#------------------------------------------------------------------------------ #$Date: 2016-02-19 22:18:51 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176760 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/12/2011215.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2011215 loop_ _publ_author_name 'Corbier, Catherine' 'Didierjean, Claude' 'Th\'evenet, Laurent' 'Vanderesse, Regis' 'Marraud, Michel' _publ_section_title ; Piv-Pro\y[CH~2~--NH--O]Gly--NH^i^Pr ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 995 _journal_page_last 996 _journal_paper_doi 10.1107/S0108270100006478 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C15 H29 N3 O3' _chemical_formula_weight 299.41 _chemical_name_common Piv-Pro\y[CH2-NH-O]Gly-NH^i^Pr _chemical_name_systematic ; (S)-N-(tert-butylcarbonyl)-2-[[O-(N-isopropylacetamidyl)] -hydroxylaminomethylene]-pyrrolidine ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.3860(5) _cell_length_b 11.470(2) _cell_length_c 27.539(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.2 _cell_measurement_theta_min 9.7 _cell_volume 1701.3(4) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'maXus (Mackay et al., 1999)' _computing_molecular_graphics maXus _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .985 _diffrn_measured_fraction_theta_max .985 _diffrn_measurement_device_type 'Nonius Mach3 diffractometer' _diffrn_measurement_method '\w/2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Nonius FR591 rotating Cu anode' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54060 _diffrn_reflns_av_R_equivalents .0000 _diffrn_reflns_av_sigmaI/netI .0132 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1877 _diffrn_reflns_theta_full 69.69 _diffrn_reflns_theta_max 69.69 _diffrn_reflns_theta_min 3.21 _diffrn_standards_decay_% 3.7 _diffrn_standards_interval_time 60 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu .658 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 656 _exptl_crystal_size_max .6 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _refine_diff_density_max .276 _refine_diff_density_min -.331 _refine_ls_extinction_coef .0125(16) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 197 _refine_ls_number_reflns 1877 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all .0590 _refine_ls_R_factor_gt .0541 _refine_ls_shift/su_max .019 _refine_ls_shift/su_mean .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1120P)^2^+0.3040P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1573 _reflns_number_gt 1702 _reflns_number_total 1877 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gs1085.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M P212121 _cod_database_code 2011215 _cod_database_fobs_code 2011215 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O2 .3926(4) .23774(17) .07053(7) .0442(5) Uani d . 1 . . O O3 .9164(4) .4192(2) .04322(9) .0580(6) Uani d . 1 . . O O1 .2749(5) .25799(18) .25725(7) .0562(6) Uani d . 1 . . O N1 .2908(4) .08643(17) .21961(8) .0383(5) Uani d . 1 . . N N3 .5056(5) .4479(2) .02998(10) .0468(6) Uani d D 1 . . N H3 .328(3) .416(3) .0294(14) .061 Uiso d D 1 . . H N2 .3164(5) .29575(19) .11501(8) .0453(6) Uani d D 1 . . N H2 .178(5) .348(3) .1018(12) .059 Uiso d D 1 . . H C12 .7006(5) .3856(2) .04434(10) .0431(6) Uani d . 1 . . C C6 .4081(5) .1432(2) .17694(10) .0397(6) Uani d . 1 . . C H6 .5377 .1974 .1876 .052 Uiso calc R 1 . . H C5 .2316(5) .1526(2) .25858(9) .0389(6) Uani d . 1 . . C C10 .2102(6) .2081(2) .14761(10) .0431(6) Uani d . 1 . . C H10A .1162 .1523 .1286 .056 Uiso calc R 1 . . H H10B .0961 .2461 .1698 .056 Uiso calc R 1 . . H C13 .5235(6) .5661(3) .01026(12) .0530(8) Uani d . 1 . . C H13 .6978 .5904 .0090 .069 Uiso calc R 1 . . H C1 .1008(5) .1012(3) .30359(11) .0475(7) Uani d . 1 . . C C9 .2741(7) -.0412(2) .21346(11) .0506(7) Uani d . 1 . . C H9A .1070 -.0689 .2198 .066 Uiso calc R 1 . . H H9B .3889 -.0813 .2349 .066 Uiso calc R 1 . . H C11 .6451(6) .2631(3) .06192(13) .0534(8) Uani d . 1 . . C H11A .7075 .2083 .0380 .069 Uiso calc R 1 . . H H11B .7366 .2499 .0918 .069 Uiso calc R 1 . . H C7 .5233(7) .0403(3) .15064(12) .0575(8) Uani d . 1 . . C H7A .5368 .0556 .1161 .075 Uiso calc R 1 . . H H7B .6870 .0229 .1634 .075 Uiso calc R 1 . . H C4 .1954(8) -.0178(3) .32134(14) .0700(10) Uani d . 1 . . C H4A .3667 -.0113 .3305 .091 Uiso calc R 1 . . H H4B .1792 -.0741 .2957 .091 Uiso calc R 1 . . H H4C .0992 -.0424 .3488 .091 Uiso calc R 1 . . H C8 .3446(8) -.0588(3) .16046(13) .0613(9) Uani d . 1 . . C H8A .4242 -.1338 .1556 .080 Uiso calc R 1 . . H H8B .1999 -.0537 .1396 .080 Uiso calc R 1 . . H C3 .1355(9) .1880(4) .34519(13) .0760(12) Uani d . 1 . . C H3A .3088 .1944 .3529 .099 Uiso calc R 1 . . H H3B .0463 .1613 .3732 .099 Uiso calc R 1 . . H H3C .0731 .2629 .3356 .099 Uiso calc R 1 . . H C14 .3775(11) .6485(3) .04224(18) .0863(13) Uani d . 1 . . C H14A .4540 .6527 .0737 .112 Uiso calc R 1 . . H H14B .2104 .6204 .0456 .112 Uiso calc R 1 . . H H14C .3753 .7246 .0278 .112 Uiso calc R 1 . . H C2 -.1714(6) .0938(6) .29024(17) .0955(18) Uani d . 1 . . C H2A -.1928 .0384 .2644 .124 Uiso calc R 1 . . H H2B -.2286 .1689 .2798 .124 Uiso calc R 1 . . H H2C -.2653 .0692 .3180 .124 Uiso calc R 1 . . H C15 .416(2) .5665(4) -.03952(14) .132(3) Uani d . 1 . . C H15A .5136 .5174 -.0603 .171 Uiso calc R 1 . . H H15B .4160 .6446 -.0520 .171 Uiso calc R 1 . . H H15C .2486 .5378 -.0383 .171 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O2 .0472(11) .0398(9) .0454(10) -.0002(9) .0024(9) .0028(8) O3 .0357(10) .0630(13) .0752(14) -.0026(11) .0017(10) .0116(12) O1 .0694(15) .0398(10) .0594(11) -.0068(12) .0066(11) -.0005(8) N1 .0369(11) .0300(9) .0482(11) -.0010(10) .0008(10) .0092(8) N3 .0353(12) .0434(12) .0618(14) -.0006(11) .0025(11) .0166(11) N2 .0566(14) .0330(10) .0465(12) .0043(12) .0063(11) .0051(9) C12 .0388(13) .0448(14) .0458(13) .0017(13) .0065(12) .0052(11) C6 .0325(12) .0371(12) .0494(14) .0023(12) .0012(11) .0086(11) C5 .0298(12) .0390(13) .0479(13) -.0029(12) -.0021(11) .0077(10) C10 .0400(13) .0396(13) .0496(14) .0069(13) .0042(12) .0109(11) C13 .0462(15) .0431(15) .0696(18) -.0064(15) .0037(14) .0191(13) C1 .0316(13) .0607(17) .0501(14) -.0036(14) .0017(11) .0094(13) C9 .0568(18) .0307(12) .0643(16) -.0012(13) -.0017(15) .0071(11) C11 .0420(15) .0473(16) .0711(18) .0086(14) .0122(14) .0144(14) C7 .0558(18) .0535(17) .0630(17) .0232(16) .0121(15) .0089(14) C4 .068(2) .070(2) .072(2) -.009(2) .0076(19) .0344(18) C8 .077(2) .0377(14) .0690(18) .0118(16) .0012(19) -.0010(13) C3 .085(3) .090(3) .0534(17) -.006(3) .0084(19) .0026(17) C14 .105(4) .0549(19) .099(3) .008(3) -.004(3) -.005(2) C2 .0302(16) .177(6) .080(2) -.011(3) .0022(16) .015(3) C15 .267(9) .074(2) .054(2) -.014(5) -.008(4) .0246(19) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C11 O2 N2 108.6(2) C5 N1 C9 129.3(2) C5 N1 C6 118.8(2) C9 N1 C6 111.7(2) C12 N3 C13 123.7(3) O2 N2 C10 108.2(2) O3 C12 N3 124.9(3) O3 C12 C11 119.1(3) N3 C12 C11 115.9(3) N1 C6 C7 102.2(2) N1 C6 C10 109.6(2) C7 C6 C10 114.3(3) O1 C5 N1 118.9(2) O1 C5 C1 119.1(3) N1 C5 C1 122.0(2) N2 C10 C6 112.7(2) N3 C13 C15 108.6(3) N3 C13 C14 109.2(3) C15 C13 C14 109.4(4) C2 C1 C3 109.7(4) C2 C1 C4 110.4(4) C3 C1 C4 107.4(3) C2 C1 C5 105.6(3) C3 C1 C5 107.3(3) C4 C1 C5 116.3(3) N1 C9 C8 103.1(2) O2 C11 C12 115.7(2) C8 C7 C6 103.8(2) C7 C8 C9 103.3(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O2 C11 . 1.411(4) ? O2 N2 . 1.453(3) ? O3 C12 . 1.225(4) ? O1 C5 . 1.232(4) ? N1 C5 . 1.353(4) ? N1 C9 . 1.477(3) ? N1 C6 . 1.485(3) ? N3 C12 . 1.330(4) ? N3 C13 . 1.464(4) ? N2 C10 . 1.464(3) ? C12 C11 . 1.516(4) ? C6 C7 . 1.518(4) ? C6 C10 . 1.531(4) ? C5 C1 . 1.543(4) ? C13 C15 . 1.489(6) ? C13 C14 . 1.513(6) ? C1 C2 . 1.514(4) ? C1 C3 . 1.530(5) ? C1 C4 . 1.536(5) ? C9 C8 . 1.522(5) ? C7 C8 . 1.514(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N3 H3 O2 . 1.022(10) 2.37(4) 2.725(3) 99(2) N3 H3 O3 1_455 1.022(10) 2.250(18) 3.211(3) 156(3) N2 H2 O3 1_455 1.022(10) 2.293(18) 3.249(3) 155(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_publ_flag C13 N3 C12 O3 .6(5) ? C5 N1 C6 C7 161.1(3) ? C9 N1 C6 C7 -14.6(3) ? C1 C5 N1 C6 177.8(2) y C5 N1 C6 C10 -77.4(3) y N1 C6 C10 N2 161.3(2) y C6 C10 N2 O2 83.8(3) y C10 N2 O2 C11 -125.4(2) y N2 O2 C11 C12 -73.8(3) y O2 C11 C12 N3 -12.6(4) y C11 C12 N3 C13 -177.7(3) y C9 N1 C6 C10 107.0(3) ? C9 N1 C5 O1 175.4(3) ? C6 N1 C5 O1 .6(4) ? C9 N1 C5 C1 -7.5(5) ? C7 C6 C10 N2 -84.7(3) ? C12 N3 C13 C15 121.0(5) ? C12 N3 C13 C14 -119.8(4) ? O1 C5 C1 C2 96.9(4) ? N1 C5 C1 C2 -80.3(4) ? O1 C5 C1 C3 -20.0(4) ? N1 C5 C1 C3 162.8(3) ? O1 C5 C1 C4 -140.3(3) ? N1 C5 C1 C4 42.6(4) ? C5 N1 C9 C8 174.9(3) ? C6 N1 C9 C8 -10.0(4) ? O3 C12 C11 O2 169.0(3) ? N1 C6 C7 C8 33.5(3) ? C10 C6 C7 C8 -84.7(3) ? C6 C7 C8 C9 -40.5(3) ? N1 C9 C8 C7 30.7(3) ?