# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_3a _database_code_depnum_ccdc_archive 'CCDC 891057' #TrackingRef 'cif pub Samira.cif' _audit_creation_date 2010-03-30T09:18:39-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H12 N2 O' _chemical_formula_sum 'C18 H12 N2 O' _chemical_formula_weight 272.3 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.7576(3) _cell_length_b 6.0070(2) _cell_length_c 14.7572(6) _cell_angle_alpha 90 _cell_angle_beta 93.710(2) _cell_angle_gamma 90 _cell_volume 686.24(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5150 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 27.5 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description blade _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.864 _exptl_absorpt_correction_T_max 0.998 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_unetI/netI 0.0221 _diffrn_reflns_number 8178 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 1721 _reflns_number_gt 1649 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0327P)^2^+0.1328P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1721 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0295 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.067 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_diff_density_max 0.227 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.033 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.24761(12) 0.2641(2) 0.84425(7) 0.0158(2) Uani 1 1 d . . . C2 C 0.07322(17) 0.1712(3) 0.82810(10) 0.0142(3) Uani 1 1 d . . . H2 H 0.0703 0.0184 0.8549 0.017 Uiso 1 1 calc R . . C3 C -0.05765(19) 0.3166(3) 0.87151(10) 0.0147(3) Uani 1 1 d . . . C4 C -0.1032(2) 0.5241(3) 0.83444(10) 0.0169(3) Uani 1 1 d . . . H4 H -0.0494 0.5759 0.7824 0.02 Uiso 1 1 calc R . . C5 C -0.2264(2) 0.6551(3) 0.87305(11) 0.0223(3) Uani 1 1 d . . . H5 H -0.2572 0.7959 0.8475 0.027 Uiso 1 1 calc R . . C6 C -0.3045(2) 0.5787(4) 0.94958(11) 0.0248(4) Uani 1 1 d . . . H6 H -0.3892 0.6674 0.9761 0.03 Uiso 1 1 calc R . . C7 C -0.2591(2) 0.3741(3) 0.98702(11) 0.0232(4) Uani 1 1 d . . . H7 H -0.3122 0.3233 1.0394 0.028 Uiso 1 1 calc R . . C8 C -0.13560(18) 0.2422(3) 0.94807(10) 0.0176(3) Uani 1 1 d . . . H8 H -0.1049 0.1017 0.9739 0.021 Uiso 1 1 calc R . . C9 C 0.05074(18) 0.1545(3) 0.72686(10) 0.0136(3) Uani 1 1 d . . . H9 H -0.0477 0.0903 0.6953 0.016 Uiso 1 1 calc R . . C10 C 0.18315(17) 0.2389(3) 0.68600(9) 0.0127(3) Uani 1 1 d . . . C11 C 0.21799(17) 0.2416(3) 0.58893(9) 0.0138(3) Uani 1 1 d . . . C12 C 0.15322(19) 0.0705(3) 0.53202(10) 0.0187(3) Uani 1 1 d . . . H12 H 0.086 -0.0451 0.556 0.022 Uiso 1 1 calc R . . C13 C 0.1869(2) 0.0690(3) 0.44064(11) 0.0223(3) Uani 1 1 d . . . H13 H 0.1427 -0.0478 0.4025 0.027 Uiso 1 1 calc R . . C14 C 0.28468(18) 0.2373(3) 0.40473(10) 0.0198(3) Uani 1 1 d . . . H14 H 0.3066 0.2361 0.3421 0.024 Uiso 1 1 calc R . . C15 C 0.3502(2) 0.4069(3) 0.46056(11) 0.0210(3) Uani 1 1 d . . . H15 H 0.4177 0.5217 0.4362 0.025 Uiso 1 1 calc R . . C16 C 0.31742(19) 0.4093(3) 0.55211(10) 0.0185(3) Uani 1 1 d . . . H16 H 0.3629 0.526 0.59 0.022 Uiso 1 1 calc R . . C17 C 0.31266(19) 0.3262(3) 0.76076(10) 0.0137(3) Uani 1 1 d . . . C18 C 0.48836(18) 0.2292(3) 0.75228(9) 0.0138(3) Uani 1 1 d . . . N19 N 0.62141(16) 0.1568(3) 0.74195(9) 0.0203(3) Uani 1 1 d . . . C20 C 0.32823(19) 0.5747(3) 0.75974(10) 0.0161(3) Uani 1 1 d . . . N21 N 0.33205(19) 0.7645(3) 0.76212(11) 0.0245(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0109(4) 0.0222(6) 0.0145(5) 0.0006(5) 0.0011(4) -0.0012(5) C2 0.0113(6) 0.0140(7) 0.0175(7) 0.0009(6) 0.0014(5) -0.0018(6) C3 0.0123(6) 0.0172(7) 0.0145(6) -0.0029(6) -0.0011(5) -0.0002(6) C4 0.0151(7) 0.0178(8) 0.0177(7) -0.0016(6) 0.0002(5) -0.0004(6) C5 0.0175(7) 0.0227(8) 0.0257(8) -0.0067(7) -0.0062(6) 0.0052(7) C6 0.0137(7) 0.0358(10) 0.0247(8) -0.0133(8) -0.0011(6) 0.0059(8) C7 0.0152(7) 0.0379(11) 0.0167(7) -0.0059(7) 0.0027(6) -0.0035(7) C8 0.0136(6) 0.0225(8) 0.0164(6) -0.0003(7) -0.0007(5) -0.0015(7) C9 0.0122(6) 0.0118(7) 0.0167(7) -0.0021(6) 0.0008(5) 0.0008(6) C10 0.0109(6) 0.0109(6) 0.0160(6) -0.0014(6) -0.0005(5) 0.0013(6) C11 0.0098(6) 0.0162(7) 0.0152(6) 0.0020(6) 0.0007(5) 0.0014(6) C12 0.0167(7) 0.0198(8) 0.0198(7) -0.0010(7) 0.0018(5) -0.0039(7) C13 0.0211(8) 0.0253(9) 0.0202(7) -0.0063(7) -0.0006(6) -0.0029(7) C14 0.0167(7) 0.0284(9) 0.0143(6) -0.0001(7) 0.0013(5) 0.0029(7) C15 0.0193(7) 0.0236(9) 0.0205(8) 0.0045(7) 0.0039(6) -0.0030(7) C16 0.0174(7) 0.0191(8) 0.0191(7) -0.0002(7) 0.0008(6) -0.0034(7) C17 0.0109(6) 0.0135(7) 0.0168(7) 0.0001(6) 0.0009(5) 0.0010(6) C18 0.0135(6) 0.0128(7) 0.0149(6) -0.0012(6) 0.0000(5) -0.0021(6) N19 0.0153(6) 0.0226(7) 0.0228(6) -0.0050(6) -0.0004(5) 0.0007(6) C20 0.0121(7) 0.0191(9) 0.0170(7) -0.0010(6) 0.0006(5) 0.0002(6) N21 0.0236(7) 0.0162(9) 0.0336(8) -0.0019(7) 0.0010(6) -0.0007(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C17 1.4114(18) . ? O1 C2 1.4687(17) . ? C2 C9 1.4963(19) . ? C2 C3 1.513(2) . ? C2 H2 1 . ? C3 C8 1.389(2) . ? C3 C4 1.397(2) . ? C4 C5 1.389(2) . ? C4 H4 0.95 . ? C5 C6 1.393(3) . ? C5 H5 0.95 . ? C6 C7 1.383(3) . ? C6 H6 0.95 . ? C7 C8 1.396(2) . ? C7 H7 0.95 . ? C8 H8 0.95 . ? C9 C10 1.325(2) . ? C9 H9 0.95 . ? C10 C11 1.4750(19) . ? C10 C17 1.536(2) . ? C11 C12 1.400(2) . ? C11 C16 1.400(2) . ? C12 C13 1.390(2) . ? C12 H12 0.95 . ? C13 C14 1.389(3) . ? C13 H13 0.95 . ? C14 C15 1.386(2) . ? C14 H14 0.95 . ? C15 C16 1.391(2) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 C18 1.495(2) . ? C17 C20 1.498(2) . ? C18 N19 1.139(2) . ? C20 N21 1.141(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C17 O1 C2 109.67(10) . . ? O1 C2 C9 103.53(11) . . ? O1 C2 C3 110.37(13) . . ? C9 C2 C3 115.05(13) . . ? O1 C2 H2 109.2 . . ? C9 C2 H2 109.2 . . ? C3 C2 H2 109.2 . . ? C8 C3 C4 119.53(15) . . ? C8 C3 C2 119.87(15) . . ? C4 C3 C2 120.59(14) . . ? C5 C4 C3 120.55(15) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.51(18) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 120.24(16) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.24(15) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C3 C8 C7 119.93(16) . . ? C3 C8 H8 120 . . ? C7 C8 H8 120 . . ? C10 C9 C2 112.65(13) . . ? C10 C9 H9 123.7 . . ? C2 C9 H9 123.7 . . ? C9 C10 C11 129.95(14) . . ? C9 C10 C17 107.11(12) . . ? C11 C10 C17 122.80(12) . . ? C12 C11 C16 118.76(13) . . ? C12 C11 C10 119.57(14) . . ? C16 C11 C10 121.66(14) . . ? C13 C12 C11 120.26(15) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.45(16) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 119.77(14) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.14(16) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.61(15) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? O1 C17 C18 110.45(12) . . ? O1 C17 C20 107.80(13) . . ? C18 C17 C20 108.25(14) . . ? O1 C17 C10 106.42(12) . . ? C18 C17 C10 111.38(13) . . ? C20 C17 C10 112.48(13) . . ? N19 C18 C17 177.09(15) . . ? N21 C20 C17 175.97(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C17 O1 C2 C9 7.60(16) . . . . ? C17 O1 C2 C3 -116.04(13) . . . . ? O1 C2 C3 C8 -108.79(15) . . . . ? C9 C2 C3 C8 134.53(15) . . . . ? O1 C2 C3 C4 72.25(17) . . . . ? C9 C2 C3 C4 -44.4(2) . . . . ? C8 C3 C4 C5 -0.5(2) . . . . ? C2 C3 C4 C5 178.44(14) . . . . ? C3 C4 C5 C6 0.2(2) . . . . ? C4 C5 C6 C7 0.2(2) . . . . ? C5 C6 C7 C8 -0.4(2) . . . . ? C4 C3 C8 C7 0.4(2) . . . . ? C2 C3 C8 C7 -178.61(14) . . . . ? C6 C7 C8 C3 0.1(2) . . . . ? O1 C2 C9 C10 -4.27(18) . . . . ? C3 C2 C9 C10 116.24(16) . . . . ? C2 C9 C10 C11 175.17(16) . . . . ? C2 C9 C10 C17 -0.45(19) . . . . ? C9 C10 C11 C12 -28.9(3) . . . . ? C17 C10 C11 C12 146.14(15) . . . . ? C9 C10 C11 C16 152.32(17) . . . . ? C17 C10 C11 C16 -32.7(2) . . . . ? C16 C11 C12 C13 -0.3(2) . . . . ? C10 C11 C12 C13 -179.15(14) . . . . ? C11 C12 C13 C14 -0.1(2) . . . . ? C12 C13 C14 C15 0.5(2) . . . . ? C13 C14 C15 C16 -0.4(2) . . . . ? C14 C15 C16 C11 -0.1(2) . . . . ? C12 C11 C16 C15 0.4(2) . . . . ? C10 C11 C16 C15 179.24(15) . . . . ? C2 O1 C17 C18 -129.04(13) . . . . ? C2 O1 C17 C20 112.87(14) . . . . ? C2 O1 C17 C10 -8.01(16) . . . . ? C9 C10 C17 O1 5.26(17) . . . . ? C11 C10 C17 O1 -170.75(14) . . . . ? C9 C10 C17 C18 125.69(15) . . . . ? C11 C10 C17 C18 -50.3(2) . . . . ? C9 C10 C17 C20 -112.57(16) . . . . ? C11 C10 C17 C20 71.42(19) . . . . ? data_3b _database_code_depnum_ccdc_archive 'CCDC 891058' #TrackingRef 'cif pub Samira.cif' _audit_creation_date 2010-03-30T15:45:57-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C36 H22 Cl2 N4 O2' _chemical_formula_sum 'C36 H22 Cl2 N4 O2' _chemical_formula_weight 613.48 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.0917(5) _cell_length_b 17.5158(6) _cell_length_c 16.2080(6) _cell_angle_alpha 90 _cell_angle_beta 109.615(2) _cell_angle_gamma 90 _cell_volume 2966.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8736 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 27.38 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.784 _exptl_absorpt_correction_T_max 0.925 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_unetI/netI 0.0395 _diffrn_reflns_number 20379 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.41 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 6660 _reflns_number_gt 6009 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0835P)^2^+0.9906P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6660 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1369 _refine_ls_wR_factor_gt 0.131 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.336 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.052 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.63903(6) 1.00009(3) 0.37200(4) 0.03269(16) Uani 1 1 d . . . C2 C 0.5174(2) 0.95253(13) 0.39730(14) 0.0224(4) Uani 1 1 d . . . C3 C 0.5486(2) 0.89983(14) 0.46487(14) 0.0245(5) Uani 1 1 d . . . H3 H 0.6355 0.8896 0.498 0.029 Uiso 1 1 calc R . . C4 C 0.4500(2) 0.86200(13) 0.48336(13) 0.0216(4) Uani 1 1 d . . . H4 H 0.4702 0.8256 0.5294 0.026 Uiso 1 1 calc R . . C5 C 0.3223(2) 0.87688(12) 0.43524(12) 0.0169(4) Uani 1 1 d . . . C6 C 0.2937(2) 0.93092(13) 0.36820(13) 0.0213(4) Uani 1 1 d . . . H6 H 0.2069 0.9417 0.3353 0.026 Uiso 1 1 calc R . . C7 C 0.3907(2) 0.96906(13) 0.34896(14) 0.0237(5) Uani 1 1 d . . . H7 H 0.3708 1.006 0.3034 0.028 Uiso 1 1 calc R . . C8 C 0.2169(2) 0.83306(12) 0.45441(12) 0.0179(4) Uani 1 1 d . . . H8 H 0.2562 0.7932 0.4996 0.022 Uiso 1 1 calc R . . C9 C 0.1220(2) 0.79610(11) 0.37623(12) 0.0178(4) Uani 1 1 d . . . H9 H 0.1441 0.758 0.3421 0.021 Uiso 1 1 calc R . . C10 C 0.0041(2) 0.82204(11) 0.35962(12) 0.0165(4) Uani 1 1 d . . . N11 O 0.13825(15) 0.88423(9) 0.48718(9) 0.0222(3) Uani 1 1 d . . . C12 C 0.0099(2) 0.88275(12) 0.42986(12) 0.0176(4) Uani 1 1 d . . . C13 C -0.0756(2) 0.86018(12) 0.48055(13) 0.0187(4) Uani 1 1 d . . . N14 N -0.13852(19) 0.83903(11) 0.51907(12) 0.0244(4) Uani 1 1 d . . . C15 C -0.0255(2) 0.96063(12) 0.39251(14) 0.0214(4) Uani 1 1 d . . . N16 N -0.0467(2) 1.02055(11) 0.36313(13) 0.0307(5) Uani 1 1 d . . . C17 C -0.1169(2) 0.79819(11) 0.29218(12) 0.0153(4) Uani 1 1 d . . . C18 C -0.1241(2) 0.72466(12) 0.25603(12) 0.0178(4) Uani 1 1 d . . . H18 H -0.0522 0.6916 0.2751 0.021 Uiso 1 1 calc R . . C19 C -0.2363(2) 0.70025(12) 0.19242(13) 0.0208(4) Uani 1 1 d . . . H19 H -0.2404 0.6505 0.1682 0.025 Uiso 1 1 calc R . . C20 C -0.3424(2) 0.74769(13) 0.16386(12) 0.0215(4) Uani 1 1 d . . . H20 H -0.4188 0.7305 0.1205 0.026 Uiso 1 1 calc R . . C21 C -0.3366(2) 0.82086(12) 0.19914(13) 0.0198(4) Uani 1 1 d . . . H21 H -0.4086 0.8538 0.1792 0.024 Uiso 1 1 calc R . . C22 C -0.2247(2) 0.84552(11) 0.26374(12) 0.0175(4) Uani 1 1 d . . . H22 H -0.2217 0.8949 0.2886 0.021 Uiso 1 1 calc R . . Cl2 Cl 1.06954(5) -0.01052(3) 0.13455(4) 0.02777(15) Uani 1 1 d . . . C32 C 0.9261(2) 0.04020(12) 0.10928(13) 0.0194(4) Uani 1 1 d . . . C33 C 0.9080(2) 0.10524(12) 0.05778(14) 0.0206(4) Uani 1 1 d . . . H33 H 0.9737 0.1232 0.0373 0.025 Uiso 1 1 calc R . . C34 C 0.7915(2) 0.14369(12) 0.03665(13) 0.0188(4) Uani 1 1 d . . . H34 H 0.7773 0.188 0.0008 0.023 Uiso 1 1 calc R . . C35 C 0.6957(2) 0.11798(12) 0.06748(12) 0.0160(4) Uani 1 1 d . . . C36 C 0.7168(2) 0.05254(13) 0.11999(13) 0.0212(4) Uani 1 1 d . . . H36 H 0.6521 0.0349 0.1417 0.025 Uiso 1 1 calc R . . C37 C 0.8319(2) 0.01325(13) 0.14051(14) 0.0215(4) Uani 1 1 d . . . H37 H 0.8459 -0.0316 0.1755 0.026 Uiso 1 1 calc R . . C38 C 0.5707(2) 0.16082(12) 0.04420(12) 0.0170(4) Uani 1 1 d . . . H38 H 0.5677 0.2004 -0.0009 0.02 Uiso 1 1 calc R . . C39 C 0.5455(2) 0.19802(11) 0.12042(12) 0.0174(4) Uani 1 1 d . . . H39 H 0.5982 0.2369 0.1553 0.021 Uiso 1 1 calc R . . C40 C 0.4417(2) 0.17084(11) 0.13379(12) 0.0152(4) Uani 1 1 d . . . N41 O 0.46238(15) 0.10856(8) 0.00926(9) 0.0180(3) Uani 1 1 d . . . C42 C 0.3836(2) 0.11023(11) 0.06245(12) 0.0160(4) Uani 1 1 d . . . C43 C 0.2506(2) 0.13375(12) 0.00877(13) 0.0171(4) Uani 1 1 d . . . N44 N 0.15160(19) 0.15734(11) -0.02991(12) 0.0237(4) Uani 1 1 d . . . C45 C 0.3824(2) 0.03185(12) 0.09936(13) 0.0180(4) Uani 1 1 d . . . N46 N 0.3890(2) -0.02770(11) 0.12955(12) 0.0240(4) Uani 1 1 d . . . C47 C 0.3819(2) 0.19270(11) 0.19927(12) 0.0161(4) Uani 1 1 d . . . C48 C 0.4109(2) 0.26351(12) 0.24201(13) 0.0202(4) Uani 1 1 d . . . H48 H 0.4678 0.2975 0.2279 0.024 Uiso 1 1 calc R . . C49 C 0.3570(2) 0.28439(13) 0.30509(13) 0.0249(5) Uani 1 1 d . . . H49 H 0.3772 0.3325 0.3334 0.03 Uiso 1 1 calc R . . C50 C 0.2741(2) 0.23532(14) 0.32660(13) 0.0241(5) Uani 1 1 d . . . H50 H 0.2384 0.2495 0.3701 0.029 Uiso 1 1 calc R . . C51 C 0.2432(2) 0.16507(13) 0.28421(13) 0.0227(5) Uani 1 1 d . . . H51 H 0.1869 0.1311 0.2991 0.027 Uiso 1 1 calc R . . C52 C 0.2951(2) 0.14475(12) 0.21998(13) 0.0191(4) Uani 1 1 d . . . H52 H 0.2712 0.0977 0.1898 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0302(3) 0.0282(3) 0.0490(3) -0.0119(2) 0.0257(3) -0.0112(2) C2 0.0218(11) 0.0208(10) 0.0293(10) -0.0097(8) 0.0146(9) -0.0066(9) C3 0.0166(10) 0.0291(12) 0.0266(10) -0.0061(9) 0.0056(8) 0.0006(9) C4 0.0202(11) 0.0248(11) 0.0192(9) 0.0000(8) 0.0057(8) 0.0034(9) C5 0.0159(10) 0.0184(10) 0.0168(8) -0.0043(7) 0.0062(7) -0.0018(8) C6 0.0182(10) 0.0244(11) 0.0204(9) -0.0002(8) 0.0053(8) 0.0015(9) C7 0.0281(12) 0.0194(10) 0.0264(10) 0.0019(8) 0.0128(9) 0.0002(9) C8 0.0166(10) 0.0213(10) 0.0169(8) 0.0002(7) 0.0069(8) 0.0015(8) C9 0.0193(10) 0.0162(9) 0.0190(9) -0.0010(7) 0.0080(8) -0.0019(8) C10 0.0210(11) 0.0142(9) 0.0151(8) -0.0017(7) 0.0070(8) -0.0025(8) N11 0.0156(7) 0.0318(9) 0.0200(7) -0.0108(6) 0.0068(6) -0.0038(7) C12 0.0155(10) 0.0199(10) 0.0180(9) -0.0043(7) 0.0065(8) -0.0022(8) C13 0.0152(10) 0.0215(10) 0.0178(9) -0.0049(7) 0.0035(8) -0.0010(8) N14 0.0220(10) 0.0291(10) 0.0228(8) -0.0038(7) 0.0086(7) -0.0024(8) C15 0.0229(11) 0.0192(11) 0.0239(10) -0.0091(8) 0.0104(8) -0.0063(9) N16 0.0365(12) 0.0193(10) 0.0348(10) -0.0055(8) 0.0101(9) -0.0029(9) C17 0.0187(10) 0.0148(9) 0.0132(8) 0.0003(7) 0.0062(7) -0.0016(8) C18 0.0220(11) 0.0149(9) 0.0170(8) 0.0004(7) 0.0072(8) 0.0002(8) C19 0.0268(12) 0.0173(10) 0.0182(9) -0.0038(7) 0.0073(8) -0.0037(9) C20 0.0234(11) 0.0246(11) 0.0132(8) 0.0001(8) 0.0017(8) -0.0042(9) C21 0.0209(11) 0.0206(10) 0.0165(8) 0.0040(7) 0.0045(8) 0.0006(9) C22 0.0221(11) 0.0145(9) 0.0167(8) 0.0001(7) 0.0078(8) -0.0014(8) Cl2 0.0173(3) 0.0239(3) 0.0401(3) -0.0053(2) 0.0070(2) 0.0031(2) C32 0.0145(10) 0.0192(10) 0.0227(9) -0.0066(8) 0.0040(8) 0.0013(8) C33 0.0180(11) 0.0213(10) 0.0257(10) -0.0037(8) 0.0119(8) -0.0035(9) C34 0.0208(11) 0.0183(10) 0.0185(9) -0.0007(7) 0.0081(8) -0.0021(8) C35 0.0173(10) 0.0165(9) 0.0145(8) -0.0027(7) 0.0057(7) -0.0008(8) C36 0.0193(11) 0.0246(11) 0.0215(9) 0.0045(8) 0.0090(8) 0.0006(9) C37 0.0229(11) 0.0187(10) 0.0225(9) 0.0038(8) 0.0070(8) 0.0007(9) C38 0.0160(10) 0.0174(9) 0.0175(8) 0.0008(7) 0.0056(7) -0.0025(8) C39 0.0175(10) 0.0144(9) 0.0191(9) -0.0013(7) 0.0047(7) 0.0007(8) C40 0.0164(10) 0.0116(9) 0.0153(8) -0.0001(7) 0.0022(7) 0.0010(8) N41 0.0166(7) 0.0211(7) 0.0172(6) -0.0043(5) 0.0069(5) -0.0029(6) C42 0.0161(10) 0.0148(9) 0.0174(8) -0.0020(7) 0.0062(7) -0.0005(8) C43 0.0183(11) 0.0150(9) 0.0183(9) -0.0031(7) 0.0068(8) -0.0036(8) N44 0.0227(10) 0.0219(9) 0.0248(9) -0.0005(7) 0.0059(8) -0.0001(8) C45 0.0178(10) 0.0175(10) 0.0189(9) -0.0047(8) 0.0064(8) -0.0005(8) N46 0.0294(11) 0.0191(9) 0.0253(9) -0.0027(7) 0.0115(8) -0.0027(8) C47 0.0179(10) 0.0148(9) 0.0137(8) 0.0008(7) 0.0027(7) 0.0036(8) C48 0.0184(10) 0.0197(11) 0.0201(9) -0.0034(8) 0.0035(8) -0.0013(8) C49 0.0275(12) 0.0257(11) 0.0174(9) -0.0083(8) 0.0023(8) 0.0023(10) C50 0.0260(12) 0.0313(12) 0.0151(8) -0.0006(8) 0.0071(8) 0.0070(10) C51 0.0246(12) 0.0252(11) 0.0199(9) 0.0066(8) 0.0094(8) 0.0050(9) C52 0.0213(11) 0.0153(9) 0.0215(9) 0.0013(7) 0.0083(8) 0.0027(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.748(2) . ? C2 C3 1.384(3) . ? C2 C7 1.390(3) . ? C3 C4 1.394(3) . ? C3 H3 0.95 . ? C4 C5 1.393(3) . ? C4 H4 0.95 . ? C5 C6 1.395(3) . ? C5 C8 1.515(3) . ? C6 C7 1.388(3) . ? C6 H6 0.95 . ? C7 H7 0.95 . ? C8 N11 1.469(2) . ? C8 C9 1.496(3) . ? C8 H8 1 . ? C9 C10 1.324(3) . ? C9 H9 0.95 . ? C10 C17 1.478(3) . ? C10 C12 1.543(3) . ? N11 C12 1.415(3) . ? C12 C15 1.491(3) . ? C12 C13 1.502(3) . ? C13 N14 1.143(3) . ? C15 N16 1.144(3) . ? C17 C22 1.400(3) . ? C17 C18 1.406(3) . ? C18 C19 1.390(3) . ? C18 H18 0.95 . ? C19 C20 1.387(3) . ? C19 H19 0.95 . ? C20 C21 1.396(3) . ? C20 H20 0.95 . ? C21 C22 1.396(3) . ? C21 H21 0.95 . ? C22 H22 0.95 . ? Cl2 C32 1.746(2) . ? C32 C33 1.387(3) . ? C32 C37 1.388(3) . ? C33 C34 1.394(3) . ? C33 H33 0.95 . ? C34 C35 1.392(3) . ? C34 H34 0.95 . ? C35 C36 1.400(3) . ? C35 C38 1.509(3) . ? C36 C37 1.389(3) . ? C36 H36 0.95 . ? C37 H37 0.95 . ? C38 N41 1.464(2) . ? C38 C39 1.503(3) . ? C38 H38 1 . ? C39 C40 1.329(3) . ? C39 H39 0.95 . ? C40 C47 1.478(3) . ? C40 C42 1.542(3) . ? N41 C42 1.419(2) . ? C42 C43 1.497(3) . ? C42 C45 1.499(3) . ? C43 N44 1.144(3) . ? C45 N46 1.144(3) . ? C47 C52 1.401(3) . ? C47 C48 1.404(3) . ? C48 C49 1.396(3) . ? C48 H48 0.95 . ? C49 C50 1.386(4) . ? C49 H49 0.95 . ? C50 C51 1.395(3) . ? C50 H50 0.95 . ? C51 C52 1.394(3) . ? C51 H51 0.95 . ? C52 H52 0.95 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C2 C7 121.4(2) . . ? C3 C2 Cl1 119.72(18) . . ? C7 C2 Cl1 118.84(18) . . ? C2 C3 C4 118.8(2) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 120.9(2) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 119.0(2) . . ? C4 C5 C8 119.98(18) . . ? C6 C5 C8 120.96(19) . . ? C7 C6 C5 120.7(2) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C2 119.1(2) . . ? C6 C7 H7 120.5 . . ? C2 C7 H7 120.5 . . ? N11 C8 C9 103.65(16) . . ? N11 C8 C5 110.96(16) . . ? C9 C8 C5 114.66(16) . . ? N11 C8 H8 109.1 . . ? C9 C8 H8 109.1 . . ? C5 C8 H8 109.1 . . ? C10 C9 C8 112.95(18) . . ? C10 C9 H9 123.5 . . ? C8 C9 H9 123.5 . . ? C9 C10 C17 130.02(18) . . ? C9 C10 C12 107.00(17) . . ? C17 C10 C12 122.89(18) . . ? C12 N11 C8 109.88(14) . . ? N11 C12 C15 108.65(17) . . ? N11 C12 C13 109.08(16) . . ? C15 C12 C13 109.53(18) . . ? N11 C12 C10 106.31(16) . . ? C15 C12 C10 113.00(16) . . ? C13 C12 C10 110.15(17) . . ? N14 C13 C12 176.3(2) . . ? N16 C15 C12 176.4(2) . . ? C22 C17 C18 118.85(18) . . ? C22 C17 C10 122.62(18) . . ? C18 C17 C10 118.52(19) . . ? C19 C18 C17 120.1(2) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 120.74(19) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 119.7(2) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C20 C21 C22 119.9(2) . . ? C20 C21 H21 120 . . ? C22 C21 H21 120 . . ? C21 C22 C17 120.62(19) . . ? C21 C22 H22 119.7 . . ? C17 C22 H22 119.7 . . ? C33 C32 C37 121.6(2) . . ? C33 C32 Cl2 119.70(17) . . ? C37 C32 Cl2 118.67(17) . . ? C32 C33 C34 118.66(19) . . ? C32 C33 H33 120.7 . . ? C34 C33 H33 120.7 . . ? C35 C34 C33 120.78(19) . . ? C35 C34 H34 119.6 . . ? C33 C34 H34 119.6 . . ? C34 C35 C36 119.4(2) . . ? C34 C35 C38 119.83(18) . . ? C36 C35 C38 120.73(19) . . ? C37 C36 C35 120.3(2) . . ? C37 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C32 C37 C36 119.23(19) . . ? C32 C37 H37 120.4 . . ? C36 C37 H37 120.4 . . ? N41 C38 C39 103.55(16) . . ? N41 C38 C35 110.58(16) . . ? C39 C38 C35 114.74(16) . . ? N41 C38 H38 109.3 . . ? C39 C38 H38 109.3 . . ? C35 C38 H38 109.3 . . ? C40 C39 C38 112.87(18) . . ? C40 C39 H39 123.6 . . ? C38 C39 H39 123.6 . . ? C39 C40 C47 130.26(18) . . ? C39 C40 C42 106.93(17) . . ? C47 C40 C42 122.76(18) . . ? C42 N41 C38 110.15(14) . . ? N41 C42 C43 109.88(15) . . ? N41 C42 C45 108.25(16) . . ? C43 C42 C45 110.18(17) . . ? N41 C42 C40 106.39(16) . . ? C43 C42 C40 109.18(16) . . ? C45 C42 C40 112.87(15) . . ? N44 C43 C42 174.7(2) . . ? N46 C45 C42 176.1(2) . . ? C52 C47 C48 118.25(18) . . ? C52 C47 C40 121.81(18) . . ? C48 C47 C40 119.94(19) . . ? C49 C48 C47 120.6(2) . . ? C49 C48 H48 119.7 . . ? C47 C48 H48 119.7 . . ? C50 C49 C48 120.4(2) . . ? C50 C49 H49 119.8 . . ? C48 C49 H49 119.8 . . ? C49 C50 C51 119.8(2) . . ? C49 C50 H50 120.1 . . ? C51 C50 H50 120.1 . . ? C52 C51 C50 119.9(2) . . ? C52 C51 H51 120 . . ? C50 C51 H51 120 . . ? C51 C52 C47 121.0(2) . . ? C51 C52 H52 119.5 . . ? C47 C52 H52 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 C2 C3 C4 1.0(3) . . . . ? Cl1 C2 C3 C4 -179.37(16) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C3 C4 C5 C8 177.84(19) . . . . ? C4 C5 C6 C7 0.5(3) . . . . ? C8 C5 C6 C7 -177.82(19) . . . . ? C5 C6 C7 C2 0.2(3) . . . . ? C3 C2 C7 C6 -1.0(3) . . . . ? Cl1 C2 C7 C6 179.37(16) . . . . ? C4 C5 C8 N11 115.5(2) . . . . ? C6 C5 C8 N11 -66.2(2) . . . . ? C4 C5 C8 C9 -127.5(2) . . . . ? C6 C5 C8 C9 50.8(3) . . . . ? N11 C8 C9 C10 2.6(2) . . . . ? C5 C8 C9 C10 -118.5(2) . . . . ? C8 C9 C10 C17 -176.53(19) . . . . ? C8 C9 C10 C12 0.0(2) . . . . ? C9 C8 N11 C12 -4.4(2) . . . . ? C5 C8 N11 C12 119.19(18) . . . . ? C8 N11 C12 C15 -117.43(18) . . . . ? C8 N11 C12 C13 123.23(18) . . . . ? C8 N11 C12 C10 4.5(2) . . . . ? C9 C10 C12 N11 -2.8(2) . . . . ? C17 C10 C12 N11 174.07(17) . . . . ? C9 C10 C12 C15 116.3(2) . . . . ? C17 C10 C12 C15 -66.8(2) . . . . ? C9 C10 C12 C13 -120.84(19) . . . . ? C17 C10 C12 C13 56.0(2) . . . . ? C9 C10 C17 C22 -158.4(2) . . . . ? C12 C10 C17 C22 25.5(3) . . . . ? C9 C10 C17 C18 22.3(3) . . . . ? C12 C10 C17 C18 -153.74(18) . . . . ? C22 C17 C18 C19 0.8(3) . . . . ? C10 C17 C18 C19 -179.95(18) . . . . ? C17 C18 C19 C20 -0.1(3) . . . . ? C18 C19 C20 C21 0.2(3) . . . . ? C19 C20 C21 C22 -0.9(3) . . . . ? C20 C21 C22 C17 1.5(3) . . . . ? C18 C17 C22 C21 -1.5(3) . . . . ? C10 C17 C22 C21 179.28(18) . . . . ? C37 C32 C33 C34 -0.5(3) . . . . ? Cl2 C32 C33 C34 178.41(15) . . . . ? C32 C33 C34 C35 0.8(3) . . . . ? C33 C34 C35 C36 -0.3(3) . . . . ? C33 C34 C35 C38 179.63(18) . . . . ? C34 C35 C36 C37 -0.6(3) . . . . ? C38 C35 C36 C37 179.55(19) . . . . ? C33 C32 C37 C36 -0.3(3) . . . . ? Cl2 C32 C37 C36 -179.23(16) . . . . ? C35 C36 C37 C32 0.8(3) . . . . ? C34 C35 C38 N41 129.29(18) . . . . ? C36 C35 C38 N41 -50.8(2) . . . . ? C34 C35 C38 C39 -114.1(2) . . . . ? C36 C35 C38 C39 65.8(2) . . . . ? N41 C38 C39 C40 2.7(2) . . . . ? C35 C38 C39 C40 -117.9(2) . . . . ? C38 C39 C40 C47 -178.24(19) . . . . ? C38 C39 C40 C42 -0.9(2) . . . . ? C39 C38 N41 C42 -3.4(2) . . . . ? C35 C38 N41 C42 119.95(17) . . . . ? C38 N41 C42 C43 121.09(17) . . . . ? C38 N41 C42 C45 -118.54(17) . . . . ? C38 N41 C42 C40 3.0(2) . . . . ? C39 C40 C42 N41 -1.3(2) . . . . ? C47 C40 C42 N41 176.28(17) . . . . ? C39 C40 C42 C43 -119.83(18) . . . . ? C47 C40 C42 C43 57.7(2) . . . . ? C39 C40 C42 C45 117.28(19) . . . . ? C47 C40 C42 C45 -65.1(2) . . . . ? C39 C40 C47 C52 -161.8(2) . . . . ? C42 C40 C47 C52 21.3(3) . . . . ? C39 C40 C47 C48 18.8(3) . . . . ? C42 C40 C47 C48 -158.18(18) . . . . ? C52 C47 C48 C49 1.7(3) . . . . ? C40 C47 C48 C49 -178.87(19) . . . . ? C47 C48 C49 C50 0.1(3) . . . . ? C48 C49 C50 C51 -0.8(3) . . . . ? C49 C50 C51 C52 -0.5(3) . . . . ? C50 C51 C52 C47 2.4(3) . . . . ? C48 C47 C52 C51 -2.9(3) . . . . ? C40 C47 C52 C51 177.62(19) . . . . ? data_3c _database_code_depnum_ccdc_archive 'CCDC 891059' #TrackingRef 'cif pub Samira.cif' _audit_creation_date 2010-05-25T15:00:25-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H14 N2 O2' _chemical_formula_sum 'C19 H14 N2 O2' _chemical_formula_weight 302.32 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.446(4) _cell_length_b 7.670(3) _cell_length_c 16.378(10) _cell_angle_alpha 96.97(4) _cell_angle_beta 102.06(2) _cell_angle_gamma 118.99(2) _cell_volume 772.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3689 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 27.05 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.26 _exptl_crystal_density_diffrn 1.3 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.722 _exptl_absorpt_correction_T_max 0.978 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_unetI/netI 0.0552 _diffrn_reflns_number 8622 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.963 _reflns_number_total 3395 _reflns_number_gt 2690 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.11(3) _refine_ls_number_reflns 3395 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.102 _refine_ls_R_factor_gt 0.0897 _refine_ls_wR_factor_ref 0.292 _refine_ls_wR_factor_gt 0.2758 _refine_ls_goodness_of_fit_ref 1.173 _refine_ls_restrained_S_all 1.173 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.414 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.083 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.4105(5) 0.4816(4) 0.74292(19) 0.0287(7) Uani 1 1 d . . . C2 C 0.5421(5) 0.4051(5) 0.7128(2) 0.0344(8) Uani 1 1 d . . . N3 N 0.6449(5) 0.3467(6) 0.6922(2) 0.0482(9) Uani 1 1 d . . . C4 C 0.5040(5) 0.7013(5) 0.7372(2) 0.0344(8) Uani 1 1 d . . . N5 N 0.5704(6) 0.8687(5) 0.7342(2) 0.0500(9) Uani 1 1 d . . . O6 O 0.4303(4) 0.4791(3) 0.83033(14) 0.0333(6) Uani 1 1 d . . . C7 C 0.1700(5) 0.3491(4) 0.6926(2) 0.0274(7) Uani 1 1 d . . . C8 C 0.0843(5) 0.3009(5) 0.5979(2) 0.0303(7) Uani 1 1 d . . . C9 C 0.2109(6) 0.4054(6) 0.5474(2) 0.0387(8) Uani 1 1 d . . . H9 H 0.3583 0.5105 0.5742 0.046 Uiso 1 1 calc R . . C10 C 0.1208(8) 0.3555(7) 0.4584(2) 0.0510(11) Uani 1 1 d . . . H10 H 0.2073 0.4251 0.4243 0.061 Uiso 1 1 calc R . . C11 C -0.0952(8) 0.2041(8) 0.4192(2) 0.0545(12) Uani 1 1 d . . . H11 H -0.1575 0.173 0.3585 0.065 Uiso 1 1 calc R . . C12 C -0.2189(7) 0.0993(7) 0.4683(3) 0.0530(11) Uani 1 1 d . . . H12 H -0.3655 -0.0069 0.4407 0.064 Uiso 1 1 calc R . . C13 C -0.1340(6) 0.1454(6) 0.5568(2) 0.0396(9) Uani 1 1 d . . . H13 H -0.2223 0.0728 0.5899 0.048 Uiso 1 1 calc R . . C14 C 0.0662(5) 0.2909(5) 0.7511(2) 0.0302(7) Uani 1 1 d . . . H14 H -0.0866 0.2146 0.7369 0.036 Uiso 1 1 calc R . . C15 C 0.2132(5) 0.3571(5) 0.8405(2) 0.0306(7) Uani 1 1 d . . . H15 H 0.1878 0.449 0.8789 0.037 Uiso 1 1 calc R . . C16 C 0.1989(5) 0.1855(5) 0.8800(2) 0.0285(7) Uani 1 1 d . . . C17 C 0.2679(5) 0.2204(5) 0.9694(2) 0.0280(7) Uani 1 1 d . . . H17 H 0.3162 0.3516 1.0051 0.034 Uiso 1 1 calc R . . C18 C 0.2682(5) 0.0688(5) 1.00802(19) 0.0283(7) Uani 1 1 d . . . H18 H 0.3204 0.0976 1.0691 0.034 Uiso 1 1 calc R . . C19 C 0.1907(5) -0.1268(5) 0.9558(2) 0.0288(7) Uani 1 1 d . . . C20 C 0.1167(5) -0.1657(5) 0.8660(2) 0.0339(8) Uani 1 1 d . . . H20 H 0.0635 -0.2984 0.8303 0.041 Uiso 1 1 calc R . . C21 C 0.1203(5) -0.0125(5) 0.8289(2) 0.0321(7) Uani 1 1 d . . . H21 H 0.0689 -0.0412 0.7677 0.039 Uiso 1 1 calc R . . O22 O 0.1803(4) -0.2877(3) 0.98648(15) 0.0348(6) Uani 1 1 d . . . C23 C 0.2620(5) -0.2510(5) 1.0781(2) 0.0336(8) Uani 1 1 d . . . H23A H 0.4131 -0.1371 1.0991 0.05 Uiso 1 1 calc R . . H23B H 0.2522 -0.376 1.0914 0.05 Uiso 1 1 calc R . . H23C H 0.1766 -0.2149 1.1065 0.05 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0242(15) 0.0227(14) 0.0374(16) 0.0101(12) 0.0094(12) 0.0107(12) C2 0.0267(16) 0.0326(17) 0.0420(18) 0.0132(13) 0.0097(13) 0.0139(14) N3 0.0418(19) 0.056(2) 0.056(2) 0.0146(15) 0.0159(15) 0.0321(17) C4 0.0259(16) 0.0301(17) 0.0418(17) 0.0116(13) 0.0086(13) 0.0111(13) N5 0.0426(18) 0.0305(15) 0.060(2) 0.0157(13) 0.0053(15) 0.0104(14) O6 0.0235(11) 0.0321(12) 0.0341(12) 0.0099(9) 0.0063(9) 0.0079(9) C7 0.0222(15) 0.0235(14) 0.0379(16) 0.0115(11) 0.0098(12) 0.0122(12) C8 0.0302(17) 0.0285(15) 0.0357(16) 0.0099(12) 0.0081(13) 0.0184(13) C9 0.043(2) 0.0419(18) 0.0423(18) 0.0174(14) 0.0174(15) 0.0275(17) C10 0.074(3) 0.067(3) 0.043(2) 0.0267(19) 0.028(2) 0.054(3) C11 0.071(3) 0.081(3) 0.0333(18) 0.0088(19) 0.0063(18) 0.061(3) C12 0.046(2) 0.059(2) 0.048(2) -0.0082(19) -0.0029(18) 0.034(2) C13 0.0341(19) 0.0388(18) 0.0422(18) 0.0044(14) 0.0050(14) 0.0203(16) C14 0.0239(15) 0.0283(15) 0.0405(17) 0.0132(12) 0.0106(12) 0.0140(13) C15 0.0277(16) 0.0279(15) 0.0364(16) 0.0098(12) 0.0122(12) 0.0135(13) C16 0.0224(15) 0.0288(15) 0.0372(16) 0.0106(12) 0.0124(12) 0.0139(12) C17 0.0240(15) 0.0236(14) 0.0352(15) 0.0074(11) 0.0112(12) 0.0107(12) C18 0.0239(15) 0.0278(15) 0.0305(14) 0.0085(11) 0.0081(11) 0.0114(12) C19 0.0202(14) 0.0254(15) 0.0382(16) 0.0095(12) 0.0098(12) 0.0095(12) C20 0.0298(17) 0.0308(16) 0.0355(16) 0.0034(12) 0.0060(13) 0.0145(14) C21 0.0281(16) 0.0331(16) 0.0303(15) 0.0049(12) 0.0048(12) 0.0150(13) O22 0.0354(13) 0.0247(11) 0.0415(13) 0.0102(9) 0.0095(10) 0.0144(10) C23 0.0268(16) 0.0314(16) 0.0435(18) 0.0153(13) 0.0104(13) 0.0150(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O6 1.412(4) . ? C1 C2 1.495(5) . ? C1 C4 1.504(5) . ? C1 C7 1.528(4) . ? C2 N3 1.143(5) . ? C4 N5 1.143(5) . ? O6 C15 1.483(4) . ? C7 C14 1.340(5) . ? C7 C8 1.472(4) . ? C8 C9 1.403(5) . ? C8 C13 1.410(5) . ? C9 C10 1.389(5) . ? C9 H9 0.95 . ? C10 C11 1.387(7) . ? C10 H10 0.95 . ? C11 C12 1.375(7) . ? C11 H11 0.95 . ? C12 C13 1.379(5) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 C15 1.486(4) . ? C14 H14 0.95 . ? C15 C16 1.504(5) . ? C15 H15 1 . ? C16 C17 1.392(4) . ? C16 C21 1.406(4) . ? C17 C18 1.390(5) . ? C17 H17 0.95 . ? C18 C19 1.400(4) . ? C18 H18 0.95 . ? C19 O22 1.362(4) . ? C19 C20 1.396(4) . ? C20 C21 1.379(5) . ? C20 H20 0.95 . ? C21 H21 0.95 . ? O22 C23 1.432(4) . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 C1 C2 108.7(3) . . ? O6 C1 C4 108.6(2) . . ? C2 C1 C4 107.5(3) . . ? O6 C1 C7 107.1(3) . . ? C2 C1 C7 113.6(3) . . ? C4 C1 C7 111.3(3) . . ? N3 C2 C1 178.1(4) . . ? N5 C4 C1 177.7(4) . . ? C1 O6 C15 109.9(2) . . ? C14 C7 C8 130.1(3) . . ? C14 C7 C1 106.4(3) . . ? C8 C7 C1 123.5(3) . . ? C9 C8 C13 118.9(3) . . ? C9 C8 C7 122.5(3) . . ? C13 C8 C7 118.5(3) . . ? C10 C9 C8 120.1(4) . . ? C10 C9 H9 120 . . ? C8 C9 H9 120 . . ? C11 C10 C9 120.2(4) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 119.9(4) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 121.2(4) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C8 119.6(4) . . ? C12 C13 H13 120.2 . . ? C8 C13 H13 120.2 . . ? C7 C14 C15 113.5(3) . . ? C7 C14 H14 123.2 . . ? C15 C14 H14 123.2 . . ? O6 C15 C14 103.0(3) . . ? O6 C15 C16 109.8(3) . . ? C14 C15 C16 115.6(3) . . ? O6 C15 H15 109.4 . . ? C14 C15 H15 109.4 . . ? C16 C15 H15 109.4 . . ? C17 C16 C21 117.9(3) . . ? C17 C16 C15 120.4(3) . . ? C21 C16 C15 121.7(3) . . ? C18 C17 C16 121.9(3) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C17 C18 C19 119.2(3) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? O22 C19 C20 116.1(3) . . ? O22 C19 C18 124.3(3) . . ? C20 C19 C18 119.6(3) . . ? C21 C20 C19 120.3(3) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C16 121.0(3) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? C19 O22 C23 117.6(2) . . ? O22 C23 H23A 109.5 . . ? O22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C2 C1 O6 C15 -125.1(3) . . . . ? C4 C1 O6 C15 118.2(3) . . . . ? C7 C1 O6 C15 -2.0(3) . . . . ? O6 C1 C7 C14 4.0(3) . . . . ? C2 C1 C7 C14 123.9(3) . . . . ? C4 C1 C7 C14 -114.5(3) . . . . ? O6 C1 C7 C8 -175.3(3) . . . . ? C2 C1 C7 C8 -55.3(4) . . . . ? C4 C1 C7 C8 66.2(4) . . . . ? C14 C7 C8 C9 167.6(3) . . . . ? C1 C7 C8 C9 -13.3(5) . . . . ? C14 C7 C8 C13 -11.6(5) . . . . ? C1 C7 C8 C13 167.5(3) . . . . ? C13 C8 C9 C10 0.1(5) . . . . ? C7 C8 C9 C10 -179.1(3) . . . . ? C8 C9 C10 C11 0.9(5) . . . . ? C9 C10 C11 C12 -1.8(6) . . . . ? C10 C11 C12 C13 1.9(6) . . . . ? C11 C12 C13 C8 -0.9(6) . . . . ? C9 C8 C13 C12 -0.1(5) . . . . ? C7 C8 C13 C12 179.1(3) . . . . ? C8 C7 C14 C15 174.7(3) . . . . ? C1 C7 C14 C15 -4.5(4) . . . . ? C1 O6 C15 C14 -0.4(3) . . . . ? C1 O6 C15 C16 123.2(3) . . . . ? C7 C14 C15 O6 3.2(3) . . . . ? C7 C14 C15 C16 -116.4(3) . . . . ? O6 C15 C16 C17 86.2(3) . . . . ? C14 C15 C16 C17 -157.9(3) . . . . ? O6 C15 C16 C21 -92.6(3) . . . . ? C14 C15 C16 C21 23.3(5) . . . . ? C21 C16 C17 C18 2.5(5) . . . . ? C15 C16 C17 C18 -176.4(3) . . . . ? C16 C17 C18 C19 -2.1(5) . . . . ? C17 C18 C19 O22 -179.0(3) . . . . ? C17 C18 C19 C20 0.7(5) . . . . ? O22 C19 C20 C21 179.9(3) . . . . ? C18 C19 C20 C21 0.2(5) . . . . ? C19 C20 C21 C16 0.3(5) . . . . ? C17 C16 C21 C20 -1.6(5) . . . . ? C15 C16 C21 C20 177.3(3) . . . . ? C20 C19 O22 C23 177.8(3) . . . . ? C18 C19 O22 C23 -2.5(5) . . . . ? data_5'a _database_code_depnum_ccdc_archive 'CCDC 891060' #TrackingRef 'cif pub Samira.cif' _audit_creation_date 2010-07-13T10:06:57-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H10 N2 O3' _chemical_formula_sum 'C14 H10 N2 O3' _chemical_formula_weight 254.24 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.355 _cell_length_b 8.01 _cell_length_c 24.798 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1262.4 _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 20387 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'no color' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_T_max 0.981 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_unetI/netI 0.0278 _diffrn_reflns_number 18424 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 2876 _reflns_number_gt 2380 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0617P)^2^+0.2933P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2876 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.103 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 0.946 _refine_ls_restrained_S_all 0.946 _refine_ls_shift/su_max 0.027 _refine_ls_shift/su_mean 0.002 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(12) _refine_diff_density_max 0.188 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.041 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.2977(3) 0.3682(2) 0.03560(7) 0.0353(4) Uani 1 1 d . . . H1 H 0.1576 0.3304 0.0301 0.042 Uiso 1 1 calc R . . C2 C 0.3736(4) 0.5036(3) 0.00655(8) 0.0488(5) Uani 1 1 d . . . H2 H 0.285 0.5585 -0.0187 0.059 Uiso 1 1 calc R . . C3 C 0.5759(4) 0.5584(3) 0.01411(8) 0.0518(6) Uani 1 1 d . . . H3 H 0.6274 0.6506 -0.0061 0.062 Uiso 1 1 calc R . . C4 C 0.7046(3) 0.4798(3) 0.05100(9) 0.0469(5) Uani 1 1 d . . . H4 H 0.8441 0.519 0.0565 0.056 Uiso 1 1 calc R . . C5 C 0.6316(3) 0.3438(2) 0.08004(7) 0.0357(4) Uani 1 1 d . . . H5 H 0.7215 0.2888 0.1049 0.043 Uiso 1 1 calc R . . C6 C 0.4264(3) 0.2881(2) 0.07265(6) 0.0283(4) Uani 1 1 d . . . C7 C 0.3409(3) 0.1422(2) 0.10416(6) 0.0274(4) Uani 1 1 d . . . H7 H 0.1933 0.118 0.0925 0.033 Uiso 1 1 calc R . . C8 C 0.3488(2) 0.1628(2) 0.16461(6) 0.0264(3) Uani 1 1 d . . . C9 C 0.2259(3) 0.2857(2) 0.19678(6) 0.0276(4) Uani 1 1 d . . . O10 O 0.2648(2) 0.31785(16) 0.24302(5) 0.0381(3) Uani 1 1 d . . . O11 O 0.06319(19) 0.34640(17) 0.16924(5) 0.0372(3) Uani 1 1 d . . . C12 C -0.0654(3) 0.4654(3) 0.19888(9) 0.0509(6) Uani 1 1 d . . . H12A H -0.1187 0.4128 0.2318 0.076 Uiso 1 1 calc R . . H12B H -0.1842 0.5007 0.1764 0.076 Uiso 1 1 calc R . . H12C H 0.0199 0.563 0.2084 0.076 Uiso 1 1 calc R . . C13 C 0.4712(3) 0.0502(2) 0.18750(7) 0.0293(4) Uani 1 1 d . . . H13 H 0.5051 0.0451 0.2248 0.035 Uiso 1 1 calc R . . C14 C 0.5483(3) -0.0688(2) 0.14488(7) 0.0301(4) Uani 1 1 d . . . C15 C 0.4631(3) -0.2404(2) 0.15496(7) 0.0330(4) Uani 1 1 d . . . N16 N 0.4004(3) -0.3694(2) 0.16442(7) 0.0475(4) Uani 1 1 d . . . C17 C 0.7827(3) -0.0824(2) 0.14214(8) 0.0355(4) Uani 1 1 d . . . N18 N 0.9603(3) -0.0919(3) 0.13925(8) 0.0514(5) Uani 1 1 d . . . O19 O 0.4733(2) -0.00492(15) 0.09515(4) 0.0345(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0415(10) 0.0356(10) 0.0289(8) -0.0005(8) -0.0048(7) 0.0045(8) C2 0.0710(15) 0.0395(11) 0.0359(10) 0.0076(9) -0.0030(10) 0.0069(11) C3 0.0805(16) 0.0331(11) 0.0417(11) 0.0060(9) 0.0147(11) -0.0044(11) C4 0.0466(11) 0.0393(11) 0.0548(12) -0.0067(10) 0.0144(10) -0.0102(10) C5 0.0353(9) 0.0342(10) 0.0376(9) -0.0002(8) 0.0008(7) 0.0008(8) C6 0.0324(8) 0.0291(8) 0.0233(7) -0.0020(6) 0.0011(6) 0.0032(7) C7 0.0276(8) 0.0278(8) 0.0270(8) -0.0012(7) -0.0014(6) 0.0043(7) C8 0.0252(8) 0.0288(8) 0.0252(7) 0.0012(7) 0.0008(6) -0.0028(7) C9 0.0292(8) 0.0256(8) 0.0280(8) -0.0008(7) -0.0001(6) -0.0020(7) O10 0.0469(7) 0.0390(7) 0.0282(6) -0.0060(5) -0.0034(5) 0.0046(6) O11 0.0325(6) 0.0406(7) 0.0385(6) -0.0087(6) -0.0055(5) 0.0093(6) C12 0.0408(11) 0.0539(14) 0.0580(12) -0.0165(10) -0.0020(10) 0.0185(10) C13 0.0314(8) 0.0296(9) 0.0269(8) 0.0009(7) -0.0010(7) -0.0014(7) C14 0.0313(8) 0.0280(9) 0.0309(8) 0.0031(7) 0.0016(7) 0.0026(7) C15 0.0327(8) 0.0303(10) 0.0359(9) 0.0010(7) 0.0033(7) 0.0034(8) N16 0.0523(10) 0.0345(10) 0.0558(10) 0.0007(8) 0.0047(8) -0.0045(8) C17 0.0381(10) 0.0311(9) 0.0372(9) 0.0077(8) 0.0061(8) -0.0006(8) N18 0.0362(9) 0.0593(11) 0.0586(10) 0.0160(9) 0.0088(8) 0.0007(9) O19 0.0465(7) 0.0304(6) 0.0265(6) -0.0007(5) 0.0022(5) 0.0091(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.387(2) . ? C1 C2 1.388(3) . ? C1 H1 0.95 . ? C2 C3 1.371(4) . ? C2 H2 0.95 . ? C3 C4 1.380(3) . ? C3 H3 0.95 . ? C4 C5 1.386(3) . ? C4 H4 0.95 . ? C5 C6 1.390(3) . ? C5 H5 0.95 . ? C6 C7 1.507(2) . ? C7 O19 1.465(2) . ? C7 C8 1.509(2) . ? C7 H7 1 . ? C8 C13 1.319(2) . ? C8 C9 1.489(2) . ? C9 O10 1.2011(19) . ? C9 O11 1.331(2) . ? O11 C12 1.455(2) . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 C14 1.505(2) . ? C13 H13 0.95 . ? C14 O19 1.418(2) . ? C14 C17 1.495(2) . ? C14 C15 1.498(2) . ? C15 N16 1.132(2) . ? C17 N18 1.134(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.98(18) . . ? C6 C1 H1 120 . . ? C2 C1 H1 120 . . ? C3 C2 C1 120.34(19) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.02(19) . . ? C2 C3 H3 120 . . ? C4 C3 H3 120 . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 119.87(19) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 119.47(17) . . ? C1 C6 C7 119.28(15) . . ? C5 C6 C7 121.25(15) . . ? O19 C7 C8 102.72(13) . . ? O19 C7 C6 109.72(13) . . ? C8 C7 C6 114.73(14) . . ? O19 C7 H7 109.8 . . ? C8 C7 H7 109.8 . . ? C6 C7 H7 109.8 . . ? C13 C8 C9 122.06(14) . . ? C13 C8 C7 111.87(15) . . ? C9 C8 C7 125.95(14) . . ? O10 C9 O11 124.86(15) . . ? O10 C9 C8 123.05(15) . . ? O11 C9 C8 111.98(13) . . ? C9 O11 C12 114.62(14) . . ? O11 C12 H12A 109.5 . . ? O11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C13 C14 108.83(15) . . ? C8 C13 H13 125.6 . . ? C14 C13 H13 125.6 . . ? O19 C14 C17 108.75(14) . . ? O19 C14 C15 110.79(15) . . ? C17 C14 C15 107.53(15) . . ? O19 C14 C13 105.82(13) . . ? C17 C14 C13 113.72(16) . . ? C15 C14 C13 110.25(14) . . ? N16 C15 C14 177.6(2) . . ? N18 C17 C14 178.9(2) . . ? C14 O19 C7 110.54(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.3(3) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C5 0.9(3) . . . . ? C3 C4 C5 C6 -1.1(3) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? C2 C1 C6 C7 179.52(16) . . . . ? C4 C5 C6 C1 0.9(3) . . . . ? C4 C5 C6 C7 -179.11(16) . . . . ? C1 C6 C7 O19 122.78(16) . . . . ? C5 C6 C7 O19 -57.2(2) . . . . ? C1 C6 C7 C8 -122.22(17) . . . . ? C5 C6 C7 C8 57.8(2) . . . . ? O19 C7 C8 C13 1.84(18) . . . . ? C6 C7 C8 C13 -117.15(17) . . . . ? O19 C7 C8 C9 -174.35(14) . . . . ? C6 C7 C8 C9 66.7(2) . . . . ? C13 C8 C9 O10 18.1(3) . . . . ? C7 C8 C9 O10 -166.06(16) . . . . ? C13 C8 C9 O11 -158.22(16) . . . . ? C7 C8 C9 O11 17.6(2) . . . . ? O10 C9 O11 C12 2.8(3) . . . . ? C8 C9 O11 C12 179.04(15) . . . . ? C9 C8 C13 C14 172.17(14) . . . . ? C7 C8 C13 C14 -4.19(19) . . . . ? C8 C13 C14 O19 4.94(19) . . . . ? C8 C13 C14 C17 124.24(17) . . . . ? C8 C13 C14 C15 -114.91(17) . . . . ? O19 C14 C15 N16 -161(5) . . . . ? C17 C14 C15 N16 80(5) . . . . ? C13 C14 C15 N16 -44(5) . . . . ? O19 C14 C17 N18 -5(13) . . . . ? C15 C14 C17 N18 115(13) . . . . ? C13 C14 C17 N18 -123(13) . . . . ? C17 C14 O19 C7 -126.29(15) . . . . ? C15 C14 O19 C7 115.73(15) . . . . ? C13 C14 O19 C7 -3.76(18) . . . . ? C8 C7 O19 C14 1.44(17) . . . . ? C6 C7 O19 C14 123.87(14) . . . . ? data_5b _database_code_depnum_ccdc_archive 'CCDC 891061' #TrackingRef 'cif pub Samira.cif' _audit_creation_date 2010-11-10T15:06:02-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H9 Cl N2 O3' _chemical_formula_sum 'C14 H9 Cl N2 O3' _chemical_formula_weight 288.68 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0681(3) _cell_length_b 9.2126(3) _cell_length_c 13.3847(3) _cell_angle_alpha 90 _cell_angle_beta 90.0100(10) _cell_angle_gamma 90 _cell_volume 1364.78(7) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 3606 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 27.27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.11 _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.867 _exptl_absorpt_correction_T_max 0.969 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_unetI/netI 0.031 _diffrn_reflns_number 10042 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 3101 _reflns_number_gt 2394 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0383P)^2^+0.4011P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3101 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.098 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.209 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.041 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.34164(15) -0.04142(18) 0.83447(11) 0.0366(4) Uani 1 1 d . . . C2 C 0.25859(18) -0.0903(2) 0.76578(13) 0.0478(5) Uani 1 1 d . . . H2 H 0.1988 -0.1591 0.7844 0.057 Uiso 1 1 calc R . . C3 C 0.26378(17) -0.0373(2) 0.66889(13) 0.0482(5) Uani 1 1 d . . . H3 H 0.2065 -0.0697 0.6209 0.058 Uiso 1 1 calc R . . C4 C 0.35141(13) 0.06228(18) 0.64118(11) 0.0319(3) Uani 1 1 d . . . C5 C 0.43242(15) 0.11133(19) 0.71196(12) 0.0388(4) Uani 1 1 d . . . H5 H 0.4921 0.1806 0.6939 0.047 Uiso 1 1 calc R . . C6 C 0.42722(15) 0.0599(2) 0.80968(12) 0.0413(4) Uani 1 1 d . . . H6 H 0.4823 0.0946 0.8586 0.05 Uiso 1 1 calc R . . C7 C 0.35900(14) 0.12012(18) 0.53519(11) 0.0338(4) Uani 1 1 d . . . H7 H 0.4412 0.1618 0.5234 0.041 Uiso 1 1 calc R . . C8 C 0.26547(14) 0.23114(17) 0.51016(11) 0.0321(3) Uani 1 1 d . . . H8 H 0.2575 0.3219 0.5433 0.038 Uiso 1 1 calc R . . C9 C 0.19519(13) 0.18755(16) 0.43630(10) 0.0292(3) Uani 1 1 d . . . C10 C 0.23498(13) 0.03748(17) 0.40328(11) 0.0307(3) Uani 1 1 d . . . O11 O 0.33659(9) 0.00345(13) 0.46328(7) 0.0367(3) Uani 1 1 d . . . C12 C 0.13790(15) -0.07341(18) 0.41840(11) 0.0346(4) Uani 1 1 d . . . N13 N 0.06442(15) -0.15711(18) 0.43259(12) 0.0506(4) Uani 1 1 d . . . C14 C 0.27011(14) 0.03575(18) 0.29547(11) 0.0345(4) Uani 1 1 d . . . N15 N 0.29653(13) 0.03793(19) 0.21346(10) 0.0483(4) Uani 1 1 d . . . C16 C 0.09086(14) 0.25604(17) 0.38599(10) 0.0305(3) Uani 1 1 d . . . O17 O 0.03074(11) 0.19190(13) 0.32515(9) 0.0440(3) Uani 1 1 d . . . O18 O 0.07433(10) 0.39228(11) 0.41439(8) 0.0350(3) Uani 1 1 d . . . C19 C -0.02736(17) 0.4652(2) 0.36743(13) 0.0473(5) Uani 1 1 d . . . H19A H -0.0198 0.4581 0.2946 0.071 Uiso 1 1 calc R . . H19B H -0.028 0.5676 0.3872 0.071 Uiso 1 1 calc R . . H19C H -0.1028 0.419 0.3888 0.071 Uiso 1 1 calc R . . Cl1 Cl 0.33871(4) -0.11121(5) 0.95594(3) 0.05043(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0420(9) 0.0400(9) 0.0278(7) 0.0032(7) -0.0004(6) 0.0117(8) C2 0.0546(11) 0.0511(11) 0.0377(9) 0.0087(8) -0.0035(8) -0.0137(9) C3 0.0519(11) 0.0581(12) 0.0344(9) 0.0075(8) -0.0129(8) -0.0179(9) C4 0.0291(8) 0.0366(9) 0.0299(7) 0.0020(6) -0.0043(6) 0.0030(7) C5 0.0331(8) 0.0479(10) 0.0354(8) 0.0021(7) -0.0036(7) -0.0044(7) C6 0.0363(9) 0.0558(11) 0.0318(8) -0.0026(8) -0.0079(7) 0.0010(8) C7 0.0318(8) 0.0394(9) 0.0301(7) 0.0022(7) -0.0048(6) -0.0037(7) C8 0.0385(8) 0.0310(8) 0.0267(7) 0.0025(6) -0.0021(6) -0.0046(7) C9 0.0334(8) 0.0282(8) 0.0258(7) 0.0011(6) 0.0002(6) -0.0003(6) C10 0.0325(8) 0.0339(8) 0.0255(7) -0.0001(6) -0.0012(6) 0.0020(7) O11 0.0375(6) 0.0419(7) 0.0308(6) -0.0023(5) -0.0051(5) 0.0092(5) C12 0.0429(9) 0.0315(9) 0.0295(8) -0.0037(6) 0.0020(7) 0.0025(7) N13 0.0568(10) 0.0416(9) 0.0535(9) -0.0024(7) 0.0072(8) -0.0098(8) C14 0.0327(8) 0.0396(9) 0.0311(8) -0.0025(7) -0.0023(6) 0.0022(7) N15 0.0438(8) 0.0682(11) 0.0328(8) -0.0012(7) 0.0017(6) 0.0038(8) C16 0.0362(8) 0.0304(8) 0.0249(7) 0.0004(6) -0.0011(6) 0.0005(7) O17 0.0477(7) 0.0425(7) 0.0417(7) -0.0098(5) -0.0174(5) 0.0043(6) O18 0.0438(6) 0.0288(6) 0.0323(5) 0.0004(4) -0.0079(5) 0.0048(5) C19 0.0593(11) 0.0412(10) 0.0414(9) 0.0006(8) -0.0121(8) 0.0182(9) Cl1 0.0635(3) 0.0566(3) 0.0312(2) 0.00989(19) -0.00312(19) 0.0099(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.371(2) . ? C1 C2 1.376(2) . ? C1 Cl1 1.7486(15) . ? C2 C3 1.387(2) . ? C2 H2 0.95 . ? C3 C4 1.386(2) . ? C3 H3 0.95 . ? C4 C5 1.380(2) . ? C4 C7 1.518(2) . ? C5 C6 1.392(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O11 1.4640(19) . ? C7 C8 1.493(2) . ? C7 H7 1 . ? C8 C9 1.320(2) . ? C8 H8 0.95 . ? C9 C16 1.478(2) . ? C9 C10 1.517(2) . ? C10 O11 1.4169(17) . ? C10 C14 1.495(2) . ? C10 C12 1.496(2) . ? C12 N13 1.137(2) . ? C14 N15 1.136(2) . ? C16 O17 1.2062(17) . ? C16 O18 1.3241(18) . ? O18 C19 1.4535(19) . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.52(15) . . ? C6 C1 Cl1 119.24(12) . . ? C2 C1 Cl1 119.24(14) . . ? C1 C2 C3 118.81(17) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 120.83(16) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 119.19(14) . . ? C5 C4 C7 119.37(14) . . ? C3 C4 C7 121.43(13) . . ? C4 C5 C6 120.42(16) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 119.20(15) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? O11 C7 C8 103.77(11) . . ? O11 C7 C4 110.32(13) . . ? C8 C7 C4 114.31(13) . . ? O11 C7 H7 109.4 . . ? C8 C7 H7 109.4 . . ? C4 C7 H7 109.4 . . ? C9 C8 C7 111.59(14) . . ? C9 C8 H8 124.2 . . ? C7 C8 H8 124.2 . . ? C8 C9 C16 132.17(14) . . ? C8 C9 C10 108.92(13) . . ? C16 C9 C10 118.90(12) . . ? O11 C10 C14 109.77(12) . . ? O11 C10 C12 110.01(12) . . ? C14 C10 C12 108.07(12) . . ? O11 C10 C9 105.49(11) . . ? C14 C10 C9 111.51(13) . . ? C12 C10 C9 111.98(12) . . ? C10 O11 C7 110.15(11) . . ? N13 C12 C10 178.15(17) . . ? N15 C14 C10 178.37(19) . . ? O17 C16 O18 125.58(14) . . ? O17 C16 C9 121.96(14) . . ? O18 C16 C9 112.45(12) . . ? C16 O18 C19 114.90(12) . . ? O18 C19 H19A 109.5 . . ? O18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.3(3) . . . . ? Cl1 C1 C2 C3 -178.21(15) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C5 -1.5(3) . . . . ? C2 C3 C4 C7 179.40(17) . . . . ? C3 C4 C5 C6 0.9(3) . . . . ? C7 C4 C5 C6 179.97(15) . . . . ? C2 C1 C6 C5 -1.9(3) . . . . ? Cl1 C1 C6 C5 177.58(13) . . . . ? C4 C5 C6 C1 0.8(3) . . . . ? C5 C4 C7 O11 140.57(15) . . . . ? C3 C4 C7 O11 -40.3(2) . . . . ? C5 C4 C7 C8 -102.96(17) . . . . ? C3 C4 C7 C8 76.1(2) . . . . ? O11 C7 C8 C9 1.36(17) . . . . ? C4 C7 C8 C9 -118.85(15) . . . . ? C7 C8 C9 C16 179.26(15) . . . . ? C7 C8 C9 C10 0.32(17) . . . . ? C8 C9 C10 O11 -1.94(16) . . . . ? C16 C9 C10 O11 178.96(12) . . . . ? C8 C9 C10 C14 -121.05(14) . . . . ? C16 C9 C10 C14 59.85(17) . . . . ? C8 C9 C10 C12 117.71(14) . . . . ? C16 C9 C10 C12 -61.39(17) . . . . ? C14 C10 O11 C7 123.07(13) . . . . ? C12 C10 O11 C7 -118.14(13) . . . . ? C9 C10 O11 C7 2.81(15) . . . . ? C8 C7 O11 C10 -2.61(15) . . . . ? C4 C7 O11 C10 120.27(13) . . . . ? C8 C9 C16 O17 -172.90(16) . . . . ? C10 C9 C16 O17 5.9(2) . . . . ? C8 C9 C16 O18 8.1(2) . . . . ? C10 C9 C16 O18 -173.06(13) . . . . ? O17 C16 O18 C19 1.2(2) . . . . ? C9 C16 O18 C19 -179.87(13) . . . . ? data_8a _database_code_depnum_ccdc_archive 'CCDC 891062' #TrackingRef 'cif pub Samira.cif' _audit_creation_date 2010-07-12T18:52:10-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C15 H12 N2 O3' _chemical_formula_sum 'C15 H12 N2 O3' _chemical_formula_weight 268.27 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.5077(4) _cell_length_b 9.6154(5) _cell_length_c 9.3240(4) _cell_angle_alpha 90 _cell_angle_beta 116.932(7) _cell_angle_gamma 90 _cell_volume 680.02(6) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 14677 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.31 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.960 _exptl_absorpt_correction_T_max 0.993 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_unetI/netI 0.0223 _diffrn_reflns_number 10464 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 1659 _reflns_number_gt 1509 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+0.1264P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1659 _refine_ls_number_parameters 183 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_diff_density_max 0.164 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.3671(3) 0.2550(3) 1.0784(3) 0.0413(6) Uani 1 1 d . . . H2 H 0.3859 0.2504 1.1868 0.05 Uiso 1 1 calc R . . C3 C 0.4542(3) 0.3530(3) 1.0336(3) 0.0452(6) Uani 1 1 d . . . H3 H 0.5344 0.4152 1.1118 0.054 Uiso 1 1 calc R . . C4 C 0.4260(3) 0.3620(3) 0.8750(3) 0.0366(5) Uani 1 1 d . . . H4 H 0.4856 0.4306 0.8447 0.044 Uiso 1 1 calc R . . C5 C 0.3108(2) 0.2706(2) 0.7613(2) 0.0262(4) Uani 1 1 d . . . C6 C 0.2244(3) 0.1709(2) 0.8068(2) 0.0313(4) Uani 1 1 d . . . H6 H 0.1458 0.1075 0.7293 0.038 Uiso 1 1 calc R . . C7 C 0.2523(3) 0.1633(3) 0.9655(3) 0.0376(5) Uani 1 1 d . . . H7 H 0.1925 0.0952 0.9963 0.045 Uiso 1 1 calc R . . C8 C 0.2821(3) 0.2787(2) 0.5888(2) 0.0269(4) Uani 1 1 d . . . H8 H 0.3653 0.3479 0.5804 0.032 Uiso 1 1 calc R . . C9 C 0.2998(3) 0.1421(2) 0.5201(2) 0.0273(4) Uani 1 1 d . . . C10 C 0.4682(3) 0.0640(2) 0.5891(2) 0.0297(4) Uani 1 1 d . . . O11 O 0.4850(2) -0.05510(18) 0.5611(2) 0.0435(4) Uani 1 1 d . . . O12 O 0.59813(19) 0.14500(18) 0.68920(18) 0.0366(4) Uani 1 1 d . . . C13 C 0.7710(3) 0.0820(3) 0.7670(3) 0.0426(6) Uani 1 1 d . . . H13A H 0.7717 0.0091 0.8409 0.064 Uiso 1 1 calc R . . H13B H 0.8588 0.153 0.8275 0.064 Uiso 1 1 calc R . . H13C H 0.7998 0.041 0.6855 0.064 Uiso 1 1 calc R . . C14 C 0.1509(3) 0.1021(2) 0.3958(2) 0.0281(4) Uani 1 1 d . . . C15 C 0.1037(3) -0.0235(2) 0.2915(3) 0.0377(5) Uani 1 1 d . . . H15A H 0.2088 -0.0812 0.3211 0.057 Uiso 1 1 calc R . . H15B H 0.0573 0.0049 0.1787 0.057 Uiso 1 1 calc R . . H15C H 0.0138 -0.077 0.3059 0.057 Uiso 1 1 calc R . . C16 C 0.0159(3) 0.2169(2) 0.3665(2) 0.0293(4) Uani 1 1 d . . . O17 O 0.09980(19) 0.32028(16) 0.48358(16) 0.0328(3) Uani 1 1 d . . . C18 C -0.0429(3) 0.2795(2) 0.2029(2) 0.0328(5) Uani 1 1 d . . . N19 N -0.0819(3) 0.3271(3) 0.0801(2) 0.0473(5) Uani 1 1 d . . . C20 C -0.1432(3) 0.1660(2) 0.3792(2) 0.0329(5) Uani 1 1 d . . . N21 N -0.2620(3) 0.1287(3) 0.3935(3) 0.0457(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0421(12) 0.0550(16) 0.0280(10) -0.0005(10) 0.0168(9) 0.0048(12) C3 0.0454(13) 0.0559(16) 0.0299(11) -0.0130(11) 0.0130(10) -0.0087(12) C4 0.0348(11) 0.0394(12) 0.0344(11) -0.0075(10) 0.0145(9) -0.0078(10) C5 0.0231(9) 0.0270(10) 0.0274(9) -0.0017(8) 0.0106(8) 0.0029(8) C6 0.0296(9) 0.0317(11) 0.0318(10) -0.0023(9) 0.0132(8) -0.0017(9) C7 0.0386(11) 0.0418(13) 0.0384(11) 0.0045(10) 0.0228(9) 0.0013(10) C8 0.0245(9) 0.0276(10) 0.0273(9) -0.0008(8) 0.0107(8) 0.0014(8) C9 0.0314(9) 0.0272(10) 0.0271(9) 0.0000(8) 0.0167(8) 0.0003(8) C10 0.0345(10) 0.0323(12) 0.0277(9) 0.0004(8) 0.0189(8) 0.0032(9) O11 0.0455(9) 0.0334(9) 0.0535(10) -0.0045(8) 0.0242(8) 0.0069(8) O12 0.0286(7) 0.0389(9) 0.0382(8) -0.0031(7) 0.0115(6) 0.0051(7) C13 0.0279(10) 0.0548(15) 0.0419(12) 0.0040(11) 0.0129(9) 0.0091(11) C14 0.0334(10) 0.0271(10) 0.0268(9) -0.0004(8) 0.0163(8) -0.0005(8) C15 0.0448(13) 0.0326(12) 0.0363(11) -0.0079(9) 0.0189(10) -0.0036(10) C16 0.0320(10) 0.0278(10) 0.0264(10) -0.0002(8) 0.0117(8) 0.0004(9) O17 0.0303(7) 0.0307(8) 0.0292(7) -0.0055(6) 0.0062(6) 0.0036(6) C18 0.0331(10) 0.0325(11) 0.0297(10) -0.0007(9) 0.0114(8) -0.0036(9) N19 0.0540(12) 0.0485(13) 0.0353(10) 0.0070(10) 0.0165(9) 0.0001(11) C20 0.0334(10) 0.0330(11) 0.0302(10) 0.0032(9) 0.0125(8) 0.0028(9) N21 0.0398(10) 0.0483(12) 0.0505(11) 0.0079(11) 0.0218(9) 0.0013(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 C3 1.376(4) . ? C2 C7 1.381(3) . ? C2 H2 0.95 . ? C3 C4 1.389(3) . ? C3 H3 0.95 . ? C4 C5 1.384(3) . ? C4 H4 0.95 . ? C5 C6 1.386(3) . ? C5 C8 1.516(3) . ? C6 C7 1.391(3) . ? C6 H6 0.95 . ? C7 H7 0.95 . ? C8 O17 1.466(2) . ? C8 C9 1.499(3) . ? C8 H8 1 . ? C9 C14 1.328(3) . ? C9 C10 1.481(3) . ? C10 O11 1.198(3) . ? C10 O12 1.329(3) . ? O12 C13 1.446(3) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 C15 1.488(3) . ? C14 C16 1.526(3) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 O17 1.409(3) . ? C16 C20 1.493(3) . ? C16 C18 1.500(3) . ? C18 N19 1.134(3) . ? C20 N21 1.136(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C2 C7 119.9(2) . . ? C3 C2 H2 120.1 . . ? C7 C2 H2 120.1 . . ? C2 C3 C4 120.6(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 119.8(2) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 119.64(18) . . ? C4 C5 C8 119.88(19) . . ? C6 C5 C8 120.47(18) . . ? C5 C6 C7 120.2(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C2 C7 C6 119.9(2) . . ? C2 C7 H7 120 . . ? C6 C7 H7 120 . . ? O17 C8 C9 103.50(16) . . ? O17 C8 C5 109.72(15) . . ? C9 C8 C5 114.19(17) . . ? O17 C8 H8 109.7 . . ? C9 C8 H8 109.7 . . ? C5 C8 H8 109.7 . . ? C14 C9 C10 125.78(19) . . ? C14 C9 C8 112.69(18) . . ? C10 C9 C8 121.53(18) . . ? O11 C10 O12 124.7(2) . . ? O11 C10 C9 125.3(2) . . ? O12 C10 C9 109.97(18) . . ? C10 O12 C13 116.14(18) . . ? O12 C13 H13A 109.5 . . ? O12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C14 C15 132.4(2) . . ? C9 C14 C16 106.87(18) . . ? C15 C14 C16 120.76(18) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O17 C16 C20 109.20(17) . . ? O17 C16 C18 108.87(18) . . ? C20 C16 C18 108.38(17) . . ? O17 C16 C14 107.19(16) . . ? C20 C16 C14 112.66(18) . . ? C18 C16 C14 110.49(17) . . ? C16 O17 C8 109.71(16) . . ? N19 C18 C16 177.8(2) . . ? N21 C20 C16 177.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 C2 C3 C4 0.9(4) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C3 C4 C5 C8 -179.0(2) . . . . ? C4 C5 C6 C7 0.5(3) . . . . ? C8 C5 C6 C7 179.5(2) . . . . ? C3 C2 C7 C6 -0.4(4) . . . . ? C5 C6 C7 C2 -0.3(3) . . . . ? C4 C5 C8 O17 -114.6(2) . . . . ? C6 C5 C8 O17 66.4(2) . . . . ? C4 C5 C8 C9 129.8(2) . . . . ? C6 C5 C8 C9 -49.2(2) . . . . ? O17 C8 C9 C14 -2.0(2) . . . . ? C5 C8 C9 C14 117.18(19) . . . . ? O17 C8 C9 C10 178.40(16) . . . . ? C5 C8 C9 C10 -62.4(2) . . . . ? C14 C9 C10 O11 -13.7(3) . . . . ? C8 C9 C10 O11 165.8(2) . . . . ? C14 C9 C10 O12 167.28(19) . . . . ? C8 C9 C10 O12 -13.2(2) . . . . ? O11 C10 O12 C13 0.5(3) . . . . ? C9 C10 O12 C13 179.50(17) . . . . ? C10 C9 C14 C15 0.3(3) . . . . ? C8 C9 C14 C15 -179.2(2) . . . . ? C10 C9 C14 C16 -178.70(18) . . . . ? C8 C9 C14 C16 1.8(2) . . . . ? C9 C14 C16 O17 -0.8(2) . . . . ? C15 C14 C16 O17 -179.92(18) . . . . ? C9 C14 C16 C20 -120.93(19) . . . . ? C15 C14 C16 C20 59.9(2) . . . . ? C9 C14 C16 C18 117.70(19) . . . . ? C15 C14 C16 C18 -61.4(2) . . . . ? C20 C16 O17 C8 121.82(18) . . . . ? C18 C16 O17 C8 -120.03(18) . . . . ? C14 C16 O17 C8 -0.5(2) . . . . ? C9 C8 O17 C16 1.4(2) . . . . ? C5 C8 O17 C16 -120.82(18) . . . . ? data_8b _database_code_depnum_ccdc_archive 'CCDC 891063' #TrackingRef 'cif pub Samira.cif' _audit_creation_date 2012-06-27T13:39:32-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C15 H11 Cl1 N2 O3' _chemical_formula_sum 'C15 H11 Cl1 N2 O3' _chemical_formula_weight 302.71 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.545 _cell_length_b 10.072 _cell_length_c 11.676 _cell_angle_alpha 107.83 _cell_angle_beta 101.23 _cell_angle_gamma 92.8 _cell_volume 713.8 _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 10080 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.911 _exptl_absorpt_correction_T_max 0.946 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'Kappa CCD, Nonius' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_unetI/netI 0.0504 _diffrn_reflns_number 11348 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 3257 _reflns_number_gt 2050 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.3152P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3257 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0973 _refine_ls_R_factor_gt 0.047 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.224 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2 C 0.7736(4) -0.0894(2) 0.85799(19) 0.0366(5) Uani 1 1 d . . . C3 C 0.6348(4) 0.0003(2) 0.8293(2) 0.0432(6) Uani 1 1 d . . . H3 H 0.5088 0.0077 0.8586 0.052 Uiso 1 1 calc R . . C4 C 0.6808(4) 0.0794(2) 0.7575(2) 0.0385(5) Uani 1 1 d . . . H4 H 0.5866 0.1423 0.7383 0.046 Uiso 1 1 calc R . . C5 C 0.9562(4) -0.1021(2) 0.8166(2) 0.0378(5) Uani 1 1 d . . . H5 H 1.051 -0.1637 0.8376 0.045 Uiso 1 1 calc R . . C6 C 1.0000(4) -0.0232(2) 0.7435(2) 0.0348(5) Uani 1 1 d . . . H6 H 1.1257 -0.0319 0.714 0.042 Uiso 1 1 calc R . . C7 C 0.8638(3) 0.0679(2) 0.71302(19) 0.0303(5) Uani 1 1 d . . . C8 C 0.9199(3) 0.1535(2) 0.63571(19) 0.0322(5) Uani 1 1 d . . . H8 H 1.0521 0.126 0.6089 0.039 Uiso 1 1 calc R . . C9 C 0.9414(3) 0.3090(2) 0.69839(19) 0.0312(5) Uani 1 1 d . . . C10 C 1.1174(4) 0.3765(2) 0.8064(2) 0.0358(5) Uani 1 1 d . . . O11 O 1.2711(3) 0.32046(18) 0.82947(16) 0.0507(5) Uani 1 1 d . . . O12 O 1.0837(3) 0.50332(16) 0.87177(15) 0.0464(4) Uani 1 1 d . . . C13 C 1.2547(5) 0.5825(3) 0.9729(3) 0.0630(8) Uani 1 1 d . . . H13A H 1.2829 0.5327 1.0335 0.095 Uiso 1 1 calc R . . H13B H 1.2161 0.6757 1.0124 0.095 Uiso 1 1 calc R . . H13C H 1.3807 0.5926 0.9413 0.095 Uiso 1 1 calc R . . C14 C 0.8025(3) 0.3717(2) 0.6404(2) 0.0326(5) Uani 1 1 d . . . C15 C 0.7591(4) 0.5204(2) 0.6643(2) 0.0464(6) Uani 1 1 d . . . H15A H 0.8544 0.5798 0.7405 0.07 Uiso 1 1 calc R . . H15B H 0.6137 0.5278 0.6729 0.07 Uiso 1 1 calc R . . H15C H 0.7805 0.5513 0.5952 0.07 Uiso 1 1 calc R . . C16 C 0.6771(3) 0.2585(2) 0.52448(19) 0.0321(5) Uani 1 1 d . . . C17 C 0.7113(3) 0.2911(2) 0.4129(2) 0.0363(5) Uani 1 1 d . . . N18 N 0.7365(3) 0.3222(2) 0.3302(2) 0.0516(6) Uani 1 1 d . . . C19 C 0.4493(4) 0.2534(2) 0.5210(2) 0.0367(5) Uani 1 1 d . . . N20 N 0.2759(4) 0.2573(2) 0.5215(2) 0.0500(5) Uani 1 1 d . . . O21 O 0.7491(3) 0.13009(15) 0.52744(13) 0.0384(4) Uani 1 1 d . . . Cl1 Cl 0.71810(12) -0.18719(7) 0.95007(6) 0.0552(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0489(14) 0.0287(11) 0.0299(11) 0.0083(9) 0.0077(10) -0.0059(10) C3 0.0409(14) 0.0436(13) 0.0455(14) 0.0110(11) 0.0174(11) -0.0012(11) C4 0.0382(13) 0.0360(12) 0.0435(13) 0.0143(10) 0.0112(11) 0.0065(10) C5 0.0439(14) 0.0317(11) 0.0375(12) 0.0124(10) 0.0055(11) 0.0051(10) C6 0.0358(12) 0.0315(11) 0.0378(12) 0.0115(9) 0.0093(10) 0.0040(9) C7 0.0328(12) 0.0255(10) 0.0299(11) 0.0068(8) 0.0049(9) 0.0001(9) C8 0.0333(12) 0.0300(10) 0.0332(11) 0.0112(9) 0.0056(10) 0.0044(9) C9 0.0327(12) 0.0291(10) 0.0318(11) 0.0104(9) 0.0072(9) -0.0016(9) C10 0.0340(13) 0.0377(12) 0.0373(12) 0.0165(10) 0.0065(10) -0.0030(10) O11 0.0411(10) 0.0529(10) 0.0525(11) 0.0177(9) -0.0043(8) 0.0060(8) O12 0.0429(10) 0.0375(9) 0.0450(9) 0.0011(7) -0.0006(8) -0.0046(7) C13 0.0560(17) 0.0564(16) 0.0524(17) -0.0024(13) -0.0056(14) -0.0193(14) C14 0.0337(12) 0.0301(10) 0.0348(11) 0.0118(9) 0.0081(10) -0.0005(9) C15 0.0491(15) 0.0320(12) 0.0540(15) 0.0123(11) 0.0033(12) 0.0075(11) C16 0.0341(12) 0.0317(11) 0.0331(11) 0.0140(9) 0.0073(9) 0.0048(9) C17 0.0333(12) 0.0389(12) 0.0378(12) 0.0139(10) 0.0070(10) 0.0070(10) N18 0.0536(14) 0.0645(14) 0.0477(13) 0.0279(11) 0.0187(11) 0.0154(11) C19 0.0400(14) 0.0383(12) 0.0319(12) 0.0137(10) 0.0056(10) -0.0009(10) N20 0.0429(13) 0.0590(13) 0.0507(13) 0.0219(11) 0.0117(10) -0.0009(10) O21 0.0494(10) 0.0275(7) 0.0338(8) 0.0088(6) 0.0002(7) 0.0046(7) Cl1 0.0822(5) 0.0428(3) 0.0434(4) 0.0173(3) 0.0192(3) -0.0088(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 C5 1.371(3) . ? C2 C3 1.379(3) . ? C2 Cl1 1.739(2) . ? C3 C4 1.384(3) . ? C3 H3 0.95 . ? C4 C7 1.392(3) . ? C4 H4 0.95 . ? C5 C6 1.389(3) . ? C5 H5 0.95 . ? C6 C7 1.385(3) . ? C6 H6 0.95 . ? C7 C8 1.506(3) . ? C8 O21 1.464(2) . ? C8 C9 1.499(3) . ? C8 H8 1 . ? C9 C14 1.327(3) . ? C9 C10 1.487(3) . ? C10 O11 1.202(3) . ? C10 O12 1.327(3) . ? O12 C13 1.451(3) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 C15 1.489(3) . ? C14 C16 1.529(3) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 O21 1.406(2) . ? C16 C19 1.481(3) . ? C16 C17 1.492(3) . ? C17 N18 1.140(3) . ? C19 N20 1.139(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C2 C3 121.4(2) . . ? C5 C2 Cl1 119.16(18) . . ? C3 C2 Cl1 119.46(19) . . ? C2 C3 C4 119.3(2) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C7 120.7(2) . . ? C3 C4 H4 119.7 . . ? C7 C4 H4 119.7 . . ? C2 C5 C6 118.9(2) . . ? C2 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C7 C6 C5 121.2(2) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C4 118.6(2) . . ? C6 C7 C8 119.4(2) . . ? C4 C7 C8 122.04(19) . . ? O21 C8 C9 103.48(16) . . ? O21 C8 C7 109.66(16) . . ? C9 C8 C7 114.06(18) . . ? O21 C8 H8 109.8 . . ? C9 C8 H8 109.8 . . ? C7 C8 H8 109.8 . . ? C14 C9 C10 127.6(2) . . ? C14 C9 C8 112.54(18) . . ? C10 C9 C8 119.59(18) . . ? O11 C10 O12 125.1(2) . . ? O11 C10 C9 122.8(2) . . ? O12 C10 C9 112.12(19) . . ? C10 O12 C13 116.2(2) . . ? O12 C13 H13A 109.5 . . ? O12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C14 C15 133.5(2) . . ? C9 C14 C16 107.02(18) . . ? C15 C14 C16 119.47(19) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O21 C16 C19 110.60(18) . . ? O21 C16 C17 111.22(18) . . ? C19 C16 C17 107.56(18) . . ? O21 C16 C14 106.81(16) . . ? C19 C16 C14 111.15(18) . . ? C17 C16 C14 109.53(17) . . ? N18 C17 C16 176.9(2) . . ? N20 C19 C16 176.2(3) . . ? C16 O21 C8 110.05(15) . . ? 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 C5 C2 C3 C4 -0.1(3) . . . . ? Cl1 C2 C3 C4 179.08(17) . . . . ? C2 C3 C4 C7 0.8(3) . . . . ? C3 C2 C5 C6 -0.5(3) . . . . ? Cl1 C2 C5 C6 -179.71(16) . . . . ? C2 C5 C6 C7 0.5(3) . . . . ? C5 C6 C7 C4 0.2(3) . . . . ? C5 C6 C7 C8 178.76(19) . . . . ? C3 C4 C7 C6 -0.8(3) . . . . ? C3 C4 C7 C8 -179.4(2) . . . . ? C6 C7 C8 O21 125.6(2) . . . . ? C4 C7 C8 O21 -55.9(3) . . . . ? C6 C7 C8 C9 -118.9(2) . . . . ? C4 C7 C8 C9 59.6(3) . . . . ? O21 C8 C9 C14 1.6(2) . . . . ? C7 C8 C9 C14 -117.5(2) . . . . ? O21 C8 C9 C10 -173.22(18) . . . . ? C7 C8 C9 C10 67.7(3) . . . . ? C14 C9 C10 O11 -156.0(2) . . . . ? C8 C9 C10 O11 18.0(3) . . . . ? C14 C9 C10 O12 23.8(3) . . . . ? C8 C9 C10 O12 -162.30(19) . . . . ? O11 C10 O12 C13 4.9(3) . . . . ? C9 C10 O12 C13 -174.8(2) . . . . ? C10 C9 C14 C15 -5.8(4) . . . . ? C8 C9 C14 C15 179.9(2) . . . . ? C10 C9 C14 C16 171.3(2) . . . . ? C8 C9 C14 C16 -2.9(3) . . . . ? C9 C14 C16 O21 3.2(2) . . . . ? C15 C14 C16 O21 -179.2(2) . . . . ? C9 C14 C16 C19 124.0(2) . . . . ? C15 C14 C16 C19 -58.4(3) . . . . ? C9 C14 C16 C17 -117.3(2) . . . . ? C15 C14 C16 C17 60.3(3) . . . . ? O21 C16 C17 N18 -161(4) . . . . ? C19 C16 C17 N18 78(5) . . . . ? C14 C16 C17 N18 -43(5) . . . . ? O21 C16 C19 N20 152(4) . . . . ? C17 C16 C19 N20 -86(4) . . . . ? C14 C16 C19 N20 34(4) . . . . ? C19 C16 O21 C8 -123.36(19) . . . . ? C17 C16 O21 C8 117.19(19) . . . . ? C14 C16 O21 C8 -2.3(2) . . . . ? C9 C8 O21 C16 0.6(2) . . . . ? C7 C8 O21 C16 122.70(19) . . . . ?