#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$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/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2203355
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_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
3-[2-(N,N-Diethylamino)glyoxyloyl]-1H-indol-4-yl acetate monohydrate
;
_symmetry_cell_setting         Monoclinic
_symmetry_space_group_name_Hall '-P 2yab'
_symmetry_space_group_name_H-M 'P 21/a'
_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_detector_area_resol_mean ?
_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_count ?
_diffrn_standards_interval_time 0
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.094
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_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_coef     ?
_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_disorder_assembly
_atom_site_disorder_group
_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_site_symmetry_1
_geom_angle_site_symmetry_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_site_symmetry_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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_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