#------------------------------------------------------------------------------ #$Date: 2009-11-16 03:43:51 +0200 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2203355.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_2203355 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _[local]_cod_cif_authors_sg_H-M 'P 21/a' loop_ _publ_author_name 'Wu, Hai-Qiang' 'Zhou, Jin-Lin' 'Huang, Zhi-Shu' 'Gu, Lian-Quan' 'Ng, Seik Weng' _publ_section_title ; 3-[2-(N,N-Diethylamino)glyoxyloyl]-1H-indol-4-yl acetate monohydrate ; _journal_issue 3 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o337 _journal_page_last o338 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C16 H18 N2 O4, H2 O' _chemical_formula_moiety 'C16 H18 N2 O4, H2 O' _chemical_formula_sum 'C16 H20 N2 O5' _chemical_formula_weight 320.34 _chemical_name_systematic ; 3-[2-(N,N-Diethylamino)glyoxyloyl]-1H-indol-4-yl acetate monohydrate ; _symmetry_cell_setting Monoclinic _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 98.703(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.646(2) _cell_length_b 10.5180(10) _cell_length_c 12.904(2) _cell_measurement_reflns_used 931 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.8 _cell_measurement_theta_min 2.5 _cell_volume 1696.7(4) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_av_sigmaI/netI 0.014 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 9454 _diffrn_reflns_theta_full 27.0 _diffrn_reflns_theta_max 27.0 _diffrn_reflns_theta_min 2.5 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.36 _refine_diff_density_max 0.30 _refine_diff_density_min -0.17 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 3695 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.019 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0404 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0694P)^2^+0.3054P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1164 _refine_ls_wR_factor_ref 0.1279 _reflns_number_gt 2880 _reflns_number_total 3695 _reflns_threshold_expression I>2\s(I) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z' '-x, -y, -z' '-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_type_symbol O1 0.26650(10) 0.44090(10) 0.13670(10) 0.0527(3) Uani d . 1 O O2 0.43820(10) 0.4820(2) 0.12480(10) 0.0725(4) Uani d . 1 O O3 0.28480(10) 0.71450(10) 0.14120(10) 0.0566(3) Uani d . 1 O O4 0.30460(10) 0.94700(10) 0.29260(10) 0.0594(3) Uani d . 1 O O1W 0.40430(10) 0.5287(2) 0.69340(10) 0.0906(5) Uani d D 1 O N1 0.37760(10) 0.57930(10) 0.48250(10) 0.0504(3) Uani d D 1 N N2 0.45930(10) 0.90520(10) 0.23130(10) 0.0534(3) Uani d . 1 N C1 0.3058(2) 0.5067(2) -0.02730(10) 0.0705(5) Uani d . 1 C C2 0.34640(10) 0.4771(2) 0.08430(10) 0.0541(4) Uani d . 1 C C3 0.29430(10) 0.41440(10) 0.24390(10) 0.0465(3) Uani d . 1 C C4 0.28610(10) 0.2909(2) 0.27580(10) 0.0590(4) Uani d . 1 C C5 0.30880(10) 0.2578(2) 0.38140(10) 0.0630(4) Uani d . 1 C C6 0.34030(10) 0.3477(2) 0.45660(10) 0.0570(4) Uani d . 1 C C7 0.34760(10) 0.47270(10) 0.42300(10) 0.0453(3) Uani d . 1 C C8 0.32410(10) 0.51080(10) 0.31720(10) 0.0407(3) Uani d . 1 C C9 0.34080(10) 0.64700(10) 0.31640(10) 0.0408(3) Uani d . 1 C C10 0.37370(10) 0.68120(10) 0.41980(10) 0.0475(3) Uani d . 1 C C11 0.32740(10) 0.73650(10) 0.23110(10) 0.0415(3) Uani d . 1 C C12 0.36480(10) 0.87270(10) 0.25560(10) 0.0435(3) Uani d . 1 C C13 0.52900(10) 0.8154(2) 0.1867(2) 0.0646(4) Uani d . 1 C C14 0.5200(2) 0.8246(2) 0.0695(2) 0.0863(6) Uani d . 1 C C15 0.4968(2) 1.0366(2) 0.2478(2) 0.0752(5) Uani d . 1 C C16 0.5466(2) 1.0606(3) 0.3574(2) 0.1068(9) Uani d . 1 C H1W1 0.4540(10) 0.528(2) 0.7460(10) 0.096(7) Uiso d D 1 H H1W2 0.3470(10) 0.497(2) 0.708(2) 0.105(8) Uiso d D 1 H H1N 0.395(2) 0.578(2) 0.5500(10) 0.069(5) Uiso d D 1 H H1A 0.3633 0.5382 -0.0607 0.106 Uiso calc R 1 H H1B 0.2507 0.5700 -0.0308 0.106 Uiso calc R 1 H H1C 0.2770 0.4309 -0.0623 0.106 Uiso calc R 1 H H4 0.2649 0.2282 0.2262 0.071 Uiso calc R 1 H H5 0.3025 0.1734 0.4011 0.076 Uiso calc R 1 H H6 0.3562 0.3260 0.5271 0.068 Uiso calc R 1 H H10 0.3908 0.7636 0.4425 0.057 Uiso calc R 1 H H13A 0.5110 0.7295 0.2053 0.078 Uiso calc R 1 H H13B 0.6026 0.8312 0.2176 0.078 Uiso calc R 1 H H14A 0.5668 0.7635 0.0448 0.129 Uiso calc R 1 H H14B 0.5398 0.9086 0.0505 0.129 Uiso calc R 1 H H14C 0.4476 0.8077 0.0382 0.129 Uiso calc R 1 H H15A 0.4368 1.0940 0.2297 0.090 Uiso calc R 1 H H15B 0.5486 1.0546 0.2014 0.090 Uiso calc R 1 H H16A 0.5703 1.1473 0.3644 0.160 Uiso calc R 1 H H16B 0.6067 1.0048 0.3753 0.160 Uiso calc R 1 H H16C 0.4951 1.0451 0.4035 0.160 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 O1 0.0507(6) 0.0592(6) 0.0466(6) -0.0074(4) 0.0024(4) -0.0101(4) O2 0.0499(6) 0.1190(10) 0.0491(6) 0.0037(6) 0.0085(5) -0.0023(6) O3 0.0649(6) 0.0573(6) 0.0443(6) -0.0048(5) -0.0027(5) 0.0019(4) O4 0.0512(6) 0.0546(6) 0.0748(7) 0.0051(5) 0.0170(5) -0.0119(5) O1W 0.0534(7) 0.166(2) 0.0506(7) -0.0115(8) 0.0004(6) 0.0323(8) N1 0.0543(7) 0.0594(7) 0.0369(6) -0.0005(5) 0.0043(5) 0.0002(5) N2 0.0441(6) 0.0470(7) 0.0710(8) -0.0022(5) 0.0143(6) -0.0019(6) C1 0.0770(10) 0.0900(10) 0.0419(8) -0.0017(9) 0.0026(7) -0.0105(8) C2 0.0550(8) 0.0641(9) 0.0431(8) 0.0009(7) 0.0068(6) -0.0131(6) C3 0.0420(7) 0.0486(7) 0.0491(8) -0.0022(5) 0.0076(6) -0.0043(6) C4 0.0601(9) 0.0480(8) 0.0700(10) -0.0055(7) 0.0133(7) -0.0087(7) C5 0.0650(10) 0.0465(8) 0.0800(10) -0.0016(7) 0.0164(8) 0.0084(8) C6 0.0554(8) 0.0588(9) 0.0581(9) 0.0034(7) 0.0127(7) 0.0154(7) C7 0.0397(6) 0.0516(7) 0.0455(7) 0.0011(5) 0.0094(5) 0.0027(6) C8 0.0349(6) 0.0447(7) 0.0430(7) -0.0003(5) 0.0079(5) -0.0003(5) C9 0.0368(6) 0.0445(7) 0.0412(7) -0.0015(5) 0.0063(5) -0.0021(5) C10 0.0479(7) 0.0499(7) 0.0445(7) -0.0026(6) 0.0060(6) -0.0042(6) C11 0.0351(6) 0.0462(7) 0.0436(7) 0.0008(5) 0.0074(5) -0.0008(5) C12 0.0391(6) 0.0446(7) 0.0460(7) 0.0024(5) 0.0040(5) 0.0011(5) C13 0.0447(8) 0.0620(9) 0.0910(10) 0.0064(7) 0.0226(8) 0.0027(8) C14 0.0900(10) 0.0870(10) 0.091(2) 0.0080(10) 0.0400(10) -0.0040(10) C15 0.0690(10) 0.0610(10) 0.100(2) -0.0215(8) 0.0290(10) -0.0130(10) C16 0.085(2) 0.136(2) 0.104(2) -0.0440(10) 0.0270(10) -0.042(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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 O1 C3 117.00(10) yes C7 N1 C10 109.40(10) yes C12 N2 C13 122.90(10) yes C12 N2 C15 119.50(10) yes C13 N2 C15 117.60(10) yes O1 C2 O2 122.80(10) yes O1 C2 C1 111.60(10) yes O2 C2 C1 125.6(2) yes O1 C3 C4 117.70(10) yes O1 C3 C8 121.70(10) yes C4 C3 C8 120.50(10) yes C3 C4 C5 121.1(2) yes C4 C5 C6 121.0(2) yes C5 C6 C7 117.20(10) yes N1 C7 C6 128.40(10) yes N1 C7 C8 108.00(10) yes C6 C7 C8 123.70(10) yes C3 C8 C7 116.50(10) yes C3 C8 C9 137.40(10) yes C7 C8 C9 106.10(10) yes C8 C9 C10 105.90(10) yes C10 C9 C11 123.40(10) yes C11 C9 C8 130.70(10) yes N1 C10 C9 110.70(10) yes O3 C11 C9 125.80(10) yes O3 C11 C12 116.90(10) yes C9 C11 C12 117.30(10) yes O4 C12 N2 124.00(10) yes O4 C12 C11 118.90(10) yes N2 C12 C11 117.00(10) yes N2 C13 C14 113.2(2) yes N2 C15 C16 112.4(2) yes C10 N1 H1N 127.0(10) no C7 N1 H1N 124.0(10) no H1W1 O1W H1W2 112(2) no C2 C1 H1A 109.5 no C2 C1 H1B 109.5 no H1A C1 H1B 109.5 no C2 C1 H1C 109.5 no H1A C1 H1C 109.5 no H1B C1 H1C 109.5 no C3 C4 H4 119.4 no C5 C4 H4 119.4 no C6 C5 H5 119.5 no C4 C5 H5 119.5 no C5 C6 H6 121.4 no C7 C6 H6 121.4 no N1 C10 H10 124.7 no C9 C10 H10 124.7 no N2 C13 H13A 108.9 no C14 C13 H13A 108.9 no N2 C13 H13B 108.9 no C14 C13 H13B 108.9 no H13A C13 H13B 107.8 no C13 C14 H14A 109.5 no C13 C14 H14B 109.5 no H14A C14 H14B 109.5 no C13 C14 H14C 109.5 no H14A C14 H14C 109.5 no H14B C14 H14C 109.5 no N2 C15 H15A 109.1 no C16 C15 H15A 109.1 no N2 C15 H15B 109.1 no C16 C15 H15B 109.1 no H15A C15 H15B 107.9 no C15 C16 H16A 109.5 no C15 C16 H16B 109.5 no H16A C16 H16B 109.5 no C15 C16 H16C 109.5 no H16A C16 H16C 109.5 no H16B C16 H16C 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.353(2) yes O1 C3 1.402(2) yes O2 C2 1.199(2) yes O3 C11 1.225(2) yes O4 C12 1.236(2) yes N1 C7 1.379(2) yes N1 C10 1.339(2) yes N2 C12 1.327(2) yes N2 C15 1.467(2) yes N2 C13 1.467(2) yes C1 C2 1.487(2) yes C3 C4 1.372(2) yes C3 C8 1.399(2) yes C4 C5 1.393(2) yes C5 C6 1.370(2) yes C6 C7 1.392(2) yes C7 C8 1.410(2) yes C8 C9 1.449(2) yes C9 C10 1.383(2) yes C9 C11 1.439(2) yes C11 C12 1.526(2) yes C13 C14 1.503(3) yes C15 C16 1.480(3) yes O1W H1W1 0.850(10) no O1W H1W2 0.850(10) no N1 H1N 0.860(10) no C1 H1A 0.96 no C1 H1B 0.96 no C1 H1C 0.96 no C4 H4 0.93 no C5 H5 0.93 no C6 H6 0.93 no C10 H10 0.93 no C13 H13A 0.97 no C13 H13B 0.97 no C14 H14A 0.96 no C14 H14B 0.96 no C14 H14C 0.96 no C15 H15A 0.97 no C15 H15B 0.97 no C16 H16A 0.96 no C16 H16B 0.96 no C16 H16C 0.96 no 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 H1N O1W . 0.860(10) 1.910(10) 2.743(2) 161(2) yes O1W H1W1 O2 3_666 0.850(10) 1.990(10) 2.841(2) 175(2) yes O1W H1W2 O4 4_656 0.850(10) 1.980(10) 2.810(2) 165(2) 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 C3 O1 C2 O2 3.0(2) no C3 O1 C2 C1 -177.90(10) no C2 O1 C3 C4 -112.5(2) no C2 O1 C3 C8 70.9(2) no O1 C3 C4 C5 -177.80(10) no C8 C3 C4 C5 -1.2(2) no C3 C4 C5 C6 -0.1(3) no C4 C5 C6 C7 0.5(2) no C10 N1 C7 C6 -179.80(10) no C10 N1 C7 C8 0.1(2) no C5 C6 C7 N1 -179.70(10) no C5 C6 C7 C8 0.3(2) no C4 C3 C8 C7 1.9(2) no O1 C3 C8 C7 178.50(10) no C4 C3 C8 C9 -179.6(2) no O1 C3 C8 C9 -3.0(2) no N1 C7 C8 C3 178.50(10) no C6 C7 C8 C3 -1.5(2) no N1 C7 C8 C9 -0.40(10) no C6 C7 C8 C9 179.50(10) no C3 C8 C9 C10 -178.1(2) no C7 C8 C9 C10 0.60(10) no C3 C8 C9 C11 2.5(2) no C7 C8 C9 C11 -178.90(10) no C7 N1 C10 C9 0.2(2) no C11 C9 C10 N1 179.00(10) no C8 C9 C10 N1 -0.5(2) no C10 C9 C11 O3 -169.30(10) no C8 C9 C11 O3 10.1(2) no C10 C9 C11 C12 7.7(2) no C8 C9 C11 C12 -173.00(10) no C15 N2 C12 O4 -0.3(2) no C13 N2 C12 O4 -179.5(2) no C15 N2 C12 C11 176.80(10) no C13 N2 C12 C11 -2.5(2) no O3 C11 C12 O4 94.3(2) no C9 C11 C12 O4 -82.9(2) no O3 C11 C12 N2 -82.9(2) no C9 C11 C12 N2 99.9(2) no C12 N2 C13 C14 98.0(2) no C15 N2 C13 C14 -81.3(2) no C12 N2 C15 C16 82.8(2) no C13 N2 C15 C16 -98.0(2) no