data_2100372
_journal_coeditor_code         DE5020
_journal_date_accepted         2005-11-19
_journal_date_recd_electronic  2005-04-29
_journal_issue                 1
_journal_name_full             'Acta Crystallographica, Section B'
_journal_page_first            109
_journal_page_last             117
_journal_paper_category        FA
_journal_volume                62
_journal_year                  2006
_chemical_formula_moiety       'C7 H3 I2 N O'
_chemical_formula_sum          'C7 H3 I2 N O'
_chemical_formula_weight       370.90
_chemical_melting_point        ?
_chemical_name_common          Iodoxynil
_chemical_name_systematic
;
 3,5-diiodo-4-hydroxybenzonitrile / polymorph C
;
_symmetry_cell_setting         monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         SHELXTL
_cell_angle_alpha              90.00
_cell_angle_beta               91.900(10)
_cell_angle_gamma              90.00
_cell_formula_units_Z          8
_cell_length_a                 15.657(4)
_cell_length_b                 14.320(4)
_cell_length_c                 7.724(2)
_cell_measurement_reflns_used  3574
_cell_measurement_temperature  173(2)
_cell_measurement_theta_max    27.5
_cell_measurement_theta_min    2.6
_cell_volume                   1730.8(8)
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_collection     'SMART (Bruker, 2002)'
_computing_data_reduction      SAINT
_computing_molecular_graphics  SHELXTL
_computing_publication_material SHELXTL
_computing_structure_refinement SHELXTL
_computing_structure_solution  'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature    173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
;
Siemens area detector diffractometer
;
_diffrn_measurement_method     '\w scans'
_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 0.038
_diffrn_reflns_av_sigmaI/netI  0.029
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_h_min     -20
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_l_max     10
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_number          16090
_diffrn_reflns_theta_full      27.50
_diffrn_reflns_theta_max       27.48
_diffrn_reflns_theta_min       1.31
_diffrn_standards_decay_%      'less than 1'
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  7.208
_exptl_absorpt_correction_T_max 0.60
_exptl_absorpt_correction_T_min 0.47
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
 SADABS;  Sheldrick, 1996;  Blessing, 1995'
;
_exptl_crystal_colour          colorless
_exptl_crystal_density_diffrn  2.841
_exptl_crystal_density_meas    'not measured'
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     needle
_exptl_crystal_F_000           1328
_exptl_crystal_size_max        0.50
_exptl_crystal_size_mid        0.10
_exptl_crystal_size_min        0.07
_refine_diff_density_max       0.60
_refine_diff_density_min       -0.54
_refine_ls_extinction_coef     0.00378(9)
_refine_ls_extinction_method   SHELXTL
_refine_ls_goodness_of_fit_ref 1.04
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_parameters   200
_refine_ls_number_reflns       3936
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.04
_refine_ls_R_factor_all        0.024
_refine_ls_R_factor_gt         0.020
_refine_ls_shift/su_max        0.006
_refine_ls_shift/su_mean       0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 calc w=1/[\s^2^(Fo^2^)+(0.014P)^2^+1.59P] where
P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.044
_refine_ls_wR_factor_ref       0.046
_reflns_number_gt              3587
_reflns_number_total           3931
_reflns_threshold_expression   '>2\s(I) '
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_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
I13 0.646356(10) 0.465381(13) 0.63572(2) 0.02125(6) Uani d . 1 . . I
I15 0.349835(11) 0.687241(12) 0.88878(2) 0.02308(6) Uani d . 1 . . I
O14 0.52408(12) 0.63736(13) 0.7359(2) 0.0248(4) Uani d . 1 . . O
H14 0.5761 0.6281 0.7184 0.030 Uiso calc R 1 . . H
N17 0.32264(16) 0.23472(18) 0.9129(4) 0.0354(6) Uani d . 1 . . N
C11 0.39844(16) 0.38959(18) 0.8398(3) 0.0189(5) Uani d . 1 . . C
C12 0.47917(15) 0.38600(19) 0.7684(3) 0.0189(5) Uani d . 1 . . C
H12 0.5043 0.3274 0.7429 0.023 Uiso calc R 1 . . H
C13 0.52267(15) 0.46812(18) 0.7347(3) 0.0174(5) Uani d . 1 . . C
C14 0.48550(16) 0.55495(18) 0.7689(3) 0.0179(5) Uani d . 1 . . C
C15 0.40463(15) 0.55699(17) 0.8405(3) 0.0167(5) Uani d . 1 . . C
C16 0.36027(15) 0.47558(19) 0.8771(3) 0.0181(5) Uani d . 1 . . C
H16 0.3055 0.4781 0.9261 0.022 Uiso calc R 1 . . H
C17 0.35481(17) 0.3039(2) 0.8807(4) 0.0246(6) Uani d . 1 . . C
I23 1.138156(11) 0.827849(13) 0.60680(2) 0.02323(6) Uani d . 1 . . I
I25 0.847294(11) 1.048985(13) 0.89008(2) 0.02429(6) Uani d . 1 . . I
O24 1.01711(12) 1.00074(13) 0.7181(3) 0.0262(4) Uani d . 1 . . O
H24 1.0643 0.9914 0.6725 0.039 Uiso calc R 1 . . H
N27 0.82339(16) 0.59508(18) 0.9021(3) 0.0319(6) Uani d . 1 . . N
C21 0.89493(16) 0.75212(18) 0.8299(3) 0.0192(5) Uani d . 1 . . C
C22 0.97489(16) 0.74859(18) 0.7543(3) 0.0199(5) Uani d . 1 . . C
H22 1.0002 0.6901 0.7285 0.024 Uiso calc R 1 . . H
C23 1.01709(16) 0.83144(19) 0.7173(3) 0.0189(5) Uani d . 1 . . C
C24 0.98030(16) 0.91772(18) 0.7545(3) 0.0188(5) Uani d . 1 . . C
C25 0.90055(16) 0.91920(18) 0.8323(3) 0.0186(5) Uani d . 1 . . C
C26 0.85755(15) 0.83761(19) 0.8708(3) 0.0195(5) Uani d . 1 . . C
H26 0.8037 0.8397 0.9239 0.023 Uiso calc R 1 . . H
C27 0.85282(16) 0.6653(2) 0.8709(3) 0.0241(6) Uani d . 1 . . C
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
I13 0.01725(9) 0.02018(10) 0.02665(10) 0.00015(6) 0.00579(6) 0.00036(7)
I15 0.02349(10) 0.01406(10) 0.03225(11) 0.00244(6) 0.00940(7) 0.00079(7)
O14 0.0221(10) 0.0151(10) 0.0380(11) -0.0018(8) 0.0113(8) 0.0012(8)
N17 0.0341(14) 0.0178(13) 0.0556(17) -0.0033(11) 0.0185(12) -0.0002(12)
C11 0.0194(12) 0.0147(13) 0.0227(12) -0.0007(10) 0.0012(10) -0.0006(10)
C12 0.0190(12) 0.0153(13) 0.0226(12) 0.0015(10) 0.0017(10) -0.0005(10)
C13 0.0132(11) 0.0177(13) 0.0214(12) 0.0010(10) 0.0034(9) 0.0005(10)
C14 0.0185(12) 0.0162(13) 0.0190(12) -0.0020(10) 0.0008(9) 0.0017(10)
C15 0.0176(12) 0.0130(12) 0.0196(12) 0.0035(9) 0.0013(9) -0.0011(10)
C16 0.0184(12) 0.0169(14) 0.0192(12) -0.0018(10) 0.0042(10) 0.0008(10)
C17 0.0229(14) 0.0179(15) 0.0336(16) 0.0017(11) 0.0094(12) -0.0009(11)
I23 0.01934(10) 0.01976(11) 0.03114(11) -0.00083(7) 0.00923(7) -0.00137(7)
I25 0.02248(10) 0.01767(11) 0.03318(11) 0.00277(7) 0.00763(7) 0.00025(7)
O24 0.0228(10) 0.0170(10) 0.0394(11) -0.0003(8) 0.0110(8) 0.0032(8)
N27 0.0282(13) 0.0182(13) 0.0496(15) -0.0018(10) 0.0029(11) -0.0017(11)
C21 0.0188(12) 0.0163(13) 0.0226(13) -0.0023(10) 0.0012(9) 0.0031(10)
C22 0.0212(13) 0.0144(13) 0.0241(13) -0.0017(10) 0.0008(10) -0.0011(10)
C23 0.0144(12) 0.0211(14) 0.0214(12) 0.0005(10) 0.0047(9) -0.0008(10)
C24 0.0197(12) 0.0155(14) 0.0214(12) -0.0017(10) 0.0021(10) 0.0013(10)
C25 0.0191(12) 0.0168(13) 0.0201(12) 0.0030(10) 0.0018(9) -0.0004(10)
C26 0.0162(12) 0.0183(14) 0.0242(13) -0.0015(10) 0.0033(10) 0.0015(10)
C27 0.0196(14) 0.0246(16) 0.0286(15) 0.0021(11) 0.0066(11) -0.0012(11)
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'
I I -0.4742 1.8119 '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
C14 O14 H14 . . 109.5 ?
C12 C11 C16 . . 120.7(2) ?
C12 C11 C17 . . 119.7(2) ?
C16 C11 C17 . . 119.5(2) ?
C13 C12 C11 . . 119.9(2) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.5(2) ?
C12 C13 I13 . . 121.01(19) ?
C14 C13 I13 . . 118.53(18) ?
O14 C14 C15 . . 118.1(2) ?
O14 C14 C13 . . 123.2(2) ?
C15 C14 C13 . . 118.7(2) ?
C16 C15 C14 . . 121.8(2) ?
C16 C15 I15 . . 120.04(18) ?
C14 C15 I15 . . 118.11(18) ?
C15 C16 C11 . . 118.4(2) ?
C15 C16 H16 . . 120.8 ?
C11 C16 H16 . . 120.8 ?
N17 C17 C11 . . 177.9(3) ?
C24 O24 H24 . . 109.5 ?
C22 C21 C26 . . 120.8(2) ?
C22 C21 C27 . . 118.7(2) ?
C26 C21 C27 . . 120.4(2) ?
C23 C22 C21 . . 119.5(2) ?
C23 C22 H22 . . 120.3 ?
C21 C22 H22 . . 120.3 ?
C22 C23 C24 . . 120.6(2) ?
C22 C23 I23 . . 120.15(19) ?
C24 C23 I23 . . 119.21(19) ?
O24 C24 C23 . . 123.5(2) ?
O24 C24 C25 . . 117.8(2) ?
C23 C24 C25 . . 118.7(2) ?
C26 C25 C24 . . 121.6(2) ?
C26 C25 I25 . . 120.25(18) ?
C24 C25 I25 . . 118.12(19) ?
C25 C26 C21 . . 118.7(2) ?
C25 C26 H26 . . 120.6 ?
C21 C26 H26 . . 120.6 ?
N27 C27 C21 . . 176.7(3) ?
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
I13 C13 . 2.106(2) ?
I15 C15 . 2.092(2) ?
O14 C14 . 1.354(3) ?
O14 H14 . 0.8400 ?
N17 C17 . 1.143(4) ?
C11 C12 . 1.397(3) ?
C11 C16 . 1.403(4) ?
C11 C17 . 1.444(4) ?
C12 C13 . 1.388(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.402(4) ?
C14 C15 . 1.399(3) ?
C15 C16 . 1.391(3) ?
C16 H16 . 0.9500 ?
I23 C23 . 2.105(2) ?
I25 C25 . 2.091(3) ?
O24 C24 . 1.355(3) ?
O24 H24 . 0.8400 ?
N27 C27 . 1.135(4) ?
C21 C22 . 1.400(3) ?
C21 C26 . 1.398(4) ?
C21 C27 . 1.447(4) ?
C22 C23 . 1.392(4) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.397(4) ?
C24 C25 . 1.404(3) ?
C25 C26 . 1.386(4) ?
C26 H26 . 0.9500 ?