#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/10/2011006.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_2011006 loop_ _publ_author_name ' Zhao, Yuekun' 'Helliwell, Madeleine' ' Joule, John A.' _publ_section_title ; The conversion of a pyrrole trimer derivative into a 4,5,6,7-tetrahydro-4-(pyrrol-2-yl)indol-7-yltosylaminoindole ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 714 _journal_page_last 715 _journal_paper_doi 10.1107/S0108270100003541 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C21 H21 N3 O4 S' _chemical_formula_weight 411.47 _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.788(2) _cell_length_b 6.6204(16) _cell_length_c 25.057(3) _cell_measurement_reflns_used 17 _cell_measurement_temperature 293.2 _cell_measurement_theta_max 39.8 _cell_measurement_theta_min 38.5 _cell_volume 1955.5(6) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1995)' _computing_publication_material TEXSAN _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al. 1993)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .968 _diffrn_measured_fraction_theta_max .968 _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents .0000 _diffrn_reflns_av_sigmaI/netI .0196 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 2102 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 79.07 _diffrn_reflns_theta_max 79.07 _diffrn_reflns_theta_min 3.53 _diffrn_standards_decay_% 1.18 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.761 _exptl_absorpt_correction_T_max .768 _exptl_absorpt_correction_T_min .544 _exptl_absorpt_correction_type '\y scans (North et al., 1968)' _exptl_crystal_colour pink _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_description tabular _exptl_crystal_F_000 864 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .40 _exptl_crystal_size_min .15 _refine_diff_density_max .218 _refine_diff_density_min -.197 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 264 _refine_ls_number_reflns 2102 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all .0452 _refine_ls_R_factor_gt .0380 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.3269P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1071 _reflns_number_gt 1919 _reflns_number_total 2102 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gd1093.cif _cod_data_source_block (2) _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.3269P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.3269P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2011006 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' '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_assembly _atom_site_disorder_group _atom_site_type_symbol S1 .21915(7) -.11439(13) .40862(3) .0452(2) Uani d . 1 . . S O1 .2935(2) -.2699(4) .38861(12) .0599(7) Uani d . 1 . . O O2 .1228(2) -.1706(5) .43971(11) .0641(8) Uani d . 1 . . O O3 -.2094(2) -.4180(4) .25519(11) .0519(6) Uani d . 1 . . O O4 .3506(4) -.0257(7) .11228(16) .0953(13) Uani d . 1 . . O N1 .1756(3) .0101(6) .35761(11) .0529(8) Uani d . 1 . . N H1 .2182 .0078 .3298 .063 Uiso calc R 1 . . H N2 -.0576(2) -.1086(4) .30046(11) .0387(6) Uani d . 1 . . N H2 -.0721 -.1917 .3259 .046 Uiso calc R 1 . . H N3 .2003(2) .2209(5) .17757(12) .0462(7) Uani d . 1 . . N H3 .2169 .1140 .1954 .055 Uiso calc R 1 . . H C1 .0696(3) .1280(5) .35373(14) .0424(7) Uani d . 1 . . C H1A .0228 .1041 .3854 .051 Uiso calc R 1 . . H C2 .0919(4) .3553(6) .34740(18) .0599(11) Uani d . 1 . . C H2A .0207 .4278 .3502 .072 Uiso calc R 1 . . H H2B .1409 .4007 .3761 .072 Uiso calc R 1 . . H C3 .1474(4) .4046(6) .29404(16) .0553(9) Uani d . 1 . . C H3A .2169 .3273 .2905 .066 Uiso calc R 1 . . H H3B .1672 .5468 .2932 .066 Uiso calc R 1 . . H C4 .0690(3) .3568(5) .24688(16) .0461(8) Uani d . 1 . . C H4 .0098 .4607 .2464 .055 Uiso calc R 1 . . H C5 .0102(3) .1553(5) .25561(13) .0394(7) Uani d . 1 . . C C6 .0069(3) .0602(4) .30458(13) .0376(6) Uani d . 1 . . C C7 -.0532(3) .0384(5) .22032(14) .0422(7) Uani d . 1 . . C H7 -.0646 .0649 .1843 .051 Uiso calc R 1 . . H C8 -.0962(3) -.1252(5) .24869(13) .0393(7) Uani d . 1 . . C C9 -.1691(3) -.2796(5) .22912(13) .0434(7) Uani d . 1 . . C H9 -.1877 -.2748 .1931 .052 Uiso calc R 1 . . H C10 .1285(3) .3660(5) .19395(15) .0461(8) Uani d . 1 . . C C11 .1241(4) .5107(7) .15453(19) .0665(12) Uani d . 1 . . C H11 .0806 .6278 .1551 .080 Uiso calc R 1 . . H C12 .1959(4) .4509(8) .11400(19) .0679(12) Uani d . 1 . . C H12 .2098 .5218 .0826 .082 Uiso calc R 1 . . H C13 .2435(3) .2687(7) .12794(14) .0532(9) Uani d . 1 . . C C14 .3179(4) .1401(9) .09877(17) .0672(12) Uani d . 1 . . C H14 .3439 .1881 .0661 .081 Uiso calc R 1 . . H C15 .3036(3) .0469(5) .44833(13) .0409(7) Uani d . 1 . . C C16 .4077(3) -.0159(6) .46530(15) .0486(8) Uani d . 1 . . C H16 .4363 -.1404 .4546 .058 Uiso calc R 1 . . H C17 .4704(3) .1085(7) .49879(17) .0578(10) Uani d . 1 . . C H17 .5409 .0648 .5108 .069 Uiso calc R 1 . . H C18 .4309(3) .2954(6) .51467(14) .0502(8) Uani d . 1 . . C C19 .3263(5) .3549(7) .49646(19) .0701(13) Uani d . 1 . . C H19 .2986 .4817 .5058 .084 Uiso calc R 1 . . H C20 .2614(4) .2302(8) .46457(19) .0705(13) Uani d . 1 . . C H20 .1892 .2703 .4541 .085 Uiso calc R 1 . . H C21 .4998(5) .4280(8) .5517(2) .0766(14) Uani d . 1 . . C H21A .5542 .5033 .5314 .115 Uiso calc R 1 . . H H21B .5386 .3450 .5773 .115 Uiso calc R 1 . . H H21C .4502 .5197 .5701 .115 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 S1 .0459(4) .0519(4) .0379(3) -.0048(3) -.0023(4) -.0088(4) O1 .0728(18) .0518(15) .0550(14) .0041(12) -.0077(13) -.0121(12) O2 .0577(16) .0798(19) .0547(16) -.0191(15) .0007(13) .0010(15) O3 .0545(14) .0518(13) .0496(13) -.0133(12) .0049(11) -.0079(12) O4 .109(3) .105(3) .071(2) .024(3) .034(2) .012(2) N1 .0464(16) .080(2) .0322(13) .0037(16) -.0029(12) -.0086(14) N2 .0389(13) .0378(12) .0393(13) -.0030(10) .0009(11) .0044(11) N3 .0481(15) .0498(16) .0407(13) -.0022(13) .0025(12) .0119(12) C1 .0430(18) .0459(17) .0382(15) -.0032(14) .0048(13) -.0064(14) C2 .073(3) .051(2) .056(2) -.0121(19) .013(2) -.0173(18) C3 .064(2) .0423(18) .060(2) -.0150(16) .0084(19) -.0072(17) C4 .0437(18) .0342(15) .060(2) .0010(13) .0059(16) .0079(15) C5 .0309(15) .0405(15) .0468(17) .0032(12) .0026(13) .0049(13) C6 .0339(15) .0365(14) .0425(16) .0006(12) .0023(13) -.0002(13) C7 .0369(15) .0488(17) .0409(16) .0040(14) -.0003(13) .0080(14) C8 .0352(15) .0427(16) .0398(15) .0036(12) .0001(12) -.0010(14) C9 .0408(17) .0488(18) .0406(16) .0026(14) -.0010(13) -.0059(15) C10 .0412(17) .0424(17) .055(2) -.0065(14) -.0029(15) .0140(15) C11 .064(2) .060(2) .075(3) .0014(19) -.009(2) .030(2) C12 .068(3) .080(3) .056(2) -.012(2) -.004(2) .032(2) C13 .053(2) .066(2) .0406(16) -.0153(18) -.0020(16) .0137(17) C14 .070(3) .089(3) .0426(19) -.018(2) .0086(19) .004(2) C15 .0411(16) .0477(17) .0340(14) -.0016(14) -.0025(12) -.0062(13) C16 .0474(18) .053(2) .0457(17) .0051(15) -.0062(15) .0001(16) C17 .0421(19) .074(2) .057(2) -.0001(17) -.0123(17) .002(2) C18 .055(2) .058(2) .0381(16) -.0137(17) -.0061(15) .0017(15) C19 .091(3) .059(2) .060(2) .017(2) -.023(2) -.022(2) C20 .064(2) .079(3) .069(3) .025(2) -.028(2) -.033(2) C21 .089(3) .080(3) .061(3) -.026(3) -.020(2) -.008(2) 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' N N .0311 .0180 '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' S S .3331 .5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 6 -1 1 -2 2 1 3 2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O2 S1 O1 119.18(19) O2 S1 N1 108.29(18) O1 S1 N1 106.52(17) O2 S1 C15 107.38(16) O1 S1 C15 106.56(16) N1 S1 C15 108.57(18) C1 N1 S1 126.5(2) C1 N1 H1 116.7 S1 N1 H1 116.7 C6 N2 C8 108.8(3) C6 N2 H2 125.6 C8 N2 H2 125.6 C10 N3 C13 110.1(3) C10 N3 H3 124.9 C13 N3 H3 124.9 N1 C1 C6 108.2(3) N1 C1 C2 112.3(3) C6 C1 C2 107.0(3) N1 C1 H1A 109.8 C6 C1 H1A 109.8 C2 C1 H1A 109.8 C3 C2 C1 112.0(3) C3 C2 H2A 109.2 C1 C2 H2A 109.2 C3 C2 H2B 109.2 C1 C2 H2B 109.2 H2A C2 H2B 107.9 C2 C3 C4 111.9(3) C2 C3 H3A 109.2 C4 C3 H3A 109.2 C2 C3 H3B 109.2 C4 C3 H3B 109.2 H3A C3 H3B 107.9 C10 C4 C5 112.1(3) C10 C4 C3 113.0(3) C5 C4 C3 110.2(3) C10 C4 H4 107.1 C5 C4 H4 107.1 C3 C4 H4 107.1 C6 C5 C7 107.2(3) C6 C5 C4 122.8(3) C7 C5 C4 129.9(3) N2 C6 C5 108.9(3) N2 C6 C1 125.7(3) C5 C6 C1 125.3(3) C8 C7 C5 107.7(3) C8 C7 H7 126.2 C5 C7 H7 126.2 N2 C8 C7 107.3(3) N2 C8 C9 125.5(3) C7 C8 C9 127.1(3) O3 C9 C8 126.1(3) O3 C9 H9 116.9 C8 C9 H9 116.9 N3 C10 C11 107.5(4) N3 C10 C4 122.3(3) C11 C10 C4 130.1(4) C10 C11 C12 107.8(4) C10 C11 H11 126.1 C12 C11 H11 126.1 C13 C12 C11 108.3(4) C13 C12 H12 125.8 C11 C12 H12 125.8 C12 C13 N3 106.2(4) C12 C13 C14 130.2(4) N3 C13 C14 123.6(4) O4 C14 C13 126.4(4) O4 C14 H14 116.8 C13 C14 H14 116.8 C16 C15 C20 120.2(3) C16 C15 S1 119.9(3) C20 C15 S1 119.8(3) C15 C16 C17 119.1(4) C15 C16 H16 120.4 C17 C16 H16 120.4 C18 C17 C16 121.7(4) C18 C17 H17 119.1 C16 C17 H17 119.1 C19 C18 C17 117.7(3) C19 C18 C21 121.3(4) C17 C18 C21 121.0(4) C18 C19 C20 121.2(4) C18 C19 H19 119.4 C20 C19 H19 119.4 C15 C20 C19 120.0(4) C15 C20 H20 120.0 C19 C20 H20 120.0 C18 C21 H21A 109.5 C18 C21 H21B 109.5 H21A C21 H21B 109.5 C18 C21 H21C 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 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 S1 O2 . 1.427(3) ? S1 O1 . 1.443(3) ? S1 N1 . 1.605(3) ? S1 C15 . 1.767(3) ? O3 C9 . 1.222(4) ? O4 C14 . 1.212(7) ? N1 C1 . 1.476(5) ? N1 H1 . .8600 ? N2 C6 . 1.356(4) ? N2 C8 . 1.379(4) ? N2 H2 . .8600 ? N3 C10 . 1.344(5) ? N3 C13 . 1.381(5) ? N3 H3 . .8600 ? C1 C6 . 1.505(5) ? C1 C2 . 1.536(5) ? C1 H1A . .9800 ? C2 C3 . 1.524(6) ? C2 H2A . .9700 ? C2 H2B . .9700 ? C3 C4 . 1.533(6) ? C3 H3A . .9700 ? C3 H3B . .9700 ? C4 C10 . 1.501(5) ? C4 C5 . 1.519(4) ? C4 H4 . .9800 ? C5 C6 . 1.380(5) ? C5 C7 . 1.392(5) ? C7 C8 . 1.392(5) ? C7 H7 . .9300 ? C8 C9 . 1.422(5) ? C9 H9 . .9300 ? C10 C11 . 1.377(5) ? C11 C12 . 1.380(7) ? C11 H11 . .9300 ? C12 C13 . 1.376(7) ? C12 H12 . .9300 ? C13 C14 . 1.423(7) ? C14 H14 . .9300 ? C15 C16 . 1.364(5) ? C15 C20 . 1.373(6) ? C16 C17 . 1.389(5) ? C16 H16 . .9300 ? C17 C18 . 1.381(6) ? C17 H17 . .9300 ? C18 C19 . 1.372(6) ? C18 C21 . 1.514(6) ? C19 C20 . 1.380(6) ? C19 H19 . .9300 ? C20 H20 . .9300 ? C21 H21A . .9600 ? C21 H21B . .9600 ? C21 H21C . .9600 ? 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 N1 H1 O3 4_545 .86 2.14 2.966(4) 161 yes N2 H2 O1 4_445 .86 2.25 2.934(4) 137 yes N3 H3 O3 4_545 .86 2.16 2.989(4) 161 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 O2 S1 N1 C1 25.9(4) O1 S1 N1 C1 155.3(3) C15 S1 N1 C1 -90.3(3) S1 N1 C1 C6 -128.0(3) S1 N1 C1 C2 114.1(4) N1 C1 C2 C3 67.1(5) C6 C1 C2 C3 -51.5(5) C1 C2 C3 C4 64.8(5) C2 C3 C4 C10 -169.0(3) C2 C3 C4 C5 -42.7(4) C10 C4 C5 C6 142.0(3) C3 C4 C5 C6 15.2(4) C10 C4 C5 C7 -41.9(5) C3 C4 C5 C7 -168.7(3) C8 N2 C6 C5 .4(3) C8 N2 C6 C1 -176.9(3) C7 C5 C6 N2 -.9(4) C4 C5 C6 N2 176.0(3) C7 C5 C6 C1 176.3(3) C4 C5 C6 C1 -6.8(5) N1 C1 C6 N2 79.7(4) C2 C1 C6 N2 -159.1(3) N1 C1 C6 C5 -97.1(4) C2 C1 C6 C5 24.1(5) C6 C5 C7 C8 1.1(4) C4 C5 C7 C8 -175.5(3) C6 N2 C8 C7 .3(3) C6 N2 C8 C9 -178.2(3) C5 C7 C8 N2 -.9(4) C5 C7 C8 C9 177.5(3) N2 C8 C9 O3 1.2(6) C7 C8 C9 O3 -177.1(3) C13 N3 C10 C11 .2(4) C13 N3 C10 C4 -179.4(3) C5 C4 C10 N3 -50.6(5) C3 C4 C10 N3 74.7(4) C5 C4 C10 C11 129.9(4) C3 C4 C10 C11 -104.8(5) N3 C10 C11 C12 -.6(5) C4 C10 C11 C12 178.9(4) C10 C11 C12 C13 .7(5) C11 C12 C13 N3 -.6(5) C11 C12 C13 C14 176.3(4) C10 N3 C13 C12 .3(4) C10 N3 C13 C14 -176.9(4) C12 C13 C14 O4 -174.7(5) N3 C13 C14 O4 1.8(8) O2 S1 C15 C16 112.6(3) O1 S1 C15 C16 -16.2(3) N1 S1 C15 C16 -130.5(3) O2 S1 C15 C20 -63.6(4) O1 S1 C15 C20 167.6(4) N1 S1 C15 C20 53.3(4) C20 C15 C16 C17 -.5(6) S1 C15 C16 C17 -176.6(3) C15 C16 C17 C18 -1.0(6) C16 C17 C18 C19 .4(6) C16 C17 C18 C21 179.2(4) C17 C18 C19 C20 1.8(7) C21 C18 C19 C20 -177.1(5) C16 C15 C20 C19 2.6(7) S1 C15 C20 C19 178.7(4) C18 C19 C20 C15 -3.3(8) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 11774252