#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006233.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_2006233
loop_
_publ_author_name
'Elmali, A.'
'Elerman, Y.'
_publ_section_title
;
 2-[(2-Iodophenyl)iminomethyl]phenol
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              791
_journal_page_last               793
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C13 H10 I N O'
_chemical_formula_weight         323.12
_chemical_name_systematic
;
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4538(6)
_cell_length_b                   12.563(2)
_cell_length_c                   12.9830(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      12.13
_cell_measurement_theta_min      3.24
_cell_volume                     1215.8(2)
_computing_cell_refinement       SDP
_computing_data_collection       'SDP (Frenz, 1985)'
_computing_data_reduction        SDP
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990); direct methods'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0122
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2251
_diffrn_reflns_theta_max         23
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.61
_exptl_absorpt_correction_T_max  0.593
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_type   '\y scan (SDP; Frenz, 1985)'
_exptl_crystal_colour            'light beige'
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_description       Prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.63
_refine_diff_density_min         -0.19
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.093
_refine_ls_goodness_of_fit_obs   1.093
_refine_ls_hydrogen_treatment
;
H atoms: riding with fixed U's, except for those bonded to C7 and O1
which were freely refined
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_restrained_S_obs      1.093
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_obs          0.0217
_refine_ls_shift/esd_max         0.007
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0325P)^2^+0.5571P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.0589
_refine_ls_wR_factor_obs         0.0577
_reflns_number_observed          1634
_reflns_number_total             1695
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    mu1303.cif
_[local]_cod_data_source_block   I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2006233
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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 0.068(2) 0.056(2) 0.066(2) 0.000(2) 0.007(2) -0.008(2)
C2 0.079(3) 0.067(3) 0.084(3) -0.005(2) 0.019(3) -0.012(3)
C3 0.118(4) 0.069(3) 0.071(3) -0.022(3) 0.033(3) -0.016(3)
C4 0.119(4) 0.089(4) 0.052(2) -0.019(3) 0.003(3) -0.005(2)
C5 0.094(3) 0.077(3) 0.062(3) -0.015(3) -0.005(2) -0.004(3)
C6 0.079(3) 0.049(2) 0.056(2) -0.008(2) 0.004(2) -0.005(2)
C7 0.065(3) 0.055(2) 0.069(3) -0.003(2) -0.002(2) -0.003(2)
C8 0.058(2) 0.051(2) 0.063(2) -0.008(2) -0.005(2) -0.004(2)
C9 0.069(3) 0.060(2) 0.077(2) 0.006(2) -0.001(2) 0.008(2)
C10 0.064(2) 0.067(3) 0.086(3) 0.002(2) 0.009(2) 0.000(2)
C11 0.065(3) 0.071(3) 0.076(3) -0.008(2) 0.010(2) 0.000(2)
C12 0.077(3) 0.054(2) 0.064(2) -0.008(2) -0.009(2) 0.007(2)
C13 0.055(2) 0.052(2) 0.060(2) -0.006(2) -0.005(2) -0.004(2)
N1 0.065(2) 0.057(2) 0.060(2) -0.003(2) 0.002(2) 0.006(2)
O1 0.067(2) 0.106(3) 0.080(2) -0.008(2) -0.006(2) 0.010(2)
I1 0.0650(2) 0.0800(2) 0.0921(2) 0.0111(2) -0.0056(2) 0.00507(14)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.1860(6) 0.6058(4) 0.9490(3) 0.0633(10) Uani d . 1 C
C2 0.0803(7) 0.5589(4) 1.0249(4) 0.0766(13) Uani d . 1 C
H2A -0.0388(7) 0.5418(4) 1.0112(4) 0.092 Uiso calc R 1 H
C3 0.1520(9) 0.5382(4) 1.1198(4) 0.086(2) Uani d . 1 C
H3A 0.0808(9) 0.5067(4) 1.1701(4) 0.103 Uiso calc R 1 H
C4 0.3263(9) 0.5628(4) 1.1422(4) 0.087(2) Uani d . 1 C
H4A 0.3730(9) 0.5474(4) 1.2069(4) 0.104 Uiso calc R 1 H
C5 0.4312(7) 0.6099(4) 1.0694(3) 0.0780(12) Uani d . 1 C
H5A 0.5491(7) 0.6278(4) 1.0852(3) 0.094 Uiso calc R 1 H
C6 0.3636(6) 0.6316(3) 0.9713(3) 0.0615(11) Uani d . 1 C
C7 0.4831(7) 0.6769(3) 0.8930(3) 0.0632(11) Uani d . 1 C
H7 0.606(6) 0.683(3) 0.914(3) 0.053(11) Uiso d . 1 H
C8 0.5551(5) 0.7311(3) 0.7286(3) 0.0573(9) Uani d . 1 C
C9 0.7225(6) 0.6849(3) 0.7182(3) 0.0689(11) Uani d . 1 C
H9A 0.7555(6) 0.6307(3) 0.7631(3) 0.083 Uiso calc R 1 H
C10 0.8406(6) 0.7165(4) 0..6438(4) 0.0722(12) Uani d . 1 C
H10A 0.9524(6) 0.6840(4) 0.6389(4) 0.087 Uiso calc R 1 H
C11 0.7950(6) 0.7958(4) 0.5767(4) 0.0703(12) Uani d . 1 C
H11A 0.8753(6) 0.8169(4) 0.5258(4) 0.084 Uiso calc R 1 H
C12 0.6300(6) 0.8444(4) 0.5845(3) 0.0649(11) Uani d . 1 C
H12A 0.5990(6) 0.8991(4) 0.5396(3) 0.078 Uiso calc R 1 H
C13 0.5104(5) 0.8113(3) 0.6597(3) 0.0556(9) Uani d . 1 C
N1 0.4302(5) 0.6965(3) 0.8022(3) 0.0608(8) Uani d . 1 N
O1 0.1139(4) 0.6237(3) 0.8561(3) 0.0844(10) Uani d . 1 O
H1O 0.191(6) 0.662(4) 0.822(3) 0.066(13) Uiso d . 1 H
I1 0.26081(4) 0.88602(2) 0.66965(2) 0.07903(14) Uani d . 1 I
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
_geom_angle_publ_flag
O1 C1 C6 122.0(4) y
O1 C1 C2 118.8(4) y
C6 C1 C2 119.3(4) ?
C3 C2 C1 119.8(5) ?
C3 C2 H2A 120.1(3) ?
C1 C2 H2A 120.1(3) ?
C2 C3 C4 121.4(5) ?
C2 C3 H3A 119.3(3) ?
C4 C3 H3A 119.3(3) ?
C5 C4 C3 119.8(5) ?
C5 C4 H4A 120.1(3) ?
C3 C4 H4A 120.1(3) ?
C4 C5 C6 120.7(5) ?
C4 C5 H5A 119.7(3) ?
C6 C5 H5A 119.7(3) ?
C1 C6 C5 119.1(4) ?
C1 C6 C7 121.6(4) ?
C5 C6 C7 119.2(4) ?
N1 C7 C6 122.1(4) y
N1 C7 H7 123.(2) ?
C6 C7 H7 114.(2) ?
C9 C8 C13 117.3(4) ?
C9 C8 N1 122.3(4) y
C13 C8 N1 120.3(4) y
C10 C9 C8 121.9(4) ?
C10 C9 H9A 119.0(3) ?
C8 C9 H9A 119.0(3) ?
C9 C10 C11 120.1(4) ?
C9 C10 H10A 119.9(3) ?
C11 C10 H10A 119.9(3) ?
C10 C11 C12 119.9(4) ?
C10 C11 H11A 120.0(3) ?
C12 C11 H11A 120.0(3) ?
C11 C12 C13 119.6(4) ?
C11 C12 H12A 120.2(3) ?
C13 C12 H12A 120.2(2) ?
C12 C13 C8 121.1(4) ?
C12 C13 I1 118.8(3) y
C8 C13 I1 120.0(3) y
C7 N1 C8 119.2(4) y
C1 O1 H1O 107.(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.339(5) y
C1 C6 1.393(6) no
C1 C2 1.393(6) no
C2 C3 1.367(8) no
C2 H2A 0.93 ?
C3 C4 1.366(8) no
C3 H3A 0.93 ?
C4 C5 1.362(7) no
C4 H4A 0.93 ?
C5 C6 1.397(6) no
C5 H5A 0.93 ?
C6 C7 1.466(6) y
C7 N1 1.267(5) y
C7 H7 0.96(4) ?
C8 C9 1.382(6) no
C8 C13 1.388(6) no
C8 N1 1.404(5) y
C9 C10 1.366(6) no
C9 H9A 0.93 ?
C10 C11 1.367(6) no
C10 H10A 0.93 ?
C11 C12 1.377(6) no
C11 H11A 0.93 ?
C12 C13 1.386(6) no
C12 H12A 0.93 ?
C13 I1 2.088(4) y
O1 H1O 0.87(4) ?
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
O1 C1 C2 C3 178.8(5)
C6 C1 C2 C3 -0.5(7)
C1 C2 C3 C4 0.2(8)
C2 C3 C4 C5 0.7(9)
C3 C4 C5 C6 -1.2(9)
O1 C1 C6 C5 -179.4(4)
C2 C1 C6 C5 -0.1(7)
O1 C1 C6 C7 -1.9(7)
C2 C1 C6 C7 177.4(4)
C4 C5 C6 C1 1.0(8)
C4 C5 C6 C7 -176.6(5)
C1 C6 C7 N1 1.3(7)
C5 C6 C7 N1 178.8(5)
C13 C8 C9 C10 0.3(6)
N1 C8 C9 C10 177.6(4)
C8 C9 C10 C11 -0.2(7)
C9 C10 C11 C12 0.5(7)
C10 C11 C12 C13 -0.9(7)
C11 C12 C13 C8 1.1(6)
C11 C12 C13 I1 -179.8(3)
C9 C8 C13 C12 -0.8(6)
N1 C8 C13 C12 -178.1(4)
C9 C8 C13 I1 -179.8(3)
N1 C8 C13 I1 2.9(5)
C6 C7 N1 C8 -174.5(4)
C9 C8 N1 C7 43.8(6)
C13 C8 N1 C7 -139.1(4)