#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:48:18 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180449 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/18/7211841.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7211841
loop_
_publ_author_name
'Labat, Gaël'
'Behrnd, Norwid-Rasmus'
'Couderc, Gaëtan'
'Bonin, Michel'
'Tsuwi, Julius'
'Batagiannis, Athanasios'
'Berger, Ricarda'
'Bertoni, Mariana'
'Prodi-Schwab, Anna'
'Hulliger, Jürg'
_publ_section_title
;
 Polymorphism, polar morphology and absolute structure determination of
 4-iodo-4′-nitrobiphenyl (INBP)
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              1252
_journal_paper_doi               10.1039/b915469h
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C12 H8 I N O2'
_chemical_formula_sum            'C12 H8 I N O2'
_chemical_formula_weight         325.11
_chemical_name_systematic
;
?
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.074(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.405(3)
_cell_length_b                   14.441(5)
_cell_length_c                   8.194(2)
_cell_measurement_reflns_used    3101
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.99
_cell_measurement_theta_min      2.54
_cell_volume                     1141.0(6)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1K'
_diffrn_measurement_method       'omega scan method'
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12315
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.788
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.758742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'refined from Sadabs (Bruker)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0215P)²+0.3692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0511
_refine_ls_wR_factor_ref         0.0576
_reflns_number_gt                1624
_reflns_number_total             2340
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b915469h.txt
_cod_data_source_block           CCDC724434
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               7211841
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1A I 0.5000 -0.02031(2) 0.2500 0.06917(13) Uani 1 2 d S
O1A O 0.3922(3) 0.75566(18) 0.1671(4) 0.0910(8) Uani 1 1 d .
N1A N 0.5000 0.7160(3) 0.2500 0.0661(11) Uani 1 2 d S
C4A C 0.5000 0.3194(3) 0.2500 0.0536(11) Uani 1 2 d S
C3A C 0.4077(3) 0.2683(2) 0.1099(4) 0.0659(9) Uani 1 1 d .
H3A H 0.3448 0.2999 0.0143 0.079 Uiso 1 1 calc R
C2A C 0.4067(4) 0.1729(2) 0.1086(4) 0.0665(9) Uani 1 1 d .
H2A H 0.3440 0.1408 0.0136 0.080 Uiso 1 1 calc R
C1A C 0.5000 0.1254(3) 0.2500 0.0577(12) Uani 1 2 d S
C14A C 0.5000 0.4223(3) 0.2500 0.0558(12) Uani 1 2 d S
C13A C 0.6209(3) 0.4723(2) 0.3367(5) 0.0722(10) Uani 1 1 d .
H13A H 0.7033 0.4408 0.3961 0.087 Uiso 1 1 calc R
C12A C 0.6209(4) 0.5680(2) 0.3363(5) 0.0726(10) Uani 1 1 d .
H12A H 0.7024 0.6007 0.3943 0.087 Uiso 1 1 calc R
C11A C 0.5000 0.6135(4) 0.2500 0.0622(12) Uani 1 2 d S
I2A I 1.0000 -0.35694(2) 0.2500 0.08179(15) Uani 1 2 d S
O2A O 1.1089(3) 0.41869(19) 0.2833(4) 0.1075(10) Uani 1 1 d .
N2A N 1.0000 0.3803(4) 0.2500 0.0788(13) Uani 1 2 d S
C24A C 1.0000 -0.0170(3) 0.2500 0.0556(12) Uani 1 2 d S
C23A C 1.0932(3) -0.0680(2) 0.1998(4) 0.0604(8) Uani 1 1 d .
H23A H 1.1568 -0.0367 0.1650 0.072 Uiso 1 1 calc R
C22A C 1.0934(3) -0.1636(2) 0.2003(4) 0.0655(9) Uani 1 1 d .
H22A H 1.1571 -0.1957 0.1670 0.079 Uiso 1 1 calc R
C21A C 1.0000 -0.2116(4) 0.2500 0.0629(13) Uani 1 2 d S
C34A C 1.0000 0.0847(3) 0.2500 0.0537(11) Uani 1 2 d S
C33A C 0.8791(4) 0.1354(2) 0.2200(4) 0.0658(9) Uani 1 1 d .
H33A H 0.7967 0.1037 0.1994 0.079 Uiso 1 1 calc R
C32A C 0.8773(4) 0.2308(3) 0.2198(4) 0.0682(9) Uani 1 1 d .
H32A H 0.7958 0.2635 0.1998 0.082 Uiso 1 1 calc R
C31A C 1.0000 0.2759(4) 0.2500 0.0639(13) Uani 1 2 d S
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1A N1A O1A 123.8(5) 2_655 .
O1A N1A C11A 118.1(2) 2_655 .
O1A N1A C11A 118.1(2) . .
C3A C4A C3A 116.3(4) . 2_655
C3A C4A C14A 121.8(2) . .
C3A C4A C14A 121.8(2) 2_655 .
C2A C3A C4A 122.3(3) . .
C2A C3A H3A 118.8 . .
C4A C3A H3A 118.8 . .
C3A C2A C1A 119.3(3) . .
C3A C2A H2A 120.4 . .
C1A C2A H2A 120.4 . .
C2A C1A C2A 120.5(4) 2_655 .
C2A C1A I1A 119.8(2) 2_655 .
C2A C1A I1A 119.8(2) . .
C13A C14A C13A 117.5(4) 2_655 .
C13A C14A C4A 121.2(2) 2_655 .
C13A C14A C4A 121.2(2) . .
C12A C13A C14A 121.2(3) . .
C12A C13A H13A 119.4 . .
C14A C13A H13A 119.4 . .
C11A C12A C13A 119.0(3) . .
C11A C12A H12A 120.5 . .
C13A C12A H12A 120.5 . .
C12A C11A C12A 122.1(5) 2_655 .
C12A C11A N1A 118.9(2) 2_655 .
C12A C11A N1A 118.9(2) . .
O2A N2A O2A 124.8(6) . 2_755
O2A N2A C31A 117.6(3) . .
O2A N2A C31A 117.6(3) 2_755 .
C23A C24A C23A 116.3(4) 2_755 .
C23A C24A C34A 121.8(2) 2_755 .
C23A C24A C34A 121.8(2) . .
C22A C23A C24A 121.8(3) . .
C22A C23A H23A 119.1 . .
C24A C23A H23A 119.1 . .
C21A C22A C23A 120.3(4) . .
C21A C22A H22A 119.9 . .
C23A C22A H22A 119.9 . .
C22A C21A C22A 119.5(5) 2_755 .
C22A C21A I2A 120.3(2) 2_755 .
C22A C21A I2A 120.3(2) . .
C33A C34A C33A 116.7(4) 2_755 .
C33A C34A C24A 121.7(2) 2_755 .
C33A C34A C24A 121.7(2) . .
C32A C33A C34A 122.4(3) . .
C32A C33A H33A 118.8 . .
C34A C33A H33A 118.8 . .
C31A C32A C33A 117.6(4) . .
C31A C32A H32A 121.2 . .
C33A C32A H32A 121.2 . .
C32A C31A C32A 123.3(5) . 2_755
C32A C31A N2A 118.4(2) . .
C32A C31A N2A 118.4(2) 2_755 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1A C1A 2.104(5) .
O1A N1A 1.214(3) .
N1A O1A 1.214(3) 2_655
N1A C11A 1.481(6) .
C4A C3A 1.398(4) .
C4A C3A 1.398(4) 2_655
C4A C14A 1.486(6) .
C3A C2A 1.378(4) .
C3A H3A 0.9300 .
C2A C1A 1.382(4) .
C2A H2A 0.9300 .
C1A C2A 1.382(4) 2_655
C14A C13A 1.392(4) 2_655
C14A C13A 1.392(4) .
C13A C12A 1.381(4) .
C13A H13A 0.9300 .
C12A C11A 1.359(4) .
C12A H12A 0.9300 .
C11A C12A 1.359(4) 2_655
I2A C21A 2.099(5) .
O2A N2A 1.197(3) .
N2A O2A 1.197(3) 2_755
N2A C31A 1.508(7) .
C24A C23A 1.397(4) 2_755
C24A C23A 1.397(4) .
C24A C34A 1.469(6) .
C23A C22A 1.381(4) .
C23A H23A 0.9300 .
C22A C21A 1.374(4) .
C22A H22A 0.9300 .
C21A C22A 1.374(4) 2_755
C34A C33A 1.396(4) 2_755
C34A C33A 1.396(4) .
C33A C32A 1.378(4) .
C33A H33A 0.9300 .
C32A C31A 1.370(4) .
C32A H32A 0.9300 .
C31A C32A 1.370(4) 2_755
