#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/01/2100141.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_2100141
loop_
_publ_author_name
'Glidewell, Christopher'
'Low, John N.'
'Skakle, Janet M.S.'
'Wardell, Solange M. S. V.'
'Wardell, James L.'
_publ_section_title
;
 Isomeric N-(iodophenyl)nitrophthalimides: interplay of
 C---H···O hydrogen bonds,
 iodo···nitro and
 iodo···carbonyl interactions, and aromatic
 π···π stacking interactions
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              227
_journal_page_last               237
_journal_paper_doi               10.1107/S0108768105004234
_journal_volume                  61
_journal_year                    2005
_chemical_formula_moiety         'C14 H7 I N2 O4'
_chemical_formula_sum            'C14 H7 I N2 O4'
_chemical_formula_weight         394.12
_chemical_name_systematic
;
N-(3-Iodophenyl)-4-nitrophthalimide
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.960(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9592(9)
_cell_length_b                   6.5708(7)
_cell_length_c                   25.648(3)
_cell_measurement_reflns_used    4808
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      32.59
_cell_measurement_theta_min      2.58
_cell_volume                     1328.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'OSCAIL &SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'OSCAIL (McArdle, 2003) & SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0855
_diffrn_reflns_av_sigmaI/netI    0.1574
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            13842
_diffrn_reflns_theta_full        32.59
_diffrn_reflns_theta_max         32.59
_diffrn_reflns_theta_min         2.58
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    2.428
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.971
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.347
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.766
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.766
_refine_ls_R_factor_all          0.2007
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0320P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                1564
_reflns_number_total             4808
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm5022.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2100141
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
N1 0.2572(4) 0.3057(5) 0.23850(13) 0.0359(8) Uani d . 1 . . N
C1 0.3679(6) 0.3800(7) 0.28155(19) 0.0469(12) Uani d . 1 . . C
O1 0.4498(4) 0.5353(6) 0.28135(13) 0.0664(10) Uani d . 1 . . O
C2 0.1811(5) 0.1229(7) 0.25127(18) 0.0392(11) Uani d . 1 . . C
O2 0.0761(4) 0.0303(5) 0.22220(12) 0.0498(8) Uani d . 1 . . O
C3 0.2518(5) 0.0768(7) 0.30601(17) 0.0418(11) Uani d . 1 . . C
C4 0.2227(6) -0.0859(7) 0.3380(2) 0.0492(12) Uani d . 1 . . C
C5 0.3031(6) -0.0746(8) 0.3891(2) 0.0519(13) Uani d . 1 . . C
N5 0.2700(6) -0.2417(8) 0.4253(2) 0.0704(14) Uani d . 1 . . N
O51 0.3144(5) -0.2137(7) 0.47317(17) 0.1032(15) Uani d . 1 . . O
O52 0.2001(6) -0.3948(7) 0.40603(19) 0.0953(15) Uani d . 1 . . O
C6 0.4063(6) 0.0804(9) 0.4095(2) 0.0590(14) Uani d . 1 . . C
C7 0.4379(6) 0.2369(8) 0.3764(2) 0.0552(13) Uani d . 1 . . C
C8 0.3598(6) 0.2327(7) 0.32509(18) 0.0428(12) Uani d . 1 . . C
C11 0.2265(5) 0.3960(7) 0.18761(18) 0.0387(11) Uani d . 1 . . C
C12 0.2393(5) 0.2767(7) 0.14373(17) 0.0411(11) Uani d . 1 . . C
C13 0.1986(5) 0.3555(7) 0.09433(17) 0.0457(11) Uani d . 1 . . C
C14 0.1423(6) 0.5562(8) 0.0878(2) 0.0530(13) Uani d . 1 . . C
C15 0.1326(5) 0.6747(8) 0.1317(2) 0.0500(12) Uani d . 1 . . C
C16 0.1756(5) 0.5957(7) 0.1812(2) 0.0471(12) Uani d . 1 . . C
I13 0.21726(5) 0.16750(6) 0.029415(13) 0.06463(15) Uani d . 1 . . I
H4 0.1537 -0.1950 0.3259 0.059 Uiso calc R 1 . . H
H6 0.4538 0.0803 0.4447 0.071 Uiso calc R 1 . . H
H7 0.5104 0.3429 0.3885 0.066 Uiso calc R 1 . . H
H12 0.2758 0.1425 0.1480 0.049 Uiso calc R 1 . . H
H14 0.1117 0.6094 0.0543 0.064 Uiso calc R 1 . . H
H15 0.0966 0.8092 0.1276 0.060 Uiso calc R 1 . . H
H16 0.1704 0.6773 0.2106 0.057 Uiso calc R 1 . . H
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'
I I -0.4742 1.8119 '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
C1 N1 C2 111.0(4)
C1 N1 C11 125.9(4)
C2 N1 C11 123.1(3)
O1 C1 N1 124.7(4)
O1 C1 C8 129.1(5)
N1 C1 C8 106.1(4)
O2 C2 N1 124.9(4)
O2 C2 C3 128.9(4)
N1 C2 C3 106.2(4)
C8 C3 C4 120.5(4)
C8 C3 C2 108.8(4)
C4 C3 C2 130.6(5)
C5 C4 C3 115.3(5)
C5 C4 H4 122.3
C3 C4 H4 122.3
C6 C5 C4 125.5(5)
C6 C5 N5 117.4(5)
C4 C5 N5 117.1(5)
O52 N5 O51 125.0(5)
O52 N5 C5 117.8(5)
O51 N5 C5 117.3(6)
C5 C6 C7 118.2(5)
C5 C6 H6 120.9
C7 C6 H6 120.9
C8 C7 C6 118.5(5)
C8 C7 H7 120.8
C6 C7 H7 120.8
C7 C8 C3 122.0(4)
C7 C8 C1 130.2(5)
C3 C8 C1 107.8(4)
C16 C11 C12 119.7(4)
C16 C11 N1 121.1(4)
C12 C11 N1 119.1(4)
C13 C12 C11 120.2(4)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C14 120.0(4)
C12 C13 I13 118.7(4)
C14 C13 I13 121.3(4)
C15 C14 C13 119.4(5)
C15 C14 H14 120.3
C13 C14 H14 120.3
C16 C15 C14 120.4(5)
C16 C15 H15 119.8
C14 C15 H15 119.8
C15 C16 C11 120.2(5)
C15 C16 H16 119.9
C11 C16 H16 119.9
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
N1 C1 . 1.402(6) ?
N1 C2 . 1.404(5) ?
N1 C11 . 1.424(5) ?
C1 O1 . 1.212(5) ?
C1 C8 . 1.486(6) ?
C2 O2 . 1.205(5) ?
C2 C3 . 1.470(6) ?
C3 C8 . 1.382(6) ?
C3 C4 . 1.387(6) ?
C4 C5 . 1.377(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.366(7) ?
C5 N5 . 1.486(6) ?
N5 O52 . 1.221(6) ?
N5 O51 . 1.243(6) ?
C6 C7 . 1.378(6) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.376(6) ?
C7 H7 . 0.9300 ?
C11 C16 . 1.376(6) ?
C11 C12 . 1.387(6) ?
C12 C13 . 1.366(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.395(6) ?
C13 I13 . 2.095(5) ?
C14 C15 . 1.378(6) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.373(6) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
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
C16 H16 O2 1_565 0.93 2.47 3.181(6) 133 y
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
C2 N1 C1 O1 -179.9(4)
C11 N1 C1 O1 1.9(7)
C2 N1 C1 C8 -0.5(5)
C11 N1 C1 C8 -178.7(4)
C1 N1 C2 O2 177.2(4)
C11 N1 C2 O2 -4.5(6)
C1 N1 C2 C3 -1.2(4)
C11 N1 C2 C3 177.1(4)
O2 C2 C3 C8 -175.7(4)
N1 C2 C3 C8 2.5(5)
O2 C2 C3 C4 2.6(8)
N1 C2 C3 C4 -179.2(4)
C8 C3 C4 C5 2.2(6)
C2 C3 C4 C5 -176.0(4)
C3 C4 C5 C6 -0.1(7)
C3 C4 C5 N5 177.7(4)
C6 C5 N5 O52 -169.1(5)
C4 C5 N5 O52 12.9(7)
C6 C5 N5 O51 11.6(7)
C4 C5 N5 O51 -166.4(4)
C4 C5 C6 C7 -2.0(7)
N5 C5 C6 C7 -179.8(4)
C5 C6 C7 C8 2.1(7)
C6 C7 C8 C3 -0.2(7)
C6 C7 C8 C1 178.9(4)
C4 C3 C8 C7 -2.1(7)
C2 C3 C8 C7 176.4(4)
C4 C3 C8 C1 178.7(4)
C2 C3 C8 C1 -2.8(5)
O1 C1 C8 C7 2.3(8)
N1 C1 C8 C7 -177.1(4)
O1 C1 C8 C3 -178.5(5)
N1 C1 C8 C3 2.1(5)
C1 N1 C11 C16 -54.9(6)
C2 N1 C11 C16 127.0(4)
C1 N1 C11 C12 128.7(4)
C2 N1 C11 C12 -49.4(5)
C16 C11 C12 C13 -1.2(6)
N1 C11 C12 C13 175.2(4)
C11 C12 C13 C14 -0.6(6)
C11 C12 C13 I13 -179.2(3)
C12 C13 C14 C15 1.6(7)
I13 C13 C14 C15 -179.8(3)
C13 C14 C15 C16 -0.9(7)
C14 C15 C16 C11 -1.0(7)
C12 C11 C16 C15 2.0(6)
N1 C11 C16 C15 -174.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 935447
