# 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 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 N2, Cl, H2 O' _chemical_formula_sum 'C13 H13 Cl N2 O' _chemical_formula_weight 248.70 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8765(7) _cell_length_b 8.8951(8) _cell_length_c 9.7980(9) _cell_angle_alpha 111.508(8) _cell_angle_beta 96.724(7) _cell_angle_gamma 103.525(8) _cell_volume 605.14(11) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4260 _cell_measurement_theta_min 3.62 _cell_measurement_theta_max 25.25 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.833 _exptl_absorpt_correction_T_max 0.939 _exptl_absorpt_process_details ; CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd., 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(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 'Oxford Diffraction Ruby CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.4002 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4260 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2184 _reflns_number_gt 1880 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_cell_refinement 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 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^)+(0.0471P)^2^+0.0739P] 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 2184 _refine_ls_number_parameters 160 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.041 _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 0.7752(2) 0.1519(2) 0.52900(19) 0.0443(4) Uani 1 1 d . . . H1 H 0.8694 0.1807 0.6095 0.053 Uiso 1 1 calc R . . C2 C 0.7704(2) 0.0336(2) 0.3913(2) 0.0501(4) Uani 1 1 d . . . H2 H 0.8615 -0.0171 0.3784 0.060 Uiso 1 1 calc R . . C3 C 0.6284(2) -0.0119(2) 0.26857(19) 0.0521(4) Uani 1 1 d . . . H3 H 0.6265 -0.0924 0.1749 0.063 Uiso 1 1 calc R . . C4 C 0.4935(2) 0.0607(2) 0.28558(18) 0.0474(4) Uani 1 1 d . . . H4 H 0.3992 0.0287 0.2042 0.057 Uiso 1 1 calc R . . C5 C 0.2138(2) 0.44744(19) 0.58308(19) 0.0452(4) Uani 1 1 d . . . H5 H 0.1227 0.4101 0.4981 0.054 Uiso 1 1 calc R . . C6 C 0.2073(2) 0.5679(2) 0.7149(2) 0.0498(4) Uani 1 1 d . . . H6 H 0.1115 0.6126 0.7196 0.060 Uiso 1 1 calc R . . C7 C 0.3440(2) 0.6254(2) 0.8442(2) 0.0491(4) Uani 1 1 d . . . H7 H 0.3380 0.7079 0.9338 0.059 Uiso 1 1 calc R . . C8 C 0.4854(2) 0.56123(19) 0.83908(17) 0.0428(4) Uani 1 1 d . . . H8 H 0.5752 0.6007 0.9253 0.051 Uiso 1 1 calc R . . C9 C 0.6405(2) 0.35981(17) 0.69320(16) 0.0360(3) Uani 1 1 d . . . N10 N 0.36354(17) 0.25833(15) 0.44215(14) 0.0405(3) Uani 1 1 d . . . H10 H 0.2787 0.2276 0.3648 0.049 Uiso 1 1 calc R . . C11 C 0.6384(2) 0.23148(17) 0.55108(16) 0.0361(3) Uani 1 1 d . . . C12 C 0.4973(2) 0.18421(18) 0.42658(16) 0.0377(3) Uani 1 1 d . . . C13 C 0.49713(19) 0.43500(17) 0.70376(16) 0.0357(3) Uani 1 1 d . . . C14 C 0.3584(2) 0.37898(17) 0.57498(17) 0.0368(3) Uani 1 1 d . . . N15 N 0.77201(18) 0.40770(16) 0.81169(14) 0.0477(4) Uani 1 1 d . . . H15A H 0.8572 0.3619 0.8040 0.057 Uiso 1 1 calc R . . H15B H 0.7722 0.4847 0.8964 0.057 Uiso 1 1 calc R . . Cl16 Cl 1.05918(6) 0.23259(5) 0.90035(4) 0.05196(17) Uani 1 1 d . . . O17 O 0.0811(2) 0.16600(16) 0.19881(13) 0.0609(4) Uani 1 1 d D . . H17A H 0.042(3) 0.063(2) 0.174(3) 0.091 Uiso 1 1 d D . . H17B H 0.085(3) 0.186(3) 0.121(2) 0.091 Uiso 1 1 d 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 0.0429(9) 0.0458(9) 0.0410(9) 0.0156(7) 0.0079(7) 0.0120(7) C2 0.0535(10) 0.0497(9) 0.0481(10) 0.0162(8) 0.0195(8) 0.0192(8) C3 0.0646(11) 0.0448(9) 0.0379(9) 0.0077(7) 0.0179(8) 0.0121(8) C4 0.0542(10) 0.0437(9) 0.0328(8) 0.0102(7) 0.0041(7) 0.0057(8) C5 0.0413(9) 0.0462(9) 0.0460(9) 0.0210(8) -0.0008(7) 0.0110(7) C6 0.0465(9) 0.0514(10) 0.0557(11) 0.0232(8) 0.0104(8) 0.0205(8) C7 0.0553(10) 0.0457(9) 0.0443(9) 0.0139(8) 0.0111(8) 0.0190(8) C8 0.0465(9) 0.0416(8) 0.0346(8) 0.0115(7) 0.0033(7) 0.0123(7) C9 0.0398(8) 0.0313(7) 0.0328(8) 0.0132(6) 0.0029(6) 0.0057(6) N10 0.0425(7) 0.0396(7) 0.0312(7) 0.0118(6) -0.0035(5) 0.0079(6) C11 0.0394(8) 0.0330(7) 0.0331(8) 0.0139(6) 0.0068(6) 0.0055(6) C12 0.0432(8) 0.0334(7) 0.0335(8) 0.0146(6) 0.0068(7) 0.0050(6) C13 0.0391(8) 0.0332(7) 0.0330(8) 0.0146(6) 0.0049(6) 0.0076(6) C14 0.0402(8) 0.0319(7) 0.0352(8) 0.0152(6) 0.0034(6) 0.0052(6) N15 0.0502(8) 0.0470(7) 0.0341(7) 0.0037(6) -0.0040(6) 0.0210(6) Cl16 0.0646(3) 0.0450(2) 0.0369(2) 0.00745(18) -0.00381(19) 0.0222(2) O17 0.0718(9) 0.0540(7) 0.0377(7) 0.0129(6) -0.0079(6) 0.0034(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.363(2) . ? C1 C11 1.417(2) . ? C1 H1 0.9300 . ? C2 C3 1.406(2) . ? C2 H2 0.9300 . ? C3 C4 1.363(2) . ? C3 H3 0.9300 . ? C4 C12 1.407(2) . ? C4 H4 0.9300 . ? C5 C6 1.358(2) . ? C5 C14 1.409(2) . ? C5 H5 0.9300 . ? C6 C7 1.405(2) . ? C6 H6 0.9300 . ? C7 C8 1.363(2) . ? C7 H7 0.9300 . ? C8 C13 1.419(2) . ? C8 H8 0.9300 . ? C9 N15 1.3232(19) . ? C9 C11 1.436(2) . ? C9 C13 1.437(2) . ? N10 C14 1.362(2) . ? N10 C12 1.363(2) . ? N10 H10 0.8600 . ? C11 C12 1.410(2) . ? C13 C14 1.413(2) . ? N15 H15A 0.8600 . ? N15 H15B 0.8600 . ? O17 H17A 0.828(15) . ? O17 H17B 0.843(15) . ? 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 C11 120.84(15) . . ? C2 C1 H1 119.6 . . ? C11 C1 H1 119.6 . . ? C1 C2 C3 120.30(16) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.61(15) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C12 119.83(15) . . ? C3 C4 H4 120.1 . . ? C12 C4 H4 120.1 . . ? C6 C5 C14 120.09(15) . . ? C6 C5 H5 120.0 . . ? C14 C5 H5 120.0 . . ? C5 C6 C7 120.56(15) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 120.42(16) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C13 120.82(15) . . ? C7 C8 H8 119.6 . . ? C13 C8 H8 119.6 . . ? N15 C9 C11 120.62(14) . . ? N15 C9 C13 120.82(14) . . ? C11 C9 C13 118.56(13) . . ? C14 N10 C12 122.82(13) . . ? C14 N10 H10 118.6 . . ? C12 N10 H10 118.6 . . ? C12 C11 C1 118.00(14) . . ? C12 C11 C9 119.30(14) . . ? C1 C11 C9 122.69(14) . . ? N10 C12 C4 119.51(14) . . ? N10 C12 C11 120.08(14) . . ? C4 C12 C11 120.42(15) . . ? C14 C13 C8 117.88(14) . . ? C14 C13 C9 119.02(14) . . ? C8 C13 C9 123.09(14) . . ? N10 C14 C5 119.56(13) . . ? N10 C14 C13 120.21(14) . . ? C5 C14 C13 120.23(14) . . ? C9 N15 H15A 120.0 . . ? C9 N15 H15B 120.0 . . ? H15A N15 H15B 120.0 . . ? H17A O17 H17B 109.9(19) . . ? 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 C11 C1 C2 C3 -0.3(3) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C12 0.9(3) . . . . ? C14 C5 C6 C7 0.0(3) . . . . ? C5 C6 C7 C8 0.1(3) . . . . ? C6 C7 C8 C13 -0.2(3) . . . . ? C2 C1 C11 C12 0.2(2) . . . . ? C2 C1 C11 C9 -178.32(15) . . . . ? N15 C9 C11 C12 -179.45(13) . . . . ? C13 C9 C11 C12 0.5(2) . . . . ? N15 C9 C11 C1 -0.9(2) . . . . ? C13 C9 C11 C1 179.00(14) . . . . ? C14 N10 C12 C4 -179.87(14) . . . . ? C14 N10 C12 C11 0.0(2) . . . . ? C3 C4 C12 N10 178.92(14) . . . . ? C3 C4 C12 C11 -1.0(2) . . . . ? C1 C11 C12 N10 -179.48(14) . . . . ? C9 C11 C12 N10 -0.9(2) . . . . ? C1 C11 C12 C4 0.4(2) . . . . ? C9 C11 C12 C4 179.02(14) . . . . ? C7 C8 C13 C14 0.3(2) . . . . ? C7 C8 C13 C9 -178.26(14) . . . . ? N15 C9 C13 C14 -179.35(14) . . . . ? C11 C9 C13 C14 0.7(2) . . . . ? N15 C9 C13 C8 -0.8(2) . . . . ? C11 C9 C13 C8 179.25(14) . . . . ? C12 N10 C14 C5 -178.76(13) . . . . ? C12 N10 C14 C13 1.2(2) . . . . ? C6 C5 C14 N10 -179.97(15) . . . . ? C6 C5 C14 C13 0.1(2) . . . . ? C8 C13 C14 N10 179.82(13) . . . . ? C9 C13 C14 N10 -1.6(2) . . . . ? C8 C13 C14 C5 -0.2(2) . . . . ? C9 C13 C14 C5 178.41(14) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.180 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 934871' ####################################################################### # # 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_Global2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 N2, Br, H2 O' _chemical_formula_sum 'C13 H13 Br N2 O' _chemical_formula_weight 293.16 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8111(3) _cell_length_b 9.2247(4) _cell_length_c 9.9092(4) _cell_angle_alpha 112.132(4) _cell_angle_beta 94.384(3) _cell_angle_gamma 105.209(3) _cell_volume 625.84(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 13785 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 25.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 3.269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.316 _exptl_absorpt_correction_T_max 0.751 _exptl_absorpt_process_details ; CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd., 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(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 'Oxford Diffraction Ruby CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.4002 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13875 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2327 _reflns_number_gt 1957 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_cell_refinement 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 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^)+(0.0372P)^2^+0.8349P] 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 2327 _refine_ls_number_parameters 160 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 0.2340(5) 0.8447(5) 0.4723(4) 0.0442(9) Uani 1 1 d . . . H1 H 0.1415 0.8164 0.3932 0.053 Uiso 1 1 calc R . . C2 C 0.2376(6) 0.9613(5) 0.6076(5) 0.0526(10) Uani 1 1 d . . . H2 H 0.1477 1.0115 0.6207 0.063 Uiso 1 1 calc R . . C3 C 0.3767(6) 1.0057(5) 0.7275(4) 0.0542(11) Uani 1 1 d . . . H3 H 0.3785 1.0860 0.8196 0.065 Uiso 1 1 calc R . . C4 C 0.5088(6) 0.9335(5) 0.7111(4) 0.0481(10) Uani 1 1 d . . . H4 H 0.6004 0.9643 0.7917 0.058 Uiso 1 1 calc R . . C5 C 0.7868(5) 0.5507(5) 0.4170(4) 0.0465(9) Uani 1 1 d . . . H5 H 0.8763 0.5869 0.5004 0.056 Uiso 1 1 calc R . . C6 C 0.7929(6) 0.4315(5) 0.2872(5) 0.0518(10) Uani 1 1 d . . . H6 H 0.8865 0.3859 0.2824 0.062 Uiso 1 1 calc R . . C7 C 0.6596(6) 0.3760(5) 0.1602(4) 0.0497(10) Uani 1 1 d . . . H7 H 0.6656 0.2942 0.0718 0.060 Uiso 1 1 calc R . . C8 C 0.5218(5) 0.4409(5) 0.1655(4) 0.0419(8) Uani 1 1 d . . . H8 H 0.4343 0.4029 0.0804 0.050 Uiso 1 1 calc R . . C9 C 0.3682(5) 0.6406(4) 0.3100(4) 0.0371(8) Uani 1 1 d . . . N10 N 0.6386(4) 0.7388(4) 0.5562(3) 0.0426(7) Uani 1 1 d . . . H10 H 0.7217 0.7689 0.6323 0.051 Uiso 1 1 calc R . . C11 C 0.3689(5) 0.7658(4) 0.4500(4) 0.0361(8) Uani 1 1 d . . . C12 C 0.5073(5) 0.8120(4) 0.5722(4) 0.0389(8) Uani 1 1 d . . . C13 C 0.5093(5) 0.5652(4) 0.2981(4) 0.0355(8) Uani 1 1 d . . . C14 C 0.6449(5) 0.6199(4) 0.4255(4) 0.0381(8) Uani 1 1 d . . . N15 N 0.2409(4) 0.5950(4) 0.1936(3) 0.0483(8) Uani 1 1 d . . . H15A H 0.1571 0.6407 0.2013 0.058 Uiso 1 1 calc R . . H15B H 0.2415 0.5196 0.1099 0.058 Uiso 1 1 calc R . . Br16 Br -0.05379(6) 0.76771(5) 0.10272(4) 0.05522(17) Uani 1 1 d . . . O17 O 0.9166(5) 0.8286(4) 0.7954(3) 0.0630(8) Uani 1 1 d D . . H17A H 0.899(8) 0.811(6) 0.870(4) 0.094 Uiso 1 1 d D . . H17B H 0.964(7) 0.931(3) 0.820(5) 0.094 Uiso 1 1 d 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 0.044(2) 0.047(2) 0.039(2) 0.0174(18) 0.0076(17) 0.0112(17) C2 0.055(3) 0.054(2) 0.047(2) 0.016(2) 0.019(2) 0.020(2) C3 0.067(3) 0.046(2) 0.035(2) 0.0063(18) 0.016(2) 0.010(2) C4 0.059(3) 0.042(2) 0.0312(19) 0.0101(17) 0.0029(17) 0.0063(19) C5 0.044(2) 0.047(2) 0.048(2) 0.0225(19) -0.0005(17) 0.0127(18) C6 0.045(2) 0.052(2) 0.064(3) 0.028(2) 0.008(2) 0.0202(19) C7 0.057(3) 0.047(2) 0.042(2) 0.0141(18) 0.0117(19) 0.019(2) C8 0.047(2) 0.043(2) 0.0342(19) 0.0143(16) 0.0043(16) 0.0144(17) C9 0.0385(19) 0.0356(18) 0.0334(18) 0.0152(15) 0.0036(15) 0.0052(15) N10 0.0458(18) 0.0425(17) 0.0301(16) 0.0125(14) -0.0052(13) 0.0062(14) C11 0.0393(19) 0.0327(18) 0.0331(18) 0.0156(15) 0.0050(15) 0.0036(15) C12 0.042(2) 0.0361(19) 0.0339(18) 0.0169(16) 0.0049(15) 0.0029(16) C13 0.041(2) 0.0322(18) 0.0307(17) 0.0142(15) 0.0027(15) 0.0072(15) C14 0.041(2) 0.0360(19) 0.0373(19) 0.0202(16) 0.0022(15) 0.0051(15) N15 0.0512(19) 0.0478(19) 0.0345(16) 0.0032(14) -0.0065(14) 0.0221(16) Br16 0.0701(3) 0.0469(2) 0.0410(2) 0.00894(17) -0.00479(18) 0.0245(2) O17 0.075(2) 0.0578(18) 0.0402(16) 0.0180(14) -0.0093(15) 0.0042(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 C1 C2 1.359(5) . ? C1 C11 1.416(5) . ? C1 H1 0.9300 . ? C2 C3 1.400(6) . ? C2 H2 0.9300 . ? C3 C4 1.357(6) . ? C3 H3 0.9300 . ? C4 C12 1.406(5) . ? C4 H4 0.9300 . ? C5 C6 1.355(6) . ? C5 C14 1.410(5) . ? C5 H5 0.9300 . ? C6 C7 1.401(6) . ? C6 H6 0.9300 . ? C7 C8 1.358(5) . ? C7 H7 0.9300 . ? C8 C13 1.412(5) . ? C8 H8 0.9300 . ? C9 N15 1.318(4) . ? C9 C11 1.430(5) . ? C9 C13 1.440(5) . ? N10 C12 1.357(5) . ? N10 C14 1.360(5) . ? N10 H10 0.8600 . ? C11 C12 1.410(5) . ? C13 C14 1.415(5) . ? N15 H15A 0.8600 . ? N15 H15B 0.8600 . ? O17 H17A 0.831(19) . ? O17 H17B 0.845(19) . ? 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 C11 121.0(4) . . ? C2 C1 H1 119.5 . . ? C11 C1 H1 119.5 . . ? C1 C2 C3 120.1(4) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.9(4) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C12 120.0(4) . . ? C3 C4 H4 120.0 . . ? C12 C4 H4 120.0 . . ? C6 C5 C14 120.0(4) . . ? C6 C5 H5 120.0 . . ? C14 C5 H5 120.0 . . ? C5 C6 C7 120.7(4) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 120.3(4) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C13 121.1(3) . . ? C7 C8 H8 119.5 . . ? C13 C8 H8 119.5 . . ? N15 C9 C11 120.7(3) . . ? N15 C9 C13 120.4(3) . . ? C11 C9 C13 118.9(3) . . ? C12 N10 C14 123.1(3) . . ? C12 N10 H10 118.5 . . ? C14 N10 H10 118.5 . . ? C12 C11 C1 118.0(3) . . ? C12 C11 C9 119.2(3) . . ? C1 C11 C9 122.7(3) . . ? N10 C12 C4 119.9(3) . . ? N10 C12 C11 120.1(3) . . ? C4 C12 C11 120.0(4) . . ? C8 C13 C14 117.9(3) . . ? C8 C13 C9 123.6(3) . . ? C14 C13 C9 118.5(3) . . ? N10 C14 C5 119.8(3) . . ? N10 C14 C13 120.3(3) . . ? C5 C14 C13 119.9(3) . . ? C9 N15 H15A 120.0 . . ? C9 N15 H15B 120.0 . . ? H15A N15 H15B 120.0 . . ? H17A O17 H17B 110(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 C11 C1 C2 C3 0.4(6) . . . . ? C1 C2 C3 C4 -0.3(6) . . . . ? C2 C3 C4 C12 0.0(6) . . . . ? C14 C5 C6 C7 0.3(6) . . . . ? C5 C6 C7 C8 -0.2(6) . . . . ? C6 C7 C8 C13 0.0(6) . . . . ? C2 C1 C11 C12 -0.1(5) . . . . ? C2 C1 C11 C9 178.9(4) . . . . ? N15 C9 C11 C12 -179.8(3) . . . . ? C13 C9 C11 C12 0.0(5) . . . . ? N15 C9 C11 C1 1.2(5) . . . . ? C13 C9 C11 C1 -179.0(3) . . . . ? C14 N10 C12 C4 179.6(3) . . . . ? C14 N10 C12 C11 0.0(5) . . . . ? C3 C4 C12 N10 -179.4(4) . . . . ? C3 C4 C12 C11 0.2(6) . . . . ? C1 C11 C12 N10 179.5(3) . . . . ? C9 C11 C12 N10 0.5(5) . . . . ? C1 C11 C12 C4 -0.2(5) . . . . ? C9 C11 C12 C4 -179.2(3) . . . . ? C7 C8 C13 C14 0.0(5) . . . . ? C7 C8 C13 C9 179.0(4) . . . . ? N15 C9 C13 C8 0.0(5) . . . . ? C11 C9 C13 C8 -179.8(3) . . . . ? N15 C9 C13 C14 179.0(3) . . . . ? C11 C9 C13 C14 -0.8(5) . . . . ? C12 N10 C14 C5 179.3(3) . . . . ? C12 N10 C14 C13 -0.9(5) . . . . ? C6 C5 C14 N10 179.5(4) . . . . ? C6 C5 C14 C13 -0.3(6) . . . . ? C8 C13 C14 N10 -179.7(3) . . . . ? C9 C13 C14 N10 1.3(5) . . . . ? C8 C13 C14 C5 0.2(5) . . . . ? C9 C13 C14 C5 -178.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.316 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 934872' ####################################################################### # # 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_Global3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 N2, I, H2 O' _chemical_formula_sum 'C13 H13 I N2 O' _chemical_formula_weight 340.15 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/c' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.087(2) _cell_length_b 18.483(4) _cell_length_c 7.299(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.53(3) _cell_angle_gamma 90.00 _cell_volume 1323.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 9813 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 25.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 2.406 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.460 _exptl_absorpt_correction_T_max 0.839 _exptl_absorpt_process_details ; CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd., 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(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 'Oxford Diffraction Ruby CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.4002 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9813 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.0712 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2460 _reflns_number_gt 1337 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_cell_refinement 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 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^)+(0.0341P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2460 _refine_ls_number_parameters 160 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0905 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0753 _refine_ls_wR_factor_gt 0.0663 _refine_ls_goodness_of_fit_ref 0.858 _refine_ls_restrained_S_all 0.858 _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 0.5428(5) 0.2472(3) 0.5675(6) 0.0511(13) Uani 1 1 d . . . H1 H 0.5860 0.2908 0.6072 0.061 Uiso 1 1 calc R . . C2 C 0.6082(5) 0.1846(3) 0.6228(6) 0.0585(13) Uani 1 1 d . . . H2 H 0.6951 0.1850 0.7021 0.070 Uiso 1 1 calc R . . C3 C 0.5447(7) 0.1190(3) 0.5603(8) 0.0731(16) Uani 1 1 d . . . H3 H 0.5909 0.0760 0.5972 0.088 Uiso 1 1 calc R . . C4 C 0.4173(6) 0.1167(3) 0.4473(8) 0.0679(16) Uani 1 1 d . . . H4 H 0.3763 0.0725 0.4073 0.081 Uiso 1 1 calc R . . C5 C 0.0139(5) 0.2321(3) 0.1053(6) 0.0548(13) Uani 1 1 d . . . H5 H -0.0220 0.1864 0.0711 0.066 Uiso 1 1 calc R . . C6 C -0.0604(5) 0.2918(3) 0.0439(7) 0.0606(14) Uani 1 1 d . . . H6 H -0.1481 0.2869 -0.0314 0.073 Uiso 1 1 calc R . . C7 C -0.0073(6) 0.3610(3) 0.0922(7) 0.0671(15) Uani 1 1 d . . . H7 H -0.0589 0.4018 0.0477 0.081 Uiso 1 1 calc R . . C8 C 0.1200(5) 0.3684(3) 0.2043(7) 0.0555(13) Uani 1 1 d . . . H8 H 0.1545 0.4146 0.2362 0.067 Uiso 1 1 calc R . . C9 C 0.3364(5) 0.3134(3) 0.3892(6) 0.0456(11) Uani 1 1 d . . . N10 N 0.2197(4) 0.1793(2) 0.2811(5) 0.0510(10) Uani 1 1 d . . . H10 H 0.1833 0.1379 0.2477 0.061 Uiso 1 1 calc R . . C11 C 0.4088(5) 0.2479(2) 0.4494(6) 0.0389(11) Uani 1 1 d . . . C12 C 0.3492(5) 0.1810(3) 0.3921(6) 0.0479(12) Uani 1 1 d . . . C13 C 0.2004(5) 0.3082(3) 0.2730(6) 0.0447(12) Uani 1 1 d . . . C14 C 0.1460(5) 0.2393(3) 0.2213(6) 0.0421(11) Uani 1 1 d . . . N15 N 0.3915(4) 0.3772(2) 0.4392(5) 0.0581(11) Uani 1 1 d . . . H15A H 0.4727 0.3800 0.5094 0.070 Uiso 1 1 calc R . . H15B H 0.3462 0.4160 0.4016 0.070 Uiso 1 1 calc R . . I16 I 0.74503(4) 0.437411(19) 0.60423(5) 0.07324(17) Uani 1 1 d . . . O17 O 0.1108(4) 0.0398(2) 0.2185(7) 0.0954(13) Uani 1 1 d D . . H17B H 0.147(6) 0.006(3) 0.170(9) 0.143 Uiso 1 1 d D . . H17A H 0.025(2) 0.038(4) 0.180(10) 0.143 Uiso 1 1 d 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 0.044(3) 0.056(4) 0.052(3) 0.006(3) 0.010(3) -0.005(3) C2 0.044(3) 0.066(4) 0.063(3) 0.008(3) 0.007(3) 0.000(3) C3 0.074(5) 0.066(4) 0.080(4) 0.016(3) 0.017(4) 0.021(3) C4 0.068(4) 0.056(4) 0.073(4) 0.001(3) 0.003(3) 0.002(3) C5 0.048(3) 0.069(3) 0.047(3) -0.015(3) 0.011(3) -0.019(3) C6 0.038(3) 0.083(5) 0.058(3) -0.009(3) 0.007(3) 0.000(3) C7 0.048(4) 0.079(4) 0.071(4) 0.003(3) 0.009(3) 0.021(3) C8 0.043(3) 0.054(3) 0.066(4) -0.006(3) 0.007(3) -0.004(3) C9 0.052(3) 0.049(3) 0.039(3) -0.007(2) 0.017(2) -0.005(3) N10 0.050(3) 0.049(2) 0.055(3) -0.009(2) 0.015(2) -0.012(2) C11 0.031(3) 0.052(3) 0.038(3) 0.004(2) 0.015(2) 0.000(2) C12 0.047(3) 0.052(3) 0.046(3) -0.004(3) 0.013(3) -0.003(3) C13 0.038(3) 0.051(3) 0.049(3) -0.001(3) 0.018(3) 0.001(3) C14 0.040(3) 0.052(3) 0.038(3) -0.002(2) 0.016(2) -0.001(3) N15 0.039(2) 0.053(3) 0.075(3) 0.001(2) -0.004(2) -0.009(2) I16 0.0483(2) 0.0514(2) 0.1085(3) 0.0040(2) -0.00497(18) -0.0061(2) O17 0.067(3) 0.072(3) 0.139(4) -0.035(2) 0.008(3) -0.011(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 C1 C2 1.346(6) . ? C1 C11 1.423(6) . ? C1 H1 0.9300 . ? C2 C3 1.397(7) . ? C2 H2 0.9300 . ? C3 C4 1.356(8) . ? C3 H3 0.9300 . ? C4 C12 1.386(7) . ? C4 H4 0.9300 . ? C5 C6 1.350(7) . ? C5 C14 1.408(6) . ? C5 H5 0.9300 . ? C6 C7 1.400(7) . ? C6 H6 0.9300 . ? C7 C8 1.359(7) . ? C7 H7 0.9300 . ? C8 C13 1.400(6) . ? C8 H8 0.9300 . ? C9 N15 1.319(6) . ? C9 C11 1.429(6) . ? C9 C13 1.437(6) . ? N10 C14 1.350(6) . ? N10 C12 1.367(6) . ? N10 H10 0.8600 . ? C11 C12 1.396(6) . ? C13 C14 1.402(6) . ? N15 H15A 0.8600 . ? N15 H15B 0.8600 . ? O17 H17B 0.841(19) . ? O17 H17A 0.847(19) . ? 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 C11 121.3(5) . . ? C2 C1 H1 119.4 . . ? C11 C1 H1 119.4 . . ? C1 C2 C3 119.5(5) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 121.6(5) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C12 118.9(5) . . ? C3 C4 H4 120.5 . . ? C12 C4 H4 120.5 . . ? C6 C5 C14 119.7(5) . . ? C6 C5 H5 120.2 . . ? C14 C5 H5 120.2 . . ? C5 C6 C7 120.9(5) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 119.7(5) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C13 121.5(5) . . ? C7 C8 H8 119.3 . . ? C13 C8 H8 119.3 . . ? N15 C9 C11 121.4(4) . . ? N15 C9 C13 120.4(4) . . ? C11 C9 C13 118.2(4) . . ? C14 N10 C12 123.4(4) . . ? C14 N10 H10 118.3 . . ? C12 N10 H10 118.3 . . ? C12 C11 C1 117.1(4) . . ? C12 C11 C9 120.3(4) . . ? C1 C11 C9 122.6(4) . . ? N10 C12 C4 119.5(5) . . ? N10 C12 C11 118.9(4) . . ? C4 C12 C11 121.6(5) . . ? C8 C13 C14 117.9(4) . . ? C8 C13 C9 123.4(4) . . ? C14 C13 C9 118.7(4) . . ? N10 C14 C13 120.5(4) . . ? N10 C14 C5 119.2(5) . . ? C13 C14 C5 120.3(5) . . ? C9 N15 H15A 120.0 . . ? C9 N15 H15B 120.0 . . ? H15A N15 H15B 120.0 . . ? H17B O17 H17A 111(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 C11 C1 C2 C3 1.3(7) . . . . ? C1 C2 C3 C4 -1.1(8) . . . . ? C2 C3 C4 C12 0.3(8) . . . . ? C14 C5 C6 C7 0.8(7) . . . . ? C5 C6 C7 C8 -0.9(8) . . . . ? C6 C7 C8 C13 0.2(8) . . . . ? C2 C1 C11 C12 -0.7(6) . . . . ? C2 C1 C11 C9 179.6(4) . . . . ? N15 C9 C11 C12 -178.9(4) . . . . ? C13 C9 C11 C12 1.5(6) . . . . ? N15 C9 C11 C1 0.8(6) . . . . ? C13 C9 C11 C1 -178.8(4) . . . . ? C14 N10 C12 C4 179.9(4) . . . . ? C14 N10 C12 C11 0.8(6) . . . . ? C3 C4 C12 N10 -178.7(5) . . . . ? C3 C4 C12 C11 0.3(7) . . . . ? C1 C11 C12 N10 178.9(4) . . . . ? C9 C11 C12 N10 -1.4(6) . . . . ? C1 C11 C12 C4 -0.1(6) . . . . ? C9 C11 C12 C4 179.6(4) . . . . ? C7 C8 C13 C14 0.5(7) . . . . ? C7 C8 C13 C9 178.9(4) . . . . ? N15 C9 C13 C8 0.9(6) . . . . ? C11 C9 C13 C8 -179.5(4) . . . . ? N15 C9 C13 C14 179.3(4) . . . . ? C11 C9 C13 C14 -1.0(6) . . . . ? C12 N10 C14 C13 -0.4(6) . . . . ? C12 N10 C14 C5 179.2(4) . . . . ? C8 C13 C14 N10 179.1(4) . . . . ? C9 C13 C14 N10 0.5(6) . . . . ? C8 C13 C14 C5 -0.6(6) . . . . ? C9 C13 C14 C5 -179.1(4) . . . . ? C6 C5 C14 N10 -179.7(4) . . . . ? C6 C5 C14 C13 -0.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.526 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.079 _database_code_depnum_ccdc_archive 'CCDC 934873' ####################################################################### # # 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_Global4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 N2, C H4 O, Cl' _chemical_formula_sum 'C14 H15 Cl N2 O' _chemical_formula_weight 262.73 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' 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' N N 0.0061 0.0033 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0907(10) _cell_length_b 9.6958(9) _cell_length_c 10.6145(12) _cell_angle_alpha 98.732(9) _cell_angle_beta 101.034(11) _cell_angle_gamma 110.132(11) _cell_volume 653.46(15) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4352 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 25.50 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.282 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.871 _exptl_absorpt_correction_T_max 0.963 _exptl_absorpt_process_details ; CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd., 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(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 'Oxford Diffraction Ruby CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.4002 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4352 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2416 _reflns_number_gt 2017 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_cell_refinement 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 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^)+(0.0601P)^2^+0.1293P] 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 2416 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1146 _refine_ls_wR_factor_gt 0.1067 _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 C1 C 0.1108(3) 0.6907(2) 0.21213(18) 0.0482(5) Uani 1 1 d . . . H1 H 0.0979 0.5963 0.2272 0.058 Uiso 1 1 calc R . . C2 C 0.0724(3) 0.7075(2) 0.0856(2) 0.0566(5) Uani 1 1 d . . . H2 H 0.0301 0.6240 0.0154 0.068 Uiso 1 1 calc R . . C3 C 0.0961(3) 0.8489(2) 0.06083(19) 0.0535(5) Uani 1 1 d . . . H3 H 0.0741 0.8600 -0.0256 0.064 Uiso 1 1 calc R . . C4 C 0.1511(3) 0.9704(2) 0.16252(19) 0.0472(5) Uani 1 1 d . . . H4 H 0.1665 1.0644 0.1454 0.057 Uiso 1 1 calc R . . C5 C 0.3146(3) 1.2021(2) 0.6203(2) 0.0497(5) Uani 1 1 d . . . H5 H 0.3196 1.2915 0.5964 0.060 Uiso 1 1 calc R . . C6 C 0.3520(3) 1.1971(2) 0.7497(2) 0.0562(5) Uani 1 1 d . . . H6 H 0.3831 1.2839 0.8143 0.067 Uiso 1 1 calc R . . C7 C 0.3443(3) 1.0642(2) 0.7868(2) 0.0542(5) Uani 1 1 d . . . H7 H 0.3703 1.0627 0.8757 0.065 Uiso 1 1 calc R . . C8 C 0.2988(3) 0.9361(2) 0.69337(18) 0.0451(4) Uani 1 1 d . . . H8 H 0.2935 0.8478 0.7194 0.054 Uiso 1 1 calc R . . C9 C 0.2119(2) 0.80355(18) 0.45563(17) 0.0359(4) Uani 1 1 d . . . N10 N 0.2330(2) 1.07691(16) 0.39333(15) 0.0417(4) Uani 1 1 d . . . H10 H 0.2416 1.1616 0.3742 0.050 Uiso 1 1 calc R . . C11 C 0.1695(2) 0.81432(19) 0.32028(17) 0.0361(4) Uani 1 1 d . . . C12 C 0.1849(2) 0.95485(19) 0.29329(17) 0.0376(4) Uani 1 1 d . . . C13 C 0.2595(2) 0.93528(19) 0.55761(17) 0.0363(4) Uani 1 1 d . . . C14 C 0.2682(2) 1.07075(19) 0.52248(18) 0.0382(4) Uani 1 1 d . . . N15 N 0.2086(2) 0.67544(17) 0.48497(15) 0.0461(4) Uani 1 1 d . . . H15B H 0.2351 0.6700 0.5662 0.055 Uiso 1 1 calc R . . H15A H 0.1798 0.5974 0.4229 0.055 Uiso 1 1 calc R . . Cl16 Cl 0.17839(8) 0.36139(5) 0.30289(5) 0.0574(2) Uani 1 1 d . . . O17 O 0.3838(3) 0.6034(2) 0.72784(15) 0.0764(5) Uani 1 1 d . . . H17 H 0.4924 0.6050 0.7108 0.115 Uiso 1 1 calc R . . C18 C 0.4137(5) 0.6369(3) 0.8643(2) 0.0816(7) Uani 1 1 d . . . H18A H 0.5575 0.6987 0.9064 0.122 Uiso 1 1 calc R . . H18B H 0.3756 0.5447 0.8939 0.122 Uiso 1 1 calc R . . H18C H 0.3286 0.6903 0.8867 0.122 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 C1 0.0653(12) 0.0335(10) 0.0446(10) 0.0077(8) 0.0075(9) 0.0217(9) C2 0.0779(13) 0.0438(11) 0.0446(11) 0.0042(9) 0.0062(10) 0.0270(10) C3 0.0664(12) 0.0563(12) 0.0414(11) 0.0165(9) 0.0068(9) 0.0300(10) C4 0.0537(11) 0.0413(10) 0.0504(11) 0.0187(9) 0.0068(9) 0.0233(9) C5 0.0495(10) 0.0352(10) 0.0630(13) 0.0019(9) 0.0116(9) 0.0203(8) C6 0.0562(11) 0.0497(12) 0.0557(13) -0.0078(10) 0.0106(9) 0.0227(10) C7 0.0586(11) 0.0586(13) 0.0415(11) 0.0011(9) 0.0116(9) 0.0233(10) C8 0.0472(10) 0.0446(10) 0.0440(10) 0.0090(8) 0.0116(8) 0.0190(8) C9 0.0337(8) 0.0318(9) 0.0429(9) 0.0096(7) 0.0091(7) 0.0138(7) N10 0.0481(8) 0.0290(8) 0.0496(9) 0.0101(7) 0.0081(7) 0.0191(6) C11 0.0360(8) 0.0322(9) 0.0415(9) 0.0100(7) 0.0071(7) 0.0158(7) C12 0.0353(8) 0.0330(9) 0.0453(10) 0.0099(8) 0.0064(7) 0.0163(7) C13 0.0321(8) 0.0346(9) 0.0418(9) 0.0060(7) 0.0082(7) 0.0144(7) C14 0.0324(8) 0.0346(9) 0.0478(10) 0.0062(8) 0.0082(7) 0.0157(7) N15 0.0671(10) 0.0332(8) 0.0401(8) 0.0104(7) 0.0117(7) 0.0222(7) Cl16 0.0805(4) 0.0384(3) 0.0630(3) 0.0143(2) 0.0193(3) 0.0333(3) O17 0.0878(11) 0.0979(13) 0.0583(10) 0.0235(9) 0.0196(8) 0.0511(10) C18 0.1030(19) 0.0824(19) 0.0612(15) 0.0214(13) 0.0311(14) 0.0309(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 1.364(3) . ? C1 C11 1.408(2) . ? C1 H1 0.9300 . ? C2 C3 1.395(3) . ? C2 H2 0.9300 . ? C3 C4 1.357(3) . ? C3 H3 0.9300 . ? C4 C12 1.403(3) . ? C4 H4 0.9300 . ? C5 C6 1.360(3) . ? C5 C14 1.410(3) . ? C5 H5 0.9300 . ? C6 C7 1.391(3) . ? C6 H6 0.9300 . ? C7 C8 1.363(3) . ? C7 H7 0.9300 . ? C8 C13 1.413(3) . ? C8 H8 0.9300 . ? C9 N15 1.319(2) . ? C9 C13 1.435(2) . ? C9 C11 1.438(2) . ? N10 C12 1.359(2) . ? N10 C14 1.360(2) . ? N10 H10 0.8600 . ? C11 C12 1.407(2) . ? C13 C14 1.404(2) . ? N15 H15B 0.8600 . ? N15 H15A 0.8600 . ? O17 C18 1.393(3) . ? O17 H17 0.8200 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C11 120.97(17) . . ? C2 C1 H1 119.5 . . ? C11 C1 H1 119.5 . . ? C1 C2 C3 120.46(19) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 120.20(18) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C12 120.30(16) . . ? C3 C4 H4 119.8 . . ? C12 C4 H4 119.8 . . ? C6 C5 C14 119.47(18) . . ? C6 C5 H5 120.3 . . ? C14 C5 H5 120.3 . . ? C5 C6 C7 120.92(19) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C8 C7 C6 120.29(19) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C13 121.08(18) . . ? C7 C8 H8 119.5 . . ? C13 C8 H8 119.5 . . ? N15 C9 C13 120.95(15) . . ? N15 C9 C11 120.49(16) . . ? C13 C9 C11 118.56(14) . . ? C12 N10 C14 122.72(14) . . ? C12 N10 H10 118.6 . . ? C14 N10 H10 118.6 . . ? C12 C11 C1 117.76(16) . . ? C12 C11 C9 118.77(16) . . ? C1 C11 C9 123.46(15) . . ? N10 C12 C4 119.30(15) . . ? N10 C12 C11 120.48(15) . . ? C4 C12 C11 120.22(17) . . ? C14 C13 C8 117.64(16) . . ? C14 C13 C9 119.20(15) . . ? C8 C13 C9 123.16(15) . . ? N10 C14 C13 120.22(16) . . ? N10 C14 C5 119.17(16) . . ? C13 C14 C5 120.60(17) . . ? C9 N15 H15B 120.0 . . ? C9 N15 H15A 120.0 . . ? H15B N15 H15A 120.0 . . ? C18 O17 H17 109.5 . . ? O17 C18 H18A 109.5 . . ? O17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C1 C2 C3 1.7(3) . . . . ? C1 C2 C3 C4 -2.2(3) . . . . ? C2 C3 C4 C12 0.1(3) . . . . ? C14 C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 0.0(3) . . . . ? C6 C7 C8 C13 0.3(3) . . . . ? C2 C1 C11 C12 0.7(3) . . . . ? C2 C1 C11 C9 -179.97(18) . . . . ? N15 C9 C11 C12 -176.82(15) . . . . ? C13 C9 C11 C12 2.7(2) . . . . ? N15 C9 C11 C1 3.8(3) . . . . ? C13 C9 C11 C1 -176.66(15) . . . . ? C14 N10 C12 C4 -179.92(15) . . . . ? C14 N10 C12 C11 0.0(2) . . . . ? C3 C4 C12 N10 -177.80(16) . . . . ? C3 C4 C12 C11 2.3(3) . . . . ? C1 C11 C12 N10 177.44(15) . . . . ? C9 C11 C12 N10 -1.9(2) . . . . ? C1 C11 C12 C4 -2.7(2) . . . . ? C9 C11 C12 C4 177.93(15) . . . . ? C7 C8 C13 C14 -0.3(3) . . . . ? C7 C8 C13 C9 179.70(16) . . . . ? N15 C9 C13 C14 177.95(15) . . . . ? C11 C9 C13 C14 -1.5(2) . . . . ? N15 C9 C13 C8 -2.0(2) . . . . ? C11 C9 C13 C8 178.46(15) . . . . ? C12 N10 C14 C13 1.3(2) . . . . ? C12 N10 C14 C5 -179.16(15) . . . . ? C8 C13 C14 N10 179.60(15) . . . . ? C9 C13 C14 N10 -0.4(2) . . . . ? C8 C13 C14 C5 0.0(2) . . . . ? C9 C13 C14 C5 -179.98(15) . . . . ? C6 C5 C14 N10 -179.34(16) . . . . ? C6 C5 C14 C13 0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.195 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 934874' ####################################################################### # # 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_Global5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 N2, C H4 O, Br' _chemical_formula_sum 'C14 H15 Br N2 O' _chemical_formula_weight 307.18 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' Br Br -0.2901 2.4595 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1357(9) _cell_length_b 9.8039(14) _cell_length_c 10.6502(17) _cell_angle_alpha 73.234(13) _cell_angle_beta 79.126(13) _cell_angle_gamma 69.980(12) _cell_volume 666.93(18) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4485 _cell_measurement_theta_min 3.39 _cell_measurement_theta_max 25.50 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 3.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.281 _exptl_absorpt_correction_T_max 0.799 _exptl_absorpt_process_details ; CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd., 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(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 'Oxford Diffraction Ruby CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.4002 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4485 _diffrn_reflns_av_R_equivalents 0.0567 _diffrn_reflns_av_sigmaI/netI 0.0876 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2466 _reflns_number_gt 1747 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_cell_refinement 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _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^+0.0000P] 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_number_reflns 2466 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1086 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _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 0.6039(6) 0.8069(4) 0.2155(4) 0.0438(11) Uani 1 1 d . . . H1 H 0.5288 0.8998 0.2312 0.053 Uiso 1 1 calc R . . C2 C 0.6574(7) 0.7933(5) 0.0905(5) 0.0513(13) Uani 1 1 d . . . H2 H 0.6211 0.8772 0.0210 0.062 Uiso 1 1 calc R . . C3 C 0.7669(7) 0.6544(5) 0.0636(5) 0.0516(12) Uani 1 1 d . . . H3 H 0.8001 0.6456 -0.0232 0.062 Uiso 1 1 calc R . . C4 C 0.8249(6) 0.5319(5) 0.1652(5) 0.0450(12) Uani 1 1 d . . . H4 H 0.8971 0.4394 0.1478 0.054 Uiso 1 1 calc R . . C5 C 0.8741(6) 0.2943(5) 0.6209(5) 0.0473(12) Uani 1 1 d . . . H5 H 0.9517 0.2062 0.5968 0.057 Uiso 1 1 calc R . . C6 C 0.8319(7) 0.2977(5) 0.7492(5) 0.0541(13) Uani 1 1 d . . . H6 H 0.8807 0.2106 0.8134 0.065 Uiso 1 1 calc R . . C7 C 0.7175(7) 0.4277(5) 0.7880(5) 0.0528(13) Uani 1 1 d . . . H7 H 0.6909 0.4273 0.8771 0.063 Uiso 1 1 calc R . . C8 C 0.6438(6) 0.5564(5) 0.6947(4) 0.0434(11) Uani 1 1 d . . . H8 H 0.5680 0.6435 0.7211 0.052 Uiso 1 1 calc R . . C9 C 0.6056(5) 0.6915(4) 0.4571(4) 0.0334(10) Uani 1 1 d . . . N10 N 0.8402(5) 0.4227(3) 0.3956(4) 0.0414(9) Uani 1 1 d . . . H10 H 0.9101 0.3392 0.3762 0.050 Uiso 1 1 calc R . . C11 C 0.6596(5) 0.6826(4) 0.3235(4) 0.0332(10) Uani 1 1 d . . . C12 C 0.7762(6) 0.5454(4) 0.2946(4) 0.0356(10) Uani 1 1 d . . . C13 C 0.6809(5) 0.5589(4) 0.5607(4) 0.0328(10) Uani 1 1 d . . . C14 C 0.7991(6) 0.4261(4) 0.5236(4) 0.0360(10) Uani 1 1 d . . . N15 N 0.4890(5) 0.8158(3) 0.4882(4) 0.0444(9) Uani 1 1 d . . . H15A H 0.4436 0.8943 0.4270 0.053 Uiso 1 1 calc R . . H15B H 0.4580 0.8188 0.5697 0.053 Uiso 1 1 calc R . . Br16 Br 0.17674(7) 1.12770(5) 0.30304(5) 0.0547(2) Uani 1 1 d . . . O17 O 0.2549(5) 0.8896(4) 0.7293(3) 0.0726(11) Uani 1 1 d . . . H17 H 0.1468 0.8954 0.7088 0.109 Uiso 1 1 calc R . . C18 C 0.2502(9) 0.8520(6) 0.8661(5) 0.0740(16) Uani 1 1 d . . . H16C H 0.1992 0.7684 0.9026 0.111 Uiso 1 1 calc R . . H16B H 0.1650 0.9359 0.8999 0.111 Uiso 1 1 calc R . . H16A H 0.3833 0.8256 0.8902 0.111 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 C1 0.045(3) 0.035(2) 0.040(3) -0.007(2) -0.003(2) -0.0001(19) C2 0.056(3) 0.043(3) 0.040(3) -0.003(2) -0.001(2) -0.004(2) C3 0.049(3) 0.058(3) 0.040(3) -0.015(2) 0.001(2) -0.007(2) C4 0.040(2) 0.040(2) 0.049(3) -0.018(2) 0.007(2) -0.0044(19) C5 0.041(3) 0.037(2) 0.056(3) -0.004(2) -0.009(2) -0.0070(19) C6 0.053(3) 0.044(3) 0.054(3) 0.009(2) -0.018(3) -0.011(2) C7 0.058(3) 0.057(3) 0.038(3) -0.001(2) -0.007(2) -0.018(2) C8 0.044(2) 0.040(2) 0.044(3) -0.010(2) -0.004(2) -0.010(2) C9 0.027(2) 0.029(2) 0.045(3) -0.0108(18) -0.0049(19) -0.0078(16) N10 0.037(2) 0.0289(18) 0.050(3) -0.0113(17) -0.0026(18) 0.0007(15) C11 0.029(2) 0.034(2) 0.033(3) -0.0096(18) 0.0015(19) -0.0057(17) C12 0.026(2) 0.032(2) 0.042(3) -0.0077(19) 0.0021(19) -0.0042(16) C13 0.027(2) 0.033(2) 0.038(3) -0.0071(18) -0.0025(19) -0.0108(17) C14 0.029(2) 0.034(2) 0.042(3) -0.0058(19) -0.005(2) -0.0083(17) N15 0.057(2) 0.0292(18) 0.037(2) -0.0071(15) -0.0040(18) -0.0016(16) Br16 0.0498(3) 0.0388(3) 0.0632(4) -0.0134(2) -0.0082(2) 0.0038(2) O17 0.062(2) 0.105(3) 0.052(2) -0.029(2) -0.0047(19) -0.020(2) C18 0.091(4) 0.082(4) 0.055(4) -0.020(3) -0.008(3) -0.032(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 C2 1.344(6) . ? C1 C11 1.412(5) . ? C1 H1 0.9300 . ? C2 C3 1.400(6) . ? C2 H2 0.9300 . ? C3 C4 1.363(6) . ? C3 H3 0.9300 . ? C4 C12 1.386(6) . ? C4 H4 0.9300 . ? C5 C6 1.348(7) . ? C5 C14 1.411(6) . ? C5 H5 0.9300 . ? C6 C7 1.387(7) . ? C6 H6 0.9300 . ? C7 C8 1.369(6) . ? C7 H7 0.9300 . ? C8 C13 1.394(6) . ? C8 H8 0.9300 . ? C9 N15 1.312(5) . ? C9 C11 1.419(6) . ? C9 C13 1.453(5) . ? N10 C14 1.345(5) . ? N10 C12 1.368(5) . ? N10 H10 0.8600 . ? C11 C12 1.405(6) . ? C13 C14 1.408(6) . ? N15 H15A 0.8600 . ? N15 H15B 0.8600 . ? O17 C18 1.390(6) . ? O17 H17 0.8200 . ? C18 H16C 0.9600 . ? C18 H16B 0.9600 . ? C18 H16A 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C11 121.2(4) . . ? C2 C1 H1 119.4 . . ? C11 C1 H1 119.4 . . ? C1 C2 C3 120.8(4) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 119.7(5) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C12 120.1(4) . . ? C3 C4 H4 120.0 . . ? C12 C4 H4 120.0 . . ? C6 C5 C14 119.2(4) . . ? C6 C5 H5 120.4 . . ? C14 C5 H5 120.4 . . ? C5 C6 C7 121.7(4) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C8 C7 C6 119.8(5) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C13 120.9(4) . . ? C7 C8 H8 119.5 . . ? C13 C8 H8 119.5 . . ? N15 C9 C11 121.5(4) . . ? N15 C9 C13 119.8(4) . . ? C11 C9 C13 118.7(3) . . ? C14 N10 C12 123.3(3) . . ? C14 N10 H10 118.4 . . ? C12 N10 H10 118.4 . . ? C12 C11 C1 117.2(4) . . ? C12 C11 C9 119.7(3) . . ? C1 C11 C9 123.2(4) . . ? N10 C12 C4 119.5(4) . . ? N10 C12 C11 119.5(4) . . ? C4 C12 C11 121.0(4) . . ? C8 C13 C14 118.3(4) . . ? C8 C13 C9 123.5(4) . . ? C14 C13 C9 118.2(4) . . ? N10 C14 C13 120.6(3) . . ? N10 C14 C5 119.2(4) . . ? C13 C14 C5 120.1(4) . . ? C9 N15 H15A 120.0 . . ? C9 N15 H15B 120.0 . . ? H15A N15 H15B 120.0 . . ? C18 O17 H17 109.5 . . ? O17 C18 H16C 109.5 . . ? O17 C18 H16B 109.5 . . ? H16C C18 H16B 109.5 . . ? O17 C18 H16A 109.5 . . ? H16C C18 H16A 109.5 . . ? H16B C18 H16A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C1 C2 C3 1.3(7) . . . . ? C1 C2 C3 C4 -1.8(7) . . . . ? C2 C3 C4 C12 -0.3(7) . . . . ? C14 C5 C6 C7 -0.4(7) . . . . ? C5 C6 C7 C8 0.3(7) . . . . ? C6 C7 C8 C13 0.4(7) . . . . ? C2 C1 C11 C12 1.2(6) . . . . ? C2 C1 C11 C9 -179.6(4) . . . . ? N15 C9 C11 C12 -176.7(4) . . . . ? C13 C9 C11 C12 2.9(6) . . . . ? N15 C9 C11 C1 4.1(6) . . . . ? C13 C9 C11 C1 -176.3(4) . . . . ? C14 N10 C12 C4 -179.9(4) . . . . ? C14 N10 C12 C11 -0.7(6) . . . . ? C3 C4 C12 N10 -178.1(4) . . . . ? C3 C4 C12 C11 2.8(6) . . . . ? C1 C11 C12 N10 177.7(4) . . . . ? C9 C11 C12 N10 -1.6(6) . . . . ? C1 C11 C12 C4 -3.2(6) . . . . ? C9 C11 C12 C4 177.5(4) . . . . ? C7 C8 C13 C14 -1.1(6) . . . . ? C7 C8 C13 C9 179.5(4) . . . . ? N15 C9 C13 C8 -3.0(6) . . . . ? C11 C9 C13 C8 177.4(4) . . . . ? N15 C9 C13 C14 177.6(4) . . . . ? C11 C9 C13 C14 -2.0(5) . . . . ? C12 N10 C14 C13 1.6(6) . . . . ? C12 N10 C14 C5 -179.1(4) . . . . ? C8 C13 C14 N10 -179.7(4) . . . . ? C9 C13 C14 N10 -0.2(6) . . . . ? C8 C13 C14 C5 1.0(6) . . . . ? C9 C13 C14 C5 -179.5(4) . . . . ? C6 C5 C14 N10 -179.6(4) . . . . ? C6 C5 C14 C13 -0.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.366 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 934875' ####################################################################### # # 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_Global6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 N2, C H4 O, I' _chemical_formula_sum 'C14 H15 I N2 O' _chemical_formula_weight 354.18 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.9960(11) _cell_length_b 18.6186(17) _cell_length_c 7.3756(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.184(11) _cell_angle_gamma 90.00 _cell_volume 1442.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 9486 _cell_measurement_theta_min 3.63 _cell_measurement_theta_max 25.50 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.631 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 2.210 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.729 _exptl_absorpt_correction_T_max 0.834 _exptl_absorpt_process_details ; CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd., 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(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 'Oxford Diffraction Ruby CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.4002 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9486 _diffrn_reflns_av_R_equivalents 0.0759 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2670 _reflns_number_gt 1522 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_cell_refinement 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 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^)+(0.0315P)^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_number_reflns 2670 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _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 0.8536(6) 0.3570(4) 0.8228(8) 0.0695(17) Uani 1 1 d . . . H1 H 0.8246 0.4038 0.7954 0.083 Uiso 1 1 calc R . . C2 C 0.9747(6) 0.3454(4) 0.9386(9) 0.083(2) Uani 1 1 d . . . H2 H 1.0269 0.3839 0.9919 0.099 Uiso 1 1 calc R . . C3 C 1.0189(6) 0.2745(4) 0.9757(9) 0.079(2) Uani 1 1 d . . . H3 H 1.1019 0.2666 1.0512 0.094 Uiso 1 1 calc R . . C4 C 0.9450(6) 0.2186(4) 0.9057(8) 0.0705(18) Uani 1 1 d . . . H4 H 0.9765 0.1722 0.9342 0.085 Uiso 1 1 calc R . . C5 C 0.5502(7) 0.1156(4) 0.5389(10) 0.081(2) Uani 1 1 d . . . H5 H 0.5855 0.0705 0.5743 0.097 Uiso 1 1 calc R . . C6 C 0.4289(7) 0.1218(4) 0.4237(11) 0.090(2) Uani 1 1 d . . . H6 H 0.3809 0.0806 0.3829 0.108 Uiso 1 1 calc R . . C7 C 0.3753(6) 0.1886(4) 0.3658(10) 0.082(2) Uani 1 1 d . . . H7 H 0.2929 0.1914 0.2837 0.098 Uiso 1 1 calc R . . C8 C 0.4411(6) 0.2496(3) 0.4272(8) 0.0678(17) Uani 1 1 d . . . H8 H 0.4035 0.2940 0.3896 0.081 Uiso 1 1 calc R . . C9 C 0.6447(6) 0.3081(3) 0.6219(7) 0.0535(15) Uani 1 1 d . . . N10 N 0.7428(4) 0.1717(3) 0.7203(6) 0.0640(13) Uani 1 1 d . . . H10 H 0.7727 0.1294 0.7526 0.077 Uiso 1 1 calc R . . C11 C 0.7714(5) 0.2987(3) 0.7435(8) 0.0564(15) Uani 1 1 d . . . C12 C 0.8185(5) 0.2289(4) 0.7876(8) 0.0575(15) Uani 1 1 d . . . C13 C 0.5693(5) 0.2457(3) 0.5505(8) 0.0532(15) Uani 1 1 d . . . C14 C 0.6220(6) 0.1778(4) 0.6043(8) 0.0587(15) Uani 1 1 d . . . N15 N 0.5970(4) 0.3730(3) 0.5743(7) 0.0735(15) Uani 1 1 d . . . H15A H 0.6425 0.4103 0.6167 0.088 Uiso 1 1 calc R . . H15B H 0.5205 0.3778 0.5009 0.088 Uiso 1 1 calc R . . I16 I 0.72634(4) 0.55900(3) 0.66295(6) 0.0815(2) Uani 1 1 d . . . O17 O 0.8248(5) 0.0344(3) 0.8317(7) 0.1079(18) Uani 1 1 d . . . H17 H 0.7739 0.0116 0.8711 0.162 Uiso 1 1 calc R . . C18 C 0.8900(6) -0.0124(5) 0.7474(10) 0.097(2) Uani 1 1 d . . . H18C H 0.8319 -0.0330 0.6360 0.146 Uiso 1 1 calc R . . H18B H 0.9280 -0.0499 0.8353 0.146 Uiso 1 1 calc R . . H18A H 0.9553 0.0134 0.7126 0.146 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 C1 0.060(4) 0.071(5) 0.070(4) 0.004(3) 0.008(3) -0.005(3) C2 0.064(5) 0.098(6) 0.075(5) 0.004(4) 0.004(4) -0.014(4) C3 0.053(4) 0.107(7) 0.069(4) 0.016(4) 0.007(3) 0.002(4) C4 0.070(5) 0.075(5) 0.063(4) 0.021(4) 0.013(3) 0.009(4) C5 0.078(5) 0.067(5) 0.089(5) 0.008(4) 0.013(4) -0.005(4) C6 0.074(5) 0.080(6) 0.105(6) 0.000(5) 0.009(4) -0.028(4) C7 0.069(5) 0.079(6) 0.088(5) -0.006(4) 0.008(4) -0.013(4) C8 0.063(4) 0.063(5) 0.073(4) 0.002(4) 0.013(3) 0.005(3) C9 0.067(4) 0.048(4) 0.048(3) 0.005(3) 0.022(3) 0.007(3) N10 0.062(3) 0.059(3) 0.067(3) 0.014(3) 0.011(3) 0.007(3) C11 0.049(4) 0.066(4) 0.054(3) -0.007(3) 0.016(3) -0.003(3) C12 0.049(4) 0.071(5) 0.054(4) 0.003(3) 0.018(3) -0.001(3) C13 0.050(4) 0.056(4) 0.054(3) 0.004(3) 0.016(3) -0.002(3) C14 0.059(4) 0.063(4) 0.055(4) 0.006(3) 0.018(3) -0.004(3) N15 0.057(3) 0.070(4) 0.082(4) -0.002(3) 0.001(3) -0.001(3) I16 0.0670(3) 0.0747(4) 0.0872(4) -0.0087(3) -0.0012(2) 0.0147(2) O17 0.139(5) 0.076(4) 0.121(4) 0.032(3) 0.059(4) 0.038(3) C18 0.074(5) 0.117(7) 0.094(6) -0.003(5) 0.012(4) 0.013(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.370(8) . ? C1 C11 1.422(8) . ? C1 H1 0.9300 . ? C2 C3 1.405(9) . ? C2 H2 0.9300 . ? C3 C4 1.328(8) . ? C3 H3 0.9300 . ? C4 C12 1.419(8) . ? C4 H4 0.9300 . ? C5 C6 1.358(8) . ? C5 C14 1.405(8) . ? C5 H5 0.9300 . ? C6 C7 1.389(9) . ? C6 H6 0.9300 . ? C7 C8 1.351(8) . ? C7 H7 0.9300 . ? C8 C13 1.435(7) . ? C8 H8 0.9300 . ? C9 N15 1.323(7) . ? C9 C11 1.427(8) . ? C9 C13 1.433(8) . ? N10 C12 1.352(7) . ? N10 C14 1.356(7) . ? N10 H10 0.8600 . ? C11 C12 1.402(8) . ? C13 C14 1.398(8) . ? N15 H15A 0.8600 . ? N15 H15B 0.8600 . ? O17 C18 1.386(7) . ? O17 H17 0.8200 . ? C18 H18C 0.9600 . ? C18 H18B 0.9600 . ? C18 H18A 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C11 121.3(6) . . ? C2 C1 H1 119.4 . . ? C11 C1 H1 119.4 . . ? C1 C2 C3 119.1(7) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 121.6(7) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C12 120.5(7) . . ? C3 C4 H4 119.7 . . ? C12 C4 H4 119.7 . . ? C6 C5 C14 119.5(7) . . ? C6 C5 H5 120.2 . . ? C14 C5 H5 120.2 . . ? C5 C6 C7 121.2(7) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C8 C7 C6 120.8(7) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C13 119.9(6) . . ? C7 C8 H8 120.0 . . ? C13 C8 H8 120.0 . . ? N15 C9 C11 121.0(6) . . ? N15 C9 C13 120.1(6) . . ? C11 C9 C13 118.9(5) . . ? C12 N10 C14 123.2(5) . . ? C12 N10 H10 118.4 . . ? C14 N10 H10 118.4 . . ? C12 C11 C1 117.7(6) . . ? C12 C11 C9 119.0(5) . . ? C1 C11 C9 123.3(6) . . ? N10 C12 C11 120.0(5) . . ? N10 C12 C4 120.3(6) . . ? C11 C12 C4 119.8(6) . . ? C14 C13 C9 118.8(5) . . ? C14 C13 C8 118.2(5) . . ? C9 C13 C8 123.0(6) . . ? N10 C14 C13 120.1(6) . . ? N10 C14 C5 119.6(6) . . ? C13 C14 C5 120.3(6) . . ? C9 N15 H15A 120.0 . . ? C9 N15 H15B 120.0 . . ? H15A N15 H15B 120.0 . . ? C18 O17 H17 109.5 . . ? O17 C18 H18C 109.5 . . ? O17 C18 H18B 109.5 . . ? H18C C18 H18B 109.5 . . ? O17 C18 H18A 109.5 . . ? H18C C18 H18A 109.5 . . ? H18B C18 H18A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C1 C2 C3 1.5(10) . . . . ? C1 C2 C3 C4 -1.9(11) . . . . ? C2 C3 C4 C12 1.0(10) . . . . ? C14 C5 C6 C7 1.4(11) . . . . ? C5 C6 C7 C8 -2.0(12) . . . . ? C6 C7 C8 C13 1.4(10) . . . . ? C2 C1 C11 C12 -0.1(9) . . . . ? C2 C1 C11 C9 -179.9(6) . . . . ? N15 C9 C11 C12 -179.0(5) . . . . ? C13 C9 C11 C12 0.7(8) . . . . ? N15 C9 C11 C1 0.8(9) . . . . ? C13 C9 C11 C1 -179.6(5) . . . . ? C14 N10 C12 C11 2.3(8) . . . . ? C14 N10 C12 C4 -178.8(5) . . . . ? C1 C11 C12 N10 178.1(5) . . . . ? C9 C11 C12 N10 -2.2(8) . . . . ? C1 C11 C12 C4 -0.8(8) . . . . ? C9 C11 C12 C4 178.9(5) . . . . ? C3 C4 C12 N10 -178.5(6) . . . . ? C3 C4 C12 C11 0.4(9) . . . . ? N15 C9 C13 C14 -179.6(5) . . . . ? C11 C9 C13 C14 0.7(8) . . . . ? N15 C9 C13 C8 -0.2(8) . . . . ? C11 C9 C13 C8 -179.9(5) . . . . ? C7 C8 C13 C14 -0.3(9) . . . . ? C7 C8 C13 C9 -179.7(6) . . . . ? C12 N10 C14 C13 -0.9(8) . . . . ? C12 N10 C14 C5 179.3(6) . . . . ? C9 C13 C14 N10 -0.7(8) . . . . ? C8 C13 C14 N10 179.9(5) . . . . ? C9 C13 C14 C5 179.2(6) . . . . ? C8 C13 C14 C5 -0.3(8) . . . . ? C6 C5 C14 N10 179.6(6) . . . . ? C6 C5 C14 C13 -0.3(10) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.367 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 934876' ####################################################################### # # 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 __audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 N2, F, 2(H2 O)' _chemical_formula_sum 'C13 H15 F N2 O2' _chemical_formula_weight 250.27 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' F F 0.0171 0.0103 '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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 16.712(2) _cell_length_b 10.3361(10) _cell_length_c 7.5219(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.794(13) _cell_angle_gamma 90.00 _cell_volume 1214.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 8217 _cell_measurement_theta_min 3.36 _cell_measurement_theta_max 25.50 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.985 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details ; CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd., 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(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 'Oxford Diffraction Ruby CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.4002 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8217 _diffrn_reflns_av_R_equivalents 0.0614 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1129 _reflns_number_gt 749 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_cell_refinement 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 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^)+(0.0694P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1129 _refine_ls_number_parameters 90 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0785 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.019 _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 0.85449(12) 0.39708(19) 0.4973(2) 0.0456(5) Uani 1 1 d . . . H1 H 0.8514 0.3072 0.4921 0.055 Uiso 1 1 calc R . . C2 C 0.78759(13) 0.4680(2) 0.3830(3) 0.0529(6) Uani 1 1 d . . . H2 H 0.7390 0.4266 0.3015 0.063 Uiso 1 1 calc R . . C3 C 0.79155(13) 0.6032(2) 0.3877(3) 0.0525(6) Uani 1 1 d . . . H3 H 0.7459 0.6510 0.3073 0.063 Uiso 1 1 calc R . . C4 C 0.86111(13) 0.66545(19) 0.5079(2) 0.0485(5) Uani 1 1 d . . . H4 H 0.8628 0.7554 0.5106 0.058 Uiso 1 1 calc R . . C9 C 1.0000 0.3873(2) 0.7500 0.0371(6) Uani 1 2 d S . . N10 N 1.0000 0.6566(2) 0.7500 0.0423(6) Uani 1 2 d S . . H10 H 1.0000 0.7398 0.7500 0.051 Uiso 1 2 calc SR . . C11 C 0.92859(12) 0.45743(17) 0.6241(2) 0.0387(5) Uani 1 1 d . . . C12 C 0.93075(12) 0.59385(19) 0.6287(2) 0.0386(5) Uani 1 1 d . . . N15 N 1.0000 0.2594(2) 0.7500 0.0491(6) Uani 1 2 d S . . H15A H 0.9548 0.2159 0.6708 0.059 Uiso 1 1 d R . . F16 F 1.0000 0.90974(15) 0.7500 0.0642(6) Uani 1 2 d S . . O17 O 0.90051(10) 0.06905(15) 0.4737(2) 0.0626(5) Uani 1 1 d D . . H17B H 0.9290(16) 0.067(3) 0.395(3) 0.094 Uiso 1 1 d D . . H17A H 0.9257(16) 0.007(2) 0.556(3) 0.094 Uiso 1 1 d 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 0.0427(13) 0.0483(12) 0.0429(11) -0.0042(8) 0.0118(9) -0.0009(9) C2 0.0377(13) 0.0687(15) 0.0442(11) -0.0061(9) 0.0047(10) 0.0006(10) C3 0.0417(13) 0.0653(15) 0.0454(11) 0.0047(9) 0.0093(10) 0.0129(10) C4 0.0497(13) 0.0506(12) 0.0453(11) 0.0036(8) 0.0169(10) 0.0098(10) C9 0.0373(16) 0.0406(16) 0.0342(12) 0.000 0.0139(12) 0.000 N10 0.0425(14) 0.0388(13) 0.0434(12) 0.000 0.0124(11) 0.000 C11 0.0368(12) 0.0464(12) 0.0333(9) -0.0013(7) 0.0131(8) 0.0000(8) C12 0.0391(12) 0.0438(12) 0.0350(10) 0.0000(7) 0.0156(9) 0.0021(9) N15 0.0419(14) 0.0436(14) 0.0507(13) 0.000 0.0026(11) 0.000 F16 0.0840(14) 0.0492(10) 0.0556(10) 0.000 0.0202(9) 0.000 O17 0.0520(11) 0.0627(10) 0.0640(10) -0.0002(7) 0.0092(8) 0.0038(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.358(3) . ? C1 C11 1.412(3) . ? C1 H1 0.9300 . ? C2 C3 1.399(3) . ? C2 H2 0.9300 . ? C3 C4 1.355(3) . ? C3 H3 0.9300 . ? C4 C12 1.406(3) . ? C4 H4 0.9300 . ? C9 N15 1.322(3) . ? C9 C11 1.430(2) 2_756 ? C9 C11 1.430(2) . ? N10 C12 1.357(2) . ? N10 C12 1.357(2) 2_756 ? N10 H10 0.8600 . ? C11 C12 1.411(3) . ? N15 H15A 0.8991 . ? O17 H17B 0.881(16) . ? O17 H17A 0.883(16) . ? 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 C11 121.11(19) . . ? C2 C1 H1 119.4 . . ? C11 C1 H1 119.4 . . ? C1 C2 C3 120.16(18) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.84(18) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C12 119.90(19) . . ? C3 C4 H4 120.1 . . ? C12 C4 H4 120.1 . . ? N15 C9 C11 120.48(11) . 2_756 ? N15 C9 C11 120.48(11) . . ? C11 C9 C11 119.0(2) 2_756 . ? C12 N10 C12 122.9(2) . 2_756 ? C12 N10 H10 118.5 . . ? C12 N10 H10 118.5 2_756 . ? C12 C11 C1 117.83(16) . . ? C12 C11 C9 118.87(17) . . ? C1 C11 C9 123.29(18) . . ? N10 C12 C4 119.71(17) . . ? N10 C12 C11 120.14(16) . . ? C4 C12 C11 120.15(17) . . ? C9 N15 H15A 120.0 . . ? H17B O17 H17A 102.2(19) . . ? 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 C11 C1 C2 C3 0.7(3) . . . . ? C1 C2 C3 C4 -1.2(3) . . . . ? C2 C3 C4 C12 0.6(3) . . . . ? C2 C1 C11 C12 0.2(3) . . . . ? C2 C1 C11 C9 178.72(15) . . . . ? N15 C9 C11 C12 179.76(11) . . . . ? C11 C9 C11 C12 -0.24(11) 2_756 . . . ? N15 C9 C11 C1 1.28(19) . . . . ? C11 C9 C11 C1 -178.72(19) 2_756 . . . ? C12 N10 C12 C4 179.59(18) 2_756 . . . ? C12 N10 C12 C11 -0.25(11) 2_756 . . . ? C3 C4 C12 N10 -179.45(15) . . . . ? C3 C4 C12 C11 0.4(3) . . . . ? C1 C11 C12 N10 179.04(14) . . . . ? C9 C11 C12 N10 0.5(2) . . . . ? C1 C11 C12 C4 -0.8(2) . . . . ? C9 C11 C12 C4 -179.35(14) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.163 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 934877' ####################################################################### # # 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_Global8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 N2, Cl, 2(H2 O)' _chemical_formula_sum 'C13 H15 Cl N2 O2' _chemical_formula_weight 266.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.0430(12) _cell_length_b 7.0446(6) _cell_length_c 20.792(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2642.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 13875 _cell_measurement_theta_min 4.25 _cell_measurement_theta_max 65.49 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 2.534 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.597 _exptl_absorpt_correction_T_max 0.841 _exptl_absorpt_process_details ; CrysAlis RED, Version 1.171.32.15 (Oxford Diffraction Ltd., 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Ruby CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.4002 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7567 _diffrn_reflns_av_R_equivalents 0.1064 _diffrn_reflns_av_sigmaI/netI 0.0842 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.25 _diffrn_reflns_theta_max 65.49 _reflns_number_total 2218 _reflns_number_gt 1075 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_cell_refinement 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlis RED,Version 1.171.32.15 (Oxford Diffraction Ltd., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 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^)+(0.0998P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2218 _refine_ls_number_parameters 175 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1570 _refine_ls_R_factor_gt 0.0738 _refine_ls_wR_factor_ref 0.2130 _refine_ls_wR_factor_gt 0.1642 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.992 _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 0.2445(3) 0.5183(7) 0.2104(2) 0.0637(14) Uani 1 1 d . . . H1A H 0.1993 0.5350 0.1897 0.076 Uiso 1 1 calc R . . C2 C 0.3087(3) 0.5370(8) 0.1773(3) 0.0740(17) Uani 1 1 d . . . H2A H 0.3069 0.5689 0.1339 0.089 Uiso 1 1 calc R . . C3 C 0.3775(3) 0.5097(8) 0.2064(3) 0.0773(17) Uani 1 1 d . . . H3A H 0.4208 0.5217 0.1825 0.093 Uiso 1 1 calc R . . C4 C 0.3809(3) 0.4650(8) 0.2704(3) 0.0688(16) Uani 1 1 d . . . H4A H 0.4267 0.4473 0.2901 0.083 Uiso 1 1 calc R . . C5 C 0.2694(3) 0.3299(7) 0.4724(2) 0.0610(15) Uani 1 1 d . . . H5A H 0.3167 0.3139 0.4893 0.073 Uiso 1 1 calc R . . C6 C 0.2085(3) 0.3069(9) 0.5111(3) 0.0713(17) Uani 1 1 d . . . H6A H 0.2144 0.2764 0.5543 0.086 Uiso 1 1 calc R . . C7 C 0.1376(3) 0.3299(9) 0.4851(3) 0.0754(18) Uani 1 1 d . . . H7A H 0.0964 0.3132 0.5114 0.090 Uiso 1 1 calc R . . C8 C 0.1278(3) 0.3756(8) 0.4230(3) 0.0679(16) Uani 1 1 d . . . H8A H 0.0800 0.3911 0.4071 0.082 Uiso 1 1 calc R . . C9 C 0.1813(3) 0.4502(7) 0.3153(2) 0.0531(13) Uani 1 1 d . . . N10 N 0.3205(2) 0.3993(6) 0.3692(2) 0.0590(12) Uani 1 1 d . . . H10A H 0.3637 0.3829 0.3858 0.071 Uiso 1 1 calc R . . C11 C 0.2469(3) 0.4728(6) 0.2769(2) 0.0501(12) Uani 1 1 d . . . C12 C 0.3160(3) 0.4460(7) 0.3062(2) 0.0528(13) Uani 1 1 d . . . C13 C 0.1889(3) 0.4005(7) 0.3817(2) 0.0532(13) Uani 1 1 d . . . C14 C 0.2603(3) 0.3771(7) 0.4076(2) 0.0529(13) Uani 1 1 d . . . N15 N 0.1150(2) 0.4754(6) 0.2901(2) 0.0672(13) Uani 1 1 d . . . H15A H 0.0761 0.4620 0.3135 0.081 Uiso 1 1 calc R . . H15B H 0.1107 0.5052 0.2501 0.081 Uiso 1 1 calc R . . Cl16 Cl 0.05084(7) 0.5231(2) 0.14538(7) 0.0744(5) Uani 1 1 d . . . O17 O 0.46538(19) 0.3539(6) 0.4210(2) 0.0761(12) Uani 1 1 d D . . H17A H 0.485(3) 0.270(6) 0.398(3) 0.114 Uiso 1 1 d D . . H17B H 0.491(3) 0.454(5) 0.423(3) 0.114 Uiso 1 1 d D . . O18 O 0.4424(3) 0.3368(6) 0.5535(2) 0.0900(13) Uani 1 1 d D . . H18A H 0.451(4) 0.240(6) 0.576(2) 0.135 Uiso 1 1 d D . . H18B H 0.451(4) 0.313(9) 0.5144(11) 0.135 Uiso 1 1 d 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 0.066(3) 0.068(4) 0.057(3) 0.007(3) -0.007(3) -0.003(3) C2 0.080(4) 0.086(4) 0.057(4) 0.019(3) 0.003(3) 0.003(4) C3 0.069(3) 0.089(4) 0.074(4) 0.014(4) 0.014(3) 0.003(4) C4 0.052(3) 0.079(4) 0.075(4) 0.009(3) 0.005(3) 0.009(3) C5 0.055(3) 0.062(4) 0.066(4) 0.005(3) -0.007(3) 0.006(3) C6 0.074(4) 0.085(5) 0.056(3) -0.001(3) -0.004(3) -0.008(4) C7 0.057(3) 0.097(5) 0.072(4) 0.007(4) 0.007(3) -0.003(3) C8 0.050(3) 0.090(4) 0.064(4) 0.007(3) 0.001(3) -0.003(3) C9 0.050(3) 0.052(3) 0.057(3) -0.002(3) -0.004(3) 0.000(3) N10 0.043(2) 0.073(3) 0.061(3) 0.008(2) -0.002(2) 0.004(2) C11 0.055(3) 0.046(3) 0.050(3) 0.004(2) -0.001(3) 0.005(3) C12 0.049(3) 0.054(3) 0.055(3) 0.001(3) 0.001(3) 0.006(2) C13 0.053(3) 0.054(3) 0.053(3) 0.002(3) -0.004(2) -0.001(3) C14 0.055(3) 0.047(3) 0.056(3) 0.000(3) -0.001(3) 0.003(3) N15 0.055(2) 0.090(3) 0.056(3) 0.007(2) -0.004(2) -0.001(2) Cl16 0.0574(8) 0.1022(12) 0.0636(9) 0.0020(8) -0.0075(7) 0.0000(8) O17 0.059(2) 0.088(3) 0.081(3) -0.009(2) -0.004(2) 0.006(2) O18 0.078(3) 0.103(3) 0.089(3) 0.008(3) 0.000(3) 0.004(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 C2 1.354(7) . ? C1 C11 1.420(6) . ? C1 H1A 0.9300 . ? C2 C3 1.394(7) . ? C2 H2A 0.9300 . ? C3 C4 1.369(7) . ? C3 H3A 0.9300 . ? C4 C12 1.392(6) . ? C4 H4A 0.9300 . ? C5 C6 1.370(7) . ? C5 C14 1.398(6) . ? C5 H5A 0.9300 . ? C6 C7 1.399(7) . ? C6 H6A 0.9300 . ? C7 C8 1.342(7) . ? C7 H7A 0.9300 . ? C8 C13 1.409(7) . ? C8 H8A 0.9300 . ? C9 N15 1.318(6) . ? C9 C13 1.430(7) . ? C9 C11 1.436(7) . ? N10 C12 1.354(6) . ? N10 C14 1.356(6) . ? N10 H10A 0.8600 . ? C11 C12 1.401(6) . ? C13 C14 1.406(6) . ? N15 H15A 0.8600 . ? N15 H15B 0.8600 . ? O17 H17A 0.834(19) . ? O17 H17B 0.845(19) . ? O18 H18A 0.84(2) . ? O18 H18B 0.844(19) . ? 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 C11 119.5(5) . . ? C2 C1 H1A 120.3 . . ? C11 C1 H1A 120.3 . . ? C1 C2 C3 121.8(5) . . ? C1 C2 H2A 119.1 . . ? C3 C2 H2A 119.1 . . ? C4 C3 C2 119.7(5) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? C3 C4 C12 120.2(5) . . ? C3 C4 H4A 119.9 . . ? C12 C4 H4A 119.9 . . ? C6 C5 C14 120.0(5) . . ? C6 C5 H5A 120.0 . . ? C14 C5 H5A 120.0 . . ? C5 C6 C7 119.5(5) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C8 C7 C6 121.3(5) . . ? C8 C7 H7A 119.3 . . ? C6 C7 H7A 119.3 . . ? C7 C8 C13 120.9(5) . . ? C7 C8 H8A 119.6 . . ? C13 C8 H8A 119.6 . . ? N15 C9 C13 120.3(5) . . ? N15 C9 C11 120.8(4) . . ? C13 C9 C11 118.9(4) . . ? C12 N10 C14 123.3(4) . . ? C12 N10 H10A 118.3 . . ? C14 N10 H10A 118.3 . . ? C12 C11 C1 118.7(5) . . ? C12 C11 C9 118.5(4) . . ? C1 C11 C9 122.8(5) . . ? N10 C12 C4 119.3(5) . . ? N10 C12 C11 120.4(4) . . ? C4 C12 C11 120.3(5) . . ? C14 C13 C8 118.0(5) . . ? C14 C13 C9 119.1(5) . . ? C8 C13 C9 122.9(5) . . ? N10 C14 C5 120.1(4) . . ? N10 C14 C13 119.7(4) . . ? C5 C14 C13 120.3(5) . . ? C9 N15 H15A 120.0 . . ? C9 N15 H15B 120.0 . . ? H15A N15 H15B 120.0 . . ? H17A O17 H17B 113(3) . . ? H18A O18 H18B 111(3) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 65.49 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.266 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 934878'