#------------------------------------------------------------------------------
#$Date: 2016-06-18 11:02:44 +0200 (Sat 18 de Jun de 2016) $
#$Revision: 183742 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/53/7055334.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_7055334
loop_
_publ_author_name
'Kleisath, Elizabeth'
'Yutronkie, Nathan J.'
'Korobkov, Ilia'
'Gabidullin, Bulat M.'
'Brusso, Jaclyn L.'
_publ_section_title
;
 Alkyl-functionalization of 3,5-bis(2-pyridyl)-1,2,4,6-thiatriazine
;
_journal_issue                   5
_journal_name_full               'New J. Chem.'
_journal_page_first              4472
_journal_paper_doi               10.1039/C5NJ02611C
_journal_volume                  40
_journal_year                    2016
_chemical_formula_sum            'C14 H13 I N5 Na S'
_chemical_formula_weight         433.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-09-24 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                109.4798(8)
_cell_angle_beta                 116.3682(8)
_cell_angle_gamma                102.2525(9)
_cell_formula_units_Z            2
_cell_length_a                   10.1629(3)
_cell_length_b                   10.3262(3)
_cell_length_c                   10.3488(3)
_cell_measurement_reflns_used    7857
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.43
_cell_measurement_theta_min      2.31
_cell_volume                     829.70(4)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0109
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8711
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.425
_diffrn_reflns_theta_min         2.313
_exptl_absorpt_coefficient_mu    2.084
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0176
_refine_ls_R_factor_gt           0.0167
_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)+(0.0237P)²+0.3038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0434
_refine_ls_wR_factor_ref         0.0439
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3897
_reflns_number_total             4062
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5nj02611c2.cif
_cod_data_source_block           jb039
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7055334--7055337.cif.
;
_cod_original_cell_volume        829.69(4)
_cod_database_code               7055334
_shelx_shelxl_version_number     2014/7
_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_min   0.705
_shelx_estimated_absorpt_t_max   0.732
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
I1 I 0.75968(2) 0.04125(2) 0.56392(2) 0.03518(4) Uani 1 1 d . .
S1 S 0.60155(5) 0.60958(4) 0.27252(5) 0.03222(8) Uani 1 1 d . .
Na1 Na 0.52228(8) 0.19303(7) 0.46150(7) 0.03443(13) Uani 1 1 d . .
N1 N 0.59578(15) 0.37739(13) 0.37772(15) 0.0280(2) Uani 1 1 d . .
N2 N 0.72441(16) 0.45065(15) 0.69839(16) 0.0331(3) Uani 1 1 d . .
N3 N 0.39042(15) 0.08347(14) 0.16271(15) 0.0306(2) Uani 1 1 d . .
N007 N 0.50880(16) 0.42240(14) 0.14498(16) 0.0326(3) Uani 1 1 d . .
N008 N 0.65440(18) 0.64023(15) 0.45951(17) 0.0361(3) Uani 1 1 d . .
C1 C 0.65872(17) 0.52481(16) 0.48652(17) 0.0274(3) Uani 1 1 d . .
C2 C 0.51721(16) 0.33691(16) 0.21526(17) 0.0268(3) Uani 1 1 d . .
C3 C 0.73999(17) 0.56564(17) 0.66494(17) 0.0286(3) Uani 1 1 d . .
C4 C 0.83017(19) 0.71758(18) 0.7873(2) 0.0358(3) Uani 1 1 d . .
H4A H 0.8381 0.7962 0.7591 0.043 Uiso 1 1 calc R U
C5 C 0.9081(2) 0.7514(2) 0.9512(2) 0.0413(4) Uani 1 1 d . .
H5A H 0.9692 0.8539 1.0376 0.050 Uiso 1 1 calc R U
C6 C 0.8957(2) 0.6344(2) 0.9869(2) 0.0427(4) Uani 1 1 d . .
H6A H 0.9503 0.6545 1.0982 0.051 Uiso 1 1 calc R U
C7 C 0.8024(2) 0.4868(2) 0.8577(2) 0.0401(3) Uani 1 1 d . .
H7A H 0.7930 0.4066 0.8834 0.048 Uiso 1 1 calc R U
C8 C 0.41963(16) 0.16930(16) 0.09775(17) 0.0272(3) Uani 1 1 d . .
C9 C 0.3610(2) 0.11054(19) -0.06852(19) 0.0365(3) Uani 1 1 d . .
H9A H 0.3868 0.1747 -0.1096 0.044 Uiso 1 1 calc R U
C10 C 0.2638(2) -0.0442(2) -0.1736(2) 0.0435(4) Uani 1 1 d . .
H10A H 0.2215 -0.0881 -0.2881 0.052 Uiso 1 1 calc R U
C11 C 0.2300(2) -0.13250(19) -0.1086(2) 0.0431(4) Uani 1 1 d . .
H11A H 0.1621 -0.2383 -0.1778 0.052 Uiso 1 1 calc R U
C12 C 0.2964(2) -0.06485(18) 0.0598(2) 0.0382(3) Uani 1 1 d . .
H12A H 0.2739 -0.1271 0.1040 0.046 Uiso 1 1 calc R U
C13 C 0.7922(2) 0.66557(19) 0.2917(2) 0.0401(3) Uani 1 1 d . .
H13A H 0.7701 0.6436 0.1815 0.048 Uiso 1 1 calc R U
H13B H 0.8548 0.7768 0.3653 0.048 Uiso 1 1 calc R U
C14 C 0.8962(3) 0.5899(2) 0.3579(3) 0.0547(5) Uani 1 1 d . .
H14A H 0.9969 0.6274 0.3639 0.082 Uiso 1 1 calc R U
H14B H 0.9222 0.6133 0.4686 0.082 Uiso 1 1 calc R U
H14C H 0.8372 0.4798 0.2844 0.082 Uiso 1 1 calc R U
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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
Na1 I1 Na1 85.589(16) . 2_656
N008 S1 N007 108.54(7) . .
N008 S1 C13 103.52(8) . .
N007 S1 C13 103.37(8) . .
N3 Na1 N1 66.47(4) . .
N3 Na1 N2 133.06(5) . .
N1 Na1 N2 66.64(4) . .
N3 Na1 N008 105.48(5) . 2_666
N1 Na1 N008 84.42(4) . 2_666
N2 Na1 N008 72.05(4) . 2_666
N3 Na1 I1 104.15(4) . .
N1 Na1 I1 116.04(4) . .
N2 Na1 I1 94.02(4) . .
N008 Na1 I1 148.99(3) 2_666 .
N3 Na1 I1 94.96(3) . 2_656
N1 Na1 I1 146.92(4) . 2_656
N2 Na1 I1 126.78(4) . 2_656
N008 Na1 I1 74.18(3) 2_666 2_656
I1 Na1 I1 94.410(16) . 2_656
C1 N1 C2 117.47(12) . .
C1 N1 Na1 117.11(9) . .
C2 N1 Na1 119.81(9) . .
C7 N2 C3 117.13(14) . .
C7 N2 Na1 125.29(12) . .
C3 N2 Na1 116.94(10) . .
C12 N3 C8 117.44(13) . .
C12 N3 Na1 121.70(11) . .
C8 N3 Na1 120.69(10) . .
C2 N007 S1 115.98(11) . .
C1 N008 S1 116.05(11) . .
C1 N008 Na1 121.35(10) . 2_666
S1 N008 Na1 104.86(6) . 2_666
N008 C1 N1 129.35(13) . .
N008 C1 C3 114.25(13) . .
N1 C1 C3 116.34(12) . .
N007 C2 N1 129.72(13) . .
N007 C2 C8 115.01(12) . .
N1 C2 C8 115.22(12) . .
N2 C3 C4 123.04(14) . .
N2 C3 C1 117.09(13) . .
C4 C3 C1 119.85(14) . .
C5 C4 C3 118.42(16) . .
C6 C5 C4 119.00(16) . .
C5 C6 C7 118.72(16) . .
N2 C7 C6 123.67(17) . .
N3 C8 C9 123.14(14) . .
N3 C8 C2 115.98(12) . .
C9 C8 C2 120.86(13) . .
C8 C9 C10 118.52(15) . .
C11 C10 C9 118.68(15) . .
C10 C11 C12 118.98(15) . .
N3 C12 C11 123.21(15) . .
C14 C13 S1 115.40(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 Na1 3.1373(7) .
I1 Na1 3.1775(6) 2_656
S1 N008 1.6522(14) .
S1 N007 1.6693(13) .
S1 C13 1.7986(17) .
Na1 N3 2.4453(14) .
Na1 N1 2.4508(13) .
Na1 N2 2.4828(15) .
Na1 N008 2.9213(16) 2_666
Na1 I1 3.1775(6) 2_656
N1 C1 1.3409(18) .
N1 C2 1.3550(18) .
N2 C7 1.337(2) .
N2 C3 1.341(2) .
N3 C12 1.3342(19) .
N3 C8 1.3374(18) .
N007 C2 1.3117(18) .
N008 C1 1.3168(19) .
N008 Na1 2.9213(16) 2_666
C1 C3 1.4992(19) .
C2 C8 1.5014(19) .
C3 C4 1.392(2) .
C4 C5 1.386(2) .
C5 C6 1.373(3) .
C6 C7 1.382(3) .
C8 C9 1.387(2) .
C9 C10 1.389(2) .
C10 C11 1.372(3) .
C11 C12 1.386(2) .
C13 C14 1.503(3) .
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_4
N008 S1 N007 C2 -10.43(14) . .
C13 S1 N007 C2 99.04(13) . .
N007 S1 N008 C1 18.25(14) . .
C13 S1 N008 C1 -91.11(13) . .
N007 S1 N008 Na1 -118.53(6) . 2_666
C13 S1 N008 Na1 132.11(7) . 2_666
S1 N008 C1 N1 -15.2(2) . .
Na1 N008 C1 N1 113.98(15) 2_666 .
S1 N008 C1 C3 167.73(10) . .
Na1 N008 C1 C3 -63.07(15) 2_666 .
C2 N1 C1 N008 1.0(2) . .
Na1 N1 C1 N008 -152.62(13) . .
C2 N1 C1 C3 177.98(12) . .
Na1 N1 C1 C3 24.38(16) . .
S1 N007 C2 N1 -2.9(2) . .
S1 N007 C2 C8 174.35(10) . .
C1 N1 C2 N007 9.6(2) . .
Na1 N1 C2 N007 162.47(13) . .
C1 N1 C2 C8 -167.65(12) . .
Na1 N1 C2 C8 -14.78(16) . .
C7 N2 C3 C4 -1.0(2) . .
Na1 N2 C3 C4 170.25(11) . .
C7 N2 C3 C1 177.33(13) . .
Na1 N2 C3 C1 -11.40(16) . .
N008 C1 C3 N2 169.01(14) . .
N1 C1 C3 N2 -8.45(19) . .
N008 C1 C3 C4 -12.6(2) . .
N1 C1 C3 C4 169.95(13) . .
N2 C3 C4 C5 0.3(2) . .
C1 C3 C4 C5 -177.96(14) . .
C3 C4 C5 C6 1.0(2) . .
C4 C5 C6 C7 -1.6(2) . .
C3 N2 C7 C6 0.3(2) . .
Na1 N2 C7 C6 -170.12(13) . .
C5 C6 C7 N2 1.0(3) . .
C12 N3 C8 C9 -1.9(2) . .
Na1 N3 C8 C9 173.51(12) . .
C12 N3 C8 C2 176.34(13) . .
Na1 N3 C8 C2 -8.24(16) . .
N007 C2 C8 N3 -162.74(13) . .
N1 C2 C8 N3 14.93(18) . .
N007 C2 C8 C9 15.6(2) . .
N1 C2 C8 C9 -166.77(14) . .
N3 C8 C9 C10 1.7(2) . .
C2 C8 C9 C10 -176.44(15) . .
C8 C9 C10 C11 -0.1(3) . .
C9 C10 C11 C12 -1.3(3) . .
C8 N3 C12 C11 0.5(2) . .
Na1 N3 C12 C11 -174.90(14) . .
C10 C11 C12 N3 1.1(3) . .
N008 S1 C13 C14 54.27(17) . .
N007 S1 C13 C14 -58.89(16) . .
