#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/30/2013075.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_2013075 loop_ _publ_author_name 'Lynch, Daniel E.' 'Ian McClenaghan' _publ_section_title ; 2-(Pyrrolidin-1-yl)-1,4-naphthoquinone and 2-phenylsulfanyl-3-(pyrrolidin-1-yl)-1,4-naphthoquinone ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o704 _journal_page_last o707 _journal_paper_doi 10.1107/S0108270102019194 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C20 H17 N O2 S' _chemical_formula_moiety 'C20 H17 N O2 S' _chemical_formula_sum 'C20 H17 N O2 S' _chemical_formula_weight 335.42 _chemical_name_systematic ; 2-(phenylthio)-3-(pyrrolidin-1-yl)-1,4-naphthoquinone ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 93.12(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.205(3) _cell_length_b 11.387(2) _cell_length_c 11.220(2) _cell_measurement_reflns_used 8654 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _cell_volume 1684.6(6) _computing_cell_refinement 'DENZO and COLLECT' _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO and COLLECT' _computing_molecular_graphics 'PLUTON94 (Spek, 1994) and PLATON97 (Spek, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full 0.963 _diffrn_measured_fraction_theta_max 0.963 _diffrn_measurement_device_type 'Bruker--Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Bruker--Nonius FR591 rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0753 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 11174 _diffrn_reflns_theta_full 27.45 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.9 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.204 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_correction_T_min 0.912 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.16 _refine_diff_density_min -0.22 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 3716 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.951 _refine_ls_R_factor_all 0.1100 _refine_ls_R_factor_gt 0.0482 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0633P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1035 _refine_ls_wR_factor_ref 0.1260 _reflns_number_gt 2088 _reflns_number_total 3716 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gg1143.cif _cod_data_source_block II _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. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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_Hall -P2ybc _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2013075 _cod_database_fobs_code 2013075 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -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 C1 0.40096(16) 0.74543(19) -0.03400(17) 0.0485(5) Uani d . 1 . . C O1 0.47061(12) 0.81306(15) -0.05171(15) 0.0744(5) Uani d . 1 . . O C2 0.31222(14) 0.78222(18) 0.03657(15) 0.0409(5) Uani d . 1 . . C N21 0.27978(12) 0.89343(15) 0.02664(13) 0.0467(4) Uani d . 1 . . N C22 0.17644(17) 0.93098(19) 0.05505(18) 0.0570(6) Uani d . 1 . . C H221 0.1748 0.9568 0.1392 0.071 Uiso calc R 1 . . H H222 0.1270 0.8665 0.0409 0.071 Uiso calc R 1 . . H C23 0.15373(19) 1.0331(2) -0.0305(2) 0.0693(7) Uani d . 1 . . C H231 0.1290 1.0047 -0.1102 0.087 Uiso calc R 1 . . H H232 0.1028 1.0870 0.0010 0.087 Uiso calc R 1 . . H C24 0.2560(2) 1.0924(2) -0.0356(2) 0.0769(8) Uani d . 1 . . C H241 0.2711 1.1412 0.0362 0.096 Uiso calc R 1 . . H H242 0.2588 1.1423 -0.1076 0.096 Uiso calc R 1 . . H C25 0.32974(18) 0.98972(18) -0.04050(19) 0.0585(6) Uani d . 1 . . C H251 0.3393 0.9660 -0.1240 0.073 Uiso calc R 1 . . H H252 0.3965 1.0103 -0.0017 0.073 Uiso calc R 1 . . H C3 0.27236(14) 0.69487(18) 0.11022(15) 0.0435(5) Uani d . 1 . . C S3 0.22008(4) 0.73593(5) 0.24541(4) 0.0527(2) Uani d . 1 . . S C31 0.08772(15) 0.71279(18) 0.23074(16) 0.0472(5) Uani d . 1 . . C C32 0.0299(2) 0.7770(2) 0.3067(2) 0.0748(7) Uani d . 1 . . C H32 0.0620 0.8313 0.3608 0.093 Uiso calc R 1 . . H C33 -0.0739(2) 0.7628(3) 0.3043(3) 0.0905(9) Uani d . 1 . . C H33 -0.1126 0.8075 0.3570 0.113 Uiso calc R 1 . . H C34 -0.12134(19) 0.6862(3) 0.2280(2) 0.0761(7) Uani d . 1 . . C H34 -0.1928 0.6763 0.2276 0.095 Uiso calc R 1 . . H C35 -0.0653(2) 0.6227(3) 0.1513(2) 0.0817(8) Uani d . 1 . . C H35 -0.0984 0.5695 0.0969 0.102 Uiso calc R 1 . . H C36 0.03861(18) 0.6353(2) 0.1523(2) 0.0713(7) Uani d . 1 . . C H36 0.0766 0.5906 0.0989 0.089 Uiso calc R 1 . . H C4 0.28995(15) 0.57049(19) 0.08875(17) 0.0482(5) Uani d . 1 . . C O4 0.25770(12) 0.49153(13) 0.15308(13) 0.0696(5) Uani d . 1 . . O C5 0.34672(17) 0.4205(2) -0.0580(2) 0.0628(6) Uani d . 1 . . C H5 0.3114 0.3617 -0.0168 0.078 Uiso calc R 1 . . H C6 0.39965(18) 0.3910(2) -0.1568(2) 0.0748(7) Uani d . 1 . . C H6 0.3990 0.3122 -0.1845 0.094 Uiso calc R 1 . . H C7 0.45313(19) 0.4748(3) -0.2154(2) 0.0757(8) Uani d . 1 . . C H7 0.4884 0.4537 -0.2838 0.095 Uiso calc R 1 . . H C8 0.45590(16) 0.5905(2) -0.17482(19) 0.0651(7) Uani d . 1 . . C H8 0.4951 0.6475 -0.2134 0.081 Uiso calc R 1 . . H C9 0.40071(14) 0.62191(19) -0.07721(17) 0.0472(5) Uani d . 1 . . C C10 0.34553(14) 0.53670(18) -0.01917(16) 0.0462(5) Uani d . 1 . . C 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 C1 0.0413(12) 0.0558(15) 0.0483(12) -0.0027(10) 0.0011(9) 0.0128(10) O1 0.0555(10) 0.0679(12) 0.1015(12) -0.0126(9) 0.0204(9) 0.0143(10) C2 0.0432(12) 0.0439(13) 0.0352(10) -0.0073(9) -0.0023(8) -0.0002(8) N21 0.0546(11) 0.0412(11) 0.0443(9) -0.0049(8) 0.0039(7) 0.0006(7) C22 0.0644(15) 0.0480(15) 0.0590(13) 0.0039(11) 0.0067(10) -0.0024(10) C23 0.0832(19) 0.0497(16) 0.0745(15) 0.0118(13) 0.0008(12) 0.0029(12) C24 0.109(2) 0.0426(16) 0.0787(17) -0.0033(14) 0.0045(14) 0.0052(12) C25 0.0741(16) 0.0428(14) 0.0588(13) -0.0144(12) 0.0050(10) 0.0072(10) C3 0.0452(12) 0.0465(14) 0.0385(10) -0.0030(9) 0.0013(8) 0.0027(9) S3 0.0553(4) 0.0670(4) 0.0358(3) -0.0066(3) 0.0016(2) -0.0014(2) C31 0.0538(13) 0.0488(13) 0.0394(10) -0.0003(10) 0.0059(9) 0.0075(9) C32 0.0685(18) 0.083(2) 0.0739(17) -0.0019(14) 0.0136(13) -0.0202(14) C33 0.071(2) 0.109(3) 0.094(2) 0.0108(17) 0.0256(16) -0.0120(17) C34 0.0525(16) 0.090(2) 0.0860(18) -0.0001(15) 0.0057(13) 0.0237(16) C35 0.0639(18) 0.090(2) 0.0899(19) -0.0077(15) -0.0096(14) -0.0066(15) C36 0.0583(16) 0.082(2) 0.0732(15) -0.0025(13) 0.0029(12) -0.0227(13) C4 0.0452(12) 0.0473(15) 0.0520(12) -0.0054(10) 0.0009(9) 0.0086(10) O4 0.0844(13) 0.0510(11) 0.0753(10) -0.0041(8) 0.0220(8) 0.0151(8) C5 0.0550(15) 0.0571(17) 0.0757(15) 0.0020(11) -0.0004(11) -0.0072(12) C6 0.0621(17) 0.076(2) 0.0859(18) 0.0122(14) -0.0018(13) -0.0267(15) C7 0.0593(17) 0.102(2) 0.0659(15) 0.0185(15) 0.0056(12) -0.0232(15) C8 0.0517(14) 0.084(2) 0.0610(14) 0.0104(12) 0.0104(10) 0.0044(13) C9 0.0381(12) 0.0551(15) 0.0481(11) 0.0047(10) -0.0005(8) 0.0035(10) C10 0.0407(12) 0.0482(14) 0.0490(11) 0.0023(10) -0.0036(8) -0.0014(10) 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' S S 0.1246 0.1234 '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 O1 C1 C9 122.03(19) O1 C1 C2 121.5(2) C9 C1 C2 116.45(17) N21 C2 C3 125.91(18) N21 C2 C1 118.22(16) C3 C2 C1 115.85(18) C2 N21 C22 123.32(16) C2 N21 C25 125.74(16) C22 N21 C25 109.38(16) N21 C22 C23 103.67(16) N21 C22 H221 111.0 C23 C22 H221 111.0 N21 C22 H222 111.0 C23 C22 H222 111.0 H221 C22 H222 109.0 C24 C23 C22 102.61(19) C24 C23 H231 111.2 C22 C23 H231 111.2 C24 C23 H232 111.2 C22 C23 H232 111.2 H231 C23 H232 109.2 C23 C24 C25 103.44(19) C23 C24 H241 111.1 C25 C24 H241 111.1 C23 C24 H242 111.1 C25 C24 H242 111.1 H241 C24 H242 109.0 N21 C25 C24 104.06(18) N21 C25 H251 110.9 C24 C25 H251 110.9 N21 C25 H252 110.9 C24 C25 H252 110.9 H251 C25 H252 109.0 C2 C3 C4 121.31(18) C2 C3 S3 119.48(16) C4 C3 S3 118.23(14) C3 S3 C31 108.18(10) C36 C31 C32 118.3(2) C36 C31 S3 125.59(17) C32 C31 S3 116.10(18) C33 C32 C31 120.5(2) C33 C32 H32 119.8 C31 C32 H32 119.8 C34 C33 C32 120.9(3) C34 C33 H33 119.5 C32 C33 H33 119.5 C33 C34 C35 119.3(2) C33 C34 H34 120.3 C35 C34 H34 120.3 C34 C35 C36 120.8(2) C34 C35 H35 119.6 C36 C35 H35 119.6 C35 C36 C31 120.2(2) C35 C36 H36 119.9 C31 C36 H36 119.9 O4 C4 C3 122.99(19) O4 C4 C10 118.79(19) C3 C4 C10 118.17(17) C6 C5 C10 119.7(2) C6 C5 H5 120.2 C10 C5 H5 120.2 C7 C6 C5 120.6(2) C7 C6 H6 119.7 C5 C6 H6 119.7 C6 C7 C8 120.3(2) C6 C7 H7 119.8 C8 C7 H7 119.8 C7 C8 C9 119.6(2) C7 C8 H8 120.2 C9 C8 H8 120.2 C8 C9 C10 119.7(2) C8 C9 C1 120.4(2) C10 C9 C1 119.81(18) C5 C10 C9 119.95(19) C5 C10 C4 120.68(19) C9 C10 C4 119.29(18) 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 C1 O1 . 1.224(2) ? C1 C9 . 1.488(3) ? C1 C2 . 1.509(3) ? C2 N21 . 1.340(2) ? C2 C3 . 1.413(3) ? N21 C22 . 1.481(3) ? N21 C25 . 1.503(2) ? C22 C23 . 1.527(3) ? C22 H221 . 0.99 ? C22 H222 . 0.99 ? C23 C24 . 1.514(3) ? C23 H231 . 0.99 ? C23 H232 . 0.99 ? C24 C25 . 1.524(3) ? C24 H241 . 0.99 ? C24 H242 . 0.99 ? C25 H251 . 0.99 ? C25 H252 . 0.99 ? C3 C4 . 1.457(3) ? C3 S3 . 1.7636(19) ? S3 C31 . 1.766(2) ? C31 C36 . 1.383(3) ? C31 C32 . 1.384(3) ? C32 C33 . 1.379(3) ? C32 H32 . 0.95 ? C33 C34 . 1.352(4) ? C33 H33 . 0.95 ? C34 C35 . 1.371(3) ? C34 H34 . 0.95 ? C35 C36 . 1.379(3) ? C35 H35 . 0.95 ? C36 H36 . 0.95 ? C4 O4 . 1.243(2) ? C4 C10 . 1.500(3) ? C5 C6 . 1.384(3) ? C5 C10 . 1.394(3) ? C5 H5 . 0.95 ? C6 C7 . 1.375(4) ? C6 H6 . 0.95 ? C7 C8 . 1.393(4) ? C7 H7 . 0.95 ? C8 C9 . 1.395(3) ? C8 H8 . 0.95 ? C9 C10 . 1.396(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 _geom_hbond_publ_flag C7 H7 O1 2_644 0.95 2.52 3.395(3) 152 yes 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 C1 C2 N21 C22 158.33(18) yes C2 N21 C22 C23 -148.64(18) yes N21 C22 C23 C24 -36.2(2) yes C22 C23 C24 C25 41.0(2) yes C23 C24 C25 N21 -29.9(2) yes C24 C25 N21 C2 173.47(18) yes C25 N21 C2 C1 -5.9(3) yes O1 C1 C2 N21 35.0(3) ? C9 C1 C2 N21 -146.92(17) ? O1 C1 C2 C3 -143.5(2) ? C9 C1 C2 C3 34.5(2) ? C3 C2 N21 C22 -23.3(3) ? C3 C2 N21 C25 172.44(18) ? C25 N21 C22 C23 17.9(2) ? C22 N21 C25 C24 7.4(2) ? N21 C2 C3 C4 160.75(18) ? C1 C2 C3 C4 -20.9(3) ? N21 C2 C3 S3 -30.7(3) ? C1 C2 C3 S3 147.67(15) ? C2 C3 S3 C31 110.91(16) ? C4 C3 S3 C31 -80.22(17) ? C3 S3 C31 C36 23.9(2) ? C3 S3 C31 C32 -157.36(17) ? C36 C31 C32 C33 0.6(4) ? S3 C31 C32 C33 -178.3(2) ? C31 C32 C33 C34 0.0(4) ? C32 C33 C34 C35 -0.6(4) ? C33 C34 C35 C36 0.8(4) ? C34 C35 C36 C31 -0.3(4) ? C32 C31 C36 C35 -0.4(4) ? S3 C31 C36 C35 178.30(18) ? C2 C3 C4 O4 178.57(19) ? S3 C3 C4 O4 9.9(3) ? C2 C3 C4 C10 -4.3(3) ? S3 C3 C4 C10 -172.91(13) ? C10 C5 C6 C7 1.6(3) ? C5 C6 C7 C8 0.9(4) ? C6 C7 C8 C9 -2.6(3) ? C7 C8 C9 C10 1.7(3) ? C7 C8 C9 C1 -178.76(19) ? O1 C1 C9 C8 -24.7(3) ? C2 C1 C9 C8 157.19(18) ? O1 C1 C9 C10 154.8(2) ? C2 C1 C9 C10 -23.3(3) ? C6 C5 C10 C9 -2.4(3) ? C6 C5 C10 C4 -179.12(18) ? C8 C9 C10 C5 0.7(3) ? C1 C9 C10 C5 -178.76(19) ? C8 C9 C10 C4 177.50(18) ? C1 C9 C10 C4 -2.0(3) ? O4 C4 C10 C5 10.5(3) ? C3 C4 C10 C5 -166.84(18) ? O4 C4 C10 C9 -166.27(18) ? C3 C4 C10 C9 16.4(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 5238465