#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/11/2211150.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_2211150
loop_
_publ_author_name
'Nagarajan Vembu'
'Anthony Linden'
'Jean Lee'
'John G. Kelly'
'Kevin B. Nolan'
'Marc Devocelle'
_publ_section_title
;
 2-Amino-5-iodobenzohydroxamic acid: supramolecular aggregation through
 two-dimensional networks of N---H···O,
 O---H···N and C---H···O
 interactions
;
_journal_coeditor_code           OB2080
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5083
_journal_page_last               o5085
_journal_paper_doi               10.1107/S1600536806042383
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C7 H7 I N2 O2'
_chemical_formula_moiety         'C7 H7 I N2 O2'
_chemical_formula_sum            'C7 H7 I N2 O2'
_chemical_formula_weight         278.05
_chemical_name_common            '5-iodoanthranilichydroxamic acid'
_chemical_name_systematic
;
2-amino-5-iodobenzohydroxamic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.6614(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5332(4)
_cell_length_b                   4.8500(2)
_cell_length_c                   13.2820(4)
_cell_measurement_reflns_used    67557
_cell_measurement_temperature    160.0(10)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     843.39(5)
_computing_cell_refinement       'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO--SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      160.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR590 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22968
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         3.11
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.756
_exptl_absorpt_correction_T_max  0.773
_exptl_absorpt_correction_T_min  0.512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         2.178
_refine_diff_density_min         -1.181
_refine_ls_extinction_coef       0.0189(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0534P)²+0.3155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                2084
_reflns_number_total             2458
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob2080.cif
_cod_data_source_block           I
_cod_database_code               2211150
_cod_database_fobs_code          2211150
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
C C1 0.3334(2) 0.6155(6) 0.3337(2) 0.0205(5) Uani d 1
C C2 0.2717(2) 0.7521(7) 0.3890(2) 0.0223(5) Uani d 1
C C3 0.1660(2) 0.7087(7) 0.3591(3) 0.0256(6) Uani d 1
C C4 0.1216(2) 0.5382(7) 0.2753(2) 0.0255(6) Uani d 1
C C5 0.1838(2) 0.4073(7) 0.2215(2) 0.0227(6) Uani d 1
C C6 0.2887(2) 0.4446(6) 0.2502(2) 0.0215(6) Uani d 1
C C7 0.4463(2) 0.6624(6) 0.3619(2) 0.0197(6) Uani d 1
N N8 0.50113(18) 0.4420(6) 0.3552(2) 0.0237(5) Uani d 1
N N9 0.3137(2) 0.9087(6) 0.4775(2) 0.0259(5) Uani d 1
O O10 0.48448(17) 0.8926(5) 0.38795(19) 0.0265(5) Uani d 1
O O11 0.60607(16) 0.4718(5) 0.3671(2) 0.0296(5) Uani d 1
I I 0.119249(15) 0.16606(5) 0.090077(15) 0.02907(12) Uani d 1
H H3 0.127(3) 0.805(8) 0.393(4) 0.028(11) Uiso d 1
H H4 0.046(3) 0.511(7) 0.254(3) 0.015(8) Uiso d 1
H H6 0.329(3) 0.369(7) 0.212(3) 0.016(8) Uiso d 1
H H8 0.482(4) 0.263(11) 0.350(4) 0.039(12) Uiso d 1
H H9A 0.370(3) 0.974(8) 0.478(3) 0.022(9) Uiso d 1
H H9B 0.273(4) 1.031(10) 0.492(4) 0.043(12) Uiso d 1
H H11 0.629(3) 0.349(8) 0.422(4) 0.034(12) Uiso d 1
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
C1 0.0192(12) 0.0211(14) 0.0209(13) -0.0013(10) 0.0042(10) -0.0005(11)
C2 0.0245(14) 0.0223(13) 0.0202(13) 0.0008(12) 0.0058(11) 0.0001(12)
C3 0.0221(14) 0.0319(17) 0.0249(15) 0.0012(12) 0.0099(12) -0.0005(13)
C4 0.0207(13) 0.0313(17) 0.0249(14) -0.0004(12) 0.0065(11) 0.0004(13)
C5 0.0229(13) 0.0246(13) 0.0191(13) -0.0033(11) 0.0026(10) 0.0000(11)
C6 0.0211(12) 0.0223(15) 0.0224(13) -0.0017(11) 0.0079(10) -0.0016(11)
C7 0.0222(14) 0.0198(14) 0.0179(12) -0.0020(10) 0.0065(11) 0.0002(10)
N8 0.0176(11) 0.0222(14) 0.0319(13) -0.0017(10) 0.0074(10) -0.0011(11)
N9 0.0249(13) 0.0276(13) 0.0257(13) 0.0016(12) 0.0074(11) -0.0062(11)
O10 0.0250(11) 0.0216(10) 0.0307(12) -0.0037(9) 0.0028(9) -0.0037(9)
O11 0.0181(10) 0.0316(13) 0.0403(13) 0.0003(9) 0.0093(9) 0.0080(10)
I 0.02542(15) 0.03572(17) 0.02536(15) -0.00795(7) 0.00510(9) -0.00667(7)
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 for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
I I 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 0.0106 0.0060
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O -0.4742 1.8119
; International Tables for Crystallography (1992).
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
C6 C1 C2 119.9(3)
C6 C1 C7 120.0(3)
C2 C1 C7 120.0(3)
N9 C2 C3 119.4(3)
N9 C2 C1 121.7(3)
C3 C2 C1 118.6(3)
C4 C3 C2 121.3(3)
C4 C3 H3 121(3)
C2 C3 H3 118(3)
C5 C4 C3 119.1(3)
C5 C4 H4 120.2(19)
C3 C4 H4 120.7(19)
C6 C5 C4 120.8(3)
C6 C5 I 118.9(2)
C4 C5 I 120.3(2)
C5 C6 C1 120.3(3)
C5 C6 H6 120(2)
C1 C6 H6 119(2)
O10 C7 N8 123.2(3)
O10 C7 C1 122.2(3)
N8 C7 C1 114.6(2)
C7 N8 O11 118.9(3)
C7 N8 H8 129(3)
O11 N8 H8 112(3)
C2 N9 H9A 113(3)
C2 N9 H9B 114(3)
H9A N9 H9B 112(4)
N8 O11 H11 99(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.394(4)
C1 C2 1.410(4)
C1 C7 1.496(4)
C2 N9 1.394(4)
C2 C3 1.399(4)
C3 C4 1.395(5)
C3 H3 0.90(5)
C4 C5 1.388(4)
C4 H4 1.00(3)
C5 C6 1.386(4)
C5 I 2.100(3)
C6 H6 0.91(4)
C7 O10 1.242(4)
C7 N8 1.317(4)
N8 O11 1.396(3)
N8 H8 0.91(5)
N9 H9A 0.82(4)
N9 H9B 0.87(5)
O11 H11 0.93(4)
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
N8 H8 O10 1_545 0.91(5) 1.86(5) 2.718(4) 157(4) yes
N9 H9A O10 . 0.82(4) 2.22(4) 2.855(4) 135(3) yes
N9 H9A O10 3_676 0.82(4) 2.39(4) 3.018(4) 134(3) yes
N9 H9B I 4_576 0.87(5) 3.09(5) 3.925(3) 163(4) yes
O11 H11 N9 3_666 0.93(4) 1.85(5) 2.777(4) 173(4) yes
C6 H6 O11 2_645 0.91(4) 2.46(4) 3.292(4) 152(3) 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
C6 C1 C2 N9 175.3(3)
C7 C1 C2 N9 -7.1(5)
C6 C1 C2 C3 0.9(5)
C7 C1 C2 C3 178.5(3)
N9 C2 C3 C4 -175.6(3)
C1 C2 C3 C4 -1.1(5)
C2 C3 C4 C5 0.6(5)
C3 C4 C5 C6 0.0(5)
C3 C4 C5 I -176.7(2)
C4 C5 C6 C1 -0.2(5)
I C5 C6 C1 176.6(2)
C2 C1 C6 C5 -0.3(5)
C7 C1 C6 C5 -177.9(3)
C6 C1 C7 O10 139.3(3)
C2 C1 C7 O10 -38.3(4)
C6 C1 C7 N8 -39.6(4)
C2 C1 C7 N8 142.8(3)
O10 C7 N8 O11 -6.9(4)
C1 C7 N8 O11 172.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9805246
