 C14 C13 177.5(3) . . . . ? C12 C13 C14 C9 1.1(6) . . . . ? C2 C1 N1 N2 0.4(4) . . . . ? C2 C1 N1 C9 177.0(3) . . . . ? C14 C9 N1 C1 165.6(3) . . . . ? C10 C9 N1 C1 -15.3(5) . . . . ? C14 C9 N1 N2 -18.0(5) . . . . ? C10 C9 N1 N2 161.1(3) . . . . ? C1 N1 N2 N3 -0.1(4) . . . . ? C9 N1 N2 N3 -177.2(3) . . . . ? N1 N2 N3 C2 -0.1(4) . . . . ? C1 C2 N3 N2 0.4(4) . . . . ? C3 C2 N3 N2 -179.8(3) . . . . ? C11 C12 N4 O1 179.5(4) . . . . ? C13 C12 N4 O1 0.0(5) . . . . ? C11 C12 N4 O2 0.6(5) . . . . ? C13 C12 N4 O2 -178.9(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C10 H10 O2 0.95 2.60 3.465(4) 151.7 2_647 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.658 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 914834' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #===END data_4n3i #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1354970842.Comb_cif_iodo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 I N4 O2' _chemical_formula_sum 'C14 H9 I N4 O2' _chemical_formula_weight 392.15 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.8521(11) _cell_length_b 7.0890(10) _cell_length_c 24.500(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.151(2) _cell_angle_gamma 90.00 _cell_volume 1363.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 8017 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 28.12 _exptl_crystal_description 'thin plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.910 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 2.358 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3781 _exptl_absorpt_correction_T_max 0.9544 _exptl_absorpt_process_details "bruker's sadabs" _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12720 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2415 _reflns_number_gt 2307 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^+1.1181P] 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_extinction_coef ? _refine_ls_number_reflns 2415 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0672 _refine_ls_wR_factor_gt 0.0662 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_restrained_S_all 1.172 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.6214(4) 0.6827(4) 0.18847(12) 0.0356(6) Uani 1 1 d . . . H1 H 0.6734 0.5659 0.1977 0.043 Uiso 1 1 calc R . . C2 C 0.6419(4) 0.8508(4) 0.21425(12) 0.0355(6) Uani 1 1 d . . . C3 C 0.7534(4) 0.9061(4) 0.25996(12) 0.0350(6) Uani 1 1 d . . . C4 C 0.7962(4) 1.0947(4) 0.26701(13) 0.0424(7) Uani 1 1 d . . . H4 H 0.7512 1.1869 0.2428 0.051 Uiso 1 1 calc R . . C5 C 0.9031(5) 1.1492(5) 0.30861(15) 0.0487(8) Uani 1 1 d . . . H5 H 0.9301 1.2789 0.3133 0.058 Uiso 1 1 calc R . . C6 C 0.9716(4) 1.0164(5) 0.34363(13) 0.0463(8) Uani 1 1 d . . . H6 H 1.0464 1.0537 0.3722 0.056 Uiso 1 1 calc R . . C7 C 0.9299(4) 0.8289(4) 0.33659(12) 0.0364(6) Uani 1 1 d . . . C8 C 0.8209(4) 0.7720(4) 0.29529(12) 0.0368(6) Uani 1 1 d . . . H8 H 0.7925 0.6425 0.2911 0.044 Uiso 1 1 calc R . . C9 C 0.4465(3) 0.5908(4) 0.10650(11) 0.0323(6) Uani 1 1 d . . . C10 C 0.4902(4) 0.4015(4) 0.10722(12) 0.0392(7) Uani 1 1 d . . . H10 H 0.5637 0.3544 0.1349 0.047 Uiso 1 1 calc R . . C11 C 0.4274(4) 0.2816(4) 0.06783(12) 0.0399(7) Uani 1 1 d . . . H11 H 0.4574 0.1518 0.0678 0.048 Uiso 1 1 calc R . . C12 C 0.3202(4) 0.3540(4) 0.02850(12) 0.0350(6) Uani 1 1 d . . . C13 C 0.2743(4) 0.5414(5) 0.02706(12) 0.0399(7) Uani 1 1 d . . . H13 H 0.2002 0.5871 -0.0007 0.048 Uiso 1 1 calc R . . C14 C 0.3374(4) 0.6622(4) 0.06644(13) 0.0404(7) Uani 1 1 d . . . H14 H 0.3071 0.7919 0.0663 0.049 Uiso 1 1 calc R . . I1 I 1.03801(3) 0.62771(3) 0.389895(8) 0.04839(11) Uani 1 1 d . . . N1 N 0.5114(3) 0.7159(3) 0.14691(9) 0.0328(5) Uani 1 1 d . . . N2 N 0.4636(4) 0.9002(4) 0.14719(12) 0.0463(7) Uani 1 1 d . . . N3 N 0.5431(4) 0.9813(4) 0.18775(11) 0.0464(6) Uani 1 1 d . . . N4 N 0.2522(3) 0.2249(4) -0.01271(10) 0.0447(6) Uani 1 1 d . . . O1 O 0.1537(4) 0.2884(4) -0.04670(11) 0.0744(9) Uani 1 1 d . . . O2 O 0.2954(4) 0.0605(4) -0.01211(11) 0.0667(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 0.0351(15) 0.0388(16) 0.0330(15) 0.0017(12) -0.0060(12) 0.0047(12) C2 0.0353(15) 0.0374(16) 0.0337(16) 0.0012(12) -0.0013(12) 0.0012(12) C3 0.0331(15) 0.0411(16) 0.0309(15) -0.0050(12) 0.0016(12) -0.0014(12) C4 0.0479(18) 0.0404(17) 0.0390(17) -0.0038(13) 0.0026(14) -0.0034(14) C5 0.054(2) 0.0436(18) 0.049(2) -0.0100(15) 0.0050(16) -0.0128(15) C6 0.0404(17) 0.060(2) 0.0386(17) -0.0109(15) 0.0001(14) -0.0079(15) C7 0.0313(15) 0.0450(17) 0.0331(15) -0.0042(13) -0.0013(12) -0.0003(12) C8 0.0371(16) 0.0400(16) 0.0331(15) -0.0044(13) -0.0014(12) -0.0022(13) C9 0.0295(14) 0.0390(16) 0.0283(14) 0.0041(11) -0.0023(12) -0.0019(11) C10 0.0404(16) 0.0424(17) 0.0349(17) 0.0044(12) -0.0115(13) 0.0055(13) C11 0.0460(18) 0.0368(16) 0.0368(16) 0.0019(13) -0.0094(13) 0.0051(13) C12 0.0375(16) 0.0395(16) 0.0279(14) 0.0005(12) -0.0031(12) -0.0026(12) C13 0.0389(16) 0.0479(18) 0.0328(15) 0.0071(13) -0.0093(13) 0.0026(14) C14 0.0451(18) 0.0375(16) 0.0386(17) 0.0038(13) -0.0087(14) 0.0066(13) I1 0.04536(15) 0.06100(17) 0.03876(15) -0.00493(9) -0.01135(10) 0.00567(9) N1 0.0339(12) 0.0345(13) 0.0298(12) 0.0021(10) -0.0058(10) 0.0027(10) N2 0.0560(17) 0.0360(14) 0.0467(16) -0.0022(12) -0.0174(13) 0.0087(12) N3 0.0560(17) 0.0377(14) 0.0455(15) -0.0041(12) -0.0151(13) 0.0054(12) N4 0.0477(16) 0.0525(17) 0.0340(14) -0.0001(12) -0.0091(12) -0.0034(13) O1 0.103(2) 0.0609(16) 0.0588(16) -0.0009(14) -0.0487(16) 0.0027(16) O2 0.087(2) 0.0487(15) 0.0640(17) -0.0154(13) -0.0279(14) 0.0099(14) _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 N1 1.354(4) . ? C1 C2 1.358(4) . ? C1 H1 0.9500 . ? C2 N3 1.370(4) . ? C2 C3 1.473(4) . ? C3 C4 1.389(4) . ? C3 C8 1.390(4) . ? C4 C5 1.374(5) . ? C4 H4 0.9500 . ? C5 C6 1.382(5) . ? C5 H5 0.9500 . ? C6 C7 1.379(5) . ? C6 H6 0.9500 . ? C7 C8 1.384(4) . ? C7 I1 2.111(3) . ? C8 H8 0.9500 . ? C9 C10 1.385(4) . ? C9 C14 1.396(4) . ? C9 N1 1.423(4) . ? C10 C11 1.377(4) . ? C10 H10 0.9500 . ? C11 C12 1.377(4) . ? C11 H11 0.9500 . ? C12 C13 1.377(4) . ? C12 N4 1.462(4) . ? C13 C14 1.381(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? N1 N2 1.359(3) . ? N2 N3 1.306(4) . ? N4 O2 1.214(4) . ? N4 O1 1.221(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 N1 C1 C2 105.7(3) . . ? N1 C1 H1 127.1 . . ? C2 C1 H1 127.1 . . ? C1 C2 N3 107.8(3) . . ? C1 C2 C3 131.1(3) . . ? N3 C2 C3 121.0(3) . . ? C4 C3 C8 119.3(3) . . ? C4 C3 C2 119.6(3) . . ? C8 C3 C2 121.1(3) . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.3(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 119.1(3) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C8 121.3(3) . . ? C6 C7 I1 118.6(2) . . ? C8 C7 I1 120.2(2) . . ? C7 C8 C3 119.3(3) . . ? C7 C8 H8 120.3 . . ? C3 C8 H8 120.3 . . ? C10 C9 C14 120.8(3) . . ? C10 C9 N1 120.4(3) . . ? C14 C9 N1 118.8(3) . . ? C11 C10 C9 120.0(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 118.5(3) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C11 C12 C13 122.5(3) . . ? C11 C12 N4 118.1(3) . . ? C13 C12 N4 119.4(3) . . ? C12 C13 C14 119.1(3) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C13 C14 C9 119.0(3) . . ? C13 C14 H14 120.5 . . ? C9 C14 H14 120.5 . . ? C1 N1 N2 109.8(2) . . ? C1 N1 C9 129.9(3) . . ? N2 N1 C9 120.3(2) . . ? N3 N2 N1 107.2(2) . . ? N2 N3 C2 109.4(3) . . ? O2 N4 O1 122.6(3) . . ? O2 N4 C12 119.4(3) . . ? O1 N4 C12 118.0(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N3 0.3(3) . . . . ? N1 C1 C2 C3 -175.7(3) . . . . ? C1 C2 C3 C4 157.6(3) . . . . ? N3 C2 C3 C4 -17.9(4) . . . . ? C1 C2 C3 C8 -20.4(5) . . . . ? N3 C2 C3 C8 164.0(3) . . . . ? C8 C3 C4 C5 -0.5(5) . . . . ? C2 C3 C4 C5 -178.5(3) . . . . ? C3 C4 C5 C6 0.9(5) . . . . ? C4 C5 C6 C7 -0.6(5) . . . . ? C5 C6 C7 C8 -0.1(5) . . . . ? C5 C6 C7 I1 179.3(2) . . . . ? C6 C7 C8 C3 0.6(4) . . . . ? I1 C7 C8 C3 -178.8(2) . . . . ? C4 C3 C8 C7 -0.3(4) . . . . ? C2 C3 C8 C7 177.7(3) . . . . ? C14 C9 C10 C11 0.6(5) . . . . ? N1 C9 C10 C11 -179.7(3) . . . . ? C9 C10 C11 C12 -0.5(5) . . . . ? C10 C11 C12 C13 0.3(5) . . . . ? C10 C11 C12 N4 -179.2(3) . . . . ? C11 C12 C13 C14 -0.1(5) . . . . ? N4 C12 C13 C14 179.3(3) . . . . ? C12 C13 C14 C9 0.2(5) . . . . ? C10 C9 C14 C13 -0.5(5) . . . . ? N1 C9 C14 C13 179.9(3) . . . . ? C2 C1 N1 N2 -0.5(3) . . . . ? C2 C1 N1 C9 179.3(3) . . . . ? C10 C9 N1 C1 2.4(5) . . . . ? C14 C9 N1 C1 -177.9(3) . . . . ? C10 C9 N1 N2 -177.7(3) . . . . ? C14 C9 N1 N2 2.0(4) . . . . ? C1 N1 N2 N3 0.6(3) . . . . ? C9 N1 N2 N3 -179.3(3) . . . . ? N1 N2 N3 C2 -0.4(4) . . . . ? C1 C2 N3 N2 0.1(4) . . . . ? C3 C2 N3 N2 176.5(3) . . . . ? C11 C12 N4 O2 -2.0(4) . . . . ? C13 C12 N4 O2 178.5(3) . . . . ? C11 C12 N4 O1 178.2(3) . . . . ? C13 C12 N4 O1 -1.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C6 H6 O1 0.95 2.43 3.341(4) 160.6 4_676 C11 H11 N2 0.95 2.64 3.342(4) 131.1 1_545 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.581 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.098 _database_code_depnum_ccdc_archive 'CCDC 914835' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global #===END data_4n4i #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1354970842.Comb_cif_iodo.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 I N4 O2' _chemical_formula_sum 'C14 H9 I N4 O2' _chemical_formula_weight 392.15 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.638(6) _cell_length_b 5.5912(13) _cell_length_c 17.974(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.932(6) _cell_angle_gamma 90.00 _cell_volume 2757.2(11) _cell_formula_units_Z 8 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 4325 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 27.80 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.889 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 2.333 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4422 _exptl_absorpt_correction_T_max 0.9592 _exptl_absorpt_process_details "bruker's sadabs" _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12416 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2437 _reflns_number_gt 2114 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0392P)^2^+8.1003P] 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_extinction_coef ? _refine_ls_number_reflns 2437 _refine_ls_number_parameters 226 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0757 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.19466(14) 1.0328(7) 0.9300(2) 0.0283(9) Uani 1 1 d . . . H1 H 0.1940 1.2024 0.9272 0.034 Uiso 1 1 calc R . . C2 C 0.22652(14) 0.8806(7) 0.9007(2) 0.0269(8) Uani 1 1 d . . . C3 C 0.26720(14) 0.9345(7) 0.8587(2) 0.0264(8) Uani 1 1 d . . . C4 C 0.28180(14) 0.7711(7) 0.8075(2) 0.0296(9) Uani 1 1 d . . . H4 H 0.2649 0.6235 0.7998 0.036 Uiso 1 1 calc R . . C5 C 0.32022(15) 0.8189(7) 0.7675(2) 0.0336(9) Uani 1 1 d D . . H5 H 0.3298 0.7053 0.7328 0.040 Uiso 1 1 calc R . . C6 C 0.34495(14) 1.0357(8) 0.7786(2) 0.0324(9) Uani 1 1 d D . . C7 C 0.33074(14) 1.2000(8) 0.8293(2) 0.0324(9) Uani 1 1 d D . . H7 H 0.3477 1.3476 0.8368 0.039 Uiso 1 1 calc R . . C8 C 0.29221(14) 1.1512(7) 0.8689(2) 0.0319(9) Uani 1 1 d . . . H8 H 0.2826 1.2655 0.9034 0.038 Uiso 1 1 calc R . . C9 C 0.12330(14) 0.9510(7) 1.0013(2) 0.0274(9) Uani 1 1 d . . . C10 C 0.09893(15) 1.1617(7) 0.9826(2) 0.0365(10) Uani 1 1 d . . . H10 H 0.1089 1.2631 0.9448 0.044 Uiso 1 1 calc R . . C11 C 0.05941(15) 1.2229(8) 1.0202(2) 0.0379(10) Uani 1 1 d . . . H11 H 0.0420 1.3675 1.0087 0.045 Uiso 1 1 calc R . . C12 C 0.04608(14) 1.0704(8) 1.0741(2) 0.0352(10) Uani 1 1 d D . . C13 C 0.07004(15) 0.8576(8) 1.0927(2) 0.0368(10) Uani 1 1 d . . . H13 H 0.0598 0.7554 1.1301 0.044 Uiso 1 1 calc R . . C14 C 0.10943(14) 0.7976(8) 1.0554(2) 0.0322(9) Uani 1 1 d . . . H14 H 0.1267 0.6527 1.0668 0.039 Uiso 1 1 calc R . . I1' I -0.0114(3) 1.209(2) 1.1305(5) 0.097(3) Uani 0.10 1 d PD . 1 N4 N 0.0053(2) 1.1330(11) 1.1131(3) 0.0471(15) Uani 0.90 1 d PD . 2 O1 O -0.00892(15) 0.9904(9) 1.1591(2) 0.0619(11) Uani 0.90 1 d PD . 2 O2 O -0.0152(2) 1.3341(11) 1.0978(4) 0.0748(19) Uani 0.90 1 d PD . 2 N1 N 0.16449(12) 0.8889(6) 0.96381(18) 0.0300(7) Uani 1 1 d . . . N2 N 0.17729(13) 0.6558(6) 0.95682(19) 0.0330(8) Uani 1 1 d . . . N3 N 0.21500(12) 0.6517(6) 0.91870(19) 0.0330(8) Uani 1 1 d . . . I1 I 0.404642(12) 1.11649(8) 0.720460(19) 0.04661(16) Uani 0.90 1 d P . 1 O1' O 0.3941(16) 0.926(7) 0.693(2) 0.092(14) Uani 0.10 1 d PDU . 2 N4' N 0.3796(13) 1.095(5) 0.729(2) 0.052(12) Uani 0.10 1 d PDU . 2 O2' O 0.3951(14) 1.303(5) 0.730(2) 0.077(12) Uani 0.10 1 d PDU . 2 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 0.034(2) 0.021(2) 0.031(2) 0.0020(16) 0.0081(17) -0.0013(17) C2 0.030(2) 0.022(2) 0.029(2) -0.0020(16) 0.0048(16) -0.0005(16) C3 0.025(2) 0.027(2) 0.0264(19) 0.0033(16) 0.0025(15) 0.0027(16) C4 0.033(2) 0.023(2) 0.033(2) -0.0024(17) 0.0028(17) 0.0010(17) C5 0.036(2) 0.033(2) 0.033(2) -0.0056(18) 0.0079(18) 0.0026(18) C6 0.025(2) 0.041(2) 0.031(2) 0.0082(18) 0.0075(17) 0.0016(18) C7 0.031(2) 0.027(2) 0.038(2) 0.0021(18) 0.0026(18) -0.0038(17) C8 0.034(2) 0.028(2) 0.034(2) -0.0048(17) 0.0046(17) 0.0025(17) C9 0.0241(19) 0.028(2) 0.030(2) -0.0054(16) 0.0041(16) -0.0035(16) C10 0.038(2) 0.031(2) 0.042(2) 0.0053(19) 0.0125(19) -0.0017(19) C11 0.032(2) 0.034(2) 0.049(3) -0.001(2) 0.0052(19) 0.0041(19) C12 0.026(2) 0.043(3) 0.037(2) -0.0060(19) 0.0087(18) -0.0027(18) C13 0.037(2) 0.042(3) 0.033(2) 0.0060(19) 0.0102(18) -0.006(2) C14 0.030(2) 0.032(2) 0.036(2) 0.0034(18) 0.0077(17) 0.0016(17) I1' 0.054(4) 0.160(10) 0.078(5) -0.038(5) 0.013(3) -0.002(5) N4 0.034(3) 0.060(4) 0.050(3) -0.014(3) 0.015(2) 0.007(3) O1 0.060(3) 0.074(3) 0.058(3) 0.013(2) 0.034(2) 0.006(2) O2 0.070(4) 0.076(4) 0.085(4) 0.013(3) 0.037(3) 0.039(3) N1 0.0318(18) 0.0257(18) 0.0337(18) 0.0009(14) 0.0090(14) 0.0006(14) N2 0.0375(19) 0.0235(19) 0.0396(19) 0.0020(15) 0.0115(16) 0.0009(15) N3 0.0350(19) 0.0287(19) 0.0368(19) -0.0003(15) 0.0108(15) 0.0021(15) I1 0.0319(2) 0.0705(3) 0.0398(2) 0.00591(18) 0.01427(15) -0.00715(17) O1' 0.091(16) 0.094(17) 0.093(16) -0.003(10) 0.019(10) -0.006(10) N4' 0.045(14) 0.052(15) 0.059(15) 0.001(9) 0.006(10) -0.007(10) O2' 0.080(14) 0.074(14) 0.079(14) -0.003(10) 0.021(10) -0.007(10) _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 N1 1.354(5) . ? C1 C2 1.374(5) . ? C1 H1 0.9500 . ? C2 N3 1.368(5) . ? C2 C3 1.459(5) . ? C3 C4 1.391(5) . ? C3 C8 1.396(5) . ? C4 C5 1.378(6) . ? C4 H4 0.9500 . ? C5 C6 1.394(6) . ? C5 H5 0.9500 . ? C6 C7 1.383(6) . ? C6 N4' 1.422(16) . ? C6 I1 2.106(4) . ? C7 C8 1.379(6) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.378(6) . ? C9 C14 1.385(6) . ? C9 N1 1.434(5) . ? C10 C11 1.395(6) . ? C10 H10 0.9500 . ? C11 C12 1.375(6) . ? C11 H11 0.9500 . ? C12 C13 1.383(6) . ? C12 N4 1.439(6) . ? C12 I1' 2.130(8) . ? C13 C14 1.387(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? I1' I1 3.140(7) 8_476 ? N4 O1 1.246(7) . ? N4 O2 1.275(8) . ? N1 N2 1.360(4) . ? N2 N3 1.315(5) . ? I1 I1' 3.140(8) 8_575 ? O1' N4' 1.238(18) . ? N4' O2' 1.238(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 105.2(3) . . ? N1 C1 H1 127.4 . . ? C2 C1 H1 127.4 . . ? N3 C2 C1 108.1(3) . . ? N3 C2 C3 122.1(3) . . ? C1 C2 C3 129.8(4) . . ? C4 C3 C8 118.6(4) . . ? C4 C3 C2 120.7(3) . . ? C8 C3 C2 120.8(3) . . ? C5 C4 C3 121.4(4) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 119.3(4) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C7 C6 C5 119.9(4) . . ? C7 C6 N4' 121.5(12) . . ? C5 C6 N4' 118.0(12) . . ? C7 C6 I1 119.1(3) . . ? C5 C6 I1 121.0(3) . . ? C8 C7 C6 120.5(4) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C3 120.3(4) . . ? C7 C8 H8 119.8 . . ? C3 C8 H8 119.8 . . ? C10 C9 C14 122.1(4) . . ? C10 C9 N1 119.0(4) . . ? C14 C9 N1 118.9(4) . . ? C9 C10 C11 118.7(4) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C12 C11 C10 118.8(4) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C11 C12 C13 122.9(4) . . ? C11 C12 N4 119.0(4) . . ? C13 C12 N4 118.1(4) . . ? C11 C12 I1' 112.9(5) . . ? C13 C12 I1' 124.1(5) . . ? C12 C13 C14 118.2(4) . . ? C12 C13 H13 120.9 . . ? C14 C13 H13 120.9 . . ? C9 C14 C13 119.3(4) . . ? C9 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C12 I1' I1 176.2(6) . 8_476 ? O1 N4 O2 122.6(6) . . ? O1 N4 C12 119.7(6) . . ? O2 N4 C12 117.7(5) . . ? C1 N1 N2 110.3(3) . . ? C1 N1 C9 129.3(3) . . ? N2 N1 C9 120.4(3) . . ? N3 N2 N1 107.2(3) . . ? N2 N3 C2 109.2(3) . . ? C6 I1 I1' 173.9(2) . 8_575 ? O1' N4' O2' 126(3) . . ? O1' N4' C6 116(2) . . ? O2' N4' C6 118(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 N1 C1 C2 N3 -0.9(4) . . . . ? N1 C1 C2 C3 -179.5(4) . . . . ? N3 C2 C3 C4 29.4(6) . . . . ? C1 C2 C3 C4 -152.1(4) . . . . ? N3 C2 C3 C8 -150.8(4) . . . . ? C1 C2 C3 C8 27.7(6) . . . . ? C8 C3 C4 C5 0.4(6) . . . . ? C2 C3 C4 C5 -179.8(4) . . . . ? C3 C4 C5 C6 -0.1(6) . . . . ? C4 C5 C6 C7 -0.1(6) . . . . ? C4 C5 C6 N4' -171(2) . . . . ? C4 C5 C6 I1 179.0(3) . . . . ? C5 C6 C7 C8 0.0(6) . . . . ? N4' C6 C7 C8 171(2) . . . . ? I1 C6 C7 C8 -179.1(3) . . . . ? C6 C7 C8 C3 0.3(6) . . . . ? C4 C3 C8 C7 -0.5(6) . . . . ? C2 C3 C8 C7 179.7(4) . . . . ? C14 C9 C10 C11 0.8(6) . . . . ? N1 C9 C10 C11 -178.9(4) . . . . ? C9 C10 C11 C12 -0.4(6) . . . . ? C10 C11 C12 C13 -0.2(7) . . . . ? C10 C11 C12 N4 180.0(4) . . . . ? C10 C11 C12 I1' 175.6(4) . . . . ? C11 C12 C13 C14 0.4(6) . . . . ? N4 C12 C13 C14 -179.8(4) . . . . ? I1' C12 C13 C14 -174.9(4) . . . . ? C10 C9 C14 C13 -0.6(6) . . . . ? N1 C9 C14 C13 179.1(4) . . . . ? C12 C13 C14 C9 0.0(6) . . . . ? C11 C12 N4 O1 176.0(5) . . . . ? C13 C12 N4 O1 -3.9(7) . . . . ? I1' C12 N4 O1 -150(3) . . . . ? C11 C12 N4 O2 -3.1(8) . . . . ? C13 C12 N4 O2 177.1(5) . . . . ? I1' C12 N4 O2 31(3) . . . . ? C2 C1 N1 N2 0.8(4) . . . . ? C2 C1 N1 C9 -177.6(4) . . . . ? C10 C9 N1 C1 24.6(6) . . . . ? C14 C9 N1 C1 -155.1(4) . . . . ? C10 C9 N1 N2 -153.6(4) . . . . ? C14 C9 N1 N2 26.6(5) . . . . ? C1 N1 N2 N3 -0.3(4) . . . . ? C9 N1 N2 N3 178.3(3) . . . . ? N1 N2 N3 C2 -0.3(4) . . . . ? C1 C2 N3 N2 0.8(4) . . . . ? C3 C2 N3 N2 179.5(3) . . . . ? C7 C6 N4' O1' 171(4) . . . . ? C5 C6 N4' O1' -18(5) . . . . ? I1 C6 N4' O1' 94(9) . . . . ? C7 C6 N4' O2' -4(5) . . . . ? C5 C6 N4' O2' 167(4) . . . . ? I1 C6 N4' O2' -81(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 N3 0.95 2.59 3.515(5) 165.8 1_565 C1 H1 N2 0.95 2.64 3.557(5) 161.8 1_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.626 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.083 #===END _database_code_depnum_ccdc_archive 'CCDC 914836'