#------------------------------------------------------------------------------
#$Date: 2016-07-04 16:20:59 +0300 (Mon, 04 Jul 2016) $
#$Revision: 184186 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/36/1543603.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_1543603
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 Cl2'
_chemical_formula_sum            'C8 H14 Cl2 I2 N2 O2'
_chemical_formula_weight         494.91
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.689(3)
_cell_angle_beta                 105.261(3)
_cell_angle_gamma                106.876(3)
_cell_formula_units_Z            1
_cell_length_a                   5.6207(10)
_cell_length_b                   6.9699(12)
_cell_length_c                   10.1484(17)
_cell_measurement_reflns_used    3838
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.77
_cell_measurement_theta_min      3.10
_cell_volume                     361.61(11)
_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  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7759
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.707
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.572
_refine_diff_density_min         -1.148
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0497P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0716
_reflns_number_gt                1589
_reflns_number_total             1711
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL dap_icl in P-1
CELL 0.71073   5.6207   6.9699  10.1484  94.689 105.261 106.876
ZERR    1.00   0.0010   0.0012   0.0017   0.003   0.003   0.003
LATT  1
SFAC C H N O CL I
UNIT 8 14 2 2 2 2
TEMP -163.000
 
ACTA
CONF
HTAB
 
L.S. 8
BOND $H
FMAP 2
PLAN 20
 
OMIT    -3   0   3
OMIT     0   1   0
OMIT    -4  -3   4
OMIT    -4  -1   3
OMIT    -2   0   1
OMIT    -2   1   3
OMIT    -3  -1   3
 
OMIT     1   1   0
OMIT    -1  -1   1
OMIT    -2  -2   2
OMIT    -2  -2   1
OMIT    -1  -2   1
OMIT    -3  -1   1
OMIT    -2  -3   1
OMIT     1   0   0
OMIT     2   2   1
OMIT     3   2   0
OMIT    -1  -2   2
OMIT     2   1   1
OMIT     1   1   1
OMIT    -2  -1   1
OMIT    -1  -3   1
OMIT     3   3   0
OMIT    -2  -2   3
OMIT     1   2   1
OMIT    -3  -1   2
OMIT    -3  -2   3
OMIT    -4  -2   2
OMIT    -3  -3   2
OMIT     2   4   0
OMIT    -2  -3   3
OMIT     1   3   1
OMIT    -4  -3   2
OMIT    -4  -1   2
 
WGHT    0.049700
FVAR       0.69101
I1    6    0.105436    0.557659    0.274078    11.00000    0.01357    0.01409 =
         0.01857    0.00260    0.00558    0.00203
CL1   5   -0.088139    0.750974    0.396384    11.00000    0.02428    0.02532 =
         0.02480    0.00613    0.01187    0.01300
O1    4    0.284850    0.363850    0.147149    11.00000    0.02645    0.02073 =
         0.01986    0.00486    0.00934    0.01107
N1    3    0.480865    0.139558    0.103714    11.00000    0.01821    0.01486 =
         0.01646    0.00394    0.00532    0.00513
C1    1    0.633781    0.003361    0.142790    11.00000    0.02118    0.01949 =
         0.01874    0.00352    0.00535    0.01034
AFIX   3
H1A   2    0.626881   -0.030499    0.231630    11.00000   -1.20000
H1B   2    0.812231    0.071771    0.149600    11.00000   -1.20000
AFIX   0
C2    1    0.470777    0.190308   -0.034669    11.00000    0.02303    0.01750 =
         0.01997    0.00626    0.00954    0.00613
AFIX   3
H2A   2    0.641907    0.267168   -0.035589    11.00000   -1.20000
H2B   2    0.360137    0.272228   -0.056939    11.00000   -1.20000
AFIX   0
C3    1    0.399209    0.239399    0.190748    11.00000    0.01333    0.01121 =
         0.02116    0.00173    0.00717    0.00013
C4    1    0.439482    0.199990    0.336771    11.00000    0.02320    0.01970 =
         0.01822    0.00276    0.00775    0.00648
AFIX 137
H4A   2    0.369777    0.285860    0.386777    11.00000   -1.50000
H4B   2    0.626252    0.231897    0.383192    11.00000   -1.50000
H4C   2    0.348736    0.056460    0.335770    11.00000   -1.50000
 
HKLF 4
 
REM  dap_icl in P-1
REM R1 =  0.0265 for   1589 Fo > 4sig(Fo)  and  0.0295 for all   1711 data
REM     74 parameters refined using      0 restraints
 
END  
;
_cod_data_source_file            jp6b02192_si_003.cif
_cod_data_source_block           compiiib
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               1543603
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.10544(4) 0.55766(3) 0.27408(2) 0.01583(10) Uani 1 1 d .
Cl1 Cl -0.08814(19) 0.75097(15) 0.39638(10) 0.0227(2) Uani 1 1 d .
O1 O 0.2849(6) 0.3638(4) 0.1471(3) 0.0210(5) Uani 1 1 d .
N1 N 0.4809(6) 0.1396(4) 0.1037(3) 0.0165(6) Uani 1 1 d .
C1 C 0.6338(7) 0.0034(6) 0.1428(4) 0.0191(7) Uani 1 1 d .
H1A H 0.6269 -0.0305 0.2316 0.023 Uiso 1 1 d R
H1B H 0.8122 0.0718 0.1496 0.023 Uiso 1 1 d R
C2 C 0.4708(7) 0.1903(5) -0.0347(4) 0.0195(7) Uani 1 1 d .
H2A H 0.6419 0.2672 -0.0356 0.023 Uiso 1 1 d R
H2B H 0.3601 0.2722 -0.0569 0.023 Uiso 1 1 d R
C3 C 0.3992(7) 0.2394(5) 0.1907(4) 0.0158(6) Uani 1 1 d .
C4 C 0.4395(8) 0.2000(6) 0.3368(4) 0.0202(7) Uani 1 1 d .
H4A H 0.3698 0.2859 0.3868 0.030 Uiso 1 1 calc R
H4B H 0.6263 0.2319 0.3832 0.030 Uiso 1 1 calc R
H4C H 0.3487 0.0565 0.3358 0.030 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 0.01357(13) 0.01409(14) 0.01857(14) 0.00260(9) 0.00558(9) 0.00203(9)
Cl1 0.0243(4) 0.0253(5) 0.0248(4) 0.0061(4) 0.0119(4) 0.0130(4)
O1 0.0265(14) 0.0207(13) 0.0199(13) 0.0049(10) 0.0093(11) 0.0111(12)
N1 0.0182(14) 0.0149(14) 0.0165(13) 0.0039(11) 0.0053(11) 0.0051(11)
C1 0.0212(17) 0.0195(17) 0.0187(17) 0.0035(13) 0.0053(13) 0.0103(14)
C2 0.0230(18) 0.0175(17) 0.0200(17) 0.0063(13) 0.0095(14) 0.0061(14)
C3 0.0133(15) 0.0112(15) 0.0212(16) 0.0017(12) 0.0072(13) 0.0001(12)
C4 0.0232(18) 0.0197(17) 0.0182(16) 0.0028(13) 0.0078(14) 0.0065(14)
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'
Cl Cl 0.1484 0.1585 '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
O1 I1 Cl1 178.22(7) . .
C3 O1 I1 127.0(2) . .
C3 N1 C2 121.2(3) . .
C3 N1 C1 124.6(3) . .
C2 N1 C1 113.0(3) . .
N1 C1 C2 110.5(3) . 2_655
N1 C1 H1A 109.7 . .
C2 C1 H1A 109.9 2_655 .
N1 C1 H1B 109.3 . .
C2 C1 H1B 109.3 2_655 .
H1A C1 H1B 108.2 . .
N1 C2 C1 110.3(3) . 2_655
N1 C2 H2A 109.8 . .
C1 C2 H2A 109.4 2_655 .
N1 C2 H2B 109.4 . .
C1 C2 H2B 109.7 2_655 .
H2A C2 H2B 108.2 . .
O1 C3 N1 118.8(3) . .
O1 C3 C4 121.3(3) . .
N1 C3 C4 119.8(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 O1 2.386(3) .
I1 Cl1 2.4142(9) .
O1 C3 1.264(4) .
N1 C3 1.332(4) .
N1 C2 1.467(4) .
N1 C1 1.467(4) .
C1 C2 1.526(5) 2_655
C1 H1A 0.9581 .
C1 H1B 0.9584 .
C2 C1 1.526(5) 2_655
C2 H2A 0.9585 .
C2 H2B 0.9576 .
C3 C4 1.500(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
Cl1 I1 O1 C3 -135(2) .
C3 N1 C1 C2 136.2(3) 2_655
C2 N1 C1 C2 -55.8(4) 2_655
C3 N1 C2 C1 -135.9(3) 2_655
C1 N1 C2 C1 55.7(4) 2_655
I1 O1 C3 N1 178.0(2) .
I1 O1 C3 C4 -0.8(5) .
C2 N1 C3 O1 7.9(5) .
C1 N1 C3 O1 175.0(3) .
C2 N1 C3 C4 -173.2(3) .
C1 N1 C3 C4 -6.2(5) .
