#------------------------------------------------------------------------------
#$Date: 2015-10-09 16:25:09 +0300 (Fri, 09 Oct 2015) $
#$Revision: 162136 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/50/7055016.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_7055016
loop_
_publ_author_name
'Magnan, François'
'Korobkov, Ilia'
'Brusso, Jaclyn'
_publ_section_title
;
 Influence of substitution pattern and enhanced π-conjugation on a family
 of thiophene functionalized 1,5-dithia-2,4,6,8-tetrazocines
;
_journal_issue                   9
_journal_name_full               'New J. Chem.'
_journal_page_first              7272
_journal_paper_doi               10.1039/C5NJ01345C
_journal_volume                  39
_journal_year                    2015
_chemical_formula_sum            'C15 H17 N2 S3'
_chemical_formula_weight         321.48
_chemical_melting_point          456
_chemical_name_common            b(HTT08MR
_chemical_name_systematic
3,7-bis[5-(5-hexylthiophen-2-yl)thienyl]-1,5,2,4,6,8-dithiatetrazocine
_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
;
2015-05-27 deposited with the CCDC.
2015-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                98.497(3)
_cell_angle_beta                 102.934(4)
_cell_angle_gamma                107.792(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6627(4)
_cell_length_b                   9.3450(6)
_cell_length_c                   13.5348(7)
_cell_measurement_reflns_used    4401
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.35
_cell_volume                     760.54(8)
_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 0.986
_diffrn_measured_fraction_theta_max 0.981
_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  0.0199
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_laue_measured_fraction_full 0.986
_diffrn_reflns_laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7798
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.344
_diffrn_reflns_theta_min         1.587
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             338
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0312
_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)+(0.0542P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0853
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3021
_reflns_number_total             3723
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5nj01345c2.cif
_cod_data_source_block           jb037
_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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7055016--7055018.cif.
;
_cod_database_code               7055016
_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   0.847
_shelx_estimated_absorpt_t_max   0.986
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
S1 S -0.22437(6) 0.49590(4) 0.57484(3) 0.03289(11) Uani 1 1 d . .
S2 S 0.04266(6) 0.85584(4) 0.41348(3) 0.02727(10) Uani 1 1 d . .
S3 S 0.16658(6) 1.18104(4) 0.21377(3) 0.03399(11) Uani 1 1 d . .
N1 N -0.2116(2) 0.61133(13) 0.50172(9) 0.0292(3) Uani 1 1 d . .
N2 N -0.5639(2) 0.61195(13) 0.40773(9) 0.0302(3) Uani 1 1 d . .
C1 C -0.3460(2) 0.65704(15) 0.43621(10) 0.0257(3) Uani 1 1 d . .
C2 C -0.2393(2) 0.77731(15) 0.38697(10) 0.0260(3) Uani 1 1 d . .
C3 C -0.3426(2) 0.84247(17) 0.31744(12) 0.0344(3) Uani 1 1 d . .
H3A H -0.4978 0.8142 0.2933 0.041 Uiso 1 1 calc R U
C4 C -0.1943(2) 0.95586(18) 0.28539(12) 0.0353(3) Uani 1 1 d . .
H4A H -0.2396 1.0119 0.2371 0.042 Uiso 1 1 calc R U
C5 C 0.0222(2) 0.97783(15) 0.33060(10) 0.0268(3) Uani 1 1 d . .
C6 C 0.2111(2) 1.08583(15) 0.31213(10) 0.0270(3) Uani 1 1 d . .
C7 C 0.4310(2) 1.13015(16) 0.35984(11) 0.0305(3) Uani 1 1 d . .
H7A H 0.4902 1.0909 0.4159 0.037 Uiso 1 1 calc R U
C8 C 0.5627(2) 1.24108(16) 0.31723(11) 0.0320(3) Uani 1 1 d . .
H8A H 0.7187 1.2832 0.3420 0.038 Uiso 1 1 calc R U
C9 C 0.4434(2) 1.28089(15) 0.23749(11) 0.0293(3) Uani 1 1 d . .
C10 C 0.5112(2) 1.39152(18) 0.17097(12) 0.0364(3) Uani 1 1 d . .
H10A H 0.4514 1.4751 0.1840 0.044 Uiso 1 1 calc R U
H10B H 0.4415 1.3359 0.0969 0.044 Uiso 1 1 calc R U
C11 C 0.7570(2) 1.46527(16) 0.18714(11) 0.0304(3) Uani 1 1 d . .
H11A H 0.8205 1.3837 0.1745 0.036 Uiso 1 1 calc R U
H11B H 0.8293 1.5258 0.2600 0.036 Uiso 1 1 calc R U
C12 C 0.7987(2) 1.57084(17) 0.11267(11) 0.0332(3) Uani 1 1 d . .
H12A H 0.7335 1.5071 0.0404 0.040 Uiso 1 1 calc R U
H12B H 0.7206 1.6445 0.1213 0.040 Uiso 1 1 calc R U
C13 C 1.0392(2) 1.66259(17) 0.12665(11) 0.0324(3) Uani 1 1 d . .
H13A H 1.1045 1.7305 0.1977 0.039 Uiso 1 1 calc R U
H13B H 1.1198 1.5903 0.1196 0.039 Uiso 1 1 calc R U
C14 C 1.0660(3) 1.76067(18) 0.04713(12) 0.0388(4) Uani 1 1 d . .
H14A H 1.0037 1.6916 -0.0236 0.047 Uiso 1 1 calc R U
H14B H 0.9794 1.8292 0.0526 0.047 Uiso 1 1 calc R U
C15 C 1.3021(3) 1.8594(2) 0.05929(14) 0.0496(4) Uani 1 1 d . .
H15A H 1.3054 1.9188 0.0054 0.074 Uiso 1 1 calc R U
H15B H 1.3644 1.9304 0.1283 0.074 Uiso 1 1 calc R U
H15C H 1.3888 1.7926 0.0520 0.074 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'
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
N2 S1 N1 126.68(7) 2_466 .
C2 S2 C5 91.88(7) . .
C9 S3 C6 92.91(7) . .
C1 N1 S1 139.10(11) . .
C1 N2 S1 143.89(10) . 2_466
N1 C1 N2 130.32(12) . .
N1 C1 C2 115.74(12) . .
N2 C1 C2 113.94(12) . .
C3 C2 C1 126.39(13) . .
C3 C2 S2 111.35(11) . .
C1 C2 S2 122.26(10) . .
C2 C3 C4 112.70(13) . .
C5 C4 C3 113.53(13) . .
C4 C5 C6 126.01(13) . .
C4 C5 S2 110.54(11) . .
C6 C5 S2 123.45(11) . .
C7 C6 C5 131.38(13) . .
C7 C6 S3 110.10(10) . .
C5 C6 S3 118.52(11) . .
C6 C7 C8 113.25(13) . .
C9 C8 C7 113.40(13) . .
C8 C9 C10 131.76(13) . .
C8 C9 S3 110.34(11) . .
C10 C9 S3 117.90(11) . .
C9 C10 C11 116.22(13) . .
C10 C11 C12 109.93(12) . .
C13 C12 C11 115.42(12) . .
C14 C13 C12 111.91(12) . .
C15 C14 C13 114.48(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 N2 1.5531(13) 2_466
S1 N1 1.5644(12) .
S2 C2 1.7247(14) .
S2 C5 1.7266(13) .
S3 C9 1.7236(15) .
S3 C6 1.7280(14) .
N1 C1 1.3266(18) .
N2 C1 1.3272(18) .
N2 S1 1.5532(12) 2_466
C1 C2 1.4689(18) .
C2 C3 1.3658(19) .
C3 C4 1.405(2) .
C4 C5 1.373(2) .
C5 C6 1.4507(19) .
C6 C7 1.3645(19) .
C7 C8 1.423(2) .
C8 C9 1.360(2) .
C9 C10 1.5017(19) .
C10 C11 1.520(2) .
C11 C12 1.5226(19) .
C12 C13 1.522(2) .
C13 C14 1.519(2) .
C14 C15 1.518(2) .
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
N2 S1 N1 C1 -0.6(2) 2_466
S1 N1 C1 N2 -0.6(3) .
S1 N1 C1 C2 179.04(12) .
S1 N2 C1 N1 1.9(3) 2_466
S1 N2 C1 C2 -177.77(14) 2_466
N1 C1 C2 C3 -179.89(14) .
N2 C1 C2 C3 -0.2(2) .
N1 C1 C2 S2 -0.67(17) .
N2 C1 C2 S2 179.05(10) .
C5 S2 C2 C3 0.12(12) .
C5 S2 C2 C1 -179.21(11) .
C1 C2 C3 C4 179.31(13) .
S2 C2 C3 C4 0.02(17) .
C2 C3 C4 C5 -0.2(2) .
C3 C4 C5 C6 179.54(14) .
C3 C4 C5 S2 0.28(18) .
C2 S2 C5 C4 -0.23(12) .
C2 S2 C5 C6 -179.51(12) .
C4 C5 C6 C7 171.77(15) .
S2 C5 C6 C7 -9.1(2) .
C4 C5 C6 S3 -8.3(2) .
S2 C5 C6 S3 170.90(8) .
C9 S3 C6 C7 -0.30(11) .
C9 S3 C6 C5 179.72(11) .
C5 C6 C7 C8 -179.81(14) .
S3 C6 C7 C8 0.22(16) .
C6 C7 C8 C9 0.02(19) .
C7 C8 C9 C10 179.76(15) .
C7 C8 C9 S3 -0.24(16) .
C6 S3 C9 C8 0.31(12) .
C6 S3 C9 C10 -179.69(12) .
C8 C9 C10 C11 5.8(2) .
S3 C9 C10 C11 -174.19(11) .
C9 C10 C11 C12 178.66(13) .
C10 C11 C12 C13 175.19(13) .
C11 C12 C13 C14 178.16(13) .
C12 C13 C14 C15 178.00(14) .
