#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/68/1506849.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_1506849
loop_
_publ_author_name
'Hu, Jun'
'Liu, Yubiao'
'Khemtong, Chalermchai'
'El Khoury, Jouliana M.'
'McAfoos, Timothy J.'
'Taschner, Ian S.'
_publ_section_title
;
 Photochemical Patterning of a Self-Assembled Monolayer of
 7-Diazomethylcarbonyl-2,4,9-trithiaadmantane on Gold Films via Wolff
 Rearrangement
;
_journal_issue                   12
_journal_name_full               Langmuir
_journal_page_first              4933
_journal_paper_doi               10.1021/la049629w
_journal_volume                  20
_journal_year                    2004
_chemical_formula_moiety         'C9 H10 N2 O S3'
_chemical_formula_sum            'C9 H10 N2 O S3'
_chemical_formula_weight         258.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.701(3)
_cell_angle_beta                 87.867(3)
_cell_angle_gamma                87.491(3)
_cell_formula_units_Z            4
_cell_length_a                   7.3568(14)
_cell_length_b                   9.8242(18)
_cell_length_c                   15.334(3)
_cell_measurement_reflns_used    6232
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.42
_cell_volume                     1105.6(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9429
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  0.9097
_exptl_absorpt_correction_T_min  0.7477
_exptl_absorpt_correction_type   'multi-scan SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0560
_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)+(0.0688P)²+0.7012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                4261
_reflns_number_total             4892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            la049629wsi20040211_061150.cif
_cod_data_source_block           yubio
_cod_database_code               1506849
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.16582(10) 0.57526(7) 0.24745(5) 0.02720(18) Uani 1 1 d .
S2 S 0.10454(10) 0.28157(7) 0.20369(4) 0.02484(18) Uani 1 1 d .
S3 S -0.12613(9) 0.41863(7) 0.34889(5) 0.02755(18) Uani 1 1 d .
S4 S 0.73811(11) 1.09974(7) 0.15071(5) 0.02960(19) Uani 1 1 d .
S5 S 0.43239(11) 0.95662(7) 0.25322(5) 0.0327(2) Uani 1 1 d .
S6 S 0.82973(13) 0.89488(8) 0.29903(5) 0.0383(2) Uani 1 1 d .
O1 O 0.4309(3) 0.3301(2) 0.52901(13) 0.0367(5) Uani 1 1 d .
O2 O 0.6530(3) 0.6839(2) -0.02274(13) 0.0366(5) Uani 1 1 d .
N1 N 0.6859(3) 0.1358(2) 0.4924(2) 0.0354(6) Uani 1 1 d .
N2 N 0.7827(5) 0.1139(3) 0.54137(19) 0.0479(8) Uani 1 1 d .
N3 N 0.7771(4) 0.4334(2) 0.02358(17) 0.0335(6) Uani 1 1 d .
N4 N 0.7756(4) 0.3583(3) -0.02786(18) 0.0412(7) Uani 1 1 d .
C1 C 0.0657(4) 0.5306(3) 0.35500(18) 0.0258(6) Uani 1 1 d .
H1 H 0.0159 0.6174 0.3802 0.031 Uiso 1 1 calc R
C2 C 0.0067(4) 0.2668(3) 0.31548(17) 0.0236(5) Uani 1 1 d .
H2 H -0.0794 0.1907 0.3165 0.028 Uiso 1 1 calc R
C3 C 0.2718(4) 0.4074(3) 0.22460(17) 0.0235(5) Uani 1 1 d .
H3 H 0.3485 0.4190 0.1698 0.028 Uiso 1 1 calc R
C4 C 0.2084(4) 0.4707(3) 0.41715(17) 0.0233(5) Uani 1 1 d .
H4A H 0.1502 0.4554 0.4758 0.028 Uiso 1 1 calc R
H4B H 0.3039 0.5375 0.4224 0.028 Uiso 1 1 calc R
C5 C 0.1531(4) 0.2253(3) 0.38114(17) 0.0218(5) Uani 1 1 d .
H5A H 0.2142 0.1381 0.3639 0.026 Uiso 1 1 calc R
H5B H 0.0941 0.2100 0.4396 0.026 Uiso 1 1 calc R
C6 C 0.3998(4) 0.3564(3) 0.29658(16) 0.0213(5) Uani 1 1 d .
H6A H 0.4950 0.4233 0.3021 0.026 Uiso 1 1 calc R
H6B H 0.4608 0.2691 0.2796 0.026 Uiso 1 1 calc R
C7 C 0.2985(4) 0.3347(2) 0.38672(16) 0.0205(5) Uani 1 1 d .
C8 C 0.4332(4) 0.2825(3) 0.45620(17) 0.0252(6) Uani 1 1 d .
C9 C 0.5629(4) 0.1739(3) 0.43188(19) 0.0292(6) Uani 1 1 d .
H9 H 0.5615 0.1323 0.3770 0.035 Uiso 1 1 calc R
C10 C 0.8839(4) 0.9537(3) 0.18666(19) 0.0297(6) Uani 1 1 d .
H10 H 1.0114 0.9852 0.1854 0.036 Uiso 1 1 calc R
C11 C 0.6087(5) 0.8255(3) 0.27957(19) 0.0339(7) Uani 1 1 d .
H11 H 0.5676 0.7778 0.3352 0.041 Uiso 1 1 calc R
C12 C 0.5277(4) 1.0096(3) 0.14632(17) 0.0252(6) Uani 1 1 d .
H12 H 0.4361 1.0749 0.1192 0.030 Uiso 1 1 calc R
C13 C 0.8811(4) 0.8366(3) 0.12287(18) 0.0244(6) Uani 1 1 d .
H13A H 0.9700 0.7633 0.1411 0.029 Uiso 1 1 calc R
H13B H 0.9190 0.8707 0.0636 0.029 Uiso 1 1 calc R
C14 C 0.6287(4) 0.7177(3) 0.21011(19) 0.0296(6) Uani 1 1 d .
H14A H 0.5105 0.6746 0.2052 0.035 Uiso 1 1 calc R
H14B H 0.7189 0.6458 0.2291 0.035 Uiso 1 1 calc R
C15 C 0.5520(4) 0.8883(3) 0.08600(18) 0.0283(6) Uani 1 1 d .
H15A H 0.5939 0.9219 0.0273 0.034 Uiso 1 1 calc R
H15B H 0.4326 0.8475 0.0802 0.034 Uiso 1 1 calc R
C16 C 0.6896(4) 0.7769(2) 0.11970(17) 0.0214(5) Uani 1 1 d .
C17 C 0.7013(4) 0.6629(3) 0.05235(18) 0.0240(6) Uani 1 1 d .
C18 C 0.7716(5) 0.5299(3) 0.0826(2) 0.0366(7) Uani 1 1 d .
H18 H 0.8109 0.5125 0.1405 0.044 Uiso 1 1 calc R
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
C1 S1 C3 97.48(12)
C3 S2 C2 96.99(12)
C2 S3 C1 96.98(12)
C12 S4 C10 97.25(13)
C12 S5 C11 97.02(13)
C11 S6 C10 97.56(13)
N2 N1 C9 175.5(3)
N4 N3 C18 176.1(3)
C4 C1 S1 111.83(19)
C4 C1 S3 111.60(19)
S1 C1 S3 112.37(14)
C5 C2 S3 111.40(17)
C5 C2 S2 111.33(18)
S3 C2 S2 113.67(14)
C6 C3 S2 111.54(17)
C6 C3 S1 111.76(18)
S2 C3 S1 112.53(15)
C1 C4 C7 113.0(2)
C2 C5 C7 112.6(2)
C3 C6 C7 112.7(2)
C8 C7 C4 108.0(2)
C8 C7 C6 110.4(2)
C4 C7 C6 110.4(2)
C8 C7 C5 107.3(2)
C4 C7 C5 110.4(2)
C6 C7 C5 110.3(2)
O1 C8 C9 121.3(3)
O1 C8 C7 121.7(3)
C9 C8 C7 117.0(2)
N1 C9 C8 115.5(3)
C13 C10 S6 111.52(19)
C13 C10 S4 111.4(2)
S6 C10 S4 112.77(16)
C14 C11 S6 110.4(2)
C14 C11 S5 111.9(2)
S6 C11 S5 113.44(16)
C15 C12 S4 111.0(2)
C15 C12 S5 111.16(19)
S4 C12 S5 113.96(15)
C10 C13 C16 112.1(2)
C11 C14 C16 112.9(2)
C12 C15 C16 113.1(2)
C14 C16 C15 111.3(2)
C14 C16 C17 110.0(2)
C15 C16 C17 107.2(2)
C14 C16 C13 110.8(2)
C15 C16 C13 109.6(2)
C17 C16 C13 107.7(2)
O2 C17 C18 121.5(2)
O2 C17 C16 121.8(2)
C18 C17 C16 116.8(2)
N3 C18 C17 115.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.826(3)
S1 C3 1.834(3)
S2 C3 1.827(3)
S2 C2 1.837(3)
S3 C2 1.827(3)
S3 C1 1.834(3)
S4 C12 1.821(3)
S4 C10 1.832(3)
S5 C12 1.824(3)
S5 C11 1.832(3)
S6 C11 1.830(4)
S6 C10 1.831(3)
O1 C8 1.227(3)
O2 C17 1.225(3)
N1 N2 1.063(4)
N1 C9 1.352(4)
N3 N4 1.102(3)
N3 C18 1.335(4)
C1 C4 1.528(4)
C2 C5 1.533(4)
C3 C6 1.532(4)
C4 C7 1.546(3)
C5 C7 1.557(4)
C6 C7 1.557(3)
C7 C8 1.539(4)
C8 C9 1.451(4)
C10 C13 1.541(4)
C11 C14 1.531(4)
C12 C15 1.538(3)
C13 C16 1.553(4)
C14 C16 1.540(4)
C15 C16 1.545(4)
C16 C17 1.550(3)
C17 C18 1.450(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21374729
