# 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_shelxl _database_code_depnum_ccdc_archive 'CCDC 902843' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid - S-pyrrolidinium-2-carboxylate (1:1) ; _chemical_name_common ; L-Prolinium cocrystal of S-Naproxen ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 O3, C5 H9 N O2' _chemical_formula_sum 'C19 H23 N O5' _chemical_formula_weight 345.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.6999(2) _cell_length_b 6.5428(3) _cell_length_c 23.1874(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.835(4) _cell_angle_gamma 90.00 _cell_volume 861.66(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1272 _cell_measurement_theta_min 3.8213 _cell_measurement_theta_max 67.4749 _exptl_crystal_description plaquet _exptl_crystal_colour colourless _exptl_crystal_preparation ethanol _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.793 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7969 _exptl_absorpt_correction_T_max 0.9766 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3712 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3516 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 67.60 _reflns_number_total 2241 _reflns_number_gt 2113 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0669P)^2^+0.1287P] 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 _chemical_absolute_configuration rm _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(3) _refine_ls_number_reflns 2241 _refine_ls_number_parameters 239 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 0.9047(5) 0.8874(5) 0.58505(13) 0.0525(7) Uani 1 1 d . . . H1A H 1.0692 0.9147 0.5804 0.063 Uiso 1 1 calc R . . H1B H 0.8136 1.0098 0.5754 0.063 Uiso 1 1 calc R . . C2 C 0.8718(5) 0.8182(5) 0.64541(12) 0.0532(7) Uani 1 1 d . . . H2A H 0.8653 0.9336 0.6715 0.064 Uiso 1 1 calc R . . H2B H 0.9977 0.7272 0.6599 0.064 Uiso 1 1 calc R . . C3 C 0.6382(5) 0.7073(6) 0.63829(11) 0.0513(7) Uani 1 1 d . . . H3A H 0.5084 0.8033 0.6380 0.062 Uiso 1 1 calc R . . H3B H 0.6253 0.6102 0.6695 0.062 Uiso 1 1 calc R . . C4 C 0.6374(4) 0.5968(5) 0.57996(10) 0.0379(6) Uani 1 1 d . . . H4 H 0.6853 0.4540 0.5859 0.045 Uiso 1 1 calc R . . C5 C 0.3983(4) 0.6081(5) 0.54528(10) 0.0399(6) Uani 1 1 d . . . C6 C 0.2399(4) 0.3342(4) 0.78589(10) 0.0403(6) Uani 1 1 d . . . C7 C 0.3855(4) 0.4056(5) 0.83141(11) 0.0413(6) Uani 1 1 d . . . H7 H 0.5270 0.3383 0.8411 0.050 Uiso 1 1 calc R . . C8 C 0.3288(4) 0.5770(4) 0.86412(10) 0.0390(6) Uani 1 1 d . . . C9 C 0.4776(5) 0.6531(5) 0.91181(11) 0.0467(7) Uani 1 1 d . . . H9 H 0.6170 0.5845 0.9230 0.056 Uiso 1 1 calc R . . C10 C 0.4218(5) 0.8215(5) 0.94112(12) 0.0493(7) Uani 1 1 d . . . H10 H 0.5222 0.8670 0.9722 0.059 Uiso 1 1 calc R . . C11 C 0.2112(5) 0.9299(5) 0.92496(11) 0.0455(6) Uani 1 1 d . . . C12 C 0.0596(5) 0.8605(5) 0.88084(12) 0.0452(6) Uani 1 1 d . . . H12 H -0.0808 0.9295 0.8711 0.054 Uiso 1 1 calc R . . C13 C 0.1153(4) 0.6831(4) 0.84965(11) 0.0401(6) Uani 1 1 d . . . C14 C -0.0362(4) 0.6054(5) 0.80333(11) 0.0465(7) Uani 1 1 d . . . H14 H -0.1794 0.6700 0.7935 0.056 Uiso 1 1 calc R . . C15 C 0.0229(4) 0.4380(5) 0.77277(11) 0.0447(7) Uani 1 1 d . . . H15 H -0.0810 0.3905 0.7427 0.054 Uiso 1 1 calc R . . C16 C 0.2985(4) 0.1520(5) 0.74955(11) 0.0430(6) Uani 1 1 d . . . H16 H 0.1551 0.0698 0.7430 0.052 Uiso 1 1 calc R . . C17 C 0.3647(4) 0.2251(5) 0.69045(11) 0.0435(6) Uani 1 1 d . . . C18 C 0.4910(6) 0.0129(5) 0.77661(12) 0.0519(7) Uani 1 1 d . . . H18A H 0.5159 -0.0978 0.7507 0.078 Uiso 1 1 calc R . . H18B H 0.4444 -0.0406 0.8125 0.078 Uiso 1 1 calc R . . H18C H 0.6342 0.0894 0.7838 0.078 Uiso 1 1 calc R . . C19 C -0.0186(6) 1.2257(6) 0.94020(14) 0.0605(8) Uani 1 1 d . . . H19A H -0.0230 1.3393 0.9663 0.091 Uiso 1 1 calc R . . H19B H -0.1599 1.1465 0.9414 0.091 Uiso 1 1 calc R . . H19C H -0.0070 1.2753 0.9016 0.091 Uiso 1 1 calc R . . N1 N 0.8164(3) 0.7100(4) 0.54815(9) 0.0432(5) Uani 1 1 d . . . O1 O 0.3689(3) 0.7351(4) 0.50673(9) 0.0598(6) Uani 1 1 d . . . O2 O 0.2400(3) 0.4867(3) 0.56097(7) 0.0449(5) Uani 1 1 d . . . O3 O 0.5619(4) 0.2272(5) 0.67659(9) 0.0655(7) Uani 1 1 d . . . O4 O 0.1831(3) 0.2931(4) 0.65701(9) 0.0615(7) Uani 1 1 d . . . O5 O 0.1794(4) 1.1015(4) 0.95695(9) 0.0594(6) Uani 1 1 d . . . H1D H 0.958(7) 0.639(7) 0.5425(16) 0.075(11) Uiso 1 1 d . . . H1C H 0.760(6) 0.759(6) 0.5124(15) 0.056(9) Uiso 1 1 d . . . H4O H 0.228(6) 0.335(7) 0.6226(18) 0.075(12) Uiso 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 0.0467(14) 0.0480(17) 0.0613(16) -0.0004(15) -0.0040(12) -0.0079(13) C2 0.0483(14) 0.0548(19) 0.0538(15) -0.0121(15) -0.0110(11) -0.0029(14) C3 0.0525(14) 0.0614(19) 0.0393(13) -0.0071(14) -0.0004(10) -0.0103(15) C4 0.0329(11) 0.0407(14) 0.0389(11) 0.0001(11) -0.0035(9) 0.0003(10) C5 0.0330(12) 0.0490(17) 0.0371(11) -0.0020(12) -0.0015(9) 0.0009(11) C6 0.0395(12) 0.0440(15) 0.0372(12) 0.0051(12) 0.0025(9) -0.0007(11) C7 0.0346(12) 0.0456(16) 0.0426(13) 0.0040(13) -0.0023(9) 0.0046(11) C8 0.0364(12) 0.0413(15) 0.0385(11) 0.0047(12) -0.0009(9) 0.0012(11) C9 0.0421(13) 0.0521(17) 0.0438(13) 0.0017(13) -0.0079(10) 0.0028(12) C10 0.0488(14) 0.0556(18) 0.0415(13) -0.0036(13) -0.0078(10) -0.0005(14) C11 0.0501(14) 0.0466(16) 0.0401(13) -0.0011(12) 0.0051(11) 0.0002(13) C12 0.0424(13) 0.0470(17) 0.0455(13) 0.0021(13) 0.0006(10) 0.0062(12) C13 0.0362(12) 0.0424(15) 0.0411(12) 0.0049(12) 0.0003(9) 0.0024(11) C14 0.0368(12) 0.0501(17) 0.0506(14) -0.0036(14) -0.0081(10) 0.0052(12) C15 0.0377(12) 0.0498(17) 0.0450(13) -0.0019(13) -0.0065(10) 0.0007(12) C16 0.0412(12) 0.0434(16) 0.0437(13) 0.0017(12) -0.0008(10) -0.0018(11) C17 0.0456(14) 0.0397(14) 0.0446(13) -0.0017(12) -0.0005(10) 0.0027(12) C18 0.0635(16) 0.0444(17) 0.0477(14) 0.0061(13) 0.0042(12) 0.0074(14) C19 0.0673(18) 0.0492(19) 0.0661(18) -0.0081(17) 0.0120(14) 0.0090(16) N1 0.0339(10) 0.0536(15) 0.0413(11) 0.0034(11) -0.0023(8) 0.0014(11) O1 0.0451(10) 0.0744(16) 0.0572(11) 0.0260(12) -0.0124(8) -0.0072(11) O2 0.0356(8) 0.0545(12) 0.0439(9) 0.0034(9) -0.0007(7) -0.0033(9) O3 0.0521(11) 0.0830(18) 0.0624(12) 0.0237(14) 0.0107(9) 0.0126(12) O4 0.0442(10) 0.0901(19) 0.0491(11) 0.0204(12) -0.0034(8) 0.0011(11) O5 0.0698(13) 0.0547(14) 0.0523(11) -0.0128(12) -0.0030(9) 0.0089(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.498(4) . ? C1 N1 1.503(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.513(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.533(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N1 1.503(3) . ? C4 C5 1.525(3) . ? C4 H4 0.9800 . ? C5 O1 1.222(3) . ? C5 O2 1.278(3) . ? C6 C7 1.368(4) . ? C6 C15 1.421(4) . ? C6 C16 1.513(4) . ? C7 C8 1.407(4) . ? C7 H7 0.9300 . ? C8 C13 1.416(3) . ? C8 C9 1.425(4) . ? C9 C10 1.347(4) . ? C9 H9 0.9300 . ? C10 C11 1.417(4) . ? C10 H10 0.9300 . ? C11 C12 1.360(4) . ? C11 O5 1.366(4) . ? C12 C13 1.418(4) . ? C12 H12 0.9300 . ? C13 C14 1.415(4) . ? C14 C15 1.362(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C18 1.520(4) . ? C16 C17 1.528(4) . ? C16 H16 0.9800 . ? C17 O3 1.195(3) . ? C17 O4 1.317(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 O5 1.418(4) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N1 H1D 0.95(4) . ? N1 H1C 0.92(4) . ? O4 H4O 0.90(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 103.7(3) . . ? C2 C1 H1A 111.0 . . ? N1 C1 H1A 111.0 . . ? C2 C1 H1B 111.0 . . ? N1 C1 H1B 111.0 . . ? H1A C1 H1B 109.0 . . ? C1 C2 C3 102.8(2) . . ? C1 C2 H2A 111.2 . . ? C3 C2 H2A 111.2 . . ? C1 C2 H2B 111.2 . . ? C3 C2 H2B 111.2 . . ? H2A C2 H2B 109.1 . . ? C2 C3 C4 105.0(2) . . ? C2 C3 H3A 110.7 . . ? C4 C3 H3A 110.7 . . ? C2 C3 H3B 110.7 . . ? C4 C3 H3B 110.7 . . ? H3A C3 H3B 108.8 . . ? N1 C4 C5 109.3(2) . . ? N1 C4 C3 104.4(2) . . ? C5 C4 C3 112.2(2) . . ? N1 C4 H4 110.2 . . ? C5 C4 H4 110.2 . . ? C3 C4 H4 110.2 . . ? O1 C5 O2 125.1(2) . . ? O1 C5 C4 118.7(2) . . ? O2 C5 C4 116.2(2) . . ? C7 C6 C15 117.5(3) . . ? C7 C6 C16 123.4(2) . . ? C15 C6 C16 119.1(2) . . ? C6 C7 C8 122.4(2) . . ? C6 C7 H7 118.8 . . ? C8 C7 H7 118.8 . . ? C7 C8 C13 119.6(2) . . ? C7 C8 C9 123.2(2) . . ? C13 C8 C9 117.1(3) . . ? C10 C9 C8 121.8(3) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C9 C10 C11 120.5(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 O5 125.3(3) . . ? C12 C11 C10 120.1(3) . . ? O5 C11 C10 114.6(2) . . ? C11 C12 C13 120.1(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C8 117.5(3) . . ? C14 C13 C12 122.2(2) . . ? C8 C13 C12 120.3(2) . . ? C15 C14 C13 121.4(2) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C6 121.5(2) . . ? C14 C15 H15 119.3 . . ? C6 C15 H15 119.3 . . ? C6 C16 C18 115.3(2) . . ? C6 C16 C17 109.6(2) . . ? C18 C16 C17 109.5(2) . . ? C6 C16 H16 107.4 . . ? C18 C16 H16 107.4 . . ? C17 C16 H16 107.4 . . ? O3 C17 O4 123.2(3) . . ? O3 C17 C16 123.6(2) . . ? O4 C17 C16 113.1(2) . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O5 C19 H19A 109.5 . . ? O5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O5 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1 N1 C4 108.0(2) . . ? C1 N1 H1D 102(3) . . ? C4 N1 H1D 116(3) . . ? C1 N1 H1C 108(3) . . ? C4 N1 H1C 114(2) . . ? H1D N1 H1C 106(3) . . ? C17 O4 H4O 111(2) . . ? C11 O5 C19 117.5(2) . . ? _iucr_refine_instructions_details ; TITL bn_TLnaproxprol in P2(1) CELL 1.54184 5.6999 6.5428 23.1874 90.000 94.835 90.000 ZERR 2.00 0.0002 0.0003 0.0010 0.000 0.004 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N O UNIT 38 46 2 10 MERG 2 FMAP 2 PLAN 10 SIZE 0.03 0.22 0.30 ACTA BOND $H L.S. 10 TEMP 20.00 WGHT 0.066900 0.128700 EXTI 0.018752 FVAR 21.71486 C1 1 0.904669 0.887417 0.585048 11.00000 0.04673 0.04801 = 0.06131 -0.00038 -0.00400 -0.00787 AFIX 23 H1A 2 1.069236 0.914743 0.580354 11.00000 -1.20000 H1B 2 0.813588 1.009762 0.575382 11.00000 -1.20000 AFIX 0 C2 1 0.871825 0.818206 0.645413 11.00000 0.04834 0.05478 = 0.05381 -0.01213 -0.01101 -0.00288 AFIX 23 H2A 2 0.865344 0.933584 0.671500 11.00000 -1.20000 H2B 2 0.997669 0.727225 0.659885 11.00000 -1.20000 AFIX 0 C3 1 0.638196 0.707313 0.638286 11.00000 0.05252 0.06136 = 0.03927 -0.00709 -0.00044 -0.01029 AFIX 23 H3A 2 0.508387 0.803271 0.638023 11.00000 -1.20000 H3B 2 0.625256 0.610219 0.669472 11.00000 -1.20000 AFIX 0 C4 1 0.637424 0.596840 0.579960 11.00000 0.03293 0.04069 = 0.03894 0.00014 -0.00354 0.00033 AFIX 13 H4 2 0.685312 0.454006 0.585882 11.00000 -1.20000 AFIX 0 C5 1 0.398292 0.608086 0.545278 11.00000 0.03296 0.04898 = 0.03707 -0.00202 -0.00155 0.00089 C6 1 0.239926 0.334221 0.785893 11.00000 0.03953 0.04399 = 0.03725 0.00514 0.00254 -0.00070 C7 1 0.385454 0.405589 0.831408 11.00000 0.03459 0.04565 = 0.04261 0.00396 -0.00228 0.00465 AFIX 43 H7 2 0.527037 0.338288 0.841073 11.00000 -1.20000 AFIX 0 C8 1 0.328775 0.577044 0.864124 11.00000 0.03641 0.04131 = 0.03847 0.00475 -0.00087 0.00119 C9 1 0.477625 0.653063 0.911810 11.00000 0.04214 0.05211 = 0.04382 0.00166 -0.00792 0.00276 AFIX 43 H9 2 0.617033 0.584527 0.922983 11.00000 -1.20000 AFIX 0 C10 1 0.421805 0.821470 0.941120 11.00000 0.04877 0.05563 = 0.04146 -0.00358 -0.00778 -0.00047 AFIX 43 H10 2 0.522152 0.866962 0.972177 11.00000 -1.20000 AFIX 0 C11 1 0.211165 0.929857 0.924959 11.00000 0.05008 0.04659 = 0.04007 -0.00106 0.00509 0.00023 C12 1 0.059557 0.860501 0.880841 11.00000 0.04244 0.04702 = 0.04554 0.00208 0.00055 0.00618 AFIX 43 H12 2 -0.080845 0.929546 0.871123 11.00000 -1.20000 AFIX 0 C13 1 0.115290 0.683090 0.849652 11.00000 0.03621 0.04238 = 0.04114 0.00491 0.00028 0.00244 C14 1 -0.036244 0.605382 0.803329 11.00000 0.03677 0.05009 = 0.05061 -0.00360 -0.00814 0.00520 AFIX 43 H14 2 -0.179389 0.670007 0.793526 11.00000 -1.20000 AFIX 0 C15 1 0.022938 0.437975 0.772773 11.00000 0.03769 0.04983 = 0.04497 -0.00191 -0.00648 0.00068 AFIX 43 H15 2 -0.080960 0.390534 0.742660 11.00000 -1.20000 AFIX 0 C16 1 0.298499 0.152046 0.749552 11.00000 0.04118 0.04341 = 0.04371 0.00173 -0.00079 -0.00179 AFIX 13 H16 2 0.155067 0.069753 0.743008 11.00000 -1.20000 AFIX 0 C17 1 0.364666 0.225099 0.690455 11.00000 0.04559 0.03969 = 0.04462 -0.00166 -0.00053 0.00272 C18 1 0.490994 0.012927 0.776609 11.00000 0.06350 0.04439 = 0.04771 0.00610 0.00415 0.00743 AFIX 33 H18A 2 0.515929 -0.097836 0.750668 11.00000 -1.50000 H18B 2 0.444410 -0.040637 0.812460 11.00000 -1.50000 H18C 2 0.634232 0.089382 0.783787 11.00000 -1.50000 AFIX 0 C19 1 -0.018601 1.225659 0.940202 11.00000 0.06734 0.04918 = 0.06613 -0.00808 0.01203 0.00905 AFIX 33 H19A 2 -0.022956 1.339278 0.966287 11.00000 -1.50000 H19B 2 -0.159920 1.146498 0.941394 11.00000 -1.50000 H19C 2 -0.006971 1.275269 0.901584 11.00000 -1.50000 AFIX 0 N1 3 0.816431 0.710028 0.548150 11.00000 0.03388 0.05360 = 0.04128 0.00339 -0.00225 0.00138 O1 4 0.368880 0.735125 0.506729 11.00000 0.04512 0.07435 = 0.05718 0.02601 -0.01236 -0.00721 O2 4 0.240022 0.486732 0.560974 11.00000 0.03556 0.05451 = 0.04393 0.00339 -0.00071 -0.00326 O3 4 0.561868 0.227186 0.676593 11.00000 0.05209 0.08305 = 0.06235 0.02373 0.01068 0.01260 O4 4 0.183066 0.293108 0.657011 11.00000 0.04420 0.09006 = 0.04912 0.02038 -0.00335 0.00106 O5 4 0.179354 1.101503 0.956952 11.00000 0.06980 0.05472 = 0.05233 -0.01276 -0.00305 0.00895 H1D 2 0.957818 0.638951 0.542525 11.00000 0.07543 H1C 2 0.760164 0.759216 0.512401 11.00000 0.05584 H4O 2 0.227567 0.334927 0.622621 11.00000 0.07494 HKLF 4 REM bn_TLnaproxprol in P2(1) REM R1 = 0.0389 for 2113 Fo > 4sig(Fo) and 0.0411 for all 2241 data REM 239 parameters refined using 1 restraints END WGHT 0.0659 0.1300 REM Highest difference peak 0.148, deepest hole -0.187, 1-sigma level 0.037 Q1 1 0.3916 0.6590 0.9411 11.00000 0.05 0.15 Q2 1 0.6287 0.5850 0.6185 11.00000 0.05 0.14 Q3 1 0.2113 0.3816 0.6865 11.00000 0.05 0.14 Q4 1 0.4630 0.0239 0.8222 11.00000 0.05 0.14 Q5 1 -0.0828 1.2590 0.8927 11.00000 0.05 0.13 Q6 1 0.2144 0.9205 0.8932 11.00000 0.05 0.13 Q7 1 0.1820 0.4251 0.7666 11.00000 0.05 0.13 Q8 1 -0.2255 1.1808 0.9220 11.00000 0.05 0.13 Q9 1 0.6108 0.2311 0.6378 11.00000 0.05 0.13 Q10 1 0.5085 0.9093 0.5779 11.00000 0.05 0.13 ; _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 67.60 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.148 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.037 data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 902844' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid - R-pyrrolidinium-2-carboxylate (1:1) ; _chemical_name_common ; D-Prolinium cocrystal of S-Naproxen ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 O3, C5 H9 N O2' _chemical_formula_sum 'C19 H23 N O5' _chemical_formula_weight 345.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.7713(2) _cell_length_b 6.2520(3) _cell_length_c 23.8346(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.047(4) _cell_angle_gamma 90.00 _cell_volume 859.46(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1815 _cell_measurement_theta_min 3.7093 _cell_measurement_theta_max 67.5182 _exptl_crystal_description plaquet _exptl_crystal_colour colourless _exptl_crystal_preparation ethanol _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.795 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.6920 _exptl_absorpt_correction_T_max 0.9765 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3712 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3519 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 67.59 _reflns_number_total 2233 _reflns_number_gt 2141 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution Sir2011 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0904P)^2^+0.6329P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration rm _refine_ls_number_reflns 2233 _refine_ls_number_parameters 248 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.1811 _refine_ls_wR_factor_gt 0.1795 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 C4 C 0.123(9) -0.079(7) 0.5834(13) 0.045(10) Uani 0.30 1 d P A 1 H4A H 0.1675 0.0557 0.5668 0.054 Uiso 0.30 1 calc PR A 1 H4B H -0.0444 -0.0856 0.5854 0.054 Uiso 0.30 1 calc PR A 1 C3 C 0.242(3) -0.114(3) 0.6403(8) 0.061(5) Uani 0.30 1 d P A 1 H3A H 0.2802 0.0236 0.6571 0.074 Uiso 0.30 1 calc PR A 1 H3B H 0.1369 -0.1870 0.6647 0.074 Uiso 0.30 1 calc PR A 1 C2 C 0.420(5) -0.220(9) 0.6368(17) 0.046(2) Uani 0.30 1 d P A 1 H2A H 0.4392 -0.3075 0.6703 0.055 Uiso 0.30 1 calc PR A 1 H2B H 0.5512 -0.1232 0.6360 0.055 Uiso 0.30 1 calc PR A 1 C4' C 0.156(4) -0.079(4) 0.5845(9) 0.065(6) Uani 0.70 1 d P A 2 H4'1 H 0.1106 0.0370 0.5595 0.078 Uiso 0.70 1 calc PR A 2 H4'2 H 0.0280 -0.1116 0.6082 0.078 Uiso 0.70 1 calc PR A 2 C3' C 0.3550(12) -0.0208(14) 0.6176(3) 0.0587(19) Uani 0.70 1 d P A 2 H3'1 H 0.3107 0.0543 0.6512 0.070 Uiso 0.70 1 calc PR A 2 H3'2 H 0.4562 0.0707 0.5966 0.070 Uiso 0.70 1 calc PR A 2 C2' C 0.4791(15) -0.237(3) 0.6333(6) 0.046(2) Uani 0.70 1 d P A 2 H2'1 H 0.6450 -0.2174 0.6390 0.055 Uiso 0.70 1 calc PR A 2 H2'2 H 0.4170 -0.2995 0.6668 0.055 Uiso 0.70 1 calc PR A 2 C1 C 0.4241(6) -0.3741(8) 0.58228(16) 0.0423(9) Uani 1 1 d . . . H4 H 0.3871 -0.5215 0.5927 0.051 Uiso 1 1 calc R A 1 C5 C 0.6341(7) -0.3702(8) 0.54531(17) 0.0441(10) Uani 1 1 d . A . C6 C 0.4943(9) 0.3162(11) 0.9432(2) 0.0706(15) Uani 1 1 d . . . H6A H 0.4865 0.4347 0.9687 0.106 Uiso 1 1 calc R . . H6B H 0.3570 0.2306 0.9457 0.106 Uiso 1 1 calc R . . H6C H 0.5059 0.3688 0.9056 0.106 Uiso 1 1 calc R . . C7 C 0.7291(8) 0.0123(9) 0.9255(2) 0.0536(11) Uani 1 1 d . . . C8 C 0.5851(8) -0.0563(9) 0.8824(2) 0.0524(12) Uani 1 1 d . . . H8 H 0.4485 0.0172 0.8736 0.063 Uiso 1 1 calc R . . C9 C 0.6451(7) -0.2407(8) 0.85100(17) 0.0453(10) Uani 1 1 d . . . C10 C 0.8546(7) -0.3506(8) 0.86401(18) 0.0467(10) Uani 1 1 d . . . C11 C 0.9970(7) -0.2759(10) 0.91008(19) 0.0559(12) Uani 1 1 d . . . H11 H 1.1334 -0.3480 0.9199 0.067 Uiso 1 1 calc R . . C12 C 0.9349(8) -0.0994(10) 0.9399(2) 0.0610(13) Uani 1 1 d . . . H12 H 1.0291 -0.0527 0.9699 0.073 Uiso 1 1 calc R . . C13 C 0.5012(8) -0.3183(9) 0.8062(2) 0.0537(12) Uani 1 1 d . . . H13 H 0.3607 -0.2509 0.7976 0.064 Uiso 1 1 calc R . . C14 C 0.5657(7) -0.4902(9) 0.7754(2) 0.0512(11) Uani 1 1 d . . . H14 H 0.4683 -0.5385 0.7461 0.061 Uiso 1 1 calc R . . C15 C 0.7783(7) -0.5970(8) 0.78703(18) 0.0461(10) Uani 1 1 d . . . C16 C 0.9172(7) -0.5290(8) 0.83104(19) 0.0486(11) Uani 1 1 d . . . H16 H 1.0551 -0.6009 0.8395 0.058 Uiso 1 1 calc R . . C17 C 0.8426(8) -0.7786(8) 0.74812(19) 0.0515(11) Uani 1 1 d . . . H17 H 0.7057 -0.8690 0.7414 0.062 Uiso 1 1 calc R . . C18 C 0.9076(7) -0.6773(8) 0.69231(19) 0.0480(10) Uani 1 1 d . . . C19 C 1.0414(9) -0.9186(10) 0.7699(2) 0.0642(14) Uani 1 1 d . . . H19A H 1.1848 -0.8419 0.7674 0.096 Uiso 1 1 calc R . . H19B H 1.0475 -1.0464 0.7477 0.096 Uiso 1 1 calc R . . H19C H 1.0174 -0.9560 0.8083 0.096 Uiso 1 1 calc R . . N1 N 0.2202(6) -0.2727(7) 0.55125(14) 0.0459(9) Uani 1 1 d . A . H1C H 0.1075 -0.3709 0.5460 0.055 Uiso 1 1 calc R B 1 H1D H 0.2642 -0.2292 0.5172 0.055 Uiso 1 1 calc R B 1 O1 O 0.8001(5) -0.4971(6) 0.55949(13) 0.0503(8) Uani 1 1 d . . . O2 O 0.6390(5) -0.2387(7) 0.50677(13) 0.0598(9) Uani 1 1 d . . . O3 O 0.6929(7) 0.1892(6) 0.95758(15) 0.0659(10) Uani 1 1 d . . . O4 O 0.7525(6) -0.7126(7) 0.65214(14) 0.0645(10) Uani 1 1 d . . . H4E H 0.8003 -0.6677 0.6224 0.084 Uiso 1 1 calc R . . O5 O 1.0814(7) -0.5789(9) 0.68515(16) 0.0893(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 C4 0.047(16) 0.053(19) 0.036(13) -0.032(12) -0.001(10) 0.003(13) C3 0.046(8) 0.066(11) 0.075(11) -0.012(10) 0.038(9) -0.015(8) C2 0.027(6) 0.071(5) 0.042(3) -0.010(3) 0.012(4) 0.006(6) C4' 0.036(6) 0.065(10) 0.094(13) 0.005(8) 0.020(6) 0.014(5) C3' 0.056(4) 0.065(5) 0.056(4) -0.011(4) 0.011(3) -0.005(4) C2' 0.027(6) 0.071(5) 0.042(3) -0.010(3) 0.012(4) 0.006(6) C1 0.0299(18) 0.048(2) 0.050(2) 0.002(2) 0.0061(15) -0.0011(18) C5 0.036(2) 0.052(3) 0.046(2) -0.003(2) 0.0056(16) -0.001(2) C6 0.071(3) 0.066(4) 0.075(3) -0.001(3) 0.014(3) 0.008(3) C7 0.057(3) 0.053(3) 0.052(2) 0.005(2) 0.0071(19) -0.004(2) C8 0.043(2) 0.058(3) 0.056(2) 0.009(2) 0.0024(18) 0.005(2) C9 0.0358(19) 0.049(3) 0.051(2) 0.010(2) 0.0038(16) 0.0006(19) C10 0.040(2) 0.050(3) 0.051(2) 0.008(2) 0.0002(17) 0.0004(19) C11 0.039(2) 0.069(3) 0.059(2) 0.004(3) -0.0058(18) 0.006(2) C12 0.048(2) 0.077(4) 0.058(3) 0.001(3) -0.003(2) 0.001(3) C13 0.039(2) 0.060(3) 0.062(3) 0.006(2) -0.0025(18) 0.011(2) C14 0.041(2) 0.056(3) 0.056(2) 0.005(2) -0.0015(17) 0.005(2) C15 0.039(2) 0.050(3) 0.050(2) 0.009(2) 0.0071(16) 0.0007(19) C16 0.0328(19) 0.057(3) 0.056(2) 0.011(2) 0.0027(16) 0.003(2) C17 0.049(2) 0.046(3) 0.060(2) 0.008(2) 0.0062(19) 0.001(2) C18 0.038(2) 0.051(3) 0.056(2) 0.002(2) 0.0095(17) 0.002(2) C19 0.055(3) 0.060(3) 0.077(3) 0.013(3) 0.006(2) 0.007(3) N1 0.0366(17) 0.052(2) 0.0491(18) -0.0022(18) 0.0042(13) -0.0017(17) O1 0.0351(14) 0.0592(19) 0.0568(17) 0.0057(16) 0.0041(12) 0.0044(15) O2 0.0512(17) 0.073(3) 0.0557(17) 0.0153(18) 0.0149(13) 0.0076(17) O3 0.072(2) 0.060(2) 0.0661(19) -0.0063(18) -0.0014(16) 0.0070(19) O4 0.0586(18) 0.073(3) 0.0617(19) 0.0139(18) -0.0050(14) -0.0197(19) O5 0.061(2) 0.136(4) 0.071(2) 0.029(3) -0.0015(17) -0.043(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C4 C3 1.52(4) . ? C4 N1 1.55(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C3 C2 1.23(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C2 C1 1.62(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C4' C3' 1.42(2) . ? C4' N1 1.50(2) . ? C4' H4'1 0.9700 . ? C4' H4'2 0.9700 . ? C3' C2' 1.569(19) . ? C3' H3'1 0.9700 . ? C3' H3'2 0.9700 . ? C2' C1 1.511(16) . ? C2' H2'1 0.9700 . ? C2' H2'2 0.9700 . ? C1 N1 1.507(5) . ? C1 C5 1.524(5) . ? C1 H4 0.9800 . ? C5 O2 1.234(6) . ? C5 O1 1.280(5) . ? C6 O3 1.426(7) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 O3 1.365(7) . ? C7 C8 1.367(7) . ? C7 C12 1.410(7) . ? C8 C9 1.424(7) . ? C8 H8 0.9300 . ? C9 C13 1.416(7) . ? C9 C10 1.415(6) . ? C10 C16 1.419(7) . ? C10 C11 1.426(7) . ? C11 C12 1.367(8) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.361(8) . ? C13 H13 0.9300 . ? C14 C15 1.415(6) . ? C14 H14 0.9300 . ? C15 C16 1.365(6) . ? C15 C17 1.520(7) . ? C16 H16 0.9300 . ? C17 C19 1.520(7) . ? C17 C18 1.532(6) . ? C17 H17 0.9800 . ? C18 O5 1.194(6) . ? C18 O4 1.306(6) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N1 H1C 0.9000 . ? N1 H1D 0.9000 . ? O4 H4E 0.8200 . ? 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 C4 N1 100(3) . . ? C3 C4 H4A 111.8 . . ? N1 C4 H4A 111.8 . . ? C3 C4 H4B 111.8 . . ? N1 C4 H4B 111.8 . . ? H4A C4 H4B 109.5 . . ? C2 C3 C4 112(3) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C3 C2 C1 114(3) . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C3' C4' N1 107.0(15) . . ? C3' C4' H4'1 110.3 . . ? N1 C4' H4'1 110.3 . . ? C3' C4' H4'2 110.3 . . ? N1 C4' H4'2 110.3 . . ? H4'1 C4' H4'2 108.6 . . ? C4' C3' C2' 105.3(13) . . ? C4' C3' H3'1 110.7 . . ? C2' C3' H3'1 110.7 . . ? C4' C3' H3'2 110.7 . . ? C2' C3' H3'2 110.7 . . ? H3'1 C3' H3'2 108.8 . . ? C1 C2' C3' 102.5(9) . . ? C1 C2' H2'1 111.3 . . ? C3' C2' H2'1 111.3 . . ? C1 C2' H2'2 111.3 . . ? C3' C2' H2'2 111.3 . . ? H2'1 C2' H2'2 109.2 . . ? N1 C1 C2' 107.1(6) . . ? N1 C1 C5 109.4(3) . . ? C2' C1 C5 107.9(5) . . ? N1 C1 C2 96.3(14) . . ? C5 C1 C2 119.3(14) . . ? N1 C1 H4 110.3 . . ? C2' C1 H4 111.7 . . ? C5 C1 H4 110.3 . . ? C2 C1 H4 110.3 . . ? O2 C5 O1 124.9(4) . . ? O2 C5 C1 118.8(4) . . ? O1 C5 C1 116.1(4) . . ? O3 C6 H6A 109.5 . . ? O3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O3 C7 C8 125.1(5) . . ? O3 C7 C12 114.2(4) . . ? C8 C7 C12 120.8(5) . . ? C7 C8 C9 119.7(4) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C13 C9 C10 118.2(4) . . ? C13 C9 C8 121.8(4) . . ? C10 C9 C8 120.0(4) . . ? C9 C10 C16 119.5(4) . . ? C9 C10 C11 118.3(4) . . ? C16 C10 C11 122.2(4) . . ? C12 C11 C10 120.6(4) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C7 120.6(5) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? C14 C13 C9 120.9(4) . . ? C14 C13 H13 119.6 . . ? C9 C13 H13 119.6 . . ? C13 C14 C15 121.3(4) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C16 C15 C14 119.0(5) . . ? C16 C15 C17 123.5(4) . . ? C14 C15 C17 117.5(4) . . ? C15 C16 C10 121.1(4) . . ? C15 C16 H16 119.5 . . ? C10 C16 H16 119.5 . . ? C19 C17 C15 114.8(4) . . ? C19 C17 C18 109.2(4) . . ? C15 C17 C18 107.1(4) . . ? C19 C17 H17 108.5 . . ? C15 C17 H17 108.5 . . ? C18 C17 H17 108.5 . . ? O5 C18 O4 122.7(4) . . ? O5 C18 C17 124.7(4) . . ? O4 C18 C17 112.6(4) . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C4' N1 C1 106.4(9) . . ? C1 N1 C4 112.1(16) . . ? C4' N1 H1C 115.7 . . ? C1 N1 H1C 109.2 . . ? C4 N1 H1C 109.2 . . ? C4' N1 H1D 108.3 . . ? C1 N1 H1D 109.2 . . ? C4 N1 H1D 109.2 . . ? H1C N1 H1D 107.9 . . ? C7 O3 C6 117.0(4) . . ? C18 O4 H4E 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 N1 C4 C3 C2 24(4) . . . . ? C4 C3 C2 C1 -25(5) . . . . ? N1 C4' C3' C2' -33.8(17) . . . . ? C4' C3' C2' C1 32.5(13) . . . . ? C3' C2' C1 N1 -18.6(8) . . . . ? C3' C2' C1 C5 99.2(5) . . . . ? C3' C2' C1 C2 -53(11) . . . . ? C3 C2 C1 N1 14(4) . . . . ? C3 C2 C1 C2' 160(15) . . . . ? C3 C2 C1 C5 130(3) . . . . ? N1 C1 C5 O2 21.9(6) . . . . ? C2' C1 C5 O2 -94.4(8) . . . . ? C2 C1 C5 O2 -88(2) . . . . ? N1 C1 C5 O1 -162.5(4) . . . . ? C2' C1 C5 O1 81.2(8) . . . . ? C2 C1 C5 O1 88(2) . . . . ? O3 C7 C8 C9 178.4(4) . . . . ? C12 C7 C8 C9 -1.0(7) . . . . ? C7 C8 C9 C13 179.8(5) . . . . ? C7 C8 C9 C10 -0.8(7) . . . . ? C13 C9 C10 C16 2.0(6) . . . . ? C8 C9 C10 C16 -177.5(4) . . . . ? C13 C9 C10 C11 -178.4(4) . . . . ? C8 C9 C10 C11 2.1(6) . . . . ? C9 C10 C11 C12 -1.6(7) . . . . ? C16 C10 C11 C12 177.9(5) . . . . ? C10 C11 C12 C7 -0.2(8) . . . . ? O3 C7 C12 C11 -178.0(5) . . . . ? C8 C7 C12 C11 1.5(8) . . . . ? C10 C9 C13 C14 -1.8(7) . . . . ? C8 C9 C13 C14 177.6(4) . . . . ? C9 C13 C14 C15 -0.1(7) . . . . ? C13 C14 C15 C16 1.9(7) . . . . ? C13 C14 C15 C17 -176.2(4) . . . . ? C14 C15 C16 C10 -1.7(7) . . . . ? C17 C15 C16 C10 176.3(4) . . . . ? C9 C10 C16 C15 -0.2(6) . . . . ? C11 C10 C16 C15 -179.8(5) . . . . ? C16 C15 C17 C19 15.3(7) . . . . ? C14 C15 C17 C19 -166.6(4) . . . . ? C16 C15 C17 C18 -106.1(5) . . . . ? C14 C15 C17 C18 71.9(5) . . . . ? C19 C17 C18 O5 -52.7(7) . . . . ? C15 C17 C18 O5 72.2(6) . . . . ? C19 C17 C18 O4 126.3(5) . . . . ? C15 C17 C18 O4 -108.8(5) . . . . ? C3' C4' N1 C1 22.0(17) . . . . ? C3' C4' N1 C4 166(23) . . . . ? C2' C1 N1 C4' -0.5(12) . . . . ? C5 C1 N1 C4' -117.2(11) . . . . ? C2 C1 N1 C4' 7(2) . . . . ? C2' C1 N1 C4 -5(2) . . . . ? C5 C1 N1 C4 -122(2) . . . . ? C2 C1 N1 C4 3(3) . . . . ? C3 C4 N1 C4' -51(20) . . . . ? C3 C4 N1 C1 -14(3) . . . . ? C8 C7 O3 C6 -2.8(7) . . . . ? C12 C7 O3 C6 176.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 67.59 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.234 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.062 _iucr_refine_instructions_details ; TITL nprx-dprol in P2(1) CELL 1.54184 5.7713 6.2520 23.8346 90.000 92.047 90.000 ZERR 2.00 0.0002 0.0003 0.0011 0.000 0.004 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N O UNIT 38 46 2 10 MERG 2 TWIN EADP C2 C2' FMAP 2 PLAN 10 SIZE 0.03 0.20 0.50 ACTA BOND $H CONF L.S. 30 TEMP 20.00 WGHT 0.090400 0.632900 FVAR 13.46033 PART 1 C4 1 0.123007 -0.079221 0.583404 10.30000 0.04669 0.05317 = 0.03555 -0.03189 -0.00111 0.00334 AFIX 23 H4A 2 0.167507 0.055674 0.566810 10.30000 -1.20000 H4B 2 -0.044427 -0.085598 0.585402 10.30000 -1.20000 AFIX 0 C3 1 0.242263 -0.114019 0.640335 10.30000 0.04595 0.06569 = 0.07484 -0.01193 0.03752 -0.01490 AFIX 23 H3A 2 0.280198 0.023563 0.657082 10.30000 -1.20000 H3B 2 0.136945 -0.187048 0.664718 10.30000 -1.20000 AFIX 0 C2 1 0.420001 -0.219982 0.636849 10.30000 0.02670 0.07080 = 0.04186 -0.01038 0.01209 0.00550 AFIX 23 H2A 2 0.439206 -0.307474 0.670301 10.30000 -1.20000 H2B 2 0.551234 -0.123250 0.635994 10.30000 -1.20000 AFIX 0 PART 2 C4' 1 0.156378 -0.079150 0.584450 10.70000 0.03592 0.06544 = 0.09441 0.00478 0.02016 0.01397 AFIX 23 H4'1 2 0.110618 0.037044 0.559464 10.70000 -1.20000 H4'2 2 0.028023 -0.111557 0.608225 10.70000 -1.20000 AFIX 0 C3' 1 0.355031 -0.020817 0.617643 10.70000 0.05580 0.06475 = 0.05633 -0.01077 0.01146 -0.00545 AFIX 23 H3'1 2 0.310708 0.054333 0.651210 10.70000 -1.20000 H3'2 2 0.456220 0.070707 0.596602 10.70000 -1.20000 AFIX 0 C2' 1 0.479148 -0.237182 0.633283 10.70000 0.02670 0.07080 = 0.04186 -0.01038 0.01209 0.00550 AFIX 23 H2'1 2 0.645023 -0.217353 0.638964 10.70000 -1.20000 H2'2 2 0.416984 -0.299466 0.666849 10.70000 -1.20000 AFIX 0 PART 0 C1 1 0.424081 -0.374063 0.582279 11.00000 0.02989 0.04757 = 0.04978 0.00244 0.00612 -0.00112 AFIX 13 H4 2 0.387077 -0.521477 0.592692 11.00000 -1.20000 AFIX 0 C5 1 0.634053 -0.370172 0.545308 11.00000 0.03554 0.05158 = 0.04562 -0.00303 0.00560 -0.00132 C6 1 0.494343 0.316205 0.943219 11.00000 0.07067 0.06637 = 0.07549 -0.00141 0.01435 0.00755 AFIX 33 H6A 2 0.486506 0.434658 0.968710 11.00000 -1.50000 H6B 2 0.356962 0.230642 0.945690 11.00000 -1.50000 H6C 2 0.505878 0.368839 0.905584 11.00000 -1.50000 AFIX 0 C7 1 0.729083 0.012310 0.925462 11.00000 0.05686 0.05257 = 0.05172 0.00454 0.00711 -0.00355 C8 1 0.585110 -0.056295 0.882376 11.00000 0.04348 0.05792 = 0.05572 0.00895 0.00242 0.00454 AFIX 43 H8 2 0.448489 0.017196 0.873587 11.00000 -1.20000 AFIX 0 C9 1 0.645128 -0.240726 0.851003 11.00000 0.03583 0.04949 = 0.05067 0.01023 0.00384 0.00055 C10 1 0.854628 -0.350621 0.864011 11.00000 0.03954 0.04999 = 0.05052 0.00828 0.00022 0.00041 C11 1 0.997033 -0.275947 0.910080 11.00000 0.03918 0.06873 = 0.05921 0.00444 -0.00581 0.00588 AFIX 43 H11 2 1.133436 -0.348025 0.919950 11.00000 -1.20000 AFIX 0 C12 1 0.934877 -0.099445 0.939851 11.00000 0.04786 0.07659 = 0.05806 0.00103 -0.00293 0.00090 AFIX 43 H12 2 1.029133 -0.052683 0.969852 11.00000 -1.20000 AFIX 0 C13 1 0.501197 -0.318319 0.806169 11.00000 0.03875 0.05989 = 0.06201 0.00603 -0.00246 0.01091 AFIX 43 H13 2 0.360677 -0.250908 0.797636 11.00000 -1.20000 AFIX 0 C14 1 0.565727 -0.490236 0.775391 11.00000 0.04082 0.05650 = 0.05606 0.00547 -0.00153 0.00451 AFIX 43 H14 2 0.468309 -0.538483 0.746148 11.00000 -1.20000 AFIX 0 C15 1 0.778262 -0.597020 0.787033 11.00000 0.03906 0.04967 = 0.04985 0.00880 0.00706 0.00067 C16 1 0.917195 -0.529039 0.831043 11.00000 0.03282 0.05662 = 0.05642 0.01110 0.00274 0.00277 AFIX 43 H16 2 1.055118 -0.600875 0.839550 11.00000 -1.20000 AFIX 0 C17 1 0.842569 -0.778580 0.748119 11.00000 0.04879 0.04566 = 0.06034 0.00750 0.00624 0.00078 AFIX 13 H17 2 0.705694 -0.869030 0.741402 11.00000 -1.20000 AFIX 0 C18 1 0.907569 -0.677286 0.692305 11.00000 0.03772 0.05070 = 0.05611 0.00189 0.00945 0.00161 C19 1 1.041386 -0.918647 0.769891 11.00000 0.05536 0.05995 = 0.07745 0.01287 0.00620 0.00682 AFIX 137 H19A 2 1.184772 -0.841944 0.767444 11.00000 -1.50000 H19B 2 1.047519 -1.046437 0.747662 11.00000 -1.50000 H19C 2 1.017442 -0.956026 0.808318 11.00000 -1.50000 AFIX 0 N1 3 0.220239 -0.272694 0.551248 11.00000 0.03664 0.05226 = 0.04910 -0.00216 0.00417 -0.00169 AFIX 23 H1C 2 0.107526 -0.370920 0.546022 11.00000 -1.20000 H1D 2 0.264227 -0.229203 0.517242 11.00000 -1.20000 AFIX 0 O1 4 0.800075 -0.497145 0.559491 11.00000 0.03511 0.05921 = 0.05685 0.00568 0.00412 0.00436 O2 4 0.639014 -0.238653 0.506772 11.00000 0.05120 0.07338 = 0.05569 0.01528 0.01492 0.00763 O3 4 0.692881 0.189187 0.957583 11.00000 0.07154 0.05976 = 0.06606 -0.00627 -0.00136 0.00700 O4 4 0.752453 -0.712628 0.652138 11.00000 0.05860 0.07277 = 0.06168 0.01386 -0.00501 -0.01972 AFIX 143 H4E 2 0.800252 -0.667692 0.622370 11.00000 -1.30000 AFIX 0 O5 4 1.081431 -0.578944 0.685154 11.00000 0.06060 0.13623 = 0.07064 0.02927 -0.00155 -0.04287 HKLF 4 REM nprx-dprol in P2(1) REM R1 = 0.0642 for 2141 Fo > 4sig(Fo) and 0.0658 for all 2233 data REM 248 parameters refined using 1 restraints END WGHT 0.0904 0.5582 REM Highest difference peak 0.234, deepest hole -0.241, 1-sigma level 0.062 Q1 1 1.1217 -0.5828 0.7830 11.00000 0.05 0.23 Q2 1 0.3763 -0.0455 0.9425 11.00000 0.05 0.23 Q3 1 0.2999 -0.2014 0.5058 11.00000 0.05 0.22 Q4 1 0.4350 -0.6702 0.6880 11.00000 0.05 0.21 Q5 1 1.0491 0.1345 0.9437 11.00000 0.05 0.21 Q6 1 0.4049 -0.6810 0.6518 11.00000 0.05 0.21 Q7 1 0.7783 -0.2350 0.6381 11.00000 0.05 0.20 Q8 1 0.6525 0.6812 0.9335 11.00000 0.05 0.20 Q9 1 0.5711 -0.4637 0.4805 11.00000 0.05 0.19 Q10 1 0.8452 0.2127 0.9386 11.00000 0.05 0.19 ; data_shelxl _database_code_depnum_ccdc_archive 'CCDC 914593' #TrackingRef '15950_web_deposit_cif_file_0_AnaelleTilborg_1354811900.bn_at_DLproRSnprx.cif' _audit_update_record ; 2012-12-06 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Pyrrolidinium-2-carboxylate-2-(6-methoxynaphthalen-2-yl)propanoic acid hydrate(1:1:1) ; _chemical_name_common ; DL-Prolinium cocrystal of RS-Naproxen ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 O3, C5 H9 N O2, H2 O' _chemical_formula_sum 'C19 H25 N O6' _chemical_formula_weight 363.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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' '-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 6.1054(2) _cell_length_b 12.4750(5) _cell_length_c 49.1664(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3744.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2695 _cell_measurement_theta_min 2.6938 _cell_measurement_theta_max 67.4044 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.795 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7416 _exptl_absorpt_correction_T_max 0.9765 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3712 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10064 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -54 _diffrn_reflns_limit_l_max 58 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 66.58 _reflns_number_total 3307 _reflns_number_gt 2495 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution Sir2011 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0795P)^2^+0.9701P] 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 3307 _refine_ls_number_parameters 247 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1566 _refine_ls_wR_factor_gt 0.1415 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4567(3) 0.13956(15) 0.71657(4) 0.0442(4) Uani 1 1 d . . . C2 C 0.5976(4) 0.21574(16) 0.70031(4) 0.0474(5) Uani 1 1 d . . . H2 H 0.5013 0.2628 0.6898 0.057 Uiso 1 1 calc R . . C3 C 0.7636(5) 0.1661(2) 0.68107(5) 0.0704(7) Uani 1 1 d . . . H3A H 0.8311 0.1032 0.6891 0.084 Uiso 1 1 calc R . . H3B H 0.6956 0.1460 0.6640 0.084 Uiso 1 1 calc R . . C4 C 0.9293(5) 0.2543(3) 0.67699(6) 0.0784(8) Uani 1 1 d . . . H4A H 1.0707 0.2248 0.6720 0.094 Uiso 1 1 calc R . . H4B H 0.8819 0.3030 0.6628 0.094 Uiso 1 1 calc R . . C11 C 1.2263(5) -0.05251(18) 0.64743(5) 0.0607(6) Uani 1 1 d . . . C12 C 1.2272(5) -0.08773(19) 0.61768(5) 0.0659(6) Uani 1 1 d . . . H12 H 1.3796 -0.0980 0.6120 0.079 Uiso 1 1 calc R . . C13 C 1.1077(6) -0.1911(2) 0.61385(7) 0.0923(10) Uani 1 1 d . . . H13A H 1.1748 -0.2457 0.6248 0.139 Uiso 1 1 calc R . . H13B H 1.1139 -0.2117 0.5951 0.139 Uiso 1 1 calc R . . H13C H 0.9576 -0.1823 0.6192 0.139 Uiso 1 1 calc R . . C14 C 1.1287(4) 0.00253(19) 0.60077(4) 0.0615(6) Uani 1 1 d . . . C15 C 1.2350(4) 0.04217(19) 0.57855(4) 0.0608(6) Uani 1 1 d . . . H15 H 1.3666 0.0111 0.5732 0.073 Uiso 1 1 calc R . . C16 C 1.1508(4) 0.12926(19) 0.56332(4) 0.0558(5) Uani 1 1 d . . . C17 C 0.9510(4) 0.1770(2) 0.57111(4) 0.0578(6) Uani 1 1 d . . . C5 C 0.9424(5) 0.3109(2) 0.70363(5) 0.0729(7) Uani 1 1 d . . . H5A H 0.9538 0.3877 0.7009 0.087 Uiso 1 1 calc R . . H5B H 1.0693 0.2868 0.7138 0.087 Uiso 1 1 calc R . . C18 C 0.8380(5) 0.1310(2) 0.59345(5) 0.0734(7) Uani 1 1 d . . . H18 H 0.7024 0.1584 0.5986 0.088 Uiso 1 1 calc R . . C19 C 0.9258(5) 0.0472(2) 0.60752(5) 0.0725(7) Uani 1 1 d . . . H19 H 0.8482 0.0189 0.6221 0.087 Uiso 1 1 calc R . . C20 C 1.2642(5) 0.1731(2) 0.54088(5) 0.0681(7) Uani 1 1 d . . . H20 H 1.3939 0.1413 0.5351 0.082 Uiso 1 1 calc R . . C21 C 1.1877(5) 0.2604(2) 0.52768(5) 0.0691(7) Uani 1 1 d . . . H21 H 1.2654 0.2882 0.5130 0.083 Uiso 1 1 calc R . . C22 C 0.9905(4) 0.3100(2) 0.53598(5) 0.0612(6) Uani 1 1 d . . . C23 C 0.8734(4) 0.2685(2) 0.55690(5) 0.0629(6) Uani 1 1 d . . . H23 H 0.7417 0.3001 0.5620 0.076 Uiso 1 1 calc R . . C24 C 0.7376(6) 0.4513(2) 0.52770(7) 0.0881(9) Uani 1 1 d . . . H24A H 0.7194 0.5127 0.5162 0.132 Uiso 1 1 calc R . . H24B H 0.7399 0.4739 0.5464 0.132 Uiso 1 1 calc R . . H24C H 0.6182 0.4025 0.5249 0.132 Uiso 1 1 calc R . . N1 N 0.7356(3) 0.28386(13) 0.71857(3) 0.0479(4) Uani 1 1 d . . . H1A H 0.7671 0.2481 0.7340 0.057 Uiso 1 1 calc R . . H1B H 0.6632 0.3442 0.7230 0.057 Uiso 1 1 calc R . . O1 O 0.4462(2) 0.15167(12) 0.74149(3) 0.0531(4) Uani 1 1 d . . . O2 O 0.3569(3) 0.06845(13) 0.70335(3) 0.0649(5) Uani 1 1 d . . . O5 O 1.3732(4) 0.01983(17) 0.65248(4) 0.0833(6) Uani 1 1 d D . . O6 O 1.1038(4) -0.08708(16) 0.66441(4) 0.0859(6) Uani 1 1 d . . . O7 O 0.9379(3) 0.39940(15) 0.52129(4) 0.0751(5) Uani 1 1 d . . . O8 O 0.4675(4) 0.45261(15) 0.73241(5) 0.0806(6) Uani 1 1 d D . . H5C H 1.362(7) 0.032(3) 0.6696(4) 0.128(14) Uiso 1 1 d D . . H8A H 0.533(5) 0.503(2) 0.7405(6) 0.112(13) Uiso 1 1 d D . . H8B H 0.389(5) 0.482(3) 0.7201(6) 0.115(13) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0441(10) 0.0409(10) 0.0476(10) -0.0001(8) -0.0006(9) 0.0030(9) C2 0.0518(11) 0.0449(10) 0.0456(10) 0.0025(9) -0.0021(9) -0.0011(9) C3 0.0738(15) 0.0747(15) 0.0628(13) -0.0161(12) 0.0204(13) -0.0147(14) C4 0.0704(16) 0.094(2) 0.0709(15) -0.0025(15) 0.0199(13) -0.0181(16) C11 0.0793(15) 0.0470(11) 0.0558(12) 0.0049(10) -0.0074(12) -0.0034(12) C12 0.0804(16) 0.0554(12) 0.0618(12) -0.0065(11) -0.0066(12) 0.0047(13) C13 0.116(2) 0.0673(17) 0.094(2) -0.0210(16) -0.021(2) 0.0027(17) C14 0.0758(15) 0.0588(13) 0.0498(11) -0.0102(10) -0.0022(11) 0.0037(12) C15 0.0652(13) 0.0625(13) 0.0547(11) -0.0113(11) -0.0004(11) 0.0058(12) C16 0.0603(13) 0.0604(12) 0.0466(10) -0.0090(10) -0.0012(10) 0.0017(11) C17 0.0601(13) 0.0631(13) 0.0502(11) -0.0053(10) 0.0010(10) -0.0017(12) C5 0.0679(15) 0.0766(17) 0.0741(15) -0.0039(13) 0.0156(13) -0.0229(14) C18 0.0699(15) 0.0834(17) 0.0671(14) 0.0011(14) 0.0151(13) 0.0121(15) C19 0.0864(18) 0.0741(16) 0.0571(13) 0.0072(12) 0.0123(13) -0.0010(15) C20 0.0651(14) 0.0796(16) 0.0596(12) -0.0024(13) 0.0094(12) 0.0061(14) C21 0.0730(16) 0.0784(16) 0.0558(12) 0.0055(12) 0.0068(12) -0.0036(14) C22 0.0702(15) 0.0607(13) 0.0527(11) -0.0021(11) -0.0082(11) -0.0029(12) C23 0.0607(13) 0.0697(14) 0.0583(12) -0.0023(11) 0.0017(11) 0.0068(12) C24 0.090(2) 0.0785(18) 0.0954(19) 0.0085(16) -0.0160(18) 0.0154(17) N1 0.0537(9) 0.0395(8) 0.0505(8) 0.0004(7) 0.0026(8) -0.0033(8) O1 0.0551(8) 0.0570(8) 0.0472(7) 0.0007(6) 0.0054(6) -0.0046(7) O2 0.0771(11) 0.0601(9) 0.0575(8) -0.0071(7) 0.0039(8) -0.0242(9) O5 0.1108(15) 0.0810(12) 0.0581(10) -0.0061(9) 0.0012(10) -0.0360(12) O6 0.1117(15) 0.0786(12) 0.0674(10) 0.0022(10) 0.0037(11) -0.0315(12) O7 0.0855(12) 0.0731(11) 0.0666(10) 0.0106(9) -0.0057(9) 0.0039(10) O8 0.0918(14) 0.0581(10) 0.0919(13) -0.0220(10) -0.0298(12) 0.0237(10) _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 O1 1.236(2) . ? C1 O2 1.257(3) . ? C1 C2 1.511(3) . ? C2 N1 1.496(3) . ? C2 C3 1.519(3) . ? C2 H2 0.9800 . ? C3 C4 1.509(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.490(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C11 O6 1.201(3) . ? C11 O5 1.296(3) . ? C11 C12 1.527(3) . ? C12 C13 1.493(4) . ? C12 C14 1.523(4) . ? C12 H12 0.9800 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.364(3) . ? C14 C19 1.398(4) . ? C15 C16 1.416(3) . ? C15 H15 0.9300 . ? C16 C17 1.410(3) . ? C16 C20 1.413(3) . ? C17 C18 1.418(4) . ? C17 C23 1.420(4) . ? C5 N1 1.499(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C18 C19 1.363(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.351(4) . ? C20 H20 0.9300 . ? C21 C22 1.414(4) . ? C21 H21 0.9300 . ? C22 C23 1.356(4) . ? C22 O7 1.367(3) . ? C23 H23 0.9300 . ? C24 O7 1.419(4) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? O5 H5C 0.856(19) . ? O8 H8A 0.845(18) . ? O8 H8B 0.852(17) . ? 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 C1 O2 125.0(2) . . ? O1 C1 C2 118.49(18) . . ? O2 C1 C2 116.50(18) . . ? N1 C2 C1 111.13(16) . . ? N1 C2 C3 103.30(18) . . ? C1 C2 C3 116.93(18) . . ? N1 C2 H2 108.4 . . ? C1 C2 H2 108.4 . . ? C3 C2 H2 108.4 . . ? C4 C3 C2 103.4(2) . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3B 111.1 . . ? C2 C3 H3B 111.1 . . ? H3A C3 H3B 109.0 . . ? C5 C4 C3 105.4(2) . . ? C5 C4 H4A 110.7 . . ? C3 C4 H4A 110.7 . . ? C5 C4 H4B 110.7 . . ? C3 C4 H4B 110.7 . . ? H4A C4 H4B 108.8 . . ? O6 C11 O5 123.2(2) . . ? O6 C11 C12 124.4(2) . . ? O5 C11 C12 112.4(2) . . ? C13 C12 C14 112.1(2) . . ? C13 C12 C11 111.6(2) . . ? C14 C12 C11 107.97(19) . . ? C13 C12 H12 108.4 . . ? C14 C12 H12 108.4 . . ? C11 C12 H12 108.4 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 117.8(2) . . ? C15 C14 C12 121.2(2) . . ? C19 C14 C12 121.0(2) . . ? C14 C15 C16 121.9(2) . . ? C14 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C17 C16 C20 118.2(2) . . ? C17 C16 C15 119.6(2) . . ? C20 C16 C15 122.1(2) . . ? C16 C17 C18 117.4(2) . . ? C16 C17 C23 119.6(2) . . ? C18 C17 C23 122.9(2) . . ? C4 C5 N1 106.2(2) . . ? C4 C5 H5A 110.5 . . ? N1 C5 H5A 110.5 . . ? C4 C5 H5B 110.5 . . ? N1 C5 H5B 110.5 . . ? H5A C5 H5B 108.7 . . ? C19 C18 C17 120.7(3) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C14 122.3(2) . . ? C18 C19 H19 118.9 . . ? C14 C19 H19 118.9 . . ? C21 C20 C16 121.2(2) . . ? C21 C20 H20 119.4 . . ? C16 C20 H20 119.4 . . ? C20 C21 C22 120.6(2) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C23 C22 O7 126.1(2) . . ? C23 C22 C21 120.1(2) . . ? O7 C22 C21 113.9(2) . . ? C22 C23 C17 120.3(2) . . ? C22 C23 H23 119.9 . . ? C17 C23 H23 119.9 . . ? O7 C24 H24A 109.5 . . ? O7 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O7 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C2 N1 C5 107.93(17) . . ? C2 N1 H1A 110.1 . . ? C5 N1 H1A 110.1 . . ? C2 N1 H1B 110.1 . . ? C5 N1 H1B 110.1 . . ? H1A N1 H1B 108.4 . . ? C11 O5 H5C 105(3) . . ? C22 O7 C24 117.2(2) . . ? H8A O8 H8B 107(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 O1 C1 C2 N1 10.1(3) . . . . ? O2 C1 C2 N1 -170.42(18) . . . . ? O1 C1 C2 C3 128.3(2) . . . . ? O2 C1 C2 C3 -52.2(3) . . . . ? N1 C2 C3 C4 -36.0(2) . . . . ? C1 C2 C3 C4 -158.4(2) . . . . ? C2 C3 C4 C5 35.2(3) . . . . ? O6 C11 C12 C13 -17.0(4) . . . . ? O5 C11 C12 C13 163.2(3) . . . . ? O6 C11 C12 C14 106.6(3) . . . . ? O5 C11 C12 C14 -73.2(3) . . . . ? C13 C12 C14 C15 -108.4(3) . . . . ? C11 C12 C14 C15 128.4(3) . . . . ? C13 C12 C14 C19 71.5(3) . . . . ? C11 C12 C14 C19 -51.8(3) . . . . ? C19 C14 C15 C16 3.1(4) . . . . ? C12 C14 C15 C16 -177.1(2) . . . . ? C14 C15 C16 C17 -0.2(3) . . . . ? C14 C15 C16 C20 177.6(2) . . . . ? C20 C16 C17 C18 179.2(2) . . . . ? C15 C16 C17 C18 -2.9(3) . . . . ? C20 C16 C17 C23 -1.8(3) . . . . ? C15 C16 C17 C23 176.1(2) . . . . ? C3 C4 C5 N1 -20.4(3) . . . . ? C16 C17 C18 C19 3.1(4) . . . . ? C23 C17 C18 C19 -175.8(3) . . . . ? C17 C18 C19 C14 -0.1(4) . . . . ? C15 C14 C19 C18 -3.0(4) . . . . ? C12 C14 C19 C18 177.2(2) . . . . ? C17 C16 C20 C21 2.0(4) . . . . ? C15 C16 C20 C21 -175.8(2) . . . . ? C16 C20 C21 C22 -0.3(4) . . . . ? C20 C21 C22 C23 -1.7(4) . . . . ? C20 C21 C22 O7 177.9(2) . . . . ? O7 C22 C23 C17 -177.7(2) . . . . ? C21 C22 C23 C17 1.8(4) . . . . ? C16 C17 C23 C22 0.0(4) . . . . ? C18 C17 C23 C22 178.8(2) . . . . ? C1 C2 N1 C5 150.11(19) . . . . ? C3 C2 N1 C5 23.9(2) . . . . ? C4 C5 N1 C2 -2.4(3) . . . . ? C23 C22 O7 C24 -2.9(4) . . . . ? C21 C22 O7 C24 177.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 66.58 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.420 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.039 _iucr_refine_instructions_details ; TITL bn_AT-dlpro-rsnprxCu in Pbca CELL 1.54184 6.1054 12.4750 49.1664 90.000 90.000 90.000 ZERR 8.00 0.0002 0.0005 0.0013 0.000 0.000 0.000 LATT 1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 152 200 8 48 MERG 2 OMIT 6 6 23 OMIT 4 1 1 OMIT 1 1 27 SHEL 99 0.84 DANG 1.36 0.001 H8a H8b DFIX 0.82 O8 H8A O8 H8B O5 H5c FMAP 2 PLAN 10 SIZE 0.03 0.05 0.40 ACTA BOND $H CONF L.S. 10 TEMP 20.00 WGHT 0.079500 0.970100 FVAR 4.58041 C1 1 0.456650 0.139555 0.716568 11.00000 0.04406 0.04093 = 0.04762 -0.00010 -0.00061 0.00298 C2 1 0.597612 0.215743 0.700310 11.00000 0.05180 0.04486 = 0.04556 0.00251 -0.00214 -0.00114 AFIX 13 H2 2 0.501266 0.262834 0.689756 11.00000 -1.20000 AFIX 0 C3 1 0.763587 0.166053 0.681067 11.00000 0.07376 0.07467 = 0.06277 -0.01606 0.02042 -0.01473 AFIX 23 H3A 2 0.831053 0.103185 0.689103 11.00000 -1.20000 H3B 2 0.695643 0.146024 0.663972 11.00000 -1.20000 AFIX 0 C4 1 0.929291 0.254342 0.676988 11.00000 0.07040 0.09393 = 0.07090 -0.00254 0.01986 -0.01810 AFIX 23 H4A 2 1.070724 0.224805 0.672027 11.00000 -1.20000 H4B 2 0.881943 0.303031 0.662773 11.00000 -1.20000 AFIX 0 C11 1 1.226316 -0.052506 0.647429 11.00000 0.07929 0.04702 = 0.05584 0.00494 -0.00735 -0.00344 C12 1 1.227187 -0.087735 0.617678 11.00000 0.08042 0.05537 = 0.06182 -0.00650 -0.00657 0.00473 AFIX 13 H12 2 1.379550 -0.097981 0.611972 11.00000 -1.20000 AFIX 0 C13 1 1.107706 -0.191099 0.613855 11.00000 0.11611 0.06730 = 0.09362 -0.02104 -0.02091 0.00272 AFIX 33 H13A 2 1.174778 -0.245675 0.624815 11.00000 -1.50000 H13B 2 1.113922 -0.211728 0.595060 11.00000 -1.50000 H13C 2 0.957611 -0.182339 0.619232 11.00000 -1.50000 AFIX 0 C14 1 1.128658 0.002529 0.600771 11.00000 0.07584 0.05882 = 0.04982 -0.01022 -0.00217 0.00370 C15 1 1.234960 0.042168 0.578546 11.00000 0.06517 0.06246 = 0.05472 -0.01132 -0.00042 0.00579 AFIX 43 H15 2 1.366632 0.011083 0.573232 11.00000 -1.20000 AFIX 0 C16 1 1.150754 0.129259 0.563322 11.00000 0.06028 0.06043 = 0.04665 -0.00902 -0.00124 0.00168 C17 1 0.951000 0.176971 0.571106 11.00000 0.06012 0.06312 = 0.05023 -0.00527 0.00104 -0.00175 C5 1 0.942423 0.310891 0.703633 11.00000 0.06793 0.07663 = 0.07413 -0.00387 0.01564 -0.02286 AFIX 23 H5A 2 0.953786 0.387700 0.700908 11.00000 -1.20000 H5B 2 1.069298 0.286809 0.713815 11.00000 -1.20000 AFIX 0 C18 1 0.837978 0.131043 0.593453 11.00000 0.06986 0.08339 = 0.06708 0.00109 0.01510 0.01209 AFIX 43 H18 2 0.702397 0.158395 0.598568 11.00000 -1.20000 AFIX 0 C19 1 0.925848 0.047247 0.607520 11.00000 0.08637 0.07410 = 0.05714 0.00717 0.01235 -0.00101 AFIX 43 H19 2 0.848182 0.018853 0.622110 11.00000 -1.20000 AFIX 0 C20 1 1.264236 0.173132 0.540878 11.00000 0.06510 0.07955 = 0.05955 -0.00239 0.00942 0.00609 AFIX 43 H20 2 1.393896 0.141344 0.535090 11.00000 -1.20000 AFIX 0 C21 1 1.187712 0.260439 0.527678 11.00000 0.07301 0.07842 = 0.05584 0.00550 0.00678 -0.00360 AFIX 43 H21 2 1.265427 0.288161 0.513009 11.00000 -1.20000 AFIX 0 C22 1 0.990520 0.309991 0.535979 11.00000 0.07018 0.06070 = 0.05267 -0.00212 -0.00817 -0.00292 C23 1 0.873430 0.268496 0.556904 11.00000 0.06072 0.06975 = 0.05835 -0.00232 0.00170 0.00684 AFIX 43 H23 2 0.741691 0.300125 0.561980 11.00000 -1.20000 AFIX 0 C24 1 0.737644 0.451329 0.527695 11.00000 0.09047 0.07852 = 0.09539 0.00848 -0.01604 0.01540 AFIX 33 H24A 2 0.719367 0.512742 0.516150 11.00000 -1.50000 H24B 2 0.739905 0.473859 0.546363 11.00000 -1.50000 H24C 2 0.618180 0.402519 0.524903 11.00000 -1.50000 AFIX 0 N1 3 0.735599 0.283864 0.718574 11.00000 0.05370 0.03946 = 0.05045 0.00041 0.00256 -0.00329 AFIX 23 H1A 2 0.767100 0.248095 0.733982 11.00000 -1.20000 H1B 2 0.663202 0.344237 0.723001 11.00000 -1.20000 AFIX 0 O1 4 0.446154 0.151668 0.741490 11.00000 0.05514 0.05703 = 0.04721 0.00068 0.00535 -0.00461 O2 4 0.356948 0.068449 0.703346 11.00000 0.07707 0.06007 = 0.05746 -0.00711 0.00391 -0.02418 O5 4 1.373241 0.019834 0.652476 11.00000 0.11077 0.08096 = 0.05809 -0.00606 0.00120 -0.03602 O6 4 1.103786 -0.087084 0.664408 11.00000 0.11169 0.07855 = 0.06743 0.00221 0.00375 -0.03152 O7 4 0.937908 0.399397 0.521293 11.00000 0.08552 0.07308 = 0.06659 0.01064 -0.00571 0.00387 O8 4 0.467524 0.452615 0.732409 11.00000 0.09176 0.05806 = 0.09187 -0.02198 -0.02983 0.02373 H5C 2 1.361728 0.031642 0.669557 11.00000 0.12761 H8A 2 0.533004 0.503009 0.740524 11.00000 0.11180 H8B 2 0.388886 0.481680 0.720140 11.00000 0.11536 HKLF 4 REM bn_AT-dlpro-rsnprxCu in Pbca REM R1 = 0.0524 for 2495 Fo > 4sig(Fo) and 0.0717 for all 3307 data REM 247 parameters refined using 4 restraints END WGHT 0.0802 0.9924 REM Highest difference peak 0.420, deepest hole -0.233, 1-sigma level 0.039 Q1 1 1.3020 -0.1629 0.6086 11.00000 0.05 0.42 Q2 1 1.0661 -0.0920 0.6193 11.00000 0.05 0.36 Q3 1 0.5729 0.4865 0.7188 11.00000 0.05 0.23 Q4 1 1.0794 -0.0514 0.6472 11.00000 0.05 0.18 Q5 1 0.9556 -0.0883 0.6674 11.00000 0.05 0.15 Q6 1 0.3868 0.2109 0.7355 11.00000 0.05 0.15 Q7 1 0.7133 0.1662 0.7009 11.00000 0.05 0.14 Q8 1 1.2211 0.0407 0.6487 11.00000 0.05 0.13 Q9 1 1.1790 0.0998 0.5644 11.00000 0.05 0.13 Q10 1 1.1117 0.0252 0.5802 11.00000 0.05 0.13 ; data_test _database_code_depnum_ccdc_archive 'CCDC 915284' #TrackingRef '16082_web_deposit_cif_file_0_AnaelleTilborg_1355240225.bn_at_Lpro-RSnprx.cif' _audit_update_record ; 2012-12-11 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Pyrrolidinium-2-carboxylate-2-(6-methoxynaphthalen-2-yl)propanoic acid hydrate(1:1:1) ; _chemical_name_common ; L-Prolinium cocrystal of RS-Naproxen ; _chemical_melting_point ? _chemical_formula_moiety C14H14O3,C5H9NO2,H2O _chemical_formula_sum 'C19 H25 N1 O6' _chemical_absolute_configuration rm _chemical_formula_weight 363.40 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.122(2) _cell_length_b 5.8980(10) _cell_length_c 24.075(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.560(5) _cell_angle_gamma 90.00 _cell_volume 1854.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3521 _diffrn_reflns_theta_min 3.3054 _diffrn_reflns_theta_max 29.1253 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9623 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3712 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10708 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _reflns_number_total 5930 _reflns_number_gt 5138 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0686P)^2^+0.5674P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 5930 _refine_ls_number_parameters 530 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 0.832 _refine_ls_restrained_S_all 0.837 _refine_ls_shift/su_max 0.005 _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 0.33377(17) 0.7428(5) 0.06475(10) 0.0430(6) Uani 1 1 d . . . C2 C 0.36653(16) 0.5125(4) 0.08711(9) 0.0404(5) Uani 1 1 d . . . C3 C 0.3923(2) 0.4873(6) 0.14951(10) 0.0661(8) Uani 1 1 d . . . H3A H 0.3309 0.4649 0.1683 0.079 Uiso 1 1 calc R . . H3B H 0.4285 0.6196 0.1651 0.079 Uiso 1 1 calc R . . C4 C 0.4604(2) 0.2780(6) 0.15460(12) 0.0743(10) Uani 1 1 d . . . H4A H 0.5074 0.2854 0.1882 0.089 Uiso 1 1 calc R . . H4B H 0.4194 0.1416 0.1559 0.089 Uiso 1 1 calc R . . C5 C 0.5175(2) 0.2784(6) 0.10418(11) 0.0599(8) Uani 1 1 d . . . H5A H 0.5203 0.1266 0.0889 0.072 Uiso 1 1 calc R . . H5B H 0.5869 0.3323 0.1134 0.072 Uiso 1 1 calc R . . C6 C 0.16598(16) 0.5670(4) -0.06381(9) 0.0359(5) Uani 1 1 d . . . C7 C 0.09755(16) 0.7284(4) -0.09930(9) 0.0372(5) Uani 1 1 d . . . H7 H 0.0573 0.6386 -0.1278 0.045 Uiso 1 1 calc R . . C8 C 0.1459(2) 0.9234(5) -0.12861(11) 0.0530(6) Uani 1 1 d . . . H8A H 0.1972 1.0003 -0.1036 0.064 Uiso 1 1 calc R . . H8B H 0.1772 0.8708 -0.1611 0.064 Uiso 1 1 calc R . . C9 C 0.0552(2) 1.0771(5) -0.14513(11) 0.0571(7) Uani 1 1 d . . . H9A H 0.0773 1.2334 -0.1477 0.068 Uiso 1 1 calc R . . H9B H 0.0208 1.0317 -0.1809 0.068 Uiso 1 1 calc R . . C10 C -0.01519(19) 1.0503(5) -0.09934(11) 0.0547(7) Uani 1 1 d . . . H10A H -0.0136 1.1850 -0.0762 0.066 Uiso 1 1 calc R . . H10B H -0.0851 1.0243 -0.1151 0.066 Uiso 1 1 calc R . . C14 C 0.22597(19) 0.0542(6) 0.29649(10) 0.0562(7) Uani 1 1 d D . . C12 C 0.1326(3) -0.0562(9) 0.26190(16) 0.0475(10) Uani 0.80 1 d PD A 1 H12 H 0.1262 -0.2139 0.2739 0.057 Uiso 0.80 1 calc PR A 1 C11 C 0.1524(3) -0.0534(7) 0.20092(15) 0.0418(9) Uani 0.80 1 d PD A 1 O5 O 0.2149(3) -0.2104(5) 0.18848(16) 0.0643(10) Uani 0.80 1 d PD A 1 H5 H 0.2225 -0.2037 0.1551 0.096 Uiso 0.80 1 calc PR A 1 O6 O 0.1190(6) 0.0920(19) 0.1684(3) 0.085(3) Uani 0.80 1 d PD A 1 C13 C 0.0352(3) 0.0708(9) 0.27179(18) 0.0667(11) Uani 0.80 1 d PD A 1 H13A H 0.0255 0.0666 0.3108 0.100 Uiso 0.80 1 calc PR A 1 H13B H -0.0222 0.0005 0.2508 0.100 Uiso 0.80 1 calc PR A 1 H13C H 0.0408 0.2255 0.2601 0.100 Uiso 0.80 1 calc PR A 1 C12' C 0.1378(12) 0.069(4) 0.2607(6) 0.074(7) Uani 0.20 1 d PD A 2 H12' H 0.1080 0.2191 0.2654 0.089 Uiso 0.20 1 calc PR A 2 C11' C 0.1584(12) 0.045(3) 0.1990(7) 0.0418(9) Uani 0.20 1 d PD A 2 O5' O 0.2247(15) -0.122(3) 0.1938(8) 0.0643(10) Uani 0.20 1 d PD A 2 H5' H 0.2344 -0.1369 0.1609 0.096 Uiso 0.20 1 calc PR A 2 O6' O 0.096(2) 0.085(7) 0.1611(11) 0.070(7) Uani 0.20 1 d PD A 2 C13' C 0.0671(17) -0.099(5) 0.2799(8) 0.097(7) Uani 0.20 1 d PD A 2 H13D H 0.0035 -0.0935 0.2566 0.146 Uiso 0.20 1 calc PR A 2 H13E H 0.0550 -0.0665 0.3178 0.146 Uiso 0.20 1 calc PR A 2 H13F H 0.0964 -0.2477 0.2780 0.146 Uiso 0.20 1 calc PR A 2 C15 C 0.2672(2) 0.2636(7) 0.28241(11) 0.0660(9) Uani 1 1 d . A . H15 H 0.2341 0.3468 0.2532 0.079 Uiso 1 1 calc R . . C16 C 0.3546(2) 0.3493(6) 0.31025(11) 0.0633(8) Uani 1 1 d . . . H16 H 0.3806 0.4870 0.2992 0.076 Uiso 1 1 calc R A . C17 C 0.4059(2) 0.2303(5) 0.35569(10) 0.0492(6) Uani 1 1 d . A . C18 C 0.36158(19) 0.0268(5) 0.37170(9) 0.0483(6) Uani 1 1 d . . . C19 C 0.2720(2) -0.0573(6) 0.34119(10) 0.0566(7) Uani 1 1 d . A . H19 H 0.2440 -0.1931 0.3522 0.068 Uiso 1 1 calc R . . C20 C 0.4997(2) 0.3050(5) 0.38397(10) 0.0539(7) Uani 1 1 d . . . H20 H 0.5291 0.4398 0.3734 0.065 Uiso 1 1 calc R A . C21 C 0.5468(2) 0.1805(5) 0.42638(10) 0.0528(7) Uani 1 1 d . A . C22 C 0.5005(2) -0.0177(6) 0.44390(11) 0.0586(8) Uani 1 1 d . . . H22 H 0.5316 -0.0984 0.4741 0.070 Uiso 1 1 calc R A . C23 C 0.4110(2) -0.0936(6) 0.41747(11) 0.0599(7) Uani 1 1 d . A . H23 H 0.3818 -0.2262 0.4296 0.072 Uiso 1 1 calc R . . C24 C 0.6881(2) 0.4344(7) 0.44193(14) 0.0757(9) Uani 1 1 d . A . H24A H 0.7513 0.4491 0.4652 0.114 Uiso 1 1 calc R . . H24B H 0.6446 0.5611 0.4480 0.114 Uiso 1 1 calc R . . H24C H 0.7017 0.4309 0.4035 0.114 Uiso 1 1 calc R . . C28 C -0.2648(2) -0.2002(6) 0.30039(11) 0.0578(7) Uani 1 1 d D . . C26 C -0.3578(3) -0.0904(7) 0.26630(14) 0.0487(8) Uani 0.80 1 d PD B 1 H26 H -0.3617 0.0697 0.2768 0.058 Uiso 0.80 1 calc PR B 1 C25 C -0.3427(10) -0.1065(18) 0.2049(2) 0.0572(16) Uani 0.80 1 d PD B 1 O8 O -0.2730(2) 0.0305(7) 0.19025(14) 0.0646(9) Uani 0.80 1 d PD B 1 H8 H -0.2657 0.0121 0.1571 0.097 Uiso 0.80 1 calc PR B 1 O9 O -0.3928(2) -0.2318(7) 0.17245(13) 0.0817(10) Uani 0.80 1 d PD B 1 C27 C -0.4552(3) -0.2088(9) 0.2788(2) 0.0635(12) Uani 0.80 1 d PD B 1 H27A H -0.4645 -0.1911 0.3176 0.095 Uiso 0.80 1 calc PR B 1 H27B H -0.4505 -0.3671 0.2701 0.095 Uiso 0.80 1 calc PR B 1 H27C H -0.5124 -0.1433 0.2565 0.095 Uiso 0.80 1 calc PR B 1 C26' C -0.3557(11) -0.197(3) 0.2665(6) 0.0487(8) Uani 0.20 1 d PD B 2 H26' H -0.3802 -0.3535 0.2614 0.058 Uiso 0.20 1 calc PR B 2 C25' C -0.330(5) -0.107(7) 0.2102(10) 0.0572(16) Uani 0.20 1 d PD B 2 O8' O -0.277(3) 0.081(5) 0.2110(9) 0.211(17) Uani 0.20 1 d PD B 2 H8' H -0.2729 0.1244 0.1789 0.316 Uiso 0.20 1 calc PR B 2 O9' O -0.3442(11) -0.229(3) 0.1702(6) 0.0817(10) Uani 0.20 1 d PD B 2 C27' C -0.4358(17) -0.063(5) 0.2889(10) 0.104(9) Uani 0.20 1 d PD B 2 H27D H -0.4931 -0.0486 0.2611 0.156 Uiso 0.20 1 calc PR B 2 H27E H -0.4096 0.0850 0.2990 0.156 Uiso 0.20 1 calc PR B 2 H27F H -0.4574 -0.1368 0.3213 0.156 Uiso 0.20 1 calc PR B 2 C29 C -0.2244(2) -0.4096(7) 0.28623(12) 0.0671(9) Uani 1 1 d . B . H29 H -0.2576 -0.4913 0.2568 0.081 Uiso 1 1 calc R . . C30 C -0.1377(2) -0.4982(6) 0.31427(12) 0.0663(8) Uani 1 1 d . . . H30 H -0.1132 -0.6381 0.3037 0.080 Uiso 1 1 calc R B . C31 C -0.0850(2) -0.3788(5) 0.35908(11) 0.0526(7) Uani 1 1 d . B . C32 C -0.1283(2) -0.1723(5) 0.37532(10) 0.0520(6) Uani 1 1 d . . . C33 C -0.2181(2) -0.0909(6) 0.34508(11) 0.0580(7) Uani 1 1 d . B . H33 H -0.2464 0.0440 0.3564 0.070 Uiso 1 1 calc R . . C34 C 0.0092(2) -0.4539(6) 0.38705(11) 0.0579(7) Uani 1 1 d . . . H34 H 0.0380 -0.5894 0.3764 0.070 Uiso 1 1 calc R B . C35 C 0.0575(2) -0.3301(5) 0.42903(11) 0.0546(7) Uani 1 1 d . B . C36 C 0.0126(2) -0.1279(6) 0.44631(11) 0.0643(8) Uani 1 1 d . . . H36 H 0.0452 -0.0452 0.4758 0.077 Uiso 1 1 calc R B . C37 C -0.0767(2) -0.0534(6) 0.42061(11) 0.0638(8) Uani 1 1 d . B . H37 H -0.1052 0.0796 0.4329 0.077 Uiso 1 1 calc R . . C38 C 0.1979(3) -0.5853(7) 0.44422(15) 0.0815(10) Uani 1 1 d . B . H38A H 0.2616 -0.6012 0.4672 0.122 Uiso 1 1 calc R . . H38B H 0.2108 -0.5837 0.4056 0.122 Uiso 1 1 calc R . . H38C H 0.1539 -0.7104 0.4508 0.122 Uiso 1 1 calc R . . O1 O 0.37387(13) 0.8155(4) 0.02402(8) 0.0629(5) Uani 1 1 d . . . O2 O 0.26660(14) 0.8449(4) 0.08936(7) 0.0580(5) Uani 1 1 d . . . O3 O 0.23755(12) 0.4784(3) -0.08742(6) 0.0539(5) Uani 1 1 d . . . O4 O 0.14507(12) 0.5258(3) -0.01608(6) 0.0496(4) Uani 1 1 d . . . O7 O 0.63858(15) 0.2305(4) 0.45531(7) 0.0667(6) Uani 1 1 d . . . O10 O 0.15021(15) -0.3803(4) 0.45745(8) 0.0684(6) Uani 1 1 d . . . O11 O 0.37859(11) 0.2068(3) -0.03065(7) 0.0472(4) Uani 1 1 d . . . O12 O 0.13196(11) 1.0938(3) 0.02257(7) 0.0456(4) Uani 1 1 d . . . N1 N 0.46076(13) 0.4332(4) 0.06313(8) 0.0413(5) Uani 1 1 d . . . N2 N 0.02447(13) 0.8498(3) -0.06595(8) 0.0390(5) Uani 1 1 d . . . H2B H 0.0612 0.8947 -0.0351 0.042 Uiso 1 1 d . . . H11B H 0.3507 0.1014 -0.0134 0.111 Uiso 1 1 d . . . H11A H 0.3290 0.2773 -0.0490 0.074 Uiso 1 1 d . . . H2C H -0.0213 0.7510 -0.0573 0.063 Uiso 1 1 d . . . H2A H 0.3155 0.4070 0.0719 0.043 Uiso 1 1 d . . . H1A H 0.4399 0.3620 0.0322 0.040 Uiso 1 1 d . . . H1B H 0.5003 0.5487 0.0608 0.046 Uiso 1 1 d . . . H12A H 0.1782 1.0282 0.0440 0.071 Uiso 1 1 d . . . H12B H 0.1564 1.2175 0.0123 0.096 Uiso 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 0.0384(12) 0.0481(15) 0.0418(12) 0.0032(12) 0.0005(10) 0.0054(12) C2 0.0342(11) 0.0433(14) 0.0440(12) 0.0055(11) 0.0051(9) -0.0014(10) C3 0.0759(18) 0.078(2) 0.0461(14) 0.0160(15) 0.0128(13) 0.0274(17) C4 0.088(2) 0.075(2) 0.0607(17) 0.0220(17) 0.0110(16) 0.0296(19) C5 0.0569(16) 0.0548(19) 0.0674(17) 0.0133(15) 0.0024(13) 0.0136(15) C6 0.0369(11) 0.0327(13) 0.0376(12) -0.0029(10) 0.0018(9) -0.0032(10) C7 0.0407(11) 0.0351(12) 0.0357(11) -0.0040(10) 0.0031(9) -0.0014(10) C8 0.0644(15) 0.0466(15) 0.0506(14) 0.0112(13) 0.0187(12) 0.0042(13) C9 0.0774(18) 0.0403(16) 0.0525(15) 0.0097(12) 0.0015(13) 0.0001(14) C10 0.0546(14) 0.0500(18) 0.0591(15) 0.0147(14) 0.0025(12) 0.0157(14) C14 0.0522(15) 0.077(2) 0.0410(13) -0.0010(15) 0.0146(12) 0.0002(16) C12 0.043(2) 0.051(3) 0.050(2) -0.010(2) 0.0147(16) -0.012(2) C11 0.0347(13) 0.046(2) 0.0443(15) -0.004(2) 0.0002(11) -0.001(2) O5 0.0844(17) 0.061(3) 0.0486(13) -0.0038(19) 0.0134(12) 0.022(2) O6 0.068(4) 0.129(6) 0.054(3) -0.002(3) -0.010(2) 0.053(4) C13 0.051(2) 0.083(3) 0.069(3) -0.008(2) 0.0205(18) 0.008(2) C12' 0.075(12) 0.098(17) 0.051(10) -0.035(12) 0.013(8) -0.052(13) C11' 0.0347(13) 0.046(2) 0.0443(15) -0.004(2) 0.0002(11) -0.001(2) O5' 0.0844(17) 0.061(3) 0.0486(13) -0.0038(19) 0.0134(12) 0.022(2) O6' 0.040(9) 0.114(16) 0.054(10) 0.015(9) -0.009(7) 0.005(9) C13' 0.081(14) 0.14(2) 0.062(10) 0.004(14) -0.012(10) -0.028(16) C15 0.0644(17) 0.090(3) 0.0422(14) 0.0112(16) 0.0005(13) 0.0148(18) C16 0.0737(18) 0.061(2) 0.0554(16) 0.0143(15) 0.0060(14) 0.0012(16) C17 0.0598(15) 0.0493(16) 0.0395(12) 0.0014(13) 0.0091(11) 0.0060(13) C18 0.0549(14) 0.0552(17) 0.0362(12) -0.0020(13) 0.0115(11) 0.0053(14) C19 0.0591(15) 0.0694(19) 0.0434(14) -0.0048(15) 0.0160(12) -0.0068(15) C20 0.0658(16) 0.0472(16) 0.0489(14) 0.0025(13) 0.0063(12) -0.0038(15) C21 0.0606(15) 0.0585(19) 0.0396(13) -0.0048(14) 0.0056(11) 0.0023(14) C22 0.0710(17) 0.062(2) 0.0424(13) 0.0101(14) 0.0032(13) 0.0102(16) C23 0.0766(18) 0.0546(17) 0.0498(14) 0.0103(14) 0.0118(14) 0.0004(16) C24 0.0707(19) 0.076(2) 0.079(2) -0.015(2) -0.0009(16) -0.0108(19) C28 0.0614(16) 0.070(2) 0.0449(14) -0.0009(15) 0.0201(12) 0.0009(16) C26 0.0602(16) 0.038(2) 0.0495(15) 0.006(2) 0.0141(13) 0.009(2) C25 0.059(4) 0.062(2) 0.050(2) 0.0032(19) 0.007(2) 0.001(2) O8 0.0692(16) 0.085(2) 0.0407(17) -0.0030(16) 0.0127(12) -0.0312(16) O9 0.081(2) 0.105(2) 0.0642(13) -0.0102(16) 0.0321(17) -0.046(2) C27 0.065(2) 0.072(3) 0.057(2) 0.006(2) 0.0248(19) 0.008(2) C26' 0.0602(16) 0.038(2) 0.0495(15) 0.006(2) 0.0141(13) 0.009(2) C25' 0.059(4) 0.062(2) 0.050(2) 0.0032(19) 0.007(2) 0.001(2) O8' 0.33(3) 0.21(3) 0.089(17) 0.062(18) -0.004(17) -0.13(3) O9' 0.081(2) 0.105(2) 0.0642(13) -0.0102(16) 0.0321(17) -0.046(2) C27' 0.089(15) 0.14(3) 0.084(13) -0.014(17) 0.013(11) 0.059(17) C29 0.0693(18) 0.080(2) 0.0519(16) -0.0110(16) 0.0026(14) -0.0103(18) C30 0.0751(19) 0.060(2) 0.0637(17) -0.0153(16) 0.0064(15) 0.0028(16) C31 0.0608(16) 0.0513(17) 0.0470(14) -0.0001(13) 0.0120(12) -0.0025(14) C32 0.0634(15) 0.0520(16) 0.0429(13) 0.0011(13) 0.0168(12) 0.0007(14) C33 0.0692(17) 0.0600(18) 0.0476(14) -0.0016(15) 0.0206(13) 0.0088(15) C34 0.0680(17) 0.0514(17) 0.0557(15) -0.0012(15) 0.0123(13) 0.0030(15) C35 0.0618(16) 0.0554(19) 0.0473(14) 0.0075(14) 0.0100(12) -0.0065(15) C36 0.080(2) 0.061(2) 0.0513(16) -0.0087(15) 0.0023(14) -0.0097(17) C37 0.0828(19) 0.0580(19) 0.0516(15) -0.0101(15) 0.0124(14) 0.0067(17) C38 0.075(2) 0.078(2) 0.090(2) 0.010(2) 0.0011(18) 0.005(2) O1 0.0589(10) 0.0593(12) 0.0734(12) 0.0299(11) 0.0218(9) 0.0133(10) O2 0.0627(10) 0.0676(14) 0.0441(9) 0.0069(10) 0.0073(8) 0.0291(11) O3 0.0514(9) 0.0655(13) 0.0452(9) -0.0027(10) 0.0062(8) 0.0200(10) O4 0.0541(10) 0.0522(11) 0.0439(9) 0.0116(9) 0.0122(7) 0.0103(9) O7 0.0671(12) 0.0763(15) 0.0545(11) -0.0036(11) -0.0051(9) -0.0039(12) O10 0.0681(12) 0.0749(16) 0.0610(12) 0.0042(11) -0.0002(9) -0.0005(12) O11 0.0407(8) 0.0500(11) 0.0510(9) 0.0054(9) 0.0044(7) 0.0056(8) O12 0.0402(8) 0.0458(10) 0.0503(9) 0.0047(8) 0.0021(7) 0.0055(8) N1 0.0391(10) 0.0393(11) 0.0456(10) 0.0014(9) 0.0042(8) -0.0014(9) N2 0.0342(9) 0.0346(11) 0.0488(10) 0.0043(9) 0.0065(8) 0.0006(8) _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 O1 1.234(3) . ? C1 O2 1.261(3) . ? C1 C2 1.508(4) . ? C2 N1 1.490(3) . ? C2 C3 1.515(3) . ? C2 H2A 0.9596 . ? C3 C4 1.522(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.486(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.490(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O4 1.231(3) . ? C6 O3 1.257(3) . ? C6 C7 1.515(3) . ? C7 N2 1.492(3) . ? C7 C8 1.520(3) . ? C7 H7 0.9800 . ? C8 C9 1.518(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.514(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N2 1.495(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C14 C19 1.353(4) . ? C14 C12' 1.377(15) . ? C14 C15 1.403(5) . ? C14 C12 1.556(5) . ? C12 C11 1.515(5) . ? C12 C13 1.520(5) . ? C12 H12 0.9800 . ? C11 O6 1.214(8) . ? C11 O5 1.291(5) . ? O5 H5 0.8200 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C12' C13' 1.462(16) . ? C12' C11' 1.542(14) . ? C12' H12' 0.9800 . ? C11' O6' 1.190(17) . ? C11' O5' 1.328(15) . ? O5' H5' 0.8200 . ? C13' H13D 0.9600 . ? C13' H13E 0.9600 . ? C13' H13F 0.9600 . ? C15 C16 1.368(4) . ? C15 H15 0.9300 . ? C16 C17 1.414(4) . ? C16 H16 0.9300 . ? C17 C18 1.404(4) . ? C17 C20 1.418(4) . ? C18 C19 1.414(4) . ? C18 C23 1.414(4) . ? C19 H19 0.9300 . ? C20 C21 1.357(4) . ? C20 H20 0.9300 . ? C21 O7 1.364(3) . ? C21 C22 1.401(4) . ? C22 C23 1.357(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 O7 1.418(4) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C28 C33 1.350(4) . ? C28 C26' 1.379(14) . ? C28 C29 1.399(5) . ? C28 C26 1.545(5) . ? C26 C27 1.513(5) . ? C26 C25 1.514(5) . ? C26 H26 0.9800 . ? C25 O9 1.220(6) . ? C25 O8 1.294(6) . ? O8 H8 0.8200 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C26' C27' 1.461(15) . ? C26' C25' 1.522(16) . ? C26' H26' 0.9800 . ? C25' O9' 1.205(16) . ? C25' O8' 1.309(16) . ? O8' H8' 0.8200 . ? C27' H27D 0.9600 . ? C27' H27E 0.9600 . ? C27' H27F 0.9600 . ? C29 C30 1.369(4) . ? C29 H29 0.9300 . ? C30 C31 1.412(4) . ? C30 H30 0.9300 . ? C31 C32 1.415(4) . ? C31 C34 1.420(4) . ? C32 C33 1.408(4) . ? C32 C37 1.413(4) . ? C33 H33 0.9300 . ? C34 C35 1.353(4) . ? C34 H34 0.9300 . ? C35 O10 1.369(3) . ? C35 C36 1.410(4) . ? C36 C37 1.345(4) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? C38 O10 1.412(5) . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? O11 H11B 0.8505 . ? O11 H11A 0.8571 . ? O12 H12A 0.8505 . ? O12 H12B 0.8440 . ? N1 H1A 0.8755 . ? N1 H1B 0.8614 . ? N2 H2B 0.8865 . ? N2 H2C 0.8758 . ? 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 C1 O2 125.4(3) . . ? O1 C1 C2 117.9(2) . . ? O2 C1 C2 116.7(2) . . ? N1 C2 C1 111.30(19) . . ? N1 C2 C3 103.86(18) . . ? C1 C2 C3 118.1(2) . . ? N1 C2 H2A 102.9 . . ? C1 C2 H2A 106.5 . . ? C3 C2 H2A 113.2 . . ? C2 C3 C4 103.4(2) . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3B 111.1 . . ? C4 C3 H3B 111.1 . . ? H3A C3 H3B 109.0 . . ? C5 C4 C3 105.7(2) . . ? C5 C4 H4A 110.6 . . ? C3 C4 H4A 110.6 . . ? C5 C4 H4B 110.6 . . ? C3 C4 H4B 110.6 . . ? H4A C4 H4B 108.7 . . ? C4 C5 N1 106.5(2) . . ? C4 C5 H5A 110.4 . . ? N1 C5 H5A 110.4 . . ? C4 C5 H5B 110.4 . . ? N1 C5 H5B 110.4 . . ? H5A C5 H5B 108.6 . . ? O4 C6 O3 125.7(2) . . ? O4 C6 C7 118.5(2) . . ? O3 C6 C7 115.73(19) . . ? N2 C7 C6 112.02(17) . . ? N2 C7 C8 101.88(19) . . ? C6 C7 C8 119.08(19) . . ? N2 C7 H7 107.8 . . ? C6 C7 H7 107.8 . . ? C8 C7 H7 107.8 . . ? C9 C8 C7 102.80(19) . . ? C9 C8 H8A 111.2 . . ? C7 C8 H8A 111.2 . . ? C9 C8 H8B 111.2 . . ? C7 C8 H8B 111.2 . . ? H8A C8 H8B 109.1 . . ? C10 C9 C8 105.4(2) . . ? C10 C9 H9A 110.7 . . ? C8 C9 H9A 110.7 . . ? C10 C9 H9B 110.7 . . ? C8 C9 H9B 110.7 . . ? H9A C9 H9B 108.8 . . ? N2 C10 C9 105.6(2) . . ? N2 C10 H10A 110.6 . . ? C9 C10 H10A 110.6 . . ? N2 C10 H10B 110.6 . . ? C9 C10 H10B 110.6 . . ? H10A C10 H10B 108.7 . . ? C19 C14 C12' 144.3(9) . . ? C19 C14 C15 117.8(3) . . ? C12' C14 C15 96.6(10) . . ? C19 C14 C12 119.4(3) . . ? C12' C14 C12 28.4(9) . . ? C15 C14 C12 122.8(3) . . ? C11 C12 C13 111.8(3) . . ? C11 C12 C14 108.3(3) . . ? C13 C12 C14 109.9(3) . . ? C11 C12 H12 108.9 . . ? C13 C12 H12 108.9 . . ? C14 C12 H12 108.9 . . ? O6 C11 O5 123.7(5) . . ? O6 C11 C12 123.2(5) . . ? O5 C11 C12 112.9(4) . . ? C11 O5 H5 109.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C14 C12' C13' 106.3(16) . . ? C14 C12' C11' 112.4(12) . . ? C13' C12' C11' 114.7(15) . . ? C14 C12' H12' 107.7 . . ? C13' C12' H12' 107.7 . . ? C11' C12' H12' 107.7 . . ? O6' C11' O5' 119(2) . . ? O6' C11' C12' 123(2) . . ? O5' C11' C12' 109.7(15) . . ? C11' O5' H5' 109.5 . . ? C12' C13' H13D 109.5 . . ? C12' C13' H13E 109.5 . . ? H13D C13' H13E 109.5 . . ? C12' C13' H13F 109.5 . . ? H13D C13' H13F 109.5 . . ? H13E C13' H13F 109.5 . . ? C16 C15 C14 122.1(3) . . ? C16 C15 H15 118.9 . . ? C14 C15 H15 118.9 . . ? C15 C16 C17 120.6(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C18 C17 C16 117.3(3) . . ? C18 C17 C20 119.8(2) . . ? C16 C17 C20 122.9(3) . . ? C17 C18 C19 120.2(2) . . ? C17 C18 C23 118.2(2) . . ? C19 C18 C23 121.6(3) . . ? C14 C19 C18 121.8(3) . . ? C14 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C21 C20 C17 120.3(3) . . ? C21 C20 H20 119.9 . . ? C17 C20 H20 119.9 . . ? C20 C21 O7 125.6(3) . . ? C20 C21 C22 120.0(3) . . ? O7 C21 C22 114.4(2) . . ? C23 C22 C21 121.0(3) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C18 120.7(3) . . ? C22 C23 H23 119.6 . . ? C18 C23 H23 119.6 . . ? O7 C24 H24A 109.5 . . ? O7 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O7 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C33 C28 C26' 140.0(7) . . ? C33 C28 C29 117.5(3) . . ? C26' C28 C29 101.2(7) . . ? C33 C28 C26 119.8(3) . . ? C26' C28 C26 24.1(7) . . ? C29 C28 C26 122.6(3) . . ? C27 C26 C25 111.0(4) . . ? C27 C26 C28 109.9(3) . . ? C25 C26 C28 108.7(7) . . ? C27 C26 H26 109.1 . . ? C25 C26 H26 109.1 . . ? C28 C26 H26 109.1 . . ? O9 C25 O8 123.8(4) . . ? O9 C25 C26 123.3(5) . . ? O8 C25 C26 112.9(4) . . ? C25 O8 H8 109.5 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C28 C26' C27' 113.6(14) . . ? C28 C26' C25' 106(2) . . ? C27' C26' C25' 112(2) . . ? C28 C26' H26' 108.5 . . ? C27' C26' H26' 108.5 . . ? C25' C26' H26' 108.5 . . ? O9' C25' O8' 124.0(19) . . ? O9' C25' C26' 118.1(19) . . ? O8' C25' C26' 116.6(18) . . ? C25' O8' H8' 109.5 . . ? C26' C27' H27D 109.5 . . ? C26' C27' H27E 109.5 . . ? H27D C27' H27E 109.5 . . ? C26' C27' H27F 109.5 . . ? H27D C27' H27F 109.5 . . ? H27E C27' H27F 109.5 . . ? C30 C29 C28 122.2(3) . . ? C30 C29 H29 118.9 . . ? C28 C29 H29 118.9 . . ? C29 C30 C31 120.6(3) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C30 C31 C32 117.4(3) . . ? C30 C31 C34 123.1(3) . . ? C32 C31 C34 119.5(3) . . ? C33 C32 C37 123.0(3) . . ? C33 C32 C31 119.3(3) . . ? C37 C32 C31 117.7(3) . . ? C28 C33 C32 122.8(3) . . ? C28 C33 H33 118.6 . . ? C32 C33 H33 118.6 . . ? C35 C34 C31 120.6(3) . . ? C35 C34 H34 119.7 . . ? C31 C34 H34 119.7 . . ? C34 C35 O10 125.9(3) . . ? C34 C35 C36 119.9(3) . . ? O10 C35 C36 114.3(3) . . ? C37 C36 C35 120.7(3) . . ? C37 C36 H36 119.7 . . ? C35 C36 H36 119.7 . . ? C36 C37 C32 121.6(3) . . ? C36 C37 H37 119.2 . . ? C32 C37 H37 119.2 . . ? O10 C38 H38A 109.5 . . ? O10 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O10 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C21 O7 C24 117.9(2) . . ? C35 O10 C38 117.7(3) . . ? H11B O11 H11A 105.4 . . ? H12A O12 H12B 107.6 . . ? C2 N1 C5 108.38(18) . . ? C2 N1 H1A 106.1 . . ? C5 N1 H1A 111.4 . . ? C2 N1 H1B 107.7 . . ? C5 N1 H1B 105.2 . . ? H1A N1 H1B 117.7 . . ? C7 N2 C10 107.38(18) . . ? C7 N2 H2B 105.6 . . ? C10 N2 H2B 110.3 . . ? C7 N2 H2C 107.4 . . ? C10 N2 H2C 116.3 . . ? H2B N2 H2C 109.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 N1 12.9(3) . . . . ? O2 C1 C2 N1 -167.5(2) . . . . ? O1 C1 C2 C3 132.9(3) . . . . ? O2 C1 C2 C3 -47.5(3) . . . . ? N1 C2 C3 C4 -34.1(3) . . . . ? C1 C2 C3 C4 -157.8(2) . . . . ? C2 C3 C4 C5 32.3(3) . . . . ? C3 C4 C5 N1 -17.8(3) . . . . ? O4 C6 C7 N2 11.2(3) . . . . ? O3 C6 C7 N2 -171.9(2) . . . . ? O4 C6 C7 C8 129.8(2) . . . . ? O3 C6 C7 C8 -53.3(3) . . . . ? N2 C7 C8 C9 -41.1(2) . . . . ? C6 C7 C8 C9 -164.8(2) . . . . ? C7 C8 C9 C10 33.1(3) . . . . ? C8 C9 C10 N2 -12.1(3) . . . . ? C19 C14 C12 C11 -128.6(3) . . . . ? C12' C14 C12 C11 74.8(14) . . . . ? C15 C14 C12 C11 49.4(4) . . . . ? C19 C14 C12 C13 108.9(4) . . . . ? C12' C14 C12 C13 -47.6(14) . . . . ? C15 C14 C12 C13 -73.1(4) . . . . ? C13 C12 C11 O6 24.5(8) . . . . ? C14 C12 C11 O6 -96.8(7) . . . . ? C13 C12 C11 O5 -160.8(4) . . . . ? C14 C12 C11 O5 77.9(4) . . . . ? C19 C14 C12' C13' 2(2) . . . . ? C15 C14 C12' C13' -163.0(15) . . . . ? C12 C14 C12' C13' 38.4(15) . . . . ? C19 C14 C12' C11' -124.4(11) . . . . ? C15 C14 C12' C11' 70.7(15) . . . . ? C12 C14 C12' C11' -88(2) . . . . ? C14 C12' C11' O6' -168(3) . . . . ? C13' C12' C11' O6' 70(4) . . . . ? C14 C12' C11' O5' 43(2) . . . . ? C13' C12' C11' O5' -78(2) . . . . ? C19 C14 C15 C16 3.9(4) . . . . ? C12' C14 C15 C16 173.9(8) . . . . ? C12 C14 C15 C16 -174.2(3) . . . . ? C14 C15 C16 C17 -1.5(5) . . . . ? C15 C16 C17 C18 -1.9(4) . . . . ? C15 C16 C17 C20 176.4(3) . . . . ? C16 C17 C18 C19 3.0(4) . . . . ? C20 C17 C18 C19 -175.4(2) . . . . ? C16 C17 C18 C23 -179.3(3) . . . . ? C20 C17 C18 C23 2.3(4) . . . . ? C12' C14 C19 C18 -165.7(14) . . . . ? C15 C14 C19 C18 -2.8(4) . . . . ? C12 C14 C19 C18 175.3(3) . . . . ? C17 C18 C19 C14 -0.6(4) . . . . ? C23 C18 C19 C14 -178.3(2) . . . . ? C18 C17 C20 C21 0.0(4) . . . . ? C16 C17 C20 C21 -178.2(3) . . . . ? C17 C20 C21 O7 177.6(3) . . . . ? C17 C20 C21 C22 -2.7(4) . . . . ? C20 C21 C22 C23 3.0(4) . . . . ? O7 C21 C22 C23 -177.3(3) . . . . ? C21 C22 C23 C18 -0.5(4) . . . . ? C17 C18 C23 C22 -2.1(4) . . . . ? C19 C18 C23 C22 175.6(3) . . . . ? C33 C28 C26 C27 -105.7(4) . . . . ? C26' C28 C26 C27 46.2(15) . . . . ? C29 C28 C26 C27 75.8(4) . . . . ? C33 C28 C26 C25 132.6(4) . . . . ? C26' C28 C26 C25 -75.4(17) . . . . ? C29 C28 C26 C25 -45.9(5) . . . . ? C27 C26 C25 O9 -11.9(16) . . . . ? C28 C26 C25 O9 109.0(13) . . . . ? C27 C26 C25 O8 166.4(8) . . . . ? C28 C26 C25 O8 -72.6(11) . . . . ? C33 C28 C26' C27' -13(2) . . . . ? C29 C28 C26' C27' 152.1(17) . . . . ? C26 C28 C26' C27' -52.9(19) . . . . ? C33 C28 C26' C25' 109(2) . . . . ? C29 C28 C26' C25' -85.0(18) . . . . ? C26 C28 C26' C25' 70(2) . . . . ? C28 C26' C25' O9' 118(5) . . . . ? C27' C26' C25' O9' -118(5) . . . . ? C28 C26' C25' O8' -50(6) . . . . ? C27' C26' C25' O8' 74(6) . . . . ? C33 C28 C29 C30 -3.3(4) . . . . ? C26' C28 C29 C30 -172.9(7) . . . . ? C26 C28 C29 C30 175.2(3) . . . . ? C28 C29 C30 C31 -0.2(5) . . . . ? C29 C30 C31 C32 3.2(4) . . . . ? C29 C30 C31 C34 -175.3(3) . . . . ? C30 C31 C32 C33 -2.7(4) . . . . ? C34 C31 C32 C33 175.8(3) . . . . ? C30 C31 C32 C37 179.2(3) . . . . ? C34 C31 C32 C37 -2.3(4) . . . . ? C26' C28 C33 C32 167.8(10) . . . . ? C29 C28 C33 C32 3.8(4) . . . . ? C26 C28 C33 C32 -174.8(3) . . . . ? C37 C32 C33 C28 177.2(3) . . . . ? C31 C32 C33 C28 -0.8(4) . . . . ? C30 C31 C34 C35 178.6(3) . . . . ? C32 C31 C34 C35 0.1(4) . . . . ? C31 C34 C35 O10 -177.2(3) . . . . ? C31 C34 C35 C36 1.8(4) . . . . ? C34 C35 C36 C37 -1.6(4) . . . . ? O10 C35 C36 C37 177.5(3) . . . . ? C35 C36 C37 C32 -0.6(5) . . . . ? C33 C32 C37 C36 -175.5(3) . . . . ? C31 C32 C37 C36 2.5(4) . . . . ? C20 C21 O7 C24 2.8(4) . . . . ? C22 C21 O7 C24 -177.0(2) . . . . ? C34 C35 O10 C38 -3.7(4) . . . . ? C36 C35 O10 C38 177.3(2) . . . . ? C1 C2 N1 C5 152.0(2) . . . . ? C3 C2 N1 C5 23.9(3) . . . . ? C4 C5 N1 C2 -3.9(3) . . . . ? C6 C7 N2 C10 162.80(19) . . . . ? C8 C7 N2 C10 34.4(2) . . . . ? C9 C10 N2 C7 -14.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.203 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.029 _iucr_refine_instructions_details ; TITL bn_at_lpro-nprx01 in P2(1) CELL 0.71073 13.1220 5.8980 24.0750 90.000 95.560 90.000 ZERR 4.00 0.0020 0.0010 0.0030 0.000 0.005 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N O UNIT 76 100 4 24 MERG 2 TWIN SHEL 99 0.84 FMAP 2 PLAN 20 SIZE 0.05 0.20 0.40 BOND $H CONF L.S. 15 EADP C25 C25' EADP C11 C11' EADP C26 C26' EADP O5 O5' EADP O9 O9' ACTA TEMP 20.00 WGHT 0.068600 0.567400 FVAR 4.32196 0.80000 C1 1 0.333766 0.742839 0.064755 11.00000 0.03837 0.04811 = 0.04182 0.00320 0.00054 0.00541 C2 1 0.366527 0.512544 0.087107 11.00000 0.03418 0.04332 = 0.04402 0.00550 0.00507 -0.00138 C3 1 0.392299 0.487320 0.149512 11.00000 0.07589 0.07755 = 0.04614 0.01598 0.01283 0.02735 AFIX 23 H3A 2 0.330914 0.464872 0.168275 11.00000 -1.20000 H3B 2 0.428469 0.619592 0.165143 11.00000 -1.20000 AFIX 0 C4 1 0.460428 0.278016 0.154598 11.00000 0.08772 0.07519 = 0.06067 0.02198 0.01105 0.02956 AFIX 23 H4A 2 0.507428 0.285409 0.188225 11.00000 -1.20000 H4B 2 0.419404 0.141633 0.155855 11.00000 -1.20000 AFIX 0 C5 1 0.517472 0.278413 0.104181 11.00000 0.05691 0.05475 = 0.06740 0.01335 0.00243 0.01361 AFIX 23 H5A 2 0.520322 0.126612 0.088907 11.00000 -1.20000 H5B 2 0.586888 0.332280 0.113429 11.00000 -1.20000 AFIX 0 C6 1 0.165983 0.566995 -0.063814 11.00000 0.03694 0.03270 = 0.03756 -0.00286 0.00178 -0.00322 C7 1 0.097545 0.728430 -0.099300 11.00000 0.04069 0.03505 = 0.03571 -0.00397 0.00314 -0.00141 AFIX 13 H7 2 0.057275 0.638607 -0.127800 11.00000 -1.20000 AFIX 0 C8 1 0.145915 0.923376 -0.128607 11.00000 0.06445 0.04658 = 0.05056 0.01125 0.01870 0.00417 AFIX 23 H8A 2 0.197153 1.000293 -0.103638 11.00000 -1.20000 H8B 2 0.177213 0.870811 -0.161148 11.00000 -1.20000 AFIX 0 C9 1 0.055212 1.077132 -0.145134 11.00000 0.07740 0.04033 = 0.05253 0.00969 0.00150 0.00009 AFIX 23 H9A 2 0.077283 1.233422 -0.147706 11.00000 -1.20000 H9B 2 0.020821 1.031699 -0.180882 11.00000 -1.20000 AFIX 0 C10 1 -0.015194 1.050274 -0.099337 11.00000 0.05458 0.04995 = 0.05911 0.01469 0.00254 0.01568 AFIX 23 H10A 2 -0.013589 1.185044 -0.076176 11.00000 -1.20000 H10B 2 -0.085075 1.024285 -0.115098 11.00000 -1.20000 AFIX 0 same C14 C12 C14 C12' C14 1 0.225970 0.054151 0.296489 11.00000 0.05224 0.07747 = 0.04102 -0.00099 0.01462 0.00025 PART 1 same C12' > C13' C12 1 0.132580 -0.056193 0.261898 10.80000 0.04326 0.05104 = 0.05019 -0.01007 0.01469 -0.01247 AFIX 13 H12 2 0.126197 -0.213864 0.273929 10.80000 -1.20000 AFIX 0 C11 1 0.152369 -0.053414 0.200921 10.80000 0.03474 0.04560 = 0.04433 -0.00445 0.00016 -0.00052 O5 4 0.214873 -0.210379 0.188477 10.80000 0.08442 0.06114 = 0.04857 -0.00376 0.01345 0.02176 AFIX 83 H5 2 0.222496 -0.203691 0.155111 10.80000 -1.50000 AFIX 0 O6 4 0.119007 0.092041 0.168423 10.80000 0.06827 0.12943 = 0.05446 -0.00216 -0.00957 0.05304 C13 1 0.035210 0.070785 0.271788 10.80000 0.05087 0.08278 = 0.06919 -0.00816 0.02051 0.00823 AFIX 33 H13A 2 0.025537 0.066556 0.310792 10.80000 -1.50000 H13B 2 -0.022195 0.000527 0.250756 10.80000 -1.50000 H13C 2 0.040774 0.225493 0.260063 10.80000 -1.50000 AFIX 0 PART 2 C12' 1 0.137761 0.068731 0.260701 10.20000 0.07485 0.09760 = 0.05144 -0.03473 0.01335 -0.05185 AFIX 13 H12' 2 0.108001 0.219089 0.265414 10.20000 -1.20000 AFIX 0 C11' 1 0.158372 0.044556 0.199001 10.20000 0.03474 0.04560 = 0.04433 -0.00445 0.00016 -0.00052 O5' 4 0.224700 -0.122428 0.193809 10.20000 0.08442 0.06114 = 0.04857 -0.00376 0.01345 0.02176 AFIX 83 H5' 2 0.234438 -0.136934 0.160864 10.20000 -1.50000 AFIX 0 O6' 4 0.096083 0.085173 0.161051 10.20000 0.03976 0.11441 = 0.05376 0.01468 -0.00920 0.00460 C13' 1 0.067107 -0.099168 0.279917 10.20000 0.08111 0.14409 = 0.06204 0.00421 -0.01241 -0.02753 AFIX 33 H13D 2 0.003522 -0.093514 0.256602 10.20000 -1.50000 H13E 2 0.054958 -0.066513 0.317780 10.20000 -1.50000 H13F 2 0.096448 -0.247729 0.277988 10.20000 -1.50000 AFIX 0 PART 0 C15 1 0.267240 0.263594 0.282409 11.00000 0.06445 0.09045 = 0.04217 0.01122 0.00053 0.01482 AFIX 43 H15 2 0.234092 0.346815 0.253215 11.00000 -1.20000 AFIX 0 C16 1 0.354648 0.349257 0.310245 11.00000 0.07369 0.06092 = 0.05539 0.01426 0.00604 0.00119 AFIX 43 H16 2 0.380611 0.487028 0.299179 11.00000 -1.20000 AFIX 0 C17 1 0.405886 0.230268 0.355687 11.00000 0.05976 0.04933 = 0.03947 0.00140 0.00913 0.00600 C18 1 0.361577 0.026764 0.371697 11.00000 0.05491 0.05523 = 0.03622 -0.00197 0.01147 0.00530 C19 1 0.272047 -0.057346 0.341187 11.00000 0.05912 0.06937 = 0.04343 -0.00475 0.01597 -0.00682 AFIX 43 H19 2 0.244044 -0.193131 0.352152 11.00000 -1.20000 AFIX 0 C20 1 0.499702 0.304950 0.383972 11.00000 0.06575 0.04722 = 0.04894 0.00248 0.00631 -0.00375 AFIX 43 H20 2 0.529091 0.439789 0.373406 11.00000 -1.20000 AFIX 0 C21 1 0.546754 0.180502 0.426379 11.00000 0.06056 0.05846 = 0.03957 -0.00480 0.00561 0.00228 C22 1 0.500494 -0.017663 0.443905 11.00000 0.07099 0.06213 = 0.04237 0.01006 0.00316 0.01018 AFIX 43 H22 2 0.531609 -0.098383 0.474118 11.00000 -1.20000 AFIX 0 C23 1 0.410989 -0.093593 0.417467 11.00000 0.07658 0.05456 = 0.04977 0.01032 0.01184 0.00036 AFIX 43 H23 2 0.381810 -0.226209 0.429570 11.00000 -1.20000 AFIX 0 C24 1 0.688055 0.434356 0.441933 11.00000 0.07075 0.07590 = 0.07897 -0.01453 -0.00087 -0.01082 AFIX 33 H24A 2 0.751345 0.449116 0.465229 11.00000 -1.50000 H24B 2 0.644582 0.561056 0.448029 11.00000 -1.50000 H24C 2 0.701727 0.430885 0.403485 11.00000 -1.50000 AFIX 0 same C28 C26 C28 C26' C28 1 -0.264799 -0.200241 0.300387 11.00000 0.06141 0.06997 = 0.04494 -0.00088 0.02008 0.00090 PART 1 same C26' > C27' C26 1 -0.357753 -0.090357 0.266296 10.80000 0.06023 0.03823 = 0.04952 0.00606 0.01412 0.00907 AFIX 13 H26 2 -0.361741 0.069748 0.276755 10.80000 -1.20000 AFIX 0 C25 1 -0.342663 -0.106468 0.204850 10.80000 0.05946 0.06244 = 0.04999 0.00323 0.00740 0.00118 O8 4 -0.272975 0.030520 0.190250 10.80000 0.06921 0.08526 = 0.04066 -0.00304 0.01266 -0.03117 AFIX 83 H8 2 -0.265717 0.012096 0.157104 10.80000 -1.50000 AFIX 0 O9 4 -0.392798 -0.231798 0.172451 10.80000 0.08140 0.10453 = 0.06419 -0.01023 0.03215 -0.04600 C27 1 -0.455198 -0.208790 0.278778 10.80000 0.06537 0.07203 = 0.05678 0.00552 0.02482 0.00798 AFIX 33 H27A 2 -0.464538 -0.191094 0.317598 10.80000 -1.50000 H27B 2 -0.450526 -0.367135 0.270147 10.80000 -1.50000 H27C 2 -0.512380 -0.143312 0.256510 10.80000 -1.50000 AFIX 0 PART 2 C26' 1 -0.355666 -0.197242 0.266455 10.20000 0.06023 0.03823 = 0.04952 0.00606 0.01412 0.00907 AFIX 13 H26' 2 -0.380193 -0.353511 0.261374 10.20000 -1.20000 AFIX 0 C25' 1 -0.330154 -0.106766 0.210237 10.20000 0.05946 0.06244 = 0.04999 0.00323 0.00740 0.00118 O8' 4 -0.276839 0.081037 0.211004 10.20000 0.33117 0.20735 = 0.08917 0.06235 -0.00408 -0.12550 AFIX 83 H8' 2 -0.272861 0.124409 0.178926 10.20000 -1.50000 AFIX 0 O9' 4 -0.344205 -0.229350 0.170180 10.20000 0.08140 0.10453 = 0.06419 -0.01023 0.03215 -0.04600 C27' 1 -0.435821 -0.062897 0.288871 10.20000 0.08877 0.13985 = 0.08353 -0.01422 0.01270 0.05861 AFIX 33 H27D 2 -0.493099 -0.048617 0.261101 10.20000 -1.50000 H27E 2 -0.409639 0.084985 0.298960 10.20000 -1.50000 H27F 2 -0.457384 -0.136801 0.321280 10.20000 -1.50000 AFIX 0 PART 0 C29 1 -0.224398 -0.409557 0.286235 11.00000 0.06929 0.07952 = 0.05185 -0.01100 0.00264 -0.01027 AFIX 43 H29 2 -0.257570 -0.491341 0.256789 11.00000 -1.20000 AFIX 0 C30 1 -0.137654 -0.498152 0.314265 11.00000 0.07509 0.05995 = 0.06374 -0.01534 0.00643 0.00281 AFIX 43 H30 2 -0.113238 -0.638130 0.303688 11.00000 -1.20000 AFIX 0 C31 1 -0.084977 -0.378804 0.359082 11.00000 0.06084 0.05131 = 0.04704 -0.00009 0.01204 -0.00250 C32 1 -0.128286 -0.172327 0.375325 11.00000 0.06341 0.05204 = 0.04291 0.00109 0.01676 0.00075 C33 1 -0.218077 -0.090881 0.345080 11.00000 0.06917 0.06005 = 0.04765 -0.00156 0.02061 0.00884 AFIX 43 H33 2 -0.246397 0.044031 0.356383 11.00000 -1.20000 AFIX 0 C34 1 0.009191 -0.453916 0.387048 11.00000 0.06802 0.05136 = 0.05570 -0.00117 0.01234 0.00296 AFIX 43 H34 2 0.037963 -0.589371 0.376427 11.00000 -1.20000 AFIX 0 C35 1 0.057470 -0.330141 0.429032 11.00000 0.06183 0.05544 = 0.04730 0.00754 0.00995 -0.00652 C36 1 0.012641 -0.127906 0.446312 11.00000 0.07981 0.06096 = 0.05125 -0.00871 0.00231 -0.00966 AFIX 43 H36 2 0.045182 -0.045202 0.475781 11.00000 -1.20000 AFIX 0 C37 1 -0.076708 -0.053392 0.420607 11.00000 0.08282 0.05801 = 0.05165 -0.01009 0.01243 0.00674 AFIX 43 H37 2 -0.105199 0.079611 0.432945 11.00000 -1.20000 AFIX 0 C38 1 0.197937 -0.585312 0.444217 11.00000 0.07527 0.07820 = 0.08961 0.01003 0.00109 0.00521 AFIX 33 H38A 2 0.261555 -0.601153 0.467171 11.00000 -1.50000 H38B 2 0.210796 -0.583735 0.405637 11.00000 -1.50000 H38C 2 0.153903 -0.710408 0.450846 11.00000 -1.50000 AFIX 0 O1 4 0.373874 0.815489 0.024020 11.00000 0.05888 0.05932 = 0.07343 0.02988 0.02178 0.01327 O2 4 0.266604 0.844851 0.089358 11.00000 0.06270 0.06759 = 0.04410 0.00687 0.00726 0.02909 O3 4 0.237555 0.478445 -0.087419 11.00000 0.05136 0.06550 = 0.04519 -0.00272 0.00622 0.01998 O4 4 0.145068 0.525769 -0.016076 11.00000 0.05412 0.05215 = 0.04394 0.01159 0.01217 0.01032 O7 4 0.638578 0.230495 0.455312 11.00000 0.06714 0.07627 = 0.05447 -0.00362 -0.00514 -0.00394 O10 4 0.150207 -0.380272 0.457453 11.00000 0.06807 0.07494 = 0.06100 0.00417 -0.00022 -0.00053 O11 4 0.378595 0.206803 -0.030649 11.00000 0.04070 0.05003 = 0.05098 0.00542 0.00443 0.00560 O12 4 0.131957 1.093773 0.022574 11.00000 0.04021 0.04580 = 0.05030 0.00471 0.00212 0.00549 N1 3 0.460756 0.433185 0.063131 11.00000 0.03910 0.03926 = 0.04555 0.00136 0.00417 -0.00142 N2 3 0.024474 0.849806 -0.065954 11.00000 0.03422 0.03458 = 0.04877 0.00430 0.00652 0.00056 AFIX 1 H2B 2 0.061212 0.894722 -0.035074 11.00000 0.04206 H11B 2 0.350665 0.101425 -0.013364 11.00000 0.11051 H11A 2 0.329036 0.277288 -0.048969 11.00000 0.07415 H2C 2 -0.021261 0.750965 -0.057343 11.00000 0.06327 H2A 2 0.315546 0.407032 0.071936 11.00000 0.04258 H1A 2 0.439894 0.362002 0.032193 11.00000 0.03959 H1B 2 0.500282 0.548706 0.060816 11.00000 0.04554 H12A 2 0.178243 1.028194 0.043975 11.00000 0.07060 H12B 2 0.156412 1.217479 0.012270 11.00000 0.09612 HKLF 4 REM bn_at_lpro-nprx01 in P2(1) REM R1 = 0.0421 for 5138 Fo > 4sig(Fo) and 0.0500 for all 5930 data REM 530 parameters refined using 25 restraints END WGHT 0.0523 0.2174 REM Highest difference peak 0.203, deepest hole -0.195, 1-sigma level 0.029 Q1 1 -0.2901 -0.1766 0.1694 11.00000 0.05 0.20 Q2 1 0.3619 0.5483 0.1836 11.00000 0.05 0.13 Q3 1 0.0520 0.2545 0.2720 11.00000 0.05 0.13 Q4 1 -0.2790 -0.3511 0.3018 11.00000 0.05 0.12 Q5 1 0.3802 0.0312 0.4033 11.00000 0.05 0.12 Q6 1 0.2077 0.0395 0.1658 11.00000 0.05 0.12 Q7 1 0.2228 0.1990 0.2999 11.00000 0.05 0.11 Q8 1 0.2594 0.4201 0.2724 11.00000 0.05 0.11 Q9 1 -0.2598 -0.0362 0.1423 11.00000 0.05 0.11 Q10 1 0.3982 0.8884 0.0572 11.00000 0.05 0.11 Q11 1 0.4679 0.5996 0.1497 11.00000 0.05 0.11 Q12 1 -0.3591 -0.3796 0.1542 11.00000 0.05 0.11 Q13 1 -0.0863 -0.5960 0.2932 11.00000 0.05 0.11 Q14 1 0.5618 0.1302 0.0640 11.00000 0.05 0.11 Q15 1 0.5846 0.2149 0.0930 11.00000 0.05 0.11 Q16 1 0.5051 0.3064 0.4190 11.00000 0.05 0.10 Q17 1 -0.1115 -0.1706 0.4049 11.00000 0.05 0.10 Q18 1 -0.2293 -0.1280 0.1916 11.00000 0.05 0.10 Q19 1 0.2449 -0.1377 0.1422 11.00000 0.05 0.10 Q20 1 0.4389 0.3323 -0.0180 11.00000 0.05 0.09 ;