#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/45/4114571.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_4114571
loop_
_publ_author_name
'Yoshihiko Yamamoto'
'Hideyuki Takagishi'
'Kenji Itoh'
_publ_section_title
;
 Ruthenium-Catalyzed Cycloaddition of 1,6-Diynes with Isothiocyanates and
 Carbon Disulfide: First Transition-Metal Catalyzed [2 + 2 + 2]
 Cocyclotrimerization Involving CS Double Bond
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              28
_journal_page_last               29
_journal_paper_doi               10.1021/ja016510q
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C15 H17 N O6 S'
_chemical_formula_weight         339.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.057(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9808(10)
_cell_length_b                   11.2342(16)
_cell_length_c                   20.146(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1579.9(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7657
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   'empirical (SADABS) '
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.637
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.637
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.202
_refine_ls_shift/su_mean         0.024
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1808P)²+1.9580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1556
_reflns_number_gt                2005
_reflns_number_total             2279
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja016510q_s3.cif
_cod_data_source_block           yamamot
_cod_database_code               4114571
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S1 S 0.15621(10) 0.48005(5) 0.25882(3) 0.0399(3) Uani 1 1 d .
O2 O 0.6134(3) 0.28337(15) 0.16627(10) 0.0463(5) Uani 1 1 d .
N1 N 0.3428(3) 0.27732(18) 0.22376(11) 0.0413(6) Uani 1 1 d .
O1 O 0.4797(3) 0.45757(17) 0.19364(11) 0.0542(6) Uani 1 1 d .
O4 O -0.5526(3) 0.12732(18) 0.42734(12) 0.0576(6) Uani 1 1 d .
C4 C -0.3484(4) 0.2840(2) 0.39795(12) 0.0368(6) Uani 1 1 d .
O5 O -0.1477(3) 0.2039(2) 0.48518(11) 0.0670(7) Uani 1 1 d .
O6 O -0.2542(4) 0.38839(18) 0.49452(10) 0.0637(7) Uani 1 1 d .
C12 C -0.5509(4) 0.2429(2) 0.41452(12) 0.0406(6) Uani 1 1 d .
C14 C -0.2355(4) 0.2858(2) 0.46372(13) 0.0399(6) Uani 1 1 d .
C9 C 0.4757(4) 0.3493(2) 0.19482(12) 0.0384(6) Uani 1 1 d .
O3 O -0.6879(3) 0.3056(2) 0.41579(13) 0.0669(7) Uani 1 1 d .
C8 C 0.1928(4) 0.3255(2) 0.25311(12) 0.0371(6) Uani 1 1 d .
C6 C -0.1040(4) 0.2814(2) 0.31496(12) 0.0364(6) Uani 1 1 d .
C1 C -0.0558(4) 0.4938(2) 0.30176(13) 0.0397(6) Uani 1 1 d .
H1 H -0.1006 0.5704 0.3098 0.048 Uiso 1 1 calc R
C5 C -0.2475(4) 0.2011(2) 0.34777(14) 0.0430(7) Uani 1 1 d .
H5A H -0.1845 0.1355 0.3702 0.052 Uiso 1 1 calc R
H5B H -0.3378 0.1695 0.3157 0.052 Uiso 1 1 calc R
C7 C 0.0561(4) 0.2472(2) 0.28244(13) 0.0402(6) Uani 1 1 d .
H7 H 0.0790 0.1659 0.2789 0.048 Uiso 1 1 calc R
C2 C -0.1616(4) 0.4027(2) 0.32452(12) 0.0356(6) Uani 1 1 d .
C3 C -0.3456(4) 0.4067(2) 0.36311(13) 0.0395(6) Uani 1 1 d .
H3A H -0.4550 0.4160 0.3339 0.047 Uiso 1 1 calc R
H3B H -0.3448 0.4711 0.3952 0.047 Uiso 1 1 calc R
C13 C -0.7356(4) 0.0738(3) 0.44305(18) 0.0630(9) Uani 1 1 d .
H13A H -0.8080 0.1270 0.4706 0.094 Uiso 1 1 calc R
H13B H -0.7152 0.0002 0.4662 0.094 Uiso 1 1 calc R
H13C H -0.8051 0.0588 0.4028 0.094 Uiso 1 1 calc R
C11 C 0.8964(5) 0.2612(3) 0.10229(18) 0.0651(9) Uani 1 1 d .
H11A H 0.9424 0.2086 0.1363 0.098 Uiso 1 1 calc R
H11B H 1.0026 0.3025 0.0827 0.098 Uiso 1 1 calc R
H11C H 0.8312 0.2159 0.0688 0.098 Uiso 1 1 calc R
C10 C 0.7607(4) 0.3496(3) 0.13205(15) 0.0509(8) Uani 1 1 d .
H10A H 0.8280 0.4010 0.1629 0.061 Uiso 1 1 calc R
H10B H 0.7043 0.3986 0.0975 0.061 Uiso 1 1 calc R
C15 C -0.1542(6) 0.4019(4) 0.55715(16) 0.0770(11) Uani 1 1 d .
H15A H -0.1957 0.3411 0.5874 0.116 Uiso 1 1 calc R
H15B H -0.1819 0.4788 0.5756 0.116 Uiso 1 1 calc R
H15C H -0.0188 0.3946 0.5500 0.116 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 C8 104.26(12)
C9 O2 C10 115.5(2)
C8 N1 C9 119.3(2)
C12 O4 C13 117.3(2)
C12 C4 C14 106.8(2)
C12 C4 C5 112.6(2)
C14 C4 C5 109.7(2)
C12 C4 C3 112.4(2)
C14 C4 C3 111.8(2)
C5 C4 C3 103.5(2)
C14 O6 C15 117.0(3)
O3 C12 O4 124.7(3)
O3 C12 C4 124.9(3)
O4 C12 C4 110.4(2)
O5 C14 O6 124.0(3)
O5 C14 C4 124.5(2)
O6 C14 C4 111.5(2)
O1 C9 O2 121.8(2)
O1 C9 N1 128.1(2)
O2 C9 N1 110.1(2)
N1 C8 C7 117.6(2)
N1 C8 S1 123.39(19)
C7 C8 S1 119.0(2)
C7 C6 C2 124.5(2)
C7 C6 C5 126.5(2)
C2 C6 C5 109.0(2)
C2 C1 S1 125.2(2)
C6 C5 C4 103.3(2)
C6 C7 C8 125.4(2)
C1 C2 C6 121.6(2)
C1 C2 C3 128.7(2)
C6 C2 C3 109.7(2)
C2 C3 C4 102.7(2)
O2 C10 C11 107.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.722(3)
S1 C8 1.758(3)
O2 C9 1.343(3)
O2 C10 1.445(3)
N1 C8 1.319(3)
N1 C9 1.363(3)
O1 C9 1.216(3)
O4 C12 1.324(3)
O4 C13 1.447(3)
C4 C12 1.524(4)
C4 C14 1.541(4)
C4 C5 1.545(4)
C4 C3 1.546(3)
O5 C14 1.187(3)
O6 C14 1.315(3)
O6 C15 1.449(4)
C12 O3 1.188(3)
C8 C7 1.427(4)
C6 C7 1.352(4)
C6 C2 1.434(3)
C6 C5 1.501(4)
C1 C2 1.343(4)
C2 C3 1.503(4)
C11 C10 1.498(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660524
