# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_pml029_0m _database_code_depnum_ccdc_archive 'CCDC 904317' #TrackingRef 'PyrNN_OFN_DCM.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C23 H21 N2 O2), C10 F8, 2(C H2 Cl2)' _chemical_formula_sum 'C58 H46 Cl4 F8 N4 O4' _chemical_formula_weight 1156.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.8838(8) _cell_length_b 10.1039(6) _cell_length_c 18.7348(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.125(1) _cell_angle_gamma 90.00 _cell_volume 2511.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9857 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 28.26 _exptl_crystal_description Plate _exptl_crystal_colour violet _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1188 _exptl_absorpt_coefficient_mu 0.321 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8284 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2009)' _exptl_special_details ; The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5 deg. in omega, colllected at phi = 0.00, 90.00 and 180.00 deg. and 2 sets of 800 frames, each of width 0.45 deg in phi, collected at omega = -30.00 and 210.00 deg. The scan time was 30 sec/frame. ; _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 'Bruker Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 42521 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.28 _reflns_number_total 6228 _reflns_number_gt 4902 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2 (Bruker-AXS, 2010)' _computing_cell_refinement 'Bruker SAINT (Bruker-AXS, 2009)' _computing_data_reduction 'Bruker SAINT (Bruker-AXS, 2009)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker-AXS, 2008)' _computing_publication_material 'Bruker SHELXTL (Bruker-AXS, 2008)' _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. H-atoms were placed in calculated positions (C---H = 0.95 - 0.98 \%A) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms. Atom Cl2 of the solvent dichloromethane is disordered over two resolved sites in a 9:1 ratio. The disorder was treated satisfactorily with a split atom model. ; _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^)+(0.0440P)^2^+2.0672P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6228 _refine_ls_number_parameters 360 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1161 _refine_ls_wR_factor_gt 0.1029 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 O1 O 0.48149(11) 0.35343(13) 0.30167(8) 0.0281(3) Uani 1 1 d . . . O2 O 0.37444(10) -0.07066(13) 0.22345(7) 0.0245(3) Uani 1 1 d . . . N1 N 0.44013(11) 0.23913(15) 0.29787(8) 0.0197(3) Uani 1 1 d . . . N2 N 0.38786(11) 0.03913(15) 0.25983(8) 0.0190(3) Uani 1 1 d . . . C1 C 0.43601(13) 0.14698(17) 0.24481(10) 0.0181(3) Uani 1 1 d . . . C2 C 0.40496(14) 0.18470(17) 0.36038(10) 0.0186(3) Uani 1 1 d . . . C3 C 0.33903(14) 0.06712(18) 0.32011(10) 0.0197(4) Uani 1 1 d . . . C4 C 0.50014(16) 0.1413(2) 0.42070(11) 0.0276(4) Uani 1 1 d . . . H4A H 0.5340 0.0715 0.4009 0.041 Uiso 1 1 calc R . . H4B H 0.4818 0.1076 0.4640 0.041 Uiso 1 1 calc R . . H4C H 0.5456 0.2172 0.4359 0.041 Uiso 1 1 calc R . . C5 C 0.34884(16) 0.28977(19) 0.39034(11) 0.0255(4) Uani 1 1 d . . . H5A H 0.3954 0.3612 0.4134 0.038 Uiso 1 1 calc R . . H5B H 0.3210 0.2503 0.4278 0.038 Uiso 1 1 calc R . . H5C H 0.2939 0.3257 0.3492 0.038 Uiso 1 1 calc R . . C6 C 0.34149(16) -0.05464(19) 0.36761(11) 0.0268(4) Uani 1 1 d . . . H6A H 0.2973 -0.1227 0.3378 0.040 Uiso 1 1 calc R . . H6B H 0.3182 -0.0315 0.4106 0.040 Uiso 1 1 calc R . . H6C H 0.4106 -0.0886 0.3853 0.040 Uiso 1 1 calc R . . C7 C 0.23047(14) 0.1071(2) 0.27889(11) 0.0249(4) Uani 1 1 d . . . H7A H 0.2310 0.1854 0.2481 0.037 Uiso 1 1 calc R . . H7B H 0.1944 0.1277 0.3153 0.037 Uiso 1 1 calc R . . H7C H 0.1966 0.0340 0.2469 0.037 Uiso 1 1 calc R . . C8 C 0.48248(13) 0.16059(17) 0.18432(10) 0.0179(3) Uani 1 1 d . . . C9 C 0.58630(14) 0.17839(18) 0.20343(10) 0.0201(4) Uani 1 1 d . . . H9 H 0.6241 0.1865 0.2545 0.024 Uiso 1 1 calc R . . C10 C 0.63526(14) 0.18437(17) 0.14874(10) 0.0203(4) Uani 1 1 d . . . H10 H 0.7064 0.1944 0.1629 0.024 Uiso 1 1 calc R . . C11 C 0.58115(13) 0.17578(16) 0.07318(10) 0.0178(3) Uani 1 1 d . . . C12 C 0.62997(14) 0.17920(17) 0.01508(10) 0.0200(4) Uani 1 1 d . . . H12 H 0.7012 0.1871 0.0284 0.024 Uiso 1 1 calc R . . C13 C 0.57653(14) 0.17135(17) -0.05781(10) 0.0205(4) Uani 1 1 d . . . H13 H 0.6109 0.1726 -0.0948 0.025 Uiso 1 1 calc R . . C14 C 0.46801(14) 0.16103(17) -0.08038(10) 0.0190(3) Uani 1 1 d . . . C15 C 0.41143(15) 0.15464(18) -0.15561(10) 0.0223(4) Uani 1 1 d . . . H15 H 0.4446 0.1572 -0.1933 0.027 Uiso 1 1 calc R . . C16 C 0.30743(15) 0.14455(19) -0.17550(11) 0.0243(4) Uani 1 1 d . . . H16 H 0.2699 0.1413 -0.2268 0.029 Uiso 1 1 calc R . . C17 C 0.25715(15) 0.13910(18) -0.12142(10) 0.0234(4) Uani 1 1 d . . . H17 H 0.1858 0.1319 -0.1361 0.028 Uiso 1 1 calc R . . C18 C 0.31102(14) 0.14411(17) -0.04536(10) 0.0202(4) Uani 1 1 d . . . C19 C 0.26277(14) 0.13581(18) 0.01233(10) 0.0218(4) Uani 1 1 d . . . H19 H 0.1915 0.1274 -0.0012 0.026 Uiso 1 1 calc R . . C20 C 0.31589(13) 0.13960(18) 0.08559(10) 0.0204(4) Uani 1 1 d . . . H20 H 0.2813 0.1327 0.1223 0.024 Uiso 1 1 calc R . . C21 C 0.42384(13) 0.15390(16) 0.10882(9) 0.0160(3) Uani 1 1 d . . . C22 C 0.47437(13) 0.16238(16) 0.05272(10) 0.0169(3) Uani 1 1 d . . . C23 C 0.41789(13) 0.15641(16) -0.02432(10) 0.0180(3) Uani 1 1 d . . . C24 C 0.66122(15) 0.51896(18) 0.10477(11) 0.0252(4) Uani 1 1 d . . . C25 C 0.58386(16) 0.51613(19) 0.13850(11) 0.0260(4) Uani 1 1 d . . . C26 C 0.48662(15) 0.50477(18) 0.09613(11) 0.0235(4) Uani 1 1 d . . . C27 C 0.46037(14) 0.49787(17) 0.01730(10) 0.0202(4) Uani 1 1 d . . . C28 C 0.36014(14) 0.48830(18) -0.02935(11) 0.0231(4) Uani 1 1 d . . . F1 F 0.75675(9) 0.52668(12) 0.14845(7) 0.0349(3) Uani 1 1 d . . . F2 F 0.60766(10) 0.52486(12) 0.21309(6) 0.0355(3) Uani 1 1 d . . . F3 F 0.41421(10) 0.50216(13) 0.13025(7) 0.0345(3) Uani 1 1 d . . . F4 F 0.28289(9) 0.48704(13) -0.00005(7) 0.0338(3) Uani 1 1 d . . . Cl1 Cl 0.89458(4) 0.29172(5) 0.13878(3) 0.03414(14) Uani 1 1 d . . . C29 C 0.98982(17) 0.1697(2) 0.16191(12) 0.0335(5) Uani 0.910(4) 1 d PD A 1 H29A H 0.9641 0.0904 0.1815 0.040 Uiso 0.910(4) 1 calc PR A 1 H29B H 1.0483 0.2039 0.2018 0.040 Uiso 0.910(4) 1 calc PR A 1 Cl2 Cl 1.02916(12) 0.12425(8) 0.08372(4) 0.0346(3) Uani 0.910(4) 1 d PD A 1 C29A C 0.98982(17) 0.1697(2) 0.16191(12) 0.0335(5) Uani 0.090(4) 1 d PD A 2 H29C H 0.9751 0.1014 0.1951 0.040 Uiso 0.090(4) 1 calc PR A 2 H29D H 1.0566 0.2093 0.1865 0.040 Uiso 0.090(4) 1 calc PR A 2 Cl2A Cl 0.9849(11) 0.1022(9) 0.0731(5) 0.0346(3) Uani 0.090(4) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0384(8) 0.0177(6) 0.0323(8) -0.0051(6) 0.0165(6) -0.0085(6) O2 0.0314(7) 0.0182(6) 0.0235(7) -0.0061(5) 0.0073(6) -0.0041(5) N1 0.0256(8) 0.0170(7) 0.0177(7) -0.0009(6) 0.0081(6) -0.0019(6) N2 0.0224(7) 0.0177(7) 0.0158(7) -0.0014(6) 0.0040(6) -0.0003(6) C1 0.0199(8) 0.0185(8) 0.0143(8) 0.0006(6) 0.0027(6) -0.0001(7) C2 0.0240(8) 0.0184(8) 0.0140(8) 0.0005(6) 0.0063(7) -0.0004(7) C3 0.0232(9) 0.0174(8) 0.0197(9) 0.0001(7) 0.0081(7) -0.0011(7) C4 0.0307(10) 0.0274(10) 0.0202(9) -0.0016(8) 0.0006(8) 0.0005(8) C5 0.0355(10) 0.0214(9) 0.0224(10) -0.0029(7) 0.0128(8) 0.0008(8) C6 0.0379(11) 0.0193(9) 0.0270(10) 0.0033(7) 0.0155(9) -0.0008(8) C7 0.0221(9) 0.0263(10) 0.0269(10) 0.0002(8) 0.0079(8) -0.0008(7) C8 0.0215(8) 0.0166(8) 0.0158(8) 0.0000(6) 0.0059(7) 0.0007(7) C9 0.0224(8) 0.0193(8) 0.0165(8) 0.0002(7) 0.0022(7) -0.0013(7) C10 0.0201(8) 0.0177(8) 0.0230(9) 0.0008(7) 0.0063(7) -0.0007(7) C11 0.0183(8) 0.0126(8) 0.0226(9) 0.0016(6) 0.0061(7) 0.0010(6) C12 0.0206(8) 0.0164(8) 0.0234(9) -0.0003(7) 0.0071(7) 0.0000(7) C13 0.0257(9) 0.0156(8) 0.0230(9) 0.0008(7) 0.0113(7) 0.0005(7) C14 0.0263(9) 0.0131(8) 0.0179(9) 0.0005(6) 0.0070(7) 0.0018(7) C15 0.0322(10) 0.0180(8) 0.0171(9) 0.0010(7) 0.0081(7) 0.0018(7) C16 0.0322(10) 0.0206(9) 0.0169(9) 0.0003(7) 0.0022(7) 0.0025(8) C17 0.0230(9) 0.0208(9) 0.0224(9) -0.0004(7) 0.0007(7) 0.0024(7) C18 0.0232(9) 0.0162(8) 0.0201(9) -0.0009(6) 0.0046(7) 0.0016(7) C19 0.0192(8) 0.0214(9) 0.0220(9) 0.0008(7) 0.0017(7) 0.0022(7) C20 0.0202(8) 0.0209(9) 0.0203(9) -0.0008(7) 0.0065(7) 0.0023(7) C21 0.0176(8) 0.0136(7) 0.0160(8) -0.0003(6) 0.0038(6) 0.0010(6) C22 0.0202(8) 0.0126(7) 0.0179(8) 0.0002(6) 0.0055(7) 0.0015(6) C23 0.0235(8) 0.0129(8) 0.0170(8) 0.0008(6) 0.0050(7) 0.0021(6) C24 0.0269(9) 0.0156(8) 0.0281(10) -0.0003(7) 0.0005(8) 0.0025(7) C25 0.0389(11) 0.0192(9) 0.0178(9) -0.0012(7) 0.0051(8) 0.0059(8) C26 0.0328(10) 0.0184(9) 0.0220(9) 0.0020(7) 0.0124(8) 0.0057(7) C27 0.0245(9) 0.0144(8) 0.0238(9) 0.0008(7) 0.0103(7) 0.0027(7) C28 0.0237(9) 0.0185(9) 0.0288(10) 0.0023(7) 0.0106(8) 0.0033(7) F1 0.0286(6) 0.0304(6) 0.0362(7) -0.0020(5) -0.0050(5) 0.0034(5) F2 0.0525(8) 0.0328(7) 0.0175(6) -0.0007(5) 0.0045(5) 0.0090(6) F3 0.0429(7) 0.0397(7) 0.0285(7) 0.0043(5) 0.0223(6) 0.0096(6) F4 0.0268(6) 0.0372(7) 0.0417(7) 0.0035(6) 0.0166(5) 0.0020(5) Cl1 0.0227(2) 0.0364(3) 0.0425(3) 0.0015(2) 0.0084(2) 0.0035(2) C29 0.0378(11) 0.0382(12) 0.0261(11) 0.0098(9) 0.0117(9) 0.0115(10) Cl2 0.0526(7) 0.0266(3) 0.0304(3) 0.0043(2) 0.0210(4) 0.0064(4) C29A 0.0378(11) 0.0382(12) 0.0261(11) 0.0098(9) 0.0117(9) 0.0115(10) Cl2A 0.0526(7) 0.0266(3) 0.0304(3) 0.0043(2) 0.0210(4) 0.0064(4) _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 N1 1.2825(19) . ? O2 N2 1.2864(19) . ? N1 C1 1.351(2) . ? N1 C2 1.500(2) . ? N2 C1 1.351(2) . ? N2 C3 1.505(2) . ? C1 C8 1.466(2) . ? C2 C5 1.519(2) . ? C2 C4 1.528(3) . ? C2 C3 1.553(2) . ? C3 C6 1.513(2) . ? C3 C7 1.532(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.391(2) . ? C8 C21 1.411(2) . ? C9 C10 1.388(2) . ? C9 H9 0.9500 . ? C10 C11 1.396(3) . ? C10 H10 0.9500 . ? C11 C22 1.424(2) . ? C11 C12 1.442(2) . ? C12 C13 1.351(3) . ? C12 H12 0.9500 . ? C13 C14 1.444(3) . ? C13 H13 0.9500 . ? C14 C15 1.398(3) . ? C14 C23 1.421(2) . ? C15 C16 1.385(3) . ? C15 H15 0.9500 . ? C16 C17 1.390(3) . ? C16 H16 0.9500 . ? C17 C18 1.402(3) . ? C17 H17 0.9500 . ? C18 C23 1.424(2) . ? C18 C19 1.432(3) . ? C19 C20 1.354(3) . ? C19 H19 0.9500 . ? C20 C21 1.440(2) . ? C20 H20 0.9500 . ? C21 C22 1.428(2) . ? C22 C23 1.427(2) . ? C24 F1 1.340(2) . ? C24 C28 1.357(3) 3_665 ? C24 C25 1.398(3) . ? C25 F2 1.341(2) . ? C25 C26 1.355(3) . ? C26 F3 1.341(2) . ? C26 C27 1.415(3) . ? C27 C28 1.412(3) . ? C27 C27 1.433(3) 3_665 ? C28 F4 1.341(2) . ? C28 C24 1.358(3) 3_665 ? Cl1 C29 1.766(2) . ? C29 Cl2 1.768(2) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? 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 O1 N1 C1 125.64(15) . . ? O1 N1 C2 122.03(14) . . ? C1 N1 C2 111.65(14) . . ? O2 N2 C1 126.07(15) . . ? O2 N2 C3 122.17(14) . . ? C1 N2 C3 111.38(14) . . ? N2 C1 N1 108.61(15) . . ? N2 C1 C8 126.45(16) . . ? N1 C1 C8 124.83(16) . . ? N1 C2 C5 110.65(14) . . ? N1 C2 C4 105.85(15) . . ? C5 C2 C4 110.67(15) . . ? N1 C2 C3 100.49(13) . . ? C5 C2 C3 114.91(15) . . ? C4 C2 C3 113.43(15) . . ? N2 C3 C6 110.57(14) . . ? N2 C3 C7 105.37(14) . . ? C6 C3 C7 111.08(16) . . ? N2 C3 C2 100.19(13) . . ? C6 C3 C2 115.36(15) . . ? C7 C3 C2 113.24(15) . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C21 120.85(16) . . ? C9 C8 C1 118.14(16) . . ? C21 C8 C1 121.01(15) . . ? C10 C9 C8 120.75(17) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 120.77(16) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C22 119.04(16) . . ? C10 C11 C12 122.12(16) . . ? C22 C11 C12 118.84(16) . . ? C13 C12 C11 121.42(17) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 121.03(16) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C23 119.43(17) . . ? C15 C14 C13 121.78(16) . . ? C23 C14 C13 118.80(16) . . ? C16 C15 C14 120.42(17) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 120.95(17) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C16 C17 C18 120.48(18) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C23 119.03(17) . . ? C17 C18 C19 122.48(17) . . ? C23 C18 C19 118.49(16) . . ? C20 C19 C18 121.82(17) . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C19 C20 C21 121.15(17) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C8 C21 C22 118.15(15) . . ? C8 C21 C20 123.37(16) . . ? C22 C21 C20 118.48(15) . . ? C11 C22 C23 119.66(16) . . ? C11 C22 C21 120.38(16) . . ? C23 C22 C21 119.96(15) . . ? C14 C23 C18 119.68(16) . . ? C14 C23 C22 120.22(16) . . ? C18 C23 C22 120.09(16) . . ? F1 C24 C28 120.82(18) . 3_665 ? F1 C24 C25 118.64(18) . . ? C28 C24 C25 120.53(18) 3_665 . ? F2 C25 C26 120.90(18) . . ? F2 C25 C24 118.92(18) . . ? C26 C25 C24 120.18(18) . . ? F3 C26 C25 118.69(17) . . ? F3 C26 C27 119.86(17) . . ? C25 C26 C27 121.45(18) . . ? C28 C27 C26 123.60(17) . . ? C28 C27 C27 118.1(2) . 3_665 ? C26 C27 C27 118.3(2) . 3_665 ? F4 C28 C24 118.01(17) . 3_665 ? F4 C28 C27 120.57(17) . . ? C24 C28 C27 121.42(17) 3_665 . ? Cl1 C29 Cl2 111.68(12) . . ? Cl1 C29 H29A 109.3 . . ? Cl2 C29 H29A 109.3 . . ? Cl1 C29 H29B 109.3 . . ? Cl2 C29 H29B 109.3 . . ? H29A C29 H29B 107.9 . . ? 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 O2 N2 C1 N1 -176.26(16) . . . . ? C3 N2 C1 N1 10.7(2) . . . . ? O2 N2 C1 C8 0.0(3) . . . . ? C3 N2 C1 C8 -173.02(16) . . . . ? O1 N1 C1 N2 179.20(16) . . . . ? C2 N1 C1 N2 8.5(2) . . . . ? O1 N1 C1 C8 2.9(3) . . . . ? C2 N1 C1 C8 -167.81(16) . . . . ? O1 N1 C2 C5 44.4(2) . . . . ? C1 N1 C2 C5 -144.54(16) . . . . ? O1 N1 C2 C4 -75.6(2) . . . . ? C1 N1 C2 C4 95.52(17) . . . . ? O1 N1 C2 C3 166.22(15) . . . . ? C1 N1 C2 C3 -22.71(18) . . . . ? O2 N2 C3 C6 40.6(2) . . . . ? C1 N2 C3 C6 -146.11(16) . . . . ? O2 N2 C3 C7 -79.55(19) . . . . ? C1 N2 C3 C7 93.78(17) . . . . ? O2 N2 C3 C2 162.72(15) . . . . ? C1 N2 C3 C2 -23.94(18) . . . . ? N1 C2 C3 N2 25.80(16) . . . . ? C5 C2 C3 N2 144.58(15) . . . . ? C4 C2 C3 N2 -86.71(17) . . . . ? N1 C2 C3 C6 144.51(15) . . . . ? C5 C2 C3 C6 -96.72(19) . . . . ? C4 C2 C3 C6 32.0(2) . . . . ? N1 C2 C3 C7 -85.93(17) . . . . ? C5 C2 C3 C7 32.8(2) . . . . ? C4 C2 C3 C7 161.55(16) . . . . ? N2 C1 C8 C9 -115.9(2) . . . . ? N1 C1 C8 C9 59.8(2) . . . . ? N2 C1 C8 C21 63.2(3) . . . . ? N1 C1 C8 C21 -121.1(2) . . . . ? C21 C8 C9 C10 -2.7(3) . . . . ? C1 C8 C9 C10 176.33(16) . . . . ? C8 C9 C10 C11 1.5(3) . . . . ? C9 C10 C11 C22 0.8(3) . . . . ? C9 C10 C11 C12 -178.82(16) . . . . ? C10 C11 C12 C13 -179.71(17) . . . . ? C22 C11 C12 C13 0.7(3) . . . . ? C11 C12 C13 C14 0.9(3) . . . . ? C12 C13 C14 C15 179.11(17) . . . . ? C12 C13 C14 C23 -1.3(3) . . . . ? C23 C14 C15 C16 0.3(3) . . . . ? C13 C14 C15 C16 179.89(17) . . . . ? C14 C15 C16 C17 -0.7(3) . . . . ? C15 C16 C17 C18 0.2(3) . . . . ? C16 C17 C18 C23 0.7(3) . . . . ? C16 C17 C18 C19 -178.55(17) . . . . ? C17 C18 C19 C20 179.40(18) . . . . ? C23 C18 C19 C20 0.1(3) . . . . ? C18 C19 C20 C21 0.8(3) . . . . ? C9 C8 C21 C22 1.6(2) . . . . ? C1 C8 C21 C22 -177.43(15) . . . . ? C9 C8 C21 C20 -178.08(16) . . . . ? C1 C8 C21 C20 2.9(3) . . . . ? C19 C20 C21 C8 178.91(17) . . . . ? C19 C20 C21 C22 -0.8(3) . . . . ? C10 C11 C22 C23 178.63(16) . . . . ? C12 C11 C22 C23 -1.8(2) . . . . ? C10 C11 C22 C21 -1.9(2) . . . . ? C12 C11 C22 C21 177.76(15) . . . . ? C8 C21 C22 C11 0.7(2) . . . . ? C20 C21 C22 C11 -179.62(15) . . . . ? C8 C21 C22 C23 -179.82(16) . . . . ? C20 C21 C22 C23 -0.1(2) . . . . ? C15 C14 C23 C18 0.6(2) . . . . ? C13 C14 C23 C18 -179.00(16) . . . . ? C15 C14 C23 C22 179.80(16) . . . . ? C13 C14 C23 C22 0.2(2) . . . . ? C17 C18 C23 C14 -1.1(3) . . . . ? C19 C18 C23 C14 178.20(16) . . . . ? C17 C18 C23 C22 179.69(16) . . . . ? C19 C18 C23 C22 -1.0(2) . . . . ? C11 C22 C23 C14 1.3(2) . . . . ? C21 C22 C23 C14 -178.21(15) . . . . ? C11 C22 C23 C18 -179.49(15) . . . . ? C21 C22 C23 C18 1.0(2) . . . . ? F1 C24 C25 F2 1.8(3) . . . . ? C28 C24 C25 F2 -179.33(17) 3_665 . . . ? F1 C24 C25 C26 -178.22(17) . . . . ? C28 C24 C25 C26 0.6(3) 3_665 . . . ? F2 C25 C26 F3 -0.1(3) . . . . ? C24 C25 C26 F3 179.90(17) . . . . ? F2 C25 C26 C27 178.85(16) . . . . ? C24 C25 C26 C27 -1.1(3) . . . . ? F3 C26 C27 C28 0.1(3) . . . . ? C25 C26 C27 C28 -178.87(18) . . . . ? F3 C26 C27 C27 179.44(19) . . . 3_665 ? C25 C26 C27 C27 0.5(3) . . . 3_665 ? C26 C27 C28 F4 0.9(3) . . . . ? C27 C27 C28 F4 -178.45(19) 3_665 . . . ? C26 C27 C28 C24 -179.55(18) . . . 3_665 ? C27 C27 C28 C24 1.1(3) 3_665 . . 3_665 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C6 H6B F4 0.98 2.49 3.441(2) 164 2_545 C7 H7B F3 0.98 2.41 3.174(2) 134 2_545 C9 H9 F1 0.95 2.62 3.352(2) 134 2_645 C13 H13 O2 0.95 2.68 3.518(2) 147 3_655 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.529 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.063 _iucr_refine_instructions_details ; TITL PML029_0m in P2(1)/n CELL 0.71073 13.8838 10.1039 18.7348 90.000 107.125 90.000 ZERR 2.00 0.0008 0.0006 0.0011 0.000 0.001 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O F Cl UNIT 116 92 8 8 16 8 L.S. 6 ACTA BOND $H FMAP 2 PLAN 5 EQIV $1 -x+0.5, y-0.5, -z+0.5 EQIV $2 -x+1.5, y-0.5, -z+0.5 EQIV $3 1-x, -y, -z HTAB C6 F4_$1 HTAB C7 F3_$1 HTAB C9 F1_$2 HTAB C13 O2_$3 SIZE 0.04 0.21 0.21 SADI C29 Cl2 C29a Cl2a EADP Cl2 Cl2a EADP C29 C29a EXYZ C29 C29a MPLA C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 MPLA 5 C24 C25 C26 C27 C28 C22 C23 CONF TEMP -173 WGHT 0.044000 2.067200 FVAR 0.08347 0.91040 MOLE 2 O1 4 0.481491 0.353433 0.301668 11.00000 0.03835 0.01770 = 0.03227 -0.00510 0.01648 -0.00852 O2 4 0.374442 -0.070656 0.223454 11.00000 0.03144 0.01816 = 0.02350 -0.00614 0.00734 -0.00405 N1 3 0.440128 0.239125 0.297874 11.00000 0.02555 0.01699 = 0.01767 -0.00093 0.00810 -0.00187 N2 3 0.387860 0.039132 0.259828 11.00000 0.02245 0.01765 = 0.01575 -0.00137 0.00404 -0.00031 C1 1 0.436005 0.146975 0.244814 11.00000 0.01995 0.01852 = 0.01431 0.00063 0.00270 -0.00007 C2 1 0.404959 0.184699 0.360379 11.00000 0.02398 0.01838 = 0.01397 0.00053 0.00627 -0.00040 C3 1 0.339032 0.067117 0.320109 11.00000 0.02316 0.01741 = 0.01973 0.00013 0.00813 -0.00110 C4 1 0.500142 0.141348 0.420705 11.00000 0.03071 0.02744 = 0.02024 -0.00161 0.00065 0.00049 AFIX 137 H4A 2 0.534021 0.071465 0.400893 11.00000 -1.50000 H4B 2 0.481839 0.107613 0.464010 11.00000 -1.50000 H4C 2 0.545598 0.217170 0.435892 11.00000 -1.50000 AFIX 0 C5 1 0.348840 0.289768 0.390337 11.00000 0.03545 0.02142 = 0.02241 -0.00288 0.01282 0.00084 AFIX 137 H5A 2 0.395415 0.361175 0.413350 11.00000 -1.50000 H5B 2 0.320979 0.250271 0.427768 11.00000 -1.50000 H5C 2 0.293912 0.325656 0.349224 11.00000 -1.50000 AFIX 0 C6 1 0.341493 -0.054638 0.367606 11.00000 0.03794 0.01925 = 0.02703 0.00333 0.01549 -0.00083 AFIX 137 H6A 2 0.297291 -0.122722 0.337760 11.00000 -1.50000 H6B 2 0.318191 -0.031499 0.410564 11.00000 -1.50000 H6C 2 0.410591 -0.088568 0.385262 11.00000 -1.50000 AFIX 0 C7 1 0.230473 0.107147 0.278887 11.00000 0.02209 0.02627 = 0.02689 0.00017 0.00791 -0.00080 AFIX 137 H7A 2 0.230977 0.185368 0.248070 11.00000 -1.50000 H7B 2 0.194418 0.127667 0.315311 11.00000 -1.50000 H7C 2 0.196569 0.034019 0.246907 11.00000 -1.50000 AFIX 0 C8 1 0.482477 0.160595 0.184319 11.00000 0.02151 0.01661 = 0.01583 0.00003 0.00590 0.00071 C9 1 0.586303 0.178385 0.203434 11.00000 0.02242 0.01928 = 0.01647 0.00021 0.00221 -0.00135 AFIX 43 H9 2 0.624139 0.186529 0.254515 11.00000 -1.20000 AFIX 0 C10 1 0.635258 0.184374 0.148740 11.00000 0.02011 0.01766 = 0.02302 0.00084 0.00632 -0.00068 AFIX 43 H10 2 0.706418 0.194442 0.162873 11.00000 -1.20000 AFIX 0 C11 1 0.581154 0.175778 0.073184 11.00000 0.01828 0.01265 = 0.02262 0.00158 0.00608 0.00097 C12 1 0.629967 0.179196 0.015083 11.00000 0.02059 0.01639 = 0.02336 -0.00034 0.00713 0.00002 AFIX 43 H12 2 0.701238 0.187139 0.028356 11.00000 -1.20000 AFIX 0 C13 1 0.576532 0.171348 -0.057807 11.00000 0.02571 0.01557 = 0.02301 0.00081 0.01134 0.00051 AFIX 43 H13 2 0.610894 0.172638 -0.094790 11.00000 -1.20000 AFIX 0 C14 1 0.468011 0.161030 -0.080381 11.00000 0.02627 0.01306 = 0.01790 0.00055 0.00700 0.00182 C15 1 0.411432 0.154641 -0.155610 11.00000 0.03216 0.01801 = 0.01714 0.00097 0.00808 0.00180 AFIX 43 H15 2 0.444562 0.157241 -0.193312 11.00000 -1.20000 AFIX 0 C16 1 0.307434 0.144550 -0.175497 11.00000 0.03217 0.02058 = 0.01692 0.00027 0.00215 0.00250 AFIX 43 H16 2 0.269891 0.141304 -0.226832 11.00000 -1.20000 AFIX 0 C17 1 0.257153 0.139098 -0.121419 11.00000 0.02302 0.02080 = 0.02241 -0.00041 0.00067 0.00240 AFIX 43 H17 2 0.185773 0.131922 -0.136125 11.00000 -1.20000 AFIX 0 C18 1 0.311025 0.144112 -0.045361 11.00000 0.02325 0.01618 = 0.02014 -0.00086 0.00459 0.00161 C19 1 0.262772 0.135809 0.012331 11.00000 0.01921 0.02141 = 0.02201 0.00081 0.00174 0.00223 AFIX 43 H19 2 0.191517 0.127408 -0.001172 11.00000 -1.20000 AFIX 0 C20 1 0.315892 0.139601 0.085585 11.00000 0.02021 0.02095 = 0.02028 -0.00079 0.00647 0.00227 AFIX 43 H20 2 0.281330 0.132708 0.122296 11.00000 -1.20000 AFIX 0 C21 1 0.423844 0.153898 0.108819 11.00000 0.01755 0.01358 = 0.01598 -0.00031 0.00376 0.00098 C22 1 0.474371 0.162383 0.052721 11.00000 0.02015 0.01256 = 0.01794 0.00023 0.00552 0.00147 C23 1 0.417890 0.156412 -0.024317 11.00000 0.02347 0.01290 = 0.01696 0.00083 0.00502 0.00209 MOLE 1 C24 1 0.661220 0.518959 0.104772 11.00000 0.02692 0.01561 = 0.02812 -0.00034 0.00050 0.00253 C25 1 0.583860 0.516129 0.138503 11.00000 0.03895 0.01917 = 0.01779 -0.00124 0.00509 0.00588 C26 1 0.486618 0.504771 0.096133 11.00000 0.03278 0.01836 = 0.02201 0.00200 0.01238 0.00566 C27 1 0.460374 0.497867 0.017297 11.00000 0.02451 0.01435 = 0.02380 0.00082 0.01026 0.00274 C28 1 0.360140 0.488304 -0.029355 11.00000 0.02373 0.01852 = 0.02878 0.00230 0.01060 0.00328 F1 5 0.756747 0.526680 0.148452 11.00000 0.02864 0.03035 = 0.03617 -0.00203 -0.00503 0.00337 F2 5 0.607657 0.524864 0.213086 11.00000 0.05254 0.03284 = 0.01752 -0.00066 0.00455 0.00904 F3 5 0.414211 0.502161 0.130254 11.00000 0.04294 0.03966 = 0.02846 0.00427 0.02235 0.00960 F4 5 0.282888 0.487036 -0.000052 11.00000 0.02681 0.03716 = 0.04168 0.00349 0.01663 0.00201 CL1 6 0.894577 0.291721 0.138776 11.00000 0.02271 0.03639 = 0.04252 0.00147 0.00837 0.00348 PART 1 C29 1 0.989816 0.169656 0.161912 21.00000 0.03779 0.03821 = 0.02607 0.00976 0.01169 0.01147 AFIX 23 H29A 2 0.964121 0.090413 0.181500 21.00000 -1.20000 H29B 2 1.048350 0.203864 0.201769 21.00000 -1.20000 AFIX 0 CL2 6 1.029162 0.124249 0.083720 21.00000 0.05257 0.02656 = 0.03040 0.00426 0.02101 0.00636 PART 2 C29A 1 0.989816 0.169656 0.161912 -21.00000 0.03779 0.03821 = 0.02607 0.00976 0.01169 0.01147 AFIX 23 H29C 2 0.975057 0.101356 0.195109 -21.00000 -1.20000 H29D 2 1.056573 0.209282 0.186501 -21.00000 -1.20000 AFIX 0 CL2A 6 0.984921 0.102233 0.073079 -21.00000 0.05257 0.02656 = 0.03040 0.00426 0.02101 0.00636 PART HKLF 4 REM PML029_0m in P2(1)/n REM R1 = 0.0442 for 4902 Fo > 4sig(Fo) and 0.0618 for all 6228 data REM 360 parameters refined using 1 restraints END WGHT 0.0440 2.0671 REM Highest difference peak 0.529, deepest hole -0.312, 1-sigma level 0.063 Q1 1 0.3226 -0.0987 0.2393 11.00000 0.05 0.53 Q2 1 0.5000 0.5000 0.0000 10.50000 0.05 0.47 Q3 1 0.2844 0.1405 -0.0185 11.00000 0.05 0.44 Q4 1 0.7842 0.5397 0.1101 11.00000 0.05 0.40 Q5 1 0.3766 0.1260 0.2315 11.00000 0.05 0.39 ;