#------------------------------------------------------------------------------
#$Date: 2016-03-26 04:00:09 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180205 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/99/7109947.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_7109947
loop_
_publ_author_name
'Peng An'
'Zhipeng Yu'
'Qing Lin'
_publ_section_title
;
 Design of oligothiophene-based tetrazoles for laser-triggered photoclick
 chemistry in living cells
;
_journal_name_full               Chem.Commun.
_journal_page_first              9920
_journal_paper_doi               10.1039/c3cc45752d
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C17 H10 N4 S4'
_chemical_formula_sum            'C17 H10 N4 S4'
_chemical_formula_weight         398.53
_chemical_name_common            ubql08
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.335(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1335(10)
_cell_length_b                   5.6166(4)
_cell_length_c                   22.0910(16)
_cell_measurement_reflns_used    3995
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      33.74
_cell_measurement_theta_min      2.78
_cell_volume                     1674.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, ω scans per φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0943
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            70918
_diffrn_reflns_theta_full        34.97
_diffrn_reflns_theta_max         34.97
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  0.9342
_exptl_absorpt_correction_T_min  0.8648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2008)'
_exptl_crystal_colour            orange-brown
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         7326
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0564P)²+0.6354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                5086
_reflns_number_total             7326
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc45752d.txt
_cod_data_source_block           ubql08
_cod_database_code               7109947
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.58725(3) 0.20502(8) 0.54976(2) 0.01802(9) Uani 1 1 d . A .
S2 S 0.23224(3) 0.17841(8) 0.73102(2) 0.01974(10) Uani 1 1 d . A .
S3 S 0.83982(4) -0.09582(9) 0.50194(2) 0.02547(11) Uani 1 1 d . A .
N1 N 0.45162(12) -0.0633(3) 0.66842(7) 0.0193(3) Uani 1 1 d . . .
N2 N 0.47799(12) 0.0735(3) 0.62689(7) 0.0180(3) Uani 0.619(18) 1 d P A 1
C17 C 0.37978(12) 0.0673(3) 0.67927(8) 0.0188(3) Uani 0.619(18) 1 d P A 1
N2' N 0.37978(12) 0.0673(3) 0.67927(8) 0.0188(3) Uani 0.381(18) 1 d P A 5
C17' C 0.47799(12) 0.0735(3) 0.62689(7) 0.0180(3) Uani 0.381(18) 1 d P A 5
N3 N 0.36391(13) 0.2754(3) 0.64692(8) 0.0241(3) Uani 1 1 d . . .
N4 N 0.42665(13) 0.2777(3) 0.61348(8) 0.0237(3) Uani 1 1 d . A .
C1 C 0.55332(13) 0.0094(3) 0.59941(8) 0.0173(3) Uani 1 1 d . . .
C2 C 0.60563(13) -0.1988(3) 0.60808(8) 0.0190(3) Uani 1 1 d . A .
H2 H 0.5965 -0.3263 0.6341 0.023 Uiso 1 1 calc R . .
C3 C 0.67524(13) -0.2002(3) 0.57333(8) 0.0191(3) Uani 1 1 d . . .
H3 H 0.7183 -0.3303 0.5735 0.023 Uiso 1 1 calc R A .
C4 C 0.67432(13) 0.0052(3) 0.53946(8) 0.0171(3) Uani 1 1 d . A .
C5 C 0.32377(13) -0.0043(3) 0.72026(8) 0.0192(3) Uani 1 1 d . . .
C6 C 0.33153(14) -0.2131(3) 0.75295(9) 0.0205(3) Uani 1 1 d . A .
H6 H 0.3774 -0.3358 0.7521 0.025 Uiso 1 1 calc R . .
C7 C 0.26288(13) -0.2247(3) 0.78829(9) 0.0191(3) Uani 1 1 d . . .
H7 H 0.2580 -0.3567 0.8141 0.023 Uiso 1 1 calc R A .
C8 C 0.20427(13) -0.0263(3) 0.78151(8) 0.0174(3) Uani 1 1 d . A .
C9 C 0.73545(13) 0.0675(3) 0.49943(8) 0.0183(3) Uani 1 1 d . . .
C10 C 0.72354(13) 0.2597(3) 0.45783(8) 0.0198(3) Uani 1 1 d . A .
H10 H 0.6713 0.3726 0.4504 0.024 Uiso 1 1 calc R . .
C11 C 0.80022(15) 0.2645(4) 0.42792(9) 0.0255(4) Uani 1 1 d . . .
H11 H 0.8038 0.3805 0.3974 0.031 Uiso 1 1 calc R A .
C12 C 0.86786(15) 0.0858(4) 0.44759(9) 0.0268(4) Uani 1 1 d D A .
H12 H 0.9239 0.0648 0.4328 0.032 Uiso 1 1 calc R . .
C13 C 0.1259(4) 0.0239(6) 0.8102(3) 0.0170(5) Uani 0.905(2) 1 d PD A 1
C14 C 0.0609(5) 0.2074(10) 0.7999(3) 0.0213(7) Uani 0.905(2) 1 d PD A 1
H14 H 0.0616 0.3349 0.7718 0.026 Uiso 0.905(2) 1 calc PR A 1
C15 C -0.0083(2) 0.1925(4) 0.83478(17) 0.0219(5) Uani 0.905(2) 1 d PD A 1
H15 H -0.0590 0.3062 0.8325 0.026 Uiso 0.905(2) 1 calc PR A 1
C16 C 0.00693(19) -0.0058(5) 0.87213(13) 0.0234(5) Uani 0.905(2) 1 d PD A 1
H16 H -0.0320 -0.0465 0.8990 0.028 Uiso 0.905(2) 1 calc PR A 1
S4 S 0.10422(6) -0.17283(13) 0.86494(4) 0.02171(15) Uani 0.905(2) 1 d PD A 1
C13' C 0.127(4) -0.010(7) 0.810(3) 0.0170(5) Uani 0.095(2) 1 d PD A 5
C14' C 0.108(3) -0.141(6) 0.8556(18) 0.02171(15) Uani 0.095(2) 1 d PD A 5
H14' H 0.1466 -0.2741 0.8749 0.026 Uiso 0.095(2) 1 calc PR A 5
C15' C 0.025(2) -0.058(5) 0.8720(14) 0.0234(5) Uani 0.095(2) 1 d PD A 5
H15' H -0.0006 -0.1313 0.9026 0.028 Uiso 0.095(2) 1 calc PR A 5
C16' C -0.014(2) 0.140(5) 0.8385(19) 0.0219(5) Uani 0.095(2) 1 d PD A 5
H16' H -0.0730 0.2134 0.8407 0.026 Uiso 0.095(2) 1 calc PR A 5
S4' S 0.0553(15) 0.244(3) 0.7917(9) 0.0213(7) Uani 0.095(2) 1 d PD A 5
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
C1 S1 C4 90.80(9)
C5 S2 C8 91.05(9)
C12 S3 C9 92.02(10)
C17 N1 N2 101.00(15)
N1 N2 N4 113.65(15)
N1 N2 C1 123.18(15)
N4 N2 C1 123.17(16)
N1 C17 N3 113.34(16)
N1 C17 C5 123.79(16)
N3 C17 C5 122.86(16)
N4 N3 C17 105.79(16)
N3 N4 N2 106.20(15)
C2 C1 N2 126.90(17)
C2 C1 S1 113.23(14)
N2 C1 S1 119.88(13)
C1 C2 C3 111.28(16)
C1 C2 H2 124.4
C3 C2 H2 124.4
C4 C3 C2 113.29(16)
C4 C3 H3 123.4
C2 C3 H3 123.4
C3 C4 C9 128.61(17)
C3 C4 S1 111.41(14)
C9 C4 S1 119.98(13)
C6 C5 C17 127.29(17)
C6 C5 S2 112.60(14)
C17 C5 S2 120.09(14)
C5 C6 C7 111.76(17)
C5 C6 H6 124.1
C7 C6 H6 124.1
C8 C7 C6 113.19(17)
C8 C7 H7 123.4
C6 C7 H7 123.4
C7 C8 C13' 121.7(8)
C7 C8 C13 128.55(18)
C7 C8 S2 111.38(14)
C13' C8 S2 126.7(8)
C13 C8 S2 120.06(15)
C10 C9 C4 127.66(17)
C10 C9 S3 111.54(14)
C4 C9 S3 120.75(13)
C9 C10 C11 111.11(17)
C9 C10 H10 124.4
C11 C10 H10 124.4
C12 C11 C10 113.27(18)
C12 C11 H11 123.4
C10 C11 H11 123.4
C11 C12 S3 112.06(16)
C11 C12 H12 124.0
S3 C12 H12 124.0
C14 C13 C8 129.8(4)
C14 C13 S4 110.5(3)
C8 C13 S4 119.67(19)
C13 C14 C15 114.0(3)
C13 C14 H14 123.0
C15 C14 H14 123.0
C16 C15 C14 111.5(3)
C16 C15 H15 124.2
C14 C15 H15 124.2
C15 C16 S4 112.2(2)
C15 C16 H16 123.9
S4 C16 H16 123.9
C16 S4 C13 91.67(12)
C14' C13' C8 131(2)
C14' C13' S4' 113.3(12)
C8 C13' S4' 115.2(13)
C13' C14' C15' 112.4(17)
C13' C14' H14' 123.8
C15' C14' H14' 123.8
C16' C15' C14' 111.2(18)
C16' C15' H15' 124.4
C14' C15' H15' 124.4
C15' C16' S4' 113.5(16)
C15' C16' H16' 123.2
S4' C16' H16' 123.2
C16' S4' C13' 88.5(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7185(18)
S1 C4 1.7301(18)
S2 C5 1.7222(18)
S2 C8 1.7278(18)
S3 C12 1.710(2)
S3 C9 1.7237(18)
N1 C17 1.331(2)
N1 N2 1.332(2)
N2 N4 1.342(2)
N2 C1 1.420(2)
C17 N3 1.353(2)
C17 C5 1.427(2)
N3 N4 1.312(2)
C1 C2 1.367(2)
C2 C3 1.417(3)
C2 H2 0.9500
C3 C4 1.373(2)
C3 H3 0.9500
C4 C9 1.451(3)
C5 C6 1.365(3)
C6 C7 1.416(3)
C6 H6 0.9500
C7 C8 1.370(2)
C7 H7 0.9500
C8 C13' 1.418(10)
C8 C13 1.458(3)
C9 C10 1.395(3)
C10 C11 1.428(3)
C10 H10 0.9500
C11 C12 1.365(3)
C11 H11 0.9500
C12 H12 0.9500
C13 C14 1.354(5)
C13 S4 1.732(3)
C14 C15 1.417(7)
C14 H14 0.9500
C15 C16 1.364(3)
C15 H15 0.9500
C16 S4 1.711(2)
C16 H16 0.9500
C13' C14' 1.338(17)
C13' S4' 1.727(10)
C14' C15' 1.405(19)
C14' H14' 0.9500
C15' C16' 1.356(17)
C15' H15' 0.9500
C16' S4' 1.723(18)
C16' H16' 0.9500
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
C17 N1 N2 N4 0.80(19)
C17 N1 N2 C1 -179.21(16)
N2 N1 C17 N3 -1.0(2)
N2 N1 C17 C5 178.33(17)
N1 C17 N3 N4 0.8(2)
C5 C17 N3 N4 -178.49(17)
C17 N3 N4 N2 -0.3(2)
N1 N2 N4 N3 -0.3(2)
C1 N2 N4 N3 179.66(17)
N1 N2 C1 C2 3.4(3)
N4 N2 C1 C2 -176.64(17)
N1 N2 C1 S1 -176.25(13)
N4 N2 C1 S1 3.7(2)
C4 S1 C1 C2 0.08(14)
C4 S1 C1 N2 179.75(14)
N2 C1 C2 C3 -179.75(17)
S1 C1 C2 C3 -0.1(2)
C1 C2 C3 C4 0.1(2)
C2 C3 C4 C9 179.25(17)
C2 C3 C4 S1 0.0(2)
C1 S1 C4 C3 -0.03(14)
C1 S1 C4 C9 -179.37(15)
N1 C17 C5 C6 -1.9(3)
N3 C17 C5 C6 177.39(18)
N1 C17 C5 S2 -179.99(14)
N3 C17 C5 S2 -0.7(3)
C8 S2 C5 C6 0.87(15)
C8 S2 C5 C17 179.26(15)
C17 C5 C6 C7 -179.12(18)
S2 C5 C6 C7 -0.9(2)
C5 C6 C7 C8 0.4(2)
C6 C7 C8 C13' 176(4)
C6 C7 C8 C13 179.7(4)
C6 C7 C8 S2 0.3(2)
C5 S2 C8 C7 -0.65(14)
C5 S2 C8 C13' -176(4)
C5 S2 C8 C13 179.9(4)
C3 C4 C9 C10 169.21(18)
S1 C4 C9 C10 -11.6(3)
C3 C4 C9 S3 -13.7(3)
S1 C4 C9 S3 165.56(10)
C12 S3 C9 C10 -0.62(15)
C12 S3 C9 C4 -178.19(16)
C4 C9 C10 C11 178.56(18)
S3 C9 C10 C11 1.2(2)
C9 C10 C11 C12 -1.4(3)
C10 C11 C12 S3 0.9(2)
C9 S3 C12 C11 -0.16(17)
C7 C8 C13 C14 -173.2(6)
S2 C8 C13 C14 6.2(9)
C7 C8 C13 S4 5.1(7)
S2 C8 C13 S4 -175.5(3)
C8 C13 C14 C15 177.5(6)
S4 C13 C14 C15 -0.9(8)
C13 C14 C15 C16 0.7(8)
C14 C15 C16 S4 -0.1(5)
C15 C16 S4 C13 -0.4(3)
C14 C13 S4 C16 0.7(6)
C8 C13 S4 C16 -177.9(5)
C7 C8 C13' C14' 16(10)
S2 C8 C13' C14' -169(6)
C7 C8 C13' S4' -176(3)
S2 C8 C13' S4' -1(7)
C8 C13' C14' C15' 177(6)
S4' C13' C14' C15' 9(7)
C13' C14' C15' C16' -2(6)
C14' C15' C16' S4' -5(5)
C15' C16' S4' C13' 8(4)
C14' C13' S4' C16' -10(6)
C8 C13' S4' C16' 180(5)
