#------------------------------------------------------------------------------
#$Date: 2025-08-18 15:30:32 +0200 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/1/50/47/1504701.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_1504701
loop_
_publ_author_name
'Tan, Jing'
'Liang, Fushun'
'Wang, Yeming'
'Cheng, Xin'
'Liu, Qun'
'Yuan, Hongjuan'
_publ_section_title
;
 Carbon tetrabromide-mediated carbon-sulfur bond formation via a sulfenyl
 bromide intermediate
;
_journal_coden_ASTM              ORLEF7
_journal_issue                   12
_journal_name_full               'Organic Letters'
_journal_page_first              2485
_journal_page_last               2488
_journal_paper_doi               10.1021/ol800765s
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C8 H13 N O2 S2'
_chemical_formula_weight         219.32
_space_group_IT_number           14
_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                 111.621(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1184(13)
_cell_length_b                   27.326(6)
_cell_length_c                   7.1032(15)
_cell_measurement_temperature    293(2)
_cell_volume                     1104.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6129
_diffrn_reflns_theta_full        26.06
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.756
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.000(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          4.345
_refine_ls_shift/su_mean         0.037
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0705P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                1725
_reflns_number_total             2170
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800765s-file002.cif
_cod_data_source_block           3aa
_cod_depositor_comments
;
 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-20
;
_cod_database_code               1504701
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 0.42102(10) 0.10914(2) 0.65676(8) 0.0557(2) Uani 1 1 d .
S2 S 0.74024(10) 0.17866(2) 0.54759(10) 0.0616(2) Uani 1 1 d .
N N 0.5687(3) 0.19297(6) 0.8358(3) 0.0522(4) Uani 1 1 d .
C8 C 0.5836(3) 0.16507(7) 0.6884(3) 0.0432(4) Uani 1 1 d .
C5 C 0.4525(4) 0.08173(7) 0.4454(3) 0.0492(5) Uani 1 1 d .
C7 C 0.2761(4) 0.08749(8) 0.2552(3) 0.0537(5) Uani 1 1 d .
O2 O 0.2911(3) 0.06579(7) 0.0988(2) 0.0735(5) Uani 1 1 d .
H2 H 0.4159 0.0509 0.1322 0.110 Uiso 1 1 calc R
C4 C 0.6526(4) 0.05224(8) 0.4703(4) 0.0585(6) Uani 1 1 d .
O1 O 0.6698(3) 0.03125(6) 0.3156(3) 0.0789(5) Uani 1 1 d .
C3 C 0.8450(5) 0.04438(9) 0.6690(4) 0.0749(7) Uani 1 1 d .
H3A H 0.9459 0.0186 0.6571 0.112 Uiso 1 1 calc R
H3B H 0.7793 0.0354 0.7678 0.112 Uiso 1 1 calc R
H3C H 0.9342 0.0740 0.7107 0.112 Uiso 1 1 calc R
C6 C 0.0609(4) 0.11751(11) 0.2130(4) 0.0773(7) Uani 1 1 d .
H6A H 0.1005 0.1472 0.2905 0.116 Uiso 1 1 calc R
H6B H -0.0519 0.0994 0.2497 0.116 Uiso 1 1 calc R
H6C H -0.0049 0.1253 0.0713 0.116 Uiso 1 1 calc R
C1 C 0.4243(5) 0.18095(10) 0.9528(4) 0.0750(7) Uani 1 1 d .
H1A H 0.2750 0.1686 0.8638 0.113 Uiso 1 1 calc R
H1B H 0.4005 0.2098 1.0199 0.113 Uiso 1 1 calc R
H1C H 0.5022 0.1565 1.0518 0.113 Uiso 1 1 calc R
C2 C 0.7069(5) 0.23771(9) 0.8967(4) 0.0782(8) Uani 1 1 d .
H2A H 0.8672 0.2311 0.9138 0.117 Uiso 1 1 calc R
H2B H 0.7006 0.2492 1.0223 0.117 Uiso 1 1 calc R
H2C H 0.6439 0.2622 0.7942 0.117 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0627(4) 0.0557(4) 0.0571(4) -0.0099(2) 0.0319(3) -0.0156(3)
S2 0.0664(4) 0.0556(4) 0.0743(5) -0.0018(3) 0.0395(3) -0.0099(3)
N 0.0548(10) 0.0516(10) 0.0469(10) -0.0060(8) 0.0148(8) 0.0008(8)
C8 0.0404(10) 0.0422(10) 0.0424(10) 0.0010(8) 0.0096(8) 0.0019(8)
C5 0.0531(11) 0.0441(11) 0.0536(12) -0.0074(9) 0.0233(10) -0.0077(9)
C7 0.0585(13) 0.0499(11) 0.0529(13) -0.0039(10) 0.0207(11) -0.0077(10)
O2 0.0811(12) 0.0787(12) 0.0560(10) -0.0113(9) 0.0199(9) 0.0018(9)
C4 0.0583(13) 0.0458(11) 0.0684(15) -0.0055(10) 0.0198(12) -0.0050(10)
O1 0.0783(12) 0.0779(11) 0.0819(13) -0.0236(9) 0.0311(11) 0.0118(9)
C3 0.0617(15) 0.0627(15) 0.0853(19) -0.0039(13) 0.0094(14) 0.0060(12)
C6 0.0655(16) 0.0863(18) 0.0760(18) 0.0039(14) 0.0214(14) 0.0124(13)
C1 0.0944(19) 0.0841(17) 0.0586(15) -0.0123(12) 0.0424(15) 0.0014(14)
C2 0.0862(18) 0.0583(14) 0.0744(17) -0.0204(13) 0.0110(14) -0.0093(12)
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
C5 S1 C8 103.93(9)
C8 N C1 123.65(18)
C8 N C2 121.05(19)
C1 N C2 115.27(19)
N C8 S2 124.72(15)
N C8 S1 113.14(15)
S2 C8 S1 122.13(12)
C7 C5 C4 120.62(19)
C7 C5 S1 119.50(16)
C4 C5 S1 119.83(17)
O2 C7 C5 120.4(2)
O2 C7 C6 114.7(2)
C5 C7 C6 124.8(2)
O1 C4 C5 119.2(2)
O1 C4 C3 117.7(2)
C5 C4 C3 123.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.751(2)
S1 C8 1.7921(19)
S2 C8 1.662(2)
N C8 1.325(2)
N C1 1.456(3)
N C2 1.459(3)
C5 C7 1.393(3)
C5 C4 1.421(3)
C7 O2 1.292(2)
C7 C6 1.485(3)
C4 O1 1.278(3)
C4 C3 1.483(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168302240
