#------------------------------------------------------------------------------
#$Date: 2016-02-13 20:28:24 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/09/4030979.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_4030979
loop_
_publ_author_name
'Postnikov, Pavel S.'
'Guselnikova, Olga A.'
'Yusubov, Mekhman S.'
'Yoshimura, Akira'
'Nemykin, Victor N.'
'Zhdankin, Viktor V.'
_publ_section_related_literature
; 
? 
;
_publ_section_title
;
 Preparation and X-ray Structural Study of Dibenziodolium Derivatives.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5783
_journal_page_last               5788
_journal_paper_doi               10.1021/acs.joc.5b00741
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C12 H8 I1 N3'
_chemical_formula_sum            'C12 H8 I N3'
_chemical_formula_weight         321.12
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             15-03-22
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                113.251(8)
_cell_angle_beta                 92.400(7)
_cell_angle_gamma                111.062(8)
_cell_formula_units_Z            2
_cell_length_a                   7.4374(6)
_cell_length_b                   8.7655(8)
_cell_length_c                   9.8437(9)
_cell_measurement_reflns_used    6953
_cell_measurement_temperature    123
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_volume                     537.44(10)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6953
_diffrn_reflns_theta_full        27.475
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         2.305
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  2
_diffrn_standards_number         6953
_exptl_absorpt_coefficient_mu    2.952
_exptl_absorpt_correction_T_max  0.61
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.984
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.170
_refine_diff_density_max         2.00
_refine_diff_density_min         -1.95
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9344
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.0004859
_refine_ls_shift/su_mean         0.0000117
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 7.62P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1225
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1225
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              10
_reflns_limit_k_min              -11
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2202
_reflns_number_total             2466
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0519
_oxford_refine_ls_scale          0.658(2)
_oxford_reflns_number_all        2449
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title '_10252014-1'
_cod_data_source_file            jo5b00741_si_001.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 4030978--4030981.cif.'
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C12 H8 I1 N3'
_cod_database_code               4030979
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   5,X'S) H   (  41,X'S) 
RIDE C   (   4,X'S) H   (  51,X'S) 
RIDE C   (   3,X'S) H   (  61,X'S) 
RIDE C   (   2,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   ( 101,X'S) 
RIDE C   (  10,X'S) H   ( 111,X'S) 
RIDE C   (  11,X'S) H   ( 121,X'S) 
RIDE C   (  12,X'S) H   ( 131,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
#END Tags that were not found in dictionaries
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
I1 I 0.79519(6) 0.67342(5) 0.95297(5) 0.0194 1.0000 Uani .
C1 C 0.7393(9) 0.5499(8) 1.1011(7) 0.0170 1.0000 Uani .
C6 C 0.7153(9) 0.3680(9) 1.0306(7) 0.0197 1.0000 Uani .
C5 C 0.6773(9) 0.2709(9) 1.1168(8) 0.0232 1.0000 Uani .
C4 C 0.6633(10) 0.3557(9) 1.2672(8) 0.0241 1.0000 Uani .
C3 C 0.6877(10) 0.5367(10) 1.3327(8) 0.0235 1.0000 Uani .
C2 C 0.7260(10) 0.6353(9) 1.2485(8) 0.0226 1.0000 Uani .
C7 C 0.7310(9) 0.2948(8) 0.8711(8) 0.0202 1.0000 Uani .
C8 C 0.7693(10) 0.4128(9) 0.8036(7) 0.0204 1.0000 Uani .
C9 C 0.7911(10) 0.3637(10) 0.6561(8) 0.0264 1.0000 Uani .
C10 C 0.7716(11) 0.1845(10) 0.5698(8) 0.0278 1.0000 Uani .
C11 C 0.7346(11) 0.0648(9) 0.6353(9) 0.0298 1.0000 Uani .
C12 C 0.7147(10) 0.1185(9) 0.7823(8) 0.0234 1.0000 Uani .
N1 N 0.8721(10) 0.7752(9) 0.7235(7) 0.0324 1.0000 Uani .
N2 N 1.0295(9) 0.8968(7) 0.7672(6) 0.0227 1.0000 Uani .
N3 N 1.1870(10) 1.0165(8) 0.8091(7) 0.0296 1.0000 Uani .
H41 H 0.6623 0.1499 1.0751 0.0297 1.0000 Uiso R
H51 H 0.6397 0.2888 1.3234 0.0296 1.0000 Uiso R
H61 H 0.6764 0.5923 1.4339 0.0307 1.0000 Uiso R
H71 H 0.7436 0.7566 1.2908 0.0320 1.0000 Uiso R
H101 H 0.8175 0.4464 0.6142 0.0363 1.0000 Uiso R
H111 H 0.7828 0.1439 0.4679 0.0369 1.0000 Uiso R
H121 H 0.7239 -0.0526 0.5784 0.0389 1.0000 Uiso R
H131 H 0.6892 0.0371 0.8249 0.0295 1.0000 Uiso 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 0.0209(2) 0.0164(2) 0.0223(2) 0.01039(17) 0.00335(17) 0.00709(17)
C1 0.016(3) 0.015(3) 0.023(3) 0.014(2) 0.004(2) 0.003(2)
C6 0.015(3) 0.024(3) 0.024(3) 0.011(3) 0.004(3) 0.012(3)
C5 0.017(3) 0.022(3) 0.034(4) 0.014(3) 0.003(3) 0.009(3)
C4 0.028(3) 0.021(3) 0.023(3) 0.012(3) 0.004(3) 0.008(3)
C3 0.021(3) 0.028(3) 0.025(3) 0.014(3) 0.009(3) 0.011(3)
C2 0.021(3) 0.024(3) 0.022(3) 0.011(3) 0.005(3) 0.007(3)
C7 0.018(3) 0.013(3) 0.023(3) 0.006(2) -0.005(3) 0.004(2)
C8 0.021(3) 0.018(3) 0.020(3) 0.007(3) 0.003(3) 0.008(3)
C9 0.026(3) 0.023(3) 0.029(4) 0.013(3) 0.000(3) 0.009(3)
C10 0.036(4) 0.024(3) 0.022(3) 0.005(3) 0.004(3) 0.016(3)
C11 0.032(4) 0.018(3) 0.036(4) 0.009(3) 0.009(3) 0.010(3)
C12 0.025(3) 0.020(3) 0.027(3) 0.012(3) 0.010(3) 0.009(3)
N1 0.039(4) 0.028(3) 0.029(3) 0.014(3) 0.005(3) 0.012(3)
N2 0.040(4) 0.015(3) 0.020(3) 0.009(2) 0.012(3) 0.017(3)
N3 0.038(4) 0.021(3) 0.032(3) 0.012(3) 0.016(3) 0.013(3)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 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
C1 I1 C8 81.4(2) yes
I1 C1 C6 111.9(4) yes
I1 C1 C2 124.5(5) yes
C6 C1 C2 123.6(6) yes
C1 C6 C5 117.4(6) yes
C1 C6 C7 117.3(6) yes
C5 C6 C7 125.3(6) yes
C6 C5 C4 119.7(6) yes
C6 C5 H41 120.5 no
C4 C5 H41 119.8 no
C5 C4 C3 120.9(6) yes
C5 C4 H51 118.4 no
C3 C4 H51 120.7 no
C4 C3 C2 120.0(6) yes
C4 C3 H61 120.3 no
C2 C3 H61 119.6 no
C3 C2 C1 118.2(6) yes
C3 C2 H71 121.1 no
C1 C2 H71 120.7 no
C6 C7 C8 117.0(6) yes
C6 C7 C12 125.8(6) yes
C8 C7 C12 117.2(6) yes
C7 C8 I1 112.5(5) yes
C7 C8 C9 123.2(6) yes
I1 C8 C9 124.3(5) yes
C8 C9 C10 117.9(6) yes
C8 C9 H101 121.1 no
C10 C9 H101 120.9 no
C9 C10 C11 119.8(7) yes
C9 C10 H111 121.0 no
C11 C10 H111 119.2 no
C10 C11 C12 120.7(7) yes
C10 C11 H121 119.5 no
C12 C11 H121 119.8 no
C7 C12 C11 121.2(6) yes
C7 C12 H131 118.8 no
C11 C12 H131 120.0 no
N1 N2 N3 179.1(7) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C1 2.108(6) yes
I1 C8 2.104(6) yes
C1 C6 1.402(9) yes
C1 C2 1.372(9) yes
C6 C5 1.394(9) yes
C6 C7 1.471(9) yes
C5 C4 1.398(10) yes
C5 H41 0.935 no
C4 C3 1.393(10) yes
C4 H51 0.934 no
C3 C2 1.387(9) yes
C3 H61 0.943 no
C2 H71 0.931 no
C7 C8 1.393(9) yes
C7 C12 1.399(9) yes
C8 C9 1.377(10) yes
C9 C10 1.408(10) yes
C9 H101 0.935 no
C10 C11 1.391(10) yes
C10 H111 0.941 no
C11 C12 1.367(10) yes
C11 H121 0.928 no
C12 H131 0.931 no
N1 N2 1.179(9) yes
N2 N3 1.174(8) yes
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_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C2 H71 N3 2_777 133.1(2) 0.931 2.458 3.167(11) yes
C9 H101 N1 . 132.2(2) 0.935 2.510 3.214(11) yes
C10 H111 N3 2_766 170.3(2) 0.941 2.591 3.522(11) yes
#BEGIN Loops that were not found in dictionaries:
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
3 2 7 x
1 4 7 x
-4 4 8 x
-4 6 7 x
3 4 5 x
-5 4 8 x
-3 4 9 x
-5 5 7 x
-8 1 7 x
-5 6 5 x
#END Loops that were not found in dictionaries
