#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/36/1543604.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_1543604
loop_
_publ_author_name
'Suponitsky, Kyrill Yu'
'Burakov, N. I.'
'Kanibolotsky, Alexander L.'
'Mikhailov, Vasilii A.'
_publ_section_title
;
 Multiple Noncovalent Bonding in Halogen Complexes with Oxygen Organics.
 I. Tertiary Amides.
;
_journal_issue                   24
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              4179
_journal_page_last               4190
_journal_paper_doi               10.1021/acs.jpca.6b02192
_journal_volume                  120
_journal_year                    2016
_chemical_formula_moiety         'C8 H14 N2 O2, I2'
_chemical_formula_sum            'C8 H14 I2 N2 O2'
_chemical_formula_weight         424.01
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 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                 119.780(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.369(3)
_cell_length_b                   5.6645(7)
_cell_length_c                   11.4780(14)
_cell_measurement_reflns_used    844
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.19
_cell_volume                     1205.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5455
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.55
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.196
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.963
_refine_diff_density_min         -1.068
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0275
_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)+(0.0380P)²+7.6500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0683
_reflns_number_gt                1319
_reflns_number_total             1434
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL dap_i2 in C2/c
CELL 0.71073  21.3687   5.6645  11.4780  90.000 119.780  90.000
ZERR    8.00   0.0027   0.0007   0.0014   0.000   0.002   0.000
LATT  7
SYMM -X, Y, 0.5-Z
SFAC C H N O I
UNIT 32 56 8 8 8
 
ACTA
TEMP -163.0
CONF
HTAB
 
L.S. 4
BOND $H
FMAP 2
PLAN 20
 
OMIT    -6   0   2
OMIT     4   0   2
OMIT    -5   1   2
OMIT     0   0   4
OMIT     1   1   0
OMIT     2   0   0
OMIT    -2   0   4
OMIT     3   1   2
OMIT   -18   0  14
OMIT    -3   1   1
OMIT    -7   1   6
OMIT     9   1   0
OMIT    -7   1  10
 
OMIT    -8   4  11
OMIT    -9   5  11
OMIT   -11   1  11
OMIT     0   2   0
OMIT     7   1   9
OMIT    16   4   2
OMIT     4   2   2
 
OMIT    -7   5  11
OMIT    12   6   0
OMIT   -14   6   8
OMIT     0   4  11
OMIT    -4   6   2
OMIT     5   1   6
OMIT   -10   0   4
 
WGHT    0.038000    7.650000
FVAR       0.24682
I1    5    0.451674    0.052700    0.617028    11.00000    0.01311    0.01814 =
         0.01172   -0.00074    0.00495   -0.00082
O1    4    0.349777    0.088994    0.341358    11.00000    0.01412    0.02413 =
         0.00531    0.00162    0.00166   -0.00673
N1    3    0.292245    0.277329    0.140860    11.00000    0.01395    0.01123 =
         0.01305    0.00095    0.00342   -0.00306
C1    1    0.279831    0.477358    0.052262    11.00000    0.01614    0.01018 =
         0.01316    0.00188    0.00378   -0.00217
AFIX  23
H1A   2    0.322315    0.583120    0.093208    11.00000   -1.20000
H1B   2    0.237566    0.568067    0.040953    11.00000   -1.20000
AFIX   0
C2    1    0.233503    0.105556    0.084713    11.00000    0.00951    0.01371 =
         0.01611    0.00235    0.00451    0.00067
AFIX  23
H2A   2    0.189108    0.178483    0.075257    11.00000   -1.20000
H2B   2    0.246105   -0.031263    0.146021    11.00000   -1.20000
AFIX   0
C3    1    0.346543    0.257604    0.268691    11.00000    0.01504    0.01703 =
         0.01221    0.00024    0.00561    0.00085
C4    1    0.404234    0.447262    0.319683    11.00000    0.01570    0.02122 =
         0.01349    0.00092    0.00226   -0.00568
AFIX 137
H4A   2    0.441770    0.409170    0.411468    11.00000   -1.50000
H4B   2    0.382615    0.600154    0.319091    11.00000   -1.50000
H4C   2    0.425599    0.455023    0.261442    11.00000   -1.50000
 
HKLF 4
 
REM  dap_i2 in C2/c
REM R1 =  0.0275 for   1319 Fo > 4sig(Fo)  and  0.0292 for all   1434 data
REM     65 parameters refined using      0 restraints
 
END  
;
_cod_data_source_file            jp6b02192_si_002.cif
_cod_data_source_block           compiiia
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1543604
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
I1 I 0.451674(11) 0.05270(4) 0.617028(19) 0.01486(10) Uani 1 1 d .
O1 O 0.34978(14) 0.0890(5) 0.3414(2) 0.0159(5) Uani 1 1 d .
N1 N 0.29224(14) 0.2773(5) 0.1409(3) 0.0142(5) Uani 1 1 d .
C1 C 0.27983(19) 0.4774(6) 0.0523(3) 0.0147(6) Uani 1 1 d .
H1A H 0.3223 0.5831 0.0932 0.018 Uiso 1 1 calc R
H1B H 0.2376 0.5681 0.0410 0.018 Uiso 1 1 calc R
C2 C 0.23350(17) 0.1056(6) 0.0847(3) 0.0139(6) Uani 1 1 d .
H2A H 0.1891 0.1785 0.0753 0.017 Uiso 1 1 calc R
H2B H 0.2461 -0.0313 0.1460 0.017 Uiso 1 1 calc R
C3 C 0.34654(17) 0.2576(7) 0.2687(3) 0.0153(6) Uani 1 1 d .
C4 C 0.4042(2) 0.4473(6) 0.3197(4) 0.0190(7) Uani 1 1 d .
H4A H 0.4418 0.4092 0.4115 0.028 Uiso 1 1 calc R
H4B H 0.3826 0.6002 0.3191 0.028 Uiso 1 1 calc R
H4C H 0.4256 0.4550 0.2614 0.028 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01311(14) 0.01814(16) 0.01172(14) -0.00074(7) 0.00495(10) -0.00082(7)
O1 0.0141(11) 0.0241(13) 0.0053(10) 0.0016(9) 0.0017(9) -0.0067(9)
N1 0.0139(12) 0.0112(13) 0.0131(13) 0.0010(11) 0.0034(10) -0.0031(11)
C1 0.0161(16) 0.0102(15) 0.0132(15) 0.0019(12) 0.0038(12) -0.0022(12)
C2 0.0095(13) 0.0137(15) 0.0161(15) 0.0023(13) 0.0045(12) 0.0007(12)
C3 0.0150(14) 0.0170(16) 0.0122(14) 0.0002(13) 0.0056(12) 0.0008(13)
C4 0.0157(16) 0.0212(19) 0.0135(15) 0.0009(13) 0.0023(13) -0.0057(13)
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_site_symmetry_1
_geom_angle_site_symmetry_3
C3 N1 C1 125.7(3) . .
C3 N1 C2 120.7(3) . .
C1 N1 C2 113.1(2) . .
N1 C1 C2 110.9(3) . 7
N1 C1 H1A 109.5 . .
C2 C1 H1A 109.5 7 .
N1 C1 H1B 109.5 . .
C2 C1 H1B 109.5 7 .
H1A C1 H1B 108.1 . .
N1 C2 C1 109.8(3) . 7
N1 C2 H2A 109.7 . .
C1 C2 H2A 109.7 7 .
N1 C2 H2B 109.7 . .
C1 C2 H2B 109.7 7 .
H2A C2 H2B 108.2 . .
O1 C3 N1 121.5(3) . .
O1 C3 C4 121.3(3) . .
N1 C3 C4 117.1(3) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 I1 2.7057(5) 2_656
O1 C3 1.247(4) .
N1 C3 1.349(4) .
N1 C1 1.456(4) .
N1 C2 1.461(4) .
C1 C2 1.526(5) 7
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.516(5) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
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
_geom_torsion_site_symmetry_4
C3 N1 C1 C2 131.9(3) 7
C2 N1 C1 C2 -56.2(4) 7
C3 N1 C2 C1 -132.0(3) 7
C1 N1 C2 C1 55.6(4) 7
C1 N1 C3 O1 173.8(3) .
C2 N1 C3 O1 2.5(5) .
C1 N1 C3 C4 -7.1(5) .
C2 N1 C3 C4 -178.5(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139048810
