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#$Date: 2017-04-05 13:03:37 +0300 (Wed, 05 Apr 2017) $
#$Revision: 195155 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/60/7056016.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_7056016
loop_
_publ_author_name
'Yutronkie, Nathan J.'
'Tami, Perrine'
'Singh, Simarpreet'
'Kleisath, Elizabeth'
'Gabidullin, Bulat M.'
'Davis, Rebecca'
'Brusso, Jaclyn L.'
_publ_section_title
;
 S-Functionalization of 3,5-bis(2-pyridyl)-1,2,4,6-thiatriazine: probing
 the effect of alkyl chain length in the development of tethered materials
;
_journal_issue                   6
_journal_name_full               'New J. Chem.'
_journal_page_first              2268
_journal_paper_doi               10.1039/C6NJ03721F
_journal_volume                  41
_journal_year                    2017
_chemical_formula_sum            'C36 H40 Cl4 N10 S2'
_chemical_formula_weight         818.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-11-23 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 122.227(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9919(12)
_cell_length_b                   14.2910(8)
_cell_length_c                   16.4594(16)
_cell_measurement_reflns_used    1992
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.78
_cell_measurement_theta_min      2.54
_cell_volume                     3779.1(5)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0381
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7805
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.239
_diffrn_reflns_theta_max         25.239
_diffrn_reflns_theta_min         1.907
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       plate
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.715
_exptl_crystal_size_mid          0.441
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3374
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0872
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1393P)²+7.7477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2195
_refine_ls_wR_factor_ref         0.2481
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2241
_reflns_number_total             3374
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6nj03721f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7056015--7056016.cif.'
_cod_database_code               7056016
_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   0.731
_shelx_estimated_absorpt_t_max   0.880
loop_
_space_group_symop_operation_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_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
C2 C 0.7371(3) 0.4907(4) 0.8971(4) 0.0393(14) Uani 1 1 d . . . . .
H2 H 0.7779 0.4468 0.9392 0.047 Uiso 1 1 calc R U . . .
C3 C 0.6742(4) 0.5129(4) 0.9116(4) 0.0489(16) Uani 1 1 d . . . . .
H3 H 0.6701 0.4830 0.9606 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6178(4) 0.5789(5) 0.8540(5) 0.0582(18) Uani 1 1 d . . . . .
H4 H 0.5740 0.5964 0.8625 0.070 Uiso 1 1 calc R U . . .
C5 C 0.6250(4) 0.6200(4) 0.7832(4) 0.0412(14) Uani 1 1 d . . . . .
H5 H 0.5860 0.6659 0.7421 0.049 Uiso 1 1 calc R U . . .
C6 C 0.6886(3) 0.5943(3) 0.7727(3) 0.0273(11) Uani 1 1 d . . . . .
C7 C 0.6998(3) 0.6392(3) 0.6974(3) 0.0239(11) Uani 1 1 d . . . . .
C9 C 0.6449(3) 0.7498(3) 0.5753(3) 0.0244(11) Uani 1 1 d . . . . .
C10 C 0.5727(3) 0.8133(3) 0.5168(3) 0.0212(10) Uani 1 1 d . . . . .
C11 C 0.5090(3) 0.8201(4) 0.5343(4) 0.0332(12) Uani 1 1 d . . . . .
H11 H 0.5120 0.7870 0.5861 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4413(3) 0.8757(4) 0.4751(4) 0.0387(14) Uani 1 1 d . . . . .
H12 H 0.3962 0.8806 0.4844 0.046 Uiso 1 1 calc R U . . .
C13 C 0.4402(3) 0.9241(4) 0.4022(4) 0.0392(14) Uani 1 1 d . . . . .
H13 H 0.3945 0.9630 0.3600 0.047 Uiso 1 1 calc R U . . .
C14 C 0.5066(3) 0.9146(4) 0.3923(4) 0.0354(13) Uani 1 1 d . . . . .
H14 H 0.5059 0.9492 0.3426 0.042 Uiso 1 1 calc R U . . .
C18 C 0.8583(3) 0.7399(3) 0.6882(3) 0.0260(11) Uani 1 1 d . . . . .
H18A H 0.9098 0.7020 0.7234 0.031 Uiso 1 1 calc R U . . .
H18B H 0.8659 0.7849 0.6478 0.031 Uiso 1 1 calc R U . . .
C19 C 0.8504(3) 0.7953(3) 0.7615(3) 0.0263(11) Uani 1 1 d . . . . .
H19A H 0.8439 0.7519 0.8039 0.032 Uiso 1 1 calc R U . . .
H19B H 0.8002 0.8355 0.7281 0.032 Uiso 1 1 calc R U . . .
C20 C 0.9278(3) 0.8565(4) 0.8222(3) 0.0285(11) Uani 1 1 d . . . . .
H20A H 0.9780 0.8165 0.8508 0.034 Uiso 1 1 calc R U . . .
H20B H 0.9316 0.9027 0.7799 0.034 Uiso 1 1 calc R U . . .
C21 C 0.9264(3) 0.9084(3) 0.9024(3) 0.0269(11) Uani 1 1 d . . . . .
H21A H 0.9260 0.8620 0.9467 0.032 Uiso 1 1 calc R U . . .
H21B H 0.8743 0.9451 0.8739 0.032 Uiso 1 1 calc R U . . .
C22 C 1.0001(3) 0.9743(4) 0.9598(3) 0.0309(12) Uani 1 1 d . . . . .
H22A H 1.0522 0.9376 0.9876 0.037 Uiso 1 1 calc R U . . .
H22B H 1.0002 1.0209 0.9154 0.037 Uiso 1 1 calc R U . . .
N1 N 0.7440(3) 0.5272(3) 0.8275(3) 0.0314(10) Uani 1 1 d . . . . .
N8 N 0.6482(2) 0.7121(3) 0.6531(3) 0.0263(9) Uani 1 1 d . . . . .
N15 N 0.5724(3) 0.8605(3) 0.4469(3) 0.0328(11) Uani 1 1 d . . . . .
N16 N 0.7551(2) 0.6030(3) 0.6827(3) 0.0286(10) Uani 1 1 d . . . . .
N17 N 0.6938(2) 0.7341(3) 0.5433(3) 0.0271(10) Uani 1 1 d . . . . .
S1 S 0.77355(7) 0.66192(8) 0.60890(8) 0.0236(4) Uani 1 1 d . . . . .
C23 C 0.6875(5) 0.8800(5) 0.8144(6) 0.075(2) Uani 1 1 d D U . . .
H23A H 0.7123 0.9430 0.8240 0.090 Uiso 1 1 calc R U . A 1
H23B H 0.6809 0.8532 0.7553 0.090 Uiso 1 1 calc R U . A 1
Cl1 Cl 0.75570(17) 0.80850(18) 0.91315(19) 0.0978(9) Uani 1 1 d D U . . .
Cl2 Cl 0.5909(9) 0.8903(13) 0.7994(14) 0.136(4) Uani 0.57(4) 1 d D U P B 1
Cl2' Cl 0.6138(9) 0.9287(16) 0.8307(12) 0.095(5) Uani 0.43(4) 1 d D U P B 2
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'
Cl Cl 0.1484 0.1585 '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
N1 C2 C3 123.7(5) .
N1 C2 H2 118.1 .
C3 C2 H2 118.1 .
C4 C3 C2 118.1(5) .
C4 C3 H3 121.0 .
C2 C3 H3 121.0 .
C3 C4 C5 119.4(6) .
C3 C4 H4 120.3 .
C5 C4 H4 120.3 .
C6 C5 C4 119.2(5) .
C6 C5 H5 120.4 .
C4 C5 H5 120.4 .
N1 C6 C5 122.4(5) .
N1 C6 C7 116.7(4) .
C5 C6 C7 120.9(4) .
N16 C7 N8 129.2(4) .
N16 C7 C6 117.6(4) .
N8 C7 C6 113.2(4) .
N17 C9 N8 128.7(4) .
N17 C9 C10 116.8(4) .
N8 C9 C10 114.4(4) .
N15 C10 C11 122.8(4) .
N15 C10 C9 116.4(4) .
C11 C10 C9 120.8(4) .
C12 C11 C10 118.8(5) .
C12 C11 H11 120.6 .
C10 C11 H11 120.6 .
C13 C12 C11 118.7(6) .
C13 C12 H12 120.6 .
C11 C12 H12 120.6 .
C14 C13 C12 118.1(5) .
C14 C13 H13 121.0 .
C12 C13 H13 121.0 .
N15 C14 C13 125.0(5) .
N15 C14 H14 117.5 .
C13 C14 H14 117.5 .
C19 C18 S1 117.9(3) .
C19 C18 H18A 107.8 .
S1 C18 H18A 107.8 .
C19 C18 H18B 107.8 .
S1 C18 H18B 107.8 .
H18A C18 H18B 107.2 .
C18 C19 C20 110.4(4) .
C18 C19 H19A 109.6 .
C20 C19 H19A 109.6 .
C18 C19 H19B 109.6 .
C20 C19 H19B 109.6 .
H19A C19 H19B 108.1 .
C21 C20 C19 112.8(4) .
C21 C20 H20A 109.0 .
C19 C20 H20A 109.0 .
C21 C20 H20B 109.0 .
C19 C20 H20B 109.0 .
H20A C20 H20B 107.8 .
C20 C21 C22 113.7(4) .
C20 C21 H21A 108.8 .
C22 C21 H21A 108.8 .
C20 C21 H21B 108.8 .
C22 C21 H21B 108.8 .
H21A C21 H21B 107.7 .
C22 C22 C21 114.2(5) 5_777
C22 C22 H22A 108.7 5_777
C21 C22 H22A 108.7 .
C22 C22 H22B 108.7 5_777
C21 C22 H22B 108.7 .
H22A C22 H22B 107.6 .
C2 N1 C6 117.0(5) .
C7 N8 C9 118.1(4) .
C14 N15 C10 116.5(5) .
C7 N16 S1 116.0(3) .
C9 N17 S1 116.1(3) .
N16 S1 N17 108.3(2) .
N16 S1 C18 103.7(2) .
N17 S1 C18 103.7(2) .
Cl2' C23 Cl1 110.6(6) .
Cl2 C23 Cl1 112.6(6) .
Cl2 C23 H23A 109.1 .
Cl1 C23 H23A 109.1 .
Cl2 C23 H23B 109.1 .
Cl1 C23 H23B 109.1 .
H23A C23 H23B 107.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 N1 1.328(6) .
C2 C3 1.375(8) .
C2 H2 0.9500 .
C3 C4 1.361(8) .
C3 H3 0.9500 .
C4 C5 1.375(8) .
C4 H4 0.9500 .
C5 C6 1.358(7) .
C5 H5 0.9500 .
C6 N1 1.352(6) .
C6 C7 1.509(7) .
C7 N16 1.305(6) .
C7 N8 1.347(6) .
C9 N17 1.308(6) .
C9 N8 1.359(6) .
C9 C10 1.491(7) .
C10 N15 1.332(6) .
C10 C11 1.388(7) .
C11 C12 1.378(7) .
C11 H11 0.9500 .
C12 C13 1.375(8) .
C12 H12 0.9500 .
C13 C14 1.361(8) .
C13 H13 0.9500 .
C14 N15 1.330(6) .
C14 H14 0.9500 .
C18 C19 1.516(7) .
C18 S1 1.815(5) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.536(6) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.526(7) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.526(6) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C22 1.516(10) 5_777
C22 H22A 0.9900 .
C22 H22B 0.9900 .
N16 S1 1.662(4) .
N17 S1 1.667(4) .
C23 Cl2' 1.707(11) .
C23 Cl2 1.720(12) .
C23 Cl1 1.765(9) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
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
C3 H3 S1 0.95 3.00 3.716(6) 133.4 6_566
C13 H13 N1 0.95 2.62 3.316(7) 130.8 8_465
C14 H14 Cl2' 0.95 2.78 3.520(15) 135.7 6_575
C23 H23A N16 0.99 2.39 3.361(9) 167.9 4_656
C23 H23B N8 0.99 2.48 3.355(8) 146.6 .
C3 H3 S1 0.95 3.00 3.716(6) 133.4 6_566
C13 H13 N1 0.95 2.62 3.316(7) 130.8 8_465
C14 H14 Cl2' 0.95 2.78 3.520(15) 135.7 6_575
C23 H23A N16 0.99 2.39 3.361(9) 167.9 4_656
C23 H23B N8 0.99 2.48 3.355(8) 146.6 .
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
N1 C2 C3 C4 -2.8(10) .
C2 C3 C4 C5 0.7(10) .
C3 C4 C5 C6 -0.4(10) .
C4 C5 C6 N1 2.1(9) .
C4 C5 C6 C7 -178.6(5) .
N1 C6 C7 N16 8.1(6) .
C5 C6 C7 N16 -171.3(5) .
N1 C6 C7 N8 -173.1(4) .
C5 C6 C7 N8 7.6(7) .
N17 C9 C10 N15 -11.0(6) .
N8 C9 C10 N15 172.2(4) .
N17 C9 C10 C11 167.5(4) .
N8 C9 C10 C11 -9.3(6) .
N15 C10 C11 C12 2.0(7) .
C9 C10 C11 C12 -176.4(4) .
C10 C11 C12 C13 -1.4(7) .
C11 C12 C13 C14 -0.1(8) .
C12 C13 C14 N15 1.2(8) .
S1 C18 C19 C20 179.6(3) .
C18 C19 C20 C21 -175.6(4) .
C19 C20 C21 C22 -176.4(4) .
C20 C21 C22 C22 -179.5(5) 5_777
C3 C2 N1 C6 4.4(8) .
C5 C6 N1 C2 -4.0(7) .
C7 C6 N1 C2 176.7(4) .
N16 C7 N8 C9 7.4(7) .
C6 C7 N8 C9 -171.3(4) .
N17 C9 N8 C7 -10.5(7) .
C10 C9 N8 C7 165.8(4) .
C13 C14 N15 C10 -0.8(8) .
C11 C10 N15 C14 -0.9(7) .
C9 C10 N15 C14 177.6(4) .
N8 C7 N16 S1 8.4(7) .
C6 C7 N16 S1 -173.0(3) .
N8 C9 N17 S1 -3.1(6) .
C10 C9 N17 S1 -179.3(3) .
C7 N16 S1 N17 -18.9(4) .
C7 N16 S1 C18 90.8(4) .
C9 N17 S1 N16 16.6(4) .
C9 N17 S1 C18 -93.1(4) .
C19 C18 S1 N16 -47.9(4) .
C19 C18 S1 N17 65.2(4) .
