# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_name_full Org.Biomol.Chem.
_journal_coden_Cambridge 0177
_publ_contact_author_name 'Dekker, Frank'
_publ_contact_author_email f.j.dekker@rug.nl
_publ_section_title
;
Isothiazolones; thiol-reactive inhibitors of the histone
acetyl transferase PCAF and cysteine protease Cathepsin B
;
loop_
_publ_author_name
R.Wisastra
M.Ghizzoni
A.J.Minnaard
H.Maarsingh
H.Haisma
;
F.Dekker
;
data_q1569
_database_code_depnum_ccdc_archive 'CCDC 763228'
#TrackingRef 'q1569.cif'
#==============================================================================
# 0. AUDIT DETAILS
_audit_creation_date '2009-10-27 08:14:40'
_audit_creation_method
;
PLATON
option (version :: 300909)
SHELXL97-2 & Manual Editing
;
_audit_update_record
;
?
2010-01-25 # Formatted by publCIF
;
#===============================================================================
# 4. TEXT
_publ_section_synopsis .
_publ_section_abstract
;
(type here to add abstract)
;
# Insert blank lines between paragraphs
_publ_section_comment
;
(type here to add)
;
_publ_section_exptl_prep
;
;
_publ_section_exptl_refinement
;
All hydrogen atoms were located in a difference Fourier map and refined with
isotropic displacement parameters.
C---H distances were in the range of 0.91 -- 0.99(3) \%A.
;
_publ_section_related_literature
;
;
# Insert blank lines between references
_publ_section_references
;
Bruker, (2007). SMART (Version 5.632), SAINT-Plus (Version
7.46a) and SADABS (Version 2.10). Bruker AXS Inc., Madison, Wisconsin,
USA.
Meetsma, A. (2009). Extended version of the program PLUTO. University of
Groningen, The Netherlands. (unpublished).
Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7--13.
;
_publ_section_figure_captions
;
Fig. 1. Perspective PLUTO drawings of the molecule illustrating the
configuration and the adopted numbering scheme.
Fig. 2. Molecular packing viewed down unit cell axes.
Fig. 3. Perspective ORTEP drawing of the title compound. Displacement
ellipsoids for non-H atoms are represented at the 50% probability level. The
H-atoms are drawn with an arbitrary radius.
;
_publ_section_acknowledgements
;
?
;
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C9 H6 Cl N O S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural ?
_chemical_formula_sum 'C9 H6 Cl N O S'
_chemical_formula_iupac ?
_chemical_formula_weight 211.67
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall '-P 2ac 2ab'
_symmetry_space_group_name_H-M 'P b c a'
_symmetry_Int_Tables_number 61
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+z
_cell_length_a 13.912(3)
_cell_length_b 5.9518(12)
_cell_length_c 21.173(4)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1753.2(6)
_cell_formula_units_Z 8
_cell_measurement_temperature 100(1)
_cell_measurement_reflns_used 3992
_cell_measurement_theta_min 2.42
_cell_measurement_theta_max 28.91
_cell_special_details
;
The final unit cell was obtained from the xyz centroids of
3992 reflections after integration using the SAINTPLUS
software package (Bruker, 2007).
Reduced cell calculations did not indicate any higher metric lattice symmetry
and examination of the final atomic coordinates of the structure did not
yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988)
;
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.45
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_min 0.10
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.604
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 864
_exptl_absorpt_coefficient_mu 0.625
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS, (Bruker, 2007))'
_exptl_absorpt_correction_T_min 0.7649
_exptl_absorpt_correction_T_max 0.9394
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 100(1)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine focus sealed Siemens Mo tube '
_diffrn_radiation_monochromator 'parallel mounted graphite'
_diffrn_radiation_detector
;
CCD area-detector
;
_diffrn_measurement_device_type
;
Bruker Smart Apex; CCD area detector
;
_diffrn_measurement_method '\f and \w scans'
_diffrn_special_details
;
Crystal into the cold nitrogen stream of the low-temparature unit
(KRYOFLEX, (Bruker, 2007)).
;
_diffrn_detector_area_resol_mean 66.06
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% 0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
# number of measured reflections (redundant set)
_diffrn_reflns_number 14622
_diffrn_reflns_av_R_equivalents 0.0407
_diffrn_reflns_av_sigmaI/netI 0.0255
_diffrn_reflns_limit_h_min -18
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_theta_min 2.93
_diffrn_reflns_theta_max 28.28
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process
;
Intensity data were corrected for Lorentz and polarization
effects, decay and absorption and reduced to F~o~^2^
using SAINT-Plus & SADABS (Bruker, 2007).
;
# number of unique reflections
_reflns_number_total 2168
_reflns_number_gt 1801
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'SMART (Bruker, 2007)'
_computing_cell_refinement 'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction SAINT-Plus
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
PLATON (Spek, 2003)
PLUTO (Meetsma, 2009)
;
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.8096P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary direct
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details ?
_chemical_absolute_configuration .
_refine_ls_abs_structure_Flack ?
_refine_ls_number_reflns 2168
_refine_ls_number_parameters 142
_refine_ls_number_restraints 0
_refine_ls_number_constraints ?
_refine_ls_R_factor_all 0.0456
_refine_ls_R_factor_gt 0.0360
_refine_ls_wR_factor_ref 0.0937
_refine_ls_wR_factor_gt 0.0875
_refine_ls_goodness_of_fit_ref 1.040
_refine_ls_restrained_S_all 1.040
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.409
_refine_diff_density_min -0.290
_refine_diff_density_rms 0.069
_vrn_publ_code_number_frames 1800
_vrn_publ_code_frame_time_sec 10.0
_vrn_publ_code_meas_time_hour 7.8
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Cl Cl Uani 0.17092(3) 0.44509(8) 0.59628(2) 1.0 0.0263(2) . .
S S Uani 0.16876(3) 0.37608(7) 0.45906(2) 1.0 0.0205(1) . .
O O Uani 0.02924(9) 0.8986(2) 0.41276(6) 1.0 0.0228(4) . .
N N Uani 0.11372(11) 0.5653(2) 0.41070(7) 1.0 0.0185(4) . .
C1 C Uani 0.13737(13) 0.5391(3) 0.52330(8) 1.0 0.0198(5) . .
C2 C Uani 0.08770(12) 0.7262(3) 0.50887(9) 1.0 0.0201(5) . .
C3 C Uani 0.07209(12) 0.7489(3) 0.44129(8) 1.0 0.0187(5) . .
C4 C Uani 0.11732(12) 0.5358(3) 0.34355(8) 1.0 0.0171(5) . .
C5 C Uani 0.15529(12) 0.7083(3) 0.30646(9) 1.0 0.0201(5) . .
C6 C Uani 0.15666(12) 0.6820(3) 0.24151(9) 1.0 0.0215(5) . .
C7 C Uani 0.12153(13) 0.4857(3) 0.21387(9) 1.0 0.0213(5) . .
C8 C Uani 0.08561(12) 0.3135(3) 0.25157(8) 1.0 0.0205(5) . .
C9 C Uani 0.08293(12) 0.3376(3) 0.31681(9) 1.0 0.0192(5) . .
H1 H Uiso 0.0614(16) 0.824(4) 0.5386(10) 1.0 0.029(6) . .
H5 H Uiso 0.1760(12) 0.837(3) 0.3250(9) 1.0 0.013(5) . .
H6 H Uiso 0.1830(15) 0.798(4) 0.2171(10) 1.0 0.032(6) . .
H7 H Uiso 0.1207(14) 0.471(3) 0.1683(10) 1.0 0.020(5) . .
H8 H Uiso 0.0605(15) 0.181(4) 0.2323(10) 1.0 0.024(5) . .
H9 H Uiso 0.0570(13) 0.217(3) 0.3445(9) 1.0 0.021(5) . .
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
Cl 0.0349(3) 0.0265(3) 0.0174(2) 0.0037(2) -0.0047(2) -0.0010(2)
S 0.0255(3) 0.0179(2) 0.0182(2) 0.0004(2) -0.0033(2) 0.0042(2)
O 0.0269(7) 0.0192(6) 0.0223(7) 0.0001(5) -0.0009(5) 0.0053(5)
N 0.0233(7) 0.0164(7) 0.0159(8) 0.0002(5) -0.0015(5) 0.0034(5)
C1 0.0228(9) 0.0207(8) 0.0159(9) 0.0007(6) -0.0019(7) -0.0039(7)
C2 0.0211(8) 0.0195(8) 0.0196(9) -0.0023(7) 0.0021(7) -0.0017(7)
C3 0.0175(8) 0.0167(8) 0.0218(9) -0.0013(7) 0.0004(7) -0.0002(6)
C4 0.0167(8) 0.0190(8) 0.0157(8) -0.0007(6) -0.0011(6) 0.0027(6)
C5 0.0187(8) 0.0183(9) 0.0234(9) -0.0005(7) -0.0020(7) -0.0014(6)
C6 0.0188(8) 0.0225(9) 0.0231(9) 0.0050(7) 0.0020(7) 0.0002(7)
C7 0.0194(8) 0.0280(9) 0.0165(9) -0.0008(7) 0.0005(6) 0.0043(7)
C8 0.0190(8) 0.0187(8) 0.0237(10) -0.0046(7) -0.0011(7) 0.0013(6)
C9 0.0177(8) 0.0173(8) 0.0226(9) 0.0005(7) -0.0012(7) 0.0002(6)
#===============================================================================
# 10. MOLECULAR GEOMETRY
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl C1 1.7084(18) . . yes
S N 1.7038(15) . . yes
S C1 1.7269(18) . . yes
O C3 1.231(2) . . yes
N C3 1.396(2) . . yes
N C4 1.433(2) . . yes
C1 C2 1.346(3) . . no
C2 C3 1.454(3) . . no
C4 C5 1.396(3) . . no
C4 C9 1.393(3) . . no
C5 C6 1.384(3) . . no
C6 C7 1.395(3) . . no
C7 C8 1.392(3) . . no
C8 C9 1.389(3) . . no
C2 H1 0.93(2) . . no
C5 H5 0.908(18) . . no
C6 H6 0.94(2) . . no
C7 H7 0.97(2) . . no
C8 H8 0.95(2) . . no
C9 H9 0.995(18) . . no
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N S C1 89.33(8) . . . yes
S N C3 115.15(12) . . . yes
S N C4 119.96(11) . . . yes
C3 N C4 124.79(14) . . . yes
Cl C1 S 117.34(10) . . . yes
Cl C1 C2 128.07(14) . . . yes
S C1 C2 114.58(14) . . . yes
C1 C2 C3 112.16(16) . . . no
O C3 N 122.68(15) . . . yes
O C3 C2 128.53(16) . . . yes
N C3 C2 108.78(15) . . . yes
N C4 C5 118.75(15) . . . yes
N C4 C9 119.66(15) . . . yes
C5 C4 C9 121.60(16) . . . no
C4 C5 C6 118.74(16) . . . no
C5 C6 C7 120.44(17) . . . no
C6 C7 C8 120.12(17) . . . no
C7 C8 C9 120.25(16) . . . no
C4 C9 C8 118.83(16) . . . no
C1 C2 H1 124.4(14) . . . no
C3 C2 H1 123.2(14) . . . no
C4 C5 H5 119.8(12) . . . no
C6 C5 H5 121.4(12) . . . no
C5 C6 H6 118.0(14) . . . no
C7 C6 H6 121.5(14) . . . no
C6 C7 H7 119.8(11) . . . no
C8 C7 H7 120.0(11) . . . no
C7 C8 H8 119.7(13) . . . no
C9 C8 H8 120.0(13) . . . no
C4 C9 H9 119.7(11) . . . no
C8 C9 H9 121.4(11) . . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 S N C3 0.00(14) . . . . no
C1 S N C4 176.51(14) . . . . no
N S C1 Cl 179.46(11) . . . . no
N S C1 C2 0.17(15) . . . . no
S N C3 O -179.48(14) . . . . no
S N C3 C2 -0.19(18) . . . . no
C4 N C3 O 4.2(3) . . . . no
C4 N C3 C2 -176.49(15) . . . . no
S N C4 C5 -123.01(15) . . . . no
S N C4 C9 57.2(2) . . . . no
C3 N C4 C5 53.1(2) . . . . no
C3 N C4 C9 -126.70(18) . . . . no
Cl C1 C2 C3 -179.50(14) . . . . no
S C1 C2 C3 -0.3(2) . . . . no
C1 C2 C3 O 179.55(18) . . . . no
C1 C2 C3 N 0.3(2) . . . . no
N C4 C5 C6 -178.48(15) . . . . no
C9 C4 C5 C6 1.3(3) . . . . no
N C4 C9 C8 178.99(15) . . . . no
C5 C4 C9 C8 -0.8(3) . . . . no
C4 C5 C6 C7 -0.6(3) . . . . no
C5 C6 C7 C8 -0.6(3) . . . . no
C6 C7 C8 C9 1.2(3) . . . . no
C7 C8 C9 C4 -0.4(3) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl O 3.4605(15) . 5_566 no
Cl C7 3.639(2) . 8_555 no
Cl H6 2.99(2) . 8_565 no
Cl H7 2.991(19) . 8_555 no
S S 3.7370(10) . 7_555 no
S C2 3.6826(19) . 5_566 no
S S 3.7370(10) . 7_545 no
S C1 3.626(2) . 7_545 no
S C2 3.6589(19) . 7_545 no
S H9 3.033(19) . . no
O C5 3.070(2) . . no
O C9 3.393(2) . 1_565 no
O Cl 3.4605(15) . 5_566 no
O C2 3.223(2) . 5_576 no
O H7 2.74(2) . 4_555 no
O H5 2.785(18) . . no
O H9 2.414(18) . 1_565 no
O H1 2.32(2) . 5_576 no
C1 C2 3.572(3) . 5_566 no
C1 C3 3.463(3) . 5_566 no
C1 S 3.626(2) . 7_555 no
C2 S 3.6826(19) . 5_566 no
C2 O 3.223(2) . 5_576 no
C2 C1 3.572(3) . 5_566 no
C2 S 3.6589(19) . 7_555 no
C3 C1 3.463(3) . 5_566 no
C5 O 3.070(2) . . no
C6 C8 3.463(2) . 4_555 no
C7 Cl 3.639(2) . 8_554 no
C7 C9 3.592(3) . 4_555 no
C7 C8 3.556(3) . 4_555 no
C8 C6 3.463(2) . 4_545 no
C8 C7 3.556(3) . 4_545 no
C9 C7 3.592(3) . 4_545 no
C9 O 3.393(2) . 1_545 no
C3 H5 2.903(19) . . no
C4 H8 3.07(2) . 4_555 no
C6 H8 3.07(2) . 4_555 no
C7 H6 2.94(2) . 7_545 no
C7 H8 3.01(2) . 4_555 no
C7 H9 3.097(18) . 4_555 no
C8 H8 3.01(2) . 4_555 no
C9 H8 3.04(2) . 4_555 no
H1 O 2.32(2) . 5_576 no
H5 O 2.785(18) . . no
H5 C3 2.903(19) . . no
H6 C7 2.94(2) . 7_555 no
H6 Cl 2.99(2) . 8_564 no
H7 O 2.74(2) . 4_545 no
H7 Cl 2.991(19) . 8_554 no
H8 C4 3.07(2) . 4_545 no
H8 C6 3.07(2) . 4_545 no
H8 C7 3.01(2) . 4_545 no
H8 C8 3.01(2) . 4_545 no
H8 C9 3.04(2) . 4_545 no
H9 S 3.033(19) . . no
H9 O 2.414(18) . 1_545 no
H9 C7 3.097(18) . 4_545 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
C2 H1 O 0.93(2) 2.32(2) 3.223(2) 163.3(19) 5_576 yes
C9 H9 O 0.995(18) 2.414(18) 3.393(2) 167.8(15) 1_545 yes
data_q1570
_database_code_depnum_ccdc_archive 'CCDC 763229'
#TrackingRef 'q1570.cif'
#==============================================================================
# 0. AUDIT DETAILS
_audit_creation_date '2009-10-27 16:16:27'
_audit_creation_method
;
PLATON option (version :: 300909)
SHELXL97-2 & Manual Editing
;
_audit_update_record
;
?
2010-01-25 # Formatted by publCIF
;
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C9 H7 N O S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural ?
_chemical_formula_sum 'C9 H7 N O S'
_chemical_formula_iupac ?
_chemical_formula_weight 177.23
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_Int_Tables_number 14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
_cell_length_a 17.363(19)
_cell_length_b 6.389(7)
_cell_length_c 7.471(8)
_cell_angle_alpha 90
_cell_angle_beta 95.868(18)
_cell_angle_gamma 90
_cell_volume 824.4(16)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(1)
_cell_measurement_reflns_used 1437
_cell_measurement_theta_min 3.40
_cell_measurement_theta_max 25.08
_cell_special_details
;
The final unit cell was obtained from the xyz centroids of
1437 reflections after integration using the SAINTPLUS
software package (Bruker, 2007).
Reduced cell calculations did not indicate any higher metric lattice symmetry
and examination of the final atomic coordinates of the structure did not
yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988)
;
_exptl_crystal_description platelet
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.02
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.428
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 368
_exptl_absorpt_coefficient_mu 0.336
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS, (Bruker, 2007))'
_exptl_absorpt_correction_T_min 0.8791
_exptl_absorpt_correction_T_max 0.9900
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 100(1)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine focus sealed Siemens Mo tube '
_diffrn_radiation_monochromator 'parallel mounted graphite'
_diffrn_radiation_detector
;
CCD area-detector
;
_diffrn_measurement_device_type
;
Bruker Smart Apex; CCD area detector
;
_diffrn_measurement_method '\f and \w scans'
_diffrn_special_details
;
Crystal into the cold nitrogen stream of the low-temparature unit
(KRYOFLEX, (Bruker, 2007)).
;
_diffrn_detector_area_resol_mean 66.06
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% 0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
# number of measured reflections (redundant set)
_diffrn_reflns_number 4894
_diffrn_reflns_av_R_equivalents 0.0957
_diffrn_reflns_av_sigmaI/netI 0.0943
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_theta_min 3.40
_diffrn_reflns_theta_max 23.82
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 23.82
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_reduction_process
;
Intensity data were corrected for Lorentz and polarization
effects, decay and absorption and reduced to F~o~^2^
using SAINT-Plus & SADABS (Bruker, 2007).
;
# number of unique reflections
_reflns_number_total 1270
_reflns_number_gt 920
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'SMART (Bruker, 2007)'
_computing_cell_refinement 'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction SAINT-Plus
_computing_structure_solution
;
DIRDIF-08 (Beurskens et al., 2008)
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
PLATON (Spek, 2003)
PLUTO (Meetsma, 2009)
;
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1140P)^2^+0.7626P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary heavy
_atom_sites_solution_secondary direct
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack ?
_refine_ls_number_reflns 1270
_refine_ls_number_parameters 109
_refine_ls_number_restraints 0
_refine_ls_number_constraints ?
_refine_ls_R_factor_all 0.1081
_refine_ls_R_factor_gt 0.0767
_refine_ls_wR_factor_ref 0.2014
_refine_ls_wR_factor_gt 0.1824
_refine_ls_goodness_of_fit_ref 1.039
_refine_ls_restrained_S_all 1.039
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 1.312
_refine_diff_density_min -0.353
_refine_diff_density_rms 0.133
_vrn_publ_code_number_frames 1800
_vrn_publ_code_frame_time_sec 10.0
_vrn_publ_code_meas_time_hour 7.8
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
S S Uani 0.17419(8) 0.07046(18) 0.33877(15) 1.0 0.0253(5) . .
O O Uani 0.1166(2) 0.6419(5) 0.3879(4) 1.0 0.0287(13) . .
N N Uani 0.1856(3) 0.3371(6) 0.3433(5) 1.0 0.0228(14) . .
C1 C Uani 0.0803(3) 0.0975(7) 0.3815(6) 1.0 0.0257(18) . .
C2 C Uani 0.0579(3) 0.2974(7) 0.3985(6) 1.0 0.0226(18) . .
C3 C Uani 0.1190(3) 0.4479(7) 0.3774(6) 1.0 0.0212(18) . .
C4 C Uani 0.2608(3) 0.4235(7) 0.3276(6) 1.0 0.0240(18) . .
C5 C Uani 0.2681(3) 0.6121(7) 0.2358(6) 1.0 0.0268(18) . .
C6 C Uani 0.3414(3) 0.6890(8) 0.2184(7) 1.0 0.0323(19) . .
C7 C Uani 0.4076(4) 0.5819(9) 0.2876(7) 1.0 0.043(2) . .
C8 C Uani 0.3990(4) 0.3925(9) 0.3781(7) 1.0 0.041(2) . .
C9 C Uani 0.3270(3) 0.3139(9) 0.4009(6) 1.0 0.0313(19) . .
H1 H Uiso 0.04675 -0.01825 0.39228 1.0 0.0307 . .
H2 H Uiso 0.00712 0.33628 0.42202 1.0 0.0272 . .
H5 H Uiso 0.22347 0.68613 0.18633 1.0 0.0322 . .
H6 H Uiso 0.34662 0.81811 0.15772 1.0 0.0386 . .
H7 H Uiso 0.45764 0.63598 0.27372 1.0 0.0512 . .
H8 H Uiso 0.44378 0.31704 0.42456 1.0 0.0493 . .
H9 H Uiso 0.32196 0.18726 0.46533 1.0 0.0377 . .
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
S 0.0439(11) 0.0162(8) 0.0159(7) -0.0020(4) 0.0037(6) 0.0035(6)
O 0.045(3) 0.0153(19) 0.0267(19) -0.0006(14) 0.0084(18) 0.0018(16)
N 0.038(3) 0.016(2) 0.015(2) -0.0010(16) 0.005(2) 0.002(2)
C1 0.044(4) 0.023(3) 0.009(2) 0.0019(19) -0.002(2) -0.008(2)
C2 0.035(4) 0.017(3) 0.017(2) -0.0001(19) 0.008(2) 0.001(2)
C3 0.037(4) 0.018(3) 0.008(2) 0.0014(18) -0.001(2) 0.004(2)
C4 0.042(4) 0.023(3) 0.008(2) -0.0065(19) 0.007(2) -0.001(3)
C5 0.049(4) 0.023(3) 0.009(2) -0.0060(19) 0.006(2) 0.000(3)
C6 0.045(4) 0.037(3) 0.016(3) -0.001(2) 0.008(3) -0.008(3)
C7 0.048(4) 0.056(4) 0.025(3) 0.003(3) 0.008(3) -0.011(3)
C8 0.046(4) 0.053(4) 0.025(3) 0.003(3) 0.006(3) 0.006(3)
C9 0.044(4) 0.037(3) 0.013(3) 0.003(2) 0.004(3) 0.004(3)
#===============================================================================
# 10. MOLECULAR GEOMETRY
_geom_special_details
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S N 1.715(4) . . yes
S C1 1.702(6) . . yes
O C3 1.243(6) . . yes
N C3 1.401(7) . . yes
N C4 1.433(7) . . yes
C1 C2 1.345(7) . . no
C2 C3 1.452(7) . . no
C4 C5 1.399(7) . . no
C4 C9 1.408(7) . . no
C5 C6 1.383(7) . . no
C6 C7 1.391(8) . . no
C7 C8 1.402(8) . . no
C8 C9 1.374(9) . . no
C1 H1 0.95 . . no
C2 H2 0.95 . . no
C5 H5 0.95 . . no
C6 H6 0.95 . . no
C7 H7 0.95 . . no
C8 H8 0.95 . . no
C9 H9 0.95 . . no
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N S C1 90.4(2) . . . yes
S N C3 114.2(4) . . . yes
S N C4 119.0(4) . . . yes
C3 N C4 126.6(4) . . . yes
S C1 C2 114.0(4) . . . yes
C1 C2 C3 113.4(5) . . . no
O C3 N 123.3(5) . . . yes
O C3 C2 128.6(5) . . . yes
N C3 C2 108.1(4) . . . yes
N C4 C5 120.1(4) . . . yes
N C4 C9 119.4(4) . . . yes
C5 C4 C9 120.5(5) . . . no
C4 C5 C6 118.9(5) . . . no
C5 C6 C7 121.6(5) . . . no
C6 C7 C8 118.6(6) . . . no
C7 C8 C9 121.2(6) . . . no
C4 C9 C8 119.1(5) . . . no
S C1 H1 123 . . . no
C2 C1 H1 123 . . . no
C1 C2 H2 123 . . . no
C3 C2 H2 123 . . . no
C4 C5 H5 121 . . . no
C6 C5 H5 121 . . . no
C5 C6 H6 119 . . . no
C7 C6 H6 119 . . . no
C6 C7 H7 121 . . . no
C8 C7 H7 121 . . . no
C7 C8 H8 119 . . . no
C9 C8 H8 119 . . . no
C4 C9 H9 120 . . . no
C8 C9 H9 120 . . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 S N C3 0.2(3) . . . . no
C1 S N C4 175.2(3) . . . . no
N S C1 C2 0.1(4) . . . . no
S N C3 O 179.1(3) . . . . no
S N C3 C2 -0.3(5) . . . . no
C4 N C3 O 4.5(7) . . . . no
C4 N C3 C2 -174.9(4) . . . . no
S N C4 C5 144.9(4) . . . . no
S N C4 C9 -33.3(5) . . . . no
C3 N C4 C5 -40.7(6) . . . . no
C3 N C4 C9 141.0(5) . . . . no
S C1 C2 C3 -0.2(5) . . . . no
C1 C2 C3 O -179.0(5) . . . . no
C1 C2 C3 N 0.4(5) . . . . no
N C4 C5 C6 -178.2(4) . . . . no
C9 C4 C5 C6 0.0(7) . . . . no
N C4 C9 C8 177.0(4) . . . . no
C5 C4 C9 C8 -1.3(7) . . . . no
C4 C5 C6 C7 0.9(7) . . . . no
C5 C6 C7 C8 -0.5(8) . . . . no
C6 C7 C8 C9 -0.8(8) . . . . no
C7 C8 C9 C4 1.7(8) . . . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S O 2.951(5) . 1_545 no
S C5 3.476(6) . 1_545 no
S C5 3.439(6) . 4_555 no
S C3 3.484(6) . 4_554 no
S H9 2.75 . . no
S H5 2.87 . 1_545 no
S H5 3.12 . 4_555 no
O S 2.951(5) . 1_565 no
O C1 2.978(6) . 1_565 no
O C5 2.976(7) . . no
O H1 2.49 . 1_565 no
O H5 2.52 . . no
O H2 2.70 . 3_566 no
C1 O 2.978(6) . 1_545 no
C1 C2 3.575(8) . 2_545 no
C2 C1 3.575(8) . 2_555 no
C3 S 3.484(6) . 4_555 no
C5 S 3.439(6) . 4_554 no
C5 O 2.976(7) . . no
C5 S 3.476(6) . 1_565 no
C1 H1 2.96 . 3_556 no
C1 H2 3.09 . 2_545 no
C2 H2 2.98 . 3_566 no
C2 H1 3.08 . 3_556 no
C2 H1 2.93 . 2_555 no
C3 H5 2.86 . . no
C4 H9 3.09 . 4_554 no
C5 H9 3.00 . 4_554 no
C6 H9 3.06 . 4_554 no
C8 H6 3.00 . 4_565 no
C9 H6 3.03 . 4_565 no
H1 O 2.49 . 1_545 no
H1 C2 2.93 . 2_545 no
H1 C1 2.96 . 3_556 no
H1 C2 3.08 . 3_556 no
H1 H1 2.41 . 3_556 no
H2 C1 3.09 . 2_555 no
H2 O 2.70 . 3_566 no
H2 C2 2.98 . 3_566 no
H2 H2 2.42 . 3_566 no
H5 S 2.87 . 1_565 no
H5 O 2.52 . . no
H5 C3 2.86 . . no
H5 S 3.12 . 4_554 no
H6 C8 3.00 . 4_564 no
H6 C9 3.03 . 4_564 no
H9 S 2.75 . . no
H9 C4 3.09 . 4_555 no
H9 C5 3.00 . 4_555 no
H9 C6 3.06 . 4_555 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
C1 H1 O 0.9500 2.4900 2.978(6) 112 1_545 yes
C5 H5 S 0.9500 2.8700 3.476(6) 122 1_565 yes
C5 H5 O 0.9500 2.5200 2.976(7) 109 . yes
C9 H9 S 0.9500 2.7500 3.070(6) 101 . yes
#===END of Crystallographic Information File