#------------------------------------------------------------------------------
#$Date: 2022-09-14 23:33:16 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/00/4020058.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_4020058
loop_
_publ_author_name
'Tung Siu'
'Christine J. Picard'
'Andrei K. Yudin'
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              932
_journal_page_last               937
_journal_paper_doi               10.1021/jo048591p
_journal_volume                  70
_journal_year                    2005
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H14 N2 O3 S'
_chemical_formula_sum            'C16 H14 N2 O3 S'
_chemical_formula_weight         314.35
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.9615(2)
_cell_length_b                   9.9599(2)
_cell_length_c                   38.3334(10)
_cell_measurement_reflns_used    14432
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     3039.68(13)
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0737
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            12041
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.59
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
  Sortav (Blessing 1995)
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         6335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0342P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0936
_reflns_number_gt                5034
_reflns_number_total             6335
_reflns_threshold_expression     I>2σ(I)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4020058
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'
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
S1A S 0.77529(8) 0.28801(6) 0.237661(17) 0.03128(16) Uani 1 1 d . . .
O1A O 0.8399(2) 0.10045(18) 0.15836(5) 0.0376(4) Uani 1 1 d . . .
O2A O 0.3587(2) 0.31354(18) 0.19308(4) 0.0366(4) Uani 1 1 d . . .
O3A O 0.8800(2) 0.17222(18) 0.24450(4) 0.0430(5) Uani 1 1 d . . .
N1A N 0.6228(2) 0.21786(19) 0.18476(5) 0.0272(4) Uani 1 1 d . . .
N2A N 0.7197(2) 0.3234(2) 0.19963(5) 0.0294(5) Uani 1 1 d . . .
C1A C 0.6917(3) 0.1183(3) 0.16282(6) 0.0285(6) Uani 1 1 d . . .
C2A C 0.5461(3) 0.0464(2) 0.14802(6) 0.0271(6) Uani 1 1 d . . .
C3A C 0.5415(3) -0.0663(2) 0.12663(6) 0.0325(6) Uani 1 1 d . . .
H3AA H 0.6416 -0.1064 0.1181 0.039 Uiso 1 1 calc R . .
C4A C 0.3848(4) -0.1176(3) 0.11835(7) 0.0396(6) Uani 1 1 d . . .
H4AA H 0.3772 -0.1950 0.1040 0.047 Uiso 1 1 calc R . .
C5A C 0.2383(4) -0.0579(3) 0.13068(7) 0.0392(7) Uani 1 1 d . . .
H5AA H 0.1328 -0.0961 0.1247 0.047 Uiso 1 1 calc R . .
C6A C 0.2428(3) 0.0565(3) 0.15163(6) 0.0345(6) Uani 1 1 d . . .
H6AA H 0.1429 0.0980 0.1599 0.041 Uiso 1 1 calc R . .
C7A C 0.4000(3) 0.1068(2) 0.15980(6) 0.0265(5) Uani 1 1 d . . .
C8A C 0.4478(3) 0.2257(2) 0.18113(6) 0.0280(5) Uani 1 1 d . . .
C9A C 0.8788(4) 0.4380(3) 0.24890(7) 0.0444(7) Uani 1 1 d . . .
H9AA H 0.9784 0.4490 0.2342 0.067 Uiso 1 1 calc R . .
H9AB H 0.9129 0.4343 0.2734 0.067 Uiso 1 1 calc R . .
H9AC H 0.8027 0.5141 0.2454 0.067 Uiso 1 1 calc R . .
C10A C 0.5989(3) 0.2763(2) 0.26564(6) 0.0271(5) Uani 1 1 d . . .
C11A C 0.4745(3) 0.3736(2) 0.26330(6) 0.0302(6) Uani 1 1 d . . .
H11A H 0.4886 0.4488 0.2483 0.036 Uiso 1 1 calc R . .
C12A C 0.3305(3) 0.3600(3) 0.28289(6) 0.0338(6) Uani 1 1 d . . .
H12A H 0.2459 0.4271 0.2815 0.041 Uiso 1 1 calc R . .
C13A C 0.3067(3) 0.2505(3) 0.30455(6) 0.0363(7) Uani 1 1 d . . .
C14A C 0.4333(4) 0.1558(3) 0.30690(6) 0.0388(7) Uani 1 1 d . . .
H14A H 0.4185 0.0806 0.3219 0.047 Uiso 1 1 calc R . .
C15A C 0.5818(4) 0.1677(2) 0.28794(6) 0.0355(6) Uani 1 1 d . . .
H15A H 0.6690 0.1031 0.2902 0.043 Uiso 1 1 calc R . .
C16A C 0.1447(4) 0.2343(3) 0.32459(7) 0.0514(8) Uani 1 1 d . . .
H16A H 0.1648 0.1793 0.3454 0.077 Uiso 1 1 calc R . .
H16B H 0.0609 0.1904 0.3097 0.077 Uiso 1 1 calc R . .
H16C H 0.1031 0.3229 0.3317 0.077 Uiso 1 1 calc R . .
S1B S 0.11681(7) 0.48893(6) 0.114333(15) 0.02698(15) Uani 1 1 d . . .
O1B O -0.0756(2) 0.79037(17) 0.08815(4) 0.0388(4) Uani 1 1 d . . .
O2B O 0.0507(3) 0.43914(18) 0.01598(5) 0.0478(5) Uani 1 1 d . . .
O3B O 0.1846(2) 0.60634(17) 0.13161(4) 0.0354(4) Uani 1 1 d . . .
N1B N 0.0131(3) 0.59478(19) 0.06036(5) 0.0287(5) Uani 1 1 d . . .
N2B N -0.0303(2) 0.5028(2) 0.08726(5) 0.0302(5) Uani 1 1 d . . .
C1B C -0.0223(3) 0.7332(2) 0.06280(7) 0.0321(6) Uani 1 1 d . . .
C2B C 0.0131(3) 0.7867(3) 0.02720(6) 0.0341(6) Uani 1 1 d . . .
C3B C 0.0127(4) 0.9180(3) 0.01536(8) 0.0449(7) Uani 1 1 d . . .
H3BA H -0.0095 0.9910 0.0306 0.054 Uiso 1 1 calc R . .
C4B C 0.0461(4) 0.9384(3) -0.01965(8) 0.0534(8) Uani 1 1 d . . .
H4BA H 0.0455 1.0272 -0.0287 0.064 Uiso 1 1 calc R . .
C5B C 0.0805(4) 0.8320(3) -0.04180(8) 0.0548(9) Uani 1 1 d . . .
H5BA H 0.1044 0.8490 -0.0657 0.066 Uiso 1 1 calc R . .
C6B C 0.0806(4) 0.7007(3) -0.02955(7) 0.0452(7) Uani 1 1 d . . .
H6BA H 0.1031 0.6275 -0.0447 0.054 Uiso 1 1 calc R . .
C7B C 0.0471(3) 0.6801(3) 0.00515(6) 0.0344(6) Uani 1 1 d . . .
C8B C 0.0397(3) 0.5548(3) 0.02575(6) 0.0337(6) Uani 1 1 d . . .
C9B C 0.0242(3) 0.3786(3) 0.14406(6) 0.0345(6) Uani 1 1 d . . .
H9BA H -0.0743 0.4213 0.1546 0.052 Uiso 1 1 calc R . .
H9BB H 0.1054 0.3559 0.1623 0.052 Uiso 1 1 calc R . .
H9BC H -0.0104 0.2965 0.1319 0.052 Uiso 1 1 calc R . .
C10B C 0.2929(3) 0.3988(2) 0.09763(6) 0.0261(5) Uani 1 1 d . . .
C11B C 0.2714(3) 0.2941(2) 0.07431(6) 0.0327(6) Uani 1 1 d . . .
H11B H 0.1625 0.2709 0.0662 0.039 Uiso 1 1 calc R . .
C12B C 0.4108(3) 0.2236(3) 0.06300(7) 0.0357(6) Uani 1 1 d . . .
H12B H 0.3966 0.1509 0.0472 0.043 Uiso 1 1 calc R . .
C13B C 0.5716(3) 0.2572(2) 0.07431(6) 0.0302(6) Uani 1 1 d . . .
C14B C 0.5888(3) 0.3628(2) 0.09763(6) 0.0315(6) Uani 1 1 d . . .
H14B H 0.6976 0.3869 0.1057 0.038 Uiso 1 1 calc R . .
C15B C 0.4509(3) 0.4335(2) 0.10939(6) 0.0296(6) Uani 1 1 d . . .
H15B H 0.4646 0.5054 0.1254 0.036 Uiso 1 1 calc R . .
C16B C 0.7255(3) 0.1828(3) 0.06156(7) 0.0421(7) Uani 1 1 d . . .
H16D H 0.8171 0.2469 0.0576 0.063 Uiso 1 1 calc R . .
H16E H 0.6992 0.1366 0.0397 0.063 Uiso 1 1 calc R . .
H16F H 0.7600 0.1168 0.0791 0.063 Uiso 1 1 calc R . .
