# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Ashwini Nangia' _publ_contact_author_email ashwini.nangia@gmail.com _publ_section_title ; Blonanserin HCl salt and its monohydrate ; loop_ _publ_author_name A.Nangia D.Maddileti R.Thakuria S.Cherukuvada # Attachment '- BLN HCl H2O.cif' data_mono _database_code_depnum_ccdc_archive 'CCDC 849050' #TrackingRef '- BLN HCl H2O.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H33 Cl F N3 O' _chemical_formula_weight 421.97 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.0708(14) _cell_length_b 11.9644(10) _cell_length_c 11.0576(9) _cell_angle_alpha 90.00 _cell_angle_beta 106.1890(10) _cell_angle_gamma 90.00 _cell_volume 2168.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4437 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 25.98 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.204 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9451 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8198 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 25.98 _reflns_number_total 4199 _reflns_number_gt 3511 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0406P)^2^+1.6455P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4199 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H1A H 0.3909(19) 0.817(3) 0.326(3) 0.066(10) Uiso 1 1 d . . . H1B H 0.3949(18) 0.775(3) 0.452(3) 0.057(9) Uiso 1 1 d . . . O1 O 0.41057(10) 0.83430(14) 0.40914(17) 0.0311(4) Uani 1 1 d . . . C1 C 0.73228(11) 0.77618(16) 0.31331(18) 0.0158(4) Uani 1 1 d . . . C2 C 0.77112(11) 0.78995(16) 0.21850(18) 0.0167(4) Uani 1 1 d . . . H2 H 0.7595 0.7408 0.1482 0.020 Uiso 1 1 calc R . . C3 C 0.82658(11) 0.87576(16) 0.22816(18) 0.0166(4) Uani 1 1 d . . . C4 C 0.84668(11) 0.94438(16) 0.33560(18) 0.0171(4) Uani 1 1 d . . . C5 C 0.80899(11) 0.91942(16) 0.42904(18) 0.0167(4) Uani 1 1 d . . . C6 C 0.90481(12) 1.04140(17) 0.34849(19) 0.0210(5) Uani 1 1 d . . . H6A H 0.9454 1.0237 0.3025 0.025 Uiso 1 1 calc R . . H6B H 0.9346 1.0508 0.4385 0.025 Uiso 1 1 calc R . . C7 C 0.86275(14) 1.15237(18) 0.2982(2) 0.0249(5) Uani 1 1 d . . . H7A H 0.9035 1.2132 0.3218 0.030 Uiso 1 1 calc R . . H7B H 0.8446 1.1486 0.2051 0.030 Uiso 1 1 calc R . . C8 C 0.78966(13) 1.18306(18) 0.3449(2) 0.0264(5) Uani 1 1 d . . . H8A H 0.7464 1.1267 0.3129 0.032 Uiso 1 1 calc R . . H8B H 0.7683 1.2560 0.3079 0.032 Uiso 1 1 calc R . . C9 C 0.80616(14) 1.19079(18) 0.4884(2) 0.0258(5) Uani 1 1 d . . . H9A H 0.8653 1.2037 0.5258 0.031 Uiso 1 1 calc R . . H9B H 0.7771 1.2571 0.5078 0.031 Uiso 1 1 calc R . . C10 C 0.78112(13) 1.08914(18) 0.55310(19) 0.0223(5) Uani 1 1 d . . . H10A H 0.7228 1.0736 0.5119 0.027 Uiso 1 1 calc R . . H10B H 0.7859 1.1094 0.6417 0.027 Uiso 1 1 calc R . . C11 C 0.82906(12) 0.98097(17) 0.55313(18) 0.0179(4) Uani 1 1 d . . . H11A H 0.8880 0.9990 0.5782 0.021 Uiso 1 1 calc R . . H11B H 0.8189 0.9302 0.6178 0.021 Uiso 1 1 calc R . . C12 C 0.86306(12) 0.89046(17) 0.12097(18) 0.0178(4) Uani 1 1 d . . . C13 C 0.92064(12) 0.81451(18) 0.1042(2) 0.0223(5) Uani 1 1 d . . . H13 H 0.9384 0.7560 0.1636 0.027 Uiso 1 1 calc R . . C14 C 0.95271(13) 0.82254(19) 0.0021(2) 0.0254(5) Uani 1 1 d . . . H14 H 0.9920 0.7704 -0.0093 0.031 Uiso 1 1 calc R . . C15 C 0.92589(12) 0.90790(19) -0.08174(19) 0.0239(5) Uani 1 1 d . . . C16 C 0.86857(13) 0.98429(19) -0.0700(2) 0.0253(5) Uani 1 1 d . . . H16 H 0.8511 1.0424 -0.1301 0.030 Uiso 1 1 calc R . . C17 C 0.83683(13) 0.97434(18) 0.03171(19) 0.0219(5) Uani 1 1 d . . . H17 H 0.7964 1.0257 0.0408 0.026 Uiso 1 1 calc R . . C18 C 0.63303(12) 0.68098(18) 0.40305(19) 0.0202(4) Uani 1 1 d . . . H18A H 0.6415 0.7469 0.4593 0.024 Uiso 1 1 calc R . . H18B H 0.6611 0.6164 0.4526 0.024 Uiso 1 1 calc R . . C19 C 0.54270(12) 0.65660(17) 0.35364(19) 0.0190(4) Uani 1 1 d . . . H19A H 0.5204 0.6389 0.4250 0.023 Uiso 1 1 calc R . . H19B H 0.5141 0.7237 0.3106 0.023 Uiso 1 1 calc R . . C20 C 0.56507(12) 0.58486(17) 0.15955(18) 0.0202(4) Uani 1 1 d . . . H20A H 0.5376 0.6502 0.1108 0.024 Uiso 1 1 calc R . . H20B H 0.5573 0.5199 0.1019 0.024 Uiso 1 1 calc R . . C21 C 0.65519(12) 0.60889(17) 0.21187(19) 0.0194(4) Uani 1 1 d . . . H21A H 0.6833 0.5419 0.2559 0.023 Uiso 1 1 calc R . . H21B H 0.6789 0.6269 0.1421 0.023 Uiso 1 1 calc R . . C22 C 0.43878(12) 0.53344(18) 0.2128(2) 0.0224(5) Uani 1 1 d . . . H22A H 0.4319 0.4763 0.1458 0.027 Uiso 1 1 calc R . . H22B H 0.4090 0.6014 0.1744 0.027 Uiso 1 1 calc R . . C23 C 0.40203(12) 0.49035(18) 0.3134(2) 0.0239(5) Uani 1 1 d . . . H23A H 0.4326 0.4248 0.3541 0.036 Uiso 1 1 calc R . . H23B H 0.3450 0.4695 0.2749 0.036 Uiso 1 1 calc R . . H23C H 0.4046 0.5489 0.3764 0.036 Uiso 1 1 calc R . . F1 F 0.95827(8) 0.91703(12) -0.18065(11) 0.0348(3) Uani 1 1 d . . . H3 H 0.5531(14) 0.497(2) 0.305(2) 0.029(6) Uiso 1 1 d . . . N1 N 0.75203(9) 0.83857(13) 0.41798(15) 0.0167(4) Uani 1 1 d . . . N2 N 0.66742(10) 0.70240(14) 0.29921(15) 0.0185(4) Uani 1 1 d . . . N3 N 0.52773(10) 0.56060(14) 0.26369(16) 0.0172(4) Uani 1 1 d . . . Cl1 Cl 0.60960(3) 0.34597(4) 0.39044(5) 0.02719(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0396(10) 0.0255(9) 0.0285(10) 0.0018(8) 0.0100(8) 0.0001(7) C1 0.0154(9) 0.0141(10) 0.0167(10) 0.0013(8) 0.0027(8) 0.0030(8) C2 0.0200(10) 0.0134(10) 0.0163(10) -0.0009(8) 0.0041(8) 0.0016(8) C3 0.0152(9) 0.0158(10) 0.0180(10) 0.0034(8) 0.0031(8) 0.0043(7) C4 0.0157(9) 0.0166(10) 0.0181(10) 0.0017(8) 0.0034(8) 0.0005(8) C5 0.0154(9) 0.0158(10) 0.0174(10) 0.0027(8) 0.0022(8) 0.0025(8) C6 0.0205(10) 0.0262(11) 0.0166(10) -0.0012(9) 0.0056(8) -0.0055(9) C7 0.0340(12) 0.0199(11) 0.0201(11) 0.0002(9) 0.0061(9) -0.0095(9) C8 0.0312(12) 0.0170(11) 0.0268(12) 0.0010(9) 0.0012(9) -0.0022(9) C9 0.0285(12) 0.0221(11) 0.0255(12) -0.0033(9) 0.0054(9) 0.0006(9) C10 0.0232(11) 0.0258(12) 0.0179(11) -0.0055(9) 0.0059(8) -0.0014(9) C11 0.0188(10) 0.0193(10) 0.0156(10) 0.0002(8) 0.0046(8) -0.0034(8) C12 0.0186(10) 0.0182(10) 0.0158(10) -0.0037(8) 0.0033(8) -0.0045(8) C13 0.0231(11) 0.0234(11) 0.0207(11) 0.0027(9) 0.0064(9) 0.0025(9) C14 0.0204(11) 0.0332(13) 0.0241(12) -0.0018(10) 0.0084(9) 0.0024(9) C15 0.0204(10) 0.0371(13) 0.0151(10) -0.0043(9) 0.0063(8) -0.0100(9) C16 0.0290(11) 0.0264(12) 0.0175(11) 0.0051(9) 0.0019(9) -0.0036(9) C17 0.0237(11) 0.0200(11) 0.0207(11) 0.0008(9) 0.0042(9) 0.0007(9) C18 0.0228(11) 0.0204(11) 0.0177(10) -0.0027(8) 0.0060(8) -0.0050(8) C19 0.0232(10) 0.0168(10) 0.0180(10) -0.0029(8) 0.0071(8) -0.0016(8) C20 0.0265(11) 0.0183(10) 0.0155(10) -0.0018(8) 0.0054(8) -0.0037(8) C21 0.0242(11) 0.0157(10) 0.0197(11) -0.0027(8) 0.0084(8) -0.0005(8) C22 0.0201(10) 0.0215(11) 0.0219(11) -0.0012(9) -0.0005(8) -0.0046(8) C23 0.0227(10) 0.0224(11) 0.0257(11) -0.0030(9) 0.0050(9) -0.0062(9) F1 0.0317(7) 0.0575(10) 0.0184(7) 0.0004(6) 0.0120(6) -0.0075(6) N1 0.0164(8) 0.0170(9) 0.0152(8) 0.0002(7) 0.0023(7) -0.0005(7) N2 0.0211(9) 0.0189(9) 0.0168(9) -0.0037(7) 0.0076(7) -0.0044(7) N3 0.0193(9) 0.0132(8) 0.0177(9) 0.0002(7) 0.0029(7) -0.0021(7) Cl1 0.0388(3) 0.0191(3) 0.0226(3) 0.0031(2) 0.0068(2) 0.0067(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.339(2) . ? C1 N2 1.390(2) . ? C1 C2 1.398(3) . ? C2 C3 1.380(3) . ? C3 C4 1.406(3) . ? C3 C12 1.495(3) . ? C4 C5 1.393(3) . ? C4 C6 1.508(3) . ? C5 N1 1.353(2) . ? C5 C11 1.510(3) . ? C6 C7 1.538(3) . ? C7 C8 1.522(3) . ? C8 C9 1.535(3) . ? C9 C10 1.531(3) . ? C10 C11 1.531(3) . ? C12 C13 1.389(3) . ? C12 C17 1.391(3) . ? C13 C14 1.389(3) . ? C14 C15 1.369(3) . ? C15 F1 1.360(2) . ? C15 C16 1.371(3) . ? C16 C17 1.383(3) . ? C18 N2 1.451(3) . ? C18 C19 1.514(3) . ? C19 N3 1.494(2) . ? C20 N3 1.492(3) . ? C20 C21 1.512(3) . ? C21 N2 1.455(3) . ? C22 N3 1.500(2) . ? C22 C23 1.512(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 116.84(18) . . ? N1 C1 C2 121.66(18) . . ? N2 C1 C2 121.35(17) . . ? C3 C2 C1 119.22(18) . . ? C2 C3 C4 120.02(19) . . ? C2 C3 C12 117.03(18) . . ? C4 C3 C12 122.95(18) . . ? C5 C4 C3 116.57(18) . . ? C5 C4 C6 121.51(18) . . ? C3 C4 C6 121.91(18) . . ? N1 C5 C4 123.71(18) . . ? N1 C5 C11 113.97(17) . . ? C4 C5 C11 122.32(17) . . ? C4 C6 C7 113.69(17) . . ? C8 C7 C6 115.46(17) . . ? C7 C8 C9 115.70(18) . . ? C10 C9 C8 116.13(18) . . ? C9 C10 C11 116.92(17) . . ? C5 C11 C10 115.23(16) . . ? C13 C12 C17 118.50(19) . . ? C13 C12 C3 119.71(18) . . ? C17 C12 C3 121.64(18) . . ? C12 C13 C14 121.2(2) . . ? C15 C14 C13 117.9(2) . . ? F1 C15 C14 118.0(2) . . ? F1 C15 C16 118.9(2) . . ? C14 C15 C16 123.1(2) . . ? C15 C16 C17 118.1(2) . . ? C16 C17 C12 121.2(2) . . ? N2 C18 C19 110.16(16) . . ? N3 C19 C18 110.87(16) . . ? N3 C20 C21 110.47(16) . . ? N2 C21 C20 110.03(16) . . ? N3 C22 C23 112.47(16) . . ? C1 N1 C5 118.57(17) . . ? C1 N2 C18 120.58(16) . . ? C1 N2 C21 121.68(17) . . ? C18 N2 C21 112.01(16) . . ? C20 N3 C19 109.50(15) . . ? C20 N3 C22 110.99(15) . . ? C19 N3 C22 112.55(16) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.293 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.052 # Attachment '- BLN HCl.cif' data_an1385 _database_code_depnum_ccdc_archive 'CCDC 849051' #TrackingRef '- BLN HCl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H31 Cl F N3' _chemical_formula_sum 'C23 H31 Cl F N3' _chemical_formula_weight 403.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.485(10) _cell_length_b 8.578(9) _cell_length_c 16.794(18) _cell_angle_alpha 82.718(17) _cell_angle_beta 85.478(17) _cell_angle_gamma 84.883(11) _cell_volume 1063(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3486 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 26.09 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9494 _exptl_absorpt_correction_T_max 0.9665 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany The values quoted are generated by SHELX based on crystal size and the corrections are not significant for small crystals composed of light atoms. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9615 _diffrn_reflns_av_R_equivalents 0.0783 _diffrn_reflns_av_sigmaI/netI 0.0858 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 26.15 _reflns_number_total 4082 _reflns_number_gt 2863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1569P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4082 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1063 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.2420 _refine_ls_wR_factor_gt 0.1953 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5760(4) 0.4966(4) 0.31083(17) 0.0193(7) Uani 1 1 d . . . C2 C 0.4334(4) 0.4511(4) 0.27163(18) 0.0200(7) Uani 1 1 d . . . H2 H 0.3681 0.3649 0.2951 0.024 Uiso 1 1 calc R . . C3 C 0.3891(4) 0.5331(4) 0.19861(18) 0.0204(7) Uani 1 1 d . . . C4 C 0.4858(4) 0.6632(4) 0.16551(18) 0.0209(7) Uani 1 1 d . . . C5 C 0.6288(4) 0.6976(4) 0.20874(18) 0.0210(7) Uani 1 1 d . . . C6 C 0.4295(5) 0.7725(4) 0.09242(18) 0.0250(8) Uani 1 1 d . . . H6A H 0.3760 0.7109 0.0556 0.030 Uiso 1 1 calc R . . H6B H 0.5374 0.8171 0.0636 0.030 Uiso 1 1 calc R . . C7 C 0.2934(5) 0.9079(4) 0.1134(2) 0.0289(8) Uani 1 1 d . . . H7A H 0.1785 0.8634 0.1338 0.035 Uiso 1 1 calc R . . H7B H 0.2705 0.9791 0.0635 0.035 Uiso 1 1 calc R . . C8 C 0.3505(5) 1.0058(4) 0.1760(2) 0.0298(8) Uani 1 1 d . . . H8A H 0.3539 0.9380 0.2283 0.036 Uiso 1 1 calc R . . H8B H 0.2562 1.0927 0.1826 0.036 Uiso 1 1 calc R . . C9 C 0.5326(5) 1.0779(4) 0.1582(2) 0.0307(8) Uani 1 1 d . . . H9A H 0.5650 1.0831 0.0996 0.037 Uiso 1 1 calc R . . H9B H 0.5181 1.1874 0.1719 0.037 Uiso 1 1 calc R . . C10 C 0.6884(5) 0.9897(4) 0.2028(2) 0.0293(8) Uani 1 1 d . . . H10A H 0.6521 0.9777 0.2611 0.035 Uiso 1 1 calc R . . H10B H 0.7917 1.0558 0.1944 0.035 Uiso 1 1 calc R . . C11 C 0.7522(5) 0.8259(4) 0.17857(19) 0.0232(7) Uani 1 1 d . . . H11A H 0.7664 0.8340 0.1191 0.028 Uiso 1 1 calc R . . H11B H 0.8721 0.7942 0.1991 0.028 Uiso 1 1 calc R . . C12 C 0.2443(5) 0.4730(4) 0.15647(18) 0.0206(7) Uani 1 1 d . . . C13 C 0.2816(5) 0.4224(4) 0.08084(18) 0.0230(7) Uani 1 1 d . . . H13 H 0.3968 0.4350 0.0538 0.028 Uiso 1 1 calc R . . C14 C 0.1532(5) 0.3539(4) 0.04428(19) 0.0273(8) Uani 1 1 d . . . H14 H 0.1795 0.3188 -0.0071 0.033 Uiso 1 1 calc R . . C15 C -0.0126(5) 0.3381(4) 0.0842(2) 0.0263(8) Uani 1 1 d . . . C16 C -0.0584(5) 0.3873(4) 0.1583(2) 0.0272(8) Uani 1 1 d . . . H16 H -0.1748 0.3756 0.1842 0.033 Uiso 1 1 calc R . . C17 C 0.0735(5) 0.4556(4) 0.19460(19) 0.0252(8) Uani 1 1 d . . . H17 H 0.0458 0.4906 0.2459 0.030 Uiso 1 1 calc R . . C18 C 0.7669(5) 0.4792(4) 0.42337(18) 0.0209(7) Uani 1 1 d . . . H18A H 0.7539 0.5959 0.4169 0.025 Uiso 1 1 calc R . . H18B H 0.8836 0.4449 0.3964 0.025 Uiso 1 1 calc R . . C19 C 0.7623(5) 0.4164(4) 0.51255(18) 0.0212(7) Uani 1 1 d . . . H19A H 0.8632 0.4549 0.5372 0.025 Uiso 1 1 calc R . . H19B H 0.6486 0.4566 0.5399 0.025 Uiso 1 1 calc R . . C20 C 0.6326(5) 0.1798(4) 0.48289(18) 0.0208(7) Uani 1 1 d . . . H20A H 0.5138 0.2090 0.5096 0.025 Uiso 1 1 calc R . . H20B H 0.6497 0.0633 0.4875 0.025 Uiso 1 1 calc R . . C21 C 0.6357(5) 0.2462(3) 0.39470(18) 0.0217(7) Uani 1 1 d . . . H21A H 0.7495 0.2083 0.3666 0.026 Uiso 1 1 calc R . . H21B H 0.5348 0.2088 0.3695 0.026 Uiso 1 1 calc R . . C22 C 0.7665(5) 0.1754(4) 0.61191(17) 0.0230(7) Uani 1 1 d . . . H22A H 0.7501 0.0613 0.6168 0.028 Uiso 1 1 calc R . . H22B H 0.6606 0.2277 0.6398 0.028 Uiso 1 1 calc R . . C23 C 0.9347(5) 0.1997(5) 0.6525(2) 0.0371(10) Uani 1 1 d . . . H23A H 1.0413 0.1631 0.6201 0.056 Uiso 1 1 calc R . . H23B H 0.9326 0.1396 0.7062 0.056 Uiso 1 1 calc R . . H23C H 0.9387 0.3120 0.6573 0.056 Uiso 1 1 calc R . . Cl1 Cl 0.16185(11) 0.20548(9) 0.44481(5) 0.0281(3) Uani 1 1 d . . . F1 F -0.1393(3) 0.2696(2) 0.04881(12) 0.0392(6) Uani 1 1 d . . . H3 H 0.896(5) 0.203(4) 0.504(2) 0.018(8) Uiso 1 1 d . . . N1 N 0.6726(4) 0.6158(3) 0.27936(15) 0.0196(6) Uani 1 1 d . . . N2 N 0.6202(4) 0.4194(3) 0.38638(15) 0.0194(6) Uani 1 1 d . . . N3 N 0.7765(4) 0.2408(3) 0.52434(15) 0.0187(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0202(18) 0.0211(16) 0.0179(15) -0.0048(12) -0.0027(13) -0.0043(13) C2 0.0193(17) 0.0222(16) 0.0195(15) -0.0036(12) 0.0001(13) -0.0062(13) C3 0.0217(18) 0.0213(16) 0.0199(15) -0.0063(12) -0.0040(13) -0.0028(13) C4 0.0228(19) 0.0220(16) 0.0187(15) -0.0038(12) -0.0014(13) -0.0038(13) C5 0.0219(18) 0.0230(16) 0.0188(15) -0.0042(12) -0.0009(13) -0.0044(13) C6 0.0260(19) 0.0316(18) 0.0191(15) -0.0017(13) -0.0059(14) -0.0105(15) C7 0.026(2) 0.0331(19) 0.0272(17) 0.0047(14) -0.0048(15) -0.0065(15) C8 0.035(2) 0.0253(17) 0.0273(17) 0.0011(13) -0.0025(16) -0.0004(15) C9 0.041(2) 0.0219(17) 0.0306(18) -0.0043(13) -0.0049(16) -0.0051(15) C10 0.040(2) 0.0287(18) 0.0223(16) -0.0014(13) -0.0048(16) -0.0168(16) C11 0.0219(19) 0.0265(17) 0.0224(16) -0.0005(12) -0.0035(14) -0.0107(14) C12 0.0247(19) 0.0190(15) 0.0189(15) 0.0005(11) -0.0058(13) -0.0057(13) C13 0.0239(19) 0.0267(17) 0.0186(15) -0.0016(12) 0.0020(13) -0.0073(14) C14 0.038(2) 0.0277(17) 0.0178(15) -0.0041(12) -0.0072(15) -0.0073(15) C15 0.030(2) 0.0247(17) 0.0274(17) -0.0016(13) -0.0136(15) -0.0117(15) C16 0.024(2) 0.0316(18) 0.0278(17) -0.0062(14) -0.0018(15) -0.0095(15) C17 0.031(2) 0.0257(17) 0.0215(16) -0.0071(13) -0.0044(15) -0.0067(14) C18 0.0218(18) 0.0211(16) 0.0219(16) -0.0044(12) -0.0049(13) -0.0075(13) C19 0.0247(19) 0.0205(15) 0.0203(15) -0.0051(12) -0.0041(13) -0.0057(13) C20 0.0235(18) 0.0193(15) 0.0212(16) -0.0023(12) -0.0052(13) -0.0085(13) C21 0.0276(19) 0.0206(16) 0.0187(15) -0.0025(12) -0.0082(14) -0.0054(13) C22 0.032(2) 0.0241(16) 0.0141(15) -0.0015(12) -0.0021(14) -0.0075(14) C23 0.037(2) 0.055(2) 0.0213(17) 0.0041(16) -0.0128(16) -0.0214(19) Cl1 0.0233(5) 0.0267(5) 0.0351(5) -0.0059(3) 0.0009(4) -0.0047(3) F1 0.0437(14) 0.0444(13) 0.0357(12) -0.0069(9) -0.0181(10) -0.0215(10) N1 0.0208(15) 0.0206(13) 0.0188(13) -0.0037(10) -0.0038(11) -0.0053(11) N2 0.0211(15) 0.0191(13) 0.0195(13) -0.0024(10) -0.0053(11) -0.0067(11) N3 0.0192(15) 0.0199(13) 0.0176(13) -0.0018(10) -0.0038(11) -0.0027(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.335(4) . ? C1 N2 1.404(4) . ? C1 C2 1.405(4) . ? C2 C3 1.383(4) . ? C3 C4 1.415(4) . ? C3 C12 1.502(4) . ? C4 C5 1.411(4) . ? C4 C6 1.511(4) . ? C5 N1 1.348(4) . ? C5 C11 1.513(4) . ? C6 C7 1.532(5) . ? C7 C8 1.534(5) . ? C8 C9 1.540(5) . ? C9 C10 1.526(5) . ? C10 C11 1.537(5) . ? C12 C13 1.394(5) . ? C12 C17 1.396(5) . ? C13 C14 1.390(5) . ? C14 C15 1.372(5) . ? C15 F1 1.369(4) . ? C15 C16 1.373(5) . ? C16 C17 1.406(5) . ? C18 N2 1.464(4) . ? C18 C19 1.525(4) . ? C19 N3 1.489(4) . ? C20 N3 1.493(4) . ? C20 C21 1.517(4) . ? C21 N2 1.469(4) . ? C22 N3 1.505(4) . ? C22 C23 1.520(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 117.1(3) . . ? N1 C1 C2 122.1(3) . . ? N2 C1 C2 120.8(3) . . ? C3 C2 C1 119.4(3) . . ? C2 C3 C4 119.4(3) . . ? C2 C3 C12 117.3(3) . . ? C4 C3 C12 123.2(3) . . ? C5 C4 C3 116.8(3) . . ? C5 C4 C6 120.3(3) . . ? C3 C4 C6 122.6(3) . . ? N1 C5 C4 123.4(3) . . ? N1 C5 C11 113.5(3) . . ? C4 C5 C11 123.1(3) . . ? C4 C6 C7 113.0(3) . . ? C6 C7 C8 115.2(3) . . ? C7 C8 C9 116.8(3) . . ? C10 C9 C8 115.4(3) . . ? C9 C10 C11 116.1(3) . . ? C5 C11 C10 115.0(3) . . ? C13 C12 C17 118.6(3) . . ? C13 C12 C3 120.5(3) . . ? C17 C12 C3 120.7(3) . . ? C14 C13 C12 121.1(3) . . ? C15 C14 C13 118.4(3) . . ? F1 C15 C14 118.7(3) . . ? F1 C15 C16 118.0(3) . . ? C14 C15 C16 123.3(3) . . ? C15 C16 C17 117.5(3) . . ? C12 C17 C16 121.1(3) . . ? N2 C18 C19 109.5(3) . . ? N3 C19 C18 111.1(2) . . ? N3 C20 C21 111.3(3) . . ? N2 C21 C20 110.3(2) . . ? N3 C22 C23 112.0(3) . . ? C1 N1 C5 118.8(3) . . ? C1 N2 C18 116.5(3) . . ? C1 N2 C21 116.3(2) . . ? C18 N2 C21 111.2(2) . . ? C19 N3 C20 110.3(2) . . ? C19 N3 C22 112.3(2) . . ? C20 N3 C22 109.8(2) . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 26.15 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.838 _refine_diff_density_min -0.538 _refine_diff_density_rms 0.140