#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/24/7002494.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_7002494
loop_
_publ_author_name
'Siemeling, Ulrich'
'Bruhn, Clemens'
'Bretthauer, Frauke'
'Borg, Marta'
'Träger, Frank'
'Vogel, Florian'
'Azzam, Waleed'
'Badin, Mihaela'
'Strunskus, Thomas'
'Wöll, Christof'
_publ_section_title
;
 Photoresponsive SAMs on gold fabricated from azobenzene-functionalised
 asparagusic acid derivatives
;
_journal_issue                   40
_journal_name_full               'Dalton Transactions'
_journal_page_first              8593
_journal_page_last               8604
_journal_paper_doi               10.1039/b905025f
_journal_year                    2009
_chemical_formula_moiety         'C16 H14 N2 O2 S2'
_chemical_formula_sum            'C16 H14 N2 O2 S2'
_chemical_formula_weight         330.41
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 91.690(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1961(13)
_cell_length_b                   5.0195(3)
_cell_length_c                   26.472(3)
_cell_measurement_reflns_used    7545
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.09
_cell_measurement_theta_min      2.00
_cell_volume                     1487.0(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      ' 148 frames, detector distance = 130 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7146
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.54
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_source_voltage           50
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.366
_exptl_absorpt_correction_T_max  0.9689
_exptl_absorpt_correction_T_min  0.8538
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-red ver. 1.31 (Stoe & Cie. 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0448P)²+0.8068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                1999
_reflns_number_total             2605
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905025f.txt
_cod_data_source_block           i0097
_cod_original_cell_volume        1487.1(3)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7002494
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1445(2) 0.7948(5) 0.34301(9) 0.0270(5) Uani 1 1 d . . .
C2 C 0.1528(2) 1.0278(5) 0.37884(10) 0.0288(6) Uani 1 1 d . . .
H2 H 0.1443 1.1949 0.3585 0.035 Uiso 1 1 calc R . .
C3 C 0.0530(2) 1.0224(5) 0.41651(10) 0.0309(6) Uani 1 1 d . . .
H3A H -0.0239 0.9797 0.3989 0.037 Uiso 1 1 calc R . .
H3B H 0.0456 1.1990 0.4328 0.037 Uiso 1 1 calc R . .
C4 C 0.2715(2) 1.0411(5) 0.40848(10) 0.0324(6) Uani 1 1 d . . .
H4A H 0.2792 1.2139 0.4263 0.039 Uiso 1 1 calc R . .
H4B H 0.3389 1.0229 0.3853 0.039 Uiso 1 1 calc R . .
C5 C 0.2542(2) 0.5845(5) 0.27806(9) 0.0294(6) Uani 1 1 d . . .
C6 C 0.1731(2) 0.5785(5) 0.23773(10) 0.0312(6) Uani 1 1 d . . .
H6 H 0.1077 0.6991 0.2361 0.037 Uiso 1 1 calc R . .
C7 C 0.1888(2) 0.3937(5) 0.19977(9) 0.0302(6) Uani 1 1 d . . .
H7 H 0.1329 0.3851 0.1721 0.036 Uiso 1 1 calc R . .
C8 C 0.2856(2) 0.2203(5) 0.20172(10) 0.0272(5) Uani 1 1 d . . .
C9 C 0.3666(2) 0.2284(6) 0.24266(10) 0.0341(6) Uani 1 1 d . . .
H9 H 0.4325 0.1091 0.2443 0.041 Uiso 1 1 calc R . .
C10 C 0.3505(2) 0.4113(6) 0.28101(10) 0.0359(6) Uani 1 1 d . . .
H10A H 0.4052 0.4180 0.3091 0.043 Uiso 1 1 calc R . .
C11 C 0.3931(2) -0.2816(5) 0.11952(9) 0.0265(5) Uani 1 1 d . . .
C12 C 0.3032(2) -0.3236(5) 0.08266(10) 0.0314(6) Uani 1 1 d . . .
H12 H 0.2318 -0.2211 0.0828 0.038 Uiso 1 1 calc R . .
C13 C 0.3188(2) -0.5150(6) 0.04605(10) 0.0339(6) Uani 1 1 d . . .
H13 H 0.2574 -0.5450 0.0211 0.041 Uiso 1 1 calc R . .
C14 C 0.4231(2) -0.6642(5) 0.04518(10) 0.0333(6) Uani 1 1 d . . .
H14 H 0.4332 -0.7952 0.0198 0.040 Uiso 1 1 calc R . .
C15 C 0.5122(2) -0.6213(5) 0.08141(10) 0.0344(6) Uani 1 1 d . . .
H15 H 0.5840 -0.7219 0.0808 0.041 Uiso 1 1 calc R . .
C16 C 0.4972(2) -0.4317(5) 0.11878(10) 0.0307(6) Uani 1 1 d . . .
H16 H 0.5582 -0.4045 0.1439 0.037 Uiso 1 1 calc R . .
N1 N 0.29215(17) 0.0377(4) 0.16027(8) 0.0291(5) Uani 1 1 d . . .
N2 N 0.38766(17) -0.0941(4) 0.16018(8) 0.0299(5) Uani 1 1 d . . .
O1 O 0.24694(15) 0.7759(4) 0.31619(7) 0.0342(4) Uani 1 1 d . . .
O2 O 0.06124(15) 0.6463(4) 0.33685(7) 0.0330(4) Uani 1 1 d . . .
S1 S 0.08828(5) 0.76938(14) 0.46420(2) 0.0321(2) Uani 1 1 d . . .
S2 S 0.27297(5) 0.76876(14) 0.45371(3) 0.0333(2) Uani 1 1 d . . .
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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
O2 C1 O1 123.0(2) . . ?
O2 C1 C2 126.9(2) . . ?
O1 C1 C2 110.0(2) . . ?
C1 C2 C3 111.5(2) . . ?
C1 C2 C4 113.3(2) . . ?
C3 C2 C4 108.0(2) . . ?
C1 C2 H2 108.0 . . ?
C3 C2 H2 108.0 . . ?
C4 C2 H2 108.0 . . ?
C2 C3 S1 108.54(17) . . ?
C2 C3 H3A 110.0 . . ?
S1 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
S1 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
C2 C4 S2 107.29(17) . . ?
C2 C4 H4A 110.3 . . ?
S2 C4 H4A 110.3 . . ?
C2 C4 H4B 110.3 . . ?
S2 C4 H4B 110.3 . . ?
H4A C4 H4B 108.5 . . ?
C6 C5 C10 121.5(2) . . ?
C6 C5 O1 121.5(2) . . ?
C10 C5 O1 116.9(2) . . ?
C5 C6 C7 118.8(2) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 N1 115.4(2) . . ?
C9 C8 N1 124.6(2) . . ?
C10 C9 C8 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C5 119.5(2) . . ?
C9 C10 H10A 120.3 . . ?
C5 C10 H10A 120.3 . . ?
C16 C11 C12 119.8(2) . . ?
C16 C11 N2 115.0(2) . . ?
C12 C11 N2 125.3(2) . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.8(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
N2 N1 C8 113.6(2) . . ?
N1 N2 C11 113.7(2) . . ?
C1 O1 C5 119.29(19) . . ?
C3 S1 S2 95.95(8) . . ?
C4 S2 S1 95.53(8) . . ?
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
C1 O2 1.201(3) . ?
C1 O1 1.370(3) . ?
C1 C2 1.507(3) . ?
C2 C3 1.520(3) . ?
C2 C4 1.524(4) . ?
C2 H2 1.0000 . ?
C3 S1 1.826(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 S2 1.817(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.382(4) . ?
C5 C10 1.386(4) . ?
C5 O1 1.398(3) . ?
C6 C7 1.382(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(4) . ?
C8 N1 1.433(3) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C16 1.388(4) . ?
C11 C12 1.398(4) . ?
C11 N2 1.433(3) . ?
C12 C13 1.380(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N1 N2 1.257(3) . ?
S1 S2 2.0944(9) . ?
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
O2 C1 C2 C3 13.1(4) . . . . ?
O1 C1 C2 C3 -168.4(2) . . . . ?
O2 C1 C2 C4 135.2(3) . . . . ?
O1 C1 C2 C4 -46.4(3) . . . . ?
C1 C2 C3 S1 76.0(2) . . . . ?
C4 C2 C3 S1 -49.0(2) . . . . ?
C1 C2 C4 S2 -70.9(2) . . . . ?
C3 C2 C4 S2 53.1(2) . . . . ?
C10 C5 C6 C7 0.3(4) . . . . ?
O1 C5 C6 C7 176.5(2) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 C9 1.2(4) . . . . ?
C6 C7 C8 N1 179.9(2) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
N1 C8 C9 C10 -179.1(2) . . . . ?
C8 C9 C10 C5 -0.2(4) . . . . ?
C6 C5 C10 C9 0.3(4) . . . . ?
O1 C5 C10 C9 -176.0(2) . . . . ?
C16 C11 C12 C13 0.3(4) . . . . ?
N2 C11 C12 C13 -178.6(2) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C14 C15 C16 C11 -0.9(4) . . . . ?
C12 C11 C16 C15 0.4(4) . . . . ?
N2 C11 C16 C15 179.5(2) . . . . ?
C7 C8 N1 N2 172.1(2) . . . . ?
C9 C8 N1 N2 -9.3(3) . . . . ?
C8 N1 N2 C11 178.50(19) . . . . ?
C16 C11 N2 N1 -179.4(2) . . . . ?
C12 C11 N2 N1 -0.4(4) . . . . ?
O2 C1 O1 C5 3.2(4) . . . . ?
C2 C1 O1 C5 -175.3(2) . . . . ?
C6 C5 O1 C1 57.9(3) . . . . ?
C10 C5 O1 C1 -125.8(3) . . . . ?
C2 C3 S1 S2 23.04(18) . . . . ?
C2 C4 S2 S1 -31.63(17) . . . . ?
C3 S1 S2 C4 4.74(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652637
