#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/42/2204272.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_2204272 loop_ _publ_author_name 'N. Sampath' 'M. N. Ponnuswamy' 'M. Poornachandran' 'R. Raghunathan' _publ_section_title 4'-(2-Chlorophenyl)-2,3-dihydro-1'-methyl-3'-nitrospiro[1H-indole-3,2'-pyrrolidin]-2-one _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1862 _journal_page_last o1864 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C18 H16 Cl N3 O3' _chemical_formula_moiety 'C18 H16 Cl N3 O3' _chemical_formula_sum 'C18 H16 Cl N3 O3' _chemical_formula_weight 357.79 _chemical_name_systematic ; 4'-(2-Chlorophenyl)-2,3-dihydro-1'-methyl-3'-nitrospiro[1H-indole-3,2'- pyrrolidin]-2-one ; _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 SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 102.086(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.1473(3) _cell_length_b 7.8193(12) _cell_length_c 17.4268(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.99 _cell_measurement_theta_min 1.58 _cell_volume 1751.8(3) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics ; ZORTEP (Zsolnai, 1998) and PLATON (Spek, 1999) ; _computing_publication_material 'SHELXL97 AND PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0747 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 5298 _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 1.58 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 744 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.354 _refine_diff_density_min -0.385 _refine_ls_extinction_coef 0.0091(15) _refine_ls_extinction_expression ; Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ ; _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 5099 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.009 _refine_ls_R_factor_all 0.1596 _refine_ls_R_factor_gt 0.0566 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0667P)^2^+0.4302P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1358 _refine_ls_wR_factor_ref 0.1658 _reflns_number_gt 2375 _reflns_number_total 5099 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt6518.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2204272 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_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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_type_symbol Cl1 0.00855(5) 0.30503(12) 0.09834(5) 0.0788(3) Uani d . 1 Cl O1 -0.38338(13) 0.8936(2) 0.05631(9) 0.0537(5) Uani d . 1 O C13 -0.33124(16) 0.7170(3) -0.11936(12) 0.0357(5) Uani d . 1 C N1 -0.19079(14) 0.7858(3) -0.00432(11) 0.0416(5) Uani d . 1 N C2 -0.29774(16) 0.7248(3) -0.03118(12) 0.0358(5) Uani d . 1 C N7 -0.45145(16) 0.8792(3) -0.07620(11) 0.0512(6) Uani d . 1 N H7 -0.5066 0.9395 -0.0779 0.061 Uiso calc R 1 H C12 -0.28471(18) 0.6440(3) -0.17474(13) 0.0432(6) Uani d . 1 C H12 -0.2220 0.5858 -0.1598 0.052 Uiso calc R 1 H C6 -0.38241(17) 0.8432(3) -0.00992(13) 0.0423(6) Uani d . 1 C C8 -0.42314(18) 0.8071(3) -0.14246(13) 0.0419(5) Uani d . 1 C C11 -0.33246(19) 0.6579(3) -0.25341(13) 0.0479(6) Uani d . 1 C H11 -0.3018 0.6085 -0.2915 0.057 Uiso calc R 1 H C4 -0.18697(18) 0.5267(3) 0.05986(13) 0.0447(6) Uani d . 1 C H4 -0.1487 0.4717 0.0240 0.054 Uiso calc R 1 H C5 -0.14895(18) 0.7109(3) 0.07209(14) 0.0480(6) Uani d . 1 C H5A -0.1766 0.7667 0.1131 0.058 Uiso calc R 1 H H5B -0.0736 0.7167 0.0850 0.058 Uiso calc R 1 H C14 -0.17087(19) 0.4209(3) 0.13395(14) 0.0477(6) Uani d . 1 C C9 -0.4718(2) 0.8208(4) -0.22034(13) 0.0530(7) Uani d . 1 C H9 -0.5343 0.8796 -0.2355 0.064 Uiso calc R 1 H C3 -0.29810(18) 0.5540(3) 0.01558(13) 0.0429(6) Uani d . 1 C H3 -0.3422 0.5696 0.0539 0.051 Uiso calc R 1 H C15 -0.0837(2) 0.3198(4) 0.15615(16) 0.0565(7) Uani d . 1 C C20 -0.1750(2) 0.9685(3) -0.01102(17) 0.0623(8) Uani d . 1 C H20A -0.2051 1.0052 -0.0634 0.093 Uiso calc R 1 H H20B -0.1018 0.9929 0.0003 0.093 Uiso calc R 1 H H20C -0.2075 1.0282 0.0256 0.093 Uiso calc R 1 H C10 -0.4244(2) 0.7441(3) -0.27499(14) 0.0516(7) Uani d . 1 C H10 -0.4559 0.7512 -0.3279 0.062 Uiso calc R 1 H N21 -0.3415(3) 0.4080(4) -0.03798(15) 0.0808(9) Uani d . 1 N C16 -0.0650(3) 0.2277(4) 0.2258(2) 0.0815(11) Uani d . 1 C H16 -0.0058 0.1601 0.2394 0.098 Uiso calc R 1 H C19 -0.2397(3) 0.4263(5) 0.18401(16) 0.0756(9) Uani d . 1 C H19 -0.2997 0.4920 0.1705 0.091 Uiso calc R 1 H O2 -0.2806(3) 0.3252(4) -0.06665(16) 0.1325(14) Uani d . 1 O C17 -0.1333(3) 0.2372(5) 0.2736(2) 0.0984(14) Uani d . 1 C H17 -0.1208 0.1761 0.3205 0.118 Uiso calc R 1 H O3 -0.4342(3) 0.3953(5) -0.05334(18) 0.1611(17) Uani d . 1 O C18 -0.2209(3) 0.3359(6) 0.25375(19) 0.0956(13) Uani d . 1 C H18 -0.2676 0.3421 0.2870 0.115 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 Cl1 0.0456(4) 0.0828(6) 0.1029(6) 0.0146(4) 0.0040(4) 0.0001(5) O1 0.0555(10) 0.0726(13) 0.0335(9) 0.0170(9) 0.0102(8) -0.0071(8) C13 0.0373(11) 0.0382(13) 0.0311(10) 0.0041(10) 0.0058(9) 0.0001(10) N1 0.0378(10) 0.0442(12) 0.0400(10) 0.0014(9) 0.0020(8) 0.0024(9) C2 0.0363(11) 0.0403(13) 0.0297(10) 0.0071(10) 0.0047(8) 0.0007(9) N7 0.0455(11) 0.0694(15) 0.0370(10) 0.0258(11) 0.0046(9) -0.0041(10) C12 0.0416(13) 0.0463(14) 0.0423(13) 0.0052(11) 0.0104(10) -0.0036(11) C6 0.0397(12) 0.0523(15) 0.0351(12) 0.0106(11) 0.0082(10) -0.0007(11) C8 0.0438(12) 0.0463(14) 0.0351(11) 0.0103(11) 0.0070(9) -0.0013(10) C11 0.0566(15) 0.0543(16) 0.0351(12) -0.0010(13) 0.0148(11) -0.0049(12) C4 0.0474(13) 0.0477(15) 0.0376(12) 0.0116(12) 0.0062(10) 0.0031(11) C5 0.0386(12) 0.0604(16) 0.0401(12) 0.0010(12) -0.0026(10) 0.0028(12) C14 0.0530(14) 0.0463(15) 0.0401(13) 0.0095(12) 0.0015(11) 0.0074(11) C9 0.0563(15) 0.0575(17) 0.0387(13) 0.0186(13) -0.0050(11) 0.0006(12) C3 0.0506(14) 0.0431(14) 0.0323(11) -0.0007(11) 0.0027(10) 0.0004(10) C15 0.0489(14) 0.0487(16) 0.0636(17) -0.0027(13) -0.0073(12) 0.0054(14) C20 0.0662(18) 0.0473(17) 0.0706(19) -0.0090(14) 0.0081(15) 0.0050(14) C10 0.0694(17) 0.0531(16) 0.0290(11) 0.0018(13) 0.0029(11) 0.0016(11) N21 0.114(3) 0.0634(19) 0.0514(15) -0.0219(18) -0.0143(16) 0.0069(14) C16 0.066(2) 0.072(2) 0.092(2) -0.0054(17) -0.0170(18) 0.0388(19) C19 0.078(2) 0.103(3) 0.0466(16) 0.0207(19) 0.0148(15) 0.0212(17) O2 0.227(4) 0.0623(17) 0.0858(19) 0.043(2) -0.018(2) -0.0244(14) C17 0.093(3) 0.107(3) 0.076(2) -0.029(2) -0.024(2) 0.051(2) O3 0.129(3) 0.231(4) 0.114(2) -0.115(3) 0.003(2) -0.041(2) C18 0.099(3) 0.133(4) 0.0559(19) -0.013(3) 0.0192(19) 0.026(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C15 1.736(3) y O1 C6 1.222(3) y C13 C12 1.371(3) ? C13 C8 1.384(3) ? C13 C2 1.508(3) ? N1 C20 1.452(3) y N1 C5 1.453(3) ? N1 C2 1.466(3) ? C2 C6 1.551(3) ? C2 C3 1.565(3) ? N7 C6 1.341(3) y N7 C8 1.403(3) y N7 H7 0.8600 ? C12 C11 1.388(3) ? C12 H12 0.9300 ? C8 C9 1.378(3) ? C11 C10 1.366(3) ? C11 H11 0.9300 ? C4 C14 1.511(3) ? C4 C3 1.518(3) ? C4 C5 1.525(4) ? C4 H4 0.9800 ? C5 H5A 0.9700 ? C5 H5B 0.9700 ? C14 C15 1.378(3) ? C14 C19 1.383(4) ? C9 C10 1.380(4) ? C9 H9 0.9300 ? C3 N21 1.508(4) y C3 H3 0.9800 ? C15 C16 1.389(4) ? C20 H20A 0.9600 ? C20 H20B 0.9600 ? C20 H20C 0.9600 ? C10 H10 0.9300 ? N21 O3 1.196(4) y N21 O2 1.214(4) y C16 C17 1.349(5) ? C16 H16 0.9300 ? C19 C18 1.383(4) ? C19 H19 0.9300 ? C17 C18 1.369(5) ? C17 H17 0.9300 ? C18 H18 0.9300 ? 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 C12 C13 C8 119.9(2) ? C12 C13 C2 130.98(19) ? C8 C13 C2 109.08(18) ? C20 N1 C5 115.9(2) y C20 N1 C2 116.01(19) y C5 N1 C2 108.38(18) y N1 C2 C13 113.23(18) y N1 C2 C6 114.71(19) y C13 C2 C6 101.33(16) y N1 C2 C3 102.63(16) y C13 C2 C3 117.64(19) y C6 C2 C3 107.71(18) y C6 N7 C8 112.08(19) ? C6 N7 H7 124.0 ? C8 N7 H7 124.0 ? C13 C12 C11 119.1(2) ? C13 C12 H12 120.4 ? C11 C12 H12 120.4 ? O1 C6 N7 127.3(2) ? O1 C6 C2 124.6(2) ? N7 C6 C2 108.05(18) ? C9 C8 C13 121.6(2) ? C9 C8 N7 129.1(2) ? C13 C8 N7 109.32(19) ? C10 C11 C12 120.1(2) ? C10 C11 H11 119.9 ? C12 C11 H11 119.9 ? C14 C4 C3 117.3(2) ? C14 C4 C5 114.5(2) ? C3 C4 C5 100.99(18) ? C14 C4 H4 107.8 ? C3 C4 H4 107.8 ? C5 C4 H4 107.8 ? N1 C5 C4 101.68(18) ? N1 C5 H5A 111.4 ? C4 C5 H5A 111.4 ? N1 C5 H5B 111.4 ? C4 C5 H5B 111.4 ? H5A C5 H5B 109.3 ? C15 C14 C19 117.1(2) ? C15 C14 C4 120.9(2) ? C19 C14 C4 122.0(2) ? C8 C9 C10 117.5(2) ? C8 C9 H9 121.2 ? C10 C9 H9 121.2 ? N21 C3 C4 114.0(2) ? N21 C3 C2 111.43(18) ? C4 C3 C2 106.09(18) ? N21 C3 H3 108.4 ? C4 C3 H3 108.4 ? C2 C3 H3 108.4 ? C14 C15 C16 121.8(3) ? C14 C15 Cl1 121.1(2) ? C16 C15 Cl1 117.1(2) ? N1 C20 H20A 109.5 ? N1 C20 H20B 109.5 ? H20A C20 H20B 109.5 ? N1 C20 H20C 109.5 ? H20A C20 H20C 109.5 ? H20B C20 H20C 109.5 ? C11 C10 C9 121.7(2) ? C11 C10 H10 119.1 ? C9 C10 H10 119.1 ? O3 N21 O2 126.3(4) y O3 N21 C3 115.9(4) y O2 N21 C3 117.5(3) y C17 C16 C15 119.5(3) ? C17 C16 H16 120.3 ? C15 C16 H16 120.3 ? C14 C19 C18 121.2(3) ? C14 C19 H19 119.4 ? C18 C19 H19 119.4 ? C16 C17 C18 120.5(3) ? C16 C17 H17 119.7 ? C18 C17 H17 119.7 ? C17 C18 C19 119.8(3) ? C17 C18 H18 120.1 ? C19 C18 H18 120.1 ? 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 C20 N1 C2 C13 76.1(3) ? C5 N1 C2 C13 -151.52(19) ? C20 N1 C2 C6 -39.6(3) ? C5 N1 C2 C6 92.8(2) ? C20 N1 C2 C3 -156.1(2) ? C5 N1 C2 C3 -23.7(2) y C12 C13 C2 N1 50.9(3) ? C8 C13 C2 N1 -126.7(2) ? C12 C13 C2 C6 174.2(2) ? C8 C13 C2 C6 -3.4(2) ? C12 C13 C2 C3 -68.7(3) ? C8 C13 C2 C3 113.7(2) ? C8 C13 C12 C11 -1.7(4) ? C2 C13 C12 C11 -179.1(2) ? C8 N7 C6 O1 176.7(3) ? C8 N7 C6 C2 -2.8(3) ? N1 C2 C6 O1 -53.5(3) ? C13 C2 C6 O1 -175.8(2) ? C3 C2 C6 O1 60.1(3) ? N1 C2 C6 N7 126.0(2) ? C13 C2 C6 N7 3.7(3) ? C3 C2 C6 N7 -120.4(2) ? C12 C13 C8 C9 2.3(4) ? C2 C13 C8 C9 -179.8(2) ? C12 C13 C8 N7 -175.9(2) ? C2 C13 C8 N7 2.0(3) ? C6 N7 C8 C9 -177.4(3) ? C6 N7 C8 C13 0.6(3) ? C13 C12 C11 C10 0.3(4) ? C20 N1 C5 C4 175.4(2) y C2 N1 C5 C4 42.9(2) ? C14 C4 C5 N1 -170.28(19) ? C3 C4 C5 N1 -43.2(2) y C3 C4 C14 C15 147.4(2) ? C5 C4 C14 C15 -94.5(3) ? C3 C4 C14 C19 -35.4(4) ? C5 C4 C14 C19 82.7(3) ? C13 C8 C9 C10 -1.3(4) ? N7 C8 C9 C10 176.5(3) ? C14 C4 C3 N21 -82.6(3) ? C5 C4 C3 N21 152.3(2) y C14 C4 C3 C2 154.4(2) ? C5 C4 C3 C2 29.3(2) y N1 C2 C3 N21 -129.4(2) y C13 C2 C3 N21 -4.4(3) ? C6 C2 C3 N21 109.2(3) ? N1 C2 C3 C4 -4.8(2) y C13 C2 C3 C4 120.2(2) ? C6 C2 C3 C4 -126.21(19) ? C19 C14 C15 C16 -0.3(4) ? C4 C14 C15 C16 177.0(3) ? C19 C14 C15 Cl1 -179.3(2) ? C4 C14 C15 Cl1 -2.1(4) ? C12 C11 C10 C9 0.7(4) ? C8 C9 C10 C11 -0.2(4) ? C4 C3 N21 O3 156.2(3) ? C2 C3 N21 O3 -83.8(3) ? C4 C3 N21 O2 -30.2(4) ? C2 C3 N21 O2 89.9(3) ? C14 C15 C16 C17 -0.2(5) ? Cl1 C15 C16 C17 178.8(3) ? C15 C14 C19 C18 0.8(5) ? C4 C14 C19 C18 -176.4(3) ? C15 C16 C17 C18 0.3(6) ? C16 C17 C18 C19 0.2(6) ? C14 C19 C18 C17 -0.8(6) ? 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 C4 H4 Cl1 1_555 0.98 2.55 3.056(2) 112 C3 H3 O1 1_555 0.98 2.59 3.024(3) 107 N7 H7 O1 3_475 0.86 2.04 2.882(3) 166 _cod_database_fobs_code 2204272 _journal_paper_doi 10.1107/S1600536804023529