#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/41/1504118.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_1504118
loop_
_publ_author_name
'Palsuledesai, Charuta C.'
'Murru, Siva'
'Sahoo, Santosh K.'
'Patel, Bhisma K.'
_publ_section_title
;
 Acyl-isothiocyanates as efficient thiocyanate transfer reagents.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3382
_journal_page_last               3385
_journal_paper_doi               10.1021/ol901561j
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C10 H9 N O2 S'
_chemical_formula_sum            'C10 H9 N O2 S'
_chemical_formula_weight         207.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.4658(2)
_cell_length_b                   10.2821(2)
_cell_length_c                   19.9354(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1940.28(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.97
_diffrn_measured_fraction_theta_max 0.97
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25598
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0372
_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)+(0.1200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1581
_reflns_number_gt                2597
_reflns_number_total             3268
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901561j_si_004.cif
_cod_data_source_block           siva1
_cod_database_code               1504118
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
S1 S 0.10777(3) 0.63553(3) 0.232557(16) 0.04618(15) Uani 1 1 d .
O1 O 0.35951(10) 1.18822(8) 0.50256(5) 0.0500(2) Uani 1 1 d .
O2 O -0.00309(10) 0.81770(10) 0.31532(5) 0.0575(3) Uani 1 1 d .
C1 C 0.27308(17) 1.26289(12) 0.54605(7) 0.0555(3) Uani 1 1 d .
H1A H 0.2106 1.3162 0.5199 0.083 Uiso 1 1 calc R
H1B H 0.3315 1.3173 0.5736 0.083 Uiso 1 1 calc R
H1C H 0.2186 1.2057 0.5740 0.083 Uiso 1 1 calc R
C5 C 0.18778(11) 0.91997(9) 0.37056(5) 0.0332(2) Uani 1 1 d .
C2 C 0.29686(12) 1.10252(9) 0.46058(5) 0.0371(2) Uani 1 1 d .
C7 C 0.38726(12) 1.02630(11) 0.42202(6) 0.0405(3) Uani 1 1 d .
H7 H 0.4845 1.0363 0.4262 0.049 Uiso 1 1 calc R
C4 C 0.09845(11) 0.99738(10) 0.40914(6) 0.0376(2) Uani 1 1 d .
H4 H 0.0012 0.9877 0.4047 0.045 Uiso 1 1 calc R
C6 C 0.33350(11) 0.93605(9) 0.37762(6) 0.0367(2) Uani 1 1 d .
H6 H 0.3949 0.8855 0.3522 0.044 Uiso 1 1 calc R
C3 C 0.15056(12) 1.08835(10) 0.45397(6) 0.0387(2) Uani 1 1 d .
H3 H 0.0893 1.1392 0.4793 0.046 Uiso 1 1 calc R
C8 C 0.12443(11) 0.82561(10) 0.32322(6) 0.0360(2) Uani 1 1 d .
C9 C 0.22094(11) 0.73755(9) 0.28400(5) 0.0356(2) Uani 1 1 d .
H9A H 0.2772 0.6846 0.3141 0.043 Uiso 1 1 calc R
H9B H 0.2841 0.7883 0.2560 0.043 Uiso 1 1 calc R
C10 C 0.23585(13) 0.54891(10) 0.19455(6) 0.0422(3) Uani 1 1 d .
N1 N 0.31767(15) 0.48580(12) 0.16772(7) 0.0642(4) 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'
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'
N N 0.0061 0.0033 '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
C10 S1 C9 97.75(5)
C2 O1 C1 118.57(10)
C4 C5 C6 118.45(9)
C4 C5 C8 118.72(9)
C6 C5 C8 122.82(9)
O1 C2 C7 116.05(10)
O1 C2 C3 124.08(10)
C7 C2 C3 119.87(10)
C6 C7 C2 120.41(10)
C3 C4 C5 121.74(10)
C7 C6 C5 120.57(10)
C4 C3 C2 118.94(10)
O2 C8 C5 121.78(10)
O2 C8 C9 119.57(10)
C5 C8 C9 118.65(9)
C8 C9 S1 106.42(7)
N1 C10 S1 176.55(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C10 1.6844(13)
S1 C9 1.8165(10)
O1 C2 1.3523(13)
O1 C1 1.4178(15)
O2 C8 1.2200(14)
C5 C4 1.3928(14)
C5 C6 1.3963(15)
C5 C8 1.4805(14)
C2 C7 1.3918(16)
C2 C3 1.3986(16)
C7 C6 1.3796(15)
C4 C3 1.3846(15)
C8 C9 1.5052(14)
C10 N1 1.1433(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4203432
