# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Francois Diederich' _publ_contact_author_email DIEDERICH@ORG.CHEM.ETHZ.CH _publ_section_title ; Self-Association Based on Orthogonal C=O***C=O Interactions in the Solid and Liquid State ; loop_ _publ_author_name 'Francois Diederich' 'Marc-Olivier Ebert' 'Christoph Fah' 'W. Bernd Schweizer' # Attachment 'Compound-1.cif' # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_1 _database_code_depnum_ccdc_archive 'CCDC 736727' _audit_creation_method maXus _publ_section_abstract ; We present the crystal and molecular structure of d290108 ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All diagrams and calculations were performed using maXus (Bruker Nonius, Delft & MacScience, Japan). ; _publ_section_synopsis ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _chemical_compound_source 'Diederich laboratory' _exptl_crystal_description needle _exptl_crystal_size_max .36 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .08 _exptl_crystal_F_000 984.0 _exptl_crystal_colour Colourless _cell_measurement_temperature 223 _refine_ls_hydrogen_treatment constr _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 -0.08112 _diffrn_orient_matrix_UB_12 0.14202 _diffrn_orient_matrix_UB_13 0.02619 _diffrn_orient_matrix_UB_21 -0.00153 _diffrn_orient_matrix_UB_22 0.00609 _diffrn_orient_matrix_UB_23 -0.03774 _diffrn_orient_matrix_UB_31 -0.06112 _diffrn_orient_matrix_UB_32 -0.02246 _diffrn_orient_matrix_UB_33 -0.00114 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 463.568 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_cell_setting Monoclinic _chemical_formula_moiety 'C29 H31 F2 N O2 ' _chemical_formula_sum 'C29 H31 F2 N O2 ' _chemical_name_systematic ; (R)-N-((3,3-difluoro-4-oxocyclopentyl)methyl)-2-(naphthalen-2-yl)-N- (4-pentylphenyl)acetamide ; _cell_length_a 6.1172(2) _cell_length_b 26.1410(10) _cell_length_c 15.5575(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.276(2) _cell_angle_gamma 90.00 _cell_volume 2455.3(2) _diffrn_reflns_number 6501 _diffrn_reflns_theta_max 22.98 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_full 22.98 _cell_measurement_reflns_used 20682 _cell_measurement_theta_min 2.425 _cell_measurement_theta_max 22.986 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97(Altomare et al., J. Appl. Cryst.,1999)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' F F 0.0171 0.0103 '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' _exptl_absorpt_coefficient_mu 0.088 _reflns_number_total 3364 _reflns_number_gt 2312 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Pentyl group heavily disordered, refined with constraint bond lengths. There is an indication that the cyclopentyl ring is disordered with 10% of the fluorine and carbonyl oxygen substituents exchanging positions. This explains the residual electron density (0.7 e/A^3^) in bonding distance to C8. The quality of the data did not allow to refine this disorder. ; _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^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3364 _refine_ls_number_parameters 302 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1358 _refine_ls_R_factor_gt 0.1031 _refine_ls_wR_factor_ref 0.2907 _refine_ls_wR_factor_gt 0.2748 _refine_ls_goodness_of_fit_ref 1.762 _refine_ls_restrained_S_all 1.782 _refine_ls_shift/su_max 0.247 _refine_ls_shift/su_mean 0.011 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 F11 F 0.0983(15) 0.02550(17) 0.2799(5) 0.268(5) Uani 1 1 d . . . F12 F 0.2693(6) -0.05164(12) 0.2728(2) 0.1081(12) Uani 1 1 d . . . N3 N 0.4301(6) 0.11287(14) 0.0248(3) 0.0645(11) Uani 1 1 d . . . O34 O -0.0774(7) -0.03440(16) 0.1346(3) 0.1024(14) Uani 1 1 d . . . O5 O 0.6154(7) 0.06968(14) -0.0669(2) 0.0866(11) Uani 1 1 d . . . C1 C 0.3763(8) 0.13632(18) -0.1324(3) 0.0676(13) Uani 1 1 d . . . C2 C 0.4835(8) 0.10335(19) -0.0552(3) 0.0633(12) Uani 1 1 d . . . C4 C 0.5247(8) 0.07954(19) 0.0975(3) 0.0678(13) Uani 1 1 d . . . C6 C 0.3517(8) 0.06133(18) 0.1496(3) 0.0682(14) Uani 1 1 d . . . C7 C 0.1535(8) 0.03457(19) 0.0943(3) 0.0719(14) Uani 1 1 d . . . C8 C 0.0752(11) -0.0035(2) 0.1546(4) 0.0917(18) Uani 1 1 d . . . C9 C 0.2423(12) -0.0082(2) 0.2320(4) 0.0973(19) Uani 1 1 d . . . C10 C 0.4452(10) 0.02065(18) 0.2170(3) 0.0789(15) Uani 1 1 d . . . C13 C 0.3172(7) 0.15825(18) 0.0456(3) 0.0595(12) Uani 1 1 d . . . C14 C 0.4352(9) 0.19607(19) 0.0958(3) 0.0688(13) Uani 1 1 d . . . C15 C 0.3323(10) 0.2414(2) 0.1106(3) 0.0824(16) Uani 1 1 d . . . C16 C 0.1103(11) 0.2493(2) 0.0750(4) 0.0853(17) Uani 1 1 d . B . C17 C -0.0058(9) 0.2104(2) 0.0292(4) 0.0812(16) Uani 1 1 d . . . C18 C 0.0955(8) 0.1651(2) 0.0159(3) 0.0722(14) Uani 1 1 d . . . C19 C 0.5158(7) 0.18184(17) -0.1479(3) 0.0585(12) Uani 1 1 d . . . C20 C 0.7070(8) 0.1751(2) -0.1863(3) 0.0691(14) Uani 1 1 d . . . C21 C 0.8322(8) 0.2160(2) -0.2031(3) 0.0744(14) Uani 1 1 d . . . C22 C 0.8977(10) 0.3097(3) -0.2015(4) 0.096(2) Uani 1 1 d . . . C23 C 0.8355(16) 0.3576(3) -0.1807(5) 0.121(3) Uani 1 1 d . . . C24 C 0.6513(15) 0.3644(3) -0.1416(5) 0.113(2) Uani 1 1 d . . . C25 C 0.5263(10) 0.3238(2) -0.1260(4) 0.0877(17) Uani 1 1 d . . . C26 C 0.4551(7) 0.23036(18) -0.1290(3) 0.0618(12) Uani 1 1 d . . . C27 C 0.7731(9) 0.2660(2) -0.1840(3) 0.0726(15) Uani 1 1 d . . . C28 C 0.5797(8) 0.27372(18) -0.1455(3) 0.0653(13) Uani 1 1 d . . . C29 C -0.0078(16) 0.2999(3) 0.0831(5) 0.137(3) Uani 1 1 d D . . C30 C 0.087(3) 0.3415(6) 0.1273(10) 0.130(6) Uiso 0.50 1 d PD B 1 C31 C 0.188(3) 0.3610(6) 0.0547(10) 0.119(5) Uiso 0.50 1 d PD B 1 C32 C 0.197(4) 0.4157(7) 0.0855(15) 0.172 Uiso 0.50 1 d PD B 1 C33 C 0.353(3) 0.4479(7) 0.0432(13) 0.148(6) Uiso 0.50 1 d PD B 1 C50 C 0.149(3) 0.3453(6) 0.0860(17) 0.135(6) Uiso 0.50 1 d PD B 2 C51 C 0.020(3) 0.3954(5) 0.0845(10) 0.121(5) Uiso 0.50 1 d PD B 2 C52 C 0.167(5) 0.4434(9) 0.1077(16) 0.221(12) Uiso 0.50 1 d PD B 2 C53 C 0.204(5) 0.4497(11) 0.0143(17) 0.227(12) Uiso 0.50 1 d PD B 2 H1A H 0.3516 0.1152 -0.1851 0.081 Uiso 1 1 calc R . . H1B H 0.2316 0.1483 -0.1213 0.081 Uiso 1 1 calc R . . H4A H 0.6401 0.0983 0.1360 0.081 Uiso 1 1 calc R . . H4B H 0.5941 0.0498 0.0745 0.081 Uiso 1 1 calc R . . H6 H 0.2976 0.0908 0.1801 0.082 Uiso 1 1 calc R . . H7A H 0.0364 0.0592 0.0733 0.086 Uiso 1 1 calc R . . H7B H 0.1991 0.0174 0.0441 0.086 Uiso 1 1 calc R . . H10A H 0.5500 -0.0019 0.1940 0.095 Uiso 1 1 calc R . . H10B H 0.5195 0.0366 0.2709 0.095 Uiso 1 1 calc R . . H14 H 0.5847 0.1908 0.1196 0.083 Uiso 1 1 calc R . . H15 H 0.4117 0.2671 0.1447 0.099 Uiso 1 1 calc R . . H17 H -0.1566 0.2149 0.0067 0.097 Uiso 1 1 calc R . . H18 H 0.0124 0.1384 -0.0139 0.087 Uiso 1 1 calc R . . H20 H 0.7490 0.1420 -0.2005 0.083 Uiso 1 1 calc R . . H21 H 0.9604 0.2105 -0.2280 0.089 Uiso 1 1 calc R . . H22 H 1.0245 0.3054 -0.2277 0.116 Uiso 1 1 calc R . . H23 H 0.9188 0.3861 -0.1932 0.145 Uiso 1 1 calc R . . H24 H 0.6121 0.3974 -0.1255 0.135 Uiso 1 1 calc R . . H25 H 0.3983 0.3295 -0.1011 0.105 Uiso 1 1 calc R . . H26 H 0.3263 0.2350 -0.1041 0.074 Uiso 1 1 calc R . . H29A H -0.0606 0.3115 0.0234 0.164 Uiso 1 1 calc R A 1 H29B H -0.1401 0.2918 0.1085 0.164 Uiso 1 1 calc R A 1 H30A H 0.1960 0.3322 0.1780 0.156 Uiso 0.50 1 calc PR B 1 H30B H -0.0232 0.3651 0.1445 0.156 Uiso 0.50 1 calc PR B 1 H31A H 0.0936 0.3563 -0.0019 0.143 Uiso 0.50 1 calc PR B 1 H31B H 0.3355 0.3465 0.0534 0.143 Uiso 0.50 1 calc PR B 1 H32A H 0.0476 0.4305 0.0727 0.206 Uiso 0.50 1 calc PR B 1 H32B H 0.2431 0.4164 0.1488 0.206 Uiso 0.50 1 calc PR B 1 H33A H 0.2974 0.4509 -0.0186 0.222 Uiso 0.50 1 calc PR B 1 H33B H 0.4978 0.4319 0.0516 0.222 Uiso 0.50 1 calc PR B 1 H33C H 0.3642 0.4817 0.0694 0.222 Uiso 0.50 1 calc PR B 1 H50A H 0.2273 0.3440 0.0358 0.162 Uiso 0.50 1 calc PR B 2 H50B H 0.2593 0.3437 0.1391 0.162 Uiso 0.50 1 calc PR B 2 H51A H -0.0850 0.3927 0.1257 0.145 Uiso 0.50 1 calc PR B 2 H51B H -0.0665 0.4000 0.0262 0.145 Uiso 0.50 1 calc PR B 2 H52A H 0.0869 0.4721 0.1287 0.265 Uiso 0.50 1 calc PR B 2 H52B H 0.3033 0.4362 0.1482 0.265 Uiso 0.50 1 calc PR B 2 H53A H 0.3500 0.4373 0.0086 0.340 Uiso 0.50 1 calc PR B 2 H53B H 0.1913 0.4856 -0.0017 0.340 Uiso 0.50 1 calc PR B 2 H53C H 0.0928 0.4302 -0.0238 0.340 Uiso 0.50 1 calc PR B 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 F11 0.451(11) 0.098(3) 0.343(8) -0.042(4) 0.326(9) -0.020(4) F12 0.156(3) 0.075(2) 0.096(2) 0.0218(18) 0.030(2) 0.002(2) N3 0.055(2) 0.059(2) 0.075(3) 0.011(2) -0.0048(19) -0.0005(19) O34 0.089(3) 0.093(3) 0.124(3) 0.016(2) 0.015(2) -0.033(2) O5 0.105(3) 0.070(2) 0.083(2) 0.0047(19) 0.010(2) 0.016(2) C1 0.066(3) 0.067(3) 0.064(3) 0.006(2) -0.007(2) -0.010(2) C2 0.068(3) 0.060(3) 0.059(3) 0.007(2) 0.001(2) -0.012(3) C4 0.066(3) 0.065(3) 0.068(3) 0.015(2) -0.005(2) -0.003(2) C6 0.086(4) 0.053(3) 0.064(3) 0.002(2) 0.005(3) -0.002(2) C7 0.059(3) 0.061(3) 0.094(4) 0.014(3) 0.009(3) 0.000(2) C8 0.085(4) 0.076(4) 0.119(5) 0.027(3) 0.031(4) 0.015(3) C9 0.144(6) 0.074(4) 0.077(4) 0.013(3) 0.029(4) -0.016(4) C10 0.112(4) 0.058(3) 0.062(3) 0.004(2) -0.002(3) -0.012(3) C13 0.053(3) 0.064(3) 0.057(3) 0.013(2) -0.004(2) -0.005(2) C14 0.068(3) 0.072(3) 0.064(3) 0.014(3) 0.002(2) -0.001(3) C15 0.107(5) 0.073(4) 0.066(3) 0.005(3) 0.008(3) -0.004(3) C16 0.107(5) 0.085(4) 0.071(3) 0.022(3) 0.034(3) 0.036(4) C17 0.075(4) 0.091(4) 0.080(4) 0.025(3) 0.018(3) 0.012(3) C18 0.061(3) 0.081(4) 0.071(3) 0.022(3) 0.002(2) -0.002(3) C19 0.062(3) 0.057(3) 0.053(3) 0.005(2) -0.001(2) -0.001(2) C20 0.062(3) 0.081(3) 0.063(3) 0.000(2) 0.004(2) 0.010(3) C21 0.059(3) 0.096(4) 0.067(3) 0.012(3) 0.009(2) -0.001(3) C22 0.081(4) 0.111(5) 0.088(4) 0.037(4) -0.013(3) -0.028(4) C23 0.148(7) 0.084(5) 0.110(5) 0.050(4) -0.040(5) -0.043(5) C24 0.142(7) 0.062(4) 0.122(6) 0.019(4) -0.015(5) 0.000(4) C25 0.095(4) 0.062(3) 0.096(4) 0.011(3) -0.013(3) 0.004(3) C26 0.053(3) 0.074(3) 0.056(3) 0.012(2) 0.003(2) 0.003(2) C27 0.071(3) 0.082(4) 0.058(3) 0.021(3) -0.007(3) -0.012(3) C28 0.070(3) 0.059(3) 0.060(3) 0.012(2) -0.009(2) 0.004(3) C29 0.196(8) 0.105(5) 0.119(6) 0.019(5) 0.051(6) 0.043(6) _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 F11 C9 1.523(8) . ? F12 C9 1.298(6) . ? N3 C2 1.360(6) . ? N3 C13 1.435(6) . ? N3 C4 1.470(6) . ? O34 C8 1.236(7) . ? O5 C2 1.227(6) . ? C1 C19 1.506(6) . ? C1 C2 1.537(6) . ? C4 C6 1.509(7) . ? C6 C7 1.537(7) . ? C6 C10 1.537(6) . ? C7 C8 1.498(7) . ? C8 C9 1.454(9) . ? C9 C10 1.503(8) . ? C13 C18 1.372(6) . ? C13 C14 1.388(7) . ? C14 C15 1.379(7) . ? C15 C16 1.397(8) . ? C16 C17 1.373(8) . ? C16 C29 1.522(9) . ? C17 C18 1.368(7) . ? C19 C26 1.367(6) . ? C19 C20 1.407(7) . ? C20 C21 1.364(7) . ? C21 C27 1.401(7) . ? C22 C23 1.364(10) . ? C22 C27 1.423(8) . ? C23 C24 1.376(10) . ? C24 C25 1.353(9) . ? C25 C28 1.394(7) . ? C26 C28 1.413(7) . ? C27 C28 1.423(7) . ? C29 C30 1.364(14) . ? C29 C50 1.522(15) . ? C30 C31 1.465(16) . ? C31 C32 1.508(16) . ? C32 C33 1.502(16) . ? C50 C51 1.526(16) . ? C51 C52 1.554(17) . ? C52 C53 1.514(18) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C6 H6 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C14 H14 0.9400 . ? C15 H15 0.9400 . ? C17 H17 0.9400 . ? C18 H18 0.9400 . ? C20 H20 0.9400 . ? C21 H21 0.9400 . ? C22 H22 0.9400 . ? C23 H23 0.9400 . ? C24 H24 0.9400 . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 H33C 0.9700 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C53 H53C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N3 C13 123.5(4) . . ? C2 N3 C4 118.2(4) . . ? C13 N3 C4 117.5(4) . . ? C19 C1 C2 112.8(4) . . ? O5 C2 N3 121.9(4) . . ? O5 C2 C1 119.6(4) . . ? N3 C2 C1 118.5(5) . . ? N3 C4 C6 112.1(4) . . ? C4 C6 C7 113.7(4) . . ? C4 C6 C10 111.6(4) . . ? C7 C6 C10 103.9(4) . . ? C8 C7 C6 104.8(5) . . ? O34 C8 C9 123.7(5) . . ? O34 C8 C7 125.5(6) . . ? C9 C8 C7 108.8(5) . . ? F12 C9 C8 119.7(5) . . ? F12 C9 C10 118.2(6) . . ? C8 C9 C10 108.4(5) . . ? F12 C9 F11 107.8(5) . . ? C8 C9 F11 88.3(6) . . ? C10 C9 F11 110.1(5) . . ? C9 C10 C6 103.2(5) . . ? C18 C13 C14 119.5(5) . . ? C18 C13 N3 121.1(4) . . ? C14 C13 N3 119.3(4) . . ? C15 C14 C13 119.8(5) . . ? C14 C15 C16 120.1(5) . . ? C17 C16 C15 119.0(5) . . ? C17 C16 C29 118.3(6) . . ? C15 C16 C29 122.7(7) . . ? C18 C17 C16 120.8(5) . . ? C17 C18 C13 120.6(5) . . ? C26 C19 C20 118.7(4) . . ? C26 C19 C1 121.2(4) . . ? C20 C19 C1 120.0(4) . . ? C21 C20 C19 120.9(5) . . ? C20 C21 C27 121.2(5) . . ? C23 C22 C27 120.9(7) . . ? C22 C23 C24 120.2(6) . . ? C25 C24 C23 120.3(7) . . ? C24 C25 C28 122.6(6) . . ? C19 C26 C28 122.1(4) . . ? C21 C27 C22 122.9(6) . . ? C21 C27 C28 118.8(4) . . ? C22 C27 C28 118.3(6) . . ? C25 C28 C26 124.1(5) . . ? C25 C28 C27 117.7(5) . . ? C26 C28 C27 118.2(4) . . ? C30 C29 C50 31.8(9) . . ? C30 C29 C16 124.5(11) . . ? C50 C29 C16 112.0(9) . . ? C29 C30 C31 94.9(12) . . ? C30 C31 C32 94.7(12) . . ? C33 C32 C31 112.6(17) . . ? C29 C50 C51 110.2(13) . . ? C50 C51 C52 114.2(16) . . ? C53 C52 C51 91.9(18) . . ? C19 C1 H1A 109.0 . . ? C2 C1 H1A 109.0 . . ? C19 C1 H1B 109.0 . . ? C2 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? N3 C4 H4A 109.2 . . ? C6 C4 H4A 109.2 . . ? N3 C4 H4B 109.2 . . ? C6 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C4 C6 H6 109.2 . . ? C7 C6 H6 109.2 . . ? C10 C6 H6 109.2 . . ? C8 C7 H7A 110.8 . . ? C6 C7 H7A 110.8 . . ? C8 C7 H7B 110.8 . . ? C6 C7 H7B 110.8 . . ? H7A C7 H7B 108.9 . . ? C9 C10 H10A 111.1 . . ? C6 C10 H10A 111.1 . . ? C9 C10 H10B 111.1 . . ? C6 C10 H10B 111.1 . . ? H10A C10 H10B 109.1 . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 H21 119.4 . . ? C27 C21 H21 119.4 . . ? C23 C22 H22 119.5 . . ? C27 C22 H22 119.5 . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 H25 118.7 . . ? C28 C25 H25 118.7 . . ? C19 C26 H26 118.9 . . ? C28 C26 H26 118.9 . . ? C30 C29 H29A 106.2 . . ? C50 C29 H29A 84.1 . . ? C16 C29 H29A 106.2 . . ? C30 C29 H29B 106.2 . . ? C50 C29 H29B 135.6 . . ? C16 C29 H29B 106.2 . . ? H29A C29 H29B 106.4 . . ? C29 C30 H30A 112.8 . . ? C31 C30 H30A 112.7 . . ? C29 C30 H30B 112.8 . . ? C31 C30 H30B 112.8 . . ? H30A C30 H30B 110.2 . . ? C30 C31 H31A 112.8 . . ? C32 C31 H31A 112.6 . . ? C30 C31 H31B 112.8 . . ? C32 C31 H31B 113.0 . . ? H31A C31 H31B 110.2 . . ? C33 C32 H32A 109.2 . . ? C31 C32 H32A 109.3 . . ? C33 C32 H32B 108.9 . . ? C31 C32 H32B 108.9 . . ? H32A C32 H32B 107.8 . . ? C32 C33 H33A 109.3 . . ? C32 C33 H33B 109.6 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C29 C50 H50A 109.6 . . ? C51 C50 H50A 109.6 . . ? C29 C50 H50B 109.6 . . ? C51 C50 H50B 109.6 . . ? H50A C50 H50B 108.1 . . ? C50 C51 H51A 108.7 . . ? C52 C51 H51A 108.7 . . ? C50 C51 H51B 108.7 . . ? C52 C51 H51B 108.7 . . ? H51A C51 H51B 107.6 . . ? C53 C52 H52A 113.2 . . ? C51 C52 H52A 113.2 . . ? C53 C52 H52B 113.4 . . ? C51 C52 H52B 113.4 . . ? H52A C52 H52B 110.6 . . ? C52 C53 H53A 109.4 . . ? C52 C53 H53B 109.6 . . ? H53A C53 H53B 109.5 . . ? C52 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 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 C13 N3 C2 O5 165.7(4) . . . . ? C4 N3 C2 O5 -3.6(7) . . . . ? C13 N3 C2 C1 -13.7(6) . . . . ? C4 N3 C2 C1 177.0(4) . . . . ? C19 C1 C2 O5 -86.3(6) . . . . ? C19 C1 C2 N3 93.1(5) . . . . ? C2 N3 C4 C6 -132.2(4) . . . . ? C13 N3 C4 C6 57.8(5) . . . . ? N3 C4 C6 C7 54.8(5) . . . . ? N3 C4 C6 C10 171.9(4) . . . . ? C4 C6 C7 C8 149.8(4) . . . . ? C10 C6 C7 C8 28.4(5) . . . . ? C6 C7 C8 O34 -177.2(5) . . . . ? C6 C7 C8 C9 -12.8(6) . . . . ? O34 C8 C9 F12 16.5(9) . . . . ? C7 C8 C9 F12 -148.2(5) . . . . ? O34 C8 C9 C10 156.3(6) . . . . ? C7 C8 C9 C10 -8.4(7) . . . . ? O34 C8 C9 F11 -93.1(7) . . . . ? C7 C8 C9 F11 102.2(5) . . . . ? F12 C9 C10 C6 166.5(5) . . . . ? C8 C9 C10 C6 26.0(6) . . . . ? F11 C9 C10 C6 -69.1(6) . . . . ? C4 C6 C10 C9 -155.9(4) . . . . ? C7 C6 C10 C9 -33.0(5) . . . . ? C2 N3 C13 C18 73.8(6) . . . . ? C4 N3 C13 C18 -116.8(5) . . . . ? C2 N3 C13 C14 -105.6(5) . . . . ? C4 N3 C13 C14 63.8(5) . . . . ? C18 C13 C14 C15 -4.2(7) . . . . ? N3 C13 C14 C15 175.2(4) . . . . ? C13 C14 C15 C16 -0.1(7) . . . . ? C14 C15 C16 C17 3.3(7) . . . . ? C14 C15 C16 C29 -175.2(5) . . . . ? C15 C16 C17 C18 -2.2(7) . . . . ? C29 C16 C17 C18 176.4(5) . . . . ? C16 C17 C18 C13 -2.2(7) . . . . ? C14 C13 C18 C17 5.4(7) . . . . ? N3 C13 C18 C17 -173.9(4) . . . . ? C2 C1 C19 C26 -108.3(5) . . . . ? C2 C1 C19 C20 74.6(5) . . . . ? C26 C19 C20 C21 1.1(7) . . . . ? C1 C19 C20 C21 178.2(4) . . . . ? C19 C20 C21 C27 -0.9(7) . . . . ? C27 C22 C23 C24 0.6(10) . . . . ? C22 C23 C24 C25 -2.2(11) . . . . ? C23 C24 C25 C28 2.2(10) . . . . ? C20 C19 C26 C28 -0.9(6) . . . . ? C1 C19 C26 C28 -178.0(4) . . . . ? C20 C21 C27 C22 -179.2(5) . . . . ? C20 C21 C27 C28 0.6(7) . . . . ? C23 C22 C27 C21 -179.1(5) . . . . ? C23 C22 C27 C28 1.1(8) . . . . ? C24 C25 C28 C26 179.0(5) . . . . ? C24 C25 C28 C27 -0.5(8) . . . . ? C19 C26 C28 C25 -178.9(5) . . . . ? C19 C26 C28 C27 0.6(7) . . . . ? C21 C27 C28 C25 179.1(4) . . . . ? C22 C27 C28 C25 -1.1(7) . . . . ? C21 C27 C28 C26 -0.4(7) . . . . ? C22 C27 C28 C26 179.4(4) . . . . ? C17 C16 C29 C30 179.3(10) . . . . ? C15 C16 C29 C30 -2.1(12) . . . . ? C17 C16 C29 C50 -147.2(12) . . . . ? C15 C16 C29 C50 31.3(13) . . . . ? C50 C29 C30 C31 8.8(18) . . . . ? C16 C29 C30 C31 84.7(13) . . . . ? C29 C30 C31 C32 155.0(15) . . . . ? C30 C31 C32 C33 162.9(17) . . . . ? C30 C29 C50 C51 -65(2) . . . . ? C16 C29 C50 C51 174.1(13) . . . . ? C29 C50 C51 C52 167.1(16) . . . . ? C50 C51 C52 C53 86(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.713 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.056 _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. ; _chemical_name_common ; (R)-N-((3,3-difluoro-4-oxocyclopentyl)methyl)-2-(naphthalen-2- yl)-N-(4-pentylphenyl)acetamide ;