#------------------------------------------------------------------------------
#$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $
#$Revision: 32112 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/69/2006913.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006913
loop_
_publ_author_name
'Fu, Tai Y.'
'Scheffer, John R.'
'Trotter, James'
_publ_section_title
;
 Photocleavage Reactions of Monothioimides
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              103
_journal_page_last               107
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C22 H19 N O S'
_chemical_formula_sum            'C22 H19 N O S'
_chemical_formula_weight         345.46
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.022(4)
_cell_length_b                   38.685(4)
_cell_length_c                   5.847(3)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    294
_cell_measurement_theta_max      54.3
_cell_measurement_theta_min      44.3
_cell_volume                     1814.5(13)
_computing_cell_refinement
;
MSC/AFC Diffractometer Control Software
;
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 19??)
;
_computing_data_reduction
;
TEXSAN (Molecular Structure Corporation, 1995)
;
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution
;
SIR92 (Altomare et al., 1993)
;
_diffrn_ambient_temperature      294
_diffrn_measurement_device       'Rigaku AFC-6S'
_diffrn_measurement_method       '\w-2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_sigmaI/netI    0.040
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2113
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         77.42
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        0.17
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.598
_exptl_absorpt_correction_T_max  0.787
_exptl_absorpt_correction_T_min  0.633
_exptl_absorpt_correction_type
;
\y scans (North, Phillips & Matthews, 1968)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.21
_refine_ls_extinction_coef       0.0000043(7)
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_ref   1.71
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2113
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/esd_max         0.019
_refine_ls_shift/esd_mean        0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
w = 1/[\s^2^(F~o~^2^) + 0.00022(F~o~^2^)^2^]
;
_refine_ls_wR_factor_ref
;
0.0845 (0.1132 for the enantiomeric structure)
;
_reflns_number_gt                1861
_reflns_number_total             2113
_reflns_threshold_expression     I>3.00\s(I)
_[local]_cod_data_source_file    fg1342.cif
_[local]_cod_data_source_block   1a
_[local]_cod_cif_authors_sg_H-M  'P 21 21 21 '
_[local]_cod_chemical_formula_sum_orig 'C22 H19 N O S '
_cod_original_cell_volume        1815.0(10)
_cod_database_code               2006913
loop_
_symmetry_equiv_pos_as_xyz
'  +x,  +y,  +z'
'1/2-x,  -y,1/2+z'
'1/2+x,1/2-y,  -z'
'  -x,1/2+y,1/2-z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
S1 .92041(7) .214950(10) .98850(10) .05250(10) Uani d ? . 1.000
O1 .7305(2) .10993(4) 1.0831(3) .0556(5) Uani d ? . 1.000
N1 .7563(2) .15855(4) .8610(3) .0398(4) Uani d ? . 1.000
C1 .8953(2) .17299(5) .9630(4) .0401(5) Uani d ? . 1.000
C2 1.0297(2) .14878(5) 1.0347(4) .0429(5) Uani d ? . 1.000
C3 1.0747(3) .12097(6) .8990(5) .0520(6) Uani d ? . 1.000
C4 1.2044(3) .09944(6) .9664(6) .0656(8) Uani d ? . 1.000
C5 1.2885(3) .10565(8) 1.1673(6) .0694(8) Uani d ? . 1.000
C6 1.2457(3) .13329(8) 1.3011(5) .0668(8) Uani d ? . 1.000
C7 1.1166(3) .15500(6) 1.2358(4) .0541(6) Uani d ? . 1.000
C8 .6392(2) .18012(5) .7379(4) .0375(5) Uani d ? . 1.000
C9 .4834(3) .18597(5) .8300(4) .0441(5) Uani d ? . 1.000
C10 .3694(3) .20595(6) .7108(5) .0536(6) Uani d ? . 1.000
C11 .4114(3) .21979(5) .5024(5) .0538(6) Uani d ? . 1.000
C12 .5678(3) .21387(6) .4107(4) .0522(6) Uani d ? . 1.000
C13 .6817(3) .19374(6) .5275(4) .0468(5) Uani d ? . 1.000
C14 .7037(2) .12378(5) .9027(4) .0433(5) Uani d ? . 1.000
C15 .6146(3) .10699(6) .7068(5) .0628(7) Uani d ? . 1.000
C16 .6109(3) .06751(6) .7242(6) .0685(8) Uani d ? . 1.000
C17 .7787(3) .05020(5) .6938(4) .0510(6) Uani d ? . 1.000
C18 .8379(3) .02802(6) .8590(5) .0570(7) Uani d ? . 1.000
C19 .9865(4) .01083(7) .8291(6) .0689(8) Uani d ? . 1.000
C20 1.0786(4) .01542(8) .6360(7) .0783(9) Uani d ? . 1.000
C21 1.0234(4) .03766(8) .4707(6) .0793(9) Uani d ? . 1.000
C22 .8730(4) .05492(7) .4988(5) .0701(8) Uani d ? . 1.000
H1 1.0173 .1167 .7600 .062 Uiso c ? . 1.000
H2 1.2351 .0803 .8733 .078 Uiso c ? . 1.000
H3 1.3761 .0907 1.2135 .083 Uiso c ? . 1.000
H4 1.3045 .1376 1.4388 .080 Uiso c ? . 1.000
H5 1.0877 .1742 1.3288 .065 Uiso c ? . 1.000
H6 .4547 .1764 .9742 .053 Uiso c ? . 1.000
H7 .2619 .2101 .7732 .064 Uiso c ? . 1.000
H8 .3332 .2335 .4213 .065 Uiso c ? . 1.000
H9 .5968 .2236 .2671 .062 Uiso c ? . 1.000
H10 .7883 .1893 .4637 .056 Uiso c ? . 1.000
H11 .5031 .1152 .7035 .075 Uiso c ? . 1.000
H12 .6694 .1132 .5688 .075 Uiso c ? . 1.000
H13 .5690 .0615 .8706 .082 Uiso c ? . 1.000
H14 .5379 .0590 .6093 .082 Uiso c ? . 1.000
H15 .7756 .0245 .9949 .068 Uiso c ? . 1.000
H16 1.0250 -.0044 .9446 .082 Uiso c ? . 1.000
H17 1.1804 .0033 .6161 .094 Uiso c ? . 1.000
H18 1.0883 .0414 .3369 .095 Uiso c ? . 1.000
H19 .8345 .0701 .3826 .084 Uiso c ? . 1.000
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 .0504(3) .0457(2) .0614(4) -.0048(2) .0003(3) -.0006(3)
O1 .0508(9) .0563(8) .0600(10) -.0026(7) -.0059(9) .0198(8)
N1 .0365(7) .0416(8) .0410(10) .0005(6) -.0059(8) .0058(7)
C1 .0370(8) .0490(10) .0340(10) -.0011(8) .0033(9) .0023(9)
C2 .0345(8) .0510(10) .0430(10) -.0026(8) -.0001(9) .0030(10)
C3 .0390(10) .0590(10) .0580(10) .0000(10) -.0040(10) -.0050(10)
C4 .0450(10) .0590(10) .093(2) .0080(10) -.001(2) -.0050(10)
C5 .0430(10) .079(2) .086(2) .0100(10) -.008(2) .022(2)
C6 .0480(10) .095(2) .058(2) .0040(10) -.0130(10) .0110(10)
C7 .0420(10) .0720(10) .0480(10) .0000(10) -.0080(10) .0010(10)
C8 .0371(9) .0383(8) .0370(10) .0023(7) -.0021(9) .0034(8)
C9 .0430(10) .0440(10) .0450(10) -.0015(8) .0050(10) .0030(9)
C10 .0400(10) .0510(10) .070(2) .0089(9) .0010(10) -.0020(10)
C11 .0510(10) .0450(10) .065(2) .0094(9) -.0130(10) .0080(10)
C12 .0600(10) .0530(10) .0440(10) .0020(10) -.0060(10) .0110(10)
C13 .0430(10) .0550(10) .0430(10) .0046(9) .0050(10) .0070(10)
C14 .0345(9) .0430(10) .0520(10) .0047(8) -.0050(10) .0070(10)
C15 .0600(10) .0450(10) .084(2) .0070(10) -.031(2) -.0050(10)
C16 .0560(10) .0460(10) .103(2) .0010(10) -.022(2) -.0070(10)
C17 .0550(10) .0390(10) .0590(10) -.0006(9) -.0120(10) .0000(10)
C18 .0600(10) .0550(10) .0560(10) -.0030(10) -.0010(10) .0090(10)
C19 .067(2) .0620(10) .078(2) .0110(10) -.009(2) .0190(10)
C20 .063(2) .072(2) .100(2) .0110(10) .009(2) -.002(2)
C21 .092(2) .084(2) .063(2) -.002(2) .024(2) -.001(2)
C22 .098(2) .0590(10) .053(2) .0020(10) -.010(2) .0120(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . . 1.643(2) no
O1 C14 . . 1.202(3) no
N1 C1 . . 1.383(2) no
N1 C8 . . 1.448(2) no
N1 C14 . . 1.431(2) no
C1 C2 . . 1.488(3) no
C2 C3 . . 1.385(3) no
C2 C7 . . 1.388(3) no
C3 C4 . . 1.390(3) no
C3 H1 . . .95 no
C4 C5 . . 1.376(4) no
C4 H2 . . .95 no
C5 C6 . . 1.368(4) no
C5 H3 . . .95 no
C6 C7 . . 1.387(3) no
C6 H4 . . .95 no
C7 H5 . . .95 no
C8 C9 . . 1.380(3) no
C8 C13 . . 1.381(3) no
C9 C10 . . 1.386(3) no
C9 H6 . . .95 no
C10 C11 . . 1.373(4) no
C10 H7 . . .95 no
C11 C12 . . 1.383(3) no
C11 H8 . . .95 no
C12 C13 . . 1.381(3) no
C12 H9 . . .95 no
C13 H10 . . .95 no
C14 C15 . . 1.499(3) no
C15 C16 . . 1.531(3) no
C15 H11 . . .95 no
C15 H12 . . .95 no
C16 C17 . . 1.514(3) no
C16 H13 . . .95 no
C16 H14 . . .95 no
C17 C18 . . 1.377(3) no
C17 C22 . . 1.380(4) no
C18 C19 . . 1.376(4) no
C18 H15 . . .95 no
C19 C20 . . 1.361(5) no
C19 H16 . . .95 no
C20 C21 . . 1.368(5) no
C20 H17 . . .95 no
C21 C22 . . 1.388(4) no
C21 H18 . . .95 no
C22 H19 . . .95 no
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O 0.049 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S 0.333 0.557
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 8 -1
2 4 -1
2 4 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C8 120.3(2) no
C1 N1 C14 123.0(2) no
C8 N1 C14 115.8(2) no
S1 C1 N1 122.50(10) no
S1 C1 C2 120.50(10) no
N1 C1 C2 116.9(2) no
C1 C2 C3 121.1(2) no
C1 C2 C7 119.6(2) no
C3 C2 C7 119.3(2) no
C2 C3 C4 119.9(2) no
C2 C3 H1 120.0 no
C4 C3 H1 120.1 no
C3 C4 C5 120.3(2) no
C3 C4 H2 119.8 no
C5 C4 H2 119.9 no
C4 C5 C6 120.1(2) no
C4 C5 H3 119.9 no
C6 C5 H3 120.0 no
C5 C6 C7 120.2(3) no
C5 C6 H4 120.0 no
C7 C6 H4 119.8 no
C2 C7 C6 120.2(2) no
C2 C7 H5 119.9 no
C6 C7 H5 119.9 no
N1 C8 C9 119.2(2) no
N1 C8 C13 120.2(2) no
C9 C8 C13 120.6(2) no
C8 C9 C10 119.5(2) no
C8 C9 H6 120.2 no
C10 C9 H6 120.3 no
C9 C10 C11 120.1(2) no
C9 C10 H7 120.0 no
C11 C10 H7 119.9 no
C10 C11 C12 120.2(2) no
C10 C11 H8 120.0 no
C12 C11 H8 119.9 no
C11 C12 C13 120.1(2) no
C11 C12 H9 120.0 no
C13 C12 H9 119.9 no
C8 C13 C12 119.5(2) no
C8 C13 H10 120.2 no
C12 C13 H10 120.3 no
O1 C14 N1 121.1(2) no
O1 C14 C15 124.2(2) no
N1 C14 C15 114.7(2) no
C14 C15 C16 113.0(2) no
C14 C15 H11 108.7 no
C14 C15 H12 108.6 no
C16 C15 H11 108.5 no
C16 C15 H12 108.5 no
H11 C15 H12 109.5 no
C15 C16 C17 114.6(2) no
C15 C16 H13 108.1 no
C15 C16 H14 108.1 no
C17 C16 H13 108.2 no
C17 C16 H14 108.2 no
H13 C16 H14 109.6 no
C16 C17 C18 120.0(3) no
C16 C17 C22 121.7(2) no
C18 C17 C22 118.2(2) no
C17 C18 C19 120.8(3) no
C17 C18 H15 119.6 no
C19 C18 H15 119.6 no
C18 C19 C20 120.8(3) no
C18 C19 H16 119.5 no
C20 C19 H16 119.6 no
C19 C20 C21 119.5(3) no
C19 C20 H17 120.3 no
C21 C20 H17 120.2 no
C20 C21 C22 120.0(3) no
C20 C21 H18 120.0 no
C22 C21 H18 120.0 no
C17 C22 C21 120.7(3) no
C17 C22 H19 119.6 no
C21 C22 H19 119.7 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 C10 3.553(2) 3_557 no
O1 C22 3.427(3) 1_556 no
O1 C5 3.583(3) 1_455 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
S1 C1 N1 C8 10.4(3) no
S1 C1 N1 C14 -158.3(2) no
S1 C1 C2 C3 -135.4(2) no
S1 C1 C2 C7 41.6(3) no
O1 C14 N1 C1 29.9(3) no
O1 C14 N1 C8 -139.3(2) no
O1 C14 C15 C16 -19.0(4) no
N1 C1 C2 C3 40.2(3) no
N1 C1 C2 C7 -142.8(2) no
N1 C8 C9 C10 -178.6(2) no
N1 C8 C13 C12 179.1(2) no
N1 C14 C15 C16 161.2(2) no
C1 N1 C8 C9 -109.4(2) no
C1 N1 C8 C13 72.6(3) no
C1 N1 C14 C15 -150.3(2) no
C1 C2 C3 C4 177.8(2) no
C1 C2 C7 C6 -177.9(2) no
C2 C1 N1 C8 -165.2(2) no
C2 C1 N1 C14 26.1(3) no
C2 C3 C4 C5 -0.1(4) no
C2 C7 C6 C5 0.2(4) no
C3 C2 C7 C6 -0.8(3) no
C3 C4 C5 C6 -0.6(4) no
C4 C3 C2 C7 0.8(4) no
C4 C5 C6 C7 0.5(4) no
C8 N1 C14 C15 40.5(3) no
C8 C9 C10 C11 0.0(3) no
C8 C13 C12 C11 -1.1(3) no
C9 C8 N1 C14 60.1(3) no
C9 C8 C13 C12 1.1(3) no
C9 C10 C11 C12 0.0(3) no
C10 C9 C8 C13 -0.5(3) no
C10 C11 C12 C13 0.6(4) no
C13 C8 N1 C14 -117.9(2) no
C14 C15 C16 C17 -68.6(3) no
C15 C16 C17 C18 125.2(3) no
C15 C16 C17 C22 -57.4(4) no
C16 C17 C18 C19 176.9(2) no
C16 C17 C22 C21 -177.4(2) no
C17 C18 C19 C20 0.2(4) no
C17 C22 C21 C20 0.7(5) no
C18 C17 C22 C21 0.1(4) no
C18 C19 C20 C21 0.6(5) no
C19 C18 C17 C22 -0.5(4) no
C19 C20 C21 C22 -1.1(5) no