#------------------------------------------------------------------------------ #$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/00/2200036.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_2200036 loop_ _publ_author_name 'Coles, Simon J.' 'Hibbs, David E.' 'Hursthouse, Michael B' _publ_section_title ; 5-tert-Butylperoxy-5-(oxiran-2-yl)-1-(prop-2-ynyl)pyrrolidin-2-one ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o66 _journal_page_last o67 _journal_paper_doi 10.1107/S1600536800020018 _journal_volume 57 _journal_year 2001 _chemical_formula_sum 'C13 H19 N O4' _chemical_formula_weight 253.29 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 112.423(13) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.2870(14) _cell_length_b 10.729(2) _cell_length_c 13.1233(13) _cell_measurement_reflns_used 5318 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 24.9 _cell_measurement_theta_min 2.5 _cell_volume 1338.9(4) _computing_cell_refinement MADNES _computing_data_collection 'MADNES (Pflugrath & Messerschmidt, 1989)' _computing_data_reduction 'ABSMAD (Karaulov, 1992)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1993)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_measurement_device 'FAST TV area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .073 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 5318 _diffrn_reflns_theta_max 24.9 _diffrn_reflns_theta_min 2.5 _exptl_absorpt_coefficient_mu .093 _exptl_absorpt_correction_T_max .989 _exptl_absorpt_correction_T_min .985 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details '(Walker & Stuart, 1983)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.257 _exptl_crystal_description block _exptl_crystal_F_000 544 _exptl_crystal_size_max .2 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .15 _refine_diff_density_max .23 _refine_diff_density_min -.19 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .91 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 2041 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .91 _refine_ls_R_factor_gt .040 _refine_ls_shift/su_max .003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0482P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .096 _reflns_number_gt 1516 _reflns_number_total 2041 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cf6025.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/a' _cod_database_code 2200036 _cod_database_fobs_code 2200036 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' 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_group _atom_site_type_symbol N1 .33428(13) .50201(12) .30627(12) .0190(4) Uani d . 1 . N O1 .57416(12) .51488(11) .38099(10) .0290(4) Uani d . 1 . O O2 .14074(12) .62273(11) .19129(10) .0255(3) Uani d . 1 . O O3 .23830(12) .71414(11) .17439(10) .0278(3) Uani d . 1 . O O4 .01181(12) .53935(11) .36334(11) .0318(4) Uani d . 1 . O C1 .3271(2) .3980(2) .2334(2) .0273(5) Uani d . 1 . C H1A .4181 .3880 .2282 .033 Uiso calc R 1 . H H1B .2593 .4175 .1602 .033 Uiso calc R 1 . H C2 .2873(2) .2796(2) .2693(2) .0264(5) Uani d . 1 . C C3 .2535(2) .1852(2) .2981(2) .0364(5) Uani d . 1 . C H3 .2268 .1107 .3208 .044 Uiso d R 1 . H C4 .4584(2) .5569(2) .36907(14) .0212(4) Uani d . 1 . C C5 .4280(2) .6738(2) .41816(15) .0235(4) Uani d . 1 . C H5A .4534 .7467 .38615 .028 Uiso calc R 1 . H H5B .4797 .6752 .49731 .028 Uiso calc R 1 . H C6 .2695(2) .6708(2) .39061(15) .0229(4) Uani d . 1 . C H6A .2504 .6479 .45502 .028 Uiso calc R 1 . H H6B .2280 .7518 .36488 .028 Uiso calc R 1 . H C7 .2102(2) .5729(2) .29977(14) .0208(4) Uani d . 1 . C C8 .0963(2) .48882(15) .3084(2) .0223(4) Uani d . 1 . C H8 .0459 .43817 .2431 .027 Uiso calc R 1 . H C9 .1048(2) .4362(2) .4126(2) .0317(5) Uani d . 1 . C H9A .0629 .3549 .4114 .038 Uiso calc R 1 . H H9B .1888 .4529 .4774 .038 Uiso calc R 1 . H C10 .1530(2) .8031(2) .09353(15) .0224(4) Uani d . 1 . C C11 .0782(2) .7378(2) -.0160(2) .0354(5) Uani d . 1 . C H11A .0201 .7966 -.0690 .053 Uiso calc R 1 . H H11B .0206 .6719 -.0066 .053 Uiso calc R 1 . H H11C .1464 .7036 -.0416 .053 Uiso calc R 1 . H C12 .0529(2) .8694(2) .1350(2) .0313(5) Uani d . 1 . C H12A .0007 .9309 .0821 .047 Uiso calc R 1 . H H12B .1054 .9092 .2040 .047 Uiso calc R 1 . H H12C -.0109 .8099 .1451 .047 Uiso calc R 1 . H C13 .2633(2) .8938(2) .0877(2) .0323(5) Uani d . 1 . C H13A .2183 .9591 .0363 .048 Uiso calc R 1 . H H13B .3283 .8506 .0638 .048 Uiso calc R 1 . H H13C .3131 .9292 .1593 .048 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 N1 .0203(8) .0166(8) .0198(8) -.0004(6) .0074(6) -.0026(6) O1 .0222(7) .0344(8) .0295(8) .0050(6) .0087(6) .0017(6) O2 .0234(7) .0265(7) .0232(7) -.0051(6) .0053(5) .0096(6) O3 .0198(7) .0318(7) .0306(8) .0001(6) .0084(5) .0136(6) O4 .0306(7) .0284(7) .0427(9) .0031(6) .0209(6) .0029(6) C1 .0319(11) .0256(11) .0258(11) .0008(9) .0125(8) -.0032(9) C2 .0268(11) .0218(10) .0271(11) .0012(9) .0064(8) -.0068(9) C3 .0399(12) .0247(11) .0383(13) -.0042(10) .0079(10) -.0044(10) C4 .0225(10) .0229(10) .0170(10) .0014(9) .0064(7) .0063(8) C5 .0252(10) .0187(10) .0237(11) -.0028(8) .0062(8) .0007(8) C6 .0272(10) .0191(9) .0227(11) .0004(8) .0097(8) .0002(8) C7 .0217(9) .0185(9) .0212(10) .0021(8) .0069(8) .0042(8) C8 .0218(9) .0190(9) .0259(11) .0018(8) .0090(8) .0003(8) C9 .0292(11) .0308(11) .0328(12) -.0021(9) .0094(9) .0107(9) C10 .0220(10) .0230(10) .0215(10) .0040(8) .0075(8) .0088(8) C11 .0420(12) .0391(12) .0247(12) -.0020(10) .0124(9) .0037(9) C12 .0336(11) .0272(11) .0363(13) .0031(9) .0170(9) .0065(9) C13 .0264(11) .0365(11) .0338(12) .0019(9) .0114(9) .0136(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 '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 _geom_angle_publ_flag C4 N1 C1 122.10(14) ? C4 N1 C7 114.00(13) yes C1 N1 C7 122.54(13) ? C7 O2 O3 106.66(11) yes C10 O3 O2 106.92(11) yes C8 O4 C9 60.63(11) yes N1 C1 C2 113.8(2) yes C3 C2 C1 179.0(2) ? O1 C4 N1 124.0(2) ? O1 C4 C5 127.3(2) ? N1 C4 C5 108.76(14) yes C4 C5 C6 105.05(13) yes C7 C6 C5 105.71(14) yes O2 C7 N1 110.28(13) ? O2 C7 C8 100.92(13) ? N1 C7 C8 111.62(13) ? O2 C7 C6 114.72(14) ? N1 C7 C6 103.43(13) ? C8 C7 C6 116.09(15) ? O4 C8 C9 60.15(11) yes O4 C8 C7 116.58(14) ? C9 C8 C7 122.1(2) ? O4 C9 C8 59.22(11) ? O3 C10 C12 110.57(14) ? O3 C10 C13 101.79(13) ? C12 C10 C13 109.94(15) ? O3 C10 C11 109.63(14) ? C12 C10 C11 112.8(2) ? C13 C10 C11 111.5(2) ? 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 N1 C4 . 1.361(2) yes N1 C1 . 1.453(2) ? N1 C7 . 1.460(2) yes O1 C4 . 1.227(2) ? O2 C7 . 1.431(2) yes O2 O3 . 1.479(2) yes O3 C10 . 1.448(2) yes O4 C8 . 1.431(2) yes O4 C9 . 1.445(2) yes C1 C2 . 1.467(3) ? C2 C3 . 1.179(3) ? C4 C5 . 1.496(2) yes C5 C6 . 1.529(2) yes C6 C7 . 1.530(2) yes C7 C8 . 1.517(2) ? C8 C9 . 1.451(3) ? C10 C12 . 1.513(2) ? C10 C13 . 1.519(2) ? C10 C11 . 1.518(3) ? 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 C12 H12B O1 4_575 .96 2.59 3.387(2) 140.1 C3 H3 O1 4_565 .93 2.42 3.275(3) 152.9 C9 H9B O1 3_666 .97 2.46 3.420(2) 169.1 C5 H5A O4 4_675 .97 2.42 3.348(2) 159.9