#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/24/7002497.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_7002497
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 H13 I N2 O2 S2'
_chemical_formula_sum            'C16 H13 I N2 O2 S2'
_chemical_formula_weight         456.30
_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                 96.528(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.938(3)
_cell_length_b                   5.0191(3)
_cell_length_c                   11.4987(12)
_cell_measurement_reflns_used    9454
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.15
_cell_volume                     1659.3(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      ' 152 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  0.0718
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8385
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.56
_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    2.191
_exptl_absorpt_correction_T_max  0.8572
_exptl_absorpt_correction_T_min  0.6304
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-red ver.1.31 (Stoe & Cie. 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.064
_refine_diff_density_max         1.009
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0434P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                2372
_reflns_number_total             2891
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905025f.txt
_cod_data_source_block           i0194
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7002497
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
C1 C 0.35544(14) 2.3061(9) 1.3107(3) 0.0351(9) Uani 1 1 d . . .
C2 C 0.38807(16) 2.5408(9) 1.3162(4) 0.0404(10) Uani 1 1 d . . .
H2 H 0.3693 2.7069 1.3215 0.048 Uiso 1 1 calc R . .
C3 C 0.42406(17) 2.5274(9) 1.4232(4) 0.0436(11) Uani 1 1 d . . .
H3A H 0.4089 2.4756 1.4928 0.052 Uiso 1 1 calc R . .
H3B H 0.4386 2.7044 1.4382 0.052 Uiso 1 1 calc R . .
C4 C 0.41437(17) 2.5622(10) 1.2078(4) 0.0468(11) Uani 1 1 d . . .
H4A H 0.4309 2.7349 1.2077 0.056 Uiso 1 1 calc R . .
H4B H 0.3923 2.5503 1.1355 0.056 Uiso 1 1 calc R . .
C5 C 0.29616(15) 2.0961(9) 1.1800(4) 0.0379(10) Uani 1 1 d . . .
C6 C 0.26028(16) 2.0594(10) 1.2478(4) 0.0438(10) Uani 1 1 d . . .
H6 H 0.2582 2.1649 1.3156 0.053 Uiso 1 1 calc R . .
C7 C 0.22766(17) 1.8666(10) 1.2149(5) 0.0537(13) Uani 1 1 d . . .
H7 H 0.2031 1.8369 1.2614 0.064 Uiso 1 1 calc R . .
C8 C 0.22996(16) 1.7163(10) 1.1160(5) 0.0553(15) Uani 1 1 d . . .
C9 C 0.2666(2) 1.7541(11) 1.0487(5) 0.0593(15) Uani 1 1 d . . .
H9 H 0.2686 1.6483 0.9810 0.071 Uiso 1 1 calc R . .
C10 C 0.30037(17) 1.9474(11) 1.0809(4) 0.0480(11) Uani 1 1 d . . .
H10 H 0.3255 1.9756 1.0359 0.058 Uiso 1 1 calc R . .
C11 C 0.15367(18) 1.2207(10) 0.9879(5) 0.0555(14) Uani 1 1 d . . .
C12 C 0.1199(2) 1.1457(10) 1.0594(4) 0.0592(17) Uani 1 1 d . . .
H12 H 0.1197 1.2242 1.1346 0.071 Uiso 1 1 calc R . .
C13 C 0.08616(18) 0.9551(9) 1.0206(4) 0.0440(11) Uani 1 1 d . . .
H13 H 0.0632 0.9025 1.0687 0.053 Uiso 1 1 calc R . .
C14 C 0.08723(15) 0.8455(8) 0.9105(3) 0.0346(9) Uani 1 1 d . . .
C15 C 0.12098(14) 0.9199(9) 0.8397(4) 0.0389(10) Uani 1 1 d . . .
H15 H 0.1214 0.8425 0.7644 0.047 Uiso 1 1 calc R . .
C16 C 0.15382(18) 1.1079(10) 0.8803(5) 0.0513(12) Uani 1 1 d . . .
H16 H 0.1769 1.1592 0.8323 0.062 Uiso 1 1 calc R . .
I I 0.036852(9) 0.56800(6) 0.84273(2) 0.03723(11) Uani 1 1 d . . .
N1 N 0.1885(2) 1.5140(11) 1.0984(4) 0.0721(16) Uani 1 1 d . . .
N2 N 0.19468(18) 1.4284(10) 1.0089(4) 0.0637(13) Uani 1 1 d . . .
O1 O 0.32887(11) 2.2986(7) 1.2052(3) 0.0443(8) Uani 1 1 d . . .
O2 O 0.35159(11) 2.1471(6) 1.3871(3) 0.0410(7) Uani 1 1 d . . .
S1 S 0.46829(4) 2.2822(3) 1.39684(10) 0.0443(3) Uani 1 1 d . . .
S2 S 0.45558(4) 2.2892(3) 1.21412(10) 0.0467(3) 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'
I I -0.4742 1.8119 '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 122.9(4) . . ?
O2 C1 C2 126.8(4) . . ?
O1 C1 C2 110.3(4) . . ?
C1 C2 C3 111.6(4) . . ?
C1 C2 C4 112.8(4) . . ?
C3 C2 C4 107.6(4) . . ?
C1 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
C4 C2 H2 108.2 . . ?
C2 C3 S1 108.9(3) . . ?
C2 C3 H3A 109.9 . . ?
S1 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
S1 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C2 C4 S2 107.4(3) . . ?
C2 C4 H4A 110.2 . . ?
S2 C4 H4A 110.2 . . ?
C2 C4 H4B 110.2 . . ?
S2 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C10 C5 C6 122.5(4) . . ?
C10 C5 O1 116.3(4) . . ?
C6 C5 O1 121.1(4) . . ?
C7 C6 C5 118.4(5) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C8 C7 C6 121.3(5) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 119.7(5) . . ?
C7 C8 N1 110.8(5) . . ?
C9 C8 N1 129.5(5) . . ?
C8 C9 C10 120.0(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 C9 118.1(5) . . ?
C5 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
C16 C11 C12 119.8(5) . . ?
C16 C11 N2 109.5(5) . . ?
C12 C11 N2 130.7(5) . . ?
C11 C12 C13 120.2(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 118.4(5) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 121.2(4) . . ?
C13 C14 I 121.1(3) . . ?
C15 C14 I 117.7(3) . . ?
C16 C15 C14 119.1(5) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C11 C16 C15 121.2(5) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
N2 N1 C8 99.4(6) . . ?
N1 N2 C11 101.1(5) . . ?
C1 O1 C5 120.4(3) . . ?
C3 S1 S2 96.26(16) . . ?
C4 S2 S1 95.33(16) . . ?
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(5) . ?
C1 O1 1.362(5) . ?
C1 C2 1.506(6) . ?
C2 C3 1.521(6) . ?
C2 C4 1.536(7) . ?
C2 H2 1.0000 . ?
C3 S1 1.826(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 S2 1.813(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.379(7) . ?
C5 C6 1.380(7) . ?
C5 O1 1.397(5) . ?
C6 C7 1.375(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.372(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(8) . ?
C8 N1 1.567(8) . ?
C9 C10 1.397(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.361(8) . ?
C11 C12 1.399(9) . ?
C11 N2 1.577(7) . ?
C12 C13 1.402(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(6) . ?
C14 I 2.101(4) . ?
C15 C16 1.382(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N1 N2 1.148(6) . ?
S1 S2 2.0916(16) . ?
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 11.7(7) . . . . ?
O1 C1 C2 C3 -169.7(4) . . . . ?
O2 C1 C2 C4 133.0(5) . . . . ?
O1 C1 C2 C4 -48.4(5) . . . . ?
C1 C2 C3 S1 76.5(4) . . . . ?
C4 C2 C3 S1 -47.7(4) . . . . ?
C1 C2 C4 S2 -70.2(4) . . . . ?
C3 C2 C4 S2 53.3(4) . . . . ?
C10 C5 C6 C7 0.1(7) . . . . ?
O1 C5 C6 C7 176.4(4) . . . . ?
C5 C6 C7 C8 -1.1(7) . . . . ?
C6 C7 C8 C9 1.6(7) . . . . ?
C6 C7 C8 N1 -179.5(4) . . . . ?
C7 C8 C9 C10 -1.1(8) . . . . ?
N1 C8 C9 C10 -179.7(4) . . . . ?
C6 C5 C10 C9 0.4(7) . . . . ?
O1 C5 C10 C9 -176.0(4) . . . . ?
C8 C9 C10 C5 0.1(8) . . . . ?
C16 C11 C12 C13 0.0(7) . . . . ?
N2 C11 C12 C13 179.4(4) . . . . ?
C11 C12 C13 C14 -0.3(7) . . . . ?
C12 C13 C14 C15 0.5(7) . . . . ?
C12 C13 C14 I -178.0(3) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
I C14 C15 C16 178.1(3) . . . . ?
C12 C11 C16 C15 0.2(7) . . . . ?
N2 C11 C16 C15 -179.4(4) . . . . ?
C14 C15 C16 C11 0.0(7) . . . . ?
C7 C8 N1 N2 174.2(4) . . . . ?
C9 C8 N1 N2 -7.0(7) . . . . ?
C8 N1 N2 C11 179.6(3) . . . . ?
C16 C11 N2 N1 176.5(4) . . . . ?
C12 C11 N2 N1 -3.0(7) . . . . ?
O2 C1 O1 C5 -1.8(6) . . . . ?
C2 C1 O1 C5 179.6(4) . . . . ?
C10 C5 O1 C1 -124.1(5) . . . . ?
C6 C5 O1 C1 59.4(6) . . . . ?
C2 C3 S1 S2 21.5(4) . . . . ?
C2 C4 S2 S1 -33.0(3) . . . . ?
C3 S1 S2 C4 6.4(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652638
