#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2001820.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_2001820
loop_
_publ_author_name
'Nielsen, B. B.'
'Larsen, I. K.'
_publ_section_title
;
 3,4,5-Trihydroxybenzohydroxamic acid monohydrate, a ribonucleotide
 reductase inhibitor
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              810
_journal_page_last               813
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C7 H7 N1 O5, H2 O'
_chemical_formula_sum            'C7 H9 N O6'
_chemical_formula_weight         203.15
_chemical_name_systematic
'3,4,5-trihydroxybenzohydroxamic acid, monohydrate'
_chemical_temperature_decomposition 503.0(10)
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.0
_cell_angle_beta                 94.020(6)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   11.5961(8)
_cell_length_b                   3.6323(4)
_cell_length_c                   18.5310(10)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    110
_cell_measurement_theta_max      46.17
_cell_measurement_theta_min      39.91
_cell_volume                     778.61(11)
_computing_data_reduction        'BEGIN, SDP (Frenz, 1982)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_structure_refinement  'LSFM, SDP (Frenz, 1982)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110
_diffrn_measurement_device       'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         xray_tube
_diffrn_radiation_type           'Copper K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4298
_diffrn_reflns_theta_max         75.00
_diffrn_reflns_theta_min         1.000
_diffrn_standards_decay_%        -4.0
_diffrn_standards_interval_count 300
_diffrn_standards_interval_time  166
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.2944
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_description       'rectangular thin plates'
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.819
_refine_ls_goodness_of_fit_obs   2.091
_refine_ls_hydrogen_treatment
;refall except H102 and H4  for which both positional and displacement
parameters were fixed
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1231
_refine_ls_R_factor_obs          0.045
_refine_ls_shift/esd_max         0.00
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      1/(\s^2^(F)+(0.02F)^2^+2.00)
_refine_ls_wR_factor_obs         0.064
_reflns_number_observed          1231
_reflns_number_total             1609
_reflns_observed_criterion       >5sigma
_[local]_cod_data_source_file    ab1042.cif
_[local]_cod_data_source_block   OHBHA
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_[local]_cod_chemical_formula_sum_orig 'C7 H9 N1 O6'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been given
as '502-504 (decomp.)'. The value was changed to '503.0(10)' - the
average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        778.6(2)
_cod_database_code               2001820
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
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
_atom_site_aniso_type_symbol
O3 0.0112(6) 0.0286(9) 0.0119(6) -0.0021(7) 0.0020(6) 0.0060(7) O
O4 0.0134(7) 0.0280(10) 0.0122(7) 0.0029(7) -0.0019(6) -0.0006(7) O
O5 0.0126(6) 0.0175(8) 0.0090(6) 0.0002(6) 0.0022(5) 0.0037(6) O
O7 0.0182(7) 0.0234(9) 0.0100(7) 0.0045(7) -0.0008(6) -0.0021(7) O
O9 0.0114(7) 0.0315(9) 0.0165(7) 0.0019(8) -0.0021(6) 0.0085(8) O
O10 0.0430(10) 0.0420(10) 0.0460(10) 0.0280(10) -0.0330(9) -0.0281(9) O
N8 0.0129(8) 0.0210(10) 0.0099(8) 0.0037(8) -0.0025(7) -0.0003(8) N
C1 0.0125(9) 0.0073(9) 0.0109(8) 0.0007(8) 0.0001(7) -0.0015(8) C
C2 0.0155(9) 0.0110(10) 0.0089(8) 0.0015(9) 0.0012(7) -0.0003(8) C
C3 0.0121(9) 0.0120(10) 0.0126(9) -0.0006(9) 0.0027(7) -0.0010(8) C
C4 0.0121(9) 0.0110(10) 0.0112(9) -0.0003(8) -0.0016(8) -0.0005(8) C
C5 0.0145(9) 0.0086(9) 0.0097(9) -0.0014(8) 0.0024(8) -0.0005(8) C
C6 0.0115(9) 0.0110(10) 0.0126(9) -0.0014(8) 0.0025(8) -0.0005(8) C
C7 0.0151(9) 0.0094(9) 0.0118(9) -0.0007(9) 0.0002(8) -0.0006(8) C
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_thermal_displace_type
_atom_site_type_symbol
O3 0.42630(10) 0.5576(6) 0.37376(8) Beq O
O4 0.39930(10) 0.2770(6) 0.50631(9) Beq O
O5 0.17970(10) 0.0761(5) 0.54529(8) Beq O
O7 0.01540(10) 0.4181(5) 0.24199(8) Beq O
O9 -0.18310(10) 0.6263(6) 0.29423(9) Beq O
O10 0.3516(2) -0.2028(7) 0.63580(10) Beq O
N8 -0.0858(2) 0.5377(6) 0.33900(10) Beq N
C1 0.1130(2) 0.3939(6) 0.36090(10) Beq C
C2 0.2219(2) 0.4892(7) 0.33950(10) Beq C
C3 0.3175(2) 0.4545(7) 0.38820(10) Beq C
C4 0.3057(2) 0.3120(6) 0.45730(10) Beq C
C5 0.1964(2) 0.2138(6) 0.47800(10) Beq C
C6 0.0999(2) 0.2586(6) 0.43020(10) Beq C
C7 0.0114(2) 0.4496(6) 0.30840(10) Beq C
H2 0.231(2) 0.604(9) 0.2920(10) Biso H
H3 0.432(2) 0.650(9) 0.3330(10) Biso H
H4 0.461 0.332 0.484 Biso H
H5 0.254(3) 0.020(10) 0.567(2) Biso H
H6 0.026(2) 0.196(8) 0.4430(10) Biso H
H8 -0.088(3) 0.620(10) 0.383(2) Biso H
H9 -0.232(3) 0.480(10) 0.307(2) Biso H
H101 0.388(4) -0.12(2) 0.672(2) Biso H
H102 0.400 -0.416 0.617 Biso H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.017 0.009 International_Tables_Vol_IV_Table_2.3.1
H 0 0 International_Tables_Vol_IV_Table_2.3.1
N 0.029 0.018 International_Tables_Vol_IV_Table_2.3.1
O 0.047 0.032 International_Tables_Vol_IV_Table_2.3.1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 1 -2
0 1 3
2 0 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 C2 C3 . 119.5(2) yes
C1 C6 C5 . 119.6(2) yes
C2 C1 C6 . 120.6(2) yes
C2 C1 C7 . 118.1(2) yes
C2 C3 C4 . 120.3(2) yes
C3 C4 C5 . 119.7(2) yes
C4 C5 C6 . 120.2(2) yes
C6 C1 C7 . 121.3(2) yes
O3 C3 C2 . 124.0(2) yes
O3 C3 C4 . 115.8(2) yes
O4 C4 C3 . 121.1(2) yes
O4 C4 C5 . 119.2(2) yes
O5 C5 C6 . 117.8(2) yes
O5 C5 C4 . 122.1(2) yes
O7 C7 C1 . 123.6(2) yes
O7 C7 N8 . 122.4(2) yes
N8 C7 C1 . 114.1(2) yes
O9 N8 C7 . 118.4(2) yes
O3 H3 O7 2 162(3) yes
O4 H4 O3 . 115 yes
O4 H4 O4 3_656 107 yes
O4 H4 O4 3_666 139 yes
O5 H5 O4 . 112(3) yes
O5 H5 O10 . 154(3) yes
N8 H8 O5 3_566 146(3) yes
O9 H9 O9 2_445 112(3) yes
O9 H9 O10 3_556 163(3) yes
O10 H101 O7 4 163(4) yes
O10 H102 O3 3_656 135 yes
O10 H102 O4 1_545 133 yes
C3 O3 H3 . 115.(2) ?
C4 O4 H4 . 107.9(2) ?
C5 O5 H5 . 107.(2) ?
N8 O9 H9 . 103.(3) ?
H101 O10 H102 . 107.(3) ?
O9 N8 H8 . 114.(2) ?
C7 N8 H8 . 124.(2) ?
C1 C6 H6 . 119.0(10) ?
C5 C6 H6 . 121.0(10) ?
C1 C2 H2 . 121.(2) ?
C3 C2 H2 . 119.(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.394(3) yes
C1 C6 1.394(3) yes
C1 C7 1.489(3) yes
C2 C3 1.386(3) yes
C3 C4 1.398(3) yes
C4 C5 1.396(3) yes
C5 C6 1.386(3) yes
O3 C3 1.361(3) yes
O4 C4 1.371(3) yes
O5 C5 1.371(3) yes
O7 C7 1.240(3) yes
N8 C7 1.336(3) yes
O9 N8 1.390(2) yes
O3 H3 0.84(3) ?
C6 H6 0.94(3) ?
O4 H4 0.870(2) ?
O5 H5 0.95(3) ?
O9 H9 0.82(4) ?
O10 H101 0.83(4) ?
O10 H102 1.033(2) ?
N8 H8 0.88(3) ?
C2 H2 0.98(3) ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O3 O7 2.641(2) 2 yes
H3 O7 1.83(3) 2 yes
O4 O3 2.698 . yes
H4 O3 2.22 . yes
O4 O4 3.104 3_656 yes
H4 O4 2.74 3_656 yes
O4 O4 2.865 3_666 yes
H4 O4 2.15 3_666 yes
O5 O4 2.792(2) . yes
H5 O4 2.30(3) . yes
O5 O10 2.710(3) . yes
H5 O10 1.82(3) . yes
N8 O5 2.842(3) 3_566 yes
H8 O5 2.07(3) 3_566 yes
O9 O9 2.835(3) 2_445 yes
H9 O9 2.42(4) 2_445 yes
O9 O10 2.867(3) 3_556 yes
H9 O10 2.07(4) 3_556 yes
O10 O7 2.834(3) 4 yes
H101 O7 2.03(4) 4 yes
O10 O3 2.896 3_656 yes
H102 O3 2.07 3_656 yes
O10 O4 3.134 1_545 yes
H102 O4 2.34 1_545 yes
O9 O9 2.835(3) 2_455 yes
O3 O4 2.959(2) 3_666 yes
O4 O10 3.047(3) . yes
O9 O10 3.005(3) 4_454 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
C1 C2 C3 O3 -176.5(2) ?
C1 C2 C3 C4 2.4(4) ?
C2 C1 C6 C5 -0.9(4) ?
C2 C1 C7 O7 32.7(3) ?
C2 C1 C7 N8 -147.3(2) yes
C2 C3 C4 O4 -179.8(2) ?
C2 C3 C4 C5 -1.8(4) ?
C3 C4 C5 O5 -179.4(2) ?
C3 C4 C5 C6 -0.2(4) ?
C4 C5 C6 C1 1.5(3) ?
C6 C1 C7 O7 -148.8(2) ?
C6 C1 C7 N8 31.2(3) ?
C6 C1 C2 C3 -1.1(4) ?
C7 C1 C2 C3 177.4(2) ?
C7 C1 C6 C5 -179.3(2) ?
O3 C3 C4 C5 177.3(2) ?
O3 C3 C4 O4 -0.7(3) ?
O4 C4 C5 O5 -1.3(3) ?
O4 C4 C5 C6 177.8(2) ?
O5 C5 C6 C1 -179.3(2) ?
O9 N8 C7 O7 -5.4(4) yes
O9 N8 C7 C1 174.6(2) ?
H9 O9 N8 C7 123(3) yes
H3 O3 C3 C4 -178(2) ?
H4 O4 C4 C5 176 ?
H5 O5 C5 C6 169(2) ?
H3 O3 C3 C2 1(2) ?
H4 O4 C4 C3 -6.4(3) ?
H5 O5 C5 C4 -12(2) ?
H2 C2 C3 O3 -3(2) ?
H9 O9 N8 H8 -77(4) ?
H2 C2 C3 C4 176(2) ?
H8 N8 C7 O7 -163(3) ?
H8 N8 C7 C1 17(3) ?
C6 C1 C2 H2 -175(2) ?
C7 C1 C2 H2 4(2) ?
C2 C1 C6 H6 -179.9(8) ?
O5 C5 C6 H6 0(2) ?
C7 C1 C6 H6 2(2) ?
C4 C5 C6 H6 -179(2) ?