#------------------------------------------------------------------------------ #$Date: 2016-02-19 14:29:56 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/65/2006538.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_2006538 loop_ _publ_author_name 'Kubicki, Maciej' 'Szkaradzi\'nska, Maria B.' 'Codding, Penelope W.' _publ_section_title (11R,11aS-trans)-11-Ethylthio-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1288 _journal_page_last 1290 _journal_paper_doi 10.1107/S0108270197005581 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C14 H18 N2 O S' _chemical_formula_sum 'C14 H18 N2 O S' _chemical_formula_weight 262.36 _chemical_name_systematic ; (11R-trans)-11-ethylthio-1,2,3,10,11,11a-hexahydro--5H-pyrrolo[2,1-c][1,4] benzodiazepin-5-one ; _space_group_IT_number 78 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall 'P 4cw' _symmetry_space_group_name_H-M 'P 43' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.9850(8) _cell_length_b 8.9850(8) _cell_length_c 17.1652(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 39 _cell_measurement_theta_min 14 _cell_volume 1385.75(19) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'ENPROC (Rettig, 1978)' _computing_molecular_graphics 'Stereochemical Workstation (Siemens, 1989)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Enraf-Nonius CAD-4F diffractometer' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator Ni-filter _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3162 _diffrn_reflns_theta_max 74.73 _diffrn_reflns_theta_min 4.92 _diffrn_standards_decay_% 4 _diffrn_standards_interval_time 33 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.989 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.230 _refine_diff_density_min -0.236 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.06(5) _refine_ls_extinction_coef 0.0041(16) _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_goodness_of_fit_all 1.083 _refine_ls_goodness_of_fit_obs 1.115 _refine_ls_matrix_type full _refine_ls_number_parameters 223 _refine_ls_number_reflns 1472 _refine_ls_number_restraints 27 _refine_ls_restrained_S_all 1.240 _refine_ls_restrained_S_obs 1.283 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_obs .0529 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0780P)^2^+0.3355P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1476 _refine_ls_wR_factor_obs .1443 _reflns_number_gt 1347 _reflns_number_total 1472 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk1103.cif _cod_data_source_block brm1 _cod_original_cell_volume 1385.8(2) _cod_original_sg_symbol_H-M P4~3~ _cod_database_code 2006538 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' 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 C11A .124(5) .050(2) .040(2) -.007(3) -.006(3) -.001(2) C1' .090(10) .074(8) .049(6) -.009(7) -.004(6) -.016(6) C2' .198(19) .119(14) .091(11) -.055(15) -.024(14) -.020(11) C3' .100(14) .050(7) .063(8) -.006(9) -.001(9) -.002(5) N4 .080(3) .047(2) .052(2) .006(2) .006(2) .005(2) C1 .114(10) .070(7) .065(6) -.018(7) .010(7) -.029(5) C2 .083(7) .048(5) .086(7) -.018(5) .023(6) -.022(5) C3 .080(9) .050(6) .114(12) -.003(7) .004(8) .013(7) C5 .037(2) .073(3) .051(2) .004(2) -.002(2) .013(2) O5 .057(2) .104(3) .054(2) -.011(2) .0004(15) .030(2) C5A .040(2) .092(3) .040(2) -.007(2) -.002(2) -.007(2) C6 .080(4) .127(6) .060(3) -.024(4) .021(3) -.023(3) C7 .119(6) .142(7) .079(4) -.032(5) .040(4) -.050(5) C8 .093(5) .106(5) .091(5) -.020(4) .001(4) -.052(4) C9 .058(3) .085(3) .069(3) -.018(2) -.001(2) -.024(3) C9A .041(2) .080(3) .040(2) -.004(2) -.005(2) -.011(2) N10 .067(2) .061(2) .046(2) -.011(2) .012(2) -.001(2) C11 .086(3) .058(3) .043(2) .017(2) .021(2) .012(2) S12 .074(2) .049(2) .075(2) .0104(14) .027(2) .012(2) C13 .095(8) .088(8) .138(12) .009(7) .052(8) .030(9) C14 .081(8) .134(12) .180(15) .019(8) .021(10) .036(12) S12' .0403(12) .049(2) .053(2) .0038(10) .0048(10) .0125(15) C13' .057(6) .085(9) .081(9) -.013(6) .005(6) .018(7) C14' .062(8) .136(16) .128(15) -.023(9) -.001(9) .049(13) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol C11a .8622(8) .5068(6) .0558(3) .072(2) Uani d . 1 . C H1A1 .9432(8) .4429(6) .0745(3) .086 Uiso calc PR .554(9) 1 H H1A2 .9347(8) .4253(6) .0554(3) .086 Uiso calc PR .446(9) 2 H C1' .923(2) .6125(15) .1232(7) .071(4) Uani d PD .446(9) 2 C H1C .840(2) .6514(15) .1529(7) .085 Uiso calc PR .446(9) 2 H H1D .985(2) .5549(15) .1582(7) .085 Uiso calc PR .446(9) 2 H C2' 1.010(4) .736(3) .0919(11) .136(8) Uani d PDU .446(9) 2 C H2C 1.115(4) .717(3) .0977(11) .163 Uiso calc PR .446(9) 2 H H2D .985(4) .827(3) .1189(11) .163 Uiso calc PR .446(9) 2 H C3' .969(2) .747(2) .0069(8) .071(5) Uani d PD .446(9) 2 C H3C 1.056(2) .768(2) -.0246(8) .085 Uiso calc PR .446(9) 2 H H3D .896(2) .826(2) -.0014(8) .085 Uiso calc PR .446(9) 2 H N4 .9004(5) .5900(4) -.0146(2) .0596(10) Uani d . 1 . N C1 .8217(19) .6383(13) .1147(7) .083(4) Uani d PD .554(9) 1 C H1A .7154(19) .6573(13) .1153(7) .100 Uiso calc PR .554(9) 1 H H1B .8544(19) .6152(13) .1672(7) .100 Uiso calc PR .554(9) 1 H C2 .9030(15) .7650(10) .0832(7) .072(3) Uani d PD .554(9) 1 C H2A 1.0040(15) .7669(10) .1032(7) .087 Uiso calc PR .554(9) 1 H H2B .8542(15) .8575(10) .0971(7) .087 Uiso calc PR .554(9) 1 H C3 .9033(18) .7444(18) -.0041(9) .082(5) Uani d PD .554(9) 1 C H3A .8166(18) .7907(18) -.0275(9) .098 Uiso calc PR .554(9) 1 H H3B .9922(18) .7872(18) -.0270(9) .098 Uiso calc PR .554(9) 1 H C5 .9054(4) .5374(6) -.0869(3) .0536(10) Uani d . 1 . C O5 .9357(4) .6250(5) -.1410(2) .0715(11) Uani d . 1 . O C5a .8824(5) .3762(6) -.1028(3) .0573(11) Uani d . 1 . C C6 .9484(8) .3293(9) -.1731(4) .089(2) Uani d . 1 . C H6 1.0011(8) .3985(9) -.2025(4) .107 Uiso calc R 1 . H C7 .9381(10) .1857(11) -.1999(5) .113(3) Uani d . 1 . C H7 .9808(10) .1597(11) -.2474(5) .136 Uiso calc R 1 . H C8 .8646(8) .0808(9) -.1566(4) .097(2) Uani d . 1 . C H8 .8609(8) -.0175(9) -.1734(4) .116 Uiso calc R 1 . H C9 .7959(6) .1216(7) -.0878(3) .0705(14) Uani d . 1 . C H9 .7434(6) .0504(7) -.0597(3) .085 Uiso calc R 1 . H C9a .8034(5) .2672(6) -.0594(3) .0539(11) Uani d . 1 . C N10 .7297(5) .2914(5) .0094(2) .0579(10) Uani d . 1 . N H10 .689(5) .215(5) .033(3) .043(11) Uiso d . 1 . H C11 .7132(6) .4247(5) .0479(3) .0625(12) Uani d D 1 . C H11B .6843(6) .3982(5) .1012(3) .075 Uiso calc PR .554(9) 1 H H11A .6757(6) .4037(5) .1004(3) .075 Uiso calc PR .446(9) 2 H S12 .5940(4) .5820(4) .0213(2) .0659(13) Uani d PD .554(9) 1 S C13 .4168(10) .4902(17) .0413(11) .107(5) Uani d PDU .554(9) 1 C H13A .4149(10) .3950(17) .0147(11) .129 Uiso calc PR .554(9) 1 H H13B .4095(10) .4710(17) .0968(11) .129 Uiso calc PR .554(9) 1 H C14 .2918(13) .575(2) .0176(14) .132(6) Uani d PDU .554(9) 1 C H14A .2022(13) .521(2) .0295(14) .171 Uiso calc PR .554(9) 1 H H14B .2970(13) .592(2) -.0376(14) .171 Uiso calc PR .554(9) 1 H H14C .2915(13) .668(2) .0446(14) .171 Uiso calc PR .554(9) 1 H S12' .5589(3) .5194(5) -.0093(2) .0475(12) Uani d PD .446(9) 2 S C13' .4125(11) .3852(17) .0036(9) .074(4) Uani d PD .446(9) 2 C H13C .4478(11) .2881(17) -.0128(9) .089 Uiso calc PR .446(9) 2 H H13D .3875(11) .3790(17) .0585(9) .089 Uiso calc PR .446(9) 2 H C14' .2811(13) .422(2) -.0398(12) .109(7) Uani d PD .446(9) 2 C H14D .2063(13) .348(2) -.0311(12) .141 Uiso calc PR .446(9) 2 H H14E .3048(13) .427(2) -.0943(12) .141 Uiso calc PR .446(9) 2 H H14F .2445(13) .517(2) -.0230(12) .141 Uiso calc PR .446(9) 2 H 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' S S 0.3331 0.5567 '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 N4 C11A C11 112.2(4) N4 C11A C1' 102.3(6) C11 C11A C1' 130.7(7) N4 C11A C1 101.4(5) C11 C11A C1 102.3(7) N4 C11A H1A1 113.3(3) C11 C11A H1A1 113.3(3) C1 C11A H1A1 113.3(7) N4 C11A H1A2 102.7(3) C11 C11A H1A2 102.7(3) C1' C11A H1A2 102.7(7) C2' C1' C11A 111.7(10) C2' C1' H1C 109.3(15) C11A C1' H1C 109.3(7) C2' C1' H1D 109.3(14) C11A C1' H1D 109.3(6) H1C C1' H1D 107.9 C1' C2' C3' 106.2(11) C1' C2' H2C 110.5(16) C3' C2' H2C 110.5(15) C1' C2' H2D 110.5(13) C3' C2' H2D 110.5(14) H2C C2' H2D 108.7 C2' C3' N4 105.0(10) C2' C3' H3C 110.7(13) N4 C3' H3C 110.7(7) C2' C3' H3D 110.7(15) N4 C3' H3D 110.7(8) H3C C3' H3D 108.8 C5 N4 C3 118.2(7) C5 N4 C11A 126.7(4) C3 N4 C11A 113.9(7) C5 N4 C3' 121.5(6) C11A N4 C3' 110.8(6) C2 C1 C11A 103.2(8) C2 C1 H1A 111.1(9) C11A C1 H1A 111.1(7) C2 C1 H1B 111.1(8) C11A C1 H1B 111.1(6) H1A C1 H1B 109.1 C1 C2 C3 105.9(9) C1 C2 H2A 110.6(9) C3 C2 H2A 110.6(8) C1 C2 H2B 110.6(7) C3 C2 H2B 110.6(8) H2A C2 H2B 108.7 N4 C3 C2 104.5(9) N4 C3 H3A 110.9(7) C2 C3 H3A 110.9(8) N4 C3 H3B 110.9(6) C2 C3 H3B 110.9(7) H3A C3 H3B 108.9 O5 C5 N4 118.6(5) O5 C5 C5A 120.5(4) N4 C5 C5A 120.9(4) C6 C5A C9A 117.0(5) C6 C5A C5 112.9(5) C9A C5A C5 130.1(4) C7 C6 C5A 122.7(7) C7 C6 H6 118.7(4) C5A C6 H6 118.7(4) C8 C7 C6 119.7(6) C8 C7 H7 120.1(4) C6 C7 H7 120.1(4) C7 C8 C9 119.8(7) C7 C8 H8 120.1(4) C9 C8 H8 120.1(4) C8 C9 C9A 121.6(6) C8 C9 H9 119.2(4) C9A C9 H9 119.2(3) N10 C9A C9 115.1(5) N10 C9A C5A 125.7(5) C9 C9A C5A 119.1(4) C9A N10 C11 127.1(4) C9A N10 H10 118.(3) C11 N10 H10 115.(3) N10 C11 C11A 111.5(4) N10 C11 S12 128.0(4) C11A C11 S12 99.3(4) N10 C11 S12' 102.7(4) C11A C11 S12' 117.9(4) N10 C11 H11B 105.4(3) C11A C11 H11B 105.4(3) S12 C11 H11B 105.4(2) N10 C11 H11A 108.1(3) C11A C11 H11A 108.1(3) S12' C11 H11A 108.1(2) C13 S12 C11 96.5(4) C14 C13 S12 113.2(9) C14 C13 H13A 108.9(13) S12 C13 H13A 108.9(6) C14 C13 H13B 108.9(11) S12 C13 H13B 108.9(6) H13A C13 H13B 107.8 C13 C14 H14A 109.5(8) C13 C14 H14B 109.5(11) H14A C14 H14B 109.5 C13 C14 H14C 109.5(13) H14A C14 H14C 109.5 H14B C14 H14C 109.5 C13' S12' C11 99.8(4) C14' C13' S12' 112.4(9) C14' C13' H13C 109.1(11) S12' C13' H13C 109.1(5) C14' C13' H13D 109.1(10) S12' C13' H13D 109.1(5) H13C C13' H13D 107.9 C13' C14' H14D 109.5(7) C13' C14' H14E 109.5(10) H14D C14' H14E 109.5 C13' C14' H14F 109.5(11) H14D C14' H14F 109.5 H14E C14' H14F 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 C11A N4 . 1.463(6) ? C11A C11 . 1.535(8) ? C11A C1' . 1.595(12) ? C11A C1 . 1.598(12) ? C11A H1A1 . .98 ? C11A H1A2 . .98 ? C1' C2' . 1.46(2) ? C1' H1C . .97 ? C1' H1D . .97 ? C2' C3' . 1.51(2) ? C2' H2C . .97 ? C2' H2D . .97 ? C3' N4 . 1.59(2) ? C3' H3C . .97 ? C3' H3D . .97 ? N4 C5 . 1.328(6) ? N4 C3 . 1.40(2) ? C1 C2 . 1.457(13) ? C1 H1A . .97 ? C1 H1B . .97 ? C2 C3 . 1.51(2) ? C2 H2A . .97 ? C2 H2B . .97 ? C3 H3A . .97 ? C3 H3B . .97 ? C5 O5 . 1.247(5) ? C5 C5A . 1.488(8) ? C5A C6 . 1.408(7) ? C5A C9A . 1.420(7) ? C6 C7 . 1.374(12) ? C6 H6 . .93 ? C7 C8 . 1.371(12) ? C7 H7 . .93 ? C8 C9 . 1.381(9) ? C8 H8 . .93 ? C9 C9A . 1.398(7) ? C9 H9 . .93 ? C9A N10 . 1.372(6) ? N10 C11 . 1.376(6) ? N10 H10 . .87(5) ? C11 S12 . 1.832(5) ? C11 S12' . 1.900(6) ? C11 H11B . .98 ? C11 H11A . .98 ? S12 C13 . 1.826(10) ? C13 C14 . 1.417(15) ? C13 H13A . .97 ? C13 H13B . .97 ? C14 H14A . .96 ? C14 H14B . .96 ? C14 H14C . .96 ? S12' C13' . 1.799(9) ? C13' C14' . 1.435(15) ? C13' H13C . .97 ? C13' H13D . .97 ? C14' H14D . .96 ? C14' H14E . .96 ? C14' H14F . .96 ? 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 N10 H10 O5 4_565 0.87(5) 1.97(5) 2.823(6) 165(4) 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 C5 C5a C9a N10 -0.3(7) yes C5a C9a N10 C11 2.7(8) yes C9a N10 C11 C11a -48.7(6) yes N10 C11 C11a N4 82.3(5) yes C11 C11a N4 C5 -52.7(7) yes C11a N4 C5 C5a -5.0(8) yes N4 C5 C5a C9a 25.7(7) yes C11a C1 C2 C3 33.4(15) yes C11a C1' C2' C3' 18(3) yes C1 C2 C3 N4 -30.2(16) yes C2 C3 N4 C11a 14.0(13) yes C3 N4 C11a C1 6.1(11) yes N4 C11a C1 C2 -24.3(12) yes C11 C11a C1' C2' -142.2(17) no C1' C2' C3' N4 -20(3) yes C2' C3' N4 C11a 15.7(19) yes C3' N4 C11a C1' -5.0(12) yes N4 C11a C1' C2' -8(2) yes C9a N10 C11 S12 73.2(7) yes C1 C11a C11 S12 53.0(7) yes N10 C11 S12 C13 69.1(8) yes C11 S12 C13 C14 -172.5(16) yes C9a N10 C11 S12' 78.5(5) yes C1' C11a C11 S12 75.9(9) yes N10 C11 S12' C13' 59.9(7) yes C11 S12' C13' C14' -175.2(13) yes C1' C11a N4 C5 163.2(8) no C1 C11a N4 C5 -161.2(8) no C11 C11a N4 C3 114.5(9) no C11 C11a N4 C3' 139.0(9) no C2' C3' N4 C5 -153.2(15) no C11 C11a C1 C2 -140.3(10) no C5 N4 C3 C2 -177.6(8) no C3 N4 C5 O5 11.0(10) no C11a N4 C5 O5 177.8(5) no C3' N4 C5 O5 -15.1(11) no C3 N4 C5 C5a -171.8(8) no C3' N4 C5 C5a 162.1(10) no O5 C5 C5a C6 21.4(6) no N4 C5 C5a C6 -155.7(5) no O5 C5 C5a C9a -157.1(5) no C9a C5a C6 C7 0.2(10) no C5 C5a C6 C7 -178.5(7) no C5a C6 C7 C8 -1.8(14) no C6 C7 C8 C9 2.8(13) no C7 C8 C9 C9a -2.2(11) no C8 C9 C9a N10 179.9(5) no C8 C9 C9a C5a 0.6(8) no C6 C5a C9a N10 -178.9(5) no C6 C5a C9a C9 0.4(7) no C5 C5a C9a C9 178.9(5) no C9 C9a N10 C11 -176.6(5) no C1' C11a C11 N10 -146.8(9) no C1 C11a C11 N10 -169.8(7) no N4 C11a C11 S12 -54.9(5) no N4 C11a C11 S12' -36.1(6) no C1' C11a C11 S12' 94.7(9) no C1 C11a C11 S12' 71.8(7) no C11a C11 S12 C13 -164.1(7) no C11a C11 S12' C13' -177.2(6) no