#------------------------------------------------------------------------------ #$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206651.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_2206651 _space_group_IT_number 15 _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _[local]_cod_cif_authors_sg_H-M 'C 2/c' loop_ _publ_author_name 'Sundar, T. V.' 'Parthasarathi, V.' 'Walfort, B.' 'Lang, H.' 'Piplani, P.' 'Malik, R.' _publ_section_title ; N-[4-(Pyrrolidin-1-ylcarbonylmethoxy)phenyl]acetamide ; _journal_coeditor_code CI6620 _journal_issue 9 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o2868 _journal_page_last o2870 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C14 H18 N2 O3' _chemical_formula_moiety 'C14 H18 N2 O3' _chemical_formula_sum 'C14 H18 N2 O3' _chemical_formula_weight 262.30 _chemical_melting_point 447 _chemical_name_systematic ; N-[4-(Pyrrolidin-1-ylcarbonylmethoxy)phenyl]acetamide ; _symmetry_cell_setting monoclinic _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 111.12(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 21.08(2) _cell_length_b 10.927(11) _cell_length_c 12.767(9) _cell_measurement_reflns_used 745 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 28.33 _cell_measurement_theta_min 2.25 _cell_volume 2743(4) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker SMART CCD 1K' _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 0.0606 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 14787 _diffrn_reflns_theta_full 26.45 _diffrn_reflns_theta_max 26.45 _diffrn_reflns_theta_min 2.07 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 0.99999 _exptl_absorpt_correction_T_min 0.96464 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 1120 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.284 _refine_diff_density_min -0.206 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 187 _refine_ls_number_reflns 2787 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0932 _refine_ls_R_factor_gt 0.0588 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1129P)^2^+0.0652] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1582 _refine_ls_wR_factor_ref 0.1825 _reflns_number_gt 1837 _reflns_number_total 2787 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6620.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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' 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 N1 0.12634(9) 1.22874(16) 0.16236(15) 0.0483(5) Uani d . 1 . . N H1 0.1206(12) 1.213(2) 0.225(2) 0.065(7) Uiso d . 1 . . H N2 0.39361(9) 0.72766(15) -0.04710(14) 0.0489(5) Uani d . 1 A . N O1 0.30451(8) 0.86981(14) 0.11528(12) 0.0606(5) Uani d . 1 . . O O2 0.38889(8) 0.68802(14) 0.12343(12) 0.0609(5) Uani d . 1 . . O O3 0.10220(9) 1.36064(15) 0.01383(14) 0.0750(6) Uani d . 1 . . O C1 0.17405(10) 1.14630(17) 0.14558(16) 0.0418(5) Uani d . 1 . . C C2 0.19523(11) 1.1487(2) 0.05328(17) 0.0517(6) Uani d . 1 . . C H2 0.1799 1.2103 -0.0002 0.062 Uiso calc R 1 . . H C3 0.23930(11) 1.05894(19) 0.04153(17) 0.0531(6) Uani d . 1 . . C H3 0.2531 1.0615 -0.0199 0.064 Uiso calc R 1 . . H C4 0.26287(10) 0.96604(19) 0.11996(16) 0.0465(5) Uani d . 1 . . C C5 0.24302(10) 0.96529(19) 0.21399(17) 0.0486(6) Uani d . 1 . . C H5 0.2592 0.9049 0.2685 0.058 Uiso calc R 1 . . H C6 0.19944(10) 1.05437(19) 0.22529(16) 0.0461(5) Uani d . 1 . . C H6 0.1867 1.0529 0.2879 0.055 Uiso calc R 1 . . H C7 0.32446(12) 0.86173(19) 0.01997(18) 0.0523(6) Uani d . 1 . . C H7A 0.3481 0.9357 0.0130 0.063 Uiso calc R 1 . . H H7B 0.2848 0.8518 -0.0480 0.063 Uiso calc R 1 . . H C8 0.37137(10) 0.75118(18) 0.03700(17) 0.0463(5) Uani d . 1 . . C C9 0.37673(13) 0.7968(2) -0.15273(19) 0.0634(7) Uani d . 1 . . C H9A 0.3755 0.8841 -0.1399 0.076 Uiso calc PR 0.646(15) A 1 H H9B 0.3333 0.7713 -0.2071 0.076 Uiso calc PR 0.646(15) A 1 H H9C 0.3980 0.8769 -0.1395 0.076 Uiso calc PR 0.354(15) A 2 H H9D 0.3279 0.8068 -0.1890 0.076 Uiso calc PR 0.354(15) A 2 H C10 0.4358(5) 0.7633(7) -0.1924(6) 0.0694(19) Uani d P 0.646(15) A 1 C H10A 0.4204 0.7625 -0.2737 0.083 Uiso calc PR 0.646(15) A 1 H H10B 0.4728 0.8215 -0.1637 0.083 Uiso calc PR 0.646(15) A 1 H C10' 0.4050(7) 0.7184(12) -0.2222(9) 0.060(3) Uani d P 0.354(15) A 2 C H10C 0.3691 0.6692 -0.2742 0.072 Uiso calc PR 0.354(15) A 2 H H10D 0.4243 0.7695 -0.2652 0.072 Uiso calc PR 0.354(15) A 2 H C11 0.45816(15) 0.6381(2) -0.1457(2) 0.0783(8) Uani d . 1 . . C H11A 0.5066 0.6282 -0.1282 0.094 Uiso calc PR 0.646(15) A 1 H H11B 0.4344 0.5760 -0.2000 0.094 Uiso calc PR 0.646(15) A 1 H H11C 0.5028 0.6742 -0.1285 0.094 Uiso calc PR 0.354(15) A 2 H H11D 0.4576 0.5586 -0.1798 0.094 Uiso calc PR 0.354(15) A 2 H C12 0.44137(12) 0.62584(19) -0.03952(19) 0.0540(6) Uani d . 1 A . C H12A 0.4202 0.5475 -0.0375 0.065 Uiso calc R 1 . . H H12B 0.4821 0.6336 0.0271 0.065 Uiso calc R 1 . . H C13 0.09393(11) 1.3259(2) 0.10030(18) 0.0498(5) Uani d . 1 . . C C14 0.04501(12) 1.3887(2) 0.1450(2) 0.0636(7) Uani d . 1 . . C H14A 0.0149 1.4404 0.0878 0.095 Uiso calc R 1 . . H H14B 0.0701 1.4374 0.2092 0.095 Uiso calc R 1 . . H H14C 0.0190 1.3282 0.1665 0.095 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 0.0597(11) 0.0589(11) 0.0349(10) 0.0045(9) 0.0271(9) 0.0017(8) N2 0.0612(11) 0.0580(11) 0.0389(10) 0.0014(8) 0.0319(9) 0.0000(8) O1 0.0808(11) 0.0744(11) 0.0447(9) 0.0191(8) 0.0443(8) 0.0092(7) O2 0.0843(12) 0.0684(10) 0.0441(9) 0.0104(8) 0.0401(8) 0.0075(8) O3 0.0934(13) 0.0851(12) 0.0614(11) 0.0164(10) 0.0460(10) 0.0239(9) C1 0.0451(11) 0.0511(12) 0.0325(10) -0.0061(9) 0.0181(9) -0.0064(9) C2 0.0679(15) 0.0577(13) 0.0387(12) 0.0033(11) 0.0301(11) 0.0049(9) C3 0.0737(15) 0.0640(13) 0.0362(11) 0.0029(11) 0.0375(11) 0.0012(10) C4 0.0531(12) 0.0581(12) 0.0354(11) 0.0011(10) 0.0246(10) -0.0027(9) C5 0.0537(13) 0.0637(14) 0.0341(11) 0.0026(10) 0.0225(10) 0.0041(9) C6 0.0516(12) 0.0644(13) 0.0300(10) -0.0033(10) 0.0243(9) -0.0027(9) C7 0.0658(14) 0.0654(14) 0.0391(11) 0.0014(11) 0.0349(11) -0.0012(10) C8 0.0549(13) 0.0545(12) 0.0383(11) -0.0072(10) 0.0276(10) -0.0053(9) C9 0.0812(17) 0.0769(16) 0.0466(14) 0.0060(13) 0.0407(13) 0.0064(12) C10 0.087(5) 0.088(4) 0.058(3) 0.005(3) 0.056(3) 0.004(3) C10' 0.073(7) 0.075(6) 0.049(5) -0.013(5) 0.044(5) -0.001(4) C11 0.094(2) 0.093(2) 0.0735(18) 0.0093(16) 0.0608(17) -0.0010(15) C12 0.0615(14) 0.0589(13) 0.0491(13) 0.0008(11) 0.0292(11) -0.0057(10) C13 0.0532(13) 0.0575(13) 0.0431(12) -0.0046(10) 0.0227(10) -0.0014(10) C14 0.0659(15) 0.0682(15) 0.0636(15) 0.0093(12) 0.0315(13) 0.0061(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C13 1.353(3) N1 C1 1.423(3) N1 H1 0.87(3) N2 C8 1.342(2) N2 C9 1.473(3) N2 C12 1.480(3) O1 C4 1.385(3) O1 C7 1.426(2) O2 C8 1.240(2) O3 C13 1.238(3) C1 C6 1.392(3) C1 C2 1.403(3) C2 C3 1.396(3) C2 H2 0.93 C3 C4 1.386(3) C3 H3 0.93 C4 C5 1.407(3) C5 C6 1.381(3) C5 H5 0.93 C6 H6 0.93 C7 C8 1.526(3) C7 H7A 0.97 C7 H7B 0.97 C9 C10' 1.503(10) C9 C10 1.548(6) C9 H9A 0.97 C9 H9B 0.97 C9 H9C 0.97 C9 H9D 0.97 C10 C11 1.499(7) C10 H10A 0.97 C10 H10B 0.97 C10' C11 1.480(11) C10' H10C 0.97 C10' H10D 0.97 C11 C12 1.526(3) C11 H11A 0.97 C11 H11B 0.97 C11 H11C 0.97 C11 H11D 0.97 C12 H12A 0.97 C12 H12B 0.97 C13 C14 1.512(3) C14 H14A 0.96 C14 H14B 0.96 C14 H14C 0.96 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C13 N1 C1 130.06(18) C13 N1 H1 118.9(15) C1 N1 H1 110.9(15) C8 N2 C9 126.53(19) C8 N2 C12 121.14(17) C9 N2 C12 112.31(16) C4 O1 C7 118.05(16) C6 C1 C2 118.23(18) C6 C1 N1 116.94(17) C2 C1 N1 124.79(18) C3 C2 C1 120.16(19) C3 C2 H2 119.9 C1 C2 H2 119.9 C4 C3 C2 121.09(18) C4 C3 H3 119.5 C2 C3 H3 119.5 O1 C4 C3 126.36(17) O1 C4 C5 114.87(18) C3 C4 C5 118.77(19) C6 C5 C4 119.91(19) C6 C5 H5 120.0 C4 C5 H5 120.0 C5 C6 C1 121.80(18) C5 C6 H6 119.1 C1 C6 H6 119.1 O1 C7 C8 107.61(16) O1 C7 H7A 110.2 C8 C7 H7A 110.2 O1 C7 H7B 110.2 C8 C7 H7B 110.2 H7A C7 H7B 108.5 O2 C8 N2 121.8(2) O2 C8 C7 122.51(17) N2 C8 C7 115.64(18) N2 C9 C10' 103.4(4) N2 C9 C10 102.7(3) N2 C9 H9A 111.2 C10' C9 H9A 134.5 C10 C9 H9A 111.2 N2 C9 H9B 111.2 C10' C9 H9B 83.5 C10 C9 H9B 111.2 H9A C9 H9B 109.1 N2 C9 H9C 111.1 C10' C9 H9C 111.1 C10 C9 H9C 83.9 N2 C9 H9D 111.1 C10' C9 H9D 111.1 C10 C9 H9D 135.2 H9C C9 H9D 109.1 C11 C10 C9 105.1(4) C11 C10 H10A 110.7 C9 C10 H10A 110.7 C11 C10 H10B 110.7 C9 C10 H10B 110.7 H10A C10 H10B 108.8 C11 C10' C9 108.4(7) C11 C10' H10C 110.0 C9 C10' H10C 110.0 C11 C10' H10D 110.0 C9 C10' H10D 110.0 H10C C10' H10D 108.4 C10' C11 C12 106.0(4) C10 C11 C12 107.0(3) C10' C11 H11A 134.6 C10 C11 H11A 110.3 C12 C11 H11A 110.3 C10' C11 H11B 82.5 C10 C11 H11B 110.3 C12 C11 H11B 110.3 H11A C11 H11B 108.6 C10' C11 H11C 110.5 C10 C11 H11C 81.9 C12 C11 H11C 110.5 C10' C11 H11D 110.5 C10 C11 H11D 133.5 C12 C11 H11D 110.5 H11C C11 H11D 108.7 N2 C12 C11 104.25(18) N2 C12 H12A 110.9 C11 C12 H12A 110.9 N2 C12 H12B 110.9 C11 C12 H12B 110.9 H12A C12 H12B 108.9 O3 C13 N1 124.0(2) O3 C13 C14 122.1(2) N1 C13 C14 113.84(19) C13 C14 H14A 109.5 C13 C14 H14B 109.5 H14A C14 H14B 109.5 C13 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 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 C13 N1 C1 C6 179.5(2) yes C13 N1 C1 C2 -2.7(3) yes C6 C1 C2 C3 1.5(3) ? N1 C1 C2 C3 -176.16(19) ? C1 C2 C3 C4 0.1(3) ? C7 O1 C4 C3 -1.7(3) y C7 O1 C4 C5 177.50(18) ? C2 C3 C4 O1 177.5(2) ? C2 C3 C4 C5 -1.7(3) ? O1 C4 C5 C6 -177.62(18) ? C3 C4 C5 C6 1.6(3) ? C4 C5 C6 C1 0.0(3) ? C2 C1 C6 C5 -1.6(3) ? N1 C1 C6 C5 176.28(18) ? C4 O1 C7 C8 178.33(17) y C9 N2 C8 O2 -179.4(2) ? C12 N2 C8 O2 -1.1(3) ? C9 N2 C8 C7 -0.6(3) ? C12 N2 C8 C7 177.77(17) ? O1 C7 C8 O2 -3.0(3) y O1 C7 C8 N2 178.16(17) ? C8 N2 C9 C10' -170.5(7) ? C12 N2 C9 C10' 11.1(7) ? C8 N2 C9 C10 158.6(5) ? C12 N2 C9 C10 -19.8(5) ? N2 C9 C10 C11 28.5(7) ? C10' C9 C10 C11 -66.2(10) ? N2 C9 C10' C11 -21.8(10) ? C10 C9 C10' C11 70.5(12) ? C9 C10' C11 C10 -72.1(10) ? C9 C10' C11 C12 24.5(10) ? C9 C10 C11 C10' 65.2(9) ? C9 C10 C11 C12 -27.6(7) ? C8 N2 C12 C11 -175.19(19) ? C9 N2 C12 C11 3.4(2) ? C10' C11 C12 N2 -16.8(7) ? C10 C11 C12 N2 15.4(5) ? C1 N1 C13 O3 -0.8(4) yes C1 N1 C13 C14 178.30(19) ? 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 O2 4 0.87(3) 2.03(3) 2.900(3) 176(2) yes C2 H2 O3 . 0.93 2.37 2.958(4) 121 yes C7 H7A O3 7_575 0.97 2.54 3.501(4) 174 yes