#------------------------------------------------------------------------------
#$Date: 2022-08-24 01:33:25 +0300 (Wed, 24 Aug 2022) $
#$Revision: 277360 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/53/7245360.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_7245360
loop_
_publ_author_name
'Peloquin, Andrew J.'
'McMillen, Colin'
'Pennington, William'
_publ_section_title
;
 Isolation of unique heterocycles formed from pyridine-thiocarboxamides as
 diiodine, iodide, or polyiodide salts
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00904H
_journal_year                    2022
_chemical_formula_moiety         'I, C12 H9 N4 S, 0.5(C4 H6 N2)'
_chemical_formula_sum            'C14 H12 I N5 S'
_chemical_formula_weight         409.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-03-14
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8620(2)
_cell_length_b                   6.3853(2)
_cell_length_c                   25.0333(5)
_cell_measurement_reflns_used    6150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.3790
_cell_measurement_theta_min      1.6210
_cell_volume                     1576.39(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11018
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.627
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.164
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.129
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0198P)²+0.9690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0529
_refine_ls_wR_factor_ref         0.0578
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1508
_reflns_number_total             1756
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00904h2.cif
_cod_data_source_block           4jul20_ajp7_xprep_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7245360
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.768
_shelx_estimated_absorpt_t_min   0.680
_olex2_refinement_description
;
1. Others
 Fixed Sof: H14A(0.5) H14B(0.5) H14C(0.5)
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.91214(2) 0.750000 0.67279(2) 0.02523(11) Uani 1 2 d S T P . .
HN3 H 0.663(4) 0.750000 0.6344(17) 0.033(13) Uiso 1 2 d S . P . .
S1 S 0.26470(9) 0.750000 0.43254(4) 0.0183(2) Uani 1 2 d S T P . .
N1 N 0.3787(3) 0.750000 0.48076(12) 0.0166(7) Uani 1 2 d S T P . .
C1 C 0.3112(3) 0.750000 0.52658(15) 0.0134(8) Uani 1 2 d S T P . .
N2 N 0.1736(3) 0.750000 0.52609(12) 0.0129(7) Uani 1 2 d S T P . .
C2 C 0.3810(3) 0.750000 0.57850(15) 0.0142(8) Uani 1 2 d S T P . .
N3 N 0.5795(3) 0.750000 0.63025(14) 0.0172(7) Uani 1 2 d S T P . .
C3 C 0.5220(4) 0.750000 0.58195(16) 0.0164(9) Uani 1 2 d S T P . .
H3 H 0.576194 0.750000 0.550571 0.020 Uiso 1 2 calc R U P . .
C4 C 0.5094(4) 0.750000 0.67583(16) 0.0193(9) Uani 1 2 d S T P . .
H4 H 0.555673 0.750000 0.709113 0.023 Uiso 1 2 calc R U P . .
N4 N -0.2435(3) 0.750000 0.49420(12) 0.0148(7) Uani 1 2 d S T P . .
C5 C 0.3705(4) 0.750000 0.67450(15) 0.0195(9) Uani 1 2 d S T P . .
H5 H 0.319733 0.750000 0.706753 0.023 Uiso 1 2 calc R U P . .
N5 N 0.5022(4) 0.250000 0.66769(15) 0.0334(10) Uani 1 2 d S T P . .
C6 C 0.3054(4) 0.750000 0.62581(15) 0.0171(9) Uani 1 2 d S T P . .
H6 H 0.209129 0.750000 0.624348 0.021 Uiso 1 2 calc R U P . .
C7 C 0.1312(3) 0.750000 0.47686(15) 0.0142(8) Uani 1 2 d S T P . .
C9 C -0.1091(3) 0.750000 0.50301(16) 0.0145(8) Uani 1 2 d S T P . .
H9 H -0.078065 0.750000 0.538928 0.017 Uiso 1 2 calc R U P . .
C8 C -0.0134(3) 0.750000 0.46247(15) 0.0130(8) Uani 1 2 d S T P . .
C10 C -0.2842(4) 0.750000 0.44316(15) 0.0167(9) Uani 1 2 d S T P . .
H10 H -0.378844 0.750000 0.436144 0.020 Uiso 1 2 calc R U P . .
C11 C -0.1958(4) 0.750000 0.39977(15) 0.0175(9) Uani 1 2 d S T P . .
H11 H -0.229524 0.750000 0.364217 0.021 Uiso 1 2 calc R U P . .
C12 C -0.0575(3) 0.750000 0.40972(15) 0.0158(8) Uani 1 2 d S T P . .
H12 H 0.005817 0.750000 0.381112 0.019 Uiso 1 2 calc R U P . .
C13 C 0.5700(4) 0.250000 0.70416(18) 0.0268(10) Uani 1 2 d S T P . .
C14 C 0.6575(6) 0.250000 0.7512(2) 0.0649(18) Uani 1 2 d S T P . .
H14A H 0.748160 0.299325 0.741208 0.097 Uiso 0.5 1 calc R U P . .
H14B H 0.663916 0.107529 0.765538 0.097 Uiso 0.5 1 calc R U P . .
H14C H 0.619304 0.343146 0.778423 0.097 Uiso 0.5 1 calc R U P . .
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.1211
-1.00 0.00 0.00 0.0760
-2.00 1.00 1.99 0.0764
2.00 1.00 0.98 0.0954
0.00 1.00 1.98 0.0922
-2.00 0.00 1.01 0.0730
-2.00 -1.00 -0.98 0.0693
0.00 -1.00 -1.98 0.0572
-1.00 -1.00 -0.98 0.0574
1.00 1.00 0.98 0.1000
-2.01 -2.00 -0.96 0.0555
-1.01 -2.00 -1.96 0.0588
-1.00 0.00 1.00 0.0707
-2.00 -1.00 0.02 0.0630
-1.00 0.00 2.00 0.0627
-1.00 -1.00 2.02 0.0674
1.00 0.00 -2.00 0.1043
1.00 1.00 -2.02 0.0922
-1.00 -2.00 2.04 0.0630
0.00 -1.00 0.02 0.0557
1.00 -2.00 -1.97 0.0579
0.00 -1.00 2.02 0.0592
1.00 -2.00 1.03 0.0474
0.00 1.00 -2.02 0.0795
0.00 0.00 1.00 0.0767
0.00 0.00 -1.00 0.0526
1.00 -1.00 -0.99 0.0675
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
_geom_angle_publ_flag
N1 S1 C7 92.85(17) . . ?
C1 N1 S1 106.9(2) . . ?
N1 C1 N2 119.6(3) . . ?
N1 C1 C2 122.0(3) . . ?
N2 C1 C2 118.4(3) . . ?
C7 N2 C1 109.3(3) . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 C6 118.6(3) . . ?
C6 C2 C1 119.9(3) . . ?
C3 N3 HN3 122(3) . . ?
C4 N3 HN3 114(3) . . ?
C4 N3 C3 123.7(3) . . ?
C2 C3 H3 120.7 . . ?
N3 C3 C2 118.7(4) . . ?
N3 C3 H3 120.7 . . ?
N3 C4 H4 120.1 . . ?
N3 C4 C5 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C10 N4 C9 116.9(3) . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
C2 C6 H6 120.0 . . ?
C5 C6 C2 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
N2 C7 S1 111.4(3) . . ?
N2 C7 C8 122.9(3) . . ?
C8 C7 S1 125.7(3) . . ?
N4 C9 H9 118.3 . . ?
N4 C9 C8 123.5(3) . . ?
C8 C9 H9 118.3 . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 C12 118.9(3) . . ?
C12 C8 C7 122.4(3) . . ?
N4 C10 H10 118.1 . . ?
N4 C10 C11 123.8(3) . . ?
C11 C10 H10 118.1 . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.4(4) . . ?
C12 C11 H11 120.8 . . ?
C8 C12 H12 120.7 . . ?
C11 C12 C8 118.6(3) . . ?
C11 C12 H12 120.7 . . ?
N5 C13 C14 180.0(5) . . ?
C13 C14 H14A 109.5(6) . 7_565 ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5(3) . 7_565 ?
C13 C14 H14C 109.5 . . ?
C13 C14 H14C 109.5(9) . 7_565 ?
H14A C14 H14A 37.5 . 7_565 ?
H14A C14 H14B 109.5 7_565 7_565 ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14B 74.7 . 7_565 ?
H14A C14 H14C 136.3 . 7_565 ?
H14A C14 H14C 109.5 7_565 7_565 ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14A 74.7 . 7_565 ?
H14B C14 H14B 136.3 . 7_565 ?
H14B C14 H14C 37.5 . 7_565 ?
H14B C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 7_565 7_565 ?
H14C C14 H14A 136.3 . 7_565 ?
H14C C14 H14B 37.5 . 7_565 ?
H14C C14 H14C 74.7 . 7_565 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 N1 1.650(3) . ?
S1 C7 1.722(4) . ?
N1 C1 1.326(4) . ?
C1 N2 1.357(4) . ?
C1 C2 1.471(5) . ?
N2 C7 1.302(5) . ?
C2 C3 1.394(5) . ?
C2 C6 1.399(5) . ?
N3 HN3 0.83(4) . ?
N3 C3 1.335(5) . ?
N3 C4 1.334(5) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.370(5) . ?
N4 C9 1.343(4) . ?
N4 C10 1.339(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(5) . ?
N5 C13 1.131(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.471(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.386(5) . ?
C8 C12 1.390(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.460(6) . ?
C14 H14A 0.98(3) 7_565 ?
C14 H14A 0.9800 . ?
C14 H14B 0.980(13) 7_565 ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 H14C 0.98(4) 7_565 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 HN3 I1 0.83(4) 2.64(4) 3.449(3) 166(4) . yes
C3 H3 N4 0.95 2.27 3.190(5) 162.7 1_655 yes
C4 H4 I1 0.95 3.28 3.909(4) 125.7 6_557 yes
C5 H5 I1 0.95 3.15 3.845(4) 131.4 6_557 yes
C10 H10 N1 0.95 2.64 3.455(5) 144.3 1_455 yes
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 N2 0.000(1) . . . . ?
S1 N1 C1 C2 180.000(1) . . . . ?
S1 C7 C8 C9 180.000(1) . . . . ?
S1 C7 C8 C12 0.000(1) . . . . ?
N1 S1 C7 N2 0.000(1) . . . . ?
N1 S1 C7 C8 180.000(1) . . . . ?
N1 C1 N2 C7 0.000(1) . . . . ?
N1 C1 C2 C3 0.000(1) . . . . ?
N1 C1 C2 C6 180.000(1) . . . . ?
C1 N2 C7 S1 0.000(1) . . . . ?
C1 N2 C7 C8 180.000(1) . . . . ?
C1 C2 C3 N3 180.000(1) . . . . ?
C1 C2 C6 C5 180.000(1) . . . . ?
N2 C1 C2 C3 180.000(1) . . . . ?
N2 C1 C2 C6 0.000(1) . . . . ?
N2 C7 C8 C9 0.000(1) . . . . ?
N2 C7 C8 C12 180.000(1) . . . . ?
C2 C1 N2 C7 180.000(1) . . . . ?
N3 C4 C5 C6 0.000(2) . . . . ?
C3 C2 C6 C5 0.000(2) . . . . ?
C3 N3 C4 C5 0.000(2) . . . . ?
C4 N3 C3 C2 0.000(2) . . . . ?
C4 C5 C6 C2 0.000(2) . . . . ?
N4 C9 C8 C7 180.000(1) . . . . ?
N4 C9 C8 C12 0.000(1) . . . . ?
N4 C10 C11 C12 0.000(1) . . . . ?
C6 C2 C3 N3 0.000(1) . . . . ?
C7 S1 N1 C1 0.000(1) . . . . ?
C7 C8 C12 C11 180.000(1) . . . . ?
C9 N4 C10 C11 0.000(1) . . . . ?
C9 C8 C12 C11 0.000(1) . . . . ?
C10 N4 C9 C8 0.000(1) . . . . ?
C10 C11 C12 C8 0.000(1) . . . . ?
