#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/03/2230393.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_2230393
loop_
_publ_author_name
'Miao, Yanqing'
'Zhang, Xiaoqing'
'Liu, Chunye'
'You, Jing'
_publ_section_title
;
 Tris(3-hydroxyimino-1-methylindolin-2-one) monohydrate
;
_journal_coeditor_code           JJ2082
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1291
_journal_paper_doi               10.1107/S1600536811015418
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '3C9 H8 N2 O2, H2 O'
_chemical_formula_moiety         '3(C9 H8 N2 O2), H2 O'
_chemical_formula_sum            'C27 H26 N6 O7'
_chemical_formula_weight         546.54
_chemical_name_systematic
;
Tris(3-hydroxyimino-1-methylindolin-2-one) monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.335(3)
_cell_angle_beta                 101.013(3)
_cell_angle_gamma                112.784(3)
_cell_formula_units_Z            2
_cell_length_a                   8.920(3)
_cell_length_b                   10.811(4)
_cell_length_c                   14.915(5)
_cell_measurement_reflns_used    3022
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.8
_cell_volume                     1294.1(8)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7872
_diffrn_reflns_theta_full        25.12
_diffrn_reflns_theta_max         25.12
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.214
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0716P)²+0.1735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1400
_reflns_number_gt                3154
_reflns_number_total             4512
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jj2082.cif
_cod_data_source_block           I
_cod_original_cell_volume        1294.1(7)
_cod_database_code               2230393
_cod_database_fobs_code          2230393
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 1.0271(3) -0.0706(3) 0.09769(15) 0.0623(7) Uani d . 1 1 . .
H H1C 0.9774 -0.0060 0.0908 0.093 Uiso calc R 1 1 . .
H H1D 0.9527 -0.1539 0.0614 0.093 Uiso calc R 1 1 . .
H H1E 1.1302 -0.0366 0.0774 0.093 Uiso calc R 1 1 . .
C C2 1.1891(3) -0.2589(2) 0.18264(15) 0.0521(6) Uani d . 1 1 . .
H H2A 1.1852 -0.2568 0.1200 0.063 Uiso calc R 1 1 . .
C C3 1.2550(3) -0.3391(2) 0.23265(16) 0.0574(6) Uani d . 1 1 . .
H H3A 1.2959 -0.3919 0.2030 0.069 Uiso calc R 1 1 . .
C C4 1.2614(3) -0.3426(2) 0.32544(16) 0.0557(6) Uani d . 1 1 . .
H H4A 1.3074 -0.3967 0.3576 0.067 Uiso calc R 1 1 . .
C C5 1.1999(3) -0.2663(2) 0.37148(15) 0.0478(5) Uani d . 1 1 . .
H H5A 1.2032 -0.2694 0.4341 0.057 Uiso calc R 1 1 . .
C C6 1.0575(2) -0.0964(2) 0.34600(13) 0.0407(5) Uani d . 1 1 . .
C C7 1.0105(3) -0.0384(2) 0.25993(14) 0.0448(5) Uani d . 1 1 . .
C C8 1.1296(2) -0.18248(19) 0.22847(13) 0.0399(5) Uani d . 1 1 . .
C C9 1.1338(2) -0.18576(19) 0.32271(13) 0.0386(5) Uani d . 1 1 . .
C C10 0.8968(3) 0.2792(3) 0.09247(17) 0.0675(7) Uani d . 1 1 . .
H H10A 0.8865 0.2812 0.0273 0.101 Uiso calc R 1 1 . .
H H10B 0.8290 0.1906 0.1050 0.101 Uiso calc R 1 1 . .
H H10C 1.0111 0.3012 0.1215 0.101 Uiso calc R 1 1 . .
C C11 0.7880(3) 0.4583(2) 0.07539(15) 0.0517(6) Uani d . 1 1 . .
C C12 0.7441(3) 0.5409(2) 0.13851(16) 0.0500(6) Uani d . 1 1 . .
C C13 0.7619(3) 0.5382(2) 0.31557(18) 0.0624(7) Uani d . 1 1 . .
H H13A 0.7203 0.6035 0.3235 0.075 Uiso calc R 1 1 . .
C C14 0.8102(3) 0.4762(3) 0.38937(18) 0.0704(7) Uani d . 1 1 . .
H H14A 0.8017 0.5010 0.4477 0.084 Uiso calc R 1 1 . .
C C15 0.8700(3) 0.3796(3) 0.37811(17) 0.0649(7) Uani d . 1 1 . .
H H15A 0.9010 0.3399 0.4291 0.078 Uiso calc R 1 1 . .
C C16 0.8857(3) 0.3390(2) 0.29342(15) 0.0536(6) Uani d . 1 1 . .
H H16A 0.9263 0.2730 0.2861 0.064 Uiso calc R 1 1 . .
C C17 0.7775(3) 0.5000(2) 0.22938(15) 0.0476(5) Uani d . 1 1 . .
C C18 0.8386(2) 0.4006(2) 0.22021(14) 0.0437(5) Uani d . 1 1 . .
C C19 0.5818(3) 0.0036(2) 0.3080(2) 0.0684(7) Uani d . 1 1 . .
H H19A 0.6085 -0.0336 0.2572 0.103 Uiso calc R 1 1 . .
H H19B 0.5085 -0.0682 0.3355 0.103 Uiso calc R 1 1 . .
H H19C 0.6822 0.0540 0.3528 0.103 Uiso calc R 1 1 . .
C C20 0.4430(3) 0.1584(3) 0.42273(17) 0.0636(7) Uani d . 1 1 . .
H H20A 0.4850 0.1037 0.4570 0.076 Uiso calc R 1 1 . .
C C21 0.3780(4) 0.2375(3) 0.4624(2) 0.0796(8) Uani d . 1 1 . .
H H21A 0.3765 0.2360 0.5245 0.096 Uiso calc R 1 1 . .
C C22 0.3155(4) 0.3182(3) 0.4117(2) 0.0831(9) Uani d . 1 1 . .
H H22A 0.2712 0.3696 0.4399 0.100 Uiso calc R 1 1 . .
C C23 0.3178(3) 0.3241(2) 0.31945(18) 0.0641(7) Uani d . 1 1 . .
H H23A 0.2765 0.3796 0.2856 0.077 Uiso calc R 1 1 . .
C C24 0.4038(3) 0.2266(2) 0.18659(15) 0.0457(5) Uani d . 1 1 . .
C C25 0.4784(3) 0.1244(2) 0.18822(17) 0.0513(6) Uani d . 1 1 . .
C C26 0.4435(3) 0.1635(2) 0.33104(15) 0.0469(5) Uani d . 1 1 . .
C C27 0.3819(3) 0.2464(2) 0.27895(15) 0.0459(5) Uani d . 1 1 . .
N N1 1.0252(2) -0.05933(18) 0.41960(11) 0.0495(5) Uani d . 1 1 . .
N N2 1.0588(2) -0.09364(18) 0.19319(11) 0.0463(4) Uani d . 1 1 . .
N N3 0.6924(2) 0.6279(2) 0.10394(15) 0.0642(6) Uani d . 1 1 . .
N N4 0.8424(2) 0.37665(18) 0.12804(12) 0.0487(5) Uani d . 1 1 . .
N N5 0.3804(2) 0.27722(18) 0.11122(13) 0.0546(5) Uani d . 1 1 . .
N N6 0.5003(2) 0.09227(17) 0.27555(13) 0.0506(5) Uani d . 1 1 . .
O O1 1.0755(2) -0.11735(17) 0.49500(10) 0.0646(5) Uani d . 1 1 . .
H H1B 1.0526 -0.0908 0.5404 0.097 Uiso calc R 1 1 . .
O O2 0.9441(2) 0.04077(16) 0.25021(11) 0.0622(5) Uani d . 1 1 . .
O O3 0.6579(2) 0.69901(18) 0.16874(15) 0.0858(6) Uani d . 1 1 . .
H H3C 0.6297 0.7564 0.1448 0.129 Uiso calc R 1 1 . .
O O4 0.7795(2) 0.46187(18) -0.00736(11) 0.0718(5) Uani d . 1 1 . .
O O5 0.3164(2) 0.37245(16) 0.12083(12) 0.0681(5) Uani d . 1 1 . .
H H5C 0.3017 0.4030 0.0716 0.102 Uiso calc R 1 1 . .
O O6 0.5143(2) 0.07832(18) 0.12371(13) 0.0762(5) Uani d . 1 1 . .
O O7W 0.5777(4) 0.8629(2) 0.06685(15) 0.1353(11) Uani d . 1 1 . .
H H7WA 0.5613 0.9341 0.0977 0.162 Uiso d R 1 1 . .
H H7WB 0.5520 0.8683 0.0019 0.162 Uiso d R 1 1 . .
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
N2 C1 H1C . . 109.5 ?
N2 C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
N2 C1 H1E . . 109.5 ?
H1C C1 H1E . . 109.5 ?
H1D C1 H1E . . 109.5 ?
C8 C2 C3 . . 117.9(2) ?
C8 C2 H2A . . 121.1 ?
C3 C2 H2A . . 121.1 ?
C4 C3 C2 . . 121.4(2) ?
C4 C3 H3A . . 119.3 ?
C2 C3 H3A . . 119.3 ?
C3 C4 C5 . . 120.7(2) ?
C3 C4 H4A . . 119.6 ?
C5 C4 H4A . . 119.6 ?
C9 C5 C4 . . 118.7(2) ?
C9 C5 H5A . . 120.7 ?
C4 C5 H5A . . 120.7 ?
N1 C6 C9 . . 135.00(19) ?
N1 C6 C7 . . 117.56(17) ?
C9 C6 C7 . . 107.45(16) ?
O2 C7 N2 . . 126.5(2) ?
O2 C7 C6 . . 128.18(19) ?
N2 C7 C6 . . 105.36(16) ?
C2 C8 N2 . . 128.31(19) ?
C2 C8 C9 . . 121.50(19) ?
N2 C8 C9 . . 110.19(16) ?
C5 C9 C8 . . 119.85(17) ?
C5 C9 C6 . . 134.28(19) ?
C8 C9 C6 . . 105.86(17) ?
N4 C10 H10A . . 109.5 ?
N4 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
N4 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O4 C11 N4 . . 125.8(2) ?
O4 C11 C12 . . 127.9(2) ?
N4 C11 C12 . . 106.29(18) ?
N3 C12 C17 . . 135.8(2) ?
N3 C12 C11 . . 117.3(2) ?
C17 C12 C11 . . 106.83(18) ?
C14 C13 C17 . . 118.1(2) ?
C14 C13 H13A . . 121.0 ?
C17 C13 H13A . . 121.0 ?
C15 C14 C13 . . 121.3(2) ?
C15 C14 H14A . . 119.3 ?
C13 C14 H14A . . 119.3 ?
C14 C15 C16 . . 121.9(2) ?
C14 C15 H15A . . 119.1 ?
C16 C15 H15A . . 119.1 ?
C15 C16 C18 . . 117.0(2) ?
C15 C16 H16A . . 121.5 ?
C18 C16 H16A . . 121.5 ?
C13 C17 C18 . . 119.1(2) ?
C13 C17 C12 . . 134.5(2) ?
C18 C17 C12 . . 106.35(18) ?
C16 C18 C17 . . 122.6(2) ?
C16 C18 N4 . . 127.6(2) ?
C17 C18 N4 . . 109.79(18) ?
N6 C19 H19A . . 109.5 ?
N6 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
N6 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C26 C20 C21 . . 117.7(2) ?
C26 C20 H20A . . 121.2 ?
C21 C20 H20A . . 121.2 ?
C22 C21 C20 . . 121.2(3) ?
C22 C21 H21A . . 119.4 ?
C20 C21 H21A . . 119.4 ?
C21 C22 C23 . . 120.9(3) ?
C21 C22 H22A . . 119.5 ?
C23 C22 H22A . . 119.5 ?
C27 C23 C22 . . 118.7(2) ?
C27 C23 H23A . . 120.7 ?
C22 C23 H23A . . 120.7 ?
N5 C24 C27 . . 135.82(19) ?
N5 C24 C25 . . 117.7(2) ?
C27 C24 C25 . . 106.41(18) ?
O6 C25 N6 . . 126.0(2) ?
O6 C25 C24 . . 127.1(2) ?
N6 C25 C24 . . 106.86(19) ?
C20 C26 N6 . . 128.3(2) ?
C20 C26 C27 . . 121.6(2) ?
N6 C26 C27 . . 110.07(19) ?
C23 C27 C26 . . 119.9(2) ?
C23 C27 C24 . . 133.9(2) ?
C26 C27 C24 . . 106.19(18) ?
C6 N1 O1 . . 112.81(16) ?
C7 N2 C8 . . 111.12(16) ?
C7 N2 C1 . . 123.47(17) ?
C8 N2 C1 . . 125.22(17) ?
C12 N3 O3 . . 112.1(2) ?
C11 N4 C18 . . 110.72(17) ?
C11 N4 C10 . . 123.89(18) ?
C18 N4 C10 . . 125.39(18) ?
C24 N5 O5 . . 111.20(18) ?
C25 N6 C26 . . 110.46(17) ?
C25 N6 C19 . . 124.4(2) ?
C26 N6 C19 . . 125.0(2) ?
N1 O1 H1B . . 109.5 ?
N3 O3 H3C . . 109.5 ?
N5 O5 H5C . . 109.5 ?
H7WA O7W H7WB . . 108.0 ?
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
C1 N2 . 1.445(3) ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
C1 H1E . 0.9600 ?
C2 C8 . 1.372(3) ?
C2 C3 . 1.383(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.376(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.385(3) ?
C4 H4A . 0.9300 ?
C5 C9 . 1.378(3) ?
C5 H5A . 0.9300 ?
C6 N1 . 1.280(2) ?
C6 C9 . 1.449(3) ?
C6 C7 . 1.501(3) ?
C7 O2 . 1.212(2) ?
C7 N2 . 1.367(3) ?
C8 N2 . 1.402(2) ?
C8 C9 . 1.401(3) ?
C10 N4 . 1.447(3) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 O4 . 1.224(3) ?
C11 N4 . 1.360(3) ?
C11 C12 . 1.487(3) ?
C12 N3 . 1.277(3) ?
C12 C17 . 1.448(3) ?
C13 C14 . 1.387(4) ?
C13 C17 . 1.389(3) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.365(4) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.377(3) ?
C15 H15A . 0.9300 ?
C16 C18 . 1.374(3) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.396(3) ?
C18 N4 . 1.402(3) ?
C19 N6 . 1.452(3) ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 C26 . 1.371(3) ?
C20 C21 . 1.381(4) ?
C20 H20A . 0.9300 ?
C21 C22 . 1.375(4) ?
C21 H21A . 0.9300 ?
C22 C23 . 1.383(4) ?
C22 H22A . 0.9300 ?
C23 C27 . 1.370(3) ?
C23 H23A . 0.9300 ?
C24 N5 . 1.279(3) ?
C24 C27 . 1.450(3) ?
C24 C25 . 1.492(3) ?
C25 O6 . 1.223(3) ?
C25 N6 . 1.354(3) ?
C26 N6 . 1.402(3) ?
C26 C27 . 1.400(3) ?
N1 O1 . 1.385(2) ?
N3 O3 . 1.372(3) ?
N5 O5 . 1.373(2) ?
O1 H1B . 0.8200 ?
O3 H3C . 0.8200 ?
O5 H5C . 0.8200 ?
O7W H7WA . 0.9600 ?
O7W H7WB . 0.9600 ?
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
O7W H7WA O6 1_565 0.96 1.82 2.752(3) 164
O1 H1B N1 2_756 0.82 2.11 2.780(3) 139
O7W H7WB O6 2_665 0.96 2.02 2.958(3) 165
O7W H7WB N5 2_665 0.96 2.59 3.181(3) 120
O3 H3C O7W . 0.82 1.78 2.579(3) 165
O5 H5C O4 3_665 0.82 2.05 2.753(3) 144
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656711
